Bis{N,N,N-trimethyl-2-oxo-2-[2-(2,3,4- trihydroxy-benzyl-idene)hydrazin-yl]ethanaminium} tetra-chlorido-zincate(II) methanol solvate.

The asymmetric unit of the title compound, (C(12)H(18)N(3)O(4))(2)[ZnCl(4)]·CH(3)OH, consists of two Girard reagent-based cations, a tetra-chlorido-zincate anion and a mol-ecule of methanol as solvate. These components are inter-connected in the crystal structure by an extensive network of O-H⋯O, N-H⋯O, C-H⋯O, O-H⋯N, O-H⋯Cl, N-H⋯Cl and C-H⋯Cl hydrogen bonds. The shortest inter-molecular inter-action is realized between the cation and anion [H⋯Cl = 2.29 (5) Å; O-H⋯Cl = 167 (3)°]. C-H⋯O inter-actions also play a important role in the inter-connection of the cations.

Related literature

For the crystal structures of the related Girard reagent-based ligands and coordination compounds, see: Leovac et al. (2006 ▶, 2007 ▶); Vojinović et al. (2004 ▶) and references therein; Vojinović-Ješić et al. (2008 ▶, 2010 ▶); Revenko et al. (2009 ▶). For the crystal structures containing the tetra­chlorido­zincate ion, see: Jin et al. (2005 ▶); Valkonen et al. (2006 ▶).

Experimental

Crystal data

(C12H18N3O4)2[ZnCl4]·CH4O

M = 775.82

Triclinic,

a = 9.471 (3) Å

b = 13.389 (4) Å

c = 14.986 (5) Å

α = 110.90 (4)°

β = 94.91 (4)°

γ = 103.94 (5)°

V = 1691.9 (12) Å3

Z = 2

Mo Kα radiation

μ = 1.10 mm−1

T = 295 K

0.33 × 0.21 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

7056 measured reflections

6632 independent reflections

5226 reflections with I > 2σ(I)

R int = 0.017

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.128

S = 1.05

6632 reflections

440 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.81 e Å−3

Δρmin = −0.58 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000615X/rk2191sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000615X/rk2191Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C12H18N3O4)2[ZnCl4]·CH4O	Z = 2
Mr = 775.82	F(000) = 804
Triclinic, P1	Dx = 1.523 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.471 (3) Å	Cell parameters from 25 reflections
b = 13.389 (4) Å	θ = 11.5–19.4°
c = 14.986 (5) Å	µ = 1.10 mm−1
α = 110.90 (4)°	T = 295 K
β = 94.91 (4)°	Prism, light-green
γ = 103.94 (5)°	0.33 × 0.21 × 0.18 mm
V = 1691.9 (12) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 1.5°
graphite	h = 0→11
ω/2θ–scans	k = −16→16
7056 measured reflections	l = −18→18
6632 independent reflections	3 standard reflections every 60 min
5226 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0754P)2 + 0.7588P] where P = (Fo2 + 2Fc2)/3
6632 reflections	(Δ/σ)max = 0.001
440 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

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

	x	y	z	Uiso*/Ueq
Zn1	0.12662 (4)	0.97209 (3)	0.27361 (2)	0.03615 (12)
Cl1	0.08234 (9)	0.87169 (6)	0.36739 (6)	0.0457 (2)
Cl2	−0.02229 (10)	0.86775 (8)	0.12557 (6)	0.0582 (2)
Cl3	0.07728 (10)	1.13575 (7)	0.34252 (7)	0.0550 (2)
Cl4	0.36959 (9)	0.99260 (7)	0.25977 (7)	0.0542 (2)
O1A	0.3976 (3)	0.5823 (2)	0.2618 (2)	0.0630 (7)
O4A	0.0152 (3)	0.3662 (2)	0.11211 (17)	0.0436 (5)
O5A	−0.2207 (3)	0.1888 (2)	−0.00766 (19)	0.0516 (6)
O6A	−0.4465 (3)	0.2247 (2)	−0.10178 (19)	0.0547 (6)
O1B	0.6208 (3)	0.44499 (19)	0.23238 (19)	0.0510 (6)
O4B	0.9987 (2)	0.63770 (19)	0.40319 (17)	0.0425 (5)
O5B	1.2379 (3)	0.80292 (19)	0.52686 (19)	0.0508 (6)
O6B	1.4654 (3)	0.7511 (2)	0.60703 (17)	0.0484 (6)
N1A	0.1257 (3)	0.5816 (2)	0.19456 (18)	0.0365 (5)
N2A	0.2344 (3)	0.6776 (2)	0.25321 (19)	0.0382 (6)
N3A	0.6305 (3)	0.7890 (2)	0.36455 (18)	0.0427 (6)
N1B	0.8729 (2)	0.4242 (2)	0.31181 (16)	0.0327 (5)
N2B	0.7550 (3)	0.3346 (2)	0.25584 (18)	0.0336 (5)
N3B	0.3590 (3)	0.2561 (2)	0.14515 (17)	0.0354 (5)
C1A	0.3662 (3)	0.6692 (3)	0.2858 (2)	0.0390 (6)
C2A	0.0097 (3)	0.5939 (3)	0.1539 (2)	0.0365 (6)
H2A	0.0015	0.6651	0.1655	0.044*
C3A	−0.1076 (3)	0.4967 (2)	0.0901 (2)	0.0340 (6)
C4A	−0.1013 (3)	0.3874 (3)	0.0709 (2)	0.0338 (6)
C5A	−0.2159 (3)	0.2969 (3)	0.0080 (2)	0.0373 (6)
C6A	−0.3357 (3)	0.3144 (3)	−0.0383 (2)	0.0402 (7)
C7A	−0.3442 (3)	0.4209 (3)	−0.0204 (2)	0.0424 (7)
H7A	−0.4253	0.4316	−0.0513	0.051*
C8A	−0.2319 (3)	0.5109 (3)	0.0430 (2)	0.0395 (7)
H9A	−0.2381	0.5827	0.0553	0.047*
C9A	0.4695 (3)	0.7812 (3)	0.3546 (3)	0.0446 (7)
H9A1	0.4536	0.8381	0.3324	0.054*
H9A2	0.4432	0.7981	0.4184	0.054*
C10A	0.6698 (4)	0.7172 (4)	0.4147 (3)	0.0652 (11)
H10B	0.7738	0.7245	0.4196	0.098*
H10A	0.6142	0.6405	0.3777	0.098*
H10C	0.6465	0.7408	0.4786	0.098*
C11A	0.7131 (5)	0.9079 (3)	0.4276 (4)	0.0787 (14)
H11A	0.6905	0.9560	0.3975	0.118*
H11C	0.8177	0.9167	0.4358	0.118*
H11B	0.6841	0.9272	0.4900	0.118*
C12A	0.6778 (5)	0.7560 (5)	0.2689 (3)	0.0796 (14)
H12C	0.7816	0.7622	0.2784	0.119*
H12A	0.6598	0.8042	0.2377	0.119*
H12B	0.6226	0.6801	0.2288	0.119*
C1B	0.6326 (3)	0.3538 (2)	0.2203 (2)	0.0338 (6)
C2B	0.9820 (3)	0.4038 (2)	0.3508 (2)	0.0329 (6)
H2B	0.9809	0.3303	0.3378	0.039*
C3B	1.1081 (3)	0.4953 (2)	0.41539 (19)	0.0307 (6)
C4B	1.1095 (3)	0.6063 (2)	0.4389 (2)	0.0319 (6)
C5B	1.2296 (3)	0.6925 (2)	0.5024 (2)	0.0346 (6)
C6B	1.3468 (3)	0.6685 (2)	0.54445 (19)	0.0347 (6)
C7B	1.3446 (3)	0.5582 (3)	0.5228 (2)	0.0377 (6)
H7B	1.4223	0.5420	0.5516	0.045*
C8B	1.2270 (3)	0.4731 (2)	0.4586 (2)	0.0356 (6)
H8B	1.2266	0.3994	0.4437	0.043*
C9B	0.5121 (3)	0.2445 (2)	0.1623 (2)	0.0368 (6)
H9B2	0.5382	0.2095	0.0997	0.044*
H9B1	0.5101	0.1948	0.1963	0.044*
C10B	0.3479 (4)	0.3179 (3)	0.0803 (2)	0.0470 (8)
H10D	0.3735	0.2794	0.0193	0.071*
H10F	0.4148	0.3921	0.1108	0.071*
H10E	0.2484	0.3218	0.0693	0.071*
C11B	0.2541 (4)	0.1409 (3)	0.0978 (3)	0.0578 (9)
H11D	0.2795	0.1022	0.0368	0.087*
H11E	0.1549	0.1453	0.0868	0.087*
H11F	0.2607	0.1012	0.1394	0.087*
C12B	0.3156 (4)	0.3150 (3)	0.2399 (2)	0.0504 (8)
H12D	0.2158	0.3178	0.2276	0.076*
H12E	0.3813	0.3896	0.2711	0.076*
H12F	0.3221	0.2751	0.2813	0.076*
H4B	0.940 (4)	0.579 (3)	0.370 (3)	0.051 (11)*
H5B	1.166 (6)	0.804 (4)	0.500 (4)	0.085 (17)*
H6B	1.454 (5)	0.816 (4)	0.621 (3)	0.075 (15)*
H4A	0.075 (5)	0.430 (4)	0.143 (3)	0.070 (14)*
H5A	−0.147 (5)	0.177 (4)	−0.030 (3)	0.067 (14)*
H6A	−0.427 (6)	0.165 (5)	−0.114 (4)	0.10 (2)*
H2NB	0.758 (4)	0.276 (3)	0.254 (2)	0.038 (9)*
H2NA	0.212 (4)	0.731 (3)	0.267 (3)	0.044 (11)*
C13	0.7289 (7)	0.0438 (5)	0.1584 (4)	0.1002 (18)
H13A	0.8041	0.0717	0.1271	0.150*
H13B	0.6329	0.0310	0.1224	0.150*
H13C	0.7380	−0.0251	0.1608	0.150*
O7	0.7452 (4)	0.1197 (3)	0.2501 (3)	0.0843 (10)
H7O	0.8265	0.1296	0.2811	0.126*

	U11	U22	U33	U12	U13	U23
Zn1	0.03453 (19)	0.03438 (19)	0.0375 (2)	0.00982 (14)	−0.00078 (14)	0.01356 (14)
Cl1	0.0518 (4)	0.0427 (4)	0.0458 (4)	0.0134 (3)	0.0046 (3)	0.0223 (3)
Cl2	0.0511 (5)	0.0706 (6)	0.0384 (4)	0.0232 (4)	−0.0089 (4)	0.0048 (4)
Cl3	0.0607 (5)	0.0396 (4)	0.0602 (5)	0.0222 (4)	−0.0016 (4)	0.0122 (4)
Cl4	0.0351 (4)	0.0513 (5)	0.0666 (5)	0.0088 (3)	0.0055 (4)	0.0155 (4)
O1A	0.0412 (13)	0.0405 (13)	0.0897 (19)	0.0182 (11)	−0.0098 (13)	0.0062 (13)
O4A	0.0375 (11)	0.0466 (13)	0.0444 (12)	0.0177 (10)	−0.0002 (10)	0.0134 (10)
O5A	0.0532 (15)	0.0411 (13)	0.0540 (14)	0.0108 (11)	0.0069 (12)	0.0139 (11)
O6A	0.0368 (12)	0.0543 (16)	0.0525 (14)	0.0054 (11)	−0.0063 (10)	0.0058 (12)
O1B	0.0411 (12)	0.0402 (12)	0.0673 (15)	0.0134 (10)	−0.0047 (11)	0.0181 (11)
O4B	0.0375 (12)	0.0382 (12)	0.0512 (13)	0.0121 (10)	−0.0059 (10)	0.0194 (11)
O5B	0.0522 (14)	0.0348 (12)	0.0558 (15)	0.0079 (10)	−0.0105 (12)	0.0146 (10)
O6B	0.0395 (12)	0.0476 (14)	0.0423 (12)	0.0020 (10)	−0.0094 (10)	0.0104 (11)
O7	0.076 (2)	0.0651 (19)	0.097 (2)	0.0241 (16)	−0.0165 (17)	0.0207 (17)
N1A	0.0286 (12)	0.0391 (13)	0.0355 (13)	0.0067 (10)	0.0029 (10)	0.0103 (10)
N2A	0.0276 (12)	0.0362 (14)	0.0430 (14)	0.0110 (11)	−0.0006 (10)	0.0071 (11)
N3A	0.0303 (13)	0.0478 (15)	0.0376 (13)	0.0064 (11)	−0.0032 (10)	0.0081 (11)
N1B	0.0280 (11)	0.0372 (12)	0.0299 (11)	0.0070 (10)	0.0008 (9)	0.0123 (10)
N2B	0.0293 (12)	0.0325 (13)	0.0351 (12)	0.0083 (10)	−0.0018 (10)	0.0109 (10)
N3B	0.0281 (11)	0.0474 (14)	0.0318 (12)	0.0092 (10)	0.0002 (9)	0.0192 (11)
C1A	0.0309 (14)	0.0390 (16)	0.0417 (16)	0.0099 (12)	0.0029 (12)	0.0108 (13)
C2A	0.0346 (15)	0.0411 (16)	0.0329 (14)	0.0120 (12)	0.0046 (12)	0.0131 (12)
C3A	0.0288 (13)	0.0432 (16)	0.0303 (14)	0.0108 (12)	0.0056 (11)	0.0147 (12)
C4A	0.0286 (13)	0.0459 (16)	0.0292 (13)	0.0141 (12)	0.0068 (11)	0.0149 (12)
C5A	0.0355 (15)	0.0454 (17)	0.0315 (14)	0.0123 (13)	0.0098 (12)	0.0146 (13)
C6A	0.0302 (14)	0.0538 (18)	0.0302 (14)	0.0070 (13)	0.0049 (11)	0.0129 (13)
C7A	0.0305 (15)	0.061 (2)	0.0365 (15)	0.0159 (14)	0.0002 (12)	0.0190 (14)
C8A	0.0364 (15)	0.0487 (17)	0.0365 (15)	0.0168 (13)	0.0044 (12)	0.0177 (13)
C9A	0.0315 (15)	0.0401 (16)	0.0526 (19)	0.0124 (13)	−0.0024 (13)	0.0081 (14)
C10A	0.054 (2)	0.078 (3)	0.064 (2)	0.029 (2)	−0.0094 (18)	0.027 (2)
C11A	0.046 (2)	0.054 (2)	0.096 (3)	−0.0037 (18)	−0.015 (2)	0.003 (2)
C12A	0.048 (2)	0.129 (4)	0.041 (2)	0.008 (2)	0.0077 (17)	0.019 (2)
C1B	0.0295 (13)	0.0395 (16)	0.0304 (13)	0.0096 (12)	0.0018 (11)	0.0126 (12)
C2B	0.0329 (14)	0.0347 (14)	0.0302 (14)	0.0123 (11)	0.0061 (11)	0.0101 (11)
C3B	0.0273 (13)	0.0377 (14)	0.0278 (13)	0.0101 (11)	0.0057 (10)	0.0131 (11)
C4B	0.0277 (13)	0.0418 (15)	0.0299 (13)	0.0107 (11)	0.0049 (11)	0.0182 (12)
C5B	0.0359 (15)	0.0365 (15)	0.0304 (14)	0.0079 (12)	0.0036 (11)	0.0143 (12)
C6B	0.0306 (14)	0.0435 (16)	0.0238 (13)	0.0063 (12)	0.0030 (11)	0.0096 (12)
C7B	0.0307 (14)	0.0494 (17)	0.0338 (14)	0.0165 (13)	0.0029 (11)	0.0148 (13)
C8B	0.0365 (15)	0.0371 (15)	0.0343 (14)	0.0156 (12)	0.0045 (12)	0.0126 (12)
C9B	0.0318 (14)	0.0387 (15)	0.0370 (15)	0.0123 (12)	−0.0016 (12)	0.0121 (12)
C10B	0.0419 (17)	0.068 (2)	0.0420 (17)	0.0188 (16)	0.0038 (14)	0.0324 (16)
C11B	0.0422 (18)	0.058 (2)	0.058 (2)	−0.0027 (16)	−0.0138 (16)	0.0210 (18)
C12B	0.0444 (18)	0.073 (2)	0.0389 (17)	0.0214 (17)	0.0149 (14)	0.0230 (16)
C13	0.108 (4)	0.094 (4)	0.089 (4)	0.060 (3)	0.002 (3)	0.009 (3)

Zn1—Cl3	2.2467 (13)	O4B—C4B	1.357 (3)
Zn1—Cl1	2.2661 (11)	O4B—H4B	0.80 (4)
Zn1—Cl2	2.2731 (18)	O5B—C5B	1.371 (4)
Zn1—Cl4	2.2870 (12)	O5B—H5B	0.77 (5)
O1A—C1A	1.208 (4)	O6B—C6B	1.359 (4)
O4A—C4A	1.356 (3)	O6B—H6B	0.85 (5)
O4A—H4A	0.84 (4)	N1B—C2B	1.276 (4)
O5A—C5A	1.369 (4)	N1B—N2B	1.366 (3)
O5A—H5A	0.82 (5)	N2B—C1B	1.352 (4)
O6A—C6A	1.362 (4)	N2B—H2NB	0.79 (3)
O6A—H6A	0.82 (6)	N3B—C11B	1.493 (4)
N1A—C2A	1.285 (4)	N3B—C10B	1.495 (4)
N1A—N2A	1.373 (4)	N3B—C12B	1.504 (4)
N2A—C1A	1.346 (4)	N3B—C9B	1.506 (4)
N2A—H2NA	0.75 (4)	C1B—C9B	1.523 (4)
N3A—C12A	1.484 (5)	C2B—C3B	1.454 (4)
N3A—C9A	1.494 (4)	C2B—H2B	0.9300
N3A—C11A	1.497 (5)	C3B—C4B	1.396 (4)
N3A—C10A	1.505 (5)	C3B—C8B	1.397 (4)
C1A—C9A	1.513 (4)	C4B—C5B	1.390 (4)
C2A—C3A	1.441 (4)	C5B—C6B	1.389 (4)
C2A—H2A	0.9300	C6B—C7B	1.388 (4)
C3A—C4A	1.405 (4)	C7B—C8B	1.373 (4)
C3A—C8A	1.407 (4)	C7B—H7B	0.9300
C4A—C5A	1.382 (4)	C8B—H8B	0.9300
C5A—C6A	1.390 (4)	C9B—H9B2	0.9700
C6A—C7A	1.378 (5)	C9B—H9B1	0.9700
C7A—C8A	1.371 (5)	C10B—H10D	0.9600
C7A—H7A	0.9300	C10B—H10F	0.9600
C8A—H9A	0.9300	C10B—H10E	0.9600
C9A—H9A1	0.9700	C11B—H11D	0.9600
C9A—H9A2	0.9700	C11B—H11E	0.9600
C10A—H10B	0.9600	C11B—H11F	0.9600
C10A—H10A	0.9600	C12B—H12D	0.9600
C10A—H10C	0.9600	C12B—H12E	0.9600
C11A—H11A	0.9600	C12B—H12F	0.9600
C11A—H11C	0.9600	C13—O7	1.355 (6)
C11A—H11B	0.9600	O7—H7O	0.8200
C12A—H12C	0.9600	C13—H13A	0.9600
C12A—H12A	0.9600	C13—H13B	0.9600
C12A—H12B	0.9600	C13—H13C	0.9600
O1B—C1B	1.203 (4)
Cl3—Zn1—Cl1	109.97 (5)	H10A—C10A—H10C	109.5
Cl3—Zn1—Cl2	110.89 (5)	N3A—C11A—H11A	109.5
Cl1—Zn1—Cl2	107.16 (5)	N3A—C11A—H11C	109.5
Cl3—Zn1—Cl4	113.17 (6)	H11A—C11A—H11C	109.5
Cl1—Zn1—Cl4	105.36 (5)	N3A—C11A—H11B	109.5
Cl2—Zn1—Cl4	109.97 (6)	H11A—C11A—H11B	109.5
C4A—O4A—H4A	103 (3)	H11C—C11A—H11B	109.5
C5A—O5A—H5A	108 (3)	N3A—C12A—H12C	109.5
C6A—O6A—H6A	113 (4)	N3A—C12A—H12A	109.5
C4B—O4B—H4B	102 (3)	H12C—C12A—H12A	109.5
C5B—O5B—H5B	106 (4)	N3A—C12A—H12B	109.5
C6B—O6B—H6B	112 (3)	H12C—C12A—H12B	109.5
C13—O7—H7O	109.5	H12A—C12A—H12B	109.5
C2A—N1A—N2A	116.7 (3)	O1B—C1B—N2B	124.5 (3)
C1A—N2A—N1A	118.6 (3)	O1B—C1B—C9B	124.6 (3)
C1A—N2A—H2NA	126 (3)	N2B—C1B—C9B	110.9 (2)
N1A—N2A—H2NA	116 (3)	N1B—C2B—C3B	120.2 (3)
C12A—N3A—C9A	112.0 (3)	N1B—C2B—H2B	119.9
C12A—N3A—C11A	110.4 (3)	C3B—C2B—H2B	119.9
C9A—N3A—C11A	106.7 (3)	C4B—C3B—C8B	118.9 (3)
C12A—N3A—C10A	108.2 (3)	C4B—C3B—C2B	120.9 (2)
C9A—N3A—C10A	112.0 (3)	C8B—C3B—C2B	120.2 (3)
C11A—N3A—C10A	107.4 (3)	O4B—C4B—C5B	116.0 (3)
C2B—N1B—N2B	117.1 (2)	O4B—C4B—C3B	124.0 (3)
C1B—N2B—N1B	118.6 (3)	C5B—C4B—C3B	120.0 (3)
C1B—N2B—H2NB	124 (2)	O5B—C5B—C6B	117.4 (3)
N1B—N2B—H2NB	116 (2)	O5B—C5B—C4B	122.5 (3)
C11B—N3B—C10B	109.3 (2)	C6B—C5B—C4B	120.1 (3)
C11B—N3B—C12B	108.3 (3)	O6B—C6B—C7B	118.6 (3)
C10B—N3B—C12B	109.5 (3)	O6B—C6B—C5B	121.4 (3)
C11B—N3B—C9B	107.3 (2)	C7B—C6B—C5B	120.1 (3)
C10B—N3B—C9B	111.6 (2)	C8B—C7B—C6B	119.7 (3)
C12B—N3B—C9B	110.8 (2)	C8B—C7B—H7B	120.1
O1A—C1A—N2A	123.6 (3)	C6B—C7B—H7B	120.1
O1A—C1A—C9A	124.5 (3)	C7B—C8B—C3B	121.2 (3)
N2A—C1A—C9A	112.0 (3)	C7B—C8B—H8B	119.4
N1A—C2A—C3A	119.6 (3)	C3B—C8B—H8B	119.4
N1A—C2A—H2A	120.2	N3B—C9B—C1B	114.8 (2)
C3A—C2A—H2A	120.2	N3B—C9B—H9B2	108.6
C4A—C3A—C8A	118.3 (3)	C1B—C9B—H9B2	108.6
C4A—C3A—C2A	122.4 (3)	N3B—C9B—H9B1	108.6
C8A—C3A—C2A	119.2 (3)	C1B—C9B—H9B1	108.6
O4A—C4A—C5A	117.7 (3)	H9B2—C9B—H9B1	107.5
O4A—C4A—C3A	122.1 (3)	N3B—C10B—H10D	109.5
C5A—C4A—C3A	120.2 (3)	N3B—C10B—H10F	109.5
O5A—C5A—C4A	122.5 (3)	H10D—C10B—H10F	109.5
O5A—C5A—C6A	117.6 (3)	N3B—C10B—H10E	109.5
C4A—C5A—C6A	119.8 (3)	H10D—C10B—H10E	109.5
O6A—C6A—C7A	119.7 (3)	H10F—C10B—H10E	109.5
O6A—C6A—C5A	119.4 (3)	N3B—C11B—H11D	109.5
C7A—C6A—C5A	121.0 (3)	N3B—C11B—H11E	109.5
C8A—C7A—C6A	119.5 (3)	H11D—C11B—H11E	109.5
C8A—C7A—H7A	120.3	N3B—C11B—H11F	109.5
C6A—C7A—H7A	120.3	H11D—C11B—H11F	109.5
C7A—C8A—C3A	121.3 (3)	H11E—C11B—H11F	109.5
C7A—C8A—H9A	119.4	N3B—C12B—H12D	109.5
C3A—C8A—H9A	119.4	N3B—C12B—H12E	109.5
N3A—C9A—C1A	115.2 (3)	H12D—C12B—H12E	109.5
N3A—C9A—H9A1	108.5	N3B—C12B—H12F	109.5
C1A—C9A—H9A1	108.5	H12D—C12B—H12F	109.5
N3A—C9A—H9A2	108.5	H12E—C12B—H12F	109.5
C1A—C9A—H9A2	108.5	O7—C13—H13A	109.5
H9A1—C9A—H9A2	107.5	O7—C13—H13B	109.5
N3A—C10A—H10B	109.5	H13A—C13—H13B	109.5
N3A—C10A—H10A	109.5	O7—C13—H13C	109.5
H10B—C10A—H10A	109.5	H13A—C13—H13C	109.5
N3A—C10A—H10C	109.5	H13B—C13—H13C	109.5
H10B—C10A—H10C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O4A—H4A···N1A	0.84 (5)	1.82 (5)	2.592 (4)	153 (5)
O5A—H5A···Cl2i	0.83 (5)	2.29 (5)	3.094 (4)	167 (3)
O6A—H6A···O5A	0.82 (7)	2.30 (6)	2.693 (4)	110 (5)
O6A—H6A···Cl4i	0.82 (7)	2.64 (6)	3.317 (3)	141 (5)
O4B—H4B···N1B	0.80 (4)	1.86 (4)	2.599 (4)	155 (4)
O5B—H5B···O4B	0.77 (6)	2.28 (6)	2.721 (4)	118 (5)
O5B—H5B···Cl1ii	0.77 (6)	2.60 (5)	3.217 (3)	139 (5)
O6B—H6B···O5B	0.85 (5)	2.32 (5)	2.728 (4)	110 (4)
O6B—H6B···Cl4iii	0.85 (5)	2.59 (5)	3.193 (3)	129 (4)
C10A—H10A···O1A	0.96	2.34	2.992 (5)	124
C10B—H10F···O1B	0.96	2.33	2.978 (4)	124
C10B—H10E···O4A	0.96	2.50	3.404 (5)	157
C10B—H10F···O1B	0.96	2.33	2.978 (4)	124
C12A—H12A···O6Ai	0.96	2.60	3.307 (6)	131
C12A—H12B···O1A	0.96	2.41	3.043 (7)	123
C12B—H12E···O1B	0.96	2.40	3.028 (5)	123
C12A—H12C···Cl1ii	0.96	2.83	3.715 (5)	154
O7—H7O···Cl3iv	0.82	2.44	3.251 (4)	169
N2A—H2NA···Cl1	0.77 (4)	2.59 (4)	3.287 (3)	154 (4)
N2B—H2NB···O7	0.78 (4)	2.05 (4)	2.826 (5)	175 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4A—H4A⋯N1A	0.84 (5)	1.82 (5)	2.592 (4)	153 (5)
O5A—H5A⋯Cl2i	0.83 (5)	2.29 (5)	3.094 (4)	167 (3)
O6A—H6A⋯O5A	0.82 (7)	2.30 (6)	2.693 (4)	110 (5)
O6A—H6A⋯Cl4i	0.82 (7)	2.64 (6)	3.317 (3)	141 (5)
O4B—H4B⋯N1B	0.80 (4)	1.86 (4)	2.599 (4)	155 (4)
O5B—H5B⋯O4B	0.77 (6)	2.28 (6)	2.721 (4)	118 (5)
O5B—H5B⋯Cl1ii	0.77 (6)	2.60 (5)	3.217 (3)	139 (5)
O6B—H6B⋯O5B	0.85 (5)	2.32 (5)	2.728 (4)	110 (4)
O6B—H6B⋯Cl4iii	0.85 (5)	2.59 (5)	3.193 (3)	129 (4)
C10A—H10A⋯O1A	0.96	2.34	2.992 (5)	124
C10B—H10F⋯O1B	0.96	2.33	2.978 (4)	124
C10B—H10E⋯O4A	0.96	2.50	3.404 (5)	157
C10B—H10F⋯O1B	0.96	2.33	2.978 (4)	124
C12A—H12A⋯O6Ai	0.96	2.60	3.307 (6)	131
C12A—H12B⋯O1A	0.96	2.41	3.043 (7)	123
C12B—H12E⋯O1B	0.96	2.40	3.028 (5)	123
C12A—H12C⋯Cl1ii	0.96	2.83	3.715 (5)	154
O7—H7O⋯Cl3iv	0.82	2.44	3.251 (4)	169
N2A—H2NA⋯Cl1	0.77 (4)	2.59 (4)	3.287 (3)	154 (4)
N2B—H2NB⋯O7	0.78 (4)	2.05 (4)	2.826 (5)	175 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .