(2-Meth­oxy­benz­yl)(2-meth­oxy­benzyl­idene)aza­nium (2-meth­oxy­phen­yl)methanaminium tetra­chloridozincate(II) monohydrate

The title compound, (C₈H₁₂NO)(C₁₆H₁₈NO₂)[ZnCl₄]·H₂O, was obtained as a by-product of the Zn²⁺ and HCl catalyzed condensation of (2-meth­oxy­phen­yl)methanamine in water. Both cations feature an intra­molecular N—H...O hydrogen bond. In the crystal, the components are linked by an extensive three-dimensional network of N—H...O, O—H...Cl and N—H...Cl hydrogen bonds (three of them bifurcated). Weak C—H...O intera­ctions also occur.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.087
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          7
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of         Zn1
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B    ..  CL3     ..       2.98 Ang.
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600       1415

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)       1000 Deg.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

As a part of our ongoing investigations in molecular salts containing meta-chlorido complexes (Ben Gharbia et al., 2005; Ben Gharbia et al., 2008), we report here the crystal structure of one such compound, (C₁₆H₁₈NO₂)(C₈H₁₂NO)[ZnCl₄].H₂O. The title compound was obtained as a byproduct of the Zn²⁺ and HCl catalyzed condensation of (2-methoxyphenyl) methanamine in water. Subsequent crystallization from the reaction mixture yielded among the main reaction products crystals of the title compound that consist of one N-(2-methoxybenzylidene)-1-(2-methoxyphenyl)methanaminnium cation, one (2-methoxyphenyl) methanaminium cation, one ZnCl₄^2- anion and one interstitial water molecule (Fig. 1).

The distance N1—C9 [1.273 (2) Å] is substantially shorter than the one of N1—C8 [1.477 (2) Å], indicating the presence of a double bond in the condensation product, thus indicating the nature of the organic molecules in the crystal as indictated in Scheme 1. Preliminary NMR data on the material indicate that the bulk of the reaction product is not identical with the title compound. Further investigations into the nature of the bulk material are under way.

The Cl—Zn—Cl bond angles in the title compound show relatively little distortion from a regular tetrahedron [spread values 104.45 (3)–111.78 (2)] (Gayathri et al., 2008, Hosseinian et al., 2009). Classic N—H···O, O—H···Cl and N—H···Cl hydrogen bonds are observed, which link the two types of organic ammonium cations, the anionic complexes [ZnCl₄]^2- and the uncoordinated water molecules into a 3-D hydrogen bonded network, as shown in Fig. 2. Three of the hydrogen bonds are bifurcated: N1—H1··· (Cl2,O2), N2—H2A···(O3,O4) and N2—H2B···(O4,Cl3).

Related literature

For related meta-chlorido complexes, see: Ben Gharbia et al. (2005, 2008). For Zn—Cl distances and Cl—Zn—Cl bond angles, see: Gayathri et al. (2008); Hosseinian et al. (2009).

S2. Experimental

An aqueous solution of (2-methoxyphenyl) methanamine (2-methoxybenzylamine), zinc chloride and 1 M hydrochloric acid in a Petri disk was slowly evaporated at room temperature. A colourless block of (I), which remained stable under normal conditions of temperature and humidity, was isolated as a byproduct of the reaction.

S3. Refinement

C—H and ammonium H atoms were placed in calculated positions with C—H in the range 0.93–0.97 and N—H equal to 0.89 Å. The imminium and the water hydrogen atom postitions were refined with N—H and O—H distance restraints of 0.89 (2) and 0.82 (2) Å. The U_iso(H) values of all H atoms were constrained to 1.2 or 1.5 times U_eq of the respective parent atom.

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. A view of the title compound, showing 50% probability displacement ellipsoids (arbitrary spheres for the H atoms).
	Fig. 2. Projection of the structure along the a axis. Hydrogen bonds are denoted by dotted lines.

(2-Methoxybenzyl)(2-methoxybenzylidene)azanium (2-methoxyphenyl)methanaminium tetrachloridozincate(II) monohydrate

Crystal data

(C8H12NO)(C16H18NO2)[ZnCl4]·H2O	Z = 2
Mr = 619.69	F(000) = 640
Triclinic, P1	Dx = 1.422 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.0884 (9) Å	Cell parameters from 5313 reflections
b = 12.424 (2) Å	θ = 3.0–29.2°
c = 14.678 (2) Å	µ = 1.25 mm^−1
α = 98.23 (1)°	T = 293 K
β = 97.43 (1)°	Block, colourless
γ = 90.29 (1)°	0.54 × 0.47 × 0.25 mm
V = 1447.1 (3) Å^3

Data collection

Oxford Diffraction Xcalibur diffractometer	6583 independent reflections
Radiation source: fine-focus sealed tube	4644 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 29.5°, θmin = 3.0°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009; Clark & Reid, 1995)	h = −10→11
Tmin = 0.576, Tmax = 0.749	k = −15→16
12584 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0435P)^2] where P = (Fo^2 + 2Fc^2)/3
6583 reflections	(Δ/σ)max = 0.001
329 parameters	Δρmax = 0.72 e Å^−3
3 restraints	Δρmin = −0.64 e Å^−3

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
C1	0.2523 (3)	0.0313 (2)	0.58855 (19)	0.0669 (8)
H1A	0.2600	−0.0055	0.5272	0.100*
H1B	0.1579	0.0778	0.5869	0.100*
H1C	0.2392	−0.0214	0.6292	0.100*
C2	0.5461 (3)	0.04191 (18)	0.63917 (14)	0.0377 (5)
C3	0.5657 (3)	−0.06829 (19)	0.61983 (16)	0.0486 (6)
H3	0.4754	−0.1130	0.5916	0.058*
C4	0.7185 (3)	−0.1128 (2)	0.64206 (17)	0.0559 (6)
H4	0.7313	−0.1875	0.6285	0.067*
C5	0.8521 (3)	−0.0475 (2)	0.68406 (17)	0.0535 (6)
H5	0.9549	−0.0779	0.6999	0.064*
C6	0.8333 (3)	0.06297 (19)	0.70261 (14)	0.0421 (5)
H6	0.9247	0.1070	0.7303	0.051*
C7	0.6816 (2)	0.11022 (17)	0.68108 (13)	0.0331 (4)
C8	0.6598 (3)	0.23148 (16)	0.70157 (13)	0.0367 (5)
H8A	0.5629	0.2461	0.7336	0.044*
H8B	0.7568	0.2646	0.7418	0.044*
C9	0.5018 (2)	0.31536 (16)	0.57852 (13)	0.0331 (4)
H9	0.4129	0.3162	0.6129	0.040*
C10	0.4693 (2)	0.35513 (16)	0.49025 (13)	0.0326 (4)
C11	0.3132 (2)	0.39947 (17)	0.46852 (15)	0.0390 (5)
H11	0.2380	0.4048	0.5117	0.047*
C12	0.2683 (3)	0.43548 (18)	0.38452 (16)	0.0485 (6)
H12	0.1641	0.4649	0.3709	0.058*
C13	0.3800 (3)	0.42721 (19)	0.32143 (16)	0.0536 (6)
H13	0.3498	0.4506	0.2643	0.064*
C14	0.5355 (3)	0.3854 (2)	0.34018 (15)	0.0469 (6)
H14	0.6098	0.3814	0.2965	0.056*
C15	0.5808 (2)	0.34898 (17)	0.42502 (14)	0.0360 (5)
C16	0.8537 (3)	0.2994 (3)	0.38782 (19)	0.0764 (9)
H16A	0.8119	0.2554	0.3301	0.115*
H16B	0.9527	0.2678	0.4153	0.115*
H16C	0.8797	0.3714	0.3766	0.115*
C17	0.2513 (3)	0.1890 (3)	0.1188 (2)	0.0783 (9)
H17A	0.2140	0.1149	0.0986	0.117*
H17B	0.1647	0.2370	0.1003	0.117*
H17C	0.2776	0.2010	0.1852	0.117*
C18	0.5273 (3)	0.14345 (19)	0.08828 (15)	0.0467 (6)
C19	0.5371 (4)	0.0578 (2)	0.14046 (17)	0.0616 (7)
H19	0.4496	0.0425	0.1722	0.074*
C20	0.6792 (4)	−0.0042 (2)	0.14433 (19)	0.0741 (8)
H20	0.6864	−0.0621	0.1783	0.089*
C21	0.8083 (4)	0.0192 (3)	0.0987 (2)	0.0772 (9)
H21	0.9038	−0.0221	0.1023	0.093*
C22	0.7973 (3)	0.1043 (2)	0.04706 (19)	0.0641 (7)
H22	0.8862	0.1200	0.0164	0.077*
C23	0.6558 (3)	0.16659 (19)	0.04026 (15)	0.0435 (5)
C24	0.6378 (3)	0.2543 (2)	−0.02067 (16)	0.0512 (6)
H24A	0.7340	0.2540	−0.0539	0.061*
H24B	0.5397	0.2379	−0.0663	0.061*
Cl3	0.40847 (6)	0.41374 (5)	0.81903 (4)	0.04914 (15)
Cl2	0.04753 (7)	0.32552 (5)	0.63718 (3)	0.05224 (16)
Cl1	0.03902 (8)	0.57253 (6)	0.81699 (4)	0.06066 (18)
Cl4	0.03288 (9)	0.29378 (6)	0.88415 (4)	0.0746 (2)
N1	0.6383 (2)	0.27933 (13)	0.61445 (11)	0.0334 (4)
H1	0.729 (2)	0.2772 (17)	0.5852 (13)	0.040*
N2	0.6225 (2)	0.36549 (15)	0.03186 (13)	0.0488 (5)
H2A	0.5218	0.3717	0.0501	0.073*
H2B	0.6365	0.4152	−0.0047	0.073*
H2C	0.7000	0.3756	0.0814	0.073*
O1	0.40047 (18)	0.09490 (13)	0.62188 (11)	0.0508 (4)
O2	0.72997 (17)	0.30455 (13)	0.44960 (10)	0.0458 (4)
O3	0.3943 (2)	0.20972 (14)	0.07819 (12)	0.0616 (5)
O4	0.2655 (2)	0.45092 (16)	0.04551 (11)	0.0573 (5)
H4B	0.220 (3)	0.412 (2)	0.0009 (15)	0.086*
H4A	0.208 (3)	0.473 (3)	0.0836 (17)	0.086*
Zn1	0.12911 (3)	0.39816 (2)	0.786811 (15)	0.03902 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0402 (13)	0.079 (2)	0.0807 (19)	−0.0143 (13)	0.0011 (13)	0.0147 (16)
C2	0.0393 (12)	0.0406 (14)	0.0358 (11)	−0.0040 (10)	0.0081 (9)	0.0113 (10)
C3	0.0548 (14)	0.0362 (14)	0.0524 (14)	−0.0100 (11)	0.0027 (11)	0.0031 (12)
C4	0.0713 (18)	0.0304 (14)	0.0637 (16)	0.0043 (12)	0.0050 (13)	0.0018 (12)
C5	0.0504 (14)	0.0428 (16)	0.0665 (16)	0.0090 (11)	0.0044 (12)	0.0085 (13)
C6	0.0401 (12)	0.0393 (14)	0.0461 (13)	−0.0011 (10)	0.0011 (10)	0.0075 (11)
C7	0.0400 (11)	0.0314 (12)	0.0299 (10)	−0.0007 (9)	0.0076 (8)	0.0080 (9)
C8	0.0462 (12)	0.0327 (12)	0.0311 (10)	0.0012 (9)	0.0046 (9)	0.0050 (9)
C9	0.0349 (11)	0.0276 (11)	0.0367 (11)	−0.0013 (8)	0.0073 (9)	0.0024 (9)
C10	0.0343 (10)	0.0275 (11)	0.0357 (11)	−0.0030 (8)	0.0015 (8)	0.0061 (9)
C11	0.0349 (11)	0.0307 (12)	0.0504 (13)	−0.0035 (9)	0.0017 (10)	0.0061 (10)
C12	0.0416 (12)	0.0413 (14)	0.0599 (15)	−0.0027 (10)	−0.0104 (11)	0.0142 (12)
C13	0.0635 (16)	0.0510 (16)	0.0454 (13)	−0.0112 (12)	−0.0118 (12)	0.0208 (12)
C14	0.0510 (14)	0.0531 (15)	0.0377 (12)	−0.0075 (11)	0.0052 (10)	0.0118 (11)
C15	0.0355 (11)	0.0327 (12)	0.0393 (11)	−0.0066 (9)	0.0008 (9)	0.0073 (10)
C16	0.0522 (16)	0.116 (3)	0.0707 (18)	0.0130 (16)	0.0307 (14)	0.0248 (18)
C17	0.0612 (17)	0.080 (2)	0.104 (2)	0.0048 (15)	0.0403 (17)	0.0217 (19)
C18	0.0518 (14)	0.0454 (15)	0.0433 (13)	0.0018 (11)	0.0046 (11)	0.0090 (12)
C19	0.0748 (18)	0.0559 (18)	0.0588 (16)	0.0021 (14)	0.0137 (14)	0.0202 (14)
C20	0.101 (2)	0.058 (2)	0.0637 (18)	0.0116 (17)	−0.0055 (17)	0.0245 (16)
C21	0.069 (2)	0.075 (2)	0.084 (2)	0.0259 (16)	−0.0060 (16)	0.0126 (18)
C22	0.0508 (15)	0.066 (2)	0.0751 (18)	0.0077 (13)	0.0082 (13)	0.0080 (16)
C23	0.0402 (12)	0.0427 (14)	0.0457 (13)	0.0002 (10)	0.0025 (10)	0.0019 (11)
C24	0.0579 (15)	0.0516 (16)	0.0472 (13)	−0.0012 (12)	0.0177 (11)	0.0080 (12)
Cl3	0.0335 (3)	0.0638 (4)	0.0473 (3)	0.0050 (3)	0.0046 (2)	−0.0010 (3)
Cl2	0.0449 (3)	0.0768 (5)	0.0322 (3)	−0.0055 (3)	0.0033 (2)	0.0003 (3)
Cl1	0.0586 (4)	0.0643 (5)	0.0540 (4)	0.0230 (3)	−0.0034 (3)	0.0003 (3)
Cl4	0.0860 (5)	0.0963 (6)	0.0413 (3)	−0.0483 (4)	0.0023 (3)	0.0165 (4)
N1	0.0369 (9)	0.0298 (10)	0.0347 (9)	−0.0008 (8)	0.0067 (7)	0.0067 (8)
N2	0.0512 (11)	0.0436 (12)	0.0522 (11)	−0.0044 (9)	0.0039 (9)	0.0118 (10)
O1	0.0377 (8)	0.0492 (10)	0.0652 (10)	−0.0031 (7)	0.0023 (7)	0.0120 (8)
O2	0.0374 (8)	0.0595 (11)	0.0444 (8)	0.0057 (7)	0.0109 (7)	0.0159 (8)
O3	0.0493 (10)	0.0612 (12)	0.0850 (13)	0.0119 (8)	0.0259 (9)	0.0309 (10)
O4	0.0568 (11)	0.0688 (13)	0.0442 (10)	−0.0155 (9)	0.0040 (8)	0.0048 (10)
Zn1	0.03518 (14)	0.05046 (18)	0.03133 (14)	−0.00161 (11)	0.00427 (10)	0.00579 (12)

Geometric parameters (Å, º)

C1—O1	1.424 (3)	C16—O2	1.431 (2)
C1—H1A	0.9600	C16—H16A	0.9600
C1—H1B	0.9600	C16—H16B	0.9600
C1—H1C	0.9600	C16—H16C	0.9600
C2—O1	1.365 (2)	C17—O3	1.407 (3)
C2—C3	1.372 (3)	C17—H17A	0.9600
C2—C7	1.402 (3)	C17—H17B	0.9600
C3—C4	1.377 (3)	C17—H17C	0.9600
C3—H3	0.9300	C18—O3	1.364 (3)
C4—C5	1.372 (3)	C18—C23	1.380 (3)
C4—H4	0.9300	C18—C19	1.394 (3)
C5—C6	1.374 (3)	C19—C20	1.386 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.382 (3)	C20—C21	1.362 (4)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.509 (3)	C21—C22	1.384 (4)
C8—N1	1.477 (2)	C21—H21	0.9300
C8—H8A	0.9700	C22—C23	1.386 (3)
C8—H8B	0.9700	C22—H22	0.9300
C9—N1	1.273 (2)	C23—C24	1.501 (3)
C9—C10	1.445 (3)	C24—N2	1.497 (3)
C9—H9	0.9300	C24—H24A	0.9700
C10—C15	1.392 (3)	C24—H24B	0.9700
C10—C11	1.397 (3)	Cl3—Zn1	2.2495 (6)
C11—C12	1.377 (3)	Cl2—Zn1	2.2639 (6)
C11—H11	0.9300	Cl1—Zn1	2.2903 (8)
C12—C13	1.369 (3)	Cl4—Zn1	2.2664 (7)
C12—H12	0.9300	N1—H1	0.893 (14)
C13—C14	1.373 (3)	N2—H2A	0.8900
C13—H13	0.9300	N2—H2B	0.8900
C14—C15	1.391 (3)	N2—H2C	0.8900
C14—H14	0.9300	O4—H4B	0.801 (17)
C15—O2	1.357 (2)	O4—H4A	0.795 (17)
O1—C1—H1A	109.5	H16A—C16—H16B	109.5
O1—C1—H1B	109.5	O2—C16—H16C	109.5
H1A—C1—H1B	109.5	H16A—C16—H16C	109.5
O1—C1—H1C	109.5	H16B—C16—H16C	109.5
H1A—C1—H1C	109.5	O3—C17—H17A	109.5
H1B—C1—H1C	109.5	O3—C17—H17B	109.5
O1—C2—C3	125.4 (2)	H17A—C17—H17B	109.5
O1—C2—C7	114.2 (2)	O3—C17—H17C	109.5
C3—C2—C7	120.4 (2)	H17A—C17—H17C	109.5
C2—C3—C4	120.2 (2)	H17B—C17—H17C	109.5
C2—C3—H3	119.9	O3—C18—C23	114.11 (19)
C4—C3—H3	119.9	O3—C18—C19	124.9 (2)
C5—C4—C3	120.3 (2)	C23—C18—C19	121.0 (2)
C5—C4—H4	119.9	C20—C19—C18	119.1 (2)
C3—C4—H4	119.9	C20—C19—H19	120.4
C4—C5—C6	119.6 (2)	C18—C19—H19	120.4
C4—C5—H5	120.2	C21—C20—C19	120.4 (3)
C6—C5—H5	120.2	C21—C20—H20	119.8
C5—C6—C7	121.5 (2)	C19—C20—H20	119.8
C5—C6—H6	119.3	C20—C21—C22	120.1 (3)
C7—C6—H6	119.3	C20—C21—H21	120.0
C6—C7—C2	118.0 (2)	C22—C21—H21	120.0
C6—C7—C8	121.79 (19)	C21—C22—C23	121.0 (3)
C2—C7—C8	120.23 (18)	C21—C22—H22	119.5
N1—C8—C7	110.25 (16)	C23—C22—H22	119.5
N1—C8—H8A	109.6	C18—C23—C22	118.4 (2)
C7—C8—H8A	109.6	C18—C23—C24	120.1 (2)
N1—C8—H8B	109.6	C22—C23—C24	121.5 (2)
C7—C8—H8B	109.6	N2—C24—C23	113.39 (18)
H8A—C8—H8B	108.1	N2—C24—H24A	108.9
N1—C9—C10	127.33 (18)	C23—C24—H24A	108.9
N1—C9—H9	116.3	N2—C24—H24B	108.9
C10—C9—H9	116.3	C23—C24—H24B	108.9
C15—C10—C11	118.40 (18)	H24A—C24—H24B	107.7
C15—C10—C9	124.36 (18)	C9—N1—C8	124.65 (17)
C11—C10—C9	117.20 (18)	C9—N1—H1	120.6 (13)
C12—C11—C10	121.4 (2)	C8—N1—H1	114.6 (13)
C12—C11—H11	119.3	C24—N2—H2A	109.5
C10—C11—H11	119.3	C24—N2—H2B	109.5
C13—C12—C11	118.8 (2)	H2A—N2—H2B	109.5
C13—C12—H12	120.6	C24—N2—H2C	109.5
C11—C12—H12	120.6	H2A—N2—H2C	109.5
C12—C13—C14	121.8 (2)	H2B—N2—H2C	109.5
C12—C13—H13	119.1	C2—O1—C1	118.18 (19)
C14—C13—H13	119.1	C15—O2—C16	119.14 (17)
C13—C14—C15	119.4 (2)	C18—O3—C17	119.08 (19)
C13—C14—H14	120.3	H4B—O4—H4A	115 (3)
C15—C14—H14	120.3	Cl3—Zn1—Cl2	111.78 (2)
O2—C15—C14	123.99 (19)	Cl3—Zn1—Cl4	108.77 (3)
O2—C15—C10	115.83 (17)	Cl2—Zn1—Cl4	110.35 (3)
C14—C15—C10	120.17 (19)	Cl3—Zn1—Cl1	104.45 (3)
O2—C16—H16A	109.5	Cl2—Zn1—Cl1	111.19 (3)
O2—C16—H16B	109.5	Cl4—Zn1—Cl1	110.14 (3)
O1—C2—C3—C4	−178.8 (2)	C11—C10—C15—C14	−0.7 (3)
C7—C2—C3—C4	0.5 (3)	C9—C10—C15—C14	177.2 (2)
C2—C3—C4—C5	0.3 (4)	O3—C18—C19—C20	179.4 (2)
C3—C4—C5—C6	−1.0 (4)	C23—C18—C19—C20	0.5 (4)
C4—C5—C6—C7	0.9 (3)	C18—C19—C20—C21	0.8 (4)
C5—C6—C7—C2	−0.2 (3)	C19—C20—C21—C22	−0.9 (5)
C5—C6—C7—C8	179.77 (18)	C20—C21—C22—C23	−0.4 (4)
O1—C2—C7—C6	178.82 (17)	O3—C18—C23—C22	179.3 (2)
C3—C2—C7—C6	−0.5 (3)	C19—C18—C23—C22	−1.7 (4)
O1—C2—C7—C8	−1.1 (3)	O3—C18—C23—C24	−3.2 (3)
C3—C2—C7—C8	179.54 (18)	C19—C18—C23—C24	175.8 (2)
C6—C7—C8—N1	108.7 (2)	C21—C22—C23—C18	1.6 (4)
C2—C7—C8—N1	−71.3 (2)	C21—C22—C23—C24	−175.8 (2)
N1—C9—C10—C15	7.4 (3)	C18—C23—C24—N2	64.7 (3)
N1—C9—C10—C11	−174.7 (2)	C22—C23—C24—N2	−117.9 (2)
C15—C10—C11—C12	0.7 (3)	C10—C9—N1—C8	−174.76 (19)
C9—C10—C11—C12	−177.4 (2)	C7—C8—N1—C9	108.3 (2)
C10—C11—C12—C13	0.0 (3)	C3—C2—O1—C1	5.8 (3)
C11—C12—C13—C14	−0.8 (4)	C7—C2—O1—C1	−173.46 (18)
C12—C13—C14—C15	0.8 (4)	C14—C15—O2—C16	3.6 (3)
C13—C14—C15—O2	178.8 (2)	C10—C15—O2—C16	−177.5 (2)
C13—C14—C15—C10	−0.1 (3)	C23—C18—O3—C17	175.7 (2)
C11—C10—C15—O2	−179.57 (19)	C19—C18—O3—C17	−3.3 (4)
C9—C10—C15—O2	−1.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.89 (1)	2.07 (2)	2.680 (2)	125 (2)
N1—H1···Cl2^i	0.89 (1)	2.64 (2)	3.3221 (18)	135 (2)
N2—H2A···O4	0.89	2.30	3.102 (3)	151
N2—H2A···O3	0.89	2.37	2.877 (2)	116
N2—H2B···O4^ii	0.89	2.04	2.881 (3)	158
N2—H2B···Cl3^iii	0.89	2.98	3.502 (2)	120
N2—H2C···Cl1^iv	0.89	2.45	3.306 (2)	162
O4—H4B···Cl4^iii	0.80 (2)	2.44 (2)	3.2323 (19)	168 (3)
O4—H4A···Cl1^v	0.80 (2)	2.72 (2)	3.4165 (19)	147 (3)
C8—H8A···Cl3	0.97	2.67	3.474 (2)	140
C11—H11···Cl2	0.93	2.82	3.687 (2)	155
C24—H24A···Cl4^vi	0.97	2.76	3.707 (3)	166

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