A systematic structural study of halogen bonding versus hydrogen bonding within competitive supramolecular systems

As halogen bonds gain prevalence in supramolecular synthesis and materials chemistry, it has become necessary to examine more closely how such interactions compete with or complement hydrogen bonds whenever both are present within the same system. As hydrogen and halogen bonds have several fundamental features in common, it is often difficult to predict which will be the primary interaction in a supramolecular system, especially as they have comparable strength and geometric requirements. To address this challenge, a series of molecules containing both hydrogen- and halogen-bond donors were co-crystallized with various monotopic, ditopic symmetric and ditopic asymmetric acceptor molecules. The outcome of each reaction was examined using IR spectroscopy and, whenever possible, single-crystal X-ray diffraction. 24 crystal structures were obtained and subsequently analyzed, and the synthon preferences of the competing hydrogen- and halogen-bond donors were rationalized against a background of calculated molecular electrostatic potential values. It has been shown that readily accessible electrostatic potentials can offer useful practical guidelines for predicting the most likely primary synthons in these co-crystals as long as the potential differences are weighted appropriately.

1. Introduction

Practical synthetic crystal engineering requires the ability to organize and connect molecular building blocks into desired solid-state motifs and architectures. Such endeavors rely on site-specific intermolecular interactions that facilitate the preparation of homomeric constructions as well as of heteromeric co-crystals via selective and hierarchical self-assembly. To develop robust, versatile supramolecular synthetic strategies, we need more information about the relative importance of two of the most useful non-covalent synthetic tools; hydrogen bonds (HBs) and halogen bonds (XBs).

The nature of the hydrogen bond, and its role in structural chemistry, has been extensively documented since the early twentieth century. Pauling devoted considerable attention to `hydrogen bonding' in his seminal book from 1939 entitled Nature of the Chemical Bond (Pauling, 1960), and 20 years later, Piementel and McLellan summarized most of the available experimental data and relevant theoretical interpretations in `The Hydrogen Bond' (Pimentel & McClellan, 1960). The abundance of papers on this topic has, almost inevitably, created occasional confusion regarding vocabulary as well as of the fundamentals of this interaction. It is interesting to note then that the most recent attempt by IUPAC (Arunan et al., 2011) at unifying the language and terminology by which hydrogen bonding can be defined comes almost a century after Latimer and Rodebush proposed the concept of hydrogen bonding without actually using the term itself (Latimer & Rodebush, 1920). The basis of the IUPAC report is a broad analysis of the relevance and magnitude of the physical forces that drive hydrogen bonding and the dominant contribution in most hydrogen-bond interactions is the electrostatic component. However, the hydrogen bond is partially covalent in nature (McWeeny, 1979; Del Bene, 1970), and induction and dispersion, in addition to exchange correlation from short range repulsion, all have to be considered in order to fully appreciate the complexity of this chemical bond (Dykstra & Lisy, 2000; Umeyama & Morokuma, 1977). The IUPAC team also used crystallographic data in order to find unique bond lengths, angles and energies characteristic of hydrogen bonding. However, since it was deemed difficult to choose definitive hydrogen-bond distances (Raghavendra et al., 2006; Klein, 2006) or energies (Pauling, 1960; Jeffrey & Saenger, 1991; Desiraju & Steiner, 1999), the linearity of a hydrogen bond was identified as the `discriminative attribute' (Elghobashi & González, 2006). Spectroscopic data were also examined to find characteristic IR stretches and NMR shifts which would commonly accompany hydrogen bonds (e.g. frequent red-shift of X—H bands in the IR (Scheiner, 1997; Badger & Bauer, 1937) and a down-field shift in NMR (Hobza & Havlas, 2000)). However, alternative interpretations and views remain as to whether these spectroscopic methods produce consistent changes in response to the influence of hydrogen-bond interactions (Scheiner & Kar, 2002; Joseph & Jemmis, 2007). The efforts by the IUPAC task force clearly demonstrate that this topic is still hugely important and very complex.

Following closely behind the hydrogen bond, the halogen bond was highlighted as a viable non-covalent interaction some 60 years ago by Hassel (Hassel, 1970). It subsequently went through a rather quiet patch until Metrangolo and Resnati rejuvenated this field through a number of key articles (Metrangolo et al., 2005). The halogen bond displays many fundamental similarities to the hydrogen bond, and it has been dissected and debated recently in ways that are very reminiscent of the way in which hydrogen bonding has been described. This attention to halogen bonding is fully justified given its importance in supramolecular synthesis, materials chemistry, biological systems and drug design (Bauzá et al., 2011; Sarwar et al., 2010). Halogen bonds are also `tunable' through covalent modifications to the molecule on which the donor sites are found (Riley & Hobza, 2008, 2011). Electron-withdrawing groups facilitate the redistribution of electron density away from the tip of the halogen atom, thus making it more electropositive and a more effective halogen-bond donor. However, electrostatic forces are not solely responsible for defining the halogen bond as dispersion and induction also play a role (Jeziorski et al., 1994), which means that the debate about the nature and strengths of different halogen-bond interactions is remarkably similar to that which has accompanied the hydrogen bond (Řezáč et al., 2012; Riley & Hobza, 2013).

The question is, where does all this information leave the practitioner of synthetic crystal engineering? Hydrogen bonds and halogen bonds are complicated and subtle, directional yet reversible, chemical bonds, so how do we develop strategies that fully utilize the synthetic possibilities that these interactions offer, without having to resort to a serendipitous supramolecular combinatorial approach? One way of getting some answers may be through systematic structural studies where relatively simple custom-designed probe molecules, equipped with potentially competing hydrogen- and halogen-bond donor sites are introduced to a series of molecules decorated with different acceptor sites. By examining the structural outcome of a sufficient number of experiments, it may be possible to identify some of the finer details in the structural landscape that surrounds competing (or complementary) hydrogen and halogen bonds.

Studies that clearly address the balance between HBs and XBs are still quite unusual, but Desiraju and co-workers examined supramolecular synthons created through aniline–phenol interactions which included an analysis of the role played by secondary halogen bonds and π–π interactions (Mukherjee & Desiraju, 2014). Bruce and co-workers examined the outcome of reactions between 4-halo-tetrafluorophenols, which can act as both XB and HB donors, and a series of amines, and found that in each of the 11 structures that were reported (eight iodo- and three bromo-based donors) the outcome was a salt which was dominated by charge-assisted N—H⁺⋯O⁻ (phenolate) hydrogen bonds (Takemura, McAllister, Hart et al., 2014). The loss of the —OH moiety as a hydrogen-bond donor (due to deprotonation) made it difficult to draw any conclusions about the possible competition between XB and HB donor sites. In another study with 4-iodotetrafluorobenzoic acid, 4-iodotetrafluorophenol and 4-bromotetrafluorophenol, Bruce and co-workers used dithiane as an acceptor molecule (Takemura, McAllister, Karadakov et al., 2014) and found that careful co-former selection can lead to halogen-bond preference over hydrogen bonding consistent with an iodine basicity scale (Laurence et al., 2011), but the study only had access to four crystal structures of neutral co-crystals. Finally, Aakeröy and co-workers showed that in molecules containing both pyridine and amino-pyrimidine sites, hydrogen bonds are responsible for the assembly of the primary structural motif while halogen bonds play supporting roles (Aakeröy et al., 2009), and they also demonstrated that both hydrogen and halogen bonds can be used as simultaneous without structural interference if the main molecular recognition events are based upon a careful combination of geometric and electrostatic complementarity (Aakeröy et al., 2011).

The goal of our study is primarily to utilize crystallographic data on co-crystals of a wide range of ditopic molecules, each carrying a hydrogen-bond donor and a halogen-bond donor, in order to determine which is the more effective supramolecular synthetic vector. Second, we want to explore a simplified electrostatic view of hydrogen/halogen-bond interactions as a versatile and practical method for a priori identifying the most likely or dominant synthon in a competitive molecular recognition event (the protocol and work plan are outlined in Figs. 1–3).

Figure 1 The three postulated outcomes of co-crystallizations with a monotopic acceptor (X = halogen-bond donor; H = hydrogen-bond donor, A = halogen-/hydrogen-bond acceptor).

Figure 2 The three possible outcomes of co-crystallizations with a ditopic symmetric acceptor.

Figure 3 The four possible outcomes of co-crystallizations with a ditopic asymmetric acceptor (A1 = best acceptor; A2 = second best acceptor).

The first part of the study examines combinations of ditopic donors and monotopic acceptors with postulated outcomes presented in Fig. 1.

Second, ditopic symmetric acceptors were included in order to determine if the two donors were comparable in strength; this could be inferred if the HB donor formed an interaction with one acceptor site and the XB donor engaged with the other acceptor site, Fig. 2.

Finally, ditopic asymmetric acceptors were introduced, Fig. 3, to the HB/XB donors in order to probe how XB/HB donors would compete for acceptors sites offering electrostatic potential surfaces of different magnitudes (Etter, 1990).

In order to eliminate potentially misleading data resulting from possible solubility differences between hydrogen-bond donors and halogen-bond donors, the two donor sites were attached to the same molecular backbone, Fig. 4.

Figure 4 The hydrogen-/halogen-bond donors used in this study. X = I, Br.

For the carboxylic acid and oxime donors, both the fluorinated and non-fluorinated versions of the iodo and bromo derivatives were used. However, the non-fluorinated phenolic ligands were not considered due to very low electrostatic potential values on the halogen-bond donors, indicating that they would not be competitive.

The results of this study may help us answer several key questions: which is more effective, the hydrogen-bond donor or the halogen-bond donor? Additionally, when in direct competition with one another for acceptor molecules, what is the most likely outcome? Even though numerous physical forces are needed to give a full account of either interaction, is it possible to use readily accessible electrostatic potential surfaces as a way of ranking competing donors as well as predicting the most likely synthons? The overall outcome of this study may help to formulate versatile and useful synthetic crystal engineering strategies that facilitate the directed assembly of specific solid-state motifs through predictable synthons.

2. Experimental

2.1. Synthesis of ligands

Unless otherwise noted, the donor and acceptor ligands, in addition to the solvents, used throughout these experiments were obtained commercially and without further purification. Melting points were taken using a Gallenkamp melting point apparatus (see Table 1).

Table 1
Melting points of synthesized ditopic donors

Donor	Observed melting point (°C)	Literature data (°C)
IF4-COOH	136–139 dec.	140 dec. (Aakeröy et al., 2011)
BrF4-COOH	130–133	128–130 (Aakeröy et al., 2011)
IF4-OX	165–167	165–169 (Aakeröy, Sinha et al., 2012)
BrF4-OX	138–140	173–175 (Aakeröy, Sinha et al., 2012)
I-OX	101–108	101–103 (Aakeröy, Sinha et al., 2012)
Br-OX	100–105	110–112 (Narsaiah & Nagaiah, 2004)
IF4-OH	47–50	46–46.5 (Wen et al., 1994)

2,3,5,6-Tetrafluoro-4-iodobenzoic acid (IF₄-COOH) and 4-bromo-2,3,5,6-tetrafluorobenzoic acid (BrF₄-COOH) were synthesized according to previously reported methods in the literature (Aakeröy et al., 2011), whereas 4-iodobenzoic acid (I-COOH) and 4-bromobenzoic acid (Br-COOH) were purchased. (E)-2,3,5,6-Tetrafluoro-4-iodobenzaldehyde oxime (IF­₄-OX), (E)-4-bromo-2,3,5,6-tetrafluorobenzaldehyde oxime (BrF­₄-OX), (E)-4-iodobenzaldehyde oxime (I-OX) and (E)-4-bromobenzaldehyde oxime (Br-OX) were synthesized using a mechanochemical route (Aakeröy, Sinha et al., 2012). 2,3,5,6-Tetrafluoro-4-iodophenol (IF₄-OH) was synthesized by treating the corresponding pentafluoro­iodo­benzene with tert-butyl alcohol under reflux (Wen et al., 1994) and 4-bromo-2,3,5,6-tetrafluorophenol (BrF­₄-OH) was obtained commercially.

4-(Pyridine-4-yl)pyridine-1-oxide, pyrazine-1-oxide and 2,3,5,6-tetramethylpyrazine-1-oxide were synthesized according to literature methods (Aakeröy et al., 2014a). 5,6-Dimethyl-1-(pyridin-3-ylmethyl)-1H-benzo[D]imidazole, 5,6-dimethyl-1-(pyridin-4-ylmethyl)-1H-benzo[D]imidazole (Aakeröy, Desper & Smith, 2007) and 1-(pyridin-4-ylmethyl)-1H-benzo[D]imidazole (Aakeröy, Epa, Forbes, Schultheiss & Desper, 2013) were synthesized according to published procedures (see Table 2).

Table 2
Melting points of synthesized acceptors

Acceptor	Observed melting point (°C)	Literature data (°C)
A15	170–172	170–171 (Aakeröy et al., 2014a)
A16	110–113	113–115 (Aakeröy et al., 2014a)
A17	98–100	113–115 (Aakeröy et al., 2014a)
A18	126–131	150–153 (Aakeröy, Desper & Smith, 2007)
A19	98–108	105–110 (Aakeröy, Epa, Forbes, Schultheiss & Desper, 2013)
A20	179–184	182–190 (Aakeröy, Desper & Smith, 2007)

2.2. Electrostatic potential calculations

Calculations of molecular electrostatic surface potentials were carried out using DFT with the B3LYP level of theory and a 6-31++G** basis set in vacuum. All calculations were carried out using Spartan'08 software. All molecules were geometry optimized with the maxima and minima in the electrostatic potential surface (0.002 e a.u.⁻¹ isosurface) determined using a positive point charge in the vacuum as a probe. The numbers indicate the interaction energy (kJ mol⁻¹) between the positive point probe and the surface of the molecule at that particular point. These numbers could be correlated to the electrostatic charges on the atoms with the negative number corresponding to negative charge and positive number corresponding to positive charge. The program automatically identifies the maximum/minimum points on the surface.

2.3. IR analysis

The outcome of each attempted co-crystallization was analyzed using IR spectroscopy (Nicolet 380 FT-IR). Vibrational spectroscopy provides information about whether the two reactants have formed a heteromeric solid based on characteristic shifts or new key bands. For example, O—H⋯N(heterocycle) hydrogen bonds tend to produce two broad bands around 1900 and 2500 cm⁻¹, Fig. 5.

Figure 5 IR spectrum of BrF4-COOH – 1, showing O—H⋯N features at 1900 and 2450 cm^−1.

2.4. Synthesis of co-crystals

Ten HB/XB ditopic donor molecules were combined with 20 different acceptors in a series of co-crystallization experiments, Fig. 6.

Figure 6 (a) Halogen-/hydrogen-bond donors, and (b) HB/XB acceptors.

Stoichiometric amounts of the two reactants were mixed with a few drops of solvent and put through a solvent-assisted grinding protocol (James et al., 2012; Aakeröy, Sinha et al., 2012; Aakeröy, Chopade et al., 2012). The details for the preparation of compounds that yielded crystals suitable for single-crystal X-ray diffraction are shown in Table 3.

Table 3
Synthesis, melting points and crystal habit

D—A	D:A ratio	Solvent†	Melting point (°C)	Shape/color
IF4-COOH – 2	1:1	MeOH/CH2Cl2	125–129	Colorless blocks
IF4-COOH – 4	1:4	EtOH/CH2Cl2	102–104	Large colorless needles
IF4-COOH – 12	1:1	MeOH/trace CH2Cl2	165–170 dec.	Colorless thin plates
IF4-COOH – 13	1:1	MeOH	138–141 dec	Colorless rectangular prisms
IF4-COOH – 16	1:2	EtOAc/NitroMe	111–115	Colorless blocks
BrF4-COOH – 11	1:1	Chloroform	137–139	Off-white prisms
I-COOH – 11	1:1	MeOH/EtOH	190–192	Opaque prisms
I-COOH – 12	1:2	MeOH/EtOH	179–182	Colorless plates
Br-COOH – 2	1:4	MeOH	210–221	Colorless, flat, large plates
Br-COOH – 3	1:4	EtOAc	151–153	Colorless blocks
Br-COOH – 5	1:4	EtOAc	159–162	Colorless, short, thin needles
Br-COOH – 12	1:2	MeOH	159–164 dec.	Colorless blocks
Br-COOH – 11	1:2	MeOH/EtOH	140–142	Colorless blocks
IF4-OX – 3	1:1	MeOH	90–94 dec.	Yellow, wide needles
IF4-OX – 11	1:1	MeOH	135–142	Opaque, rectangular prisms
IF4-OX – 13	1:1	EtOAc/NitroMe	133–135	Colorless thin needles
BrF4-OX – 14	1:1	MeOH/EtOH	141–145	Colorless long, thin needles
Br-OX – 5	1:1	MeOH	108–112	Colorless, rectangular prisms
IF4-OH – 2	1:1	MeOH	97–98 dec.	Light yellow needles
IF4-OH – 16	1:1	MeOH	102–106 dec.	Large orange rectangular prism
BrF4-OH – 2	1:1	MeOH	100–103 dec.	Light yellow needles
BrF4-OH – 11	1:1	MeOH	125–130	Colorless, long needles
BrF4-OH – 12	1:1	MeOH	118–119	Colorless, long, thin needles
BrF4-OH – 13	1:1	MeOH	119–121 dec.	Flat colorless rectangular plate

†MeOH = methanol, EtOH = ethanol, CH₂Cl₂ = dichloromethane, EtOAc = ethyl acetate, NitroMe = nitromethane.

2.5. Crystal structure analysis

Crystallographic data can be found in the supporting information for all 24 structure determinations.

3. Results

3.1. Electrostatic potential calculations

The results for the ten HB/XB donors are displayed in Table 4, and the corresponding results for the 20 acceptors are included in the supporting information.

Table 4
Molecular electrostatic potential values for the HB/XB donors

Donor ligand	Hydrogen atom (kJ mol^−1)	Halogen atom (kJ mol^−1)
IF4-COOH	301.5	167.1
BrF4-COOH	288.3	139.1
I-COOH	266.9	112.8
Br-COOH	273.7	87.3
IF4-OX	273.8	158.9
BrF4-OX	279.0	127.8
I-OX	256.1	100.6
Br-OX	258.7	77.2
IF4-OH	304.8	149.6
BrF4-OH	315.3	125.8

3.2. IR analysis

Table 5 describes the outcomes of all 200 (10 × 20) attempted co-crystallizations as established by IR spectroscopy. The relative success rate for each donor, as well as for each acceptor, is also given.

Table 5
Outcome of co-crystal synthesis

In this table () indicates a co-crystal and (–) indicates no reaction.

		Donors
		IF4-COOH	BrF4-COOH	I-COOH	Br-COOH	IF4-OX	BrF4-OX	I- OX	Br- OX	IF4-OH	BrF4-OH
XB potential (kJ mol^−1)		167	139	113	87	159	128	101	77	150	126
HB potential (kJ mol^−1)		302	288	267	274	247	279	256	259	305	315	% Success
Acceptors	1			–				–	–			70
	2								–			90
	3	–	–	–	–					–		50
	4		–	–	–	–	–	–	–			30
	5	–	–	–	–					–		50
	6			–	–	–	–	–	–	–	–	20
	7			–	–	–	–	–	–		–	30
	8		–		–		–	–	–			50
	9								–			90
	10		–	–	–		–		–	–	–	30
	11	–	–						–	–		60
	12	–	–					–	–			60
	13			–	–		–	–	–			50
	14	–	–					–				70
	15	–	–	–	–							60
	16						–		–	–	–	60
	17			–	–	–		–			–	50
	18		–			–	–	–			–	50
	19	–	–	–	–	–	–	–	–			20
	20	–	–		–			–	–			50
		12/20	8/20	9/20	8/20	14/20	11/20	8/20	6/20	14/20	14/20
% Success		60	40	45	40	70	55	40	30	70	70

Table 5 has been split into columns in order to emphasize the relationship between the different halogen-bond donors. For example, the first two columns show the fluorinated iodo- and bromo-species of benzoic acid, whereas the two columns to their right show the non-fluorinated analogues. This arrangement highlights the percent success for each donor type. It can be seen that in every case, the iodo-donor has an equivalent or higher percentage success than its analogous bromo-donor. Furthermore, the fluorinated analogues are more successful at co-crystal formation than their non-fluorinated counterparts, which is in agreement with the electrostatic potential values on the HB and XB donors, as shown at the top of the table.

3.3. Co-crystal results

Over half of the 200 different donor:acceptor reactions carried out produced co-crystals and 24 of them yielded crystals suitable for single-crystal X-ray diffraction. Each acceptor can be placed in one of three categories: monotopic, ditopic symmetric and ditopic asymmetric. The possible connectivities and stoichiometries of the resulting supramolecular assemblies were described in Figs. 1–3. The results from the 24 new crystal structures are summarized in Tables 6–8.

Table 6
Monotopic acceptors (X = halogen-bond donor; H = hydrogen-bond donor; A = acceptor)

Crystal structures	Scheme	Codes
1/5		IF4-COOH – 4
4/5		IF4-OX – 3
		Br-OX – 5
		Br-COOH – 5
		Br-COOH – 3
0		–

Table 7
Ditopic symmetric acceptors (X = halogen-bond donor; H = hydrogen-bond donor; A = acceptor)

Crystal structures	Scheme	Codes
8/13		I-COOH – 12
		I-COOH – 11
		BrF4-OH – 13
		BrF4-COOH – 11
		IF4-OX – 13
		IF4-OX – 11
		IF4-COOH – 13
		IF4-COOH – 12
5/13		Br-COOH – 11
		Br-COOH – 12
		BrF4-OX – 14
		BrF4-OH – 11
		BrF4-OH – 12
0		–

Table 8
Ditopic asymmetric acceptors (X = halogen-bond donor; H = hydrogen-bond donor)

Crystal structures	Scheme	Codes
4/4		IF4-OH – 16
		IF4-OH – 2
		Br-COOH – 2
		BrF4-OH – 2
0		–
0		–
0		–
The crystal structures of IF4-COOH – 16 and IF4-COOH – 2 were both disordered in such a way that no determination of binding preference of the HB and XB donor moieties could be made.

Detailed crystallographic data has been included in the supporting information and deposited with the CCDC (1059404–1059416, 1059418–1059428), but relevant information about the primary hydrogen and halogen bonds is shown in Table 9. During the course of this study we were also able to isolate the structures for IF4-OH--5 (Takemura, McAllister, Hart et al., 2014) and IF4-OH--12 (Takemura, McAllister, Karadakov et al., 2014), but since they were recently reported by Bruce and co-workers, we have not included them in our results and will instead examine them as part of the discussion.

Table 9
Summary of hydrogen and halogen bond lengths (Å) and angles (°)

Code	HB distance (Å) heavy atom–A	HB angle (°)	XB distance (Å) X—A	% van der Waals radii reduction	XB angle (°)
IF4-OX – 3	2.649 (3)	164.2	–	–	–
Br-OX – 5	2.678 (2)	171 (3)	–	–	–
Br-COOH – 5	2.509 (3)	173 (4)	–	–	–
	2.690 (3)	172 (4)	–	–	–
Br-COOH – 3	2.7077 (16)	173.1 (18)	–	–	–
IF4-COOH – 4	2.531 (16)	164	2.788 (10)	21	173.7 (5)
I-COOH – 12	2.666 (9)	173.9	2.941 (8)	17	177.8 (3)
I-COOH – 11	2.681 (12)	173.1	2.950 (8)	16	176.2 (7)
BrF4-OH – 13	2.659 (3)	152 (4)	3.017 (2)	11	168.89 (11)
BrF4-COOH – 11	2.5975 (18)	175 (2)	2.7921 (14)	18	177.45 (7)
IF4-OX – 13	2.746 (3)	173 (3)	2.9972 (18)	15	173.15 (6)
IF4-OX – 11	2.690 (2)	174 (3)	2.8395 (18)	20	175.29 (7)
IF4-COOH – 13	2.550 (7)	162	3.093 (6)	12	174.8 (2)
IF4-COOH – 12	2.5285 (17)	176 (2)	2.7935 (14)	21	177.65 (5)
Br-COOH – 11	2.626 (2)	174 (3)	–	–	–
Br-COOH – 12	2.628 (4)	168.4	–	–	–
BrF4-OX – 14	2.693 (2)	173 (3)	–	–	–
BrF4-OH – 12	2.633 (3)	164 (5)	–	–	–
BrF4-OH – 11	2.556 (3)	158 (3)	–	–	–
IF4-OH – 16	2.644 (2)	156 (3)	2.9218 (15)	17	172.05 (6)
IF4-OH – 2	2.619 (2)	158 (3)	3.0486 (18)	14	174.76 (6)
IF4-COOH – 16	2.6469 (18)	155.7	2.8102 (11)	20	170.36 (4)
IF4-COOH – 2	2.653 (5)	174.8	2.997 (4)	15	176.48 (13)
Br-COOH – 2	2.663 (3)	160 (3)	3.224 (4)	5	170.94 (9)
BrF4-OH – 2	2.608 (2)	153.5	3.009 (2)	12	173.82 (7)

4. Discussion

The 24 crystal structures were analyzed and classified according to acceptor type in order to elucidate any patterns of behavior regarding the competition between hydrogen and halogen bonds.

4.1. Monotopic acceptors

Five crystal structures were obtained with monotopic acceptors and the predominant outcome (4/5) was a co-crystal in a 1:1 stoichiometry assembled from hydrogen bonds with no discernable contributions from halogen bonds (Fig. 7). Three of the four representatives in this group (IF₄-OX – 3, Br-OX – 5 and Br-COOH – 3) displayed near-identical behavior (as postulated in Fig. 1, bottom left) with the two reactants held together by near-linear hydrogen bonds resulting in 1:1 dimeric species with no evidence of proton transfer, Fig. 8.

Figure 7 Distribution of motifs with monotopic acceptors.

Figure 8 The main interaction in the crystal structure of IF4-OX – 3 (A = acceptor, H = hydrogen-bond donor).

However, in the fourth representative of this group, Br-COOH – 5, the outcome was somewhat different, even though only hydrogen bonding was noted as the structure-directing interactions. As a result of proton transfer from 4-bromobenzoic acid to 4-pyrrolidinopyridine (Fig. 9), an organic salt was created containing a carboxylate moiety as the key acceptor site. In addition to the benzoate:pyridinium ions, the lattice also included one equivalent of 4-bromobenzoic acid. The pyrrolidinium ring is disordered, and the carboxylate site forms two hydrogen bonds, O—H⋯C—O and N—H⋯C—O.

Figure 9 The salient intermolecular features in the crystal structure of 4-pyrrolidinopyridinium 4-bromobenzoate 4-bromobenzoic acid (1:1:1) (A = acceptor, H = hydrogen-bond donor).

The presence of an `extra' neutral molecule in pyridinum carboxylates is not unexpected as it has been demonstrated (Aakeröy, Fasulo & Desper, 2007) that close to 40% of organic carboxylate salts appear either as solvates/hydrates or with an additional neutral acid molecule in the crystal lattice. The likely explanation for this behavior is that a carboxylate moiety represents a powerful charge-assisted two-atom hydrogen-bond acceptor site which is not readily satisfied by a single hydrogen-bond donor, thus making it necessary to bring in a `free' carboxylic acid or a suitable solvent molecule. In contrast, the charge distribution around a neutral carboxylic acid makes it a less powerful or demanding hydrogen-bond acceptor site. Strictly speaking, Br-COOH – 5 may not fit exactly with any of the postulated outcomes in Fig. 1, but since no halogen bonding was observed, it belongs in the category of structures of monotopic acceptors where hydrogen-bonding dominates over halogen bonding.

In the remaining crystal structure with a monotopic acceptor, both halogen bonds and hydrogen bonds participate in the structure-directing process. The crystal structure of tetrafluoro-4-iodobenzoic acid 4-benzoylpyridine (IF₄-COOH – 4) displays interactions involving both the carboxylic acid and the activated iodine atom, and the outcome is a trimeric supermolecule in a 1:2 ratio, Fig. 10 (as postulated in Fig. 1). Note that we are considering 4-benzoylpyridine as a monotopic species since ketones are generally regarded as very poor acceptor sites and compared to the capability of a pyridyl moiety, it is reasonable to classify benzoylpyridine as a monotopic acceptor.

Figure 10 The trimeric supermolecule in the crystal structure of IF4-COOH – 4 (A = acceptor, H = hydrogen-bond donor, X = halogen-bond donor).

Based on the five structures with monotopic acceptors, it seems that hydrogen bonding is marginally favored (we found no system when halogen bonds were present and hydrogen bonds were absent). However, it should be noted that in three of the four structures where hydrogen bonding was dominant, the potential halogen-bond donors were not activated through the presence of electron-withdrawing groups or an adjacent sp-hybridized C atom. On the other hand, in the case where hydrogen bonds and halogen bonds were present simultaneously, the latter were represented by strongly activated iodine atoms; IF₄-COOH. These observations are discussed in detail later in the context of calculated molecular electrostatic potential values. It should be noted that the crystal structure of IF4-OH – 5 has been previously reported by Bruce and co-workers (Takemura, McAllister, Hart et al., 2014) (CCDC code: BIYFOG). The primary motifs in that structure are not the same as was found in IF₄-COOH-4, due to the deprotonation of the hydroxyl group. The phenolate site has become the sole acceptor site and acts as a bifurcated acceptor to a charge-assisted N—H⁺ hydrogen bond and a C—I halogen bond. The bifurcated XB/HB interaction is almost symmetric with both C—O⋯H—N bond C—O⋯I bond angles close to 131°. The similarity in bond angles may indicate that the two interactions are very comparable in importance and that the two donors are equally competitive for the most prominent charge-rich regions around the phenolate oxygen atom.

4.2. Ditopic symmetric acceptors

Co-crystallizations involving ditopic molecules with two equivalent acceptor sites produced 13 crystal structures. We anticipated three different modes of assembly as shown in Fig. 2: hydrogen bonds at both sites, halogen bonds at both sites or a halogen bond at one end and a hydrogen bond at the other end of the acceptor, producing an infinite one-dimensional chain. In eight co-crystals both donor types were involved in the assembly of supramolecular infinite chains, and in the remaining five structures both sides of the acceptor form a hydrogen bond, Fig. 11. There was no instance where a halogen bond was solely responsible for the co-crystal assembly.

Figure 11 Distribution of motifs with ditopic symmetric acceptors.

The infinite chains resulting from alternating donor and acceptor molecules are all very similar in terms of connectivity and geometry, Fig. 12 (in some cases the HB/XB donor molecule was disordered over two positions).

Figure 12 Primary interactions in the crystal structures of (a) BrF4-OH – 13 and (b) IF4-OX – 11 (bottom) (A = acceptor, H = hydrogen-bond donor, X = halogen-bond donor).

The second assembly type, found in five of the 13 structures with ditopic acceptors, in which only hydrogen bonding is observed, effectively leads to discrete supramolecular trimers, Fig. 13, with none of the main acceptor moieties engaged in a halogen bond.

Figure 13 Supramolecular trimers in the structures of (a) Br-COOH – 12 and (b) BrF4-OX – 14 (A = acceptor, H = hydrogen-bond donor).

The five structures where only hydrogen bonds appeared all involved bromo-substituted donors (Br-COOH, BrF₄-OX and BrF₄-OH). The lower polarizability of bromine compared with that of iodine clearly puts the XB donor at a significant disadvantage. Most of the eight chain-like motifs utilized an iodine-based HB donor (I-COOH, IF₄-OX, IF₄-COOH) even though some bromo-substituted donor molecules did produce a C—Br⋯A halogen bond alongside the HB donor, as long as the aromatic backbone was decorated with F atoms to activate the XB donor (as in BrF₄-OH and BrF₄-COOH).

4.3. Ditopic asymmetric acceptors

The final selection of co-crystals contained a ditopic molecule with two acceptor sites with different calculated electrostatic potentials (Fig. 14). The combination of these acceptors with the HB/XB donors could give rise to four possible scenarios, Fig. 3. Either the HB donor interacts with the stronger acceptor, leaving the XB donor to interact with the weaker, or vice versa. Alternatively, only one of the two donor types engage with both acceptors. Six crystal structures were obtained in this group but two of them, (IF₄-COOH—2 and IF₄-COOH—16), displayed disorder such that any assignment of binding preference could not be made. The four remaining structures were obtained with two different acceptor molecules, pyrazine-mono-N-oxide (16) and 4-CN-py (2). In the crystal structure of the co-crystal of the former, the HB donor interacts with the better acceptor and the XB donor interacts with the second best acceptor (ranking based upon electrostatic potentials (Aakeröy et al., 2014b; Aakeröy, Baldrighi et al., 2013; Aakeröy, Chopade & Desper, 2013; Aakeröy, Epa, Forbes & Desper, 2013; Aakeröy, Epa, Forbes, Schultheiss & Desper, 2013; Aakeröy, Wijethunga & Desper, 2015) and keeping in mind that the potential on the N-oxide has to be distributed among several lone-pairs), Fig. 15.

Figure 14 Distribution of motifs with ditopic asymmetric acceptor ligands.

Figure 15 One-dimensional chains in the crystal structures of tetrafluoro-4-iodophenol pyrazine-1-oxide (A1 = best acceptor, A2 = second-best acceptor, H = hydrogen-bond donor, X = halogen-bond donor).

The three co-crystals with 4-CN-py displayed very consistent behavior; in each instance, the HB donor engaged with the py moiety, and the XB donor formed a halogen bond with the nitrile acceptor, Fig. 16.

Figure 16 One-dimensional chains in the crystal structure of 4-bromobenzoic acid 4-cyanopyridine (A1 = best acceptor, A2 = second-best acceptor, H = hydrogen-bond donor, X = halogen-bond donor).

We were surprised to note, however, that the DFT calculations indicated that the C=N group should be ranked as a better acceptor site than the py moiety as the calculated electrostatic potentials were −159 and −145 kJ mol⁻¹, respectively. This ranking, (C=N) > (py), certainly seems counterintuitive, especially when considering extensive crystallographic data on reported co-crystals with 4-cyanopyridine; an analysis of existing relevant data clearly shows that the pyridine moiety is the preferred acceptor site. A few examples of motifs displayed by representative crystal structures are shown in Fig. 17.

Figure 17 Common hydrogen-bond patterns (a)–(b) (Mukherjee & Desiraju, 2014) and (c) (Zheng, 2012) and halogen-bond pattern (d) (Bailey et al., 1997) in co-crystals with 4-CN-pyridine.

Ultimately, this particular asymmetric acceptor must be examined in more detail with competing XB and HB donor moieties on the same molecule. However, based upon extensive crystallographic data, we will, for the purpose of this study, assign a ranking of (py) > (C=N) as indicated by the symbols A₁ and A₂, respectively in Fig. 16. The analysis presented in Fig. 14 is also based upon the same assignment.

Theoretical electrostatic potential calculations are known to offer valuable information about the relative strength of hydrogen bonds and halogen bonds (Murray & Politzer, 1991; Murray et al., 1990), and our results also indicate that a relatively simple electrostatic description of such interactions provide a useful tool for predicting the most likely practical supramolecular outcome, even in relatively complex systems with multiple binding possibilities. An advantage of this simplistic approach for practical co-crystal synthesis is that the ranking of the different donors and acceptors can be achieved using readily available computational tools. It can be seen from Table 4 that the electrostatic potential value on the HB donor is significantly higher than on the halogen bond site, and this holds true for all ten ditopic donors. However, it is not possible to make a prediction of the outcome purely based upon electrostatic potentials when the system under consideration contains both XB and HB donors. Although the expected relative importance of hydrogen-bond donor and halogen-bond donors can be ranked within each group based on electrostatic potentials, it does not mean that we can use the potential values in a direct comparison between the two different types of donor moieties.

However, the systematic study presented herein does offer some insight into how the potential values of competing HB and XB donors can be utilized as a tool for predicting structural outcomes. First, every one of the 24 co-crystals presented here displays hydrogen bonding as one of the primary stabilizing interactions, but not every structure contains an obvious structure-directing halogen bond. The crystal structures of monotopic and ditopic symmetric acceptors fall into two groups; those with halogen bonding (9/18), and those without (9/18). Second, a closer analysis of the electrostatic potential values on each of the halogen bond donors in these systems showed that those structures with halogen bonding present had an average potential on the XB donor of 146 kJ mol⁻¹, whereas those without halogen bonding had an average potential of the XB donor of 107 kJ mol⁻¹. Clearly, unless the XB donor is sufficiently electrophilic, it will not match the structural impact of the competing HB donor.

Another way of predicting the structural outcome in these systems involves using the relative differences in electrostatic potential of competing HB and XB donors. Therefore, for the purpose of this study, we define a single value, Q, as the difference in the electrostatic potential of the HB donor and the XB donor; Q = HB (potential) − XB (potential). The average Q value for the 11 structures that contained both hydrogen and halogen bonding (with monotopic or symmetric ditopic donors) was 142 kJ mol⁻¹, whereas the average Q value for the nine structures that only displayed hydrogen bonding was 175 kJ mol⁻¹. This underscores that the difference in electrostatic potential between competing sites can offer a good indication of what the outcome is likely to be in competitive supramolecular systems, Fig. 18.

Figure 18 Correlation between difference in electrostatic potential (Q value) between HB and XB donor and structural outcome.

If we were to rely on the average Q values as a way of estimating the outcome in the 20 structures with monotopic and symmetric ditopic acceptors, the correct primary structural features are predicting 89% of the time (in 16/18 structures). Only two outliers are observed, the first being the crystal structure of IF₄-OX – 3, Fig. 8, where a hydrogen-bonded dimer was formed when we would have anticipated an HB/XB trimeric motif, with one donor molecule and two acceptors (the Q value in this case is 115 kJ mol⁻¹). The second outlier among this group is the structure of BrF₄-OH – 13, where the Q value for the donor is 189 kJ mol⁻¹, and one would expect that HB would be formed exclusively resulting in a trimer. Instead, both the XB and the HB moieties act as donors and the result is an infinite chain, Fig. 12 (top).

In the case of the interactions between a dual XB/HB donor molecule with either monotopic or symmetric ditopic acceptor molecules, we have been able to correlate the structural behavior with the relative difference in the electrostatic potential values of the two donor sites. In order to examine how well (or poorly) these Q values work for predicting the primary outcomes of co-crystallizations with XB/HB ditopic donor molecules and monotopic and ditopic acceptors, we found five structures in the CSD of direct relevance to this work. There are four neutral co-crystals with IF₄-OH which has a Q value of 155 kJ mol⁻¹ (TONMIT/TONMAL (Präsang et al., 2008), HIZRIT/HIZROZ (Takemura, McAllister, Karadakov et al., 2014)) and one co-crystal with BrF₄-OH, which has a Q value of 190 kJ mol⁻¹ (HIZREP (Takemura, McAllister, Karadakov et al., 2014)), Fig. 19.

Figure 19 Supramolecular trimers observed in CSD structures with (a) IF4-OH (Präsang et al., 2008) and (b) BrF4-OH (Takemura, McAllister, Karadakov et al., 2014) (A = acceptor, H = hydrogen-bond donor, X = halogen-bond donor).

Based on the relative differences in electrostatic potentials for the two donors, one would expect the first group to contain both hydrogen and halogen bonds, since it is nearer to the average Q value of 142 kJ mol⁻¹ exhibited in those cases. The latter structure would be expected to display only hydrogen bonds, since it exceeds the average Q value of 175 kJ mol⁻¹ in which no XB exist. These are, in fact, the outcomes for each of the five crystal structures (Fig. 19). Even though there is still a relatively small amount of crystallographic data on co-crystals of molecules that contain one XB and one HB donor on the same molecular backbone, we have developed a simple electrostatic-based guideline for predicting the most likely practical outcome in systems with competing hydrogen bonds and halogen bonds. Once more relevant experimental data is added, the initial average Q values can be adjusted to better reflect the pattern preferences of a larger group of molecules. The work presented herein can offer a complement to studies that have examined connections and interrelationships between synthons, electron densities and structure or packing features in solids. For example, Hathwar and co-coworkers (Hathwar et al., 2011) have proposed a Supramolecular Synthon Based Fragments Approach (SBFA) that relies on the robustness and modularity of the supramolecular synthons to provide transferability of charge-density-derived parameters for structural fragments, thereby providing a tool for accessing charge densities of unknown compounds. The SBFA approach has been validated against experimental charge density data in order to examine the reliability of this methodology (Dubey et al., 2014).

The relationship between electron density and intermolecular bond energy has been examined for halogen bonds both theoretically (Amezaga et al., 2010) and experimentally (Pavan et al., 2013). Similarly, the nature and strength of hydrogen bonds have also been the subject of careful analyses using electron densities as a critical component (Jarzembska et al., 2013) and such studies are not restricted to small molecules (Liebschner et al., 2011). Furthermore, the balance between intermolecular interactions is obviously not always going to be dominated by hydrogen and halogen bonds and other forces, including dispersion, are always present to a greater or lesser extent (Maloney et al., 2014).

In our study we have selected XB and HB donors–acceptors where steric hindrance is unlikely to play a role, but the importance of geometric factors for synthon reliability and crystal packing features has been highlighted through the use of long-range synthon Aufbau modules (LSAM) that carry the imprint of the synthons (Ganguly & Desiraju, 2010). Each LSAM can be characterized by specific geometries and relative orientations that may strongly influence the final assembly of the crystal lattice. This approach offers a complementary way of examining crystal assembly from individual molecules (or functional groups) to the final three-dimensional architecture and it may be particularly useful for constructing solids with specific unit-cell dimensions (Mukherjee et al., 2014). The geometric disposition of chemical functionalities or binding sites can obviously influence the propensity for co-crystal formation and a multi-layered approach is especially necessary for rationalizing structures that defy expectations (Kaur et al., 2015).

It is fair to say that sophisticated charge/electron-density studies remain non-routine and therefore a simplistic approach, based on extensive crystallographic information and readily accessible computational data as demonstrated in our work, can offer guidelines for how to predict key structural features in complex organic compounds with multiple co-existing synthons that may be of considerable practical value.

5. Conclusions

This extensive structural study on the competition between hydrogen and halogen bonding in co-crystals has helped clarify the competition and balance between them in a practical supramolecular synthetic system. Building on a systematic co-crystal screen of 10 HB/XB donor molecules with 20 acceptors it has been shown that generally speaking hydrogen bonding is likely to be a more effective synthetic vector as a result of its presence in every one of the 24 structures obtained. However, halogen bonding is clearly also important for organizing molecules into well defined supramolecular motifs and extended architectures since such interactions appeared in 13 of the 24 structures. Whether a halogen bond appears alongside a hydrogen bond in any of the crystal structures herein or not is largely predicted upon the difference in electrostatic potential value between the HB donor and the XB donor (represented by the Q value). In structures of monotopic and symmetric ditopic acceptors where both XB and HB interactions were involved (9/18 occurrences) the average Q value was 142 kJ mol⁻¹, whereas in the nine structures where only hydrogen bonding was present as a structure directing force, the average Q value was 175 kJ mol⁻¹. We have deliberately avoided any discussions about how our results may or may not reflect the actual bond strengths of HB and XB interactions and instead simply focused on observed structural outcomes. The straightforward and readily applicable approach that comes out of this study for predicting the primary synthons is admittedly only based on electrostatics, but it nevertheless yields the correct synthons in 16 of the 18 structures. Obviously, further exceptions to our observations will arise, and it is clear that the structural landscape needs to be defined and examined with even greater resolution, but the information presented herein may offer a useful `rule-of-thumb' for how the balance between potentially competing XBs and HBs will manifest itself in practical co-crystal synthesis.

Supporting information

Computing details

For all compounds, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

(IF4OX3) CS—AS-9–3 4-I—F4-PhCHO oxime, 4-(Me2N)-pyridine

Crystal data

(C7H2F4INO)(C7H10N2)	F(000) = 1712
Mr = 441.17	Dx = 1.853 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.9735 (9) Å	Cell parameters from 9973 reflections
b = 17.2451 (11) Å	θ = 2.8–31.9°
c = 13.6166 (8) Å	µ = 2.07 mm^−1
β = 105.489 (2)°	T = 120 K
V = 3162.1 (3) Å^3	Plate, colourless
Z = 8	0.38 × 0.22 × 0.08 mm

Data collection

Bruker APEX-II CCD diffractometer	10414 independent reflections
Radiation source: fine-focus sealed tube	7877 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 32.1°, θmin = 2.4°
Absorption correction: multi-scan SADABS	h = −20→18
Tmin = 0.506, Tmax = 0.852	k = −25→25
33827 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 2.5P] where P = (Fo^2 + 2Fc^2)/3
10414 reflections	(Δ/σ)max = 0.002
415 parameters	Δρmax = 1.70 e Å^−3
0 restraints	Δρmin = −0.74 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1_1	0.238568 (15)	0.619982 (11)	0.666171 (15)	0.03923 (7)
C11_1	−0.01738 (18)	0.82016 (13)	0.63176 (18)	0.0224 (4)
C12_1	0.08197 (19)	0.83847 (13)	0.64211 (18)	0.0240 (5)
F12_1	0.11069 (13)	0.91197 (8)	0.64024 (14)	0.0352 (4)
C13_1	0.15294 (18)	0.78177 (15)	0.65205 (19)	0.0251 (5)
F13_1	0.24662 (12)	0.80315 (11)	0.66036 (13)	0.0385 (4)
C14_1	0.1301 (2)	0.70361 (14)	0.65328 (18)	0.0259 (5)
C15_1	0.03219 (19)	0.68451 (13)	0.64337 (18)	0.0241 (5)
F15_1	0.00362 (13)	0.61034 (8)	0.64230 (13)	0.0337 (4)
C16_1	−0.03839 (18)	0.74151 (13)	0.63359 (18)	0.0231 (4)
F16_1	−0.13304 (12)	0.71959 (9)	0.62407 (13)	0.0331 (3)
C17_1	−0.0984 (2)	0.87517 (15)	0.6183 (2)	0.0319 (6)
H17A_1	−0.1646	0.8564	0.6039	0.038*
N17_1	−0.08309 (18)	0.94832 (12)	0.62526 (17)	0.0297 (5)
O17_1	−0.17064 (17)	0.98850 (12)	0.61126 (19)	0.0446 (5)
H17_1	−0.1596	1.0363	0.6090	0.054*
N21_1	−0.1006 (2)	1.13091 (13)	0.60770 (18)	0.0350 (5)
C22_1	−0.1521 (2)	1.19717 (15)	0.5983 (2)	0.0304 (5)
H22_1	−0.2217	1.1939	0.5898	0.036*
C23_1	−0.1107 (2)	1.26982 (15)	0.60030 (18)	0.0276 (5)
H23_1	−0.1515	1.3146	0.5935	0.033*
C24_1	−0.0082 (2)	1.27793 (15)	0.61227 (18)	0.0282 (5)
N24_1	0.03490 (19)	1.34865 (14)	0.6159 (2)	0.0366 (5)
C25_1	0.0461 (2)	1.20751 (17)	0.6207 (2)	0.0337 (6)
H25_1	0.1156	1.2083	0.6282	0.040*
C26_1	−0.0032 (3)	1.13844 (17)	0.6178 (2)	0.0376 (7)
H26_1	0.0349	1.0922	0.6235	0.045*
C27_1	−0.0225 (3)	1.41944 (16)	0.6111 (2)	0.0393 (7)
H27A_1	−0.0921	1.4063	0.6048	0.059*
H27B_1	−0.0180	1.4501	0.5519	0.059*
H27C_1	0.0039	1.4497	0.6734	0.059*
C28_1	0.1398 (3)	1.3573 (3)	0.6216 (3)	0.0534 (9)
H28A_1	0.1698	1.3060	0.6211	0.080*
H28B_1	0.1732	1.3845	0.6846	0.080*
H28C_1	0.1470	1.3873	0.5628	0.080*
I2_2	0.730582 (16)	0.585320 (12)	0.653752 (16)	0.04150 (7)
C11_2	0.47960 (19)	0.38121 (13)	0.62297 (18)	0.0229 (4)
C12_2	0.57873 (19)	0.36455 (14)	0.63092 (19)	0.0255 (5)
F12_2	0.60984 (13)	0.29107 (9)	0.63154 (14)	0.0373 (4)
C13_2	0.6482 (2)	0.42215 (15)	0.6392 (2)	0.0280 (5)
F13_2	0.74224 (12)	0.40172 (11)	0.64725 (15)	0.0408 (4)
C14_2	0.6241 (2)	0.50016 (15)	0.63947 (19)	0.0272 (5)
C15_2	0.5258 (2)	0.51757 (13)	0.63106 (19)	0.0259 (5)
F15_2	0.49552 (14)	0.59136 (8)	0.62980 (14)	0.0372 (4)
C16_2	0.45687 (19)	0.45980 (14)	0.62307 (19)	0.0240 (5)
F16_2	0.36211 (11)	0.48065 (9)	0.61532 (13)	0.0334 (3)
C17_2	0.4006 (2)	0.32475 (15)	0.6164 (2)	0.0294 (5)
H17A_2	0.3349	0.3428	0.6092	0.035*
N17_2	0.41665 (18)	0.25214 (12)	0.61980 (18)	0.0315 (5)
O17_2	0.33054 (17)	0.21115 (11)	0.61452 (19)	0.0421 (5)
H17_2	0.3424	0.1634	0.6145	0.051*
N21_2	0.4036 (2)	0.07053 (13)	0.61670 (18)	0.0346 (5)
C22_2	0.3514 (2)	0.00439 (15)	0.6041 (2)	0.0315 (5)
H22_2	0.2815	0.0077	0.5935	0.038*
C23_2	0.3930 (2)	−0.06779 (15)	0.60575 (19)	0.0282 (5)
H23_2	0.3519	−0.1125	0.5965	0.034*
C24_2	0.4960 (2)	−0.07611 (15)	0.62095 (18)	0.0274 (5)
N24_2	0.5392 (2)	−0.14630 (14)	0.6256 (2)	0.0367 (5)
C25_2	0.5504 (2)	−0.00587 (16)	0.63217 (19)	0.0312 (5)
H25_2	0.6202	−0.0067	0.6415	0.037*
C26_2	0.5018 (2)	0.06301 (16)	0.6295 (2)	0.0353 (6)
H26_2	0.5403	0.1091	0.6373	0.042*
C27_2	0.4802 (3)	−0.21685 (17)	0.6117 (3)	0.0437 (7)
H27A_2	0.4108	−0.2038	0.6066	0.066*
H27B_2	0.5055	−0.2514	0.6700	0.066*
H27C_2	0.4845	−0.2429	0.5491	0.066*
C28_2	0.6447 (2)	−0.1546 (2)	0.6345 (3)	0.0464 (8)
H28A_2	0.6761	−0.1033	0.6428	0.070*
H28B_2	0.6539	−0.1792	0.5728	0.070*
H28C_2	0.6753	−0.1868	0.6939	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1_1	0.03648 (11)	0.03669 (11)	0.04441 (11)	0.01578 (8)	0.01063 (8)	0.00106 (7)
C11_1	0.0247 (11)	0.0178 (9)	0.0271 (10)	−0.0014 (8)	0.0111 (9)	−0.0002 (8)
C12_1	0.0274 (12)	0.0183 (10)	0.0282 (11)	−0.0051 (9)	0.0105 (9)	0.0010 (8)
F12_1	0.0344 (9)	0.0198 (7)	0.0532 (10)	−0.0080 (6)	0.0147 (8)	0.0021 (6)
C13_1	0.0198 (11)	0.0289 (11)	0.0288 (11)	−0.0039 (9)	0.0102 (9)	−0.0010 (9)
F13_1	0.0215 (8)	0.0443 (9)	0.0506 (10)	−0.0050 (7)	0.0116 (7)	0.0012 (7)
C14_1	0.0283 (12)	0.0241 (10)	0.0263 (11)	0.0029 (9)	0.0089 (9)	0.0011 (9)
C15_1	0.0297 (12)	0.0164 (9)	0.0268 (11)	−0.0016 (9)	0.0084 (9)	0.0008 (8)
F15_1	0.0405 (9)	0.0153 (6)	0.0458 (9)	−0.0035 (6)	0.0123 (7)	0.0006 (6)
C16_1	0.0213 (11)	0.0204 (10)	0.0286 (11)	−0.0032 (8)	0.0085 (9)	−0.0001 (8)
F16_1	0.0229 (7)	0.0248 (7)	0.0536 (9)	−0.0080 (6)	0.0135 (7)	0.0004 (6)
C17_1	0.0266 (13)	0.0237 (11)	0.0465 (15)	0.0012 (10)	0.0116 (11)	0.0037 (10)
N17_1	0.0314 (11)	0.0225 (9)	0.0349 (11)	0.0054 (9)	0.0085 (9)	0.0020 (8)
O17_1	0.0372 (12)	0.0229 (9)	0.0707 (15)	0.0091 (8)	0.0089 (11)	0.0026 (9)
N21_1	0.0479 (15)	0.0253 (10)	0.0337 (11)	0.0066 (10)	0.0144 (10)	0.0014 (9)
C22_1	0.0362 (14)	0.0253 (11)	0.0309 (12)	0.0021 (10)	0.0111 (11)	0.0016 (9)
C23_1	0.0346 (14)	0.0241 (11)	0.0259 (11)	0.0071 (10)	0.0111 (10)	0.0032 (9)
C24_1	0.0344 (14)	0.0273 (11)	0.0234 (11)	0.0036 (10)	0.0089 (10)	−0.0012 (9)
N24_1	0.0342 (13)	0.0326 (12)	0.0453 (13)	−0.0032 (10)	0.0147 (11)	−0.0033 (10)
C25_1	0.0351 (15)	0.0370 (14)	0.0296 (12)	0.0136 (12)	0.0095 (11)	−0.0016 (10)
C26_1	0.0526 (19)	0.0301 (13)	0.0308 (13)	0.0149 (13)	0.0123 (12)	0.0022 (10)
C27_1	0.0493 (18)	0.0242 (12)	0.0436 (16)	−0.0022 (12)	0.0109 (14)	−0.0004 (11)
C28_1	0.0347 (17)	0.065 (2)	0.058 (2)	−0.0094 (16)	0.0090 (15)	−0.0100 (18)
I2_2	0.04046 (12)	0.03715 (11)	0.04750 (12)	−0.01716 (8)	0.01279 (9)	−0.00109 (8)
C11_2	0.0245 (11)	0.0197 (10)	0.0263 (11)	0.0013 (8)	0.0101 (9)	−0.0005 (8)
C12_2	0.0265 (12)	0.0202 (10)	0.0311 (12)	0.0028 (9)	0.0099 (9)	−0.0037 (9)
F12_2	0.0324 (9)	0.0208 (7)	0.0591 (10)	0.0077 (6)	0.0126 (8)	−0.0069 (7)
C13_2	0.0230 (12)	0.0288 (12)	0.0345 (12)	0.0013 (9)	0.0117 (10)	−0.0026 (10)
F13_2	0.0240 (8)	0.0409 (9)	0.0598 (11)	0.0026 (7)	0.0154 (8)	−0.0079 (8)
C14_2	0.0282 (13)	0.0252 (11)	0.0292 (11)	−0.0049 (9)	0.0093 (10)	−0.0005 (9)
C15_2	0.0336 (13)	0.0158 (9)	0.0290 (11)	0.0027 (9)	0.0096 (10)	0.0012 (8)
F15_2	0.0437 (10)	0.0160 (6)	0.0507 (10)	0.0034 (6)	0.0107 (8)	0.0030 (6)
C16_2	0.0234 (11)	0.0215 (10)	0.0286 (11)	0.0040 (9)	0.0094 (9)	0.0014 (8)
F16_2	0.0242 (8)	0.0251 (7)	0.0509 (9)	0.0065 (6)	0.0101 (7)	−0.0020 (6)
C17_2	0.0244 (12)	0.0245 (11)	0.0411 (13)	0.0011 (9)	0.0122 (10)	−0.0019 (10)
N17_2	0.0350 (12)	0.0218 (9)	0.0381 (12)	−0.0043 (9)	0.0107 (10)	−0.0008 (8)
O17_2	0.0382 (12)	0.0230 (9)	0.0672 (14)	−0.0074 (8)	0.0177 (11)	0.0022 (9)
N21_2	0.0426 (14)	0.0237 (10)	0.0359 (12)	−0.0057 (10)	0.0080 (10)	0.0030 (9)
C22_2	0.0305 (13)	0.0279 (12)	0.0351 (13)	−0.0039 (10)	0.0073 (11)	0.0017 (10)
C23_2	0.0310 (13)	0.0237 (11)	0.0299 (12)	−0.0089 (10)	0.0083 (10)	0.0000 (9)
C24_2	0.0313 (13)	0.0275 (11)	0.0239 (11)	−0.0055 (10)	0.0086 (10)	0.0009 (9)
N24_2	0.0352 (13)	0.0321 (11)	0.0459 (13)	−0.0019 (10)	0.0161 (11)	0.0025 (10)
C25_2	0.0284 (13)	0.0356 (13)	0.0283 (12)	−0.0083 (11)	0.0054 (10)	0.0030 (10)
C26_2	0.0435 (16)	0.0274 (12)	0.0319 (13)	−0.0154 (12)	0.0047 (12)	0.0011 (10)
C27_2	0.0490 (19)	0.0262 (13)	0.0566 (19)	0.0027 (13)	0.0155 (15)	−0.0035 (12)
C28_2	0.0337 (16)	0.059 (2)	0.0459 (17)	0.0067 (15)	0.0091 (13)	0.0016 (15)

Geometric parameters (Å, º)

I1_1—C14_1	2.066 (3)	I2_2—C14_2	2.063 (3)
C11_1—C16_1	1.389 (3)	C11_2—C12_2	1.390 (4)
C11_1—C12_1	1.394 (4)	C11_2—C16_2	1.392 (3)
C11_1—C17_1	1.450 (4)	C11_2—C17_2	1.457 (4)
C12_1—F12_1	1.332 (3)	C12_2—F12_2	1.339 (3)
C12_1—C13_1	1.373 (4)	C12_2—C13_2	1.372 (4)
C13_1—F13_1	1.335 (3)	C13_2—F13_2	1.336 (3)
C13_1—C14_1	1.386 (3)	C13_2—C14_2	1.387 (4)
C14_1—C15_1	1.378 (4)	C14_2—C15_2	1.380 (4)
C15_1—F15_1	1.339 (3)	C15_2—F15_2	1.340 (3)
C15_1—C16_1	1.373 (3)	C15_2—C16_2	1.370 (4)
C16_1—F16_1	1.348 (3)	C16_2—F16_2	1.349 (3)
C17_1—N17_1	1.279 (3)	C17_2—N17_2	1.271 (3)
C17_1—H17A_1	0.9500	C17_2—H17A_2	0.9500
N17_1—O17_1	1.374 (3)	N17_2—O17_2	1.381 (3)
O17_1—H17_1	0.8400	O17_2—H17_2	0.8400
N21_1—C26_1	1.337 (4)	N21_2—C22_2	1.340 (3)
N21_1—C22_1	1.339 (3)	N21_2—C26_2	1.342 (4)
C22_1—C23_1	1.378 (4)	C22_2—C23_2	1.372 (4)
C22_1—H22_1	0.9500	C22_2—H22_2	0.9500
C23_1—C24_1	1.404 (4)	C23_2—C24_2	1.406 (4)
C23_1—H23_1	0.9500	C23_2—H23_2	0.9500
C24_1—N24_1	1.356 (4)	C24_2—N24_2	1.346 (4)
C24_1—C25_1	1.420 (4)	C24_2—C25_2	1.416 (4)
N24_1—C27_1	1.453 (4)	N24_2—C27_2	1.453 (4)
N24_1—C28_1	1.454 (4)	N24_2—C28_2	1.454 (4)
C25_1—C26_1	1.371 (4)	C25_2—C26_2	1.364 (4)
C25_1—H25_1	0.9500	C25_2—H25_2	0.9500
C26_1—H26_1	0.9500	C26_2—H26_2	0.9500
C27_1—H27A_1	0.9800	C27_2—H27A_2	0.9800
C27_1—H27B_1	0.9800	C27_2—H27B_2	0.9800
C27_1—H27C_1	0.9800	C27_2—H27C_2	0.9800
C28_1—H28A_1	0.9800	C28_2—H28A_2	0.9800
C28_1—H28B_1	0.9800	C28_2—H28B_2	0.9800
C28_1—H28C_1	0.9800	C28_2—H28C_2	0.9800
C16_1—C11_1—C12_1	115.4 (2)	C12_2—C11_2—C16_2	115.1 (2)
C16_1—C11_1—C17_1	118.6 (2)	C12_2—C11_2—C17_2	126.1 (2)
C12_1—C11_1—C17_1	126.0 (2)	C16_2—C11_2—C17_2	118.8 (2)
F12_1—C12_1—C13_1	117.8 (2)	F12_2—C12_2—C13_2	117.6 (2)
F12_1—C12_1—C11_1	120.7 (2)	F12_2—C12_2—C11_2	120.7 (2)
C13_1—C12_1—C11_1	121.5 (2)	C13_2—C12_2—C11_2	121.7 (2)
F13_1—C13_1—C12_1	118.5 (2)	F13_2—C13_2—C12_2	118.3 (2)
F13_1—C13_1—C14_1	119.4 (2)	F13_2—C13_2—C14_2	119.3 (2)
C12_1—C13_1—C14_1	122.1 (2)	C12_2—C13_2—C14_2	122.3 (2)
C15_1—C14_1—C13_1	117.2 (2)	C15_2—C14_2—C13_2	116.6 (2)
C15_1—C14_1—I1_1	121.89 (18)	C15_2—C14_2—I2_2	121.98 (18)
C13_1—C14_1—I1_1	120.91 (19)	C13_2—C14_2—I2_2	121.4 (2)
F15_1—C15_1—C16_1	118.6 (2)	F15_2—C15_2—C16_2	118.4 (2)
F15_1—C15_1—C14_1	121.0 (2)	F15_2—C15_2—C14_2	120.8 (2)
C16_1—C15_1—C14_1	120.4 (2)	C16_2—C15_2—C14_2	120.8 (2)
F16_1—C16_1—C15_1	118.0 (2)	F16_2—C16_2—C15_2	117.9 (2)
F16_1—C16_1—C11_1	118.6 (2)	F16_2—C16_2—C11_2	118.6 (2)
C15_1—C16_1—C11_1	123.4 (2)	C15_2—C16_2—C11_2	123.5 (2)
N17_1—C17_1—C11_1	121.8 (3)	N17_2—C17_2—C11_2	122.2 (2)
N17_1—C17_1—H17A_1	119.1	N17_2—C17_2—H17A_2	118.9
C11_1—C17_1—H17A_1	119.1	C11_2—C17_2—H17A_2	118.9
C17_1—N17_1—O17_1	111.2 (2)	C17_2—N17_2—O17_2	111.1 (2)
N17_1—O17_1—H17_1	109.5	N17_2—O17_2—H17_2	109.5
C26_1—N21_1—C22_1	115.7 (3)	C22_2—N21_2—C26_2	115.9 (2)
N21_1—C22_1—C23_1	124.2 (3)	N21_2—C22_2—C23_2	123.8 (3)
N21_1—C22_1—H22_1	117.9	N21_2—C22_2—H22_2	118.1
C23_1—C22_1—H22_1	117.9	C23_2—C22_2—H22_2	118.1
C22_1—C23_1—C24_1	120.2 (2)	C22_2—C23_2—C24_2	120.5 (2)
C22_1—C23_1—H23_1	119.9	C22_2—C23_2—H23_2	119.7
C24_1—C23_1—H23_1	119.9	C24_2—C23_2—H23_2	119.7
N24_1—C24_1—C23_1	121.6 (2)	N24_2—C24_2—C23_2	121.8 (2)
N24_1—C24_1—C25_1	122.9 (3)	N24_2—C24_2—C25_2	122.9 (3)
C23_1—C24_1—C25_1	115.5 (2)	C23_2—C24_2—C25_2	115.3 (2)
C24_1—N24_1—C27_1	121.3 (3)	C24_2—N24_2—C27_2	121.0 (3)
C24_1—N24_1—C28_1	121.8 (3)	C24_2—N24_2—C28_2	121.6 (3)
C27_1—N24_1—C28_1	116.9 (3)	C27_2—N24_2—C28_2	117.1 (3)
C26_1—C25_1—C24_1	119.2 (3)	C26_2—C25_2—C24_2	119.6 (3)
C26_1—C25_1—H25_1	120.4	C26_2—C25_2—H25_2	120.2
C24_1—C25_1—H25_1	120.4	C24_2—C25_2—H25_2	120.2
N21_1—C26_1—C25_1	125.2 (3)	N21_2—C26_2—C25_2	124.9 (2)
N21_1—C26_1—H26_1	117.4	N21_2—C26_2—H26_2	117.6
C25_1—C26_1—H26_1	117.4	C25_2—C26_2—H26_2	117.6
N24_1—C27_1—H27A_1	109.5	N24_2—C27_2—H27A_2	109.5
N24_1—C27_1—H27B_1	109.5	N24_2—C27_2—H27B_2	109.5
H27A_1—C27_1—H27B_1	109.5	H27A_2—C27_2—H27B_2	109.5
N24_1—C27_1—H27C_1	109.5	N24_2—C27_2—H27C_2	109.5
H27A_1—C27_1—H27C_1	109.5	H27A_2—C27_2—H27C_2	109.5
H27B_1—C27_1—H27C_1	109.5	H27B_2—C27_2—H27C_2	109.5
N24_1—C28_1—H28A_1	109.5	N24_2—C28_2—H28A_2	109.5
N24_1—C28_1—H28B_1	109.5	N24_2—C28_2—H28B_2	109.5
H28A_1—C28_1—H28B_1	109.5	H28A_2—C28_2—H28B_2	109.5
N24_1—C28_1—H28C_1	109.5	N24_2—C28_2—H28C_2	109.5
H28A_1—C28_1—H28C_1	109.5	H28A_2—C28_2—H28C_2	109.5
H28B_1—C28_1—H28C_1	109.5	H28B_2—C28_2—H28C_2	109.5
C16_1—C11_1—C12_1—F12_1	179.2 (2)	C16_2—C11_2—C12_2—F12_2	−179.9 (2)
C17_1—C11_1—C12_1—F12_1	0.0 (4)	C17_2—C11_2—C12_2—F12_2	1.1 (4)
C16_1—C11_1—C12_1—C13_1	0.8 (4)	C16_2—C11_2—C12_2—C13_2	0.6 (4)
C17_1—C11_1—C12_1—C13_1	−178.4 (2)	C17_2—C11_2—C12_2—C13_2	−178.4 (3)
F12_1—C12_1—C13_1—F13_1	0.7 (3)	F12_2—C12_2—C13_2—F13_2	0.1 (4)
C11_1—C12_1—C13_1—F13_1	179.2 (2)	C11_2—C12_2—C13_2—F13_2	179.6 (2)
F12_1—C12_1—C13_1—C14_1	−179.0 (2)	F12_2—C12_2—C13_2—C14_2	−180.0 (2)
C11_1—C12_1—C13_1—C14_1	−0.6 (4)	C11_2—C12_2—C13_2—C14_2	−0.5 (4)
F13_1—C13_1—C14_1—C15_1	−179.3 (2)	F13_2—C13_2—C14_2—C15_2	−179.9 (2)
C12_1—C13_1—C14_1—C15_1	0.4 (4)	C12_2—C13_2—C14_2—C15_2	0.1 (4)
F13_1—C13_1—C14_1—I1_1	−0.7 (3)	F13_2—C13_2—C14_2—I2_2	−0.8 (3)
C12_1—C13_1—C14_1—I1_1	179.06 (18)	C12_2—C13_2—C14_2—I2_2	179.3 (2)
C13_1—C14_1—C15_1—F15_1	179.0 (2)	C13_2—C14_2—C15_2—F15_2	−179.5 (2)
I1_1—C14_1—C15_1—F15_1	0.4 (3)	I2_2—C14_2—C15_2—F15_2	1.4 (3)
C13_1—C14_1—C15_1—C16_1	−0.5 (4)	C13_2—C14_2—C15_2—C16_2	0.1 (4)
I1_1—C14_1—C15_1—C16_1	−179.13 (18)	I2_2—C14_2—C15_2—C16_2	−179.09 (18)
F15_1—C15_1—C16_1—F16_1	0.4 (3)	F15_2—C15_2—C16_2—F16_2	−0.6 (3)
C14_1—C15_1—C16_1—F16_1	180.0 (2)	C14_2—C15_2—C16_2—F16_2	179.8 (2)
F15_1—C15_1—C16_1—C11_1	−178.7 (2)	F15_2—C15_2—C16_2—C11_2	179.7 (2)
C14_1—C15_1—C16_1—C11_1	0.8 (4)	C14_2—C15_2—C16_2—C11_2	0.1 (4)
C12_1—C11_1—C16_1—F16_1	179.9 (2)	C12_2—C11_2—C16_2—F16_2	179.8 (2)
C17_1—C11_1—C16_1—F16_1	−0.8 (4)	C17_2—C11_2—C16_2—F16_2	−1.1 (4)
C12_1—C11_1—C16_1—C15_1	−0.9 (4)	C12_2—C11_2—C16_2—C15_2	−0.5 (4)
C17_1—C11_1—C16_1—C15_1	178.3 (2)	C17_2—C11_2—C16_2—C15_2	178.6 (2)
C16_1—C11_1—C17_1—N17_1	173.4 (3)	C12_2—C11_2—C17_2—N17_2	1.7 (4)
C12_1—C11_1—C17_1—N17_1	−7.4 (4)	C16_2—C11_2—C17_2—N17_2	−177.3 (3)
C11_1—C17_1—N17_1—O17_1	−179.0 (2)	C11_2—C17_2—N17_2—O17_2	178.5 (2)
C26_1—N21_1—C22_1—C23_1	−1.1 (4)	C26_2—N21_2—C22_2—C23_2	1.2 (4)
N21_1—C22_1—C23_1—C24_1	0.3 (4)	N21_2—C22_2—C23_2—C24_2	−0.2 (4)
C22_1—C23_1—C24_1—N24_1	−179.1 (2)	C22_2—C23_2—C24_2—N24_2	178.2 (3)
C22_1—C23_1—C24_1—C25_1	0.6 (4)	C22_2—C23_2—C24_2—C25_2	−1.0 (4)
C23_1—C24_1—N24_1—C27_1	2.2 (4)	C23_2—C24_2—N24_2—C27_2	2.1 (4)
C25_1—C24_1—N24_1—C27_1	−177.5 (3)	C25_2—C24_2—N24_2—C27_2	−178.8 (3)
C23_1—C24_1—N24_1—C28_1	−175.9 (3)	C23_2—C24_2—N24_2—C28_2	175.8 (3)
C25_1—C24_1—N24_1—C28_1	4.4 (4)	C25_2—C24_2—N24_2—C28_2	−5.0 (4)
N24_1—C24_1—C25_1—C26_1	179.0 (3)	N24_2—C24_2—C25_2—C26_2	−178.1 (3)
C23_1—C24_1—C25_1—C26_1	−0.7 (4)	C23_2—C24_2—C25_2—C26_2	1.1 (4)
C22_1—N21_1—C26_1—C25_1	1.0 (4)	C22_2—N21_2—C26_2—C25_2	−1.1 (4)
C24_1—C25_1—C26_1—N21_1	−0.1 (4)	C24_2—C25_2—C26_2—N21_2	0.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O17_1—H17_1···N21_1	0.84	1.83	2.649 (3)	164
O17_2—H17_2···N21_2	0.84	1.81	2.628 (3)	163

(BrOX5) S—AV-14–5 4-Br-PhCH(=NOH), 4-(1-pyrrolidinyl)-pyridine

Crystal data

(C7H6BrNO)(C9H12N2)	Z = 2
Mr = 348.24	F(000) = 356
Triclinic, P1	Dx = 1.518 Mg m^−3
a = 7.8090 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6156 (14) Å	Cell parameters from 9017 reflections
c = 11.4520 (18) Å	θ = 2.4–31.4°
α = 101.314 (5)°	µ = 2.70 mm^−1
β = 94.225 (5)°	T = 120 K
γ = 113.541 (4)°	Prism, colourless
V = 761.9 (2) Å^3	0.30 × 0.22 × 0.08 mm

Data collection

Bruker APEX-II CCD diffractometer	4635 independent reflections
Radiation source: fine-focus sealed tube	3909 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 31.5°, θmin = 2.4°
Absorption correction: multi-scan SADABS	h = −11→11
Tmin = 0.498, Tmax = 0.813	k = −14→13
16077 measured reflections	l = −15→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.030P)^2 + 0.4P] where P = (Fo^2 + 2Fc^2)/3
4635 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.10553 (3)	0.80402 (2)	−0.024168 (18)	0.03188 (7)
C11	0.5557 (2)	0.64997 (19)	0.12443 (15)	0.0223 (3)
C12	0.5998 (2)	0.7564 (2)	0.05288 (16)	0.0256 (3)
H12	0.7241	0.7989	0.0344	0.031*
C13	0.4664 (2)	0.8019 (2)	0.00795 (16)	0.0255 (3)
H13	0.4976	0.8738	−0.0418	0.031*
C14	0.2871 (2)	0.7407 (2)	0.03695 (16)	0.0237 (3)
C15	0.2382 (2)	0.6339 (2)	0.10828 (16)	0.0260 (3)
H15	0.1139	0.5925	0.1271	0.031*
C16	0.3728 (3)	0.5890 (2)	0.15132 (16)	0.0255 (3)
H16	0.3404	0.5157	0.1999	0.031*
C17	0.7029 (2)	0.6042 (2)	0.16581 (16)	0.0243 (3)
H17A	0.8241	0.6485	0.1432	0.029*
N17	0.6731 (2)	0.50698 (17)	0.23105 (14)	0.0262 (3)
O17	0.83261 (19)	0.48073 (17)	0.25530 (13)	0.0313 (3)
H17	0.802 (4)	0.422 (3)	0.290 (2)	0.038*
N21	0.7593 (2)	0.2624 (2)	0.38141 (16)	0.0347 (4)
C22	0.8170 (3)	0.2995 (2)	0.50056 (19)	0.0332 (4)
H22	0.8601	0.4061	0.5427	0.040*
C23	0.8186 (3)	0.1963 (2)	0.56604 (17)	0.0293 (4)
H23	0.8624	0.2314	0.6508	0.035*
C24	0.7548 (2)	0.0370 (2)	0.50742 (16)	0.0248 (3)
C25	0.6942 (3)	−0.0027 (2)	0.38201 (17)	0.0293 (4)
H25	0.6498	−0.1081	0.3367	0.035*
C26	0.6996 (3)	0.1112 (3)	0.32567 (19)	0.0353 (4)
H26	0.6580	0.0810	0.2408	0.042*
N31	0.7529 (2)	−0.07022 (18)	0.56773 (14)	0.0310 (3)
C32A	0.8044 (3)	−0.0347 (2)	0.69838 (18)	0.0343 (4)	0.818 (7)
H32A	0.7451	0.0309	0.7391	0.041*	0.818 (7)
H32B	0.9436	0.0214	0.7234	0.041*	0.818 (7)
C33A	0.7314 (5)	−0.1901 (3)	0.7287 (3)	0.0353 (6)	0.818 (7)
H33A	0.5990	−0.2232	0.7431	0.042*	0.818 (7)
H33B	0.8114	−0.1879	0.8009	0.042*	0.818 (7)
C34A	0.7439 (6)	−0.2973 (4)	0.6157 (3)	0.0375 (7)	0.818 (7)
H34A	0.6535	−0.4072	0.6077	0.045*	0.818 (7)
H34B	0.8736	−0.2917	0.6182	0.045*	0.818 (7)
C35A	0.6923 (3)	−0.2352 (2)	0.5101 (2)	0.0343 (4)	0.818 (7)
H35A	0.7619	−0.2493	0.4432	0.041*	0.818 (7)
H35B	0.5544	−0.2875	0.4788	0.041*	0.818 (7)
C32B	0.8044 (3)	−0.0347 (2)	0.69838 (18)	0.0343 (4)	0.182 (7)
H32C	0.7126	−0.0074	0.7417	0.041*	0.182 (7)
H32D	0.9342	0.0486	0.7286	0.041*	0.182 (7)
C33B	0.789 (2)	−0.2045 (17)	0.7034 (14)	0.0353 (6)	0.182 (7)
H33C	0.9172	−0.2030	0.7083	0.042*	0.182 (7)
H33D	0.7390	−0.2313	0.7768	0.042*	0.182 (7)
C34B	0.663 (3)	−0.3258 (18)	0.5944 (15)	0.0375 (7)	0.182 (7)
H34C	0.7027	−0.4117	0.5715	0.045*	0.182 (7)
H34D	0.5288	−0.3698	0.6059	0.045*	0.182 (7)
C35B	0.6923 (3)	−0.2352 (2)	0.5101 (2)	0.0343 (4)	0.182 (7)
H35C	0.5733	−0.2730	0.4522	0.041*	0.182 (7)
H35D	0.7900	−0.2476	0.4642	0.041*	0.182 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02771 (10)	0.03555 (11)	0.03907 (12)	0.01677 (8)	0.00721 (7)	0.01594 (8)
C11	0.0270 (8)	0.0180 (7)	0.0207 (8)	0.0092 (6)	0.0029 (6)	0.0034 (6)
C12	0.0249 (8)	0.0228 (8)	0.0295 (9)	0.0090 (6)	0.0086 (6)	0.0076 (7)
C13	0.0291 (8)	0.0225 (8)	0.0281 (9)	0.0122 (7)	0.0081 (6)	0.0096 (7)
C14	0.0264 (8)	0.0218 (7)	0.0238 (8)	0.0114 (6)	0.0043 (6)	0.0053 (6)
C15	0.0250 (8)	0.0255 (8)	0.0284 (9)	0.0094 (7)	0.0083 (6)	0.0098 (7)
C16	0.0298 (8)	0.0224 (8)	0.0255 (8)	0.0097 (7)	0.0065 (6)	0.0106 (6)
C17	0.0265 (8)	0.0223 (8)	0.0240 (8)	0.0098 (6)	0.0042 (6)	0.0070 (6)
N17	0.0267 (7)	0.0246 (7)	0.0263 (7)	0.0108 (6)	0.0011 (5)	0.0051 (6)
O17	0.0295 (7)	0.0320 (7)	0.0363 (8)	0.0140 (6)	0.0031 (5)	0.0155 (6)
N21	0.0307 (8)	0.0372 (9)	0.0414 (9)	0.0155 (7)	0.0073 (7)	0.0178 (7)
C22	0.0316 (9)	0.0254 (9)	0.0421 (11)	0.0114 (7)	0.0074 (8)	0.0081 (8)
C23	0.0366 (10)	0.0242 (8)	0.0258 (9)	0.0120 (7)	0.0036 (7)	0.0058 (7)
C24	0.0282 (8)	0.0231 (8)	0.0251 (8)	0.0107 (7)	0.0068 (6)	0.0094 (6)
C25	0.0341 (9)	0.0271 (8)	0.0254 (9)	0.0115 (7)	0.0041 (7)	0.0072 (7)
C26	0.0345 (10)	0.0433 (11)	0.0280 (9)	0.0154 (9)	0.0036 (7)	0.0117 (8)
N31	0.0429 (9)	0.0243 (7)	0.0258 (8)	0.0138 (7)	0.0067 (6)	0.0069 (6)
C32A	0.0403 (10)	0.0358 (10)	0.0278 (9)	0.0148 (8)	0.0046 (8)	0.0129 (8)
C33A	0.0378 (16)	0.0400 (13)	0.0359 (14)	0.0186 (11)	0.0094 (11)	0.0210 (11)
C34A	0.0378 (18)	0.0326 (13)	0.0502 (16)	0.0195 (14)	0.0082 (14)	0.0179 (12)
C35A	0.0379 (10)	0.0227 (8)	0.0424 (11)	0.0133 (8)	0.0087 (8)	0.0063 (8)
C32B	0.0403 (10)	0.0358 (10)	0.0278 (9)	0.0148 (8)	0.0046 (8)	0.0129 (8)
C33B	0.0378 (16)	0.0400 (13)	0.0359 (14)	0.0186 (11)	0.0094 (11)	0.0210 (11)
C34B	0.0378 (18)	0.0326 (13)	0.0502 (16)	0.0195 (14)	0.0082 (14)	0.0179 (12)
C35B	0.0379 (10)	0.0227 (8)	0.0424 (11)	0.0133 (8)	0.0087 (8)	0.0063 (8)

Geometric parameters (Å, º)

Br1—C14	1.8927 (17)	C24—C25	1.405 (3)
C11—C12	1.388 (2)	C25—C26	1.365 (3)
C11—C16	1.395 (2)	C25—H25	0.9500
C11—C17	1.465 (2)	C26—H26	0.9500
C12—C13	1.384 (2)	N31—C32A	1.455 (2)
C12—H12	0.9500	N31—C35A	1.456 (2)
C13—C14	1.380 (2)	C32A—C33A	1.494 (3)
C13—H13	0.9500	C32A—H32A	0.9900
C14—C15	1.389 (2)	C32A—H32B	0.9900
C15—C16	1.380 (3)	C33A—C34A	1.524 (4)
C15—H15	0.9500	C33A—H33A	0.9900
C16—H16	0.9500	C33A—H33B	0.9900
C17—N17	1.270 (2)	C34A—C35A	1.545 (4)
C17—H17A	0.9500	C34A—H34A	0.9900
N17—O17	1.385 (2)	C34A—H34B	0.9900
O17—H17	0.72 (3)	C35A—H35A	0.9900
N21—C22	1.335 (3)	C35A—H35B	0.9900
N21—C26	1.337 (3)	C33B—C34B	1.49 (2)
C22—C23	1.359 (3)	C33B—H33C	0.9900
C22—H22	0.9500	C33B—H33D	0.9900
C23—C24	1.408 (2)	C34B—H34C	0.9900
C23—H23	0.9500	C34B—H34D	0.9900
C24—N31	1.345 (2)
C12—C11—C16	118.69 (16)	N21—C26—C25	124.68 (19)
C12—C11—C17	118.21 (15)	N21—C26—H26	117.7
C16—C11—C17	123.08 (15)	C25—C26—H26	117.7
C13—C12—C11	121.40 (16)	C24—N31—C32A	123.51 (16)
C13—C12—H12	119.3	C24—N31—C35A	123.72 (16)
C11—C12—H12	119.3	C32A—N31—C35A	112.73 (16)
C14—C13—C12	118.59 (16)	N31—C32A—C33A	105.09 (18)
C14—C13—H13	120.7	N31—C32A—H32A	110.7
C12—C13—H13	120.7	C33A—C32A—H32A	110.7
C13—C14—C15	121.53 (16)	N31—C32A—H32B	110.7
C13—C14—Br1	118.44 (13)	C33A—C32A—H32B	110.7
C15—C14—Br1	120.03 (13)	H32A—C32A—H32B	108.8
C16—C15—C14	118.97 (16)	C32A—C33A—C34A	102.5 (2)
C16—C15—H15	120.5	C32A—C33A—H33A	111.3
C14—C15—H15	120.5	C34A—C33A—H33A	111.3
C15—C16—C11	120.82 (16)	C32A—C33A—H33B	111.3
C15—C16—H16	119.6	C34A—C33A—H33B	111.3
C11—C16—H16	119.6	H33A—C33A—H33B	109.2
N17—C17—C11	121.93 (16)	C33A—C34A—C35A	104.7 (2)
N17—C17—H17A	119.0	C33A—C34A—H34A	110.8
C11—C17—H17A	119.0	C35A—C34A—H34A	110.8
C17—N17—O17	110.65 (15)	C33A—C34A—H34B	110.8
N17—O17—H17	103 (2)	C35A—C34A—H34B	110.8
C22—N21—C26	115.57 (17)	H34A—C34A—H34B	108.9
N21—C22—C23	124.90 (18)	N31—C35A—C34A	101.86 (19)
N21—C22—H22	117.6	N31—C35A—H35A	111.4
C23—C22—H22	117.6	C34A—C35A—H35A	111.4
C22—C23—C24	119.53 (17)	N31—C35A—H35B	111.4
C22—C23—H23	120.2	C34A—C35A—H35B	111.4
C24—C23—H23	120.2	H35A—C35A—H35B	109.3
N31—C24—C25	122.13 (16)	C34B—C33B—H33C	109.4
N31—C24—C23	122.06 (16)	C34B—C33B—H33D	109.4
C25—C24—C23	115.81 (16)	H33C—C33B—H33D	108.0
C26—C25—C24	119.51 (17)	C33B—C34B—H34C	111.8
C26—C25—H25	120.2	C33B—C34B—H34D	111.8
C24—C25—H25	120.2	H34C—C34B—H34D	109.5
C16—C11—C12—C13	−0.3 (3)	C22—C23—C24—C25	0.4 (3)
C17—C11—C12—C13	178.31 (16)	N31—C24—C25—C26	−179.91 (18)
C11—C12—C13—C14	0.8 (3)	C23—C24—C25—C26	−0.2 (3)
C12—C13—C14—C15	−0.8 (3)	C22—N21—C26—C25	0.2 (3)
C12—C13—C14—Br1	179.73 (13)	C24—C25—C26—N21	−0.1 (3)
C13—C14—C15—C16	0.3 (3)	C25—C24—N31—C32A	−176.39 (18)
Br1—C14—C15—C16	179.70 (13)	C23—C24—N31—C32A	3.9 (3)
C14—C15—C16—C11	0.3 (3)	C25—C24—N31—C35A	1.2 (3)
C12—C11—C16—C15	−0.3 (3)	C23—C24—N31—C35A	−178.51 (18)
C17—C11—C16—C15	−178.82 (16)	C24—N31—C32A—C33A	164.5 (2)
C12—C11—C17—N17	−179.69 (16)	C35A—N31—C32A—C33A	−13.3 (3)
C16—C11—C17—N17	−1.2 (3)	N31—C32A—C33A—C34A	30.3 (3)
C11—C17—N17—O17	178.51 (14)	C32A—C33A—C34A—C35A	−36.6 (3)
C26—N21—C22—C23	0.1 (3)	C24—N31—C35A—C34A	172.7 (2)
N21—C22—C23—C24	−0.4 (3)	C32A—N31—C35A—C34A	−9.6 (2)
C22—C23—C24—N31	−179.88 (18)	C33A—C34A—C35A—N31	28.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O17—H17···N21	0.72 (3)	1.96 (3)	2.678 (2)	171 (3)

(BrCO5) SD-1–27-6–4 4-(1-pyrrolidinyl)-pyridine, (4-Br-PhCOOH)2

Crystal data

(C9H12N2)(C7H5BrO2)2	Z = 2
Mr = 550.25	F(000) = 552
Triclinic, P1	Dx = 1.650 Mg m^−3
a = 9.3718 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6497 (6) Å	Cell parameters from 9903 reflections
c = 14.1666 (9) Å	θ = 2.4–31.6°
α = 98.672 (3)°	µ = 3.69 mm^−1
β = 105.769 (2)°	T = 120 K
γ = 110.884 (3)°	Prism, colourless
V = 1107.38 (12) Å^3	0.32 × 0.18 × 0.12 mm

Data collection

Bruker APEX-II CCD diffractometer	6911 independent reflections
Radiation source: fine-focus sealed tube	4410 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 31.7°, θmin = 1.6°
Absorption correction: multi-scan SADABS	h = −13→13
Tmin = 0.385, Tmax = 0.666	k = −13→14
26091 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.030P)^2 + 3.P] where P = (Fo^2 + 2Fc^2)/3
6911 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 1.97 e Å^−3
10 restraints	Δρmin = −2.73 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N11	−0.1715 (3)	0.2991 (3)	0.3082 (2)	0.0244 (6)
C12A	−0.2259 (4)	0.1317 (4)	0.2865 (3)	0.0300 (7)	0.525 (10)
H12A	−0.2358	0.0976	0.3479	0.036*	0.525 (10)
H12B	−0.1475	0.1002	0.2649	0.036*	0.525 (10)
C13A	−0.3877 (10)	0.0633 (9)	0.2028 (7)	0.0354 (16)	0.525 (10)
H13A	−0.4388	−0.0333	0.1525	0.043*	0.525 (10)
H13B	−0.4573	−0.0001	0.2356	0.043*	0.525 (10)
C14A	−0.4517 (12)	0.1888 (13)	0.2184 (8)	0.034 (2)	0.525 (10)
H14A	−0.5300	0.1831	0.1533	0.041*	0.525 (10)
H14B	−0.5072	0.1759	0.2689	0.041*	0.525 (10)
C15A	−0.3005 (4)	0.3439 (4)	0.2575 (3)	0.0280 (7)	0.525 (10)
H15A	−0.2797	0.3858	0.2006	0.034*	0.525 (10)
H15B	−0.3118	0.4208	0.3062	0.034*	0.525 (10)
C12B	−0.2259 (4)	0.1317 (4)	0.2865 (3)	0.0300 (7)	0.475 (10)
H12C	−0.1938	0.1001	0.3495	0.036*	0.475 (10)
H12D	−0.1831	0.0923	0.2370	0.036*	0.475 (10)
C13B	−0.4176 (11)	0.0761 (10)	0.2393 (8)	0.0354 (16)	0.475 (10)
H13C	−0.4697	−0.0272	0.1899	0.043*	0.475 (10)
H13D	−0.4659	0.0721	0.2935	0.043*	0.475 (10)
C14B	−0.4385 (14)	0.1958 (15)	0.1870 (8)	0.034 (2)	0.475 (10)
H14C	−0.5454	0.1987	0.1795	0.041*	0.475 (10)
H14D	−0.4295	0.1753	0.1187	0.041*	0.475 (10)
C15B	−0.3005 (4)	0.3439 (4)	0.2575 (3)	0.0280 (7)	0.475 (10)
H15C	−0.2618	0.4173	0.2186	0.034*	0.475 (10)
H15D	−0.3355	0.3927	0.3081	0.034*	0.475 (10)
N21	0.2961 (3)	0.6070 (3)	0.4839 (2)	0.0260 (6)
H21	0.398 (5)	0.671 (5)	0.514 (3)	0.031*
C22	0.2560 (4)	0.4557 (4)	0.4657 (3)	0.0285 (7)
H22	0.3374	0.4213	0.4934	0.034*
C23	0.1019 (4)	0.3494 (4)	0.4084 (3)	0.0267 (7)
H23	0.0760	0.2423	0.3972	0.032*
C24	−0.0198 (3)	0.3998 (4)	0.3655 (2)	0.0218 (6)
C25	0.0279 (4)	0.5598 (4)	0.3871 (2)	0.0252 (7)
H25	−0.0497	0.5989	0.3607	0.030*
C26	0.1840 (4)	0.6595 (4)	0.4454 (2)	0.0261 (7)
H26	0.2143	0.7675	0.4592	0.031*
Br1	1.36401 (5)	1.32683 (5)	0.91260 (4)	0.05505 (16)
C31	0.8659 (4)	1.0224 (3)	0.6520 (2)	0.0233 (6)
C37	0.7054 (4)	0.9209 (4)	0.5673 (2)	0.0255 (7)
O31	0.6915 (3)	0.9462 (3)	0.48119 (18)	0.0361 (6)
O32	0.6023 (3)	0.8208 (3)	0.58871 (18)	0.0311 (5)
C32	1.0031 (4)	1.1022 (4)	0.6297 (3)	0.0259 (7)
H32	0.9945	1.0948	0.5606	0.031*
C33	1.1523 (4)	1.1926 (4)	0.7070 (3)	0.0306 (8)
H33	1.2464	1.2451	0.6915	0.037*
C34	1.1607 (4)	1.2045 (4)	0.8062 (3)	0.0327 (8)
C35	1.0270 (4)	1.1293 (4)	0.8314 (3)	0.0351 (8)
H35	1.0355	1.1407	0.9008	0.042*
C36	0.8789 (4)	1.0361 (4)	0.7529 (3)	0.0288 (7)
H36	0.7860	0.9815	0.7688	0.035*
Br2	−0.24046 (6)	0.17510 (8)	−0.01179 (3)	0.0838 (3)
C41	0.2627 (4)	0.5240 (4)	0.2247 (2)	0.0243 (6)
C47	0.4233 (4)	0.6324 (4)	0.3042 (2)	0.0253 (7)
O41	0.4400 (3)	0.7745 (3)	0.32983 (18)	0.0319 (5)
H41	0.529 (5)	0.828 (5)	0.382 (3)	0.038*
O42	0.5255 (3)	0.5872 (3)	0.34142 (19)	0.0343 (6)
C42	0.2287 (5)	0.3708 (4)	0.1964 (3)	0.0389 (9)
H42	0.3090	0.3359	0.2254	0.047*
C43	0.0783 (6)	0.2653 (5)	0.1258 (3)	0.0511 (12)
H43	0.0547	0.1588	0.1062	0.061*
C44	−0.0355 (4)	0.3186 (5)	0.0851 (3)	0.0440 (11)
C45	−0.0052 (4)	0.4707 (6)	0.1121 (3)	0.0459 (11)
H45	−0.0858	0.5051	0.0829	0.055*
C46	0.1453 (4)	0.5744 (5)	0.1830 (3)	0.0342 (8)
H46	0.1679	0.6807	0.2030	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0206 (12)	0.0198 (13)	0.0268 (13)	0.0060 (10)	0.0055 (10)	0.0011 (11)
C12A	0.0273 (16)	0.0208 (16)	0.0335 (18)	0.0042 (13)	0.0089 (13)	0.0023 (13)
C13A	0.027 (3)	0.027 (3)	0.032 (4)	−0.001 (2)	0.001 (3)	0.002 (3)
C14A	0.015 (2)	0.046 (3)	0.031 (5)	0.0087 (19)	0.006 (3)	−0.005 (4)
C15A	0.0193 (14)	0.0302 (17)	0.0285 (16)	0.0086 (13)	0.0028 (12)	0.0064 (14)
C12B	0.0273 (16)	0.0208 (16)	0.0335 (18)	0.0042 (13)	0.0089 (13)	0.0023 (13)
C13B	0.027 (3)	0.027 (3)	0.032 (4)	−0.001 (2)	0.001 (3)	0.002 (3)
C14B	0.015 (2)	0.046 (3)	0.031 (5)	0.0087 (19)	0.006 (3)	−0.005 (4)
C15B	0.0193 (14)	0.0302 (17)	0.0285 (16)	0.0086 (13)	0.0028 (12)	0.0064 (14)
N21	0.0176 (12)	0.0292 (15)	0.0215 (13)	0.0039 (11)	0.0031 (10)	0.0019 (11)
C22	0.0195 (14)	0.0346 (19)	0.0305 (17)	0.0117 (13)	0.0064 (12)	0.0106 (14)
C23	0.0226 (14)	0.0236 (16)	0.0336 (17)	0.0093 (13)	0.0097 (13)	0.0083 (13)
C24	0.0193 (13)	0.0204 (15)	0.0225 (14)	0.0060 (11)	0.0076 (11)	0.0024 (12)
C25	0.0212 (14)	0.0233 (16)	0.0269 (16)	0.0091 (12)	0.0048 (12)	0.0027 (13)
C26	0.0250 (15)	0.0220 (16)	0.0250 (15)	0.0062 (12)	0.0070 (12)	0.0015 (12)
Br1	0.02810 (19)	0.0427 (2)	0.0558 (3)	0.00294 (16)	−0.01606 (17)	−0.00567 (19)
C31	0.0193 (13)	0.0174 (14)	0.0260 (15)	0.0070 (11)	0.0010 (11)	0.0003 (12)
C37	0.0229 (14)	0.0197 (15)	0.0246 (15)	0.0064 (12)	0.0019 (12)	−0.0011 (12)
O31	0.0326 (13)	0.0299 (13)	0.0253 (12)	0.0003 (10)	−0.0002 (10)	0.0026 (10)
O32	0.0213 (11)	0.0269 (12)	0.0311 (12)	0.0016 (9)	0.0028 (9)	0.0027 (10)
C32	0.0228 (14)	0.0212 (15)	0.0291 (16)	0.0091 (12)	0.0050 (12)	0.0020 (13)
C33	0.0196 (14)	0.0201 (16)	0.045 (2)	0.0058 (12)	0.0065 (14)	0.0052 (14)
C34	0.0197 (14)	0.0202 (16)	0.0398 (19)	0.0050 (12)	−0.0070 (13)	−0.0014 (14)
C35	0.0290 (17)	0.035 (2)	0.0269 (17)	0.0095 (15)	0.0000 (13)	−0.0032 (15)
C36	0.0226 (14)	0.0249 (17)	0.0291 (17)	0.0052 (13)	0.0041 (13)	0.0012 (13)
Br2	0.0346 (2)	0.1141 (5)	0.0307 (2)	−0.0294 (3)	0.00512 (17)	−0.0155 (3)
C41	0.0198 (13)	0.0272 (16)	0.0191 (14)	0.0048 (12)	0.0050 (11)	0.0035 (12)
C47	0.0193 (13)	0.0303 (17)	0.0209 (14)	0.0060 (13)	0.0056 (11)	0.0058 (13)
O41	0.0286 (12)	0.0266 (13)	0.0260 (12)	0.0049 (10)	−0.0006 (10)	0.0031 (10)
O42	0.0244 (11)	0.0394 (14)	0.0325 (13)	0.0130 (11)	0.0014 (10)	0.0076 (11)
C42	0.040 (2)	0.034 (2)	0.0296 (18)	0.0110 (16)	0.0008 (15)	0.0038 (15)
C43	0.059 (3)	0.032 (2)	0.032 (2)	−0.0036 (19)	0.0057 (19)	0.0018 (17)
C44	0.0254 (17)	0.056 (3)	0.0193 (16)	−0.0095 (17)	0.0044 (13)	−0.0037 (17)
C45	0.0241 (16)	0.078 (3)	0.0235 (17)	0.0214 (19)	−0.0011 (13)	−0.0035 (18)
C46	0.0281 (16)	0.042 (2)	0.0242 (16)	0.0150 (15)	0.0019 (13)	−0.0013 (15)

Geometric parameters (Å, º)

N11—C24	1.332 (4)	C26—H26	0.9500
N11—C12A	1.464 (4)	Br1—C34	1.897 (3)
N11—C15A	1.469 (4)	C31—C36	1.382 (5)
C12A—C13A	1.488 (8)	C31—C32	1.391 (5)
C12A—H12A	0.9900	C31—C37	1.508 (4)
C12A—H12B	0.9900	C37—O32	1.241 (4)
C13A—C14A	1.545 (12)	C37—O31	1.262 (4)
C13A—H13A	0.9500	C32—C33	1.387 (4)
C13A—H13B	0.9900	C32—H32	0.9500
C14A—C15A	1.538 (11)	C33—C34	1.371 (5)
C14A—H14A	0.9900	C33—H33	0.9500
C14A—H14B	0.9900	C34—C35	1.378 (5)
C15A—H15A	0.9900	C35—C36	1.393 (4)
C15A—H15B	0.9900	C35—H35	0.9500
C13B—C14B	1.504 (13)	C36—H36	0.9500
C13B—H13B	0.6815	Br2—C44	1.894 (3)
C13B—H13C	0.9900	C41—C42	1.365 (5)
C13B—H13D	0.9900	C41—C46	1.382 (5)
C14B—H14C	0.9900	C41—C47	1.493 (4)
C14B—H14D	0.9900	C47—O42	1.216 (4)
N21—C22	1.335 (4)	C47—O41	1.305 (4)
N21—C26	1.344 (4)	O41—H41	0.87 (4)
N21—H21	0.87 (4)	C42—C43	1.388 (5)
C22—C23	1.361 (4)	C42—H42	0.9500
C22—H22	0.9500	C43—C44	1.371 (7)
C23—C24	1.419 (4)	C43—H43	0.9500
C23—H23	0.9500	C44—C45	1.363 (6)
C24—C25	1.403 (4)	C45—C46	1.385 (5)
C25—C26	1.360 (4)	C45—H45	0.9500
C25—H25	0.9500	C46—H46	0.9500
C24—N11—C12A	123.5 (3)	C26—C25—H25	119.6
C24—N11—C15A	123.7 (3)	C24—C25—H25	119.6
C12A—N11—C15A	112.8 (2)	N21—C26—C25	120.8 (3)
N11—C12A—C13A	106.0 (4)	N21—C26—H26	119.6
N11—C12A—H12A	110.5	C25—C26—H26	119.6
C13A—C12A—H12A	110.5	C36—C31—C32	119.1 (3)
N11—C12A—H12B	110.5	C36—C31—C37	120.4 (3)
C13A—C12A—H12B	110.5	C32—C31—C37	120.5 (3)
H12A—C12A—H12B	108.7	O32—C37—O31	126.8 (3)
C12A—C13A—C14A	102.5 (7)	O32—C37—C31	117.3 (3)
C12A—C13A—H13A	128.7	O31—C37—C31	115.8 (3)
C14A—C13A—H13A	128.7	C33—C32—C31	120.9 (3)
C12A—C13A—H13B	100.8	C33—C32—H32	119.5
C14A—C13A—H13B	91.7	C31—C32—H32	119.5
H13A—C13A—H13B	80.0	C34—C33—C32	118.4 (3)
C15A—C14A—C13A	105.8 (7)	C34—C33—H33	120.8
C15A—C14A—H14A	110.6	C32—C33—H33	120.8
C13A—C14A—H14A	110.6	C33—C34—C35	122.4 (3)
C15A—C14A—H14B	110.6	C33—C34—Br1	118.9 (3)
C13A—C14A—H14B	110.6	C35—C34—Br1	118.7 (3)
H14A—C14A—H14B	108.7	C34—C35—C36	118.4 (3)
N11—C15A—C14A	101.6 (5)	C34—C35—H35	120.8
N11—C15A—H15A	111.5	C36—C35—H35	120.8
C14A—C15A—H15A	111.5	C31—C36—C35	120.7 (3)
N11—C15A—H15B	111.5	C31—C36—H36	119.7
C14A—C15A—H15B	111.5	C35—C36—H36	119.7
H15A—C15A—H15B	109.3	C42—C41—C46	119.5 (3)
C14B—C13B—H13B	140.1	C42—C41—C47	119.0 (3)
C14B—C13B—H13C	110.9	C46—C41—C47	121.4 (3)
H13B—C13B—H13C	38.4	O42—C47—O41	124.7 (3)
C14B—C13B—H13D	110.9	O42—C47—C41	121.1 (3)
H13B—C13B—H13D	73.8	O41—C47—C41	114.2 (3)
H13C—C13B—H13D	108.9	C47—O41—H41	109 (3)
C13B—C14B—H14C	111.1	C41—C42—C43	120.8 (4)
C13B—C14B—H14D	111.1	C41—C42—H42	119.6
H14C—C14B—H14D	109.1	C43—C42—H42	119.6
C22—N21—C26	120.6 (3)	C44—C43—C42	118.5 (4)
C22—N21—H21	119 (3)	C44—C43—H43	120.8
C26—N21—H21	120 (3)	C42—C43—H43	120.8
N21—C22—C23	121.8 (3)	C45—C44—C43	122.0 (3)
N21—C22—H22	119.1	C45—C44—Br2	119.5 (3)
C23—C22—H22	119.1	C43—C44—Br2	118.6 (3)
C22—C23—C24	119.5 (3)	C44—C45—C46	118.8 (4)
C22—C23—H23	120.3	C44—C45—H45	120.6
C24—C23—H23	120.3	C46—C45—H45	120.6
N11—C24—C25	122.2 (3)	C41—C46—C45	120.4 (4)
N11—C24—C23	121.1 (3)	C41—C46—H46	119.8
C25—C24—C23	116.6 (3)	C45—C46—H46	119.8
C26—C25—C24	120.7 (3)
C24—N11—C12A—C13A	−167.5 (5)	C37—C31—C32—C33	−178.3 (3)
C15A—N11—C12A—C13A	10.8 (5)	C31—C32—C33—C34	−1.5 (5)
N11—C12A—C13A—C14A	−27.1 (8)	C32—C33—C34—C35	0.4 (5)
C12A—C13A—C14A—C15A	34.2 (10)	C32—C33—C34—Br1	179.7 (2)
C24—N11—C15A—C14A	−171.1 (5)	C33—C34—C35—C36	1.0 (5)
C12A—N11—C15A—C14A	10.6 (5)	Br1—C34—C35—C36	−178.2 (3)
C13A—C14A—C15A—N11	−27.3 (8)	C32—C31—C36—C35	0.4 (5)
C26—N21—C22—C23	−0.2 (5)	C37—C31—C36—C35	179.8 (3)
N21—C22—C23—C24	0.8 (5)	C34—C35—C36—C31	−1.4 (5)
C12A—N11—C24—C25	−178.4 (3)	C42—C41—C47—O42	2.3 (5)
C15A—N11—C24—C25	3.5 (5)	C46—C41—C47—O42	179.3 (3)
C12A—N11—C24—C23	1.3 (5)	C42—C41—C47—O41	−176.3 (3)
C15A—N11—C24—C23	−176.8 (3)	C46—C41—C47—O41	0.6 (5)
C22—C23—C24—N11	179.3 (3)	C46—C41—C42—C43	0.4 (6)
C22—C23—C24—C25	−1.0 (5)	C47—C41—C42—C43	177.4 (4)
N11—C24—C25—C26	−179.6 (3)	C41—C42—C43—C44	0.0 (6)
C23—C24—C25—C26	0.7 (5)	C42—C43—C44—C45	−0.3 (6)
C22—N21—C26—C25	−0.1 (5)	C42—C43—C44—Br2	179.7 (3)
C24—C25—C26—N21	−0.1 (5)	C43—C44—C45—C46	0.0 (6)
C36—C31—C37—O32	−19.3 (5)	Br2—C44—C45—C46	−179.9 (3)
C32—C31—C37—O32	160.1 (3)	C42—C41—C46—C45	−0.7 (6)
C36—C31—C37—O31	161.5 (3)	C47—C41—C46—C45	−177.6 (3)
C32—C31—C37—O31	−19.1 (4)	C44—C45—C46—C41	0.5 (6)
C36—C31—C32—C33	1.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O32	0.87 (4)	1.83 (4)	2.690 (3)	172 (4)
O41—H41···O31	0.87 (4)	1.64 (4)	2.509 (3)	173 (4)

(BrCO3) D-1–27-6–2 4-(Me2N)-pyridine, 4-Br-PhCOOH

Crystal data

(C7H10N2)(C7H5BrO2)	F(000) = 656
Mr = 323.19	Dx = 1.578 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.5603 (12) Å	Cell parameters from 9987 reflections
b = 8.1700 (8) Å	θ = 2.9–31.9°
c = 12.2863 (12) Å	µ = 3.02 mm^−1
β = 92.157 (3)°	T = 120 K
V = 1360.2 (2) Å^3	Prism, colourless
Z = 4	0.32 × 0.22 × 0.18 mm

Data collection

Bruker APEX-II CCD diffractometer	4543 independent reflections
Radiation source: fine-focus sealed tube	3653 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 33.1°, θmin = 2.9°
Absorption correction: multi-scan SADABS	h = −19→19
Tmin = 0.659, Tmax = 0.747	k = −8→12
19711 measured reflections	l = −17→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.030P)^2 + 0.4P] where P = (Fo^2 + 2Fc^2)/3
4543 reflections	(Δ/σ)max = 0.002
177 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.992962 (10)	0.129265 (18)	0.285184 (13)	0.03245 (6)
N11	0.49287 (8)	0.78104 (14)	0.56978 (10)	0.0223 (2)
H11	0.5384 (13)	0.723 (2)	0.5621 (14)	0.027*
C12	0.47955 (10)	0.85247 (16)	0.66676 (11)	0.0225 (3)
H12	0.5262	0.8332	0.7250	0.027*
C13	0.40089 (10)	0.95167 (16)	0.68368 (11)	0.0212 (2)
H13	0.3934	1.0010	0.7529	0.025*
C14	0.33011 (9)	0.98126 (15)	0.59780 (10)	0.0199 (2)
N14	0.24969 (8)	1.07262 (15)	0.61198 (9)	0.0228 (2)
C17	0.23290 (11)	1.14745 (18)	0.71750 (12)	0.0265 (3)
H17A	0.2338	1.0626	0.7739	0.040*
H17B	0.1686	1.2024	0.7151	0.040*
H17C	0.2850	1.2277	0.7344	0.040*
C18	0.17896 (11)	1.10311 (18)	0.52190 (12)	0.0274 (3)
H18A	0.1533	0.9986	0.4938	0.041*
H18B	0.2117	1.1617	0.4638	0.041*
H18C	0.1244	1.1696	0.5476	0.041*
C15	0.34862 (10)	0.90663 (17)	0.49649 (11)	0.0227 (3)
H15	0.3048	0.9253	0.4356	0.027*
C16	0.42899 (10)	0.80807 (17)	0.48574 (11)	0.0234 (3)
H16	0.4398	0.7578	0.4175	0.028*
C21	0.74314 (10)	0.46646 (15)	0.41008 (10)	0.0206 (2)
C27	0.65733 (10)	0.56540 (16)	0.45032 (11)	0.0213 (2)
O21	0.65932 (8)	0.60196 (13)	0.55052 (8)	0.0272 (2)
O22	0.59097 (8)	0.60303 (13)	0.38245 (8)	0.0286 (2)
C22	0.73759 (11)	0.40222 (17)	0.30519 (11)	0.0239 (3)
H22	0.6817	0.4257	0.2589	0.029*
C23	0.81242 (11)	0.30440 (17)	0.26715 (11)	0.0254 (3)
H23	0.8079	0.2603	0.1956	0.030*
C24	0.89362 (10)	0.27209 (16)	0.33510 (12)	0.0244 (3)
C25	0.90260 (10)	0.33761 (18)	0.43889 (12)	0.0268 (3)
H25	0.9596	0.3166	0.4840	0.032*
C26	0.82671 (10)	0.43473 (17)	0.47604 (11)	0.0239 (3)
H26	0.8319	0.4800	0.5472	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02564 (8)	0.02917 (9)	0.04322 (10)	0.00354 (5)	0.01028 (6)	−0.00146 (6)
N11	0.0208 (5)	0.0236 (6)	0.0228 (6)	0.0007 (4)	0.0037 (4)	−0.0006 (4)
C12	0.0216 (6)	0.0262 (6)	0.0195 (6)	−0.0019 (5)	−0.0015 (5)	0.0015 (5)
C13	0.0235 (6)	0.0228 (6)	0.0174 (6)	−0.0017 (5)	0.0002 (5)	0.0001 (5)
C14	0.0204 (6)	0.0198 (6)	0.0196 (6)	−0.0034 (4)	0.0009 (5)	0.0023 (5)
N14	0.0220 (5)	0.0259 (5)	0.0204 (5)	0.0016 (4)	−0.0004 (4)	0.0009 (4)
C17	0.0267 (7)	0.0296 (7)	0.0236 (7)	0.0037 (5)	0.0051 (5)	−0.0011 (5)
C18	0.0242 (6)	0.0290 (7)	0.0284 (7)	0.0018 (5)	−0.0044 (5)	0.0036 (5)
C15	0.0241 (6)	0.0268 (6)	0.0170 (6)	−0.0026 (5)	−0.0022 (5)	0.0006 (5)
C16	0.0255 (6)	0.0265 (7)	0.0184 (6)	−0.0035 (5)	0.0025 (5)	−0.0022 (5)
C21	0.0231 (6)	0.0191 (6)	0.0195 (6)	−0.0014 (4)	0.0019 (5)	0.0031 (4)
C27	0.0222 (6)	0.0222 (6)	0.0197 (6)	−0.0016 (5)	0.0015 (5)	0.0020 (5)
O21	0.0265 (5)	0.0358 (6)	0.0194 (5)	0.0044 (4)	0.0007 (4)	−0.0025 (4)
O22	0.0274 (5)	0.0367 (6)	0.0215 (5)	0.0076 (4)	−0.0020 (4)	−0.0002 (4)
C22	0.0261 (6)	0.0248 (6)	0.0206 (6)	0.0009 (5)	−0.0001 (5)	0.0024 (5)
C23	0.0319 (7)	0.0231 (6)	0.0213 (6)	0.0014 (5)	0.0040 (5)	−0.0003 (5)
C24	0.0219 (6)	0.0202 (6)	0.0315 (7)	0.0005 (5)	0.0072 (5)	0.0017 (5)
C25	0.0225 (6)	0.0286 (7)	0.0290 (7)	−0.0005 (5)	−0.0021 (5)	0.0017 (5)
C26	0.0249 (6)	0.0257 (6)	0.0211 (6)	−0.0009 (5)	0.0001 (5)	0.0007 (5)

Geometric parameters (Å, º)

Br1—C24	1.9012 (14)	C18—H18C	0.9800
N11—C16	1.3409 (18)	C15—C16	1.365 (2)
N11—C12	1.3450 (18)	C15—H15	0.9500
N11—H11	0.787 (18)	C16—H16	0.9500
C12—C13	1.3618 (19)	C21—C22	1.3909 (19)
C12—H12	0.9500	C21—C26	1.3924 (18)
C13—C14	1.4202 (17)	C21—C27	1.5149 (19)
C13—H13	0.9500	C27—O22	1.2424 (16)
C14—N14	1.3383 (17)	C27—O21	1.2660 (16)
C14—C15	1.4169 (19)	C22—C23	1.387 (2)
N14—C18	1.4584 (17)	C22—H22	0.9500
N14—C17	1.4590 (18)	C23—C24	1.382 (2)
C17—H17A	0.9800	C23—H23	0.9500
C17—H17B	0.9800	C24—C25	1.384 (2)
C17—H17C	0.9800	C25—C26	1.390 (2)
C18—H18A	0.9800	C25—H25	0.9500
C18—H18B	0.9800	C26—H26	0.9500
C16—N11—C12	120.42 (12)	C16—C15—C14	120.48 (12)
C16—N11—H11	119.6 (13)	C16—C15—H15	119.8
C12—N11—H11	120.0 (13)	C14—C15—H15	119.8
N11—C12—C13	121.70 (12)	N11—C16—C15	121.16 (13)
N11—C12—H12	119.1	N11—C16—H16	119.4
C13—C12—H12	119.1	C15—C16—H16	119.4
C12—C13—C14	119.95 (12)	C22—C21—C26	118.91 (13)
C12—C13—H13	120.0	C22—C21—C27	119.23 (12)
C14—C13—H13	120.0	C26—C21—C27	121.85 (12)
N14—C14—C15	121.77 (12)	O22—C27—O21	125.64 (13)
N14—C14—C13	121.97 (12)	O22—C27—C21	117.31 (12)
C15—C14—C13	116.25 (12)	O21—C27—C21	117.05 (11)
C14—N14—C18	120.82 (12)	C23—C22—C21	121.00 (13)
C14—N14—C17	120.30 (11)	C23—C22—H22	119.5
C18—N14—C17	118.86 (12)	C21—C22—H22	119.5
N14—C17—H17A	109.5	C24—C23—C22	118.88 (13)
N14—C17—H17B	109.5	C24—C23—H23	120.6
H17A—C17—H17B	109.5	C22—C23—H23	120.6
N14—C17—H17C	109.5	C23—C24—C25	121.54 (13)
H17A—C17—H17C	109.5	C23—C24—Br1	118.72 (11)
H17B—C17—H17C	109.5	C25—C24—Br1	119.71 (11)
N14—C18—H18A	109.5	C24—C25—C26	118.86 (13)
N14—C18—H18B	109.5	C24—C25—H25	120.6
H18A—C18—H18B	109.5	C26—C25—H25	120.6
N14—C18—H18C	109.5	C25—C26—C21	120.77 (13)
H18A—C18—H18C	109.5	C25—C26—H26	119.6
H18B—C18—H18C	109.5	C21—C26—H26	119.6
C16—N11—C12—C13	1.0 (2)	C26—C21—C27—O22	172.17 (13)
N11—C12—C13—C14	0.3 (2)	C22—C21—C27—O21	170.39 (12)
C12—C13—C14—N14	177.33 (13)	C26—C21—C27—O21	−8.14 (19)
C12—C13—C14—C15	−1.79 (18)	C26—C21—C22—C23	1.7 (2)
C15—C14—N14—C18	−1.88 (19)	C27—C21—C22—C23	−176.84 (12)
C13—C14—N14—C18	179.05 (12)	C21—C22—C23—C24	−0.4 (2)
C15—C14—N14—C17	179.91 (12)	C22—C23—C24—C25	−1.3 (2)
C13—C14—N14—C17	0.83 (19)	C22—C23—C24—Br1	176.96 (10)
N14—C14—C15—C16	−177.05 (13)	C23—C24—C25—C26	1.6 (2)
C13—C14—C15—C16	2.08 (19)	Br1—C24—C25—C26	−176.60 (11)
C12—N11—C16—C15	−0.7 (2)	C24—C25—C26—C21	−0.3 (2)
C14—C15—C16—N11	−0.9 (2)	C22—C21—C26—C25	−1.4 (2)
C22—C21—C27—O22	−9.31 (18)	C27—C21—C26—C25	177.15 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O21	0.787 (18)	1.925 (19)	2.7077 (16)	173.1 (18)

(IF4CO4) SD—A-1–4 4-I—F4-PhCOOH, 4-benzoylpyridine

Crystal data

(C7HF4IO2)(C12H9NO)2	F(000) = 1360
Mr = 686.38	Dx = 1.638 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 25.216 (2) Å	Cell parameters from 9991 reflections
b = 6.0746 (5) Å	θ = 2.2–32.6°
c = 19.0419 (16) Å	µ = 1.22 mm^−1
β = 107.453 (3)°	T = 120 K
V = 2782.5 (4) Å^3	Prism, colourless
Z = 4	0.34 × 0.28 × 0.22 mm

Data collection

Bruker APEX-II CCD diffractometer	8074 independent reflections
Radiation source: fine-focus sealed tube	7262 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 32.6°, θmin = 1.1°
Absorption correction: multi-scan TWINABS	h = −28→37
Tmin = 0.682, Tmax = 0.775	k = −8→9
20908 measured reflections	l = −28→28

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.217	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + (0.060P)^2 + 40.P] where P = (Fo^2 + 2Fc^2)/3
8074 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 1.00 e Å^−3
45 restraints	Δρmin = −2.48 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1	0.59562 (5)	0.2770 (4)	0.40541 (5)	0.02201 (14)	0.4641 (14)
C31A	0.4643 (4)	0.5518 (15)	0.1783 (5)	0.0181 (17)*	0.4641 (14)
C32A	0.4558 (4)	0.3530 (14)	0.2060 (5)	0.0165 (17)*	0.4641 (14)
C33A	0.4926 (5)	0.2706 (17)	0.2714 (6)	0.0144 (17)*	0.4641 (14)
C34A	0.5396 (4)	0.3967 (16)	0.3088 (5)	0.0170 (18)*	0.4641 (14)
C35A	0.5458 (4)	0.5959 (16)	0.2785 (6)	0.0149 (18)*	0.4641 (14)
C36A	0.5107 (4)	0.6721 (19)	0.2164 (6)	0.025 (2)*	0.4641 (14)
F32A	0.4112 (4)	0.2308 (16)	0.1719 (5)	0.0190 (12)*	0.4641 (14)
F33A	0.4792 (5)	0.0734 (18)	0.2971 (6)	0.0272 (15)*	0.4641 (14)
F35A	0.5879 (4)	0.7332 (18)	0.3140 (5)	0.0199 (13)*	0.4641 (14)
F36A	0.5164 (5)	0.8619 (19)	0.1882 (7)	0.0242 (14)*	0.4641 (14)
C37A	0.4260 (4)	0.6389 (13)	0.1083 (5)	0.02201 (14)	0.4641 (14)
O31A	0.3748 (4)	0.6668 (19)	0.1055 (6)	0.026 (2)*	0.4641 (14)
H31A	0.3558	0.6930	0.0619	0.031*	0.4641 (14)
O32A	0.4453 (5)	0.681 (2)	0.0547 (6)	0.041 (4)*	0.4641 (14)
I2	0.40382 (4)	0.6333 (4)	0.09502 (4)	0.02201 (14)	0.5359 (14)
C31B	0.5366 (4)	0.3763 (17)	0.3242 (5)	0.0170 (18)*	0.5359 (14)
C32B	0.5440 (4)	0.5745 (17)	0.2943 (5)	0.0149 (18)*	0.5359 (14)
C33B	0.5081 (5)	0.641 (2)	0.2265 (6)	0.025 (2)*	0.5359 (14)
C34B	0.4631 (4)	0.5066 (18)	0.1876 (5)	0.0181 (17)*	0.5359 (14)
C35B	0.4586 (5)	0.3087 (18)	0.2199 (5)	0.0165 (17)*	0.5359 (14)
C36B	0.4919 (5)	0.2474 (18)	0.2859 (5)	0.0144 (17)*	0.5359 (14)
F32B	0.5840 (3)	0.7156 (14)	0.3312 (4)	0.0199 (13)*	0.5359 (14)
F33B	0.5158 (5)	0.8477 (16)	0.2015 (6)	0.0242 (14)*	0.5359 (14)
F35B	0.4143 (3)	0.1796 (14)	0.1865 (4)	0.0190 (12)*	0.5359 (14)
F36B	0.4841 (4)	0.0619 (16)	0.3147 (5)	0.0272 (15)*	0.5359 (14)
C37B	0.5743 (5)	0.296 (2)	0.3959 (6)	0.02201 (14)	0.5359 (14)
O31B	0.6274 (3)	0.3176 (13)	0.4024 (4)	0.0112 (13)*	0.5359 (14)
H31B	0.6463	0.2451	0.4389	0.013*	0.5359 (14)
O32B	0.5547 (4)	0.1831 (19)	0.4389 (5)	0.031 (2)*	0.5359 (14)
N11_1	0.3184 (3)	0.8189 (16)	−0.0181 (4)	0.0308 (16)*
C12_1	0.2691 (2)	0.7378 (12)	−0.0533 (3)	0.0116 (10)*
H12_1	0.2598	0.5959	−0.0396	0.014*
C13_1	0.2308 (3)	0.8461 (14)	−0.1083 (4)	0.0181 (13)*
H13_1	0.1956	0.7813	−0.1315	0.022*
C14_1	0.2444 (3)	1.0625 (13)	−0.1311 (4)	0.0160 (12)*
C15_1	0.2950 (3)	1.1214 (14)	−0.0934 (4)	0.0207 (13)*
H15_1	0.3078	1.2510	−0.1110	0.025*
C16_1	0.3296 (3)	1.0372 (16)	−0.0380 (4)	0.0264 (16)*
H16_1	0.3618	1.1153	−0.0106	0.032*
C17_1	0.2008 (3)	1.1916 (11)	−0.1892 (3)	0.0123 (11)*
O17_1	0.21480 (19)	1.3916 (9)	−0.1917 (2)	0.0163 (8)*
C21_1	0.1647 (2)	1.0873 (12)	−0.2531 (3)	0.0120 (11)*
C22_1	0.1668 (3)	0.8773 (15)	−0.2843 (4)	0.0200 (14)*
H22_1	0.1972	0.7865	−0.2592	0.024*
C23_1	0.1331 (3)	0.7959 (15)	−0.3413 (4)	0.0227 (14)*
H23_1	0.1377	0.6517	−0.3579	0.027*
C24_1	0.0836 (3)	0.9450 (14)	−0.3829 (4)	0.0220 (14)*
H24_1	0.0568	0.8951	−0.4266	0.026*
C25_1	0.0791 (2)	1.1601 (12)	−0.3538 (3)	0.0148 (11)*
H25_1	0.0488	1.2534	−0.3775	0.018*
C26_1	0.1163 (3)	1.2253 (15)	−0.2954 (4)	0.0211 (14)*
H26_1	0.1130	1.3696	−0.2779	0.025*
N11_2	0.6851 (3)	0.0892 (12)	0.5165 (3)	0.0196 (12)*
C12_2	0.7388 (4)	0.1722 (18)	0.5551 (5)	0.035 (2)*
H12_2	0.7514	0.3060	0.5396	0.041*
C13_2	0.7724 (3)	0.0607 (14)	0.6141 (4)	0.0179 (13)*
H13_2	0.8069	0.1232	0.6417	0.021*
C14_2	0.7574 (3)	−0.1324 (13)	0.6330 (3)	0.0142 (12)*
C15_2	0.7056 (2)	−0.2453 (11)	0.5933 (3)	0.0114 (10)*
H15_2	0.6958	−0.3907	0.6029	0.014*
C16_2	0.6706 (3)	−0.0943 (14)	0.5350 (4)	0.0208 (14)*
H16_2	0.6340	−0.1424	0.5098	0.025*
C17_2	0.7899 (2)	−0.2734 (11)	0.6943 (3)	0.0117 (10)*
O17_2	0.7955 (2)	−0.4771 (10)	0.6828 (3)	0.0249 (11)*
C21_2	0.8389 (3)	−0.1773 (15)	0.7588 (4)	0.0205 (14)*
C22_2	0.8288 (3)	0.0327 (14)	0.7789 (4)	0.0179 (13)*
H22_2	0.7983	0.1209	0.7525	0.021*
C23_2	0.8721 (3)	0.1045 (15)	0.8475 (4)	0.0228 (14)*
H23_2	0.8679	0.2464	0.8661	0.027*
C24_2	0.9125 (3)	−0.0043 (16)	0.8819 (4)	0.0257 (16)*
H24_2	0.9379	0.0524	0.9256	0.031*
C25_2	0.9204 (3)	−0.2004 (13)	0.8575 (4)	0.0202 (13)*
H25_2	0.9525	−0.2815	0.8836	0.024*
C26_2	0.8813 (3)	−0.3001 (13)	0.7909 (4)	0.0171 (13)*
H26_2	0.8869	−0.4418	0.7733	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0217 (3)	0.0243 (2)	0.0185 (2)	0.0022 (2)	0.00375 (17)	0.00311 (16)
C37A	0.0217 (3)	0.0243 (2)	0.0185 (2)	0.0022 (2)	0.00375 (17)	0.00311 (16)
I2	0.0217 (3)	0.0243 (2)	0.0185 (2)	0.0022 (2)	0.00375 (17)	0.00311 (16)
C37B	0.0217 (3)	0.0243 (2)	0.0185 (2)	0.0022 (2)	0.00375 (17)	0.00311 (16)

Geometric parameters (Å, º)

I1—C34A	2.086 (9)	C15_1—H15_1	0.9500
C31A—C32A	1.360 (11)	C16_1—H16_1	0.9500
C31A—C36A	1.386 (13)	C17_1—O17_1	1.270 (8)
C31A—C37A	1.489 (12)	C17_1—C21_1	1.431 (8)
C32A—F32A	1.341 (11)	C21_1—C22_1	1.414 (11)
C32A—C33A	1.403 (11)	C21_1—C26_1	1.500 (10)
C33A—F33A	1.374 (12)	C22_1—C23_1	1.263 (10)
C33A—C34A	1.412 (13)	C22_1—H22_1	0.9500
C34A—C35A	1.370 (12)	C23_1—C24_1	1.553 (11)
C35A—C36A	1.329 (11)	C23_1—H23_1	0.9500
C35A—F35A	1.360 (11)	C24_1—C25_1	1.437 (11)
C36A—F36A	1.298 (12)	C24_1—H24_1	0.9500
C37A—O32A	1.280 (12)	C25_1—C26_1	1.283 (9)
C37A—O31A	1.288 (12)	C25_1—H25_1	0.9500
O31A—H31A	0.8400	C26_1—H26_1	0.9500
I2—C34B	2.087 (9)	N11_2—C16_2	1.257 (11)
C31B—C32B	1.369 (11)	N11_2—C12_2	1.425 (11)
C31B—C36B	1.387 (13)	C12_2—C13_2	1.367 (11)
C31B—C37B	1.493 (12)	C12_2—H12_2	0.9500
C32B—F32B	1.350 (10)	C13_2—C14_2	1.316 (11)
C32B—C33B	1.395 (11)	C13_2—H13_2	0.9500
C33B—F33B	1.379 (12)	C14_2—C15_2	1.468 (9)
C33B—C34B	1.412 (13)	C14_2—C17_2	1.480 (9)
C34B—C35B	1.371 (11)	C15_2—C16_2	1.505 (9)
C35B—C36B	1.338 (11)	C15_2—H15_2	0.9500
C35B—F35B	1.357 (10)	C16_2—H16_2	0.9500
C36B—F36B	1.294 (11)	C17_2—O17_2	1.272 (8)
C37B—O32B	1.274 (12)	C17_2—C21_2	1.570 (10)
C37B—O31B	1.315 (12)	C21_2—C26_2	1.297 (10)
O31B—H31B	0.8400	C21_2—C22_2	1.377 (11)
N11_1—C12_1	1.318 (10)	C22_2—C23_2	1.494 (10)
N11_1—C16_1	1.431 (13)	C22_2—H22_2	0.9500
C12_1—C13_1	1.363 (9)	C23_2—C24_2	1.227 (11)
C12_1—H12_1	0.9500	C23_2—H23_2	0.9500
C13_1—C14_1	1.457 (11)	C24_2—C25_2	1.315 (12)
C13_1—H13_1	0.9500	C24_2—H24_2	0.9500
C14_1—C15_1	1.313 (9)	C25_2—C26_2	1.482 (9)
C14_1—C17_1	1.522 (9)	C25_2—H25_2	0.9500
C15_1—C16_1	1.258 (10)	C26_2—H26_2	0.9500
C32A—C31A—C36A	118.1 (9)	N11_1—C16_1—H16_1	121.4
C32A—C31A—C37A	121.8 (8)	O17_1—C17_1—C21_1	120.3 (6)
C36A—C31A—C37A	120.0 (7)	O17_1—C17_1—C14_1	111.9 (6)
F32A—C32A—C31A	120.7 (8)	C21_1—C17_1—C14_1	121.7 (6)
F32A—C32A—C33A	117.9 (8)	C22_1—C21_1—C17_1	131.5 (6)
C31A—C32A—C33A	121.4 (9)	C22_1—C21_1—C26_1	113.9 (6)
F33A—C33A—C32A	117.4 (9)	C17_1—C21_1—C26_1	114.6 (6)
F33A—C33A—C34A	123.5 (9)	C23_1—C22_1—C21_1	127.9 (8)
C32A—C33A—C34A	119.1 (9)	C23_1—C22_1—H22_1	116.0
C35A—C34A—C33A	116.8 (9)	C21_1—C22_1—H22_1	116.0
C35A—C34A—I1	123.2 (7)	C22_1—C23_1—C24_1	116.2 (8)
C33A—C34A—I1	120.0 (7)	C22_1—C23_1—H23_1	121.9
C36A—C35A—F35A	116.1 (9)	C24_1—C23_1—H23_1	121.9
C36A—C35A—C34A	123.6 (9)	C25_1—C24_1—C23_1	118.5 (6)
F35A—C35A—C34A	120.2 (9)	C25_1—C24_1—H24_1	120.8
F36A—C36A—C35A	123.4 (10)	C23_1—C24_1—H24_1	120.8
F36A—C36A—C31A	115.6 (9)	C26_1—C25_1—C24_1	119.6 (7)
C35A—C36A—C31A	121.0 (10)	C26_1—C25_1—H25_1	120.2
O32A—C37A—O31A	123.8 (10)	C24_1—C25_1—H25_1	120.2
O32A—C37A—C31A	119.0 (9)	C25_1—C26_1—C21_1	123.9 (8)
O31A—C37A—C31A	117.2 (8)	C25_1—C26_1—H26_1	118.1
C37A—O31A—H31A	109.5	C21_1—C26_1—H26_1	118.1
C32B—C31B—C36B	117.9 (8)	C16_2—N11_2—C12_2	118.7 (7)
C32B—C31B—C37B	122.8 (9)	C13_2—C12_2—N11_2	120.5 (9)
C36B—C31B—C37B	119.3 (9)	C13_2—C12_2—H12_2	119.8
F32B—C32B—C31B	121.1 (8)	N11_2—C12_2—H12_2	119.8
F32B—C32B—C33B	118.4 (8)	C14_2—C13_2—C12_2	120.6 (8)
C31B—C32B—C33B	120.4 (9)	C14_2—C13_2—H13_2	119.7
F33B—C33B—C32B	117.6 (9)	C12_2—C13_2—H13_2	119.7
F33B—C33B—C34B	121.2 (9)	C13_2—C14_2—C15_2	124.0 (6)
C32B—C33B—C34B	121.1 (9)	C13_2—C14_2—C17_2	126.6 (6)
C35B—C34B—C33B	115.6 (8)	C15_2—C14_2—C17_2	109.4 (6)
C35B—C34B—I2	124.5 (7)	C14_2—C15_2—C16_2	109.3 (6)
C33B—C34B—I2	119.3 (7)	C14_2—C15_2—H15_2	125.4
C36B—C35B—F35B	118.5 (8)	C16_2—C15_2—H15_2	125.4
C36B—C35B—C34B	123.5 (9)	N11_2—C16_2—C15_2	126.3 (7)
F35B—C35B—C34B	117.7 (8)	N11_2—C16_2—H16_2	116.9
F36B—C36B—C35B	120.5 (9)	C15_2—C16_2—H16_2	116.9
F36B—C36B—C31B	118.1 (8)	O17_2—C17_2—C14_2	119.4 (6)
C35B—C36B—C31B	121.3 (9)	O17_2—C17_2—C21_2	113.2 (6)
O32B—C37B—O31B	125.1 (10)	C14_2—C17_2—C21_2	121.4 (6)
O32B—C37B—C31B	120.0 (10)	C26_2—C21_2—C22_2	126.6 (7)
O31B—C37B—C31B	113.8 (8)	C26_2—C21_2—C17_2	119.9 (7)
C37B—O31B—H31B	109.5	C22_2—C21_2—C17_2	113.3 (6)
C12_1—N11_1—C16_1	116.3 (8)	C21_2—C22_2—C23_2	111.5 (7)
N11_1—C12_1—C13_1	123.6 (7)	C21_2—C22_2—H22_2	124.2
N11_1—C12_1—H12_1	118.2	C23_2—C22_2—H22_2	124.2
C13_1—C12_1—H12_1	118.2	C24_2—C23_2—C22_2	125.5 (8)
C12_1—C13_1—C14_1	119.2 (6)	C24_2—C23_2—H23_2	117.2
C12_1—C13_1—H13_1	120.4	C22_2—C23_2—H23_2	117.2
C14_1—C13_1—H13_1	120.4	C23_2—C24_2—C25_2	119.3 (8)
C15_1—C14_1—C13_1	111.1 (7)	C23_2—C24_2—H24_2	120.4
C15_1—C14_1—C17_1	129.0 (7)	C25_2—C24_2—H24_2	120.4
C13_1—C14_1—C17_1	119.9 (6)	C24_2—C25_2—C26_2	122.7 (7)
C16_1—C15_1—C14_1	131.6 (8)	C24_2—C25_2—H25_2	118.7
C16_1—C15_1—H15_1	114.2	C26_2—C25_2—H25_2	118.7
C14_1—C15_1—H15_1	114.2	C21_2—C26_2—C25_2	114.3 (7)
C15_1—C16_1—N11_1	117.2 (8)	C21_2—C26_2—H26_2	122.9
C15_1—C16_1—H16_1	121.4	C25_2—C26_2—H26_2	122.9
C36A—C31A—C32A—F32A	179.1 (12)	C32B—C31B—C37B—O32B	145.0 (14)
C37A—C31A—C32A—F32A	−2.1 (12)	C36B—C31B—C37B—O32B	−35 (2)
C36A—C31A—C32A—C33A	0.2 (6)	C32B—C31B—C37B—O31B	−46.3 (18)
C37A—C31A—C32A—C33A	178.9 (5)	C36B—C31B—C37B—O31B	133.9 (13)
F32A—C32A—C33A—F33A	−2.1 (11)	C16_1—N11_1—C12_1—C13_1	2.9 (11)
C31A—C32A—C33A—F33A	176.9 (12)	N11_1—C12_1—C13_1—C14_1	1.0 (10)
F32A—C32A—C33A—C34A	−179.4 (12)	C12_1—C13_1—C14_1—C15_1	1.0 (9)
C31A—C32A—C33A—C34A	−0.4 (8)	C12_1—C13_1—C14_1—C17_1	−176.3 (6)
F33A—C33A—C34A—C35A	−176.4 (13)	C13_1—C14_1—C15_1—C16_1	−8.8 (12)
C32A—C33A—C34A—C35A	0.7 (11)	C17_1—C14_1—C15_1—C16_1	168.2 (8)
F33A—C33A—C34A—I1	3.8 (15)	C14_1—C15_1—C16_1—N11_1	13.2 (13)
C32A—C33A—C34A—I1	−179.2 (5)	C12_1—N11_1—C16_1—C15_1	−9.0 (11)
C33A—C34A—C35A—C36A	−0.8 (12)	C15_1—C14_1—C17_1—O17_1	−10.4 (10)
I1—C34A—C35A—C36A	179.0 (6)	C13_1—C14_1—C17_1—O17_1	166.3 (6)
C33A—C34A—C35A—F35A	175.6 (12)	C15_1—C14_1—C17_1—C21_1	142.1 (7)
I1—C34A—C35A—F35A	−4.6 (14)	C13_1—C14_1—C17_1—C21_1	−41.2 (9)
F35A—C35A—C36A—F36A	2.8 (15)	O17_1—C17_1—C21_1—C22_1	136.2 (7)
C34A—C35A—C36A—F36A	179.3 (14)	C14_1—C17_1—C21_1—C22_1	−14.1 (10)
F35A—C35A—C36A—C31A	−175.9 (11)	O17_1—C17_1—C21_1—C26_1	−43.0 (8)
C34A—C35A—C36A—C31A	0.6 (12)	C14_1—C17_1—C21_1—C26_1	166.8 (6)
C32A—C31A—C36A—F36A	−179.1 (13)	C17_1—C21_1—C22_1—C23_1	179.9 (8)
C37A—C31A—C36A—F36A	2.2 (14)	C26_1—C21_1—C22_1—C23_1	−0.9 (11)
C32A—C31A—C36A—C35A	−0.3 (9)	C21_1—C22_1—C23_1—C24_1	0.6 (12)
C37A—C31A—C36A—C35A	−179.0 (7)	C22_1—C23_1—C24_1—C25_1	−0.7 (10)
C32A—C31A—C37A—O32A	−119.9 (10)	C23_1—C24_1—C25_1—C26_1	1.3 (10)
C36A—C31A—C37A—O32A	58.8 (11)	C24_1—C25_1—C26_1—C21_1	−1.6 (11)
C32A—C31A—C37A—O31A	59.8 (9)	C22_1—C21_1—C26_1—C25_1	1.4 (10)
C36A—C31A—C37A—O31A	−121.5 (10)	C17_1—C21_1—C26_1—C25_1	−179.3 (7)
C36B—C31B—C32B—F32B	174.9 (12)	C16_2—N11_2—C12_2—C13_2	−4.1 (12)
C37B—C31B—C32B—F32B	−4.9 (19)	N11_2—C12_2—C13_2—C14_2	4.8 (12)
C36B—C31B—C32B—C33B	−1.3 (18)	C12_2—C13_2—C14_2—C15_2	1.3 (11)
C37B—C31B—C32B—C33B	178.9 (13)	C12_2—C13_2—C14_2—C17_2	178.6 (7)
F32B—C32B—C33B—F33B	−0.1 (19)	C13_2—C14_2—C15_2—C16_2	−6.9 (9)
C31B—C32B—C33B—F33B	176.1 (14)	C17_2—C14_2—C15_2—C16_2	175.4 (5)
F32B—C32B—C33B—C34B	−175.6 (13)	C12_2—N11_2—C16_2—C15_2	−2.7 (11)
C31B—C32B—C33B—C34B	1 (2)	C14_2—C15_2—C16_2—N11_2	7.7 (9)
F33B—C33B—C34B—C35B	−177.0 (15)	C13_2—C14_2—C17_2—O17_2	−132.4 (7)
C32B—C33B—C34B—C35B	−1.7 (19)	C15_2—C14_2—C17_2—O17_2	45.3 (8)
F33B—C33B—C34B—I2	−5 (2)	C13_2—C14_2—C17_2—C21_2	18.6 (10)
C32B—C33B—C34B—I2	170.6 (10)	C15_2—C14_2—C17_2—C21_2	−163.8 (6)
C33B—C34B—C35B—C36B	3.7 (18)	O17_2—C17_2—C21_2—C26_2	4.6 (9)
I2—C34B—C35B—C36B	−168.1 (10)	C14_2—C17_2—C21_2—C26_2	−147.9 (7)
C33B—C34B—C35B—F35B	176.5 (13)	O17_2—C17_2—C21_2—C22_2	−170.5 (6)
I2—C34B—C35B—F35B	4.7 (18)	C14_2—C17_2—C21_2—C22_2	36.9 (8)
F35B—C35B—C36B—F36B	4.5 (19)	C26_2—C21_2—C22_2—C23_2	−3.6 (11)
C34B—C35B—C36B—F36B	177.2 (14)	C17_2—C21_2—C22_2—C23_2	171.2 (6)
F35B—C35B—C36B—C31B	−177.4 (13)	C21_2—C22_2—C23_2—C24_2	1.6 (11)
C34B—C35B—C36B—C31B	−4.6 (19)	C22_2—C23_2—C24_2—C25_2	1.0 (12)
C32B—C31B—C36B—F36B	−178.6 (13)	C23_2—C24_2—C25_2—C26_2	−2.0 (12)
C37B—C31B—C36B—F36B	1.2 (19)	C22_2—C21_2—C26_2—C25_2	2.9 (11)
C32B—C31B—C36B—C35B	3.2 (18)	C17_2—C21_2—C26_2—C25_2	−171.6 (6)
C37B—C31B—C36B—C35B	−177.0 (12)	C24_2—C25_2—C26_2—C21_2	0.1 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O31A—H31A···N11_1	0.84	1.71	2.531 (13)	164
O31B—H31B···N11_2	0.84	1.78	2.620 (10)	179

(ICO12) CS—AE-5–12 4-iodobenzoic acid, 4,4'-bipyridyl

Crystal data

(C7H5IO2)(C10H8N2)	Z = 1
Mr = 404.19	F(000) = 198
Triclinic, P1	Dx = 1.803 Mg m^−3
a = 6.2888 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4027 (6) Å	Cell parameters from 6673 reflections
c = 8.1348 (6) Å	θ = 2.5–33.1°
α = 84.773 (3)°	µ = 2.16 mm^−1
β = 82.604 (3)°	T = 120 K
γ = 83.781 (2)°	Plate, colorless
V = 372.20 (5) Å^3	0.32 × 0.22 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	2379 independent reflections
Radiation source: fine-focus sealed tube	2262 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 33.1°, θmin = 2.5°
Absorption correction: multi-scan SADABS	h = −9→9
Tmin = 0.612, Tmax = 0.747	k = −11→10
8430 measured reflections	l = −10→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.056	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.025P)^2 + 0.2P] where P = (Fo^2 + 2Fc^2)/3
2379 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.46 e Å^−3
13 restraints	Δρmin = −0.28 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N11	0.4372 (9)	0.5876 (12)	0.3152 (12)	0.0249 (9)	0.50
C12	0.6240 (11)	0.6622 (17)	0.2859 (18)	0.0276 (10)	0.50
H12	0.7394	0.6027	0.2174	0.033*	0.50
C13	0.658 (2)	0.823 (3)	0.351 (3)	0.0270 (13)	0.50
H13	0.7895	0.8754	0.3191	0.032*	0.50
C14	0.500 (2)	0.906 (2)	0.461 (3)	0.0198 (15)	0.50
C15	0.3029 (19)	0.830 (2)	0.489 (2)	0.0263 (11)	0.50
H15	0.1844	0.8873	0.5564	0.032*	0.50
C16	0.2821 (12)	0.6715 (15)	0.4167 (16)	0.0277 (10)	0.50
H16	0.1490	0.6193	0.4412	0.033*	0.50
N21	0.6213 (9)	1.3923 (12)	0.6674 (12)	0.0249 (9)	0.50
C22	0.4307 (11)	1.3265 (17)	0.7036 (18)	0.0276 (10)	0.50
H22	0.3239	1.3878	0.7780	0.033*	0.50
C23	0.382 (2)	1.172 (3)	0.637 (3)	0.0270 (13)	0.50
H23	0.2412	1.1335	0.6621	0.032*	0.50
C24	0.537 (2)	1.074 (2)	0.535 (3)	0.0198 (15)	0.50
C25	0.7346 (19)	1.149 (2)	0.491 (2)	0.0263 (11)	0.50
H25	0.8424	1.0949	0.4125	0.032*	0.50
C26	0.7685 (12)	1.3040 (15)	0.5654 (16)	0.0277 (10)	0.50
H26	0.9060	1.3488	0.5414	0.033*	0.50
C31	0.0777 (15)	0.1553 (11)	0.0867 (10)	0.0185 (11)	0.50
C32	−0.1309 (13)	0.1875 (8)	0.0276 (11)	0.0195 (10)	0.50
H32	−0.2157	0.3005	0.0416	0.023*	0.50
C33	−0.2052 (18)	0.0544 (9)	−0.0485 (12)	0.0213 (12)	0.50
H33	−0.3403	0.0754	−0.0909	0.026*	0.50
C34	−0.0803 (16)	−0.1147 (12)	−0.0639 (11)	0.0224 (13)	0.50
I1	−0.21158 (3)	−0.31720 (3)	−0.17736 (3)	0.02283 (7)	0.50
C35	0.1174 (15)	−0.1417 (8)	−0.0098 (11)	0.0230 (12)	0.50
H35	0.2012	−0.2555	−0.0223	0.028*	0.50
C36	0.1979 (18)	−0.0068 (8)	0.0627 (12)	0.0193 (11)	0.50
H36	0.3383	−0.0268	0.0963	0.023*	0.50
C37	0.1482 (7)	0.3093 (6)	0.1669 (5)	0.02283 (7)	0.50
O31	0.3553 (4)	0.2924 (3)	0.1788 (3)	0.0321 (5)	0.50
H31	0.3886	0.3862	0.2162	0.039*	0.50
O32	0.0231 (4)	0.4336 (4)	0.2171 (4)	0.0504 (8)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.033 (3)	0.0217 (18)	0.0222 (18)	−0.007 (2)	−0.004 (2)	−0.0055 (11)
C12	0.030 (3)	0.0270 (14)	0.0265 (17)	−0.004 (3)	0.000 (3)	−0.0069 (10)
C13	0.027 (5)	0.0293 (12)	0.026 (3)	−0.012 (3)	−0.001 (3)	−0.0028 (10)
C14	0.022 (4)	0.020 (3)	0.0199 (12)	−0.006 (3)	−0.008 (3)	0.0004 (19)
C15	0.026 (3)	0.029 (3)	0.026 (3)	−0.012 (3)	0.004 (2)	−0.0105 (14)
C16	0.026 (3)	0.028 (3)	0.032 (2)	−0.012 (2)	−0.002 (3)	−0.0069 (15)
N21	0.033 (3)	0.0217 (18)	0.0222 (18)	−0.007 (2)	−0.004 (2)	−0.0055 (11)
C22	0.030 (3)	0.0270 (14)	0.0265 (17)	−0.004 (3)	0.000 (3)	−0.0069 (10)
C23	0.027 (5)	0.0293 (12)	0.026 (3)	−0.012 (3)	−0.001 (3)	−0.0028 (10)
C24	0.022 (4)	0.020 (3)	0.0199 (12)	−0.006 (3)	−0.008 (3)	0.0004 (19)
C25	0.026 (3)	0.029 (3)	0.026 (3)	−0.012 (3)	0.004 (2)	−0.0105 (14)
C26	0.026 (3)	0.028 (3)	0.032 (2)	−0.012 (2)	−0.002 (3)	−0.0069 (15)
C31	0.0221 (14)	0.022 (3)	0.015 (2)	−0.011 (2)	−0.0041 (15)	−0.0062 (17)
C32	0.0207 (18)	0.010 (3)	0.030 (2)	−0.002 (2)	−0.0039 (13)	−0.0074 (19)
C33	0.0231 (15)	0.013 (3)	0.030 (2)	−0.005 (3)	−0.0074 (15)	−0.002 (2)
C34	0.0300 (18)	0.026 (4)	0.016 (2)	−0.017 (2)	−0.0044 (16)	−0.0091 (18)
I1	0.02846 (13)	0.02027 (9)	0.02241 (9)	−0.00802 (8)	−0.00482 (8)	−0.00674 (6)
C35	0.0271 (17)	0.011 (3)	0.031 (2)	0.003 (2)	−0.0051 (15)	−0.006 (2)
C36	0.0227 (18)	0.013 (3)	0.0251 (19)	−0.007 (3)	−0.0070 (13)	−0.003 (2)
C37	0.02846 (13)	0.02027 (9)	0.02241 (9)	−0.00802 (8)	−0.00482 (8)	−0.00674 (6)
O31	0.0262 (12)	0.0292 (11)	0.0461 (14)	−0.0081 (8)	−0.0105 (9)	−0.0163 (10)
O32	0.0325 (11)	0.0453 (15)	0.080 (2)	−0.0080 (10)	−0.0018 (12)	−0.0433 (15)

Geometric parameters (Å, º)

N11—C16	1.332 (6)	C25—C26	1.394 (9)
N11—C12	1.336 (8)	C25—H25	0.9500
C12—C13	1.391 (9)	C26—H26	0.9500
C12—H12	0.9500	C31—C36	1.363 (9)
C13—C14	1.381 (10)	C31—C32	1.443 (13)
C13—H13	0.9500	C31—C37	1.497 (6)
C14—C15	1.400 (9)	C32—C33	1.363 (9)
C14—C24	1.482 (3)	C32—H32	0.9500
C15—C16	1.387 (9)	C33—C34	1.411 (11)
C15—H15	0.9500	C33—H33	0.9500
C16—H16	0.9500	C34—C35	1.360 (15)
N21—C26	1.320 (7)	C34—I1	2.121 (6)
N21—C22	1.330 (8)	C35—C36	1.377 (10)
C22—C23	1.387 (9)	C35—H35	0.9500
C22—H22	0.9500	C36—H36	0.9500
C23—C24	1.386 (9)	C37—O32	1.208 (5)
C23—H23	0.9500	C37—O31	1.310 (4)
C24—C25	1.405 (9)	O31—H31	0.8400
C16—N11—C12	116.6 (8)	C26—C25—H25	120.8
N11—C12—C13	123.2 (7)	C24—C25—H25	120.8
N11—C12—H12	118.4	N21—C26—C25	124.0 (7)
C13—C12—H12	118.4	N21—C26—H26	118.0
C14—C13—C12	120.3 (10)	C25—C26—H26	118.0
C14—C13—H13	119.9	C36—C31—C32	119.2 (6)
C12—C13—H13	119.9	C36—C31—C37	124.8 (8)
C13—C14—C15	116.3 (10)	C32—C31—C37	116.0 (7)
C13—C14—C24	120.7 (7)	C33—C32—C31	119.5 (7)
C15—C14—C24	122.9 (6)	C33—C32—H32	120.3
C16—C15—C14	119.4 (8)	C31—C32—H32	120.3
C16—C15—H15	120.3	C32—C33—C34	119.6 (10)
C14—C15—H15	120.3	C32—C33—H33	120.2
N11—C16—C15	124.0 (8)	C34—C33—H33	120.2
N11—C16—H16	118.0	C35—C34—C33	120.1 (7)
C15—C16—H16	118.0	C35—C34—I1	122.6 (6)
C26—N21—C22	117.7 (8)	C33—C34—I1	117.3 (7)
N21—C22—C23	122.7 (8)	C34—C35—C36	121.0 (8)
N21—C22—H22	118.7	C34—C35—H35	119.5
C23—C22—H22	118.7	C36—C35—H35	119.5
C24—C23—C22	120.2 (10)	C31—C36—C35	120.5 (10)
C24—C23—H23	119.9	C31—C36—H36	119.7
C22—C23—H23	119.9	C35—C36—H36	119.7
C23—C24—C25	116.7 (10)	O32—C37—O31	124.5 (3)
C23—C24—C14	123.9 (7)	O32—C37—C31	122.3 (5)
C25—C24—C14	119.3 (6)	O31—C37—C31	113.1 (5)
C26—C25—C24	118.3 (8)	C37—O31—H31	109.5
C16—N11—C12—C13	−2 (3)	C14—C24—C25—C26	−178.1 (12)
N11—C12—C13—C14	5 (4)	C22—N21—C26—C25	1 (2)
C12—C13—C14—C15	−6 (4)	C24—C25—C26—N21	−4 (3)
C12—C13—C14—C24	178.2 (18)	C36—C31—C32—C33	1.1 (12)
C13—C14—C15—C16	5 (4)	C37—C31—C32—C33	179.3 (7)
C24—C14—C15—C16	−179.3 (12)	C31—C32—C33—C34	1.9 (12)
C12—N11—C16—C15	1 (2)	C32—C33—C34—C35	−3.0 (13)
C14—C15—C16—N11	−3 (3)	C32—C33—C34—I1	178.2 (7)
C26—N21—C22—C23	−1 (3)	C33—C34—C35—C36	1.0 (13)
N21—C22—C23—C24	3 (4)	I1—C34—C35—C36	179.7 (7)
C22—C23—C24—C25	−6 (4)	C32—C31—C36—C35	−3.1 (12)
C22—C23—C24—C14	178.7 (17)	C37—C31—C36—C35	178.9 (8)
C13—C14—C24—C23	175 (4)	C34—C35—C36—C31	2.1 (12)
C15—C14—C24—C23	0 (2)	C36—C31—C37—O32	−164.1 (8)
C13—C14—C24—C25	0.1 (19)	C32—C31—C37—O32	17.8 (10)
C15—C14—C24—C25	−175 (3)	C36—C31—C37—O31	14.7 (10)
C23—C24—C25—C26	6 (4)	C32—C31—C37—O31	−163.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O31—H31···N11	0.84	1.83	2.666 (9)	174
O31—H31···N21^i	0.84	1.96	2.773 (8)	163

Symmetry code: (i) −x+1, −y+2, −z+1.

(ICO11) SD—A-1–5 4-iodobenzoic acid, 1,2-bis(4-pyridyl)ethane

Crystal data

(C7H5IO2)(C12H12N2)	F(000) = 428
Mr = 432.25	Dx = 1.679 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 10.7653 (5) Å	Cell parameters from 4247 reflections
b = 7.3634 (4) Å	θ = 2.3–31.8°
c = 11.4066 (6) Å	µ = 1.89 mm^−1
β = 109.025 (2)°	T = 120 K
V = 854.80 (8) Å^3	Block, colourless
Z = 2	0.26 × 0.22 × 0.16 mm

Data collection

Bruker APEX-II CCD diffractometer	11346 independent reflections
Radiation source: fine-focus sealed tube	9582 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 32.2°, θmin = 2.3°
Absorption correction: multi-scan TWINABS	h = −16→15
Tmin = 0.640, Tmax = 0.752	k = −10→10
11340 measured reflections	l = 0→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.070P)^2 + 0.030P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
11346 reflections	Δρmax = 0.59 e Å^−3
189 parameters	Δρmin = −1.18 e Å^−3
97 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.12 (2)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N11	0.2946 (5)	0.2753 (5)	0.5771 (4)	0.0514 (6)
C12	0.4217 (5)	0.3002 (5)	0.6277 (4)	0.0455 (5)
H12	0.4688	0.3444	0.5762	0.055*
C13	0.4914 (4)	0.2664 (5)	0.7503 (4)	0.0368 (4)
H13	0.5833	0.2888	0.7822	0.044*
C14	0.4239 (4)	0.1987 (5)	0.8264 (3)	0.0296 (4)
C15	0.2902 (4)	0.1714 (5)	0.7748 (4)	0.0349 (4)
H15	0.2407	0.1265	0.8240	0.042*
C16	0.2292 (5)	0.2104 (6)	0.6502 (4)	0.0482 (7)
H16	0.1373	0.1903	0.6151	0.058*
C17	0.4926 (5)	0.1595 (6)	0.9602 (3)	0.0417 (5)
H17A	0.5774	0.0991	0.9694	0.050*
H17B	0.4385	0.0746	0.9905	0.050*
N21	0.7022 (5)	0.2166 (5)	1.4309 (4)	0.0514 (6)
C22	0.5770 (5)	0.1843 (5)	1.3724 (4)	0.0455 (5)
H22	0.5264	0.1342	1.4189	0.055*
C23	0.5151 (5)	0.2179 (6)	1.2498 (4)	0.0368 (4)
H23	0.4242	0.1913	1.2138	0.044*
C24	0.5840 (4)	0.2910 (5)	1.1767 (3)	0.0296 (4)
C25	0.7170 (4)	0.3242 (5)	1.2371 (4)	0.0349 (4)
H25	0.7702	0.3729	1.1927	0.042*
C26	0.7709 (5)	0.2858 (6)	1.3621 (5)	0.0482 (7)
H26	0.8617	0.3098	1.4015	0.058*
C27	0.5181 (5)	0.3311 (5)	1.0396 (3)	0.0417 (5)
H27A	0.5746	0.4142	1.0110	0.050*
H27B	0.4335	0.3937	1.0281	0.050*
I1	0.15116 (3)	0.26724 (4)	0.30827 (2)	0.02559 (10)	0.6234 (11)
C31A	0.0614 (14)	0.2582 (19)	0.1163 (9)	0.0283 (14)	0.6234 (11)
C32A	−0.0576 (14)	0.1734 (19)	0.0642 (9)	0.0288 (12)	0.6234 (11)
H32A	−0.0976	0.1130	0.1163	0.035*	0.6234 (11)
C33A	−0.1204 (16)	0.174 (2)	−0.0627 (10)	0.0297 (14)	0.6234 (11)
H33A	−0.2035	0.1172	−0.0969	0.036*	0.6234 (11)
C34A	−0.0622 (13)	0.258 (2)	−0.1395 (9)	0.0283 (14)	0.6234 (11)
C35A	0.0603 (13)	0.3488 (18)	−0.0873 (10)	0.0288 (12)	0.6234 (11)
H35A	0.1000	0.4097	−0.1394	0.035*	0.6234 (11)
C36A	0.1215 (16)	0.347 (2)	0.0402 (10)	0.0297 (14)	0.6234 (11)
H36A	0.2038	0.4063	0.0758	0.036*	0.6234 (11)
C37A	−0.1187 (8)	0.2654 (12)	−0.2772 (7)	0.0273 (2)	0.6234 (11)
O31A	−0.2302 (4)	0.1740 (6)	−0.3228 (4)	0.0393 (6)	0.6234 (11)
H31A	−0.2569	0.1821	−0.4005	0.047*	0.6234 (11)
O32A	−0.0606 (5)	0.3283 (7)	−0.3440 (4)	0.0504 (8)	0.6234 (11)
I2	−0.14357 (6)	0.23818 (10)	−0.30640 (5)	0.0273 (2)	0.3766 (11)
C31B	−0.050 (2)	0.250 (3)	−0.1126 (16)	0.0283 (14)	0.3766 (11)
C32B	0.069 (2)	0.332 (3)	−0.0617 (16)	0.0288 (12)	0.3766 (11)
H32B	0.1128	0.3847	−0.1133	0.035*	0.3766 (11)
C33B	0.126 (3)	0.337 (4)	0.0666 (17)	0.0297 (14)	0.3766 (11)
H33B	0.2081	0.3952	0.1025	0.036*	0.3766 (11)
C34B	0.063 (2)	0.259 (3)	0.1427 (15)	0.0283 (14)	0.3766 (11)
C35B	−0.058 (2)	0.164 (3)	0.0896 (16)	0.0288 (12)	0.3766 (11)
H35B	−0.1000	0.1059	0.1409	0.035*	0.3766 (11)
C36B	−0.113 (3)	0.159 (4)	−0.0375 (18)	0.0297 (14)	0.3766 (11)
H36B	−0.1922	0.0947	−0.0750	0.036*	0.3766 (11)
C37B	0.1174 (12)	0.2586 (15)	0.2793 (10)	0.02559 (10)	0.3766 (11)
O31B	0.2390 (7)	0.3219 (11)	0.3235 (6)	0.0393 (6)	0.3766 (11)
H31B	0.2663	0.3122	0.4011	0.047*	0.3766 (11)
O32B	0.0646 (8)	0.1927 (12)	0.3464 (6)	0.0504 (8)	0.3766 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0844 (17)	0.0354 (9)	0.0202 (9)	0.0157 (9)	−0.0023 (10)	−0.0057 (7)
C12	0.0798 (16)	0.0370 (10)	0.0232 (10)	0.0014 (11)	0.0215 (10)	−0.0003 (8)
C13	0.0411 (10)	0.0417 (11)	0.0291 (11)	−0.0067 (8)	0.0136 (9)	−0.0064 (8)
C14	0.0405 (9)	0.0301 (8)	0.0166 (8)	−0.0020 (7)	0.0074 (7)	−0.0047 (6)
C15	0.0387 (9)	0.0284 (8)	0.0388 (11)	−0.0031 (7)	0.0144 (8)	−0.0074 (7)
C16	0.0426 (12)	0.0320 (10)	0.0485 (14)	0.0073 (8)	−0.0147 (10)	−0.0158 (9)
C17	0.0671 (14)	0.0356 (10)	0.0170 (9)	−0.0007 (10)	0.0062 (8)	−0.0036 (8)
N21	0.0844 (17)	0.0354 (9)	0.0202 (9)	0.0157 (9)	−0.0023 (10)	−0.0057 (7)
C22	0.0798 (16)	0.0370 (10)	0.0232 (10)	0.0014 (11)	0.0215 (10)	−0.0003 (8)
C23	0.0411 (10)	0.0417 (11)	0.0291 (11)	−0.0067 (8)	0.0136 (9)	−0.0064 (8)
C24	0.0405 (9)	0.0301 (8)	0.0166 (8)	−0.0020 (7)	0.0074 (7)	−0.0047 (6)
C25	0.0387 (9)	0.0284 (8)	0.0388 (11)	−0.0031 (7)	0.0144 (8)	−0.0074 (7)
C26	0.0426 (12)	0.0320 (10)	0.0485 (14)	0.0073 (8)	−0.0147 (10)	−0.0158 (9)
C27	0.0671 (14)	0.0356 (10)	0.0170 (9)	−0.0007 (10)	0.0062 (8)	−0.0036 (8)
I1	0.0334 (2)	0.02608 (14)	0.01443 (16)	0.0037 (3)	0.00380 (10)	0.0028 (3)
C31A	0.0313 (16)	0.0297 (11)	0.023 (5)	0.0042 (10)	0.007 (3)	−0.001 (3)
C32A	0.0346 (13)	0.029 (2)	0.025 (4)	−0.0012 (12)	0.013 (3)	0.005 (3)
C33A	0.0308 (16)	0.033 (2)	0.025 (5)	−0.0003 (15)	0.007 (3)	0.001 (3)
C34A	0.0313 (16)	0.0297 (11)	0.023 (5)	0.0042 (10)	0.007 (3)	−0.001 (3)
C35A	0.0346 (13)	0.029 (2)	0.025 (4)	−0.0012 (12)	0.013 (3)	0.005 (3)
C36A	0.0308 (16)	0.033 (2)	0.025 (5)	−0.0003 (15)	0.007 (3)	0.001 (3)
C37A	0.0355 (4)	0.0269 (4)	0.0166 (4)	0.0008 (3)	0.0043 (3)	−0.0005 (3)
O31A	0.0398 (16)	0.0534 (17)	0.0188 (13)	−0.0046 (14)	0.0013 (11)	0.0027 (12)
O32A	0.0574 (19)	0.076 (2)	0.0168 (13)	−0.0144 (18)	0.0109 (13)	0.0088 (14)
I2	0.0355 (4)	0.0269 (4)	0.0166 (4)	0.0008 (3)	0.0043 (3)	−0.0005 (3)
C31B	0.0313 (16)	0.0297 (11)	0.023 (5)	0.0042 (10)	0.007 (3)	−0.001 (3)
C32B	0.0346 (13)	0.029 (2)	0.025 (4)	−0.0012 (12)	0.013 (3)	0.005 (3)
C33B	0.0308 (16)	0.033 (2)	0.025 (5)	−0.0003 (15)	0.007 (3)	0.001 (3)
C34B	0.0313 (16)	0.0297 (11)	0.023 (5)	0.0042 (10)	0.007 (3)	−0.001 (3)
C35B	0.0346 (13)	0.029 (2)	0.025 (4)	−0.0012 (12)	0.013 (3)	0.005 (3)
C36B	0.0308 (16)	0.033 (2)	0.025 (5)	−0.0003 (15)	0.007 (3)	0.001 (3)
C37B	0.0334 (2)	0.02608 (14)	0.01443 (16)	0.0037 (3)	0.00380 (10)	0.0028 (3)
O31B	0.0398 (16)	0.0534 (17)	0.0188 (13)	−0.0046 (14)	0.0013 (11)	0.0027 (12)
O32B	0.0574 (19)	0.076 (2)	0.0168 (13)	−0.0144 (18)	0.0109 (13)	0.0088 (14)

Geometric parameters (Å, º)

N11—C12	1.313 (7)	C31A—C36A	1.403 (15)
N11—C16	1.342 (8)	C32A—C33A	1.384 (14)
C12—C13	1.377 (6)	C32A—H32A	0.9500
C12—H12	0.9500	C33A—C34A	1.378 (15)
C13—C14	1.393 (5)	C33A—H33A	0.9500
C13—H13	0.9500	C34A—C35A	1.423 (17)
C14—C15	1.381 (5)	C34A—C37A	1.488 (12)
C14—C17	1.492 (5)	C35A—C36A	1.387 (14)
C15—C16	1.388 (6)	C35A—H35A	0.9500
C15—H15	0.9500	C36A—H36A	0.9500
C16—H16	0.9500	C37A—O32A	1.224 (9)
C17—C27	1.526 (4)	C37A—O31A	1.326 (8)
C17—H17A	0.9900	O31A—H31A	0.8400
C17—H17B	0.9900	I2—C31B	2.112 (17)
N21—C22	1.316 (6)	C31B—C32B	1.36 (3)
N21—C26	1.342 (8)	C31B—C36B	1.42 (2)
C22—C23	1.362 (6)	C32B—C33B	1.39 (2)
C22—H22	0.9500	C32B—H32B	0.9500
C23—C24	1.393 (5)	C33B—C34B	1.39 (2)
C23—H23	0.9500	C33B—H33B	0.9500
C24—C25	1.393 (5)	C34B—C35B	1.43 (3)
C24—C27	1.521 (5)	C34B—C37B	1.475 (17)
C25—C26	1.382 (6)	C35B—C36B	1.38 (2)
C25—H25	0.9500	C35B—H35B	0.9500
C26—H26	0.9500	C36B—H36B	0.9500
C27—H27A	0.9900	C37B—O32B	1.195 (12)
C27—H27B	0.9900	C37B—O31B	1.325 (12)
I1—C31A	2.086 (10)	O31B—H31B	0.8400
C31A—C32A	1.375 (17)
C12—N11—C16	117.3 (4)	C32A—C31A—C36A	119.9 (10)
N11—C12—C13	124.5 (4)	C32A—C31A—I1	121.0 (8)
N11—C12—H12	117.7	C36A—C31A—I1	119.0 (10)
C13—C12—H12	117.7	C31A—C32A—C33A	121.2 (10)
C12—C13—C14	118.3 (4)	C31A—C32A—H32A	119.4
C12—C13—H13	120.8	C33A—C32A—H32A	119.4
C14—C13—H13	120.8	C34A—C33A—C32A	120.0 (13)
C15—C14—C13	118.0 (3)	C34A—C33A—H33A	120.0
C15—C14—C17	120.5 (3)	C32A—C33A—H33A	120.0
C13—C14—C17	121.4 (4)	C33A—C34A—C35A	119.6 (10)
C14—C15—C16	119.1 (4)	C33A—C34A—C37A	124.9 (11)
C14—C15—H15	120.5	C35A—C34A—C37A	115.4 (10)
C16—C15—H15	120.5	C36A—C35A—C34A	119.6 (10)
N11—C16—C15	122.8 (4)	C36A—C35A—H35A	120.2
N11—C16—H16	118.6	C34A—C35A—H35A	120.2
C15—C16—H16	118.6	C35A—C36A—C31A	119.7 (13)
C14—C17—C27	112.3 (3)	C35A—C36A—H36A	120.2
C14—C17—H17A	109.1	C31A—C36A—H36A	120.2
C27—C17—H17A	109.1	O32A—C37A—O31A	121.9 (6)
C14—C17—H17B	109.1	O32A—C37A—C34A	123.7 (8)
C27—C17—H17B	109.1	O31A—C37A—C34A	113.8 (8)
H17A—C17—H17B	107.9	C37A—O31A—H31A	109.5
C22—N21—C26	116.2 (4)	C32B—C31B—C36B	121.2 (17)
N21—C22—C23	124.4 (4)	C32B—C31B—I2	121.7 (14)
N21—C22—H22	117.8	C36B—C31B—I2	117.0 (15)
C23—C22—H22	117.8	C31B—C32B—C33B	119.3 (18)
C22—C23—C24	120.5 (4)	C31B—C32B—H32B	120.4
C22—C23—H23	119.8	C33B—C32B—H32B	120.4
C24—C23—H23	119.8	C34B—C33B—C32B	121 (2)
C23—C24—C25	115.7 (3)	C34B—C33B—H33B	119.6
C23—C24—C27	122.0 (4)	C32B—C33B—H33B	119.6
C25—C24—C27	122.3 (3)	C33B—C34B—C35B	120.0 (17)
C26—C25—C24	119.6 (4)	C33B—C34B—C37B	123.7 (18)
C26—C25—H25	120.2	C35B—C34B—C37B	116.2 (15)
C24—C25—H25	120.2	C36B—C35B—C34B	118.6 (17)
N21—C26—C25	123.6 (4)	C36B—C35B—H35B	120.7
N21—C26—H26	118.2	C34B—C35B—H35B	120.7
C25—C26—H26	118.2	C35B—C36B—C31B	120 (2)
C24—C27—C17	112.5 (3)	C35B—C36B—H36B	120.0
C24—C27—H27A	109.1	C31B—C36B—H36B	120.0
C17—C27—H27A	109.1	O32B—C37B—O31B	121.2 (10)
C24—C27—H27B	109.1	O32B—C37B—C34B	124.6 (13)
C17—C27—H27B	109.1	O31B—C37B—C34B	113.9 (12)
H27A—C27—H27B	107.8	C37B—O31B—H31B	109.5
C16—N11—C12—C13	−0.9 (6)	C32A—C33A—C34A—C37A	178.7 (13)
N11—C12—C13—C14	1.0 (6)	C33A—C34A—C35A—C36A	2 (2)
C12—C13—C14—C15	−0.8 (5)	C37A—C34A—C35A—C36A	−179.0 (13)
C12—C13—C14—C17	−179.8 (4)	C34A—C35A—C36A—C31A	−1 (2)
C13—C14—C15—C16	0.6 (5)	C32A—C31A—C36A—C35A	0 (2)
C17—C14—C15—C16	179.6 (4)	I1—C31A—C36A—C35A	−177.3 (12)
C12—N11—C16—C15	0.6 (6)	C33A—C34A—C37A—O32A	−174.0 (13)
C14—C15—C16—N11	−0.5 (6)	C35A—C34A—C37A—O32A	6.7 (17)
C15—C14—C17—C27	−100.2 (4)	C33A—C34A—C37A—O31A	−3.2 (18)
C13—C14—C17—C27	78.7 (5)	C35A—C34A—C37A—O31A	177.5 (10)
C26—N21—C22—C23	−0.6 (6)	C36B—C31B—C32B—C33B	−5 (3)
N21—C22—C23—C24	0.1 (6)	I2—C31B—C32B—C33B	179 (2)
C22—C23—C24—C25	0.5 (6)	C31B—C32B—C33B—C34B	1 (4)
C22—C23—C24—C27	−179.7 (4)	C32B—C33B—C34B—C35B	3 (4)
C23—C24—C25—C26	−0.6 (5)	C32B—C33B—C34B—C37B	180 (2)
C27—C24—C25—C26	179.6 (4)	C33B—C34B—C35B—C36B	−3 (3)
C22—N21—C26—C25	0.5 (6)	C37B—C34B—C35B—C36B	−179 (2)
C24—C25—C26—N21	0.2 (6)	C34B—C35B—C36B—C31B	−1 (4)
C23—C24—C27—C17	−75.6 (5)	C32B—C31B—C36B—C35B	5 (4)
C25—C24—C27—C17	104.2 (4)	I2—C31B—C36B—C35B	−179 (2)
C14—C17—C27—C24	178.1 (4)	C33B—C34B—C37B—O32B	180 (2)
C36A—C31A—C32A—C33A	−0.2 (19)	C35B—C34B—C37B—O32B	−4 (3)
I1—C31A—C32A—C33A	176.9 (12)	C33B—C34B—C37B—O31B	−7 (3)
C31A—C32A—C33A—C34A	1 (2)	C35B—C34B—C37B—O31B	169.5 (17)
C32A—C33A—C34A—C35A	−2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O31A—H31A···N21^i	0.84	1.85	2.681 (6)	173
O31B—H31B···N11	0.84	1.95	2.778 (8)	169

Symmetry code: (i) x−1, y, z−2.

(BrF4OH13) SD-1–20-12–7 4-Br—F4-PhOH, 2,3,5,6-Me4-pyrazine

Crystal data

(C6HBrF4O)(C8H12N2)	Z = 2
Mr = 381.17	F(000) = 380
Triclinic, P1	Dx = 1.732 Mg m^−3
a = 4.4175 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.5878 (13) Å	Cell parameters from 4524 reflections
c = 13.4274 (14) Å	θ = 3.3–30.5°
α = 80.827 (4)°	µ = 2.86 mm^−1
β = 82.672 (3)°	T = 120 K
γ = 87.809 (4)°	Rod, colourless
V = 730.96 (13) Å^3	0.24 × 0.08 × 0.04 mm

Data collection

Bruker APEX-II CCD diffractometer	4088 independent reflections
Radiation source: fine-focus sealed tube	3211 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 31.7°, θmin = 2.1°
Absorption correction: multi-scan SADABS	h = −6→5
Tmin = 0.547, Tmax = 0.894	k = −16→17
11188 measured reflections	l = −19→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.085P)^2] where P = (Fo^2 + 2Fc^2)/3
4088 reflections	(Δ/σ)max < 0.001
206 parameters	Δρmax = 1.09 e Å^−3
0 restraints	Δρmin = −1.72 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C11	0.4210 (7)	0.2966 (3)	0.3636 (2)	0.0239 (6)
O11	0.5184 (6)	0.3194 (2)	0.44741 (16)	0.0305 (5)
H11	0.398 (9)	0.276 (3)	0.505 (3)	0.037*
C12	0.5258 (7)	0.3579 (2)	0.2701 (2)	0.0233 (6)
F12	0.7180 (4)	0.43861 (15)	0.26876 (14)	0.0311 (4)
C13	0.4397 (7)	0.3373 (2)	0.1803 (2)	0.0233 (6)
F13	0.5457 (5)	0.40086 (15)	0.09433 (13)	0.0308 (4)
C14	0.2469 (7)	0.2552 (3)	0.1781 (2)	0.0245 (6)
Br1	0.13777 (7)	0.22463 (3)	0.05528 (2)	0.02877 (13)
C15	0.1391 (7)	0.1944 (3)	0.2704 (2)	0.0247 (6)
F15	−0.0526 (4)	0.11337 (16)	0.27309 (14)	0.0310 (4)
C16	0.2264 (7)	0.2148 (3)	0.3596 (2)	0.0243 (6)
F16	0.1205 (5)	0.15136 (16)	0.44743 (13)	0.0317 (4)
N21	0.2616 (6)	0.2449 (2)	0.63431 (18)	0.0253 (5)
C22	0.0607 (7)	0.3098 (2)	0.6785 (2)	0.0233 (6)
C23	−0.0373 (7)	0.2876 (3)	0.7828 (2)	0.0243 (6)
N24	0.0694 (6)	0.2004 (2)	0.83937 (18)	0.0249 (5)
C25	0.2694 (7)	0.1351 (2)	0.7952 (2)	0.0237 (6)
C26	0.3686 (7)	0.1571 (3)	0.6908 (2)	0.0243 (6)
C32	−0.0503 (8)	0.4062 (3)	0.6115 (2)	0.0323 (7)
H32A	−0.0793	0.3865	0.5457	0.048*
H32B	0.1006	0.4633	0.6012	0.048*
H32C	−0.2448	0.4321	0.6437	0.048*
C33	−0.2548 (8)	0.3599 (3)	0.8359 (2)	0.0322 (7)
H33A	−0.3240	0.3238	0.9048	0.048*
H33B	−0.4310	0.3768	0.7983	0.048*
H33C	−0.1524	0.4266	0.8396	0.048*
C35	0.3892 (8)	0.0398 (3)	0.8621 (2)	0.0294 (7)
H35A	0.2471	0.0232	0.9245	0.044*
H35B	0.5892	0.0565	0.8793	0.044*
H35C	0.4095	−0.0224	0.8260	0.044*
C36	0.5879 (8)	0.0850 (3)	0.6375 (2)	0.0322 (7)
H36A	0.6472	0.1195	0.5673	0.048*
H36B	0.4904	0.0164	0.6374	0.048*
H36C	0.7697	0.0720	0.6729	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0282 (15)	0.0318 (16)	0.0123 (12)	−0.0002 (12)	−0.0011 (11)	−0.0062 (11)
O11	0.0390 (13)	0.0409 (14)	0.0129 (10)	−0.0106 (11)	−0.0017 (9)	−0.0068 (9)
C12	0.0254 (14)	0.0269 (16)	0.0179 (13)	−0.0044 (12)	0.0005 (11)	−0.0060 (11)
F12	0.0376 (11)	0.0352 (11)	0.0209 (9)	−0.0108 (8)	0.0003 (8)	−0.0068 (7)
C13	0.0301 (15)	0.0286 (16)	0.0098 (12)	0.0008 (12)	0.0041 (10)	−0.0045 (10)
F13	0.0438 (11)	0.0341 (10)	0.0127 (8)	−0.0060 (8)	0.0041 (7)	−0.0028 (7)
C14	0.0279 (15)	0.0362 (17)	0.0098 (12)	0.0037 (13)	−0.0015 (10)	−0.0070 (11)
Br1	0.0367 (2)	0.0372 (2)	0.01414 (16)	−0.00015 (14)	−0.00392 (12)	−0.00882 (12)
C15	0.0264 (15)	0.0294 (16)	0.0183 (13)	0.0000 (12)	0.0004 (11)	−0.0065 (11)
F15	0.0363 (10)	0.0364 (11)	0.0220 (9)	−0.0094 (8)	−0.0024 (8)	−0.0088 (8)
C16	0.0282 (15)	0.0328 (17)	0.0106 (12)	−0.0015 (12)	0.0031 (10)	−0.0038 (11)
F16	0.0424 (11)	0.0381 (11)	0.0124 (8)	−0.0108 (9)	0.0034 (7)	−0.0005 (7)
N21	0.0313 (14)	0.0328 (14)	0.0129 (11)	−0.0063 (11)	−0.0020 (9)	−0.0062 (9)
C22	0.0313 (16)	0.0266 (15)	0.0135 (13)	−0.0046 (12)	−0.0050 (11)	−0.0055 (11)
C23	0.0283 (15)	0.0289 (16)	0.0171 (13)	−0.0052 (12)	−0.0025 (11)	−0.0067 (11)
N24	0.0317 (14)	0.0310 (14)	0.0129 (11)	−0.0066 (11)	−0.0016 (10)	−0.0054 (9)
C25	0.0287 (15)	0.0275 (16)	0.0163 (13)	−0.0055 (12)	−0.0050 (11)	−0.0046 (11)
C26	0.0276 (15)	0.0303 (16)	0.0157 (13)	−0.0050 (12)	−0.0016 (11)	−0.0051 (11)
C32	0.046 (2)	0.0346 (18)	0.0163 (14)	0.0024 (15)	−0.0075 (13)	−0.0031 (12)
C33	0.0360 (18)	0.0386 (19)	0.0208 (15)	0.0041 (15)	0.0007 (13)	−0.0051 (13)
C35	0.0392 (18)	0.0317 (17)	0.0177 (14)	−0.0001 (14)	−0.0056 (13)	−0.0034 (12)
C36	0.0369 (18)	0.0378 (19)	0.0212 (15)	0.0012 (14)	0.0015 (13)	−0.0070 (13)

Geometric parameters (Å, º)

C11—O11	1.331 (4)	C23—C33	1.492 (4)
C11—C16	1.379 (5)	N24—C25	1.332 (4)
C11—C12	1.398 (4)	C25—C26	1.402 (4)
O11—H11	0.98 (4)	C25—C35	1.501 (4)
C12—F12	1.345 (4)	C26—C36	1.496 (4)
C12—C13	1.375 (4)	C32—H32A	0.9800
C13—F13	1.337 (3)	C32—H32B	0.9800
C13—C14	1.369 (5)	C32—H32C	0.9800
C14—C15	1.387 (4)	C33—H33A	0.9800
C14—Br1	1.877 (3)	C33—H33B	0.9800
C15—F15	1.344 (4)	C33—H33C	0.9800
C15—C16	1.367 (4)	C35—H35A	0.9800
C16—F16	1.355 (3)	C35—H35B	0.9800
N21—C22	1.331 (4)	C35—H35C	0.9800
N21—C26	1.343 (4)	C36—H36A	0.9800
C22—C23	1.398 (4)	C36—H36B	0.9800
C22—C32	1.498 (4)	C36—H36C	0.9800
C23—N24	1.338 (4)
O11—C11—C16	125.5 (3)	C26—C25—C35	121.9 (3)
O11—C11—C12	118.8 (3)	N21—C26—C25	119.9 (3)
C16—C11—C12	115.7 (3)	N21—C26—C36	117.5 (3)
C11—O11—H11	107 (3)	C25—C26—C36	122.6 (3)
F12—C12—C13	119.6 (3)	C22—C32—H32A	109.5
F12—C12—C11	118.6 (3)	C22—C32—H32B	109.5
C13—C12—C11	121.8 (3)	H32A—C32—H32B	109.5
F13—C13—C14	120.4 (3)	C22—C32—H32C	109.5
F13—C13—C12	118.1 (3)	H32A—C32—H32C	109.5
C14—C13—C12	121.4 (3)	H32B—C32—H32C	109.5
C13—C14—C15	117.3 (3)	C23—C33—H33A	109.5
C13—C14—Br1	121.5 (2)	C23—C33—H33B	109.5
C15—C14—Br1	121.2 (2)	H33A—C33—H33B	109.5
F15—C15—C16	118.9 (3)	C23—C33—H33C	109.5
F15—C15—C14	119.9 (3)	H33A—C33—H33C	109.5
C16—C15—C14	121.1 (3)	H33B—C33—H33C	109.5
F16—C16—C15	118.9 (3)	C25—C35—H35A	109.5
F16—C16—C11	118.5 (3)	C25—C35—H35B	109.5
C15—C16—C11	122.6 (3)	H35A—C35—H35B	109.5
C22—N21—C26	119.3 (3)	C25—C35—H35C	109.5
N21—C22—C23	120.6 (3)	H35A—C35—H35C	109.5
N21—C22—C32	116.8 (3)	H35B—C35—H35C	109.5
C23—C22—C32	122.6 (3)	C26—C36—H36A	109.5
N24—C23—C22	120.2 (3)	C26—C36—H36B	109.5
N24—C23—C33	117.4 (3)	H36A—C36—H36B	109.5
C22—C23—C33	122.4 (3)	C26—C36—H36C	109.5
C25—N24—C23	119.3 (3)	H36A—C36—H36C	109.5
N24—C25—C26	120.7 (3)	H36B—C36—H36C	109.5
N24—C25—C35	117.5 (3)
O11—C11—C12—F12	−0.9 (4)	O11—C11—C16—F16	0.4 (5)
C16—C11—C12—F12	−179.6 (3)	C12—C11—C16—F16	179.0 (3)
O11—C11—C12—C13	178.6 (3)	O11—C11—C16—C15	−178.8 (3)
C16—C11—C12—C13	−0.1 (5)	C12—C11—C16—C15	−0.3 (5)
F12—C12—C13—F13	−1.7 (4)	C26—N21—C22—C23	0.5 (5)
C11—C12—C13—F13	178.8 (3)	C26—N21—C22—C32	−179.9 (3)
F12—C12—C13—C14	179.4 (3)	N21—C22—C23—N24	−0.3 (5)
C11—C12—C13—C14	−0.2 (5)	C32—C22—C23—N24	−179.9 (3)
F13—C13—C14—C15	−178.2 (3)	N21—C22—C23—C33	178.1 (3)
C12—C13—C14—C15	0.7 (5)	C32—C22—C23—C33	−1.5 (5)
F13—C13—C14—Br1	2.8 (4)	C22—C23—N24—C25	−0.1 (5)
C12—C13—C14—Br1	−178.3 (2)	C33—C23—N24—C25	−178.5 (3)
C13—C14—C15—F15	179.5 (3)	C23—N24—C25—C26	0.2 (5)
Br1—C14—C15—F15	−1.5 (4)	C23—N24—C25—C35	178.4 (3)
C13—C14—C15—C16	−1.0 (5)	C22—N21—C26—C25	−0.3 (5)
Br1—C14—C15—C16	178.0 (2)	C22—N21—C26—C36	178.5 (3)
F15—C15—C16—F16	1.1 (5)	N24—C25—C26—N21	0.0 (5)
C14—C15—C16—F16	−178.4 (3)	C35—C25—C26—N21	−178.2 (3)
F15—C15—C16—C11	−179.7 (3)	N24—C25—C26—C36	−178.8 (3)
C14—C15—C16—C11	0.8 (5)	C35—C25—C26—C36	3.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···N21	0.98 (4)	1.75 (4)	2.659 (3)	152 (4)

(BrF4CO11) SD-1–22-2–5 4-Br—F4-PhCOOH, 1,2-bis(4-pyridyl)ethane

Crystal data

(C7HBrF4O2)(C12H12N2)	Z = 2
Mr = 457.22	F(000) = 456
Triclinic, P1	Dx = 1.762 Mg m^−3
a = 4.8727 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7621 (7) Å	Cell parameters from 9988 reflections
c = 16.595 (1) Å	θ = 2.5–32.8°
α = 87.808 (2)°	µ = 2.45 mm^−1
β = 85.332 (2)°	T = 120 K
γ = 83.646 (2)°	Prism, colourless
V = 861.66 (9) Å^3	0.28 × 0.16 × 0.16 mm

Data collection

Bruker APEX-II CCD diffractometer	6066 independent reflections
Radiation source: fine-focus sealed tube	5273 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 32.9°, θmin = 1.2°
Absorption correction: multi-scan SADABS	h = −3→7
Tmin = 0.548, Tmax = 0.696	k = −15→15
23701 measured reflections	l = −24→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.040P)^2 + 0.4P] where P = (Fo^2 + 2Fc^2)/3
6066 reflections	(Δ/σ)max = 0.002
287 parameters	Δρmax = 0.68 e Å^−3
35 restraints	Δρmin = −0.68 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N11	0.3858 (3)	0.30864 (13)	0.46600 (8)	0.0194 (2)
H11	0.228 (5)	0.318 (2)	0.5008 (14)	0.023*
C12	0.5240 (3)	0.19460 (15)	0.45556 (10)	0.0211 (3)
H12	0.4667	0.1254	0.4873	0.025*
C13	0.7477 (3)	0.17679 (15)	0.39945 (9)	0.0204 (3)
H13	0.8425	0.0956	0.3918	0.024*
C14	0.8342 (3)	0.27918 (14)	0.35383 (9)	0.0179 (3)
C15	0.6911 (3)	0.39700 (15)	0.36797 (9)	0.0199 (3)
H15	0.7494	0.4688	0.3393	0.024*
C16	0.4651 (3)	0.40876 (15)	0.42368 (9)	0.0199 (3)
H16	0.3646	0.4886	0.4322	0.024*
C17	1.0651 (3)	0.26262 (15)	0.28824 (9)	0.0199 (3)
H17A	1.1730	0.1801	0.2957	0.024*
H17B	1.1910	0.3280	0.2920	0.024*
N21	1.6385 (3)	0.21284 (15)	0.02475 (8)	0.0255 (3)
C22	1.5143 (4)	0.32680 (18)	0.04051 (10)	0.0273 (3)
H22	1.5839	0.3959	0.0115	0.033*
C23	1.2899 (4)	0.35082 (16)	0.09667 (10)	0.0233 (3)
H23	1.2104	0.4342	0.1058	0.028*
C24	1.1830 (3)	0.25104 (15)	0.13940 (9)	0.0189 (3)
C25	1.3093 (3)	0.13176 (16)	0.12278 (10)	0.0227 (3)
H25	1.2420	0.0606	0.1500	0.027*
C26	1.5351 (4)	0.11773 (17)	0.06598 (10)	0.0246 (3)
H26	1.6209	0.0356	0.0560	0.029*
C27	0.9508 (3)	0.27147 (16)	0.20431 (9)	0.0206 (3)
H27A	0.8208	0.2077	0.2010	0.025*
H27B	0.8477	0.3550	0.1961	0.025*
Br1	−0.95931 (4)	0.21285 (2)	0.894916 (10)	0.02096 (6)	0.9464 (7)
C31A	−0.2783 (4)	0.22968 (15)	0.67721 (11)	0.0167 (3)	0.9464 (7)
C37A	−0.0532 (4)	0.2303 (2)	0.60814 (13)	0.02269 (16)	0.9464 (7)
O31A	−0.0390 (3)	0.33718 (12)	0.57136 (8)	0.02269 (16)	0.9464 (7)
O32A	0.0911 (3)	0.13414 (11)	0.59292 (7)	0.02269 (16)	0.9464 (7)
C32A	−0.4270 (4)	0.12706 (16)	0.69192 (11)	0.0173 (3)	0.9464 (7)
F32A	−0.3781 (3)	0.02825 (10)	0.64405 (9)	0.0229 (2)	0.9464 (7)
C33A	−0.6290 (4)	0.12269 (15)	0.75460 (12)	0.0182 (3)	0.9464 (7)
F33A	−0.7688 (3)	0.02185 (10)	0.76404 (11)	0.0249 (3)	0.9464 (7)
C34A	−0.6930 (4)	0.22050 (17)	0.80673 (11)	0.0185 (3)	0.9464 (7)
C35A	−0.5457 (4)	0.32324 (17)	0.79339 (13)	0.0187 (3)	0.9464 (7)
F35A	−0.5942 (3)	0.41986 (12)	0.84319 (10)	0.0259 (3)	0.9464 (7)
C36A	−0.3439 (4)	0.32729 (16)	0.73039 (12)	0.0177 (3)	0.9464 (7)
F36A	−0.2021 (4)	0.42773 (13)	0.72420 (10)	0.0241 (3)	0.9464 (7)
Br2	−0.0326 (7)	0.2663 (3)	0.6001 (2)	0.02269 (16)	0.0536 (7)
C31B	−0.706 (7)	0.242 (2)	0.8179 (18)	0.0185 (3)	0.0536 (7)
C37B	−0.945 (6)	0.2447 (17)	0.8836 (17)	0.02096 (6)	0.0536 (7)
O31B	−0.955 (4)	0.1409 (16)	0.9242 (11)	0.02096 (6)	0.0536 (7)
O32B	−1.079 (4)	0.3434 (16)	0.8966 (12)	0.02096 (6)	0.0536 (7)
C32B	−0.562 (9)	0.347 (3)	0.804 (2)	0.0187 (3)	0.0536 (7)
F32B	−0.624 (7)	0.446 (2)	0.8508 (19)	0.0259 (3)	0.0536 (7)
C33B	−0.358 (8)	0.352 (3)	0.742 (2)	0.0177 (3)	0.0536 (7)
F33B	−0.211 (7)	0.451 (3)	0.735 (2)	0.0241 (3)	0.0536 (7)
C34B	−0.298 (7)	0.259 (2)	0.6881 (17)	0.0167 (3)	0.0536 (7)
C35B	−0.435 (8)	0.153 (2)	0.702 (2)	0.0173 (3)	0.0536 (7)
F35B	−0.380 (7)	0.058 (2)	0.6519 (18)	0.0229 (2)	0.0536 (7)
C36B	−0.661 (6)	0.154 (2)	0.7580 (18)	0.0182 (3)	0.0536 (7)
F36B	−0.792 (7)	0.050 (2)	0.763 (2)	0.0249 (3)	0.0536 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0165 (6)	0.0232 (6)	0.0180 (6)	−0.0012 (5)	0.0019 (5)	−0.0030 (5)
C12	0.0222 (7)	0.0202 (7)	0.0205 (7)	−0.0031 (6)	0.0011 (6)	0.0003 (5)
C13	0.0209 (7)	0.0195 (7)	0.0200 (7)	−0.0003 (5)	0.0008 (5)	−0.0021 (5)
C14	0.0161 (6)	0.0218 (7)	0.0158 (6)	−0.0020 (5)	−0.0001 (5)	−0.0029 (5)
C15	0.0200 (7)	0.0196 (7)	0.0195 (6)	−0.0024 (5)	0.0017 (5)	−0.0003 (5)
C16	0.0206 (7)	0.0199 (7)	0.0189 (6)	−0.0004 (5)	−0.0005 (5)	−0.0028 (5)
C17	0.0171 (6)	0.0260 (7)	0.0161 (6)	−0.0011 (5)	0.0013 (5)	−0.0016 (5)
N21	0.0216 (6)	0.0349 (8)	0.0189 (6)	−0.0014 (6)	0.0026 (5)	−0.0027 (5)
C22	0.0268 (8)	0.0314 (9)	0.0225 (7)	−0.0051 (7)	0.0055 (6)	0.0038 (6)
C23	0.0245 (7)	0.0217 (7)	0.0225 (7)	−0.0008 (6)	0.0031 (6)	−0.0009 (6)
C24	0.0171 (6)	0.0234 (7)	0.0164 (6)	−0.0024 (5)	−0.0003 (5)	−0.0025 (5)
C25	0.0238 (7)	0.0225 (7)	0.0219 (7)	−0.0038 (6)	0.0001 (6)	−0.0021 (6)
C26	0.0231 (7)	0.0276 (8)	0.0222 (7)	0.0025 (6)	−0.0010 (6)	−0.0066 (6)
C27	0.0177 (6)	0.0271 (7)	0.0169 (6)	−0.0029 (6)	0.0012 (5)	−0.0019 (5)
Br1	0.01706 (8)	0.02808 (10)	0.01661 (9)	−0.00113 (7)	0.00269 (5)	0.00168 (6)
C31A	0.0147 (6)	0.0179 (8)	0.0167 (7)	0.0000 (6)	0.0012 (5)	0.0002 (6)
C37A	0.0218 (3)	0.0218 (4)	0.0223 (3)	0.0018 (3)	0.0046 (3)	0.0021 (3)
O31A	0.0218 (3)	0.0218 (4)	0.0223 (3)	0.0018 (3)	0.0046 (3)	0.0021 (3)
O32A	0.0218 (3)	0.0218 (4)	0.0223 (3)	0.0018 (3)	0.0046 (3)	0.0021 (3)
C32A	0.0186 (6)	0.0155 (8)	0.0176 (8)	−0.0014 (7)	0.0000 (6)	−0.0019 (6)
F32A	0.0250 (5)	0.0178 (6)	0.0253 (5)	−0.0028 (5)	0.0040 (4)	−0.0060 (5)
C33A	0.0171 (7)	0.0173 (8)	0.0200 (7)	−0.0029 (6)	0.0005 (5)	0.0018 (6)
F33A	0.0263 (6)	0.0216 (6)	0.0272 (5)	−0.0091 (6)	0.0039 (4)	0.0012 (6)
C34A	0.0150 (6)	0.0236 (8)	0.0161 (8)	−0.0005 (6)	0.0013 (5)	0.0009 (6)
C35A	0.0198 (7)	0.0184 (9)	0.0173 (8)	0.0002 (7)	0.0009 (6)	−0.0024 (6)
F35A	0.0308 (7)	0.0232 (7)	0.0228 (6)	−0.0024 (6)	0.0060 (4)	−0.0080 (5)
C36A	0.0186 (7)	0.0167 (8)	0.0176 (8)	−0.0027 (7)	0.0002 (6)	0.0001 (5)
F36A	0.0277 (5)	0.0203 (7)	0.0250 (7)	−0.0093 (5)	0.0041 (5)	−0.0032 (4)
Br2	0.0218 (3)	0.0218 (4)	0.0223 (3)	0.0018 (3)	0.0046 (3)	0.0021 (3)
C31B	0.0150 (6)	0.0236 (8)	0.0161 (8)	−0.0005 (6)	0.0013 (5)	0.0009 (6)
C37B	0.01706 (8)	0.02808 (10)	0.01661 (9)	−0.00113 (7)	0.00269 (5)	0.00168 (6)
O31B	0.01706 (8)	0.02808 (10)	0.01661 (9)	−0.00113 (7)	0.00269 (5)	0.00168 (6)
O32B	0.01706 (8)	0.02808 (10)	0.01661 (9)	−0.00113 (7)	0.00269 (5)	0.00168 (6)
C32B	0.0198 (7)	0.0184 (9)	0.0173 (8)	0.0002 (7)	0.0009 (6)	−0.0024 (6)
F32B	0.0308 (7)	0.0232 (7)	0.0228 (6)	−0.0024 (6)	0.0060 (4)	−0.0080 (5)
C33B	0.0186 (7)	0.0167 (8)	0.0176 (8)	−0.0027 (7)	0.0002 (6)	0.0001 (5)
F33B	0.0277 (5)	0.0203 (7)	0.0250 (7)	−0.0093 (5)	0.0041 (5)	−0.0032 (4)
C34B	0.0147 (6)	0.0179 (8)	0.0167 (7)	0.0000 (6)	0.0012 (5)	0.0002 (6)
C35B	0.0186 (6)	0.0155 (8)	0.0176 (8)	−0.0014 (7)	0.0000 (6)	−0.0019 (6)
F35B	0.0250 (5)	0.0178 (6)	0.0253 (5)	−0.0028 (5)	0.0040 (4)	−0.0060 (5)
C36B	0.0171 (7)	0.0173 (8)	0.0200 (7)	−0.0029 (6)	0.0005 (5)	0.0018 (6)
F36B	0.0263 (6)	0.0216 (6)	0.0272 (5)	−0.0091 (6)	0.0039 (4)	0.0012 (6)

Geometric parameters (Å, º)

N11—C16	1.339 (2)	Br1—C34A	1.8808 (16)
N11—C12	1.343 (2)	C31A—C32A	1.390 (2)
N11—H11	0.92 (2)	C31A—C36A	1.391 (2)
C12—C13	1.376 (2)	C31A—C37A	1.521 (3)
C12—H12	0.9500	C37A—O32A	1.208 (2)
C13—C14	1.397 (2)	C37A—O31A	1.287 (3)
C13—H13	0.9500	C32A—F32A	1.3404 (18)
C14—C15	1.396 (2)	C32A—C33A	1.376 (2)
C14—C17	1.501 (2)	C33A—F33A	1.341 (2)
C15—C16	1.377 (2)	C33A—C34A	1.381 (2)
C15—H15	0.9500	C34A—C35A	1.385 (2)
C16—H16	0.9500	C35A—F35A	1.3415 (19)
C17—C27	1.538 (2)	C35A—C36A	1.378 (2)
C17—H17A	0.9900	C36A—F36A	1.3423 (19)
C17—H17B	0.9900	Br2—C34B	1.875 (9)
N21—C22	1.332 (2)	C31B—C36B	1.387 (9)
N21—C26	1.332 (2)	C31B—C32B	1.395 (9)
C22—C23	1.386 (2)	C31B—C37B	1.527 (9)
C22—H22	0.9500	C37B—O32B	1.201 (9)
C23—C24	1.390 (2)	C37B—O31B	1.287 (9)
C23—H23	0.9500	C32B—F32B	1.338 (9)
C24—C25	1.388 (2)	C32B—C33B	1.372 (9)
C24—C27	1.501 (2)	C33B—F33B	1.343 (9)
C25—C26	1.388 (2)	C33B—C34B	1.371 (9)
C25—H25	0.9500	C34B—C35B	1.385 (9)
C26—H26	0.9500	C35B—F35B	1.336 (9)
C27—H27A	0.9900	C35B—C36B	1.382 (9)
C27—H27B	0.9900	C36B—F36B	1.343 (9)
C16—N11—C12	121.15 (14)	C17—C27—H27B	109.6
C16—N11—H11	118.7 (14)	H27A—C27—H27B	108.1
C12—N11—H11	120.1 (14)	C32A—C31A—C36A	115.88 (14)
N11—C12—C13	120.81 (15)	C32A—C31A—C37A	120.69 (15)
N11—C12—H12	119.6	C36A—C31A—C37A	123.40 (16)
C13—C12—H12	119.6	O32A—C37A—O31A	126.69 (19)
C12—C13—C14	119.42 (14)	O32A—C37A—C31A	118.82 (19)
C12—C13—H13	120.3	O31A—C37A—C31A	114.49 (16)
C14—C13—H13	120.3	F32A—C32A—C33A	117.57 (15)
C15—C14—C13	118.27 (14)	F32A—C32A—C31A	120.27 (15)
C15—C14—C17	120.55 (14)	C33A—C32A—C31A	122.16 (15)
C13—C14—C17	121.10 (14)	F33A—C33A—C32A	118.92 (16)
C16—C15—C14	119.74 (15)	F33A—C33A—C34A	119.70 (15)
C16—C15—H15	120.1	C32A—C33A—C34A	121.37 (16)
C14—C15—H15	120.1	C33A—C34A—C35A	117.32 (15)
N11—C16—C15	120.56 (14)	C33A—C34A—Br1	121.67 (13)
N11—C16—H16	119.7	C35A—C34A—Br1	120.97 (12)
C15—C16—H16	119.7	F35A—C35A—C36A	118.88 (15)
C14—C17—C27	110.88 (12)	F35A—C35A—C34A	120.02 (15)
C14—C17—H17A	109.5	C36A—C35A—C34A	121.09 (15)
C27—C17—H17A	109.5	F36A—C36A—C35A	117.16 (14)
C14—C17—H17B	109.5	F36A—C36A—C31A	120.60 (14)
C27—C17—H17B	109.5	C35A—C36A—C31A	122.17 (15)
H17A—C17—H17B	108.1	C36B—C31B—C32B	115.4 (11)
C22—N21—C26	116.60 (15)	C36B—C31B—C37B	123.4 (14)
N21—C22—C23	124.06 (16)	C32B—C31B—C37B	119.4 (11)
N21—C22—H22	118.0	O32B—C37B—O31B	128.1 (14)
C23—C22—H22	118.0	O32B—C37B—C31B	117.7 (13)
C22—C23—C24	118.99 (15)	O31B—C37B—C31B	113.7 (13)
C22—C23—H23	120.5	F32B—C32B—C33B	118.3 (13)
C24—C23—H23	120.5	F32B—C32B—C31B	120.1 (13)
C25—C24—C23	117.35 (15)	C33B—C32B—C31B	121.6 (10)
C25—C24—C27	121.08 (15)	F33B—C33B—C34B	118.9 (12)
C23—C24—C27	121.47 (14)	F33B—C33B—C32B	119.4 (12)
C24—C25—C26	119.21 (16)	C34B—C33B—C32B	121.6 (10)
C24—C25—H25	120.4	C33B—C34B—C35B	117.2 (9)
C26—C25—H25	120.4	C33B—C34B—Br2	122.9 (9)
N21—C26—C25	123.77 (16)	C35B—C34B—Br2	119.9 (9)
N21—C26—H26	118.1	F35B—C35B—C36B	119.1 (13)
C25—C26—H26	118.1	F35B—C35B—C34B	119.7 (13)
C24—C27—C17	110.36 (12)	C36B—C35B—C34B	120.2 (12)
C24—C27—H27A	109.6	F36B—C36B—C35B	115.9 (13)
C17—C27—H27A	109.6	F36B—C36B—C31B	121.1 (14)
C24—C27—H27B	109.6	C35B—C36B—C31B	121.0 (12)
C16—N11—C12—C13	−1.6 (2)	C33A—C34A—C35A—C36A	0.2 (3)
N11—C12—C13—C14	1.0 (2)	Br1—C34A—C35A—C36A	177.81 (19)
C12—C13—C14—C15	0.9 (2)	F35A—C35A—C36A—F36A	1.7 (3)
C12—C13—C14—C17	−175.91 (14)	C34A—C35A—C36A—F36A	−176.9 (2)
C13—C14—C15—C16	−2.3 (2)	F35A—C35A—C36A—C31A	178.8 (2)
C17—C14—C15—C16	174.55 (14)	C34A—C35A—C36A—C31A	0.2 (4)
C12—N11—C16—C15	0.2 (2)	C32A—C31A—C36A—F36A	176.3 (2)
C14—C15—C16—N11	1.8 (2)	C37A—C31A—C36A—F36A	−1.9 (3)
C15—C14—C17—C27	−73.61 (18)	C32A—C31A—C36A—C35A	−0.6 (3)
C13—C14—C17—C27	103.15 (17)	C37A—C31A—C36A—C35A	−178.8 (2)
C26—N21—C22—C23	0.5 (3)	C36B—C31B—C37B—O32B	−133 (4)
N21—C22—C23—C24	−0.6 (3)	C32B—C31B—C37B—O32B	32 (5)
C22—C23—C24—C25	−0.1 (2)	C36B—C31B—C37B—O31B	55 (5)
C22—C23—C24—C27	176.49 (15)	C32B—C31B—C37B—O31B	−141 (4)
C23—C24—C25—C26	0.8 (2)	C36B—C31B—C32B—F32B	169 (5)
C27—C24—C25—C26	−175.80 (14)	C37B—C31B—C32B—F32B	3 (7)
C22—N21—C26—C25	0.3 (2)	C36B—C31B—C32B—C33B	−10 (7)
C24—C25—C26—N21	−1.0 (2)	C37B—C31B—C32B—C33B	−176 (4)
C25—C24—C27—C17	77.59 (18)	F32B—C32B—C33B—F33B	6 (8)
C23—C24—C27—C17	−98.90 (18)	C31B—C32B—C33B—F33B	−175 (5)
C14—C17—C27—C24	−178.35 (13)	F32B—C32B—C33B—C34B	−175 (5)
C32A—C31A—C37A—O32A	−36.9 (3)	C31B—C32B—C33B—C34B	4 (8)
C36A—C31A—C37A—O32A	141.2 (2)	F33B—C33B—C34B—C35B	174 (5)
C32A—C31A—C37A—O31A	142.9 (2)	C32B—C33B—C34B—C35B	−5 (8)
C36A—C31A—C37A—O31A	−38.9 (3)	F33B—C33B—C34B—Br2	−4 (7)
C36A—C31A—C32A—F32A	−179.9 (2)	C32B—C33B—C34B—Br2	177 (4)
C37A—C31A—C32A—F32A	−1.6 (3)	C33B—C34B—C35B—F35B	−179 (5)
C36A—C31A—C32A—C33A	0.7 (3)	Br2—C34B—C35B—F35B	−1 (6)
C37A—C31A—C32A—C33A	178.99 (19)	C33B—C34B—C35B—C36B	13 (7)
F32A—C32A—C33A—F33A	−1.0 (3)	Br2—C34B—C35B—C36B	−169 (4)
C31A—C32A—C33A—F33A	178.4 (2)	F35B—C35B—C36B—F36B	7 (6)
F32A—C32A—C33A—C34A	−179.9 (2)	C34B—C35B—C36B—F36B	176 (4)
C31A—C32A—C33A—C34A	−0.4 (3)	F35B—C35B—C36B—C31B	172 (4)
F33A—C33A—C34A—C35A	−178.9 (2)	C34B—C35B—C36B—C31B	−20 (7)
C32A—C33A—C34A—C35A	0.0 (3)	C32B—C31B—C36B—F36B	−179 (5)
F33A—C33A—C34A—Br1	3.5 (3)	C37B—C31B—C36B—F36B	−14 (6)
C32A—C33A—C34A—Br1	−177.66 (17)	C32B—C31B—C36B—C35B	18 (6)
C33A—C34A—C35A—F35A	−178.4 (2)	C37B—C31B—C36B—C35B	−177 (4)
Br1—C34A—C35A—F35A	−0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O31A	0.92 (2)	1.68 (2)	2.5975 (18)	175 (2)

(IF4OX13) SD-1–20-9–7 4-I—F4-PhCH=NOH, Me4-pyrazine

Crystal data

(C7H2F4INO)(C8H12N2)	F(000) = 888
Mr = 455.19	Dx = 1.865 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.1573 (2) Å	Cell parameters from 9976 reflections
b = 14.8817 (8) Å	θ = 2.9–33.2°
c = 26.2084 (13) Å	µ = 2.03 mm^−1
β = 91.345 (1)°	T = 120 K
V = 1621.01 (14) Å^3	Rod, colourless
Z = 4	0.36 × 0.14 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	5424 independent reflections
Radiation source: fine-focus sealed tube	5028 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 33.1°, θmin = 2.7°
Absorption correction: multi-scan SADABS	h = −6→6
Tmin = 0.529, Tmax = 0.888	k = −18→21
19470 measured reflections	l = −40→37

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.23	w = 1/[σ^2(Fo^2) + (0.020P)^2 + 2.P] where P = (Fo^2 + 2Fc^2)/3
5424 reflections	(Δ/σ)max = 0.001
224 parameters	Δρmax = 1.00 e Å^−3
0 restraints	Δρmin = −0.92 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	−0.71982 (3)	0.240045 (9)	−0.028023 (5)	0.02385 (5)
N11	0.9309 (4)	0.33955 (12)	0.38141 (7)	0.0229 (3)
C12	0.8490 (5)	0.28645 (14)	0.34210 (8)	0.0230 (4)
C13	0.6697 (5)	0.32078 (14)	0.30044 (7)	0.0225 (4)
N14	0.5881 (5)	0.40726 (12)	0.29930 (7)	0.0234 (3)
C15	0.6735 (5)	0.46117 (14)	0.33840 (8)	0.0229 (4)
C16	0.8433 (5)	0.42582 (14)	0.38057 (8)	0.0228 (4)
C22	0.9499 (6)	0.19006 (15)	0.34550 (9)	0.0301 (4)
H22A	1.1789	0.1867	0.3551	0.045*
H22B	0.9137	0.1610	0.3123	0.045*
H22C	0.8233	0.1594	0.3713	0.045*
C23	0.5713 (6)	0.26379 (16)	0.25558 (9)	0.0297 (4)
H23A	0.4246	0.2979	0.2331	0.044*
H23B	0.4622	0.2096	0.2676	0.044*
H23C	0.7626	0.2465	0.2367	0.044*
C25	0.5846 (7)	0.55825 (16)	0.33335 (9)	0.0336 (5)
H25A	0.5152	0.5707	0.2981	0.050*
H25B	0.7717	0.5956	0.3423	0.050*
H25C	0.4087	0.5720	0.3563	0.050*
C26	0.9274 (7)	0.48030 (16)	0.42712 (9)	0.0322 (5)
H26A	0.8550	0.4487	0.4576	0.048*
H26B	0.8211	0.5390	0.4247	0.048*
H26C	1.1610	0.4888	0.4295	0.048*
C31	−0.2600 (5)	0.39935 (14)	0.12149 (7)	0.0206 (3)
C37	−0.1376 (5)	0.45268 (14)	0.16467 (8)	0.0235 (4)
H37A	−0.2292	0.5100	0.1711	0.028*
N37	0.0890 (5)	0.42394 (13)	0.19385 (7)	0.0255 (3)
O37	0.1686 (4)	0.48753 (12)	0.23083 (6)	0.0294 (3)
H37	0.305 (8)	0.461 (2)	0.2496 (14)	0.035*
C32	−0.1978 (5)	0.30871 (14)	0.11312 (7)	0.0211 (3)
F32	−0.0082 (4)	0.26174 (9)	0.14545 (5)	0.0295 (3)
C33	−0.3282 (5)	0.26346 (13)	0.07156 (8)	0.0218 (3)
F33	−0.2628 (4)	0.17566 (9)	0.06688 (5)	0.0289 (3)
C34	−0.5232 (5)	0.30598 (14)	0.03534 (7)	0.0209 (3)
C35	−0.5864 (5)	0.39591 (14)	0.04333 (8)	0.0225 (4)
F35	−0.7766 (3)	0.44116 (10)	0.01068 (5)	0.0308 (3)
C36	−0.4602 (5)	0.44086 (13)	0.08525 (8)	0.0214 (3)
F36	−0.5334 (4)	0.52774 (9)	0.09095 (5)	0.0303 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02159 (7)	0.02909 (8)	0.02090 (7)	0.00027 (5)	0.00114 (4)	−0.00444 (4)
N11	0.0254 (8)	0.0228 (8)	0.0204 (7)	−0.0039 (6)	−0.0009 (6)	0.0014 (6)
C12	0.0274 (9)	0.0209 (9)	0.0206 (8)	−0.0028 (7)	0.0021 (7)	0.0012 (7)
C13	0.0251 (9)	0.0244 (9)	0.0181 (8)	−0.0040 (7)	0.0026 (7)	−0.0004 (7)
N14	0.0271 (8)	0.0246 (8)	0.0185 (7)	−0.0026 (6)	−0.0001 (6)	0.0004 (6)
C15	0.0264 (9)	0.0222 (9)	0.0202 (8)	−0.0020 (7)	−0.0003 (7)	0.0003 (7)
C16	0.0253 (9)	0.0232 (9)	0.0199 (8)	−0.0039 (7)	−0.0013 (7)	−0.0002 (7)
C22	0.0393 (12)	0.0227 (10)	0.0284 (10)	0.0002 (8)	0.0001 (9)	−0.0003 (8)
C23	0.0397 (12)	0.0282 (10)	0.0209 (9)	−0.0031 (9)	−0.0022 (8)	−0.0034 (7)
C25	0.0484 (14)	0.0234 (10)	0.0287 (11)	0.0025 (9)	−0.0064 (10)	−0.0010 (8)
C26	0.0424 (13)	0.0270 (10)	0.0267 (10)	−0.0021 (9)	−0.0105 (9)	−0.0041 (8)
C31	0.0204 (8)	0.0234 (9)	0.0181 (8)	0.0011 (7)	0.0011 (6)	0.0021 (6)
C37	0.0261 (9)	0.0244 (9)	0.0199 (8)	−0.0002 (7)	0.0007 (7)	0.0001 (7)
N37	0.0279 (9)	0.0300 (9)	0.0184 (7)	−0.0012 (7)	−0.0007 (6)	−0.0012 (6)
O37	0.0348 (9)	0.0309 (8)	0.0221 (7)	−0.0006 (7)	−0.0067 (6)	−0.0021 (6)
C32	0.0221 (9)	0.0234 (9)	0.0178 (8)	0.0032 (7)	0.0018 (6)	0.0044 (6)
F32	0.0383 (7)	0.0278 (6)	0.0220 (6)	0.0089 (5)	−0.0058 (5)	0.0048 (5)
C33	0.0251 (9)	0.0201 (8)	0.0202 (8)	0.0019 (7)	0.0035 (7)	0.0018 (6)
F33	0.0414 (8)	0.0194 (6)	0.0258 (6)	0.0046 (5)	0.0015 (5)	0.0012 (5)
C34	0.0197 (8)	0.0248 (9)	0.0183 (8)	0.0013 (7)	0.0014 (6)	−0.0010 (7)
C35	0.0203 (9)	0.0269 (9)	0.0202 (8)	0.0050 (7)	−0.0010 (7)	0.0015 (7)
F35	0.0319 (7)	0.0323 (7)	0.0275 (6)	0.0121 (5)	−0.0096 (5)	−0.0010 (5)
C36	0.0215 (9)	0.0207 (9)	0.0218 (8)	0.0047 (7)	−0.0001 (7)	−0.0006 (7)
F36	0.0391 (8)	0.0225 (6)	0.0291 (6)	0.0097 (5)	−0.0046 (5)	−0.0033 (5)

Geometric parameters (Å, º)

I1—C34	2.080 (2)	C25—H25C	0.9800
N11—C16	1.335 (3)	C26—H26A	0.9800
N11—C12	1.336 (3)	C26—H26B	0.9800
C12—C13	1.404 (3)	C26—H26C	0.9800
C12—C22	1.497 (3)	C31—C32	1.392 (3)
C13—N14	1.331 (3)	C31—C36	1.393 (3)
C13—C23	1.499 (3)	C31—C37	1.464 (3)
N14—C15	1.343 (3)	C37—N37	1.273 (3)
C15—C16	1.400 (3)	C37—H37A	0.9500
C15—C25	1.496 (3)	N37—O37	1.389 (2)
C16—C26	1.499 (3)	O37—H37	0.84 (4)
C22—H22A	0.9800	C32—F32	1.340 (2)
C22—H22B	0.9800	C32—C33	1.380 (3)
C22—H22C	0.9800	C33—F33	1.341 (2)
C23—H23A	0.9800	C33—C34	1.387 (3)
C23—H23B	0.9800	C34—C35	1.381 (3)
C23—H23C	0.9800	C35—F35	1.334 (2)
C25—H25A	0.9800	C35—C36	1.379 (3)
C25—H25B	0.9800	C36—F36	1.338 (2)
C16—N11—C12	119.44 (18)	H25B—C25—H25C	109.5
N11—C12—C13	120.37 (19)	C16—C26—H26A	109.5
N11—C12—C22	117.06 (19)	C16—C26—H26B	109.5
C13—C12—C22	122.56 (19)	H26A—C26—H26B	109.5
N14—C13—C12	119.99 (19)	C16—C26—H26C	109.5
N14—C13—C23	117.69 (19)	H26A—C26—H26C	109.5
C12—C13—C23	122.3 (2)	H26B—C26—H26C	109.5
C13—N14—C15	119.85 (18)	C32—C31—C36	115.64 (18)
N14—C15—C16	119.83 (19)	C32—C31—C37	125.80 (18)
N14—C15—C25	116.67 (19)	C36—C31—C37	118.56 (18)
C16—C15—C25	123.48 (19)	N37—C37—C31	121.4 (2)
N11—C16—C15	120.47 (19)	N37—C37—H37A	119.3
N11—C16—C26	116.64 (19)	C31—C37—H37A	119.3
C15—C16—C26	122.9 (2)	C37—N37—O37	110.55 (19)
C12—C22—H22A	109.5	N37—O37—H37	104 (2)
C12—C22—H22B	109.5	F32—C32—C33	117.30 (18)
H22A—C22—H22B	109.5	F32—C32—C31	120.95 (18)
C12—C22—H22C	109.5	C33—C32—C31	121.75 (18)
H22A—C22—H22C	109.5	F33—C33—C32	118.09 (18)
H22B—C22—H22C	109.5	F33—C33—C34	119.91 (18)
C13—C23—H23A	109.5	C32—C33—C34	122.00 (19)
C13—C23—H23B	109.5	C35—C34—C33	116.67 (18)
H23A—C23—H23B	109.5	C35—C34—I1	120.38 (15)
C13—C23—H23C	109.5	C33—C34—I1	122.94 (15)
H23A—C23—H23C	109.5	F35—C35—C36	118.34 (18)
H23B—C23—H23C	109.5	F35—C35—C34	120.28 (18)
C15—C25—H25A	109.5	C36—C35—C34	121.37 (18)
C15—C25—H25B	109.5	F36—C36—C35	118.33 (18)
H25A—C25—H25B	109.5	F36—C36—C31	119.12 (18)
C15—C25—H25C	109.5	C35—C36—C31	122.55 (19)
H25A—C25—H25C	109.5
C16—N11—C12—C13	−0.6 (3)	C37—C31—C32—C33	179.0 (2)
C16—N11—C12—C22	−179.2 (2)	F32—C32—C33—F33	1.4 (3)
N11—C12—C13—N14	1.9 (3)	C31—C32—C33—F33	−178.41 (18)
C22—C12—C13—N14	−179.6 (2)	F32—C32—C33—C34	−178.92 (18)
N11—C12—C13—C23	−179.8 (2)	C31—C32—C33—C34	1.2 (3)
C22—C12—C13—C23	−1.3 (3)	F33—C33—C34—C35	178.43 (18)
C12—C13—N14—C15	−1.0 (3)	C32—C33—C34—C35	−1.2 (3)
C23—C13—N14—C15	−179.4 (2)	F33—C33—C34—I1	−0.9 (3)
C13—N14—C15—C16	−1.1 (3)	C32—C33—C34—I1	179.43 (15)
C13—N14—C15—C25	177.6 (2)	C33—C34—C35—F35	−178.82 (19)
C12—N11—C16—C15	−1.5 (3)	I1—C34—C35—F35	0.6 (3)
C12—N11—C16—C26	176.7 (2)	C33—C34—C35—C36	0.2 (3)
N14—C15—C16—N11	2.4 (3)	I1—C34—C35—C36	179.59 (16)
C25—C15—C16—N11	−176.2 (2)	F35—C35—C36—F36	−0.3 (3)
N14—C15—C16—C26	−175.7 (2)	C34—C35—C36—F36	−179.39 (19)
C25—C15—C16—C26	5.7 (4)	F35—C35—C36—C31	179.86 (19)
C32—C31—C37—N37	13.5 (3)	C34—C35—C36—C31	0.8 (3)
C36—C31—C37—N37	−167.3 (2)	C32—C31—C36—F36	179.40 (18)
C31—C37—N37—O37	178.18 (18)	C37—C31—C36—F36	0.1 (3)
C36—C31—C32—F32	179.95 (18)	C32—C31—C36—C35	−0.8 (3)
C37—C31—C32—F32	−0.8 (3)	C37—C31—C36—C35	179.9 (2)
C36—C31—C32—C33	−0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O37—H37···N14	0.84 (4)	1.91 (4)	2.746 (3)	173 (3)

(IF4OX11) CS—AS-9–11 4-I—F4-PhCHO oxime, 1,2-bis(4-pyridyl)ethane

Crystal data

(C7H2F4INO)(C12H12N2)	F(000) = 984
Mr = 503.23	Dx = 1.775 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.2801 (9) Å	Cell parameters from 9874 reflections
b = 11.2226 (15) Å	θ = 2.4–31.7°
c = 26.846 (4) Å	µ = 1.75 mm^−1
β = 95.661 (4)°	T = 120 K
V = 1882.8 (5) Å^3	Plate, colourless
Z = 4	0.34 × 0.28 × 0.14 mm

Data collection

Bruker APEX-II CCD diffractometer	6405 independent reflections
Radiation source: fine-focus sealed tube	5234 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 32.0°, θmin = 2.0°
Absorption correction: multi-scan SADABS	h = −8→9
Tmin = 0.587, Tmax = 0.791	k = −16→15
28823 measured reflections	l = −39→40

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.040P)^2 + 0.5P] where P = (Fo^2 + 2Fc^2)/3
6405 reflections	(Δ/σ)max = 0.003
256 parameters	Δρmax = 0.77 e Å^−3
0 restraints	Δρmin = −0.56 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C11	1.0834 (3)	0.61419 (16)	0.34975 (6)	0.0322 (3)
C12	1.0054 (3)	0.50210 (17)	0.36022 (7)	0.0344 (3)
F12	0.81031 (17)	0.46804 (11)	0.34078 (5)	0.0447 (3)
C13	1.1241 (3)	0.42204 (16)	0.39035 (7)	0.0353 (3)
F13	1.0372 (2)	0.31534 (10)	0.39857 (6)	0.0478 (3)
C14	1.3293 (3)	0.44800 (16)	0.41139 (6)	0.0341 (3)
I1	1.51017 (2)	0.328867 (12)	0.458343 (4)	0.04006 (5)
C15	1.4094 (3)	0.55835 (17)	0.40050 (6)	0.0339 (3)
F15	1.60875 (17)	0.58920 (11)	0.41906 (4)	0.0422 (3)
C16	1.2901 (3)	0.63888 (17)	0.37104 (7)	0.0332 (3)
F16	1.37725 (18)	0.74594 (10)	0.36298 (4)	0.0430 (3)
C17	0.9682 (3)	0.70613 (18)	0.31989 (7)	0.0363 (4)
H17A	1.0337	0.7817	0.3167	0.044*
N17	0.7806 (3)	0.68800 (14)	0.29777 (6)	0.0377 (3)
O17	0.7077 (2)	0.78911 (14)	0.27185 (6)	0.0449 (3)
H17	0.583 (5)	0.768 (3)	0.2586 (10)	0.054*
N21	0.3302 (3)	0.70842 (17)	0.22878 (6)	0.0424 (4)
C22	0.3054 (3)	0.5901 (2)	0.22987 (8)	0.0435 (4)
H22	0.4167	0.5434	0.2466	0.052*
C23	0.1258 (3)	0.53254 (19)	0.20789 (7)	0.0424 (4)
H23	0.1150	0.4482	0.2095	0.051*
C24	−0.0390 (3)	0.5995 (2)	0.18341 (7)	0.0406 (4)
C25	−0.0134 (3)	0.7214 (2)	0.18205 (7)	0.0429 (4)
H25	−0.1218	0.7703	0.1655	0.051*
C26	0.1709 (4)	0.7712 (2)	0.20492 (7)	0.0434 (4)
H26	0.1858	0.8554	0.2037	0.052*
C27	−0.2374 (3)	0.5415 (2)	0.15795 (8)	0.0487 (5)
H27A	−0.2659	0.4661	0.1753	0.058*
H27B	−0.3619	0.5948	0.1599	0.058*
N31	−0.7163 (3)	0.31924 (17)	0.02210 (7)	0.0463 (4)
C32	−0.7484 (3)	0.4285 (2)	0.03839 (8)	0.0513 (5)
H32	−0.8867	0.4622	0.0311	0.062*
C33	−0.5940 (4)	0.4967 (2)	0.06521 (8)	0.0479 (5)
H33	−0.6262	0.5748	0.0759	0.058*
C34	−0.3915 (3)	0.44918 (18)	0.07623 (7)	0.0396 (4)
C35	−0.3588 (4)	0.33600 (18)	0.05991 (9)	0.0444 (5)
H35	−0.2227	0.2995	0.0670	0.053*
C36	−0.5225 (4)	0.2743 (2)	0.03306 (8)	0.0466 (5)
H36	−0.4947	0.1960	0.0220	0.056*
C37	−0.2086 (4)	0.5164 (2)	0.10446 (9)	0.0570 (6)
H37A	−0.0756	0.4697	0.1031	0.068*
H37B	−0.1897	0.5931	0.0872	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0296 (7)	0.0333 (9)	0.0333 (8)	−0.0003 (6)	0.0012 (6)	−0.0042 (6)
C12	0.0283 (7)	0.0358 (9)	0.0386 (8)	−0.0026 (6)	0.0001 (6)	−0.0048 (7)
F12	0.0313 (5)	0.0417 (6)	0.0587 (7)	−0.0070 (4)	−0.0073 (5)	−0.0016 (5)
C13	0.0356 (8)	0.0311 (9)	0.0393 (9)	−0.0026 (7)	0.0033 (7)	−0.0020 (7)
F13	0.0428 (6)	0.0357 (6)	0.0640 (8)	−0.0075 (5)	0.0006 (5)	0.0072 (5)
C14	0.0342 (8)	0.0356 (9)	0.0322 (8)	0.0026 (7)	0.0022 (6)	−0.0025 (7)
I1	0.04208 (8)	0.04368 (9)	0.03394 (7)	0.00812 (5)	0.00129 (5)	0.00145 (4)
C15	0.0283 (7)	0.0403 (9)	0.0326 (8)	−0.0013 (6)	−0.0006 (6)	−0.0050 (7)
F15	0.0313 (5)	0.0484 (7)	0.0450 (6)	−0.0052 (4)	−0.0067 (4)	−0.0045 (5)
C16	0.0319 (8)	0.0323 (8)	0.0353 (8)	−0.0048 (6)	0.0024 (6)	−0.0031 (7)
F16	0.0392 (6)	0.0373 (6)	0.0513 (7)	−0.0097 (5)	−0.0019 (5)	0.0026 (5)
C17	0.0352 (8)	0.0339 (9)	0.0392 (9)	0.0000 (7)	0.0006 (7)	−0.0021 (7)
N17	0.0373 (8)	0.0366 (8)	0.0379 (8)	0.0043 (6)	−0.0025 (6)	−0.0023 (6)
O17	0.0390 (7)	0.0410 (7)	0.0521 (8)	0.0055 (6)	−0.0083 (6)	0.0036 (7)
N21	0.0430 (9)	0.0486 (10)	0.0341 (8)	−0.0011 (7)	−0.0042 (6)	0.0000 (7)
C22	0.0402 (9)	0.0481 (11)	0.0406 (10)	0.0068 (8)	−0.0046 (7)	0.0043 (8)
C23	0.0453 (10)	0.0413 (10)	0.0394 (9)	0.0012 (8)	−0.0021 (7)	0.0017 (8)
C24	0.0392 (9)	0.0525 (12)	0.0293 (8)	−0.0014 (8)	−0.0016 (6)	0.0023 (7)
C25	0.0435 (10)	0.0511 (12)	0.0327 (9)	0.0087 (9)	−0.0029 (7)	0.0054 (8)
C26	0.0524 (11)	0.0432 (11)	0.0333 (9)	0.0026 (9)	−0.0020 (7)	0.0015 (8)
C27	0.0409 (10)	0.0671 (15)	0.0370 (9)	−0.0083 (9)	−0.0023 (7)	0.0035 (9)
N31	0.0407 (9)	0.0594 (12)	0.0375 (8)	−0.0078 (7)	−0.0022 (7)	−0.0035 (7)
C32	0.0391 (10)	0.0703 (15)	0.0436 (11)	0.0154 (10)	−0.0010 (8)	0.0004 (10)
C33	0.0608 (12)	0.0399 (11)	0.0431 (10)	0.0112 (9)	0.0050 (9)	−0.0043 (8)
C34	0.0460 (10)	0.0404 (10)	0.0324 (8)	−0.0075 (8)	0.0034 (7)	−0.0023 (7)
C35	0.0390 (10)	0.0437 (11)	0.0487 (11)	0.0046 (8)	−0.0056 (8)	−0.0022 (8)
C36	0.0525 (12)	0.0354 (11)	0.0503 (11)	−0.0013 (8)	−0.0034 (9)	−0.0061 (8)
C37	0.0596 (13)	0.0696 (16)	0.0430 (11)	−0.0264 (12)	0.0109 (9)	−0.0176 (10)

Geometric parameters (Å, º)

C11—C12	1.389 (3)	C24—C25	1.378 (3)
C11—C16	1.394 (2)	C24—C27	1.509 (3)
C11—C17	1.455 (3)	C25—C26	1.375 (3)
C12—F12	1.3392 (19)	C25—H25	0.9500
C12—C13	1.378 (3)	C26—H26	0.9500
C13—F13	1.343 (2)	C27—C37	1.492 (3)
C13—C14	1.386 (2)	C27—H27A	0.9900
C14—C15	1.379 (3)	C27—H27B	0.9900
C14—I1	2.0936 (18)	N31—C36	1.323 (3)
C15—F15	1.3463 (19)	N31—C32	1.324 (3)
C15—C16	1.373 (3)	C32—C33	1.381 (3)
C16—F16	1.347 (2)	C32—H32	0.9500
C17—N17	1.282 (2)	C33—C34	1.384 (3)
C17—H17A	0.9500	C33—H33	0.9500
N17—O17	1.385 (2)	C34—C35	1.366 (3)
O17—H17	0.86 (3)	C34—C37	1.514 (3)
N21—C22	1.338 (3)	C35—C36	1.382 (3)
N21—C26	1.335 (3)	C35—H35	0.9500
C22—C23	1.380 (3)	C36—H36	0.9500
C22—H22	0.9500	C37—H37A	0.9900
C23—C24	1.391 (3)	C37—H37B	0.9900
C23—H23	0.9500
C12—C11—C16	115.47 (16)	C26—C25—H25	120.4
C12—C11—C17	125.99 (16)	C24—C25—H25	120.4
C16—C11—C17	118.53 (17)	N21—C26—C25	123.9 (2)
F12—C12—C13	117.64 (16)	N21—C26—H26	118.1
F12—C12—C11	120.47 (16)	C25—C26—H26	118.1
C13—C12—C11	121.89 (16)	C37—C27—C24	110.14 (18)
F13—C13—C12	118.21 (16)	C37—C27—H27A	109.6
F13—C13—C14	119.80 (16)	C24—C27—H27A	109.6
C12—C13—C14	121.98 (17)	C37—C27—H27B	109.6
C15—C14—C13	116.50 (16)	C24—C27—H27B	109.6
C15—C14—I1	120.92 (13)	H27A—C27—H27B	108.1
C13—C14—I1	122.58 (14)	C36—N31—C32	116.50 (19)
F15—C15—C16	118.59 (16)	N31—C32—C33	124.3 (2)
F15—C15—C14	119.85 (16)	N31—C32—H32	117.9
C16—C15—C14	121.57 (16)	C33—C32—H32	117.9
F16—C16—C15	118.19 (15)	C32—C33—C34	118.8 (2)
F16—C16—C11	119.23 (16)	C32—C33—H33	120.6
C15—C16—C11	122.58 (17)	C34—C33—H33	120.6
N17—C17—C11	121.81 (18)	C35—C34—C33	117.01 (19)
N17—C17—H17A	119.1	C35—C34—C37	119.6 (2)
C11—C17—H17A	119.1	C33—C34—C37	123.4 (2)
C17—N17—O17	110.23 (17)	C34—C35—C36	120.4 (2)
N17—O17—H17	103.0 (19)	C34—C35—H35	119.8
C22—N21—C26	116.83 (18)	C36—C35—H35	119.8
N21—C22—C23	123.17 (18)	N31—C36—C35	123.1 (2)
N21—C22—H22	118.4	N31—C36—H36	118.5
C23—C22—H22	118.4	C35—C36—H36	118.5
C22—C23—C24	119.2 (2)	C27—C37—C34	114.70 (18)
C22—C23—H23	120.4	C27—C37—H37A	108.6
C24—C23—H23	120.4	C34—C37—H37A	108.6
C25—C24—C23	117.75 (18)	C27—C37—H37B	108.6
C25—C24—C27	120.68 (18)	C34—C37—H37B	108.6
C23—C24—C27	121.5 (2)	H37A—C37—H37B	107.6
C26—C25—C24	119.19 (18)
C16—C11—C12—F12	−178.54 (16)	C12—C11—C17—N17	−3.7 (3)
C17—C11—C12—F12	2.6 (3)	C16—C11—C17—N17	177.48 (18)
C16—C11—C12—C13	1.0 (3)	C11—C17—N17—O17	−179.74 (16)
C17—C11—C12—C13	−177.79 (18)	C26—N21—C22—C23	−0.1 (3)
F12—C12—C13—F13	−0.3 (3)	N21—C22—C23—C24	−0.2 (3)
C11—C12—C13—F13	−179.89 (17)	C22—C23—C24—C25	0.5 (3)
F12—C12—C13—C14	178.67 (16)	C22—C23—C24—C27	178.95 (19)
C11—C12—C13—C14	−0.9 (3)	C23—C24—C25—C26	−0.4 (3)
F13—C13—C14—C15	178.76 (16)	C27—C24—C25—C26	−178.92 (19)
C12—C13—C14—C15	−0.2 (3)	C22—N21—C26—C25	0.2 (3)
F13—C13—C14—I1	−2.2 (2)	C24—C25—C26—N21	0.1 (3)
C12—C13—C14—I1	178.83 (14)	C25—C24—C27—C37	87.2 (3)
C13—C14—C15—F15	−179.12 (16)	C23—C24—C27—C37	−91.3 (3)
I1—C14—C15—F15	1.9 (2)	C36—N31—C32—C33	0.5 (3)
C13—C14—C15—C16	1.1 (3)	N31—C32—C33—C34	−0.1 (4)
I1—C14—C15—C16	−177.91 (14)	C32—C33—C34—C35	−0.6 (3)
F15—C15—C16—F16	−1.3 (2)	C32—C33—C34—C37	178.8 (2)
C14—C15—C16—F16	178.49 (16)	C33—C34—C35—C36	0.9 (3)
F15—C15—C16—C11	179.23 (16)	C37—C34—C35—C36	−178.5 (2)
C14—C15—C16—C11	−1.0 (3)	C32—N31—C36—C35	−0.2 (3)
C12—C11—C16—F16	−179.59 (16)	C34—C35—C36—N31	−0.5 (4)
C17—C11—C16—F16	−0.7 (3)	C24—C27—C37—C34	175.4 (2)
C12—C11—C16—C15	−0.1 (3)	C35—C34—C37—C27	−113.4 (3)
C17—C11—C16—C15	178.82 (17)	C33—C34—C37—C27	67.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O17—H17···N21	0.86 (3)	1.83 (3)	2.690 (2)	174 (3)

(IF4CO13) SD-1–8-1–7 4-I—F4-PhCOOH, 2,3,5,6-Me4-pyrazine

Crystal data

(C7HF4IO2)(C8H12N2)	Dx = 1.904 Mg m^−3
Mr = 456.17	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 5785 reflections
a = 17.5616 (10) Å	θ = 2.8–32.5°
b = 14.8078 (9) Å	µ = 2.07 mm^−1
c = 6.1199 (3) Å	T = 120 K
V = 1591.47 (15) Å^3	Plate, colourless
Z = 4	0.38 × 0.20 × 0.10 mm
F(000) = 888

Data collection

Bruker APEX-II CCD diffractometer	4502 independent reflections
Radiation source: fine-focus sealed tube	3352 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 32.5°, θmin = 1.8°
Absorption correction: multi-scan SADABS	h = −24→25
Tmin = 0.507, Tmax = 0.820	k = −22→21
12591 measured reflections	l = −5→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.095P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
4502 reflections	Δρmax = 3.16 e Å^−3
221 parameters	Δρmin = −2.34 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (3)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	−0.014819 (17)	0.25687 (2)	−0.37970 (17)	0.03077 (12)
C11	0.1458 (3)	0.3565 (4)	0.2293 (9)	0.0268 (10)
C17	0.2009 (2)	0.3857 (4)	0.4158 (9)	0.0261 (11)
O11	0.18993 (19)	0.3452 (3)	0.5886 (7)	0.0356 (9)
H11	0.2284	0.3505	0.6692	0.043*
O12	0.2450 (2)	0.4470 (3)	0.3750 (7)	0.0345 (9)
C12	0.1102 (3)	0.4171 (3)	0.0956 (10)	0.0283 (11)
F12	0.11947 (15)	0.50572 (17)	0.1205 (7)	0.0319 (6)
C13	0.0618 (3)	0.3895 (4)	−0.0732 (9)	0.0308 (11)
F13	0.02929 (19)	0.4525 (2)	−0.2000 (6)	0.0386 (8)
C14	0.0495 (3)	0.2988 (4)	−0.1124 (9)	0.0297 (11)
C15	0.0850 (4)	0.2379 (4)	0.0235 (11)	0.0298 (12)
F15	0.0750 (2)	0.1488 (2)	−0.0068 (6)	0.0386 (8)
C16	0.1312 (3)	0.2657 (4)	0.1872 (11)	0.0274 (11)
F16	0.1664 (2)	0.2016 (2)	0.3089 (6)	0.0388 (8)
N21	0.2961 (2)	0.3306 (3)	0.8706 (7)	0.0261 (9)
C22	0.3059 (4)	0.2457 (3)	0.9356 (10)	0.0262 (11)
C23	0.3564 (3)	0.2237 (3)	1.1052 (14)	0.0287 (11)
N24	0.3948 (3)	0.2901 (3)	1.2016 (8)	0.0286 (9)
C25	0.3864 (3)	0.3749 (3)	1.1362 (12)	0.0258 (9)
C26	0.3363 (3)	0.3964 (4)	0.9656 (9)	0.0270 (10)
C32	0.2621 (3)	0.1716 (4)	0.8174 (12)	0.0348 (13)
H32A	0.2268	0.1989	0.7125	0.052*
H32B	0.2333	0.1359	0.9240	0.052*
H32C	0.2979	0.1323	0.7398	0.052*
C33	0.3692 (3)	0.1286 (4)	1.1714 (10)	0.0344 (14)
H33A	0.4065	0.1266	1.2902	0.052*
H33B	0.3884	0.0942	1.0463	0.052*
H33C	0.3210	0.1022	1.2214	0.052*
C35	0.4293 (3)	0.4476 (4)	1.2547 (11)	0.0364 (13)
H35A	0.4675	0.4200	1.3506	0.055*
H35B	0.3938	0.4835	1.3425	0.055*
H35C	0.4548	0.4868	1.1483	0.055*
C36	0.3251 (3)	0.4907 (4)	0.8880 (9)	0.0318 (11)
H36A	0.2915	0.4906	0.7600	0.048*
H36B	0.3744	0.5169	0.8483	0.048*
H36C	0.3018	0.5267	1.0047	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02517 (17)	0.0469 (2)	0.02022 (17)	−0.00504 (11)	0.0003 (2)	−0.0033 (3)
C11	0.024 (2)	0.034 (3)	0.022 (2)	0.000 (2)	0.0020 (19)	0.001 (2)
C17	0.0145 (18)	0.035 (3)	0.029 (3)	−0.0005 (18)	0.0083 (19)	−0.011 (2)
O11	0.0290 (16)	0.046 (2)	0.032 (3)	−0.0051 (14)	−0.0066 (18)	0.006 (2)
O12	0.0345 (18)	0.041 (2)	0.028 (2)	−0.0043 (18)	−0.0028 (17)	0.0006 (19)
C12	0.029 (2)	0.035 (2)	0.021 (3)	−0.0023 (17)	−0.002 (2)	0.005 (2)
F12	0.0377 (13)	0.0283 (13)	0.0296 (14)	−0.0023 (10)	−0.0056 (19)	0.006 (2)
C13	0.031 (3)	0.037 (3)	0.025 (2)	−0.001 (2)	0.003 (2)	0.000 (2)
F13	0.0463 (18)	0.0364 (19)	0.0330 (19)	−0.0010 (15)	−0.0154 (16)	0.0052 (16)
C14	0.029 (2)	0.043 (3)	0.018 (2)	−0.005 (2)	−0.002 (2)	−0.005 (2)
C15	0.031 (3)	0.033 (3)	0.025 (3)	−0.001 (2)	0.002 (2)	−0.001 (2)
F15	0.0462 (18)	0.0354 (17)	0.0343 (18)	−0.0019 (16)	−0.0019 (16)	−0.0020 (16)
C16	0.027 (3)	0.030 (3)	0.025 (3)	0.003 (2)	0.004 (2)	0.004 (2)
F16	0.0470 (19)	0.0368 (19)	0.0325 (18)	0.0058 (16)	−0.0097 (17)	0.0056 (16)
N21	0.030 (2)	0.030 (2)	0.0189 (18)	0.0027 (18)	0.0027 (18)	0.0019 (18)
C22	0.027 (3)	0.033 (3)	0.018 (2)	0.0015 (18)	0.002 (2)	−0.0024 (19)
C23	0.028 (2)	0.035 (2)	0.023 (3)	−0.0002 (18)	−0.006 (3)	0.012 (3)
N24	0.032 (2)	0.030 (2)	0.024 (2)	0.0035 (19)	−0.0034 (18)	0.0004 (19)
C25	0.0246 (18)	0.030 (2)	0.023 (2)	−0.0007 (16)	−0.005 (2)	0.001 (3)
C26	0.025 (2)	0.036 (3)	0.020 (2)	−0.002 (2)	0.0038 (19)	0.000 (2)
C32	0.034 (3)	0.034 (3)	0.035 (3)	−0.002 (2)	−0.005 (2)	−0.006 (3)
C33	0.035 (3)	0.036 (3)	0.033 (3)	0.003 (2)	−0.006 (2)	0.006 (2)
C35	0.039 (3)	0.039 (3)	0.032 (3)	−0.005 (2)	−0.008 (3)	−0.003 (3)
C36	0.037 (3)	0.030 (3)	0.028 (3)	0.004 (2)	−0.002 (2)	0.003 (2)

Geometric parameters (Å, º)

I1—C14	2.083 (5)	C23—N24	1.330 (8)
C11—C12	1.367 (8)	C23—C33	1.482 (8)
C11—C16	1.391 (8)	N24—C25	1.327 (7)
C11—C17	1.558 (7)	C25—C26	1.402 (8)
C17—O12	1.220 (6)	C25—C35	1.501 (8)
C17—O11	1.231 (7)	C26—C36	1.488 (8)
O11—H11	0.8400	C32—H32A	0.9800
C12—F12	1.331 (6)	C32—H32B	0.9800
C12—C13	1.398 (8)	C32—H32C	0.9800
C13—F13	1.342 (7)	C33—H33A	0.9800
C13—C14	1.380 (8)	C33—H33B	0.9800
C14—C15	1.377 (9)	C33—H33C	0.9800
C15—F15	1.343 (6)	C35—H35A	0.9800
C15—C16	1.353 (9)	C35—H35B	0.9800
C16—F16	1.356 (7)	C35—H35C	0.9800
N21—C22	1.330 (7)	C36—H36A	0.9800
N21—C26	1.335 (7)	C36—H36B	0.9800
C22—C23	1.404 (10)	C36—H36C	0.9800
C22—C32	1.523 (8)
C12—C11—C16	116.1 (5)	N24—C25—C26	120.6 (5)
C12—C11—C17	122.7 (5)	N24—C25—C35	118.5 (5)
C16—C11—C17	121.2 (5)	C26—C25—C35	120.9 (5)
O12—C17—O11	129.6 (5)	N21—C26—C25	119.4 (5)
O12—C17—C11	116.9 (5)	N21—C26—C36	118.4 (5)
O11—C17—C11	113.4 (4)	C25—C26—C36	122.2 (5)
C17—O11—H11	109.5	C22—C32—H32A	109.5
F12—C12—C11	121.5 (5)	C22—C32—H32B	109.5
F12—C12—C13	116.6 (5)	H32A—C32—H32B	109.5
C11—C12—C13	121.8 (5)	C22—C32—H32C	109.5
F13—C13—C14	120.6 (5)	H32A—C32—H32C	109.5
F13—C13—C12	118.8 (5)	H32B—C32—H32C	109.5
C14—C13—C12	120.5 (5)	C23—C33—H33A	109.5
C15—C14—C13	117.5 (5)	C23—C33—H33B	109.5
C15—C14—I1	121.6 (4)	H33A—C33—H33B	109.5
C13—C14—I1	120.8 (4)	C23—C33—H33C	109.5
F15—C15—C16	118.7 (5)	H33A—C33—H33C	109.5
F15—C15—C14	120.1 (6)	H33B—C33—H33C	109.5
C16—C15—C14	121.2 (5)	C25—C35—H35A	109.5
C15—C16—F16	117.8 (5)	C25—C35—H35B	109.5
C15—C16—C11	122.8 (5)	H35A—C35—H35B	109.5
F16—C16—C11	119.4 (6)	C25—C35—H35C	109.5
C22—N21—C26	119.4 (5)	H35A—C35—H35C	109.5
N21—C22—C23	121.5 (5)	H35B—C35—H35C	109.5
N21—C22—C32	118.3 (5)	C26—C36—H36A	109.5
C23—C22—C32	120.2 (5)	C26—C36—H36B	109.5
N24—C23—C22	118.4 (5)	H36A—C36—H36B	109.5
N24—C23—C33	120.3 (6)	C26—C36—H36C	109.5
C22—C23—C33	121.2 (5)	H36A—C36—H36C	109.5
C25—N24—C23	120.7 (5)	H36B—C36—H36C	109.5
C12—C11—C17—O12	−41.2 (7)	F15—C15—C16—C11	179.2 (5)
C16—C11—C17—O12	137.6 (6)	C14—C15—C16—C11	0.0 (10)
C12—C11—C17—O11	135.2 (5)	C12—C11—C16—C15	0.5 (9)
C16—C11—C17—O11	−45.9 (7)	C17—C11—C16—C15	−178.4 (5)
C16—C11—C12—F12	179.7 (5)	C12—C11—C16—F16	178.0 (5)
C17—C11—C12—F12	−1.4 (8)	C17—C11—C16—F16	−0.9 (8)
C16—C11—C12—C13	0.1 (8)	C26—N21—C22—C23	1.3 (9)
C17—C11—C12—C13	179.0 (5)	C26—N21—C22—C32	−177.2 (5)
F12—C12—C13—F13	1.1 (8)	N21—C22—C23—N24	0.2 (10)
C11—C12—C13—F13	−179.3 (5)	C32—C22—C23—N24	178.7 (6)
F12—C12—C13—C14	179.3 (5)	N21—C22—C23—C33	−177.7 (6)
C11—C12—C13—C14	−1.0 (9)	C32—C22—C23—C33	0.8 (10)
F13—C13—C14—C15	179.6 (5)	C22—C23—N24—C25	−1.2 (9)
C12—C13—C14—C15	1.4 (9)	C33—C23—N24—C25	176.8 (6)
F13—C13—C14—I1	3.5 (8)	C23—N24—C25—C26	0.7 (9)
C12—C13—C14—I1	−174.7 (4)	C23—N24—C25—C35	178.3 (6)
C13—C14—C15—F15	179.9 (5)	C22—N21—C26—C25	−1.8 (8)
I1—C14—C15—F15	−4.0 (8)	C22—N21—C26—C36	179.2 (5)
C13—C14—C15—C16	−0.9 (9)	N24—C25—C26—N21	0.9 (8)
I1—C14—C15—C16	175.2 (5)	C35—C25—C26—N21	−176.8 (5)
F15—C15—C16—F16	1.6 (9)	N24—C25—C26—C36	179.8 (5)
C14—C15—C16—F16	−177.6 (6)	C35—C25—C26—C36	2.2 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···N21	0.84	1.74	2.550 (6)	162

(IF4CO12) SD—A-5–6 4-I—F4-PhCOOH, 4,4'-bipyridyl

Crystal data

(C7HIF4O2)(C10H8N2)	F(000) = 920
Mr = 476.16	Dx = 1.959 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.1699 (6) Å	Cell parameters from 9917 reflections
b = 11.1933 (6) Å	θ = 2.5–32.6°
c = 12.2448 (6) Å	µ = 2.04 mm^−1
β = 104.562 (2)°	T = 120 K
V = 1614.42 (14) Å^3	Prism, colourless
Z = 4	0.24 × 0.14 × 0.08 mm

Data collection

Bruker APEX-II CCD diffractometer	5816 independent reflections
Radiation source: fine-focus sealed tube	5229 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 32.6°, θmin = 1.7°
Absorption correction: multi-scan SADABS	h = −18→17
Tmin = 0.640, Tmax = 0.854	k = −16→16
26566 measured reflections	l = −18→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.025P)^2 + 1.5P] where P = (Fo^2 + 2Fc^2)/3
5816 reflections	(Δ/σ)max = 0.002
238 parameters	Δρmax = 0.89 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.036163 (9)	0.724735 (9)	0.828205 (9)	0.01951 (4)
N11	0.54874 (12)	0.66860 (13)	0.35776 (12)	0.0187 (2)
H11	0.4986 (19)	0.669 (2)	0.4297 (18)	0.022*
C12	0.57110 (14)	0.56961 (15)	0.30681 (15)	0.0208 (3)
H12	0.5441	0.4951	0.3265	0.025*
C13	0.63248 (14)	0.57246 (14)	0.22613 (15)	0.0203 (3)
H13	0.6451	0.5010	0.1892	0.024*
C14	0.67593 (13)	0.68080 (13)	0.19918 (13)	0.0157 (3)
C15	0.65085 (15)	0.78316 (14)	0.25372 (15)	0.0206 (3)
H15	0.6783	0.8588	0.2374	0.025*
C16	0.58658 (16)	0.77441 (14)	0.33081 (15)	0.0217 (3)
H16	0.5685	0.8449	0.3659	0.026*
N21	0.89668 (12)	0.69739 (13)	−0.02385 (13)	0.0213 (3)
C22	0.85414 (16)	0.79577 (15)	0.01063 (15)	0.0229 (3)
H22	0.8756	0.8707	−0.0139	0.027*
C23	0.78034 (15)	0.79533 (15)	0.08027 (15)	0.0208 (3)
H23	0.7515	0.8683	0.1014	0.025*
C24	0.74873 (13)	0.68641 (14)	0.11902 (13)	0.0159 (3)
C25	0.79247 (14)	0.58335 (15)	0.08219 (15)	0.0217 (3)
H25	0.7727	0.5069	0.1051	0.026*
C26	0.86508 (15)	0.59324 (15)	0.01191 (16)	0.0235 (3)
H26	0.8941	0.5219	−0.0123	0.028*
C31	0.29754 (14)	0.74777 (14)	0.57945 (13)	0.0170 (3)
C37	0.37709 (15)	0.75246 (15)	0.50208 (14)	0.0195 (3)
O31	0.44329 (11)	0.66239 (11)	0.51118 (11)	0.0241 (2)
O32	0.37174 (13)	0.83722 (12)	0.43812 (12)	0.0296 (3)
C32	0.23196 (14)	0.64774 (14)	0.58437 (14)	0.0186 (3)
F32	0.23763 (10)	0.55296 (9)	0.51917 (9)	0.0259 (2)
C33	0.15654 (14)	0.64330 (14)	0.65181 (14)	0.0188 (3)
F33	0.09572 (10)	0.54327 (9)	0.65067 (10)	0.0277 (2)
C34	0.14372 (14)	0.73845 (14)	0.71956 (14)	0.0182 (3)
C35	0.20831 (14)	0.83908 (14)	0.71431 (14)	0.0191 (3)
F35	0.20064 (10)	0.93554 (10)	0.77715 (10)	0.0295 (2)
C36	0.28269 (14)	0.84368 (14)	0.64599 (14)	0.0180 (3)
F36	0.34337 (9)	0.94427 (9)	0.64655 (9)	0.0245 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01980 (5)	0.02146 (6)	0.02006 (6)	0.00124 (3)	0.01017 (4)	−0.00028 (4)
N11	0.0197 (6)	0.0191 (6)	0.0201 (6)	0.0006 (5)	0.0101 (5)	0.0000 (5)
C12	0.0241 (7)	0.0176 (7)	0.0252 (8)	−0.0013 (5)	0.0145 (6)	0.0004 (6)
C13	0.0244 (7)	0.0151 (6)	0.0258 (8)	−0.0003 (5)	0.0144 (6)	−0.0008 (6)
C14	0.0162 (6)	0.0151 (6)	0.0171 (6)	0.0010 (5)	0.0065 (5)	0.0003 (5)
C15	0.0274 (8)	0.0149 (6)	0.0234 (8)	−0.0004 (5)	0.0136 (6)	−0.0004 (5)
C16	0.0279 (8)	0.0179 (7)	0.0233 (8)	0.0007 (6)	0.0141 (7)	−0.0017 (6)
N21	0.0219 (6)	0.0229 (6)	0.0229 (7)	0.0002 (5)	0.0130 (5)	0.0018 (5)
C22	0.0297 (8)	0.0197 (7)	0.0241 (8)	−0.0021 (6)	0.0160 (7)	0.0029 (6)
C23	0.0255 (8)	0.0170 (6)	0.0243 (8)	0.0008 (6)	0.0141 (6)	0.0011 (6)
C24	0.0161 (6)	0.0150 (6)	0.0178 (6)	0.0001 (5)	0.0064 (5)	0.0007 (5)
C25	0.0248 (8)	0.0162 (6)	0.0287 (8)	0.0003 (5)	0.0151 (7)	0.0001 (6)
C26	0.0262 (8)	0.0202 (7)	0.0301 (9)	0.0016 (6)	0.0179 (7)	−0.0012 (6)
C31	0.0195 (7)	0.0172 (6)	0.0169 (7)	0.0009 (5)	0.0092 (6)	0.0002 (5)
C37	0.0223 (7)	0.0193 (6)	0.0192 (7)	−0.0012 (5)	0.0095 (6)	0.0011 (5)
O31	0.0294 (6)	0.0219 (6)	0.0270 (6)	0.0065 (5)	0.0182 (5)	0.0053 (5)
O32	0.0392 (7)	0.0229 (6)	0.0351 (7)	0.0078 (5)	0.0248 (6)	0.0111 (5)
C32	0.0240 (7)	0.0150 (6)	0.0198 (7)	0.0001 (5)	0.0111 (6)	−0.0026 (5)
F32	0.0380 (6)	0.0163 (4)	0.0303 (5)	−0.0046 (4)	0.0215 (5)	−0.0080 (4)
C33	0.0222 (7)	0.0163 (6)	0.0214 (7)	−0.0026 (5)	0.0118 (6)	−0.0008 (5)
F33	0.0358 (6)	0.0200 (5)	0.0345 (6)	−0.0097 (4)	0.0225 (5)	−0.0057 (4)
C34	0.0205 (7)	0.0188 (7)	0.0182 (7)	0.0008 (5)	0.0104 (6)	−0.0004 (5)
C35	0.0238 (7)	0.0177 (6)	0.0182 (7)	0.0004 (5)	0.0098 (6)	−0.0047 (5)
F35	0.0416 (6)	0.0214 (5)	0.0329 (6)	−0.0061 (4)	0.0229 (5)	−0.0121 (4)
C36	0.0214 (7)	0.0155 (6)	0.0186 (7)	−0.0023 (5)	0.0081 (6)	−0.0011 (5)
F36	0.0297 (5)	0.0179 (4)	0.0297 (5)	−0.0077 (4)	0.0146 (4)	−0.0046 (4)

Geometric parameters (Å, º)

I1—C34	2.0934 (16)	C24—C25	1.392 (2)
N11—C12	1.333 (2)	C25—C26	1.384 (2)
N11—C16	1.342 (2)	C25—H25	0.9500
N11—H11	1.19 (2)	C26—H26	0.9500
C12—C13	1.381 (2)	C31—C32	1.385 (2)
C12—H12	0.9500	C31—C36	1.387 (2)
C13—C14	1.395 (2)	C31—C37	1.516 (2)
C13—H13	0.9500	C37—O32	1.221 (2)
C14—C15	1.398 (2)	C37—O31	1.278 (2)
C14—C24	1.480 (2)	O31—H11	1.34 (2)
C15—C16	1.373 (2)	C32—F32	1.3399 (17)
C15—H15	0.9500	C32—C33	1.381 (2)
C16—H16	0.9500	C33—F33	1.3404 (18)
N21—C22	1.330 (2)	C33—C34	1.383 (2)
N21—C26	1.335 (2)	C34—C35	1.384 (2)
C22—C23	1.385 (2)	C35—F35	1.3426 (18)
C22—H22	0.9500	C35—C36	1.379 (2)
C23—C24	1.397 (2)	C36—F36	1.3455 (18)
C23—H23	0.9500
C12—N11—C16	119.71 (14)	C26—C25—C24	119.41 (15)
C12—N11—H11	123.7 (11)	C26—C25—H25	120.3
C16—N11—H11	116.5 (11)	C24—C25—H25	120.3
N11—C12—C13	121.78 (15)	N21—C26—C25	123.72 (15)
N11—C12—H12	119.1	N21—C26—H26	118.1
C13—C12—H12	119.1	C25—C26—H26	118.1
C12—C13—C14	119.65 (14)	C32—C31—C36	116.02 (14)
C12—C13—H13	120.2	C32—C31—C37	121.37 (14)
C14—C13—H13	120.2	C36—C31—C37	122.57 (14)
C13—C14—C15	117.26 (14)	O32—C37—O31	126.84 (16)
C13—C14—C24	121.30 (13)	O32—C37—C31	119.21 (15)
C15—C14—C24	121.41 (14)	O31—C37—C31	113.94 (14)
C16—C15—C14	120.05 (14)	C37—O31—H11	108.3 (10)
C16—C15—H15	120.0	F32—C32—C33	117.99 (14)
C14—C15—H15	120.0	F32—C32—C31	119.84 (14)
N11—C16—C15	121.49 (15)	C33—C32—C31	122.13 (14)
N11—C16—H16	119.3	F33—C33—C32	118.17 (14)
C15—C16—H16	119.3	F33—C33—C34	120.29 (14)
C22—N21—C26	116.85 (14)	C32—C33—C34	121.55 (14)
N21—C22—C23	123.84 (15)	C33—C34—C35	116.60 (14)
N21—C22—H22	118.1	C33—C34—I1	120.51 (12)
C23—C22—H22	118.1	C35—C34—I1	122.84 (11)
C22—C23—C24	119.26 (15)	F35—C35—C36	117.93 (14)
C22—C23—H23	120.4	F35—C35—C34	120.37 (14)
C24—C23—H23	120.4	C36—C35—C34	121.70 (14)
C25—C24—C23	116.92 (14)	F36—C36—C35	118.11 (14)
C25—C24—C14	121.41 (14)	F36—C36—C31	119.90 (14)
C23—C24—C14	121.62 (14)	C35—C36—C31	121.98 (14)
C16—N11—C12—C13	−0.1 (3)	C36—C31—C32—F32	177.24 (15)
N11—C12—C13—C14	2.2 (3)	C37—C31—C32—F32	−0.5 (2)
C12—C13—C14—C15	−2.3 (3)	C36—C31—C32—C33	−0.3 (2)
C12—C13—C14—C24	175.75 (16)	C37—C31—C32—C33	−178.00 (16)
C13—C14—C15—C16	0.5 (3)	F32—C32—C33—F33	1.9 (2)
C24—C14—C15—C16	−177.55 (16)	C31—C32—C33—F33	179.43 (16)
C12—N11—C16—C15	−1.8 (3)	F32—C32—C33—C34	−178.50 (16)
C14—C15—C16—N11	1.6 (3)	C31—C32—C33—C34	−0.9 (3)
C26—N21—C22—C23	0.0 (3)	F33—C33—C34—C35	−178.94 (16)
N21—C22—C23—C24	1.0 (3)	C32—C33—C34—C35	1.4 (3)
C22—C23—C24—C25	−1.4 (3)	F33—C33—C34—I1	3.4 (2)
C22—C23—C24—C14	176.14 (16)	C32—C33—C34—I1	−176.17 (13)
C13—C14—C24—C25	−11.0 (2)	C33—C34—C35—F35	179.79 (16)
C15—C14—C24—C25	166.89 (17)	I1—C34—C35—F35	−2.7 (2)
C13—C14—C24—C23	171.50 (16)	C33—C34—C35—C36	−0.8 (3)
C15—C14—C24—C23	−10.6 (2)	I1—C34—C35—C36	176.79 (13)
C23—C24—C25—C26	1.0 (3)	F35—C35—C36—F36	0.2 (2)
C14—C24—C25—C26	−176.57 (16)	C34—C35—C36—F36	−179.27 (16)
C22—N21—C26—C25	−0.5 (3)	F35—C35—C36—C31	179.02 (16)
C24—C25—C26—N21	0.0 (3)	C34—C35—C36—C31	−0.4 (3)
C32—C31—C37—O32	128.44 (19)	C32—C31—C36—F36	179.76 (15)
C36—C31—C37—O32	−49.1 (3)	C37—C31—C36—F36	−2.5 (2)
C32—C31—C37—O31	−50.6 (2)	C32—C31—C36—C35	1.0 (2)
C36—C31—C37—O31	131.82 (17)	C37—C31—C36—C35	178.65 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O31	1.19 (2)	1.34 (2)	2.5285 (17)	176 (2)

(BrCO11) SD-1–27-6–5 1,2-bis(4-pyridyl)ethane, (4-Br-PhCOOH)2

Crystal data

(C12H12N2)(C7H5BrO2)2	Z = 1
Mr = 586.28	F(000) = 294
Triclinic, P1	Dx = 1.689 Mg m^−3
a = 7.1108 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4624 (4) Å	Cell parameters from 6775 reflections
c = 11.2299 (6) Å	θ = 2.8–32.9°
α = 93.434 (2)°	µ = 3.55 mm^−1
β = 94.022 (2)°	T = 120 K
γ = 103.373 (2)°	Plate, colourless
V = 576.53 (5) Å^3	0.34 × 0.22 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	4144 independent reflections
Radiation source: fine-focus sealed tube	3417 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 33.2°, θmin = 1.8°
Absorption correction: multi-scan SADABS	h = −10→10
Tmin = 0.378, Tmax = 0.815	k = −11→11
13290 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.065P)^2 + 0.2P] where P = (Fo^2 + 2Fc^2)/3
4144 reflections	(Δ/σ)max = 0.002
157 parameters	Δρmax = 0.77 e Å^−3
0 restraints	Δρmin = −1.01 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.2019 (3)	0.9603 (2)	0.36740 (17)	0.0222 (3)
C12	0.3794 (3)	0.9729 (3)	0.3303 (2)	0.0229 (4)
H12	0.4292	1.0683	0.2806	0.027*
C13	0.4924 (3)	0.8527 (3)	0.36146 (19)	0.0207 (4)
H13	0.6174	0.8661	0.3332	0.025*
C14	0.4231 (3)	0.7114 (3)	0.43455 (18)	0.0192 (3)
C15	0.2396 (3)	0.6999 (3)	0.47291 (19)	0.0220 (4)
H15	0.1863	0.6067	0.5233	0.026*
C16	0.1345 (3)	0.8254 (3)	0.4371 (2)	0.0234 (4)
H16	0.0087	0.8149	0.4636	0.028*
C17	0.5495 (3)	0.5830 (3)	0.46874 (19)	0.0209 (4)
H17A	0.6624	0.6542	0.5219	0.025*
H17B	0.5996	0.5385	0.3953	0.025*
Br1	−0.34658 (3)	1.87116 (3)	0.04548 (2)	0.02855 (9)
C21	−0.0148 (3)	1.4482 (3)	0.18747 (17)	0.0179 (3)
C27	0.0972 (3)	1.3182 (3)	0.23586 (18)	0.0189 (3)
O21	−0.0107 (2)	1.1762 (2)	0.28247 (16)	0.0276 (3)
H21	0.053 (5)	1.102 (5)	0.306 (3)	0.033*
O22	0.2719 (2)	1.3448 (2)	0.23445 (16)	0.0282 (3)
C22	0.0858 (3)	1.6105 (3)	0.14412 (19)	0.0208 (4)
H22	0.2230	1.6349	0.1440	0.025*
C23	−0.0119 (3)	1.7364 (3)	0.10132 (19)	0.0222 (4)
H23	0.0567	1.8477	0.0721	0.027*
C24	−0.2122 (3)	1.6972 (3)	0.10176 (19)	0.0205 (4)
C25	−0.3165 (3)	1.5356 (3)	0.1423 (2)	0.0232 (4)
H25	−0.4539	1.5106	0.1408	0.028*
C26	−0.2160 (3)	1.4107 (3)	0.1853 (2)	0.0218 (4)
H26	−0.2851	1.2988	0.2135	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0224 (8)	0.0167 (7)	0.0287 (9)	0.0073 (6)	−0.0003 (6)	0.0030 (6)
C12	0.0240 (9)	0.0175 (8)	0.0283 (10)	0.0065 (7)	0.0012 (7)	0.0051 (7)
C13	0.0197 (8)	0.0169 (8)	0.0262 (10)	0.0054 (6)	0.0023 (7)	0.0030 (7)
C14	0.0185 (8)	0.0155 (8)	0.0240 (9)	0.0059 (6)	−0.0014 (6)	0.0014 (7)
C15	0.0204 (8)	0.0194 (8)	0.0277 (10)	0.0067 (7)	0.0024 (7)	0.0056 (7)
C16	0.0197 (8)	0.0206 (9)	0.0316 (11)	0.0080 (7)	0.0019 (7)	0.0034 (8)
C17	0.0177 (8)	0.0184 (8)	0.0284 (10)	0.0074 (6)	0.0012 (7)	0.0045 (7)
Br1	0.02723 (12)	0.02552 (12)	0.03712 (15)	0.01302 (8)	0.00177 (8)	0.01073 (9)
C21	0.0169 (8)	0.0176 (8)	0.0195 (9)	0.0051 (6)	0.0008 (6)	0.0011 (6)
C27	0.0190 (8)	0.0173 (8)	0.0207 (9)	0.0052 (6)	0.0002 (6)	0.0020 (7)
O21	0.0198 (7)	0.0236 (7)	0.0432 (9)	0.0090 (6)	0.0050 (6)	0.0155 (7)
O22	0.0181 (7)	0.0273 (8)	0.0411 (9)	0.0075 (6)	0.0018 (6)	0.0094 (7)
C22	0.0159 (8)	0.0201 (8)	0.0257 (10)	0.0032 (6)	0.0002 (6)	0.0031 (7)
C23	0.0206 (8)	0.0192 (8)	0.0262 (10)	0.0030 (7)	0.0009 (7)	0.0055 (7)
C24	0.0193 (8)	0.0197 (8)	0.0246 (9)	0.0081 (7)	0.0013 (7)	0.0051 (7)
C25	0.0158 (8)	0.0224 (9)	0.0323 (11)	0.0051 (7)	0.0023 (7)	0.0066 (8)
C26	0.0170 (8)	0.0188 (8)	0.0302 (10)	0.0043 (6)	0.0027 (7)	0.0061 (7)

Geometric parameters (Å, º)

N11—C16	1.334 (3)	C21—C26	1.391 (3)
N11—C12	1.341 (3)	C21—C22	1.391 (3)
C12—C13	1.380 (3)	C21—C27	1.493 (3)
C12—H12	0.9500	C27—O22	1.213 (2)
C13—C14	1.396 (3)	C27—O21	1.316 (2)
C13—H13	0.9500	O21—H21	0.83 (4)
C14—C15	1.388 (3)	C22—C23	1.381 (3)
C14—C17	1.506 (3)	C22—H22	0.9500
C15—C16	1.387 (3)	C23—C24	1.387 (3)
C15—H15	0.9500	C23—H23	0.9500
C16—H16	0.9500	C24—C25	1.382 (3)
C17—C17^i	1.515 (4)	C25—C26	1.388 (3)
C17—H17A	0.9900	C25—H25	0.9500
C17—H17B	0.9900	C26—H26	0.9500
Br1—C24	1.8934 (19)
C16—N11—C12	117.79 (18)	C26—C21—C22	119.69 (18)
N11—C12—C13	122.58 (19)	C26—C21—C27	121.56 (17)
N11—C12—H12	118.7	C22—C21—C27	118.75 (17)
C13—C12—H12	118.7	O22—C27—O21	123.69 (18)
C12—C13—C14	119.98 (18)	O22—C27—C21	122.62 (18)
C12—C13—H13	120.0	O21—C27—C21	113.68 (16)
C14—C13—H13	120.0	C27—O21—H21	112 (2)
C15—C14—C13	117.03 (17)	C23—C22—C21	120.55 (18)
C15—C14—C17	123.78 (18)	C23—C22—H22	119.7
C13—C14—C17	119.18 (17)	C21—C22—H22	119.7
C16—C15—C14	119.52 (19)	C22—C23—C24	118.67 (18)
C16—C15—H15	120.2	C22—C23—H23	120.7
C14—C15—H15	120.2	C24—C23—H23	120.7
N11—C16—C15	123.10 (19)	C25—C24—C23	122.08 (18)
N11—C16—H16	118.5	C25—C24—Br1	119.08 (14)
C15—C16—H16	118.5	C23—C24—Br1	118.83 (15)
C14—C17—C17^i	115.1 (2)	C24—C25—C26	118.53 (18)
C14—C17—H17A	108.5	C24—C25—H25	120.7
C17^i—C17—H17A	108.5	C26—C25—H25	120.7
C14—C17—H17B	108.5	C25—C26—C21	120.45 (18)
C17^i—C17—H17B	108.5	C25—C26—H26	119.8
H17A—C17—H17B	107.5	C21—C26—H26	119.8
C16—N11—C12—C13	0.0 (3)	C26—C21—C27—O21	−4.5 (3)
N11—C12—C13—C14	−0.1 (3)	C22—C21—C27—O21	175.25 (19)
C12—C13—C14—C15	−0.1 (3)	C26—C21—C22—C23	1.4 (3)
C12—C13—C14—C17	−179.29 (19)	C27—C21—C22—C23	−178.41 (19)
C13—C14—C15—C16	0.5 (3)	C21—C22—C23—C24	−0.4 (3)
C17—C14—C15—C16	179.58 (19)	C22—C23—C24—C25	−0.7 (3)
C12—N11—C16—C15	0.3 (3)	C22—C23—C24—Br1	179.03 (16)
C14—C15—C16—N11	−0.6 (3)	C23—C24—C25—C26	0.9 (3)
C15—C14—C17—C17^i	10.2 (3)	Br1—C24—C25—C26	−178.87 (16)
C13—C14—C17—C17^i	−170.7 (2)	C24—C25—C26—C21	0.1 (3)
C26—C21—C27—O22	177.2 (2)	C22—C21—C26—C25	−1.2 (3)
C22—C21—C27—O22	−3.1 (3)	C27—C21—C26—C25	178.57 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21···N11	0.83 (4)	1.80 (4)	2.626 (2)	174 (3)

(BrCO12) CS—AL-6–12 4,4'-bipyridyl, (4-Br-PhCOOH)2

Crystal data

(C10H8N2)(C7H5BrO2)2	F(000) = 1668
Mr = 558.22	Dx = 1.720 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.0467 (6) Å	Cell parameters from 3538 reflections
b = 28.9658 (18) Å	θ = 2.7–25.5°
c = 10.7956 (7) Å	µ = 3.80 mm^−1
β = 110.603 (2)°	T = 120 K
V = 3233.4 (3) Å^3	Needle, colourless
Z = 6	0.34 × 0.08 × 0.04 mm

Data collection

Bruker APEX-II CCD diffractometer	17575 independent reflections
Radiation source: fine-focus sealed tube	9657 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 31.6°, θmin = 2.0°
Absorption correction: multi-scan TWINABS	h = −15→14
Tmin = 0.359, Tmax = 0.863	k = 0→41
17557 measured reflections	l = 0→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.080P)^2] where P = (Fo^2 + 2Fc^2)/3
17575 reflections	(Δ/σ)max = 0.002
437 parameters	Δρmax = 1.01 e Å^−3
0 restraints	Δρmin = −1.03 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11_1	−0.0362 (3)	0.38315 (10)	0.0785 (3)	0.0360 (7)
C12_1	0.0194 (3)	0.41425 (13)	0.1721 (3)	0.0387 (8)
H12_1	0.0492	0.4044	0.2618	0.046*
C13_1	0.0361 (3)	0.45971 (13)	0.1461 (3)	0.0374 (8)
H13_1	0.0773	0.4803	0.2168	0.045*
C14_1	−0.0075 (3)	0.47564 (12)	0.0157 (3)	0.0304 (7)
C15_1	−0.0650 (4)	0.44269 (13)	−0.0809 (3)	0.0433 (9)
H15_1	−0.0962	0.4510	−0.1718	0.052*
C16_1	−0.0760 (3)	0.39800 (13)	−0.0432 (3)	0.0401 (8)
H16_1	−0.1159	0.3763	−0.1112	0.048*
N11_2	0.6444 (2)	0.43767 (8)	0.5571 (2)	0.0244 (5)
C12_2	0.6315 (3)	0.41935 (10)	0.4391 (3)	0.0247 (6)
H12_2	0.6298	0.4397	0.3695	0.030*
C13_2	0.6206 (3)	0.37333 (11)	0.4135 (3)	0.0249 (6)
H13_2	0.6111	0.3622	0.3278	0.030*
C14_2	0.6234 (3)	0.34230 (10)	0.5140 (3)	0.0218 (6)
C15_2	0.6387 (3)	0.36131 (11)	0.6369 (3)	0.0253 (6)
H15_2	0.6428	0.3417	0.7088	0.030*
C16_2	0.6478 (3)	0.40815 (10)	0.6543 (3)	0.0260 (6)
H16_2	0.6570	0.4203	0.7388	0.031*
N11_3	0.5803 (2)	0.19660 (9)	0.4462 (2)	0.0266 (5)
C12_3	0.6428 (3)	0.21376 (11)	0.5672 (3)	0.0290 (7)
H12_3	0.6769	0.1928	0.6388	0.035*
C13_3	0.6599 (3)	0.26038 (10)	0.5924 (3)	0.0255 (6)
H13_3	0.7057	0.2709	0.6798	0.031*
C14_3	0.6108 (3)	0.29197 (10)	0.4910 (3)	0.0228 (6)
C15_3	0.5454 (3)	0.27387 (11)	0.3648 (3)	0.0261 (6)
H15_3	0.5093	0.2939	0.2914	0.031*
C16_3	0.5341 (3)	0.22684 (11)	0.3481 (3)	0.0286 (7)
H16_3	0.4907	0.2153	0.2614	0.034*
Br1_1	−0.02853 (3)	0.058958 (13)	0.03885 (4)	0.04202 (11)
C21_1	−0.0612 (3)	0.21896 (12)	0.0196 (3)	0.0289 (7)
C22_1	−0.0928 (3)	0.19316 (12)	−0.0965 (3)	0.0322 (7)
H22_1	−0.1199	0.2084	−0.1798	0.039*
C23_1	−0.0848 (3)	0.14594 (13)	−0.0909 (3)	0.0339 (7)
H23_1	−0.1075	0.1283	−0.1700	0.041*
C24_1	−0.0433 (3)	0.12425 (12)	0.0310 (3)	0.0306 (7)
C25_1	−0.0123 (3)	0.14940 (13)	0.1471 (3)	0.0341 (8)
H25_1	0.0155	0.1341	0.2302	0.041*
C26_1	−0.0219 (3)	0.19629 (13)	0.1411 (3)	0.0333 (7)
H26_1	−0.0017	0.2137	0.2204	0.040*
C27_1	−0.0729 (3)	0.27064 (11)	0.0080 (3)	0.0260 (6)
O21_1	−0.0295 (2)	0.29227 (8)	0.1198 (2)	0.0367 (5)
H21_1	−0.0327	0.3209	0.1060	0.044*
O22_1	−0.1230 (2)	0.28929 (9)	−0.0995 (2)	0.0394 (6)
Br2_2	0.75515 (4)	0.757335 (13)	0.52374 (5)	0.04798 (12)
C21_2	0.6899 (3)	0.59882 (11)	0.4969 (3)	0.0249 (6)
C22_2	0.6972 (3)	0.62311 (11)	0.3889 (3)	0.0290 (7)
H22_2	0.6866	0.6073	0.3086	0.035*
C23_2	0.7198 (3)	0.67004 (11)	0.3976 (3)	0.0314 (7)
H23_2	0.7264	0.6866	0.3243	0.038*
C24_2	0.7328 (3)	0.69258 (11)	0.5143 (3)	0.0328 (7)
C25_2	0.7258 (3)	0.66893 (11)	0.6233 (3)	0.0319 (7)
H25_2	0.7356	0.6849	0.7031	0.038*
C26_2	0.7044 (3)	0.62199 (11)	0.6141 (3)	0.0262 (6)
H26_2	0.6995	0.6054	0.6880	0.031*
C27_2	0.6676 (3)	0.54766 (10)	0.4837 (3)	0.0229 (6)
O21_2	0.6768 (2)	0.52714 (7)	0.59450 (19)	0.0301 (5)
H21_2	0.6555	0.4993	0.5795	0.036*
O22_2	0.6444 (2)	0.52791 (8)	0.3786 (2)	0.0343 (5)
Br3_3	0.71468 (4)	−0.123768 (12)	0.48989 (4)	0.04144 (11)
C21_3	0.6546 (3)	0.03391 (11)	0.5218 (3)	0.0236 (6)
C22_3	0.7283 (3)	0.00880 (11)	0.6331 (3)	0.0267 (7)
H22_3	0.7662	0.0241	0.7157	0.032*
C23_3	0.7467 (3)	−0.03775 (11)	0.6245 (3)	0.0287 (7)
H23_3	0.7964	−0.0549	0.7003	0.034*
C24_3	0.6910 (3)	−0.05926 (11)	0.5026 (3)	0.0270 (6)
C25_3	0.6180 (3)	−0.03526 (11)	0.3916 (3)	0.0266 (6)
H25_3	0.5814	−0.0507	0.3091	0.032*
C26_3	0.5985 (3)	0.01124 (11)	0.4013 (3)	0.0243 (6)
H26_3	0.5467	0.0280	0.3255	0.029*
C27_3	0.6380 (3)	0.08433 (10)	0.5355 (3)	0.0227 (6)
O21_3	0.5798 (2)	0.10551 (7)	0.42154 (19)	0.0298 (5)
H21_3	0.5650	0.1331	0.4358	0.036*
O22_3	0.6750 (2)	0.10421 (8)	0.6424 (2)	0.0339 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11_1	0.0322 (15)	0.0448 (18)	0.0306 (14)	−0.0016 (13)	0.0105 (12)	−0.0022 (13)
C12_1	0.0353 (18)	0.052 (2)	0.0234 (16)	0.0052 (17)	0.0043 (14)	0.0029 (15)
C13_1	0.0331 (17)	0.044 (2)	0.0266 (16)	0.0024 (16)	0.0005 (14)	−0.0049 (15)
C14_1	0.0201 (14)	0.048 (2)	0.0232 (15)	0.0020 (14)	0.0080 (12)	−0.0021 (15)
C15_1	0.049 (2)	0.057 (2)	0.0223 (16)	−0.0111 (18)	0.0112 (16)	−0.0056 (16)
C16_1	0.049 (2)	0.042 (2)	0.0326 (18)	−0.0129 (17)	0.0187 (17)	−0.0097 (16)
N11_2	0.0312 (13)	0.0241 (13)	0.0175 (11)	−0.0008 (11)	0.0079 (10)	0.0009 (10)
C12_2	0.0256 (15)	0.0263 (16)	0.0192 (13)	0.0020 (12)	0.0042 (12)	0.0025 (12)
C13_2	0.0250 (15)	0.0330 (17)	0.0150 (12)	−0.0013 (13)	0.0048 (12)	−0.0001 (12)
C14_2	0.0236 (14)	0.0245 (15)	0.0165 (13)	0.0022 (12)	0.0062 (11)	−0.0011 (11)
C15_2	0.0342 (17)	0.0264 (16)	0.0184 (13)	−0.0009 (13)	0.0130 (13)	0.0021 (12)
C16_2	0.0370 (16)	0.0252 (15)	0.0169 (13)	−0.0001 (13)	0.0109 (12)	−0.0018 (12)
N11_3	0.0318 (13)	0.0252 (13)	0.0229 (12)	0.0008 (11)	0.0097 (11)	−0.0025 (10)
C12_3	0.0344 (17)	0.0300 (17)	0.0240 (15)	0.0038 (14)	0.0122 (13)	0.0006 (13)
C13_3	0.0320 (16)	0.0269 (16)	0.0193 (13)	−0.0029 (13)	0.0109 (13)	−0.0016 (12)
C14_3	0.0224 (14)	0.0288 (16)	0.0200 (13)	−0.0025 (12)	0.0108 (12)	−0.0038 (12)
C15_3	0.0267 (15)	0.0326 (17)	0.0170 (13)	0.0005 (13)	0.0051 (12)	−0.0007 (12)
C16_3	0.0309 (16)	0.0335 (17)	0.0202 (14)	−0.0032 (14)	0.0073 (13)	−0.0071 (13)
Br1_1	0.0400 (2)	0.0444 (2)	0.03643 (19)	0.00127 (16)	0.00702 (16)	0.00074 (16)
C21_1	0.0189 (14)	0.049 (2)	0.0191 (14)	−0.0017 (14)	0.0074 (12)	−0.0033 (13)
C22_1	0.0332 (17)	0.046 (2)	0.0171 (14)	−0.0033 (15)	0.0083 (13)	0.0001 (14)
C23_1	0.0305 (17)	0.048 (2)	0.0201 (14)	−0.0045 (15)	0.0043 (13)	−0.0051 (14)
C24_1	0.0239 (15)	0.0401 (19)	0.0258 (15)	−0.0006 (13)	0.0063 (13)	0.0002 (14)
C25_1	0.0307 (17)	0.051 (2)	0.0200 (15)	0.0056 (15)	0.0076 (13)	0.0040 (14)
C26_1	0.0309 (16)	0.050 (2)	0.0201 (14)	0.0031 (15)	0.0100 (13)	−0.0014 (14)
C27_1	0.0239 (15)	0.0376 (18)	0.0206 (14)	0.0007 (13)	0.0128 (12)	0.0001 (13)
O21_1	0.0458 (13)	0.0418 (14)	0.0213 (11)	0.0019 (11)	0.0102 (10)	−0.0023 (10)
O22_1	0.0467 (14)	0.0467 (15)	0.0223 (11)	0.0005 (12)	0.0088 (11)	−0.0001 (11)
Br2_2	0.0444 (2)	0.02604 (18)	0.0724 (3)	0.00012 (15)	0.0191 (2)	0.00279 (18)
C21_2	0.0224 (14)	0.0271 (16)	0.0237 (14)	0.0043 (12)	0.0060 (12)	0.0012 (12)
C22_2	0.0297 (16)	0.0322 (17)	0.0247 (15)	0.0042 (13)	0.0092 (13)	0.0025 (13)
C23_2	0.0245 (15)	0.0324 (17)	0.0366 (18)	0.0049 (13)	0.0098 (14)	0.0107 (14)
C24_2	0.0260 (16)	0.0244 (16)	0.045 (2)	0.0049 (13)	0.0096 (15)	0.0040 (15)
C25_2	0.0285 (16)	0.0314 (18)	0.0333 (17)	0.0025 (13)	0.0078 (14)	−0.0032 (14)
C26_2	0.0243 (15)	0.0286 (16)	0.0251 (14)	0.0018 (12)	0.0080 (12)	0.0011 (13)
C27_2	0.0219 (14)	0.0264 (16)	0.0182 (13)	0.0010 (12)	0.0043 (11)	−0.0020 (12)
O21_2	0.0454 (13)	0.0240 (11)	0.0181 (10)	−0.0024 (10)	0.0078 (10)	−0.0004 (9)
O22_2	0.0491 (14)	0.0314 (13)	0.0208 (10)	−0.0023 (10)	0.0101 (10)	−0.0012 (9)
Br3_3	0.0545 (2)	0.02981 (19)	0.0400 (2)	0.00703 (16)	0.01664 (17)	0.00402 (15)
C21_3	0.0292 (15)	0.0284 (16)	0.0158 (13)	−0.0042 (12)	0.0112 (12)	0.0003 (12)
C22_3	0.0285 (15)	0.0352 (18)	0.0150 (13)	−0.0027 (13)	0.0061 (12)	0.0000 (12)
C23_3	0.0292 (16)	0.0361 (18)	0.0188 (14)	0.0025 (14)	0.0059 (12)	0.0083 (13)
C24_3	0.0276 (16)	0.0268 (16)	0.0280 (15)	0.0018 (12)	0.0118 (13)	0.0052 (13)
C25_3	0.0297 (16)	0.0297 (17)	0.0188 (13)	−0.0034 (13)	0.0064 (12)	−0.0016 (12)
C26_3	0.0249 (15)	0.0330 (17)	0.0143 (12)	−0.0016 (12)	0.0063 (12)	0.0035 (12)
C27_3	0.0258 (15)	0.0271 (15)	0.0162 (13)	−0.0027 (12)	0.0086 (12)	0.0024 (11)
O21_3	0.0454 (13)	0.0241 (11)	0.0192 (10)	0.0023 (10)	0.0107 (10)	−0.0002 (9)
O22_3	0.0465 (13)	0.0333 (13)	0.0201 (10)	−0.0029 (11)	0.0094 (10)	−0.0054 (9)

Geometric parameters (Å, º)

N11_1—C16_1	1.303 (4)	C23_1—H23_1	0.9500
N11_1—C12_1	1.332 (4)	C24_1—C25_1	1.384 (4)
C12_1—C13_1	1.373 (5)	C25_1—C26_1	1.362 (5)
C12_1—H12_1	0.9500	C25_1—H25_1	0.9500
C13_1—C14_1	1.397 (5)	C26_1—H26_1	0.9500
C13_1—H13_1	0.9500	C27_1—O22_1	1.221 (4)
C14_1—C15_1	1.391 (5)	C27_1—O21_1	1.294 (4)
C14_1—C14_1^i	1.474 (7)	O21_1—H21_1	0.8400
C15_1—C16_1	1.375 (5)	Br2_2—C24_2	1.890 (3)
C15_1—H15_1	0.9500	C21_2—C22_2	1.388 (4)
C16_1—H16_1	0.9500	C21_2—C26_2	1.390 (4)
N11_2—C12_2	1.341 (4)	C21_2—C27_2	1.501 (4)
N11_2—C16_2	1.344 (4)	C22_2—C23_2	1.379 (4)
C12_2—C13_2	1.358 (4)	C22_2—H22_2	0.9500
C12_2—H12_2	0.9500	C23_2—C24_2	1.382 (5)
C13_2—C14_2	1.401 (4)	C23_2—H23_2	0.9500
C13_2—H13_2	0.9500	C24_2—C25_2	1.386 (5)
C14_2—C15_2	1.391 (4)	C25_2—C26_2	1.377 (4)
C14_2—C14_3	1.477 (4)	C25_2—H25_2	0.9500
C15_2—C16_2	1.369 (4)	C26_2—H26_2	0.9500
C15_2—H15_2	0.9500	C27_2—O22_2	1.215 (3)
C16_2—H16_2	0.9500	C27_2—O21_2	1.307 (3)
N11_3—C16_3	1.330 (4)	O21_2—H21_2	0.8400
N11_3—C12_3	1.340 (4)	Br3_3—C24_3	1.898 (3)
C12_3—C13_3	1.377 (4)	C21_3—C26_3	1.394 (4)
C12_3—H12_3	0.9500	C21_3—C22_3	1.395 (4)
C13_3—C14_3	1.383 (4)	C21_3—C27_3	1.486 (4)
C13_3—H13_3	0.9500	C22_3—C23_3	1.372 (4)
C14_3—C15_3	1.400 (4)	C22_3—H22_3	0.9500
C15_3—C16_3	1.374 (4)	C23_3—C24_3	1.388 (4)
C15_3—H15_3	0.9500	C23_3—H23_3	0.9500
C16_3—H16_3	0.9500	C24_3—C25_3	1.375 (4)
Br1_1—C24_1	1.898 (3)	C25_3—C26_3	1.373 (4)
C21_1—C26_1	1.392 (4)	C25_3—H25_3	0.9500
C21_1—C22_1	1.394 (4)	C26_3—H26_3	0.9500
C21_1—C27_1	1.504 (5)	C27_3—O22_3	1.224 (3)
C22_1—C23_1	1.371 (5)	C27_3—O21_3	1.322 (3)
C22_1—H22_1	0.9500	O21_3—H21_3	0.8400
C23_1—C24_1	1.383 (4)
C16_1—N11_1—C12_1	116.4 (3)	C23_1—C24_1—C25_1	121.1 (3)
N11_1—C12_1—C13_1	123.6 (3)	C23_1—C24_1—Br1_1	119.3 (3)
N11_1—C12_1—H12_1	118.2	C25_1—C24_1—Br1_1	119.6 (3)
C13_1—C12_1—H12_1	118.2	C26_1—C25_1—C24_1	119.5 (3)
C12_1—C13_1—C14_1	120.0 (3)	C26_1—C25_1—H25_1	120.3
C12_1—C13_1—H13_1	120.0	C24_1—C25_1—H25_1	120.3
C14_1—C13_1—H13_1	120.0	C25_1—C26_1—C21_1	120.5 (3)
C15_1—C14_1—C13_1	115.7 (3)	C25_1—C26_1—H26_1	119.7
C15_1—C14_1—C14_1^i	122.9 (4)	C21_1—C26_1—H26_1	119.7
C13_1—C14_1—C14_1^i	121.4 (4)	O22_1—C27_1—O21_1	124.6 (3)
C16_1—C15_1—C14_1	119.3 (3)	O22_1—C27_1—C21_1	121.1 (3)
C16_1—C15_1—H15_1	120.4	O21_1—C27_1—C21_1	114.3 (3)
C14_1—C15_1—H15_1	120.4	C27_1—O21_1—H21_1	109.5
N11_1—C16_1—C15_1	125.1 (3)	C22_2—C21_2—C26_2	119.8 (3)
N11_1—C16_1—H16_1	117.4	C22_2—C21_2—C27_2	118.5 (3)
C15_1—C16_1—H16_1	117.4	C26_2—C21_2—C27_2	121.7 (3)
C12_2—N11_2—C16_2	117.0 (3)	C23_2—C22_2—C21_2	120.3 (3)
N11_2—C12_2—C13_2	123.6 (3)	C23_2—C22_2—H22_2	119.8
N11_2—C12_2—H12_2	118.2	C21_2—C22_2—H22_2	119.8
C13_2—C12_2—H12_2	118.2	C22_2—C23_2—C24_2	119.1 (3)
C12_2—C13_2—C14_2	119.7 (3)	C22_2—C23_2—H23_2	120.5
C12_2—C13_2—H13_2	120.1	C24_2—C23_2—H23_2	120.5
C14_2—C13_2—H13_2	120.1	C23_2—C24_2—C25_2	121.4 (3)
C15_2—C14_2—C13_2	116.6 (3)	C23_2—C24_2—Br2_2	119.2 (3)
C15_2—C14_2—C14_3	121.5 (3)	C25_2—C24_2—Br2_2	119.4 (3)
C13_2—C14_2—C14_3	121.9 (3)	C26_2—C25_2—C24_2	119.1 (3)
C16_2—C15_2—C14_2	120.1 (3)	C26_2—C25_2—H25_2	120.5
C16_2—C15_2—H15_2	119.9	C24_2—C25_2—H25_2	120.5
C14_2—C15_2—H15_2	119.9	C25_2—C26_2—C21_2	120.3 (3)
N11_2—C16_2—C15_2	122.9 (3)	C25_2—C26_2—H26_2	119.9
N11_2—C16_2—H16_2	118.6	C21_2—C26_2—H26_2	119.9
C15_2—C16_2—H16_2	118.6	O22_2—C27_2—O21_2	124.3 (3)
C16_3—N11_3—C12_3	117.0 (3)	O22_2—C27_2—C21_2	121.8 (3)
N11_3—C12_3—C13_3	123.0 (3)	O21_2—C27_2—C21_2	113.9 (2)
N11_3—C12_3—H12_3	118.5	C27_2—O21_2—H21_2	109.5
C13_3—C12_3—H12_3	118.5	C26_3—C21_3—C22_3	119.4 (3)
C12_3—C13_3—C14_3	120.3 (3)	C26_3—C21_3—C27_3	121.7 (3)
C12_3—C13_3—H13_3	119.9	C22_3—C21_3—C27_3	118.8 (3)
C14_3—C13_3—H13_3	119.9	C23_3—C22_3—C21_3	120.6 (3)
C13_3—C14_3—C15_3	116.5 (3)	C23_3—C22_3—H22_3	119.7
C13_3—C14_3—C14_2	122.2 (3)	C21_3—C22_3—H22_3	119.7
C15_3—C14_3—C14_2	121.2 (3)	C22_3—C23_3—C24_3	118.6 (3)
C16_3—C15_3—C14_3	119.4 (3)	C22_3—C23_3—H23_3	120.7
C16_3—C15_3—H15_3	120.3	C24_3—C23_3—H23_3	120.7
C14_3—C15_3—H15_3	120.3	C25_3—C24_3—C23_3	121.8 (3)
N11_3—C16_3—C15_3	123.8 (3)	C25_3—C24_3—Br3_3	119.2 (2)
N11_3—C16_3—H16_3	118.1	C23_3—C24_3—Br3_3	119.0 (2)
C15_3—C16_3—H16_3	118.1	C26_3—C25_3—C24_3	119.3 (3)
C26_1—C21_1—C22_1	119.4 (3)	C26_3—C25_3—H25_3	120.4
C26_1—C21_1—C27_1	122.5 (3)	C24_3—C25_3—H25_3	120.4
C22_1—C21_1—C27_1	118.1 (3)	C25_3—C26_3—C21_3	120.2 (3)
C23_1—C22_1—C21_1	120.2 (3)	C25_3—C26_3—H26_3	119.9
C23_1—C22_1—H22_1	119.9	C21_3—C26_3—H26_3	119.9
C21_1—C22_1—H22_1	119.9	O22_3—C27_3—O21_3	123.4 (3)
C22_1—C23_1—C24_1	119.3 (3)	O22_3—C27_3—C21_3	122.9 (3)
C22_1—C23_1—H23_1	120.3	O21_3—C27_3—C21_3	113.6 (2)
C24_1—C23_1—H23_1	120.3	C27_3—O21_3—H21_3	109.5
C16_1—N11_1—C12_1—C13_1	−0.2 (5)	C24_1—C25_1—C26_1—C21_1	−0.7 (5)
N11_1—C12_1—C13_1—C14_1	0.7 (5)	C22_1—C21_1—C26_1—C25_1	1.0 (5)
C12_1—C13_1—C14_1—C15_1	−0.8 (5)	C27_1—C21_1—C26_1—C25_1	−179.8 (3)
C12_1—C13_1—C14_1—C14_1^i	179.3 (3)	C26_1—C21_1—C27_1—O22_1	−170.5 (3)
C13_1—C14_1—C15_1—C16_1	0.5 (5)	C22_1—C21_1—C27_1—O22_1	8.6 (4)
C14_1^i—C14_1—C15_1—C16_1	−179.5 (4)	C26_1—C21_1—C27_1—O21_1	7.5 (4)
C12_1—N11_1—C16_1—C15_1	0.0 (5)	C22_1—C21_1—C27_1—O21_1	−173.3 (3)
C14_1—C15_1—C16_1—N11_1	−0.1 (6)	C26_2—C21_2—C22_2—C23_2	0.5 (4)
C16_2—N11_2—C12_2—C13_2	0.7 (4)	C27_2—C21_2—C22_2—C23_2	−178.9 (3)
N11_2—C12_2—C13_2—C14_2	−0.4 (5)	C21_2—C22_2—C23_2—C24_2	−1.1 (5)
C12_2—C13_2—C14_2—C15_2	−0.5 (4)	C22_2—C23_2—C24_2—C25_2	1.2 (5)
C12_2—C13_2—C14_2—C14_3	179.4 (3)	C22_2—C23_2—C24_2—Br2_2	−176.9 (2)
C13_2—C14_2—C15_2—C16_2	1.1 (4)	C23_2—C24_2—C25_2—C26_2	−0.6 (5)
C14_3—C14_2—C15_2—C16_2	−178.9 (3)	Br2_2—C24_2—C25_2—C26_2	177.5 (2)
C12_2—N11_2—C16_2—C15_2	0.0 (4)	C24_2—C25_2—C26_2—C21_2	−0.1 (5)
C14_2—C15_2—C16_2—N11_2	−0.9 (5)	C22_2—C21_2—C26_2—C25_2	0.1 (4)
C16_3—N11_3—C12_3—C13_3	0.2 (4)	C27_2—C21_2—C26_2—C25_2	179.5 (3)
N11_3—C12_3—C13_3—C14_3	0.6 (5)	C22_2—C21_2—C27_2—O22_2	−6.8 (4)
C12_3—C13_3—C14_3—C15_3	−0.5 (4)	C26_2—C21_2—C27_2—O22_2	173.9 (3)
C12_3—C13_3—C14_3—C14_2	178.2 (3)	C22_2—C21_2—C27_2—O21_2	172.6 (3)
C15_2—C14_2—C14_3—C13_3	−24.9 (4)	C26_2—C21_2—C27_2—O21_2	−6.7 (4)
C13_2—C14_2—C14_3—C13_3	155.1 (3)	C26_3—C21_3—C22_3—C23_3	0.5 (4)
C15_2—C14_2—C14_3—C15_3	153.7 (3)	C27_3—C21_3—C22_3—C23_3	−179.6 (3)
C13_2—C14_2—C14_3—C15_3	−26.3 (4)	C21_3—C22_3—C23_3—C24_3	0.4 (4)
C13_3—C14_3—C15_3—C16_3	−0.3 (4)	C22_3—C23_3—C24_3—C25_3	−0.4 (5)
C14_2—C14_3—C15_3—C16_3	−179.0 (3)	C22_3—C23_3—C24_3—Br3_3	−179.5 (2)
C12_3—N11_3—C16_3—C15_3	−1.0 (4)	C23_3—C24_3—C25_3—C26_3	−0.5 (5)
C14_3—C15_3—C16_3—N11_3	1.1 (5)	Br3_3—C24_3—C25_3—C26_3	178.7 (2)
C26_1—C21_1—C22_1—C23_1	−0.2 (5)	C24_3—C25_3—C26_3—C21_3	1.3 (4)
C27_1—C21_1—C22_1—C23_1	−179.4 (3)	C22_3—C21_3—C26_3—C25_3	−1.4 (4)
C21_1—C22_1—C23_1—C24_1	−0.9 (5)	C27_3—C21_3—C26_3—C25_3	178.7 (3)
C22_1—C23_1—C24_1—C25_1	1.3 (5)	C26_3—C21_3—C27_3—O22_3	172.4 (3)
C22_1—C23_1—C24_1—Br1_1	−178.6 (2)	C22_3—C21_3—C27_3—O22_3	−7.5 (4)
C23_1—C24_1—C25_1—C26_1	−0.4 (5)	C26_3—C21_3—C27_3—O21_3	−7.7 (4)
Br1_1—C24_1—C25_1—C26_1	179.4 (2)	C22_3—C21_3—C27_3—O21_3	172.4 (3)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21_1—H21_1···N11_1	0.84	1.83	2.667 (4)	179
O21_2—H21_2···N11_2	0.84	1.80	2.628 (3)	168
O21_3—H21_3···N11_3	0.84	1.85	2.652 (3)	160

(BrF4OX14) SD-1–20-10–8 (4-Br—F4-PhCH=NOH,)2 1,2-bis(4-pyridyl)ethylene

Crystal data

(C7H2BrF4NO)2(C12H10N2)	Z = 2
Mr = 726.23	F(000) = 712
Triclinic, P1	Dx = 1.846 Mg m^−3
a = 5.8370 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 12.8464 (5) Å	Cell parameters from 9332 reflections
c = 18.1146 (8) Å	θ = 2.5–68.3°
α = 103.537 (2)°	µ = 4.78 mm^−1
β = 96.861 (2)°	T = 200 K
γ = 93.060 (2)°	Plate, colourless
V = 1306.46 (10) Å^3	0.28 × 0.24 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	4377 independent reflections
Radiation source: fine-focus sealed tube	3946 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 68.2°, θmin = 2.5°
Absorption correction: multi-scan SADABS	h = −5→6
Tmin = 0.529, Tmax = 0.753	k = −15→15
16525 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 0.86	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
4377 reflections	(Δ/σ)max = 0.001
385 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.75028 (5)	0.54628 (2)	0.104058 (16)	0.04831 (13)
Br2	0.19535 (5)	0.32794 (2)	0.077187 (15)	0.05174 (13)
N11	−0.4211 (4)	1.02290 (16)	0.20929 (12)	0.0406 (5)
C12	−0.3903 (4)	0.9554 (2)	0.14305 (14)	0.0392 (5)
H12	−0.2540	0.9181	0.1417	0.047*
C13	−0.5456 (4)	0.93735 (18)	0.07698 (14)	0.0359 (5)
H13	−0.5160	0.8881	0.0318	0.043*
C14	−0.7462 (4)	0.99140 (17)	0.07641 (13)	0.0326 (5)
C17	−0.9088 (4)	0.97285 (18)	0.00585 (13)	0.0345 (5)
H17	−0.8812	0.9164	−0.0357	0.041*
C15	−0.7782 (4)	1.06249 (18)	0.14535 (13)	0.0368 (5)
H15	−0.9115	1.1018	0.1481	0.044*
C16	−0.6162 (4)	1.07467 (18)	0.20842 (13)	0.0375 (5)
H16	−0.6426	1.1226	0.2546	0.045*
N21	1.5188 (4)	0.27315 (15)	0.46759 (11)	0.0394 (5)
C22	1.4739 (4)	0.16716 (19)	0.43733 (13)	0.0385 (5)
H22	1.3302	0.1423	0.4058	0.046*
C23	1.6256 (4)	0.09278 (18)	0.44970 (13)	0.0372 (5)
H23	1.5860	0.0186	0.4269	0.045*
C24	1.8374 (4)	0.12641 (17)	0.49578 (12)	0.0318 (5)
C27	2.0087 (4)	0.05321 (17)	0.51359 (12)	0.0335 (5)
H27	2.1445	0.0845	0.5476	0.040*
C25	1.8837 (4)	0.23595 (18)	0.52677 (13)	0.0364 (5)
H25	2.0259	0.2630	0.5585	0.044*
C26	1.7225 (4)	0.30590 (18)	0.51140 (14)	0.0391 (5)
H26	1.7584	0.3807	0.5330	0.047*
C31	0.3041 (4)	0.79216 (17)	0.24647 (13)	0.0327 (5)
C32	0.2459 (4)	0.75038 (17)	0.16734 (13)	0.0341 (5)
F32	0.0609 (3)	0.78066 (11)	0.12896 (8)	0.0434 (3)
C33	0.3779 (4)	0.67905 (19)	0.12624 (13)	0.0383 (5)
F33	0.3118 (3)	0.64353 (13)	0.05016 (8)	0.0524 (4)
C34	0.5731 (4)	0.64462 (18)	0.16085 (14)	0.0380 (5)
C35	0.6335 (4)	0.68451 (19)	0.23865 (15)	0.0381 (5)
F35	0.8225 (3)	0.65418 (12)	0.27547 (9)	0.0477 (4)
C36	0.4991 (4)	0.75520 (17)	0.27997 (13)	0.0352 (5)
F36	0.5656 (3)	0.79102 (12)	0.35611 (8)	0.0470 (4)
C37	0.1788 (4)	0.8733 (2)	0.29382 (13)	0.0387 (5)
H37A	0.2282	0.8969	0.3474	0.046*
N37	0.0060 (4)	0.91189 (16)	0.26405 (11)	0.0390 (5)
O37	−0.0795 (4)	0.99141 (16)	0.31670 (10)	0.0512 (5)
H37	−0.203 (7)	1.008 (3)	0.286 (2)	0.077*
C41	0.7318 (4)	0.39586 (16)	0.30186 (12)	0.0304 (5)
C42	0.7586 (4)	0.31744 (17)	0.23631 (13)	0.0329 (5)
F42	0.9425 (3)	0.25940 (11)	0.23486 (8)	0.0465 (4)
C43	0.6010 (4)	0.29816 (18)	0.17110 (13)	0.0355 (5)
F43	0.6400 (3)	0.22264 (12)	0.10957 (8)	0.0489 (4)
C44	0.4055 (4)	0.35337 (19)	0.16742 (13)	0.0371 (5)
C45	0.3753 (4)	0.43112 (19)	0.23210 (14)	0.0359 (5)
F45	0.1903 (3)	0.48872 (13)	0.23144 (9)	0.0484 (4)
C46	0.5364 (4)	0.45122 (17)	0.29692 (13)	0.0327 (5)
F46	0.5000 (3)	0.53033 (11)	0.35667 (8)	0.0441 (3)
C47	0.8949 (4)	0.42297 (17)	0.37339 (13)	0.0342 (5)
H47A	0.8665	0.4802	0.4142	0.041*
N47	1.0732 (3)	0.37169 (14)	0.38198 (11)	0.0352 (4)
O47	1.1966 (3)	0.41254 (13)	0.45447 (9)	0.0409 (4)
H47	1.299 (6)	0.371 (3)	0.455 (2)	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0494 (2)	0.03977 (17)	0.0547 (2)	0.00688 (13)	0.01382 (14)	0.00525 (13)
Br2	0.0469 (2)	0.0637 (2)	0.03979 (18)	−0.00214 (14)	−0.00760 (13)	0.01121 (14)
N11	0.0400 (11)	0.0450 (11)	0.0369 (10)	0.0031 (9)	0.0011 (9)	0.0123 (8)
C12	0.0364 (13)	0.0448 (12)	0.0373 (12)	0.0087 (10)	0.0030 (10)	0.0115 (10)
C13	0.0347 (13)	0.0369 (11)	0.0359 (12)	0.0074 (9)	0.0054 (10)	0.0069 (9)
C14	0.0332 (12)	0.0319 (10)	0.0327 (11)	0.0014 (9)	0.0046 (9)	0.0080 (9)
C17	0.0352 (11)	0.0338 (10)	0.0318 (11)	0.0054 (8)	0.0048 (9)	0.0018 (8)
C15	0.0377 (13)	0.0355 (11)	0.0377 (12)	0.0093 (9)	0.0077 (10)	0.0072 (9)
C16	0.0462 (14)	0.0351 (11)	0.0282 (11)	0.0035 (10)	0.0047 (10)	0.0019 (9)
N21	0.0441 (12)	0.0380 (10)	0.0381 (10)	0.0165 (9)	0.0054 (9)	0.0105 (8)
C22	0.0342 (12)	0.0433 (12)	0.0358 (12)	0.0114 (10)	−0.0019 (9)	0.0068 (9)
C23	0.0393 (13)	0.0331 (10)	0.0346 (11)	0.0101 (9)	−0.0014 (9)	0.0007 (9)
C24	0.0339 (12)	0.0343 (10)	0.0268 (10)	0.0089 (9)	0.0024 (9)	0.0063 (8)
C27	0.0325 (12)	0.0338 (10)	0.0309 (11)	0.0076 (9)	−0.0027 (9)	0.0041 (8)
C25	0.0357 (13)	0.0324 (11)	0.0381 (12)	0.0062 (9)	−0.0023 (10)	0.0051 (9)
C26	0.0430 (14)	0.0303 (10)	0.0423 (13)	0.0105 (9)	0.0018 (10)	0.0058 (9)
C31	0.0344 (12)	0.0318 (10)	0.0301 (11)	−0.0014 (9)	−0.0002 (9)	0.0070 (8)
C32	0.0332 (12)	0.0335 (10)	0.0338 (11)	−0.0004 (9)	−0.0031 (9)	0.0090 (9)
F32	0.0454 (8)	0.0472 (7)	0.0333 (7)	0.0089 (6)	−0.0079 (6)	0.0063 (6)
C33	0.0436 (14)	0.0378 (11)	0.0303 (11)	−0.0024 (10)	−0.0004 (10)	0.0059 (9)
F33	0.0624 (10)	0.0569 (9)	0.0301 (7)	0.0113 (7)	−0.0013 (7)	−0.0024 (6)
C34	0.0387 (13)	0.0314 (10)	0.0415 (13)	−0.0023 (9)	0.0056 (10)	0.0048 (9)
C35	0.0329 (13)	0.0353 (11)	0.0453 (13)	0.0000 (9)	−0.0037 (10)	0.0134 (10)
F35	0.0368 (8)	0.0480 (8)	0.0550 (9)	0.0089 (6)	−0.0061 (7)	0.0112 (7)
C36	0.0358 (12)	0.0323 (10)	0.0328 (11)	−0.0032 (9)	−0.0045 (9)	0.0043 (9)
F36	0.0498 (9)	0.0517 (8)	0.0323 (7)	0.0072 (7)	−0.0110 (6)	0.0033 (6)
C37	0.0417 (14)	0.0434 (12)	0.0287 (11)	0.0036 (11)	−0.0005 (10)	0.0066 (9)
N37	0.0416 (12)	0.0434 (10)	0.0308 (10)	0.0100 (9)	0.0029 (8)	0.0062 (8)
O37	0.0592 (12)	0.0618 (11)	0.0317 (9)	0.0289 (10)	0.0038 (8)	0.0052 (8)
C41	0.0299 (12)	0.0277 (10)	0.0326 (11)	0.0041 (8)	0.0048 (9)	0.0046 (8)
C42	0.0299 (12)	0.0306 (10)	0.0370 (12)	0.0069 (9)	0.0071 (9)	0.0035 (9)
F42	0.0417 (8)	0.0441 (8)	0.0467 (8)	0.0184 (6)	0.0052 (6)	−0.0058 (6)
C43	0.0382 (13)	0.0338 (11)	0.0315 (11)	0.0013 (9)	0.0074 (9)	0.0011 (9)
F43	0.0502 (9)	0.0504 (8)	0.0360 (8)	0.0048 (7)	0.0067 (6)	−0.0103 (6)
C44	0.0354 (13)	0.0398 (12)	0.0345 (12)	−0.0031 (9)	0.0016 (9)	0.0087 (9)
C45	0.0291 (12)	0.0373 (11)	0.0428 (13)	0.0072 (9)	0.0052 (10)	0.0118 (10)
F45	0.0360 (8)	0.0533 (8)	0.0554 (9)	0.0165 (7)	0.0003 (7)	0.0123 (7)
C46	0.0348 (12)	0.0293 (10)	0.0332 (11)	0.0064 (9)	0.0077 (9)	0.0040 (8)
F46	0.0445 (8)	0.0432 (7)	0.0404 (7)	0.0174 (6)	0.0073 (6)	−0.0018 (6)
C47	0.0375 (13)	0.0284 (10)	0.0342 (11)	0.0084 (9)	0.0028 (9)	0.0027 (8)
N47	0.0373 (11)	0.0323 (9)	0.0343 (10)	0.0092 (8)	0.0009 (8)	0.0053 (8)
O47	0.0422 (10)	0.0372 (8)	0.0385 (9)	0.0161 (7)	−0.0056 (7)	0.0025 (7)

Geometric parameters (Å, º)

Br1—C34	1.873 (2)	C31—C32	1.401 (3)
Br2—C44	1.874 (2)	C31—C37	1.473 (3)
N11—C12	1.344 (3)	C32—F32	1.339 (3)
N11—C16	1.350 (3)	C32—C33	1.371 (4)
C12—C13	1.377 (3)	C33—F33	1.348 (3)
C12—H12	0.9500	C33—C34	1.379 (4)
C13—C14	1.393 (3)	C34—C35	1.377 (4)
C13—H13	0.9500	C35—F35	1.344 (3)
C14—C15	1.403 (3)	C35—C36	1.378 (4)
C14—C17	1.461 (3)	C36—F36	1.349 (3)
C17—C17^i	1.326 (5)	C37—N37	1.266 (3)
C17—H17	0.9500	C37—H37A	0.9500
C15—C16	1.366 (3)	N37—O37	1.384 (3)
C15—H15	0.9500	O37—H37	0.92 (4)
C16—H16	0.9500	C41—C46	1.381 (3)
N21—C26	1.337 (3)	C41—C42	1.397 (3)
N21—C22	1.342 (3)	C41—C47	1.471 (3)
C22—C23	1.375 (3)	C42—F42	1.338 (3)
C22—H22	0.9500	C42—C43	1.372 (3)
C23—C24	1.393 (3)	C43—F43	1.347 (3)
C23—H23	0.9500	C43—C44	1.379 (4)
C24—C25	1.386 (3)	C44—C45	1.386 (3)
C24—C27	1.467 (3)	C45—F45	1.342 (3)
C27—C27^ii	1.334 (4)	C45—C46	1.377 (3)
C27—C27^iii	11.720 (5)	C46—F46	1.346 (3)
C27—H27	0.9500	C47—N47	1.274 (3)
C25—C26	1.384 (3)	C47—H47A	0.9500
C25—H25	0.9500	N47—O47	1.389 (2)
C26—H26	0.9500	O47—H47	0.82 (4)
C31—C36	1.385 (3)
C12—N11—C16	116.2 (2)	F32—C32—C33	117.7 (2)
N11—C12—C13	123.5 (2)	F32—C32—C31	120.8 (2)
N11—C12—H12	118.2	C33—C32—C31	121.5 (2)
C13—C12—H12	118.2	F33—C33—C32	117.9 (2)
C12—C13—C14	120.0 (2)	F33—C33—C34	120.5 (2)
C12—C13—H13	120.0	C32—C33—C34	121.6 (2)
C14—C13—H13	120.0	C35—C34—C33	117.9 (2)
C13—C14—C15	116.7 (2)	C35—C34—Br1	121.0 (2)
C13—C14—C17	119.6 (2)	C33—C34—Br1	121.14 (19)
C15—C14—C17	123.7 (2)	F35—C35—C34	120.5 (2)
C17^i—C17—C14	126.3 (3)	F35—C35—C36	119.1 (2)
C17^i—C17—H17	116.9	C34—C35—C36	120.4 (2)
C14—C17—H17	116.9	F36—C36—C35	117.8 (2)
C16—C15—C14	119.5 (2)	F36—C36—C31	119.3 (2)
C16—C15—H15	120.3	C35—C36—C31	122.9 (2)
C14—C15—H15	120.3	N37—C37—C31	120.8 (2)
N11—C16—C15	124.1 (2)	N37—C37—H37A	119.6
N11—C16—H16	117.9	C31—C37—H37A	119.6
C15—C16—H16	117.9	C37—N37—O37	112.31 (19)
C26—N21—C22	117.1 (2)	N37—O37—H37	100 (2)
N21—C22—C23	123.2 (2)	C46—C41—C42	115.8 (2)
N21—C22—H22	118.4	C46—C41—C47	119.18 (19)
C23—C22—H22	118.4	C42—C41—C47	125.0 (2)
C22—C23—C24	119.9 (2)	F42—C42—C43	117.69 (19)
C22—C23—H23	120.0	F42—C42—C41	120.7 (2)
C24—C23—H23	120.0	C43—C42—C41	121.6 (2)
C25—C24—C23	116.8 (2)	F43—C43—C42	118.4 (2)
C25—C24—C27	119.3 (2)	F43—C43—C44	119.8 (2)
C23—C24—C27	124.0 (2)	C42—C43—C44	121.8 (2)
C27^ii—C27—C24	126.0 (3)	C43—C44—C45	117.4 (2)
C27^ii—C27—C27^iii	84.7 (2)	C43—C44—Br2	121.17 (18)
C24—C27—C27^iii	51.70 (12)	C45—C44—Br2	121.43 (19)
C27^ii—C27—H27	117.0	F45—C45—C46	119.5 (2)
C24—C27—H27	117.0	F45—C45—C44	120.0 (2)
C27^iii—C27—H27	141.5	C46—C45—C44	120.5 (2)
C26—C25—C24	120.0 (2)	F46—C46—C45	117.3 (2)
C26—C25—H25	120.0	F46—C46—C41	119.8 (2)
C24—C25—H25	120.0	C45—C46—C41	122.9 (2)
N21—C26—C25	123.0 (2)	N47—C47—C41	121.70 (19)
N21—C26—H26	118.5	N47—C47—H47A	119.2
C25—C26—H26	118.5	C41—C47—H47A	119.2
C36—C31—C32	115.7 (2)	C47—N47—O47	110.20 (18)
C36—C31—C37	119.5 (2)	N47—O47—H47	102 (2)
C32—C31—C37	124.7 (2)
C16—N11—C12—C13	−0.4 (3)	F35—C35—C36—F36	0.2 (3)
N11—C12—C13—C14	0.7 (4)	C34—C35—C36—F36	179.5 (2)
C12—C13—C14—C15	−0.3 (3)	F35—C35—C36—C31	178.8 (2)
C12—C13—C14—C17	179.2 (2)	C34—C35—C36—C31	−2.0 (4)
C13—C14—C17—C17^i	−171.6 (3)	C32—C31—C36—F36	−179.51 (19)
C15—C14—C17—C17^i	7.9 (4)	C37—C31—C36—F36	2.6 (3)
C13—C14—C15—C16	−0.4 (3)	C32—C31—C36—C35	2.0 (3)
C17—C14—C15—C16	−179.9 (2)	C37—C31—C36—C35	−175.9 (2)
C12—N11—C16—C15	−0.3 (4)	C36—C31—C37—N37	176.9 (2)
C14—C15—C16—N11	0.7 (4)	C32—C31—C37—N37	−0.7 (4)
C26—N21—C22—C23	0.3 (4)	C31—C37—N37—O37	−176.3 (2)
N21—C22—C23—C24	0.2 (4)	C46—C41—C42—F42	179.7 (2)
C22—C23—C24—C25	−0.4 (3)	C47—C41—C42—F42	0.3 (3)
C22—C23—C24—C27	178.8 (2)	C46—C41—C42—C43	0.8 (3)
C25—C24—C27—C27^ii	−178.0 (3)	C47—C41—C42—C43	−178.7 (2)
C23—C24—C27—C27^ii	2.9 (5)	F42—C42—C43—F43	−0.2 (3)
C25—C24—C27—C27^iii	137.8 (2)	C41—C42—C43—F43	178.8 (2)
C23—C24—C27—C27^iii	−41.29 (18)	F42—C42—C43—C44	179.5 (2)
C23—C24—C25—C26	0.1 (3)	C41—C42—C43—C44	−1.5 (4)
C27—C24—C25—C26	−179.1 (2)	F43—C43—C44—C45	−179.2 (2)
C22—N21—C26—C25	−0.6 (4)	C42—C43—C44—C45	1.1 (3)
C24—C25—C26—N21	0.4 (4)	F43—C43—C44—Br2	−1.6 (3)
C36—C31—C32—F32	−179.9 (2)	C42—C43—C44—Br2	178.72 (17)
C37—C31—C32—F32	−2.1 (3)	C43—C44—C45—F45	178.9 (2)
C36—C31—C32—C33	−1.2 (3)	Br2—C44—C45—F45	1.3 (3)
C37—C31—C32—C33	176.5 (2)	C43—C44—C45—C46	0.0 (3)
F32—C32—C33—F33	−0.5 (3)	Br2—C44—C45—C46	−177.61 (17)
C31—C32—C33—F33	−179.2 (2)	F45—C45—C46—F46	−1.1 (3)
F32—C32—C33—C34	179.1 (2)	C44—C45—C46—F46	177.8 (2)
C31—C32—C33—C34	0.4 (4)	F45—C45—C46—C41	−179.6 (2)
F33—C33—C34—C35	179.3 (2)	C44—C45—C46—C41	−0.7 (4)
C32—C33—C34—C35	−0.3 (4)	C42—C41—C46—F46	−178.1 (2)
F33—C33—C34—Br1	−0.9 (3)	C47—C41—C46—F46	1.4 (3)
C32—C33—C34—Br1	179.50 (17)	C42—C41—C46—C45	0.4 (3)
C33—C34—C35—F35	−179.7 (2)	C47—C41—C46—C45	179.8 (2)
Br1—C34—C35—F35	0.5 (3)	C46—C41—C47—N47	177.3 (2)
C33—C34—C35—C36	1.0 (3)	C42—C41—C47—N47	−3.2 (4)
Br1—C34—C35—C36	−178.74 (17)	C41—C47—N47—O47	−179.61 (19)

Symmetry codes: (i) −x−2, −y+2, −z; (ii) −x+4, −y, −z+1; (iii) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O37—H37···N11	0.92 (4)	1.82 (4)	2.730 (3)	168 (4)
O47—H47···N21	0.82 (4)	1.88 (4)	2.693 (2)	173 (3)

(BrF4OH12) SD-1–20-12–6 (4-Br—F4-PhOH)2, 4,4-bipyridyl

Crystal data

(C6HBrF4O)2(C10H8N2)	F(000) = 628
Mr = 646.14	Dx = 2.027 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.6342 (15) Å	Cell parameters from 4618 reflections
b = 5.8333 (6) Å	θ = 3.0–29.6°
c = 13.3118 (14) Å	µ = 3.93 mm^−1
β = 90.944 (7)°	T = 120 K
V = 1058.58 (19) Å^3	Prism, colourless
Z = 2	0.30 × 0.14 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	3352 independent reflections
Radiation source: fine-focus sealed tube	2304 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 31.5°, θmin = 3.0°
Absorption correction: multi-scan SADABS	h = −19→19
Tmin = 0.390, Tmax = 0.799	k = −8→8
11348 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.055P)^2] where P = (Fo^2 + 2Fc^2)/3
3352 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −1.12 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.12749 (15)	0.4027 (3)	0.23101 (15)	0.0189 (4)
C12	0.0640 (2)	0.2494 (4)	0.1939 (2)	0.0194 (5)
H12	0.0536	0.1121	0.2307	0.023*
C13	0.0123 (2)	0.2808 (4)	0.10399 (19)	0.0193 (5)
H13	−0.0324	0.1671	0.0805	0.023*
C14	0.02661 (18)	0.4799 (4)	0.04866 (17)	0.0167 (5)
C15	0.09434 (19)	0.6371 (4)	0.08707 (18)	0.0183 (5)
H15	0.1079	0.7738	0.0511	0.022*
C16	0.14178 (19)	0.5942 (4)	0.17746 (18)	0.0203 (5)
H16	0.1866	0.7054	0.2029	0.024*
C21	0.24544 (19)	0.2443 (4)	0.46171 (19)	0.0179 (5)
O21	0.18081 (13)	0.3928 (3)	0.42195 (13)	0.0218 (4)
H21	0.172 (4)	0.381 (8)	0.352 (4)	0.112 (17)*
C22	0.2834 (2)	0.2865 (4)	0.55779 (19)	0.0195 (5)
F22	0.25441 (11)	0.4756 (2)	0.60638 (10)	0.0247 (4)
C23	0.34722 (19)	0.1357 (5)	0.60452 (19)	0.0215 (5)
F23	0.37876 (13)	0.1862 (3)	0.69834 (12)	0.0311 (4)
C24	0.37820 (18)	−0.0614 (4)	0.55799 (19)	0.0210 (5)
Br1	0.46623 (2)	−0.26131 (5)	0.62176 (2)	0.03233 (12)
C25	0.3409 (2)	−0.1049 (4)	0.4625 (2)	0.0224 (6)
F25	0.36867 (13)	−0.2928 (3)	0.41208 (13)	0.0324 (4)
C26	0.27619 (19)	0.0434 (4)	0.41656 (17)	0.0192 (5)
F26	0.23985 (11)	−0.0072 (3)	0.32383 (10)	0.0282 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0204 (11)	0.0204 (10)	0.0159 (10)	0.0003 (9)	0.0013 (9)	0.0010 (8)
C12	0.0213 (13)	0.0196 (13)	0.0174 (11)	−0.0007 (10)	0.0025 (10)	0.0041 (9)
C13	0.0225 (13)	0.0196 (13)	0.0158 (11)	−0.0020 (11)	−0.0007 (10)	0.0009 (9)
C14	0.0188 (12)	0.0186 (11)	0.0127 (10)	0.0013 (10)	0.0014 (9)	−0.0013 (9)
C15	0.0222 (13)	0.0165 (12)	0.0162 (11)	−0.0021 (11)	−0.0011 (10)	0.0020 (9)
C16	0.0254 (14)	0.0183 (12)	0.0171 (12)	−0.0023 (11)	−0.0016 (10)	−0.0010 (9)
C21	0.0179 (12)	0.0209 (13)	0.0149 (11)	−0.0026 (10)	0.0000 (9)	0.0024 (9)
O21	0.0261 (10)	0.0234 (9)	0.0158 (8)	0.0058 (8)	−0.0013 (8)	0.0015 (7)
C22	0.0215 (13)	0.0210 (13)	0.0160 (11)	0.0000 (11)	0.0025 (10)	−0.0019 (9)
F22	0.0315 (9)	0.0247 (8)	0.0179 (7)	0.0030 (7)	−0.0012 (7)	−0.0046 (6)
C23	0.0207 (13)	0.0282 (14)	0.0156 (11)	−0.0059 (12)	−0.0023 (10)	0.0044 (10)
F23	0.0361 (10)	0.0375 (9)	0.0192 (8)	−0.0014 (8)	−0.0122 (7)	0.0013 (7)
C24	0.0178 (12)	0.0207 (12)	0.0245 (13)	−0.0012 (11)	−0.0014 (11)	0.0064 (10)
Br1	0.02364 (18)	0.02969 (19)	0.0434 (2)	0.00230 (12)	−0.00643 (14)	0.01450 (12)
C25	0.0227 (13)	0.0196 (12)	0.0251 (13)	0.0023 (11)	0.0030 (11)	−0.0012 (10)
F25	0.0387 (11)	0.0226 (8)	0.0361 (10)	0.0073 (8)	0.0029 (9)	−0.0041 (7)
C26	0.0221 (13)	0.0215 (12)	0.0139 (11)	−0.0049 (11)	0.0008 (10)	−0.0008 (9)
F26	0.0403 (10)	0.0277 (8)	0.0164 (7)	0.0034 (8)	−0.0060 (7)	−0.0045 (6)

Geometric parameters (Å, º)

N11—C12	1.334 (3)	C21—C26	1.385 (3)
N11—C16	1.341 (3)	C21—C22	1.394 (3)
C12—C13	1.391 (4)	O21—H21	0.94 (5)
C12—H12	0.9500	C22—F22	1.341 (3)
C13—C14	1.391 (3)	C22—C23	1.378 (4)
C13—H13	0.9500	C23—F23	1.347 (3)
C14—C15	1.393 (3)	C23—C24	1.376 (4)
C14—C14^i	1.493 (4)	C24—C25	1.385 (4)
C15—C16	1.380 (3)	C24—Br1	1.867 (2)
C15—H15	0.9500	C25—F25	1.343 (3)
C16—H16	0.9500	C25—C26	1.372 (3)
C21—O21	1.338 (3)	C26—F26	1.355 (3)
C12—N11—C16	117.5 (2)	C26—C21—C22	115.9 (2)
N11—C12—C13	123.1 (2)	C21—O21—H21	115 (3)
N11—C12—H12	118.4	F22—C22—C23	119.7 (2)
C13—C12—H12	118.4	F22—C22—C21	118.7 (2)
C14—C13—C12	119.5 (2)	C23—C22—C21	121.6 (2)
C14—C13—H13	120.2	F23—C23—C24	120.3 (2)
C12—C13—H13	120.2	F23—C23—C22	117.9 (2)
C13—C14—C15	117.0 (2)	C24—C23—C22	121.8 (2)
C13—C14—C14^i	121.4 (3)	C23—C24—C25	117.1 (2)
C15—C14—C14^i	121.7 (3)	C23—C24—Br1	121.13 (19)
C16—C15—C14	120.0 (2)	C25—C24—Br1	121.8 (2)
C16—C15—H15	120.0	F25—C25—C26	118.5 (2)
C14—C15—H15	120.0	F25—C25—C24	120.4 (2)
N11—C16—C15	123.0 (2)	C26—C25—C24	121.2 (2)
N11—C16—H16	118.5	F26—C26—C25	119.4 (2)
C15—C16—H16	118.5	F26—C26—C21	118.1 (2)
O21—C21—C26	125.3 (2)	C25—C26—C21	122.5 (2)
O21—C21—C22	118.7 (2)
C16—N11—C12—C13	−0.6 (4)	F23—C23—C24—C25	178.5 (2)
N11—C12—C13—C14	0.2 (4)	C22—C23—C24—C25	−1.3 (4)
C12—C13—C14—C15	0.9 (4)	F23—C23—C24—Br1	−1.2 (4)
C12—C13—C14—C14^i	179.5 (3)	C22—C23—C24—Br1	179.0 (2)
C13—C14—C15—C16	−1.7 (4)	C23—C24—C25—F25	179.3 (2)
C14^i—C14—C15—C16	179.8 (3)	Br1—C24—C25—F25	−1.1 (4)
C12—N11—C16—C15	−0.2 (4)	C23—C24—C25—C26	0.3 (4)
C14—C15—C16—N11	1.4 (4)	Br1—C24—C25—C26	179.97 (19)
O21—C21—C22—F22	−0.6 (4)	F25—C25—C26—F26	2.2 (4)
C26—C21—C22—F22	−178.4 (2)	C24—C25—C26—F26	−178.8 (2)
O21—C21—C22—C23	177.4 (2)	F25—C25—C26—C21	−178.3 (2)
C26—C21—C22—C23	−0.3 (4)	C24—C25—C26—C21	0.7 (4)
F22—C22—C23—F23	−0.4 (4)	O21—C21—C26—F26	1.2 (4)
C21—C22—C23—F23	−178.4 (2)	C22—C21—C26—F26	178.8 (2)
F22—C22—C23—C24	179.4 (2)	O21—C21—C26—C25	−178.2 (2)
C21—C22—C23—C24	1.3 (4)	C22—C21—C26—C25	−0.7 (4)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21···N11	0.94 (5)	1.72 (5)	2.633 (3)	164 (5)

(BrF4OH11) SD-1–20-12–5, 4-Br—F4-PhOH, 1,2-bis(4-pyridyl)ethane

Crystal data

(C6HBrF4O)2(C12H12N2)	F(000) = 1320
Mr = 674.19	Dx = 1.885 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.9125 (16) Å	Cell parameters from 4226 reflections
b = 4.6925 (3) Å	θ = 2.3–32.4°
c = 20.0909 (12) Å	µ = 3.50 mm^−1
β = 103.464 (3)°	T = 120 K
V = 2375.8 (3) Å^3	Prism, colourless
Z = 4	0.30 × 0.24 × 0.20 mm

Data collection

Bruker APEX-II CCD diffractometer	4064 independent reflections
Radiation source: fine-focus sealed tube	3044 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 32.6°, θmin = 2.1°
Absorption correction: multi-scan SADABS	h = −37→38
Tmin = 0.420, Tmax = 0.541	k = −7→4
11464 measured reflections	l = −26→30

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.060P)^2] where P = (Fo^2 + 2Fc^2)/3
4064 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.95 e Å^−3
0 restraints	Δρmin = −0.97 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	−0.024830 (8)	1.28914 (6)	0.063810 (12)	0.02760 (9)
N11	0.16779 (8)	0.2178 (4)	0.30189 (10)	0.0251 (4)
C12	0.21757 (8)	0.1194 (6)	0.31417 (12)	0.0261 (5)
H12	0.2395	0.1757	0.2846	0.031*
C13	0.23829 (9)	−0.0591 (6)	0.36761 (12)	0.0270 (5)
H13	0.2738	−0.1245	0.3744	0.032*
C14	0.20734 (8)	−0.1444 (5)	0.41189 (11)	0.0238 (4)
C15	0.15549 (9)	−0.0415 (6)	0.39870 (13)	0.0309 (5)
H15	0.1327	−0.0938	0.4274	0.037*
C16	0.13768 (9)	0.1363 (6)	0.34377 (13)	0.0306 (5)
H16	0.1022	0.2041	0.3353	0.037*
C17	0.22955 (9)	−0.3300 (5)	0.47264 (12)	0.0262 (5)
H17A	0.2465	−0.4994	0.4575	0.031*
H17B	0.2003	−0.3968	0.4927	0.031*
C21	0.11859 (8)	0.7168 (5)	0.17233 (11)	0.0217 (4)
O21	0.15971 (6)	0.5547 (4)	0.20005 (9)	0.0277 (4)
H21	0.1541 (11)	0.455 (7)	0.2344 (15)	0.033*
C22	0.12267 (8)	0.9117 (5)	0.12212 (12)	0.0241 (4)
F22	0.16889 (5)	0.9300 (4)	0.10234 (8)	0.0337 (3)
C23	0.08128 (8)	1.0840 (5)	0.09105 (11)	0.0232 (4)
F23	0.08858 (6)	1.2668 (3)	0.04240 (8)	0.0311 (3)
C24	0.03295 (8)	1.0692 (5)	0.10859 (11)	0.0226 (4)
C25	0.02791 (8)	0.8774 (5)	0.15865 (11)	0.0223 (4)
F25	−0.01835 (5)	0.8531 (4)	0.17655 (7)	0.0302 (3)
C26	0.06948 (8)	0.7066 (5)	0.18980 (11)	0.0216 (4)
F26	0.06272 (5)	0.5159 (3)	0.23689 (7)	0.0291 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02340 (13)	0.03170 (15)	0.02690 (14)	0.00363 (9)	0.00422 (9)	0.00545 (9)
N11	0.0209 (8)	0.0328 (11)	0.0214 (9)	0.0000 (7)	0.0050 (7)	0.0029 (8)
C12	0.0228 (9)	0.0308 (13)	0.0265 (11)	0.0026 (9)	0.0095 (8)	0.0034 (9)
C13	0.0223 (9)	0.0323 (13)	0.0270 (11)	0.0040 (9)	0.0072 (8)	0.0034 (10)
C14	0.0220 (9)	0.0271 (12)	0.0219 (10)	−0.0011 (8)	0.0043 (8)	0.0017 (9)
C15	0.0219 (9)	0.0419 (15)	0.0306 (12)	−0.0003 (10)	0.0099 (8)	0.0099 (11)
C16	0.0182 (9)	0.0438 (15)	0.0309 (12)	0.0035 (10)	0.0078 (8)	0.0105 (11)
C17	0.0260 (10)	0.0284 (14)	0.0238 (11)	0.0007 (9)	0.0052 (8)	0.0052 (9)
C21	0.0192 (9)	0.0275 (12)	0.0181 (10)	0.0001 (8)	0.0036 (7)	−0.0006 (8)
O21	0.0206 (7)	0.0357 (10)	0.0286 (8)	0.0060 (7)	0.0090 (6)	0.0085 (7)
C22	0.0187 (9)	0.0276 (13)	0.0269 (11)	−0.0026 (8)	0.0075 (8)	0.0007 (9)
F22	0.0218 (6)	0.0423 (10)	0.0411 (8)	0.0004 (6)	0.0154 (6)	0.0122 (7)
C23	0.0253 (9)	0.0241 (12)	0.0209 (10)	−0.0043 (8)	0.0069 (8)	0.0022 (8)
F23	0.0294 (7)	0.0327 (8)	0.0335 (8)	0.0001 (6)	0.0117 (6)	0.0134 (6)
C24	0.0215 (9)	0.0240 (12)	0.0216 (10)	0.0010 (8)	0.0032 (8)	0.0007 (8)
C25	0.0200 (9)	0.0287 (12)	0.0198 (9)	0.0007 (8)	0.0076 (7)	−0.0006 (9)
F25	0.0207 (6)	0.0415 (9)	0.0318 (7)	0.0062 (6)	0.0130 (5)	0.0089 (7)
C26	0.0216 (9)	0.0261 (11)	0.0183 (9)	−0.0006 (8)	0.0068 (8)	0.0020 (8)
F26	0.0277 (6)	0.0361 (9)	0.0267 (7)	0.0062 (6)	0.0130 (5)	0.0114 (6)

Geometric parameters (Å, º)

Br1—C24	1.868 (2)	C17—H17B	0.9900
N11—C16	1.330 (3)	C21—O21	1.322 (3)
N11—C12	1.338 (3)	C21—C22	1.384 (3)
C12—C13	1.369 (3)	C21—C26	1.397 (3)
C12—H12	0.9500	O21—H21	0.87 (3)
C13—C14	1.388 (3)	C22—F22	1.350 (2)
C13—H13	0.9500	C22—C23	1.372 (3)
C14—C15	1.394 (3)	C23—F23	1.346 (3)
C14—C17	1.501 (3)	C23—C24	1.379 (3)
C15—C16	1.375 (3)	C24—C25	1.378 (3)
C15—H15	0.9500	C25—F25	1.334 (2)
C16—H16	0.9500	C25—C26	1.371 (3)
C17—C17^i	1.534 (5)	C26—F26	1.343 (3)
C17—H17A	0.9900
C16—N11—C12	117.8 (2)	H17A—C17—H17B	107.9
N11—C12—C13	122.8 (2)	O21—C21—C22	119.8 (2)
N11—C12—H12	118.6	O21—C21—C26	124.5 (2)
C13—C12—H12	118.6	C22—C21—C26	115.8 (2)
C12—C13—C14	120.0 (2)	C21—O21—H21	112.0 (19)
C12—C13—H13	120.0	F22—C22—C23	118.8 (2)
C14—C13—H13	120.0	F22—C22—C21	118.7 (2)
C13—C14—C15	117.0 (2)	C23—C22—C21	122.5 (2)
C13—C14—C17	121.3 (2)	F23—C23—C22	118.61 (19)
C15—C14—C17	121.7 (2)	F23—C23—C24	120.5 (2)
C16—C15—C14	119.4 (2)	C22—C23—C24	120.9 (2)
C16—C15—H15	120.3	C25—C24—C23	117.7 (2)
C14—C15—H15	120.3	C25—C24—Br1	120.71 (16)
N11—C16—C15	123.1 (2)	C23—C24—Br1	121.50 (17)
N11—C16—H16	118.5	F25—C25—C26	119.1 (2)
C15—C16—H16	118.5	F25—C25—C24	119.7 (2)
C14—C17—C17^i	111.7 (3)	C26—C25—C24	121.12 (19)
C14—C17—H17A	109.3	F26—C26—C25	119.56 (19)
C17^i—C17—H17A	109.3	F26—C26—C21	118.4 (2)
C14—C17—H17B	109.3	C25—C26—C21	122.0 (2)
C17^i—C17—H17B	109.3
C16—N11—C12—C13	−0.1 (4)	C21—C22—C23—C24	−0.3 (4)
N11—C12—C13—C14	−0.2 (4)	F23—C23—C24—C25	179.8 (2)
C12—C13—C14—C15	0.3 (4)	C22—C23—C24—C25	0.5 (4)
C12—C13—C14—C17	−177.4 (2)	F23—C23—C24—Br1	2.4 (3)
C13—C14—C15—C16	−0.1 (4)	C22—C23—C24—Br1	−176.91 (18)
C17—C14—C15—C16	177.6 (3)	C23—C24—C25—F25	−179.1 (2)
C12—N11—C16—C15	0.4 (4)	Br1—C24—C25—F25	−1.6 (3)
C14—C15—C16—N11	−0.2 (4)	C23—C24—C25—C26	−0.2 (4)
C13—C14—C17—C17^i	69.4 (3)	Br1—C24—C25—C26	177.27 (18)
C15—C14—C17—C17^i	−108.2 (3)	F25—C25—C26—F26	0.9 (3)
O21—C21—C22—F22	0.4 (3)	C24—C25—C26—F26	−178.0 (2)
C26—C21—C22—F22	−179.3 (2)	F25—C25—C26—C21	178.5 (2)
O21—C21—C22—C23	179.5 (2)	C24—C25—C26—C21	−0.4 (4)
C26—C21—C22—C23	−0.2 (4)	O21—C21—C26—F26	−1.5 (4)
F22—C22—C23—F23	−0.6 (3)	C22—C21—C26—F26	178.2 (2)
C21—C22—C23—F23	−179.7 (2)	O21—C21—C26—C25	−179.1 (2)
F22—C22—C23—C24	178.7 (2)	C22—C21—C26—C25	0.5 (3)

Symmetry code: (i) −x+1/2, −y−1/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21···N11	0.87 (3)	1.73 (3)	2.556 (3)	158 (3)

(IF4OH16) CS—AP-11–16 pyrazine 1-oxide, 4-I—F4-PhOH

Crystal data

(C4H4N2O)(C6HF4IO)	F(000) = 736
Mr = 388.06	Dx = 2.275 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.701 (2) Å	Cell parameters from 5600 reflections
b = 4.6121 (9) Å	θ = 3.6–33.7°
c = 21.594 (4) Å	µ = 2.88 mm^−1
β = 103.591 (6)°	T = 120 K
V = 1132.7 (4) Å^3	Plate, bronze
Z = 4	0.36 × 0.26 × 0.08 mm

Data collection

Bruker APEX-II CCD diffractometer	3766 independent reflections
Radiation source: fine-focus sealed tube	3283 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 33.7°, θmin = 1.8°
Absorption correction: multi-scan SADABS	h = −17→12
Tmin = 0.424, Tmax = 0.802	k = −6→4
8224 measured reflections	l = −31→33

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.063	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.030P)^2 + 0.7P] where P = (Fo^2 + 2Fc^2)/3
3766 reflections	(Δ/σ)max = 0.002
175 parameters	Δρmax = 0.71 e Å^−3
0 restraints	Δρmin = −0.83 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.05119 (15)	−0.2042 (4)	0.08733 (8)	0.0227 (3)
O11	−0.02786 (14)	−0.4030 (4)	0.07514 (8)	0.0332 (3)
C12	0.07272 (17)	−0.0561 (5)	0.14273 (9)	0.0248 (4)
H12	0.0287	−0.0955	0.1735	0.030*
C13	0.15869 (18)	0.1516 (4)	0.15410 (10)	0.0236 (4)
H13	0.1734	0.2519	0.1936	0.028*
N14	0.22298 (15)	0.2208 (4)	0.11279 (9)	0.0244 (3)
C15	0.19978 (17)	0.0733 (5)	0.05833 (9)	0.0246 (4)
H15	0.2430	0.1192	0.0275	0.030*
C16	0.11656 (18)	−0.1420 (5)	0.04440 (10)	0.0244 (4)
H16	0.1047	−0.2460	0.0054	0.029*
C21	0.44678 (17)	0.7764 (4)	0.16067 (9)	0.0200 (3)
O21	0.35987 (14)	0.6295 (4)	0.17685 (7)	0.0269 (3)
H21	0.332 (3)	0.530 (7)	0.1519 (14)	0.032*
C22	0.51018 (16)	0.9747 (4)	0.20371 (8)	0.0202 (3)
F22	0.47836 (11)	1.0143 (3)	0.25905 (5)	0.0301 (3)
C23	0.60213 (17)	1.1296 (4)	0.19131 (9)	0.0207 (3)
F23	0.65840 (12)	1.3171 (3)	0.23534 (6)	0.0289 (3)
C24	0.63639 (15)	1.0949 (4)	0.13459 (8)	0.0196 (3)
I1	0.780400 (10)	1.31425 (3)	0.117521 (6)	0.02425 (5)
C25	0.57221 (16)	0.9036 (4)	0.09096 (8)	0.0197 (3)
F25	0.59983 (11)	0.8617 (3)	0.03494 (5)	0.0267 (2)
C26	0.47997 (17)	0.7468 (4)	0.10334 (9)	0.0200 (3)
F26	0.41980 (11)	0.5600 (3)	0.06000 (6)	0.0296 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0172 (7)	0.0231 (8)	0.0283 (7)	−0.0027 (6)	0.0065 (6)	0.0061 (6)
O11	0.0259 (7)	0.0345 (8)	0.0408 (8)	−0.0134 (7)	0.0107 (6)	0.0013 (7)
C12	0.0211 (8)	0.0264 (9)	0.0294 (8)	0.0016 (8)	0.0112 (7)	0.0072 (8)
C13	0.0203 (8)	0.0245 (9)	0.0273 (8)	0.0015 (7)	0.0083 (7)	−0.0002 (7)
N14	0.0183 (7)	0.0248 (8)	0.0313 (8)	−0.0025 (6)	0.0082 (6)	0.0011 (7)
C15	0.0195 (8)	0.0278 (9)	0.0291 (8)	−0.0019 (8)	0.0110 (7)	0.0041 (8)
C16	0.0209 (9)	0.0282 (10)	0.0254 (8)	−0.0029 (7)	0.0083 (7)	0.0018 (7)
C21	0.0168 (8)	0.0205 (8)	0.0238 (8)	0.0005 (7)	0.0070 (6)	−0.0004 (7)
O21	0.0248 (7)	0.0287 (7)	0.0299 (7)	−0.0083 (6)	0.0120 (6)	−0.0046 (6)
C22	0.0202 (8)	0.0236 (9)	0.0181 (7)	0.0000 (7)	0.0073 (6)	−0.0031 (6)
F22	0.0352 (7)	0.0364 (7)	0.0229 (5)	−0.0049 (6)	0.0152 (5)	−0.0073 (5)
C23	0.0196 (8)	0.0206 (8)	0.0209 (7)	−0.0002 (7)	0.0030 (6)	−0.0023 (6)
F23	0.0303 (6)	0.0304 (7)	0.0253 (5)	−0.0085 (5)	0.0049 (5)	−0.0098 (5)
C24	0.0162 (7)	0.0212 (8)	0.0216 (7)	0.0008 (7)	0.0051 (6)	0.0011 (7)
I1	0.01743 (7)	0.02603 (8)	0.03012 (7)	−0.00176 (4)	0.00722 (5)	0.00226 (5)
C25	0.0187 (8)	0.0242 (8)	0.0173 (7)	0.0023 (7)	0.0064 (6)	−0.0008 (7)
F25	0.0262 (6)	0.0367 (7)	0.0197 (5)	0.0000 (5)	0.0104 (4)	−0.0035 (5)
C26	0.0182 (8)	0.0218 (8)	0.0193 (7)	−0.0015 (7)	0.0029 (6)	−0.0044 (6)
F26	0.0276 (6)	0.0340 (7)	0.0271 (5)	−0.0099 (6)	0.0059 (4)	−0.0127 (5)

Geometric parameters (Å, º)

N11—O11	1.285 (2)	C21—C22	1.388 (3)
N11—C12	1.349 (3)	C21—C26	1.388 (3)
N11—C16	1.364 (2)	O21—H21	0.72 (3)
C12—C13	1.369 (3)	C22—F22	1.3452 (19)
C12—H12	0.9500	C22—C23	1.369 (3)
C13—N14	1.334 (3)	C23—F23	1.338 (2)
C13—H13	0.9500	C23—C24	1.385 (2)
N14—C15	1.330 (3)	C24—C25	1.377 (3)
C15—C16	1.374 (3)	C24—I1	2.0713 (18)
C15—H15	0.9500	C25—F25	1.3376 (19)
C16—H16	0.9500	C25—C26	1.377 (3)
C21—O21	1.335 (2)	C26—F26	1.343 (2)
O11—N11—C12	121.22 (16)	C22—C21—C26	116.36 (18)
O11—N11—C16	120.18 (18)	C21—O21—H21	111 (2)
C12—N11—C16	118.59 (17)	F22—C22—C23	119.81 (16)
N11—C12—C13	119.32 (17)	F22—C22—C21	117.92 (16)
N11—C12—H12	120.3	C23—C22—C21	122.27 (16)
C13—C12—H12	120.3	F23—C23—C22	118.45 (16)
N14—C13—C12	123.63 (19)	F23—C23—C24	120.44 (17)
N14—C13—H13	118.2	C22—C23—C24	121.11 (17)
C12—C13—H13	118.2	C25—C24—C23	117.02 (17)
C15—N14—C13	116.02 (18)	C25—C24—I1	121.78 (12)
N14—C15—C16	123.39 (17)	C23—C24—I1	121.18 (14)
N14—C15—H15	118.3	F25—C25—C26	117.82 (16)
C16—C15—H15	118.3	F25—C25—C24	120.16 (16)
N11—C16—C15	119.02 (18)	C26—C25—C24	122.01 (16)
N11—C16—H16	120.5	F26—C26—C25	120.54 (16)
C15—C16—H16	120.5	F26—C26—C21	118.26 (18)
O21—C21—C22	118.64 (17)	C25—C26—C21	121.20 (18)
O21—C21—C26	125.00 (19)
O11—N11—C12—C13	179.22 (19)	F23—C23—C24—C25	−178.32 (17)
C16—N11—C12—C13	0.2 (3)	C22—C23—C24—C25	1.5 (3)
N11—C12—C13—N14	0.8 (3)	F23—C23—C24—I1	3.2 (3)
C12—C13—N14—C15	−0.4 (3)	C22—C23—C24—I1	−177.03 (15)
C13—N14—C15—C16	−1.0 (3)	C23—C24—C25—F25	179.38 (17)
O11—N11—C16—C15	179.42 (19)	I1—C24—C25—F25	−2.1 (3)
C12—N11—C16—C15	−1.6 (3)	C23—C24—C25—C26	−1.7 (3)
N14—C15—C16—N11	2.0 (3)	I1—C24—C25—C26	176.78 (15)
O21—C21—C22—F22	−1.8 (3)	F25—C25—C26—F26	−0.5 (3)
C26—C21—C22—F22	178.31 (18)	C24—C25—C26—F26	−179.39 (18)
O21—C21—C22—C23	178.63 (19)	F25—C25—C26—C21	179.38 (18)
C26—C21—C22—C23	−1.3 (3)	C24—C25—C26—C21	0.5 (3)
F22—C22—C23—F23	0.2 (3)	O21—C21—C26—F26	1.0 (3)
C21—C22—C23—F23	179.82 (18)	C22—C21—C26—F26	−179.10 (16)
F22—C22—C23—C24	−179.58 (18)	O21—C21—C26—C25	−178.87 (18)
C21—C22—C23—C24	0.0 (3)	C22—C21—C26—C25	1.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21···N14	0.72 (3)	1.97 (3)	2.644 (2)	156 (3)

(IF4OH2) CS—AP-11–2 4-I—F4-PhOH, isonicotinonitrile

Crystal data

(C6HF4IO)(C6H4N2)	F(000) = 752
Mr = 396.08	Dx = 2.104 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.7258 (15) Å	Cell parameters from 9904 reflections
b = 4.9322 (6) Å	θ = 2.3–32.6°
c = 20.729 (2) Å	µ = 2.61 mm^−1
β = 106.074 (3)°	T = 120 K
V = 1250.2 (3) Å^3	Rod, gold
Z = 4	0.32 × 0.12 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	4266 independent reflections
Radiation source: fine-focus sealed tube	3829 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 32.0°, θmin = 2.0°
Absorption correction: multi-scan SADABS	h = −18→17
Tmin = 0.489, Tmax = 0.859	k = −6→7
15519 measured reflections	l = −30→30

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 0.6P] where P = (Fo^2 + 2Fc^2)/3
4266 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 1.20 e Å^−3
0 restraints	Δρmin = −2.00 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.74605 (15)	0.3011 (4)	0.37052 (9)	0.0248 (3)
C12	0.8062 (2)	0.2417 (4)	0.32940 (11)	0.0240 (4)
H12	0.7932	0.3400	0.2885	0.029*
C13	0.88700 (15)	0.0440 (4)	0.34269 (9)	0.0245 (3)
H13	0.9290	0.0080	0.3122	0.029*
C14	0.90382 (15)	−0.0988 (4)	0.40241 (9)	0.0227 (3)
C15	0.84104 (16)	−0.0428 (4)	0.44588 (9)	0.0264 (4)
H15	0.8510	−0.1407	0.4866	0.032*
C16	0.76328 (17)	0.1610 (4)	0.42785 (10)	0.0266 (4)
H16	0.7204	0.2030	0.4575	0.032*
C17	0.98733 (18)	−0.3062 (4)	0.41954 (10)	0.0263 (4)
N17	1.05269 (16)	−0.4690 (4)	0.43343 (9)	0.0342 (4)
C21	0.54135 (15)	0.8222 (4)	0.32944 (9)	0.0213 (3)
O21	0.62252 (14)	0.7030 (3)	0.31076 (8)	0.0273 (3)
H21	0.651 (2)	0.588 (7)	0.3361 (15)	0.033*
C22	0.51485 (18)	0.7652 (4)	0.38884 (10)	0.0231 (4)
F22	0.57362 (11)	0.5782 (3)	0.43032 (6)	0.0346 (3)
C23	0.42934 (15)	0.8953 (4)	0.40481 (9)	0.0233 (3)
F23	0.40911 (11)	0.8307 (3)	0.46300 (6)	0.0308 (3)
C24	0.36692 (15)	1.0874 (4)	0.36299 (9)	0.0239 (3)
I1	0.236138 (11)	1.27339 (3)	0.386120 (7)	0.02910 (6)
C25	0.39384 (16)	1.1485 (4)	0.30423 (9)	0.0241 (3)
F25	0.33738 (12)	1.3349 (3)	0.26192 (7)	0.0355 (3)
C26	0.47941 (15)	1.0195 (4)	0.28816 (8)	0.0231 (3)
F26	0.50402 (11)	1.0840 (3)	0.23110 (6)	0.0311 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0246 (8)	0.0256 (7)	0.0249 (7)	0.0041 (6)	0.0082 (6)	−0.0001 (6)
C12	0.0271 (10)	0.0225 (8)	0.0223 (9)	0.0051 (6)	0.0067 (7)	0.0015 (6)
C13	0.0252 (8)	0.0280 (8)	0.0216 (7)	0.0047 (7)	0.0085 (6)	−0.0010 (6)
C14	0.0223 (7)	0.0245 (8)	0.0203 (7)	0.0027 (7)	0.0043 (6)	−0.0009 (6)
C15	0.0275 (8)	0.0310 (9)	0.0216 (8)	0.0057 (7)	0.0083 (7)	0.0027 (7)
C16	0.0269 (9)	0.0316 (9)	0.0237 (8)	0.0059 (8)	0.0111 (7)	0.0002 (7)
C17	0.0260 (9)	0.0315 (9)	0.0214 (8)	0.0047 (7)	0.0066 (7)	−0.0012 (7)
N17	0.0340 (9)	0.0393 (10)	0.0298 (8)	0.0124 (8)	0.0094 (7)	0.0015 (7)
C21	0.0207 (8)	0.0260 (8)	0.0185 (7)	0.0008 (7)	0.0072 (6)	0.0008 (6)
O21	0.0275 (7)	0.0342 (7)	0.0231 (7)	0.0106 (6)	0.0119 (6)	0.0050 (5)
C22	0.0245 (9)	0.0288 (9)	0.0161 (8)	0.0042 (7)	0.0058 (7)	0.0043 (6)
F22	0.0377 (7)	0.0422 (7)	0.0254 (5)	0.0166 (6)	0.0114 (5)	0.0143 (5)
C23	0.0235 (8)	0.0297 (9)	0.0183 (7)	−0.0007 (7)	0.0083 (6)	0.0007 (6)
F23	0.0329 (6)	0.0432 (7)	0.0199 (5)	0.0037 (6)	0.0133 (5)	0.0056 (5)
C24	0.0206 (7)	0.0294 (9)	0.0224 (8)	0.0008 (7)	0.0072 (6)	−0.0006 (6)
I1	0.02417 (9)	0.03566 (9)	0.02940 (9)	0.00607 (4)	0.01063 (6)	−0.00214 (4)
C25	0.0225 (8)	0.0280 (8)	0.0215 (8)	0.0037 (7)	0.0053 (6)	0.0048 (7)
F25	0.0361 (7)	0.0395 (7)	0.0311 (6)	0.0167 (6)	0.0096 (5)	0.0136 (6)
C26	0.0245 (8)	0.0280 (8)	0.0184 (7)	0.0006 (7)	0.0084 (6)	0.0033 (6)
F26	0.0350 (6)	0.0391 (7)	0.0228 (5)	0.0058 (5)	0.0142 (5)	0.0095 (5)

Geometric parameters (Å, º)

N11—C12	1.326 (3)	C21—C26	1.388 (3)
N11—C16	1.339 (3)	C21—C22	1.393 (2)
C12—C13	1.389 (3)	O21—H21	0.79 (3)
C12—H12	0.9500	C22—F22	1.339 (2)
C13—C14	1.388 (3)	C22—C23	1.380 (3)
C13—H13	0.9500	C23—F23	1.340 (2)
C14—C15	1.387 (3)	C23—C24	1.378 (3)
C14—C17	1.447 (3)	C24—C25	1.387 (2)
C15—C16	1.387 (3)	C24—I1	2.0695 (18)
C15—H15	0.9500	C25—F25	1.335 (2)
C16—H16	0.9500	C25—C26	1.379 (3)
C17—N17	1.134 (3)	C26—F26	1.3431 (19)
C21—O21	1.336 (2)
C12—N11—C16	118.33 (17)	O21—C21—C22	124.31 (18)
N11—C12—C13	123.71 (19)	C26—C21—C22	116.83 (17)
N11—C12—H12	118.1	C21—O21—H21	112 (2)
C13—C12—H12	118.1	F22—C22—C23	120.23 (17)
C14—C13—C12	117.13 (17)	F22—C22—C21	118.54 (18)
C14—C13—H13	121.4	C23—C22—C21	121.22 (17)
C12—C13—H13	121.4	F23—C23—C24	120.59 (16)
C15—C14—C13	120.25 (17)	F23—C23—C22	117.79 (17)
C15—C14—C17	119.82 (17)	C24—C23—C22	121.62 (16)
C13—C14—C17	119.93 (17)	C23—C24—C25	117.54 (17)
C16—C15—C14	117.73 (17)	C23—C24—I1	121.30 (13)
C16—C15—H15	121.1	C25—C24—I1	121.16 (14)
C14—C15—H15	121.1	F25—C25—C26	118.44 (16)
N11—C16—C15	122.84 (18)	F25—C25—C24	120.52 (17)
N11—C16—H16	118.6	C26—C25—C24	121.03 (17)
C15—C16—H16	118.6	F26—C26—C25	119.71 (16)
N17—C17—C14	179.5 (2)	F26—C26—C21	118.55 (16)
O21—C21—C26	118.85 (16)	C25—C26—C21	121.74 (16)
C16—N11—C12—C13	−0.7 (3)	F23—C23—C24—C25	178.66 (18)
N11—C12—C13—C14	0.6 (3)	C22—C23—C24—C25	−0.7 (3)
C12—C13—C14—C15	0.2 (3)	F23—C23—C24—I1	−2.4 (3)
C12—C13—C14—C17	−179.56 (19)	C22—C23—C24—I1	178.24 (15)
C13—C14—C15—C16	−0.9 (3)	C23—C24—C25—F25	−179.26 (19)
C17—C14—C15—C16	178.90 (19)	I1—C24—C25—F25	1.8 (3)
C12—N11—C16—C15	0.0 (3)	C23—C24—C25—C26	0.6 (3)
C14—C15—C16—N11	0.8 (3)	I1—C24—C25—C26	−178.42 (15)
O21—C21—C22—F22	−0.3 (3)	F25—C25—C26—F26	0.2 (3)
C26—C21—C22—F22	−179.27 (18)	C24—C25—C26—F26	−179.59 (18)
O21—C21—C22—C23	−179.6 (2)	F25—C25—C26—C21	−179.56 (19)
C26—C21—C22—C23	1.4 (3)	C24—C25—C26—C21	0.6 (3)
F22—C22—C23—F23	1.0 (3)	O21—C21—C26—F26	−0.4 (3)
C21—C22—C23—F23	−179.68 (18)	C22—C21—C26—F26	178.63 (18)
F22—C22—C23—C24	−179.59 (19)	O21—C21—C26—C25	179.41 (19)
C21—C22—C23—C24	−0.3 (3)	C22—C21—C26—C25	−1.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21···N11	0.79 (3)	1.87 (3)	2.619 (2)	158 (3)

(IF4CO16) SD-1–8-1–10 4-I—F4-PhCOOH, pyrazine 1-oxide

Crystal data

(C7HF4IO2)(C4H4N2O)	Z = 2
Mr = 416.07	F(000) = 396
Triclinic, P1	Dx = 2.212 Mg m^−3
a = 4.2485 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6204 (8) Å	Cell parameters from 9870 reflections
c = 13.8288 (10) Å	θ = 4.9–33.3°
α = 110.206 (2)°	µ = 2.63 mm^−1
β = 95.970 (1)°	T = 120 K
γ = 98.531 (1)°	Prism, colourless
V = 624.68 (8) Å^3	0.32 × 0.26 × 0.20 mm

Data collection

Bruker APEX-II CCD diffractometer	4376 independent reflections
Radiation source: fine-focus sealed tube	4274 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 33.1°, θmin = 2.0°
Absorption correction: multi-scan SADABS	h = −6→6
Tmin = 0.487, Tmax = 0.622	k = −17→17
18348 measured reflections	l = −21→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.047	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.025P)^2 + 0.4P] where P = (Fo^2 + 2Fc^2)/3
4376 reflections	(Δ/σ)max = 0.001
233 parameters	Δρmax = 0.62 e Å^−3
35 restraints	Δρmin = −0.65 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N11	−0.2566 (3)	0.86050 (11)	0.54544 (9)	0.01790 (19)
O11	−0.4103 (3)	0.94051 (11)	0.60034 (9)	0.0274 (2)
C12	−0.1441 (4)	0.77738 (13)	0.58205 (11)	0.0213 (2)
H12	−0.1750	0.7779	0.6492	0.080*
C13	0.0154 (4)	0.69224 (14)	0.52069 (12)	0.0236 (3)
H13	0.0927	0.6343	0.5470	0.080*
N14	0.0660 (3)	0.68760 (12)	0.42565 (10)	0.0234 (2)
C15	−0.0495 (4)	0.77021 (13)	0.39113 (11)	0.0214 (2)
H15	−0.0184	0.7684	0.3236	0.080*
C16	−0.2108 (3)	0.85745 (12)	0.44873 (10)	0.0190 (2)
H16	−0.2888	0.9145	0.4215	0.080*
I1A	0.58373 (2)	0.079905 (8)	−0.188724 (6)	0.02029 (3)	0.9910 (4)
C21A	0.4607 (3)	0.36452 (12)	0.15820 (10)	0.0155 (2)	0.9910 (4)
C27A	0.4156 (4)	0.44523 (15)	0.26489 (11)	0.0183 (2)	0.9910 (4)
O21A	0.2611 (5)	0.53346 (16)	0.26287 (10)	0.0494 (5)	0.9910 (4)
H21A	0.2038	0.5655	0.3210	0.080*	0.9910 (4)
O22A	0.5074 (4)	0.42984 (13)	0.34352 (10)	0.0405 (3)	0.9910 (4)
C22A	0.6218 (4)	0.26489 (13)	0.14571 (10)	0.0176 (2)	0.9910 (4)
C23A	0.6585 (4)	0.18572 (13)	0.04836 (11)	0.0181 (2)	0.9910 (4)
C24A	0.5377 (3)	0.20158 (13)	−0.04238 (10)	0.0176 (2)	0.9910 (4)
C25A	0.3840 (3)	0.30135 (14)	−0.03092 (10)	0.0177 (2)	0.9910 (4)
C26A	0.3445 (4)	0.38037 (13)	0.06634 (10)	0.0171 (2)	0.9910 (4)
F22A	0.7498 (3)	0.24295 (9)	0.22871 (7)	0.0274 (2)	0.9910 (4)
F23A	0.8190 (2)	0.09368 (9)	0.04349 (8)	0.0264 (2)	0.9910 (4)
F25A	0.2653 (3)	0.32360 (11)	−0.11500 (7)	0.0254 (2)	0.9910 (4)
F26A	0.1857 (3)	0.47142 (11)	0.06769 (8)	0.0262 (2)	0.9910 (4)
I1B	0.348 (3)	0.4846 (11)	0.2823 (8)	0.0183 (2)	0.0090 (4)
C21B	0.58 (2)	0.190 (6)	−0.043 (3)	0.0176 (2)	0.0090 (4)
C27B	0.721 (15)	0.115 (5)	−0.135 (3)	0.02029 (3)	0.0090 (4)
O21B	0.64 (2)	0.141 (8)	−0.218 (3)	0.02029 (3)	0.0090 (4)
H21B	0.6308	0.0772	−0.2717	0.080*	0.0090 (4)
O22B	0.93 (2)	0.057 (8)	−0.128 (5)	0.02029 (3)	0.0090 (4)
C22B	0.64 (3)	0.174 (6)	0.052 (3)	0.0181 (2)	0.0090 (4)
C23B	0.58 (3)	0.257 (7)	0.144 (3)	0.0176 (2)	0.0090 (4)
C24B	0.43 (3)	0.355 (8)	0.1440 (17)	0.0155 (2)	0.0090 (4)
C25B	0.35 (3)	0.367 (8)	0.0487 (16)	0.0171 (2)	0.0090 (4)
C26B	0.43 (3)	0.289 (8)	−0.042 (2)	0.0177 (2)	0.0090 (4)
F22B	0.75 (4)	0.073 (7)	0.058 (4)	0.0264 (2)	0.0090 (4)
F23B	0.64 (3)	0.235 (8)	0.232 (3)	0.0274 (2)	0.0090 (4)
F25B	0.22 (4)	0.463 (11)	0.044 (3)	0.0262 (2)	0.0090 (4)
F26B	0.33 (4)	0.306 (11)	−0.130 (2)	0.0254 (2)	0.0090 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0223 (5)	0.0176 (4)	0.0139 (4)	0.0088 (4)	0.0040 (4)	0.0037 (4)
O11	0.0390 (6)	0.0289 (5)	0.0176 (4)	0.0224 (5)	0.0100 (4)	0.0047 (4)
C12	0.0266 (6)	0.0229 (6)	0.0183 (6)	0.0102 (5)	0.0050 (5)	0.0099 (5)
C13	0.0283 (6)	0.0201 (6)	0.0241 (6)	0.0105 (5)	0.0037 (5)	0.0080 (5)
N14	0.0266 (6)	0.0211 (5)	0.0210 (5)	0.0110 (4)	0.0048 (4)	0.0031 (4)
C15	0.0249 (6)	0.0229 (6)	0.0155 (5)	0.0081 (5)	0.0054 (5)	0.0038 (4)
C16	0.0255 (6)	0.0185 (5)	0.0142 (5)	0.0082 (4)	0.0043 (4)	0.0057 (4)
I1A	0.02195 (5)	0.02179 (5)	0.01507 (5)	0.00630 (3)	0.00646 (3)	0.00244 (3)
C21A	0.0180 (5)	0.0144 (5)	0.0134 (5)	0.0053 (4)	0.0028 (4)	0.0035 (4)
C27A	0.0216 (6)	0.0147 (6)	0.0174 (6)	0.0058 (5)	0.0048 (5)	0.0033 (5)
O21A	0.0849 (12)	0.0557 (9)	0.0174 (5)	0.0571 (9)	0.0122 (6)	0.0068 (5)
O22A	0.0747 (10)	0.0380 (7)	0.0166 (5)	0.0346 (7)	0.0108 (6)	0.0092 (5)
C22A	0.0210 (6)	0.0181 (5)	0.0143 (5)	0.0078 (5)	0.0019 (4)	0.0054 (4)
C23A	0.0195 (5)	0.0175 (5)	0.0174 (5)	0.0086 (4)	0.0041 (4)	0.0040 (4)
C24A	0.0181 (5)	0.0187 (5)	0.0144 (5)	0.0049 (4)	0.0044 (4)	0.0030 (4)
C25A	0.0211 (6)	0.0187 (5)	0.0138 (5)	0.0049 (4)	0.0023 (4)	0.0062 (4)
C26A	0.0202 (5)	0.0158 (5)	0.0161 (5)	0.0071 (4)	0.0025 (5)	0.0055 (4)
F22A	0.0400 (6)	0.0288 (4)	0.0163 (4)	0.0198 (4)	0.0006 (4)	0.0078 (3)
F23A	0.0322 (5)	0.0250 (4)	0.0240 (4)	0.0195 (4)	0.0055 (4)	0.0056 (3)
F25A	0.0366 (6)	0.0263 (5)	0.0145 (4)	0.0095 (4)	0.0005 (3)	0.0086 (3)
F26A	0.0391 (6)	0.0219 (4)	0.0208 (4)	0.0183 (4)	0.0026 (4)	0.0076 (4)
I1B	0.0216 (6)	0.0147 (6)	0.0174 (6)	0.0058 (5)	0.0048 (5)	0.0033 (5)
C21B	0.0181 (5)	0.0187 (5)	0.0144 (5)	0.0049 (4)	0.0044 (4)	0.0030 (4)
C27B	0.02195 (5)	0.02179 (5)	0.01507 (5)	0.00630 (3)	0.00646 (3)	0.00244 (3)
O21B	0.02195 (5)	0.02179 (5)	0.01507 (5)	0.00630 (3)	0.00646 (3)	0.00244 (3)
O22B	0.02195 (5)	0.02179 (5)	0.01507 (5)	0.00630 (3)	0.00646 (3)	0.00244 (3)
C22B	0.0195 (5)	0.0175 (5)	0.0174 (5)	0.0086 (4)	0.0041 (4)	0.0040 (4)
C23B	0.0210 (6)	0.0181 (5)	0.0143 (5)	0.0078 (5)	0.0019 (4)	0.0054 (4)
C24B	0.0180 (5)	0.0144 (5)	0.0134 (5)	0.0053 (4)	0.0028 (4)	0.0035 (4)
C25B	0.0202 (5)	0.0158 (5)	0.0161 (5)	0.0071 (4)	0.0025 (5)	0.0055 (4)
C26B	0.0211 (6)	0.0187 (5)	0.0138 (5)	0.0049 (4)	0.0023 (4)	0.0062 (4)
F22B	0.0322 (5)	0.0250 (4)	0.0240 (4)	0.0195 (4)	0.0055 (4)	0.0056 (3)
F23B	0.0400 (6)	0.0288 (4)	0.0163 (4)	0.0198 (4)	0.0006 (4)	0.0078 (3)
F25B	0.0391 (6)	0.0219 (4)	0.0208 (4)	0.0183 (4)	0.0026 (4)	0.0076 (4)
F26B	0.0366 (6)	0.0263 (5)	0.0145 (4)	0.0095 (4)	0.0005 (3)	0.0086 (3)

Geometric parameters (Å, º)

N11—O11	1.2895 (15)	C23A—C24A	1.3877 (19)
N11—C12	1.3572 (17)	C24A—C25A	1.3840 (19)
N11—C16	1.3605 (17)	C25A—F25A	1.3407 (15)
C12—C13	1.377 (2)	C25A—C26A	1.3855 (19)
C12—H12	0.9500	C26A—F26A	1.3324 (15)
C13—N14	1.338 (2)	I1B—C24B	2.079 (4)
C13—H13	0.9500	C21B—C26B	1.396 (4)
N14—C15	1.3409 (19)	C21B—C22B	1.400 (4)
C15—C16	1.3764 (19)	C21B—C27B	1.502 (4)
C15—H15	0.9500	C27B—O22B	1.199 (4)
C16—H16	0.9500	C27B—O21B	1.304 (5)
I1A—C24A	2.0785 (13)	O21B—H21B	0.8400
C21A—C26A	1.3963 (18)	C22B—F22B	1.339 (4)
C21A—C22A	1.3999 (17)	C22B—C23B	1.384 (4)
C21A—C27A	1.500 (2)	C23B—F23B	1.338 (4)
C27A—O22A	1.1972 (18)	C23B—C24B	1.388 (4)
C27A—O21A	1.303 (2)	C24B—C25B	1.384 (4)
O21A—H21A	0.8400	C25B—F25B	1.341 (4)
C22A—F22A	1.3386 (15)	C25B—C26B	1.386 (4)
C22A—C23A	1.3834 (18)	C26B—F26B	1.333 (4)
C23A—F23A	1.3379 (15)
O11—N11—C12	120.87 (12)	C25A—C24A—I1A	121.69 (10)
O11—N11—C16	119.83 (11)	C23A—C24A—I1A	121.32 (10)
C12—N11—C16	119.29 (11)	F25A—C25A—C24A	120.34 (12)
N11—C12—C13	119.26 (13)	F25A—C25A—C26A	117.85 (12)
N11—C12—H12	120.4	C24A—C25A—C26A	121.80 (12)
C13—C12—H12	120.4	F26A—C26A—C25A	116.55 (12)
N14—C13—C12	122.80 (13)	F26A—C26A—C21A	121.61 (12)
N14—C13—H13	118.6	C25A—C26A—C21A	121.84 (12)
C12—C13—H13	118.6	C26B—C21B—C22B	115.6 (5)
C13—N14—C15	116.70 (12)	C26B—C21B—C27B	123.7 (7)
N14—C15—C16	123.19 (13)	C22B—C21B—C27B	120.1 (7)
N14—C15—H15	118.4	O22B—C27B—O21B	122.8 (9)
C16—C15—H15	118.4	O22B—C27B—C21B	123.4 (8)
N11—C16—C15	118.76 (12)	O21B—C27B—C21B	112.3 (7)
N11—C16—H16	120.6	C27B—O21B—H21B	109.5
C15—C16—H16	120.6	F22B—C22B—C23B	117.0 (7)
C26A—C21A—C22A	115.80 (12)	F22B—C22B—C21B	120.7 (7)
C26A—C21A—C27A	123.79 (12)	C23B—C22B—C21B	122.1 (5)
C22A—C21A—C27A	120.40 (12)	F23B—C23B—C22B	118.1 (7)
O22A—C27A—O21A	123.36 (16)	F23B—C23B—C24B	120.3 (8)
O22A—C27A—C21A	123.97 (15)	C22B—C23B—C24B	121.4 (6)
O21A—C27A—C21A	112.67 (12)	C25B—C24B—C23B	116.9 (5)
C27A—O21A—H21A	109.5	C25B—C24B—I1B	121.6 (6)
F22A—C22A—C23A	117.04 (12)	C23B—C24B—I1B	121.4 (6)
F22A—C22A—C21A	120.83 (12)	F25B—C25B—C24B	120.1 (7)
C23A—C22A—C21A	122.13 (12)	F25B—C25B—C26B	117.8 (7)
F23A—C23A—C22A	118.28 (12)	C24B—C25B—C26B	121.8 (6)
F23A—C23A—C24A	120.29 (12)	F26B—C26B—C25B	116.4 (7)
C22A—C23A—C24A	121.43 (12)	F26B—C26B—C21B	121.6 (8)
C25A—C24A—C23A	116.99 (12)	C25B—C26B—C21B	121.8 (5)
O11—N11—C12—C13	179.18 (14)	C22A—C21A—C26A—F26A	179.69 (14)
C16—N11—C12—C13	0.3 (2)	C27A—C21A—C26A—F26A	0.9 (2)
N11—C12—C13—N14	0.1 (2)	C22A—C21A—C26A—C25A	0.6 (2)
C12—C13—N14—C15	−0.6 (2)	C27A—C21A—C26A—C25A	−178.17 (14)
C13—N14—C15—C16	0.5 (2)	C26B—C21B—C27B—O22B	157 (8)
O11—N11—C16—C15	−179.23 (13)	C22B—C21B—C27B—O22B	−14 (8)
C12—N11—C16—C15	−0.4 (2)	C26B—C21B—C27B—O21B	−9 (8)
N14—C15—C16—N11	−0.1 (2)	C22B—C21B—C27B—O21B	−180 (7)
C26A—C21A—C27A—O22A	177.93 (17)	C26B—C21B—C22B—F22B	171 (11)
C22A—C21A—C27A—O22A	−0.8 (2)	C27B—C21B—C22B—F22B	−18 (11)
C26A—C21A—C27A—O21A	−1.2 (2)	C26B—C21B—C22B—C23B	−5 (8)
C22A—C21A—C27A—O21A	−179.95 (16)	C27B—C21B—C22B—C23B	166 (8)
C26A—C21A—C22A—F22A	178.38 (14)	F22B—C22B—C23B—F23B	4 (13)
C27A—C21A—C22A—F22A	−2.8 (2)	C21B—C22B—C23B—F23B	180 (10)
C26A—C21A—C22A—C23A	−1.1 (2)	F22B—C22B—C23B—C24B	−170 (12)
C27A—C21A—C22A—C23A	177.73 (14)	C21B—C22B—C23B—C24B	6 (11)
F22A—C22A—C23A—F23A	−0.3 (2)	F23B—C23B—C24B—C25B	−176 (11)
C21A—C22A—C23A—F23A	179.23 (14)	C22B—C23B—C24B—C25B	−2 (12)
F22A—C22A—C23A—C24A	−179.24 (14)	F23B—C23B—C24B—I1B	9 (12)
C21A—C22A—C23A—C24A	0.3 (2)	C22B—C23B—C24B—I1B	−177 (9)
F23A—C23A—C24A—C25A	−177.87 (14)	C23B—C24B—C25B—F25B	−177 (12)
C22A—C23A—C24A—C25A	1.1 (2)	I1B—C24B—C25B—F25B	−1 (14)
F23A—C23A—C24A—I1A	2.54 (19)	C23B—C24B—C25B—C26B	−2 (13)
C22A—C23A—C24A—I1A	−178.52 (11)	I1B—C24B—C25B—C26B	173 (10)
C23A—C24A—C25A—F25A	179.04 (13)	F25B—C25B—C26B—F26B	−8 (14)
I1A—C24A—C25A—F25A	−1.37 (19)	C24B—C25B—C26B—F26B	177 (12)
C23A—C24A—C25A—C26A	−1.6 (2)	F25B—C25B—C26B—C21B	177 (12)
I1A—C24A—C25A—C26A	178.04 (12)	C24B—C25B—C26B—C21B	2 (13)
F25A—C25A—C26A—F26A	1.0 (2)	C22B—C21B—C26B—F26B	−173 (11)
C24A—C25A—C26A—F26A	−178.39 (14)	C27B—C21B—C26B—F26B	15 (12)
F25A—C25A—C26A—C21A	−179.87 (14)	C22B—C21B—C26B—C25B	1 (10)
C24A—C25A—C26A—C21A	0.7 (2)	C27B—C21B—C26B—C25B	−170 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21A—H21A···N14	0.84	1.86	2.6469 (18)	156
O21B—H21B···O11^i	0.84	1.90	2.73 (6)	175

Symmetry code: (i) x+1, y−1, z−1.

(IF4CO2) SD—A-5–1 4-I—F4-PhCOOH, isonicotinonitrile

Crystal data

(C7HIF4O2)(C6H4N2)	F(000) = 1616
Mr = 424.09	Dx = 2.134 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.4234 (3) Å	Cell parameters from 6447 reflections
b = 35.8851 (18) Å	θ = 3.0–32.5°
c = 10.0949 (5) Å	µ = 2.48 mm^−1
β = 101.028 (2)°	T = 120 K
V = 2639.5 (2) Å^3	Plate, colourless
Z = 8	0.28 × 0.24 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	8978 independent reflections
Radiation source: fine-focus sealed tube	6715 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 32.6°, θmin = 2.1°
Absorption correction: multi-scan SADABS	h = −10→10
Tmin = 0.620, Tmax = 0.747	k = −52→51
22625 measured reflections	l = −15→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 5.P] where P = (Fo^2 + 2Fc^2)/3
8978 reflections	(Δ/σ)max = 0.003
459 parameters	Δρmax = 1.51 e Å^−3
210 restraints	Δρmin = −1.04 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1A	−0.01163 (3)	0.389363 (7)	0.73489 (2)	0.02187 (8)	0.9760 (9)
C11A	0.0379 (5)	0.25289 (8)	0.7831 (3)	0.0202 (7)	0.9760 (9)
C12A	0.1173 (5)	0.27730 (8)	0.8857 (3)	0.0189 (7)	0.9760 (9)
C13A	0.1023 (5)	0.31542 (8)	0.8731 (3)	0.0197 (7)	0.9760 (9)
C14A	0.0062 (4)	0.33184 (8)	0.7561 (3)	0.0179 (6)	0.9760 (9)
C15A	−0.0731 (5)	0.30833 (8)	0.6545 (3)	0.0193 (7)	0.9760 (9)
C16A	−0.0598 (5)	0.27009 (8)	0.6664 (3)	0.0205 (7)	0.9760 (9)
F12A	0.2175 (4)	0.26422 (6)	1.0014 (2)	0.0264 (6)	0.9760 (9)
F13A	0.1826 (3)	0.33665 (6)	0.9765 (2)	0.0249 (5)	0.9760 (9)
F15A	−0.1690 (3)	0.32241 (6)	0.5392 (2)	0.0276 (5)	0.9760 (9)
F16A	−0.1457 (4)	0.25002 (6)	0.5612 (2)	0.0281 (5)	0.9760 (9)
C17A	0.0583 (7)	0.21177 (11)	0.8008 (4)	0.0322 (4)	0.9760 (9)
O11A	−0.0270 (4)	0.19256 (8)	0.6965 (3)	0.0322 (4)	0.9760 (9)
H11A	−0.0112	0.1697	0.7122	0.039*	0.9760 (9)
O12A	0.1429 (4)	0.19728 (7)	0.9010 (3)	0.0322 (4)	0.9760 (9)
I1B	0.0433 (19)	0.1995 (2)	0.7677 (13)	0.0322 (4)	0.0240 (9)
C11B	0.019 (4)	0.3366 (2)	0.748 (4)	0.0179 (6)	0.0240 (9)
C12B	−0.090 (3)	0.3140 (3)	0.652 (3)	0.0193 (7)	0.0240 (9)
C13B	−0.070 (4)	0.2758 (3)	0.650 (3)	0.0205 (7)	0.0240 (9)
C14B	0.042 (4)	0.2573 (2)	0.756 (2)	0.0202 (7)	0.0240 (9)
C15B	0.139 (5)	0.2790 (3)	0.856 (3)	0.0189 (7)	0.0240 (9)
C16B	0.137 (4)	0.3174 (3)	0.850 (3)	0.0197 (7)	0.0240 (9)
F12B	−0.232 (7)	0.3284 (6)	0.564 (6)	0.0276 (5)	0.0240 (9)
F13B	−0.149 (12)	0.2571 (6)	0.540 (5)	0.0281 (5)	0.0240 (9)
F15B	0.231 (14)	0.2629 (5)	0.969 (6)	0.0264 (6)	0.0240 (9)
F16B	0.261 (9)	0.3355 (5)	0.942 (6)	0.0249 (5)	0.0240 (9)
C17B	0.016 (6)	0.3779 (2)	0.732 (4)	0.02187 (8)	0.0240 (9)
O11B	0.078 (12)	0.3959 (4)	0.845 (5)	0.02187 (8)	0.0240 (9)
O12B	−0.024 (12)	0.3934 (6)	0.625 (5)	0.02187 (8)	0.0240 (9)
H12B	−0.0129	0.4165	0.6360	0.026*	0.0240 (9)
I2A	0.47338 (3)	0.637016 (7)	0.72384 (3)	0.02327 (8)	0.9464 (9)
C21A	0.5259 (5)	0.50070 (8)	0.7781 (3)	0.0211 (7)	0.9464 (9)
C22A	0.6034 (5)	0.52556 (8)	0.8797 (3)	0.0199 (7)	0.9464 (9)
C23A	0.5876 (5)	0.56360 (8)	0.8650 (3)	0.0195 (7)	0.9464 (9)
C24A	0.4937 (5)	0.57954 (8)	0.7463 (3)	0.0192 (7)	0.9464 (9)
C25A	0.4187 (5)	0.55559 (8)	0.6447 (3)	0.0213 (7)	0.9464 (9)
C26A	0.4305 (5)	0.51739 (8)	0.6596 (3)	0.0226 (8)	0.9464 (9)
F22A	0.6985 (5)	0.51293 (6)	0.9979 (2)	0.0260 (6)	0.9464 (9)
F23A	0.6640 (4)	0.58526 (6)	0.9684 (2)	0.0253 (7)	0.9464 (9)
F25A	0.3283 (4)	0.56911 (7)	0.5268 (2)	0.0306 (7)	0.9464 (9)
F26A	0.3461 (4)	0.49677 (6)	0.5553 (2)	0.0267 (6)	0.9464 (9)
C27A	0.5470 (6)	0.45970 (11)	0.7992 (4)	0.0311 (4)	0.9464 (9)
O21A	0.4346 (4)	0.43983 (8)	0.7101 (3)	0.0311 (4)	0.9464 (9)
H21A	0.4548	0.4171	0.7256	0.037*	0.9464 (9)
O22A	0.6547 (4)	0.44595 (8)	0.8901 (3)	0.0311 (4)	0.9464 (9)
I2B	0.5134 (8)	0.44793 (15)	0.7693 (6)	0.0311 (4)	0.0536 (9)
C21B	0.474 (5)	0.5843 (2)	0.731 (3)	0.0192 (7)	0.0536 (9)
C22B	0.398 (5)	0.5605 (3)	0.625 (2)	0.0213 (7)	0.0536 (9)
C23B	0.428 (6)	0.5227 (3)	0.6297 (18)	0.0226 (8)	0.0536 (9)
C24B	0.519 (5)	0.50544 (19)	0.7470 (17)	0.0211 (7)	0.0536 (9)
C25B	0.596 (6)	0.5284 (2)	0.851 (2)	0.0199 (7)	0.0536 (9)
C26B	0.583 (5)	0.5667 (2)	0.842 (2)	0.0195 (7)	0.0536 (9)
F22B	0.275 (7)	0.5734 (6)	0.520 (4)	0.0306 (7)	0.0536 (9)
F23B	0.353 (8)	0.5021 (4)	0.523 (2)	0.0267 (6)	0.0536 (9)
F25B	0.697 (9)	0.5138 (3)	0.964 (3)	0.0260 (6)	0.0536 (9)
F26B	0.693 (7)	0.5863 (3)	0.938 (4)	0.0253 (7)	0.0536 (9)
C27B	0.447 (4)	0.6254 (2)	0.718 (3)	0.02327 (8)	0.0536 (9)
O21B	0.567 (5)	0.6421 (8)	0.658 (4)	0.02327 (8)	0.0536 (9)
H21B	0.5509	0.6653	0.6591	0.028*	0.0536 (9)
O22B	0.316 (5)	0.6412 (7)	0.745 (4)	0.02327 (8)	0.0536 (9)
N31	0.0063 (4)	0.11941 (10)	0.7323 (3)	0.0246 (7)
C32	−0.0447 (5)	0.09553 (12)	0.6299 (4)	0.0259 (8)
H32A	−0.0842	0.1053	0.5417	0.031*
C33	−0.0424 (5)	0.05733 (11)	0.6467 (4)	0.0249 (8)
H33A	−0.0804	0.0411	0.5722	0.030*
C34	0.0172 (5)	0.04335 (11)	0.7760 (4)	0.0213 (7)
C37	0.0208 (5)	0.00342 (12)	0.7953 (4)	0.0267 (8)
N37	0.0226 (5)	−0.02800 (11)	0.8086 (4)	0.0362 (9)
C35	0.0718 (6)	0.06773 (11)	0.8833 (4)	0.0263 (8)
H35A	0.1146	0.0587	0.9722	0.032*
C36	0.0618 (6)	0.10549 (12)	0.8564 (4)	0.0261 (8)
H36A	0.0959	0.1224	0.9294	0.031*
N41	0.4891 (5)	0.36706 (10)	0.7526 (4)	0.0275 (7)
C42	0.4386 (6)	0.34410 (12)	0.6477 (4)	0.0283 (8)
H42A	0.3886	0.3546	0.5621	0.034*
C43	0.4560 (5)	0.30616 (12)	0.6582 (4)	0.0267 (8)
H43A	0.4193	0.2906	0.5816	0.032*
C44	0.5289 (5)	0.29081 (11)	0.7844 (4)	0.0230 (7)
C47	0.5450 (6)	0.25116 (12)	0.7976 (5)	0.0291 (8)
N47	0.5539 (6)	0.21959 (12)	0.8057 (5)	0.0427 (10)
C45	0.5836 (5)	0.31443 (12)	0.8941 (4)	0.0264 (8)
H45A	0.6361	0.3048	0.9805	0.032*
C46	0.5596 (5)	0.35219 (12)	0.8740 (4)	0.0266 (8)
H46A	0.5941	0.3684	0.9488	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1A	0.02847 (13)	0.01370 (12)	0.02260 (12)	0.00090 (8)	0.00278 (9)	0.00021 (9)
C11A	0.0250 (16)	0.0158 (17)	0.0196 (16)	0.0007 (13)	0.0035 (13)	−0.0007 (13)
C12A	0.0228 (16)	0.0170 (17)	0.0165 (14)	0.0019 (13)	0.0030 (12)	0.0008 (13)
C13A	0.0239 (16)	0.0152 (17)	0.0200 (15)	−0.0030 (13)	0.0041 (13)	−0.0041 (13)
C14A	0.0217 (15)	0.0142 (16)	0.0196 (15)	−0.0041 (12)	0.0086 (12)	−0.0020 (12)
C15A	0.0179 (15)	0.0219 (18)	0.0174 (14)	0.0016 (12)	0.0019 (12)	0.0026 (13)
C16A	0.0219 (15)	0.0152 (17)	0.0225 (16)	−0.0025 (12)	−0.0007 (13)	−0.0038 (13)
F12A	0.0368 (13)	0.0197 (12)	0.0194 (11)	0.0040 (9)	−0.0033 (10)	0.0016 (9)
F13A	0.0348 (12)	0.0168 (12)	0.0201 (10)	−0.0027 (9)	−0.0024 (9)	−0.0048 (9)
F15A	0.0361 (12)	0.0214 (12)	0.0210 (11)	0.0047 (10)	−0.0057 (9)	0.0011 (9)
F16A	0.0371 (12)	0.0180 (12)	0.0247 (11)	−0.0016 (10)	−0.0052 (10)	−0.0036 (9)
C17A	0.0445 (11)	0.0169 (9)	0.0311 (10)	0.0011 (8)	−0.0032 (8)	0.0012 (8)
O11A	0.0445 (11)	0.0169 (9)	0.0311 (10)	0.0011 (8)	−0.0032 (8)	0.0012 (8)
O12A	0.0445 (11)	0.0169 (9)	0.0311 (10)	0.0011 (8)	−0.0032 (8)	0.0012 (8)
I1B	0.0445 (11)	0.0169 (9)	0.0311 (10)	0.0011 (8)	−0.0032 (8)	0.0012 (8)
C11B	0.0217 (15)	0.0142 (16)	0.0196 (15)	−0.0041 (12)	0.0086 (12)	−0.0020 (12)
C12B	0.0179 (15)	0.0219 (18)	0.0174 (14)	0.0016 (12)	0.0019 (12)	0.0026 (13)
C13B	0.0219 (15)	0.0152 (17)	0.0225 (16)	−0.0025 (12)	−0.0007 (13)	−0.0038 (13)
C14B	0.0250 (16)	0.0158 (17)	0.0196 (16)	0.0007 (13)	0.0035 (13)	−0.0007 (13)
C15B	0.0228 (16)	0.0170 (17)	0.0165 (14)	0.0019 (13)	0.0030 (12)	0.0008 (13)
C16B	0.0239 (16)	0.0152 (17)	0.0200 (15)	−0.0030 (13)	0.0041 (13)	−0.0041 (13)
F12B	0.0361 (12)	0.0214 (12)	0.0210 (11)	0.0047 (10)	−0.0057 (9)	0.0011 (9)
F13B	0.0371 (12)	0.0180 (12)	0.0247 (11)	−0.0016 (10)	−0.0052 (10)	−0.0036 (9)
F15B	0.0368 (13)	0.0197 (12)	0.0194 (11)	0.0040 (9)	−0.0033 (10)	0.0016 (9)
F16B	0.0348 (12)	0.0168 (12)	0.0201 (10)	−0.0027 (9)	−0.0024 (9)	−0.0048 (9)
C17B	0.02847 (13)	0.01370 (12)	0.02260 (12)	0.00090 (8)	0.00278 (9)	0.00021 (9)
O11B	0.02847 (13)	0.01370 (12)	0.02260 (12)	0.00090 (8)	0.00278 (9)	0.00021 (9)
O12B	0.02847 (13)	0.01370 (12)	0.02260 (12)	0.00090 (8)	0.00278 (9)	0.00021 (9)
I2A	0.02768 (13)	0.01443 (13)	0.02651 (13)	0.00076 (9)	0.00223 (10)	0.00222 (10)
C21A	0.0266 (17)	0.0170 (18)	0.0185 (16)	−0.0008 (14)	0.0013 (14)	0.0023 (14)
C22A	0.0241 (16)	0.0186 (18)	0.0157 (15)	0.0010 (13)	0.0005 (13)	0.0038 (13)
C23A	0.0252 (16)	0.0154 (17)	0.0165 (15)	−0.0023 (13)	0.0005 (13)	0.0007 (13)
C24A	0.0252 (17)	0.0136 (17)	0.0201 (16)	0.0027 (13)	0.0075 (13)	−0.0001 (13)
C25A	0.0221 (16)	0.0205 (19)	0.0195 (16)	0.0010 (14)	−0.0006 (13)	0.0054 (14)
C26A	0.0254 (17)	0.0194 (19)	0.0205 (17)	−0.0046 (14)	−0.0017 (14)	0.0003 (14)
F22A	0.0382 (12)	0.0202 (12)	0.0162 (11)	0.0043 (9)	−0.0034 (12)	0.0030 (9)
F23A	0.0360 (14)	0.0186 (12)	0.0193 (11)	−0.0023 (9)	−0.0001 (10)	−0.0037 (9)
F25A	0.0362 (17)	0.0267 (14)	0.0225 (11)	0.0016 (10)	−0.0104 (11)	0.0048 (10)
F26A	0.0363 (13)	0.0231 (13)	0.0183 (11)	−0.0066 (10)	−0.0005 (11)	−0.0041 (9)
C27A	0.0383 (11)	0.0182 (10)	0.0335 (11)	0.0017 (8)	−0.0014 (8)	0.0032 (8)
O21A	0.0383 (11)	0.0182 (10)	0.0335 (11)	0.0017 (8)	−0.0014 (8)	0.0032 (8)
O22A	0.0383 (11)	0.0182 (10)	0.0335 (11)	0.0017 (8)	−0.0014 (8)	0.0032 (8)
I2B	0.0383 (11)	0.0182 (10)	0.0335 (11)	0.0017 (8)	−0.0014 (8)	0.0032 (8)
C21B	0.0252 (17)	0.0136 (17)	0.0201 (16)	0.0027 (13)	0.0075 (13)	−0.0001 (13)
C22B	0.0221 (16)	0.0205 (19)	0.0195 (16)	0.0010 (14)	−0.0006 (13)	0.0054 (14)
C23B	0.0254 (17)	0.0194 (19)	0.0205 (17)	−0.0046 (14)	−0.0017 (14)	0.0003 (14)
C24B	0.0266 (17)	0.0170 (18)	0.0185 (16)	−0.0008 (14)	0.0013 (14)	0.0023 (14)
C25B	0.0241 (16)	0.0186 (18)	0.0157 (15)	0.0010 (13)	0.0005 (13)	0.0038 (13)
C26B	0.0252 (16)	0.0154 (17)	0.0165 (15)	−0.0023 (13)	0.0005 (13)	0.0007 (13)
F22B	0.0362 (17)	0.0267 (14)	0.0225 (11)	0.0016 (10)	−0.0104 (11)	0.0048 (10)
F23B	0.0363 (13)	0.0231 (13)	0.0183 (11)	−0.0066 (10)	−0.0005 (11)	−0.0041 (9)
F25B	0.0382 (12)	0.0202 (12)	0.0162 (11)	0.0043 (9)	−0.0034 (12)	0.0030 (9)
F26B	0.0360 (14)	0.0186 (12)	0.0193 (11)	−0.0023 (9)	−0.0001 (10)	−0.0037 (9)
C27B	0.02768 (13)	0.01443 (13)	0.02651 (13)	0.00076 (9)	0.00223 (10)	0.00222 (10)
O21B	0.02768 (13)	0.01443 (13)	0.02651 (13)	0.00076 (9)	0.00223 (10)	0.00222 (10)
O22B	0.02768 (13)	0.01443 (13)	0.02651 (13)	0.00076 (9)	0.00223 (10)	0.00222 (10)
N31	0.0302 (16)	0.0171 (15)	0.0261 (15)	0.0009 (12)	0.0047 (13)	0.0005 (13)
C32	0.0323 (19)	0.022 (2)	0.0220 (16)	0.0004 (15)	0.0024 (14)	0.0007 (15)
C33	0.0302 (18)	0.0188 (19)	0.0241 (17)	−0.0005 (14)	0.0012 (14)	−0.0030 (14)
C34	0.0230 (16)	0.0151 (17)	0.0269 (17)	0.0004 (13)	0.0076 (14)	0.0020 (14)
C37	0.0287 (19)	0.0198 (19)	0.032 (2)	−0.0011 (14)	0.0060 (16)	0.0022 (15)
N37	0.045 (2)	0.023 (2)	0.039 (2)	−0.0024 (16)	0.0028 (17)	−0.0013 (16)
C35	0.037 (2)	0.0199 (19)	0.0216 (16)	0.0023 (15)	0.0040 (15)	0.0021 (14)
C36	0.037 (2)	0.0178 (19)	0.0228 (16)	0.0001 (15)	0.0036 (15)	−0.0049 (14)
N41	0.0313 (17)	0.0165 (16)	0.0332 (17)	0.0014 (12)	0.0025 (14)	0.0023 (13)
C42	0.0308 (19)	0.025 (2)	0.0279 (18)	0.0021 (15)	0.0032 (15)	0.0056 (16)
C43	0.0298 (18)	0.023 (2)	0.0258 (18)	0.0003 (15)	0.0019 (15)	−0.0045 (15)
C44	0.0215 (16)	0.0163 (17)	0.0304 (19)	0.0004 (13)	0.0033 (14)	0.0002 (14)
C47	0.0306 (19)	0.0195 (19)	0.036 (2)	0.0013 (15)	0.0022 (16)	−0.0015 (16)
N47	0.051 (2)	0.0203 (19)	0.051 (2)	0.0001 (17)	−0.0029 (19)	−0.0014 (18)
C45	0.0295 (18)	0.025 (2)	0.0232 (17)	−0.0004 (15)	0.0012 (14)	−0.0023 (15)
C46	0.0304 (18)	0.021 (2)	0.0270 (18)	0.0011 (14)	0.0020 (15)	−0.0054 (15)

Geometric parameters (Å, º)

I1A—C14A	2.077 (3)	C27A—O22A	1.202 (4)
C11A—C12A	1.398 (4)	C27A—O21A	1.314 (5)
C11A—C16A	1.403 (4)	O21A—H21A	0.8400
C11A—C17A	1.491 (5)	I2B—C24B	2.077 (3)
C12A—F12A	1.344 (3)	C21B—C22B	1.398 (4)
C12A—C13A	1.377 (4)	C21B—C26B	1.403 (4)
C13A—F13A	1.337 (3)	C21B—C27B	1.491 (5)
C13A—C14A	1.389 (4)	C22B—F22B	1.344 (3)
C14A—C15A	1.371 (4)	C22B—C23B	1.377 (4)
C15A—F15A	1.341 (3)	C23B—F23B	1.337 (3)
C15A—C16A	1.379 (4)	C23B—C24B	1.390 (4)
C16A—F16A	1.339 (3)	C24B—C25B	1.372 (4)
C17A—O12A	1.202 (4)	C25B—F25B	1.341 (3)
C17A—O11A	1.315 (4)	C25B—C26B	1.380 (4)
O11A—H11A	0.8400	C26B—F26B	1.340 (3)
I1B—C14B	2.077 (3)	C27B—O22B	1.202 (4)
C11B—C12B	1.398 (4)	C27B—O21B	1.315 (5)
C11B—C16B	1.403 (4)	O21B—H21B	0.8400
C11B—C17B	1.491 (5)	N31—C36	1.339 (5)
C12B—F12B	1.344 (3)	N31—C32	1.341 (5)
C12B—C13B	1.377 (4)	C32—C33	1.381 (6)
C13B—F13B	1.337 (3)	C32—H32A	0.9500
C13B—C14B	1.389 (4)	C33—C34	1.389 (5)
C14B—C15B	1.372 (4)	C33—H33A	0.9500
C15B—F15B	1.341 (3)	C34—C35	1.391 (5)
C15B—C16B	1.380 (4)	C34—C37	1.446 (6)
C16B—F16B	1.340 (3)	C37—N37	1.135 (6)
C17B—O12B	1.202 (4)	C35—C36	1.381 (6)
C17B—O11B	1.315 (5)	C35—H35A	0.9500
O12B—H12B	0.8400	C36—H36A	0.9500
I2A—C24A	2.077 (3)	N41—C42	1.337 (6)
C21A—C22A	1.398 (4)	N41—C46	1.347 (5)
C21A—C26A	1.403 (4)	C42—C43	1.370 (6)
C21A—C27A	1.490 (5)	C42—H42A	0.9500
C22A—F22A	1.343 (3)	C43—C44	1.398 (6)
C22A—C23A	1.376 (4)	C43—H43A	0.9500
C23A—F23A	1.337 (3)	C44—C45	1.392 (5)
C23A—C24A	1.389 (4)	C44—C47	1.432 (6)
C24A—C25A	1.372 (4)	C47—N47	1.137 (6)
C25A—F25A	1.341 (3)	C45—C46	1.377 (6)
C25A—C26A	1.380 (4)	C45—H45A	0.9500
C26A—F26A	1.340 (3)	C46—H46A	0.9500
C12A—C11A—C16A	115.1 (3)	C25A—C26A—C21A	121.8 (3)
C12A—C11A—C17A	120.8 (3)	O22A—C27A—O21A	122.9 (4)
C16A—C11A—C17A	124.1 (3)	O22A—C27A—C21A	123.4 (4)
F12A—C12A—C13A	116.7 (2)	O21A—C27A—C21A	113.7 (3)
F12A—C12A—C11A	120.7 (3)	C27A—O21A—H21A	109.5
C13A—C12A—C11A	122.6 (2)	C22B—C21B—C26B	115.0 (3)
F13A—C13A—C12A	118.6 (2)	C22B—C21B—C27B	120.6 (3)
F13A—C13A—C14A	120.1 (3)	C26B—C21B—C27B	124.3 (3)
C12A—C13A—C14A	121.3 (2)	F22B—C22B—C23B	116.6 (3)
C15A—C14A—C13A	116.9 (3)	F22B—C22B—C21B	120.6 (3)
C15A—C14A—I1A	121.6 (2)	C23B—C22B—C21B	122.5 (3)
C13A—C14A—I1A	121.4 (2)	F23B—C23B—C22B	118.5 (3)
F15A—C15A—C14A	119.9 (3)	F23B—C23B—C24B	120.0 (3)
F15A—C15A—C16A	117.9 (3)	C22B—C23B—C24B	121.1 (3)
C14A—C15A—C16A	122.2 (2)	C25B—C24B—C23B	116.8 (3)
F16A—C16A—C15A	116.8 (2)	C25B—C24B—I2B	121.8 (2)
F16A—C16A—C11A	121.4 (3)	C23B—C24B—I2B	121.2 (2)
C15A—C16A—C11A	121.9 (3)	F25B—C25B—C24B	119.9 (3)
O12A—C17A—O11A	122.7 (4)	F25B—C25B—C26B	117.8 (3)
O12A—C17A—C11A	123.6 (4)	C24B—C25B—C26B	122.1 (3)
O11A—C17A—C11A	113.6 (3)	F26B—C26B—C25B	116.8 (3)
C17A—O11A—H11A	109.5	F26B—C26B—C21B	121.2 (3)
C12B—C11B—C16B	115.0 (3)	C25B—C26B—C21B	121.7 (3)
C12B—C11B—C17B	120.6 (3)	O22B—C27B—O21B	122.6 (4)
C16B—C11B—C17B	124.2 (3)	O22B—C27B—C21B	123.3 (4)
F12B—C12B—C13B	116.6 (3)	O21B—C27B—C21B	113.5 (3)
F12B—C12B—C11B	120.6 (3)	C27B—O21B—H21B	109.5
C13B—C12B—C11B	122.5 (3)	C36—N31—C32	118.3 (4)
F13B—C13B—C12B	118.5 (3)	N31—C32—C33	123.0 (4)
F13B—C13B—C14B	120.1 (3)	N31—C32—H32A	118.5
C12B—C13B—C14B	121.2 (3)	C33—C32—H32A	118.5
C15B—C14B—C13B	116.8 (3)	C32—C33—C34	117.9 (4)
C15B—C14B—I1B	121.8 (2)	C32—C33—H33A	121.0
C13B—C14B—I1B	121.2 (2)	C34—C33—H33A	121.0
F15B—C15B—C14B	119.9 (3)	C33—C34—C35	119.8 (4)
F15B—C15B—C16B	117.8 (3)	C33—C34—C37	118.6 (4)
C14B—C15B—C16B	122.1 (3)	C35—C34—C37	121.6 (4)
F16B—C16B—C15B	116.8 (3)	N37—C37—C34	179.0 (5)
F16B—C16B—C11B	121.2 (3)	C36—C35—C34	117.9 (4)
C15B—C16B—C11B	121.8 (3)	C36—C35—H35A	121.1
O12B—C17B—O11B	122.7 (4)	C34—C35—H35A	121.1
O12B—C17B—C11B	123.4 (4)	N31—C36—C35	123.0 (4)
O11B—C17B—C11B	113.6 (3)	N31—C36—H36A	118.5
C17B—O12B—H12B	109.5	C35—C36—H36A	118.5
C22A—C21A—C26A	115.1 (3)	C42—N41—C46	118.5 (4)
C22A—C21A—C27A	120.5 (3)	N41—C42—C43	122.9 (4)
C26A—C21A—C27A	124.5 (3)	N41—C42—H42A	118.6
F22A—C22A—C23A	116.7 (2)	C43—C42—H42A	118.6
F22A—C22A—C21A	120.6 (3)	C42—C43—C44	118.5 (4)
C23A—C22A—C21A	122.7 (2)	C42—C43—H43A	120.8
F23A—C23A—C22A	118.6 (2)	C44—C43—H43A	120.8
F23A—C23A—C24A	120.1 (3)	C45—C44—C43	119.2 (4)
C22A—C23A—C24A	121.3 (2)	C45—C44—C47	121.6 (4)
C25A—C24A—C23A	116.9 (3)	C43—C44—C47	119.2 (4)
C25A—C24A—I2A	122.0 (2)	N47—C47—C44	178.3 (5)
C23A—C24A—I2A	121.1 (2)	C46—C45—C44	118.1 (4)
F25A—C25A—C24A	120.0 (3)	C46—C45—H45A	120.9
F25A—C25A—C26A	117.8 (3)	C44—C45—H45A	120.9
C24A—C25A—C26A	122.2 (3)	N41—C46—C45	122.7 (4)
F26A—C26A—C25A	117.0 (2)	N41—C46—H46A	118.6
F26A—C26A—C21A	121.2 (3)	C45—C46—H46A	118.6
C16A—C11A—C12A—F12A	−178.6 (3)	F23A—C23A—C24A—C25A	−179.9 (4)
C17A—C11A—C12A—F12A	1.6 (6)	C22A—C23A—C24A—C25A	−0.3 (6)
C16A—C11A—C12A—C13A	−0.5 (6)	F23A—C23A—C24A—I2A	1.2 (5)
C17A—C11A—C12A—C13A	179.7 (4)	C22A—C23A—C24A—I2A	−179.2 (3)
F12A—C12A—C13A—F13A	−1.9 (5)	C23A—C24A—C25A—F25A	−179.2 (4)
C11A—C12A—C13A—F13A	179.9 (3)	I2A—C24A—C25A—F25A	−0.3 (5)
F12A—C12A—C13A—C14A	178.2 (3)	C23A—C24A—C25A—C26A	1.7 (6)
C11A—C12A—C13A—C14A	0.0 (6)	I2A—C24A—C25A—C26A	−179.4 (3)
F13A—C13A—C14A—C15A	−179.7 (3)	F25A—C25A—C26A—F26A	−1.6 (6)
C12A—C13A—C14A—C15A	0.2 (5)	C24A—C25A—C26A—F26A	177.6 (4)
F13A—C13A—C14A—I1A	1.5 (5)	F25A—C25A—C26A—C21A	178.5 (4)
C12A—C13A—C14A—I1A	−178.5 (3)	C24A—C25A—C26A—C21A	−2.4 (7)
C13A—C14A—C15A—F15A	179.5 (3)	C22A—C21A—C26A—F26A	−178.5 (4)
I1A—C14A—C15A—F15A	−1.7 (5)	C27A—C21A—C26A—F26A	1.5 (7)
C13A—C14A—C15A—C16A	0.1 (5)	C22A—C21A—C26A—C25A	1.4 (6)
I1A—C14A—C15A—C16A	178.9 (3)	C27A—C21A—C26A—C25A	−178.6 (4)
F15A—C15A—C16A—F16A	−0.5 (5)	C22A—C21A—C27A—O22A	−13.8 (7)
C14A—C15A—C16A—F16A	178.9 (3)	C26A—C21A—C27A—O22A	166.3 (5)
F15A—C15A—C16A—C11A	179.9 (4)	C22A—C21A—C27A—O21A	165.3 (4)
C14A—C15A—C16A—C11A	−0.7 (6)	C26A—C21A—C27A—O21A	−14.7 (7)
C12A—C11A—C16A—F16A	−178.7 (3)	C26B—C21B—C22B—F22B	173 (3)
C17A—C11A—C16A—F16A	1.1 (6)	C27B—C21B—C22B—F22B	−11 (3)
C12A—C11A—C16A—C15A	0.8 (6)	C26B—C21B—C22B—C23B	0 (3)
C17A—C11A—C16A—C15A	−179.4 (4)	C27B—C21B—C22B—C23B	176 (3)
C12A—C11A—C17A—O12A	−0.6 (8)	F22B—C22B—C23B—F23B	8 (3)
C16A—C11A—C17A—O12A	179.7 (5)	C21B—C22B—C23B—F23B	−179 (3)
C12A—C11A—C17A—O11A	178.8 (4)	F22B—C22B—C23B—C24B	−165 (3)
C16A—C11A—C17A—O11A	−1.0 (7)	C21B—C22B—C23B—C24B	8 (2)
C16B—C11B—C12B—F12B	167 (4)	F23B—C23B—C24B—C25B	179 (3)
C17B—C11B—C12B—F12B	−17 (4)	C22B—C23B—C24B—C25B	−8 (2)
C16B—C11B—C12B—C13B	−6 (2)	F23B—C23B—C24B—I2B	−7 (3)
C17B—C11B—C12B—C13B	169 (3)	C22B—C23B—C24B—I2B	166 (3)
F12B—C12B—C13B—F13B	21 (5)	C23B—C24B—C25B—F25B	−175 (4)
C11B—C12B—C13B—F13B	−165 (4)	I2B—C24B—C25B—F25B	11 (4)
F12B—C12B—C13B—C14B	−165 (4)	C23B—C24B—C25B—C26B	1 (3)
C11B—C12B—C13B—C14B	9 (2)	I2B—C24B—C25B—C26B	−173 (3)
F13B—C13B—C14B—C15B	170 (4)	F25B—C25B—C26B—F26B	9 (4)
C12B—C13B—C14B—C15B	−3 (3)	C24B—C25B—C26B—F26B	−167 (4)
F13B—C13B—C14B—I1B	−15 (4)	F25B—C25B—C26B—C21B	−177 (3)
C12B—C13B—C14B—I1B	171 (2)	C24B—C25B—C26B—C21B	7 (3)
C13B—C14B—C15B—F15B	171 (5)	C22B—C21B—C26B—F26B	167 (4)
I1B—C14B—C15B—F15B	−3 (5)	C27B—C21B—C26B—F26B	−10 (3)
C13B—C14B—C15B—C16B	−4 (3)	C22B—C21B—C26B—C25B	−7 (2)
I1B—C14B—C15B—C16B	−179 (2)	C27B—C21B—C26B—C25B	177 (3)
F15B—C15B—C16B—F16B	16 (6)	C22B—C21B—C27B—O22B	86 (3)
C14B—C15B—C16B—F16B	−169 (5)	C26B—C21B—C27B—O22B	−98 (3)
F15B—C15B—C16B—C11B	−169 (5)	C22B—C21B—C27B—O21B	−85 (3)
C14B—C15B—C16B—C11B	7 (3)	C26B—C21B—C27B—O21B	91 (3)
C12B—C11B—C16B—F16B	174 (4)	C36—N31—C32—C33	0.0 (6)
C17B—C11B—C16B—F16B	−2 (4)	N31—C32—C33—C34	−0.6 (6)
C12B—C11B—C16B—C15B	−2 (3)	C32—C33—C34—C35	0.1 (6)
C17B—C11B—C16B—C15B	−177 (3)	C32—C33—C34—C37	−179.9 (4)
C12B—C11B—C17B—O12B	−26 (5)	C33—C34—C35—C36	0.9 (6)
C16B—C11B—C17B—O12B	149 (5)	C37—C34—C35—C36	−179.2 (4)
C12B—C11B—C17B—O11B	161 (5)	C32—N31—C36—C35	1.1 (6)
C16B—C11B—C17B—O11B	−24 (5)	C34—C35—C36—N31	−1.5 (7)
C26A—C21A—C22A—F22A	−179.8 (4)	C46—N41—C42—C43	−0.2 (6)
C27A—C21A—C22A—F22A	0.2 (6)	N41—C42—C43—C44	0.3 (7)
C26A—C21A—C22A—C23A	0.0 (6)	C42—C43—C44—C45	−0.9 (6)
C27A—C21A—C22A—C23A	−180.0 (4)	C42—C43—C44—C47	178.9 (4)
F22A—C22A—C23A—F23A	−1.1 (6)	C43—C44—C45—C46	1.4 (6)
C21A—C22A—C23A—F23A	179.1 (4)	C47—C44—C45—C46	−178.4 (4)
F22A—C22A—C23A—C24A	179.3 (4)	C42—N41—C46—C45	0.7 (6)
C21A—C22A—C23A—C24A	−0.6 (6)	C44—C45—C46—N41	−1.3 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11A—H11A···N31	0.84	1.82	2.655 (4)	175
O12B—H12B···N37^i	0.84	2.07	2.90 (3)	168
O21A—H21A···N41	0.84	1.83	2.665 (4)	177
O21B—H21B···N47^ii	0.84	2.15	2.97 (3)	163

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2.

(BrCO2) CS—AL-6–2 4-Br-PhCOOH, isonicotinonitrile

Crystal data

(C7H5BrO2)(C6H4N2)	Z = 2
Mr = 305.13	F(000) = 304
Triclinic, P1	Dx = 1.697 Mg m^−3
a = 7.3630 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4800 (12) Å	Cell parameters from 6634 reflections
c = 12.446 (2) Å	θ = 3.1–31.7°
α = 80.617 (8)°	µ = 3.44 mm^−1
β = 84.893 (7)°	T = 120 K
γ = 62.018 (5)°	Plate, colourless
V = 597.19 (17) Å^3	0.44 × 0.24 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	3871 independent reflections
Radiation source: fine-focus sealed tube	3201 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 32.6°, θmin = 1.7°
Absorption correction: multi-scan SADABS	h = −10→10
Tmin = 0.313, Tmax = 0.820	k = −10→10
12685 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.090P)^2] where P = (Fo^2 + 2Fc^2)/3
3871 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 1.55 e Å^−3
0 restraints	Δρmin = −1.67 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.29244 (3)	−0.04467 (4)	0.90536 (2)	0.02437 (11)
C11	0.2806 (4)	0.4890 (4)	0.6474 (2)	0.0196 (5)
O11	0.2129 (3)	0.6662 (3)	0.46871 (19)	0.0284 (4)
H11	0.239 (6)	0.759 (6)	0.415 (3)	0.034*
C12	0.3426 (4)	0.4672 (4)	0.7536 (2)	0.0216 (5)
H12A	0.3818	0.5617	0.7732	0.026*
O12	0.3246 (3)	0.7837 (3)	0.58816 (19)	0.0296 (5)
C13	0.3476 (4)	0.3087 (4)	0.8308 (2)	0.0228 (5)
H13A	0.3890	0.2945	0.9032	0.027*
C14	0.2913 (4)	0.1713 (4)	0.8007 (2)	0.0194 (5)
C15	0.2274 (4)	0.1899 (4)	0.6961 (2)	0.0229 (5)
H15A	0.1881	0.0951	0.6772	0.027*
C16	0.2219 (4)	0.3506 (4)	0.6191 (2)	0.0230 (5)
H16A	0.1781	0.3658	0.5472	0.028*
C17	0.2755 (4)	0.6609 (4)	0.5659 (2)	0.0220 (5)
N21	0.2064 (3)	0.9840 (3)	0.3335 (2)	0.0227 (5)
C22	0.1458 (4)	1.0281 (4)	0.2310 (3)	0.0245 (5)
H22A	0.1050	0.9407	0.2041	0.029*
C23	0.1393 (4)	1.1953 (4)	0.1613 (2)	0.0234 (5)
H23A	0.0926	1.2245	0.0888	0.028*
C24	0.2037 (4)	1.3192 (4)	0.2013 (2)	0.0204 (5)
C25	0.2672 (4)	1.2757 (4)	0.3078 (3)	0.0227 (5)
H25A	0.3099	1.3599	0.3365	0.027*
C26	0.2668 (4)	1.1055 (4)	0.3715 (2)	0.0232 (5)
H26A	0.3109	1.0736	0.4447	0.028*
C27	0.2092 (4)	1.4947 (5)	0.1274 (3)	0.0282 (6)
N27	0.2190 (4)	1.6183 (5)	0.0736 (3)	0.0366 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02002 (14)	0.02207 (16)	0.02686 (18)	−0.00737 (11)	−0.00164 (10)	0.00069 (11)
C11	0.0140 (9)	0.0193 (11)	0.0224 (13)	−0.0054 (8)	−0.0012 (9)	−0.0015 (10)
O11	0.0377 (11)	0.0270 (10)	0.0266 (11)	−0.0203 (9)	−0.0075 (9)	0.0011 (9)
C12	0.0178 (10)	0.0209 (11)	0.0272 (14)	−0.0085 (9)	−0.0020 (9)	−0.0065 (11)
O12	0.0338 (10)	0.0252 (10)	0.0339 (12)	−0.0172 (8)	−0.0072 (9)	0.0001 (9)
C13	0.0195 (10)	0.0235 (12)	0.0241 (14)	−0.0086 (9)	−0.0058 (9)	−0.0010 (11)
C14	0.0154 (9)	0.0184 (11)	0.0213 (13)	−0.0053 (8)	0.0024 (9)	−0.0036 (10)
C15	0.0233 (11)	0.0227 (12)	0.0246 (14)	−0.0119 (10)	−0.0020 (10)	−0.0038 (11)
C16	0.0238 (11)	0.0228 (12)	0.0218 (13)	−0.0100 (10)	−0.0013 (10)	−0.0034 (10)
C17	0.0164 (10)	0.0218 (12)	0.0254 (14)	−0.0068 (9)	−0.0005 (9)	−0.0029 (11)
N21	0.0161 (8)	0.0199 (10)	0.0299 (13)	−0.0069 (8)	−0.0016 (8)	−0.0018 (9)
C22	0.0215 (11)	0.0207 (12)	0.0323 (16)	−0.0100 (10)	−0.0003 (10)	−0.0056 (11)
C23	0.0219 (11)	0.0237 (12)	0.0229 (14)	−0.0088 (10)	−0.0038 (10)	−0.0024 (11)
C24	0.0141 (9)	0.0176 (11)	0.0263 (14)	−0.0052 (8)	−0.0005 (9)	−0.0010 (10)
C25	0.0198 (10)	0.0208 (11)	0.0283 (15)	−0.0101 (9)	−0.0040 (10)	−0.0016 (11)
C26	0.0205 (10)	0.0252 (12)	0.0233 (14)	−0.0100 (10)	−0.0023 (10)	−0.0023 (11)
C27	0.0161 (10)	0.0246 (13)	0.0415 (18)	−0.0043 (10)	−0.0024 (11)	−0.0132 (13)
N27	0.0297 (12)	0.0376 (15)	0.0336 (16)	−0.0089 (12)	−0.0019 (11)	−0.0021 (13)

Geometric parameters (Å, º)

Br1—C14	1.900 (3)	C16—H16A	0.9500
C11—C16	1.396 (4)	N21—C22	1.327 (4)
C11—C12	1.396 (4)	N21—C26	1.343 (4)
C11—C17	1.491 (4)	C22—C23	1.384 (4)
O11—C17	1.320 (4)	C22—H22A	0.9500
O11—H11	0.96 (4)	C23—C24	1.391 (4)
C12—C13	1.387 (4)	C23—H23A	0.9500
C12—H12A	0.9500	C24—C25	1.381 (4)
O12—C17	1.210 (3)	C24—C27	1.490 (5)
C13—C14	1.386 (4)	C25—C26	1.387 (4)
C13—H13A	0.9500	C25—H25A	0.9500
C14—C15	1.386 (4)	C26—H26A	0.9500
C15—C16	1.396 (4)	C27—N27	1.077 (5)
C15—H15A	0.9500
C16—C11—C12	119.6 (3)	O12—C17—C11	122.2 (3)
C16—C11—C17	120.7 (3)	O11—C17—C11	114.0 (2)
C12—C11—C17	119.7 (2)	C22—N21—C26	118.7 (3)
C17—O11—H11	112 (2)	N21—C22—C23	123.1 (3)
C13—C12—C11	120.6 (2)	N21—C22—H22A	118.4
C13—C12—H12A	119.7	C23—C22—H22A	118.4
C11—C12—H12A	119.7	C22—C23—C24	117.7 (3)
C14—C13—C12	118.9 (3)	C22—C23—H23A	121.2
C14—C13—H13A	120.5	C24—C23—H23A	121.2
C12—C13—H13A	120.5	C25—C24—C23	120.0 (3)
C15—C14—C13	121.8 (3)	C25—C24—C27	120.6 (2)
C15—C14—Br1	118.34 (19)	C23—C24—C27	119.4 (3)
C13—C14—Br1	119.8 (2)	C24—C25—C26	118.0 (2)
C14—C15—C16	118.8 (2)	C24—C25—H25A	121.0
C14—C15—H15A	120.6	C26—C25—H25A	121.0
C16—C15—H15A	120.6	N21—C26—C25	122.4 (3)
C11—C16—C15	120.2 (3)	N21—C26—H26A	118.8
C11—C16—H16A	119.9	C25—C26—H26A	118.8
C15—C16—H16A	119.9	N27—C27—C24	178.0 (3)
O12—C17—O11	123.7 (3)
C16—C11—C12—C13	0.4 (4)	C12—C11—C17—O12	0.3 (4)
C17—C11—C12—C13	179.8 (2)	C16—C11—C17—O11	−0.2 (4)
C11—C12—C13—C14	0.4 (4)	C12—C11—C17—O11	−179.5 (2)
C12—C13—C14—C15	−1.0 (4)	C26—N21—C22—C23	−0.8 (4)
C12—C13—C14—Br1	−179.00 (18)	N21—C22—C23—C24	1.3 (4)
C13—C14—C15—C16	0.6 (4)	C22—C23—C24—C25	−1.2 (4)
Br1—C14—C15—C16	178.71 (19)	C22—C23—C24—C27	176.9 (2)
C12—C11—C16—C15	−0.7 (4)	C23—C24—C25—C26	0.8 (4)
C17—C11—C16—C15	179.9 (2)	C27—C24—C25—C26	−177.4 (2)
C14—C15—C16—C11	0.2 (4)	C22—N21—C26—C25	0.3 (4)
C16—C11—C17—O12	179.7 (2)	C24—C25—C26—N21	−0.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···N21	0.96 (4)	1.74 (4)	2.663 (3)	160 (3)

(BrF4OH2) CS—AQ-12–2 4-Br—F4-PhOH, isonicotinonitrile

Crystal data

(C6HBrF4O)(C6H4N2)	F(000) = 680
Mr = 349.09	Dx = 1.904 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.2763 (19) Å	Cell parameters from 4952 reflections
b = 5.0037 (8) Å	θ = 3.1–32.4°
c = 20.666 (3) Å	µ = 3.42 mm^−1
β = 106.425 (4)°	T = 120 K
V = 1217.7 (3) Å^3	Plate, colourless
Z = 4	0.34 × 0.14 × 0.08 mm

Data collection

Bruker APEX-II CCD diffractometer	3721 independent reflections
Radiation source: fine-focus sealed tube	3046 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 32.6°, θmin = 3.1°
Absorption correction: multi-scan SADABS	h = −15→18
Tmin = 0.389, Tmax = 0.771	k = −7→7
9843 measured reflections	l = −28→28

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0725P)^2 + 0.2P] where P = (Fo^2 + 2Fc^2)/3
3721 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 1.49 e Å^−3
0 restraints	Δρmin = −1.42 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C11	0.46363 (17)	0.1824 (4)	0.17122 (9)	0.0216 (4)
O11	0.38185 (14)	0.3074 (3)	0.19042 (7)	0.0274 (3)
H11	0.3546	0.4306	0.1630	0.033*
C12	0.49176 (19)	0.2361 (4)	0.11178 (10)	0.0231 (4)
F12	0.43292 (12)	0.4242 (3)	0.07003 (6)	0.0352 (3)
C13	0.57729 (18)	0.0996 (4)	0.09507 (9)	0.0246 (4)
F13	0.59938 (12)	0.1610 (3)	0.03692 (6)	0.0348 (3)
C14	0.63881 (17)	−0.0951 (4)	0.13650 (10)	0.0257 (4)
Br1	0.75742 (2)	−0.27389 (5)	0.114401 (12)	0.03459 (11)
C15	0.61111 (18)	−0.1534 (4)	0.19528 (10)	0.0255 (4)
F15	0.66751 (13)	−0.3419 (3)	0.23737 (7)	0.0367 (3)
C16	0.52560 (17)	−0.0171 (4)	0.21200 (9)	0.0225 (4)
F16	0.50007 (11)	−0.0774 (3)	0.26942 (6)	0.0314 (3)
N21	0.25526 (15)	0.7037 (4)	0.13017 (9)	0.0237 (3)
C22	0.23957 (19)	0.8433 (4)	0.07281 (10)	0.0257 (4)
H22A	0.2847	0.8007	0.0437	0.031*
C23	0.16062 (18)	1.0464 (4)	0.05424 (9)	0.0256 (4)
H23A	0.1521	1.1440	0.0137	0.031*
C24	0.09421 (17)	1.1032 (4)	0.09683 (9)	0.0224 (4)
C25	0.10940 (17)	0.9608 (4)	0.15637 (9)	0.0242 (4)
H25A	0.0649	0.9974	0.1862	0.029*
C26	0.1918 (2)	0.7636 (4)	0.17063 (10)	0.0240 (4)
H26A	0.2035	0.6661	0.2115	0.029*
C27	0.00832 (19)	1.3095 (4)	0.07912 (10)	0.0260 (4)
N27	−0.05919 (17)	1.4713 (4)	0.06475 (9)	0.0344 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0251 (9)	0.0260 (9)	0.0180 (8)	0.0018 (7)	0.0132 (7)	0.0007 (7)
O11	0.0329 (8)	0.0351 (8)	0.0207 (6)	0.0110 (6)	0.0182 (6)	0.0063 (6)
C12	0.0273 (9)	0.0288 (10)	0.0168 (8)	0.0038 (7)	0.0118 (7)	0.0046 (6)
F12	0.0456 (7)	0.0422 (8)	0.0244 (5)	0.0178 (6)	0.0207 (5)	0.0143 (5)
C13	0.0305 (10)	0.0315 (10)	0.0175 (7)	−0.0012 (8)	0.0158 (7)	−0.0002 (7)
F13	0.0443 (8)	0.0462 (8)	0.0239 (6)	0.0046 (6)	0.0261 (5)	0.0050 (6)
C14	0.0263 (9)	0.0294 (10)	0.0257 (8)	0.0020 (8)	0.0144 (7)	−0.0030 (8)
Br1	0.03317 (15)	0.04001 (16)	0.03713 (15)	0.00902 (9)	0.02056 (10)	−0.00360 (9)
C15	0.0291 (10)	0.0277 (10)	0.0219 (8)	0.0042 (8)	0.0108 (7)	0.0041 (7)
F15	0.0425 (8)	0.0370 (7)	0.0330 (6)	0.0159 (6)	0.0146 (6)	0.0117 (6)
C16	0.0284 (9)	0.0271 (9)	0.0164 (7)	0.0001 (7)	0.0135 (7)	0.0029 (7)
F16	0.0426 (7)	0.0374 (7)	0.0212 (5)	0.0061 (6)	0.0203 (5)	0.0098 (5)
N21	0.0285 (9)	0.0255 (8)	0.0214 (7)	0.0023 (6)	0.0139 (6)	0.0007 (6)
C22	0.0316 (10)	0.0309 (10)	0.0201 (8)	0.0043 (8)	0.0161 (7)	0.0021 (8)
C23	0.0331 (10)	0.0280 (10)	0.0197 (8)	0.0049 (8)	0.0139 (7)	0.0029 (7)
C24	0.0270 (9)	0.0232 (9)	0.0189 (7)	0.0022 (7)	0.0093 (7)	−0.0019 (7)
C25	0.0311 (9)	0.0270 (9)	0.0190 (8)	0.0045 (8)	0.0145 (7)	−0.0006 (7)
C26	0.0335 (10)	0.0243 (9)	0.0185 (8)	0.0049 (7)	0.0143 (7)	0.0024 (6)
C27	0.0325 (10)	0.0301 (10)	0.0188 (8)	0.0048 (8)	0.0128 (7)	−0.0010 (7)
N27	0.0401 (10)	0.0386 (10)	0.0281 (8)	0.0133 (8)	0.0157 (7)	0.0011 (8)

Geometric parameters (Å, º)

C11—O11	1.335 (2)	N21—C26	1.329 (3)
C11—C16	1.387 (3)	N21—C22	1.342 (3)
C11—C12	1.393 (3)	C22—C23	1.382 (3)
O11—H11	0.8400	C22—H22A	0.9500
C12—F12	1.341 (2)	C23—C24	1.388 (3)
C12—C13	1.376 (3)	C23—H23A	0.9500
C13—F13	1.340 (2)	C24—C25	1.388 (3)
C13—C14	1.374 (3)	C24—C27	1.447 (3)
C14—C15	1.382 (3)	C25—C26	1.384 (3)
C14—Br1	1.872 (2)	C25—H25A	0.9500
C15—F15	1.336 (2)	C26—H26A	0.9500
C15—C16	1.375 (3)	C27—N27	1.136 (3)
C16—F16	1.344 (2)
O11—C11—C16	119.09 (17)	C15—C16—C11	122.05 (17)
O11—C11—C12	124.51 (18)	C26—N21—C22	118.38 (18)
C16—C11—C12	116.40 (18)	N21—C22—C23	122.84 (19)
C11—O11—H11	109.5	N21—C22—H22A	118.6
F12—C12—C13	119.81 (18)	C23—C22—H22A	118.6
F12—C12—C11	118.68 (19)	C22—C23—C24	117.78 (18)
C13—C12—C11	121.51 (18)	C22—C23—H23A	121.1
F13—C13—C14	120.43 (18)	C24—C23—H23A	121.1
F13—C13—C12	118.26 (18)	C23—C24—C25	120.10 (18)
C14—C13—C12	121.31 (17)	C23—C24—C27	120.15 (17)
C13—C14—C15	117.97 (18)	C25—C24—C27	119.74 (18)
C13—C14—Br1	121.02 (15)	C26—C25—C24	117.51 (18)
C15—C14—Br1	121.01 (16)	C26—C25—H25A	121.2
F15—C15—C16	118.57 (18)	C24—C25—H25A	121.2
F15—C15—C14	120.68 (19)	N21—C26—C25	123.38 (18)
C16—C15—C14	120.75 (18)	N21—C26—H26A	118.3
F16—C16—C15	119.71 (17)	C25—C26—H26A	118.3
F16—C16—C11	118.24 (17)	N27—C27—C24	179.5 (2)
O11—C11—C12—F12	−0.6 (3)	C14—C15—C16—F16	179.95 (19)
C16—C11—C12—F12	178.85 (18)	F15—C15—C16—C11	179.58 (19)
O11—C11—C12—C13	179.9 (2)	C14—C15—C16—C11	0.1 (3)
C16—C11—C12—C13	−0.6 (3)	O11—C11—C16—F16	0.3 (3)
F12—C12—C13—F13	0.2 (3)	C12—C11—C16—F16	−179.16 (18)
C11—C12—C13—F13	179.71 (19)	O11—C11—C16—C15	−179.87 (19)
F12—C12—C13—C14	−179.67 (19)	C12—C11—C16—C15	0.7 (3)
C11—C12—C13—C14	−0.2 (3)	C26—N21—C22—C23	0.1 (3)
F13—C13—C14—C15	−178.91 (19)	N21—C22—C23—C24	−1.0 (3)
C12—C13—C14—C15	1.0 (3)	C22—C23—C24—C25	1.0 (3)
F13—C13—C14—Br1	1.6 (3)	C22—C23—C24—C27	−178.53 (19)
C12—C13—C14—Br1	−178.47 (16)	C23—C24—C25—C26	−0.2 (3)
C13—C14—C15—F15	179.60 (19)	C27—C24—C25—C26	179.30 (19)
Br1—C14—C15—F15	−0.9 (3)	C22—N21—C26—C25	0.7 (3)
C13—C14—C15—C16	−1.0 (3)	C24—C25—C26—N21	−0.7 (3)
Br1—C14—C15—C16	178.50 (16)	C23—C24—C27—N27	26 (38)
F15—C15—C16—F16	−0.6 (3)	C25—C24—C27—N27	−154 (38)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···N21	0.84	1.83	2.608 (2)	154