Yes, one can obtain better quality structures from routine X-ray data collection

Single-crystal X-ray diffraction structural results for benzidine dihydrochloride, hydrated and protonated N,N,N,N-peri(dimethylamino)naphthalene chloride, triptycene, dichlorodimethyltriptycene and decamethylferrocene have been analysed. A critical discussion of the dependence of structural and thermal parameters on resolution for these compounds is presented. Results of refinements against X-ray data, cut off to different resolutions from the high-resolution data files, are compared to structural models derived from neutron diffraction experiments. The Independent Atom Model (IAM) and the Transferable Aspherical Atom Model (TAAM) are tested. The average differences between the X-ray and neutron structural parameters (with the exception of valence angles defined by H atoms) decrease with the increasing 2θ_max angle. The scale of differences between X-ray and neutron geometrical parameters can be significantly reduced when data are collected to the higher, than commonly used, 2θ_max diffraction angles (for Mo Kα 2θ_max > 65°). The final structural and thermal parameters obtained for the studied compounds using TAAM refinement are in better agreement with the neutron values than the IAM results for all resolutions and all compounds. By using TAAM, it is still possible to obtain accurate results even from low-resolution X-ray data. This is particularly important as TAAM is easy to apply and can routinely be used to improve the quality of structural investigations [Dominiak (2015). LSDB from UBDB. University of Buffalo, USA]. We can recommend that, in order to obtain more adequate (more accurate and precise) structural and displacement parameters during the IAM model refinement, data should be collected up to the larger diffraction angles, at least, for Mo Kα radiation to 2θ_max = 65° (sin θ_max/λ < 0.75 Å⁻¹). The TAAM approach is a very good option to obtain more adequate results even using data collected to the lower 2θ_max angles. Also the results of translation–libration–screw (TLS) analysis and vibrational entropy values are more reliable for 2θ_max > 65°.

1. Introduction

Single-crystal X-ray and neutron diffraction techniques are the most common experimental methods for obtaining detailed information about the three-dimensional structure of molecules in the crystalline state. Approximately 100 000 crystal structures of organic and inorganic compounds are determined each year using X-rays alone. Structural data is considered to be extremely useful in crystal chemistry, pharmacy, crystal engineering, materials science etc., and is stored in the crystal structure databases such as the Cambridge Structural Database (CSD; Allen, 2002) or the Inorganic Crystal Structure Database (ICSD; Bergerhoff & Brown, 1987; Belsky et al., 2002). Such data is commonly used in pharmaceutical, medical, biological and physicochemical studies or theoretical simulations. Macromolecular/protein single-crystal X-ray structural data is also compiled in the Protein Data Bank (Berman et al., 2000). Wide applications of high-quality structural data are crucial for the further development of science as they are used to estimate the energy of inter- and intramolecular interactions. As small changes in geometrical parameters of molecules in crystals can lead to significant changes in conformational energy, it is important to identify not only which structural parameters undergo changes but also to estimate the magnitude of such changes.

In the case of X-ray diffraction, the quality of the final results of structural studies depends on several factors. One of the most important ones is the maximum diffraction angle, θ_max (or 2θ_max), up to which the measured reflections are still taken into consideration during structure refinement. According to the IUCr Commission Guidelines (IUCr, 2012), the maximum diffraction angle of the measured reflections (θ_max) for a single-crystal X-ray diffraction experiment intended for publication in crystallographic journals and crystallographic databases (CSD, ICSD) should be such that (sin θ/λ)_max exceeds 0.6 Å⁻¹ (i.e. θ_max > 25° for Mo Kα; θ_max > 67° for Cu Kα).

An electron density model used in the refinement procedure is another important factor which has a crucial influence on the structural parameters obtained from an X-ray diffraction experiment. The simplest and most frequently applied model in modern structural crystallography is the Independent Atom Model (IAM) which assumes that the molecular electron density is the sum over spherical, non-interacting atoms. It was introduced by Bragg and Compton in the Max von Laue and the Braggs era. In fact, the first spherical atomic scattering factors were calculated by Hartree in 1925 (Hartree, 1925).

In more advanced models, the asphericity of the atoms is considered. These models were first introduced by Hirshfeld (1971) and later developed by Stewart (1976) and Hansen & Coppens (1978). In the Stewart and Hansen–Coppens models, the total atomic density is the sum over so-called pseudoatoms, and the electron density of each pseudoatom is given by the sum of three components (core, valence and valence deformation density). These models can be used only for the high-resolution X-ray diffraction data. As electronic parameters of the same type of atoms in identical topological environment appear to be grouped close to their average values, the idea of constructing databanks of pseudoatoms (the smallest atomic fragments of electron density), from which the full electron density distribution can be reconstructed, emerged (Brock et al., 1991). There are three pseudoatom databanks: [UBDB (Koritsanszky et al., 2002; Volkov et al., 2004; Dominiak et al., 2007; Jarzembska & Dominiak, 2012), Invariom (Dittrich et al., 2004; Dittrich, Hubschle et al., 2006; Hübschle et al., 2007) and ELMAM (Pichon-Pesme et al., 1995; Domagała et al., 2012)]. ELMAM is based on purely experimental charge densities resulting from multipole refinement against high-resolution X-ray diffraction data, whereas the other two databases are based on theoretical results. Each of them can be applied in order to conduct Transferred Aspherical Atom Model (TAAM) refinement (Pichon-Pesme et al., 1995; Dominiak et al., 2007). A careful comparison of all databases has been discussed by Pichon-Pesme et al. (2004) and Bąk et al. (2011). With all these databases, it is possible to model electron density (ED) apparently better than by using IAM, and more accurately deconvolute thermal motion within TAAM refinement (Pichon-Pesme et al., 1995; Volkov et al., 2007). In TAAM refinement, pseudoatom parameters for each species are transferred from a chosen database and only atomic coordinates and ADPs are refined. Structural parameters obtained for the same X-ray data set after IAM and TAAM refinements are not the same.

We have decided to use the current version of the UBDB databank, i.e. UBDB2011 (Jarzembska & Dominiak, 2012). In UBDB, each atom type results from averaging electron density parameters over a family of chemically unique pseudo­atoms derived from the theoretical densities of a number of small molecules. The theoretical densities are obtained from B3LYP/6-31G** single-point calculations on the basis of experimental geometries taken from the CSD (Allen, 2002). In UBDB, only the valence structure factors are applied and the core electrons are added after the fitting procedure.

Neutron radiation is scattered by atomic nuclei. In consequence, H-atom positions and their displacement parameters can be determined more accurately using neutron diffraction than by applying single-crystal X-ray radiation. However, single-crystal neutron diffraction is less commonly used because of poor availability of the neutron sources and the required size of crystals. Although the most modern neutron facilities can provide reasonable results even for the sub­millimeter size single crystals, only ca 0.3% of all crystal structures added yearly to the structural databases are determined by neutron diffraction. Hereafter, we will abbreviate the geometry obtained from refinement of single-crystal neutron diffraction data by the term `neutron geometry' written without quotation marks.

It was shown that a molecular geometry very close to the neutron geometry can be obtained after multipole refinement of high-resolution X-ray data (Hoser et al., 2009). Moreover, it was shown that the TAAM refinement against high-resolution X-ray data significantly improves the molecular geometry (Dittrich, Munshi et al., 2006; Hübschle et al., 2007; Volkov et al., 2007; Jelsch et al., 2005) with respect to the independent atom model (IAM) and also leads to ADPs closer to those obtained from multipole refinements (Volkov et al., 2007; Dittrich et al., 2008; Bąk et al., 2009). Additionally, the results of TAAM refinement appear to give molecular geometries in excellent agreement with optimized geometries from CRYSTAL09 (Dovesi et al., 2005) calculations (Jarzembska et al., 2012). Despite the fact that TAAM significantly improves the model for high-resolution data, there were also some reports which show that possibly it should also give reasonable models for low-resolution data (Bąk et al., 2011). However, the use of TAAM refinement has not gained much attention yet.

Therefore, we would like to investigate how geometrical parameters change for different maximum θ_max diffraction angles in the case of IAM and TAAM refinements. Such an analysis may indicate how similar these models can get to the neutron geometry, especially when it was only possible to measure the low-resolution data. We have focused on the comparison of the structural neutron and X-ray results for crystals of five model compounds of different complexity and quality of data in the case of IAM, and for three of them in the case of the TAAM model. We also would like to verify whether commonly used resolution limits of data allow the best atomic geometrical and thermal parameters to be obtained.

Our work also includes an analysis of thermal parameters which are obtained after the IAM and TAAM refinements against X-ray diffraction data cut to different θ_max values. When ADPs are good quality, it is possible to conduct a TLS analysis (Cruickshank, 1956; Schomaker & Trueblood, 1968) and derive frequencies for translational and librational normal modes. Recently it was shown by Madsen & Larsen (2007) that such frequencies can be utilized to estimate the vibrational entropy of a crystal. Analysis of thermal motion conducted by Madsen & Larsen (2007) rely on ADPs obtained from high-resolution X-ray data for xylitol and ribitol. Lately it was suggested by Jarzembska et al. (2014) that high-resolution data are not necessarily needed and that to estimate vibrational entropy it is enough to conduct TAAM refinement on a low-resolution data. In our study we would like to verify this possibility.

For the purpose of our analysis we have chosen the following compounds: benzidine dihydrochloride (BD²⁺ × 2Cl⁻), hydrated and protonated N,N,N,N-peri(dimethylamino)naphthalene chloride (DMANH⁺ × 2Cl⁻ × H₅O₂⁺), triptycene (T), dichlorodimethyltriptycene (DCDMT) and decamethylferrocene (Fc*) as the model systems. Most of them were already studied and their structural details have already been published elsewhere (Hazell et al., 1971; Dobrzycki & Woźniak, 2006; Hoser et al., 2010; Makal et al., 2010) or deposited in the CSD (Refcodes: CCDC 999149–999150, CCDC 999141–999142). However, the single-crystal neutron diffraction refinement results for decamethylferrocene, triptycene and dichlorodimethyltriptycene are new. All these data sets have variable quality and one of the purposes of this work is to see the influence of quality of X-ray diffraction data on results compared with the corresponding neutron results. Structural properties of T and DCDMT will soon be discussed in a separate paper (Hoser et al., 2015). For all of them, we have both single-crystal neutron reference geometries and the results of X-ray diffraction data collection. All the molecules studied are illustrated in Fig. 1 and their most important parameters are given in Table 1.

Table 1
Symmetry and the unit-cell parameters for X-ray data collection of crystals of the studied compounds

All experiments were conducted at 100 K.

	BD^2+ × 2Cl^−	DMANH^+ × 2Cl^− × H5O2^+	T	DCDMT	Fc*
System	Triclinic	Monoclinic	Orthorhombic	Monoclinic	Orthorhombic
Space group		P21/n	P212121	P21	Cmca
Unit-cell dimensions
a (Å)	6.571 (1)	10.085 (1)	8.0798 (3)	13.589 (3)	15.091 (1)
b (Å)	7.676 (1)	9.811 (1)	8.1645 (3)	8.042 (2)	11.4741 (8)
c (Å)	12.610 (2)	17.915 (1)	20.3778 (8)	14.943 (3)	9.9484 (6)
α (°)	85.17 (1)	90.0	90.0	90.0	90.0
β (°)	76.79 (1)	101.639 (1)	90.0	94.00 (2)	90
γ (°)	73.87 (2)	90.0	90.0	90.0	90.0
Rint	0.031	0.029	0.030	0.032	0.023
I/σ	37.2	57.1	19.1	11.5	47.7
Completeness (%)	92	100	98.5	84	98
sin θ/λ (Å^−1)	1.16	1.16	1.16	1.20	1.13

Figure 1 Definition of the molecules studied: (a) benzidine dihydrochloride (BD^2+ × 2Cl^−), (b) hydrated and protonated N,N,N,N-peri(dimethylamino)naphthalene chloride (DMANH^+ × 2Cl^− × H5O2^+), (c) triptycene (T), (d) dichlorodimethyltriptycene (DCDMT), (e) decamethylferrocene (Fc*).

For each compound, a series of IAM and, for BD²⁺ × 2Cl⁻, DMANH⁺ × 2Cl⁻×H₅O₂⁺ and T, also TAAM refinements against X-ray data with different values of the limiting 2θ_max diffraction angle were conducted and their results were compared to the neutron structural results used as the reference ones. We will present a number of dependences of different parameters characterizing the quality of X-ray data sets and the average differences between particular neutron and structural parameters on the 2θ_max diffraction angle.

2. Methodology

The average difference between particular neutron and X-ray structural parameters of a given type (B_θ) is defined as

where n_i is the ith value of the neutron structural parameter for a given studied molecule, r_i is the ith value of the X-ray structural parameter, and N is the total number of parameters of a given type (for example, bond lengths between the non-H atoms, valence angles for heavy atoms, or similar parameters defined including H atoms).

First of all, all structural refinements of X-ray data were carried out in SHELX (Sheldrick, 2008) by modifying the refinement instruction input files (*.ins) by adding a proper OMIT instruction. The OMIT instruction allows definition of a limiting 2θ_max angle above which reflections are ignored. The value of the θ_max diffraction angle was increased by 1° in the range of θ_max angles from 20 to 40°. Then the refinement process based on |F|² was carried out using SHELX for each of these diffraction θ_max angle values. Finally, the B_θ values were calculated and plotted. As already mentioned in §1 all X-ray data sets have different quality including intentionally incomplete data for DCDMT (see Table 1). The Friedel pairs in the hkl data sets were not merged for DCDMT as there are Cl atoms in this structure, but were merged for T as in this case the molecule consists of only H and C atoms and the anomalous differences are not significant. The results obtained are presented as a series of diagrams showing a number of dependences of different parameters characterizing the quality of X-ray data sets and the average differences between particular neutron and X-ray structural parameters as a function of the 2θ_max diffraction angle for a series of the studied model molecules.

2.1. Neutron measurements

Neutron experiments were performed on the time-of-flight (TOF) single-crystal Laue diffractometer (SXD) (Keen et al., 2006) at ISIS (Oxfordshire, UK). The data were collected at 100 K. The integration process was carried out with SXD2001 (Guttmann, 2005). The structures were refined using SHELXL (Sheldrick, 2008) with the single batch of wavelength and extinction-corrected reflections. Crystallographic data are given in the supporting information. In the case of the neutron data, we have checked the Hirshfeld rigid-bond test (see the supporting information) which supplies excellent results showing that the rigid-bond approximation is well fulfilled (practically almost no DMSDA values larger than 0.0010 Ų).

2.2. TAAM refinements

For BD²⁺ × 2Cl⁻, DMANH⁺ × 2Cl⁻ × H₅O₂⁺ and T, a series of TAAM refinements have been performed varying the resolution range. Initial atomic coordinates and ADPs for each compound were taken from the IAM refinements. Initial multipolar parameters and contraction–expansion parameters were transferred from the University of Buffalo Data Bank (UBDB) with the aid of the LSDB program (Jarzembska & Dominiak, 2012). The multipole expansion was truncated at the hexadecapole (l_max = 4) level for the non-H atoms, whereas at the quadrupole (l_max = 2) level for H atoms. TAAM refinements based on |F|² have been performed in the MOPRO package (Guillot et al., 2001). Statistical weights were used. The refinement strategy was as follows: (1) scale factor; (2) scale factor, atomic coordinates and ADPs for the non-H atoms; (3) scale factor, atomic coordinates and ADPs for the hydrogen atoms; (4) scale factor, atomic coordinates and ADPs for all atoms. MOPRO allows the resolution range for the refinement procedure to be specified. For our purpose, all refinements for a given structure started from the same initial model and were performed utilizing different specified resolution ranges.

2.3. ADP analysis

In order to investigate differences in ADPs obtained after IAM and TAAM refinements against different resolution data, we decided to employ the similarity index. This index was introduced by Whitten & Spackmann (2006) and it is defined as

where R₁₂ is a measure of the overlap between the probability density functions described by two ADPs U1 and U2 (in the Cartesian frame)

For two identical ADPs R₁₂ = 1.0, and S₁₂ = 0. The smaller value of S₁₂ the better agreement between U1 and U2.

2.4. Crystal entropy evaluation

It has been shown by Bürgi and co-workers (Aree & Bürgi, 2006, 2012; Bürgi & Capelli, 2000; Capelli et al., 2000) that analysis of multi-temperature X-ray or neutron diffraction data may afford thermodynamic information, e.g. specific heats, when a rigid-body or semi-rigid body approach is applied to the ADPs. Subsequent results reported by Madsen & Larsen (2007; Madsen et al., 2011) indicate that in the case of low-temperature structures a single-temperature high-resolution X-ray measurement may be sufficient, provided that good quality ADPs are obtained. Having accurate estimates of ADPs, it is possible to calculate vibrational entropies S_TLS corresponding to the low-frequency lattice vibrations. To derive the vibrational entropy associated with the low-frequency modes, one should conduct the TLS analysis (Schomaker & Trueblood, 1968, 1998; Cruickshank, 1956; Sands, 1982) and compute the related frequencies (and some estimated standard uncertainties, based on the standard uncertainties given for the eigenvalues of the TLS-fit matrix in the THMA program; Schomaker & Trueblood, 1968). R_TLS, which help to judge the quality of the TLS-fit and indicates how much ADPs calculated after TLS analysis differ from those obtained after the X-ray diffraction experiment, is defined as:

where w_ij is the weight used in the least-squares fit of the TLS model against the observed ADPs U_measured^ij. After TLS analysis, the vibrational entropy of crystals as a function of temperature can then be calculated as the sum of the contributions from each oscillator

where R is the gas constant, k_B is Boltzmann's constant, and v_i is a frequency of a given ith oscillator. Following the above procedure, the vibrational entropy related to the low-frequency modes was estimated on the basis of the collected X-ray diffraction data with different resolution cut-offs and approaches of obtaining ADPs.

3. Results and discussion

3.1. (Reflections/parameters) ratio versus 2θ_max diffraction angle

The ratio of the number of independent reflections to the number of calculated parameters of a model fitted during least-squares refinement informs us about the feasibility and reliability of the refinement. Strict statisticians expect this ratio to be above 10, whereas more liberal statisticians expect it to be at least 5 in order to obtain meaningful results of the refinement. Of course, this ratio strongly depends on the 2θ_max diffraction angle. This parameter is one of a few which contribute to the quality of diffraction data. However, there are a few other parameters which are equally – or even more – important than this ratio, for example: averaged I/σ(I), R_int or R_sigma. Figs. 6S and 7S in the supporting information illustrate dependences of the R_merged value on the diffraction 2θ_max angle and I/σ versus resolution of data. In fact, only the analysis of all such parameters can give a reliable estimation of the quality of measured X-ray, or neutron, diffraction data.

In general, the reflection-to-parameters ratio increases as the 2θ_max angle increases and, for data with 100% completeness, it is ca 10 reflections per parameter for 2θ_max equal to ca 50° for small organic molecules with no heavy atoms. We present the dependence of the (reflections/parameters) ratio on the 2θ_max diffraction angle for our five studied molecules in the supporting information (Fig. 1S). One may say that these are typical data sets collected with 4-axis X-ray diffractometers using Mo Kα radiation. In general, we wanted to have X-ray data sets of variable quality and one of them (DCDMT) intentionally has poor completeness over the whole resolution range.

3.2. R_all versus 2θ_max diffraction angle

An agreement between the measured diffraction data and the refined model is characterized by discrepancy factors, for example, the residual factor for all reflections included in the refinement (R_all) defined as

where F is the structure factor, and |F|² represents the intensity of reflections. All refinements applying the IAM and TAAM models were carried out on the F² values. The dependence of the discrepancy factor R_all on the diffraction 2θ_max angle in the range of angles from 44 to 70° is illustrated in Fig. 2.

Figure 2 Dependence of the Rall factor on the 2θmax diffraction angle in the range of angles 44–70°.

Firstly, one can see really significant differences in the values of R_all resulting from the use of IAM and TAAM models. Within the whole range of resolutions, the TAAM R_all values are in the range 1–2%, which are ca 2–3 times smaller than the corresponding IAM R_all parameters. This is a clear demonstration of the superiority of the TAAM model over IAM. However, similarly as in the case of the refinement of the IAM models, R_all slightly increases or decreases depending of the information content of the higher-resolution reflections.

As could be expected, because of the poor quality of the collected data, T exhibits the largest R_all discrepancy factor values. It is interesting that for the other low quality data set, the discrepancy factors are increasing with increasing values of the diffraction 2θ_max angle (see DCDMT). This means that the difference between the model refined and measured information resulting from experiment increases despite the increase in the number of measured reflections which are used in the refinement. In this case, more noise than information is added with the increasing 2θ_max diffraction angle to the hkl file. The above effect can also be attributed to the lack of description of the bonding density.

On the other hand, for two data sets, when the reflection-to-parameters ratio increases, the R_all factor value reaches a maximum (ca 56° for BD²⁺ × 2Cl⁻ and 62° for T) and after that the discrepancy factors are decreasing as a function of diffraction angle. This means that together with the higher diffraction angle data more information than noise is collected. Similar relations are observed for R_GT and wR_GT (see Figs. 2S–4S in the supporting information). It is worth stressing that the IUCr limit (2θ_max = 50° for Mo Kα) does not lead to any special values of the discrepancy factors.

3.3. Dependences of different geometrical parameters on 2θ_max diffraction angle

3.3.1. Bond lengths between the non-H atoms versus 2θ_max diffraction angle

The average differences between the neutron and X-ray bond lengths for the non-H atoms as a function of the 2θ_max diffraction angle are illustrated in Fig. 3.

Figure 3 Average differences between the neutron and X-ray bond lengths for the non-H atoms as a function of the diffraction 2θmax angle in the range of angles 44–70°.

In the case of the IAM refinements for all the model compounds analysed in this work, the average differences between the X-ray and neutron parameters decrease as a function of the increasing 2θ_max diffraction angle, with the exception of Fc*. The decrease is the most noticeable for the BD²⁺ × 2Cl⁻ data. Most of the differences occur when 2θ_max is less than ca 56°. The average difference between the neutron and X-ray bond lengths for the non-H atoms is not greater than 0.010 Å, even for the low-quality data sets with poor resolution below the IUCr diffraction angle. When using the full resolution of the data this difference can drop to ca 0.0025 Å – or even less (for BD²⁺ × 2Cl⁻). With a resolution cut-off between 50 and 60°, the differences between X-ray and neutron models continue to drop and at 2θ_max = 60° it reaches a value which is ca 50% lower than for 2θ_max = 50°. This means that in order to have geometry of molecules closer to the neutron geometry, one should collect data to the higher 2θ_max diffraction angles as is common for routine X-ray data collection (and is common for experimental X-ray charge density studies).

It appears that TAAM refinements significantly improve agreement between the neutron and X-ray bond lengths for the non-H atoms. This is the case even for the low-resolution data, and it appears that the use of the resolution limit recommended by the IUCr is sufficient when the TAAM model is applied. The agreement between all results of IAM and TAAM refinements increases with the increasing resolution of data with the exception of Fc*.

3.3.2. Bond lengths to H atoms versus the 2θ_max angle

The average differences between the neutron and X-ray bond lengths to H atoms as a function of the diffraction 2θ_max angle are illustrated in Fig. 4. When the TAAM model was applied no standardization of X—H bond lengths to the averaged neutron data were performed (although in general for other applications this is possible). The superiority of the TAAM model is obvious with the differences between the corresponding IAM and TAAM values are in the range ca 0.10–0.15 Å. Again, the TAAM average differences between the neutron and X-ray bond lengths to H atoms seem to be more or less the same within the whole range of resolutions, which means that even low-resolution data could be enough to obtain reliable geometry (when TAAM is applied).

Figure 4 Average differences between the neutron and X-ray bond lengths to H atoms as a function of the 2θmax diffraction angle.

When referring to the bond lengths of H atoms, the average differences between the neutron and X-ray data are one order of magnitude higher than those obtained for the non-H atoms. It is interesting to note that for the bond lengths to H atoms the differences between the X-ray and neutron values are quite different for all compounds (in the range ca 0.09 Å to almost 0.16 Å). All these differences are only slightly decreasing with the increase of the 2θ_max diffraction angle. As normally seen in structural analysis, the X—H bonds are constrained to the average neutron values for a given X—H bond type; the average corrections for particular compounds will be different as the compounds consist of a different number of X—H bonds of a particular type. A typical range of changes of the average differences between the neutron and X-ray bond lengths to H atoms with increasing 2θ_max diffraction angle is ca 15%.

3.3.3. Valence angles for the non-H atoms versus 2θ_max diffraction angle

The average differences between the neutron and X-ray valence angles formed by the non-H atoms as a function of the 2θ_max diffraction angle in the range of angles from 40 to 80° are shown in Fig. 5.

Figure 5 Average differences between the neutron and X-ray valence angles for the non H atom as a function of the diffraction 2θmax angle in the range of angles 40–80°.

We observe a similar pattern for the valence angles as was seen for the bond lengths between non-H atoms. The agreement between X-ray and neutron valence angles increase with the resolution. As in the case of the other previously analysed parameters, the IUCr limit does not seem to be particularly justified. However, when the higher-resolution X-ray data with reflections collected over a relatively large 2θ range are used, the average differences between the neutron and X-ray valence angles for the non-H atoms can be as small as ca 0.15–0.20°. Again the TAAM is superior to the IAM. The difference between the average X-ray and neutron valence angles for the non-H atoms obtained by applying IAM and TAAM decreases with increasing resolution. However, for the 2θ_max angle = 50° (Mo Kα) such differences are significant with the valence angles obtained from TAAM being at least two times closer to the neutron values than the corresponding parameters obtained using the IAM with the exception of data for the DMAN salt for which this difference is smaller (ca 0.05°).

3.3.4. Valence angles of H atoms versus 2θ_max diffraction angle

The average differences between the neutron and X-ray valence angles defined by H atoms as a function of the 2θ_max diffraction angle are shown in Fig. 6.

Figure 6 Average differences between the neutron and X-ray valence angles defined by H atoms as a function of the 2θmax diffraction angle.

It appears that in the case of the valence angles defined by the inclusion of an H atom, the average difference between the neutron and X-ray values increases with increasing values of the 2θ_max diffraction angle. This is opposite to the relations obtained for the other structural parameters. The worse the quality of the hkl data set (Fc*, T, DCDMT), the larger differences between the average neutron and X-ray valence angles for H atoms (ca 1.7° for Fc* and DCDMT, ca 1.2 for T and ca 0.7° for BD²⁺ × 2Cl⁻ and DMANH⁺ × 2Cl⁻ × H₅O₂⁺). Similar to the other cases, the 2θ_max IUCr limit for the Mo Kα radiation is doubtful. Above 2θ_max = 70°, the discrepancy between the average X-ray and neutron values becomes more or less constant with the exception of T for which it continuously increases in the whole range 56–80°. This means that the common assumption behind the standardization/normalization procedure of bond length to H atoms (i.e. that the valence angles to H atoms do not change when one lengthens the bond lengths to the average neutron values) is not fulfilled. This is one of the major reasons for problems with quantitative estimation of electron density distributions in charge density studies.

The average differences between the neutron and X-ray valence angles defined by H atoms as a function of the 2θ_max diffraction angle behave differently for IAM and TAAM. For TAAM they decrease with the increasing values of resolution, whereas the IAM differences increase. Again for smaller values of the TAAM average differences between the neutron and X-ray valence angles defined by H-atoms show the superiority of this model over the IAM.

3.3.5. Comparison of ADPs from IAM and TAAM refinements

In Fig. 5S (supporting information), we plotted the overall mean similarity index (S_diff) calculated when the non-H atom ADPs obtained for BD²⁺ × 2Cl⁻, DMANH⁺ × 2Cl⁻ × H₅O₂⁺, T after IAM and TAAM refinements against X-ray data cut to different resolutions are compared with the corresponding neutron values. It turns out that in the case of T and BD²⁺ × 2Cl⁻, the agreement between X-ray and neutron ADPs is significantly better when TAAM refinement is applied. This effect is less pronounced in the case of DMANH⁺ × 2Cl⁻ × H₅O₂⁺. In general, the values of the overall similarity index obtained for comparison of X-ray and neutron ADPs are high for the low-angle data. Fig. 7(a) presents visualization of the ADP values obtained for the non-H atoms forming the independent part of the triptycene molecule. There are significant differences between the ADPs calculated for data collected up to 2θ = 50° and those obtained for the larger diffraction angles (2θ = 80°). Of course the latter ones are closer to the neutron values of ADPs.

Figure 7 (a) Visualization of the ADP values obtained for the non-H atoms forming the independent part of the triptycene molecule. (b) The mean similarity index for ADPs obtained after IAM and TAAM compared with ADPs from TAAM refinement against high-resolution X-ray data as a function of the 2θmax diffraction angle.

Similar dependences are obtained when one compares the non-H atom ADPs obtained from the IAM and from TAAM refinements against different resolution data to the ADPs obtained after TAAM refinement against the high-resolution X-ray data. Results are illustrated in Fig. 7(b). It appears that ADPs obtained after TAAM refinement conducted against low-resolution X-ray data are similar to those obtained after refinement of the high-resolution X-ray data. This analysis clearly demonstrates that ADPs obtained after the IAM refinement are inaccurate when only low-resolution data are used.

3.3.6. TLS analysis and vibrational entropy estimation

We have also investigated how resolution influences properties derived from ADPs, specifically the results of a TLS analysis. The systems used for the TLS analysis should be rigid. Thus, in the case of BD²⁺ × 2Cl⁻ and DMANH⁺ × 2Cl⁻ × H₅O₂⁺, we used only the rigid cation molecules, i.e. the DMANH⁺ and BD²⁺ cations. It may be expected that these moieties for which the differences in ADPs obtained after TAAM and IAM refinements at low diffraction angles are large also exhibit significant differences in parameters obtained from the TLS analysis. First of all, R_TLS is significantly higher for triptycene and the benzidine cation after IAM refinement than after TAAM refinement below a resolution of 60° (see Fig. 8). The TLS analysis of well determined ADPs of truly rigid bodies (e.g. benzene) often gives R_TLS(U^ij) values of about 5%, especially for the low-temperature studies. For the less rigid systems values of 8–12% are common. We can immediately see that it is important to use data to at least the 2θ_max diffraction angle > 65° in order to make conclusions regarding the TLS analysis.

Figure 8 Dependences of the RTLS values on resolution of X-ray data.

Additionally, for the BD²⁺ cation and T, there are differences in frequencies obtained for normal modes related to translations and librations for IAM and TAAM refinements (see the supporting information). In the case of T, the rigid body refinement yields a non-physical result, and thus give no frequencies for resolution below 52°, and in the case of the benzidinium cation – below 48°. Application of TAAM gives a meaningful TLS refinement even at the low resolution.

In the case of the DMANH⁺ cation, for which ADPs obtained at the low resolution only slightly differ from those obtained for the high-resolution data, R_TLS and normal mode frequencies are also not changing either with resolution, or with different refinement methods applied.

The entropy estimation method proposed by Madsen & Larsen (2007) rely on frequencies obtained from TLS analysis. Thus, for triptycene and for the benzidine cation, for the IAM refinements against low-resolution data, when it is impossible to derive frequencies from TLS analysis, it is also impossible to estimate the part of vibrational entropy that is due to low-frequency phonons (Fig. 9). In such a case, the TAAM refinement, which enables estimation of normal mode frequencies even from low-resolution data, gives a unique opportunity to estimate vibrational entropy. However, it appears that entropies estimated at low-resolution data are higher by 2–3 J mol⁻¹ K⁻¹ (which at room temperature corresponds to ca 1 kJ mol⁻¹) than those from the high-resolution data for all studied compounds and both models of electron density (see Tables 2S–4S and Figs. 8S and 9S in the supporting information and Fig. 9).

Figure 9 Vibrational entropy at 100 K versus resolution of X-ray data for BD^2+, DMANH^+ and T.

Even in the case of the DMANH⁺ data which does not show significant differences between entropies obtained by using IAM and TAAM, the entropies obtained stabilize above 2θ_max > 65°. The same is true for the other compounds and for the difference in entropy values obtained at 298 and 100 K (Figs. 8S and 9S, and 9).

4. Conclusions

A detailed analysis of the dependences of structural and thermal parameters obtained by X-ray diffraction on single crystals of five model compounds has been performed as a function of resolution of X-ray data. Two models – the Independent Atom Model and Transferable Aspherical Atom Model – were used in the refinement procedures. For all compounds – benzidine dihydrochloride, hydrated and protonated N,N,N,N-peri(dimethylamino)naphthalene chloride, triptycene, dichlorodimethyltriptycene and decamethylferrocene – the dependencies of the averaged differences between the X-ray and neutron corresponding geometrical parameters on the diffraction 2θ_max angle decrease with increasing resolution (with the exception of the valence angles defined by H atoms). The differences between the X-ray and neutron geometrical parameters can be significantly reduced when data are collected to the higher than commonly used 2θ_max diffraction angles (for example, for Mo Kα 2θ_max > 65°). In the case of IAM models for the valence angles defined by H atoms, the smallest 2θ_max diffraction angles give the best agreement between the X-ray and neutron values, and discrepancy between the two increases with the increasing 2θ_max diffraction angle.

In order to obtain more adequate (more accurate and precise) structural and ADP parameters when the IAM model is used, one should collect data up to the larger diffraction angles, for Mo Kα, at least, to 2θ_max = 65° (sin θ_max/λ < 0.75 Å⁻¹). Also the results of TLS analysis and vibrational entropy values are better for 2θ_max > 65°.

Stalke and co-workers (Krause et al., 2015) suggested that it should be standard practice to collect data to the highest possible resolution when both heavy and light atoms are present. Our main conclusion is that even in the case of the light atoms only, the diffraction data should be collected to the highest resolution as this allows for refinement of more reliable structural, thermal and dependent parameters. Furthermore, the results of refinements using TAAM appear to be in better agreement with the neutron results than the corresponding IAM results for all parameters, all resolutions and all compounds, and for those who look for better quality structural parameters we advocate the use of this approach instead of the IAM.

Supporting information

Computing details

Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for BENZ_IAM_50, BENZ_IAM_80, DCDMT_IAM_50, DCDMT_IAM_80, T_IAM_50, T_IAM_80; SHELXS97 (Sheldrick, 1990) for DCDMT_N_100, DMAN_IAM_50, DMAN_IAM_80, FC_IAM_50, FC_IAM_80, FC_N_100, T_N_100. Program(s) used to refine structure: XL (Sheldrick, 2008) for BENZ_IAM_50, BENZ_IAM_80, DCDMT_IAM_50, DCDMT_IAM_80, T_IAM_50, T_IAM_80; MoPro (J. Appl. Cryst. 2005, 38, 38-54) for BENZ_TAAM_50, BENZ_TAAM_80, DMAN_TAAM_50, DMAN_TAAM_80, T_TAAM_50, T_TAAM_80; SHELXL97 (Sheldrick, 1997) for DCDMT_N_100, DMAN_IAM_50, DMAN_IAM_80, FC_IAM_50, FC_IAM_80, FC_N_100, T_N_100; olex2.refine (Bourhis et al., 2015) for DMAN_N_100. Molecular graphics: Olex2 (Dolomanov et al., 2009) for BENZ_IAM_50, BENZ_IAM_80, DCDMT_IAM_50, DCDMT_IAM_80, DMAN_N_100, T_IAM_50, T_IAM_80. Software used to prepare material for publication: Olex2 (Dolomanov et al., 2009) for BENZ_IAM_50, BENZ_IAM_80, DCDMT_IAM_50, DCDMT_IAM_80, DMAN_N_100, T_IAM_50, T_IAM_80.

(BENZ_IAM_50)

Crystal data

2(Cl)·C12H14N2	V = 594.58 (17) Å^3
Mr = 257.15	Z = 2
Triclinic, P1	F(000) = 268
a = 6.5705 (11) Å	Dx = 1.436 Mg m^−3
b = 7.6756 (14) Å	Mo Kα radiation, λ = 0.71073 Å
c = 12.6098 (18) Å	µ = 0.52 mm^−1
α = 85.165 (13)°	T = 373 K
β = 76.785 (13)°	5 × 2 × 2 mm
γ = 73.868 (16)°

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
2097 measured reflections	h = −7→7
2097 independent reflections	k = −9→9
1995 reflections with I > 2σ(I)	l = 0→14

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	All H-atom parameters refined
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 0.0728P] where P = (Fo^2 + 2Fc^2)/3
2097 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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.

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 > 2sigma(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
Cl1	0.04008 (4)	0.17613 (3)	0.080860 (19)	0.01271 (13)
Cl2	0.46029 (4)	0.32492 (3)	0.911384 (19)	0.01338 (13)
N1	1.10322 (17)	0.56634 (14)	0.11559 (8)	0.0124 (2)
N2	0.41160 (17)	0.92334 (14)	0.88628 (8)	0.0127 (2)
C1	0.99367 (17)	0.61940 (15)	0.22745 (8)	0.0118 (2)
C2	0.93463 (17)	0.49074 (14)	0.30271 (8)	0.0129 (2)
C3	0.83722 (17)	0.54286 (14)	0.40937 (8)	0.0124 (2)
C4	0.79488 (17)	0.72225 (15)	0.44146 (9)	0.0120 (2)
C5	0.85543 (17)	0.84864 (14)	0.36226 (8)	0.0130 (2)
C6	0.95636 (17)	0.79774 (14)	0.25609 (8)	0.0129 (2)
C7	0.51320 (17)	0.87060 (14)	0.77319 (8)	0.0121 (2)
C8	0.63279 (17)	0.97673 (14)	0.70679 (9)	0.0138 (2)
C9	0.72225 (17)	0.92830 (14)	0.59904 (9)	0.0135 (2)
C10	0.69359 (18)	0.77580 (14)	0.55632 (9)	0.0121 (2)
C11	0.57184 (16)	0.67220 (14)	0.62651 (8)	0.0133 (2)
C12	0.48200 (17)	0.71837 (14)	0.73452 (9)	0.0132 (2)
H1A	1.103 (2)	0.463 (2)	0.1041 (12)	0.019 (4)*
H1B	1.238 (3)	0.5741 (19)	0.1011 (12)	0.020 (4)*
H1C	1.040 (2)	0.639 (2)	0.0655 (13)	0.023 (4)*
H2	0.966 (2)	0.3674 (17)	0.2833 (9)	0.020 (3)*
H2A	0.412 (2)	1.029 (2)	0.8963 (12)	0.019 (4)*
H2B	0.477 (2)	0.851 (2)	0.9355 (13)	0.022 (4)*
H2C	0.276 (3)	0.9165 (19)	0.9036 (11)	0.017 (4)*
H3	0.804 (2)	0.4511 (17)	0.4625 (10)	0.022 (3)*
H5	0.8213 (19)	0.9757 (16)	0.3797 (9)	0.017 (3)*
H6	0.999 (2)	0.8835 (16)	0.2029 (10)	0.020 (3)*
H8	0.656 (2)	1.0784 (16)	0.7339 (9)	0.018 (3)*
H9	0.808 (2)	0.9999 (17)	0.5544 (10)	0.020 (3)*
H11	0.544 (2)	0.5682 (17)	0.6012 (9)	0.019 (3)*
H12	0.399 (2)	0.6489 (16)	0.7801 (10)	0.018 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01435 (19)	0.01171 (19)	0.01206 (18)	−0.00508 (13)	−0.00070 (12)	−0.00055 (11)
Cl2	0.01475 (19)	0.01271 (19)	0.01270 (18)	−0.00534 (13)	−0.00086 (12)	−0.00043 (12)
N1	0.0145 (5)	0.0121 (5)	0.0108 (5)	−0.0048 (4)	−0.0013 (4)	−0.0013 (4)
N2	0.0146 (5)	0.0130 (5)	0.0105 (5)	−0.0044 (4)	−0.0013 (4)	−0.0012 (4)
C1	0.0096 (5)	0.0163 (5)	0.0097 (5)	−0.0032 (4)	−0.0020 (4)	−0.0015 (4)
C2	0.0128 (5)	0.0114 (5)	0.0148 (5)	−0.0033 (4)	−0.0034 (4)	−0.0007 (4)
C3	0.0129 (5)	0.0136 (5)	0.0111 (5)	−0.0048 (4)	−0.0022 (4)	0.0015 (4)
C4	0.0094 (5)	0.0149 (5)	0.0122 (6)	−0.0033 (4)	−0.0032 (4)	−0.0008 (4)
C5	0.0136 (5)	0.0119 (5)	0.0138 (5)	−0.0032 (4)	−0.0036 (4)	−0.0001 (4)
C6	0.0140 (5)	0.0129 (5)	0.0127 (5)	−0.0049 (4)	−0.0035 (4)	0.0016 (4)
C7	0.0111 (5)	0.0144 (5)	0.0096 (5)	−0.0012 (4)	−0.0020 (4)	−0.0016 (4)
C8	0.0139 (5)	0.0136 (5)	0.0146 (5)	−0.0048 (4)	−0.0032 (4)	−0.0010 (4)
C9	0.0132 (5)	0.0146 (5)	0.0126 (5)	−0.0052 (4)	−0.0006 (4)	−0.0002 (4)
C10	0.0101 (5)	0.0135 (5)	0.0120 (6)	−0.0015 (4)	−0.0032 (4)	0.0001 (4)
C11	0.0132 (5)	0.0126 (5)	0.0147 (5)	−0.0044 (4)	−0.0026 (4)	−0.0010 (4)
C12	0.0125 (5)	0.0130 (5)	0.0135 (5)	−0.0039 (4)	−0.0015 (4)	0.0010 (4)

Geometric parameters (Å, º)

N1—C1	1.4639 (14)	C4—C10	1.4890 (19)
N1—H1A	0.818 (17)	C5—C6	1.3867 (15)
N1—H1B	0.881 (17)	C5—H5	0.971 (12)
N1—H1C	0.904 (17)	C6—H6	0.952 (12)
N2—C7	1.4680 (14)	C7—C8	1.3864 (16)
N2—H2A	0.831 (17)	C7—C12	1.3856 (16)
N2—H2B	0.900 (16)	C8—C9	1.3887 (15)
N2—H2C	0.880 (17)	C8—H8	0.941 (12)
C1—C2	1.3831 (16)	C9—C10	1.4038 (16)
C1—C6	1.3859 (15)	C9—H9	0.954 (13)
C2—C3	1.3904 (15)	C10—C11	1.4024 (16)
C2—H2	0.951 (12)	C11—C12	1.3880 (15)
C3—C4	1.4024 (15)	C11—H11	0.961 (12)
C3—H3	0.964 (13)	C12—H12	0.939 (13)
C4—C5	1.4023 (16)
C1—N1—H1A	111.7 (10)	C4—C5—H5	120.6 (7)
C1—N1—H1B	111.2 (9)	C6—C5—C4	121.21 (9)
C1—N1—H1C	112.5 (10)	C6—C5—H5	118.1 (7)
H1A—N1—H1B	109.0 (14)	C1—C6—C5	119.24 (10)
H1A—N1—H1C	106.7 (14)	C1—C6—H6	119.8 (7)
H1B—N1—H1C	105.3 (13)	C5—C6—H6	121.0 (7)
C7—N2—H2A	111.1 (10)	C8—C7—N2	119.37 (10)
C7—N2—H2B	113.4 (9)	C12—C7—N2	119.04 (10)
C7—N2—H2C	111.4 (9)	C12—C7—C8	121.56 (10)
H2A—N2—H2B	107.5 (14)	C7—C8—C9	118.72 (9)
H2A—N2—H2C	108.1 (13)	C7—C8—H8	121.2 (7)
H2B—N2—H2C	105.1 (13)	C9—C8—H8	120.0 (7)
C2—C1—N1	119.70 (9)	C8—C9—C10	121.60 (10)
C2—C1—C6	121.45 (10)	C8—C9—H9	118.2 (7)
C6—C1—N1	118.83 (10)	C10—C9—H9	120.1 (7)
C1—C2—C3	118.72 (9)	C9—C10—C4	121.20 (11)
C1—C2—H2	121.0 (7)	C11—C10—C4	121.05 (11)
C3—C2—H2	120.2 (7)	C11—C10—C9	117.72 (10)
C2—C3—C4	121.62 (10)	C10—C11—H11	121.3 (7)
C2—C3—H3	118.4 (7)	C12—C11—C10	121.40 (10)
C4—C3—H3	119.9 (7)	C12—C11—H11	117.3 (7)
C3—C4—C10	121.12 (11)	C7—C12—C11	119.00 (10)
C5—C4—C3	117.75 (10)	C7—C12—H12	120.7 (7)
C5—C4—C10	121.12 (11)	C11—C12—H12	120.3 (7)
N1—C1—C2—C3	177.90 (9)	C4—C10—C11—C12	178.18 (10)
N1—C1—C6—C5	−179.10 (9)	C5—C4—C10—C9	−22.57 (18)
N2—C7—C8—C9	−178.01 (9)	C5—C4—C10—C11	159.44 (10)
N2—C7—C12—C11	177.78 (9)	C6—C1—C2—C3	−0.46 (16)
C1—C2—C3—C4	1.03 (16)	C7—C8—C9—C10	0.23 (15)
C2—C1—C6—C5	−0.73 (16)	C8—C7—C12—C11	−0.39 (16)
C2—C3—C4—C5	−0.39 (16)	C8—C9—C10—C4	−178.41 (10)
C2—C3—C4—C10	−179.04 (10)	C8—C9—C10—C11	−0.36 (15)
C3—C4—C5—C6	−0.83 (16)	C9—C10—C11—C12	0.12 (15)
C3—C4—C10—C9	156.04 (10)	C10—C4—C5—C6	177.82 (10)
C3—C4—C10—C11	−21.95 (18)	C10—C11—C12—C7	0.24 (15)
C4—C5—C6—C1	1.38 (15)	C12—C7—C8—C9	0.16 (16)

(BENZ_IAM_80)

Crystal data

2(Cl)·C12H14N2	V = 594.58 (17) Å^3
Mr = 257.15	Z = 2
Triclinic, P1	F(000) = 268
a = 6.5705 (11) Å	Dx = 1.436 Mg m^−3
b = 7.6756 (14) Å	Mo Kα radiation, λ = 0.71073 Å
c = 12.6098 (18) Å	µ = 0.52 mm^−1
α = 85.165 (13)°	T = 373 K
β = 76.785 (13)°	5 × 2 × 2 mm
γ = 73.868 (16)°

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 40.0°, θmin = 1.7°
7364 measured reflections	h = −11→11
7364 independent reflections	k = −13→13
6831 reflections with I > 2σ(I)	l = 0→22

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) = 0.065	All H-atom parameters refined
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0404P)^2 + 0.0244P] where P = (Fo^2 + 2Fc^2)/3
7364 reflections	(Δ/σ)max = 0.004
202 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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.

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 > 2sigma(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
Cl1	0.040122 (12)	0.176093 (10)	0.080872 (6)	0.01129 (2)
Cl2	0.460286 (13)	0.324905 (10)	0.911389 (6)	0.01194 (2)
N1	1.10310 (5)	0.56615 (4)	0.11555 (2)	0.01122 (4)
N2	0.41171 (5)	0.92349 (4)	0.88630 (2)	0.01151 (5)
C1	0.99390 (5)	0.61917 (4)	0.22703 (2)	0.00955 (5)
C2	0.93455 (5)	0.49037 (4)	0.30269 (3)	0.01101 (5)
C3	0.83684 (5)	0.54270 (4)	0.40953 (3)	0.01098 (5)
C4	0.79469 (5)	0.72249 (4)	0.44159 (3)	0.00961 (5)
C5	0.85544 (6)	0.84902 (4)	0.36244 (3)	0.01134 (5)
C6	0.95685 (6)	0.79800 (4)	0.25585 (3)	0.01127 (5)
C7	0.51285 (5)	0.87098 (4)	0.77362 (3)	0.01003 (5)
C8	0.63266 (6)	0.97710 (4)	0.70679 (3)	0.01198 (5)
C9	0.72238 (6)	0.92858 (5)	0.59878 (3)	0.01188 (5)
C10	0.69380 (5)	0.77563 (4)	0.55619 (3)	0.00981 (5)
C11	0.57200 (5)	0.67197 (4)	0.62641 (3)	0.01154 (5)
C12	0.48182 (5)	0.71807 (4)	0.73482 (3)	0.01148 (5)
H1A	1.1015 (17)	0.4600 (14)	0.1025 (8)	0.027 (2)*
H1B	1.2411 (16)	0.5710 (13)	0.1010 (8)	0.024 (2)*
H1C	1.0415 (16)	0.6380 (14)	0.0659 (8)	0.024 (2)*
H2	0.9685 (14)	0.3660 (11)	0.2824 (7)	0.0245 (19)*
H2A	0.4145 (17)	1.0312 (14)	0.8973 (8)	0.024 (2)*
H2B	0.4777 (16)	0.8522 (13)	0.9355 (8)	0.022 (2)*
H2C	0.2747 (16)	0.9197 (13)	0.9036 (8)	0.023 (2)*
H3	0.8062 (14)	0.4478 (11)	0.4630 (7)	0.0254 (19)*
H5	0.8190 (13)	0.9777 (10)	0.3789 (6)	0.0221 (18)*
H6	0.9965 (14)	0.8876 (11)	0.2020 (7)	0.0256 (19)*
H8	0.6557 (13)	1.0789 (10)	0.7351 (6)	0.0219 (18)*
H9	0.8095 (14)	1.0013 (11)	0.5542 (7)	0.0236 (18)*
H11	0.5412 (13)	0.5674 (11)	0.6007 (6)	0.0230 (18)*
H12	0.3946 (14)	0.6469 (11)	0.7802 (7)	0.0255 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01284 (4)	0.01032 (4)	0.01064 (4)	−0.00456 (3)	−0.00053 (2)	−0.00021 (2)
Cl2	0.01322 (4)	0.01133 (4)	0.01126 (4)	−0.00484 (3)	−0.00073 (3)	−0.00009 (2)
N1	0.01356 (10)	0.01195 (10)	0.00791 (9)	−0.00435 (8)	−0.00036 (8)	−0.00100 (7)
N2	0.01335 (10)	0.01280 (10)	0.00793 (9)	−0.00385 (8)	−0.00056 (8)	−0.00116 (7)
C1	0.01059 (10)	0.01032 (10)	0.00762 (10)	−0.00328 (8)	−0.00105 (8)	−0.00038 (8)
C2	0.01397 (11)	0.00991 (10)	0.00890 (10)	−0.00411 (8)	−0.00067 (8)	−0.00059 (8)
C3	0.01394 (11)	0.01029 (10)	0.00857 (10)	−0.00450 (8)	−0.00054 (8)	−0.00022 (8)
C4	0.01040 (10)	0.01024 (11)	0.00811 (10)	−0.00324 (8)	−0.00109 (8)	−0.00054 (8)
C5	0.01462 (11)	0.00969 (10)	0.00914 (10)	−0.00356 (9)	−0.00094 (8)	−0.00041 (8)
C6	0.01469 (12)	0.00998 (10)	0.00895 (10)	−0.00431 (9)	−0.00103 (8)	0.00014 (8)
C7	0.01078 (11)	0.01119 (11)	0.00784 (10)	−0.00328 (8)	−0.00081 (8)	−0.00087 (8)
C8	0.01405 (11)	0.01295 (11)	0.00966 (10)	−0.00631 (9)	−0.00005 (9)	−0.00196 (8)
C9	0.01395 (12)	0.01275 (11)	0.00948 (10)	−0.00644 (9)	0.00044 (9)	−0.00159 (8)
C10	0.01041 (10)	0.01078 (11)	0.00822 (10)	−0.00353 (8)	−0.00090 (8)	−0.00082 (8)
C11	0.01337 (11)	0.01186 (11)	0.00970 (10)	−0.00561 (9)	0.00013 (8)	−0.00153 (8)
C12	0.01334 (11)	0.01160 (11)	0.00942 (10)	−0.00513 (9)	0.00016 (8)	−0.00080 (8)

Geometric parameters (Å, º)

N1—C1	1.4592 (5)	C4—C10	1.4849 (6)
N1—H1A	0.848 (10)	C5—C6	1.3921 (5)
N1—H1B	0.894 (10)	C5—H5	0.978 (8)
N1—H1C	0.891 (10)	C6—H6	0.971 (8)
N2—C7	1.4624 (5)	C7—C8	1.3894 (5)
N2—H2A	0.855 (10)	C7—C12	1.3907 (5)
N2—H2B	0.898 (10)	C8—C9	1.3920 (5)
N2—H2C	0.884 (10)	C8—H8	0.948 (8)
C1—C2	1.3874 (5)	C9—C10	1.4060 (5)
C1—C6	1.3905 (5)	C9—H9	0.966 (8)
C2—C3	1.3932 (5)	C10—C11	1.4031 (5)
C2—H2	0.961 (8)	C11—C12	1.3928 (5)
C3—C4	1.4054 (5)	C11—H11	0.977 (8)
C3—H3	0.981 (8)	C12—H12	0.962 (8)
C4—C5	1.4030 (5)
C1—N1—H1A	112.5 (7)	C4—C5—H5	121.1 (5)
C1—N1—H1B	111.5 (6)	C6—C5—C4	121.20 (3)
C1—N1—H1C	112.8 (7)	C6—C5—H5	117.6 (5)
H1A—N1—H1B	108.2 (9)	C1—C6—C5	119.22 (3)
H1A—N1—H1C	105.4 (10)	C1—C6—H6	120.7 (5)
H1B—N1—H1C	106.1 (9)	C5—C6—H6	120.1 (5)
C7—N2—H2A	111.4 (7)	C8—C7—N2	119.54 (3)
C7—N2—H2B	113.5 (6)	C8—C7—C12	121.38 (3)
C7—N2—H2C	111.7 (6)	C12—C7—N2	119.06 (3)
H2A—N2—H2B	105.7 (9)	C7—C8—C9	118.90 (3)
H2A—N2—H2C	107.7 (9)	C7—C8—H8	120.3 (5)
H2B—N2—H2C	106.4 (9)	C9—C8—H8	120.8 (5)
C2—C1—N1	119.78 (3)	C8—C9—C10	121.51 (3)
C2—C1—C6	121.31 (3)	C8—C9—H9	117.8 (5)
C6—C1—N1	118.89 (3)	C10—C9—H9	120.6 (5)
C1—C2—C3	118.81 (3)	C9—C10—C4	121.08 (3)
C1—C2—H2	120.2 (5)	C11—C10—C4	121.10 (3)
C3—C2—H2	120.9 (5)	C11—C10—C9	117.80 (3)
C2—C3—C4	121.58 (3)	C10—C11—H11	121.5 (5)
C2—C3—H3	117.5 (5)	C12—C11—C10	121.47 (3)
C4—C3—H3	120.8 (5)	C12—C11—H11	116.9 (5)
C3—C4—C10	120.98 (3)	C7—C12—C11	118.94 (3)
C5—C4—C3	117.86 (3)	C7—C12—H12	121.5 (5)
C5—C4—C10	121.14 (3)	C11—C12—H12	119.5 (5)
N1—C1—C2—C3	177.93 (3)	C4—C10—C11—C12	178.22 (3)
N1—C1—C6—C5	−179.13 (3)	C5—C4—C10—C9	−22.33 (5)
N2—C7—C8—C9	−178.04 (3)	C5—C4—C10—C11	159.50 (3)
N2—C7—C12—C11	177.78 (3)	C6—C1—C2—C3	−0.27 (5)
C1—C2—C3—C4	0.92 (5)	C7—C8—C9—C10	0.19 (5)
C2—C1—C6—C5	−0.91 (5)	C8—C7—C12—C11	−0.45 (5)
C2—C3—C4—C5	−0.37 (5)	C8—C9—C10—C4	−178.49 (3)
C2—C3—C4—C10	−178.96 (3)	C8—C9—C10—C11	−0.27 (5)
C3—C4—C5—C6	−0.84 (5)	C9—C10—C11—C12	−0.01 (5)
C3—C4—C10—C9	156.21 (3)	C10—C4—C5—C6	177.75 (3)
C3—C4—C10—C11	−21.95 (5)	C10—C11—C12—C7	0.36 (5)
C4—C5—C6—C1	1.47 (5)	C12—C7—C8—C9	0.18 (5)

(BENZ100D_phase_1)

Crystal data

C6H7ClN	α = 85.260 (11)°
Mr = 128.58	β = 76.735 (11)°
Triclinic, P1	γ = 73.823 (11)°
a = 6.5742 (10) Å	V = 595.50 (16) Å^3
b = 7.6702 (12) Å	Z = 4
c = 12.6360 (19) Å

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

	x	y	z	Uiso*/Ueq
Cl1	0.04010 (11)	0.17604 (10)	0.08085 (6)	0.00829
Cl2	0.46053 (12)	0.32479 (10)	0.91129 (6)	0.00909
N1	1.10311 (12)	0.56618 (11)	0.11560 (6)	0.00863
N2	0.41191 (12)	0.92370 (11)	0.88632 (6)	0.00885
C1	0.99395 (16)	0.61901 (14)	0.22696 (8)	0.00679
C2	0.93444 (17)	0.49031 (14)	0.30263 (8)	0.00807
C3	0.83674 (17)	0.54252 (14)	0.40961 (8)	0.00813
C4	0.79440 (15)	0.72264 (13)	0.44164 (7)	0.00657
C5	0.85536 (17)	0.84926 (14)	0.36246 (8)	0.00835
C6	0.95732 (17)	0.79810 (14)	0.25573 (8)	0.00825
C7	0.51297 (16)	0.87103 (14)	0.77363 (8)	0.00697
C8	0.63241 (17)	0.97717 (15)	0.70667 (8)	0.00928
C9	0.72195 (17)	0.92875 (15)	0.59874 (8)	0.00882
C10	0.69380 (15)	0.77567 (13)	0.55619 (7)	0.00674
C11	0.57234 (17)	0.67197 (14)	0.62643 (8)	0.00846
C12	0.48197 (17)	0.71823 (14)	0.73480 (8)	0.00845
H1	1.1026 (4)	0.4341 (3)	0.1011 (2)	0.02111
H2	1.2642 (4)	0.5753 (4)	0.0995 (2)	0.02265
H3	1.0324 (5)	0.6528 (4)	0.0579 (2)	0.02298
H4	0.9680 (5)	0.3502 (3)	0.2789 (2)	0.02541
H5	0.4122 (5)	1.0562 (4)	0.8990 (2)	0.02265
H6	0.4880 (5)	0.8378 (4)	0.9429 (2)	0.02368
H7	0.2514 (4)	0.9147 (4)	0.9055 (2)	0.02448
H8	0.7992 (5)	0.4395 (4)	0.4693 (2)	0.02464
H9	0.8200 (5)	0.9907 (3)	0.3830 (2)	0.0257
H10	1.0068 (5)	0.8976 (4)	0.1960 (2)	0.02473
H11	0.6536 (5)	1.0968 (4)	0.7385 (2)	0.02633
H12	0.8161 (5)	1.0119 (4)	0.5482 (2)	0.02757
H13	0.5450 (5)	0.5523 (4)	0.5972 (2)	0.0262
H14	0.3888 (5)	0.6353 (4)	0.7882 (2)	0.02567

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.00994 (26	0.00701 (24	0.00765 (24	−0.00326 (22	−0.00029 (19	0.00020 (20
Cl2	0.01030 (27	0.00825 (26	0.00872 (25	−0.00353 (23	−0.00094 (20	0.00029 (21
N1	0.01117 (29	0.00868 (28	0.00590 (25	−0.00315 (25	−0.00088 (21	−0.00043 (21
N2	0.01065 (29	0.00974 (29	0.00568 (25	−0.00243 (25	−0.00092 (21	−0.00094 (22
C1	0.0082 (4)	0.0067 (4)	0.00506 (33	−0.00151 (31	−0.00096 (27	−0.00055 (27
C2	0.0111 (4)	0.00640 (34	0.00616 (33	−0.00244 (32	−0.00055 (28	−0.00034 (27
C3	0.0117 (4)	0.00673 (35	0.00523 (32	−0.00266 (33	−0.00014 (28	−0.00027 (27
C4	0.0080 (4)	0.0065 (4)	0.00513 (34	−0.00198 (33	−0.00100 (29	−0.00041 (29
C5	0.0124 (4)	0.00597 (34	0.00612 (33	−0.00247 (32	−0.00088 (28	−0.00011 (27
C6	0.0119 (4)	0.00617 (34	0.00602 (33	−0.00233 (33	−0.00090 (29	0.00062 (27
C7	0.0076 (4)	0.0075 (4)	0.00581 (34	−0.00234 (32	−0.00095 (27	−0.00063 (28
C8	0.0121 (4)	0.0099 (4)	0.00669 (34	−0.00552 (35	0.00003 (29	−0.00167 (29
C9	0.0116 (4)	0.0092 (4)	0.00613 (33	−0.00541 (34	0.00094 (28	−0.00155 (29
C10	0.0076 (4)	0.0075 (4)	0.00507 (35	−0.00269 (33	−0.00026 (28	−0.00061 (30
C11	0.0110 (4)	0.0083 (4)	0.00647 (33	−0.00467 (33	0.00036 (28	−0.00140 (28
C12	0.0108 (4)	0.0081 (4)	0.00622 (33	−0.00375 (33	0.00042 (28	−0.00090 (28
H1	0.0295 (12)	0.0141 (9)	0.0199 (11)	−0.0068 (9)	−0.0037 (9)	−0.0030 (8)
H2	0.0173 (10)	0.0301 (13)	0.0201 (10)	−0.0086 (10)	0.0001 (8)	−0.0017 (9)
H3	0.0302 (13)	0.0205 (11)	0.0152 (10)	−0.0004 (10)	−0.0071 (9)	0.0008 (8)
H4	0.0411 (15)	0.0123 (9)	0.0218 (11)	−0.0085 (10)	−0.0015 (10)	−0.0044 (8)
H5	0.0344 (13)	0.0155 (10)	0.0181 (10)	−0.0068 (10)	−0.0038 (9)	−0.0053 (8)
H6	0.0297 (13)	0.0227 (11)	0.0172 (10)	−0.0016 (10)	−0.0094 (9)	0.0011 (9)
H7	0.0166 (10)	0.0353 (15)	0.0199 (11)	−0.0072 (10)	0.0003 (8)	−0.0028 (10)
H8	0.0387 (14)	0.0176 (10)	0.0157 (10)	−0.0104 (11)	−0.0002 (9)	0.0044 (8)
H9	0.0411 (15)	0.0119 (9)	0.0212 (11)	−0.0057 (10)	−0.0017 (10)	−0.0031 (8)
H10	0.0389 (14)	0.0177 (10)	0.0157 (10)	−0.0111 (11)	0.0006 (9)	0.0040 (8)
H11	0.0370 (14)	0.0248 (12)	0.0203 (11)	−0.0169 (11)	0.0013 (10)	−0.0092 (9)
H12	0.0383 (15)	0.0265 (13)	0.0210 (11)	−0.0214 (12)	0.0029 (10)	0.0007 (10)
H13	0.0350 (14)	0.0233 (12)	0.0232 (11)	−0.0166 (11)	0.0017 (10)	−0.0086 (9)
H14	0.0340 (14)	0.0243 (12)	0.0190 (11)	−0.0159 (11)	0.0032 (9)	0.0011 (9)

Geometric parameters (Å, º)

N1—C1	1.4588 (13)	C4—C10	1.4853 (13)
N1—H1	1.045 (3)	C5—C6	1.3958 (15)
N1—H2	1.052 (3)	C5—H9	1.085 (3)
N1—H3	1.046 (3)	C6—H10	1.090 (3)
N2—C7	1.4641 (13)	C7—C8	1.3902 (14)
N2—H5	1.043 (3)	C7—C12	1.3892 (14)
N2—H6	1.048 (3)	C8—C9	1.3921 (15)
N2—H7	1.047 (3)	C8—H11	1.087 (3)
C1—C2	1.3889 (14)	C9—C10	1.4046 (14)
C1—C6	1.3911 (15)	C9—H12	1.081 (3)
C2—C3	1.3958 (15)	C10—C11	1.4036 (13)
C2—H4	1.088 (3)	C11—C12	1.3941 (15)
C3—C4	1.4059 (15)	C11—H13	1.090 (3)
C3—H8	1.086 (3)	C12—H14	1.092 (3)
C4—C5	1.4061 (13)
C1—N1—H1	111.50 (16)	C4—C5—C6	121.34 (10)
C1—N1—H2	110.45 (16)	C4—C5—H9	120.21 (17)
C1—N1—H3	112.61 (17)	C6—C5—H9	118.43 (17)
H1—N1—H2	109.3 (2)	C1—C6—C5	119.03 (9)
H1—N1—H3	107.9 (2)	C1—C6—H10	120.77 (17)
H2—N1—H3	104.8 (2)	C5—C6—H10	120.20 (18)
C7—N2—H5	111.12 (16)	N2—C7—C8	119.65 (9)
C7—N2—H6	112.97 (18)	N2—C7—C12	119.09 (8)
C7—N2—H7	110.24 (16)	C8—C7—C12	121.24 (9)
H5—N2—H6	108.3 (2)	C7—C8—C9	119.07 (9)
H5—N2—H7	108.8 (2)	C7—C8—H11	120.05 (17)
H6—N2—H7	105.2 (2)	C9—C8—H11	120.88 (17)
N1—C1—C2	119.99 (9)	C8—C9—C10	121.48 (9)
N1—C1—C6	118.66 (8)	C8—C9—H12	118.00 (18)
C2—C1—C6	121.32 (9)	C10—C9—H12	120.51 (18)
C1—C2—C3	119.02 (10)	C4—C10—C9	121.06 (8)
C1—C2—H4	120.14 (17)	C4—C10—C11	121.21 (8)
C3—C2—H4	120.81 (17)	C9—C10—C11	117.71 (9)
C2—C3—C4	121.41 (9)	C10—C11—C12	121.57 (9)
C2—C3—H8	118.58 (18)	C10—C11—H13	120.54 (17)
C4—C3—H8	119.97 (17)	C12—C11—H13	117.88 (17)
C3—C4—C5	117.86 (9)	C7—C12—C11	118.93 (9)
C3—C4—C10	120.85 (8)	C7—C12—H14	120.69 (18)
C5—C4—C10	121.28 (9)	C11—C12—H14	120.38 (18)

(BENZ_TAAM_50)

Crystal data

C12H14N2Cl2	β = 76.79°
Mr = 257.15	γ = 73.87°
Triclinic, P?	V = 594.6 Å^3
Hall symbol: P ?	Z = 2
a = 6.570 Å	F(000) = 268
b = 7.676 Å	Dx = 1.437 Mg m^−3
c = 12.610 Å	Mo Kα radiation, λ = 0.71073 Å
α = 85.17°

Data collection

Radiation source: fine-focus sealed tube	h = −7→7
2076 independent reflections	k = −9→9
1999 reflections with > 2.0σ(I)	l = 0→14
θmax = 25.0°, θmin = 1.7°

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.010	Secondary atom site location: difference Fourier map
wR(F^2) = 0.070	Hydrogen site location: inferred from neighbouring sites
S = 2.97	All H-atom parameters refined
2075 reflections	Weighting scheme based on measured s.u.'s
201 parameters	(Δ/σ)max = 0.002

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
CL1	0.04005 (1)	0.17610 (1)	0.080860 (1)	0.01155 (2)
CL2	0.46033 (1)	0.32491 (1)	0.911370 (1)	0.01220 (2)
N1	1.10327 (6)	0.56608 (5)	0.11551 (3)	0.01158 (7)
N2	0.41161 (6)	0.92346 (5)	0.88634 (3)	0.01188 (7)
C1	0.99400 (6)	0.61910 (5)	0.22691 (3)	0.00998 (7)
C2	0.93459 (6)	0.49040 (5)	0.30272 (3)	0.01135 (7)
C3	0.83687 (6)	0.54264 (5)	0.40953 (3)	0.01119 (7)
C4	0.79466 (6)	0.72248 (5)	0.44167 (3)	0.01001 (7)
C5	0.85548 (6)	0.84905 (5)	0.36241 (3)	0.01160 (7)
C6	0.95684 (6)	0.79797 (5)	0.25582 (3)	0.01144 (7)
C7	0.51286 (6)	0.87098 (5)	0.77372 (3)	0.01035 (7)
C8	0.63267 (6)	0.97699 (5)	0.70682 (3)	0.01237 (7)
C9	0.72242 (6)	0.92856 (5)	0.59878 (3)	0.01225 (7)
C10	0.69385 (6)	0.77563 (5)	0.55612 (3)	0.01017 (7)
C11	0.57197 (6)	0.67200 (5)	0.62645 (3)	0.01186 (7)
C12	0.48179 (6)	0.71806 (5)	0.73480 (3)	0.01172 (7)
H1A	1.105 (1)	0.440 (1)	0.1013 (6)	0.031 (2)*
H1B	1.253 (1)	0.5779 (9)	0.0992 (6)	0.031 (2)*
H1C	1.034 (1)	0.652 (1)	0.0602 (6)	0.033 (2)*
H2	0.9692 (8)	0.3529 (7)	0.2804 (4)	0.028 (1)*
H2A	0.409 (1)	1.050 (1)	0.8986 (6)	0.029 (2)*
H2B	0.483 (1)	0.8395 (10)	0.9415 (6)	0.030 (2)*
H2C	0.259 (1)	0.9136 (9)	0.9051 (5)	0.029 (2)*
H3	0.8027 (8)	0.4403 (7)	0.4676 (4)	0.029 (1)*
H5	0.8179 (8)	0.9887 (7)	0.3816 (4)	0.027 (1)*
H6	1.0036 (8)	0.8944 (7)	0.1982 (4)	0.029 (1)*
H8	0.6563 (8)	1.0921 (7)	0.7373 (4)	0.031 (1)*
H9	0.8175 (8)	1.0083 (7)	0.5505 (4)	0.028 (1)*
H11	0.5423 (8)	0.5575 (7)	0.5982 (4)	0.028 (1)*
H12	0.3904 (8)	0.6397 (7)	0.7850 (4)	0.028 (1)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
CL1	0.01315 (7)	0.01050 (6)	0.01094 (6)	−0.00472 (4)	−0.00048 (4)	−0.00037 (4)
CL2	0.01357 (7)	0.01148 (6)	0.01160 (6)	−0.00502 (4)	−0.00069 (4)	−0.00025 (4)
N1	0.0135 (2)	0.0121 (2)	0.0091 (2)	−0.0044 (1)	−0.0008 (1)	−0.0010 (1)
N2	0.0135 (2)	0.0127 (2)	0.0089 (2)	−0.0040 (1)	−0.0007 (1)	−0.0012 (1)
C1	0.0103 (2)	0.0104 (2)	0.0096 (2)	−0.0036 (1)	−0.0020 (1)	−0.00009 (14)
C2	0.0141 (2)	0.0098 (2)	0.0099 (2)	−0.0040 (1)	−0.0008 (1)	−0.0007 (1)
C3	0.0142 (2)	0.0101 (2)	0.0090 (2)	−0.0046 (1)	−0.0005 (1)	−0.00003 (13)
C4	0.0106 (2)	0.0105 (2)	0.0090 (2)	−0.0034 (1)	−0.0012 (1)	−0.0006 (1)
C5	0.0150 (2)	0.0097 (2)	0.0096 (2)	−0.0038 (1)	−0.0010 (1)	−0.0005 (1)
C6	0.0150 (2)	0.0100 (2)	0.0093 (2)	−0.0046 (1)	−0.0011 (1)	0.00010 (13)
C7	0.0107 (2)	0.0110 (2)	0.0096 (2)	−0.0037 (1)	−0.0016 (1)	−0.0006 (1)
C8	0.0143 (2)	0.0133 (2)	0.0103 (2)	−0.0066 (1)	0.00001 (14)	−0.0021 (1)
C9	0.0144 (2)	0.0130 (2)	0.0100 (2)	−0.0069 (1)	0.0007 (1)	−0.0018 (1)
C10	0.0106 (2)	0.0111 (2)	0.0092 (2)	−0.0040 (1)	−0.0012 (1)	−0.0007 (1)
C11	0.0137 (2)	0.0121 (2)	0.0104 (2)	−0.0061 (1)	0.00013 (14)	−0.0017 (1)
C12	0.0136 (2)	0.0116 (2)	0.0101 (2)	−0.0054 (1)	0.0003 (1)	−0.0010 (1)

Geometric parameters (Å, º)

N1—C1	1.4586 (5)	C4—C5	1.4043 (5)
N1—H1B	0.984 (9)	C5—C6	1.3922 (5)
N1—H1A	0.991 (8)	C5—H5	1.067 (5)
N1—H1C	1.015 (8)	C6—H6	1.051 (5)
N2—C7	1.4620 (5)	C7—C8	1.3892 (6)
N2—H2A	0.987 (8)	C7—C12	1.3915 (5)
N2—H2C	0.998 (8)	C8—C9	1.3922 (5)
N2—H2B	1.012 (8)	C8—H8	1.055 (5)
C1—C2	1.3880 (5)	C9—C10	1.4062 (5)
C1—C6	1.3910 (6)	C9—H9	1.054 (5)
C2—C3	1.3927 (5)	C10—C11	1.4039 (5)
C2—H2	1.064 (5)	C11—C12	1.3919 (5)
C3—C4	1.4060 (5)	C11—H11	1.057 (5)
C3—H3	1.063 (5)	C12—H12	1.042 (5)
C4—C10	1.4832 (6)
N1—C1—C2	119.85 (3)	C6—C5—H5	118.2 (3)
N1—C1—C6	118.93 (3)	C7—N2—H2A	111.6 (4)
N2—C7—C8	119.61 (4)	C7—N2—H2C	110.5 (4)
N2—C7—C12	119.08 (4)	C7—N2—H2B	113.1 (4)
C1—N1—H1B	110.9 (4)	C7—C8—C9	118.98 (5)
C1—N1—H1A	112.2 (4)	C7—C8—H8	120.7 (3)
C1—N1—H1C	111.7 (4)	C7—C12—C11	118.98 (4)
C1—C2—C3	118.91 (3)	C7—C12—H12	121.1 (3)
C1—C2—H2	120.5 (3)	C8—C7—C12	121.29 (5)
C1—C6—C5	119.28 (4)	C8—C9—C10	121.51 (4)
C1—C6—H6	120.8 (3)	C8—C9—H9	117.5 (3)
C2—C1—C6	121.20 (3)	C9—C10—C11	117.72 (4)
C2—C3—C4	121.59 (4)	C9—C8—H8	120.3 (3)
C2—C3—H3	117.8 (3)	C10—C11—C12	121.53 (3)
C3—C4—C10	121.04 (4)	C10—C11—H11	120.9 (3)
C3—C4—C5	117.80 (3)	C10—C9—H9	120.9 (3)
C3—C2—H2	120.6 (3)	C11—C12—H12	119.9 (3)
C4—C10—C11	121.13 (4)	C12—C11—H11	117.6 (3)
C4—C10—C9	121.12 (4)	H1A—N1—H1B	109.5 (6)
C4—C5—C6	121.21 (5)	H1A—N1—H1C	109.1 (6)
C4—C5—H5	120.6 (3)	H1B—N1—H1C	103.1 (6)
C4—C3—H3	120.5 (3)	H2A—N2—H2C	108.1 (6)
C5—C4—C10	121.15 (3)	H2A—N2—H2B	109.5 (6)
C5—C6—H6	119.9 (3)	H2B—N2—H2C	103.6 (6)
N1—C1—C2—C3	177.90 (4)	C5—C4—C3—H3	176.2 (4)
N1—C1—C2—H2	0.4 (3)	C6—C1—N1—H1B	64.2 (4)
N1—C1—C6—C5	−179.07 (4)	C6—C1—N1—H1A	−173.0 (6)
N1—C1—C6—H6	1.2 (3)	C6—C1—N1—H1C	−50.2 (5)
N2—C7—C8—C9	−177.99 (4)	C6—C1—C2—H2	−177.7 (4)
N2—C7—C8—H8	2.3 (3)	C6—C5—C4—C10	177.78 (4)
N2—C7—C12—C11	177.76 (4)	C7—C8—C9—C10	0.19 (3)
N2—C7—C12—H12	−1.2 (3)	C7—C8—C9—H9	−177.8 (4)
C1—C2—C3—C4	0.88 (3)	C7—C12—C11—C10	0.30 (3)
C1—C2—C3—H3	−175.8 (4)	C7—C12—C11—H11	−178.2 (4)
C1—C6—C5—C4	1.45 (3)	C8—C7—N2—H2A	14.5 (4)
C1—C6—C5—H5	−175.6 (4)	C8—C7—N2—H2C	134.8 (7)
C2—C1—N1—H1B	−114.0 (5)	C8—C7—N2—H2B	−109.5 (4)
C2—C1—N1—H1A	8.8 (4)	C8—C7—C12—C11	−0.40 (4)
C2—C1—N1—H1C	131.6 (6)	C8—C7—C12—H12	−179.3 (4)
C2—C1—C6—C5	−0.90 (3)	C8—C9—C10—C11	−0.28 (4)
C2—C1—C6—H6	179.4 (4)	C9—C10—C11—C12	0.02 (4)
C2—C3—C4—C10	−178.96 (4)	C9—C10—C11—H11	178.5 (4)
C2—C3—C4—C5	−0.35 (3)	C9—C8—C7—C12	0.15 (4)
C3—C4—C10—C11	−21.92 (4)	C10—C4—C5—H5	−5.3 (3)
C3—C4—C10—C9	156.20 (3)	C10—C4—C3—H3	−2.4 (3)
C3—C4—C5—C6	−0.83 (3)	C10—C11—C12—H12	179.3 (4)
C3—C4—C5—H5	176.1 (4)	C10—C9—C8—H8	179.9 (4)
C3—C2—C1—C6	−0.25 (4)	C11—C10—C9—H9	177.6 (4)
C4—C10—C11—C12	178.21 (4)	C12—C7—N2—H2A	−163.7 (5)
C4—C10—C11—H11	−3.3 (3)	C12—C7—N2—H2C	−43.4 (4)
C4—C10—C9—C8	−178.46 (5)	C12—C7—N2—H2B	72.3 (4)
C4—C10—C9—H9	−0.6 (3)	C12—C7—C8—H8	−179.5 (4)
C4—C5—C6—H6	−178.8 (4)	H2—C2—C3—H3	1.7 (4)
C4—C3—C2—H2	178.3 (4)	H5—C5—C6—H6	4.1 (4)
C5—C4—C10—C11	159.51 (3)	H8—C8—C9—H9	1.9 (4)
C5—C4—C10—C9	−22.37 (4)	H11—C11—C12—H12	0.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···C11	1.063 (5)	2.681 (5)	2.9695 (5)	95.1 (3)
C5—H5···C9	1.067 (5)	2.696 (4)	2.9731 (5)	94.3 (2)
C9—H9···C5	1.054 (5)	2.689 (5)	2.9731 (5)	95.0 (3)
C11—H11···C3	1.057 (5)	2.690 (5)	2.9695 (5)	94.7 (4)
N2—H2A···CL2^i	0.987 (8)	2.256 (8)	3.2335 (4)	170.5 (7)
N2—H2A···CL1^ii	0.987 (8)	2.936 (7)	3.3422 (4)	105.8 (4)
N2—H2C···CL1^ii	0.998 (8)	2.954 (7)	3.3422 (4)	104.2 (4)
N2—H2C···CL1^iii	0.998 (8)	2.224 (8)	3.1950 (4)	164.2 (7)
C12—H12···CL1^iii	1.042 (5)	2.976 (5)	3.5981 (4)	119.0 (3)
N1—H1A···CL2^iv	0.991 (8)	2.936 (7)	3.3445 (3)	105.8 (4)
N1—H1B···CL2^iv	0.984 (9)	3.011 (7)	3.3445 (3)	101.2 (5)
N1—H1A···CL1^v	0.991 (8)	2.234 (8)	3.2121 (4)	168.8 (7)
C6—H6···CL1^vi	1.051 (5)	2.551 (5)	3.5835 (4)	167.3 (4)
N1—H1C···CL1^vii	1.015 (8)	2.187 (8)	3.1841 (3)	167.0 (7)
N2—H2B···CL1^viii	1.012 (8)	3.051 (7)	3.5824 (4)	113.9 (5)
N2—H2B···CL2^ix	1.012 (8)	2.198 (8)	3.1811 (3)	163.3 (6)
N2—H2A···C6^x	0.987 (8)	3.335 (7)	3.4796 (5)	90.1 (4)
N2—H2C···C6^x	0.998 (8)	3.139 (7)	3.4796 (5)	101.6 (4)
C5—H5···C7^x	1.067 (5)	3.163 (5)	3.4364 (5)	95.6 (3)
N1—H1B···CL2^xi	0.984 (9)	2.186 (9)	3.1429 (4)	163.7 (7)
C2—H2···C10^xi	1.064 (5)	3.265 (5)	3.4498 (5)	90.9 (3)
C3—H3···C3^xi	1.063 (5)	3.148 (5)	3.3814 (8)	93.4 (3)
C3—H3···C4^xi	1.063 (5)	3.029 (5)	3.4954 (5)	107.3 (3)
C3—H3···C10^xi	1.063 (5)	3.219 (5)	3.4509 (5)	93.5 (3)

Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z+1; (iii) −x, −y+1, −z+1; (iv) x+1, y, z−1; (v) x+1, y, z; (vi) x+1, y+1, z; (vii) −x+1, −y+1, −z; (viii) −x+1, −y+1, −z+1; (ix) −x+1, −y+1, −z+2; (x) −x+1, −y+2, −z+1; (xi) −x+2, −y+1, −z+1.

(BENZ_TAAM_80)

Crystal data

C12H14N2Cl2	β = 76.79°
Mr = 257.15	γ = 73.87°
Triclinic, P?	V = 594.6 Å^3
Hall symbol: P ?	Z = 2
a = 6.570 Å	F(000) = 268
b = 7.676 Å	Dx = 1.437 Mg m^−3
c = 12.610 Å	Mo Kα radiation, λ = 0.71073 Å
α = 85.17°

Data collection

Radiation source: fine-focus sealed tube	h = −11→11
7173 independent reflections	k = −13→13
6825 reflections with > 2.0σ(I)	l = 0→22
θmax = 40.0°, θmin = 1.7°

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.009	Secondary atom site location: difference Fourier map
wR(F^2) = 0.043	Hydrogen site location: inferred from neighbouring sites
S = 1.72	All H-atom parameters refined
7172 reflections	Weighting scheme based on measured s.u.'s
201 parameters	(Δ/σ)max = 0.008

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
CL1	0.040100 (1)	0.176086 (1)	0.080872 (1)	0.011260 (1)
CL2	0.460285 (1)	0.324916 (1)	0.911385 (1)	0.011909 (1)
N1	1.10316 (2)	0.56610 (2)	0.11554 (1)	0.01111 (2)
N2	0.41172 (2)	0.92349 (2)	0.88632 (1)	0.01140 (2)
C1	0.99401 (2)	0.61912 (2)	0.22694 (1)	0.00946 (2)
C2	0.93456 (2)	0.49033 (2)	0.30268 (1)	0.01089 (2)
C3	0.83682 (3)	0.54263 (2)	0.40955 (1)	0.01088 (2)
C4	0.79464 (2)	0.72249 (2)	0.44163 (1)	0.00951 (2)
C5	0.85545 (3)	0.84907 (2)	0.36245 (1)	0.01120 (2)
C6	0.95691 (3)	0.79804 (2)	0.25580 (1)	0.01115 (2)
C7	0.51278 (2)	0.87101 (2)	0.77373 (1)	0.00992 (2)
C8	0.63259 (3)	0.97714 (2)	0.70682 (1)	0.01192 (2)
C9	0.72240 (3)	0.92860 (2)	0.59874 (1)	0.01179 (2)
C10	0.69383 (2)	0.77564 (2)	0.55615 (1)	0.00973 (2)
C11	0.57204 (3)	0.67194 (2)	0.62640 (1)	0.01151 (2)
C12	0.48180 (3)	0.71802 (2)	0.73486 (1)	0.01137 (2)
H1A	1.1052 (9)	0.4393 (8)	0.1007 (5)	0.029 (1)*
H1B	1.254 (1)	0.5776 (7)	0.0988 (5)	0.031 (1)*
H1C	1.0331 (10)	0.6517 (8)	0.0593 (5)	0.031 (1)*
H2	0.9689 (7)	0.3525 (6)	0.2800 (3)	0.0279 (9)*
H2A	0.4091 (9)	1.0513 (8)	0.8989 (4)	0.028 (1)*
H2B	0.4839 (9)	0.8401 (8)	0.9423 (5)	0.028 (1)*
H2C	0.2589 (10)	0.9140 (7)	0.9050 (4)	0.029 (1)*
H3	0.8024 (7)	0.4398 (6)	0.4681 (3)	0.0283 (10)*
H5	0.8177 (7)	0.9889 (6)	0.3815 (3)	0.0267 (9)*
H6	1.0034 (7)	0.8948 (5)	0.1978 (3)	0.0276 (10)*
H8	0.6566 (7)	1.0924 (6)	0.7375 (3)	0.0298 (10)*
H9	0.8175 (7)	1.0087 (6)	0.5499 (3)	0.0277 (9)*
H11	0.5417 (7)	0.5568 (6)	0.5979 (3)	0.0276 (9)*
H12	0.3905 (7)	0.6392 (5)	0.7855 (3)	0.0283 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
CL1	0.01280 (2)	0.01027 (2)	0.01062 (1)	−0.00456 (1)	−0.00051 (1)	−0.000204 (1)
CL2	0.01319 (2)	0.01130 (2)	0.01123 (1)	−0.00484 (1)	−0.00072 (1)	−0.00008 (1)
N1	0.01335 (5)	0.01191 (5)	0.00781 (4)	−0.00429 (4)	−0.00038 (3)	−0.00096 (3)
N2	0.01316 (5)	0.01271 (5)	0.00789 (4)	−0.00383 (4)	−0.00056 (3)	−0.00118 (3)
C1	0.01078 (5)	0.00971 (5)	0.00783 (4)	−0.00335 (4)	−0.00114 (4)	−0.00021 (3)
C2	0.01423 (5)	0.00964 (5)	0.00853 (4)	−0.00422 (4)	−0.00047 (4)	−0.00054 (3)
C3	0.01415 (5)	0.00993 (5)	0.00833 (4)	−0.00446 (4)	−0.00034 (4)	−0.00036 (3)
C4	0.01063 (5)	0.00986 (5)	0.00787 (4)	−0.00325 (4)	−0.00090 (3)	−0.00052 (3)
C5	0.01479 (5)	0.00934 (5)	0.00884 (4)	−0.00361 (4)	−0.00067 (4)	−0.00048 (3)
C6	0.01484 (5)	0.00973 (5)	0.00858 (4)	−0.00430 (4)	−0.00075 (4)	0.00006 (3)
C7	0.01081 (5)	0.01086 (5)	0.00805 (4)	−0.00362 (4)	−0.00083 (4)	−0.00074 (4)
C8	0.01426 (5)	0.01295 (5)	0.00932 (5)	−0.00661 (4)	0.00029 (4)	−0.00210 (4)
C9	0.01415 (5)	0.01265 (5)	0.00919 (5)	−0.00672 (4)	0.00065 (4)	−0.00174 (4)
C10	0.01060 (5)	0.01063 (5)	0.00809 (4)	−0.00387 (4)	−0.00068 (4)	−0.00093 (3)
C11	0.01355 (5)	0.01191 (5)	0.00939 (5)	−0.00587 (4)	0.00046 (4)	−0.00169 (4)
C12	0.01351 (5)	0.01144 (5)	0.00912 (4)	−0.00536 (4)	0.00040 (4)	−0.00098 (4)

Geometric parameters (Å, º)

N1—C1	1.4584 (2)	C4—C5	1.4036 (2)
N1—H1B	0.994 (6)	C5—C6	1.3929 (2)
N1—H1A	1.003 (6)	C5—H5	1.068 (4)
N1—H1C	1.024 (6)	C6—H6	1.055 (4)
N2—C7	1.4613 (2)	C7—C8	1.3899 (2)
N2—H2C	1.000 (6)	C7—C12	1.3915 (2)
N2—H2A	1.002 (6)	C8—C9	1.3929 (2)
N2—H2B	1.021 (6)	C8—H8	1.059 (4)
C1—C2	1.3881 (2)	C9—C10	1.4061 (2)
C1—C6	1.3913 (2)	C9—H9	1.059 (4)
C2—C3	1.3935 (2)	C10—C11	1.4034 (2)
C2—H2	1.068 (4)	C11—C12	1.3933 (2)
C3—C4	1.4059 (2)	C11—H11	1.065 (4)
C3—H3	1.069 (4)	C12—H12	1.046 (4)
C4—C10	1.4841 (2)
N1—C1—C2	119.80 (1)	C6—C5—H5	118.1 (2)
N1—C1—C6	118.91 (1)	C7—N2—H2C	110.5 (3)
N2—C7—C8	119.57 (2)	C7—N2—H2A	111.7 (3)
N2—C7—C12	119.09 (2)	C7—N2—H2B	113.5 (3)
C1—N1—H1B	111.1 (3)	C7—C8—C9	118.94 (2)
C1—N1—H1A	112.5 (3)	C7—C8—H8	120.7 (3)
C1—N1—H1C	112.0 (3)	C7—C12—C11	118.96 (2)
C1—C2—C3	118.86 (1)	C7—C12—H12	121.0 (3)
C1—C2—H2	120.4 (3)	C8—C7—C12	121.32 (2)
C1—C6—C5	119.23 (1)	C8—C9—C10	121.50 (2)
C1—C6—H6	120.7 (2)	C8—C9—H9	117.7 (2)
C2—C1—C6	121.26 (1)	C9—C10—C11	117.79 (2)
C2—C3—C4	121.57 (1)	C9—C8—H8	120.4 (3)
C2—C3—H3	117.9 (2)	C10—C11—C12	121.49 (1)
C3—C4—C10	121.00 (1)	C10—C11—H11	120.9 (3)
C3—C4—C5	117.86 (1)	C10—C9—H9	120.8 (3)
C3—C2—H2	120.7 (2)	C11—C12—H12	120.1 (3)
C4—C10—C11	121.09 (1)	C12—C11—H11	117.5 (2)
C4—C10—C9	121.09 (1)	H1A—N1—H1B	109.2 (5)
C4—C5—C6	121.20 (2)	H1A—N1—H1C	108.3 (5)
C4—C5—H5	120.6 (2)	H1B—N1—H1C	103.4 (5)
C4—C3—H3	120.5 (3)	H2A—N2—H2C	108.0 (5)
C5—C4—C10	121.12 (1)	H2A—N2—H2B	108.7 (5)
C5—C6—H6	120.0 (2)	H2B—N2—H2C	104.0 (5)
N1—C1—C2—C3	177.93 (1)	C5—C4—C3—H3	176.2 (3)
N1—C1—C2—H2	0.3 (2)	C6—C1—N1—H1B	64.4 (3)
N1—C1—C6—C5	−179.11 (2)	C6—C1—N1—H1A	−172.8 (4)
N1—C1—C6—H6	1.4 (2)	C6—C1—N1—H1C	−50.6 (4)
N2—C7—C8—C9	−178.04 (2)	C6—C1—C2—H2	−177.9 (3)
N2—C7—C8—H8	2.5 (2)	C6—C5—C4—C10	177.75 (2)
N2—C7—C12—C11	177.78 (2)	C7—C8—C9—C10	0.21 (1)
N2—C7—C12—H12	−1.3 (2)	C7—C8—C9—H9	−178.0 (3)
C1—C2—C3—C4	0.93 (1)	C7—C12—C11—C10	0.34 (1)
C1—C2—C3—H3	−175.7 (3)	C7—C12—C11—H11	−178.1 (3)
C1—C6—C5—C4	1.45 (1)	C8—C7—N2—H2C	134.6 (5)
C1—C6—C5—H5	−175.5 (3)	C8—C7—N2—H2A	14.4 (3)
C2—C1—N1—H1B	−113.9 (4)	C8—C7—N2—H2B	−109.0 (4)
C2—C1—N1—H1A	8.9 (3)	C8—C7—C12—C11	−0.43 (1)
C2—C1—N1—H1C	131.2 (5)	C8—C7—C12—H12	−179.5 (3)
C2—C1—C6—C5	−0.89 (1)	C8—C9—C10—C11	−0.29 (1)
C2—C1—C6—H6	179.6 (3)	C9—C10—C11—C12	0.000 (13)
C2—C3—C4—C10	−178.96 (2)	C9—C10—C11—H11	178.3 (3)
C2—C3—C4—C5	−0.39 (1)	C9—C8—C7—C12	0.16 (1)
C3—C4—C10—C11	−21.94 (1)	C10—C4—C5—H5	−5.4 (2)
C3—C4—C10—C9	156.21 (1)	C10—C4—C3—H3	−2.4 (2)
C3—C4—C5—C6	−0.82 (1)	C10—C11—C12—H12	179.5 (3)
C3—C4—C5—H5	176.1 (3)	C10—C9—C8—H8	179.7 (3)
C3—C2—C1—C6	−0.28 (1)	C11—C10—C9—H9	177.9 (3)
C4—C10—C11—C12	178.22 (2)	C12—C7—N2—H2C	−43.6 (3)
C4—C10—C11—H11	−3.4 (2)	C12—C7—N2—H2A	−163.9 (4)
C4—C10—C9—C8	−178.50 (2)	C12—C7—N2—H2B	72.8 (3)
C4—C10—C9—H9	−0.3 (2)	C12—C7—C8—H8	−179.3 (3)
C4—C5—C6—H6	−179.1 (3)	H2—C2—C3—H3	1.9 (3)
C4—C3—C2—H2	178.6 (3)	H5—C5—C6—H6	4.0 (3)
C5—C4—C10—C11	159.54 (1)	H8—C8—C9—H9	1.5 (3)
C5—C4—C10—C9	−22.31 (1)	H11—C11—C12—H12	1.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···C11	1.069 (4)	2.678 (4)	2.9685 (2)	95.0 (2)
C5—H5···C9	1.068 (4)	2.696 (4)	2.9722 (2)	94.2 (2)
C9—H9···C5	1.059 (4)	2.683 (4)	2.9722 (2)	95.2 (3)
C11—H11···C3	1.065 (4)	2.689 (4)	2.9685 (2)	94.5 (3)
N2—H2A···CL2^i	1.002 (6)	2.240 (6)	3.2330 (1)	170.5 (5)
N2—H2A···CL1^ii	1.002 (6)	2.932 (5)	3.3425 (1)	105.5 (3)
N2—H2C···CL1^ii	1.000 (6)	2.953 (5)	3.3425 (1)	104.3 (3)
N2—H2C···CL1^iii	1.000 (6)	2.223 (6)	3.1960 (1)	164.0 (5)
C12—H12···CL1^iii	1.046 (4)	2.974 (4)	3.5980 (2)	118.9 (3)
N1—H1A···CL2^iv	1.003 (6)	2.929 (5)	3.3448 (1)	105.8 (4)
N1—H1B···CL2^iv	0.994 (6)	3.005 (6)	3.3448 (1)	101.3 (4)
N1—H1A···CL1^v	1.003 (6)	2.223 (6)	3.2120 (1)	168.7 (5)
C6—H6···CL1^vi	1.055 (4)	2.546 (4)	3.5827 (1)	167.3 (3)
N1—H1C···CL1^vii	1.024 (6)	2.178 (6)	3.1844 (1)	167.0 (5)
N2—H2B···CL1^viii	1.021 (6)	3.042 (6)	3.5814 (1)	114.0 (4)
N2—H2B···CL2^ix	1.021 (6)	2.191 (6)	3.1812 (1)	163.2 (5)
N2—H2C···C6^x	1.000 (6)	3.135 (5)	3.4798 (2)	101.8 (3)
C5—H5···C7^x	1.068 (4)	3.162 (4)	3.4363 (2)	95.7 (2)
N1—H1B···CL2^xi	0.994 (6)	2.179 (6)	3.1437 (1)	163.3 (5)
C2—H2···C10^xi	1.068 (4)	3.269 (4)	3.4500 (2)	90.6 (2)
C3—H3···C3^xi	1.069 (4)	3.147 (4)	3.3815 (3)	93.3 (2)
C3—H3···C4^xi	1.069 (4)	3.027 (4)	3.4960 (2)	107.2 (3)
C3—H3···C10^xi	1.069 (4)	3.220 (4)	3.4511 (2)	93.3 (2)

Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z+1; (iii) −x, −y+1, −z+1; (iv) x+1, y, z−1; (v) x+1, y, z; (vi) x+1, y+1, z; (vii) −x+1, −y+1, −z; (viii) −x+1, −y+1, −z+1; (ix) −x+1, −y+1, −z+2; (x) −x+1, −y+2, −z+1; (xi) −x+2, −y+1, −z+1.

(DCDMT_IAM_50)

Crystal data

C22H16Cl2	V = 1613.19 (10) Å^3
Mr = 396.11	Z = 4
Monoclinic, P21	F(000) = 808
a = 13.5510 (5) Å	Dx = 1.631 Mg m^−3
b = 8.0183 (3) Å	Mo Kα radiation, λ = 0.71073 Å
c = 14.8834 (4) Å	µ = 0.73 mm^−1
β = 94.021 (3)°	T = 293 K

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 1.4°
5664 measured reflections	h = −16→16
5664 independent reflections	k = −9→9
5640 reflections with I > 2σ(I)	l = 0→17

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)] = 0.021	H-atom parameters constrained
wR(F^2) = 0.060	w = 1/[σ^2(Fo^2) + (0.0301P)^2 + 0.3536P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
5664 reflections	Δρmax = 0.22 e Å^−3
529 parameters	Δρmin = −0.19 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: 0.00 (3)

Special details

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.

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 > 2sigma(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
Cl1	0.51132 (3)	0.73106 (5)	0.07698 (2)	0.02395 (9)
Cl2	0.48564 (3)	0.63567 (5)	0.48995 (2)	0.02455 (10)
Cl3	0.01506 (3)	0.78374 (6)	0.52918 (3)	0.02825 (10)
Cl4	−0.00915 (3)	0.84618 (6)	0.94386 (3)	0.02850 (10)
C001	0.23200 (10)	0.60912 (17)	0.19745 (9)	0.0126 (3)
C002	0.40407 (9)	0.58994 (17)	0.31459 (9)	0.0117 (3)
C003	0.32403 (10)	0.52518 (18)	0.16304 (9)	0.0131 (3)
C004	0.47794 (10)	0.65787 (19)	0.37267 (9)	0.0149 (3)
C005	0.17807 (10)	1.00859 (19)	0.83724 (9)	0.0136 (3)
C006	0.32191 (10)	0.34506 (19)	0.19691 (9)	0.0135 (3)
C007	0.41113 (9)	0.60758 (17)	0.22004 (9)	0.0112 (3)
C008	0.49091 (11)	0.69639 (18)	0.19037 (10)	0.0150 (3)
C009	0.01071 (11)	0.83644 (19)	0.82902 (10)	0.0166 (3)
C010	0.34091 (11)	0.8411 (2)	0.86837 (10)	0.0178 (3)
H010	0.3388 (13)	0.855 (2)	0.9293 (13)	0.021*
C011	0.17990 (10)	1.17509 (18)	0.78705 (10)	0.0131 (3)
C012	0.16111 (11)	0.69667 (18)	0.14494 (10)	0.0170 (3)
H012	0.1649 (13)	0.706 (2)	0.0816 (13)	0.020*
C013	0.27525 (10)	0.89715 (17)	0.71714 (10)	0.0128 (3)
C014	0.18960 (10)	0.97928 (17)	0.66073 (9)	0.0123 (3)
C015	0.22460 (10)	0.59491 (17)	0.28983 (9)	0.0129 (3)
C016	0.18012 (11)	1.4729 (2)	0.77186 (13)	0.0234 (3)
H016	0.1815 (14)	1.574 (3)	0.7987 (13)	0.028*
C017	0.18509 (10)	1.15947 (18)	0.69423 (10)	0.0128 (3)
C018	0.35337 (10)	0.81085 (18)	0.68330 (10)	0.0162 (3)
H018	0.3573 (13)	0.802 (2)	0.6203 (13)	0.019*
C019	0.02224 (10)	0.80802 (19)	0.64639 (10)	0.0164 (3)
C020	0.30931 (10)	0.49644 (18)	0.33903 (9)	0.0128 (3)
C021	0.31407 (10)	0.33011 (18)	0.28947 (10)	0.0136 (3)
C022	0.26912 (10)	0.91203 (17)	0.80972 (9)	0.0130 (3)
C023	−0.05445 (10)	0.7306 (2)	0.68783 (11)	0.0200 (3)
H023	−0.1037 (14)	0.671 (2)	0.6543 (13)	0.024*
C024	0.09605 (10)	0.89569 (17)	0.69542 (10)	0.0131 (3)
C025	0.31639 (11)	0.0312 (2)	0.27476 (13)	0.0234 (4)
H025	0.3138 (14)	−0.080 (3)	0.2970 (13)	0.028*
C026	0.08997 (10)	0.91083 (17)	0.79009 (10)	0.0126 (3)
C027	0.20553 (11)	0.9716 (2)	0.56021 (10)	0.0187 (3)
H02A	0.2123 (14)	0.861 (3)	0.5377 (13)	0.028*
H02B	0.2684 (14)	1.028 (3)	0.5489 (13)	0.028*
H02C	0.1531 (15)	1.027 (3)	0.5230 (14)	0.028*
C028	0.42434 (11)	0.7375 (2)	0.74283 (11)	0.0206 (3)
H028	0.4768 (14)	0.672 (3)	0.7217 (12)	0.025*
C029	0.55571 (10)	0.74919 (19)	0.34039 (10)	0.0182 (3)
H029	0.6048 (13)	0.798 (2)	0.3813 (12)	0.022*
C030	0.56198 (10)	0.76850 (18)	0.24985 (10)	0.0172 (3)
H030	0.6164 (13)	0.829 (2)	0.2265 (12)	0.021*
C031	0.17778 (10)	1.3318 (2)	0.82595 (11)	0.0180 (3)
H031	0.1758 (13)	1.343 (3)	0.8894 (13)	0.022*
C032	0.18411 (11)	1.4571 (2)	0.67958 (12)	0.0219 (3)
H032	0.1834 (14)	1.551 (3)	0.6411 (13)	0.026*
C033	0.32350 (11)	0.0469 (2)	0.18252 (12)	0.0222 (3)
H033	0.3279 (14)	−0.049 (3)	0.1450 (14)	0.027*
C034	0.07584 (10)	0.7589 (2)	0.27743 (11)	0.0205 (3)
H034	0.0178 (14)	0.812 (2)	0.3049 (12)	0.025*
C035	0.08314 (11)	0.77209 (19)	0.18555 (11)	0.0204 (3)
H035	0.0343 (14)	0.831 (3)	0.1501 (12)	0.025*
C036	0.14640 (11)	0.66934 (18)	0.32985 (10)	0.0157 (3)
H036	0.1399 (13)	0.656 (2)	0.3898 (13)	0.019*
C037	−0.06058 (10)	0.74515 (19)	0.77846 (11)	0.0207 (3)
H037	−0.1143 (14)	0.693 (2)	0.8128 (13)	0.025*
C038	0.41787 (11)	0.7518 (2)	0.83457 (11)	0.0220 (3)
H038	0.4683 (14)	0.700 (2)	0.8761 (13)	0.026*
C039	0.32317 (12)	0.5319 (2)	0.06097 (10)	0.0197 (3)
H03A	0.3205 (14)	0.649 (3)	0.0390 (13)	0.030*
H03B	0.2635 (15)	0.474 (3)	0.0338 (14)	0.030*
H03C	0.3817 (15)	0.479 (3)	0.0370 (13)	0.030*
C040	0.32675 (11)	0.20425 (19)	0.14346 (11)	0.0189 (3)
H040	0.3320 (13)	0.211 (2)	0.0769 (13)	0.023*
C041	0.18651 (10)	1.3005 (2)	0.64060 (11)	0.0179 (3)
H041	0.1887 (13)	1.285 (2)	0.5785 (13)	0.021*
C042	0.29069 (11)	0.4715 (2)	0.43771 (10)	0.0187 (3)
H04A	0.2267 (14)	0.409 (3)	0.4401 (13)	0.028*
H04B	0.2899 (14)	0.579 (3)	0.4707 (13)	0.028*
H04C	0.3417 (14)	0.402 (3)	0.4696 (13)	0.028*
C043	0.18114 (12)	1.0348 (2)	0.93834 (10)	0.0208 (3)
H04D	0.1246 (15)	1.095 (3)	0.9577 (13)	0.031*
H04E	0.2405 (15)	1.094 (3)	0.9545 (14)	0.031*
H04F	0.1853 (15)	0.929 (3)	0.9694 (14)	0.031*
C044	0.31176 (10)	0.1731 (2)	0.32817 (11)	0.0177 (3)
H044	0.3092 (13)	0.162 (3)	0.3895 (13)	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02271 (18)	0.0318 (2)	0.01819 (18)	−0.00508 (16)	0.00778 (14)	0.00690 (16)
Cl2	0.02303 (19)	0.0369 (2)	0.01322 (17)	−0.00449 (16)	−0.00230 (13)	−0.00400 (16)
Cl3	0.02140 (19)	0.0414 (2)	0.02121 (18)	−0.00489 (16)	−0.00355 (14)	−0.01321 (17)
Cl4	0.02438 (19)	0.0416 (2)	0.02069 (19)	−0.00296 (17)	0.00960 (14)	0.01077 (17)
C001	0.0123 (6)	0.0095 (6)	0.0160 (7)	−0.0031 (5)	0.0011 (5)	0.0002 (5)
C002	0.0109 (6)	0.0087 (6)	0.0159 (7)	0.0026 (5)	0.0023 (5)	−0.0007 (5)
C003	0.0117 (6)	0.0144 (7)	0.0133 (7)	−0.0006 (5)	0.0019 (5)	−0.0001 (5)
C004	0.0149 (6)	0.0162 (7)	0.0135 (7)	0.0031 (6)	0.0012 (5)	−0.0023 (6)
C005	0.0139 (6)	0.0137 (7)	0.0134 (7)	0.0005 (6)	0.0019 (5)	0.0008 (6)
C006	0.0080 (6)	0.0138 (7)	0.0186 (7)	−0.0006 (5)	−0.0002 (5)	−0.0009 (6)
C007	0.0123 (6)	0.0077 (6)	0.0138 (6)	0.0011 (5)	0.0016 (5)	0.0004 (5)
C008	0.0160 (7)	0.0132 (7)	0.0163 (7)	0.0031 (5)	0.0053 (5)	0.0009 (5)
C009	0.0161 (7)	0.0147 (7)	0.0197 (7)	0.0022 (6)	0.0048 (5)	0.0069 (6)
C010	0.0150 (7)	0.0194 (7)	0.0185 (7)	−0.0024 (6)	−0.0019 (6)	0.0057 (6)
C011	0.0079 (6)	0.0137 (7)	0.0178 (7)	−0.0008 (5)	0.0006 (5)	0.0000 (6)
C012	0.0152 (7)	0.0154 (7)	0.0201 (8)	−0.0023 (6)	−0.0011 (6)	0.0040 (6)
C013	0.0099 (6)	0.0104 (6)	0.0177 (7)	−0.0023 (5)	−0.0007 (5)	0.0018 (5)
C014	0.0113 (6)	0.0137 (7)	0.0119 (7)	0.0016 (5)	0.0004 (5)	0.0005 (5)
C015	0.0112 (6)	0.0091 (7)	0.0185 (7)	−0.0021 (5)	0.0011 (5)	0.0010 (5)
C016	0.0142 (7)	0.0124 (8)	0.0437 (10)	−0.0008 (6)	0.0020 (7)	−0.0039 (7)
C017	0.0065 (6)	0.0133 (7)	0.0184 (7)	0.0001 (5)	0.0004 (5)	0.0020 (6)
C018	0.0137 (7)	0.0139 (7)	0.0214 (8)	−0.0023 (6)	0.0043 (6)	−0.0023 (6)
C019	0.0126 (6)	0.0171 (7)	0.0195 (7)	0.0037 (6)	0.0002 (5)	−0.0049 (6)
C020	0.0120 (6)	0.0133 (7)	0.0134 (7)	−0.0001 (6)	0.0023 (5)	0.0019 (6)
C021	0.0079 (6)	0.0125 (7)	0.0203 (7)	0.0005 (5)	0.0008 (5)	0.0002 (6)
C022	0.0114 (6)	0.0101 (6)	0.0177 (7)	−0.0023 (5)	0.0021 (5)	0.0010 (5)
C023	0.0102 (6)	0.0139 (7)	0.0354 (9)	−0.0007 (6)	−0.0023 (6)	−0.0046 (7)
C024	0.0110 (6)	0.0101 (6)	0.0183 (7)	0.0028 (5)	0.0013 (5)	−0.0003 (5)
C025	0.0139 (7)	0.0120 (8)	0.0442 (10)	−0.0001 (6)	0.0005 (6)	0.0034 (7)
C026	0.0123 (6)	0.0089 (6)	0.0166 (7)	0.0030 (5)	0.0012 (5)	0.0014 (5)
C027	0.0165 (7)	0.0242 (8)	0.0157 (7)	0.0005 (6)	0.0025 (6)	−0.0004 (6)
C028	0.0106 (6)	0.0151 (7)	0.0363 (9)	0.0005 (6)	0.0037 (6)	0.0012 (7)
C029	0.0129 (6)	0.0169 (7)	0.0244 (7)	−0.0014 (6)	−0.0010 (6)	−0.0056 (6)
C030	0.0118 (7)	0.0141 (7)	0.0262 (8)	−0.0013 (6)	0.0055 (6)	0.0005 (6)
C031	0.0124 (7)	0.0167 (7)	0.0248 (8)	−0.0009 (6)	0.0013 (6)	−0.0061 (6)
C032	0.0127 (7)	0.0147 (7)	0.0385 (9)	0.0020 (6)	0.0033 (6)	0.0101 (7)
C033	0.0144 (7)	0.0143 (8)	0.0377 (9)	−0.0006 (6)	0.0010 (6)	−0.0075 (7)
C034	0.0121 (7)	0.0161 (7)	0.0339 (8)	0.0001 (6)	0.0056 (6)	−0.0018 (6)
C035	0.0137 (7)	0.0163 (7)	0.0307 (8)	0.0002 (6)	−0.0028 (6)	0.0046 (6)
C036	0.0158 (7)	0.0132 (7)	0.0188 (8)	−0.0033 (5)	0.0055 (6)	−0.0018 (6)
C037	0.0122 (7)	0.0150 (7)	0.0356 (9)	0.0002 (6)	0.0059 (6)	0.0051 (7)
C038	0.0137 (7)	0.0215 (8)	0.0302 (8)	0.0007 (6)	−0.0021 (6)	0.0100 (7)
C039	0.0212 (7)	0.0240 (8)	0.0139 (7)	−0.0012 (7)	0.0012 (6)	−0.0013 (6)
C040	0.0121 (7)	0.0173 (8)	0.0272 (8)	−0.0011 (6)	0.0005 (6)	−0.0071 (6)
C041	0.0094 (6)	0.0211 (8)	0.0231 (8)	0.0003 (6)	0.0012 (5)	0.0083 (6)
C042	0.0179 (7)	0.0248 (8)	0.0135 (7)	−0.0003 (6)	0.0016 (6)	0.0031 (6)
C043	0.0239 (8)	0.0252 (9)	0.0135 (7)	−0.0006 (7)	0.0028 (6)	−0.0002 (6)
C044	0.0118 (7)	0.0167 (7)	0.0243 (8)	−0.0003 (5)	0.0007 (6)	0.0071 (6)

Geometric parameters (Å, º)

Cl1—C008	1.7513 (14)	C018—C028	1.392 (2)
Cl2—C004	1.7505 (14)	C019—C023	1.391 (2)
Cl3—C019	1.7513 (15)	C019—C024	1.387 (2)
Cl4—C009	1.7505 (15)	C020—C021	1.528 (2)
C001—C003	1.5362 (18)	C020—C042	1.5208 (19)
C001—C012	1.386 (2)	C021—C044	1.386 (2)
C001—C015	1.390 (2)	C023—H023	0.93 (2)
C002—C004	1.387 (2)	C023—C037	1.362 (2)
C002—C007	1.4243 (19)	C024—C026	1.422 (2)
C002—C020	1.5520 (18)	C025—H025	0.95 (2)
C003—C006	1.531 (2)	C025—C033	1.389 (3)
C003—C007	1.5521 (18)	C025—C044	1.392 (2)
C003—C039	1.519 (2)	C027—H02A	0.95 (2)
C004—C029	1.396 (2)	C027—H02B	0.99 (2)
C005—C011	1.531 (2)	C027—H02C	0.98 (2)
C005—C022	1.5363 (19)	C028—H028	0.95 (2)
C005—C026	1.5539 (19)	C028—C038	1.379 (2)
C005—C043	1.517 (2)	C029—H029	0.953 (19)
C006—C021	1.394 (2)	C029—C030	1.365 (2)
C006—C040	1.385 (2)	C030—H030	0.968 (19)
C007—C008	1.392 (2)	C031—H031	0.950 (18)
C008—C030	1.388 (2)	C032—H032	0.95 (2)
C009—C026	1.390 (2)	C032—C041	1.385 (2)
C009—C037	1.390 (2)	C033—H033	0.95 (2)
C010—H010	0.917 (18)	C033—C040	1.391 (2)
C010—C022	1.383 (2)	C034—H034	1.006 (19)
C010—C038	1.388 (2)	C034—C035	1.382 (2)
C011—C017	1.394 (2)	C034—C036	1.391 (2)
C011—C031	1.385 (2)	C035—H035	0.94 (2)
C012—H012	0.951 (19)	C036—H036	0.908 (19)
C012—C035	1.392 (2)	C037—H037	1.01 (2)
C013—C014	1.5326 (18)	C038—H038	0.98 (2)
C013—C018	1.388 (2)	C039—H03A	1.00 (2)
C013—C022	1.391 (2)	C039—H03B	0.99 (2)
C014—C017	1.531 (2)	C039—H03C	0.99 (2)
C014—C024	1.5540 (19)	C040—H040	1.000 (19)
C014—C027	1.5278 (19)	C041—H041	0.934 (19)
C015—C020	1.5360 (19)	C042—H04A	1.00 (2)
C015—C036	1.386 (2)	C042—H04B	0.99 (2)
C016—H016	0.90 (2)	C042—H04C	0.98 (2)
C016—C031	1.390 (2)	C043—H04D	0.97 (2)
C016—C032	1.384 (3)	C043—H04E	0.95 (2)
C017—C041	1.385 (2)	C043—H04F	0.96 (2)
C018—H018	0.945 (18)	C044—H044	0.921 (19)
C012—C001—C003	125.50 (13)	C019—C023—H023	121.1 (12)
C012—C001—C015	120.26 (13)	C037—C023—C019	120.02 (14)
C015—C001—C003	114.23 (11)	C037—C023—H023	118.8 (12)
C004—C002—C007	118.76 (12)	C019—C024—C014	128.22 (13)
C004—C002—C020	128.05 (12)	C019—C024—C026	118.33 (12)
C007—C002—C020	113.17 (11)	C026—C024—C014	113.43 (11)
C001—C003—C007	103.61 (11)	C033—C025—H025	115.8 (12)
C006—C003—C001	105.61 (11)	C033—C025—C044	119.97 (14)
C006—C003—C007	104.64 (11)	C044—C025—H025	124.2 (12)
C039—C003—C001	111.62 (11)	C009—C026—C005	128.30 (13)
C039—C003—C006	111.32 (12)	C009—C026—C024	118.45 (13)
C039—C003—C007	118.93 (11)	C024—C026—C005	113.23 (11)
C002—C004—Cl2	124.85 (11)	C014—C027—H02A	113.9 (12)
C002—C004—C029	121.38 (13)	C014—C027—H02B	109.3 (12)
C029—C004—Cl2	113.76 (11)	C014—C027—H02C	113.0 (11)
C011—C005—C022	105.58 (11)	H02A—C027—H02B	105.0 (17)
C011—C005—C026	104.94 (11)	H02A—C027—H02C	107.8 (17)
C022—C005—C026	103.38 (11)	H02B—C027—H02C	107.4 (16)
C043—C005—C011	111.29 (12)	C018—C028—H028	121.3 (11)
C043—C005—C022	111.56 (12)	C038—C028—C018	120.40 (14)
C043—C005—C026	118.98 (12)	C038—C028—H028	118.2 (11)
C021—C006—C003	114.27 (12)	C004—C029—H029	120.2 (11)
C040—C006—C003	125.25 (13)	C030—C029—C004	120.00 (13)
C040—C006—C021	120.47 (14)	C030—C029—H029	119.8 (11)
C002—C007—C003	113.37 (11)	C008—C030—H030	119.5 (10)
C008—C007—C002	118.15 (12)	C029—C030—C008	119.61 (13)
C008—C007—C003	128.47 (12)	C029—C030—H030	120.8 (10)
C007—C008—Cl1	124.44 (11)	C011—C031—C016	119.64 (14)
C030—C008—Cl1	113.53 (11)	C011—C031—H031	120.0 (13)
C030—C008—C007	122.03 (13)	C016—C031—H031	120.3 (13)
C026—C009—Cl4	124.34 (12)	C016—C032—H032	121.9 (12)
C026—C009—C037	121.88 (13)	C016—C032—C041	120.18 (14)
C037—C009—Cl4	113.78 (11)	C041—C032—H032	117.9 (12)
C022—C010—H010	120.2 (12)	C025—C033—H033	121.2 (12)
C022—C010—C038	119.77 (14)	C025—C033—C040	120.12 (15)
C038—C010—H010	120.0 (11)	C040—C033—H033	118.7 (12)
C017—C011—C005	114.13 (12)	C035—C034—H034	118.9 (11)
C031—C011—C005	125.87 (13)	C035—C034—C036	120.03 (14)
C031—C011—C017	119.99 (13)	C036—C034—H034	121.1 (11)
C001—C012—H012	121.0 (11)	C012—C035—H035	120.0 (11)
C001—C012—C035	119.51 (14)	C034—C035—C012	120.37 (14)
C035—C012—H012	119.5 (11)	C034—C035—H035	119.7 (11)
C018—C013—C014	125.65 (13)	C015—C036—C034	119.83 (14)
C018—C013—C022	120.13 (13)	C015—C036—H036	120.1 (12)
C022—C013—C014	114.21 (12)	C034—C036—H036	120.0 (11)
C013—C014—C024	103.70 (11)	C009—C037—H037	116.3 (11)
C017—C014—C013	105.85 (11)	C023—C037—C009	119.51 (13)
C017—C014—C024	104.28 (11)	C023—C037—H037	124.2 (11)
C027—C014—C013	111.44 (11)	C010—C038—H038	119.9 (11)
C027—C014—C017	111.63 (12)	C028—C038—C010	120.21 (14)
C027—C014—C024	118.85 (12)	C028—C038—H038	119.9 (11)
C001—C015—C020	114.21 (12)	C003—C039—H03A	111.0 (11)
C036—C015—C001	120.00 (13)	C003—C039—H03B	109.8 (11)
C036—C015—C020	125.78 (13)	C003—C039—H03C	113.3 (11)
C031—C016—H016	118.4 (13)	H03A—C039—H03B	107.4 (17)
C032—C016—H016	121.3 (13)	H03A—C039—H03C	107.4 (17)
C032—C016—C031	120.25 (15)	H03B—C039—H03C	107.7 (16)
C011—C017—C014	114.42 (12)	C006—C040—C033	119.67 (15)
C041—C017—C011	120.11 (14)	C006—C040—H040	122.5 (11)
C041—C017—C014	125.47 (13)	C033—C040—H040	117.9 (11)
C013—C018—H018	119.6 (11)	C017—C041—H041	117.8 (12)
C013—C018—C028	119.36 (14)	C032—C041—C017	119.82 (14)
C028—C018—H018	121.0 (11)	C032—C041—H041	122.4 (12)
C023—C019—Cl3	113.64 (11)	C020—C042—H04A	107.6 (11)
C024—C019—Cl3	124.61 (11)	C020—C042—H04B	111.8 (12)
C024—C019—C023	121.75 (14)	C020—C042—H04C	112.4 (11)
C015—C020—C002	104.06 (11)	H04A—C042—H04B	112.2 (16)
C021—C020—C002	104.18 (10)	H04A—C042—H04C	106.2 (16)
C021—C020—C015	105.91 (11)	H04B—C042—H04C	106.6 (16)
C042—C020—C002	119.06 (12)	C005—C043—H04D	113.4 (12)
C042—C020—C015	111.03 (12)	C005—C043—H04E	106.5 (12)
C042—C020—C021	111.54 (12)	C005—C043—H04F	110.6 (12)
C006—C021—C020	114.25 (12)	H04D—C043—H04E	110.4 (17)
C044—C021—C006	119.63 (13)	H04D—C043—H04F	108.6 (17)
C044—C021—C020	126.12 (13)	H04E—C043—H04F	107.2 (18)
C010—C022—C005	125.56 (13)	C021—C044—C025	120.12 (14)
C010—C022—C013	120.10 (13)	C021—C044—H044	120.5 (13)
C013—C022—C005	114.33 (12)	C025—C044—H044	119.3 (13)
Cl1—C008—C030—C029	−179.12 (12)	C015—C020—C021—C006	53.50 (14)
Cl2—C004—C029—C030	176.45 (11)	C015—C020—C021—C044	−126.84 (14)
Cl3—C019—C023—C037	−177.26 (12)	C016—C032—C041—C017	−0.1 (2)
Cl3—C019—C024—C014	−4.4 (2)	C017—C011—C031—C016	0.5 (2)
Cl3—C019—C024—C026	177.39 (10)	C017—C014—C024—C019	126.51 (15)
Cl4—C009—C026—C005	2.9 (2)	C017—C014—C024—C026	−55.19 (14)
Cl4—C009—C026—C024	−178.80 (10)	C018—C013—C014—C017	−127.71 (14)
Cl4—C009—C037—C023	178.85 (12)	C018—C013—C014—C024	122.84 (14)
C001—C003—C006—C021	−53.50 (15)	C018—C013—C014—C027	−6.2 (2)
C001—C003—C006—C040	126.28 (14)	C018—C013—C022—C005	−179.18 (13)
C001—C003—C007—C002	56.57 (14)	C018—C013—C022—C010	0.1 (2)
C001—C003—C007—C008	−121.88 (14)	C018—C028—C038—C010	−0.7 (2)
C001—C012—C035—C034	−0.5 (2)	C019—C023—C037—C009	−0.6 (2)
C001—C015—C020—C002	56.43 (14)	C019—C024—C026—C005	178.83 (12)
C001—C015—C020—C021	−53.08 (14)	C019—C024—C026—C009	0.32 (19)
C001—C015—C020—C042	−174.32 (12)	C020—C002—C004—Cl2	6.1 (2)
C001—C015—C036—C034	−0.4 (2)	C020—C002—C004—C029	−175.38 (14)
C002—C004—C029—C030	−2.2 (2)	C020—C002—C007—C003	−1.57 (16)
C002—C007—C008—Cl1	−179.81 (10)	C020—C002—C007—C008	177.05 (12)
C002—C007—C008—C030	−0.7 (2)	C020—C015—C036—C034	178.28 (13)
C002—C020—C021—C006	−55.93 (14)	C020—C021—C044—C025	179.80 (14)
C002—C020—C021—C044	123.74 (14)	C021—C006—C040—C033	0.2 (2)
C003—C001—C012—C035	−177.56 (13)	C022—C005—C011—C017	54.01 (15)
C003—C001—C015—C020	−0.64 (16)	C022—C005—C011—C031	−125.38 (14)
C003—C001—C015—C036	178.17 (12)	C022—C005—C026—C009	122.47 (15)
C003—C006—C021—C020	−0.10 (16)	C022—C005—C026—C024	−55.87 (14)
C003—C006—C021—C044	−179.79 (13)	C022—C010—C038—C028	1.8 (2)
C003—C006—C040—C033	−179.60 (13)	C022—C013—C014—C017	53.49 (14)
C003—C007—C008—Cl1	−1.4 (2)	C022—C013—C014—C024	−55.96 (14)
C003—C007—C008—C030	177.68 (13)	C022—C013—C014—C027	175.03 (12)
C004—C002—C007—C003	179.72 (12)	C022—C013—C018—C028	1.0 (2)
C004—C002—C007—C008	−1.66 (18)	C023—C019—C024—C014	175.85 (13)
C004—C002—C020—C015	124.07 (15)	C023—C019—C024—C026	−2.4 (2)
C004—C002—C020—C021	−125.15 (15)	C024—C014—C017—C011	56.14 (14)
C004—C002—C020—C042	−0.1 (2)	C024—C014—C017—C041	−124.33 (14)
C004—C029—C030—C008	−0.2 (2)	C024—C019—C023—C037	2.5 (2)
C005—C011—C017—C014	−0.92 (16)	C025—C033—C040—C006	−0.6 (2)
C005—C011—C017—C041	179.52 (12)	C026—C005—C011—C017	−54.84 (14)
C005—C011—C031—C016	179.82 (13)	C026—C005—C011—C031	125.78 (14)
C006—C003—C007—C002	−53.89 (14)	C026—C005—C022—C010	−122.67 (15)
C006—C003—C007—C008	127.67 (15)	C026—C005—C022—C013	56.56 (15)
C006—C021—C044—C025	−0.6 (2)	C026—C009—C037—C023	−1.5 (2)
C007—C002—C004—Cl2	−175.35 (10)	C027—C014—C017—C011	−174.32 (11)
C007—C002—C004—C029	3.1 (2)	C027—C014—C017—C041	5.21 (19)
C007—C002—C020—C015	−54.50 (14)	C027—C014—C024—C019	1.5 (2)
C007—C002—C020—C021	56.28 (14)	C027—C014—C024—C026	179.75 (12)
C007—C002—C020—C042	−178.72 (12)	C031—C011—C017—C014	178.50 (12)
C007—C003—C006—C021	55.49 (14)	C031—C011—C017—C041	−1.1 (2)
C007—C003—C006—C040	−124.73 (14)	C031—C016—C032—C041	−0.5 (2)
C007—C008—C030—C029	1.7 (2)	C032—C016—C031—C011	0.3 (2)
C011—C005—C022—C010	127.36 (14)	C033—C025—C044—C021	0.1 (2)
C011—C005—C022—C013	−53.41 (15)	C035—C034—C036—C015	0.7 (2)
C011—C005—C026—C009	−127.09 (15)	C036—C015—C020—C002	−122.30 (14)
C011—C005—C026—C024	54.58 (14)	C036—C015—C020—C021	128.19 (14)
C011—C017—C041—C032	0.9 (2)	C036—C015—C020—C042	7.0 (2)
C012—C001—C003—C006	−127.66 (14)	C036—C034—C035—C012	−0.3 (2)
C012—C001—C003—C007	122.61 (14)	C037—C009—C026—C005	−176.65 (14)
C012—C001—C003—C039	−6.54 (19)	C037—C009—C026—C024	1.6 (2)
C012—C001—C015—C020	−179.20 (12)	C038—C010—C022—C005	177.71 (14)
C012—C001—C015—C036	−0.4 (2)	C038—C010—C022—C013	−1.5 (2)
C013—C014—C017—C011	−52.90 (14)	C039—C003—C006—C021	−174.81 (11)
C013—C014—C017—C041	126.63 (14)	C039—C003—C006—C040	4.97 (19)
C013—C014—C024—C019	−122.87 (15)	C039—C003—C007—C002	−178.90 (12)
C013—C014—C024—C026	55.42 (14)	C039—C003—C007—C008	2.7 (2)
C013—C018—C028—C038	−0.7 (2)	C040—C006—C021—C020	−179.89 (12)
C014—C013—C018—C028	−177.73 (13)	C040—C006—C021—C044	0.4 (2)
C014—C013—C022—C005	−0.31 (16)	C042—C020—C021—C006	174.41 (12)
C014—C013—C022—C010	178.97 (13)	C042—C020—C021—C044	−5.93 (19)
C014—C017—C041—C032	−178.62 (13)	C043—C005—C011—C017	175.21 (12)
C014—C024—C026—C005	0.35 (16)	C043—C005—C011—C031	−4.18 (19)
C014—C024—C026—C009	−178.16 (12)	C043—C005—C022—C010	6.3 (2)
C015—C001—C003—C006	53.87 (14)	C043—C005—C022—C013	−174.43 (12)
C015—C001—C003—C007	−55.86 (14)	C043—C005—C026—C009	−1.8 (2)
C015—C001—C003—C039	174.99 (11)	C043—C005—C026—C024	179.84 (12)
C015—C001—C012—C035	0.8 (2)	C044—C025—C033—C040	0.5 (2)

(DCDMT_IAM_80)

Crystal data

C22H16Cl2	V = 1613.19 (10) Å^3
Mr = 396.11	Z = 4
Monoclinic, P21	F(000) = 808
a = 13.5510 (5) Å	Dx = 1.631 Mg m^−3
b = 8.0183 (3) Å	Mo Kα radiation, λ = 0.71073 Å
c = 14.8834 (4) Å	µ = 0.73 mm^−1
β = 94.021 (3)°	T = 293 K

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 40.0°, θmin = 1.4°
19996 measured reflections	h = −24→24
19996 independent reflections	k = −14→14
19609 reflections with I > 2σ(I)	l = 0→26

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)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.074	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.0997P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.002
19996 reflections	Δρmax = 0.80 e Å^−3
529 parameters	Δρmin = −0.40 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: 0.008 (14)

Special details

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.

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 > 2sigma(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
Cl1	0.511331 (13)	0.73110 (3)	0.077049 (11)	0.02220 (3)
Cl2	0.485675 (13)	0.63556 (3)	0.489953 (10)	0.02255 (3)
Cl3	0.015099 (13)	0.78366 (3)	0.529138 (13)	0.02641 (4)
Cl4	−0.009209 (14)	0.84640 (3)	0.943834 (12)	0.02648 (4)
C001	0.23234 (4)	0.60905 (6)	0.19727 (3)	0.01019 (7)
C002	0.40377 (4)	0.58999 (6)	0.31466 (3)	0.00959 (7)
C003	0.32410 (4)	0.52526 (6)	0.16309 (3)	0.01035 (7)
C004	0.47804 (4)	0.65791 (7)	0.37296 (4)	0.01299 (8)
C005	0.17806 (4)	1.00833 (6)	0.83712 (3)	0.01080 (7)
C006	0.32195 (4)	0.34537 (6)	0.19686 (4)	0.01110 (7)
C007	0.41108 (4)	0.60783 (6)	0.21989 (3)	0.00950 (7)
C008	0.49096 (4)	0.69640 (7)	0.18992 (4)	0.01251 (8)
C009	0.01064 (4)	0.83653 (8)	0.82934 (4)	0.01458 (8)
C010	0.34083 (4)	0.84148 (8)	0.86884 (4)	0.01601 (9)
H010	0.3395 (10)	0.8533 (18)	0.9270 (9)	0.019*
C011	0.17985 (4)	1.17454 (6)	0.78702 (4)	0.01089 (7)
C012	0.16119 (4)	0.69649 (7)	0.14464 (4)	0.01501 (8)
H012	0.1654 (9)	0.7087 (17)	0.0849 (9)	0.018*
C013	0.27507 (4)	0.89710 (6)	0.71691 (3)	0.01013 (7)
C014	0.18950 (4)	0.97922 (6)	0.66059 (3)	0.01011 (7)
C015	0.22486 (4)	0.59479 (6)	0.28999 (3)	0.01014 (7)
C016	0.18020 (5)	1.47382 (8)	0.77176 (6)	0.02100 (11)
H016	0.1798 (10)	1.576 (2)	0.7987 (10)	0.025*
C017	0.18510 (4)	1.15908 (6)	0.69408 (4)	0.01054 (7)
C018	0.35339 (4)	0.81085 (7)	0.68312 (4)	0.01459 (8)
H018	0.3548 (9)	0.7986 (18)	0.6179 (9)	0.018*
C019	0.02221 (4)	0.80780 (7)	0.64595 (4)	0.01438 (8)
C020	0.30929 (4)	0.49633 (6)	0.33905 (3)	0.01016 (7)
C021	0.31410 (4)	0.33012 (6)	0.28949 (4)	0.01105 (7)
C022	0.26901 (4)	0.91252 (6)	0.80977 (3)	0.01072 (7)
C023	−0.05469 (4)	0.73052 (8)	0.68721 (5)	0.01871 (10)
H023	−0.1045 (10)	0.6673 (19)	0.6527 (10)	0.022*
C024	0.09622 (4)	0.89570 (6)	0.69520 (4)	0.01037 (7)
C025	0.31636 (5)	0.03080 (7)	0.27452 (6)	0.02077 (11)
H025	0.3134 (10)	−0.081 (2)	0.2969 (10)	0.025*
C026	0.09011 (4)	0.91099 (6)	0.79017 (3)	0.01040 (7)
C027	0.20573 (5)	0.97150 (9)	0.56037 (4)	0.01703 (9)
H02A	0.2124 (11)	0.861 (2)	0.5354 (10)	0.026*
H02B	0.2688 (10)	1.029 (2)	0.5478 (10)	0.026*
H02C	0.1538 (10)	1.028 (2)	0.5247 (10)	0.026*
C028	0.42469 (4)	0.73696 (9)	0.74284 (5)	0.01862 (10)
H028	0.4802 (10)	0.6712 (18)	0.7221 (9)	0.022*
C029	0.55581 (4)	0.74920 (8)	0.34073 (4)	0.01625 (9)
H029	0.6031 (9)	0.7963 (18)	0.3817 (9)	0.019*
C030	0.56227 (4)	0.76863 (8)	0.24969 (4)	0.01569 (9)
H030	0.6157 (9)	0.8306 (18)	0.2247 (9)	0.019*
C031	0.17769 (5)	1.33180 (7)	0.82612 (5)	0.01630 (9)
H031	0.1745 (10)	1.3414 (19)	0.8902 (9)	0.020*
C032	0.18408 (5)	1.45785 (8)	0.67936 (6)	0.02025 (11)
H032	0.1832 (10)	1.549 (2)	0.6422 (10)	0.024*
C033	0.32370 (5)	0.04653 (8)	0.18232 (6)	0.02063 (11)
H033	0.3288 (10)	−0.047 (2)	0.1450 (10)	0.025*
C034	0.07561 (4)	0.75915 (8)	0.27742 (5)	0.01795 (10)
H034	0.0167 (10)	0.8120 (18)	0.3041 (9)	0.022*
C035	0.08305 (4)	0.77244 (8)	0.18527 (5)	0.01844 (10)
H035	0.0348 (10)	0.8296 (19)	0.1509 (9)	0.022*
C036	0.14640 (4)	0.66877 (7)	0.33025 (4)	0.01431 (8)
H036	0.1412 (9)	0.6527 (18)	0.3905 (9)	0.017*
C037	−0.06084 (4)	0.74507 (8)	0.77855 (5)	0.01854 (10)
H037	−0.1163 (10)	0.6960 (18)	0.8163 (10)	0.022*
C038	0.41813 (5)	0.75187 (9)	0.83501 (5)	0.01983 (11)
H038	0.4675 (11)	0.7006 (19)	0.8770 (10)	0.024*
C039	0.32328 (5)	0.53199 (9)	0.06087 (4)	0.01761 (9)
H03A	0.3209 (11)	0.651 (2)	0.0408 (10)	0.026*
H03B	0.2647 (10)	0.4696 (19)	0.0358 (10)	0.026*
H03C	0.3801 (10)	0.4805 (19)	0.0367 (10)	0.026*
C040	0.32679 (4)	0.20437 (7)	0.14319 (5)	0.01622 (9)
H040	0.3322 (10)	0.2110 (17)	0.0793 (9)	0.019*
C041	0.18646 (4)	1.30002 (7)	0.64013 (4)	0.01551 (9)
H041	0.1888 (9)	1.2879 (18)	0.5788 (9)	0.019*
C042	0.29080 (5)	0.47150 (9)	0.43775 (4)	0.01689 (9)
H04A	0.2273 (10)	0.411 (2)	0.4411 (10)	0.025*
H04B	0.2879 (11)	0.580 (2)	0.4703 (10)	0.025*
H04C	0.3430 (10)	0.405 (2)	0.4689 (10)	0.025*
C043	0.18111 (5)	1.03503 (10)	0.93846 (4)	0.01921 (10)
H04D	0.1224 (11)	1.088 (2)	0.9557 (10)	0.029*
H04E	0.2406 (11)	1.094 (2)	0.9544 (10)	0.029*
H04F	0.1851 (11)	0.931 (2)	0.9688 (11)	0.029*
C044	0.31182 (4)	0.17277 (7)	0.32847 (5)	0.01576 (9)
H044	0.3084 (10)	0.1624 (18)	0.3923 (9)	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02055 (6)	0.03033 (8)	0.01655 (6)	−0.00514 (5)	0.00708 (5)	0.00693 (5)
Cl2	0.02073 (6)	0.03460 (8)	0.01176 (5)	−0.00441 (6)	−0.00279 (4)	−0.00428 (5)
Cl3	0.01960 (6)	0.03949 (10)	0.01943 (6)	−0.00507 (6)	−0.00363 (5)	−0.01287 (6)
Cl4	0.02245 (7)	0.03903 (10)	0.01900 (6)	−0.00292 (6)	0.00895 (5)	0.01029 (6)
C001	0.00994 (16)	0.00951 (16)	0.01101 (16)	−0.00029 (13)	0.00002 (13)	0.00163 (13)
C002	0.00956 (16)	0.00950 (16)	0.00972 (16)	−0.00023 (13)	0.00078 (13)	−0.00071 (12)
C003	0.01145 (17)	0.01078 (16)	0.00884 (15)	−0.00059 (13)	0.00091 (13)	−0.00012 (13)
C004	0.01137 (18)	0.0154 (2)	0.01198 (17)	−0.00015 (15)	−0.00057 (14)	−0.00336 (15)
C005	0.01211 (17)	0.01101 (17)	0.00931 (16)	−0.00024 (13)	0.00104 (13)	0.00025 (13)
C006	0.01078 (17)	0.00906 (16)	0.01343 (17)	−0.00064 (13)	0.00062 (13)	−0.00174 (14)
C007	0.00989 (16)	0.00875 (15)	0.01003 (16)	−0.00038 (13)	0.00186 (13)	0.00018 (12)
C008	0.01138 (18)	0.01242 (18)	0.01412 (18)	−0.00096 (14)	0.00363 (14)	0.00149 (14)
C009	0.01197 (18)	0.01406 (19)	0.0182 (2)	−0.00008 (15)	0.00466 (15)	0.00472 (16)
C010	0.01264 (19)	0.0185 (2)	0.0165 (2)	0.00046 (17)	−0.00241 (16)	0.00622 (18)
C011	0.01071 (17)	0.00871 (16)	0.01328 (18)	−0.00050 (13)	0.00114 (13)	−0.00104 (13)
C012	0.01249 (19)	0.0152 (2)	0.0170 (2)	0.00038 (15)	−0.00185 (16)	0.00496 (16)
C013	0.00869 (15)	0.00957 (16)	0.01215 (17)	0.00030 (13)	0.00081 (13)	0.00014 (13)
C014	0.00969 (16)	0.01160 (17)	0.00906 (15)	0.00044 (13)	0.00075 (12)	−0.00004 (13)
C015	0.00953 (16)	0.00949 (16)	0.01154 (16)	−0.00013 (13)	0.00172 (13)	0.00027 (13)
C016	0.0169 (2)	0.00890 (19)	0.0373 (4)	−0.00009 (17)	0.0025 (2)	−0.0019 (2)
C017	0.00940 (16)	0.00928 (16)	0.01292 (17)	0.00020 (13)	0.00067 (13)	0.00228 (13)
C018	0.01066 (18)	0.0140 (2)	0.0194 (2)	0.00153 (15)	0.00307 (15)	−0.00146 (16)
C019	0.00989 (17)	0.0149 (2)	0.0181 (2)	−0.00031 (15)	−0.00114 (15)	−0.00513 (16)
C020	0.01058 (16)	0.01099 (17)	0.00903 (16)	−0.00024 (13)	0.00142 (13)	0.00131 (12)
C021	0.01062 (17)	0.00848 (16)	0.01401 (18)	−0.00011 (13)	0.00057 (13)	0.00162 (14)
C022	0.01007 (16)	0.01026 (16)	0.01165 (17)	−0.00034 (13)	−0.00038 (13)	0.00208 (13)
C023	0.01029 (18)	0.0160 (2)	0.0296 (3)	−0.00262 (17)	0.00003 (18)	−0.0041 (2)
C024	0.00865 (16)	0.00973 (16)	0.01268 (17)	−0.00002 (13)	0.00038 (13)	−0.00123 (13)
C025	0.0162 (2)	0.00874 (19)	0.0373 (4)	−0.00045 (16)	0.0011 (2)	0.0027 (2)
C026	0.01004 (16)	0.00913 (16)	0.01220 (17)	−0.00023 (13)	0.00193 (13)	0.00120 (13)
C027	0.0165 (2)	0.0246 (3)	0.01010 (18)	0.00054 (19)	0.00186 (15)	−0.00081 (17)
C028	0.01054 (19)	0.0165 (2)	0.0290 (3)	0.00321 (17)	0.00234 (18)	0.0025 (2)
C029	0.01093 (18)	0.0182 (2)	0.0195 (2)	−0.00301 (16)	−0.00003 (16)	−0.00462 (18)
C030	0.01098 (18)	0.0157 (2)	0.0207 (2)	−0.00301 (15)	0.00325 (16)	−0.00100 (17)
C031	0.0151 (2)	0.01117 (18)	0.0227 (2)	−0.00044 (16)	0.00176 (17)	−0.00558 (17)
C032	0.0148 (2)	0.0111 (2)	0.0350 (3)	0.00066 (16)	0.0025 (2)	0.0074 (2)
C033	0.0159 (2)	0.01007 (19)	0.0360 (3)	−0.00104 (16)	0.0017 (2)	−0.0063 (2)
C034	0.01087 (19)	0.0162 (2)	0.0271 (3)	0.00295 (16)	0.00325 (18)	−0.00010 (19)
C035	0.01176 (19)	0.0169 (2)	0.0264 (3)	0.00274 (17)	−0.00102 (18)	0.0051 (2)
C036	0.01150 (18)	0.0148 (2)	0.0171 (2)	0.00036 (15)	0.00424 (15)	−0.00168 (16)
C037	0.01125 (19)	0.0157 (2)	0.0291 (3)	−0.00247 (16)	0.00426 (18)	0.0026 (2)
C038	0.0122 (2)	0.0202 (2)	0.0267 (3)	0.00312 (18)	−0.00168 (18)	0.0080 (2)
C039	0.0207 (2)	0.0228 (2)	0.00943 (18)	−0.0017 (2)	0.00161 (16)	−0.00016 (17)
C040	0.0140 (2)	0.0128 (2)	0.0219 (2)	−0.00139 (15)	0.00090 (17)	−0.00720 (17)
C041	0.01214 (18)	0.0138 (2)	0.0206 (2)	0.00018 (15)	0.00114 (16)	0.00795 (17)
C042	0.0171 (2)	0.0238 (2)	0.01001 (18)	−0.00079 (19)	0.00254 (16)	0.00342 (17)
C043	0.0231 (3)	0.0249 (3)	0.00975 (18)	−0.0009 (2)	0.00205 (17)	−0.00128 (18)
C044	0.0131 (2)	0.01102 (19)	0.0230 (2)	−0.00029 (15)	0.00084 (17)	0.00611 (17)

Geometric parameters (Å, º)

Cl1—C008	1.7437 (6)	C018—C028	1.3979 (9)
Cl2—C004	1.7463 (6)	C019—C023	1.3916 (9)
Cl3—C019	1.7452 (6)	C019—C024	1.3917 (7)
Cl4—C009	1.7454 (6)	C020—C021	1.5268 (7)
C001—C003	1.5313 (7)	C020—C042	1.5205 (7)
C001—C012	1.3888 (7)	C021—C044	1.3900 (8)
C001—C015	1.3956 (7)	C023—H023	0.963 (14)
C002—C004	1.3928 (7)	C023—C037	1.3728 (11)
C002—C007	1.4280 (7)	C024—C026	1.4269 (7)
C002—C020	1.5493 (7)	C025—H025	0.955 (16)
C003—C006	1.5284 (7)	C025—C033	1.3884 (12)
C003—C007	1.5500 (7)	C025—C044	1.3970 (10)
C003—C039	1.5217 (8)	C027—H02A	0.965 (16)
C004—C029	1.3955 (8)	C027—H02B	1.001 (15)
C005—C011	1.5281 (7)	C027—H02C	0.965 (15)
C005—C022	1.5314 (7)	C028—H028	0.986 (14)
C005—C026	1.5496 (7)	C028—C038	1.3860 (11)
C005—C043	1.5211 (8)	C029—H029	0.933 (14)
C006—C021	1.3955 (8)	C029—C030	1.3727 (9)
C006—C040	1.3885 (8)	C030—H030	0.974 (13)
C007—C008	1.3938 (7)	C031—H031	0.960 (13)
C008—C030	1.3929 (8)	C032—H032	0.913 (16)
C009—C026	1.3943 (7)	C032—C041	1.3950 (10)
C009—C037	1.3946 (9)	C033—H033	0.939 (15)
C010—H010	0.873 (13)	C033—C040	1.3950 (10)
C010—C022	1.3873 (8)	C034—H034	1.010 (13)
C010—C038	1.3931 (10)	C034—C035	1.3863 (10)
C011—C017	1.3956 (8)	C034—C036	1.3992 (9)
C011—C031	1.3899 (8)	C035—H035	0.923 (14)
C012—H012	0.900 (14)	C036—H036	0.914 (13)
C012—C035	1.3956 (9)	C037—H037	1.046 (14)
C013—C014	1.5311 (7)	C038—H038	0.974 (15)
C013—C018	1.3901 (7)	C039—H03A	1.002 (16)
C013—C022	1.3958 (7)	C039—H03B	0.989 (15)
C014—C017	1.5285 (7)	C039—H03C	0.965 (15)
C014—C024	1.5502 (7)	C040—H040	0.960 (14)
C014—C027	1.5242 (8)	C041—H041	0.920 (13)
C015—C020	1.5323 (7)	C042—H04A	0.993 (15)
C015—C036	1.3895 (8)	C042—H04B	0.997 (16)
C016—H016	0.915 (16)	C042—H04C	0.978 (15)
C016—C031	1.3986 (10)	C043—H04D	0.952 (15)
C016—C032	1.3859 (12)	C043—H04E	0.949 (15)
C017—C041	1.3872 (8)	C043—H04F	0.951 (17)
C018—H018	0.977 (13)	C044—H044	0.958 (13)
C012—C001—C003	125.58 (5)	C019—C023—H023	121.1 (8)
C012—C001—C015	120.23 (5)	C037—C023—C019	119.90 (6)
C015—C001—C003	114.17 (4)	C037—C023—H023	119.0 (8)
C004—C002—C007	118.62 (5)	C019—C024—C014	128.17 (5)
C004—C002—C020	128.06 (5)	C019—C024—C026	118.39 (5)
C007—C002—C020	113.31 (4)	C026—C024—C014	113.41 (4)
C001—C003—C007	103.62 (4)	C033—C025—H025	116.0 (9)
C006—C003—C001	105.68 (4)	C033—C025—C044	120.21 (6)
C006—C003—C007	104.78 (4)	C044—C025—H025	123.8 (9)
C039—C003—C001	111.55 (4)	C009—C026—C005	128.26 (5)
C039—C003—C006	111.30 (5)	C009—C026—C024	118.53 (5)
C039—C003—C007	118.82 (4)	C024—C026—C005	113.19 (4)
C002—C004—Cl2	124.80 (4)	C014—C027—H02A	115.9 (9)
C002—C004—C029	121.41 (5)	C014—C027—H02B	110.4 (9)
C029—C004—Cl2	113.78 (4)	C014—C027—H02C	111.7 (9)
C011—C005—C022	105.50 (4)	H02A—C027—H02B	104.3 (13)
C011—C005—C026	104.91 (4)	H02A—C027—H02C	107.7 (13)
C022—C005—C026	103.61 (4)	H02B—C027—H02C	106.2 (12)
C043—C005—C011	111.15 (5)	C018—C028—H028	122.4 (8)
C043—C005—C022	111.57 (5)	C038—C028—C018	120.22 (6)
C043—C005—C026	118.99 (5)	C038—C028—H028	117.4 (8)
C021—C006—C003	114.33 (4)	C004—C029—H029	119.2 (8)
C040—C006—C003	125.20 (5)	C030—C029—C004	120.05 (5)
C040—C006—C021	120.46 (5)	C030—C029—H029	120.8 (8)
C002—C007—C003	113.15 (4)	C008—C030—H030	118.0 (8)
C008—C007—C002	118.45 (5)	C029—C030—C008	119.60 (5)
C008—C007—C003	128.39 (5)	C029—C030—H030	122.4 (8)
C007—C008—Cl1	124.65 (4)	C011—C031—C016	119.63 (6)
C030—C008—Cl1	113.54 (4)	C011—C031—H031	119.5 (9)
C030—C008—C007	121.80 (5)	C016—C031—H031	120.9 (9)
C026—C009—Cl4	124.42 (5)	C016—C032—H032	121.8 (10)
C026—C009—C037	121.73 (6)	C016—C032—C041	120.18 (6)
C037—C009—Cl4	113.85 (4)	C041—C032—H032	118.0 (10)
C022—C010—H010	121.4 (9)	C025—C033—H033	121.7 (9)
C022—C010—C038	119.64 (6)	C025—C033—C040	120.09 (6)
C038—C010—H010	118.9 (9)	C040—C033—H033	118.2 (9)
C017—C011—C005	114.19 (4)	C035—C034—H034	118.1 (8)
C031—C011—C005	125.83 (5)	C035—C034—C036	120.08 (5)
C031—C011—C017	119.97 (5)	C036—C034—H034	121.8 (8)
C001—C012—H012	121.5 (8)	C012—C035—H035	120.4 (9)
C001—C012—C035	119.58 (6)	C034—C035—C012	120.34 (5)
C035—C012—H012	118.9 (8)	C034—C035—H035	119.2 (9)
C018—C013—C014	125.73 (5)	C015—C036—C034	119.60 (6)
C018—C013—C022	120.11 (5)	C015—C036—H036	118.5 (8)
C022—C013—C014	114.15 (4)	C034—C036—H036	121.8 (8)
C013—C014—C024	103.66 (4)	C009—C037—H037	113.9 (8)
C017—C014—C013	105.81 (4)	C023—C037—C009	119.56 (5)
C017—C014—C024	104.35 (4)	C023—C037—H037	126.5 (8)
C027—C014—C013	111.26 (4)	C010—C038—H038	119.1 (9)
C027—C014—C017	111.66 (5)	C028—C038—C010	120.28 (6)
C027—C014—C024	118.99 (4)	C028—C038—H038	120.7 (9)
C001—C015—C020	114.20 (4)	C003—C039—H03A	109.2 (9)
C036—C015—C001	120.15 (5)	C003—C039—H03B	108.0 (9)
C036—C015—C020	125.65 (5)	C003—C039—H03C	114.1 (9)
C031—C016—H016	118.5 (9)	H03A—C039—H03B	111.3 (13)
C032—C016—H016	121.3 (9)	H03A—C039—H03C	107.9 (13)
C032—C016—C031	120.20 (6)	H03B—C039—H03C	106.4 (12)
C011—C017—C014	114.39 (4)	C006—C040—C033	119.64 (6)
C041—C017—C011	120.33 (5)	C006—C040—H040	122.3 (8)
C041—C017—C014	125.27 (5)	C033—C040—H040	118.1 (8)
C013—C018—H018	118.6 (8)	C017—C041—C032	119.68 (6)
C013—C018—C028	119.47 (6)	C017—C041—H041	119.4 (9)
C028—C018—H018	121.9 (8)	C032—C041—H041	120.9 (9)
C023—C019—Cl3	113.55 (4)	C020—C042—H04A	108.3 (9)
C024—C019—Cl3	124.63 (5)	C020—C042—H04B	111.7 (9)
C024—C019—C023	121.82 (6)	C020—C042—H04C	111.5 (9)
C015—C020—C002	103.90 (4)	H04A—C042—H04B	109.8 (12)
C021—C020—C002	104.23 (4)	H04A—C042—H04C	107.9 (12)
C021—C020—C015	105.98 (4)	H04B—C042—H04C	107.4 (12)
C042—C020—C002	119.00 (4)	C005—C043—H04D	111.4 (9)
C042—C020—C015	111.08 (4)	C005—C043—H04E	106.3 (9)
C042—C020—C021	111.59 (5)	C005—C043—H04F	110.0 (10)
C006—C021—C020	114.18 (4)	H04D—C043—H04E	115.0 (14)
C044—C021—C006	119.83 (5)	H04D—C043—H04F	106.7 (13)
C044—C021—C020	125.99 (5)	H04E—C043—H04F	107.4 (14)
C010—C022—C005	125.42 (5)	C021—C044—C025	119.77 (6)
C010—C022—C013	120.25 (5)	C021—C044—H044	119.8 (9)
C013—C022—C005	114.32 (4)	C025—C044—H044	120.4 (9)
Cl1—C008—C030—C029	−179.21 (5)	C015—C020—C021—C006	53.42 (6)
Cl2—C004—C029—C030	176.36 (5)	C015—C020—C021—C044	−126.91 (6)
Cl3—C019—C023—C037	−177.30 (5)	C016—C032—C041—C017	−0.13 (9)
Cl3—C019—C024—C014	−4.32 (8)	C017—C011—C031—C016	0.38 (8)
Cl3—C019—C024—C026	177.34 (4)	C017—C014—C024—C019	126.52 (6)
Cl4—C009—C026—C005	3.03 (8)	C017—C014—C024—C026	−55.07 (5)
Cl4—C009—C026—C024	−178.79 (4)	C018—C013—C014—C017	−127.60 (5)
Cl4—C009—C037—C023	178.78 (5)	C018—C013—C014—C024	122.90 (5)
C001—C003—C006—C021	−53.57 (5)	C018—C013—C014—C027	−6.14 (8)
C001—C003—C006—C040	126.22 (5)	C018—C013—C022—C005	−179.11 (5)
C001—C003—C007—C002	56.68 (5)	C018—C013—C022—C010	−0.22 (8)
C001—C003—C007—C008	−121.97 (6)	C018—C028—C038—C010	−0.42 (10)
C001—C012—C035—C034	−0.81 (9)	C019—C023—C037—C009	−0.43 (10)
C001—C015—C020—C002	56.52 (5)	C019—C024—C026—C005	178.78 (5)
C001—C015—C020—C021	−53.01 (5)	C019—C024—C026—C009	0.34 (7)
C001—C015—C020—C042	−174.39 (5)	C020—C002—C004—Cl2	5.89 (8)
C001—C015—C036—C034	−0.71 (8)	C020—C002—C004—C029	−175.55 (5)
C002—C004—C029—C030	−2.35 (9)	C020—C002—C007—C003	−1.51 (6)
C002—C007—C008—Cl1	−179.74 (4)	C020—C002—C007—C008	177.29 (5)
C002—C007—C008—C030	−0.76 (8)	C020—C015—C036—C034	178.27 (5)
C002—C020—C021—C006	−55.87 (5)	C020—C021—C044—C025	179.68 (5)
C002—C020—C021—C044	123.80 (5)	C021—C006—C040—C033	0.06 (8)
C003—C001—C012—C035	−177.49 (5)	C022—C005—C011—C017	54.10 (6)
C003—C001—C015—C020	−0.69 (6)	C022—C005—C011—C031	−125.26 (6)
C003—C001—C015—C036	178.40 (5)	C022—C005—C026—C009	122.51 (6)
C003—C006—C021—C020	−0.05 (6)	C022—C005—C026—C024	−55.75 (5)
C003—C006—C021—C044	−179.74 (5)	C022—C010—C038—C028	1.53 (10)
C003—C006—C040—C033	−179.73 (5)	C022—C013—C014—C017	53.32 (5)
C003—C007—C008—Cl1	−1.14 (8)	C022—C013—C014—C024	−56.19 (5)
C003—C007—C008—C030	177.83 (5)	C022—C013—C014—C027	174.78 (5)
C004—C002—C007—C003	179.52 (5)	C022—C013—C018—C028	1.32 (8)
C004—C002—C007—C008	−1.68 (7)	C023—C019—C024—C014	176.03 (5)
C004—C002—C020—C015	124.23 (6)	C023—C019—C024—C026	−2.31 (8)
C004—C002—C020—C021	−124.95 (6)	C024—C014—C017—C011	56.05 (5)
C004—C002—C020—C042	0.12 (8)	C024—C014—C017—C041	−124.27 (5)
C004—C029—C030—C008	−0.16 (9)	C024—C019—C023—C037	2.38 (9)
C005—C011—C017—C014	−0.82 (6)	C025—C033—C040—C006	−0.35 (9)
C005—C011—C017—C041	179.48 (5)	C026—C005—C011—C017	−54.96 (6)
C005—C011—C031—C016	179.71 (6)	C026—C005—C011—C031	125.68 (6)
C006—C003—C007—C002	−53.90 (5)	C026—C005—C022—C010	−122.52 (6)
C006—C003—C007—C008	127.45 (5)	C026—C005—C022—C013	56.30 (5)
C006—C021—C044—C025	−0.66 (8)	C026—C009—C037—C023	−1.54 (10)
C007—C002—C004—Cl2	−175.31 (4)	C027—C014—C017—C011	−174.17 (5)
C007—C002—C004—C029	3.25 (8)	C027—C014—C017—C041	5.51 (7)
C007—C002—C020—C015	−54.62 (5)	C027—C014—C024—C019	1.26 (8)
C007—C002—C020—C021	56.20 (5)	C027—C014—C024—C026	179.66 (5)
C007—C002—C020—C042	−178.73 (5)	C031—C011—C017—C014	178.59 (5)
C007—C003—C006—C021	55.52 (6)	C031—C011—C017—C041	−1.12 (8)
C007—C003—C006—C040	−124.69 (5)	C031—C016—C032—C041	−0.61 (10)
C007—C008—C030—C029	1.71 (9)	C032—C016—C031—C011	0.48 (9)
C011—C005—C022—C010	127.49 (6)	C033—C025—C044—C021	0.37 (9)
C011—C005—C022—C013	−53.69 (6)	C035—C034—C036—C015	0.99 (9)
C011—C005—C026—C009	−127.07 (6)	C036—C015—C020—C002	−122.52 (5)
C011—C005—C026—C024	54.67 (5)	C036—C015—C020—C021	127.95 (6)
C011—C017—C041—C032	0.99 (8)	C036—C015—C020—C042	6.58 (7)
C012—C001—C003—C006	−127.45 (5)	C036—C034—C035—C012	−0.23 (10)
C012—C001—C003—C007	122.63 (5)	C037—C009—C026—C005	−176.62 (5)
C012—C001—C003—C039	−6.35 (7)	C037—C009—C026—C024	1.56 (8)
C012—C001—C015—C020	−179.42 (5)	C038—C010—C022—C005	177.55 (6)
C012—C001—C015—C036	−0.33 (8)	C038—C010—C022—C013	−1.21 (9)
C013—C014—C017—C011	−52.97 (6)	C039—C003—C006—C021	−174.84 (5)
C013—C014—C017—C041	126.72 (5)	C039—C003—C006—C040	4.96 (7)
C013—C014—C024—C019	−122.89 (6)	C039—C003—C007—C002	−178.93 (5)
C013—C014—C024—C026	55.52 (5)	C039—C003—C007—C008	2.41 (8)
C013—C018—C028—C038	−1.01 (9)	C040—C006—C021—C020	−179.85 (5)
C014—C013—C018—C028	−177.71 (5)	C040—C006—C021—C044	0.46 (8)
C014—C013—C022—C005	0.03 (6)	C042—C020—C021—C006	174.47 (5)
C014—C013—C022—C010	178.92 (5)	C042—C020—C021—C044	−5.86 (7)
C014—C017—C041—C032	−178.68 (5)	C043—C005—C011—C017	175.19 (5)
C014—C024—C026—C005	0.21 (6)	C043—C005—C011—C031	−4.17 (8)
C014—C024—C026—C009	−178.24 (5)	C043—C005—C022—C010	6.68 (8)
C015—C001—C003—C006	53.90 (5)	C043—C005—C022—C013	−174.50 (5)
C015—C001—C003—C007	−56.02 (5)	C043—C005—C026—C009	−2.01 (8)
C015—C001—C003—C039	175.00 (5)	C043—C005—C026—C024	179.73 (5)
C015—C001—C012—C035	1.09 (8)	C044—C025—C033—C040	0.14 (10)

(DCDMT_N_100) 1,4,-dichloro-9,10-dimethylotriptycene

Crystal data

C22H16Cl2	Z = 4
Mr = 351.28	F(000) = 422
Monoclinic, P21	Dx = 1.432 Mg m^−3
a = 13.589 (3) Å	Mo Kα radiation
b = 8.0415 (16) Å	µ = 0.14 mm^−1
c = 14.943 (3) Å	T = 100 K
β = 93.998 (13)°	, colourless
V = 1628.9 (5) Å^3	5 × 3 × 2 mm

Data collection

11 neutro detectors diffractometer	Rint = 0.000
Radiation source: ISIS neutro spallation source	θmax = 85.8°, θmin = 8.5°
π–scans	h = −31→25
12392 measured reflections	k = −17→12
12392 independent reflections	l = −34→33
12392 reflections with I > 2σ(I)

Refinement

Refinement on F^2	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.072	(Δ/σ)max = 0.001
wR(F^2) = 0.192	Δρmax = 2.23 e Å^−3
S = 1.56	Δρmin = −2.17 e Å^−3
12392 reflections	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
722 parameters	Extinction coefficient: 0.00800 (18)
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 (10)
Secondary atom site location: difference Fourier map

Special details

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.

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 > 2sigma(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
Cl1	0.51127 (17)	0.7312 (3)	0.07729 (13)	0.0189 (4)
Cl2	0.48579 (19)	0.6348 (3)	0.48998 (13)	0.0197 (5)
Cl3	0.01521 (19)	0.7833 (4)	0.52907 (14)	0.0233 (5)
Cl4	−0.00914 (19)	0.8464 (4)	0.94374 (14)	0.0238 (5)
C1	0.2324 (2)	0.6093 (3)	0.19705 (17)	0.0087 (5)
C2	0.4036 (2)	0.5899 (3)	0.31464 (16)	0.0081 (5)
C3	0.3242 (2)	0.5258 (3)	0.16314 (16)	0.0083 (5)
C4	0.4779 (2)	0.6573 (4)	0.37315 (17)	0.0109 (5)
C5	0.1778 (2)	1.0086 (4)	0.83687 (17)	0.0092 (5)
C6	0.3217 (2)	0.3455 (4)	0.19683 (16)	0.0094 (5)
C7	0.4113 (2)	0.6076 (3)	0.21972 (15)	0.0076 (5)
C8	0.4908 (2)	0.6962 (4)	0.19002 (17)	0.0104 (5)
C9	0.0107 (2)	0.8373 (4)	0.82923 (18)	0.0125 (5)
C10	0.3408 (2)	0.8415 (5)	0.86874 (19)	0.0148 (6)
C11	0.1796 (2)	1.1746 (4)	0.78701 (17)	0.0091 (5)
C12	0.1613 (2)	0.6962 (4)	0.14458 (18)	0.0120 (5)
C13	0.2755 (2)	0.8966 (3)	0.71715 (17)	0.0092 (5)
C14	0.1893 (2)	0.9793 (4)	0.66043 (17)	0.0085 (5)
C15	0.2246 (2)	0.5949 (3)	0.28973 (16)	0.0082 (5)
C16	0.1802 (3)	1.4739 (4)	0.7714 (2)	0.0190 (6)
C17	0.1853 (2)	1.1590 (3)	0.69385 (17)	0.0080 (4)
C18	0.3533 (2)	0.8104 (4)	0.68315 (19)	0.0136 (6)
C19	0.0225 (2)	0.8076 (4)	0.64590 (19)	0.0133 (5)
C20	0.3091 (2)	0.4971 (3)	0.33897 (16)	0.0085 (5)
C21	0.3140 (2)	0.3303 (4)	0.28954 (17)	0.0099 (5)
C22	0.2690 (2)	0.9124 (3)	0.80984 (17)	0.0083 (4)
C23	−0.0546 (2)	0.7300 (4)	0.6871 (2)	0.0163 (6)
C24	0.0960 (2)	0.8956 (3)	0.69511 (17)	0.0083 (5)
C25	0.3158 (3)	0.0306 (4)	0.2750 (2)	0.0189 (6)
C26	0.0900 (2)	0.9107 (3)	0.79015 (17)	0.0087 (5)
C27	0.2059 (3)	0.9711 (4)	0.56063 (18)	0.0149 (6)
C28	0.4244 (3)	0.7363 (4)	0.7428 (2)	0.0175 (6)
C29	0.5556 (2)	0.7486 (4)	0.34094 (19)	0.0134 (5)
C30	0.5626 (2)	0.7683 (4)	0.25012 (19)	0.0133 (5)
C31	0.1779 (2)	1.3317 (4)	0.8259 (2)	0.0152 (6)
C32	0.1841 (3)	1.4579 (4)	0.6792 (2)	0.0176 (6)
C33	0.3240 (3)	0.0465 (4)	0.1822 (2)	0.0179 (6)
C34	0.0751 (2)	0.7597 (4)	0.2773 (2)	0.0153 (6)
C35	0.0834 (2)	0.7722 (4)	0.1849 (2)	0.0166 (6)
C36	0.1461 (2)	0.6690 (4)	0.33004 (18)	0.0118 (5)
C37	−0.0608 (2)	0.7450 (4)	0.7786 (2)	0.0162 (6)
C38	0.4187 (3)	0.7514 (4)	0.8353 (2)	0.0179 (6)
C39	0.3235 (3)	0.5321 (4)	0.06111 (18)	0.0153 (6)
C40	0.3270 (2)	0.2044 (4)	0.1433 (2)	0.0142 (6)
C41	0.1863 (2)	1.2999 (4)	0.64016 (19)	0.0123 (5)
C42	0.2907 (3)	0.4715 (4)	0.43782 (18)	0.0162 (6)
C43	0.1806 (3)	1.0352 (5)	0.93811 (19)	0.0178 (6)
C44	0.3114 (2)	0.1726 (4)	0.3285 (2)	0.0136 (5)
H10	0.3387 (6)	0.8541 (11)	0.9411 (4)	0.0323 (16)
H12	0.1635 (6)	0.7050 (10)	0.0720 (4)	0.0306 (15)
H16	0.1793 (7)	1.5947 (10)	0.8017 (6)	0.039 (2)
H18	0.3606 (6)	0.7986 (10)	0.6110 (4)	0.0297 (15)
H23	−0.1097 (7)	0.6574 (12)	0.6475 (5)	0.040 (2)
H25	0.3140 (7)	−0.0941 (10)	0.3045 (6)	0.0367 (18)
H2A	0.2111 (6)	0.8445 (12)	0.5366 (5)	0.0330 (16)
H2B	0.2749 (6)	1.0326 (11)	0.5493 (4)	0.0324 (17)
H2C	0.1471 (7)	1.0323 (12)	0.5193 (4)	0.0350 (18)
H28	0.4866 (6)	0.6669 (11)	0.7170 (6)	0.0343 (17)
H29	0.6111 (6)	0.8061 (11)	0.3882 (5)	0.0343 (18)
H30	0.6227 (6)	0.8379 (12)	0.2254 (5)	0.0341 (18)
H31	0.1747 (7)	1.3452 (10)	0.8981 (5)	0.0331 (17)
H32	0.1852 (7)	1.5691 (10)	0.6367 (6)	0.0372 (18)
H33	0.3281 (7)	−0.0653 (11)	0.1410 (7)	0.040 (2)
H34	0.0147 (6)	0.8173 (12)	0.3086 (6)	0.039 (2)
H35	0.0282 (6)	0.8410 (11)	0.1441 (5)	0.0334 (17)
H36	0.1387 (6)	0.6567 (10)	0.4018 (4)	0.0293 (15)
H37	−0.1218 (6)	0.6866 (11)	0.8113 (6)	0.0371 (19)
H38	0.4734 (7)	0.6943 (13)	0.8818 (5)	0.040 (2)
H3A	0.3211 (7)	0.6567 (11)	0.0352 (4)	0.0338 (17)
H3B	0.2564 (6)	0.4669 (11)	0.0326 (5)	0.0343 (18)
H3C	0.3879 (6)	0.4729 (11)	0.0358 (4)	0.0307 (16)
H40	0.3332 (6)	0.2149 (11)	0.0720 (4)	0.0327 (17)
H41	0.1889 (6)	1.2878 (10)	0.5683 (4)	0.0287 (15)
H4A	0.2178 (6)	0.4100 (11)	0.4403 (5)	0.0344 (18)
H4B	0.2863 (6)	0.5900 (10)	0.4726 (5)	0.0325 (17)
H4C	0.3480 (6)	0.3939 (11)	0.4722 (4)	0.0328 (17)
H4D	0.1189 (7)	1.1065 (11)	0.9584 (5)	0.0366 (19)
H4E	0.2484 (7)	1.1040 (12)	0.9578 (5)	0.0369 (19)
H4F	0.1845 (7)	0.9196 (11)	0.9761 (4)	0.0337 (18)
H44	0.3074 (6)	0.1588 (10)	0.4005 (4)	0.0289 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0201 (11)	0.0246 (12)	0.0126 (7)	−0.0060 (8)	0.0061 (7)	0.0059 (7)
Cl2	0.0210 (12)	0.0283 (13)	0.0093 (7)	−0.0039 (8)	−0.0036 (7)	−0.0029 (7)
Cl3	0.0195 (12)	0.0346 (14)	0.0149 (8)	−0.0049 (9)	−0.0042 (8)	−0.0120 (8)
Cl4	0.0222 (12)	0.0347 (14)	0.0153 (8)	−0.0035 (9)	0.0078 (8)	0.0103 (9)
C1	0.0099 (13)	0.0067 (12)	0.0093 (9)	0.0000 (8)	0.0006 (9)	0.0000 (8)
C2	0.0084 (13)	0.0078 (12)	0.0080 (9)	−0.0015 (8)	−0.0001 (8)	−0.0006 (8)
C3	0.0099 (13)	0.0086 (13)	0.0066 (9)	−0.0017 (9)	0.0013 (8)	0.0008 (8)
C4	0.0104 (13)	0.0124 (13)	0.0096 (9)	0.0017 (9)	−0.0017 (9)	−0.0026 (9)
C5	0.0106 (14)	0.0084 (13)	0.0086 (9)	−0.0004 (8)	0.0003 (9)	0.0002 (8)
C6	0.0109 (13)	0.0077 (12)	0.0097 (9)	−0.0016 (9)	0.0008 (9)	−0.0018 (9)
C7	0.0092 (12)	0.0072 (12)	0.0066 (8)	−0.0009 (8)	0.0013 (8)	0.0012 (8)
C8	0.0087 (13)	0.0114 (13)	0.0114 (10)	−0.0022 (9)	0.0034 (9)	0.0026 (9)
C9	0.0120 (14)	0.0109 (13)	0.0150 (11)	−0.0017 (10)	0.0036 (10)	0.0049 (10)
C10	0.0135 (15)	0.0170 (15)	0.0136 (10)	0.0032 (10)	−0.0011 (10)	0.0049 (10)
C11	0.0108 (13)	0.0068 (12)	0.0096 (9)	−0.0009 (8)	0.0005 (9)	−0.0012 (8)
C12	0.0106 (14)	0.0120 (14)	0.0131 (10)	0.0002 (9)	−0.0023 (9)	0.0046 (9)
C13	0.0087 (13)	0.0097 (13)	0.0092 (9)	0.0014 (9)	0.0010 (9)	0.0003 (8)
C14	0.0086 (13)	0.0092 (12)	0.0079 (9)	−0.0010 (9)	0.0010 (9)	0.0003 (8)
C15	0.0097 (13)	0.0073 (12)	0.0077 (9)	0.0004 (8)	0.0016 (8)	0.0015 (8)
C16	0.0199 (17)	0.0056 (14)	0.0319 (16)	−0.0008 (10)	0.0049 (13)	−0.0027 (12)
C17	0.0084 (12)	0.0054 (12)	0.0103 (9)	−0.0007 (8)	0.0010 (8)	0.0008 (8)
C18	0.0133 (15)	0.0117 (14)	0.0160 (11)	0.0030 (9)	0.0035 (10)	−0.0002 (10)
C19	0.0116 (14)	0.0128 (14)	0.0153 (11)	−0.0010 (10)	−0.0001 (10)	−0.0045 (10)
C20	0.0127 (14)	0.0079 (12)	0.0050 (8)	0.0008 (8)	0.0017 (8)	0.0020 (8)
C21	0.0122 (13)	0.0061 (12)	0.0115 (10)	−0.0006 (9)	0.0011 (9)	0.0023 (9)
C22	0.0072 (12)	0.0079 (12)	0.0097 (9)	0.0001 (8)	−0.0009 (8)	0.0012 (8)
C23	0.0103 (15)	0.0131 (15)	0.0252 (14)	−0.0050 (10)	−0.0010 (11)	−0.0031 (11)
C24	0.0078 (12)	0.0077 (12)	0.0093 (9)	−0.0014 (8)	−0.0008 (9)	−0.0011 (8)
C25	0.0163 (16)	0.0097 (15)	0.0303 (16)	−0.0001 (10)	−0.0005 (12)	0.0026 (12)
C26	0.0088 (13)	0.0065 (12)	0.0110 (10)	−0.0001 (8)	0.0027 (9)	0.0008 (8)
C27	0.0165 (16)	0.0214 (16)	0.0067 (9)	0.0013 (11)	0.0009 (9)	−0.0011 (9)
C28	0.0140 (16)	0.0161 (16)	0.0228 (13)	0.0033 (11)	0.0029 (11)	0.0016 (11)
C29	0.0090 (14)	0.0148 (15)	0.0161 (11)	−0.0025 (10)	−0.0016 (10)	−0.0034 (10)
C30	0.0086 (13)	0.0127 (14)	0.0186 (12)	−0.0063 (9)	0.0022 (10)	−0.0012 (10)
C31	0.0175 (16)	0.0088 (14)	0.0194 (12)	−0.0017 (10)	0.0011 (11)	−0.0046 (11)
C32	0.0148 (15)	0.0077 (14)	0.0306 (16)	−0.0003 (10)	0.0034 (12)	0.0055 (11)
C33	0.0131 (15)	0.0078 (14)	0.0326 (16)	−0.0012 (10)	0.0005 (12)	−0.0049 (12)
C34	0.0078 (14)	0.0139 (15)	0.0244 (13)	0.0027 (9)	0.0031 (11)	0.0007 (11)
C35	0.0106 (15)	0.0167 (16)	0.0221 (13)	0.0045 (10)	−0.0016 (11)	0.0045 (11)
C36	0.0092 (14)	0.0132 (14)	0.0135 (10)	0.0002 (9)	0.0037 (9)	−0.0011 (10)
C37	0.0118 (15)	0.0127 (15)	0.0242 (13)	−0.0039 (10)	0.0027 (11)	0.0024 (11)
C38	0.0126 (16)	0.0184 (17)	0.0223 (13)	0.0023 (11)	−0.0018 (11)	0.0073 (12)
C39	0.0197 (16)	0.0199 (16)	0.0062 (9)	−0.0038 (11)	0.0003 (9)	−0.0001 (9)
C40	0.0140 (14)	0.0101 (14)	0.0185 (12)	−0.0011 (10)	0.0005 (11)	−0.0056 (10)
C41	0.0103 (13)	0.0105 (13)	0.0157 (11)	0.0000 (9)	−0.0012 (10)	0.0073 (9)
C42	0.0191 (17)	0.0219 (16)	0.0080 (10)	−0.0013 (11)	0.0041 (10)	0.0041 (10)
C43	0.0221 (17)	0.0244 (17)	0.0072 (9)	−0.0029 (12)	0.0022 (10)	−0.0010 (10)
C44	0.0121 (14)	0.0067 (13)	0.0219 (12)	−0.0010 (9)	0.0004 (11)	0.0048 (10)
H10	0.034 (4)	0.044 (5)	0.018 (2)	0.002 (3)	0.000 (3)	0.006 (3)
H12	0.034 (4)	0.036 (4)	0.021 (2)	0.006 (3)	−0.001 (3)	0.008 (3)
H16	0.048 (6)	0.016 (4)	0.052 (5)	−0.001 (3)	0.005 (4)	−0.009 (3)
H18	0.029 (4)	0.034 (4)	0.027 (3)	0.007 (3)	0.009 (3)	−0.007 (3)
H23	0.039 (5)	0.038 (5)	0.043 (4)	−0.018 (4)	−0.005 (4)	−0.010 (4)
H25	0.034 (5)	0.017 (4)	0.058 (5)	0.002 (3)	0.000 (4)	0.008 (3)
H2A	0.030 (4)	0.043 (5)	0.026 (3)	0.002 (3)	0.000 (3)	−0.008 (3)
H2B	0.025 (4)	0.051 (5)	0.021 (3)	−0.009 (3)	0.005 (3)	0.002 (3)
H2C	0.038 (5)	0.049 (5)	0.018 (2)	0.011 (4)	−0.004 (3)	0.006 (3)
H28	0.023 (4)	0.033 (4)	0.048 (4)	0.014 (3)	0.008 (3)	0.001 (3)
H29	0.028 (4)	0.042 (5)	0.032 (3)	−0.019 (3)	−0.006 (3)	−0.012 (3)
H30	0.023 (4)	0.045 (5)	0.035 (3)	−0.019 (3)	0.007 (3)	0.003 (3)
H31	0.049 (5)	0.025 (4)	0.025 (3)	−0.001 (3)	−0.001 (3)	−0.010 (3)
H32	0.049 (5)	0.018 (4)	0.045 (4)	0.002 (3)	0.004 (4)	0.010 (3)
H33	0.038 (5)	0.022 (4)	0.060 (5)	−0.002 (3)	0.007 (4)	−0.016 (4)
H34	0.026 (4)	0.044 (5)	0.048 (4)	0.019 (3)	0.013 (3)	0.000 (4)
H35	0.022 (4)	0.038 (5)	0.039 (4)	0.008 (3)	−0.006 (3)	0.014 (3)
H36	0.033 (4)	0.037 (4)	0.019 (2)	0.001 (3)	0.010 (3)	0.000 (3)
H37	0.021 (4)	0.038 (5)	0.053 (4)	−0.011 (3)	0.013 (3)	0.006 (4)
H38	0.028 (5)	0.052 (6)	0.039 (4)	0.013 (4)	−0.007 (3)	0.013 (4)
H3A	0.049 (5)	0.032 (4)	0.020 (3)	0.001 (3)	0.000 (3)	0.013 (3)
H3B	0.030 (4)	0.051 (5)	0.020 (3)	−0.014 (3)	−0.009 (3)	−0.007 (3)
H3C	0.029 (4)	0.044 (4)	0.020 (3)	−0.001 (3)	0.009 (3)	−0.007 (3)
H40	0.046 (5)	0.031 (4)	0.022 (3)	−0.006 (3)	0.007 (3)	−0.011 (3)
H41	0.033 (4)	0.033 (4)	0.020 (2)	−0.003 (3)	−0.001 (3)	0.004 (3)
H4A	0.029 (4)	0.047 (5)	0.028 (3)	−0.011 (3)	0.005 (3)	0.013 (3)
H4B	0.039 (5)	0.035 (4)	0.025 (3)	−0.003 (3)	0.010 (3)	−0.006 (3)
H4C	0.033 (4)	0.046 (5)	0.018 (2)	0.005 (3)	−0.001 (3)	0.011 (3)
H4D	0.043 (5)	0.039 (5)	0.029 (3)	0.002 (3)	0.014 (3)	−0.008 (3)
H4E	0.040 (5)	0.048 (5)	0.022 (3)	−0.014 (4)	−0.005 (3)	−0.003 (3)
H4F	0.041 (5)	0.043 (5)	0.018 (3)	0.006 (3)	0.003 (3)	0.007 (3)
H44	0.036 (4)	0.029 (4)	0.022 (3)	−0.003 (3)	0.003 (3)	0.009 (3)

Geometric parameters (Å, º)

Cl1—C8	1.749 (3)	C12—C35	1.395 (4)
Cl2—C4	1.751 (3)	C13—C18	1.390 (4)
Cl3—C19	1.753 (3)	C13—C22	1.400 (3)
Cl4—C9	1.752 (3)	C13—C14	1.547 (4)
C1—C12	1.389 (4)	C14—C27	1.525 (3)
C1—C15	1.401 (3)	C14—C17	1.531 (4)
C1—C3	1.534 (4)	C14—C24	1.556 (4)
C2—C4	1.398 (4)	C15—C36	1.395 (4)
C2—C7	1.437 (3)	C15—C20	1.536 (4)
C2—C20	1.550 (4)	C16—C32	1.387 (5)
C3—C39	1.525 (4)	C16—C31	1.406 (5)
C3—C6	1.536 (4)	C17—C41	1.389 (4)
C3—C7	1.552 (4)	C18—C28	1.401 (5)
C4—C29	1.399 (4)	C19—C24	1.392 (4)
C5—C43	1.526 (4)	C19—C23	1.399 (4)
C5—C11	1.530 (4)	C20—C42	1.529 (3)
C5—C22	1.538 (4)	C20—C21	1.535 (4)
C5—C26	1.553 (4)	C21—C44	1.397 (4)
C6—C40	1.393 (4)	C23—C37	1.382 (4)
C6—C21	1.402 (3)	C24—C26	1.433 (3)
C7—C8	1.393 (4)	C25—C44	1.398 (5)
C8—C30	1.404 (4)	C25—C33	1.405 (5)
C9—C26	1.392 (4)	C28—C38	1.395 (4)
C9—C37	1.402 (5)	C29—C30	1.376 (4)
C10—C22	1.390 (4)	C32—C41	1.399 (5)
C10—C38	1.402 (5)	C33—C40	1.398 (5)
C11—C31	1.392 (4)	C34—C35	1.398 (4)
C11—C17	1.405 (3)	C34—C36	1.406 (5)
C12—C1—C15	120.1 (2)	C13—C14—C24	103.6 (2)
C12—C1—C3	125.7 (2)	C36—C15—C1	120.3 (3)
C15—C1—C3	114.2 (2)	C36—C15—C20	125.5 (2)
C4—C2—C7	118.7 (2)	C1—C15—C2	114.2 (2)
C4—C2—C20	127.9 (2)	C32—C16—C31	120.3 (3)
C7—C2—C20	113.4 (2)	C41—C17—C11	120.2 (3)
C39—C3—C1	111.5 (2)	C41—C17—C14	125.4 (2)
C39—C3—C6	111.1 (2)	C11—C17—C14	114.4 (2)
C1—C3—C6	105.5 (2)	C13—C18—C28	119.2 (3)
C39—C3—C7	118.8 (2)	C24—C19—C23	121.8 (3)
C1—C3—C7	104.0 (2)	C24—C19—Cl3	124.8 (2)
C6—C3—C7	104.8 (2)	C23—C19—Cl3	113.4 (3)
C2—C4—C29	121.2 (2)	C42—C20—C21	111.3 (2)
C2—C4—Cl2	125.1 (2)	C42—C20—C15	111.4 (2)
C29—C4—Cl2	113.7 (2)	C21—C20—C15	105.8 (2)
C43—C5—C11	111.1 (2)	C42—C20—C2	119.0 (2)
C43—C5—C22	111.5 (3)	C21—C20—C2	104.1 (2)
C11—C5—C22	105.7 (2)	C15—C20—C2	104.2 (2)
C43—C5—C26	118.8 (2)	C44—C21—C6	119.8 (3)
C11—C5—C26	105.1 (2)	C44—C21—C20	126.1 (2)
C22—C5—C26	103.6 (2)	C6—C21—C2	114.1 (2)
C40—C6—C21	120.5 (3)	C10—C22—C13	119.9 (3)
C40—C6—C03	125.3 (2)	C10—C22—C5	125.7 (2)
C21—C6—C03	114.3 (2)	C13—C22—C5	114.4 (2)
C8—C7—C2	118.5 (3)	C37—C23—C19	119.7 (3)
C8—C7—C3	128.5 (2)	C19—C24—C26	118.6 (2)
C2—C7—C3	113.0 (2)	C19—C24—C14	128.0 (2)
C7—C8—C30	121.8 (2)	C26—C24—C14	113.4 (2)
C7—C8—Cl1	124.6 (2)	C44—C25—C33	120.0 (3)
C30—C8—Cl1	113.6 (2)	C9—C26—C24	118.6 (3)
C26—C9—C037	121.7 (3)	C9—C26—C5	128.2 (2)
C26—C9—Cl4	124.6 (3)	C24—C26—C5	113.2 (2)
C37—C9—Cl4	113.6 (2)	C38—C28—C18	120.6 (3)
C22—C10—C38	120.0 (3)	C30—C29—C4	120.4 (3)
C31—C11—C17	119.9 (3)	C29—C30—C8	119.4 (2)
C31—C11—C5	126.0 (2)	C11—C31—C16	119.6 (3)
C17—C11—C5	114.1 (2)	C16—C32—C41	120.1 (3)
C1—C12—C35	119.7 (2)	C40—C33—C25	120.0 (3)
C18—C13—C22	120.6 (3)	C35—C34—C36	119.4 (3)
C18—C13—C14	125.5 (2)	C12—C35—C34	120.8 (3)
C22—C13—C14	113.9 (2)	C15—C36—C34	119.7 (2)
C27—C14—C17	111.8 (2)	C23—C37—C9	119.5 (3)
C27—C14—C13	111.1 (2)	C28—C38—C10	119.6 (3)
C17—C14—C13	105.6 (2)	C6—C4—C33	119.7 (3)
C27—C14—C24	119.1 (3)	C17—C41—C32	119.9 (3)
C17—C14—C24	104.6 (2)	C21—C44—C25	120.0 (3)

(DMAN_IAM_50)

Crystal data

C14H24Cl2N2O2	V = 1736.1 (3) Å^3
Mr = 323.25	Z = 4
a = 10.085 (1) Å	F(000) = 688
b = 9.811 (1) Å	Dx = 1.237 Mg m^−3
c = 17.915 (1) Å	Mo Kα radiation, λ = 0.71073 Å
α = 90°	µ = 0.38 mm^−1
β = 101.639 (1)°	T = 103 K
γ = 90°

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
3048 measured reflections	h = −11→11
3048 independent reflections	k = 0→11
2914 reflections with I > 2σ(I)	l = 0→21

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)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0539P)^2 + 0.1626P] where P = (Fo^2 + 2Fc^2)/3
S = 1.29	(Δ/σ)max = 1.060
3048 reflections	Δρmax = 0.30 e Å^−3
278 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0000 (11)

Special details

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.

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 > 2sigma(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
Cl1	0.01225 (3)	0.90091 (3)	0.668004 (16)	0.02395 (13)
Cl2	0.47729 (3)	0.90903 (2)	0.846019 (16)	0.02206 (13)
O1	0.13935 (10)	0.64942 (9)	0.74330 (5)	0.0261 (2)
O2	0.38277 (10)	0.65843 (9)	0.75261 (5)	0.0298 (2)
H1OA	0.1052 (18)	0.5825 (18)	0.7183 (10)	0.048 (5)*
H1OB	0.1063 (16)	0.7129 (19)	0.7240 (9)	0.037 (4)*
H2OA	0.4105 (18)	0.720 (2)	0.7769 (10)	0.049 (5)*
H2OB	0.4168 (17)	0.5916 (18)	0.7751 (10)	0.045 (5)*
H3O	0.262 (2)	0.653 (3)	0.7471 (11)	0.087 (8)*
N1	0.83472 (9)	0.84218 (8)	0.88253 (5)	0.0179 (2)
N2	0.72549 (8)	0.75189 (8)	0.99275 (5)	0.0165 (2)
C1	0.96674 (10)	0.79636 (10)	0.92487 (6)	0.0173 (2)
C2	1.08190 (11)	0.81882 (11)	0.89707 (6)	0.0214 (2)
C3	1.20943 (11)	0.77517 (11)	0.93765 (7)	0.0231 (2)
C4	1.21940 (11)	0.70843 (10)	1.00548 (6)	0.0208 (2)
C5	1.11341 (11)	0.61116 (11)	1.10609 (6)	0.0215 (2)
C6	1.00142 (12)	0.58391 (11)	1.13570 (7)	0.0240 (3)
C7	0.87278 (11)	0.62895 (11)	1.09748 (6)	0.0214 (2)
C8	0.85937 (10)	0.69919 (10)	1.03030 (6)	0.0168 (2)
C9	0.97243 (10)	0.72663 (10)	0.99567 (6)	0.0164 (2)
C10	1.10234 (10)	0.68137 (10)	1.03587 (6)	0.0182 (2)
C11	0.79242 (12)	0.76608 (13)	0.81008 (6)	0.0258 (3)
C12	0.83140 (12)	0.99127 (12)	0.86951 (8)	0.0304 (3)
C13	0.67590 (12)	0.86052 (12)	1.03882 (6)	0.0235 (3)
C14	0.62252 (11)	0.64164 (11)	0.97233 (7)	0.0226 (3)
H2N	0.7496 (17)	0.8022 (17)	0.9411 (10)	0.052 (4)*
H2	1.0740 (15)	0.8682 (15)	0.8481 (9)	0.037 (4)*
H3	1.2877 (14)	0.7915 (13)	0.9168 (8)	0.029 (3)*
H4	1.3024 (14)	0.6761 (13)	1.0336 (7)	0.022 (3)*
H5	1.2008 (14)	0.5847 (13)	1.1306 (8)	0.024 (3)*
H6	1.0109 (13)	0.5381 (14)	1.1817 (8)	0.027 (3)*
H7	0.7931 (15)	0.6124 (13)	1.1186 (8)	0.027 (3)*
H11A	0.7925 (15)	0.6649 (15)	0.8226 (8)	0.037 (4)*
H11B	0.8522 (16)	0.7840 (15)	0.7763 (9)	0.039 (4)*
H11C	0.7009 (14)	0.7933 (13)	0.7883 (8)	0.026 (3)*
H12A	0.8624 (15)	1.0395 (16)	0.9187 (9)	0.038 (4)*
H12B	0.8895 (15)	1.0159 (16)	0.8352 (9)	0.042 (4)*
H12C	0.7395 (14)	1.0152 (14)	0.8486 (8)	0.029 (3)*
H13A	0.6566 (14)	0.8207 (15)	1.0837 (9)	0.034 (4)*
H13B	0.7457 (14)	0.9293 (14)	1.0515 (8)	0.028 (3)*
H13C	0.5940 (14)	0.8995 (13)	1.0074 (8)	0.029 (3)*
H14A	0.6061 (14)	0.5952 (14)	1.0185 (9)	0.033 (4)*
H14B	0.6572 (14)	0.5766 (14)	0.9409 (8)	0.030 (3)*
H14C	0.5432 (14)	0.6826 (14)	0.9426 (8)	0.025 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02381 (19)	0.02056 (19)	0.02535 (19)	0.00013 (9)	−0.00008 (12)	0.00149 (9)
Cl2	0.02084 (19)	0.02018 (19)	0.02559 (19)	0.00120 (9)	0.00569 (12)	0.00269 (9)
O1	0.0365 (5)	0.0173 (4)	0.0224 (4)	0.0007 (4)	0.0012 (4)	−0.0004 (3)
O2	0.0354 (5)	0.0206 (5)	0.0305 (5)	−0.0004 (4)	−0.0005 (4)	0.0023 (4)
N1	0.0187 (5)	0.0166 (5)	0.0186 (4)	0.0014 (3)	0.0039 (3)	0.0019 (3)
N2	0.0171 (4)	0.0156 (4)	0.0177 (4)	0.0000 (3)	0.0055 (3)	−0.0013 (3)
C1	0.0193 (5)	0.0143 (5)	0.0188 (5)	0.0001 (4)	0.0046 (4)	−0.0015 (4)
C2	0.0234 (6)	0.0199 (5)	0.0225 (5)	0.0002 (4)	0.0083 (4)	0.0022 (4)
C3	0.0197 (5)	0.0225 (5)	0.0297 (6)	−0.0007 (4)	0.0108 (5)	0.0006 (4)
C4	0.0171 (5)	0.0180 (5)	0.0268 (6)	0.0009 (4)	0.0034 (4)	−0.0018 (4)
C5	0.0219 (6)	0.0213 (5)	0.0199 (5)	0.0037 (4)	0.0010 (4)	−0.0008 (4)
C6	0.0290 (6)	0.0258 (6)	0.0174 (6)	0.0024 (4)	0.0051 (5)	0.0035 (4)
C7	0.0236 (6)	0.0228 (5)	0.0193 (5)	−0.0004 (4)	0.0083 (4)	0.0000 (4)
C8	0.0179 (5)	0.0151 (5)	0.0175 (5)	0.0002 (4)	0.0040 (4)	−0.0032 (4)
C9	0.0194 (5)	0.0125 (4)	0.0175 (5)	−0.0008 (4)	0.0042 (4)	−0.0033 (4)
C10	0.0203 (5)	0.0146 (5)	0.0198 (5)	−0.0001 (4)	0.0040 (4)	−0.0035 (4)
C11	0.0230 (6)	0.0370 (7)	0.0171 (5)	0.0036 (5)	0.0032 (4)	−0.0016 (5)
C12	0.0236 (6)	0.0201 (6)	0.0479 (8)	0.0023 (5)	0.0087 (6)	0.0105 (5)
C13	0.0275 (6)	0.0219 (5)	0.0226 (6)	0.0048 (4)	0.0086 (5)	−0.0034 (4)
C14	0.0200 (6)	0.0203 (5)	0.0262 (6)	−0.0042 (4)	0.0017 (5)	0.0004 (5)

Geometric parameters (Å, º)

O1—H1OA	0.830 (19)	C5—C6	1.3675 (17)
O1—H1OB	0.756 (18)	C5—C10	1.4187 (15)
O1—H3O	1.22 (2)	C5—H5	0.939 (14)
O2—H2OA	0.77 (2)	C6—C7	1.4102 (16)
O2—H2OB	0.809 (19)	C6—H6	0.926 (14)
O2—H3O	1.21 (2)	C7—C8	1.3696 (15)
N1—C1	1.4637 (13)	C7—H7	0.968 (15)
N1—C12	1.4806 (14)	C8—C9	1.4294 (15)
N1—C11	1.4834 (14)	C9—C10	1.4324 (14)
N2—C8	1.4752 (13)	C11—H11A	1.017 (15)
N2—C14	1.4930 (13)	C11—H11B	0.953 (16)
N2—C13	1.4946 (13)	C11—H11C	0.964 (14)
N2—H2N	1.118 (17)	C12—H12A	0.994 (16)
C1—C2	1.3708 (15)	C12—H12B	0.962 (17)
C1—C9	1.4320 (14)	C12—H12C	0.956 (14)
C2—C3	1.4102 (16)	C13—H13A	0.948 (15)
C2—H2	0.992 (16)	C13—H13B	0.969 (14)
C3—C4	1.3663 (16)	C13—H13C	0.979 (15)
C3—H3	0.953 (14)	C14—H14A	0.986 (15)
C4—C10	1.4212 (15)	C14—H14B	0.963 (15)
C4—H4	0.941 (14)	C14—H14C	0.956 (14)
H1OA—O1—H1OB	107.9 (17)	C6—C7—H7	120.9 (8)
H1OA—O1—H3O	110.8 (16)	C7—C8—C9	122.02 (9)
H1OB—O1—H3O	110.6 (16)	C7—C8—N2	119.75 (9)
H2OA—O2—H2OB	106.8 (18)	C9—C8—N2	118.22 (9)
H2OA—O2—H3O	109.4 (16)	C8—C9—C10	116.88 (9)
H2OB—O2—H3O	108.8 (17)	C8—C9—C1	125.55 (9)
C1—N1—C12	111.98 (8)	C10—C9—C1	117.56 (9)
C1—N1—C11	111.71 (8)	C5—C10—C4	120.50 (10)
C12—N1—C11	111.47 (9)	C5—C10—C9	119.79 (10)
C8—N2—C14	112.65 (8)	C4—C10—C9	119.71 (9)
C8—N2—C13	112.05 (8)	N1—C11—H11A	108.1 (8)
C14—N2—C13	110.99 (8)	N1—C11—H11B	110.9 (9)
C8—N2—H2N	101.5 (9)	H11A—C11—H11B	110.3 (12)
C14—N2—H2N	112.0 (9)	N1—C11—H11C	107.3 (8)
C13—N2—H2N	107.2 (9)	H11A—C11—H11C	108.5 (11)
C2—C1—C9	120.87 (9)	H11B—C11—H11C	111.6 (12)
C2—C1—N1	120.73 (9)	N1—C12—H12A	109.7 (9)
C9—C1—N1	118.39 (9)	N1—C12—H12B	110.6 (9)
C1—C2—C3	121.02 (10)	H12A—C12—H12B	109.0 (13)
C1—C2—H2	118.5 (9)	N1—C12—H12C	107.1 (8)
C3—C2—H2	120.4 (9)	H12A—C12—H12C	109.7 (12)
C4—C3—C2	119.99 (10)	H12B—C12—H12C	110.8 (12)
C4—C3—H3	120.8 (8)	N2—C13—H13A	108.8 (9)
C2—C3—H3	119.3 (8)	N2—C13—H13B	108.6 (8)
C3—C4—C10	120.83 (10)	H13A—C13—H13B	110.6 (12)
C3—C4—H4	122.4 (8)	N2—C13—H13C	107.4 (8)
C10—C4—H4	116.7 (8)	H13A—C13—H13C	110.8 (12)
C6—C5—C10	121.03 (10)	H13B—C13—H13C	110.6 (11)
C6—C5—H5	122.4 (8)	N2—C14—H14A	110.8 (9)
C10—C5—H5	116.6 (8)	N2—C14—H14B	107.9 (8)
C5—C6—C7	120.08 (11)	H14A—C14—H14B	109.1 (11)
C5—C6—H6	119.7 (8)	N2—C14—H14C	107.1 (8)
C7—C6—H6	120.2 (8)	H14A—C14—H14C	113.4 (11)
C8—C7—C6	120.16 (10)	H14B—C14—H14C	108.4 (11)
C8—C7—H7	119.0 (8)
C12—N1—C1—C2	−58.76 (13)	C7—C8—C9—C10	−2.16 (14)
C11—N1—C1—C2	67.09 (12)	N2—C8—C9—C10	176.29 (8)
C12—N1—C1—C9	121.74 (10)	C7—C8—C9—C1	178.47 (10)
C11—N1—C1—C9	−112.41 (10)	N2—C8—C9—C1	−3.08 (14)
C9—C1—C2—C3	−0.63 (16)	C2—C1—C9—C8	179.24 (10)
N1—C1—C2—C3	179.88 (9)	N1—C1—C9—C8	−1.26 (14)
C1—C2—C3—C4	0.53 (17)	C2—C1—C9—C10	−0.13 (14)
C2—C3—C4—C10	0.35 (16)	N1—C1—C9—C10	179.37 (8)
C10—C5—C6—C7	−1.74 (17)	C6—C5—C10—C4	−179.65 (10)
C5—C6—C7—C8	0.50 (17)	C6—C5—C10—C9	1.01 (16)
C6—C7—C8—C9	1.50 (16)	C3—C4—C10—C5	179.55 (10)
C6—C7—C8—N2	−176.92 (9)	C3—C4—C10—C9	−1.11 (15)
C14—N2—C8—C7	−60.06 (12)	C8—C9—C10—C5	0.90 (14)
C13—N2—C8—C7	65.95 (12)	C1—C9—C10—C5	−179.68 (9)
C14—N2—C8—C9	121.46 (10)	C8—C9—C10—C4	−178.44 (9)
C13—N2—C8—C9	−112.54 (10)	C1—C9—C10—C4	0.98 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1OA···Cl2^i	0.830 (19)	2.128 (19)	2.9575 (9)	178.5 (17)
O1—H1OB···Cl1	0.756 (18)	2.219 (19)	2.9754 (10)	179.1 (17)
O2—H2OA···Cl2	0.77 (2)	2.25 (2)	3.0183 (10)	175.9 (18)
O2—H2OB···Cl1^i	0.809 (19)	2.181 (19)	2.9865 (10)	173.9 (16)
N2—H2N···N1	1.118 (17)	1.534 (17)	2.6029 (12)	157.5 (14)

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

(DMAN_IAM_80)

Crystal data

C14H24Cl2N2O2	V = 1736.1 (3) Å^3
Mr = 323.25	Z = 4
a = 10.085 (1) Å	F(000) = 688
b = 9.811 (1) Å	Dx = 1.237 Mg m^−3
c = 17.915 (1) Å	Mo Kα radiation, λ = 0.71073 Å
α = 90°	µ = 0.38 mm^−1
β = 101.639 (1)°	T = 103 K
γ = 90°

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 40.0°, θmin = 2.2°
10756 measured reflections	h = −18→17
10756 independent reflections	k = 0→17
9608 reflections with I > 2σ(I)	l = 0→32

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0539P)^2 + 0.1626P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 14.561
10756 reflections	Δρmax = 0.63 e Å^−3
278 parameters	Δρmin = −1.00 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0000 (11)

Special details

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.

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 > 2sigma(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
Cl1	0.012259 (17)	0.900810 (16)	0.667986 (10)	0.02334 (4)
Cl2	0.477152 (15)	0.908958 (15)	0.846026 (9)	0.02149 (4)
O1	0.13898 (7)	0.64943 (5)	0.74309 (3)	0.02548 (9)
O2	0.38287 (7)	0.65850 (6)	0.75280 (4)	0.02958 (11)
H1OA	0.1034 (17)	0.5802 (17)	0.7177 (10)	0.055 (5)*
H1OB	0.1017 (15)	0.7151 (17)	0.7228 (9)	0.047 (4)*
H2OA	0.4127 (17)	0.7207 (19)	0.7791 (10)	0.057 (5)*
H2OB	0.4167 (17)	0.5884 (17)	0.7759 (10)	0.052 (5)*
H3O	0.260 (2)	0.653 (3)	0.7470 (11)	0.094 (8)*
N1	0.83484 (5)	0.84210 (5)	0.88241 (3)	0.01693 (7)
N2	0.72550 (5)	0.75178 (5)	0.99272 (3)	0.01537 (7)
C1	0.96623 (5)	0.79635 (5)	0.92480 (3)	0.01597 (8)
C2	1.08177 (6)	0.81887 (6)	0.89682 (4)	0.02035 (9)
C3	1.20957 (6)	0.77527 (7)	0.93746 (4)	0.02217 (10)
C4	1.21960 (6)	0.70838 (6)	1.00559 (4)	0.02000 (9)
C5	1.11375 (6)	0.61114 (7)	1.10614 (3)	0.02047 (9)
C6	1.00142 (7)	0.58375 (7)	1.13585 (4)	0.02314 (10)
C7	0.87252 (6)	0.62885 (7)	1.09753 (3)	0.02042 (9)
C8	0.85910 (5)	0.69927 (5)	1.03015 (3)	0.01551 (8)
C9	0.97239 (5)	0.72662 (5)	0.99564 (3)	0.01480 (7)
C10	1.10230 (5)	0.68142 (5)	1.03583 (3)	0.01665 (8)
C11	0.79225 (7)	0.76588 (8)	0.81014 (4)	0.02549 (11)
C12	0.83123 (8)	0.99092 (7)	0.86929 (6)	0.03024 (14)
C13	0.67598 (7)	0.86026 (7)	1.03869 (4)	0.02321 (10)
C14	0.62281 (6)	0.64179 (6)	0.97235 (4)	0.02177 (10)
H2N	0.7481 (16)	0.8013 (16)	0.9404 (9)	0.052 (4)*
H2	1.0742 (15)	0.8689 (14)	0.8461 (8)	0.040 (3)*
H3	1.2913 (14)	0.7906 (14)	0.9159 (8)	0.036 (3)*
H4	1.3043 (12)	0.6761 (13)	1.0338 (7)	0.028 (3)*
H5	1.2033 (13)	0.5821 (12)	1.1308 (7)	0.030 (3)*
H6	1.0111 (13)	0.5372 (14)	1.1829 (7)	0.034 (3)*
H7	0.7909 (14)	0.6124 (13)	1.1183 (8)	0.033 (3)*
H11A	0.7921 (14)	0.6662 (14)	0.8219 (8)	0.036 (3)*
H11B	0.8535 (15)	0.7831 (15)	0.7757 (9)	0.046 (4)*
H11C	0.6994 (13)	0.7945 (13)	0.7881 (8)	0.033 (3)*
H12A	0.8633 (15)	1.0408 (16)	0.9183 (9)	0.045 (4)*
H12B	0.8885 (14)	1.0164 (15)	0.8333 (9)	0.044 (4)*
H12C	0.7391 (12)	1.0137 (13)	0.8473 (7)	0.032 (3)*
H13A	0.6569 (14)	0.8222 (15)	1.0847 (8)	0.039 (3)*
H13B	0.7447 (13)	0.9260 (13)	1.0521 (8)	0.031 (3)*
H13C	0.5940 (13)	0.8989 (13)	1.0081 (8)	0.032 (3)*
H14A	0.6067 (14)	0.5954 (13)	1.0181 (8)	0.036 (3)*
H14B	0.6566 (13)	0.5784 (13)	0.9398 (8)	0.030 (3)*
H14C	0.5450 (12)	0.6811 (12)	0.9423 (7)	0.027 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02333 (7)	0.02015 (6)	0.02451 (7)	0.00010 (4)	−0.00003 (5)	0.00156 (4)
Cl2	0.02014 (6)	0.02007 (6)	0.02485 (7)	0.00123 (4)	0.00591 (5)	0.00282 (4)
O1	0.0343 (3)	0.01870 (18)	0.02177 (19)	0.00026 (16)	0.00182 (17)	−0.00069 (14)
O2	0.0342 (3)	0.0216 (2)	0.0302 (2)	−0.00044 (18)	0.0001 (2)	0.00285 (18)
N1	0.01750 (17)	0.01660 (17)	0.01726 (16)	0.00123 (13)	0.00483 (13)	0.00235 (13)
N2	0.01563 (16)	0.01527 (16)	0.01609 (16)	−0.00034 (12)	0.00532 (13)	−0.00131 (12)
C1	0.01620 (18)	0.01590 (17)	0.01678 (18)	0.00009 (14)	0.00567 (14)	0.00094 (14)
C2	0.0189 (2)	0.0222 (2)	0.0219 (2)	0.00045 (17)	0.00883 (17)	0.00387 (17)
C3	0.0172 (2)	0.0239 (2)	0.0273 (3)	0.00054 (17)	0.00918 (18)	0.00332 (19)
C4	0.01596 (19)	0.0200 (2)	0.0245 (2)	0.00072 (16)	0.00519 (17)	0.00068 (17)
C5	0.0205 (2)	0.0227 (2)	0.0177 (2)	0.00277 (17)	0.00272 (17)	0.00168 (17)
C6	0.0243 (2)	0.0283 (3)	0.0172 (2)	0.0031 (2)	0.00524 (18)	0.00518 (18)
C7	0.0212 (2)	0.0247 (2)	0.01665 (19)	0.00099 (18)	0.00681 (16)	0.00338 (17)
C8	0.01620 (18)	0.01639 (18)	0.01468 (17)	−0.00024 (14)	0.00488 (14)	−0.00029 (13)
C9	0.01568 (17)	0.01431 (16)	0.01502 (16)	−0.00055 (13)	0.00456 (14)	−0.00067 (13)
C10	0.01636 (18)	0.01628 (18)	0.01745 (18)	0.00034 (14)	0.00377 (15)	−0.00059 (14)
C11	0.0236 (2)	0.0357 (3)	0.0168 (2)	0.0036 (2)	0.00324 (18)	−0.0025 (2)
C12	0.0235 (3)	0.0188 (2)	0.0490 (4)	0.00237 (19)	0.0087 (3)	0.0105 (3)
C13	0.0268 (3)	0.0217 (2)	0.0224 (2)	0.00485 (19)	0.0081 (2)	−0.00456 (18)
C14	0.0200 (2)	0.0195 (2)	0.0247 (2)	−0.00473 (17)	0.00209 (18)	0.00050 (18)

Geometric parameters (Å, º)

O1—H1OA	0.855 (17)	C5—C6	1.3719 (9)
O1—H1OB	0.796 (17)	C5—C10	1.4202 (8)
O1—H3O	1.21 (2)	C5—H5	0.965 (13)
O2—H2OA	0.792 (19)	C6—C7	1.4131 (9)
O2—H2OB	0.839 (17)	C6—H6	0.947 (13)
O2—H3O	1.22 (2)	C7—C8	1.3737 (8)
N1—C1	1.4587 (7)	C7—H7	0.982 (14)
N1—C12	1.4782 (8)	C8—C9	1.4299 (7)
N1—C11	1.4817 (8)	C9—C10	1.4321 (8)
N2—C8	1.4717 (7)	C11—H11A	1.001 (14)
N2—C14	1.4892 (8)	C11—H11B	0.971 (15)
N2—C13	1.4921 (7)	C11—H11C	0.981 (13)
N2—H2N	1.120 (16)	C12—H12A	1.000 (16)
C1—C2	1.3760 (8)	C12—H12B	0.981 (15)
C1—C9	1.4321 (7)	C12—H12C	0.960 (12)
C2—C3	1.4126 (9)	C13—H13A	0.959 (14)
C2—H2	1.022 (14)	C13—H13B	0.942 (13)
C3—C4	1.3714 (9)	C13—H13C	0.972 (13)
C3—H3	0.990 (13)	C14—H14A	0.980 (14)
C4—C10	1.4217 (8)	C14—H14B	0.960 (13)
C4—H4	0.954 (13)	C14—H14C	0.940 (12)
H1OA—O1—H1OB	107.0 (16)	C6—C7—H7	121.6 (8)
H1OA—O1—H3O	111.5 (16)	C7—C8—C9	121.92 (5)
H1OB—O1—H3O	112.4 (16)	C7—C8—N2	119.69 (5)
H2OA—O2—H2OB	105.7 (17)	C9—C8—N2	118.38 (4)
H2OA—O2—H3O	109.9 (16)	C8—C9—C10	117.02 (5)
H2OB—O2—H3O	108.1 (16)	C8—C9—C1	125.25 (5)
C1—N1—C12	112.17 (5)	C10—C9—C1	117.72 (5)
C1—N1—C11	111.86 (5)	C5—C10—C4	120.22 (5)
C12—N1—C11	111.47 (6)	C5—C10—C9	119.91 (5)
C8—N2—C14	112.67 (4)	C4—C10—C9	119.86 (5)
C8—N2—C13	112.08 (4)	N1—C11—H11A	108.7 (8)
C14—N2—C13	111.01 (5)	N1—C11—H11B	111.0 (9)
C8—N2—H2N	102.2 (8)	H11A—C11—H11B	109.4 (12)
C14—N2—H2N	111.0 (8)	N1—C11—H11C	107.0 (8)
C13—N2—H2N	107.5 (8)	H11A—C11—H11C	108.8 (11)
C2—C1—C9	120.73 (5)	H11B—C11—H11C	111.8 (12)
C2—C1—N1	120.53 (5)	N1—C12—H12A	110.5 (9)
C9—C1—N1	118.74 (4)	N1—C12—H12B	111.0 (9)
C1—C2—C3	121.01 (5)	H12A—C12—H12B	108.8 (12)
C1—C2—H2	118.9 (8)	N1—C12—H12C	106.6 (8)
C3—C2—H2	120.0 (8)	H12A—C12—H12C	111.2 (11)
C4—C3—C2	119.96 (5)	H12B—C12—H12C	108.7 (11)
C4—C3—H3	120.2 (8)	N2—C13—H13A	110.2 (9)
C2—C3—H3	119.9 (8)	N2—C13—H13B	108.6 (8)
C3—C4—C10	120.70 (5)	H13A—C13—H13B	108.2 (12)
C3—C4—H4	121.8 (8)	N2—C13—H13C	108.0 (8)
C10—C4—H4	117.5 (7)	H13A—C13—H13C	109.9 (12)
C6—C5—C10	120.89 (5)	H13B—C13—H13C	112.0 (11)
C6—C5—H5	122.3 (8)	N2—C14—H14A	110.8 (8)
C10—C5—H5	116.8 (8)	N2—C14—H14B	107.7 (8)
C5—C6—C7	120.07 (5)	H14A—C14—H14B	110.3 (11)
C5—C6—H6	119.7 (8)	N2—C14—H14C	107.6 (7)
C7—C6—H6	120.2 (8)	H14A—C14—H14C	114.1 (11)
C8—C7—C6	120.15 (5)	H14B—C14—H14C	106.0 (11)
C8—C7—H7	118.3 (8)
C12—N1—C1—C2	−58.84 (8)	C7—C8—C9—C10	−2.14 (8)
C11—N1—C1—C2	67.27 (7)	N2—C8—C9—C10	176.28 (4)
C12—N1—C1—C9	121.70 (6)	C7—C8—C9—C1	178.46 (5)
C11—N1—C1—C9	−112.19 (6)	N2—C8—C9—C1	−3.12 (8)
C9—C1—C2—C3	−0.68 (9)	C2—C1—C9—C8	179.30 (5)
N1—C1—C2—C3	179.87 (5)	N1—C1—C9—C8	−1.25 (8)
C1—C2—C3—C4	0.54 (10)	C2—C1—C9—C10	−0.10 (8)
C2—C3—C4—C10	0.39 (10)	N1—C1—C9—C10	179.36 (5)
C10—C5—C6—C7	−1.76 (10)	C6—C5—C10—C4	−179.65 (6)
C5—C6—C7—C8	0.52 (10)	C6—C5—C10—C9	1.03 (9)
C6—C7—C8—C9	1.48 (9)	C3—C4—C10—C5	179.51 (6)
C6—C7—C8—N2	−176.92 (5)	C3—C4—C10—C9	−1.17 (9)
C14—N2—C8—C7	−60.09 (7)	C8—C9—C10—C5	0.89 (8)
C13—N2—C8—C7	65.97 (7)	C1—C9—C10—C5	−179.67 (5)
C14—N2—C8—C9	121.45 (5)	C8—C9—C10—C4	−178.44 (5)
C13—N2—C8—C9	−112.48 (5)	C1—C9—C10—C4	1.01 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1OA···Cl2^i	0.855 (17)	2.100 (17)	2.9550 (6)	177.8 (16)
O1—H1OB···Cl1	0.796 (17)	2.177 (17)	2.9720 (6)	176.4 (15)
O2—H2OA···Cl2	0.792 (19)	2.227 (19)	3.0151 (7)	173.6 (17)
O2—H2OB···Cl1^i	0.839 (17)	2.149 (17)	2.9865 (6)	175.3 (16)
O1—H3O···O2	1.21 (2)	1.22 (2)	2.4321 (10)	178 (2)
N2—H2N···N1	1.120 (16)	1.540 (16)	2.6050 (7)	156.5 (14)

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

(DMAN_N_100)

Crystal data

2(Cl)·H5O2·C14H19N2	Z = 4
Mr = 323.26	F(000) = 211.1520
Monoclinic, P21/n	Dx = 1.237 Mg m^−3
a = 10.085 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.811 (1) Å	µ = 0.20 mm^−1
c = 17.915 (1) Å	T = 100 K
β = 101.639 (1)°	5 × 3 × 1 mm
V = 1736.1 (3) Å^3

Data collection

11288 measured reflections	θmax = 49.2°, θmin = 2.2°
3189 independent reflections	h = −17→17
3170 reflections with I ≥ 2u(I)	k = −10→16
Rint = 0.126	l = −33→34

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.078	All H-atom parameters refined
wR(F^2) = 0.288	w = 1/[σ^2(Fo^2) + (0.1504P)^2 + 26.730P] where P = (Fo^2 + 2Fc^2)/3
S = 1.51	(Δ/σ)max = 0.036
3189 reflections	Δρmax = 2.70 e Å^−3
397 parameters	Δρmin = −2.58 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl1	0.0122 (3)	0.9001 (4)	0.66795 (18)	0.0213 (7)
Cl2	0.4771 (3)	0.9091 (4)	0.84604 (18)	0.0190 (7)
O1	0.1388 (6)	0.6504 (8)	0.7428 (3)	0.0234 (12)
O2	0.3829 (7)	0.6592 (8)	0.7530 (4)	0.0284 (14)
H1a	0.0992 (12)	0.5694 (12)	0.7118 (6)	0.030 (2)
H1b	0.0936 (13)	0.7335 (14)	0.7183 (6)	0.035 (3)
H2a	0.4203 (13)	0.7409 (15)	0.7830 (7)	0.039 (3)
H2b	0.4232 (13)	0.5770 (13)	0.7801 (7)	0.035 (2)
H1c	0.2595 (14)	0.6552 (14)	0.7486 (6)	0.038 (3)
N1	0.8348 (3)	0.8423 (4)	0.88226 (16)	0.0149 (6)
N2	0.7253 (3)	0.7517 (4)	0.99269 (15)	0.0132 (6)
C1	0.9657 (4)	0.7962 (5)	0.9247 (2)	0.0136 (8)
C2	1.0824 (5)	0.8186 (6)	0.8968 (2)	0.0190 (10)
C3	1.2095 (5)	0.7749 (6)	0.9375 (3)	0.0207 (10)
C4	1.2195 (4)	0.7084 (6)	1.0058 (3)	0.0175 (9)
C5	1.1134 (5)	0.6116 (6)	1.1060 (2)	0.0176 (9)
C6	1.0006 (5)	0.5833 (6)	1.1361 (2)	0.0208 (11)
C7	0.8728 (4)	0.6287 (5)	1.0975 (2)	0.0160 (9)
C8	0.8597 (4)	0.6994 (5)	1.0303 (2)	0.0132 (8)
C9	0.9723 (4)	0.7270 (5)	0.9954 (2)	0.0114 (8)
C10	1.1020 (4)	0.6814 (5)	1.0357 (2)	0.0140 (8)
C11	0.7927 (5)	0.7651 (8)	0.8102 (2)	0.0245 (13)
C12	0.8311 (5)	0.9907 (7)	0.8694 (4)	0.0273 (12)
C13	0.6762 (5)	0.8600 (6)	1.0384 (3)	0.0212 (10)
C14	0.6236 (5)	0.6417 (6)	0.9729 (3)	0.0192 (9)
H1	0.7508 (11)	0.8012 (13)	0.9379 (6)	0.031 (2)
H2	1.0741 (12)	0.8702 (15)	0.8425 (6)	0.037 (3)
H3	1.2993 (10)	0.7972 (16)	0.9148 (7)	0.039 (3)
H4	1.3184 (10)	0.6766 (15)	1.0387 (6)	0.034 (3)
H5	1.2163 (10)	0.5810 (16)	1.1361 (6)	0.036 (3)
H6	1.0107 (12)	0.5292 (17)	1.1894 (6)	0.042 (3)
H7	0.7848 (10)	0.6103 (16)	1.1223 (6)	0.038 (3)
H11a	0.7937 (17)	0.6580 (19)	0.8225 (7)	0.049 (3)
H11b	0.8583 (14)	0.784 (2)	0.7705 (6)	0.056 (5)
H11c	0.6890 (12)	0.7954 (18)	0.7845 (7)	0.044 (3)
H12a	0.8620 (18)	1.0428 (18)	0.9231 (11)	0.059 (4)
H12b	0.8964 (14)	1.0198 (19)	0.8307 (12)	0.064 (5)
H12c	0.7277 (12)	1.0200 (16)	0.8445 (9)	0.046 (3)
H13a	0.6499 (15)	0.8150 (17)	1.0890 (6)	0.046 (4)
H13b	0.7533 (14)	0.9379 (16)	1.0543 (8)	0.047 (3)
H13c	0.5868 (13)	0.9041 (17)	1.0040 (7)	0.043 (3)
H14a	0.6026 (13)	0.5943 (17)	1.0242 (7)	0.046 (3)
H14b	0.6598 (14)	0.5657 (15)	0.9369 (8)	0.043 (3)
H14c	0.5305 (12)	0.6896 (16)	0.9402 (8)	0.041 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0219 (14)	0.021 (2)	0.0196 (12)	−0.0001 (13)	0.0005 (10)	0.0013 (13)
Cl2	0.0154 (12)	0.022 (2)	0.0204 (11)	0.0007 (12)	0.0046 (9)	0.0022 (13)
O1	0.032 (3)	0.022 (4)	0.0144 (19)	0.002 (3)	0.0015 (18)	−0.002 (2)
O2	0.034 (3)	0.023 (4)	0.025 (3)	−0.003 (3)	−0.000 (2)	0.001 (3)
H1a	0.041 (6)	0.017 (6)	0.032 (5)	−0.004 (4)	0.007 (4)	−0.000 (4)
H1b	0.045 (6)	0.028 (7)	0.031 (5)	0.010 (5)	0.005 (4)	−0.005 (5)
H2a	0.045 (6)	0.033 (8)	0.039 (5)	−0.010 (5)	0.006 (5)	−0.003 (5)
H2b	0.047 (6)	0.023 (7)	0.034 (5)	0.002 (5)	0.004 (4)	0.001 (5)
H1c	0.058 (7)	0.027 (7)	0.026 (4)	0.009 (6)	0.002 (4)	0.004 (4)
N1	0.0155 (12)	0.0181 (18)	0.0115 (10)	0.0025 (12)	0.0039 (8)	0.0030 (11)
N2	0.0118 (11)	0.0179 (18)	0.0107 (9)	−0.0001 (10)	0.0045 (8)	−0.0025 (10)
C1	0.0115 (16)	0.018 (2)	0.0122 (14)	0.0013 (15)	0.0051 (11)	0.0004 (15)
C2	0.0138 (18)	0.027 (3)	0.0179 (16)	0.0012 (16)	0.0074 (13)	0.0043 (17)
C3	0.0163 (18)	0.026 (3)	0.0223 (18)	−0.0004 (18)	0.0099 (14)	0.0028 (18)
C4	0.0123 (17)	0.019 (3)	0.0218 (18)	0.0004 (16)	0.0057 (13)	−0.0014 (17)
C5	0.0176 (18)	0.023 (3)	0.0120 (15)	0.0026 (16)	0.0016 (13)	0.0022 (16)
C6	0.0184 (19)	0.032 (3)	0.0130 (15)	0.0050 (19)	0.0048 (13)	0.0082 (17)
C7	0.0182 (18)	0.019 (3)	0.0119 (14)	0.0019 (16)	0.0060 (13)	0.0045 (15)
C8	0.0146 (17)	0.017 (2)	0.0084 (13)	−0.0020 (15)	0.0032 (11)	−0.0001 (14)
C9	0.0131 (16)	0.012 (2)	0.0101 (13)	−0.0006 (13)	0.0038 (11)	0.0007 (13)
C10	0.0105 (16)	0.019 (3)	0.0127 (14)	0.0008 (15)	0.0034 (11)	−0.0013 (14)
C11	0.020 (2)	0.041 (4)	0.0122 (15)	0.007 (2)	0.0030 (13)	−0.0029 (19)
C12	0.019 (2)	0.020 (3)	0.043 (3)	0.0012 (19)	0.007 (2)	0.013 (2)
C13	0.0194 (19)	0.027 (3)	0.0193 (17)	0.0072 (19)	0.0080 (15)	−0.0041 (18)
C14	0.0174 (18)	0.020 (3)	0.0195 (17)	−0.0048 (17)	0.0032 (14)	0.0001 (17)
H1	0.029 (5)	0.034 (7)	0.028 (4)	0.001 (4)	0.003 (3)	−0.003 (4)
H2	0.040 (6)	0.047 (9)	0.029 (4)	−0.004 (5)	0.017 (4)	0.015 (5)
H3	0.017 (4)	0.053 (9)	0.051 (6)	0.001 (4)	0.017 (4)	0.018 (6)
H4	0.016 (4)	0.048 (8)	0.037 (5)	0.005 (4)	0.002 (3)	0.006 (5)
H5	0.022 (4)	0.057 (9)	0.028 (4)	0.001 (5)	0.001 (3)	0.007 (5)
H6	0.034 (5)	0.069 (10)	0.023 (4)	0.008 (6)	0.007 (4)	0.020 (5)
H7	0.023 (4)	0.065 (9)	0.029 (4)	0.001 (5)	0.013 (3)	0.015 (5)
H11a	0.067 (9)	0.041 (10)	0.036 (6)	0.006 (7)	0.008 (6)	−0.014 (6)
H11b	0.042 (7)	0.102 (15)	0.027 (5)	−0.000 (7)	0.015 (4)	−0.009 (6)
H11c	0.030 (5)	0.069 (11)	0.032 (5)	0.006 (5)	0.000 (4)	−0.002 (6)
H12a	0.059 (9)	0.031 (9)	0.081 (11)	0.000 (7)	0.003 (8)	−0.010 (8)
H12b	0.040 (7)	0.050 (11)	0.112 (14)	0.011 (6)	0.037 (8)	0.052 (10)
H12c	0.027 (5)	0.039 (8)	0.068 (8)	0.012 (5)	0.003 (5)	0.006 (7)
H13a	0.061 (8)	0.059 (10)	0.027 (4)	0.015 (7)	0.027 (5)	−0.001 (5)
H13b	0.048 (7)	0.036 (9)	0.055 (7)	−0.003 (6)	0.006 (6)	−0.024 (6)
H13c	0.037 (6)	0.049 (9)	0.040 (5)	0.022 (6)	0.002 (4)	0.002 (6)
H14a	0.043 (6)	0.056 (10)	0.038 (5)	−0.015 (6)	0.006 (5)	0.017 (6)
H14b	0.054 (8)	0.028 (8)	0.049 (7)	−0.004 (6)	0.011 (6)	−0.016 (5)
H14c	0.031 (5)	0.040 (8)	0.048 (6)	−0.007 (5)	−0.004 (4)	0.005 (6)

Geometric parameters (Å, º)

O1—H1a	1.006 (14)	C5—C6	1.381 (7)
O1—H1b	0.992 (15)	C5—C10	1.419 (6)
O1—H1c	1.201 (16)	C5—H5	1.110 (11)
O2—H2a	0.995 (16)	C6—C7	1.406 (6)
O2—H2b	0.986 (16)	C6—H6	1.080 (11)
O2—H1c	1.232 (16)	C7—C8	1.373 (6)
N1—C1	1.456 (5)	C7—H7	1.084 (10)
N1—C11	1.483 (6)	C8—C9	1.428 (5)
N1—C12	1.474 (8)	C9—C10	1.432 (6)
N1—H1	1.488 (11)	C11—H11a	1.07 (2)
N2—C8	1.478 (5)	C11—H11b	1.080 (13)
N2—C13	1.486 (6)	C11—H11c	1.096 (13)
N2—C14	1.482 (6)	C12—H12a	1.08 (2)
N2—H1	1.170 (11)	C12—H12b	1.086 (15)
C1—C2	1.386 (6)	C12—H12c	1.087 (12)
C1—C9	1.428 (6)	C13—H13a	1.088 (13)
C2—C3	1.407 (7)	C13—H13b	1.086 (16)
C2—H2	1.086 (11)	C13—H13c	1.075 (12)
C3—C4	1.373 (7)	C14—H14a	1.089 (13)
C3—H3	1.086 (10)	C14—H14b	1.095 (15)
C4—C10	1.420 (6)	C14—H14c	1.106 (14)
C4—H4	1.096 (11)
H1b—O1—H1a	108.0 (11)	C8—C7—C6	120.5 (4)
H1c—O1—H1a	111.2 (11)	H7—C7—C6	119.4 (7)
H1c—O1—H1b	112.0 (12)	H7—C7—C8	120.1 (7)
H2b—O2—H2a	108.6 (12)	C7—C8—N2	119.5 (3)
H1c—O2—H2a	109.2 (12)	C9—C8—N2	118.1 (3)
H1c—O2—H2b	108.5 (12)	C9—C8—C7	122.3 (4)
O2—H1c—O1	178.7 (11)	C8—C9—C1	125.4 (4)
C11—N1—C1	111.5 (3)	C10—C9—C1	118.0 (3)
C12—N1—C1	112.4 (4)	C10—C9—C8	116.6 (4)
C12—N1—C11	112.0 (4)	C5—C10—C4	120.1 (4)
H1—N1—C1	98.4 (5)	C9—C10—C4	119.9 (4)
H1—N1—C11	110.0 (5)	C9—C10—C5	120.0 (4)
H1—N1—C12	111.9 (6)	H11a—C11—N1	109.3 (8)
C13—N2—C8	112.0 (3)	H11b—C11—N1	112.4 (10)
C14—N2—C8	112.5 (4)	H11b—C11—H11a	108.6 (14)
C14—N2—C13	111.2 (3)	H11c—C11—N1	108.0 (9)
H1—N2—C8	101.0 (6)	H11c—C11—H11a	108.7 (14)
H1—N2—C13	108.7 (7)	H11c—C11—H11b	109.7 (11)
H1—N2—C14	111.1 (6)	H12a—C12—N1	109.6 (11)
C2—C1—N1	120.6 (4)	H12b—C12—N1	111.1 (11)
C9—C1—N1	119.1 (3)	H12b—C12—H12a	110.0 (17)
C9—C1—C2	120.3 (4)	H12c—C12—N1	108.5 (10)
C3—C2—C1	121.1 (4)	H12c—C12—H12a	108.7 (13)
H2—C2—C1	118.7 (7)	H12c—C12—H12b	108.9 (13)
H2—C2—C3	120.2 (7)	H13a—C13—N2	109.5 (9)
C4—C3—C2	120.1 (4)	H13b—C13—N2	110.3 (8)
H3—C3—C2	119.1 (8)	H13b—C13—H13a	110.5 (13)
H3—C3—C4	120.7 (8)	H13c—C13—N2	107.8 (8)
C10—C4—C3	120.5 (4)	H13c—C13—H13a	108.8 (11)
H4—C4—C3	120.7 (7)	H13c—C13—H13b	109.8 (14)
H4—C4—C10	118.7 (7)	H14a—C14—N2	110.6 (8)
C10—C5—C6	121.2 (4)	H14b—C14—N2	109.8 (8)
H5—C5—C6	121.2 (7)	H14b—C14—H14a	110.5 (13)
H5—C5—C10	117.5 (7)	H14c—C14—N2	106.8 (8)
C7—C6—C5	119.4 (4)	H14c—C14—H14a	109.9 (11)
H6—C6—C5	120.4 (7)	H14c—C14—H14b	109.1 (12)
H6—C6—C7	120.3 (7)	N2—H1—N1	157.8 (9)

(DMAN_TAAM_50)

Crystal data

C14H24N2O2Cl2	β = 101.64°
Mr = 323.25	V = 1736.1 Å^3
Monoclinic, P?	Z = 4
Hall symbol: P ?	F(000) = 688
a = 10.085 Å	Dx = 1.237 Mg m^−3
b = 9.811 Å	Mo Kα radiation, λ = 0.71073 Å
c = 17.915 Å

Data collection

Radiation source: fine-focus sealed tube	h = −11→11
3116 independent reflections	k = 0→11
2933 reflections with > 2.0σ(I)	l = 0→21
θmax = 25.0°, θmin = 2.2°

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.015	Secondary atom site location: difference Fourier map
wR(F^2) = 0.036	Hydrogen site location: inferred from neighbouring sites
S = 3.92	All H-atom parameters refined
3116 reflections	Weighting scheme based on measured s.u.'s
277 parameters	(Δ/σ)max = 0.002

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
CL1	0.01220 (2)	0.90089 (2)	0.668041 (1)	0.02272 (2)
CL2	0.47726 (2)	0.90905 (2)	0.846026 (1)	0.02083 (2)
O1	0.13957 (6)	0.64946 (6)	0.74331 (3)	0.02465 (5)
O2	0.38262 (6)	0.65858 (7)	0.75258 (3)	0.02856 (5)
H1A	0.111 (1)	0.588 (1)	0.7207 (6)	0.009 (3)*
H1B	0.108 (1)	0.712 (1)	0.7256 (6)	0.008 (3)*
H2B	0.409 (1)	0.720 (1)	0.7747 (6)	0.013 (3)*
H2C	0.412 (1)	0.597 (1)	0.7728 (6)	0.010 (3)*
H1C	0.258 (1)	0.654 (1)	0.7484 (6)	0.042 (4)*
N1	0.83470 (6)	0.84221 (5)	0.88251 (3)	0.01654 (5)
N2	0.72553 (5)	0.75184 (5)	0.99268 (3)	0.01534 (5)
C1	0.96625 (6)	0.79653 (6)	0.92479 (4)	0.01581 (5)
C2	1.08187 (7)	0.81899 (7)	0.89675 (4)	0.01988 (6)
C3	1.20975 (7)	0.77518 (7)	0.93755 (4)	0.02183 (6)
C4	1.21977 (7)	0.70839 (7)	1.00570 (4)	0.01934 (5)
C5	1.11380 (7)	0.61112 (7)	1.10620 (4)	0.01995 (6)
C6	1.00140 (7)	0.58359 (7)	1.13595 (4)	0.02248 (6)
C7	0.87234 (7)	0.62871 (7)	1.09752 (4)	0.01970 (6)
C8	0.85857 (6)	0.69937 (6)	1.03005 (4)	0.01532 (5)
C9	0.97251 (7)	0.72666 (6)	0.99568 (4)	0.01464 (5)
C10	1.10232 (7)	0.68134 (6)	1.03581 (4)	0.01648 (5)
C11	0.79234 (8)	0.76626 (8)	0.81012 (4)	0.02502 (7)
C12	0.83124 (8)	0.99099 (7)	0.86943 (6)	0.02959 (7)
C13	0.67608 (8)	0.86005 (7)	1.03853 (5)	0.02271 (6)
C14	0.62286 (7)	0.64209 (7)	0.97241 (5)	0.02162 (6)
H2	0.7507 (9)	0.8011 (9)	0.9378 (5)	0.023 (2)*
H2A	1.0725 (9)	0.8709 (9)	0.8432 (6)	0.037 (2)*
H3	1.296 (1)	0.7962 (9)	0.9144 (5)	0.039 (2)*
H4	1.3153 (10)	0.6753 (9)	1.0397 (5)	0.031 (2)*
H5	1.2145 (10)	0.5831 (9)	1.1354 (5)	0.033 (2)*
H6	1.0094 (9)	0.5323 (10)	1.1880 (5)	0.038 (2)*
H7	0.785 (1)	0.6088 (9)	1.1210 (5)	0.036 (2)*
H11A	0.793 (1)	0.659 (1)	0.8221 (6)	0.053 (3)*
H11B	0.855 (1)	0.788 (1)	0.7706 (6)	0.057 (3)*
H11C	0.690 (1)	0.7974 (10)	0.7838 (5)	0.048 (3)*
H12A	0.862 (1)	1.044 (1)	0.9234 (6)	0.058 (3)*
H12B	0.896 (1)	1.020 (1)	0.8324 (6)	0.054 (3)*
H12C	0.730 (1)	1.018 (1)	0.8456 (6)	0.049 (3)*
H13A	0.6522 (10)	0.8185 (10)	1.0867 (6)	0.047 (3)*
H13B	0.750 (1)	0.935 (1)	1.0524 (5)	0.046 (3)*
H13C	0.588 (1)	0.9032 (10)	1.0042 (6)	0.043 (3)*
H14A	0.6046 (10)	0.5930 (10)	1.0205 (6)	0.043 (3)*
H14B	0.6609 (10)	0.570 (1)	0.9389 (6)	0.045 (3)*
H14C	0.533 (1)	0.6868 (9)	0.9412 (5)	0.041 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
CL1	0.02269 (9)	0.01930 (9)	0.02411 (10)	0.000020 (6)	−0.00017 (7)	0.00140 (6)
CL2	0.01955 (9)	0.01906 (9)	0.02436 (10)	0.00121 (6)	0.00557 (7)	0.00274 (6)
O1	0.0344 (3)	0.0160 (3)	0.0217 (3)	0.0007 (2)	0.0010 (2)	−0.0009 (2)
O2	0.0343 (3)	0.0188 (3)	0.0295 (3)	−0.0004 (3)	−0.0008 (3)	0.0026 (3)
N1	0.0157 (3)	0.0165 (3)	0.0178 (3)	0.0013 (2)	0.0045 (2)	0.0019 (2)
N2	0.0160 (3)	0.0149 (3)	0.0160 (3)	−0.0004 (2)	0.0052 (2)	−0.0013 (2)
C1	0.0166 (3)	0.0156 (3)	0.0163 (3)	−0.0001 (2)	0.0057 (3)	0.0011 (2)
C2	0.0179 (3)	0.0214 (3)	0.0221 (4)	0.0006 (3)	0.0080 (3)	0.0042 (3)
C3	0.0166 (3)	0.0235 (3)	0.0273 (4)	0.0005 (3)	0.0089 (3)	0.0035 (3)
C4	0.0152 (3)	0.0191 (3)	0.0243 (4)	0.0008 (3)	0.0053 (3)	0.0007 (3)
C5	0.0199 (4)	0.0218 (3)	0.0175 (3)	0.0027 (3)	0.0022 (3)	0.0019 (3)
C6	0.0236 (4)	0.0270 (4)	0.0171 (4)	0.0031 (3)	0.0050 (3)	0.0054 (3)
C7	0.0204 (4)	0.0236 (3)	0.0162 (3)	0.0010 (3)	0.0064 (3)	0.0028 (3)
C8	0.0185 (3)	0.0145 (3)	0.0143 (3)	−0.0018 (2)	0.0066 (3)	−0.0013 (2)
C9	0.0157 (3)	0.0138 (3)	0.0150 (3)	−0.0005 (2)	0.0044 (3)	−0.0008 (2)
C10	0.0164 (3)	0.0153 (3)	0.0177 (3)	0.0006 (2)	0.0034 (3)	−0.0007 (2)
C11	0.0226 (4)	0.0352 (4)	0.0171 (4)	0.0032 (3)	0.0037 (3)	−0.0011 (3)
C12	0.0225 (4)	0.0201 (4)	0.0468 (5)	0.0022 (3)	0.0085 (4)	0.0101 (3)
C13	0.0251 (4)	0.0222 (3)	0.0218 (4)	0.0032 (3)	0.0070 (3)	−0.0024 (3)
C14	0.0202 (4)	0.0202 (3)	0.0237 (4)	−0.0020 (3)	0.0027 (3)	0.0017 (3)

Geometric parameters (Å, º)

O1—H1C	1.18 (1)	C5—C10	1.4210 (10)
O1—H1B	0.74 (1)	C5—C6	1.373 (1)
O1—H1A	0.75 (1)	C5—H5	1.080 (9)
O2—H1C	1.24 (1)	C6—C7	1.4151 (10)
O2—H2B	0.74 (1)	C6—H6	1.049 (10)
O2—H2C	0.74 (1)	C7—C8	1.3759 (10)
N1—C1	1.4592 (8)	C7—H7	1.07 (1)
N1—C12	1.4777 (9)	C8—C9	1.4340 (10)
N1—C11	1.4820 (9)	C9—C10	1.4313 (9)
N2—C8	1.4666 (8)	C11—H11B	1.06 (1)
N2—C14	1.4871 (8)	C11—H11A	1.07 (1)
N2—C13	1.4885 (9)	C11—H11C	1.09 (1)
N2—H2	1.17 (1)	C12—H12B	1.06 (1)
C1—C9	1.4334 (9)	C12—H12C	1.06 (1)
C1—C2	1.3773 (10)	C12—H12A	1.09 (1)
C2—C3	1.4148 (10)	C13—H13A	1.03 (1)
C2—H2A	1.07 (1)	C13—H13B	1.04 (1)
C3—C4	1.371 (1)	C13—H13C	1.06 (1)
C3—H3	1.05 (1)	C14—H14A	1.04 (1)
C4—C10	1.4221 (10)	C14—H14B	1.05 (1)
C4—H4	1.081 (9)	C14—H14C	1.063 (10)
O1—H1C—O2	179 (1)	C4—C10—C9	119.93 (8)
H1A—O1—H1C	110 (1)	C4—C10—C5	120.14 (7)
H1A—O1—H1B	111 (1)	C4—C3—H3	121.7 (6)
H1B—O1—H1C	110 (1)	C5—C10—C9	119.92 (7)
H2B—O2—H1C	108 (1)	C5—C6—C7	119.99 (9)
H2B—O2—H2C	110 (1)	C5—C6—H6	121.2 (6)
H2C—O2—H1C	108 (1)	C6—C5—C10	120.93 (8)
N1—C1—C9	118.66 (6)	C6—C5—H5	122.0 (6)
N1—C1—C2	120.63 (5)	C6—C7—C8	120.33 (8)
N1—C12—H12B	111.6 (6)	C6—C7—H7	120.2 (6)
N1—C12—H12C	107.8 (6)	C7—C8—C9	121.57 (7)
N1—C12—H12A	109.7 (6)	C7—C6—H6	118.7 (6)
N1—C11—H11B	112.3 (6)	C8—N2—C14	112.65 (6)
N1—C11—H11A	109.2 (6)	C8—N2—C13	112.08 (6)
N1—C11—H11C	108.5 (5)	C8—N2—H2	101.3 (4)
N2—C8—C9	118.49 (5)	C8—C9—C10	117.21 (5)
N2—C8—C7	119.92 (6)	C8—C7—H7	119.5 (6)
N2—C14—H14A	111.4 (6)	C10—C5—H5	117.0 (5)
N2—C14—H14B	108.2 (6)	C10—C4—H4	116.5 (5)
N2—C14—H14C	108.1 (5)	C11—N1—C12	111.38 (6)
N2—C13—H13A	110.0 (6)	C13—N2—C14	110.91 (6)
N2—C13—H13B	109.4 (6)	C13—N2—H2	108.9 (5)
N2—C13—H13C	107.5 (5)	C14—N2—H2	110.6 (5)
C1—N1—C12	112.06 (5)	H11A—C11—H11B	110.4 (8)
C1—N1—C11	111.79 (6)	H11A—C11—H11C	109.1 (8)
C1—C9—C8	125.02 (7)	H11B—C11—H11C	107.2 (8)
C1—C9—C10	117.77 (7)	H12A—C12—H12B	109.0 (9)
C1—C2—C3	120.89 (6)	H12A—C12—H12C	108.6 (8)
C1—C2—H2A	118.3 (6)	H12B—C12—H12C	110.1 (9)
C2—C1—C9	120.70 (7)	H13A—C13—H13B	111.0 (8)
C2—C3—C4	120.06 (7)	H13A—C13—H13C	109.4 (8)
C2—C3—H3	118.3 (6)	H13B—C13—H13C	109.4 (8)
C3—C4—C10	120.63 (7)	H14A—C14—H14B	107.9 (8)
C3—C4—H4	122.9 (6)	H14A—C14—H14C	110.6 (8)
C3—C2—H2A	120.9 (6)	H14B—C14—H14C	110.5 (8)
O1—H1C—O2—H2B	135 (1)	C7—C8—N2—H2	−178.1 (5)
O1—H1C—O2—H2C	−107 (1)	C7—C8—C9—C10	−2.06 (6)
O2—H1C—O1—H1B	−77 (1)	C7—C6—C5—C10	−1.81 (7)
O2—H1C—O1—H1A	45 (1)	C7—C6—C5—H5	176.7 (7)
N1—C1—C9—C8	−1.21 (6)	C8—N2—C14—H14A	63.5 (5)
N1—C1—C9—C10	179.30 (6)	C8—N2—C14—H14B	−55.0 (6)
N1—C1—C2—C3	179.87 (7)	C8—N2—C14—H14C	−174.8 (7)
N1—C1—C2—H2A	0.0 (5)	C8—N2—C13—H13A	−69.6 (5)
N2—C8—C9—C1	−3.18 (6)	C8—N2—C13—H13B	52.6 (6)
N2—C8—C9—C10	176.32 (5)	C8—N2—C13—H13C	171.3 (7)
N2—C8—C7—C6	−176.84 (6)	C8—C7—C6—H6	178.3 (8)
N2—C8—C7—H7	2.7 (5)	C9—C1—N1—C12	121.77 (7)
C1—N1—C12—H12B	66.8 (6)	C9—C1—N1—C11	−112.39 (6)
C1—N1—C12—H12C	−172.2 (8)	C9—C1—C2—H2A	179.4 (8)
C1—N1—C12—H12A	−54.1 (6)	C9—C8—N2—C14	121.63 (6)
C1—N1—C11—H11B	−67.2 (6)	C9—C8—N2—C13	−112.45 (6)
C1—N1—C11—H11A	55.6 (6)	C9—C8—N2—H2	3.4 (4)
C1—N1—C11—H11C	174.5 (7)	C9—C8—C7—H7	−179.0 (8)
C1—C9—C8—C7	178.44 (6)	C9—C10—C5—H5	−177.3 (7)
C1—C9—C10—C5	−179.76 (6)	C9—C10—C4—H4	177.5 (7)
C1—C9—C10—C4	1.15 (6)	C10—C5—C6—H6	−179.6 (8)
C1—C2—C3—C4	0.53 (6)	C10—C4—C3—H3	179.9 (8)
C1—C2—C3—H3	−178.9 (8)	C11—N1—C12—H12B	−59.2 (6)
C2—C1—N1—C12	−58.83 (6)	C11—N1—C12—H12C	61.7 (6)
C2—C1—N1—C11	67.01 (6)	C11—N1—C12—H12A	179.9 (9)
C2—C1—C9—C8	179.39 (6)	C12—N1—C11—H11B	59.1 (6)
C2—C1—C9—C10	−0.10 (6)	C12—N1—C11—H11A	−178.1 (9)
C2—C3—C4—C10	0.54 (6)	C12—N1—C11—H11C	−59.3 (6)
C2—C3—C4—H4	−178.3 (7)	C13—N2—C14—H14A	−63.1 (6)
C3—C4—C10—C9	−1.39 (7)	C13—N2—C14—H14B	178.4 (8)
C3—C4—C10—C5	179.52 (8)	C13—N2—C14—H14C	58.7 (5)
C3—C2—C1—C9	−0.74 (6)	C14—N2—C13—H13A	57.3 (6)
C4—C10—C9—C8	−178.39 (5)	C14—N2—C13—H13B	179.5 (8)
C4—C10—C5—C6	−179.70 (8)	C14—N2—C13—H13C	−61.8 (5)
C4—C10—C5—H5	1.8 (5)	H2—N2—C14—H14A	176 (1)
C4—C3—C2—H2A	−179.7 (8)	H2—N2—C14—H14B	57.5 (8)
C5—C10—C9—C8	0.71 (6)	H2—N2—C14—H14C	−62.3 (7)
C5—C10—C4—H4	−1.6 (5)	H2—N2—C13—H13A	179 (1)
C5—C6—C7—C8	0.46 (6)	H2—N2—C13—H13B	−58.6 (8)
C5—C6—C7—H7	−179.0 (8)	H2—N2—C13—H13C	60.2 (7)
C6—C5—C10—C9	1.20 (6)	H2A—C2—C3—H3	0.9 (8)
C6—C7—C8—C9	1.52 (6)	H3—C3—C4—H4	1.1 (8)
C7—C8—N2—C14	−59.96 (6)	H5—C5—C6—H6	−1.2 (8)
C7—C8—N2—C13	65.96 (6)	H6—C6—C7—H7	−1.2 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···CL2^i	0.75 (1)	2.21 (1)	2.9584 (6)	179 (1)
O2—H2C···CL1^i	0.74 (1)	2.25 (1)	2.9884 (7)	176 (1)
C14—H14B···CL1^i	1.05 (1)	2.848 (9)	3.5219 (7)	122.2 (7)
O1—H1B···CL1	0.74 (1)	2.24 (1)	2.9756 (6)	178 (1)
O2—H2B···CL2	0.74 (1)	2.28 (1)	3.0179 (7)	176 (1)
O1—H1C···O2	1.18 (1)	1.24 (1)	2.4248 (9)	179 (1)
N2—H2···CL2	1.17 (1)	3.098 (9)	3.5912 (5)	105.5 (5)
N2—H2···N1	1.17 (1)	1.48 (1)	2.6020 (8)	157.6 (7)
N2—H2···C1	1.17 (1)	2.233 (9)	2.9592 (9)	117.4 (4)
N2—H2···C11	1.17 (1)	2.431 (10)	3.473 (1)	147.3 (6)
N2—H2···C12	1.17 (1)	2.456 (10)	3.531 (1)	152.0 (6)
C13—H13A···C7	1.03 (1)	2.874 (10)	3.056 (1)	90.3 (8)
C14—H14A···C7	1.04 (1)	2.795 (9)	3.0158 (10)	92.1 (6)
C14—H14C···CL2	1.063 (10)	2.755 (10)	3.5779 (8)	134.2 (9)

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

(DMAN_TAAM_80)

Crystal data

C14H24N2O2Cl2	β = 101.64°
Mr = 323.25	V = 1736.1 Å^3
Monoclinic, P?	Z = 4
Hall symbol: P ?	F(000) = 688
a = 10.085 Å	Dx = 1.237 Mg m^−3
b = 9.811 Å	Mo Kα radiation, λ = 0.71073 Å
c = 17.915 Å

Data collection

Radiation source: fine-focus sealed tube	h = −18→17
10470 independent reflections	k = 0→17
9632 reflections with > 2.0σ(I)	l = 0→32
θmax = 40.0°, θmin = 2.2°

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.019	Secondary atom site location: difference Fourier map
wR(F^2) = 0.038	Hydrogen site location: inferred from neighbouring sites
S = 3.01	All H-atom parameters refined
10470 reflections	Weighting scheme based on measured s.u.'s
277 parameters	(Δ/σ)max = 0.004

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
CL1	0.012239 (1)	0.900815 (1)	0.668021 (1)	0.021983 (1)
CL2	0.477244 (1)	0.909082 (1)	0.846047 (1)	0.020186 (1)
O1	0.13931 (3)	0.64947 (3)	0.74315 (2)	0.02396 (2)
O2	0.38294 (4)	0.65867 (3)	0.75271 (2)	0.02789 (2)
H1A	0.1099 (8)	0.5851 (8)	0.7197 (4)	0.018 (2)*
H1B	0.1061 (8)	0.7163 (8)	0.7247 (4)	0.019 (2)*
H2B	0.4109 (8)	0.7229 (9)	0.7760 (4)	0.023 (2)*
H2C	0.4130 (8)	0.5938 (8)	0.7735 (4)	0.020 (2)*
H1C	0.2556 (9)	0.654 (1)	0.7485 (5)	0.044 (3)*
N1	0.83485 (3)	0.84221 (3)	0.88247 (2)	0.01574 (2)
N2	0.72547 (3)	0.75175 (3)	0.99274 (2)	0.01422 (2)
C1	0.96619 (3)	0.79644 (3)	0.92482 (2)	0.01490 (2)
C2	1.08182 (4)	0.81898 (3)	0.89674 (2)	0.01906 (2)
C3	1.20978 (4)	0.77524 (4)	0.93748 (2)	0.02094 (2)
C4	1.21979 (3)	0.70831 (3)	1.00573 (2)	0.01866 (2)
C5	1.11385 (4)	0.61106 (3)	1.10619 (2)	0.01912 (2)
C6	1.00135 (4)	0.58342 (4)	1.13598 (2)	0.02166 (2)
C7	0.87229 (4)	0.62859 (4)	1.09752 (2)	0.01902 (2)
C8	0.85880 (3)	0.69926 (3)	1.03010 (2)	0.01444 (2)
C9	0.97240 (3)	0.72661 (3)	0.99569 (2)	0.01373 (2)
C10	1.10238 (3)	0.68132 (3)	1.03584 (2)	0.01551 (2)
C11	0.79227 (4)	0.76620 (4)	0.81012 (2)	0.02411 (3)
C12	0.83123 (4)	0.99094 (4)	0.86937 (3)	0.02868 (3)
C13	0.67598 (4)	0.85999 (4)	1.03864 (2)	0.02179 (2)
C14	0.62288 (4)	0.64196 (4)	0.97237 (2)	0.02051 (2)
H2	0.7504 (7)	0.8013 (7)	0.9380 (4)	0.027 (2)*
H2A	1.0733 (7)	0.8703 (7)	0.8431 (4)	0.036 (2)*
H3	1.2961 (7)	0.7961 (7)	0.9144 (4)	0.039 (2)*
H4	1.3151 (7)	0.6745 (6)	1.0398 (4)	0.032 (2)*
H5	1.2147 (7)	0.5825 (6)	1.1354 (4)	0.033 (2)*
H6	1.0097 (7)	0.5329 (7)	1.1884 (4)	0.038 (2)*
H7	0.7847 (7)	0.6088 (7)	1.1209 (4)	0.036 (2)*
H11A	0.7935 (8)	0.6591 (8)	0.8221 (4)	0.049 (2)*
H11B	0.8546 (8)	0.7875 (8)	0.7703 (5)	0.056 (2)*
H11C	0.6896 (8)	0.7979 (7)	0.7837 (4)	0.047 (2)*
H12A	0.8620 (8)	1.0450 (9)	0.9232 (5)	0.059 (2)*
H12B	0.8952 (8)	1.0203 (8)	0.8320 (5)	0.056 (2)*
H12C	0.7301 (8)	1.0177 (7)	0.8455 (4)	0.047 (2)*
H13A	0.6520 (7)	0.8186 (7)	1.0877 (4)	0.047 (2)*
H13B	0.7492 (8)	0.9357 (8)	1.0523 (4)	0.046 (2)*
H13C	0.5876 (8)	0.9030 (7)	1.0045 (4)	0.042 (2)*
H14A	0.6035 (7)	0.5929 (7)	1.0206 (4)	0.042 (2)*
H14B	0.6606 (7)	0.5693 (7)	0.9389 (4)	0.045 (2)*
H14C	0.5317 (7)	0.6868 (7)	0.9413 (4)	0.041 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
CL1	0.02197 (4)	0.01882 (3)	0.02319 (3)	0.00010 (2)	−0.00013 (3)	0.00146 (2)
CL2	0.01887 (3)	0.01870 (3)	0.02352 (3)	0.00121 (2)	0.00556 (3)	0.00272 (2)
O1	0.0324 (1)	0.01735 (10)	0.0207 (1)	0.00042 (9)	0.0018 (1)	−0.00075 (8)
O2	0.0324 (2)	0.0201 (1)	0.0286 (1)	−0.0005 (1)	0.00008 (12)	0.00276 (9)
N1	0.0157 (1)	0.01566 (9)	0.01656 (10)	0.00112 (8)	0.00480 (8)	0.00226 (7)
N2	0.0144 (1)	0.01402 (9)	0.01503 (9)	−0.00036 (7)	0.00497 (8)	−0.00128 (7)
C1	0.0150 (1)	0.0151 (1)	0.0156 (1)	0.00015 (8)	0.00545 (9)	0.00128 (8)
C2	0.0170 (1)	0.0212 (1)	0.0209 (1)	0.00074 (9)	0.0082 (1)	0.00433 (10)
C3	0.0158 (1)	0.0230 (1)	0.0258 (1)	0.00069 (10)	0.0086 (1)	0.0041 (1)
C4	0.0145 (1)	0.0191 (1)	0.0229 (1)	0.00082 (9)	0.0052 (1)	0.00125 (10)
C5	0.0188 (1)	0.0217 (1)	0.0164 (1)	0.00257 (10)	0.00269 (10)	0.00214 (9)
C6	0.0221 (1)	0.0272 (1)	0.0162 (1)	0.0031 (1)	0.0050 (1)	0.0055 (1)
C7	0.0194 (1)	0.0234 (1)	0.0154 (1)	0.00101 (10)	0.0062 (1)	0.00360 (9)
C8	0.0157 (1)	0.0151 (1)	0.01348 (10)	−0.00057 (8)	0.00523 (9)	−0.00011 (8)
C9	0.0142 (1)	0.01360 (9)	0.01400 (10)	−0.00026 (8)	0.00432 (8)	−0.00022 (7)
C10	0.0150 (1)	0.0154 (1)	0.0163 (1)	0.00054 (8)	0.00347 (9)	−0.000077 (8)
C11	0.0220 (2)	0.0340 (2)	0.0161 (1)	0.0034 (1)	0.0034 (1)	−0.0019 (1)
C12	0.0222 (2)	0.0177 (1)	0.0467 (2)	0.0021 (1)	0.0083 (2)	0.0100 (1)
C13	0.0248 (2)	0.0207 (1)	0.0209 (1)	0.0043 (1)	0.0072 (1)	−0.0039 (1)
C14	0.0188 (1)	0.0186 (1)	0.0233 (1)	−0.00369 (10)	0.0022 (1)	0.00097 (10)

Geometric parameters (Å, º)

O1—H1C	1.159 (9)	C5—C10	1.4207 (5)
O1—H1B	0.779 (8)	C5—C6	1.3747 (5)
O1—H1A	0.783 (8)	C5—H5	1.082 (7)
O2—H1C	1.271 (9)	C6—C7	1.4153 (5)
O2—H2C	0.768 (8)	C6—H6	1.050 (7)
O2—H2B	0.777 (8)	C7—C8	1.3755 (4)
N1—C1	1.4582 (4)	C7—H7	1.069 (8)
N1—C12	1.4772 (5)	C8—C9	1.4317 (4)
N1—C11	1.4818 (5)	C9—C10	1.4327 (4)
N2—C8	1.4690 (4)	C11—H11B	1.062 (9)
N2—C14	1.4871 (4)	C11—H11A	1.072 (8)
N2—C13	1.4895 (4)	C11—H11C	1.093 (8)
N2—H2	1.166 (7)	C12—H12C	1.056 (8)
C1—C9	1.4329 (4)	C12—H12B	1.059 (9)
C1—C2	1.3778 (5)	C12—H12A	1.089 (8)
C2—C3	1.4149 (5)	C13—H13A	1.040 (8)
C2—H2A	1.073 (7)	C13—H13B	1.041 (8)
C3—C4	1.3735 (5)	C13—H13C	1.061 (7)
C3—H3	1.056 (8)	C14—H14A	1.042 (8)
C4—C10	1.4215 (5)	C14—H14B	1.051 (8)
C4—H4	1.082 (7)	C14—H14C	1.069 (7)
O1—H1C—O2	178.8 (9)	C4—C10—C9	119.97 (4)
H1A—O1—H1C	110.0 (8)	C4—C10—C5	120.13 (3)
H1A—O1—H1B	111.5 (8)	C4—C3—H3	121.5 (4)
H1B—O1—H1C	110.2 (8)	C5—C10—C9	119.90 (3)
H2B—O2—H1C	108.3 (8)	C5—C6—C7	119.95 (4)
H2B—O2—H2C	110.3 (9)	C5—C6—H6	121.1 (4)
H2C—O2—H1C	107.1 (8)	C6—C5—C10	120.94 (4)
N1—C1—C9	118.75 (3)	C6—C5—H5	122.0 (4)
N1—C1—C2	120.50 (2)	C6—C7—C8	120.23 (4)
N1—C12—H12C	107.5 (4)	C6—C7—H7	120.2 (4)
N1—C12—H12B	111.8 (5)	C7—C8—C9	121.78 (3)
N1—C12—H12A	110.3 (5)	C7—C6—H6	118.9 (4)
N1—C11—H11B	112.5 (5)	C8—N2—C14	112.67 (3)
N1—C11—H11A	109.2 (4)	C8—N2—C13	112.10 (3)
N1—C11—H11C	108.5 (4)	C8—N2—H2	101.3 (3)
N2—C8—C9	118.46 (2)	C8—C9—C10	117.15 (3)
N2—C8—C7	119.74 (3)	C8—C7—H7	119.5 (4)
N2—C14—H14A	111.7 (4)	C10—C5—H5	117.0 (4)
N2—C14—H14B	108.5 (4)	C10—C4—H4	116.2 (4)
N2—C14—H14C	108.2 (4)	C11—N1—C12	111.39 (3)
N2—C13—H13A	110.4 (4)	C13—N2—C14	110.96 (3)
N2—C13—H13B	109.8 (4)	C13—N2—H2	108.7 (4)
N2—C13—H13C	107.5 (4)	C14—N2—H2	110.7 (4)
C1—N1—C12	112.18 (3)	H11A—C11—H11B	110.0 (6)
C1—N1—C11	111.88 (3)	H11A—C11—H11C	109.7 (6)
C1—C9—C8	125.13 (3)	H11B—C11—H11C	106.9 (6)
C1—C9—C10	117.72 (3)	H12A—C12—H12C	108.5 (6)
C1—C2—C3	120.94 (3)	H12A—C12—H12B	109.0 (7)
C1—C2—H2A	118.8 (4)	H12B—C12—H12C	109.7 (6)
C2—C1—C9	120.75 (3)	H13A—C13—H13B	110.8 (6)
C2—C3—C4	119.98 (3)	H13A—C13—H13C	109.4 (6)
C2—C3—H3	118.5 (4)	H13B—C13—H13C	108.9 (6)
C3—C4—C10	120.64 (4)	H14A—C14—H14B	108.0 (6)
C3—C4—H4	123.1 (4)	H14A—C14—H14C	109.7 (6)
C3—C2—H2A	120.3 (4)	H14B—C14—H14C	110.8 (6)
O1—H1C—O2—H2C	−116.7 (8)	C7—C8—N2—H2	−178.3 (3)
O1—H1C—O2—H2B	124.3 (8)	C7—C8—C9—C10	−2.12 (3)
O2—H1C—O1—H1B	−67.5 (8)	C7—C6—C5—C10	−1.82 (3)
O2—H1C—O1—H1A	55.8 (8)	C7—C6—C5—H5	176.9 (5)
N1—C1—C9—C8	−1.20 (3)	C8—N2—C14—H14A	64.1 (4)
N1—C1—C9—C10	179.33 (3)	C8—N2—C14—H14B	−54.8 (4)
N1—C1—C2—C3	179.86 (4)	C8—N2—C14—H14C	−175.1 (5)
N1—C1—C2—H2A	−0.3 (4)	C8—N2—C13—H13A	−69.4 (4)
N2—C8—C9—C1	−3.18 (3)	C8—N2—C13—H13B	53.0 (4)
N2—C8—C9—C10	176.29 (2)	C8—N2—C13—H13C	171.4 (5)
N2—C8—C7—C6	−176.85 (3)	C8—C7—C6—H6	177.7 (5)
N2—C8—C7—H7	2.6 (4)	C9—C8—N2—C14	121.52 (3)
C1—N1—C12—H12C	−172.3 (5)	C9—C8—N2—C13	−112.46 (3)
C1—N1—C12—H12B	67.3 (4)	C9—C8—N2—H2	3.3 (3)
C1—N1—C12—H12A	−54.2 (5)	C9—C8—C7—H7	−179.0 (6)
C1—N1—C11—H11B	−67.3 (4)	C9—C1—N1—C12	121.70 (3)
C1—N1—C11—H11A	55.1 (4)	C9—C1—N1—C11	−112.27 (3)
C1—N1—C11—H11C	174.7 (5)	C9—C1—C2—H2A	179.1 (6)
C1—C9—C8—C7	178.40 (3)	C9—C10—C5—H5	−177.6 (5)
C1—C9—C10—C5	−179.72 (3)	C9—C10—C4—H4	177.9 (5)
C1—C9—C10—C4	1.11 (3)	C10—C5—C6—H6	−179.0 (6)
C1—C2—C3—C4	0.52 (3)	C10—C4—C3—H3	179.9 (6)
C1—C2—C3—H3	−178.9 (6)	C11—N1—C12—H12C	61.4 (4)
C2—C1—N1—C12	−58.87 (3)	C11—N1—C12—H12B	−59.0 (4)
C2—C1—N1—C11	67.16 (3)	C11—N1—C12—H12A	179.5 (6)
C2—C1—C9—C8	179.37 (3)	C12—N1—C11—H11B	59.2 (5)
C2—C1—C9—C10	−0.10 (3)	C12—N1—C11—H11A	−178.4 (6)
C2—C3—C4—C10	0.51 (3)	C12—N1—C11—H11C	−58.9 (4)
C2—C3—C4—H4	−178.7 (5)	C13—N2—C14—H14A	−62.5 (4)
C3—C4—C10—C9	−1.33 (3)	C13—N2—C14—H14B	178.5 (6)
C3—C4—C10—C5	179.50 (4)	C13—N2—C14—H14C	58.3 (4)
C3—C2—C1—C9	−0.72 (3)	C14—N2—C13—H13A	57.6 (4)
C4—C10—C9—C8	−178.41 (3)	C14—N2—C13—H13B	180.0 (6)
C4—C10—C5—C6	−179.65 (4)	C14—N2—C13—H13C	−61.7 (4)
C4—C10—C5—H5	1.5 (4)	H2—N2—C14—H14A	176.7 (8)
C4—C3—C2—H2A	−179.3 (6)	H2—N2—C14—H14B	57.8 (6)
C5—C10—C9—C8	0.76 (3)	H2—N2—C14—H14C	−62.5 (5)
C5—C10—C4—H4	−1.3 (4)	H2—N2—C13—H13A	179.4 (8)
C5—C6—C7—C8	0.47 (3)	H2—N2—C13—H13B	−58.2 (6)
C5—C6—C7—H7	−179.0 (6)	H2—N2—C13—H13C	60.2 (5)
C6—C5—C10—C9	1.18 (3)	H2A—C2—C3—H3	1.2 (6)
C6—C7—C8—C9	1.55 (3)	H3—C3—C4—H4	0.8 (6)
C7—C8—N2—C14	−60.03 (3)	H5—C5—C6—H6	−0.3 (6)
C7—C8—N2—C13	65.99 (3)	H6—C6—C7—H7	−1.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···CL2^i	0.783 (8)	2.173 (8)	2.9563 (3)	178.4 (8)
O2—H2C···CL1^i	0.768 (8)	2.221 (8)	2.9880 (3)	176.6 (9)
C14—H14B···CL1^i	1.051 (8)	2.845 (7)	3.5210 (4)	122.3 (5)
O1—H1B···CL1	0.779 (8)	2.194 (8)	2.9730 (3)	177.6 (9)
O2—H2B···CL2	0.777 (8)	2.241 (8)	3.0157 (3)	175.8 (9)
O1—H1C···O2	1.159 (9)	1.271 (9)	2.4300 (5)	178.8 (9)
N2—H2···CL2	1.166 (7)	3.097 (7)	3.5918 (3)	105.7 (4)
N2—H2···N1	1.166 (7)	1.489 (8)	2.6050 (4)	157.4 (5)
N2—H2···C1	1.166 (7)	2.236 (7)	2.9594 (4)	117.3 (3)
N2—H2···C11	1.166 (7)	2.436 (7)	3.4738 (5)	147.1 (5)
N2—H2···C12	1.166 (7)	2.458 (7)	3.5327 (5)	152.3 (5)
C14—H14A···C7	1.042 (8)	2.804 (7)	3.0158 (5)	91.5 (4)
C14—H14C···CL2	1.069 (7)	2.755 (7)	3.5785 (4)	133.8 (6)

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

(FC_IAM_50)

Crystal data

C20H30Fe	V = 1722.6 (2) Å^3
Mr = 326.29	Z = 4
a = 15.0905 (10) Å	F(000) = 704
b = 11.4741 (8) Å	Dx = 1.258 Mg m^−3
c = 9.9484 (6) Å	Mo Kα radiation, λ = 0.71073 Å
α = 90°	µ = 0.87 mm^−1
β = 90°	T = 90 K
γ = 90°

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 3.0°
763 measured reflections	h = 0→17
763 independent reflections	k = 0→13
736 reflections with I > 2σ(I)	l = 0→11

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.51	w = 1/[σ^2(Fo^2) + (0.0332P)^2 + 0.5477P] where P = (Fo^2 + 2Fc^2)/3
763 reflections	(Δ/σ)max = 0.042
84 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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.

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 > 2sigma(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
Fe1	0.0000	0.0000	0.0000	0.01027 (18)
C1	0.0000	−0.17490 (15)	0.04245 (19)	0.0178 (4)
C2	−0.07658 (8)	−0.12036 (11)	0.09889 (12)	0.0164 (3)
C3	−0.04738 (8)	−0.03187 (12)	0.18988 (13)	0.0137 (3)
C4	0.0000	−0.27283 (17)	−0.0577 (2)	0.0295 (5)
C5	−0.17105 (9)	−0.15349 (15)	0.07229 (16)	0.0278 (4)
C6	−0.10580 (9)	0.04373 (13)	0.27454 (14)	0.0215 (3)
H1	0.0000	−0.347 (3)	−0.012 (2)	0.030 (8)*
H2	−0.0483 (12)	−0.270 (2)	−0.116 (2)	0.053 (6)*
H4	−0.1783 (14)	−0.1796 (18)	−0.017 (2)	0.034 (5)*
H3	−0.1898 (11)	−0.2136 (16)	0.1353 (19)	0.036 (5)*
H5	−0.2103 (12)	−0.0870 (18)	0.0805 (19)	0.038 (5)*
H7	−0.1628 (12)	0.0588 (16)	0.2280 (17)	0.028 (4)*
H6	−0.1158 (14)	0.0072 (16)	0.360 (3)	0.032 (5)*
H8	−0.0772 (13)	0.1185 (19)	0.293 (2)	0.038 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0127 (2)	0.0096 (3)	0.0085 (3)	0.000	0.000	−0.00015 (10)
C1	0.0325 (10)	0.0102 (9)	0.0106 (8)	0.000	0.000	0.0016 (7)
C2	0.0208 (6)	0.0154 (6)	0.0130 (6)	−0.0049 (5)	−0.0021 (5)	0.0040 (5)
C3	0.0161 (7)	0.0145 (6)	0.0104 (6)	−0.0010 (5)	0.0017 (5)	0.0033 (5)
C4	0.0609 (15)	0.0125 (10)	0.0151 (10)	0.000	0.000	−0.0021 (8)
C5	0.0251 (8)	0.0301 (8)	0.0282 (8)	−0.0141 (6)	−0.0081 (6)	0.0090 (6)
C6	0.0237 (7)	0.0243 (8)	0.0164 (7)	0.0054 (6)	0.0067 (5)	0.0011 (6)

Geometric parameters (Å, º)

Fe1—C1	2.0507 (17)	C2—C3	1.4298 (19)
Fe1—C1^i	2.0507 (17)	C2—C5	1.4991 (18)
Fe1—C3	2.0526 (12)	C3—C3^iii	1.430 (2)
Fe1—C3^ii	2.0526 (12)	C3—C6	1.4963 (18)
Fe1—C3^i	2.0526 (12)	C4—H1	0.96 (3)
Fe1—C3^iii	2.0526 (12)	C4—H2	0.930 (19)
Fe1—C2^iii	2.0519 (12)	C5—H4	0.95 (2)
Fe1—C2	2.0519 (12)	C5—H3	0.974 (19)
Fe1—C2^i	2.0519 (12)	C5—H5	0.97 (2)
Fe1—C2^ii	2.0519 (12)	C6—H7	0.992 (18)
C1—C2	1.4291 (17)	C6—H6	0.96 (2)
C1—C2^iii	1.4291 (17)	C6—H8	0.98 (2)
C1—C4	1.502 (3)
C1—Fe1—C1^i	180.0	C3^ii—Fe1—C2^ii	40.77 (5)
C1—Fe1—C3	68.67 (6)	C3^i—Fe1—C2^ii	68.60 (5)
C1^i—Fe1—C3	111.33 (6)	C3^iii—Fe1—C2^ii	139.23 (5)
C1—Fe1—C3^ii	111.33 (6)	C2^iii—Fe1—C2^ii	180.0
C1^i—Fe1—C3^ii	68.67 (6)	C2—Fe1—C2^ii	111.45 (7)
C3—Fe1—C3^ii	139.23 (7)	C2^i—Fe1—C2^ii	68.55 (7)
C1—Fe1—C3^i	111.33 (6)	C2—C1—C2^iii	107.92 (16)
C1^i—Fe1—C3^i	68.67 (6)	C2—C1—C4	126.04 (8)
C3—Fe1—C3^i	180.00 (7)	C2^iii—C1—C4	126.04 (8)
C3^ii—Fe1—C3^i	40.77 (7)	C2—C1—Fe1	69.66 (8)
C1—Fe1—C3^iii	68.66 (6)	C2^iii—C1—Fe1	69.66 (8)
C1^i—Fe1—C3^iii	111.33 (6)	C4—C1—Fe1	126.55 (13)
C3—Fe1—C3^iii	40.77 (7)	C3—C2—C1	108.09 (11)
C3^ii—Fe1—C3^iii	180.0	C3—C2—C5	125.79 (13)
C3^i—Fe1—C3^iii	139.23 (7)	C1—C2—C5	126.06 (13)
C1—Fe1—C2^iii	40.77 (5)	C3—C2—Fe1	69.64 (7)
C1^i—Fe1—C2^iii	139.23 (5)	C1—C2—Fe1	69.57 (8)
C3—Fe1—C2^iii	68.60 (5)	C5—C2—Fe1	128.43 (9)
C3^ii—Fe1—C2^iii	139.23 (5)	C3^iii—C3—C2	107.95 (7)
C3^i—Fe1—C2^iii	111.40 (5)	C3^iii—C3—C6	126.10 (7)
C3^iii—Fe1—C2^iii	40.77 (5)	C2—C3—C6	125.91 (11)
C1—Fe1—C2	40.77 (5)	C3^iii—C3—Fe1	69.62 (3)
C1^i—Fe1—C2	139.23 (5)	C2—C3—Fe1	69.59 (7)
C3—Fe1—C2	40.77 (5)	C6—C3—Fe1	128.31 (10)
C3^ii—Fe1—C2	111.40 (5)	C1—C4—H1	110.5 (15)
C3^i—Fe1—C2	139.23 (5)	C1—C4—H2	113.0 (14)
C3^iii—Fe1—C2	68.60 (5)	H1—C4—H2	108.5 (16)
C2^iii—Fe1—C2	68.55 (7)	C2—C5—H4	110.9 (13)
C1—Fe1—C2^i	139.23 (5)	C2—C5—H3	110.0 (10)
C1^i—Fe1—C2^i	40.77 (5)	H4—C5—H3	110.3 (17)
C3—Fe1—C2^i	139.23 (5)	C2—C5—H5	111.5 (11)
C3^ii—Fe1—C2^i	68.60 (5)	H4—C5—H5	105.0 (17)
C3^i—Fe1—C2^i	40.77 (5)	H3—C5—H5	109.0 (15)
C3^iii—Fe1—C2^i	111.41 (5)	C3—C6—H7	110.4 (10)
C2^iii—Fe1—C2^i	111.45 (7)	C3—C6—H6	109.7 (12)
C2—Fe1—C2^i	180.0	H7—C6—H6	110.7 (16)
C1—Fe1—C2^ii	139.23 (5)	C3—C6—H8	110.9 (12)
C1^i—Fe1—C2^ii	40.77 (5)	H7—C6—H8	108.6 (16)
C3—Fe1—C2^ii	111.41 (5)	H6—C6—H8	106.5 (18)
C1^i—Fe1—C1—C2	130.8 (16)	C2^iii—Fe1—C2—C1	−37.78 (9)
C3—Fe1—C1—C2	37.62 (8)	C2^i—Fe1—C2—C1	92.63 (9)
C3^ii—Fe1—C1—C2	−98.45 (9)	C2^ii—Fe1—C2—C1	142.22 (9)
C3^i—Fe1—C1—C2	−142.38 (8)	C1—Fe1—C2—C5	−120.42 (17)
C3^iii—Fe1—C1—C2	81.55 (9)	C1^i—Fe1—C2—C5	59.58 (17)
C2^iii—Fe1—C1—C2	119.17 (15)	C3—Fe1—C2—C5	120.13 (16)
C2^i—Fe1—C1—C2	180.0	C3^ii—Fe1—C2—C5	−22.15 (15)
C2^ii—Fe1—C1—C2	−60.83 (15)	C3^i—Fe1—C2—C5	−59.87 (16)
C1^i—Fe1—C1—C2^iii	11.6 (16)	C3^iii—Fe1—C2—C5	157.85 (15)
C3—Fe1—C1—C2^iii	−81.55 (9)	C2^iii—Fe1—C2—C5	−158.20 (12)
C3^ii—Fe1—C1—C2^iii	142.38 (8)	C2^i—Fe1—C2—C5	−27.78 (13)
C3^i—Fe1—C1—C2^iii	98.45 (9)	C2^ii—Fe1—C2—C5	21.80 (12)
C3^iii—Fe1—C1—C2^iii	−37.62 (8)	C1—C2—C3—C3^iii	−0.12 (12)
C2—Fe1—C1—C2^iii	−119.17 (15)	C5—C2—C3—C3^iii	177.39 (11)
C2^i—Fe1—C1—C2^iii	60.83 (15)	Fe1—C2—C3—C3^iii	−59.26 (3)
C2^ii—Fe1—C1—C2^iii	180.0	C1—C2—C3—C6	−177.68 (13)
C1^i—Fe1—C1—C4	−108.8 (16)	C5—C2—C3—C6	−0.2 (2)
C3—Fe1—C1—C4	158.04 (4)	Fe1—C2—C3—C6	123.18 (13)
C3^ii—Fe1—C1—C4	21.96 (4)	C1—C2—C3—Fe1	59.14 (10)
C3^i—Fe1—C1—C4	−21.96 (4)	C5—C2—C3—Fe1	−123.36 (13)
C3^iii—Fe1—C1—C4	−158.04 (4)	C1—Fe1—C3—C3^iii	81.65 (3)
C2^iii—Fe1—C1—C4	−120.41 (8)	C1^i—Fe1—C3—C3^iii	−98.35 (3)
C2—Fe1—C1—C4	120.41 (8)	C3^ii—Fe1—C3—C3^iii	180.0
C2^i—Fe1—C1—C4	−59.58 (8)	C3^i—Fe1—C3—C3^iii	−3.43 (4)
C2^ii—Fe1—C1—C4	59.58 (8)	C2^iii—Fe1—C3—C3^iii	37.72 (5)
C2^iii—C1—C2—C3	0.19 (19)	C2—Fe1—C3—C3^iii	119.27 (7)
C4—C1—C2—C3	179.77 (16)	C2^i—Fe1—C3—C3^iii	−60.73 (7)
Fe1—C1—C2—C3	−59.18 (9)	C2^ii—Fe1—C3—C3^iii	−142.28 (5)
C2^iii—C1—C2—C5	−177.31 (9)	C1—Fe1—C3—C2	−37.62 (7)
C4—C1—C2—C5	2.3 (3)	C1^i—Fe1—C3—C2	142.38 (7)
Fe1—C1—C2—C5	123.32 (13)	C3^ii—Fe1—C3—C2	60.72 (7)
C2^iii—C1—C2—Fe1	59.37 (11)	C3^i—Fe1—C3—C2	−122.71 (9)
C4—C1—C2—Fe1	−121.05 (18)	C3^iii—Fe1—C3—C2	−119.27 (7)
C1—Fe1—C2—C3	119.46 (11)	C2^iii—Fe1—C3—C2	−81.55 (10)
C1^i—Fe1—C2—C3	−60.54 (11)	C2^i—Fe1—C3—C2	180.0
C3^ii—Fe1—C2—C3	−142.28 (8)	C2^ii—Fe1—C3—C2	98.45 (10)
C3^i—Fe1—C2—C3	180.0	C1—Fe1—C3—C6	−157.85 (13)
C3^iii—Fe1—C2—C3	37.72 (8)	C1^i—Fe1—C3—C6	22.15 (13)
C2^iii—Fe1—C2—C3	81.67 (8)	C3^ii—Fe1—C3—C6	−59.51 (11)
C2^i—Fe1—C2—C3	−147.91 (7)	C3^i—Fe1—C3—C6	117.06 (11)
C2^ii—Fe1—C2—C3	−98.33 (8)	C3^iii—Fe1—C3—C6	120.49 (11)
C1^i—Fe1—C2—C1	180.0	C2^iii—Fe1—C3—C6	158.21 (13)
C3—Fe1—C2—C1	−119.46 (11)	C2—Fe1—C3—C6	−120.23 (14)
C3^ii—Fe1—C2—C1	98.27 (9)	C2^i—Fe1—C3—C6	59.77 (14)
C3^i—Fe1—C2—C1	60.54 (11)	C2^ii—Fe1—C3—C6	−21.79 (13)
C3^iii—Fe1—C2—C1	−81.73 (9)

Symmetry codes: (i) −x, −y, −z; (ii) x, −y, −z; (iii) −x, y, z.

(FC_IAM_80)

Crystal data

C20H30Fe	V = 1722.6 (2) Å^3
Mr = 326.29	Z = 4
a = 15.0905 (10) Å	F(000) = 704
b = 11.4741 (8) Å	Dx = 1.258 Mg m^−3
c = 9.9484 (6) Å	Mo Kα radiation, λ = 0.71073 Å
α = 90°	µ = 0.87 mm^−1
β = 90°	T = 90 K
γ = 90°

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 40.0°, θmin = 3.0°
2676 measured reflections	h = 0→27
2676 independent reflections	k = 0→20
2430 reflections with I > 2σ(I)	l = 0→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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0332P)^2 + 0.5477P] where P = (Fo^2 + 2Fc^2)/3
2676 reflections	(Δ/σ)max = 0.005
84 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

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.

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 > 2sigma(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
Fe1	0.0000	0.0000	0.0000	0.00914 (4)
C1	0.0000	−0.17512 (6)	0.04196 (7)	0.01630 (11)
C2	−0.07678 (3)	−0.12035 (5)	0.09886 (5)	0.01488 (8)
C3	−0.04743 (3)	−0.03166 (4)	0.18982 (5)	0.01210 (7)
C4	0.0000	−0.27285 (7)	−0.05779 (9)	0.0293 (2)
C5	−0.17110 (5)	−0.15343 (7)	0.07266 (8)	0.02706 (13)
C6	−0.10577 (4)	0.04401 (6)	0.27489 (6)	0.02036 (10)
H1	0.0000	−0.347 (2)	−0.0130 (18)	0.031 (5)*
H2	−0.0476 (9)	−0.2701 (15)	−0.1170 (16)	0.056 (5)*
H4	−0.1786 (11)	−0.1791 (15)	−0.0153 (15)	0.039 (4)*
H3	−0.1898 (9)	−0.2141 (12)	0.1364 (14)	0.037 (3)*
H5	−0.2103 (9)	−0.0869 (13)	0.0795 (15)	0.039 (4)*
H7	−0.1628 (9)	0.0578 (12)	0.2263 (13)	0.031 (3)*
H6	−0.1156 (11)	0.0068 (12)	0.3598 (19)	0.035 (4)*
H8	−0.0777 (10)	0.1196 (14)	0.2929 (16)	0.040 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01118 (6)	0.00841 (6)	0.00783 (6)	0.000	0.000	−0.00029 (3)
C1	0.0279 (3)	0.0097 (2)	0.0113 (2)	0.000	0.000	−0.00054 (18)
C2	0.01716 (18)	0.01427 (17)	0.01322 (16)	−0.00491 (14)	−0.00201 (13)	0.00193 (13)
C3	0.01273 (15)	0.01317 (16)	0.01038 (15)	−0.00007 (12)	0.00147 (12)	0.00037 (12)
C4	0.0625 (7)	0.0113 (3)	0.0140 (3)	0.000	0.000	−0.0024 (2)
C5	0.0228 (2)	0.0306 (3)	0.0278 (3)	−0.0149 (2)	−0.0083 (2)	0.0094 (2)
C6	0.0217 (2)	0.0229 (2)	0.0165 (2)	0.00609 (18)	0.00751 (16)	0.00084 (17)

Geometric parameters (Å, º)

Fe1—C1	2.0522 (7)	C2—C3	1.4321 (7)
Fe1—C1^i	2.0522 (7)	C2—C5	1.4960 (8)
Fe1—C3	2.0519 (5)	C3—C3^iii	1.4315 (9)
Fe1—C3^ii	2.0519 (5)	C3—C6	1.4984 (7)
Fe1—C3^i	2.0519 (5)	C4—H1	0.96 (2)
Fe1—C3^iii	2.0520 (5)	C4—H2	0.929 (15)
Fe1—C2^iii	2.0534 (5)	C5—H4	0.931 (15)
Fe1—C2	2.0535 (5)	C5—H3	0.983 (14)
Fe1—C2^i	2.0535 (5)	C5—H5	0.968 (15)
Fe1—C2^ii	2.0535 (5)	C6—H7	0.999 (13)
C1—C2	1.4344 (7)	C6—H6	0.958 (18)
C1—C2^iii	1.4345 (7)	C6—H8	0.982 (16)
C1—C4	1.4974 (11)
C1—Fe1—C1^i	180.0	C3^ii—Fe1—C2^ii	40.83 (2)
C1—Fe1—C3	68.87 (2)	C3^i—Fe1—C2^ii	68.715 (19)
C1^i—Fe1—C3	111.13 (2)	C3^iii—Fe1—C2^ii	139.17 (2)
C1—Fe1—C3^ii	111.13 (2)	C2^iii—Fe1—C2^ii	180.0
C1^i—Fe1—C3^ii	68.87 (2)	C2—Fe1—C2^ii	111.30 (3)
C3—Fe1—C3^ii	139.17 (3)	C2^i—Fe1—C2^ii	68.70 (3)
C1—Fe1—C3^i	111.13 (2)	C2—C1—C2^iii	107.75 (6)
C1^i—Fe1—C3^i	68.87 (2)	C2—C1—C4	126.12 (3)
C3—Fe1—C3^i	180.00 (3)	C2^iii—C1—C4	126.13 (3)
C3^ii—Fe1—C3^i	40.83 (3)	C2—C1—Fe1	69.60 (3)
C1—Fe1—C3^iii	68.87 (2)	C2^iii—C1—Fe1	69.60 (3)
C1^i—Fe1—C3^iii	111.13 (2)	C4—C1—Fe1	126.76 (5)
C3—Fe1—C3^iii	40.83 (3)	C3—C2—C1	108.11 (4)
C3^ii—Fe1—C3^iii	180.0	C3—C2—C5	125.78 (6)
C3^i—Fe1—C3^iii	139.17 (3)	C1—C2—C5	126.06 (6)
C1—Fe1—C2^iii	40.900 (19)	C3—C2—Fe1	69.53 (3)
C1^i—Fe1—C2^iii	139.099 (19)	C1—C2—Fe1	69.50 (3)
C3—Fe1—C2^iii	68.71 (2)	C5—C2—Fe1	128.61 (4)
C3^ii—Fe1—C2^iii	139.17 (2)	C3^iii—C3—C2	108.01 (3)
C3^i—Fe1—C2^iii	111.284 (19)	C3^iii—C3—C6	125.98 (3)
C3^iii—Fe1—C2^iii	40.83 (2)	C2—C3—C6	125.95 (5)
C1—Fe1—C2	40.899 (19)	C3^iii—C3—Fe1	69.586 (13)
C1^i—Fe1—C2	139.102 (19)	C2—C3—Fe1	69.64 (3)
C3—Fe1—C2	40.83 (2)	C6—C3—Fe1	128.48 (4)
C3^ii—Fe1—C2	111.284 (19)	C1—C4—H1	110.9 (11)
C3^i—Fe1—C2	139.17 (2)	C1—C4—H2	113.3 (11)
C3^iii—Fe1—C2	68.715 (19)	H1—C4—H2	108.8 (12)
C2^iii—Fe1—C2	68.70 (3)	C2—C5—H4	111.1 (11)
C1—Fe1—C2^i	139.101 (19)	C2—C5—H3	109.9 (8)
C1^i—Fe1—C2^i	40.898 (19)	H4—C5—H3	110.3 (13)
C3—Fe1—C2^i	139.17 (2)	C2—C5—H5	111.7 (8)
C3^ii—Fe1—C2^i	68.715 (19)	H4—C5—H5	104.0 (14)
C3^i—Fe1—C2^i	40.83 (2)	H3—C5—H5	109.7 (12)
C3^iii—Fe1—C2^i	111.286 (19)	C3—C6—H7	108.9 (8)
C2^iii—Fe1—C2^i	111.30 (3)	C3—C6—H6	109.3 (9)
C2—Fe1—C2^i	180.0	H7—C6—H6	111.3 (12)
C1—Fe1—C2^ii	139.101 (19)	C3—C6—H8	111.2 (9)
C1^i—Fe1—C2^ii	40.901 (19)	H7—C6—H8	108.7 (12)
C3—Fe1—C2^ii	111.286 (19)	H6—C6—H8	107.4 (13)
C1^i—Fe1—C1—C2	130.8 (8)	C2^iii—Fe1—C2—C1	−37.91 (4)
C3—Fe1—C1—C2	37.56 (3)	C2^i—Fe1—C2—C1	92.55 (3)
C3^ii—Fe1—C1—C2	−98.52 (3)	C2^ii—Fe1—C2—C1	142.09 (4)
C3^i—Fe1—C1—C2	−142.44 (3)	C1—Fe1—C2—C5	−120.38 (7)
C3^iii—Fe1—C1—C2	81.48 (3)	C1^i—Fe1—C2—C5	59.62 (7)
C2^iii—Fe1—C1—C2	119.03 (6)	C3—Fe1—C2—C5	120.03 (7)
C2^i—Fe1—C1—C2	180.0	C3^ii—Fe1—C2—C5	−22.26 (7)
C2^ii—Fe1—C1—C2	−60.97 (6)	C3^i—Fe1—C2—C5	−59.97 (7)
C1^i—Fe1—C1—C2^iii	11.8 (8)	C3^iii—Fe1—C2—C5	157.74 (7)
C3—Fe1—C1—C2^iii	−81.48 (3)	C2^iii—Fe1—C2—C5	−158.29 (6)
C3^ii—Fe1—C1—C2^iii	142.44 (3)	C2^i—Fe1—C2—C5	−27.83 (6)
C3^i—Fe1—C1—C2^iii	98.52 (3)	C2^ii—Fe1—C2—C5	21.71 (6)
C3^iii—Fe1—C1—C2^iii	−37.56 (3)	C1—C2—C3—C3^iii	−0.23 (5)
C2—Fe1—C1—C2^iii	−119.03 (6)	C5—C2—C3—C3^iii	177.29 (5)
C2^i—Fe1—C1—C2^iii	60.97 (6)	Fe1—C2—C3—C3^iii	−59.211 (14)
C2^ii—Fe1—C1—C2^iii	180.0	C1—C2—C3—C6	−177.61 (5)
C1^i—Fe1—C1—C4	−108.7 (8)	C5—C2—C3—C6	−0.09 (9)
C3—Fe1—C1—C4	158.039 (14)	Fe1—C2—C3—C6	123.42 (5)
C3^ii—Fe1—C1—C4	21.962 (15)	C1—C2—C3—Fe1	58.98 (4)
C3^i—Fe1—C1—C4	−21.962 (15)	C5—C2—C3—Fe1	−123.50 (6)
C3^iii—Fe1—C1—C4	−158.038 (14)	C1—Fe1—C3—C3^iii	81.727 (11)
C2^iii—Fe1—C1—C4	−120.48 (3)	C1^i—Fe1—C3—C3^iii	−98.271 (11)
C2—Fe1—C1—C4	120.48 (3)	C3^ii—Fe1—C3—C3^iii	180.0
C2^i—Fe1—C1—C4	−59.52 (3)	C3^i—Fe1—C3—C3^iii	−3.412 (13)
C2^ii—Fe1—C1—C4	59.52 (3)	C2^iii—Fe1—C3—C3^iii	37.71 (2)
C2^iii—C1—C2—C3	0.37 (8)	C2—Fe1—C3—C3^iii	119.34 (3)
C4—C1—C2—C3	179.74 (7)	C2^i—Fe1—C3—C3^iii	−60.66 (3)
Fe1—C1—C2—C3	−58.99 (4)	C2^ii—Fe1—C3—C3^iii	−142.29 (2)
C2^iii—C1—C2—C5	−177.14 (4)	C1—Fe1—C3—C2	−37.62 (3)
C4—C1—C2—C5	2.23 (11)	C1^i—Fe1—C3—C2	142.38 (3)
Fe1—C1—C2—C5	123.50 (6)	C3^ii—Fe1—C3—C2	60.65 (3)
C2^iii—C1—C2—Fe1	59.36 (5)	C3^i—Fe1—C3—C2	−122.76 (3)
C4—C1—C2—Fe1	−121.26 (7)	C3^iii—Fe1—C3—C2	−119.34 (3)
C1—Fe1—C2—C3	119.59 (4)	C2^iii—Fe1—C3—C2	−81.64 (4)
C1^i—Fe1—C2—C3	−60.41 (4)	C2^i—Fe1—C3—C2	180.0
C3^ii—Fe1—C2—C3	−142.29 (3)	C2^ii—Fe1—C3—C2	98.36 (4)
C3^i—Fe1—C2—C3	180.0	C1—Fe1—C3—C6	−157.94 (5)
C3^iii—Fe1—C2—C3	37.71 (3)	C1^i—Fe1—C3—C6	22.06 (5)
C2^iii—Fe1—C2—C3	81.68 (3)	C3^ii—Fe1—C3—C6	−59.67 (5)
C2^i—Fe1—C2—C3	−147.86 (3)	C3^i—Fe1—C3—C6	116.92 (5)
C2^ii—Fe1—C2—C3	−98.32 (3)	C3^iii—Fe1—C3—C6	120.33 (5)
C1^i—Fe1—C2—C1	180.0	C2^iii—Fe1—C3—C6	158.04 (5)
C3—Fe1—C2—C1	−119.59 (4)	C2—Fe1—C3—C6	−120.32 (6)
C3^ii—Fe1—C2—C1	98.12 (3)	C2^i—Fe1—C3—C6	59.68 (6)
C3^i—Fe1—C2—C1	60.41 (4)	C2^ii—Fe1—C3—C6	−21.96 (5)
C3^iii—Fe1—C2—C1	−81.88 (3)

Symmetry codes: (i) −x, −y, −z; (ii) x, −y, −z; (iii) −x, y, z.

(FC_N_100)

Crystal data

C20H30Fe	V = 1731.7 (8) Å^3
Mr = 326.31	Z = 4
a = 15.119 (4) Å	F(000) = 121
b = 11.492 (3) Å	Dx = 1.252 Mg m^−3
c = 9.967 (3) Å	Mo Kα radiation, λ = 0.71073 Å
α = 90°	µ = 0.24 mm^−1
β = 90°	T = 293 K
γ = 90°	1.00 × 1.00 × 1.00 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 82.9°, θmin = 8.7°
3378 measured reflections	h = −33→49
3378 independent reflections	k = −26→17
3378 reflections with I > 2σ(I)	l = −22→20

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)] = 0.089	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.244	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.88	(Δ/σ)max < 0.001
3378 reflections	Δρmax = 3.16 e Å^−3
125 parameters	Δρmin = −1.50 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.000097 (18)

Special details

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.

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 > 2sigma(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
Fe1	0.0000	0.0000	0.0000	0.0079 (6)
C1	0.0000	−0.1752 (3)	0.0418 (3)	0.0131 (7)
C2	0.07671 (13)	−0.1202 (2)	0.0984 (2)	0.0120 (5)
C3	0.04739 (13)	−0.0314 (2)	0.1897 (2)	0.0101 (5)
C4	0.0000	−0.2735 (4)	−0.0576 (4)	0.0260 (10)
H1	0.0000	−0.3592 (9)	−0.0092 (10)	0.052 (3)
H2	0.0590 (6)	−0.2710 (8)	−0.1206 (7)	0.071 (3)
C5	0.17123 (16)	−0.1533 (3)	0.0730 (3)	0.0258 (7)
H3	0.1944 (4)	−0.2172 (7)	0.1431 (7)	0.053 (2)
H4	0.1797 (5)	−0.1880 (9)	−0.0267 (7)	0.066 (3)
H5	0.2152 (4)	−0.0804 (8)	0.0777 (9)	0.063 (2)
C6	0.10574 (16)	0.0432 (3)	0.2751 (2)	0.0181 (6)
H6	0.1192 (4)	0.0023 (7)	0.3715 (6)	0.0455 (17)
H7	0.1693 (4)	0.0601 (7)	0.2285 (7)	0.0494 (19)
H8	0.0755 (4)	0.1276 (6)	0.2946 (7)	0.0420 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0075 (10)	0.009 (2)	0.0075 (14)	0.000	0.000	0.0013 (12)
C1	0.0245 (14)	0.002 (2)	0.0131 (15)	0.000	0.000	−0.0012 (12)
C2	0.0145 (8)	0.0099 (14)	0.0117 (11)	0.0059 (9)	0.0016 (8)	0.0024 (9)
C3	0.0086 (7)	0.0112 (14)	0.0106 (10)	−0.0002 (8)	−0.0020 (8)	0.0008 (8)
C4	0.058 (2)	0.007 (3)	0.0131 (18)	0.000	0.000	−0.0034 (17)
H1	0.110 (8)	0.010 (6)	0.037 (5)	0.000	0.000	−0.001 (4)
H2	0.120 (7)	0.042 (6)	0.052 (4)	−0.006 (4)	0.047 (5)	−0.023 (4)
C5	0.0187 (10)	0.032 (2)	0.0267 (15)	0.0138 (12)	0.0085 (10)	0.0093 (14)
H3	0.034 (3)	0.062 (6)	0.063 (4)	0.023 (3)	0.008 (3)	0.027 (4)
H4	0.061 (4)	0.097 (8)	0.040 (4)	0.047 (4)	0.019 (3)	−0.009 (4)
H5	0.025 (3)	0.052 (6)	0.111 (7)	0.000 (3)	0.019 (3)	0.018 (5)
C6	0.0179 (9)	0.0228 (19)	0.0136 (12)	−0.0064 (12)	−0.0079 (9)	0.0016 (11)
H6	0.060 (4)	0.047 (5)	0.030 (3)	−0.013 (3)	−0.026 (3)	0.007 (3)
H7	0.029 (2)	0.074 (6)	0.045 (4)	−0.022 (3)	0.001 (3)	−0.002 (3)
H8	0.046 (3)	0.029 (4)	0.051 (4)	0.002 (3)	−0.011 (3)	−0.012 (3)

Geometric parameters (Å, º)

Fe1—C2^i	2.053 (2)	C2—C3	1.437 (3)
Fe1—C2	2.053 (2)	C2—C5	1.500 (3)
Fe1—C2^ii	2.053 (2)	C3—C3^i	1.433 (4)
Fe1—C2^iii	2.053 (2)	C3—C6	1.496 (3)
Fe1—C3^i	2.054 (2)	C4—H4A	1.096 (12)
Fe1—C3	2.054 (2)	C4—H4B	1.092 (8)
Fe1—C3^iii	2.054 (2)	C5—H5B	1.073 (8)
Fe1—C3^ii	2.054 (2)	C5—H5A	1.078 (8)
Fe1—C1	2.056 (4)	C5—H5C	1.070 (9)
Fe1—C1^iii	2.056 (4)	C6—H6B	1.089 (7)
C1—C2	1.436 (3)	C6—H6A	1.085 (6)
C1—C2^i	1.436 (3)	C6—H6C	1.089 (8)
C1—C4	1.502 (5)
C2^i—Fe1—C2	68.77 (13)	C2^iii—Fe1—C1^iii	40.91 (8)
C2^i—Fe1—C2^ii	180.00 (11)	C3^i—Fe1—C1^iii	111.02 (11)
C2—Fe1—C2^ii	111.23 (13)	C3—Fe1—C1^iii	111.02 (11)
C2^i—Fe1—C2^iii	111.23 (13)	C3^iii—Fe1—C1^iii	68.98 (11)
C2—Fe1—C2^iii	180.00 (17)	C3^ii—Fe1—C1^iii	68.98 (11)
C2^ii—Fe1—C2^iii	68.77 (13)	C1—Fe1—C1^iii	180.0
C2^i—Fe1—C3^i	40.97 (10)	C2—C1—C2^i	107.7 (3)
C2—Fe1—C3^i	68.84 (9)	C2—C1—C4	126.14 (15)
C2^ii—Fe1—C3^i	139.03 (10)	C2^i—C1—C4	126.14 (15)
C2^iii—Fe1—C3^i	111.16 (9)	C2—C1—Fe1	69.44 (18)
C2^i—Fe1—C3	68.84 (9)	C2^i—C1—Fe1	69.44 (18)
C2—Fe1—C3	40.97 (10)	C4—C1—Fe1	127.0 (3)
C2^ii—Fe1—C3	111.16 (9)	C1—C2—C3	108.18 (19)
C2^iii—Fe1—C3	139.03 (10)	C1—C2—C5	126.3 (2)
C3^i—Fe1—C3	40.84 (11)	C3—C2—C5	125.5 (2)
C2^i—Fe1—C3^iii	111.16 (9)	C1—C2—Fe1	69.65 (16)
C2—Fe1—C3^iii	139.03 (10)	C3—C2—Fe1	69.52 (13)
C2^ii—Fe1—C3^iii	68.84 (9)	C5—C2—Fe1	128.85 (17)
C2^iii—Fe1—C3^iii	40.97 (10)	C3^i—C3—C2	107.96 (12)
C3^i—Fe1—C3^iii	139.16 (11)	C3^i—C3—C6	126.13 (13)
C3—Fe1—C3^iii	180.0	C2—C3—C6	125.83 (19)
C2^i—Fe1—C3^ii	139.03 (10)	C3^i—C3—Fe1	69.58 (6)
C2—Fe1—C3^ii	111.16 (9)	C2—C3—Fe1	69.51 (12)
C2^ii—Fe1—C3^ii	40.97 (10)	C6—C3—Fe1	128.99 (19)
C2^iii—Fe1—C3^ii	68.84 (9)	C1—C4—H1	112.6 (6)
C3^i—Fe1—C3^ii	180.00 (10)	C1—C4—H2	111.1 (5)
C3—Fe1—C3^ii	139.16 (11)	H1—C4—H2	106.1 (6)
C3^iii—Fe1—C3^ii	40.84 (11)	C2—C5—H4	111.9 (4)
C2^i—Fe1—C1	40.91 (8)	C2—C5—H3	111.2 (4)
C2—Fe1—C1	40.91 (8)	H3—C5—H3	108.0 (7)
C2^ii—Fe1—C1	139.09 (8)	C2—C5—H5	112.7 (5)
C2^iii—Fe1—C1	139.09 (8)	H3—C5—H5	107.7 (6)
C3^i—Fe1—C1	68.98 (11)	H4—C5—H5	104.9 (7)
C3—Fe1—C1	68.98 (11)	C3—C6—H7	111.4 (5)
C3^iii—Fe1—C1	111.02 (11)	C3—C6—H6	112.4 (4)
C3^ii—Fe1—C1	111.02 (11)	H6—C6—H6	106.9 (6)
C2^i—Fe1—C1^iii	139.09 (8)	C3—C6—H8	111.3 (4)
C2—Fe1—C1^iii	139.09 (8)	H6—C6—H8	107.8 (6)
C2^ii—Fe1—C1^iii	40.91 (8)	H7—C6—H8	106.7 (6)

Symmetry codes: (i) −x, y, z; (ii) x, −y, −z; (iii) −x, −y, −z.

(T_IAM_50)

Crystal data

C20H14	Z = 4
Mr = 254.31	F(000) = 536
Orthorhombic, P212121	Dx = 1.257 Mg m^−3
a = 8.0798 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1645 (3) Å	µ = 0.07 mm^−1
c = 20.3778 (8) Å	T = 100 K
V = 1344.27 (9) Å^3	0.33 × 0.18 × 0.14 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 2.7°
2367 measured reflections	h = 0→9
2367 independent reflections	k = 0→9
2335 reflections with I > 2σ(I)	l = −23→24

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)] = 0.025	All H-atom parameters refined
wR(F^2) = 0.063	w = 1/[σ^2(Fo^2) + (0.0216P)^2 + 0.294P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2367 reflections	Δρmax = 0.13 e Å^−3
237 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 1 (8)

Special details

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.

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 > 2sigma(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
C1	0.43191 (15)	0.88604 (15)	0.17452 (6)	0.0176 (3)
C2	0.24538 (14)	1.09410 (14)	0.11293 (6)	0.0165 (3)
C3	0.31839 (14)	0.98300 (14)	0.22008 (6)	0.0176 (2)
C4	0.30689 (16)	0.96574 (15)	0.28750 (6)	0.0204 (3)
C5	0.19332 (17)	1.06136 (16)	0.32167 (6)	0.0232 (3)
C6	0.09330 (16)	1.17249 (15)	0.28909 (6)	0.0230 (3)
C7	0.10602 (15)	1.19170 (14)	0.22116 (6)	0.0197 (3)
C8	0.21805 (14)	1.09592 (14)	0.18710 (6)	0.0170 (2)
C9	0.31595 (15)	0.80530 (15)	0.12502 (5)	0.0173 (3)
C10	0.30107 (16)	0.63904 (15)	0.11255 (6)	0.0204 (3)
C11	0.18553 (17)	0.58556 (15)	0.06650 (6)	0.0230 (3)
C12	0.08639 (17)	0.69644 (16)	0.03330 (6)	0.0231 (3)
C13	0.10071 (16)	0.86341 (15)	0.04587 (6)	0.0199 (3)
C14	0.21464 (15)	0.91724 (14)	0.09171 (6)	0.0169 (3)
C15	0.53069 (15)	1.01307 (14)	0.13612 (5)	0.0175 (2)
C16	0.70074 (15)	1.02610 (15)	0.13256 (6)	0.0194 (3)
C17	0.77070 (15)	1.15081 (16)	0.09482 (6)	0.0204 (3)
C18	0.67154 (15)	1.26024 (15)	0.06092 (6)	0.0187 (3)
C19	0.49950 (15)	1.24751 (14)	0.06456 (6)	0.0168 (3)
C20	0.42998 (14)	1.12479 (14)	0.10236 (5)	0.0166 (2)
H7	0.0355 (17)	1.2704 (17)	0.1985 (6)	0.017 (3)*
H1	0.5027 (17)	0.8051 (17)	0.1975 (7)	0.019 (3)*
H19	0.4288 (17)	1.3262 (17)	0.0409 (7)	0.018 (3)*
H10	0.3720 (18)	0.5603 (17)	0.1368 (7)	0.021 (3)*
H2	0.1735 (18)	1.1769 (17)	0.0891 (7)	0.021 (3)*
H16	0.7724 (19)	0.9504 (18)	0.1565 (7)	0.025 (4)*
H13	0.0279 (18)	0.9435 (17)	0.0212 (7)	0.020 (3)*
H6	0.0126 (19)	1.2367 (19)	0.3135 (8)	0.030 (4)*
H5	0.1854 (18)	1.0501 (18)	0.3688 (7)	0.024 (4)*
H4	0.3796 (17)	0.8849 (18)	0.3105 (7)	0.020 (3)*
H17	0.8929 (18)	1.1594 (16)	0.0934 (6)	0.017 (3)*
H11	0.1756 (19)	0.4682 (19)	0.0574 (7)	0.029 (4)*
H18	0.7234 (17)	1.3504 (17)	0.0338 (7)	0.016 (3)*
H12	0.0052 (19)	0.6581 (19)	0.0012 (7)	0.026 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0179 (6)	0.0172 (6)	0.0178 (5)	0.0028 (5)	−0.0007 (5)	0.0019 (5)
C2	0.0158 (6)	0.0159 (6)	0.0179 (6)	0.0010 (5)	−0.0004 (5)	0.0009 (4)
C3	0.0171 (5)	0.0164 (5)	0.0194 (5)	−0.0027 (5)	0.0005 (5)	−0.0002 (5)
C4	0.0222 (6)	0.0194 (6)	0.0194 (6)	−0.0044 (5)	−0.0012 (5)	0.0006 (5)
C5	0.0272 (7)	0.0259 (6)	0.0166 (6)	−0.0082 (6)	0.0033 (5)	−0.0018 (5)
C6	0.0205 (6)	0.0228 (6)	0.0256 (6)	−0.0052 (5)	0.0053 (5)	−0.0078 (5)
C7	0.0175 (6)	0.0168 (5)	0.0249 (6)	−0.0015 (5)	0.0007 (5)	−0.0024 (5)
C8	0.0164 (6)	0.0162 (5)	0.0185 (6)	−0.0039 (5)	0.0000 (5)	−0.0005 (4)
C9	0.0155 (6)	0.0200 (6)	0.0165 (5)	0.0009 (5)	0.0029 (5)	0.0003 (4)
C10	0.0209 (6)	0.0182 (6)	0.0220 (6)	0.0031 (5)	0.0046 (5)	0.0012 (5)
C11	0.0259 (6)	0.0170 (6)	0.0260 (6)	−0.0001 (5)	0.0050 (6)	−0.0053 (5)
C12	0.0225 (7)	0.0261 (7)	0.0209 (6)	−0.0021 (6)	0.0002 (5)	−0.0041 (5)
C13	0.0197 (6)	0.0229 (6)	0.0172 (5)	0.0013 (5)	0.0008 (5)	0.0014 (5)
C14	0.0163 (6)	0.0174 (6)	0.0170 (5)	0.0007 (5)	0.0055 (5)	0.0000 (4)
C15	0.0206 (6)	0.0173 (6)	0.0146 (5)	0.0017 (5)	−0.0001 (4)	−0.0030 (5)
C16	0.0181 (6)	0.0214 (6)	0.0186 (5)	0.0039 (5)	−0.0019 (5)	−0.0023 (5)
C17	0.0151 (6)	0.0261 (6)	0.0201 (6)	−0.0012 (5)	0.0017 (5)	−0.0059 (5)
C18	0.0215 (6)	0.0200 (6)	0.0145 (6)	−0.0019 (5)	0.0029 (5)	−0.0029 (5)
C19	0.0204 (6)	0.0160 (6)	0.0141 (5)	0.0007 (5)	−0.0006 (5)	−0.0016 (5)
C20	0.0173 (6)	0.0176 (6)	0.0148 (5)	0.0014 (5)	−0.0003 (4)	−0.0037 (5)

Geometric parameters (Å, º)

C1—C3	1.5264 (16)	C9—C14	1.4022 (17)
C1—C9	1.5264 (17)	C10—C11	1.3938 (19)
C1—C15	1.5248 (17)	C10—H10	0.992 (15)
C1—H1	0.992 (14)	C11—C12	1.3852 (19)
C2—C8	1.5276 (16)	C11—H11	0.979 (16)
C2—C14	1.5276 (16)	C12—C13	1.3919 (18)
C2—C20	1.5276 (16)	C12—H12	0.977 (16)
C2—H2	1.015 (15)	C13—C14	1.3832 (18)
C3—C4	1.3842 (17)	C13—H13	1.013 (15)
C3—C8	1.3996 (17)	C15—C16	1.3800 (17)
C4—C5	1.3915 (18)	C15—C20	1.4027 (17)
C4—H4	1.000 (15)	C16—C17	1.3957 (18)
C5—C6	1.3846 (19)	C16—H16	0.977 (16)
C5—H5	0.968 (15)	C17—C18	1.3847 (18)
C6—C7	1.3968 (18)	C17—H17	0.990 (15)
C6—H6	0.974 (16)	C18—C19	1.3959 (17)
C7—C8	1.3829 (17)	C18—H18	1.011 (14)
C7—H7	0.975 (14)	C19—C20	1.3830 (17)
C9—C10	1.3862 (17)	C19—H19	0.986 (14)
C3—C1—C9	104.90 (9)	C9—C10—C11	119.23 (12)
C3—C1—H1	113.9 (8)	C9—C10—H10	119.5 (8)
C9—C1—H1	112.2 (8)	C11—C10—H10	121.3 (8)
C15—C1—C3	105.90 (10)	C10—C11—H11	119.3 (9)
C15—C1—C9	106.02 (9)	C12—C11—C10	120.76 (12)
C15—C1—H1	113.2 (8)	C12—C11—H11	120.0 (9)
C8—C2—C14	105.41 (9)	C11—C12—C13	120.14 (12)
C8—C2—C20	106.20 (9)	C11—C12—H12	120.4 (9)
C8—C2—H2	112.5 (8)	C13—C12—H12	119.5 (9)
C14—C2—C20	105.90 (9)	C12—C13—H13	119.5 (8)
C14—C2—H2	113.7 (8)	C14—C13—C12	119.39 (12)
C20—C2—H2	112.5 (8)	C14—C13—H13	121.1 (8)
C4—C3—C1	126.24 (11)	C9—C14—C2	112.59 (10)
C4—C3—C8	120.32 (11)	C13—C14—C2	126.85 (11)
C8—C3—C1	113.43 (10)	C13—C14—C9	120.56 (11)
C3—C4—C5	118.93 (11)	C16—C15—C1	126.91 (11)
C3—C4—H4	119.5 (8)	C16—C15—C20	120.11 (11)
C5—C4—H4	121.6 (8)	C20—C15—C1	112.98 (10)
C4—C5—H5	119.2 (9)	C15—C16—C17	119.24 (11)
C6—C5—C4	120.83 (11)	C15—C16—H16	121.0 (9)
C6—C5—H5	120.0 (9)	C17—C16—H16	119.8 (9)
C5—C6—C7	120.39 (12)	C16—C17—H17	118.1 (8)
C5—C6—H6	119.9 (9)	C18—C17—C16	120.75 (11)
C7—C6—H6	119.7 (9)	C18—C17—H17	121.1 (8)
C6—C7—H7	120.0 (8)	C17—C18—C19	120.11 (11)
C8—C7—C6	118.82 (12)	C17—C18—H18	120.2 (8)
C8—C7—H7	121.1 (8)	C19—C18—H18	119.7 (8)
C3—C8—C2	112.64 (10)	C18—C19—H19	120.2 (8)
C7—C8—C2	126.64 (11)	C20—C19—C18	119.21 (11)
C7—C8—C3	120.70 (11)	C20—C19—H19	120.6 (8)
C10—C9—C1	126.68 (12)	C15—C20—C2	112.99 (10)
C10—C9—C14	119.92 (11)	C19—C20—C2	126.44 (11)
C14—C9—C1	113.37 (11)	C19—C20—C15	120.57 (11)
C1—C3—C4—C5	−178.33 (11)	C9—C10—C11—C12	0.09 (18)
C1—C3—C8—C2	0.45 (14)	C10—C9—C14—C2	178.59 (10)
C1—C3—C8—C7	178.91 (10)	C10—C9—C14—C13	−0.66 (17)
C1—C9—C10—C11	178.51 (11)	C10—C11—C12—C13	−0.28 (19)
C1—C9—C14—C2	0.22 (14)	C11—C12—C13—C14	0.00 (19)
C1—C9—C14—C13	−179.03 (10)	C12—C13—C14—C2	−178.66 (12)
C1—C15—C16—C17	−179.99 (11)	C12—C13—C14—C9	0.47 (18)
C1—C15—C20—C2	0.85 (14)	C14—C2—C8—C3	56.21 (12)
C1—C15—C20—C19	−179.45 (11)	C14—C2—C8—C7	−122.14 (12)
C3—C1—C9—C10	−122.26 (13)	C14—C2—C20—C15	−56.51 (12)
C3—C1—C9—C14	55.97 (12)	C14—C2—C20—C19	123.81 (12)
C3—C1—C15—C16	123.62 (13)	C14—C9—C10—C11	0.38 (18)
C3—C1—C15—C20	−56.05 (12)	C15—C1—C3—C4	−125.63 (12)
C3—C4—C5—C6	−0.14 (18)	C15—C1—C3—C8	55.47 (12)
C4—C3—C8—C2	−178.52 (11)	C15—C1—C9—C10	125.95 (12)
C4—C3—C8—C7	−0.06 (17)	C15—C1—C9—C14	−55.82 (13)
C4—C5—C6—C7	−0.66 (18)	C15—C16—C17—C18	−0.31 (17)
C5—C6—C7—C8	1.08 (17)	C16—C15—C20—C2	−178.85 (10)
C6—C7—C8—C2	177.50 (11)	C16—C15—C20—C19	0.85 (17)
C6—C7—C8—C3	−0.73 (17)	C16—C17—C18—C19	0.46 (17)
C8—C2—C14—C9	−56.58 (12)	C17—C18—C19—C20	0.05 (18)
C8—C2—C14—C13	122.62 (12)	C18—C19—C20—C2	178.95 (11)
C8—C2—C20—C15	55.23 (13)	C18—C19—C20—C15	−0.70 (17)
C8—C2—C20—C19	−124.44 (12)	C20—C2—C8—C3	−55.87 (12)
C8—C3—C4—C5	0.50 (17)	C20—C2—C8—C7	125.77 (12)
C9—C1—C3—C4	122.50 (12)	C20—C2—C14—C9	55.73 (12)
C9—C1—C3—C8	−56.40 (13)	C20—C2—C14—C13	−125.08 (12)
C9—C1—C15—C16	−125.29 (12)	C20—C15—C16—C17	−0.34 (17)
C9—C1—C15—C20	55.04 (13)

(T_IAM_80)

Crystal data

C20H14	Z = 4
Mr = 254.31	F(000) = 536
Orthorhombic, P212121	Dx = 1.257 Mg m^−3
a = 8.0798 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1645 (3) Å	µ = 0.07 mm^−1
c = 20.3778 (8) Å	T = 100 K
V = 1344.27 (9) Å^3	0.33 × 0.18 × 0.14 mm

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 40.0°, θmin = 2.7°
8328 measured reflections	h = 0→14
8328 independent reflections	k = 0→14
8089 reflections with I > 2σ(I)	l = −36→36

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)] = 0.033	All H-atom parameters refined
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0629P)^2 + 0.0373P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
8328 reflections	Δρmax = 0.57 e Å^−3
237 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 2 (8)

Special details

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.

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 > 2sigma(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
C1	0.43212 (6)	0.88578 (6)	0.17454 (2)	0.01215 (7)
C2	0.24549 (6)	1.09418 (6)	0.11289 (2)	0.01090 (7)
C3	0.31903 (6)	0.98269 (6)	0.22001 (2)	0.01207 (7)
C4	0.30760 (7)	0.96512 (7)	0.28753 (2)	0.01532 (8)
C5	0.19354 (8)	1.06108 (7)	0.32207 (3)	0.01811 (9)
C6	0.09335 (7)	1.17276 (7)	0.28929 (3)	0.01753 (9)
C7	0.10577 (6)	1.19185 (6)	0.22109 (3)	0.01463 (8)
C8	0.21827 (6)	1.09578 (6)	0.18695 (2)	0.01166 (7)
C9	0.31626 (6)	0.80521 (6)	0.12507 (2)	0.01196 (7)
C10	0.30166 (7)	0.63879 (6)	0.11265 (3)	0.01580 (8)
C11	0.18541 (8)	0.58505 (7)	0.06644 (3)	0.01835 (9)
C12	0.08585 (8)	0.69631 (7)	0.03315 (3)	0.01772 (9)
C13	0.10039 (7)	0.86407 (6)	0.04583 (2)	0.01437 (7)
C14	0.21510 (6)	0.91768 (6)	0.09182 (2)	0.01140 (7)
C15	0.53031 (6)	1.01293 (6)	0.13618 (2)	0.01180 (7)
C16	0.70112 (6)	1.02597 (7)	0.13266 (3)	0.01464 (7)
C17	0.77113 (6)	1.15087 (7)	0.09473 (3)	0.01535 (8)
C18	0.67169 (6)	1.26062 (6)	0.06081 (2)	0.01392 (7)
C19	0.49914 (6)	1.24792 (6)	0.06450 (2)	0.01211 (7)
C20	0.42948 (6)	1.12481 (5)	0.10242 (2)	0.01095 (7)
H7	0.0418 (17)	1.2687 (16)	0.1981 (6)	0.025 (3)*
H1	0.5057 (16)	0.8019 (17)	0.1963 (7)	0.028 (3)*
H19	0.4284 (14)	1.3264 (15)	0.0406 (6)	0.016 (2)*
H10	0.3705 (16)	0.5590 (16)	0.1358 (6)	0.023 (3)*
H2	0.1750 (14)	1.1802 (14)	0.0898 (6)	0.017 (2)*
H16	0.7698 (17)	0.9522 (18)	0.1556 (7)	0.033 (3)*
H13	0.0248 (15)	0.9425 (15)	0.0205 (6)	0.021 (3)*
H6	0.0125 (17)	1.2328 (17)	0.3148 (7)	0.029 (3)*
H5	0.1864 (16)	1.0449 (17)	0.3689 (7)	0.027 (3)*
H4	0.3791 (17)	0.8847 (17)	0.3094 (7)	0.031 (3)*
H17	0.8913 (16)	1.1643 (15)	0.0932 (6)	0.022 (3)*
H11	0.1736 (17)	0.4682 (16)	0.0569 (7)	0.028 (3)*
H18	0.7307 (17)	1.3508 (17)	0.0362 (6)	0.026 (3)*
H12	0.0091 (17)	0.6586 (17)	0.0014 (7)	0.026 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.01216 (16)	0.01219 (15)	0.01210 (15)	0.00245 (12)	−0.00070 (12)	0.00120 (12)
C2	0.00963 (15)	0.01135 (14)	0.01170 (15)	0.00136 (11)	−0.00035 (12)	0.00072 (11)
C3	0.01284 (17)	0.01250 (15)	0.01086 (14)	0.00046 (13)	0.00025 (12)	0.00055 (11)
C4	0.01794 (19)	0.01692 (17)	0.01110 (15)	−0.00197 (16)	0.00039 (14)	0.00116 (13)
C5	0.0212 (2)	0.0208 (2)	0.01228 (17)	−0.00293 (17)	0.00346 (16)	−0.00208 (14)
C6	0.0171 (2)	0.01888 (19)	0.01662 (19)	−0.00158 (16)	0.00505 (16)	−0.00503 (15)
C7	0.01300 (17)	0.01447 (17)	0.01644 (18)	0.00129 (14)	0.00227 (14)	−0.00279 (14)
C8	0.01122 (16)	0.01164 (15)	0.01211 (15)	0.00068 (12)	0.00085 (12)	−0.00056 (12)
C9	0.01231 (16)	0.01128 (14)	0.01231 (15)	0.00179 (13)	0.00038 (12)	−0.00034 (12)
C10	0.01739 (19)	0.01159 (15)	0.01841 (18)	0.00220 (14)	0.00051 (16)	−0.00122 (13)
C11	0.0207 (2)	0.01347 (17)	0.0209 (2)	0.00012 (16)	0.00009 (17)	−0.00449 (15)
C12	0.0193 (2)	0.01648 (18)	0.01737 (19)	−0.00146 (16)	−0.00193 (16)	−0.00407 (15)
C13	0.01453 (18)	0.01501 (17)	0.01359 (16)	−0.00046 (14)	−0.00198 (14)	−0.00082 (13)
C14	0.01123 (15)	0.01161 (15)	0.01137 (15)	0.00074 (12)	−0.00007 (12)	−0.00017 (11)
C15	0.01026 (15)	0.01316 (15)	0.01199 (15)	0.00199 (12)	−0.00043 (12)	0.00022 (12)
C16	0.00992 (16)	0.01777 (17)	0.01624 (17)	0.00273 (14)	−0.00082 (13)	0.00019 (14)
C17	0.01004 (16)	0.02005 (19)	0.01595 (18)	0.00017 (14)	0.00083 (14)	−0.00179 (15)
C18	0.01225 (16)	0.01740 (18)	0.01210 (15)	−0.00183 (13)	0.00150 (13)	−0.00059 (13)
C19	0.01181 (16)	0.01315 (15)	0.01135 (15)	−0.00040 (12)	−0.00007 (12)	0.00078 (12)
C20	0.00968 (14)	0.01225 (15)	0.01094 (14)	0.00071 (12)	−0.00019 (12)	0.00043 (11)

Geometric parameters (Å, º)

C1—C3	1.5231 (7)	C9—C14	1.4037 (6)
C1—C9	1.5248 (7)	C10—C11	1.4006 (8)
C1—C15	1.5225 (7)	C10—H10	0.978 (13)
C1—H1	1.009 (13)	C11—C12	1.3901 (9)
C2—C8	1.5252 (6)	C11—H11	0.979 (13)
C2—C14	1.5236 (6)	C12—C13	1.3988 (8)
C2—C20	1.5225 (6)	C12—H12	0.948 (13)
C2—H2	1.019 (11)	C13—C14	1.3888 (7)
C3—C4	1.3864 (7)	C13—H13	1.024 (12)
C3—C8	1.4032 (7)	C15—C16	1.3860 (7)
C4—C5	1.3995 (8)	C15—C20	1.4041 (6)
C4—H4	0.982 (14)	C16—C17	1.3991 (8)
C5—C6	1.3903 (9)	C16—H16	0.944 (14)
C5—H5	0.966 (13)	C17—C18	1.3878 (7)
C6—C7	1.4021 (8)	C17—H17	0.978 (13)
C6—H6	0.968 (14)	C18—C19	1.4001 (7)
C7—C8	1.3876 (7)	C18—H18	1.010 (13)
C7—H7	0.938 (13)	C19—C20	1.3871 (6)
C9—C10	1.3871 (7)	C19—H19	0.987 (12)
C3—C1—C9	104.95 (4)	C9—C10—C11	119.12 (5)
C3—C1—H1	116.0 (8)	C9—C10—H10	121.1 (8)
C9—C1—H1	111.1 (8)	C11—C10—H10	119.8 (8)
C15—C1—C3	105.71 (4)	C10—C11—H11	120.3 (8)
C15—C1—C9	105.94 (4)	C12—C11—C10	120.76 (5)
C15—C1—H1	112.4 (8)	C12—C11—H11	118.9 (8)
C8—C2—H2	111.7 (7)	C11—C12—C13	120.07 (5)
C14—C2—C8	105.29 (4)	C11—C12—H12	120.0 (8)
C14—C2—H2	115.6 (6)	C13—C12—H12	120.0 (8)
C20—C2—C8	106.15 (4)	C12—C13—H13	118.0 (7)
C20—C2—C14	105.85 (4)	C14—C13—C12	119.30 (5)
C20—C2—H2	111.6 (7)	C14—C13—H13	122.7 (7)
C4—C3—C1	126.16 (4)	C9—C14—C2	112.88 (4)
C4—C3—C8	120.39 (5)	C13—C14—C2	126.57 (4)
C8—C3—C1	113.44 (4)	C13—C14—C9	120.54 (4)
C3—C4—C5	119.02 (5)	C16—C15—C1	126.71 (4)
C3—C4—H4	118.7 (9)	C16—C15—C20	120.16 (4)
C5—C4—H4	122.2 (9)	C20—C15—C1	113.13 (4)
C4—C5—H5	117.4 (8)	C15—C16—C17	119.15 (5)
C6—C5—C4	120.59 (5)	C15—C16—H16	120.8 (9)
C6—C5—H5	122.0 (8)	C17—C16—H16	120.1 (9)
C5—C6—C7	120.50 (5)	C16—C17—H17	120.0 (7)
C5—C6—H6	117.9 (8)	C18—C17—C16	120.77 (4)
C7—C6—H6	121.6 (8)	C18—C17—H17	119.1 (7)
C6—C7—H7	122.0 (8)	C17—C18—C19	120.13 (5)
C8—C7—C6	118.75 (5)	C17—C18—H18	116.4 (8)
C8—C7—H7	119.2 (8)	C19—C18—H18	123.4 (8)
C3—C8—C2	112.69 (4)	C18—C19—H19	120.1 (7)
C7—C8—C2	126.54 (4)	C20—C19—C18	119.18 (4)
C7—C8—C3	120.75 (4)	C20—C19—H19	120.7 (7)
C10—C9—C1	126.54 (4)	C15—C20—C2	113.02 (4)
C10—C9—C14	120.21 (4)	C19—C20—C2	126.39 (4)
C14—C9—C1	113.23 (4)	C19—C20—C15	120.59 (4)
C1—C3—C4—C5	−178.24 (5)	C9—C10—C11—C12	0.17 (9)
C1—C3—C8—C2	0.29 (6)	C10—C9—C14—C2	178.61 (5)
C1—C3—C8—C7	178.80 (4)	C10—C9—C14—C13	−0.51 (7)
C1—C9—C10—C11	178.43 (5)	C10—C11—C12—C13	−0.32 (9)
C1—C9—C14—C2	0.21 (6)	C11—C12—C13—C14	0.06 (9)
C1—C9—C14—C13	−178.92 (4)	C12—C13—C14—C2	−178.64 (5)
C1—C15—C16—C17	179.86 (5)	C12—C13—C14—C9	0.35 (8)
C1—C15—C20—C2	0.83 (5)	C14—C2—C8—C3	56.18 (5)
C1—C15—C20—C19	−179.40 (4)	C14—C2—C8—C7	−122.23 (5)
C3—C1—C9—C10	−122.34 (5)	C14—C2—C20—C15	−56.36 (5)
C3—C1—C9—C14	55.94 (5)	C14—C2—C20—C19	123.88 (5)
C3—C1—C15—C16	123.59 (5)	C14—C9—C10—C11	0.25 (8)
C3—C1—C15—C20	−56.06 (5)	C15—C1—C3—C4	−125.83 (5)
C3—C4—C5—C6	−0.17 (8)	C15—C1—C3—C8	55.48 (5)
C4—C3—C8—C2	−178.49 (5)	C15—C1—C9—C10	126.08 (5)
C4—C3—C8—C7	0.03 (7)	C15—C1—C9—C14	−55.64 (5)
C4—C5—C6—C7	−0.43 (8)	C15—C16—C17—C18	−0.10 (8)
C5—C6—C7—C8	0.82 (8)	C16—C15—C20—C2	−178.85 (4)
C6—C7—C8—C2	177.68 (5)	C16—C15—C20—C19	0.93 (7)
C6—C7—C8—C3	−0.62 (7)	C16—C17—C18—C19	0.31 (8)
C8—C2—C14—C9	−56.49 (5)	C17—C18—C19—C20	0.09 (7)
C8—C2—C14—C13	122.57 (5)	C18—C19—C20—C2	179.04 (4)
C8—C2—C20—C15	55.21 (5)	C18—C19—C20—C15	−0.71 (7)
C8—C2—C20—C19	−124.55 (5)	C20—C2—C8—C3	−55.78 (5)
C8—C3—C4—C5	0.37 (8)	C20—C2—C8—C7	125.80 (5)
C9—C1—C3—C4	122.42 (5)	C20—C2—C14—C9	55.68 (5)
C9—C1—C3—C8	−56.26 (5)	C20—C2—C14—C13	−125.26 (5)
C9—C1—C15—C16	−125.36 (5)	C20—C15—C16—C17	−0.52 (7)
C9—C1—C15—C20	54.99 (5)

(T_N_100) triptycene

Crystal data

C20H14	Z = 4
Mr = 254.33	F(000) = 322
Orthorhombic, P212121	Dx = 1.245 Mg m^−3
a = 8.1019 (13) Å	Mo Kα radiation
b = 8.1922 (13) Å	µ = 0.14 mm^−1
c = 20.442 (3) Å	T = 100 K
V = 1356.8 (4) Å^3	8.00 × 2.00 × 2.00 mm

Data collection

11 neutro detectors diffractometer	Rint = 0.000
Radiation source: ISIS neutro spallation source	θmax = 84.4°, θmin = 8.9°
π–scans	h = −16→6
27163 measured reflections	k = −20→21
27163 independent reflections	l = −56→49
24898 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.067	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.162	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 2.61 e Å^−3
27163 reflections	Δρmin = −1.43 e Å^−3
308 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00927 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0 (10)

Special details

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.

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 > 2sigma(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
C1	0.43240 (12)	0.88555 (8)	0.17454 (4)	0.00886 (14)
H1	0.5107 (3)	0.7977 (2)	0.20048 (9)	0.0234 (4)
C3	0.31863 (13)	0.98252 (8)	0.22006 (4)	0.00931 (14)
C8	0.21833 (12)	1.09603 (8)	0.18683 (4)	0.00840 (14)
C2	0.24566 (12)	1.09443 (8)	0.11282 (4)	0.00762 (13)
H2	0.1673 (3)	1.1827 (2)	0.08715 (9)	0.0202 (4)
C7	0.10575 (13)	1.19162 (9)	0.22120 (4)	0.01146 (15)
H7	0.0275 (3)	1.2797 (3)	0.19593 (11)	0.0268 (5)
C20	0.42955 (12)	1.12480 (8)	0.10243 (4)	0.00775 (13)
C4	0.30734 (14)	0.96513 (9)	0.28756 (4)	0.01199 (16)
H4	0.3829 (3)	0.8759 (3)	0.31301 (10)	0.0284 (5)
C14	0.21539 (12)	0.91785 (8)	0.09177 (4)	0.00802 (14)
C9	0.31613 (13)	0.80511 (8)	0.12512 (4)	0.00900 (14)
C16	0.70120 (13)	1.02599 (10)	0.13267 (4)	0.01153 (15)
H16	0.7797 (3)	0.9406 (3)	0.15882 (12)	0.0293 (5)
C18	0.67119 (13)	1.26069 (9)	0.06081 (4)	0.01070 (15)
H18	0.7279 (3)	1.3580 (3)	0.03180 (10)	0.0273 (5)
C13	0.10056 (14)	0.86427 (9)	0.04588 (4)	0.01106 (15)
H13	0.0215 (3)	0.9495 (2)	0.02008 (11)	0.0280 (5)
C12	0.08581 (14)	0.69637 (10)	0.03307 (4)	0.01395 (17)
H12	−0.0035 (4)	0.6534 (3)	−0.00277 (12)	0.0346 (6)
C15	0.53030 (12)	1.01306 (9)	0.13615 (4)	0.00894 (14)
C19	0.49916 (12)	1.24801 (9)	0.06449 (4)	0.00862 (14)
H19	0.4199 (3)	1.3344 (2)	0.03841 (10)	0.0234 (4)
C17	0.77106 (13)	1.15071 (10)	0.09470 (4)	0.01191 (16)
H17	0.9055 (3)	1.1629 (3)	0.09220 (12)	0.0308 (5)
C10	0.30156 (14)	0.63873 (9)	0.11269 (4)	0.01276 (16)
H10	0.3799 (4)	0.5516 (2)	0.13872 (12)	0.0308 (5)
C6	0.09321 (14)	1.17292 (10)	0.28929 (4)	0.01407 (17)
H6	0.0041 (4)	1.2452 (3)	0.31635 (12)	0.0335 (6)
C11	0.18545 (14)	0.58488 (9)	0.06637 (4)	0.01490 (17)
H11	0.1728 (4)	0.4552 (2)	0.05604 (13)	0.0355 (6)
C5	0.19352 (15)	1.06113 (10)	0.32217 (4)	0.01485 (18)
H5	0.1838 (4)	1.0486 (3)	0.37516 (10)	0.0343 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0064 (4)	0.0095 (2)	0.0107 (3)	0.0025 (2)	−0.0009 (3)	0.0015 (2)
H1	0.0234 (12)	0.0209 (7)	0.0258 (8)	0.0064 (7)	−0.0060 (8)	0.0056 (6)
C3	0.0095 (5)	0.0100 (2)	0.0084 (2)	0.0008 (3)	0.0001 (3)	0.00053 (19)
C8	0.0058 (4)	0.0088 (2)	0.0106 (3)	0.0018 (2)	0.0004 (3)	−0.00059 (19)
C2	0.0045 (4)	0.0082 (2)	0.0102 (2)	0.0011 (2)	−0.0003 (2)	0.00062 (19)
H2	0.0151 (10)	0.0195 (6)	0.0259 (8)	0.0053 (6)	−0.0045 (7)	0.0041 (5)
C7	0.0080 (5)	0.0119 (3)	0.0145 (3)	0.0016 (3)	0.0021 (3)	−0.0033 (2)
H7	0.0204 (13)	0.0289 (8)	0.0310 (9)	0.0107 (8)	−0.0018 (9)	0.0000 (7)
C20	0.0043 (4)	0.0090 (2)	0.0099 (3)	0.0009 (2)	−0.0006 (3)	0.00104 (19)
C4	0.0123 (5)	0.0140 (3)	0.0097 (3)	−0.0006 (3)	0.0003 (3)	0.0009 (2)
H4	0.0294 (15)	0.0320 (9)	0.0237 (8)	0.0057 (9)	−0.0036 (9)	0.0078 (6)
C14	0.0060 (4)	0.0082 (2)	0.0098 (3)	0.0008 (2)	−0.0007 (3)	−0.00007 (19)
C9	0.0084 (4)	0.0079 (2)	0.0107 (3)	0.0018 (2)	−0.0001 (3)	−0.00011 (19)
C16	0.0057 (4)	0.0144 (3)	0.0145 (3)	0.0030 (3)	−0.0008 (3)	0.0008 (2)
H16	0.0203 (14)	0.0307 (9)	0.0371 (11)	0.0078 (8)	−0.0039 (10)	0.0094 (7)
C18	0.0076 (5)	0.0137 (3)	0.0108 (3)	−0.0013 (3)	0.0014 (3)	−0.0006 (2)
H18	0.0226 (13)	0.0298 (8)	0.0296 (9)	−0.0073 (8)	0.0036 (9)	0.0090 (7)
C13	0.0085 (5)	0.0119 (3)	0.0128 (3)	−0.0003 (3)	−0.0026 (3)	−0.0012 (2)
H13	0.0255 (14)	0.0268 (8)	0.0317 (10)	0.0027 (8)	−0.0117 (9)	0.0023 (7)
C12	0.0130 (5)	0.0132 (3)	0.0157 (3)	−0.0015 (3)	−0.0020 (3)	−0.0044 (2)
H12	0.0348 (16)	0.0340 (10)	0.0350 (11)	−0.0061 (10)	−0.0140 (11)	−0.0095 (8)
C15	0.0056 (4)	0.0104 (2)	0.0108 (3)	0.0020 (2)	−0.0006 (3)	0.0007 (2)
C19	0.0055 (4)	0.0105 (2)	0.0099 (3)	0.0004 (2)	0.0000 (3)	0.0006 (2)
H19	0.0151 (11)	0.0250 (7)	0.0300 (9)	0.0025 (7)	−0.0022 (8)	0.0100 (6)
C17	0.0038 (5)	0.0169 (3)	0.0150 (3)	0.0006 (3)	0.0010 (3)	−0.0009 (2)
H17	0.0062 (11)	0.0431 (11)	0.0430 (12)	−0.0013 (8)	0.0015 (10)	0.0045 (9)
C10	0.0132 (5)	0.0084 (2)	0.0168 (3)	0.0020 (3)	0.0000 (3)	−0.0011 (2)
H10	0.0342 (15)	0.0186 (7)	0.0397 (11)	0.0074 (8)	−0.0109 (11)	0.0017 (7)
C6	0.0119 (5)	0.0156 (3)	0.0147 (3)	−0.0004 (3)	0.0051 (3)	−0.0049 (2)
H6	0.0317 (16)	0.0375 (10)	0.0313 (10)	0.0075 (10)	0.0133 (10)	−0.0089 (8)
C11	0.0157 (5)	0.0097 (2)	0.0194 (3)	0.0007 (3)	−0.0002 (4)	−0.0045 (2)
H11	0.0411 (17)	0.0164 (7)	0.0490 (13)	0.0000 (8)	−0.0103 (12)	−0.0100 (7)
C5	0.0161 (5)	0.0175 (3)	0.0110 (3)	−0.0013 (3)	0.0029 (3)	−0.0018 (2)
H5	0.0428 (18)	0.0421 (11)	0.0179 (8)	0.0004 (11)	0.0055 (10)	−0.0002 (7)

Geometric parameters (Å, º)

C1—C15	1.5285 (12)	C9—C10	1.3915 (10)
C1—C9	1.5305 (12)	C16—C15	1.3904 (15)
C1—C3	1.5319 (12)	C16—C17	1.4024 (12)
C1—H1	1.096 (2)	C16—H16	1.086 (2)
C3—C4	1.3902 (11)	C18—C17	1.3951 (12)
C3—C8	1.4094 (11)	C18—C19	1.3996 (14)
C8—C7	1.3924 (12)	C18—H18	1.094 (2)
C8—C2	1.5291 (11)	C13—C12	1.4053 (11)
C2—C20	1.5253 (13)	C13—H13	1.084 (2)
C2—C14	1.5290 (10)	C12—C11	1.3960 (13)
C2—H2	1.096 (2)	C12—H12	1.088 (3)
C7—C6	1.4040 (12)	C19—H19	1.094 (2)
C7—H7	1.091 (2)	C17—H17	1.095 (3)
C20—C19	1.3923 (11)	C10—C11	1.4058 (14)
C20—C15	1.4069 (11)	C10—H10	1.094 (2)
C4—C5	1.4034 (13)	C6—C5	1.3968 (14)
C4—H4	1.086 (2)	C6—H6	1.085 (3)
C14—C13	1.3921 (12)	C11—H11	1.088 (2)
C14—C9	1.4086 (11)	C5—H5	1.091 (2)
C15—C1—C9	105.95 (6)	C15—C16—C17	119.05 (8)
C15—C1—C3	105.65 (6)	C15—C16—H16	120.61 (16)
C9—C1—C3	104.71 (8)	C17—C16—H16	120.33 (18)
C15—C1—H1	113.38 (15)	C17—C18—C19	120.19 (8)
C9—C1—H1	113.14 (12)	C17—C18—H18	119.73 (17)
C3—C1—H1	113.25 (13)	C19—C18—H18	120.07 (16)
C4—C3—C8	120.54 (8)	C14—C13—C12	119.40 (8)
C4—C3—C1	126.11 (8)	C14—C13—H13	121.29 (13)
C8—C3—C1	113.35 (6)	C12—C13—H13	119.30 (14)
C7—C8—C3	120.37 (7)	C11—C12—C13	120.03 (8)
C7—C8—C2	126.79 (7)	C11—C12—H12	120.06 (15)
C3—C8—C2	112.81 (7)	C13—C12—H12	119.91 (16)
C20—C2—C14	105.77 (7)	C16—C15—C20	120.21 (8)
C20—C2—C8	106.12 (7)	C16—C15—C1	126.52 (7)
C14—C2—C8	105.27 (6)	C20—C15—C1	113.27 (8)
C20—C2—H2	113.06 (13)	C20—C19—C18	119.15 (8)
C14—C2—H2	113.36 (12)	C20—C19—H19	120.18 (15)
C8—C2—H2	112.58 (12)	C18—C19—H19	120.66 (14)
C8—C7—C6	119.09 (8)	C18—C17—C16	120.75 (9)
C8—C7—H7	120.94 (14)	C18—C17—H17	119.66 (14)
C6—C7—H7	119.97 (14)	C16—C17—H17	119.58 (14)
C19—C20—C15	120.63 (9)	C9—C10—C11	119.15 (8)
C19—C20—C2	126.26 (7)	C9—C10—H10	120.09 (15)
C15—C20—C2	113.10 (7)	C11—C10—H10	120.76 (14)
C3—C4—C5	119.09 (8)	C5—C6—C7	120.43 (9)
C3—C4—H4	120.48 (15)	C5—C6—H6	119.97 (16)
C5—C4—H4	120.41 (14)	C7—C6—H6	119.60 (16)
C13—C14—C9	120.44 (7)	C12—C11—C10	120.67 (7)
C13—C14—C2	126.52 (7)	C12—C11—H11	119.30 (17)
C9—C14—C2	113.03 (7)	C10—C11—H11	120.03 (17)
C10—C9—C14	120.31 (8)	C6—C5—C4	120.47 (8)
C10—C9—C1	126.48 (8)	C6—C5—H5	119.85 (18)
C14—C9—C1	113.19 (6)	C4—C5—H5	119.67 (18)

(T_TAAM_50)

Crystal data

C20H14	c = 20.378 Å
Mr = 254.31	V = 1344.3 Å^3
Orthorhombic, P?	Z = 4
Hall symbol: P ?	F(000) = 536
a = 8.080 Å	Dx = 1.257 Mg m^−3
b = 8.165 Å	Mo Kα radiation, λ = 0.71073 Å

Data collection

Radiation source: fine-focus sealed tube	h = 0→9
2373 independent reflections	k = 0→9
2341 reflections with > 2.0σ(I)	l = −23→24
θmax = 25.0°, θmin = 2.7°

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.011	Secondary atom site location: difference Fourier map
wR(F^2) = 0.033	Hydrogen site location: inferred from neighbouring sites
S = 1.23	All H-atom parameters refined
2373 reflections	Weighting scheme based on measured s.u.'s
237 parameters	(Δ/σ)max = 0.001

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
C1	0.43203 (7)	0.88584 (7)	0.17459 (2)	0.01315 (6)
C2	0.24542 (6)	1.09421 (6)	0.11287 (2)	0.01190 (6)
C3	0.31884 (6)	0.98274 (6)	0.22010 (2)	0.01299 (6)
C4	0.30750 (7)	0.96515 (7)	0.28751 (3)	0.01643 (6)
C5	0.19351 (8)	1.06126 (7)	0.32204 (3)	0.01888 (7)
C6	0.09319 (8)	1.17285 (7)	0.28926 (3)	0.01856 (7)
C7	0.10594 (7)	1.19193 (6)	0.22113 (3)	0.01544 (6)
C8	0.21834 (6)	1.09592 (6)	0.18691 (2)	0.01251 (6)
C9	0.31619 (7)	0.80513 (7)	0.12507 (2)	0.01303 (6)
C10	0.30164 (7)	0.63878 (7)	0.11271 (3)	0.01672 (6)
C11	0.18561 (8)	0.58489 (7)	0.06656 (3)	0.01885 (7)
C12	0.08607 (8)	0.69620 (7)	0.03314 (3)	0.01867 (7)
C13	0.10047 (8)	0.86396 (7)	0.04585 (3)	0.01549 (6)
C14	0.21500 (7)	0.91768 (6)	0.09171 (3)	0.01251 (6)
C15	0.53044 (7)	1.01297 (6)	0.13616 (2)	0.01270 (6)
C16	0.70126 (7)	1.02588 (7)	0.13279 (2)	0.01518 (6)
C17	0.77127 (7)	1.15085 (7)	0.09475 (3)	0.01616 (7)
C18	0.67172 (7)	1.26055 (7)	0.06079 (3)	0.01455 (6)
C19	0.49916 (7)	1.24779 (6)	0.06449 (2)	0.01277 (6)
C20	0.42954 (7)	1.12478 (6)	0.10245 (2)	0.01200 (6)
H7	0.0282 (10)	1.2756 (10)	0.1960 (3)	0.029 (2)*
H1	0.5117 (9)	0.7991 (10)	0.1991 (4)	0.029 (2)*
H19	0.4223 (10)	1.3335 (10)	0.0381 (4)	0.029 (2)*
H10	0.379 (1)	0.555 (1)	0.1391 (4)	0.036 (2)*
H2	0.1676 (10)	1.1826 (9)	0.0870 (4)	0.030 (2)*
H16	0.7763 (10)	0.9432 (10)	0.1589 (4)	0.035 (2)*
H13	0.023 (1)	0.9514 (10)	0.0201 (4)	0.035 (2)*
H6	0.004 (1)	1.242 (1)	0.3163 (4)	0.041 (2)*
H5	0.1823 (10)	1.0490 (9)	0.3739 (4)	0.036 (2)*
H4	0.3852 (10)	0.8769 (10)	0.3123 (4)	0.031 (2)*
H17	0.905 (1)	1.1608 (9)	0.0915 (4)	0.032 (2)*
H11	0.171 (1)	0.455 (1)	0.0554 (4)	0.043 (2)*
H18	0.7266 (10)	1.357 (1)	0.0315 (4)	0.031 (2)*
H12	−0.005 (1)	0.652 (1)	−0.0012 (4)	0.036 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0138 (3)	0.0126 (2)	0.0131 (2)	0.0020 (2)	−0.0002 (2)	0.0005 (2)
C2	0.0113 (3)	0.0119 (3)	0.0125 (2)	0.0010 (2)	−0.0000 (2)	−0.00001 (18)
C3	0.0137 (3)	0.0129 (2)	0.0123 (2)	0.0004 (2)	0.0007 (2)	0.0009 (2)
C4	0.0190 (3)	0.0175 (2)	0.0128 (2)	−0.0019 (2)	0.0002 (2)	0.0014 (2)
C5	0.0227 (3)	0.0215 (3)	0.0124 (2)	−0.0031 (2)	0.0038 (2)	−0.0019 (2)
C6	0.0185 (3)	0.0191 (3)	0.0180 (3)	−0.0012 (2)	0.0053 (2)	−0.0053 (2)
C7	0.0140 (3)	0.0147 (2)	0.0177 (3)	0.0017 (2)	0.0021 (2)	−0.0026 (2)
C8	0.0124 (3)	0.0127 (2)	0.0124 (2)	0.0003 (2)	0.0009 (2)	−0.0003 (2)
C9	0.0133 (3)	0.0120 (2)	0.0138 (2)	0.0020 (2)	0.0001 (2)	0.00000 (19)
C10	0.0184 (3)	0.0123 (3)	0.0194 (3)	0.0024 (2)	0.0003 (2)	−0.0005 (2)
C11	0.0218 (3)	0.0130 (3)	0.0217 (3)	0.0001 (2)	0.0005 (2)	−0.0046 (2)
C12	0.0200 (3)	0.0178 (3)	0.0182 (2)	−0.0017 (2)	−0.0021 (2)	−0.0043 (2)
C13	0.0160 (3)	0.0158 (3)	0.0147 (2)	−0.0001 (2)	−0.0019 (2)	−0.0005 (2)
C14	0.0126 (3)	0.0114 (2)	0.0136 (2)	0.0010 (2)	0.0009 (2)	0.00010 (18)
C15	0.0121 (3)	0.0132 (2)	0.0128 (2)	0.0019 (2)	−0.00011 (19)	0.0003 (2)
C16	0.0111 (3)	0.0176 (3)	0.0169 (2)	0.0027 (2)	−0.0010 (2)	0.0009 (2)
C17	0.0105 (3)	0.0207 (3)	0.0173 (2)	−0.0003 (2)	0.0013 (2)	−0.0009 (2)
C18	0.0136 (3)	0.0169 (2)	0.0131 (2)	−0.0014 (2)	0.0014 (2)	−0.0001 (2)
C19	0.0132 (3)	0.0133 (2)	0.0118 (2)	0.00002 (19)	−0.0000 (2)	0.0007 (2)
C20	0.0109 (3)	0.0127 (2)	0.0124 (2)	0.0011 (2)	0.0000 (2)	0.0003 (2)

Geometric parameters (Å, º)

C1—C3	1.5240 (7)	C9—C10	1.3862 (8)
C1—C15	1.5240 (7)	C10—C11	1.3989 (8)
C1—C9	1.5260 (7)	C10—H10	1.073 (9)
C1—H1	1.080 (8)	C11—C12	1.3916 (9)
C2—C20	1.5234 (7)	C11—H11	1.090 (9)
C2—C14	1.5243 (7)	C12—C13	1.3988 (8)
C2—C8	1.5246 (7)	C12—H12	1.076 (9)
C2—H2	1.093 (8)	C13—C14	1.3865 (8)
C3—C8	1.4038 (7)	C13—H13	1.086 (9)
C3—C4	1.3842 (8)	C15—C20	1.4036 (7)
C4—C5	1.3997 (8)	C15—C16	1.3859 (8)
C4—H4	1.081 (8)	C16—C17	1.4006 (8)
C5—C6	1.3904 (8)	C16—H16	1.052 (9)
C5—H5	1.064 (9)	C17—C18	1.3886 (8)
C6—C7	1.4009 (8)	C17—H17	1.088 (9)
C6—H6	1.068 (9)	C18—C19	1.4002 (8)
C7—C8	1.3876 (7)	C18—H18	1.084 (8)
C7—H7	1.060 (8)	C19—C20	1.3869 (7)
C9—C14	1.4053 (8)	C19—H19	1.079 (8)
C1—C3—C8	113.31 (4)	C9—C1—H1	112.9 (4)
C1—C3—C4	126.14 (5)	C9—C14—C13	120.49 (6)
C1—C15—C20	113.04 (4)	C9—C10—C11	119.15 (6)
C1—C15—C16	126.65 (5)	C9—C10—H10	119.1 (5)
C1—C9—C14	113.22 (6)	C10—C9—C14	120.23 (5)
C1—C9—C10	126.53 (7)	C10—C11—C12	120.72 (7)
C2—C20—C15	113.11 (4)	C10—C11—H11	121.1 (5)
C2—C20—C19	126.34 (5)	C11—C12—C13	120.05 (5)
C2—C14—C9	112.81 (5)	C11—C12—H12	119.8 (5)
C2—C14—C13	126.68 (6)	C11—C10—H10	121.7 (5)
C2—C8—C3	112.81 (4)	C12—C11—H11	118.2 (5)
C2—C8—C7	126.62 (5)	C12—C13—C14	119.35 (6)
C3—C1—C15	105.80 (5)	C12—C13—H13	120.4 (5)
C3—C1—C9	104.99 (5)	C13—C12—H12	120.1 (5)
C3—C1—H1	114.6 (4)	C14—C2—C20	105.84 (4)
C3—C8—C7	120.55 (6)	C14—C2—H2	113.3 (4)
C3—C4—C5	118.96 (5)	C14—C13—H13	120.3 (5)
C3—C4—H4	119.6 (5)	C15—C1—H1	111.9 (4)
C4—C3—C8	120.54 (6)	C15—C20—C19	120.56 (5)
C4—C5—C6	120.63 (6)	C15—C16—C17	119.02 (5)
C4—C5—H5	120.1 (5)	C15—C16—H16	120.0 (5)
C5—C6—C7	120.40 (7)	C16—C15—C20	120.31 (6)
C5—C6—H6	119.5 (5)	C16—C17—C18	120.78 (5)
C5—C4—H4	121.4 (5)	C16—C17—H17	119.4 (5)
C6—C5—H5	119.2 (5)	C17—C18—C19	120.13 (7)
C6—C7—C8	118.91 (6)	C17—C18—H18	120.4 (5)
C6—C7—H7	120.4 (5)	C17—C16—H16	121.0 (5)
C7—C6—H6	120.1 (5)	C18—C17—H17	119.9 (5)
C8—C2—C20	106.06 (4)	C18—C19—C20	119.19 (6)
C8—C2—C14	105.40 (4)	C18—C19—H19	119.9 (5)
C8—C2—H2	112.9 (4)	C19—C18—H18	119.4 (5)
C8—C7—H7	120.6 (5)	C20—C2—H2	112.7 (4)
C9—C1—C15	105.93 (3)	C20—C19—H19	120.9 (5)
C1—C3—C8—C2	0.42 (4)	C8—C7—C6—H6	−177.8 (7)
C1—C3—C8—C7	178.83 (5)	C9—C1—C15—C20	55.09 (5)
C1—C3—C4—C5	−178.32 (5)	C9—C1—C15—C16	−125.41 (5)
C1—C3—C4—H4	0.9 (4)	C9—C14—C2—C20	55.73 (4)
C1—C15—C20—C2	0.74 (4)	C9—C14—C2—H2	179.7 (6)
C1—C15—C20—C19	−179.38 (5)	C9—C14—C13—C12	0.19 (5)
C1—C15—C16—C17	179.87 (5)	C9—C14—C13—H13	−179.9 (6)
C1—C15—C16—H16	−0.7 (4)	C9—C10—C11—C12	0.23 (5)
C1—C9—C14—C2	0.14 (4)	C9—C10—C11—H11	179.6 (7)
C1—C9—C14—C13	−178.83 (5)	C10—C9—C1—C15	126.06 (5)
C1—C9—C10—C11	178.39 (5)	C10—C9—C1—H1	3.2 (4)
C1—C9—C10—H10	−1.0 (5)	C10—C9—C14—C13	−0.43 (5)
C2—C20—C15—C16	−178.79 (5)	C10—C11—C12—C13	−0.47 (5)
C2—C20—C19—C18	179.07 (5)	C10—C11—C12—H12	−178.2 (7)
C2—C20—C19—H19	−0.7 (4)	C11—C12—C13—C14	0.25 (5)
C2—C14—C9—C10	178.55 (5)	C11—C12—C13—H13	−179.6 (6)
C2—C14—C13—C12	−178.63 (5)	C11—C10—C9—C14	0.22 (5)
C2—C14—C13—H13	1.2 (4)	C12—C11—C10—H10	179.6 (7)
C2—C8—C3—C4	−178.45 (5)	C13—C14—C2—C20	−125.37 (5)
C2—C8—C7—C6	177.52 (5)	C13—C14—C2—H2	−1.4 (4)
C2—C8—C7—H7	−0.5 (4)	C13—C12—C11—H11	−179.9 (7)
C3—C1—C15—C20	−56.03 (4)	C14—C2—C20—C15	−56.38 (4)
C3—C1—C15—C16	123.48 (5)	C14—C2—C20—C19	123.75 (5)
C3—C1—C9—C14	56.02 (4)	C14—C9—C1—C15	−55.66 (4)
C3—C1—C9—C10	−122.26 (5)	C14—C9—C1—H1	−178.5 (6)
C3—C8—C2—C20	−55.86 (4)	C14—C9—C10—H10	−179.2 (7)
C3—C8—C2—C14	56.09 (4)	C14—C13—C12—H12	178.0 (7)
C3—C8—C2—H2	−179.8 (6)	C15—C20—C2—H2	179.3 (6)
C3—C8—C7—C6	−0.65 (5)	C15—C20—C19—C18	−0.79 (5)
C3—C8—C7—H7	−178.7 (6)	C15—C20—C19—H19	179.5 (6)
C3—C4—C5—C6	−0.06 (5)	C15—C16—C17—C18	−0.03 (5)
C3—C4—C5—H5	179.6 (7)	C15—C16—C17—H17	−179.4 (7)
C4—C3—C1—C15	−125.79 (5)	C16—C15—C1—H1	−2.0 (4)
C4—C3—C1—C9	122.43 (5)	C16—C15—C20—C19	1.08 (5)
C4—C3—C1—H1	−2.0 (4)	C16—C17—C18—C19	0.31 (5)
C4—C3—C8—C7	−0.04 (5)	C16—C17—C18—H18	179.9 (6)
C4—C5—C6—C7	−0.64 (5)	C17—C18—C19—C20	0.10 (5)
C4—C5—C6—H6	178.1 (7)	C17—C18—C19—H19	179.8 (6)
C5—C6—C7—C8	0.99 (5)	C17—C16—C15—C20	−0.66 (5)
C5—C6—C7—H7	179.0 (6)	C18—C17—C16—H16	−179.5 (7)
C5—C4—C3—C8	0.40 (5)	C19—C20—C2—H2	−0.6 (4)
C6—C5—C4—H4	−179.3 (6)	C19—C18—C17—H17	179.6 (7)
C7—C8—C2—C20	125.84 (5)	C20—C15—C1—H1	178.5 (6)
C7—C8—C2—C14	−122.20 (5)	C20—C15—C16—H16	178.8 (7)
C7—C8—C2—H2	1.9 (4)	C20—C19—C18—H18	−179.5 (6)
C7—C6—C5—H5	179.7 (7)	H7—C7—C6—H6	0.3 (7)
C8—C2—C20—C15	55.26 (4)	H19—C19—C18—H18	0.2 (7)
C8—C2—C20—C19	−124.60 (5)	H10—C10—C11—H11	−1.0 (7)
C8—C2—C14—C9	−56.38 (4)	H16—C16—C17—H17	1.2 (7)
C8—C2—C14—C13	122.52 (5)	H13—C13—C12—H12	−1.8 (7)
C8—C3—C1—C15	55.41 (4)	H6—C6—C5—H5	−1.6 (7)
C8—C3—C1—C9	−56.36 (4)	H5—C5—C4—H4	0.4 (7)
C8—C3—C1—H1	179.2 (6)	H17—C17—C18—H18	−0.8 (7)
C8—C3—C4—H4	179.6 (6)	H11—C11—C12—H12	2.3 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···C18^i	1.064 (9)	2.952 (8)	3.5937 (8)	119.2 (5)
C4—H4···C17^i	1.081 (8)	2.931 (8)	3.5702 (8)	118.1 (5)
C4—H4···C18^i	1.081 (8)	2.793 (8)	3.5178 (8)	124.3 (5)

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

(T_TAAM_80)

Crystal data

C20H14	c = 20.378 Å
Mr = 254.31	V = 1344.3 Å^3
Orthorhombic, P?	Z = 4
Hall symbol: P ?	F(000) = 536
a = 8.080 Å	Dx = 1.257 Mg m^−3
b = 8.165 Å	Mo Kα radiation, λ = 0.71073 Å

Data collection

Radiation source: fine-focus sealed tube	h = 0→14
8318 independent reflections	k = 0→14
8081 reflections with > 2.0σ(I)	l = −36→36
θmax = 40.0°, θmin = 2.7°

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.016	Secondary atom site location: difference Fourier map
wR(F^2) = 0.041	Hydrogen site location: inferred from neighbouring sites
S = 1.17	All H-atom parameters refined
8318 reflections	Weighting scheme based on measured s.u.'s
237 parameters	(Δ/σ)max = 0.002

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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
C1	0.43213 (4)	0.88579 (3)	0.17457 (1)	0.01199 (2)
C2	0.24545 (3)	1.09429 (3)	0.11290 (1)	0.01069 (2)
C3	0.31900 (4)	0.98269 (3)	0.22004 (1)	0.01186 (2)
C4	0.30754 (4)	0.96505 (4)	0.28753 (1)	0.01515 (3)
C5	0.19361 (5)	1.06112 (4)	0.32215 (1)	0.01787 (3)
C6	0.09323 (4)	1.17284 (4)	0.28930 (2)	0.01733 (3)
C7	0.10585 (4)	1.19182 (3)	0.22113 (1)	0.01441 (2)
C8	0.21841 (3)	1.09584 (3)	0.18691 (1)	0.01137 (2)
C9	0.31622 (4)	0.80520 (3)	0.12508 (1)	0.01185 (2)
C10	0.30176 (4)	0.63878 (3)	0.11266 (2)	0.01563 (3)
C11	0.18544 (5)	0.58490 (4)	0.06646 (2)	0.01814 (3)
C12	0.08591 (4)	0.69624 (4)	0.03314 (2)	0.01749 (3)
C13	0.10042 (4)	0.86408 (4)	0.04583 (1)	0.01424 (2)
C14	0.21513 (3)	0.91773 (3)	0.09177 (1)	0.01122 (2)
C15	0.53029 (4)	1.01301 (3)	0.13618 (1)	0.01154 (2)
C16	0.70127 (4)	1.02593 (4)	0.13271 (1)	0.01433 (2)
C17	0.77118 (4)	1.15086 (4)	0.09471 (1)	0.01503 (2)
C18	0.67157 (4)	1.26066 (4)	0.06076 (1)	0.01359 (2)
C19	0.49907 (4)	1.24788 (3)	0.06450 (1)	0.01187 (2)
C20	0.42939 (3)	1.12479 (3)	0.10246 (1)	0.01070 (2)
H7	0.0299 (9)	1.2771 (9)	0.1960 (3)	0.030 (2)*
H1	0.5113 (8)	0.8001 (9)	0.1995 (3)	0.028 (2)*
H19	0.4226 (8)	1.3332 (8)	0.0380 (3)	0.027 (1)*
H10	0.3789 (9)	0.5544 (9)	0.1386 (4)	0.036 (2)*
H2	0.1683 (8)	1.1821 (8)	0.0871 (3)	0.025 (1)*
H16	0.7746 (9)	0.9436 (9)	0.1587 (3)	0.036 (2)*
H13	0.0221 (9)	0.9506 (9)	0.0200 (3)	0.033 (2)*
H6	0.0049 (10)	1.2423 (9)	0.3161 (4)	0.039 (2)*
H5	0.1820 (9)	1.0493 (9)	0.3740 (4)	0.038 (2)*
H4	0.3850 (9)	0.8777 (9)	0.3117 (3)	0.032 (2)*
H17	0.9040 (10)	1.1608 (8)	0.0918 (3)	0.031 (2)*
H11	0.1716 (9)	0.4559 (10)	0.0554 (4)	0.041 (2)*
H18	0.7289 (9)	1.3567 (9)	0.0317 (3)	0.033 (2)*
H12	−0.0048 (10)	0.6530 (9)	−0.0016 (4)	0.035 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.01211 (10)	0.01194 (8)	0.01192 (8)	0.00240 (7)	−0.00063 (7)	0.00116 (7)
C2	0.00941 (9)	0.01116 (8)	0.01150 (8)	0.00128 (7)	−0.00034 (7)	0.00061 (6)
C3	0.0127 (1)	0.01253 (9)	0.01032 (8)	0.00079 (8)	0.00026 (7)	0.00059 (7)
C4	0.0180 (1)	0.01689 (10)	0.01057 (9)	−0.00132 (9)	0.00059 (8)	0.00122 (7)
C5	0.0212 (1)	0.0206 (1)	0.01185 (10)	−0.00246 (10)	0.00361 (9)	−0.00189 (8)
C6	0.0175 (1)	0.0186 (1)	0.0159 (1)	−0.00085 (9)	0.00499 (9)	−0.00476 (8)
C7	0.0130 (1)	0.01433 (10)	0.01594 (10)	0.00169 (8)	0.00226 (8)	−0.00294 (8)
C8	0.01099 (10)	0.01159 (8)	0.01153 (8)	0.00120 (7)	0.00090 (7)	−0.00048 (7)
C9	0.01236 (10)	0.01075 (8)	0.01243 (9)	0.00178 (7)	−0.000009 (7)	−0.00033 (6)
C10	0.0174 (1)	0.01102 (9)	0.0185 (1)	0.00223 (8)	−0.00014 (9)	−0.00137 (8)
C11	0.0205 (1)	0.01286 (9)	0.0211 (1)	0.00025 (9)	−0.0007 (1)	−0.00453 (8)
C12	0.0191 (1)	0.0159 (1)	0.0174 (1)	−0.00147 (9)	−0.00257 (9)	−0.00428 (8)
C13	0.0144 (1)	0.01461 (9)	0.01369 (9)	−0.00046 (8)	−0.00244 (8)	−0.00107 (7)
C14	0.01104 (9)	0.01105 (8)	0.01157 (8)	0.00072 (7)	−0.00043 (7)	−0.00022 (6)
C15	0.00967 (9)	0.01290 (9)	0.01206 (9)	0.00194 (7)	−0.00040 (7)	0.00072 (7)
C16	0.00949 (10)	0.01730 (10)	0.01619 (10)	0.00256 (8)	−0.00071 (8)	0.00058 (8)
C17	0.00947 (10)	0.0196 (1)	0.0160 (1)	0.00009 (8)	0.00093 (8)	−0.00086 (8)
C18	0.0116 (1)	0.01692 (10)	0.01222 (9)	−0.00163 (8)	0.00140 (8)	−0.00026 (7)
C19	0.01128 (10)	0.01313 (9)	0.01119 (9)	−0.00029 (7)	0.000037 (7)	0.00110 (7)
C20	0.00925 (9)	0.01184 (8)	0.01101 (8)	0.00085 (7)	−0.00013 (7)	0.00085 (6)

Geometric parameters (Å, º)

C1—C15	1.5230 (4)	C9—C10	1.3870 (4)
C1—C3	1.5232 (4)	C10—C11	1.4011 (5)
C1—C9	1.5254 (4)	C10—H10	1.069 (8)
C1—H1	1.076 (7)	C11—C12	1.3908 (5)
C2—C20	1.5219 (4)	C11—H11	1.083 (8)
C2—C8	1.5239 (4)	C12—C13	1.3994 (4)
C2—C14	1.5242 (4)	C12—H12	1.079 (8)
C2—H2	1.086 (7)	C13—C14	1.3883 (4)
C3—C8	1.4035 (4)	C13—H13	1.084 (7)
C3—C4	1.3860 (4)	C15—C20	1.4035 (4)
C4—C5	1.4002 (5)	C15—C16	1.3873 (4)
C4—H4	1.069 (7)	C16—C17	1.3997 (4)
C5—C6	1.3921 (5)	C16—H16	1.041 (7)
C5—H5	1.066 (8)	C17—C18	1.3892 (4)
C6—C7	1.4015 (4)	C17—H17	1.078 (8)
C6—H6	1.063 (8)	C18—C19	1.3997 (4)
C7—C8	1.3883 (4)	C18—H18	1.086 (7)
C7—H7	1.060 (7)	C19—C20	1.3876 (4)
C9—C14	1.4043 (4)	C19—H19	1.076 (7)
C1—C15—C20	113.11 (2)	C9—C1—H1	113.4 (4)
C1—C15—C16	126.63 (3)	C9—C14—C13	120.52 (3)
C1—C3—C8	113.37 (2)	C9—C10—C11	119.12 (3)
C1—C3—C4	126.14 (3)	C9—C10—H10	119.5 (4)
C1—C9—C14	113.23 (3)	C10—C9—C14	120.25 (2)
C1—C9—C10	126.50 (3)	C10—C11—C12	120.72 (4)
C2—C20—C15	113.10 (2)	C10—C11—H11	121.0 (5)
C2—C20—C19	126.35 (3)	C11—C12—C13	120.09 (3)
C2—C8—C3	112.80 (2)	C11—C12—H12	120.0 (5)
C2—C8—C7	126.56 (3)	C11—C10—H10	121.4 (5)
C2—C14—C9	112.88 (3)	C12—C11—H11	118.3 (4)
C2—C14—C13	126.59 (3)	C12—C13—C14	119.31 (3)
C3—C1—C15	105.70 (2)	C12—C13—H13	120.0 (4)
C3—C1—C9	104.94 (2)	C13—C12—H12	119.9 (5)
C3—C1—H1	114.1 (4)	C14—C2—C20	105.80 (2)
C3—C8—C7	120.61 (3)	C14—C2—H2	113.3 (4)
C3—C4—C5	119.06 (3)	C14—C13—H13	120.7 (4)
C3—C4—H4	119.2 (4)	C15—C1—H1	112.1 (4)
C4—C3—C8	120.47 (3)	C15—C20—C19	120.55 (3)
C4—C5—C6	120.52 (3)	C15—C16—C17	119.04 (3)
C4—C5—H5	120.5 (5)	C15—C16—H16	119.5 (4)
C5—C6—C7	120.45 (4)	C16—C15—C20	120.27 (3)
C5—C6—H6	119.6 (5)	C16—C17—C18	120.80 (3)
C5—C4—H4	121.8 (4)	C16—C17—H17	119.2 (4)
C6—C5—H5	119.0 (5)	C17—C18—C19	120.11 (4)
C6—C7—C8	118.89 (3)	C17—C18—H18	119.3 (4)
C6—C7—H7	120.6 (4)	C17—C16—H16	121.5 (5)
C7—C6—H6	120.0 (5)	C18—C17—H17	120.0 (4)
C8—C2—C20	106.08 (2)	C18—C19—C20	119.23 (3)
C8—C2—C14	105.33 (2)	C18—C19—H19	119.8 (4)
C8—C2—H2	113.0 (4)	C19—C18—H18	120.5 (4)
C8—C7—H7	120.5 (4)	C20—C2—H2	112.6 (4)
C9—C1—C15	105.93 (2)	C20—C19—H19	121.0 (4)
C1—C15—C20—C2	0.83 (2)	C8—C7—C6—H6	−177.9 (6)
C1—C15—C20—C19	−179.35 (3)	C9—C1—C15—C20	54.98 (2)
C1—C15—C16—C17	179.82 (3)	C9—C1—C15—C16	−125.38 (3)
C1—C15—C16—H16	−0.8 (4)	C9—C14—C2—C20	55.73 (2)
C1—C3—C8—C2	0.36 (2)	C9—C14—C2—H2	179.6 (5)
C1—C3—C8—C7	178.77 (2)	C9—C14—C13—C12	0.24 (3)
C1—C3—C4—C5	−178.32 (3)	C9—C14—C13—H13	180.0 (5)
C1—C3—C4—H4	1.1 (4)	C9—C10—C11—C12	0.27 (3)
C1—C9—C14—C2	0.11 (2)	C9—C10—C11—H11	179.6 (6)
C1—C9—C14—C13	−178.88 (2)	C10—C9—C1—C15	126.06 (3)
C1—C9—C10—C11	178.40 (3)	C10—C9—C1—H1	2.7 (4)
C1—C9—C10—H10	−1.3 (4)	C10—C9—C14—C13	−0.38 (3)
C2—C20—C15—C16	−178.84 (3)	C10—C11—C12—C13	−0.41 (3)
C2—C20—C19—C18	179.07 (2)	C10—C11—C12—H12	−178.8 (6)
C2—C20—C19—H19	−0.9 (4)	C11—C12—C13—C14	0.15 (3)
C2—C8—C3—C4	−178.44 (2)	C11—C12—C13—H13	−179.6 (5)
C2—C8—C7—C6	177.62 (2)	C11—C10—C9—C14	0.13 (3)
C2—C8—C7—H7	−1.8 (4)	C12—C11—C10—H10	180.0 (6)
C2—C14—C9—C10	178.61 (3)	C13—C14—C2—C20	−125.35 (3)
C2—C14—C13—C12	−178.60 (3)	C13—C14—C2—H2	−1.5 (3)
C2—C14—C13—H13	1.1 (4)	C13—C12—C11—H11	−179.8 (6)
C3—C1—C15—C20	−56.04 (2)	C14—C2—C20—C15	−56.37 (2)
C3—C1—C15—C16	123.60 (3)	C14—C2—C20—C19	123.82 (3)
C3—C1—C9—C14	56.00 (2)	C14—C9—C1—C15	−55.56 (2)
C3—C1—C9—C10	−122.38 (3)	C14—C9—C1—H1	−178.9 (5)
C3—C8—C2—C20	−55.80 (2)	C14—C9—C10—H10	−179.6 (6)
C3—C8—C2—C14	56.09 (2)	C14—C13—C12—H12	178.5 (6)
C3—C8—C2—H2	−179.7 (5)	C15—C20—C2—H2	179.3 (5)
C3—C8—C7—C6	−0.56 (3)	C15—C20—C19—C18	−0.73 (2)
C3—C8—C7—H7	−179.9 (5)	C15—C20—C19—H19	179.3 (5)
C3—C4—C5—C6	0.00 (3)	C15—C16—C17—C18	−0.08 (3)
C3—C4—C5—H5	179.6 (6)	C15—C16—C17—H17	−179.7 (6)
C4—C3—C1—C15	−125.88 (3)	C16—C15—C1—H1	−1.3 (4)
C4—C3—C1—C9	122.40 (3)	C16—C15—C20—C19	0.98 (3)
C4—C3—C1—H1	−2.3 (4)	C16—C17—C18—C19	0.32 (3)
C4—C3—C8—C7	−0.03 (3)	C16—C17—C18—H18	179.8 (6)
C4—C5—C6—C7	−0.58 (3)	C17—C18—C19—C20	0.09 (3)
C4—C5—C6—H6	178.2 (6)	C17—C18—C19—H19	−179.9 (5)
C5—C6—C7—C8	0.86 (3)	C17—C16—C15—C20	−0.56 (3)
C5—C6—C7—H7	−179.8 (5)	C18—C17—C16—H16	−179.4 (6)
C5—C4—C3—C8	0.32 (3)	C19—C20—C2—H2	−0.5 (4)
C6—C5—C4—H4	−179.4 (6)	C19—C18—C17—H17	180.0 (6)
C7—C8—C2—C20	125.90 (3)	C20—C15—C1—H1	179.1 (5)
C7—C8—C2—C14	−122.21 (3)	C20—C15—C16—H16	178.8 (6)
C7—C8—C2—H2	2.0 (3)	C20—C19—C18—H18	−179.4 (5)
C7—C6—C5—H5	179.8 (6)	H7—C7—C6—H6	1.5 (6)
C8—C2—C20—C15	55.19 (2)	H19—C19—C18—H18	0.6 (6)
C8—C2—C20—C19	−124.62 (3)	H10—C10—C11—H11	−0.7 (6)
C8—C2—C14—C9	−56.36 (2)	H16—C16—C17—H17	0.9 (6)
C8—C2—C14—C13	122.56 (3)	H13—C13—C12—H12	−1.2 (6)
C8—C3—C1—C15	55.40 (2)	H6—C6—C5—H5	−1.5 (6)
C8—C3—C1—C9	−56.32 (2)	H5—C5—C4—H4	0.2 (6)
C8—C3—C1—H1	179.0 (5)	H17—C17—C18—H18	−0.5 (6)
C8—C3—C4—H4	179.7 (6)	H11—C11—C12—H12	1.8 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···C18^i	1.066 (8)	2.953 (7)	3.5913 (4)	118.9 (5)
C4—H4···C17^i	1.069 (7)	2.943 (7)	3.5697 (4)	117.9 (5)
C4—H4···C18^i	1.069 (7)	2.806 (7)	3.5172 (4)	123.9 (5)

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