Diaqua-bis-(5-carb-oxy-2-propyl-1H-imidazole-4-carboxyl-ato-κN,O)zinc(II) 3.5-hydrate.

In the title complex, [Zn(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)]·3.5H(2)O, the Zn(II) ion is coordinated by two N,O-bidentate H(2)pimda ligands (H(3)pimda = 2-propyl-1H-imidazole-4,5-dicarb-oxy-lic acid) and two water mol-ecules in a distorted octa-hedral environment. In the crystal structure, extensive inter-molecular O-H⋯O and N-H⋯O hydrogen bonds stabilize the three-dimensional supra-molecular network. Intra-molecular O-H⋯O hydrogen bonds between the carboxyl groups are also observed. The propyl groups of the two H(2)pimda ligands are disordered each over two sites, with occupancy factors of 0.752 (5):0.248 (5) and 0.519 (7):0.481 (7). One of the water mol-ecules is half-occupied.

Related literature

For the potential uses and diverse structural types of metal complexes with imidazole-4,5-dicarb­oxy­lic acid, see: Li et al. (2006 ▶); Zou et al. (2006 ▶). For our previous structural studies of complexes derived from 2-propyl-1H-imidazole-4,5-dicarb­oxy­lic acid, see: Fan et al. (2010 ▶); He et al. (2010 ▶); Li et al. (2010 ▶); Song et al. (2010 ▶); Yan et al. (2010 ▶).

Experimental

Crystal data

[Zn(C8H9N2O4)2(H2O)2]·3.5H2O

M = 558.82

Triclinic,

a = 10.4780 (18) Å

b = 10.5729 (18) Å

c = 11.3012 (19) Å

α = 81.783 (2)°

β = 83.035 (2)°

γ = 86.852 (2)°

V = 1229.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.07 mm−1

T = 296 K

0.29 × 0.24 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.747, T max = 0.806

6393 measured reflections

4360 independent reflections

3172 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.160

S = 1.07

4360 reflections

342 parameters

24 restraints

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.72 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, 1R. DOI: 10.1107/S1600536810031478/hy2336sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031478/hy2336Isup2.hkl

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

[Zn(C8H9N2O4)2(H2O)2]·3.5H2O	Z = 2
Mr = 558.82	F(000) = 582
Triclinic, P1	Dx = 1.510 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4780 (18) Å	Cell parameters from 3600 reflections
b = 10.5729 (18) Å	θ = 1.4–28°
c = 11.3012 (19) Å	µ = 1.07 mm−1
α = 81.783 (2)°	T = 296 K
β = 83.035 (2)°	Block, colorless
γ = 86.852 (2)°	0.29 × 0.24 × 0.21 mm
V = 1229.1 (4) Å3

Bruker APEXII CCD diffractometer	4360 independent reflections
Radiation source: fine-focus sealed tube	3172 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scan	θmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→12
Tmin = 0.747, Tmax = 0.806	k = −11→12
6393 measured reflections	l = −11→13

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0755P)2 + 0.5831P] where P = (Fo2 + 2Fc2)/3
4360 reflections	(Δ/σ)max < 0.001
342 parameters	Δρmax = 0.81 e Å−3
24 restraints	Δρmin = −0.72 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.84596 (6)	0.28957 (6)	0.19279 (5)	0.0468 (3)
O1	0.8745 (5)	−0.1862 (4)	0.5169 (4)	0.0652 (12)
H1	0.8821	−0.1583	0.4450	0.098*
O2	0.8364 (4)	−0.1087 (4)	0.6884 (4)	0.0677 (12)
O3	0.8898 (4)	0.0899 (4)	0.1842 (3)	0.0505 (9)
O4	0.8972 (4)	−0.1006 (4)	0.2975 (3)	0.0604 (11)
O5	0.7797 (4)	0.4859 (3)	0.2071 (3)	0.0522 (10)
O6	0.6119 (4)	0.6225 (4)	0.1874 (4)	0.0647 (11)
O7	0.3908 (4)	0.6171 (4)	0.1402 (4)	0.0595 (11)
H7	0.4644	0.6156	0.1581	0.089*
O8	0.2581 (4)	0.4768 (4)	0.0987 (4)	0.0590 (11)
N1	0.8293 (4)	0.2124 (4)	0.3764 (4)	0.0432 (10)
N2	0.8107 (4)	0.1425 (4)	0.5690 (4)	0.0521 (12)
H2	0.7979	0.1424	0.6456	0.062*
N3	0.6451 (4)	0.2860 (4)	0.1716 (4)	0.0399 (10)
N4	0.4524 (4)	0.2803 (4)	0.1319 (4)	0.0466 (11)
H4	0.3826	0.2499	0.1168	0.056*
C1	0.8351 (5)	0.0371 (5)	0.5118 (4)	0.0412 (12)
C2	0.8473 (4)	0.0830 (5)	0.3922 (4)	0.0386 (11)
C3	0.8102 (6)	0.2472 (6)	0.4847 (5)	0.0561 (15)
C4	0.8810 (5)	0.0187 (5)	0.2833 (5)	0.0444 (13)
C5	0.8477 (5)	−0.0920 (6)	0.5795 (5)	0.0517 (14)
C6A	0.8065 (10)	0.3828 (11)	0.5113 (11)	0.070 (3)	0.753 (7)
H6A	0.8542	0.4358	0.4453	0.083*	0.753 (7)
H6B	0.8468	0.3860	0.5836	0.083*	0.753 (7)
C7A	0.6671 (10)	0.4347 (9)	0.5286 (9)	0.083 (3)	0.753 (7)
H7A	0.6233	0.4217	0.4607	0.100*	0.753 (7)
H7B	0.6222	0.3891	0.6010	0.100*	0.753 (7)
C8A	0.6658 (14)	0.5762 (10)	0.5390 (12)	0.129 (5)	0.753 (7)
H8A	0.5796	0.6054	0.5640	0.193*	0.753 (7)
H8B	0.6957	0.6228	0.4623	0.193*	0.753 (7)
H8C	0.7211	0.5900	0.5973	0.193*	0.753 (7)
C6B	0.742 (4)	0.367 (4)	0.522 (4)	0.070 (3)	0.247 (7)
H6C	0.6885	0.3479	0.5983	0.083*	0.247 (7)
H6D	0.6894	0.4072	0.4618	0.083*	0.247 (7)
C7B	0.852 (3)	0.453 (3)	0.535 (3)	0.083 (3)	0.247 (7)
H7C	0.9083	0.4631	0.4596	0.100*	0.247 (7)
H7D	0.8155	0.5368	0.5476	0.100*	0.247 (7)
C8B	0.933 (4)	0.405 (3)	0.636 (3)	0.129 (5)	0.247 (7)
H8D	0.9985	0.4647	0.6367	0.193*	0.247 (7)
H8E	0.9724	0.3233	0.6228	0.193*	0.247 (7)
H8F	0.8792	0.3969	0.7111	0.193*	0.247 (7)
C9	0.5881 (5)	0.4058 (5)	0.1698 (4)	0.0401 (12)
C10	0.4645 (5)	0.4030 (5)	0.1425 (4)	0.0408 (12)
C11	0.5583 (5)	0.2111 (5)	0.1471 (5)	0.0464 (13)
C12	0.6653 (5)	0.5103 (5)	0.1892 (5)	0.0470 (13)
C13	0.3619 (5)	0.5037 (6)	0.1269 (5)	0.0476 (14)
C14A	0.560 (3)	0.0677 (8)	0.1631 (19)	0.057 (4)	0.525 (10)
H14A	0.6447	0.0341	0.1364	0.069*	0.525 (10)
H14B	0.4986	0.0391	0.1157	0.069*	0.525 (10)
C15A	0.522 (2)	0.0179 (12)	0.3023 (15)	0.079 (4)	0.525 (10)
H15A	0.5775	0.0541	0.3504	0.095*	0.525 (10)
H15B	0.4337	0.0440	0.3269	0.095*	0.525 (10)
C16A	0.5373 (18)	−0.1247 (14)	0.3208 (18)	0.114 (6)	0.525 (10)
H16A	0.6111	−0.1500	0.3625	0.171*	0.525 (10)
H16B	0.5487	−0.1554	0.2441	0.171*	0.525 (10)
H16C	0.4618	−0.1602	0.3677	0.171*	0.525 (10)
C14B	0.590 (3)	0.0766 (10)	0.122 (2)	0.057 (4)	0.475 (10)
H14C	0.6787	0.0534	0.1332	0.069*	0.475 (10)
H14D	0.5784	0.0700	0.0387	0.069*	0.475 (10)
C15B	0.4966 (14)	−0.0173 (14)	0.2106 (15)	0.079 (4)	0.475 (10)
H15C	0.4078	0.0101	0.2028	0.095*	0.475 (10)
H15D	0.5095	−0.1032	0.1895	0.095*	0.475 (10)
C16B	0.523 (3)	−0.017 (2)	0.3369 (18)	0.114 (6)	0.475 (10)
H16D	0.4858	−0.0906	0.3866	0.171*	0.475 (10)
H16E	0.4861	0.0592	0.3656	0.171*	0.475 (10)
H16F	0.6143	−0.0210	0.3401	0.171*	0.475 (10)
O1W	0.8877 (4)	0.3308 (5)	0.0105 (4)	0.0795 (15)
H1W	0.9491	0.2983	−0.0309	0.119*
H2W	0.8511	0.3925	−0.0291	0.119*
O2W	1.0370 (4)	0.3313 (4)	0.2110 (4)	0.0789 (14)
H3W	1.0823	0.3900	0.1747	0.118*
H4W	1.0782	0.2755	0.2525	0.118*
O3W	0.9078 (8)	0.0156 (7)	0.9598 (7)	0.058 (2)	0.50
H5W	0.9780	−0.0146	0.9293	0.087*	0.50
H6W	0.9159	0.0441	1.0240	0.087*	0.50
O4W	0.7783 (6)	0.1691 (6)	0.8082 (4)	0.123 (2)
H7W	0.8323	0.1232	0.8463	0.185*
H8W	0.7604	0.2379	0.8361	0.185*
O5W	0.1009 (4)	0.2742 (4)	0.8694 (4)	0.0798 (14)
H9W	0.1112	0.3450	0.8245	0.120*
H10W	0.0969	0.2146	0.8273	0.120*
O6W	0.2574 (5)	0.1562 (6)	0.0392 (5)	0.111 (2)
H11W	0.2034	0.0991	0.0448	0.167*
H12W	0.2230	0.2297	0.0243	0.167*

	U11	U22	U33	U12	U13	U23
Zn1	0.0433 (4)	0.0509 (4)	0.0425 (4)	0.0042 (3)	−0.0065 (3)	0.0058 (3)
O1	0.080 (3)	0.051 (2)	0.060 (3)	0.000 (2)	−0.014 (2)	0.009 (2)
O2	0.067 (3)	0.081 (3)	0.044 (2)	0.009 (2)	−0.002 (2)	0.017 (2)
O3	0.056 (2)	0.058 (2)	0.034 (2)	0.0147 (18)	−0.0051 (16)	−0.0036 (17)
O4	0.083 (3)	0.049 (2)	0.050 (2)	0.011 (2)	−0.016 (2)	−0.0082 (19)
O5	0.049 (2)	0.049 (2)	0.060 (2)	−0.0048 (18)	−0.0141 (18)	−0.0019 (18)
O6	0.071 (3)	0.044 (2)	0.081 (3)	0.003 (2)	−0.016 (2)	−0.014 (2)
O7	0.049 (2)	0.054 (2)	0.074 (3)	0.0143 (19)	−0.010 (2)	−0.006 (2)
O8	0.040 (2)	0.065 (3)	0.066 (3)	0.0044 (19)	−0.0078 (19)	0.011 (2)
N1	0.044 (3)	0.046 (3)	0.038 (2)	0.002 (2)	−0.0067 (19)	−0.004 (2)
N2	0.057 (3)	0.063 (3)	0.035 (2)	0.007 (2)	−0.005 (2)	−0.006 (2)
N3	0.038 (2)	0.037 (2)	0.043 (2)	0.0037 (19)	−0.0076 (18)	0.0008 (18)
N4	0.040 (3)	0.049 (3)	0.049 (3)	−0.006 (2)	−0.008 (2)	0.003 (2)
C1	0.035 (3)	0.048 (3)	0.039 (3)	−0.003 (2)	−0.003 (2)	0.000 (2)
C2	0.033 (3)	0.043 (3)	0.039 (3)	−0.003 (2)	−0.008 (2)	−0.002 (2)
C3	0.071 (4)	0.052 (3)	0.046 (3)	0.009 (3)	−0.013 (3)	−0.007 (3)
C4	0.040 (3)	0.052 (3)	0.041 (3)	0.007 (2)	−0.011 (2)	−0.007 (3)
C5	0.041 (3)	0.062 (4)	0.048 (3)	0.001 (3)	−0.007 (3)	0.007 (3)
C6A	0.091 (10)	0.058 (6)	0.062 (5)	−0.003 (7)	−0.010 (7)	−0.015 (4)
C7A	0.100 (8)	0.062 (6)	0.086 (7)	0.005 (6)	0.000 (6)	−0.015 (5)
C8A	0.182 (14)	0.063 (6)	0.136 (11)	0.022 (7)	0.006 (10)	−0.023 (7)
C6B	0.091 (10)	0.058 (6)	0.062 (5)	−0.003 (7)	−0.010 (7)	−0.015 (4)
C7B	0.100 (8)	0.062 (6)	0.086 (7)	0.005 (6)	0.000 (6)	−0.015 (5)
C8B	0.182 (14)	0.063 (6)	0.136 (11)	0.022 (7)	0.006 (10)	−0.023 (7)
C9	0.043 (3)	0.039 (3)	0.034 (3)	0.002 (2)	−0.001 (2)	0.004 (2)
C10	0.042 (3)	0.040 (3)	0.037 (3)	−0.001 (2)	−0.005 (2)	0.004 (2)
C11	0.045 (3)	0.042 (3)	0.052 (3)	0.001 (3)	−0.014 (2)	0.001 (2)
C12	0.048 (3)	0.047 (3)	0.045 (3)	−0.002 (3)	−0.003 (2)	−0.005 (2)
C13	0.042 (3)	0.057 (4)	0.038 (3)	0.002 (3)	0.003 (2)	0.006 (3)
C14A	0.035 (12)	0.042 (4)	0.092 (13)	−0.007 (4)	−0.007 (9)	0.003 (5)
C15A	0.066 (7)	0.050 (6)	0.121 (11)	−0.004 (5)	−0.029 (7)	0.005 (7)
C16A	0.111 (11)	0.078 (9)	0.139 (13)	0.004 (10)	−0.010 (9)	0.023 (10)
C14B	0.035 (12)	0.042 (4)	0.092 (13)	−0.007 (4)	−0.007 (9)	0.003 (5)
C15B	0.066 (7)	0.050 (6)	0.121 (11)	−0.004 (5)	−0.029 (7)	0.005 (7)
C16B	0.111 (11)	0.078 (9)	0.139 (13)	0.004 (10)	−0.010 (9)	0.023 (10)
O1W	0.065 (3)	0.106 (4)	0.049 (2)	0.039 (3)	0.007 (2)	0.025 (2)
O2W	0.049 (3)	0.085 (3)	0.091 (3)	−0.013 (2)	−0.019 (2)	0.042 (3)
O3W	0.066 (5)	0.065 (5)	0.045 (4)	0.005 (4)	−0.007 (4)	−0.017 (4)
O4W	0.166 (6)	0.143 (5)	0.067 (3)	0.070 (5)	−0.032 (4)	−0.053 (3)
O5W	0.077 (3)	0.074 (3)	0.090 (3)	−0.022 (2)	0.016 (3)	−0.031 (3)
O6W	0.109 (5)	0.104 (4)	0.140 (5)	0.005 (3)	−0.061 (4)	−0.048 (4)

Zn1—O1W	2.042 (4)	C6B—H6D	0.9700
Zn1—N1	2.108 (4)	C7B—C8B	1.512 (17)
Zn1—O2W	2.113 (4)	C7B—H7C	0.9700
Zn1—O3	2.149 (4)	C7B—H7D	0.9700
Zn1—N3	2.149 (4)	C8B—H8D	0.9600
Zn1—O5	2.174 (4)	C8B—H8E	0.9600
O1—C5	1.301 (7)	C8B—H8F	0.9600
O1—H1	0.8200	C9—C10	1.370 (7)
O2—C5	1.210 (6)	C9—C12	1.460 (8)
O3—C4	1.253 (6)	C10—C13	1.479 (7)
O4—C4	1.254 (6)	C11—C14A	1.500 (10)
O5—C12	1.246 (6)	C11—C14B	1.502 (11)
O6—C12	1.282 (6)	C14A—C15A	1.594 (18)
O7—C13	1.286 (7)	C14A—H14A	0.9700
O7—H7	0.8200	C14A—H14B	0.9700
O8—C13	1.229 (7)	C15A—C16A	1.494 (15)
N1—C3	1.318 (7)	C15A—H15A	0.9700
N1—C2	1.360 (6)	C15A—H15B	0.9700
N2—C3	1.353 (7)	C16A—H16A	0.9600
N2—C1	1.363 (7)	C16A—H16B	0.9600
N2—H2	0.8600	C16A—H16C	0.9600
N3—C11	1.318 (7)	C14B—C15B	1.592 (18)
N3—C9	1.369 (6)	C14B—H14C	0.9700
N4—C11	1.311 (6)	C14B—H14D	0.9700
N4—C10	1.334 (7)	C15B—C16B	1.487 (17)
N4—H4	0.8600	C15B—H15C	0.9700
C1—C2	1.363 (7)	C15B—H15D	0.9700
C1—C5	1.474 (7)	C16B—H16D	0.9600
C2—C4	1.486 (7)	C16B—H16E	0.9600
C3—C6A	1.504 (13)	C16B—H16F	0.9600
C3—C6B	1.51 (4)	O1W—H1W	0.8363
C6A—C7A	1.531 (13)	O1W—H2W	0.8393
C6A—H6A	0.9700	O2W—H3W	0.8323
C6A—H6B	0.9700	O2W—H4W	0.8337
C7A—C8A	1.517 (13)	O3W—H5W	0.8402
C7A—H7A	0.9700	O3W—H6W	0.8405
C7A—H7B	0.9700	O4W—H7W	0.8420
C8A—H8A	0.9600	O4W—H8W	0.8374
C8A—H8B	0.9600	O5W—H9W	0.8466
C8A—H8C	0.9600	O5W—H10W	0.8485
C6B—C7B	1.539 (17)	O6W—H11W	0.8409
C6B—H6C	0.9700	O6W—H12W	0.8416
O1W—Zn1—N1	167.71 (16)	C6B—C7B—H7C	108.4
O1W—Zn1—O2W	88.74 (19)	C8B—C7B—H7D	108.4
N1—Zn1—O2W	87.04 (16)	C6B—C7B—H7D	108.4
O1W—Zn1—O3	90.84 (16)	H7C—C7B—H7D	107.5
N1—Zn1—O3	77.98 (14)	C7B—C8B—H8D	109.5
O2W—Zn1—O3	94.19 (17)	C7B—C8B—H8E	109.5
O1W—Zn1—N3	89.81 (17)	H8D—C8B—H8E	109.5
N1—Zn1—N3	96.47 (16)	C7B—C8B—H8F	109.5
O2W—Zn1—N3	169.05 (16)	H8D—C8B—H8F	109.5
O3—Zn1—N3	96.68 (15)	H8E—C8B—H8F	109.5
O1W—Zn1—O5	91.52 (16)	N3—C9—C10	109.4 (5)
N1—Zn1—O5	100.14 (15)	N3—C9—C12	118.4 (5)
O2W—Zn1—O5	91.72 (16)	C10—C9—C12	132.1 (5)
O3—Zn1—O5	173.69 (14)	N4—C10—C9	103.1 (4)
N3—Zn1—O5	77.47 (15)	N4—C10—C13	124.6 (5)
C5—O1—H1	109.5	C9—C10—C13	132.3 (5)
C4—O3—Zn1	115.7 (3)	N4—C11—N3	108.1 (5)
C12—O5—Zn1	114.6 (3)	N4—C11—C14A	121.7 (13)
C13—O7—H7	109.5	N3—C11—C14A	128.5 (14)
C3—N1—C2	106.5 (4)	N4—C11—C14B	128.3 (15)
C3—N1—Zn1	141.4 (4)	N3—C11—C14B	122.8 (15)
C2—N1—Zn1	112.0 (3)	O5—C12—O6	123.2 (5)
C3—N2—C1	108.5 (4)	O5—C12—C9	118.4 (5)
C3—N2—H2	125.8	O6—C12—C9	118.3 (5)
C1—N2—H2	125.8	O8—C13—O7	124.2 (5)
C11—N3—C9	106.7 (4)	O8—C13—C10	119.6 (5)
C11—N3—Zn1	142.0 (3)	O7—C13—C10	116.2 (5)
C9—N3—Zn1	110.9 (3)	C11—C14A—C15A	108.3 (10)
C11—N4—C10	112.7 (5)	C11—C14A—H14A	110.0
C11—N4—H4	123.6	C15A—C14A—H14A	110.0
C10—N4—H4	123.6	C11—C14A—H14B	110.0
N2—C1—C2	105.1 (4)	C15A—C14A—H14B	110.0
N2—C1—C5	121.5 (5)	H14A—C14A—H14B	108.4
C2—C1—C5	133.4 (5)	C16A—C15A—C14A	108.5 (13)
N1—C2—C1	110.1 (4)	C16A—C15A—H15A	110.0
N1—C2—C4	117.9 (4)	C14A—C15A—H15A	110.0
C1—C2—C4	131.9 (5)	C16A—C15A—H15B	110.0
N1—C3—N2	109.8 (5)	C14A—C15A—H15B	110.0
N1—C3—C6A	125.1 (7)	H15A—C15A—H15B	108.4
N2—C3—C6A	124.6 (7)	C11—C14B—C15B	108.7 (12)
N1—C3—C6B	128.2 (18)	C11—C14B—H14C	109.9
N2—C3—C6B	117.2 (18)	C15B—C14B—H14C	109.9
O3—C4—O4	125.6 (5)	C11—C14B—H14D	109.9
O3—C4—C2	116.3 (5)	C15B—C14B—H14D	109.9
O4—C4—C2	118.1 (5)	H14C—C14B—H14D	108.3
O2—C5—O1	121.8 (5)	C16B—C15B—C14B	110.1 (19)
O2—C5—C1	121.2 (6)	C16B—C15B—H15C	109.6
O1—C5—C1	117.0 (5)	C14B—C15B—H15C	109.6
C3—C6A—C7A	110.2 (9)	C16B—C15B—H15D	109.6
C3—C6A—H6A	109.6	C14B—C15B—H15D	109.6
C7A—C6A—H6A	109.6	H15C—C15B—H15D	108.1
C3—C6A—H6B	109.6	C15B—C16B—H16D	109.5
C7A—C6A—H6B	109.6	C15B—C16B—H16E	109.5
H6A—C6A—H6B	108.1	H16D—C16B—H16E	109.5
C8A—C7A—C6A	109.4 (10)	C15B—C16B—H16F	109.5
C8A—C7A—H7A	109.8	H16D—C16B—H16F	109.5
C6A—C7A—H7A	109.8	H16E—C16B—H16F	109.5
C8A—C7A—H7B	109.8	Zn1—O1W—H1W	125.4
C6A—C7A—H7B	109.8	Zn1—O1W—H2W	121.6
H7A—C7A—H7B	108.2	H1W—O1W—H2W	112.2
C3—C6B—C7B	104 (3)	Zn1—O2W—H3W	129.7
C3—C6B—H6C	110.9	Zn1—O2W—H4W	116.4
C7B—C6B—H6C	110.9	H3W—O2W—H4W	113.1
C3—C6B—H6D	110.9	H5W—O3W—H6W	111.6
C7B—C6B—H6D	110.9	H7W—O4W—H8W	111.8
H6C—C6B—H6D	109.0	H9W—O5W—H10W	110.3
C8B—C7B—C6B	115 (3)	H11W—O6W—H12W	111.4
C8B—C7B—H7C	108.4

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.82	1.68	2.502 (6)	180
O7—H7···O6	0.82	1.63	2.445 (6)	176
N2—H2···O4W	0.86	1.88	2.737 (6)	171
N4—H4···O6W	0.86	2.03	2.863 (6)	162
O1W—H1W···O5Wi	0.84	1.86	2.675 (6)	164
O1W—H2W···O8ii	0.84	1.89	2.720 (5)	170
O2W—H3W···O8iii	0.83	2.13	2.910 (6)	155
O2W—H4W···O2iv	0.83	2.00	2.802 (6)	161
O3W—H5W···O3iv	0.84	1.98	2.795 (8)	162
O3W—H6W···O3v	0.84	1.92	2.743 (8)	165
O4W—H7W···O3W	0.84	1.81	2.633 (9)	163
O4W—H8W···O7vi	0.84	2.16	2.877 (6)	143
O5W—H9W···O5vi	0.85	2.14	2.865 (6)	144
O5W—H10W···O4vii	0.85	1.98	2.812 (6)	169
O6W—H11W···O3Wvii	0.84	1.74	2.574 (10)	174
O6W—H12W···O5Wviii	0.84	2.27	2.789 (7)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	0.82	1.68	2.502 (6)	180
O7—H7⋯O6	0.82	1.63	2.445 (6)	176
N2—H2⋯O4W	0.86	1.88	2.737 (6)	171
N4—H4⋯O6W	0.86	2.03	2.863 (6)	162
O1W—H1W⋯O5Wi	0.84	1.86	2.675 (6)	164
O1W—H2W⋯O8ii	0.84	1.89	2.720 (5)	170
O2W—H3W⋯O8iii	0.83	2.13	2.910 (6)	155
O2W—H4W⋯O2iv	0.83	2.00	2.802 (6)	161
O3W—H5W⋯O3iv	0.84	1.98	2.795 (8)	162
O3W—H6W⋯O3v	0.84	1.92	2.743 (8)	165
O4W—H7W⋯O3W	0.84	1.81	2.633 (9)	163
O4W—H8W⋯O7vi	0.84	2.16	2.877 (6)	143
O5W—H9W⋯O5vi	0.85	2.14	2.865 (6)	144
O5W—H10W⋯O4vii	0.85	1.98	2.812 (6)	169
O6W—H11W⋯O3Wvii	0.84	1.74	2.574 (10)	174
O6W—H12W⋯O5Wviii	0.84	2.27	2.789 (7)	120

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .