research communications
The crystal structures of salts of N-(4-fluorophenyl)piperazine with four aromatic carboxylic acids and with picric acid
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India, bDepartment of Chemistry, Maharani's Science College for Women, Mysuru-570 001, India, cInstitute of Materials Science, Darmstadt University of Technology, Alarich-Weiss-Strasse 2, D-64287 Darmstadt, Germany, and dSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
*Correspondence e-mail: yathirajan@hotmail.com
The structures are reported for five salts formed by reactions between N-(4-fluorophenyl)piperazine and aromatic acids. In 4-(4-fluorophenyl)piperazin-1-ium 2-fluorobenzoate monohydrate, C10H14FN2+·C7H4FO2−·H2O, (I), the components are linked by a combination of N—H⋯O and O—H⋯O hydrogen bonds to form a chain of alternating R46(12) and R66(16) rings. The ionic components of 4-(4-fluorophenyl)piperazin-1-ium 2-bromobenzoate 0.353-hydrate, C10H14FN2+·C7H4BrO2−·0.353H2O, (II), are linked by N—H⋯O hydrogen bonds to form a centrosymmetric four-ion aggregate containing an R44(12) motif, and these aggregates are linked into a molecular ladder by a single C—H⋯π(arene) hydrogen bond. 4-(4-Fluorophenyl)piperazin-1-ium 2-iodobenzoate, C10H14FN2+·C7H4IO2−, (III), crystallizes with Z′ = 2 in P: the four independent ions are linked by N—H⋯O hydrogen bonds to form a non-centrosymmetric aggregate again containing an R44(12) motif, and aggregates of this type are linked into a ribbon by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds. The anion in 4-(4-fluorophenyl)piperazin-1-ium 2,4,6-trinitrophenolate, C10H14FN2+·C6H2N3O7−, (IV), shows clear evidence of extensive electronic delocalization from the phenolate O atom into the adjacent ring. The ions are linked by a combination of two-centre N—H⋯O and three-centre N—H⋯(O)2 hydrogen bonds to form centrosymmetric four-ion aggregates containing three types of ring. The ions in 4-(4-fluorophenyl)piperazin-1-ium 3,5-dinitrobenzoate, C10H14FN2+·C7H3N2O6−, (V), are again linked by N—H⋯O hydrogen bonds to form centrosymmetric R44(12) aggregates, which are themselves linked by a C—H⋯π(arene) hydrogen bond to form sheets, the stacking of which leads to the formation of narrow channels, containing disordered and/or mobile solvent entities. Comparisons are made with some related structures.
1. Chemical context
N-(4-fluorophenyl)piperazine (C10H13N2F; 4-FPP) has mild psychedelic and euphorigenic properties and, in this respect, it exhibits effects similar to those of the related compound N-(4-methoxyphenyl)piperazine (MeOPP), which has been used as a recreational drug (Nagai et al., 2007). 4-FPP is also is a major metabolite (Keane et al., 1982; Sanjuan et al., 1983) of the sedative and hypnotic drug niaprazine, N-{4-[4-(4-fluorophenyl)piperazin-1-yl]butan-2-yl}pyridine-3-carboxamide, used in the treatment of autistic disorders (Rossi et al., 1999).
We have recently reported (Harish Chinthal et al., 2020) the structures of the salts formed between 4-FPP and 2-hydroxy-3,5-dinitrobenzoic, oxalic and (2R,3R)-tartaric acids, the last of which crystallizes as a monohydrate. That work was a development from our structural studies (Kiran Kumar et al., 2019, 2020) of a wide range of salts formed between organic acids and MeOPP. As part of our study of 4-FPP, we now report the structures of five salts formed between 4-FPP and four aromatic carboxylic acids and picric acid, namely 4-(4-fluorophenyl)piperazin-1-ium 2-fluorobenzoate monohydrate (I), 4-(4-fluorophenyl)piperazin-1-ium 2-bromobenzoate 0.353(hydrate) (II), 4-(4-fluorophenyl)piperazin-1-ium 2-iodobenzoate (III), 4-(4-fluorophenyl)piperazin-1-ium 2,4,6-trinitrophenolate (IV) and 4-(4-fluorophenyl)piperazin-1-ium 3,5-dinitrobenzoate (V). (Figs. 1–5)
2. Structural commentary
The crystallization characteristics of the 2-halobenzoate salts (I)–(III) are all different (Figs. 1–3), so that no two of them are isostructural. The 2-fluorobenzoate salt (I) crystallizes as a monohydrate. However, the 2-bromobenzoate (II) crystallizes as a partial hydrate: the refined occupancy of the water molecule is 0.353 (8) and the O atom of this component, O41 (Fig. 2), lies close to an inversion centre, such that the O⋯O distance across this centre is only 0.962 (16) Å. Hence, if either of this pair of sites is occupied, the other must be vacant. By contrast, the 2-iodobenzoate (III) crystallizes in solvent-free form with Z′ = 2 in P (Fig. 3). The refined structure of the 3,5-dinitrobenzoate salt (V) contains four void spaces per each of volume 59 Å3, which lie on the twofold rotation axes, and which are connected into narrow channels lying along these axes. Examination of the refined structure using the SQUEEZE procedure (Spek, 2015) showed the the presence of 48 electrons per that were not accounted for by the ionic components, i.e. an average of 12 electrons per void, or rather less than the equivalent of one water molecule. There were two significant peaks in the difference maps, but no plausible solvent model could be developed from these. Hence the SQUEEZE procedure was used prior to the final and the nature of the solvent component remains unknown: it seem likely that the included molecules are disordered and/or mobile within the channels.
In each of the cations in compounds (I)–(V), the piperazine ring adopts an almost perfect chair conformation: in every case the reference cation was selected as one having the ring-puckering angle θ (Cremer & Pople, 1975), as calculated for the atom sequence (N1,C2,C3,N4,C5,C6), or the equivalent sequences in compound (III), close to the ideal value (Boeyens, 1978) of zero, rather than close to 180° as expected for the enantiomeric form of the cation.
The dihedral angles between the aryl ring and the carboxylate group in compounds (I)–(III) and (V) vary from 5.94 (11)° in (V) to 75.9 (2)° in the anion of (III), which contains atom I132 (Fig. 3). The corresponding angles involving the nitro groups in compounds (IV) and (V) span a much smaller range, from 5.24 (11)° for the group containing atom N35 in (V) to 29.09 (6)° for the group containing atom N36 in (IV). This contrasting behaviour may be associated with the differences in the hydrogen-bonding participation of the carboxylate and nitro groups, as discussed below (§ 3).
Within the anion of compound (IV), the distances C31—C32 and C31—C36 of 1.451 (2) and 1.449 (2) Å, respectively are very much longer than the other C—C distances in this ring, which range from 1.365 (2) Å to 1.383 (2) Å; in addition the distance C31—O31 [1.2398 (19) Å] is much close to the values typically found in than to those in (Allen et al., 1987). These values indicate significant delocalization of the negative charge from the atom O31 into the adjacent ring, as shown in the Scheme.
3. Supramolecular features
It is possible to select a compact (Fig. 1) in which the three independent components are linked by two N—H⋯O hydrogen bonds (Table 1). The supramolecular assembly of (I) is determined by a combination of two N—H⋯O hydrogen bonds and two O—H⋯O hydrogen bonds (Table 1). Together these link the three independent components into a chain of centrosymmetric rings running parallel to the [100] direction in which rings of R64(12) type (Bernstein et al., 1995) centred at (n, 0.5, 0.5) alternate with R66(16) rings centred at (n + 0.5, 0.5, 0.5), where n represents an integer in each case (Fig. 6). A weak C—H⋯O hydrogen bond (Table 1), having a fairly small C—H⋯O angle (Wood et al., 2009), links these chains into complex sheets lying parallel to (001).
for compound (I)The ionic components of compound (II) are linked by two independent N—H⋯O hydrogen bonds (Table 1) to form a centrosymmetric four-ion aggregate, characterized by an R44(12) motif, with the reference aggregate centred at (0.5, 0.5, 0.5) (Fig. 7). If the water molecules were present with full occupancy, their role would be the linking of the four-ion aggregates into chains running parallel to the [010] direction: however, the low occupancy of the water sites indicates that continuous chain formation is not possible. On the other hand, a single C—H⋯π(arene) hydrogen bond links these four-ion aggregates into a ribbon, or molecular ladder running parallel to the [100] direction (Fig. 8), in which the centrosymmetric R44(12) rings containing four N—H⋯O hydrogen bonds and centred at (n + 0.5, 0.5, 0.5) alternate with rings containing two each of N—H⋯O and C—H⋯π(arene) hydrogen bonds and centred at (n, 0.5, 0.5), where n represents an integer in each case.
As noted above, compound (III) crystallizes with Z′ = 2 (Fig. 3) and it is possible to select a compact in which the four independent ions are linked by four N—H⋯O hydrogen bonds to form a four-ion R44(12) aggregate, analogous to that in compound (II). The aggregate in (III) exhibits approximate, but non-crystallographic, inversion symmetry with its centroid close to (0.25, 0.25, 0.5): a search for possible additional found none. A combination of one C—H⋯O and one C—H⋯π(arene) hydrogen bonds (Table 1) links the four-ion aggregates into a complex molecular ribbon running parallel to the [010] direction (Fig. 9).
The component ions in compound (IV) are linked by a three-centre (bifurcated) N—H⋯(O)2 hydrogen bond within the selected (Fig. 4, Table 1), while a two centre N—H⋯O hydrogen bond links the ions to form a centrosymmetric four-ion aggregate, in which rings of R12(6), R44(12) and R44(16) types can be identified (Fig. 10): it is interesting to note the occurrence of the R44(12) ring type, exactly as in the structures of compounds (II) and (III). The structure of compound (IV) contains several short C—H⋯O contacts, but in all of these contacts the C—H⋯O angle is close to 140° (Table 1), so that their structural significance is likely to be minimal, at best (Wood et al., 2009).
Inversion-related ion pairs in compound (V) form the same type of R44(12) motif (Fig. 11) as previously seen in each of compounds (II)–(IV). In addition, an almost linear C—H⋯π(arene) hydrogen bond links these four-ion aggregates into a sheet lying parallel to (10) (Fig. 12). A second sheet of this type, related to the first by the twofold rotation axes, also passes through each but there are no direction-specific interactions between adjacent sheets. However, the stacking of the sheets leaves void space in the form of narrow channels lying along the twofold axes (Fig. 13). As noted above (§ 2), the channels appear to contain solvent molecules, which are disordered and/or mobile.
Thus the cyclic R44(12) motif can be identified in some form in each of compounds (II)–(V), although such rings are centrosymmetric in each of (II), (IV) and (V), but non-centrosymmetric in (III), and they are explicit in (II), (III) and (V) (Figs. 3, 7, 11), but masked within a more complex four-ion aggregate in (IV) (Fig. 10).
4. Database survey
It is of interest briefly to compare the structures reported here with those of some closely related compounds. One obvious comparison is between the monohydrated compound (I) reported here and a series of isostructural salts (benzoate, 4-fluorobenzoate, 4-chlorobenzoate and 4-bromobenzoate) of MeOPP [compounds (VI)–(IX)], all of which crystallize as monohydrates (Kiran Kumar et al., 2019). Compounds (VI)–(IX) all form a chain of centrosymmetric R64(12) and R66(16) rings comparable to that found here in compound (I). It is important to emphasize, however, that (I) is not isostructural with (VI)–(IX); thus, although the repeat vectors for the of (I) are somewhat similar to those in (VI)–(IX), the inter-axial angles in (I) are all greater than 90°, whereas in (VI)–(IX) they are consistently less than 90°.
The picrate salt of MeOPP (X) (Kiran Kumar et al., 2020) is analogous to the picrate salt (IV) formed by 4-FPP, and both show the same pattern of electronic delocalization within the anion. While (IV) and (X) both crystallize in P21/n, they are by no means isomorphous, and in (X) two of the nitro groups exhibit disorder. Whereas the N—H⋯O hydrogen bonds in (IV) generate a dimeric structure (Fig. 10), in (X) they generate a chain of rings, and adjacent chains are linked by a C—H⋯π(arene) hydrogen bond to form a sheet parallel to (001) (Kiran Kumar et al., 2020). Similar delocalization is apparent in the anion of the 5-hydroxy-3,5-dinitrobenzoate salts of both 4-FPP (XI) (Harish Chinthal et al., 2020) and MeOPP (XII) (Kiran Kumar et al., 2019). However, in (XI) the ions are linked into a chain of R12(4) and R12(6) rings by two independent three-centre N—H⋯(O)2 hydrogen bonds, while in (XII) a combination of N—H⋯O and C—H⋯O hydrogen bonds generates a chain of alternating R22(10) and R64(16) rings, with the chains further linked into a three-dimensional framework structure by a single C—H⋯π(arene) hydrogen bond.
5. Synthesis and crystallization
All starting materials were obtained commercially, and all were used as received: solutions of N-(4-fluorophenyl)piperazine (100 mg, 0.55 mol) in methanol (10 ml) were mixed with solutions of the appropriate acids (0.55 mol) in methanol (10 ml), viz. 2-fluorobenzoic acid (77.1 mg) for (I), 2-bromobenzoic acid (110.6 mg) for (II), 2-iodobenzoic acid (136.4 mg) for (III), picric acid (126 mg) for (IV) and 3,5-dinitrobenzoic acid (116.7 mg) for (V). The corresponding pairs of solution were mixed and then briefly held at 323 K, before being set aside to crystallize. After two days at room temperature, the resulting solid products were collected by filtration, dried in air and then crystallized, at ambient temperature and in the presence of air from mixture of ethyl acetate and acetone (initial composition 9:1, v/v) for (I), or ethyl acetate and methanol [initial composition 9:1, v/v for (II)–(IV), and 1:1 v/v for (V)]. M.p. (I) 349–351 K, (II) 411–414 K, (III) 409–411 K, (IV) 405–410 K, and (V) 426–430 K. Despite repeated efforts, we have been unable to obtain satisfactory crystals of the 2-chlorobenzoate salt, using solvents such as acetonitrile, acetone, ethyl acetate or methanol, and a number of mixtures of such solvents.
6. Refinement
Crystal data, data collection and . All H atoms, apart from those of the partial-occupancy water molecule in compound (II), were located in difference maps. The H atoms bonded to C atoms were then treated as riding atoms in geometrically idealized positions with C—H distances of 0.93 Å (aromatic) or 0.97 Å (CH2), and with Uiso(H) = 1.2Ueq(C). For the H atoms bonded to N atoms, the atomic coordinates were refined with Uiso(H) = 1.2Ueq(N) giving the N—H distances shown in Table 1. Before the final refinements for compound (V), one low-angle reflection, (110), which had been attenuated by the beam stop, and one bad outlier reflection, (004), were removed from the data set. It was not possible to reliably locate in difference maps the H atoms of the partial-occupancy water molecule in (II); hence they were included in calculated positions, riding at 0.90 Å from the atom O41, at positions calculated by interpolation along the relevant O⋯O vectors, with Uiso(H) = 1.5Ueq(O): the water atom O41 was refined isotropically and the refined occupancy of the water molecule was 0.353 (8). The largest maximum and minimum in the final difference map for (III), +2.92 and −2.00 e Å-3, respectively, were both close to atom I232, at distances of 0.92 and 0.77 Å, respectively. Examination of the difference map for compound (V) after conventional showed the presence of two significant peaks, one of 2.98 e Å−3 lying on a twofold rotation axis, at (0.5, −0.0533, 0.75), and the other, 1.94 e Å−3, lying in a general position at (0.534, 0.882, 0.760). No plausible solvent model could be developed based upon these two maxima and, accordingly, the data at this stage were subjected to the SQUEEZE procedure (Spek, 2015) prior to the final refinements, and it is the results of that which are reported here for compound (V).
details are summarized in Table 2
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Supporting information
https://doi.org/10.1107/S2056989020008749/hb7928sup1.cif
contains datablocks global, I, II, III, IV, V. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020008749/hb7928Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989020008749/hb7928IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989020008749/hb7928IIIsup4.hkl
Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989020008749/hb7928IVsup5.hkl
Structure factors: contains datablock V. DOI: https://doi.org/10.1107/S2056989020008749/hb7928Vsup6.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989020008749/hb7928Isup7.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020008749/hb7928IIIsup8.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020008749/hb7928IVsup9.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020008749/hb7928Vsup10.cml
For all structures, data collection: CrysAlis CCD (Oxford Diffraction, 2009). Cell
CrysAlis RED (Oxford Diffraction, 2009) for (I), (II), (III), (IV); CrysAlis RED (Oxford Diffraction, 2009 for (V). For all structures, data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020).C10H14FN2+·C7H4FO2−·H2O | Z = 2 |
Mr = 338.35 | F(000) = 356 |
Triclinic, P1 | Dx = 1.302 Mg m−3 |
a = 6.5873 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.6616 (6) Å | Cell parameters from 3684 reflections |
c = 17.3399 (9) Å | θ = 3.1–27.8° |
α = 97.842 (6)° | µ = 0.10 mm−1 |
β = 90.378 (6)° | T = 293 K |
γ = 95.540 (6)° | Plate, yellow |
V = 862.72 (11) Å3 | 0.46 × 0.40 × 0.14 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3567 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2350 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
ω scans | θmax = 26.6°, θmin = 3.1° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −8→8 |
Tmin = 0.871, Tmax = 0.986 | k = −9→9 |
5683 measured reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0551P)2 + 0.1332P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
3567 reflections | Δρmax = 0.20 e Å−3 |
229 parameters | Δρmin = −0.18 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.1956 (2) | 0.2775 (2) | 0.55321 (8) | 0.0526 (4) | |
H11 | 0.128 (3) | 0.248 (2) | 0.5023 (11) | 0.063* | |
H12 | 0.261 (3) | 0.397 (2) | 0.5549 (10) | 0.063* | |
C2 | 0.3525 (3) | 0.1578 (2) | 0.56592 (10) | 0.0613 (5) | |
H2A | 0.4556 | 0.1635 | 0.5264 | 0.074* | |
H2B | 0.2900 | 0.0369 | 0.5616 | 0.074* | |
C3 | 0.4500 (3) | 0.2110 (3) | 0.64506 (10) | 0.0600 (5) | |
H3A | 0.5502 | 0.1302 | 0.6533 | 0.072* | |
H3B | 0.5204 | 0.3290 | 0.6478 | 0.072* | |
N4 | 0.2988 (2) | 0.20918 (17) | 0.70635 (8) | 0.0505 (3) | |
C5 | 0.1372 (3) | 0.3200 (2) | 0.69427 (10) | 0.0564 (4) | |
H5A | 0.1933 | 0.4430 | 0.7007 | 0.068* | |
H5B | 0.0341 | 0.3071 | 0.7333 | 0.068* | |
C6 | 0.0396 (3) | 0.2714 (3) | 0.61423 (10) | 0.0601 (5) | |
H6A | −0.0311 | 0.1533 | 0.6098 | 0.072* | |
H6B | −0.0600 | 0.3533 | 0.6068 | 0.072* | |
C21 | 0.3776 (3) | 0.2198 (2) | 0.78315 (9) | 0.0529 (4) | |
C22 | 0.5444 (3) | 0.1322 (3) | 0.79801 (12) | 0.0717 (5) | |
H22 | 0.6084 | 0.0703 | 0.7567 | 0.086* | |
C23 | 0.6182 (4) | 0.1350 (3) | 0.87334 (14) | 0.0871 (7) | |
H23 | 0.7307 | 0.0756 | 0.8824 | 0.105* | |
C24 | 0.5257 (4) | 0.2242 (3) | 0.93308 (12) | 0.0856 (7) | |
F24 | 0.5993 (3) | 0.2265 (2) | 1.00693 (8) | 0.1322 (6) | |
C25 | 0.3638 (4) | 0.3123 (3) | 0.92138 (12) | 0.0915 (7) | |
H25 | 0.3023 | 0.3737 | 0.9635 | 0.110* | |
C26 | 0.2891 (3) | 0.3115 (3) | 0.84663 (11) | 0.0757 (6) | |
H26 | 0.1778 | 0.3734 | 0.8388 | 0.091* | |
C31 | 0.1143 (2) | 0.23893 (19) | 0.27760 (9) | 0.0460 (4) | |
C32 | 0.2604 (3) | 0.3128 (2) | 0.23158 (11) | 0.0608 (5) | |
F32 | 0.45031 (17) | 0.36529 (19) | 0.26186 (8) | 0.0980 (4) | |
C33 | 0.2228 (3) | 0.3407 (3) | 0.15683 (13) | 0.0800 (6) | |
H33 | 0.3239 | 0.3951 | 0.1285 | 0.096* | |
C34 | 0.0325 (4) | 0.2866 (3) | 0.12448 (12) | 0.0806 (6) | |
H34 | 0.0052 | 0.3004 | 0.0731 | 0.097* | |
C35 | −0.1176 (3) | 0.2123 (3) | 0.16775 (12) | 0.0757 (6) | |
H35 | −0.2466 | 0.1763 | 0.1457 | 0.091* | |
C36 | −0.0777 (3) | 0.1908 (2) | 0.24373 (10) | 0.0605 (5) | |
H36 | −0.1816 | 0.1431 | 0.2729 | 0.073* | |
C37 | 0.1585 (2) | 0.2067 (2) | 0.35934 (10) | 0.0485 (4) | |
O31 | 0.01691 (18) | 0.21983 (18) | 0.40748 (7) | 0.0682 (4) | |
O32 | 0.32700 (18) | 0.16218 (18) | 0.37573 (8) | 0.0718 (4) | |
O41 | 0.3280 (2) | 0.63088 (18) | 0.56039 (9) | 0.0707 (4) | |
H41 | 0.430 (4) | 0.685 (3) | 0.5852 (15) | 0.106* | |
H42 | 0.224 (4) | 0.688 (3) | 0.5795 (14) | 0.106* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0615 (9) | 0.0535 (8) | 0.0436 (8) | 0.0059 (7) | −0.0030 (7) | 0.0095 (6) |
C2 | 0.0789 (12) | 0.0603 (11) | 0.0489 (10) | 0.0238 (9) | 0.0110 (9) | 0.0097 (8) |
C3 | 0.0601 (10) | 0.0749 (12) | 0.0513 (10) | 0.0275 (9) | 0.0088 (8) | 0.0163 (8) |
N4 | 0.0562 (8) | 0.0558 (8) | 0.0426 (8) | 0.0151 (6) | 0.0054 (6) | 0.0114 (6) |
C5 | 0.0524 (10) | 0.0683 (11) | 0.0512 (10) | 0.0156 (8) | 0.0070 (8) | 0.0113 (8) |
C6 | 0.0523 (10) | 0.0705 (11) | 0.0596 (11) | 0.0083 (8) | 0.0017 (8) | 0.0157 (9) |
C21 | 0.0637 (10) | 0.0501 (9) | 0.0461 (10) | 0.0065 (8) | 0.0014 (8) | 0.0107 (7) |
C22 | 0.0830 (13) | 0.0771 (13) | 0.0580 (12) | 0.0253 (11) | −0.0088 (10) | 0.0080 (9) |
C23 | 0.1000 (17) | 0.0901 (15) | 0.0751 (15) | 0.0248 (13) | −0.0274 (13) | 0.0156 (12) |
C24 | 0.1192 (19) | 0.0878 (15) | 0.0498 (12) | 0.0060 (14) | −0.0209 (12) | 0.0130 (11) |
F24 | 0.1853 (16) | 0.1527 (14) | 0.0599 (8) | 0.0244 (12) | −0.0440 (9) | 0.0162 (8) |
C25 | 0.120 (2) | 0.1097 (18) | 0.0467 (12) | 0.0245 (16) | 0.0060 (12) | 0.0066 (11) |
C26 | 0.0880 (14) | 0.0932 (15) | 0.0497 (12) | 0.0259 (12) | 0.0062 (10) | 0.0108 (10) |
C31 | 0.0482 (9) | 0.0404 (8) | 0.0491 (9) | 0.0074 (7) | −0.0027 (7) | 0.0029 (7) |
C32 | 0.0513 (10) | 0.0673 (11) | 0.0624 (12) | −0.0003 (8) | −0.0023 (9) | 0.0086 (9) |
F32 | 0.0601 (7) | 0.1385 (11) | 0.0924 (9) | −0.0228 (7) | −0.0031 (6) | 0.0283 (8) |
C33 | 0.0815 (15) | 0.0946 (16) | 0.0662 (13) | −0.0028 (12) | 0.0108 (11) | 0.0267 (11) |
C34 | 0.0925 (16) | 0.0986 (16) | 0.0546 (12) | 0.0100 (13) | −0.0069 (11) | 0.0236 (11) |
C35 | 0.0707 (13) | 0.0935 (15) | 0.0627 (13) | −0.0016 (11) | −0.0201 (10) | 0.0178 (11) |
C36 | 0.0571 (10) | 0.0673 (11) | 0.0570 (11) | −0.0021 (8) | −0.0084 (8) | 0.0146 (8) |
C37 | 0.0472 (9) | 0.0447 (9) | 0.0521 (10) | 0.0063 (7) | −0.0065 (8) | 0.0009 (7) |
O31 | 0.0538 (7) | 0.1020 (10) | 0.0504 (7) | 0.0164 (7) | −0.0032 (6) | 0.0098 (6) |
O32 | 0.0586 (8) | 0.0929 (10) | 0.0695 (9) | 0.0283 (7) | −0.0068 (6) | 0.0163 (7) |
O41 | 0.0574 (8) | 0.0642 (8) | 0.0923 (11) | 0.0069 (6) | 0.0025 (7) | 0.0166 (7) |
N1—C2 | 1.481 (2) | C23—H23 | 0.9300 |
N1—C6 | 1.482 (2) | C24—C25 | 1.345 (3) |
N1—H11 | 0.974 (19) | C24—F24 | 1.364 (2) |
N1—H12 | 0.973 (18) | C25—C26 | 1.382 (3) |
C2—C3 | 1.499 (2) | C25—H25 | 0.9300 |
C2—H2A | 0.9700 | C26—H26 | 0.9300 |
C2—H2B | 0.9700 | C31—C32 | 1.383 (2) |
C3—N4 | 1.462 (2) | C31—C36 | 1.386 (2) |
C3—H3A | 0.9700 | C31—C37 | 1.503 (2) |
C3—H3B | 0.9700 | C32—F32 | 1.356 (2) |
N4—C21 | 1.415 (2) | C32—C33 | 1.367 (3) |
N4—C5 | 1.455 (2) | C33—C34 | 1.373 (3) |
C5—C6 | 1.510 (2) | C33—H33 | 0.9300 |
C5—H5A | 0.9700 | C34—C35 | 1.372 (3) |
C5—H5B | 0.9700 | C34—H34 | 0.9300 |
C6—H6A | 0.9700 | C35—C36 | 1.377 (3) |
C6—H6B | 0.9700 | C35—H35 | 0.9300 |
C21—C22 | 1.382 (2) | C36—H36 | 0.9300 |
C21—C26 | 1.386 (2) | C37—O32 | 1.2347 (18) |
C22—C23 | 1.387 (3) | C37—O31 | 1.2580 (19) |
C22—H22 | 0.9300 | O41—H41 | 0.84 (3) |
C23—C24 | 1.344 (3) | O41—H42 | 0.89 (3) |
C2—N1—C6 | 109.84 (13) | C21—C22—H22 | 119.4 |
C2—N1—H11 | 112.8 (10) | C23—C22—H22 | 119.4 |
C6—N1—H11 | 108.9 (10) | C24—C23—C22 | 119.5 (2) |
C2—N1—H12 | 109.1 (10) | C24—C23—H23 | 120.3 |
C6—N1—H12 | 110.1 (10) | C22—C23—H23 | 120.3 |
H11—N1—H12 | 106.0 (15) | C23—C24—C25 | 121.4 (2) |
N1—C2—C3 | 109.97 (14) | C23—C24—F24 | 119.1 (2) |
N1—C2—H2A | 109.7 | C25—C24—F24 | 119.5 (2) |
C3—C2—H2A | 109.7 | C24—C25—C26 | 119.8 (2) |
N1—C2—H2B | 109.7 | C24—C25—H25 | 120.1 |
C3—C2—H2B | 109.7 | C26—C25—H25 | 120.1 |
H2A—C2—H2B | 108.2 | C25—C26—C21 | 121.0 (2) |
N4—C3—C2 | 111.44 (15) | C25—C26—H26 | 119.5 |
N4—C3—H3A | 109.3 | C21—C26—H26 | 119.5 |
C2—C3—H3A | 109.3 | C32—C31—C36 | 116.39 (16) |
N4—C3—H3B | 109.3 | C32—C31—C37 | 122.84 (15) |
C2—C3—H3B | 109.3 | C36—C31—C37 | 120.76 (15) |
H3A—C3—H3B | 108.0 | F32—C32—C33 | 117.41 (17) |
C21—N4—C5 | 117.11 (13) | F32—C32—C31 | 119.16 (16) |
C21—N4—C3 | 115.84 (14) | C33—C32—C31 | 123.41 (17) |
C5—N4—C3 | 111.76 (12) | C32—C33—C34 | 118.53 (19) |
N4—C5—C6 | 111.74 (14) | C32—C33—H33 | 120.7 |
N4—C5—H5A | 109.3 | C34—C33—H33 | 120.7 |
C6—C5—H5A | 109.3 | C35—C34—C33 | 120.21 (19) |
N4—C5—H5B | 109.3 | C35—C34—H34 | 119.9 |
C6—C5—H5B | 109.3 | C33—C34—H34 | 119.9 |
H5A—C5—H5B | 107.9 | C34—C35—C36 | 120.10 (19) |
N1—C6—C5 | 110.66 (14) | C34—C35—H35 | 120.0 |
N1—C6—H6A | 109.5 | C36—C35—H35 | 120.0 |
C5—C6—H6A | 109.5 | C35—C36—C31 | 121.31 (18) |
N1—C6—H6B | 109.5 | C35—C36—H36 | 119.3 |
C5—C6—H6B | 109.5 | C31—C36—H36 | 119.3 |
H6A—C6—H6B | 108.1 | O32—C37—O31 | 122.88 (16) |
C22—C21—C26 | 117.06 (17) | O32—C37—C31 | 119.41 (15) |
C22—C21—N4 | 120.50 (15) | O31—C37—C31 | 117.65 (14) |
C26—C21—N4 | 122.41 (16) | H41—O41—H42 | 104 (2) |
C21—C22—C23 | 121.2 (2) | ||
C6—N1—C2—C3 | −58.4 (2) | C24—C25—C26—C21 | 0.5 (4) |
N1—C2—C3—N4 | 57.70 (19) | C22—C21—C26—C25 | −0.9 (3) |
C2—C3—N4—C21 | 166.90 (14) | N4—C21—C26—C25 | 176.88 (19) |
C2—C3—N4—C5 | −55.50 (19) | C36—C31—C32—F32 | 178.92 (16) |
C21—N4—C5—C6 | −169.07 (14) | C37—C31—C32—F32 | −2.6 (2) |
C3—N4—C5—C6 | 53.91 (19) | C36—C31—C32—C33 | 0.7 (3) |
C2—N1—C6—C5 | 57.07 (19) | C37—C31—C32—C33 | 179.14 (17) |
N4—C5—C6—N1 | −54.95 (19) | F32—C32—C33—C34 | 179.15 (19) |
C5—N4—C21—C22 | −173.58 (16) | C31—C32—C33—C34 | −2.6 (3) |
C3—N4—C21—C22 | −38.3 (2) | C32—C33—C34—C35 | 2.4 (3) |
C5—N4—C21—C26 | 8.7 (2) | C33—C34—C35—C36 | −0.3 (3) |
C3—N4—C21—C26 | 143.97 (18) | C34—C35—C36—C31 | −1.7 (3) |
C26—C21—C22—C23 | 0.6 (3) | C32—C31—C36—C35 | 1.5 (3) |
N4—C21—C22—C23 | −177.22 (18) | C37—C31—C36—C35 | −177.02 (16) |
C21—C22—C23—C24 | 0.1 (4) | C32—C31—C37—O32 | −35.4 (2) |
C22—C23—C24—C25 | −0.6 (4) | C36—C31—C37—O32 | 143.03 (17) |
C22—C23—C24—F24 | −179.9 (2) | C32—C31—C37—O31 | 147.48 (16) |
C23—C24—C25—C26 | 0.3 (4) | C36—C31—C37—O31 | −34.1 (2) |
F24—C24—C25—C26 | 179.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.975 (19) | 1.773 (19) | 2.7426 (18) | 173.2 (14) |
N1—H12···O41 | 0.970 (16) | 1.793 (16) | 2.749 (2) | 167.9 (18) |
O41—H41···O32i | 0.84 (3) | 1.95 (3) | 2.7744 (19) | 168 (2) |
O41—H42···O31ii | 0.89 (3) | 1.80 (3) | 2.6693 (18) | 164 (2) |
C3—H3A···O32iii | 0.97 | 2.44 | 3.317 (3) | 149 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y, −z+1. |
C10H14FN2+·C7H4BrO2−·0.353H2O | Z = 2 |
Mr = 387.59 | F(000) = 395.1 |
Triclinic, P1 | Dx = 1.515 Mg m−3 |
a = 7.2584 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.347 (1) Å | Cell parameters from 3585 reflections |
c = 13.767 (2) Å | θ = 3.0–27.6° |
α = 101.14 (1)° | µ = 2.44 mm−1 |
β = 95.98 (1)° | T = 293 K |
γ = 109.44 (1)° | Block, orange |
V = 849.72 (19) Å3 | 0.50 × 0.48 × 0.44 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3582 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2775 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −4→9 |
Tmin = 0.257, Tmax = 0.341 | k = −12→11 |
5475 measured reflections | l = −16→17 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0776P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
3582 reflections | Δρmax = 0.47 e Å−3 |
219 parameters | Δρmin = −0.77 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.4921 (4) | 0.5765 (3) | 0.36697 (18) | 0.0441 (5) | |
H11 | 0.577 (5) | 0.549 (4) | 0.386 (2) | 0.053* | |
H12 | 0.448 (5) | 0.616 (4) | 0.422 (2) | 0.053* | |
C2 | 0.3355 (5) | 0.4415 (3) | 0.2958 (2) | 0.0553 (7) | |
H2A | 0.2812 | 0.3601 | 0.3304 | 0.066* | |
H2B | 0.3928 | 0.3996 | 0.2417 | 0.066* | |
C3 | 0.1719 (4) | 0.4880 (3) | 0.2525 (2) | 0.0516 (7) | |
H3A | 0.0718 | 0.3979 | 0.2054 | 0.062* | |
H3B | 0.1095 | 0.5246 | 0.3061 | 0.062* | |
N4 | 0.2506 (3) | 0.6110 (2) | 0.20113 (16) | 0.0398 (5) | |
C5 | 0.4007 (4) | 0.7471 (3) | 0.2736 (2) | 0.0512 (7) | |
H5A | 0.3388 | 0.7855 | 0.3267 | 0.061* | |
H5B | 0.4530 | 0.8300 | 0.2398 | 0.061* | |
C6 | 0.5673 (4) | 0.7068 (4) | 0.3186 (2) | 0.0520 (7) | |
H6A | 0.6373 | 0.6777 | 0.2665 | 0.062* | |
H6B | 0.6605 | 0.7976 | 0.3682 | 0.062* | |
C21 | 0.1090 (4) | 0.6461 (3) | 0.1414 (2) | 0.0402 (6) | |
C22 | −0.0941 (4) | 0.5824 (3) | 0.1394 (2) | 0.0516 (7) | |
H22 | −0.1410 | 0.5151 | 0.1804 | 0.062* | |
C23 | −0.2270 (5) | 0.6168 (4) | 0.0782 (3) | 0.0658 (9) | |
H23 | −0.3628 | 0.5720 | 0.0767 | 0.079* | |
C24 | −0.1579 (6) | 0.7161 (5) | 0.0204 (2) | 0.0689 (10) | |
F24 | −0.2891 (5) | 0.7538 (4) | −0.0391 (2) | 0.1093 (9) | |
C25 | 0.0363 (7) | 0.7830 (5) | 0.0199 (3) | 0.0724 (10) | |
H25 | 0.0796 | 0.8530 | −0.0200 | 0.087* | |
C26 | 0.1726 (5) | 0.7464 (4) | 0.0798 (2) | 0.0556 (7) | |
H26 | 0.3074 | 0.7898 | 0.0784 | 0.067* | |
C31 | 0.8354 (4) | 0.2190 (3) | 0.3694 (2) | 0.0373 (5) | |
C32 | 0.7930 (4) | 0.1403 (3) | 0.2693 (2) | 0.0402 (6) | |
Br32 | 0.59370 (5) | 0.15933 (4) | 0.17735 (2) | 0.06077 (16) | |
C33 | 0.8889 (5) | 0.0410 (3) | 0.2323 (3) | 0.0552 (8) | |
H33 | 0.8575 | −0.0114 | 0.1646 | 0.066* | |
C34 | 1.0298 (5) | 0.0214 (4) | 0.2964 (3) | 0.0628 (9) | |
H34 | 1.0970 | −0.0431 | 0.2721 | 0.075* | |
C35 | 1.0731 (5) | 0.0959 (4) | 0.3964 (3) | 0.0622 (9) | |
H35 | 1.1678 | 0.0808 | 0.4400 | 0.075* | |
C36 | 0.9752 (4) | 0.1941 (4) | 0.4325 (2) | 0.0529 (7) | |
H36 | 1.0047 | 0.2439 | 0.5006 | 0.064* | |
C37 | 0.7364 (4) | 0.3310 (3) | 0.41091 (19) | 0.0417 (6) | |
O31 | 0.6248 (4) | 0.2899 (3) | 0.4701 (2) | 0.0826 (8) | |
O32 | 0.7754 (3) | 0.4539 (2) | 0.38357 (18) | 0.0584 (6) | |
O41 | 0.4360 (13) | 0.0019 (13) | 0.4890 (8) | 0.101 (4)* | 0.353 (8) |
H41 | 0.4989 | 0.0990 | 0.4825 | 0.152* | 0.353 (8) |
H42 | 0.4159 | −0.0920 | 0.5015 | 0.152* | 0.353 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0506 (14) | 0.0534 (14) | 0.0440 (12) | 0.0320 (12) | 0.0205 (11) | 0.0181 (10) |
C2 | 0.0616 (18) | 0.0406 (15) | 0.070 (2) | 0.0195 (14) | 0.0168 (15) | 0.0247 (14) |
C3 | 0.0439 (15) | 0.0436 (16) | 0.070 (2) | 0.0094 (13) | 0.0157 (14) | 0.0283 (14) |
N4 | 0.0430 (12) | 0.0293 (10) | 0.0464 (12) | 0.0086 (9) | 0.0126 (10) | 0.0130 (9) |
C5 | 0.0536 (17) | 0.0360 (14) | 0.0578 (17) | 0.0061 (13) | 0.0045 (14) | 0.0180 (12) |
C6 | 0.0431 (15) | 0.0511 (17) | 0.0627 (18) | 0.0119 (13) | 0.0139 (13) | 0.0226 (14) |
C21 | 0.0484 (15) | 0.0343 (13) | 0.0368 (12) | 0.0163 (12) | 0.0080 (11) | 0.0037 (10) |
C22 | 0.0509 (16) | 0.0463 (16) | 0.0535 (17) | 0.0147 (14) | 0.0064 (13) | 0.0098 (13) |
C23 | 0.0569 (19) | 0.068 (2) | 0.060 (2) | 0.0223 (17) | −0.0068 (16) | −0.0029 (17) |
C24 | 0.088 (3) | 0.079 (2) | 0.0451 (18) | 0.051 (2) | −0.0058 (17) | 0.0003 (17) |
F24 | 0.134 (2) | 0.143 (2) | 0.0717 (15) | 0.088 (2) | −0.0174 (15) | 0.0237 (15) |
C25 | 0.115 (3) | 0.074 (2) | 0.0461 (18) | 0.050 (2) | 0.0165 (19) | 0.0253 (16) |
C26 | 0.072 (2) | 0.0548 (18) | 0.0496 (16) | 0.0277 (16) | 0.0181 (14) | 0.0207 (14) |
C31 | 0.0367 (13) | 0.0303 (12) | 0.0491 (14) | 0.0128 (10) | 0.0180 (11) | 0.0123 (10) |
C32 | 0.0449 (14) | 0.0278 (12) | 0.0495 (14) | 0.0115 (11) | 0.0188 (11) | 0.0104 (10) |
Br32 | 0.0670 (2) | 0.0549 (2) | 0.0537 (2) | 0.02015 (17) | 0.00086 (15) | 0.00658 (14) |
C33 | 0.072 (2) | 0.0381 (15) | 0.0619 (18) | 0.0243 (15) | 0.0303 (16) | 0.0081 (13) |
C34 | 0.070 (2) | 0.0430 (16) | 0.095 (3) | 0.0350 (16) | 0.043 (2) | 0.0215 (17) |
C35 | 0.0556 (18) | 0.0560 (19) | 0.092 (3) | 0.0325 (16) | 0.0196 (17) | 0.0318 (18) |
C36 | 0.0561 (17) | 0.0517 (17) | 0.0558 (17) | 0.0244 (14) | 0.0125 (14) | 0.0139 (13) |
C37 | 0.0414 (14) | 0.0411 (14) | 0.0424 (14) | 0.0172 (12) | 0.0132 (11) | 0.0025 (11) |
O31 | 0.107 (2) | 0.0798 (17) | 0.0924 (19) | 0.0535 (16) | 0.0711 (17) | 0.0299 (14) |
O32 | 0.0564 (12) | 0.0443 (11) | 0.0858 (16) | 0.0290 (10) | 0.0240 (11) | 0.0164 (11) |
N1—C6 | 1.473 (4) | C24—C25 | 1.340 (6) |
N1—C2 | 1.476 (4) | C24—F24 | 1.369 (4) |
N1—H11 | 0.78 (3) | C25—C26 | 1.393 (5) |
N1—H12 | 0.92 (3) | C25—H25 | 0.9300 |
C2—C3 | 1.500 (4) | C26—H26 | 0.9300 |
C2—H2A | 0.9700 | C31—C36 | 1.376 (4) |
C2—H2B | 0.9700 | C31—C32 | 1.379 (4) |
C3—N4 | 1.453 (3) | C31—C37 | 1.514 (3) |
C3—H3A | 0.9700 | C32—C33 | 1.388 (4) |
C3—H3B | 0.9700 | C32—Br32 | 1.898 (3) |
N4—C21 | 1.412 (3) | C33—C34 | 1.363 (5) |
N4—C5 | 1.470 (4) | C33—H33 | 0.9300 |
C5—C6 | 1.492 (4) | C34—C35 | 1.368 (5) |
C5—H5A | 0.9700 | C34—H34 | 0.9300 |
C5—H5B | 0.9700 | C35—C36 | 1.387 (4) |
C6—H6A | 0.9700 | C35—H35 | 0.9300 |
C6—H6B | 0.9700 | C36—H36 | 0.9300 |
C21—C26 | 1.382 (4) | C37—O32 | 1.231 (3) |
C21—C22 | 1.389 (4) | C37—O31 | 1.233 (3) |
C22—C23 | 1.373 (4) | O41—O41i | 0.962 (16) |
C22—H22 | 0.9300 | O41—H41 | 0.8970 |
C23—C24 | 1.344 (5) | O41—H42 | 0.8940 |
C23—H23 | 0.9300 | ||
C6—N1—C2 | 110.7 (2) | C21—C22—H22 | 119.3 |
C6—N1—H11 | 111 (2) | C24—C23—C22 | 119.0 (3) |
C2—N1—H11 | 108 (2) | C24—C23—H23 | 120.5 |
C6—N1—H12 | 106 (2) | C22—C23—H23 | 120.5 |
C2—N1—H12 | 113 (2) | C25—C24—C23 | 122.5 (3) |
H11—N1—H12 | 108 (3) | C25—C24—F24 | 118.1 (4) |
N1—C2—C3 | 111.1 (2) | C23—C24—F24 | 119.4 (4) |
N1—C2—H2A | 109.4 | C24—C25—C26 | 119.2 (3) |
C3—C2—H2A | 109.4 | C24—C25—H25 | 120.4 |
N1—C2—H2B | 109.4 | C26—C25—H25 | 120.4 |
C3—C2—H2B | 109.4 | C21—C26—C25 | 120.5 (3) |
H2A—C2—H2B | 108.0 | C21—C26—H26 | 119.8 |
N4—C3—C2 | 110.3 (2) | C25—C26—H26 | 119.8 |
N4—C3—H3A | 109.6 | C36—C31—C32 | 117.6 (2) |
C2—C3—H3A | 109.6 | C36—C31—C37 | 119.7 (2) |
N4—C3—H3B | 109.6 | C32—C31—C37 | 122.8 (2) |
C2—C3—H3B | 109.6 | C31—C32—C33 | 121.8 (3) |
H3A—C3—H3B | 108.1 | C31—C32—Br32 | 120.83 (19) |
C21—N4—C3 | 116.1 (2) | C33—C32—Br32 | 117.3 (2) |
C21—N4—C5 | 114.7 (2) | C34—C33—C32 | 119.1 (3) |
C3—N4—C5 | 109.0 (2) | C34—C33—H33 | 120.4 |
N4—C5—C6 | 111.5 (2) | C32—C33—H33 | 120.4 |
N4—C5—H5A | 109.3 | C33—C34—C35 | 120.4 (3) |
C6—C5—H5A | 109.3 | C33—C34—H34 | 119.8 |
N4—C5—H5B | 109.3 | C35—C34—H34 | 119.8 |
C6—C5—H5B | 109.3 | C34—C35—C36 | 119.8 (3) |
H5A—C5—H5B | 108.0 | C34—C35—H35 | 120.1 |
N1—C6—C5 | 110.8 (2) | C36—C35—H35 | 120.1 |
N1—C6—H6A | 109.5 | C31—C36—C35 | 121.2 (3) |
C5—C6—H6A | 109.5 | C31—C36—H36 | 119.4 |
N1—C6—H6B | 109.5 | C35—C36—H36 | 119.4 |
C5—C6—H6B | 109.5 | O32—C37—O31 | 126.2 (3) |
H6A—C6—H6B | 108.1 | O32—C37—C31 | 117.6 (2) |
C26—C21—C22 | 117.5 (3) | O31—C37—C31 | 116.2 (3) |
C26—C21—N4 | 119.2 (3) | O41i—O41—H41 | 88.0 |
C22—C21—N4 | 123.3 (2) | O41i—O41—H42 | 72.5 |
C23—C22—C21 | 121.3 (3) | H41—O41—H42 | 160.5 |
C23—C22—H22 | 119.3 | ||
C6—N1—C2—C3 | −54.9 (3) | C22—C21—C26—C25 | 1.1 (4) |
N1—C2—C3—N4 | 58.5 (3) | N4—C21—C26—C25 | 179.9 (3) |
C2—C3—N4—C21 | 168.8 (2) | C24—C25—C26—C21 | −2.0 (5) |
C2—C3—N4—C5 | −59.8 (3) | C36—C31—C32—C33 | −1.0 (4) |
C21—N4—C5—C6 | −168.4 (2) | C37—C31—C32—C33 | 178.4 (2) |
C3—N4—C5—C6 | 59.5 (3) | C36—C31—C32—Br32 | 177.1 (2) |
C2—N1—C6—C5 | 53.7 (3) | C37—C31—C32—Br32 | −3.5 (3) |
N4—C5—C6—N1 | −56.6 (3) | C31—C32—C33—C34 | −0.4 (4) |
C3—N4—C21—C26 | −171.3 (3) | Br32—C32—C33—C34 | −178.5 (2) |
C5—N4—C21—C26 | 60.0 (3) | C32—C33—C34—C35 | 1.4 (5) |
C3—N4—C21—C22 | 7.4 (4) | C33—C34—C35—C36 | −1.0 (5) |
C5—N4—C21—C22 | −121.2 (3) | C32—C31—C36—C35 | 1.3 (4) |
C26—C21—C22—C23 | 0.4 (4) | C37—C31—C36—C35 | −178.1 (3) |
N4—C21—C22—C23 | −178.3 (3) | C34—C35—C36—C31 | −0.4 (5) |
C21—C22—C23—C24 | −1.1 (5) | C36—C31—C37—O32 | 111.7 (3) |
C22—C23—C24—C25 | 0.2 (5) | C32—C31—C37—O32 | −67.7 (3) |
C22—C23—C24—F24 | −178.5 (3) | C36—C31—C37—O31 | −67.7 (4) |
C23—C24—C25—C26 | 1.3 (6) | C32—C31—C37—O31 | 112.9 (3) |
F24—C24—C25—C26 | −180.0 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O32 | 0.78 (4) | 1.93 (4) | 2.677 (4) | 160 (3) |
N1—H12···O31ii | 0.91 (3) | 1.80 (3) | 2.707 (4) | 175 (3) |
O41—H41···O31 | 0.90 | 1.76 | 2.661 (12) | 179 |
O41—H42···O31i | 0.89 | 1.90 | 2.792 (12) | 179 |
C35—H35···O41iii | 0.93 | 2.38 | 3.257 (11) | 157 |
C2—H2A···Cg1iv | 0.97 | 2.78 | 3.598 (3) | 142 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) x−1, y, z. |
C10H14FN2+·C7H4IO2− | Z = 4 |
Mr = 428.23 | F(000) = 848 |
Triclinic, P1 | Dx = 1.634 Mg m−3 |
a = 9.8892 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.6831 (7) Å | Cell parameters from 7405 reflections |
c = 16.4547 (9) Å | θ = 2.6–27.8° |
α = 106.776 (5)° | µ = 1.86 mm−1 |
β = 93.327 (4)° | T = 293 K |
γ = 104.874 (4)° | Block, orange |
V = 1741.19 (16) Å3 | 0.50 × 0.50 × 0.48 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 7396 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 5890 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
ω scans | θmax = 27.6°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −12→6 |
Tmin = 0.383, Tmax = 0.411 | k = −14→15 |
12798 measured reflections | l = −21→20 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0543P)2 + 4.1226P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
7396 reflections | Δρmax = 2.92 e Å−3 |
427 parameters | Δρmin = −2.00 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N11 | 0.1718 (4) | 0.3441 (4) | 0.4399 (3) | 0.0473 (9) | |
H111 | 0.168 (6) | 0.371 (5) | 0.490 (4) | 0.057* | |
H112 | 0.156 (6) | 0.261 (5) | 0.425 (3) | 0.057* | |
C12 | 0.3127 (5) | 0.4007 (5) | 0.4209 (3) | 0.0592 (12) | |
H12A | 0.3831 | 0.3744 | 0.4486 | 0.071* | |
H12B | 0.3356 | 0.4909 | 0.4437 | 0.071* | |
C13 | 0.3165 (5) | 0.3626 (5) | 0.3258 (3) | 0.0546 (12) | |
H13A | 0.4093 | 0.4023 | 0.3146 | 0.066* | |
H13B | 0.3000 | 0.2730 | 0.3037 | 0.066* | |
N14 | 0.2090 (4) | 0.3984 (3) | 0.2818 (3) | 0.0450 (8) | |
C15 | 0.0698 (5) | 0.3408 (5) | 0.2987 (4) | 0.0579 (12) | |
H15A | 0.0483 | 0.2508 | 0.2752 | 0.069* | |
H15B | −0.0002 | 0.3668 | 0.2704 | 0.069* | |
C16 | 0.0617 (5) | 0.3762 (5) | 0.3932 (4) | 0.0598 (13) | |
H16A | 0.0736 | 0.4652 | 0.4155 | 0.072* | |
H16B | −0.0309 | 0.3330 | 0.4025 | 0.072* | |
C121 | 0.2253 (5) | 0.3925 (4) | 0.1963 (3) | 0.0487 (10) | |
C122 | 0.3559 (6) | 0.4465 (5) | 0.1766 (4) | 0.0597 (12) | |
H122 | 0.4329 | 0.4829 | 0.2199 | 0.072* | |
C123 | 0.3747 (7) | 0.4476 (6) | 0.0947 (4) | 0.0741 (16) | |
H123 | 0.4631 | 0.4837 | 0.0823 | 0.089* | |
C124 | 0.2606 (9) | 0.3945 (6) | 0.0319 (4) | 0.0760 (18) | |
F124 | 0.2786 (6) | 0.3960 (4) | −0.0494 (2) | 0.1097 (15) | |
C125 | 0.1323 (8) | 0.3422 (6) | 0.0477 (4) | 0.0817 (19) | |
H125 | 0.0563 | 0.3083 | 0.0037 | 0.098* | |
C126 | 0.1126 (6) | 0.3385 (5) | 0.1294 (4) | 0.0680 (15) | |
H126 | 0.0238 | 0.2999 | 0.1400 | 0.082* | |
N21 | 0.3249 (4) | 0.1830 (4) | 0.5932 (3) | 0.0481 (9) | |
H211 | 0.329 (6) | 0.157 (5) | 0.544 (4) | 0.058* | |
H212 | 0.337 (6) | 0.261 (6) | 0.611 (4) | 0.058* | |
C22 | 0.4376 (5) | 0.1501 (6) | 0.6362 (3) | 0.0589 (13) | |
H22A | 0.5290 | 0.1980 | 0.6284 | 0.071* | |
H22B | 0.4291 | 0.0623 | 0.6100 | 0.071* | |
C23 | 0.4291 (5) | 0.1759 (5) | 0.7303 (3) | 0.0550 (12) | |
H23A | 0.5000 | 0.1479 | 0.7561 | 0.066* | |
H23B | 0.4487 | 0.2651 | 0.7578 | 0.066* | |
N24 | 0.2907 (4) | 0.1127 (3) | 0.7441 (2) | 0.0445 (8) | |
C25 | 0.1819 (5) | 0.1523 (5) | 0.7055 (3) | 0.0537 (11) | |
H25A | 0.1977 | 0.2412 | 0.7318 | 0.064* | |
H25B | 0.0899 | 0.1096 | 0.7160 | 0.064* | |
C26 | 0.1841 (5) | 0.1235 (5) | 0.6102 (3) | 0.0604 (13) | |
H26A | 0.1602 | 0.0340 | 0.5832 | 0.072* | |
H26B | 0.1141 | 0.1539 | 0.5859 | 0.072* | |
C221 | 0.2749 (5) | 0.0994 (4) | 0.8257 (3) | 0.0462 (10) | |
C222 | 0.3844 (6) | 0.1474 (5) | 0.8936 (3) | 0.0604 (13) | |
H222 | 0.4722 | 0.1944 | 0.8871 | 0.072* | |
C223 | 0.3638 (7) | 0.1256 (6) | 0.9712 (4) | 0.0739 (16) | |
H223 | 0.4373 | 0.1580 | 1.0167 | 0.089* | |
C224 | 0.2374 (8) | 0.0578 (6) | 0.9801 (4) | 0.0749 (17) | |
F224 | 0.2184 (6) | 0.0351 (5) | 1.0561 (3) | 0.1125 (15) | |
C225 | 0.1270 (7) | 0.0094 (6) | 0.9158 (4) | 0.0711 (15) | |
H225 | 0.0400 | −0.0366 | 0.9240 | 0.085* | |
C226 | 0.1453 (5) | 0.0295 (5) | 0.8381 (4) | 0.0573 (12) | |
H226 | 0.0703 | −0.0041 | 0.7935 | 0.069* | |
C131 | 0.2741 (4) | 0.5826 (4) | 0.7440 (3) | 0.0436 (9) | |
C132 | 0.3185 (4) | 0.7104 (4) | 0.7577 (3) | 0.0438 (9) | |
I132 | 0.38641 (4) | 0.78363 (3) | 0.65990 (2) | 0.06260 (12) | |
C133 | 0.3235 (6) | 0.7943 (5) | 0.8376 (3) | 0.0579 (12) | |
H133 | 0.3542 | 0.8796 | 0.8461 | 0.069* | |
C134 | 0.2831 (7) | 0.7512 (6) | 0.9039 (4) | 0.0714 (16) | |
H134 | 0.2850 | 0.8074 | 0.9574 | 0.086* | |
C135 | 0.2401 (7) | 0.6259 (6) | 0.8920 (4) | 0.0755 (17) | |
H135 | 0.2128 | 0.5971 | 0.9374 | 0.091* | |
C136 | 0.2371 (6) | 0.5442 (5) | 0.8148 (4) | 0.0621 (13) | |
H136 | 0.2097 | 0.4594 | 0.8083 | 0.075* | |
C137 | 0.2666 (5) | 0.4864 (4) | 0.6585 (3) | 0.0456 (10) | |
O131 | 0.3594 (4) | 0.4325 (3) | 0.6506 (3) | 0.0648 (10) | |
O132 | 0.1659 (5) | 0.4666 (4) | 0.6041 (3) | 0.0837 (13) | |
C231 | 0.2056 (4) | −0.0826 (4) | 0.3071 (3) | 0.0408 (9) | |
C232 | 0.1850 (4) | −0.1973 (4) | 0.3215 (3) | 0.0454 (10) | |
I232 | 0.18832 (4) | −0.21282 (3) | 0.44547 (2) | 0.06302 (13) | |
C233 | 0.1639 (6) | −0.3058 (5) | 0.2536 (4) | 0.0684 (15) | |
H233 | 0.1502 | −0.3819 | 0.2640 | 0.082* | |
C234 | 0.1632 (8) | −0.3016 (6) | 0.1721 (4) | 0.0837 (19) | |
H234 | 0.1488 | −0.3748 | 0.1267 | 0.100* | |
C235 | 0.1838 (7) | −0.1889 (6) | 0.1561 (4) | 0.0732 (16) | |
H235 | 0.1839 | −0.1862 | 0.1002 | 0.088* | |
C236 | 0.2044 (5) | −0.0805 (5) | 0.2232 (3) | 0.0541 (11) | |
H236 | 0.2175 | −0.0050 | 0.2121 | 0.065* | |
C237 | 0.2275 (5) | 0.0386 (4) | 0.3779 (3) | 0.0434 (9) | |
O231 | 0.1327 (4) | 0.0902 (3) | 0.3784 (3) | 0.0689 (10) | |
O232 | 0.3391 (4) | 0.0769 (3) | 0.4284 (2) | 0.0619 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.052 (2) | 0.0355 (19) | 0.053 (2) | 0.0165 (17) | 0.0012 (18) | 0.0095 (17) |
C12 | 0.042 (2) | 0.063 (3) | 0.063 (3) | 0.006 (2) | −0.007 (2) | 0.017 (2) |
C13 | 0.034 (2) | 0.065 (3) | 0.068 (3) | 0.016 (2) | −0.001 (2) | 0.026 (3) |
N14 | 0.0333 (17) | 0.0402 (19) | 0.062 (2) | 0.0093 (14) | −0.0003 (16) | 0.0192 (17) |
C15 | 0.034 (2) | 0.067 (3) | 0.077 (3) | 0.011 (2) | −0.003 (2) | 0.033 (3) |
C16 | 0.044 (3) | 0.066 (3) | 0.081 (4) | 0.025 (2) | 0.010 (2) | 0.033 (3) |
C121 | 0.047 (2) | 0.034 (2) | 0.067 (3) | 0.0149 (18) | 0.002 (2) | 0.017 (2) |
C122 | 0.055 (3) | 0.056 (3) | 0.063 (3) | 0.010 (2) | 0.005 (2) | 0.018 (2) |
C123 | 0.083 (4) | 0.069 (4) | 0.077 (4) | 0.027 (3) | 0.023 (3) | 0.027 (3) |
C124 | 0.122 (6) | 0.061 (3) | 0.056 (3) | 0.042 (4) | 0.013 (4) | 0.021 (3) |
F124 | 0.177 (5) | 0.106 (3) | 0.066 (2) | 0.065 (3) | 0.022 (3) | 0.034 (2) |
C125 | 0.095 (5) | 0.071 (4) | 0.069 (4) | 0.023 (4) | −0.021 (4) | 0.014 (3) |
C126 | 0.058 (3) | 0.065 (3) | 0.071 (4) | 0.007 (3) | −0.016 (3) | 0.022 (3) |
N21 | 0.053 (2) | 0.043 (2) | 0.048 (2) | 0.0181 (18) | 0.0033 (18) | 0.0102 (18) |
C22 | 0.045 (3) | 0.079 (4) | 0.068 (3) | 0.030 (2) | 0.015 (2) | 0.033 (3) |
C23 | 0.033 (2) | 0.071 (3) | 0.064 (3) | 0.011 (2) | 0.002 (2) | 0.030 (3) |
N24 | 0.0348 (18) | 0.046 (2) | 0.053 (2) | 0.0125 (15) | 0.0033 (15) | 0.0151 (17) |
C25 | 0.039 (2) | 0.061 (3) | 0.068 (3) | 0.021 (2) | 0.008 (2) | 0.025 (2) |
C26 | 0.045 (3) | 0.070 (3) | 0.064 (3) | 0.014 (2) | −0.002 (2) | 0.021 (3) |
C221 | 0.047 (2) | 0.039 (2) | 0.054 (3) | 0.0155 (19) | 0.008 (2) | 0.0128 (19) |
C222 | 0.056 (3) | 0.062 (3) | 0.057 (3) | 0.010 (2) | 0.000 (2) | 0.016 (2) |
C223 | 0.084 (4) | 0.080 (4) | 0.057 (3) | 0.027 (3) | 0.000 (3) | 0.019 (3) |
C224 | 0.104 (5) | 0.080 (4) | 0.057 (3) | 0.044 (4) | 0.031 (3) | 0.027 (3) |
F224 | 0.148 (4) | 0.148 (4) | 0.075 (2) | 0.065 (3) | 0.044 (3) | 0.061 (3) |
C225 | 0.077 (4) | 0.068 (4) | 0.079 (4) | 0.025 (3) | 0.035 (3) | 0.029 (3) |
C226 | 0.051 (3) | 0.054 (3) | 0.067 (3) | 0.014 (2) | 0.015 (2) | 0.018 (2) |
C131 | 0.039 (2) | 0.040 (2) | 0.054 (2) | 0.0174 (18) | 0.0056 (18) | 0.0126 (19) |
C132 | 0.038 (2) | 0.042 (2) | 0.054 (2) | 0.0167 (18) | 0.0042 (18) | 0.0143 (19) |
I132 | 0.0718 (2) | 0.0563 (2) | 0.0754 (2) | 0.02666 (17) | 0.02048 (18) | 0.03511 (18) |
C133 | 0.062 (3) | 0.043 (3) | 0.063 (3) | 0.021 (2) | 0.004 (2) | 0.003 (2) |
C134 | 0.088 (4) | 0.073 (4) | 0.054 (3) | 0.039 (3) | 0.015 (3) | 0.007 (3) |
C135 | 0.097 (5) | 0.083 (4) | 0.067 (4) | 0.044 (4) | 0.033 (3) | 0.035 (3) |
C136 | 0.078 (4) | 0.050 (3) | 0.073 (3) | 0.027 (3) | 0.024 (3) | 0.030 (3) |
C137 | 0.040 (2) | 0.033 (2) | 0.060 (3) | 0.0088 (17) | 0.008 (2) | 0.0102 (19) |
O131 | 0.056 (2) | 0.0489 (19) | 0.082 (3) | 0.0241 (16) | 0.0081 (18) | 0.0017 (18) |
O132 | 0.074 (3) | 0.097 (3) | 0.063 (2) | 0.043 (2) | −0.013 (2) | −0.013 (2) |
C231 | 0.034 (2) | 0.039 (2) | 0.050 (2) | 0.0118 (16) | 0.0033 (17) | 0.0134 (18) |
C232 | 0.040 (2) | 0.037 (2) | 0.060 (3) | 0.0146 (17) | 0.0038 (19) | 0.0125 (19) |
I232 | 0.0707 (2) | 0.0597 (2) | 0.0752 (2) | 0.02272 (17) | 0.02547 (18) | 0.03962 (18) |
C233 | 0.079 (4) | 0.041 (3) | 0.079 (4) | 0.021 (3) | 0.006 (3) | 0.006 (3) |
C234 | 0.107 (5) | 0.059 (4) | 0.067 (4) | 0.030 (3) | −0.003 (3) | −0.011 (3) |
C235 | 0.091 (4) | 0.079 (4) | 0.046 (3) | 0.035 (3) | 0.001 (3) | 0.007 (3) |
C236 | 0.059 (3) | 0.056 (3) | 0.052 (3) | 0.023 (2) | 0.004 (2) | 0.018 (2) |
C237 | 0.050 (2) | 0.033 (2) | 0.047 (2) | 0.0059 (18) | 0.012 (2) | 0.0170 (18) |
O231 | 0.072 (2) | 0.0392 (18) | 0.090 (3) | 0.0232 (17) | 0.011 (2) | 0.0065 (18) |
O232 | 0.062 (2) | 0.061 (2) | 0.0474 (19) | 0.0034 (17) | 0.0019 (16) | 0.0074 (16) |
N11—C12 | 1.474 (6) | C25—H25B | 0.9700 |
N11—C16 | 1.483 (6) | C26—H26A | 0.9700 |
N11—H111 | 0.80 (6) | C26—H26B | 0.9700 |
N11—H112 | 0.89 (6) | C221—C222 | 1.387 (7) |
C12—C13 | 1.505 (7) | C221—C226 | 1.394 (7) |
C12—H12A | 0.9700 | C222—C223 | 1.389 (8) |
C12—H12B | 0.9700 | C222—H222 | 0.9300 |
C13—N14 | 1.463 (5) | C223—C224 | 1.338 (9) |
C13—H13A | 0.9700 | C223—H223 | 0.9300 |
C13—H13B | 0.9700 | C224—C225 | 1.354 (9) |
N14—C121 | 1.410 (6) | C224—F224 | 1.366 (7) |
N14—C15 | 1.450 (6) | C225—C226 | 1.378 (8) |
C15—C16 | 1.501 (8) | C225—H225 | 0.9300 |
C15—H15A | 0.9700 | C226—H226 | 0.9300 |
C15—H15B | 0.9700 | C131—C132 | 1.389 (6) |
C16—H16A | 0.9700 | C131—C136 | 1.400 (7) |
C16—H16B | 0.9700 | C131—C137 | 1.510 (6) |
C121—C122 | 1.385 (7) | C132—C133 | 1.383 (7) |
C121—C126 | 1.395 (7) | C132—I132 | 2.097 (5) |
C122—C123 | 1.374 (8) | C133—C134 | 1.367 (8) |
C122—H122 | 0.9300 | C133—H133 | 0.9300 |
C123—C124 | 1.364 (10) | C134—C135 | 1.366 (9) |
C123—H123 | 0.9300 | C134—H134 | 0.9300 |
C124—C125 | 1.335 (10) | C135—C136 | 1.344 (8) |
C124—F124 | 1.364 (7) | C135—H135 | 0.9300 |
C125—C126 | 1.381 (9) | C136—H136 | 0.9300 |
C125—H125 | 0.9300 | C137—O132 | 1.228 (6) |
C126—H126 | 0.9300 | C137—O131 | 1.232 (5) |
N21—C26 | 1.470 (7) | C231—C236 | 1.388 (7) |
N21—C22 | 1.475 (6) | C231—C232 | 1.393 (6) |
N21—H211 | 0.78 (6) | C231—C237 | 1.507 (6) |
N21—H212 | 0.84 (6) | C232—C233 | 1.385 (7) |
C22—C23 | 1.502 (7) | C232—I232 | 2.099 (5) |
C22—H22A | 0.9700 | C233—C234 | 1.357 (9) |
C22—H22B | 0.9700 | C233—H233 | 0.9300 |
C23—N24 | 1.444 (6) | C234—C235 | 1.383 (9) |
C23—H23A | 0.9700 | C234—H234 | 0.9300 |
C23—H23B | 0.9700 | C235—C236 | 1.377 (7) |
N24—C221 | 1.408 (6) | C235—H235 | 0.9300 |
N24—C25 | 1.456 (6) | C236—H236 | 0.9300 |
C25—C26 | 1.509 (7) | C237—O231 | 1.237 (6) |
C25—H25A | 0.9700 | C237—O232 | 1.238 (6) |
C12—N11—C16 | 110.2 (4) | N24—C25—C26 | 110.6 (4) |
C12—N11—H111 | 110 (4) | N24—C25—H25A | 109.5 |
C16—N11—H111 | 108 (4) | C26—C25—H25A | 109.5 |
C12—N11—H112 | 109 (3) | N24—C25—H25B | 109.5 |
C16—N11—H112 | 111 (3) | C26—C25—H25B | 109.5 |
H111—N11—H112 | 109 (5) | H25A—C25—H25B | 108.1 |
N11—C12—C13 | 110.8 (4) | N21—C26—C25 | 110.2 (4) |
N11—C12—H12A | 109.5 | N21—C26—H26A | 109.6 |
C13—C12—H12A | 109.5 | C25—C26—H26A | 109.6 |
N11—C12—H12B | 109.5 | N21—C26—H26B | 109.6 |
C13—C12—H12B | 109.5 | C25—C26—H26B | 109.6 |
H12A—C12—H12B | 108.1 | H26A—C26—H26B | 108.1 |
N14—C13—C12 | 110.8 (4) | C222—C221—C226 | 117.9 (5) |
N14—C13—H13A | 109.5 | C222—C221—N24 | 123.2 (4) |
C12—C13—H13A | 109.5 | C226—C221—N24 | 118.8 (4) |
N14—C13—H13B | 109.5 | C221—C222—C223 | 120.3 (5) |
C12—C13—H13B | 109.5 | C221—C222—H222 | 119.8 |
H13A—C13—H13B | 108.1 | C223—C222—H222 | 119.8 |
C121—N14—C15 | 117.6 (4) | C224—C223—C222 | 119.6 (6) |
C121—N14—C13 | 114.6 (4) | C224—C223—H223 | 120.2 |
C15—N14—C13 | 110.1 (4) | C222—C223—H223 | 120.2 |
N14—C15—C16 | 111.3 (4) | C223—C224—C225 | 122.3 (6) |
N14—C15—H15A | 109.4 | C223—C224—F224 | 119.3 (6) |
C16—C15—H15A | 109.4 | C225—C224—F224 | 118.4 (6) |
N14—C15—H15B | 109.4 | C224—C225—C226 | 119.1 (6) |
C16—C15—H15B | 109.4 | C224—C225—H225 | 120.5 |
H15A—C15—H15B | 108.0 | C226—C225—H225 | 120.5 |
N11—C16—C15 | 111.3 (4) | C225—C226—C221 | 120.8 (5) |
N11—C16—H16A | 109.4 | C225—C226—H226 | 119.6 |
C15—C16—H16A | 109.4 | C221—C226—H226 | 119.6 |
N11—C16—H16B | 109.4 | C132—C131—C136 | 116.7 (4) |
C15—C16—H16B | 109.4 | C132—C131—C137 | 123.5 (4) |
H16A—C16—H16B | 108.0 | C136—C131—C137 | 119.8 (4) |
C122—C121—C126 | 117.4 (5) | C133—C132—C131 | 120.9 (4) |
C122—C121—N14 | 120.0 (4) | C133—C132—I132 | 117.5 (4) |
C126—C121—N14 | 122.6 (5) | C131—C132—I132 | 121.6 (3) |
C123—C122—C121 | 121.7 (5) | C134—C133—C132 | 119.7 (5) |
C123—C122—H122 | 119.1 | C134—C133—H133 | 120.1 |
C121—C122—H122 | 119.1 | C132—C133—H133 | 120.1 |
C124—C123—C122 | 118.5 (6) | C135—C134—C133 | 120.3 (5) |
C124—C123—H123 | 120.8 | C135—C134—H134 | 119.8 |
C122—C123—H123 | 120.8 | C133—C134—H134 | 119.8 |
C125—C124—C123 | 122.1 (6) | C136—C135—C134 | 120.1 (6) |
C125—C124—F124 | 119.2 (7) | C136—C135—H135 | 120.0 |
C123—C124—F124 | 118.7 (7) | C134—C135—H135 | 120.0 |
C124—C125—C126 | 120.0 (6) | C135—C136—C131 | 122.2 (5) |
C124—C125—H125 | 120.0 | C135—C136—H136 | 118.9 |
C126—C125—H125 | 120.0 | C131—C136—H136 | 118.9 |
C125—C126—C121 | 120.3 (6) | O132—C137—O131 | 126.0 (5) |
C125—C126—H126 | 119.9 | O132—C137—C131 | 116.7 (4) |
C121—C126—H126 | 119.9 | O131—C137—C131 | 117.3 (4) |
C26—N21—C22 | 112.1 (4) | C236—C231—C232 | 118.2 (4) |
C26—N21—H211 | 109 (4) | C236—C231—C237 | 118.5 (4) |
C22—N21—H211 | 105 (4) | C232—C231—C237 | 123.3 (4) |
C26—N21—H212 | 107 (4) | C233—C232—C231 | 120.7 (5) |
C22—N21—H212 | 110 (4) | C233—C232—I232 | 117.4 (4) |
H211—N21—H212 | 114 (6) | C231—C232—I232 | 121.9 (3) |
N21—C22—C23 | 111.3 (4) | C234—C233—C232 | 120.2 (5) |
N21—C22—H22A | 109.4 | C234—C233—H233 | 119.9 |
C23—C22—H22A | 109.4 | C232—C233—H233 | 119.9 |
N21—C22—H22B | 109.4 | C233—C234—C235 | 120.3 (5) |
C23—C22—H22B | 109.4 | C233—C234—H234 | 119.9 |
H22A—C22—H22B | 108.0 | C235—C234—H234 | 119.9 |
N24—C23—C22 | 110.7 (4) | C236—C235—C234 | 119.9 (5) |
N24—C23—H23A | 109.5 | C236—C235—H235 | 120.0 |
C22—C23—H23A | 109.5 | C234—C235—H235 | 120.0 |
N24—C23—H23B | 109.5 | C235—C236—C231 | 120.8 (5) |
C22—C23—H23B | 109.5 | C235—C236—H236 | 119.6 |
H23A—C23—H23B | 108.1 | C231—C236—H236 | 119.6 |
C221—N24—C23 | 118.0 (4) | O231—C237—O232 | 127.0 (4) |
C221—N24—C25 | 116.3 (4) | O231—C237—C231 | 116.2 (4) |
C23—N24—C25 | 110.7 (4) | O232—C237—C231 | 116.7 (4) |
C16—N11—C12—C13 | −55.3 (6) | C222—C223—C224—C225 | −0.4 (10) |
N11—C12—C13—N14 | 57.8 (6) | C222—C223—C224—F224 | 179.0 (5) |
C12—C13—N14—C121 | 166.2 (4) | C223—C224—C225—C226 | 0.7 (10) |
C12—C13—N14—C15 | −58.5 (5) | F224—C224—C225—C226 | −178.7 (5) |
C121—N14—C15—C16 | −168.6 (4) | C224—C225—C226—C221 | −0.6 (8) |
C13—N14—C15—C16 | 57.6 (5) | C222—C221—C226—C225 | 0.3 (7) |
C12—N11—C16—C15 | 54.5 (6) | N24—C221—C226—C225 | 177.1 (5) |
N14—C15—C16—N11 | −56.1 (6) | C136—C131—C132—C133 | −0.9 (6) |
C15—N14—C121—C122 | 179.7 (4) | C137—C131—C132—C133 | −179.8 (4) |
C13—N14—C121—C122 | −48.5 (6) | C136—C131—C132—I132 | 177.2 (3) |
C15—N14—C121—C126 | 2.6 (6) | C137—C131—C132—I132 | −1.8 (6) |
C13—N14—C121—C126 | 134.4 (5) | C131—C132—C133—C134 | −0.5 (7) |
C126—C121—C122—C123 | 0.2 (8) | I132—C132—C133—C134 | −178.6 (4) |
N14—C121—C122—C123 | −177.1 (5) | C132—C133—C134—C135 | 1.0 (9) |
C121—C122—C123—C124 | 0.4 (9) | C133—C134—C135—C136 | 0.0 (10) |
C122—C123—C124—C125 | 0.2 (10) | C134—C135—C136—C131 | −1.5 (10) |
C122—C123—C124—F124 | 179.6 (5) | C132—C131—C136—C135 | 1.9 (8) |
C123—C124—C125—C126 | −1.3 (10) | C137—C131—C136—C135 | −179.1 (5) |
F124—C124—C125—C126 | 179.2 (5) | C132—C131—C137—O132 | −77.1 (6) |
C124—C125—C126—C121 | 1.9 (10) | C136—C131—C137—O132 | 103.9 (6) |
C122—C121—C126—C125 | −1.3 (8) | C132—C131—C137—O131 | 104.8 (5) |
N14—C121—C126—C125 | 175.9 (5) | C136—C131—C137—O131 | −74.1 (6) |
C26—N21—C22—C23 | −53.0 (6) | C236—C231—C232—C233 | 0.0 (7) |
N21—C22—C23—N24 | 55.1 (6) | C237—C231—C232—C233 | 179.3 (5) |
C22—C23—N24—C221 | 163.7 (4) | C236—C231—C232—I232 | 178.8 (3) |
C22—C23—N24—C25 | −58.7 (5) | C237—C231—C232—I232 | −1.8 (6) |
C221—N24—C25—C26 | −161.9 (4) | C231—C232—C233—C234 | 0.1 (8) |
C23—N24—C25—C26 | 59.8 (5) | I232—C232—C233—C234 | −178.8 (5) |
C22—N21—C26—C25 | 53.6 (6) | C232—C233—C234—C235 | 0.1 (10) |
N24—C25—C26—N21 | −56.6 (6) | C233—C234—C235—C236 | −0.4 (10) |
C23—N24—C221—C222 | 2.1 (7) | C234—C235—C236—C231 | 0.4 (9) |
C25—N24—C221—C222 | −133.2 (5) | C232—C231—C236—C235 | −0.2 (7) |
C23—N24—C221—C226 | −174.5 (4) | C237—C231—C236—C235 | −179.6 (5) |
C25—N24—C221—C226 | 50.2 (6) | C236—C231—C237—O231 | 66.0 (6) |
C226—C221—C222—C223 | −0.1 (8) | C232—C231—C237—O231 | −113.4 (5) |
N24—C221—C222—C223 | −176.7 (5) | C236—C231—C237—O232 | −112.9 (5) |
C221—C222—C223—C224 | 0.1 (9) | C232—C231—C237—O232 | 67.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H111···O132 | 0.80 (6) | 1.89 (6) | 2.680 (7) | 168 (6) |
N11—H112···O231 | 0.90 (6) | 1.87 (6) | 2.758 (6) | 171 (4) |
N21—H211···O232 | 0.79 (6) | 1.88 (6) | 2.665 (6) | 173 (6) |
N21—H212···O131 | 0.85 (7) | 1.87 (7) | 2.714 (6) | 179 (8) |
C13—H13A···O131i | 0.97 | 2.50 | 3.396 (7) | 154 |
C133—H133···Cg2ii | 0.93 | 2.69 | 3.433 (6) | 137 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z. |
C10H14FN2+·C6H2N3O7− | F(000) = 848 |
Mr = 409.34 | Dx = 1.576 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 16.658 (2) Å | Cell parameters from 3865 reflections |
b = 6.6734 (6) Å | θ = 2.6–27.8° |
c = 17.553 (3) Å | µ = 0.13 mm−1 |
β = 117.84 (2)° | T = 293 K |
V = 1725.4 (5) Å3 | Block, orange |
Z = 4 | 0.48 × 0.40 × 0.40 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 3865 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2922 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 27.8°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −21→20 |
Tmin = 0.816, Tmax = 0.949 | k = −8→8 |
12153 measured reflections | l = −23→17 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.069P)2 + 0.535P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.136 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.45 e Å−3 |
3865 reflections | Δρmin = −0.27 e Å−3 |
269 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0063 (12) |
Primary atom site location: difference Fourier map |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.40587 (10) | 0.4532 (3) | 0.63092 (10) | 0.0437 (4) | |
H11 | 0.4673 (15) | 0.458 (3) | 0.6543 (14) | 0.052* | |
H12 | 0.3839 (14) | 0.402 (3) | 0.5813 (15) | 0.052* | |
C2 | 0.37290 (12) | 0.6586 (3) | 0.62596 (14) | 0.0539 (5) | |
H2A | 0.3861 | 0.7353 | 0.5862 | 0.065* | |
H2B | 0.4045 | 0.7211 | 0.6822 | 0.065* | |
C3 | 0.27242 (12) | 0.6622 (3) | 0.59632 (15) | 0.0562 (5) | |
H3A | 0.2532 | 0.7996 | 0.5958 | 0.067* | |
H3B | 0.2408 | 0.6114 | 0.5378 | 0.067* | |
N4 | 0.24731 (9) | 0.5429 (2) | 0.65119 (9) | 0.0368 (3) | |
C5 | 0.27922 (12) | 0.3385 (3) | 0.65583 (15) | 0.0554 (5) | |
H5A | 0.2471 | 0.2767 | 0.5995 | 0.066* | |
H5B | 0.2656 | 0.2626 | 0.6955 | 0.066* | |
C6 | 0.37933 (13) | 0.3300 (4) | 0.68511 (16) | 0.0659 (6) | |
H6A | 0.4117 | 0.3765 | 0.7442 | 0.079* | |
H6B | 0.3969 | 0.1921 | 0.6837 | 0.079* | |
C21 | 0.15488 (10) | 0.5597 (3) | 0.63263 (10) | 0.0363 (4) | |
C22 | 0.10464 (13) | 0.7296 (3) | 0.59483 (14) | 0.0564 (5) | |
H22 | 0.1312 | 0.8344 | 0.5798 | 0.068* | |
C23 | 0.01531 (13) | 0.7464 (4) | 0.57899 (14) | 0.0654 (6) | |
H23 | −0.0176 | 0.8621 | 0.5539 | 0.078* | |
C24 | −0.02378 (12) | 0.5940 (4) | 0.60014 (12) | 0.0533 (5) | |
F24 | −0.11190 (7) | 0.6095 (3) | 0.58299 (9) | 0.0781 (4) | |
C25 | 0.02295 (13) | 0.4251 (3) | 0.63800 (15) | 0.0582 (5) | |
H25 | −0.0048 | 0.3218 | 0.6526 | 0.070* | |
C26 | 0.11240 (12) | 0.4082 (3) | 0.65464 (14) | 0.0530 (5) | |
H26 | 0.1448 | 0.2929 | 0.6811 | 0.064* | |
C31 | 0.66352 (10) | 0.5012 (2) | 0.76514 (10) | 0.0325 (3) | |
O31 | 0.58276 (8) | 0.4723 (2) | 0.74598 (8) | 0.0515 (4) | |
C32 | 0.69912 (10) | 0.5164 (2) | 0.70408 (9) | 0.0311 (3) | |
C33 | 0.78970 (10) | 0.5187 (2) | 0.72642 (10) | 0.0316 (3) | |
H33 | 0.8087 | 0.5195 | 0.6843 | 0.038* | |
C34 | 0.85232 (10) | 0.5198 (2) | 0.81288 (10) | 0.0310 (3) | |
C35 | 0.82562 (10) | 0.5169 (2) | 0.87651 (10) | 0.0307 (3) | |
H35 | 0.8686 | 0.5201 | 0.9343 | 0.037* | |
C36 | 0.73523 (10) | 0.5092 (2) | 0.85326 (9) | 0.0306 (3) | |
N32 | 0.63656 (10) | 0.5325 (2) | 0.61270 (9) | 0.0408 (3) | |
O32 | 0.55940 (9) | 0.5932 (3) | 0.59024 (9) | 0.0663 (4) | |
O33 | 0.66548 (10) | 0.4937 (3) | 0.56166 (9) | 0.0652 (4) | |
N34 | 0.94736 (9) | 0.5289 (2) | 0.83657 (10) | 0.0408 (3) | |
O34 | 0.97031 (9) | 0.4935 (2) | 0.78121 (10) | 0.0596 (4) | |
O35 | 1.00128 (8) | 0.5720 (3) | 0.91068 (9) | 0.0653 (4) | |
N36 | 0.71188 (10) | 0.5052 (2) | 0.92360 (9) | 0.0415 (3) | |
O36 | 0.76681 (10) | 0.4316 (2) | 0.99197 (8) | 0.0586 (4) | |
O37 | 0.64114 (10) | 0.5790 (3) | 0.91295 (10) | 0.0662 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0255 (7) | 0.0670 (10) | 0.0364 (7) | 0.0038 (7) | 0.0125 (6) | −0.0009 (7) |
C2 | 0.0398 (9) | 0.0577 (12) | 0.0692 (13) | −0.0043 (9) | 0.0296 (9) | 0.0047 (10) |
C3 | 0.0405 (10) | 0.0588 (12) | 0.0768 (14) | 0.0120 (9) | 0.0336 (10) | 0.0262 (10) |
N4 | 0.0308 (7) | 0.0434 (8) | 0.0381 (7) | 0.0044 (6) | 0.0178 (6) | 0.0026 (6) |
C5 | 0.0435 (10) | 0.0489 (11) | 0.0845 (14) | 0.0110 (8) | 0.0389 (10) | 0.0155 (10) |
C6 | 0.0454 (11) | 0.0752 (15) | 0.0866 (15) | 0.0254 (10) | 0.0389 (11) | 0.0360 (13) |
C21 | 0.0310 (8) | 0.0481 (9) | 0.0304 (7) | 0.0037 (7) | 0.0150 (6) | −0.0019 (7) |
C22 | 0.0460 (10) | 0.0672 (13) | 0.0647 (12) | 0.0181 (9) | 0.0330 (9) | 0.0228 (10) |
C23 | 0.0470 (11) | 0.0883 (17) | 0.0643 (13) | 0.0309 (11) | 0.0289 (10) | 0.0238 (12) |
C24 | 0.0305 (8) | 0.0867 (15) | 0.0421 (10) | 0.0051 (9) | 0.0165 (8) | −0.0072 (10) |
F24 | 0.0314 (6) | 0.1237 (12) | 0.0776 (9) | 0.0088 (7) | 0.0241 (6) | −0.0065 (8) |
C25 | 0.0423 (10) | 0.0666 (13) | 0.0737 (14) | −0.0085 (9) | 0.0337 (10) | −0.0089 (11) |
C26 | 0.0417 (10) | 0.0512 (11) | 0.0719 (13) | 0.0038 (8) | 0.0314 (10) | 0.0038 (10) |
C31 | 0.0254 (7) | 0.0299 (7) | 0.0367 (8) | 0.0004 (6) | 0.0099 (6) | −0.0011 (6) |
O31 | 0.0251 (6) | 0.0758 (9) | 0.0483 (7) | −0.0046 (6) | 0.0125 (5) | 0.0002 (6) |
C32 | 0.0301 (7) | 0.0278 (7) | 0.0273 (7) | −0.0015 (6) | 0.0066 (6) | −0.0006 (6) |
C33 | 0.0349 (8) | 0.0283 (7) | 0.0331 (7) | −0.0013 (6) | 0.0171 (6) | 0.0003 (6) |
C34 | 0.0241 (7) | 0.0294 (7) | 0.0366 (8) | −0.0002 (6) | 0.0119 (6) | 0.0013 (6) |
C35 | 0.0276 (7) | 0.0290 (7) | 0.0292 (7) | −0.0008 (6) | 0.0081 (6) | −0.0008 (6) |
C36 | 0.0295 (7) | 0.0308 (7) | 0.0307 (7) | −0.0008 (6) | 0.0135 (6) | −0.0021 (6) |
N32 | 0.0405 (8) | 0.0403 (8) | 0.0305 (7) | −0.0064 (6) | 0.0073 (6) | −0.0005 (6) |
O32 | 0.0406 (7) | 0.0907 (12) | 0.0437 (8) | 0.0081 (7) | −0.0003 (6) | 0.0033 (7) |
O33 | 0.0647 (9) | 0.0950 (12) | 0.0317 (7) | 0.0007 (8) | 0.0190 (6) | 0.0027 (7) |
N34 | 0.0274 (7) | 0.0446 (8) | 0.0493 (8) | 0.0015 (6) | 0.0169 (6) | 0.0076 (6) |
O34 | 0.0411 (7) | 0.0796 (10) | 0.0699 (9) | 0.0047 (7) | 0.0358 (7) | 0.0033 (8) |
O35 | 0.0281 (6) | 0.1017 (12) | 0.0520 (8) | −0.0113 (7) | 0.0069 (6) | −0.0006 (8) |
N36 | 0.0383 (7) | 0.0483 (8) | 0.0417 (8) | −0.0061 (6) | 0.0219 (6) | −0.0090 (6) |
O36 | 0.0569 (8) | 0.0831 (11) | 0.0368 (7) | 0.0005 (7) | 0.0226 (6) | 0.0068 (7) |
O37 | 0.0517 (8) | 0.0930 (12) | 0.0654 (9) | 0.0102 (8) | 0.0369 (7) | −0.0124 (8) |
N1—C2 | 1.464 (3) | C24—C25 | 1.355 (3) |
N1—C6 | 1.473 (3) | C24—F24 | 1.358 (2) |
N1—H11 | 0.91 (2) | C25—C26 | 1.383 (2) |
N1—H12 | 0.84 (2) | C25—H25 | 0.9300 |
C2—C3 | 1.503 (2) | C26—H26 | 0.9300 |
C2—H2A | 0.9700 | C31—O31 | 1.2398 (19) |
C2—H2B | 0.9700 | C31—C36 | 1.448 (2) |
C3—N4 | 1.453 (2) | C31—C32 | 1.451 (2) |
C3—H3A | 0.9700 | C32—C33 | 1.371 (2) |
C3—H3B | 0.9700 | C32—N32 | 1.4522 (19) |
N4—C21 | 1.4215 (19) | C33—C34 | 1.383 (2) |
N4—C5 | 1.452 (2) | C33—H33 | 0.9300 |
C5—C6 | 1.499 (2) | C34—C35 | 1.382 (2) |
C5—H5A | 0.9700 | C34—N34 | 1.4383 (19) |
C5—H5B | 0.9700 | C35—C36 | 1.365 (2) |
C6—H6A | 0.9700 | C35—H35 | 0.9300 |
C6—H6B | 0.9700 | C36—N36 | 1.458 (2) |
C21—C22 | 1.381 (3) | N32—O32 | 1.224 (2) |
C21—C26 | 1.388 (3) | N32—O33 | 1.227 (2) |
C22—C23 | 1.385 (3) | N34—O35 | 1.221 (2) |
C22—H22 | 0.9300 | N34—O34 | 1.222 (2) |
C23—C24 | 1.350 (3) | N36—O37 | 1.2084 (19) |
C23—H23 | 0.9300 | N36—O36 | 1.222 (2) |
C2—N1—C6 | 110.09 (15) | C24—C23—C22 | 119.7 (2) |
C2—N1—H11 | 107.8 (13) | C24—C23—H23 | 120.2 |
C6—N1—H11 | 110.0 (13) | C22—C23—H23 | 120.2 |
C2—N1—H12 | 110.5 (15) | C23—C24—C25 | 121.43 (17) |
C6—N1—H12 | 108.8 (15) | C23—C24—F24 | 119.5 (2) |
H11—N1—H12 | 109.7 (19) | C25—C24—F24 | 119.1 (2) |
N1—C2—C3 | 111.20 (16) | C24—C25—C26 | 119.2 (2) |
N1—C2—H2A | 109.4 | C24—C25—H25 | 120.4 |
C3—C2—H2A | 109.4 | C26—C25—H25 | 120.4 |
N1—C2—H2B | 109.4 | C25—C26—C21 | 121.39 (19) |
C3—C2—H2B | 109.4 | C25—C26—H26 | 119.3 |
H2A—C2—H2B | 108.0 | C21—C26—H26 | 119.3 |
N4—C3—C2 | 112.37 (16) | O31—C31—C36 | 123.02 (15) |
N4—C3—H3A | 109.1 | O31—C31—C32 | 125.20 (15) |
C2—C3—H3A | 109.1 | C36—C31—C32 | 111.63 (13) |
N4—C3—H3B | 109.1 | C33—C32—C31 | 124.38 (14) |
C2—C3—H3B | 109.1 | C33—C32—N32 | 116.20 (14) |
H3A—C3—H3B | 107.9 | C31—C32—N32 | 119.41 (14) |
C21—N4—C5 | 114.59 (14) | C32—C33—C34 | 118.65 (14) |
C21—N4—C3 | 114.90 (13) | C32—C33—H33 | 120.7 |
C5—N4—C3 | 109.90 (14) | C34—C33—H33 | 120.7 |
N4—C5—C6 | 111.98 (17) | C35—C34—C33 | 121.63 (14) |
N4—C5—H5A | 109.2 | C35—C34—N34 | 119.56 (14) |
C6—C5—H5A | 109.2 | C33—C34—N34 | 118.80 (14) |
N4—C5—H5B | 109.2 | C36—C35—C34 | 119.04 (14) |
C6—C5—H5B | 109.2 | C36—C35—H35 | 120.5 |
H5A—C5—H5B | 107.9 | C34—C35—H35 | 120.5 |
N1—C6—C5 | 112.26 (16) | C35—C36—C31 | 124.43 (14) |
N1—C6—H6A | 109.2 | C35—C36—N36 | 116.17 (13) |
C5—C6—H6A | 109.2 | C31—C36—N36 | 119.39 (13) |
N1—C6—H6B | 109.2 | O32—N32—O33 | 123.09 (15) |
C5—C6—H6B | 109.2 | O32—N32—C32 | 118.97 (15) |
H6A—C6—H6B | 107.9 | O33—N32—C32 | 117.84 (15) |
C22—C21—C26 | 117.27 (16) | O35—N34—O34 | 123.04 (15) |
C22—C21—N4 | 121.57 (16) | O35—N34—C34 | 118.74 (15) |
C26—C21—N4 | 121.12 (15) | O34—N34—C34 | 118.22 (15) |
C21—C22—C23 | 121.1 (2) | O37—N36—O36 | 123.00 (15) |
C21—C22—H22 | 119.5 | O37—N36—C36 | 119.22 (15) |
C23—C22—H22 | 119.5 | O36—N36—C36 | 117.74 (14) |
C6—N1—C2—C3 | −54.1 (2) | C36—C31—C32—N32 | −173.50 (13) |
N1—C2—C3—N4 | 56.7 (2) | C31—C32—C33—C34 | −4.4 (2) |
C2—C3—N4—C21 | 172.77 (16) | N32—C32—C33—C34 | 174.93 (13) |
C2—C3—N4—C5 | −56.2 (2) | C32—C33—C34—C35 | 0.6 (2) |
C21—N4—C5—C6 | −173.67 (16) | C32—C33—C34—N34 | −177.97 (14) |
C3—N4—C5—C6 | 55.2 (2) | C33—C34—C35—C36 | 1.2 (2) |
C2—N1—C6—C5 | 53.9 (3) | N34—C34—C35—C36 | 179.69 (14) |
N4—C5—C6—N1 | −55.2 (3) | C34—C35—C36—C31 | 0.8 (2) |
C5—N4—C21—C22 | −155.31 (19) | C34—C35—C36—N36 | 179.64 (14) |
C3—N4—C21—C22 | −26.6 (2) | O31—C31—C36—C35 | 171.87 (16) |
C5—N4—C21—C26 | 27.0 (2) | C32—C31—C36—C35 | −4.0 (2) |
C3—N4—C21—C26 | 155.66 (19) | O31—C31—C36—N36 | −6.9 (2) |
C26—C21—C22—C23 | −0.6 (3) | C32—C31—C36—N36 | 177.23 (13) |
N4—C21—C22—C23 | −178.38 (18) | C33—C32—N32—O32 | −157.44 (16) |
C21—C22—C23—C24 | −0.5 (3) | C31—C32—N32—O32 | 21.9 (2) |
C22—C23—C24—C25 | 1.1 (3) | C33—C32—N32—O33 | 19.0 (2) |
C22—C23—C24—F24 | −178.73 (19) | C31—C32—N32—O33 | −161.62 (16) |
C23—C24—C25—C26 | −0.5 (3) | C35—C34—N34—O35 | −13.8 (2) |
F24—C24—C25—C26 | 179.29 (18) | C33—C34—N34—O35 | 164.79 (16) |
C24—C25—C26—C21 | −0.6 (3) | C35—C34—N34—O34 | 166.42 (15) |
C22—C21—C26—C25 | 1.1 (3) | C33—C34—N34—O34 | −15.0 (2) |
N4—C21—C26—C25 | 178.95 (18) | C35—C36—N36—O37 | 149.59 (16) |
O31—C31—C32—C33 | −169.91 (16) | C31—C36—N36—O37 | −31.5 (2) |
C36—C31—C32—C33 | 5.8 (2) | C35—C36—N36—O36 | −28.3 (2) |
O31—C31—C32—N32 | 10.8 (2) | C31—C36—N36—O36 | 150.60 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.91 (3) | 1.85 (2) | 2.687 (2) | 153 (2) |
N1—H11···O32 | 0.91 (3) | 2.46 (3) | 3.103 (3) | 128.2 (17) |
N1—H12···O33i | 0.84 (2) | 2.35 (2) | 3.035 (2) | 138.5 (18) |
C5—H5A···O36ii | 0.97 | 2.49 | 3.318 (3) | 144 |
C6—H6B···O34iii | 0.97 | 2.40 | 3.207 (3) | 140 |
C25—H25···O37iv | 0.93 | 2.58 | 3.365 (3) | 142 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+1/2, y−1/2, −z+3/2. |
C10H14FN2+·C7H3N2O6− | F(000) = 1632 |
Mr = 392.34 | Dx = 1.362 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 19.871 (1) Å | Cell parameters from 4082 reflections |
b = 7.3420 (7) Å | θ = 3.0–27.7° |
c = 26.306 (2) Å | µ = 0.11 mm−1 |
β = 94.540 (8)° | T = 293 K |
V = 3825.8 (5) Å3 | Plate, orange |
Z = 8 | 0.46 × 0.42 × 0.22 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 4080 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2490 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 27.7°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −26→20 |
Tmin = 0.832, Tmax = 0.976 | k = −7→9 |
7938 measured reflections | l = −34→29 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.144 | w = 1/[σ2(Fo2) + (0.0501P)2 + 3.0431P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
4080 reflections | Δρmax = 0.19 e Å−3 |
259 parameters | Δρmin = −0.18 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.50399 (11) | 0.4508 (4) | 0.58562 (8) | 0.0639 (7) | |
H11 | 0.4607 (15) | 0.472 (4) | 0.5700 (10) | 0.077* | |
H12 | 0.5386 (14) | 0.469 (4) | 0.5632 (10) | 0.077* | |
C2 | 0.50591 (13) | 0.2591 (4) | 0.60334 (10) | 0.0693 (8) | |
H2A | 0.5042 | 0.1785 | 0.5741 | 0.083* | |
H2B | 0.4666 | 0.2348 | 0.6219 | 0.083* | |
C3 | 0.56927 (12) | 0.2204 (4) | 0.63747 (9) | 0.0605 (7) | |
H3A | 0.5685 | 0.0957 | 0.6496 | 0.073* | |
H3B | 0.6087 | 0.2357 | 0.6184 | 0.073* | |
N4 | 0.57304 (9) | 0.3446 (3) | 0.68058 (7) | 0.0499 (5) | |
C5 | 0.57665 (12) | 0.5329 (4) | 0.66245 (9) | 0.0578 (6) | |
H5A | 0.6160 | 0.5475 | 0.6433 | 0.069* | |
H5B | 0.5811 | 0.6152 | 0.6914 | 0.069* | |
C6 | 0.51379 (12) | 0.5795 (4) | 0.62894 (9) | 0.0601 (7) | |
H6A | 0.4749 | 0.5748 | 0.6490 | 0.072* | |
H6B | 0.5175 | 0.7026 | 0.6160 | 0.072* | |
C21 | 0.61998 (10) | 0.3004 (3) | 0.72265 (8) | 0.0474 (6) | |
C22 | 0.66827 (12) | 0.1663 (4) | 0.72083 (9) | 0.0603 (7) | |
H22 | 0.6724 | 0.1034 | 0.6906 | 0.072* | |
C23 | 0.71091 (13) | 0.1240 (4) | 0.76380 (10) | 0.0697 (8) | |
H23 | 0.7429 | 0.0319 | 0.7627 | 0.084* | |
C24 | 0.70484 (13) | 0.2199 (4) | 0.80725 (10) | 0.0616 (7) | |
F24 | 0.74665 (9) | 0.1803 (3) | 0.84952 (6) | 0.0940 (6) | |
C25 | 0.65828 (14) | 0.3538 (4) | 0.81063 (9) | 0.0649 (7) | |
H25 | 0.6553 | 0.4173 | 0.8409 | 0.078* | |
C26 | 0.61553 (12) | 0.3937 (4) | 0.76819 (9) | 0.0596 (7) | |
H26 | 0.5832 | 0.4845 | 0.7701 | 0.072* | |
C31 | 0.28091 (10) | 0.5173 (3) | 0.49463 (8) | 0.0426 (5) | |
C32 | 0.25827 (11) | 0.5776 (3) | 0.44636 (9) | 0.0488 (6) | |
H32 | 0.2890 | 0.6164 | 0.4237 | 0.059* | |
C33 | 0.19032 (12) | 0.5798 (3) | 0.43210 (8) | 0.0504 (6) | |
C34 | 0.14305 (12) | 0.5225 (3) | 0.46380 (9) | 0.0522 (6) | |
H34 | 0.0972 | 0.5242 | 0.4536 | 0.063* | |
C35 | 0.16663 (11) | 0.4623 (3) | 0.51147 (9) | 0.0463 (5) | |
C36 | 0.23450 (10) | 0.4594 (3) | 0.52782 (8) | 0.0434 (5) | |
H36 | 0.2487 | 0.4193 | 0.5605 | 0.052* | |
C37 | 0.35572 (11) | 0.5171 (3) | 0.51098 (10) | 0.0534 (6) | |
O31 | 0.37215 (8) | 0.4790 (3) | 0.55607 (7) | 0.0824 (6) | |
O32 | 0.39472 (9) | 0.5595 (4) | 0.47872 (8) | 0.0914 (7) | |
N33 | 0.16661 (14) | 0.6480 (4) | 0.38107 (9) | 0.0734 (7) | |
O33 | 0.20650 (13) | 0.7306 (3) | 0.35708 (8) | 0.0999 (8) | |
O34 | 0.10817 (12) | 0.6161 (4) | 0.36557 (8) | 0.1032 (8) | |
N35 | 0.11738 (10) | 0.3995 (3) | 0.54647 (9) | 0.0627 (6) | |
O35 | 0.05802 (9) | 0.3917 (3) | 0.53021 (9) | 0.0903 (7) | |
O36 | 0.13782 (10) | 0.3596 (3) | 0.58988 (8) | 0.0875 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0360 (10) | 0.109 (2) | 0.0463 (12) | 0.0062 (12) | −0.0019 (9) | 0.0130 (13) |
C2 | 0.0547 (15) | 0.098 (2) | 0.0529 (15) | −0.0039 (15) | −0.0078 (12) | −0.0124 (16) |
C3 | 0.0596 (15) | 0.0713 (17) | 0.0491 (14) | 0.0025 (13) | −0.0045 (11) | −0.0097 (13) |
N4 | 0.0509 (11) | 0.0569 (12) | 0.0406 (10) | 0.0022 (9) | −0.0044 (8) | −0.0004 (9) |
C5 | 0.0530 (14) | 0.0640 (16) | 0.0548 (14) | 0.0015 (12) | −0.0050 (11) | 0.0042 (13) |
C6 | 0.0490 (13) | 0.0767 (18) | 0.0541 (15) | 0.0059 (13) | 0.0015 (11) | 0.0111 (14) |
C21 | 0.0441 (12) | 0.0557 (14) | 0.0418 (12) | 0.0004 (10) | 0.0001 (10) | 0.0037 (11) |
C22 | 0.0615 (15) | 0.0680 (17) | 0.0505 (14) | 0.0122 (13) | −0.0014 (12) | −0.0038 (13) |
C23 | 0.0647 (16) | 0.0760 (19) | 0.0663 (18) | 0.0187 (14) | −0.0085 (14) | 0.0054 (15) |
C24 | 0.0579 (15) | 0.0756 (18) | 0.0486 (15) | −0.0036 (14) | −0.0125 (12) | 0.0146 (14) |
F24 | 0.0917 (12) | 0.1160 (14) | 0.0683 (10) | 0.0006 (10) | −0.0323 (9) | 0.0193 (10) |
C25 | 0.0721 (17) | 0.0804 (19) | 0.0411 (13) | −0.0046 (15) | −0.0028 (12) | −0.0039 (13) |
C26 | 0.0602 (15) | 0.0706 (17) | 0.0474 (14) | 0.0122 (13) | 0.0006 (11) | −0.0045 (13) |
C31 | 0.0402 (11) | 0.0415 (12) | 0.0455 (12) | 0.0050 (9) | −0.0005 (10) | −0.0112 (10) |
C32 | 0.0497 (13) | 0.0487 (14) | 0.0485 (13) | 0.0029 (11) | 0.0064 (10) | −0.0074 (11) |
C33 | 0.0569 (14) | 0.0505 (14) | 0.0424 (12) | 0.0085 (11) | −0.0053 (11) | −0.0033 (11) |
C34 | 0.0440 (12) | 0.0507 (14) | 0.0595 (15) | 0.0059 (11) | −0.0111 (11) | −0.0070 (12) |
C35 | 0.0416 (11) | 0.0429 (13) | 0.0539 (13) | 0.0013 (10) | 0.0017 (10) | −0.0026 (11) |
C36 | 0.0417 (11) | 0.0429 (12) | 0.0448 (12) | 0.0050 (9) | −0.0020 (10) | −0.0039 (10) |
C37 | 0.0401 (12) | 0.0620 (16) | 0.0579 (15) | 0.0044 (11) | 0.0029 (11) | −0.0119 (13) |
O31 | 0.0419 (9) | 0.1330 (19) | 0.0699 (13) | 0.0026 (11) | −0.0099 (9) | 0.0154 (13) |
O32 | 0.0466 (10) | 0.152 (2) | 0.0778 (13) | 0.0040 (12) | 0.0200 (10) | −0.0024 (14) |
N33 | 0.0852 (18) | 0.0794 (17) | 0.0537 (14) | 0.0249 (14) | −0.0067 (13) | 0.0003 (13) |
O33 | 0.1208 (19) | 0.1093 (18) | 0.0701 (14) | 0.0175 (15) | 0.0102 (13) | 0.0309 (14) |
O34 | 0.0853 (15) | 0.146 (2) | 0.0724 (14) | 0.0255 (15) | −0.0304 (12) | 0.0039 (14) |
N35 | 0.0465 (12) | 0.0626 (14) | 0.0795 (16) | 0.0019 (10) | 0.0081 (11) | 0.0074 (12) |
O35 | 0.0412 (10) | 0.1159 (18) | 0.1140 (17) | −0.0061 (11) | 0.0070 (10) | 0.0177 (14) |
O36 | 0.0689 (12) | 0.1166 (18) | 0.0783 (14) | −0.0009 (12) | 0.0146 (11) | 0.0302 (13) |
N1—C6 | 1.481 (3) | C24—C25 | 1.358 (4) |
N1—C2 | 1.482 (4) | C24—F24 | 1.366 (3) |
N1—H11 | 0.94 (3) | C25—C26 | 1.380 (3) |
N1—H12 | 0.95 (3) | C25—H25 | 0.9300 |
C2—C3 | 1.514 (3) | C26—H26 | 0.9300 |
C2—H2A | 0.9700 | C31—C32 | 1.386 (3) |
C2—H2B | 0.9700 | C31—C36 | 1.386 (3) |
C3—N4 | 1.453 (3) | C31—C37 | 1.515 (3) |
C3—H3A | 0.9700 | C32—C33 | 1.373 (3) |
C3—H3B | 0.9700 | C32—H32 | 0.9300 |
N4—C21 | 1.427 (3) | C33—C34 | 1.371 (3) |
N4—C5 | 1.466 (3) | C33—N33 | 1.474 (3) |
C5—C6 | 1.510 (3) | C34—C35 | 1.376 (3) |
C5—H5A | 0.9700 | C34—H34 | 0.9300 |
C5—H5B | 0.9700 | C35—C36 | 1.383 (3) |
C6—H6A | 0.9700 | C35—N35 | 1.470 (3) |
C6—H6B | 0.9700 | C36—H36 | 0.9300 |
C21—C22 | 1.378 (3) | C37—O32 | 1.234 (3) |
C21—C26 | 1.389 (3) | C37—O31 | 1.237 (3) |
C22—C23 | 1.393 (3) | N33—O33 | 1.214 (3) |
C22—H22 | 0.9300 | N33—O34 | 1.223 (3) |
C23—C24 | 1.356 (4) | N35—O36 | 1.217 (3) |
C23—H23 | 0.9300 | N35—O35 | 1.224 (2) |
C6—N1—C2 | 111.42 (19) | C24—C23—C22 | 118.6 (2) |
C6—N1—H11 | 107.0 (17) | C24—C23—H23 | 120.7 |
C2—N1—H11 | 107.1 (17) | C22—C23—H23 | 120.7 |
C6—N1—H12 | 109.2 (16) | C23—C24—C25 | 122.5 (2) |
C2—N1—H12 | 109.2 (17) | C23—C24—F24 | 119.1 (3) |
H11—N1—H12 | 113 (2) | C25—C24—F24 | 118.3 (2) |
N1—C2—C3 | 111.3 (2) | C24—C25—C26 | 118.7 (2) |
N1—C2—H2A | 109.4 | C24—C25—H25 | 120.7 |
C3—C2—H2A | 109.4 | C26—C25—H25 | 120.7 |
N1—C2—H2B | 109.4 | C25—C26—C21 | 121.1 (2) |
C3—C2—H2B | 109.4 | C25—C26—H26 | 119.5 |
H2A—C2—H2B | 108.0 | C21—C26—H26 | 119.5 |
N4—C3—C2 | 109.5 (2) | C32—C31—C36 | 119.43 (19) |
N4—C3—H3A | 109.8 | C32—C31—C37 | 120.0 (2) |
C2—C3—H3A | 109.8 | C36—C31—C37 | 120.5 (2) |
N4—C3—H3B | 109.8 | C33—C32—C31 | 119.7 (2) |
C2—C3—H3B | 109.8 | C33—C32—H32 | 120.2 |
H3A—C3—H3B | 108.2 | C31—C32—H32 | 120.2 |
C21—N4—C3 | 116.93 (19) | C34—C33—C32 | 122.5 (2) |
C21—N4—C5 | 114.89 (18) | C34—C33—N33 | 118.2 (2) |
C3—N4—C5 | 109.80 (19) | C32—C33—N33 | 119.3 (2) |
N4—C5—C6 | 110.1 (2) | C33—C34—C35 | 116.9 (2) |
N4—C5—H5A | 109.6 | C33—C34—H34 | 121.5 |
C6—C5—H5A | 109.6 | C35—C34—H34 | 121.5 |
N4—C5—H5B | 109.6 | C34—C35—C36 | 122.8 (2) |
C6—C5—H5B | 109.6 | C34—C35—N35 | 118.4 (2) |
H5A—C5—H5B | 108.1 | C36—C35—N35 | 118.8 (2) |
N1—C6—C5 | 110.9 (2) | C35—C36—C31 | 118.7 (2) |
N1—C6—H6A | 109.5 | C35—C36—H36 | 120.6 |
C5—C6—H6A | 109.5 | C31—C36—H36 | 120.6 |
N1—C6—H6B | 109.5 | O32—C37—O31 | 125.7 (2) |
C5—C6—H6B | 109.5 | O32—C37—C31 | 117.4 (2) |
H6A—C6—H6B | 108.1 | O31—C37—C31 | 116.8 (2) |
C22—C21—C26 | 118.3 (2) | O33—N33—O34 | 124.4 (3) |
C22—C21—N4 | 123.3 (2) | O33—N33—C33 | 117.9 (3) |
C26—C21—N4 | 118.3 (2) | O34—N33—C33 | 117.7 (3) |
C21—C22—C23 | 120.8 (2) | O36—N35—O35 | 123.9 (2) |
C21—C22—H22 | 119.6 | O36—N35—C35 | 118.3 (2) |
C23—C22—H22 | 119.6 | O35—N35—C35 | 117.8 (2) |
C6—N1—C2—C3 | −53.0 (3) | C37—C31—C32—C33 | −179.1 (2) |
N1—C2—C3—N4 | 57.3 (3) | C31—C32—C33—C34 | −0.6 (4) |
C2—C3—N4—C21 | 165.3 (2) | C31—C32—C33—N33 | 178.7 (2) |
C2—C3—N4—C5 | −61.5 (3) | C32—C33—C34—C35 | 0.3 (4) |
C21—N4—C5—C6 | −164.08 (19) | N33—C33—C34—C35 | −179.0 (2) |
C3—N4—C5—C6 | 61.7 (3) | C33—C34—C35—C36 | 0.4 (3) |
C2—N1—C6—C5 | 52.6 (3) | C33—C34—C35—N35 | −179.9 (2) |
N4—C5—C6—N1 | −56.8 (3) | C34—C35—C36—C31 | −0.8 (3) |
C3—N4—C21—C22 | 10.9 (3) | N35—C35—C36—C31 | 179.5 (2) |
C5—N4—C21—C22 | −120.0 (3) | C32—C31—C36—C35 | 0.5 (3) |
C3—N4—C21—C26 | −167.2 (2) | C37—C31—C36—C35 | 179.8 (2) |
C5—N4—C21—C26 | 61.9 (3) | C32—C31—C37—O32 | −5.1 (3) |
C26—C21—C22—C23 | 0.8 (4) | C36—C31—C37—O32 | 175.6 (2) |
N4—C21—C22—C23 | −177.3 (2) | C32—C31—C37—O31 | 173.0 (2) |
C21—C22—C23—C24 | −1.3 (4) | C36—C31—C37—O31 | −6.3 (3) |
C22—C23—C24—C25 | 0.8 (4) | C34—C33—N33—O33 | 166.0 (2) |
C22—C23—C24—F24 | −179.6 (2) | C32—C33—N33—O33 | −13.4 (4) |
C23—C24—C25—C26 | 0.0 (4) | C34—C33—N33—O34 | −14.6 (3) |
F24—C24—C25—C26 | −179.5 (2) | C32—C33—N33—O34 | 166.0 (2) |
C24—C25—C26—C21 | −0.5 (4) | C34—C35—N35—O36 | −174.5 (2) |
C22—C21—C26—C25 | 0.0 (4) | C36—C35—N35—O36 | 5.2 (3) |
N4—C21—C26—C25 | 178.2 (2) | C34—C35—N35—O35 | 5.1 (3) |
C36—C31—C32—C33 | 0.2 (3) | C36—C35—N35—O35 | −175.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O31 | 0.94 (3) | 1.77 (3) | 2.681 (3) | 164 (3) |
N1—H12···O32i | 0.95 (3) | 1.80 (3) | 2.731 (3) | 165 (3) |
C23—H23···Cg3ii | 0.93 | 2.88 | 3.787 (3) | 167 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y−1/2, −z+3/2. |
Cg1, Cg2 and Cg3 represent the centroids of the rings (C31–C36), (C221–C226) and (C21–C26), respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
I | ||||
N1—H11···O31 | 0.975 (19) | 1.773 (19) | 2.7426 (18) | 173.2 (14) |
N1—H12···O41 | 0.970 (16) | 1.793 (16) | 2.749 (2) | 167.9 (18) |
O41—H41···O32i | 0.84 (3) | 1.95 (3) | 2.7744 (19) | 168 (2) |
O41—H42···O31ii | 0.89 (3) | 1.80 (3) | 2.6693 (18) | 164 (2) |
C3—H3A···O32iii | 0.97 | 2.44 | 3.317 (3) | 149 |
(II) | ||||
N1—H11···O32 | 0.78 (4) | 1.93 (4) | 2.677 (4) | 160 (3) |
N1—H12···O3i | 0.91 (3) | 1.80 (3) | 2.707 (4) | 175 (3) |
O41—H41···O31 | 0.90 | 1.76 | 2.661 (12) | 179 |
O41—H42···O31iii | 0.89 | 1.90 | 2.792 (12) | 179 |
C35—H35···O41iv | 0.93 | 2.38 | 3.257 (11) | 157 |
C2—H2A···Cg1v | 0.97 | 2.78 | 3.598 (3) | 142 |
(III) | ||||
N11—H111···O132 | 0.80 (6) | 1.89 (6) | 2.680 (7) | 168 (6) |
N11—H112···O231 | 0.90 (6) | 1.87 (6) | 2.758 (6) | 171 (4) |
N21—H211···O232 | 0.79 (6) | 1.88 (6) | 2.665 (6) | 173 (6) |
N21—H212···O131 | 0.85 (7) | 1.87 (7) | 2.714 (6) | 179 (8) |
C13—H13A···O131i | 0.97 | 2.50 | 3.396 (7) | 154 |
C133—H133···Cg2vi | 0.93 | 2.69 | 3.433 (6) | 137 |
(IV) | ||||
N1—H11···O31 | 0.91 (3) | 1.85 (2) | 2.687 (2) | 153 (2) |
N1—H11···O32 | 0.91 (3) | 2.46 (3) | 3.103 (3) | 128.2 (17) |
N1—H12···O33i | 0.84 (2) | 2.35 (2) | 3.035 (2) | 138.5 (18) |
C5—H5A···O36vii | 0.97 | 2.49 | 3.318 (3) | 144 |
C6—H6B···O34viii | 0.97 | 2.40 | 3.207 (3) | 140 |
C25—H25···O37ix | 0.93 | 2.58 | 3.365 (3) | 142 |
(V) | ||||
N1—H11···O31 | 0.94 (3) | 1.77 (3) | 2.681 (3) | 164 (3) |
N1—H11···O32i | 0.95 (3) | 1.80 (3) | 2.731 (3) | 165 (3) |
C23—H23···Cg3viii | 0.93 | 2.88 | 3.787 (3) | 167 |
Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) -x, 1 - y, 1 - z; (iii) 1 - x, -y, 1 - z; (iv) 1 + x, y, z; (v) -1 + x, y, z; (vi) x, 1 + y, z; (vii) -1/2 + x, 1/2 - y, -1/2 + z; (viii) 3/2 - x, -1/2 + y, 3/2 - z; (ix) 1/2 - x, -1/2 + y, 3/2 - z. |
Acknowledgements
CHC thanks the University of Mysore for research facilities.
Funding information
HSY thanks the University Grants Commission, New Delhi, for the award of a BSR Faculty Fellowship for three years.
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