2-Butyl-4-chloro-1-(4-nitro­benzyl)-1H-imidazole-5-carbox­aldehyde

Gaonkar, S.L.; Yathirajan, H.S.; Nagaraj, B.; Narasegowda, R.S.; Lynch, D.E.

doi:10.1107/S1600536804031162

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 60| Part 12| December 2004| Pages o2520-o2521

https://doi.org/10.1107/S1600536804031162

2-Butyl-4-chloro-1-(4-nitrobenzyl)-1H-imidazole-5-carboxaldehyde

Santhosh L. Gaonkar,^a Hemmige S. Yathirajan,^a Basavegowda Nagaraj,^a Rajenahally S. Narasegowda ^a and Daniel E. Lynch ^b ^*

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^bSchool of Science and the Environment, Coventry University, Coventry CV1 5FB, England
^*Correspondence e-mail: apx106@coventry.ac.uk

(Received 25 November 2004; accepted 26 November 2004; online 30 November 2004)

The asymmetric unit of the title compound, C₁₅H₁₆ClN₃O₃, comprises two molecules that are each twisted about the benzyl C atom. The second and fourth C atoms of the butyl chain of one molecule are disordered (0.75:0.25 and 0.5:0.5, respectively). The dihedral angles between the imidazole and benzene rings are 76.46 (9) and 76.3 (1)°.

Comment

Imidazole derivatives are reported to be biologically active molecules, and both imidazoles and benzimidazoles are components of larger molecules used in pharmaceuticals, agrochemicals, dyestuffs and high-temperature polymer products (Rasmussen, 1999 ; Ambalvanan et al., 2003 ). With this in mind, the title compound, (I), was prepared in a series of syntheses to produce new imidazole derivatives. The Cambridge Structural Database (Version of April 2004; Allen, 2002 ) reveals that there are currently 42 known structures containing a 3-benzylimidazole moiety, but not yet the title compound.

The asymmetric unit of (I) comprises two molecules, A and B, that are each twisted about the benzyl C atom (Fig. 1). The butyl chain of molecule B is disordered, with the second and fourth C atoms in the chain occupying two sites each. The second C atom is unequally disordered, with occupancies of 0.75:0.25 for C22B and C22C, respectively, whereas the fourth C atom is equally disordered across two sites (C24B and C24C). In early refinements, the third C atom (C23B) was split (similar to C22B/C), but this proved not to be a viable option, with the lesser refining unsatisfactorily. Stable refinement was achieved with C23B being treated as a whole atom, even though it displays larger displacement ellipsoids compared with neighbouring atoms. The dihedral angles between the imidazole and benzene rings are 76.46 (9) and 76.3 (1)° for molecules A and B, respectively.

Figure 1
The molecular configurations and atom-numbering schemes for the two independent molecules, A and B, of (I

). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radii.

Experimental

The title compound was prepared by stirring an equimolar mixture of 2-butyl-5-chloro-3H-imidazole-4-carboxaldehyde, 4-nitrobenzylbromide and K₂CO₃ in dimethylformamide at room temperature for 6 h. The product was filtered and recrystallized from ethanol to yield colourless plates.

Crystal data

C₁₅H₁₆ClN₃O₃
M_r = 321.76
Triclinic, $[P\overline 1]$
a = 8.3007 (5) Å
b = 12.2295 (6) Å
c = 16.5605 (10) Å
α = 103.420 (4)°
β = 95.561 (3)°
γ = 106.758 (3)°
V = 1541.35 (15) Å³
Z = 4
D_x = 1.387 Mg m⁻³
Mo Kα radiation
Cell parameters from 6811 reflections
θ = 2.9–27.5°
μ = 0.26 mm⁻¹
T = 120 (2) K
Plate, colourless
0.36 × 0.30 × 0.04 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1997b ) T_min = 0.911, T_max = 0.990
30 632 measured reflections
6038 independent reflections
3622 reflections with I > 2σ(I)
R_int = 0.098
θ_max = 26.0°
h = −10 → 10
k = −15 → 15
l = −20 → 20

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.139
S = 1.04
6038 reflections
418 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0645P)² + 0.076P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.34 e Å⁻³

All H atoms were included in the refinement at calculated positions in the riding-model approximation, with C—H distances of 0.95 (aromatic H atoms and CHO H atoms), 0.98 (CH₃ H atoms) and 0.99 Å (CH₂ H atoms). The isotropic displacement parameters were set equal to 1.25U_eq of the carrier atom. A high R_int was the result of weak high-angle data.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON97 (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536804031162/tk6201sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536804031162/tk6201Isup2.hkl

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

2-Butyl-4-chloro-1-(4-nitrobenzyl)-1H-imidazole-5-carboxaldehyde top

Crystal data top

C₁₅H₁₆ClN₃O₃	Z = 4
M_r = 321.76	F(000) = 672
Triclinic, P1	D_x = 1.387 Mg m⁻³
Hall symbol: -P 1	Melting point: 375 K
a = 8.3007 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2295 (6) Å	Cell parameters from 6811 reflections
c = 16.5605 (10) Å	θ = 2.9–27.5°
α = 103.420 (4)°	µ = 0.26 mm⁻¹
β = 95.561 (3)°	T = 120 K
γ = 106.758 (3)°	Plate, colourless
V = 1541.35 (15) Å³	0.36 × 0.30 × 0.04 mm

Data collection top

Bruker-Nonius KappaCCD area-detector diffractometer	6038 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	3622 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.098
Detector resolution: 9.091 pixels mm^-1	θ_max = 26.0°, θ_min = 2.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1997b)	k = −15→15
T_min = 0.911, T_max = 0.990	l = −20→20
30632 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0645P)² + 0.076P] where P = (F_o² + 2F_c²)/3
6038 reflections	(Δ/σ)_max < 0.001
418 parameters	Δρ_max = 0.29 e Å⁻³
5 restraints	Δρ_min = −0.34 e Å⁻³

Special details top

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 6.8962 (0.0067) x + 4.9846 (0.0145) y - 7.8315 (0.0209) z = 1.6003 (0.0120)

* -0.0004 (0.0016) N1A * 0.0000 (0.0016) C2A * 0.0003 (0.0016) N3A * -0.0006 (0.0016) C4A * 0.0006 (0.0017) C5A

Rms deviation of fitted atoms = 0.0004

- 2.8599 (0.0085) x - 3.1842 (0.0131) y + 15.8848 (0.0052) z = 0.0246 (0.0064)

Angle to previous plane (with approximate e.s.d.) = 76.46 (0.09)

* -0.0124 (0.0019) C32A * 0.0090 (0.0019) C33A * 0.0041 (0.0019) C34A * -0.0137 (0.0019) C35A * 0.0100 (0.0019) C36A * 0.0031 (0.0019) C37A

Rms deviation of fitted atoms = 0.0096

7.1630 (0.0060) x - 4.4739 (0.0148) y + 6.9396 (0.0214) z = 6.8216 (0.0014)

Angle to previous plane (with approximate e.s.d.) = 80.19 (0.09)

* 0.0002 (0.0017) N1B * -0.0002 (0.0017) C2B * 0.0002 (0.0016) N3B * 0.0000 (0.0016) C4B * -0.0001 (0.0017) C5B

Rms deviation of fitted atoms = 0.0002

- 2.3192 (0.0090) x - 3.5959 (0.0138) y + 16.1123 (0.0044) z = 1.2353 (0.0111)

Angle to previous plane (with approximate e.s.d.) = 76.31 (0.10)

* 0.0029 (0.0019) C32B * -0.0043 (0.0020) C33B * 0.0014 (0.0020) C34B * 0.0030 (0.0020) C35B * -0.0043 (0.0020) C36B * 0.0014 (0.0020) C37B

Rms deviation of fitted atoms = 0.0031

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.1941 (3)	0.9197 (2)	0.21017 (15)	0.0320 (6)
C2A	0.1120 (4)	0.8084 (2)	0.21159 (18)	0.0291 (7)
C21A	0.0110 (4)	0.7792 (3)	0.27785 (19)	0.0341 (7)
H21A	−0.1016	0.7203	0.2497	0.043*
H22A	−0.0099	0.8520	0.3089	0.043*
C22A	0.0936 (4)	0.7298 (3)	0.34200 (18)	0.0336 (7)
H23A	0.1042	0.6525	0.3127	0.042*
H24A	0.2098	0.7850	0.3678	0.042*
C23A	−0.0126 (4)	0.7134 (3)	0.4106 (2)	0.0452 (9)
H25A	−0.0219	0.7912	0.4397	0.056*
H26A	−0.1294	0.6598	0.3840	0.056*
C24A	0.0598 (5)	0.6628 (3)	0.4755 (2)	0.0473 (9)
H27A	0.0520	0.5806	0.4490	0.059*
H28A	−0.0055	0.6649	0.5217	0.059*
H29A	0.1798	0.7103	0.4977	0.059*
N3A	0.1292 (3)	0.72747 (19)	0.14485 (14)	0.0260 (5)
C31A	0.0640 (4)	0.5979 (2)	0.12824 (19)	0.0281 (7)
H31A	0.0088	0.5623	0.0683	0.035*
H32A	−0.0239	0.5769	0.1634	0.035*
C32A	0.2046 (3)	0.5464 (2)	0.14713 (17)	0.0244 (6)
C33A	0.1713 (4)	0.4240 (2)	0.11796 (17)	0.0280 (7)
H33A	0.0601	0.3748	0.0892	0.035*
C34A	0.2970 (4)	0.3735 (2)	0.13014 (17)	0.0278 (7)
H34A	0.2740	0.2903	0.1099	0.035*
C35A	0.4576 (3)	0.4473 (2)	0.17274 (17)	0.0256 (6)
C36A	0.4929 (4)	0.5679 (2)	0.20476 (18)	0.0286 (7)
H36A	0.6029	0.6164	0.2356	0.036*
C37A	0.3659 (3)	0.6167 (2)	0.19124 (17)	0.0273 (7)
H37A	0.3892	0.6999	0.2125	0.034*
N31A	0.5943 (3)	0.3952 (2)	0.18395 (15)	0.0306 (6)
O31A	0.5619 (3)	0.28834 (18)	0.15276 (14)	0.0411 (6)
O32A	0.7355 (3)	0.46121 (18)	0.22401 (13)	0.0389 (5)
C4A	0.2293 (3)	0.7895 (2)	0.09634 (18)	0.0270 (7)
C41A	0.2801 (4)	0.7385 (3)	0.01985 (19)	0.0311 (7)
H41A	0.3513	0.7921	−0.0052	0.039*
O41A	0.2410 (3)	0.63322 (18)	−0.01605 (13)	0.0373 (5)
C5A	0.2643 (4)	0.9064 (2)	0.13975 (19)	0.0307 (7)
Cl5A	0.38198 (10)	1.02856 (6)	0.11284 (5)	0.0410 (2)
N1B	0.6628 (3)	−0.1150 (2)	0.22474 (15)	0.0313 (6)
C2B	0.6981 (4)	0.0002 (2)	0.26254 (18)	0.0300 (7)
C21B	0.6407 (5)	0.0477 (3)	0.3422 (2)	0.0454 (9)
H21B	0.5462	0.0782	0.3284	0.057*	0.50
H22B	0.7364	0.1153	0.3790	0.057*	0.50
H21C	0.5147	0.0136	0.3336	0.057*	0.50
H22C	0.6689	0.1346	0.3522	0.057*	0.50
C22B	0.5810 (7)	−0.0426 (4)	0.3902 (3)	0.0548 (14)	0.75
H23B	0.5204	−0.0093	0.4332	0.068*	0.75
H24B	0.4953	−0.1133	0.3502	0.068*	0.75
C22C	0.7160 (19)	0.0238 (10)	0.4224 (7)	0.050 (4)	0.25
H23C	0.8403	0.0667	0.4331	0.062*	0.25
H24C	0.6695	0.0639	0.4692	0.062*	0.25
C23B	0.6998 (7)	−0.0824 (5)	0.4313 (3)	0.0957 (18)
H25B	0.7781	−0.0152	0.4771	0.120*	0.50
H26B	0.7690	−0.1103	0.3907	0.120*	0.50
H25C	0.7749	−0.1123	0.3953	0.120*	0.50
H26C	0.5814	−0.1311	0.4036	0.120*	0.50
C24B	0.6138 (14)	−0.1835 (8)	0.4688 (7)	0.076 (3)	0.50
H27B	0.5378	−0.1587	0.5055	0.096*	0.50
H28B	0.7016	−0.2026	0.5016	0.096*	0.50
H29B	0.5473	−0.2538	0.4231	0.096*	0.50
C24C	0.7279 (15)	−0.1186 (9)	0.5099 (5)	0.077 (3)	0.50
H27C	0.8509	−0.0945	0.5311	0.096*	0.50
H28C	0.6787	−0.2050	0.4979	0.096*	0.50
H29C	0.6728	−0.0802	0.5525	0.096*	0.50
N3B	0.7853 (3)	0.07047 (19)	0.21787 (14)	0.0272 (6)
C31B	0.8436 (4)	0.2000 (2)	0.24006 (19)	0.0315 (7)
H31B	0.7715	0.2295	0.2783	0.039*
H32B	0.8270	0.2255	0.1882	0.039*
C32B	1.0288 (4)	0.2568 (2)	0.28223 (17)	0.0255 (6)
C33B	1.0880 (4)	0.3795 (2)	0.31769 (18)	0.0315 (7)
H33B	1.0113	0.4238	0.3160	0.039*
C34B	1.2568 (4)	0.4371 (3)	0.35520 (18)	0.0325 (7)
H34B	1.2970	0.5205	0.3798	0.041*
C35B	1.3661 (4)	0.3708 (3)	0.35625 (17)	0.0310 (7)
C36B	1.3121 (4)	0.2497 (3)	0.32099 (19)	0.0346 (7)
H36B	1.3899	0.2060	0.3219	0.043*
C37B	1.1418 (4)	0.1932 (3)	0.28422 (19)	0.0329 (7)
H37B	1.1022	0.1097	0.2601	0.041*
N31B	1.5466 (3)	0.4314 (3)	0.39535 (16)	0.0411 (7)
O31B	1.5914 (3)	0.5382 (2)	0.42867 (15)	0.0552 (7)
O32B	1.6441 (3)	0.3719 (2)	0.39210 (16)	0.0591 (7)
C4B	0.8079 (3)	−0.0049 (2)	0.14593 (17)	0.0266 (7)
C41B	0.8932 (4)	0.0287 (3)	0.07954 (19)	0.0342 (7)
H41B	0.8993	−0.0338	0.0349	0.043*
O41B	0.9582 (3)	0.12965 (18)	0.07510 (13)	0.0424 (6)
C5B	0.7303 (3)	−0.1171 (2)	0.15369 (17)	0.0274 (7)
Cl5B	0.71564 (10)	−0.24842 (6)	0.08330 (5)	0.0357 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0331 (15)	0.0262 (14)	0.0401 (16)	0.0145 (11)	0.0045 (12)	0.0103 (11)
C2A	0.0258 (17)	0.0268 (16)	0.0372 (18)	0.0137 (13)	0.0027 (13)	0.0081 (14)
C21A	0.0330 (18)	0.0349 (17)	0.0386 (18)	0.0177 (14)	0.0104 (15)	0.0079 (14)
C22A	0.0310 (18)	0.0322 (17)	0.0368 (18)	0.0106 (14)	0.0047 (14)	0.0076 (14)
C23A	0.046 (2)	0.051 (2)	0.046 (2)	0.0214 (17)	0.0163 (17)	0.0166 (17)
C24A	0.064 (2)	0.043 (2)	0.037 (2)	0.0204 (18)	0.0147 (17)	0.0091 (16)
N3A	0.0208 (13)	0.0216 (12)	0.0368 (14)	0.0084 (10)	0.0040 (11)	0.0089 (11)
C31A	0.0244 (16)	0.0208 (15)	0.0366 (17)	0.0043 (12)	0.0047 (13)	0.0067 (13)
C32A	0.0247 (16)	0.0205 (14)	0.0307 (16)	0.0071 (12)	0.0088 (13)	0.0107 (12)
C33A	0.0266 (17)	0.0240 (15)	0.0295 (16)	0.0044 (13)	0.0007 (13)	0.0060 (13)
C34A	0.0302 (17)	0.0236 (15)	0.0308 (17)	0.0094 (13)	0.0060 (13)	0.0084 (13)
C35A	0.0228 (16)	0.0262 (15)	0.0329 (16)	0.0106 (13)	0.0085 (13)	0.0128 (13)
C36A	0.0238 (16)	0.0258 (15)	0.0342 (17)	0.0048 (13)	0.0022 (13)	0.0096 (13)
C37A	0.0264 (17)	0.0185 (14)	0.0331 (17)	0.0052 (12)	0.0024 (13)	0.0036 (12)
N31A	0.0307 (15)	0.0309 (15)	0.0372 (15)	0.0138 (12)	0.0091 (12)	0.0161 (12)
O31A	0.0392 (13)	0.0263 (12)	0.0652 (16)	0.0170 (10)	0.0119 (11)	0.0170 (11)
O32A	0.0270 (13)	0.0405 (13)	0.0488 (14)	0.0119 (10)	−0.0011 (10)	0.0133 (11)
C4A	0.0207 (15)	0.0256 (15)	0.0360 (18)	0.0069 (12)	0.0036 (13)	0.0124 (13)
C41A	0.0225 (16)	0.0327 (18)	0.0392 (19)	0.0073 (13)	0.0012 (14)	0.0156 (15)
O41A	0.0344 (13)	0.0310 (12)	0.0399 (13)	0.0063 (10)	0.0046 (10)	0.0032 (10)
C5A	0.0289 (17)	0.0207 (15)	0.0433 (19)	0.0079 (13)	−0.0002 (14)	0.0130 (14)
Cl5A	0.0365 (5)	0.0269 (4)	0.0585 (5)	0.0048 (3)	0.0017 (4)	0.0192 (4)
N1B	0.0314 (15)	0.0275 (14)	0.0336 (15)	0.0085 (11)	0.0059 (12)	0.0069 (11)
C2B	0.0283 (17)	0.0290 (17)	0.0329 (17)	0.0103 (13)	0.0039 (14)	0.0083 (14)
C21B	0.063 (2)	0.0383 (19)	0.043 (2)	0.0260 (18)	0.0199 (18)	0.0098 (16)
C22B	0.079 (4)	0.040 (3)	0.060 (3)	0.028 (3)	0.041 (3)	0.019 (3)
C22C	0.065 (11)	0.023 (7)	0.046 (9)	−0.002 (7)	0.019 (8)	−0.003 (6)
C23B	0.156 (5)	0.123 (4)	0.071 (3)	0.104 (4)	0.058 (3)	0.055 (3)
C24B	0.117 (10)	0.084 (8)	0.079 (8)	0.073 (7)	0.059 (7)	0.052 (6)
C24C	0.125 (10)	0.092 (8)	0.049 (6)	0.068 (7)	0.036 (6)	0.033 (6)
N3B	0.0242 (13)	0.0220 (12)	0.0336 (14)	0.0086 (10)	−0.0008 (11)	0.0048 (11)
C31B	0.0316 (18)	0.0231 (15)	0.0405 (18)	0.0128 (13)	0.0006 (14)	0.0070 (13)
C32B	0.0293 (17)	0.0260 (15)	0.0226 (15)	0.0100 (13)	0.0032 (12)	0.0084 (12)
C33B	0.0328 (18)	0.0269 (16)	0.0384 (18)	0.0136 (14)	0.0083 (14)	0.0101 (14)
C34B	0.0360 (19)	0.0247 (15)	0.0344 (18)	0.0088 (14)	0.0073 (14)	0.0042 (13)
C35B	0.0261 (17)	0.0408 (18)	0.0256 (16)	0.0089 (14)	0.0037 (13)	0.0106 (14)
C36B	0.0330 (19)	0.0356 (18)	0.0393 (19)	0.0169 (15)	0.0024 (15)	0.0122 (14)
C37B	0.0351 (19)	0.0239 (15)	0.0381 (18)	0.0115 (14)	−0.0008 (14)	0.0057 (13)
N31B	0.0331 (17)	0.0472 (18)	0.0363 (16)	0.0033 (15)	0.0035 (13)	0.0119 (14)
O31B	0.0392 (14)	0.0497 (16)	0.0583 (16)	−0.0034 (12)	0.0022 (12)	0.0049 (13)
O32B	0.0347 (15)	0.0721 (18)	0.0692 (18)	0.0201 (14)	−0.0042 (12)	0.0184 (14)
C4B	0.0228 (16)	0.0262 (16)	0.0295 (17)	0.0079 (12)	0.0018 (13)	0.0065 (13)
C41B	0.0315 (18)	0.0335 (18)	0.0375 (19)	0.0104 (14)	0.0036 (14)	0.0103 (14)
O41B	0.0462 (14)	0.0311 (12)	0.0479 (14)	0.0051 (10)	0.0115 (11)	0.0148 (10)
C5B	0.0257 (16)	0.0254 (15)	0.0262 (16)	0.0074 (13)	−0.0013 (13)	0.0010 (12)
Cl5B	0.0403 (5)	0.0268 (4)	0.0343 (4)	0.0076 (3)	0.0046 (3)	0.0026 (3)

Geometric parameters (Å, º) top

N1A—C2A	1.341 (3)	C2B—C21B	1.494 (4)
N1A—C5A	1.351 (4)	C21B—C22B	1.504 (5)
C2A—N3A	1.351 (4)	C21B—H21B	0.99
C2A—C21A	1.491 (4)	C21B—H22B	0.99
C21A—C22A	1.537 (4)	C22B—C23B	1.405 (6)
C21A—H21A	0.99	C22B—H23B	0.99
C21A—H22A	0.99	C22B—H24B	0.99
C22A—C23A	1.518 (4)	C23B—C24B	1.534 (9)
C22A—H23A	0.99	C23B—H25B	0.99
C22A—H24A	0.99	C23B—H26B	0.99
C23A—C24A	1.515 (4)	C24B—H27B	0.98
C23A—H25A	0.99	C24B—H28B	0.98
C23A—H26A	0.99	C24B—H29B	0.98
C24A—H27A	0.98	C22C—H23C	0.99
C24A—H28A	0.98	C22C—H24C	0.99
C24A—H29A	0.98	C24C—H27C	0.98
N3A—C4A	1.400 (3)	C24C—H28C	0.98
N3A—C31A	1.467 (3)	C24C—H29C	0.98
C31A—C32A	1.518 (4)	N3B—C4B	1.392 (3)
C31A—H31A	0.99	N3B—C31B	1.460 (3)
C31A—H32A	0.99	C31B—C32B	1.511 (4)
C32A—C37A	1.386 (4)	C31B—H31B	0.99
C32A—C33A	1.395 (4)	C31B—H32B	0.99
C33A—C34A	1.378 (4)	C32B—C37B	1.383 (4)
C33A—H33A	0.95	C32B—C33B	1.396 (4)
C34A—C35A	1.385 (4)	C33B—C34B	1.380 (4)
C34A—H34A	0.95	C33B—H33B	0.95
C35A—C36A	1.378 (4)	C34B—C35B	1.381 (4)
C35A—N31A	1.469 (3)	C34B—H34B	0.95
C36A—C37A	1.378 (4)	C35B—C36B	1.379 (4)
C36A—H36A	0.95	C35B—N31B	1.470 (4)
C37A—H37A	0.95	C36B—C37B	1.386 (4)
N31A—O31A	1.227 (3)	C36B—H36B	0.95
N31A—O32A	1.233 (3)	C37B—H37B	0.95
C4A—C5A	1.373 (4)	N31B—O31B	1.222 (3)
C4A—C41A	1.436 (4)	N31B—O32B	1.233 (3)
C41A—O41A	1.217 (3)	C4B—C5B	1.379 (4)
C41A—H41A	0.95	C4B—C41B	1.439 (4)
C5A—Cl5A	1.714 (3)	C41B—O41B	1.219 (3)
N1B—C2B	1.334 (3)	C41B—H41B	0.95
N1B—C5B	1.349 (4)	C5B—Cl5B	1.716 (3)
C2B—N3B	1.360 (3)

C2A—N1A—C5A	104.4 (2)	C4A—C5A—Cl5A	126.9 (2)
N1A—C2A—N3A	111.6 (3)	C2B—N1B—C5B	104.4 (2)
N1A—C2A—C21A	123.6 (3)	N1B—C2B—N3B	112.2 (2)
N3A—C2A—C21A	124.7 (2)	N1B—C2B—C21B	124.4 (3)
C2A—C21A—C22A	115.5 (2)	N3B—C2B—C21B	123.3 (2)
C2A—C21A—H21A	108.4	C2B—N3B—C4B	106.8 (2)
C22A—C21A—H21A	108.4	C2B—N3B—C31B	127.0 (2)
C2A—C21A—H22A	108.4	C4B—N3B—C31B	126.1 (2)
C22A—C21A—H22A	108.4	N3B—C31B—C32B	114.0 (2)
H21A—C21A—H22A	107.5	N3B—C31B—H31B	108.8
C23A—C22A—C21A	110.9 (2)	C32B—C31B—H31B	108.8
C23A—C22A—H23A	109.5	N3B—C31B—H32B	108.8
C21A—C22A—H23A	109.5	C32B—C31B—H32B	108.8
C23A—C22A—H24A	109.5	H31B—C31B—H32B	107.7
C21A—C22A—H24A	109.5	C37B—C32B—C33B	119.2 (3)
H23A—C22A—H24A	108.0	C37B—C32B—C31B	122.9 (2)
C24A—C23A—C22A	113.9 (3)	C33B—C32B—C31B	117.8 (2)
C24A—C23A—H25A	108.8	C34B—C33B—C32B	120.7 (3)
C22A—C23A—H25A	108.8	C34B—C33B—H33B	119.7
C24A—C23A—H26A	108.8	C32B—C33B—H33B	119.7
C22A—C23A—H26A	108.8	C33B—C34B—C35B	118.6 (3)
H25A—C23A—H26A	107.7	C33B—C34B—H34B	120.7
C23A—C24A—H27A	109.5	C35B—C34B—H34B	120.7
C23A—C24A—H28A	109.5	C36B—C35B—C34B	122.2 (3)
H27A—C24A—H28A	109.5	C36B—C35B—N31B	118.8 (3)
C23A—C24A—H29A	109.5	C34B—C35B—N31B	119.0 (3)
H27A—C24A—H29A	109.5	C35B—C36B—C37B	118.4 (3)
H28A—C24A—H29A	109.5	C35B—C36B—H36B	120.8
C2A—N3A—C4A	107.6 (2)	C37B—C36B—H36B	120.8
C2A—N3A—C31A	126.6 (2)	C32B—C37B—C36B	120.9 (3)
C4A—N3A—C31A	125.7 (2)	C32B—C37B—H37B	119.6
N3A—C31A—C32A	112.1 (2)	C36B—C37B—H37B	119.6
N3A—C31A—H31A	109.2	O31B—N31B—O32B	123.8 (3)
C32A—C31A—H31A	109.2	O31B—N31B—C35B	118.0 (3)
N3A—C31A—H32A	109.2	O32B—N31B—C35B	118.2 (3)
C32A—C31A—H32A	109.2	C5B—C4B—N3B	104.0 (2)
H31A—C31A—H32A	107.9	C5B—C4B—C41B	128.8 (3)
C37A—C32A—C33A	118.8 (3)	N3B—C4B—C41B	127.2 (2)
C37A—C32A—C31A	122.3 (2)	O41B—C41B—C4B	126.3 (3)
C33A—C32A—C31A	118.9 (2)	O41B—C41B—H41B	116.8
C34A—C33A—C32A	121.1 (3)	C4B—C41B—H41B	116.8
C34A—C33A—H33A	119.4	N1B—C5B—C4B	112.6 (2)
C32A—C33A—H33A	119.4	N1B—C5B—Cl5B	121.4 (2)
C33A—C34A—C35A	118.2 (3)	C4B—C5B—Cl5B	126.0 (2)
C33A—C34A—H34A	120.9	C2B—C21B—C22B	113.8 (3)
C35A—C34A—H34A	120.9	C2B—C21B—H21B	108.8
C36A—C35A—C34A	122.0 (3)	C22B—C21B—H21B	108.8
C36A—C35A—N31A	119.1 (2)	C2B—C21B—H22B	108.8
C34A—C35A—N31A	118.9 (2)	C22B—C21B—H22B	108.8
C37A—C36A—C35A	118.8 (3)	H21B—C21B—H22B	107.7
C37A—C36A—H36A	120.6	C23B—C22B—C21B	120.0 (4)
C35A—C36A—H36A	120.6	C23B—C22B—H23B	107.3
C36A—C37A—C32A	121.0 (3)	C21B—C22B—H23B	107.3
C36A—C37A—H37A	119.5	C23B—C22B—H24B	107.3
C32A—C37A—H37A	119.5	C21B—C22B—H24B	107.3
O31A—N31A—O32A	123.5 (2)	H23B—C22B—H24B	106.9
O31A—N31A—C35A	118.2 (2)	C22B—C23B—C24B	112.5 (6)
O32A—N31A—C35A	118.3 (2)	C22B—C23B—H25B	109.1
C5A—C4A—N3A	103.4 (2)	C24B—C23B—H25B	109.1
C5A—C4A—C41A	130.2 (3)	C22B—C23B—H26B	109.1
N3A—C4A—C41A	126.4 (2)	C24B—C23B—H26B	109.1
O41A—C41A—C4A	126.4 (3)	H25B—C23B—H26B	107.8
O41A—C41A—H41A	116.8	H23C—C22C—H24C	106.4
C4A—C41A—H41A	116.8	H27C—C24C—H28C	109.5
N1A—C5A—C4A	112.9 (2)	H27C—C24C—H29C	109.5
N1A—C5A—Cl5A	120.2 (2)	H28C—C24C—H29C	109.5

C5A—N1A—C2A—N3A	0.0 (3)	C5B—N1B—C2B—N3B	0.0 (3)
C5A—N1A—C2A—C21A	−178.5 (3)	C5B—N1B—C2B—C21B	176.7 (3)
N1A—C2A—C21A—C22A	−106.8 (3)	N1B—C2B—N3B—C4B	0.0 (3)
N3A—C2A—C21A—C22A	74.9 (4)	C21B—C2B—N3B—C4B	−176.8 (3)
C2A—C21A—C22A—C23A	175.1 (3)	N1B—C2B—N3B—C31B	179.6 (2)
C21A—C22A—C23A—C24A	179.0 (3)	C21B—C2B—N3B—C31B	2.8 (4)
N1A—C2A—N3A—C4A	0.0 (3)	C2B—N3B—C31B—C32B	97.8 (3)
C21A—C2A—N3A—C4A	178.5 (3)	C4B—N3B—C31B—C32B	−82.7 (3)
N1A—C2A—N3A—C31A	176.8 (2)	N3B—C31B—C32B—C37B	12.5 (4)
C21A—C2A—N3A—C31A	−4.7 (4)	N3B—C31B—C32B—C33B	−170.0 (2)
C2A—N3A—C31A—C32A	−104.2 (3)	C37B—C32B—C33B—C34B	−0.7 (4)
C4A—N3A—C31A—C32A	71.9 (3)	C31B—C32B—C33B—C34B	−178.3 (3)
N3A—C31A—C32A—C37A	12.6 (4)	C32B—C33B—C34B—C35B	0.5 (4)
N3A—C31A—C32A—C33A	−166.4 (2)	C33B—C34B—C35B—C36B	0.2 (4)
C37A—C32A—C33A—C34A	−2.0 (4)	C33B—C34B—C35B—N31B	179.4 (3)
C31A—C32A—C33A—C34A	177.0 (2)	C34B—C35B—C36B—C37B	−0.7 (4)
C32A—C33A—C34A—C35A	0.4 (4)	N31B—C35B—C36B—C37B	−180.0 (3)
C33A—C34A—C35A—C36A	1.8 (4)	C33B—C32B—C37B—C36B	0.1 (4)
C33A—C34A—C35A—N31A	−178.2 (2)	C31B—C32B—C37B—C36B	177.6 (3)
C34A—C35A—C36A—C37A	−2.4 (4)	C35B—C36B—C37B—C32B	0.5 (4)
N31A—C35A—C36A—C37A	177.6 (2)	C36B—C35B—N31B—O31B	−177.7 (3)
C35A—C36A—C37A—C32A	0.7 (4)	C34B—C35B—N31B—O31B	3.0 (4)
C33A—C32A—C37A—C36A	1.4 (4)	C36B—C35B—N31B—O32B	2.8 (4)
C31A—C32A—C37A—C36A	−177.6 (3)	C34B—C35B—N31B—O32B	−176.5 (3)
C36A—C35A—N31A—O31A	−177.8 (2)	C2B—N3B—C4B—C5B	0.0 (3)
C34A—C35A—N31A—O31A	2.2 (4)	C31B—N3B—C4B—C5B	−179.6 (2)
C36A—C35A—N31A—O32A	2.1 (4)	C2B—N3B—C4B—C41B	180.0 (3)
C34A—C35A—N31A—O32A	−178.0 (2)	C31B—N3B—C4B—C41B	0.4 (4)
C2A—N3A—C4A—C5A	−0.1 (3)	C5B—C4B—C41B—O41B	179.0 (3)
C31A—N3A—C4A—C5A	−176.9 (2)	N3B—C4B—C41B—O41B	−0.9 (5)
C2A—N3A—C4A—C41A	179.7 (3)	C2B—N1B—C5B—C4B	0.0 (3)
C31A—N3A—C4A—C41A	2.9 (4)	C2B—N1B—C5B—Cl5B	−179.8 (2)
C5A—C4A—C41A—O41A	−178.4 (3)	N3B—C4B—C5B—N1B	0.0 (3)
N3A—C4A—C41A—O41A	1.8 (5)	C41B—C4B—C5B—N1B	180.0 (3)
C2A—N1A—C5A—C4A	−0.1 (3)	N3B—C4B—C5B—Cl5B	179.8 (2)
C2A—N1A—C5A—Cl5A	179.7 (2)	C41B—C4B—C5B—Cl5B	−0.2 (4)
N3A—C4A—C5A—N1A	0.1 (3)	N1B—C2B—C21B—C22B	16.0 (5)
C41A—C4A—C5A—N1A	−179.7 (3)	N3B—C2B—C21B—C22B	−167.5 (3)
N3A—C4A—C5A—Cl5A	−179.6 (2)	C2B—C21B—C22B—C23B	70.9 (6)
C41A—C4A—C5A—Cl5A	0.6 (5)	C21B—C22B—C23B—C24B	−173.9 (5)

Acknowledgements

The authors thank the EPSRC National Crystallography Service (Southampton, England) and acknowledge the use of the EPSRC's Chemical Database Service at Daresbury.

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