organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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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[Rasmussen, P. G. (1999). J. Chem. Educ. 76, 1345.]; Ambalvanan et al., 2003[Ambalvanan, P., Palani, K., Ponnuswamy, M. N., Thirumuruhan, R. A., Yathirajan, H. S., Prabhuswamy, B., Raju, C. R., Nagaraja, P. & Mohana, K. N. (2003). Mol. Cryst. Liq. Cryst. 393, 75-82.]). With this in mind, the title compound, (I[link]), was prepared in a series of syntheses to produce new imidazole derivatives. The Cambridge Structural Database (Version of April 2004; Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]) reveals that there are currently 42 known structures containing a 3-benzyl­imidazole moiety, but not yet the title compound.

[Scheme 1]

The asymmetric unit of (I[link]) comprises two mol­ecules, A and B, that are each twisted about the benzyl C atom (Fig. 1[link]). 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]
Figure 1
The molecular configurations and atom-numbering schemes for the two independent mol­ecules, A and B, of (I[link]). 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

  • Mr = 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

  • Dx = 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[Sheldrick, G. M. (1997b). SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.911, Tmax = 0.990

  • 30 632 measured reflections

  • 6038 independent reflections

  • 3622 reflections with I > 2σ(I)

  • Rint = 0.098

  • θmax = 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(Fo2) + (0.0645P)2 + 0.076P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.29 e Å−3

  • Δρmin = −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 1.25Ueq of the carrier atom. A high Rint was the result of weak high-angle data.

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a[Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a[Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON97 (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information


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
C15H16ClN3O3Z = 4
Mr = 321.76F(000) = 672
Triclinic, P1Dx = 1.387 Mg m3
Hall symbol: -P 1Melting point: 375 K
a = 8.3007 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.2295 (6) ÅCell parameters from 6811 reflections
c = 16.5605 (10) Åθ = 2.9–27.5°
α = 103.420 (4)°µ = 0.26 mm1
β = 95.561 (3)°T = 120 K
γ = 106.758 (3)°Plate, colourless
V = 1541.35 (15) Å30.36 × 0.30 × 0.04 mm
Data collection top
Bruker-Nonius KappaCCD area-detector
diffractometer
6038 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode3622 reflections with I > 2σ(I)
10 cm confocal mirrors monochromatorRint = 0.098
Detector resolution: 9.091 pixels mm-1θmax = 26.0°, θmin = 2.9°
φ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997b)
k = 1515
Tmin = 0.911, Tmax = 0.990l = 2020
30632 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0645P)2 + 0.076P]
where P = (Fo2 + 2Fc2)/3
6038 reflections(Δ/σ)max < 0.001
418 parametersΔρmax = 0.29 e Å3
5 restraintsΔρmin = 0.34 e Å3
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
xyzUiso*/UeqOcc. (<1)
N1A0.1941 (3)0.9197 (2)0.21017 (15)0.0320 (6)
C2A0.1120 (4)0.8084 (2)0.21159 (18)0.0291 (7)
C21A0.0110 (4)0.7792 (3)0.27785 (19)0.0341 (7)
H21A0.10160.72030.24970.043*
H22A0.00990.85200.30890.043*
C22A0.0936 (4)0.7298 (3)0.34200 (18)0.0336 (7)
H23A0.10420.65250.31270.042*
H24A0.20980.78500.36780.042*
C23A0.0126 (4)0.7134 (3)0.4106 (2)0.0452 (9)
H25A0.02190.79120.43970.056*
H26A0.12940.65980.38400.056*
C24A0.0598 (5)0.6628 (3)0.4755 (2)0.0473 (9)
H27A0.05200.58060.44900.059*
H28A0.00550.66490.52170.059*
H29A0.17980.71030.49770.059*
N3A0.1292 (3)0.72747 (19)0.14485 (14)0.0260 (5)
C31A0.0640 (4)0.5979 (2)0.12824 (19)0.0281 (7)
H31A0.00880.56230.06830.035*
H32A0.02390.57690.16340.035*
C32A0.2046 (3)0.5464 (2)0.14713 (17)0.0244 (6)
C33A0.1713 (4)0.4240 (2)0.11796 (17)0.0280 (7)
H33A0.06010.37480.08920.035*
C34A0.2970 (4)0.3735 (2)0.13014 (17)0.0278 (7)
H34A0.27400.29030.10990.035*
C35A0.4576 (3)0.4473 (2)0.17274 (17)0.0256 (6)
C36A0.4929 (4)0.5679 (2)0.20476 (18)0.0286 (7)
H36A0.60290.61640.23560.036*
C37A0.3659 (3)0.6167 (2)0.19124 (17)0.0273 (7)
H37A0.38920.69990.21250.034*
N31A0.5943 (3)0.3952 (2)0.18395 (15)0.0306 (6)
O31A0.5619 (3)0.28834 (18)0.15276 (14)0.0411 (6)
O32A0.7355 (3)0.46121 (18)0.22401 (13)0.0389 (5)
C4A0.2293 (3)0.7895 (2)0.09634 (18)0.0270 (7)
C41A0.2801 (4)0.7385 (3)0.01985 (19)0.0311 (7)
H41A0.35130.79210.00520.039*
O41A0.2410 (3)0.63322 (18)0.01605 (13)0.0373 (5)
C5A0.2643 (4)0.9064 (2)0.13975 (19)0.0307 (7)
Cl5A0.38198 (10)1.02856 (6)0.11284 (5)0.0410 (2)
N1B0.6628 (3)0.1150 (2)0.22474 (15)0.0313 (6)
C2B0.6981 (4)0.0002 (2)0.26254 (18)0.0300 (7)
C21B0.6407 (5)0.0477 (3)0.3422 (2)0.0454 (9)
H21B0.54620.07820.32840.057*0.50
H22B0.73640.11530.37900.057*0.50
H21C0.51470.01360.33360.057*0.50
H22C0.66890.13460.35220.057*0.50
C22B0.5810 (7)0.0426 (4)0.3902 (3)0.0548 (14)0.75
H23B0.52040.00930.43320.068*0.75
H24B0.49530.11330.35020.068*0.75
C22C0.7160 (19)0.0238 (10)0.4224 (7)0.050 (4)0.25
H23C0.84030.06670.43310.062*0.25
H24C0.66950.06390.46920.062*0.25
C23B0.6998 (7)0.0824 (5)0.4313 (3)0.0957 (18)
H25B0.77810.01520.47710.120*0.50
H26B0.76900.11030.39070.120*0.50
H25C0.77490.11230.39530.120*0.50
H26C0.58140.13110.40360.120*0.50
C24B0.6138 (14)0.1835 (8)0.4688 (7)0.076 (3)0.50
H27B0.53780.15870.50550.096*0.50
H28B0.70160.20260.50160.096*0.50
H29B0.54730.25380.42310.096*0.50
C24C0.7279 (15)0.1186 (9)0.5099 (5)0.077 (3)0.50
H27C0.85090.09450.53110.096*0.50
H28C0.67870.20500.49790.096*0.50
H29C0.67280.08020.55250.096*0.50
N3B0.7853 (3)0.07047 (19)0.21787 (14)0.0272 (6)
C31B0.8436 (4)0.2000 (2)0.24006 (19)0.0315 (7)
H31B0.77150.22950.27830.039*
H32B0.82700.22550.18820.039*
C32B1.0288 (4)0.2568 (2)0.28223 (17)0.0255 (6)
C33B1.0880 (4)0.3795 (2)0.31769 (18)0.0315 (7)
H33B1.01130.42380.31600.039*
C34B1.2568 (4)0.4371 (3)0.35520 (18)0.0325 (7)
H34B1.29700.52050.37980.041*
C35B1.3661 (4)0.3708 (3)0.35625 (17)0.0310 (7)
C36B1.3121 (4)0.2497 (3)0.32099 (19)0.0346 (7)
H36B1.38990.20600.32190.043*
C37B1.1418 (4)0.1932 (3)0.28422 (19)0.0329 (7)
H37B1.10220.10970.26010.041*
N31B1.5466 (3)0.4314 (3)0.39535 (16)0.0411 (7)
O31B1.5914 (3)0.5382 (2)0.42867 (15)0.0552 (7)
O32B1.6441 (3)0.3719 (2)0.39210 (16)0.0591 (7)
C4B0.8079 (3)0.0049 (2)0.14593 (17)0.0266 (7)
C41B0.8932 (4)0.0287 (3)0.07954 (19)0.0342 (7)
H41B0.89930.03380.03490.043*
O41B0.9582 (3)0.12965 (18)0.07510 (13)0.0424 (6)
C5B0.7303 (3)0.1171 (2)0.15369 (17)0.0274 (7)
Cl5B0.71564 (10)0.24842 (6)0.08330 (5)0.0357 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0331 (15)0.0262 (14)0.0401 (16)0.0145 (11)0.0045 (12)0.0103 (11)
C2A0.0258 (17)0.0268 (16)0.0372 (18)0.0137 (13)0.0027 (13)0.0081 (14)
C21A0.0330 (18)0.0349 (17)0.0386 (18)0.0177 (14)0.0104 (15)0.0079 (14)
C22A0.0310 (18)0.0322 (17)0.0368 (18)0.0106 (14)0.0047 (14)0.0076 (14)
C23A0.046 (2)0.051 (2)0.046 (2)0.0214 (17)0.0163 (17)0.0166 (17)
C24A0.064 (2)0.043 (2)0.037 (2)0.0204 (18)0.0147 (17)0.0091 (16)
N3A0.0208 (13)0.0216 (12)0.0368 (14)0.0084 (10)0.0040 (11)0.0089 (11)
C31A0.0244 (16)0.0208 (15)0.0366 (17)0.0043 (12)0.0047 (13)0.0067 (13)
C32A0.0247 (16)0.0205 (14)0.0307 (16)0.0071 (12)0.0088 (13)0.0107 (12)
C33A0.0266 (17)0.0240 (15)0.0295 (16)0.0044 (13)0.0007 (13)0.0060 (13)
C34A0.0302 (17)0.0236 (15)0.0308 (17)0.0094 (13)0.0060 (13)0.0084 (13)
C35A0.0228 (16)0.0262 (15)0.0329 (16)0.0106 (13)0.0085 (13)0.0128 (13)
C36A0.0238 (16)0.0258 (15)0.0342 (17)0.0048 (13)0.0022 (13)0.0096 (13)
C37A0.0264 (17)0.0185 (14)0.0331 (17)0.0052 (12)0.0024 (13)0.0036 (12)
N31A0.0307 (15)0.0309 (15)0.0372 (15)0.0138 (12)0.0091 (12)0.0161 (12)
O31A0.0392 (13)0.0263 (12)0.0652 (16)0.0170 (10)0.0119 (11)0.0170 (11)
O32A0.0270 (13)0.0405 (13)0.0488 (14)0.0119 (10)0.0011 (10)0.0133 (11)
C4A0.0207 (15)0.0256 (15)0.0360 (18)0.0069 (12)0.0036 (13)0.0124 (13)
C41A0.0225 (16)0.0327 (18)0.0392 (19)0.0073 (13)0.0012 (14)0.0156 (15)
O41A0.0344 (13)0.0310 (12)0.0399 (13)0.0063 (10)0.0046 (10)0.0032 (10)
C5A0.0289 (17)0.0207 (15)0.0433 (19)0.0079 (13)0.0002 (14)0.0130 (14)
Cl5A0.0365 (5)0.0269 (4)0.0585 (5)0.0048 (3)0.0017 (4)0.0192 (4)
N1B0.0314 (15)0.0275 (14)0.0336 (15)0.0085 (11)0.0059 (12)0.0069 (11)
C2B0.0283 (17)0.0290 (17)0.0329 (17)0.0103 (13)0.0039 (14)0.0083 (14)
C21B0.063 (2)0.0383 (19)0.043 (2)0.0260 (18)0.0199 (18)0.0098 (16)
C22B0.079 (4)0.040 (3)0.060 (3)0.028 (3)0.041 (3)0.019 (3)
C22C0.065 (11)0.023 (7)0.046 (9)0.002 (7)0.019 (8)0.003 (6)
C23B0.156 (5)0.123 (4)0.071 (3)0.104 (4)0.058 (3)0.055 (3)
C24B0.117 (10)0.084 (8)0.079 (8)0.073 (7)0.059 (7)0.052 (6)
C24C0.125 (10)0.092 (8)0.049 (6)0.068 (7)0.036 (6)0.033 (6)
N3B0.0242 (13)0.0220 (12)0.0336 (14)0.0086 (10)0.0008 (11)0.0048 (11)
C31B0.0316 (18)0.0231 (15)0.0405 (18)0.0128 (13)0.0006 (14)0.0070 (13)
C32B0.0293 (17)0.0260 (15)0.0226 (15)0.0100 (13)0.0032 (12)0.0084 (12)
C33B0.0328 (18)0.0269 (16)0.0384 (18)0.0136 (14)0.0083 (14)0.0101 (14)
C34B0.0360 (19)0.0247 (15)0.0344 (18)0.0088 (14)0.0073 (14)0.0042 (13)
C35B0.0261 (17)0.0408 (18)0.0256 (16)0.0089 (14)0.0037 (13)0.0106 (14)
C36B0.0330 (19)0.0356 (18)0.0393 (19)0.0169 (15)0.0024 (15)0.0122 (14)
C37B0.0351 (19)0.0239 (15)0.0381 (18)0.0115 (14)0.0008 (14)0.0057 (13)
N31B0.0331 (17)0.0472 (18)0.0363 (16)0.0033 (15)0.0035 (13)0.0119 (14)
O31B0.0392 (14)0.0497 (16)0.0583 (16)0.0034 (12)0.0022 (12)0.0049 (13)
O32B0.0347 (15)0.0721 (18)0.0692 (18)0.0201 (14)0.0042 (12)0.0184 (14)
C4B0.0228 (16)0.0262 (16)0.0295 (17)0.0079 (12)0.0018 (13)0.0065 (13)
C41B0.0315 (18)0.0335 (18)0.0375 (19)0.0104 (14)0.0036 (14)0.0103 (14)
O41B0.0462 (14)0.0311 (12)0.0479 (14)0.0051 (10)0.0115 (11)0.0148 (10)
C5B0.0257 (16)0.0254 (15)0.0262 (16)0.0074 (13)0.0013 (13)0.0010 (12)
Cl5B0.0403 (5)0.0268 (4)0.0343 (4)0.0076 (3)0.0046 (3)0.0026 (3)
Geometric parameters (Å, º) top
N1A—C2A1.341 (3)C2B—C21B1.494 (4)
N1A—C5A1.351 (4)C21B—C22B1.504 (5)
C2A—N3A1.351 (4)C21B—H21B0.99
C2A—C21A1.491 (4)C21B—H22B0.99
C21A—C22A1.537 (4)C22B—C23B1.405 (6)
C21A—H21A0.99C22B—H23B0.99
C21A—H22A0.99C22B—H24B0.99
C22A—C23A1.518 (4)C23B—C24B1.534 (9)
C22A—H23A0.99C23B—H25B0.99
C22A—H24A0.99C23B—H26B0.99
C23A—C24A1.515 (4)C24B—H27B0.98
C23A—H25A0.99C24B—H28B0.98
C23A—H26A0.99C24B—H29B0.98
C24A—H27A0.98C22C—H23C0.99
C24A—H28A0.98C22C—H24C0.99
C24A—H29A0.98C24C—H27C0.98
N3A—C4A1.400 (3)C24C—H28C0.98
N3A—C31A1.467 (3)C24C—H29C0.98
C31A—C32A1.518 (4)N3B—C4B1.392 (3)
C31A—H31A0.99N3B—C31B1.460 (3)
C31A—H32A0.99C31B—C32B1.511 (4)
C32A—C37A1.386 (4)C31B—H31B0.99
C32A—C33A1.395 (4)C31B—H32B0.99
C33A—C34A1.378 (4)C32B—C37B1.383 (4)
C33A—H33A0.95C32B—C33B1.396 (4)
C34A—C35A1.385 (4)C33B—C34B1.380 (4)
C34A—H34A0.95C33B—H33B0.95
C35A—C36A1.378 (4)C34B—C35B1.381 (4)
C35A—N31A1.469 (3)C34B—H34B0.95
C36A—C37A1.378 (4)C35B—C36B1.379 (4)
C36A—H36A0.95C35B—N31B1.470 (4)
C37A—H37A0.95C36B—C37B1.386 (4)
N31A—O31A1.227 (3)C36B—H36B0.95
N31A—O32A1.233 (3)C37B—H37B0.95
C4A—C5A1.373 (4)N31B—O31B1.222 (3)
C4A—C41A1.436 (4)N31B—O32B1.233 (3)
C41A—O41A1.217 (3)C4B—C5B1.379 (4)
C41A—H41A0.95C4B—C41B1.439 (4)
C5A—Cl5A1.714 (3)C41B—O41B1.219 (3)
N1B—C2B1.334 (3)C41B—H41B0.95
N1B—C5B1.349 (4)C5B—Cl5B1.716 (3)
C2B—N3B1.360 (3)
C2A—N1A—C5A104.4 (2)C4A—C5A—Cl5A126.9 (2)
N1A—C2A—N3A111.6 (3)C2B—N1B—C5B104.4 (2)
N1A—C2A—C21A123.6 (3)N1B—C2B—N3B112.2 (2)
N3A—C2A—C21A124.7 (2)N1B—C2B—C21B124.4 (3)
C2A—C21A—C22A115.5 (2)N3B—C2B—C21B123.3 (2)
C2A—C21A—H21A108.4C2B—N3B—C4B106.8 (2)
C22A—C21A—H21A108.4C2B—N3B—C31B127.0 (2)
C2A—C21A—H22A108.4C4B—N3B—C31B126.1 (2)
C22A—C21A—H22A108.4N3B—C31B—C32B114.0 (2)
H21A—C21A—H22A107.5N3B—C31B—H31B108.8
C23A—C22A—C21A110.9 (2)C32B—C31B—H31B108.8
C23A—C22A—H23A109.5N3B—C31B—H32B108.8
C21A—C22A—H23A109.5C32B—C31B—H32B108.8
C23A—C22A—H24A109.5H31B—C31B—H32B107.7
C21A—C22A—H24A109.5C37B—C32B—C33B119.2 (3)
H23A—C22A—H24A108.0C37B—C32B—C31B122.9 (2)
C24A—C23A—C22A113.9 (3)C33B—C32B—C31B117.8 (2)
C24A—C23A—H25A108.8C34B—C33B—C32B120.7 (3)
C22A—C23A—H25A108.8C34B—C33B—H33B119.7
C24A—C23A—H26A108.8C32B—C33B—H33B119.7
C22A—C23A—H26A108.8C33B—C34B—C35B118.6 (3)
H25A—C23A—H26A107.7C33B—C34B—H34B120.7
C23A—C24A—H27A109.5C35B—C34B—H34B120.7
C23A—C24A—H28A109.5C36B—C35B—C34B122.2 (3)
H27A—C24A—H28A109.5C36B—C35B—N31B118.8 (3)
C23A—C24A—H29A109.5C34B—C35B—N31B119.0 (3)
H27A—C24A—H29A109.5C35B—C36B—C37B118.4 (3)
H28A—C24A—H29A109.5C35B—C36B—H36B120.8
C2A—N3A—C4A107.6 (2)C37B—C36B—H36B120.8
C2A—N3A—C31A126.6 (2)C32B—C37B—C36B120.9 (3)
C4A—N3A—C31A125.7 (2)C32B—C37B—H37B119.6
N3A—C31A—C32A112.1 (2)C36B—C37B—H37B119.6
N3A—C31A—H31A109.2O31B—N31B—O32B123.8 (3)
C32A—C31A—H31A109.2O31B—N31B—C35B118.0 (3)
N3A—C31A—H32A109.2O32B—N31B—C35B118.2 (3)
C32A—C31A—H32A109.2C5B—C4B—N3B104.0 (2)
H31A—C31A—H32A107.9C5B—C4B—C41B128.8 (3)
C37A—C32A—C33A118.8 (3)N3B—C4B—C41B127.2 (2)
C37A—C32A—C31A122.3 (2)O41B—C41B—C4B126.3 (3)
C33A—C32A—C31A118.9 (2)O41B—C41B—H41B116.8
C34A—C33A—C32A121.1 (3)C4B—C41B—H41B116.8
C34A—C33A—H33A119.4N1B—C5B—C4B112.6 (2)
C32A—C33A—H33A119.4N1B—C5B—Cl5B121.4 (2)
C33A—C34A—C35A118.2 (3)C4B—C5B—Cl5B126.0 (2)
C33A—C34A—H34A120.9C2B—C21B—C22B113.8 (3)
C35A—C34A—H34A120.9C2B—C21B—H21B108.8
C36A—C35A—C34A122.0 (3)C22B—C21B—H21B108.8
C36A—C35A—N31A119.1 (2)C2B—C21B—H22B108.8
C34A—C35A—N31A118.9 (2)C22B—C21B—H22B108.8
C37A—C36A—C35A118.8 (3)H21B—C21B—H22B107.7
C37A—C36A—H36A120.6C23B—C22B—C21B120.0 (4)
C35A—C36A—H36A120.6C23B—C22B—H23B107.3
C36A—C37A—C32A121.0 (3)C21B—C22B—H23B107.3
C36A—C37A—H37A119.5C23B—C22B—H24B107.3
C32A—C37A—H37A119.5C21B—C22B—H24B107.3
O31A—N31A—O32A123.5 (2)H23B—C22B—H24B106.9
O31A—N31A—C35A118.2 (2)C22B—C23B—C24B112.5 (6)
O32A—N31A—C35A118.3 (2)C22B—C23B—H25B109.1
C5A—C4A—N3A103.4 (2)C24B—C23B—H25B109.1
C5A—C4A—C41A130.2 (3)C22B—C23B—H26B109.1
N3A—C4A—C41A126.4 (2)C24B—C23B—H26B109.1
O41A—C41A—C4A126.4 (3)H25B—C23B—H26B107.8
O41A—C41A—H41A116.8H23C—C22C—H24C106.4
C4A—C41A—H41A116.8H27C—C24C—H28C109.5
N1A—C5A—C4A112.9 (2)H27C—C24C—H29C109.5
N1A—C5A—Cl5A120.2 (2)H28C—C24C—H29C109.5
C5A—N1A—C2A—N3A0.0 (3)C5B—N1B—C2B—N3B0.0 (3)
C5A—N1A—C2A—C21A178.5 (3)C5B—N1B—C2B—C21B176.7 (3)
N1A—C2A—C21A—C22A106.8 (3)N1B—C2B—N3B—C4B0.0 (3)
N3A—C2A—C21A—C22A74.9 (4)C21B—C2B—N3B—C4B176.8 (3)
C2A—C21A—C22A—C23A175.1 (3)N1B—C2B—N3B—C31B179.6 (2)
C21A—C22A—C23A—C24A179.0 (3)C21B—C2B—N3B—C31B2.8 (4)
N1A—C2A—N3A—C4A0.0 (3)C2B—N3B—C31B—C32B97.8 (3)
C21A—C2A—N3A—C4A178.5 (3)C4B—N3B—C31B—C32B82.7 (3)
N1A—C2A—N3A—C31A176.8 (2)N3B—C31B—C32B—C37B12.5 (4)
C21A—C2A—N3A—C31A4.7 (4)N3B—C31B—C32B—C33B170.0 (2)
C2A—N3A—C31A—C32A104.2 (3)C37B—C32B—C33B—C34B0.7 (4)
C4A—N3A—C31A—C32A71.9 (3)C31B—C32B—C33B—C34B178.3 (3)
N3A—C31A—C32A—C37A12.6 (4)C32B—C33B—C34B—C35B0.5 (4)
N3A—C31A—C32A—C33A166.4 (2)C33B—C34B—C35B—C36B0.2 (4)
C37A—C32A—C33A—C34A2.0 (4)C33B—C34B—C35B—N31B179.4 (3)
C31A—C32A—C33A—C34A177.0 (2)C34B—C35B—C36B—C37B0.7 (4)
C32A—C33A—C34A—C35A0.4 (4)N31B—C35B—C36B—C37B180.0 (3)
C33A—C34A—C35A—C36A1.8 (4)C33B—C32B—C37B—C36B0.1 (4)
C33A—C34A—C35A—N31A178.2 (2)C31B—C32B—C37B—C36B177.6 (3)
C34A—C35A—C36A—C37A2.4 (4)C35B—C36B—C37B—C32B0.5 (4)
N31A—C35A—C36A—C37A177.6 (2)C36B—C35B—N31B—O31B177.7 (3)
C35A—C36A—C37A—C32A0.7 (4)C34B—C35B—N31B—O31B3.0 (4)
C33A—C32A—C37A—C36A1.4 (4)C36B—C35B—N31B—O32B2.8 (4)
C31A—C32A—C37A—C36A177.6 (3)C34B—C35B—N31B—O32B176.5 (3)
C36A—C35A—N31A—O31A177.8 (2)C2B—N3B—C4B—C5B0.0 (3)
C34A—C35A—N31A—O31A2.2 (4)C31B—N3B—C4B—C5B179.6 (2)
C36A—C35A—N31A—O32A2.1 (4)C2B—N3B—C4B—C41B180.0 (3)
C34A—C35A—N31A—O32A178.0 (2)C31B—N3B—C4B—C41B0.4 (4)
C2A—N3A—C4A—C5A0.1 (3)C5B—C4B—C41B—O41B179.0 (3)
C31A—N3A—C4A—C5A176.9 (2)N3B—C4B—C41B—O41B0.9 (5)
C2A—N3A—C4A—C41A179.7 (3)C2B—N1B—C5B—C4B0.0 (3)
C31A—N3A—C4A—C41A2.9 (4)C2B—N1B—C5B—Cl5B179.8 (2)
C5A—C4A—C41A—O41A178.4 (3)N3B—C4B—C5B—N1B0.0 (3)
N3A—C4A—C41A—O41A1.8 (5)C41B—C4B—C5B—N1B180.0 (3)
C2A—N1A—C5A—C4A0.1 (3)N3B—C4B—C5B—Cl5B179.8 (2)
C2A—N1A—C5A—Cl5A179.7 (2)C41B—C4B—C5B—Cl5B0.2 (4)
N3A—C4A—C5A—N1A0.1 (3)N1B—C2B—C21B—C22B16.0 (5)
C41A—C4A—C5A—N1A179.7 (3)N3B—C2B—C21B—C22B167.5 (3)
N3A—C4A—C5A—Cl5A179.6 (2)C2B—C21B—C22B—C23B70.9 (6)
C41A—C4A—C5A—Cl5A0.6 (5)C21B—C22B—C23B—C24B173.9 (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.

References

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