Chain structure of catena-poly­[[bis­[cis-1-(2,4,6-tri­methyl­phenyl)­tetrazole-κN4]copper(II)]-di-μ-chloro]

Ivashkevich, D.O.; Lyakhov, A.S.; Degtyarik, M.M.; Gaponik, P.N.

doi:10.1107/S1600536802022195

Chain structure of catena-poly[[bis[cis-1-(2,4,6-trimethylphenyl)tetrazole-κN⁴]copper(II)]-di-μ-chloro]

D. O. Ivashkevich, A. S. Lyakhov, M. M. Degtyarik and P. N. Gaponik

In the title compound, [CuCl₂(C₁₀H₁₂N₄)₂]_n, the coordination polyhedron of the Cu atom is an elongated octahedron. Its equatorial positions are occupied by two Cl atoms [Cu—Cl 2.2767 (8) and 2.2669 (8) Å] and two N⁴ atoms of substituted tetrazole ligands [Cu—N⁴ 2.016 (2) and 2.038 (2) Å]. The axial positions are occupied by two Cl atoms [Cu—Cl 2.9769 (11) and 2.8995 (11) Å], which belong to the equatorial planes of two neighbouring Cu atoms. Thus, the [CuCl₂(C₁₀H₁₂N₄)₂] units form infinite chains, extended along the a axis, which are linked together only by van der Waals interactions. The skeleton of each chain consists of Cu and Cl atoms.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022195/ya6145sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022195/ya6145Isup2.hkl Contains datablock I

CCDC reference: 202970

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.038
wR factor = 0.121
Data-to-parameter ratio = 19.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



ABSTM_02  Alert A Test not performed as the _exptl_absorpt_correction_type
          has not been identified. See test ABSTY_01.

ABSTY_01  Alert A The absorption correction should be one of the following
          *  none
          *  analytical
          *  integration
          *  numerical
          *  gaussian
          *  empirical
          *  psi-scan
          *  multi-scan
          *  refdelf
          *  sphere
          *  cylinder


 2 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 0 Alert Level C = Please check

Computing details top

Data collection: R3m Software (Nicolet, 1980); cell refinement: R3m Software; data reduction: R3m Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

catena-poly[[bis[cis-1-(2,4,6-trimethylphenyl)tetrazole-κN⁴]copper(II)]- di-µ-chloro] top

Crystal data top

[CuCl₂(C₁₀H₁₂N₄)₂]	Z = 2
M_r = 510.91	F(000) = 526
Triclinic, P1	D_x = 1.445 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.283 (2) Å	Cell parameters from 25 reflections
b = 12.032 (3) Å	θ = 15.5–17.9°
c = 13.912 (3) Å	µ = 1.18 mm⁻¹
α = 85.97 (2)°	T = 293 K
β = 84.19 (2)°	Prism, green
γ = 75.82 (2)°	0.60 × 0.10 × 0.10 mm
V = 1174.6 (5) Å³

Data collection top

Nicolet R3m four-circle diffractometer	4277 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 27.6°, θ_min = 1.5°
ω/2θ' scans	h = −2→9
Absorption correction: y scan (North et al., 1968)	k = −15→15
T_min = 0.537, T_max = 0.891	l = −18→18
6068 measured reflections	3 standard reflections every 100 reflections
5445 independent reflections	intensity decay: none

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0674P)² + 0.5007P] where P = (F_o² + 2F_c²)/3
5445 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Special details top

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

treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

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

	x	y	z	U_iso*/U_eq
Cu	0.24089 (4)	0.52686 (2)	0.94977 (2)	0.03822 (11)
Cl2	0.15836 (8)	0.36384 (5)	1.00909 (4)	0.03919 (14)
Cl1	0.34121 (8)	0.55903 (5)	1.09279 (4)	0.04137 (15)
N1A	0.3595 (3)	0.83681 (16)	0.85790 (15)	0.0369 (4)
N2A	0.2020 (3)	0.8432 (2)	0.81116 (18)	0.0530 (6)
N3A	0.1480 (3)	0.7501 (2)	0.83473 (19)	0.0561 (6)
N4A	0.2662 (3)	0.68303 (17)	0.89616 (15)	0.0396 (4)
C5A	0.3954 (3)	0.7374 (2)	0.90895 (18)	0.0380 (5)
H5A	0.4961	0.7111	0.9474	0.046*
C6A	0.4664 (3)	0.92333 (19)	0.84219 (17)	0.0361 (5)
C7A	0.3952 (3)	1.0284 (2)	0.88457 (17)	0.0386 (5)
C8A	0.5012 (4)	1.1103 (2)	0.86538 (19)	0.0430 (5)
H8A	0.4580	1.1812	0.8931	0.052*
C9A	0.6702 (4)	1.0890 (2)	0.80590 (19)	0.0440 (5)
C10A	0.7343 (4)	0.9829 (2)	0.76594 (19)	0.0444 (6)
H10A	0.8480	0.9683	0.7268	0.053*
C11A	0.6354 (3)	0.8978 (2)	0.78199 (18)	0.0400 (5)
C12A	0.2122 (4)	1.0536 (3)	0.9489 (2)	0.0537 (7)
H12A	0.1880	1.1301	0.9709	0.080*
H12B	0.2224	0.9998	1.0035	0.080*
H12C	0.1096	1.0470	0.9132	0.080*
C13A	0.7811 (5)	1.1799 (3)	0.7839 (3)	0.0673 (9)
H13A	0.7170	1.2478	0.8170	0.101*
H13B	0.7906	1.1976	0.7155	0.101*
H13C	0.9062	1.1520	0.8052	0.101*
C14A	0.7079 (4)	0.7835 (2)	0.7370 (2)	0.0541 (7)
H14A	0.6209	0.7359	0.7561	0.081*
H14B	0.8304	0.7471	0.7585	0.081*
H14C	0.7186	0.7947	0.6679	0.081*
N1B	0.1408 (3)	0.41072 (19)	0.69071 (14)	0.0430 (5)
N2B	0.2854 (4)	0.4620 (3)	0.65991 (17)	0.0589 (7)
N3B	0.3260 (4)	0.5058 (3)	0.73397 (17)	0.0600 (7)
N4B	0.2136 (3)	0.48407 (19)	0.81363 (15)	0.0433 (5)
C5B	0.1011 (4)	0.4259 (2)	0.78468 (18)	0.0435 (5)
H5B	0.0080	0.3993	0.8238	0.052*
C6B	0.0546 (4)	0.3551 (2)	0.62558 (16)	0.0407 (5)
C7B	−0.1213 (4)	0.4123 (2)	0.59582 (18)	0.0420 (5)
C8B	−0.2034 (4)	0.3551 (3)	0.53520 (19)	0.0514 (6)
H8B	−0.3225	0.3908	0.5151	0.062*
C9B	−0.1154 (5)	0.2475 (3)	0.5037 (2)	0.0568 (7)
C10B	0.0603 (5)	0.1951 (3)	0.5343 (2)	0.0590 (7)
H10B	0.1214	0.1227	0.5129	0.071*
C11B	0.1493 (4)	0.2464 (2)	0.59593 (19)	0.0494 (6)
C12B	−0.2200 (4)	0.5304 (3)	0.6274 (2)	0.0585 (7)
H12D	−0.3391	0.5552	0.5992	0.088*
H12E	−0.1415	0.5826	0.6067	0.088*
H12F	−0.2424	0.5289	0.6967	0.088*
C13B	−0.2104 (6)	0.1890 (4)	0.4365 (3)	0.0916 (13)
H13D	−0.1299	0.1151	0.4220	0.137*
H13E	−0.2312	0.2352	0.3777	0.137*
H13F	−0.3300	0.1798	0.4675	0.137*
C14B	0.3402 (5)	0.1848 (4)	0.6294 (3)	0.0828 (11)
H14D	0.3807	0.2325	0.6713	0.124*
H14E	0.4315	0.1685	0.5743	0.124*
H14F	0.3299	0.1143	0.6638	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.04527 (19)	0.03766 (17)	0.03802 (17)	−0.02066 (13)	−0.00794 (12)	−0.00013 (12)
Cl2	0.0340 (3)	0.0346 (3)	0.0511 (3)	−0.0126 (2)	−0.0059 (2)	0.0029 (2)
Cl1	0.0385 (3)	0.0497 (3)	0.0390 (3)	−0.0143 (2)	−0.0053 (2)	−0.0071 (2)
N1A	0.0323 (9)	0.0344 (10)	0.0473 (11)	−0.0133 (8)	−0.0097 (8)	0.0032 (8)
N2A	0.0460 (12)	0.0525 (13)	0.0682 (15)	−0.0232 (10)	−0.0273 (11)	0.0182 (11)
N3A	0.0516 (13)	0.0575 (14)	0.0706 (15)	−0.0297 (11)	−0.0325 (12)	0.0188 (12)
N4A	0.0382 (10)	0.0376 (10)	0.0468 (11)	−0.0143 (8)	−0.0130 (8)	0.0039 (8)
C5A	0.0330 (11)	0.0350 (11)	0.0491 (13)	−0.0127 (9)	−0.0112 (10)	0.0034 (9)
C6A	0.0332 (11)	0.0335 (11)	0.0441 (12)	−0.0132 (9)	−0.0061 (9)	0.0036 (9)
C7A	0.0338 (11)	0.0390 (12)	0.0415 (12)	−0.0066 (9)	−0.0027 (9)	−0.0003 (9)
C8A	0.0490 (14)	0.0316 (11)	0.0489 (13)	−0.0106 (10)	−0.0033 (11)	−0.0026 (10)
C9A	0.0460 (14)	0.0411 (13)	0.0493 (14)	−0.0199 (11)	−0.0051 (11)	0.0029 (10)
C10A	0.0384 (13)	0.0467 (13)	0.0500 (14)	−0.0168 (11)	0.0029 (10)	−0.0006 (11)
C11A	0.0383 (12)	0.0356 (11)	0.0461 (13)	−0.0092 (9)	−0.0022 (10)	−0.0036 (10)
C12A	0.0428 (14)	0.0531 (15)	0.0621 (17)	−0.0093 (12)	0.0059 (12)	−0.0052 (13)
C13A	0.074 (2)	0.0554 (18)	0.082 (2)	−0.0383 (16)	0.0023 (17)	0.0016 (16)
C14A	0.0512 (16)	0.0441 (14)	0.0665 (18)	−0.0107 (12)	0.0044 (13)	−0.0160 (13)
N1B	0.0400 (11)	0.0582 (13)	0.0372 (10)	−0.0234 (10)	−0.0021 (8)	−0.0053 (9)
N2B	0.0543 (14)	0.0921 (19)	0.0427 (12)	−0.0441 (14)	0.0017 (10)	−0.0019 (12)
N3B	0.0593 (15)	0.0918 (19)	0.0436 (12)	−0.0485 (14)	−0.0006 (11)	−0.0011 (12)
N4B	0.0461 (12)	0.0542 (12)	0.0370 (10)	−0.0263 (10)	−0.0029 (9)	−0.0028 (9)
C5B	0.0419 (13)	0.0560 (15)	0.0400 (12)	−0.0262 (11)	0.0002 (10)	−0.0056 (10)
C6B	0.0431 (13)	0.0518 (14)	0.0315 (11)	−0.0192 (11)	−0.0042 (9)	−0.0020 (10)
C7B	0.0417 (13)	0.0465 (13)	0.0399 (12)	−0.0154 (11)	−0.0018 (10)	−0.0011 (10)
C8B	0.0502 (15)	0.0656 (18)	0.0431 (14)	−0.0215 (13)	−0.0093 (11)	−0.0006 (12)
C9B	0.0692 (19)	0.0698 (19)	0.0412 (14)	−0.0337 (16)	−0.0038 (13)	−0.0109 (13)
C10B	0.074 (2)	0.0507 (16)	0.0525 (16)	−0.0139 (14)	0.0014 (14)	−0.0155 (13)
C11B	0.0520 (15)	0.0511 (15)	0.0430 (13)	−0.0086 (12)	−0.0027 (11)	−0.0034 (11)
C12B	0.0530 (17)	0.0523 (16)	0.0685 (19)	−0.0102 (13)	−0.0001 (14)	−0.0073 (14)
C13B	0.100 (3)	0.121 (4)	0.073 (2)	−0.054 (3)	−0.008 (2)	−0.042 (2)
C14B	0.067 (2)	0.080 (2)	0.090 (3)	0.0080 (19)	−0.020 (2)	−0.004 (2)

Geometric parameters (Å, º) top

Cu—N4A	2.016 (2)	C14A—H14A	0.9600
Cu—N4B	2.038 (2)	C14A—H14B	0.9600
Cu—Cl1	2.2767 (8)	C14A—H14C	0.9600
Cu—Cl2	2.2669 (8)	N1B—C5B	1.325 (3)
Cu—Cl1ⁱ	2.9769 (11)	N1B—N2B	1.365 (3)
Cu—Cl2ⁱⁱ	2.8995 (11)	N1B—C6B	1.438 (3)
N1A—C5A	1.330 (3)	N2B—N3B	1.281 (3)
N1A—N2A	1.358 (3)	N3B—N4B	1.359 (3)
N1A—C6A	1.438 (3)	N4B—C5B	1.309 (3)
N2A—N3A	1.287 (3)	C5B—H5B	0.9300
N3A—N4A	1.354 (3)	C6B—C7B	1.386 (4)
N4A—C5A	1.303 (3)	C6B—C11B	1.390 (4)
C5A—H5A	0.9300	C7B—C8B	1.388 (4)
C6A—C7A	1.392 (3)	C7B—C12B	1.501 (4)
C6A—C11A	1.398 (3)	C8B—C9B	1.376 (4)
C7A—C8A	1.390 (3)	C8B—H8B	0.9300
C7A—C12A	1.506 (3)	C9B—C10B	1.376 (5)
C8A—C9A	1.391 (4)	C9B—C13B	1.520 (4)
C8A—H8A	0.9300	C10B—C11B	1.385 (4)
C9A—C10A	1.383 (4)	C10B—H10B	0.9300
C9A—C13A	1.509 (4)	C11B—C14B	1.509 (4)
C10A—C11A	1.383 (3)	C12B—H12D	0.9600
C10A—H10A	0.9300	C12B—H12E	0.9600
C11A—C14A	1.503 (3)	C12B—H12F	0.9600
C12A—H12A	0.9600	C13B—H13D	0.9600
C12A—H12B	0.9600	C13B—H13E	0.9600
C12A—H12C	0.9600	C13B—H13F	0.9600
C13A—H13A	0.9600	C14B—H14D	0.9600
C13A—H13B	0.9600	C14B—H14E	0.9600
C13A—H13C	0.9600	C14B—H14F	0.9600

N4A—Cu—N4B	89.29 (9)	H13B—C13A—H13C	109.5
N4A—Cu—Cl1	90.55 (6)	C11A—C14A—H14A	109.5
N4A—Cu—Cl2	170.21 (6)	C11A—C14A—H14B	109.5
N4B—Cu—Cl1	167.31 (7)	H14A—C14A—H14B	109.5
N4B—Cu—Cl2	89.16 (6)	C11A—C14A—H14C	109.5
Cl2—Cu—Cl1	93.07 (3)	H14A—C14A—H14C	109.5
N4A—Cu—Cl2ⁱⁱ	85.43 (6)	H14B—C14A—H14C	109.5
N4B—Cu—Cl2ⁱⁱ	95.15 (7)	C5B—N1B—N2B	107.6 (2)
Cl2—Cu—Cl2ⁱⁱ	85.08 (3)	C5B—N1B—C6B	130.4 (2)
Cl1—Cu—Cl2ⁱⁱ	97.49 (3)	N2B—N1B—C6B	122.0 (2)
N4A—Cu—Cl1ⁱ	88.56 (6)	N3B—N2B—N1B	106.7 (2)
N4B—Cu—Cl1ⁱ	87.14 (7)	N2B—N3B—N4B	110.4 (2)
Cl2—Cu—Cl1ⁱ	101.02 (3)	C5B—N4B—N3B	106.1 (2)
Cl1—Cu—Cl1ⁱ	80.16 (3)	C5B—N4B—Cu	129.50 (17)
Cl2ⁱⁱ—Cu—Cl1ⁱ	173.539 (19)	N3B—N4B—Cu	124.19 (16)
C5A—N1A—N2A	107.88 (19)	N4B—C5B—N1B	109.2 (2)
C5A—N1A—C6A	130.3 (2)	N4B—C5B—H5B	125.4
N2A—N1A—C6A	121.60 (19)	N1B—C5B—H5B	125.4
N3A—N2A—N1A	106.62 (19)	C7B—C6B—C11B	122.8 (2)
N2A—N3A—N4A	110.0 (2)	C7B—C6B—N1B	118.2 (2)
C5A—N4A—N3A	106.89 (19)	C11B—C6B—N1B	119.0 (2)
C5A—N4A—Cu	129.03 (16)	C6B—C7B—C8B	116.9 (2)
N3A—N4A—Cu	124.03 (15)	C6B—C7B—C12B	122.0 (2)
N4A—C5A—N1A	108.6 (2)	C8B—C7B—C12B	121.1 (3)
N4A—C5A—H5A	125.7	C9B—C8B—C7B	122.6 (3)
N1A—C5A—H5A	125.7	C9B—C8B—H8B	118.7
C7A—C6A—C11A	123.4 (2)	C7B—C8B—H8B	118.7
C7A—C6A—N1A	119.1 (2)	C10B—C9B—C8B	118.3 (3)
C11A—C6A—N1A	117.5 (2)	C10B—C9B—C13B	121.2 (3)
C8A—C7A—C6A	117.0 (2)	C8B—C9B—C13B	120.5 (3)
C8A—C7A—C12A	120.8 (2)	C9B—C10B—C11B	122.3 (3)
C6A—C7A—C12A	122.2 (2)	C9B—C10B—H10B	118.9
C7A—C8A—C9A	121.7 (2)	C11B—C10B—H10B	118.9
C7A—C8A—H8A	119.1	C10B—C11B—C6B	117.2 (3)
C9A—C8A—H8A	119.1	C10B—C11B—C14B	120.6 (3)
C10A—C9A—C8A	118.7 (2)	C6B—C11B—C14B	122.2 (3)
C10A—C9A—C13A	120.3 (3)	C7B—C12B—H12D	109.5
C8A—C9A—C13A	121.0 (3)	C7B—C12B—H12E	109.5
C9A—C10A—C11A	122.5 (2)	H12D—C12B—H12E	109.5
C9A—C10A—H10A	118.8	C7B—C12B—H12F	109.5
C11A—C10A—H10A	118.8	H12D—C12B—H12F	109.5
C10A—C11A—C6A	116.7 (2)	H12E—C12B—H12F	109.5
C10A—C11A—C14A	121.3 (2)	C9B—C13B—H13D	109.5
C6A—C11A—C14A	122.0 (2)	C9B—C13B—H13E	109.5
C7A—C12A—H12A	109.5	H13D—C13B—H13E	109.5
C7A—C12A—H12B	109.5	C9B—C13B—H13F	109.5
H12A—C12A—H12B	109.5	H13D—C13B—H13F	109.5
C7A—C12A—H12C	109.5	H13E—C13B—H13F	109.5
H12A—C12A—H12C	109.5	C11B—C14B—H14D	109.5
H12B—C12A—H12C	109.5	C11B—C14B—H14E	109.5
C9A—C13A—H13A	109.5	H14D—C14B—H14E	109.5
C9A—C13A—H13B	109.5	C11B—C14B—H14F	109.5
H13A—C13A—H13B	109.5	H14D—C14B—H14F	109.5
C9A—C13A—H13C	109.5	H14E—C14B—H14F	109.5
H13A—C13A—H13C	109.5

C5A—N1A—N2A—N3A	0.1 (3)	C6B—N1B—N2B—N3B	178.2 (3)
C6A—N1A—N2A—N3A	175.2 (2)	N1B—N2B—N3B—N4B	0.6 (4)
N1A—N2A—N3A—N4A	0.2 (3)	N2B—N3B—N4B—C5B	−0.6 (4)
N2A—N3A—N4A—C5A	−0.5 (3)	N2B—N3B—N4B—Cu	175.2 (2)
N2A—N3A—N4A—Cu	−178.4 (2)	N4A—Cu—N4B—C5B	−140.0 (3)
N4B—Cu—N4A—C5A	−129.4 (2)	Cl2—Cu—N4B—C5B	30.4 (2)
Cl1—Cu—N4A—C5A	37.9 (2)	Cl1—Cu—N4B—C5B	130.7 (3)
Cl2ⁱⁱ—Cu—N4A—C5A	135.4 (2)	Cl2ⁱⁱ—Cu—N4B—C5B	−54.6 (3)
Cl1ⁱ—Cu—N4A—C5A	−42.2 (2)	Cl1ⁱ—Cu—N4B—C5B	131.4 (2)
N4B—Cu—N4A—N3A	48.0 (2)	N4A—Cu—N4B—N3B	45.3 (2)
Cl1—Cu—N4A—N3A	−144.7 (2)	Cl2—Cu—N4B—N3B	−144.4 (2)
Cl2ⁱⁱ—Cu—N4A—N3A	−47.2 (2)	Cl1—Cu—N4B—N3B	−44.1 (4)
Cl1ⁱ—Cu—N4A—N3A	135.2 (2)	Cl2ⁱⁱ—Cu—N4B—N3B	130.6 (2)
N3A—N4A—C5A—N1A	0.6 (3)	Cl1ⁱ—Cu—N4B—N3B	−43.3 (2)
Cu—N4A—C5A—N1A	178.37 (16)	N3B—N4B—C5B—N1B	0.3 (3)
N2A—N1A—C5A—N4A	−0.5 (3)	Cu—N4B—C5B—N1B	−175.24 (18)
C6A—N1A—C5A—N4A	−175.0 (2)	N2B—N1B—C5B—N4B	0.1 (3)
C5A—N1A—C6A—C7A	−110.0 (3)	C6B—N1B—C5B—N4B	−178.4 (3)
N2A—N1A—C6A—C7A	76.2 (3)	C5B—N1B—C6B—C7B	75.4 (4)
C5A—N1A—C6A—C11A	71.9 (3)	N2B—N1B—C6B—C7B	−102.9 (3)
N2A—N1A—C6A—C11A	−101.9 (3)	C5B—N1B—C6B—C11B	−104.0 (3)
C11A—C6A—C7A—C8A	−0.5 (4)	N2B—N1B—C6B—C11B	77.7 (3)
N1A—C6A—C7A—C8A	−178.5 (2)	C11B—C6B—C7B—C8B	1.1 (4)
C11A—C6A—C7A—C12A	179.8 (2)	N1B—C6B—C7B—C8B	−178.2 (2)
N1A—C6A—C7A—C12A	1.8 (4)	C11B—C6B—C7B—C12B	−179.0 (3)
C6A—C7A—C8A—C9A	0.5 (4)	N1B—C6B—C7B—C12B	1.7 (4)
C12A—C7A—C8A—C9A	−179.7 (2)	C6B—C7B—C8B—C9B	−1.2 (4)
C7A—C8A—C9A—C10A	−0.7 (4)	C12B—C7B—C8B—C9B	178.9 (3)
C7A—C8A—C9A—C13A	178.5 (3)	C7B—C8B—C9B—C10B	0.4 (4)
C8A—C9A—C10A—C11A	0.8 (4)	C7B—C8B—C9B—C13B	−179.4 (3)
C13A—C9A—C10A—C11A	−178.4 (3)	C8B—C9B—C10B—C11B	0.6 (5)
C9A—C10A—C11A—C6A	−0.7 (4)	C13B—C9B—C10B—C11B	−179.6 (3)
C9A—C10A—C11A—C14A	179.6 (3)	C9B—C10B—C11B—C6B	−0.7 (4)
C7A—C6A—C11A—C10A	0.6 (4)	C9B—C10B—C11B—C14B	178.7 (3)
N1A—C6A—C11A—C10A	178.6 (2)	C7B—C6B—C11B—C10B	−0.2 (4)
C7A—C6A—C11A—C14A	−179.7 (2)	N1B—C6B—C11B—C10B	179.1 (2)
N1A—C6A—C11A—C14A	−1.7 (4)	C7B—C6B—C11B—C14B	−179.6 (3)
C5B—N1B—N2B—N3B	−0.4 (3)	N1B—C6B—C11B—C14B	−0.3 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5A···Cl2ⁱ	0.93	2.58	3.458 (3)	159
C5B—H5B···Cl1ⁱⁱ	0.93	2.63	3.458 (3)	148