1,4-Dimeth­yl-1,4-diazo­niabicyclo­[2.2.2]octa­ne tetra­chloro­cuprate(II)

The title compound, (C₈H₁₈N₂)[CuCl₄], crystallizes with two cations and two anions in the asymmetric unit. The cation was obtained by methyl­ation of 1,4-diaza­bicyclo­[2.2.2]octa­ne. C—H...Cl hydrogen-bonding inter­actions link cations and anions to form an infinite three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.031
• wR factor = 0.075
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         80 PerFit

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.422
           From the CIF: _refine_ls_abs_structure_Flack_su    0.013
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.42
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu1

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C8 H18 Cl4 Cu1 N2
            Atom count from _chemical_formula_moiety:C8 H18 Cl1 Cu1 N2
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               4444
           Count of symmetry unique reflns         2553
           Completeness (_total/calc)            174.07%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1891
           Fraction of Friedel pairs measured     0.741
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1,4-Dimethyl-1,4-diazoniabicyclo[2.2.2]octane tetrachlorocuprate(II)

Crystal data

(C8H18N2)[CuCl4]	F(000) = 1416
Mr = 347.58	Dx = 1.649 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3800 reflections
a = 19.6572 (16) Å	θ = 2.0–28.3°
b = 8.0741 (7) Å	µ = 2.30 mm^−1
c = 17.6413 (15) Å	T = 298 K
V = 2799.9 (4) Å^3	Block, yellow
Z = 8	0.44 × 0.34 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4444 independent reflections
Radiation source: fine-focus sealed tube	4074 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→23
Tmin = 0.412, Tmax = 0.560	k = −9→6
13376 measured reflections	l = −17→20

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.0434P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.075	(Δ/σ)max = 0.012
S = 1.03	Δρmax = 0.32 e Å^−3
4444 reflections	Δρmin = −0.34 e Å^−3
273 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0088 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), how many Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.422 (13)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.98750 (2)	0.17093 (4)	0.51273 (3)	0.03287 (13)
Cu2	0.75845 (2)	0.67886 (4)	0.26378 (3)	0.03302 (13)
Cl1	0.76059 (7)	0.49620 (13)	0.16849 (8)	0.0539 (4)
Cl2	0.84625 (5)	0.84057 (12)	0.23143 (8)	0.0559 (3)
Cl3	0.74523 (8)	0.49756 (14)	0.35848 (8)	0.0529 (4)
Cl4	0.68310 (5)	0.87701 (12)	0.29374 (7)	0.0457 (3)
Cl5	0.89349 (5)	0.32206 (10)	0.53355 (7)	0.0496 (3)
Cl6	0.98513 (6)	−0.01845 (14)	0.60637 (7)	0.0492 (3)
Cl7	1.00403 (7)	−0.00179 (13)	0.41576 (8)	0.0529 (4)
Cl8	1.06010 (5)	0.37969 (12)	0.49128 (7)	0.0502 (3)
N1	0.70350 (14)	1.0942 (3)	0.5176 (2)	0.0362 (7)
N2	0.78896 (14)	0.8582 (3)	0.5161 (2)	0.0359 (7)
N3	1.04192 (15)	0.6038 (4)	0.2619 (2)	0.0370 (7)
N4	0.95721 (15)	0.3659 (4)	0.2633 (2)	0.0351 (7)
C1	0.9521 (2)	0.4566 (5)	0.1901 (3)	0.0467 (10)
H1A	0.9054	0.4914	0.1818	0.056*
H1B	0.9652	0.3840	0.1488	0.056*
C2	0.9985 (2)	0.6074 (6)	0.1917 (3)	0.0509 (11)
H2A	1.0273	0.6077	0.1470	0.061*
H2B	0.9713	0.7076	0.1912	0.061*
C3	1.02823 (17)	0.2993 (4)	0.2711 (3)	0.0436 (10)
H3A	1.0371	0.2187	0.2315	0.052*
H3B	1.0334	0.2448	0.3198	0.052*
C4	1.07815 (19)	0.4423 (4)	0.2648 (3)	0.0519 (11)
H4A	1.1086	0.4410	0.3081	0.062*
H4B	1.1054	0.4290	0.2194	0.062*
C5	0.9430 (2)	0.4810 (5)	0.3265 (3)	0.0453 (11)
H5A	0.9437	0.4208	0.3741	0.054*
H5B	0.8982	0.5290	0.3201	0.054*
C6	0.9956 (2)	0.6168 (5)	0.3285 (3)	0.0580 (13)
H6A	0.9731	0.7238	0.3280	0.070*
H6B	1.0218	0.6086	0.3749	0.070*
C7	1.0927 (2)	0.7427 (5)	0.2602 (4)	0.0657 (14)
H7A	1.1202	0.7386	0.3051	0.098*
H7B	1.0691	0.8467	0.2582	0.098*
H7C	1.1212	0.7315	0.2163	0.098*
C8	0.9076 (2)	0.2236 (5)	0.2634 (3)	0.0583 (12)
H8A	0.8622	0.2653	0.2571	0.087*
H8B	0.9109	0.1650	0.3106	0.087*
H8C	0.9182	0.1497	0.2224	0.087*
C9	0.7509 (2)	1.1126 (5)	0.4509 (3)	0.0444 (10)
H9A	0.7751	1.2169	0.4546	0.053*
H9B	0.7249	1.1128	0.4042	0.053*
C10	0.8009 (2)	0.9707 (5)	0.4504 (3)	0.0444 (10)
H10A	0.7961	0.9089	0.4035	0.053*
H10B	0.8469	1.0139	0.4527	0.053*
C11	0.66734 (17)	0.9317 (4)	0.5113 (3)	0.0418 (9)
H11A	0.6408	0.9294	0.4649	0.050*
H11B	0.6364	0.9188	0.5537	0.050*
C12	0.71757 (17)	0.7913 (4)	0.5108 (3)	0.0458 (10)
H12A	0.7125	0.7276	0.4645	0.055*
H12B	0.7087	0.7183	0.5534	0.055*
C13	0.7444 (2)	1.0952 (5)	0.5884 (3)	0.0446 (10)
H13A	0.7145	1.0827	0.6318	0.054*
H13B	0.7680	1.2001	0.5932	0.054*
C14	0.7959 (2)	0.9537 (5)	0.5869 (2)	0.0425 (10)
H14A	0.8416	0.9983	0.5905	0.051*
H14B	0.7884	0.8814	0.6300	0.051*
C15	0.8395 (2)	0.7190 (5)	0.5138 (4)	0.0645 (13)
H15A	0.8847	0.7632	0.5168	0.097*
H15B	0.8344	0.6589	0.4672	0.097*
H15C	0.8316	0.6459	0.5558	0.097*
C16	0.6536 (2)	1.2351 (5)	0.5183 (4)	0.0661 (13)
H16A	0.6234	1.2230	0.5607	0.099*
H16B	0.6278	1.2345	0.4721	0.099*
H16C	0.6778	1.3380	0.5226	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0344 (2)	0.0283 (2)	0.0359 (2)	0.00085 (15)	0.0002 (2)	−0.0004 (2)
Cu2	0.0343 (2)	0.0292 (2)	0.0356 (2)	−0.00030 (17)	−0.00056 (19)	−0.0018 (2)
Cl1	0.0718 (9)	0.0435 (8)	0.0464 (8)	−0.0016 (5)	0.0005 (6)	−0.0170 (5)
Cl2	0.0394 (5)	0.0427 (6)	0.0855 (9)	−0.0103 (4)	0.0015 (6)	0.0099 (5)
Cl3	0.0646 (8)	0.0482 (8)	0.0458 (8)	0.0008 (5)	0.0008 (6)	0.0139 (5)
Cl4	0.0436 (5)	0.0410 (5)	0.0526 (6)	0.0097 (4)	−0.0018 (5)	−0.0094 (5)
Cl5	0.0331 (5)	0.0373 (5)	0.0784 (9)	0.0067 (4)	−0.0030 (5)	−0.0042 (5)
Cl6	0.0580 (7)	0.0428 (7)	0.0467 (8)	0.0022 (5)	−0.0006 (6)	0.0125 (5)
Cl7	0.0744 (9)	0.0430 (8)	0.0414 (8)	0.0016 (5)	0.0006 (6)	−0.0137 (5)
Cl8	0.0418 (5)	0.0368 (5)	0.0721 (8)	−0.0068 (4)	0.0029 (5)	0.0063 (5)
N1	0.0352 (15)	0.0286 (14)	0.0448 (18)	0.0021 (12)	−0.0063 (17)	−0.0031 (17)
N2	0.0326 (15)	0.0305 (14)	0.0448 (18)	0.0005 (11)	−0.0057 (17)	−0.0002 (17)
N3	0.0357 (16)	0.0280 (15)	0.047 (2)	−0.0018 (13)	−0.0041 (17)	0.0049 (16)
N4	0.0313 (16)	0.0323 (15)	0.0415 (19)	0.0008 (12)	−0.0014 (16)	0.0056 (15)
C1	0.048 (2)	0.051 (2)	0.042 (3)	−0.001 (2)	−0.006 (2)	0.000 (2)
C2	0.049 (2)	0.063 (3)	0.040 (3)	−0.002 (2)	−0.003 (2)	0.015 (2)
C3	0.0348 (19)	0.037 (2)	0.059 (3)	0.0087 (16)	−0.007 (2)	0.000 (2)
C4	0.034 (2)	0.038 (2)	0.084 (3)	0.0052 (16)	−0.005 (2)	0.004 (2)
C5	0.048 (3)	0.050 (2)	0.038 (2)	0.0036 (19)	0.011 (2)	−0.0032 (19)
C6	0.091 (4)	0.036 (2)	0.047 (3)	0.000 (2)	0.009 (3)	−0.013 (2)
C7	0.062 (3)	0.038 (2)	0.097 (4)	−0.017 (2)	−0.020 (3)	0.014 (3)
C8	0.049 (2)	0.045 (2)	0.081 (3)	−0.021 (2)	−0.009 (3)	0.006 (2)
C9	0.051 (2)	0.047 (2)	0.035 (3)	−0.006 (2)	−0.0072 (19)	0.0075 (19)
C10	0.042 (2)	0.055 (3)	0.036 (2)	−0.007 (2)	0.008 (2)	−0.0047 (19)
C11	0.0329 (18)	0.0348 (19)	0.058 (2)	−0.0067 (15)	0.000 (2)	0.000 (2)
C12	0.0324 (19)	0.0326 (18)	0.072 (3)	−0.0089 (15)	−0.005 (2)	0.004 (2)
C13	0.056 (2)	0.038 (2)	0.040 (3)	−0.0049 (19)	0.004 (2)	−0.0120 (19)
C14	0.045 (2)	0.051 (2)	0.031 (2)	0.002 (2)	−0.0083 (19)	−0.0008 (19)
C15	0.045 (2)	0.048 (2)	0.101 (4)	0.0174 (19)	−0.012 (3)	−0.009 (3)
C16	0.052 (2)	0.046 (2)	0.100 (4)	0.0182 (19)	−0.004 (3)	−0.009 (3)

Geometric parameters (Å, º)

Cu1—Cl7	2.2309 (14)	C4—H4B	0.9700
Cu1—Cl8	2.2407 (10)	C5—C6	1.507 (6)
Cu1—Cl5	2.2448 (9)	C5—H5A	0.9700
Cu1—Cl6	2.2515 (14)	C5—H5B	0.9700
Cu2—Cl3	2.2364 (14)	C6—H6A	0.9700
Cu2—Cl1	2.2367 (13)	C6—H6B	0.9700
Cu2—Cl2	2.2382 (10)	C7—H7A	0.9600
Cu2—Cl4	2.2434 (10)	C7—H7B	0.9600
N1—C13	1.486 (5)	C7—H7C	0.9600
N1—C11	1.496 (4)	C8—H8A	0.9600
N1—C16	1.502 (4)	C8—H8B	0.9600
N1—C9	1.506 (5)	C8—H8C	0.9600
N2—C14	1.474 (5)	C9—C10	1.510 (6)
N2—C10	1.491 (5)	C9—H9A	0.9700
N2—C15	1.500 (4)	C9—H9B	0.9700
N2—C12	1.506 (4)	C10—H10A	0.9700
N3—C4	1.486 (5)	C10—H10B	0.9700
N3—C6	1.491 (5)	C11—C12	1.503 (5)
N3—C7	1.501 (5)	C11—H11A	0.9700
N3—C2	1.505 (5)	C11—H11B	0.9700
N4—C5	1.477 (5)	C12—H12A	0.9700
N4—C1	1.488 (5)	C12—H12B	0.9700
N4—C3	1.503 (4)	C13—C14	1.527 (5)
N4—C8	1.507 (5)	C13—H13A	0.9700
C1—C2	1.522 (6)	C13—H13B	0.9700
C1—H1A	0.9700	C14—H14A	0.9700
C1—H1B	0.9700	C14—H14B	0.9700
C2—H2A	0.9700	C15—H15A	0.9600
C2—H2B	0.9700	C15—H15B	0.9600
C3—C4	1.519 (5)	C15—H15C	0.9600
C3—H3A	0.9700	C16—H16A	0.9600
C3—H3B	0.9700	C16—H16B	0.9600
C4—H4A	0.9700	C16—H16C	0.9600
Cl7—Cu1—Cl8	104.36 (5)	N3—C6—C5	110.4 (3)
Cl7—Cu1—Cl5	125.81 (5)	N3—C6—H6A	109.6
Cl8—Cu1—Cl5	98.22 (4)	C5—C6—H6A	109.6
Cl7—Cu1—Cl6	98.11 (4)	N3—C6—H6B	109.6
Cl8—Cu1—Cl6	130.39 (5)	C5—C6—H6B	109.6
Cl5—Cu1—Cl6	103.42 (5)	H6A—C6—H6B	108.1
Cl3—Cu2—Cl1	97.59 (4)	N3—C7—H7A	109.5
Cl3—Cu2—Cl2	131.45 (5)	N3—C7—H7B	109.5
Cl1—Cu2—Cl2	100.28 (5)	H7A—C7—H7B	109.5
Cl3—Cu2—Cl4	102.36 (5)	N3—C7—H7C	109.5
Cl1—Cu2—Cl4	131.28 (5)	H7A—C7—H7C	109.5
Cl2—Cu2—Cl4	98.81 (4)	H7B—C7—H7C	109.5
C13—N1—C11	108.9 (3)	N4—C8—H8A	109.5
C13—N1—C16	110.0 (4)	N4—C8—H8B	109.5
C11—N1—C16	110.8 (3)	H8A—C8—H8B	109.5
C13—N1—C9	108.8 (3)	N4—C8—H8C	109.5
C11—N1—C9	108.8 (3)	H8A—C8—H8C	109.5
C16—N1—C9	109.6 (3)	H8B—C8—H8C	109.5
C14—N2—C10	109.0 (3)	N1—C9—C10	109.4 (3)
C14—N2—C15	110.7 (4)	N1—C9—H9A	109.8
C10—N2—C15	109.3 (4)	C10—C9—H9A	109.8
C14—N2—C12	109.0 (3)	N1—C9—H9B	109.8
C10—N2—C12	108.5 (3)	C10—C9—H9B	109.8
C15—N2—C12	110.3 (3)	H9A—C9—H9B	108.2
C4—N3—C6	109.1 (3)	N2—C10—C9	110.8 (3)
C4—N3—C7	109.7 (3)	N2—C10—H10A	109.5
C6—N3—C7	111.6 (4)	C9—C10—H10A	109.5
C4—N3—C2	108.5 (3)	N2—C10—H10B	109.5
C6—N3—C2	107.5 (3)	C9—C10—H10B	109.5
C7—N3—C2	110.3 (3)	H10A—C10—H10B	108.1
C5—N4—C1	109.4 (3)	N1—C11—C12	110.5 (3)
C5—N4—C3	109.4 (3)	N1—C11—H11A	109.6
C1—N4—C3	108.6 (3)	C12—C11—H11A	109.6
C5—N4—C8	111.0 (3)	N1—C11—H11B	109.6
C1—N4—C8	109.4 (3)	C12—C11—H11B	109.6
C3—N4—C8	109.1 (3)	H11A—C11—H11B	108.1
N4—C1—C2	109.7 (3)	C11—C12—N2	109.9 (3)
N4—C1—H1A	109.7	C11—C12—H12A	109.7
C2—C1—H1A	109.7	N2—C12—H12A	109.7
N4—C1—H1B	109.7	C11—C12—H12B	109.7
C2—C1—H1B	109.7	N2—C12—H12B	109.7
H1A—C1—H1B	108.2	H12A—C12—H12B	108.2
N3—C2—C1	109.9 (3)	N1—C13—C14	109.8 (3)
N3—C2—H2A	109.7	N1—C13—H13A	109.7
C1—C2—H2A	109.7	C14—C13—H13A	109.7
N3—C2—H2B	109.7	N1—C13—H13B	109.7
C1—C2—H2B	109.7	C14—C13—H13B	109.7
H2A—C2—H2B	108.2	H13A—C13—H13B	108.2
N4—C3—C4	108.7 (3)	N2—C14—C13	110.2 (3)
N4—C3—H3A	109.9	N2—C14—H14A	109.6
C4—C3—H3A	109.9	C13—C14—H14A	109.6
N4—C3—H3B	109.9	N2—C14—H14B	109.6
C4—C3—H3B	109.9	C13—C14—H14B	109.6
H3A—C3—H3B	108.3	H14A—C14—H14B	108.1
N3—C4—C3	111.1 (3)	N2—C15—H15A	109.5
N3—C4—H4A	109.4	N2—C15—H15B	109.5
C3—C4—H4A	109.4	H15A—C15—H15B	109.5
N3—C4—H4B	109.4	N2—C15—H15C	109.5
C3—C4—H4B	109.4	H15A—C15—H15C	109.5
H4A—C4—H4B	108.0	H15B—C15—H15C	109.5
N4—C5—C6	110.3 (3)	N1—C16—H16A	109.5
N4—C5—H5A	109.6	N1—C16—H16B	109.5
C6—C5—H5A	109.6	H16A—C16—H16B	109.5
N4—C5—H5B	109.6	N1—C16—H16C	109.5
C6—C5—H5B	109.6	H16A—C16—H16C	109.5
H5A—C5—H5B	108.1	H16B—C16—H16C	109.5
C5—N4—C1—C2	54.4 (4)	C13—N1—C9—C10	59.8 (4)
C3—N4—C1—C2	−64.8 (4)	C11—N1—C9—C10	−58.7 (4)
C8—N4—C1—C2	176.2 (3)	C16—N1—C9—C10	−180.0 (3)
C4—N3—C2—C1	54.2 (4)	C14—N2—C10—C9	−58.8 (4)
C6—N3—C2—C1	−63.7 (4)	C15—N2—C10—C9	−180.0 (3)
C7—N3—C2—C1	174.4 (4)	C12—N2—C10—C9	59.7 (4)
N4—C1—C2—N3	7.9 (5)	N1—C9—C10—N2	−0.9 (5)
C5—N4—C3—C4	−62.8 (5)	C13—N1—C11—C12	−58.7 (5)
C1—N4—C3—C4	56.5 (4)	C16—N1—C11—C12	−179.8 (5)
C8—N4—C3—C4	175.6 (4)	C9—N1—C11—C12	59.7 (5)
C6—N3—C4—C3	54.2 (5)	N1—C11—C12—N2	−0.6 (6)
C7—N3—C4—C3	176.8 (4)	C14—N2—C12—C11	59.6 (5)
C2—N3—C4—C3	−62.7 (5)	C10—N2—C12—C11	−58.9 (5)
N4—C3—C4—N3	6.5 (5)	C15—N2—C12—C11	−178.6 (5)
C1—N4—C5—C6	−62.7 (4)	C11—N1—C13—C14	59.5 (4)
C3—N4—C5—C6	56.1 (4)	C16—N1—C13—C14	−179.0 (3)
C8—N4—C5—C6	176.6 (4)	C9—N1—C13—C14	−59.0 (4)
C4—N3—C6—C5	−61.4 (5)	C10—N2—C14—C13	59.5 (4)
C7—N3—C6—C5	177.1 (4)	C15—N2—C14—C13	179.8 (3)
C2—N3—C6—C5	56.1 (4)	C12—N2—C14—C13	−58.7 (4)
N4—C5—C6—N3	5.5 (5)	N1—C13—C14—N2	−0.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cl2	0.97	2.77	3.604 (5)	144
C3—H3B···Cl7	0.97	2.68	3.556 (5)	151
C12—H12A···Cl3	0.97	2.71	3.626 (5)	157
C6—H6A···Cl7^i	0.97	2.77	3.446 (4)	127
C2—H2A···Cl5^ii	0.97	2.60	3.552 (5)	167
C3—H3A···Cl6^iii	0.97	2.77	3.695 (5)	160
C12—H12B···Cl1^iv	0.97	2.78	3.688 (5)	157
C13—H13B···Cl1^v	0.97	2.79	3.534 (4)	134

Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, z−1/2; (iii) −x+2, −y, z−1/2; (iv) −x+3/2, y, z+1/2; (v) −x+3/2, y+1, z+1/2.