Tetraaqua-tetrakis-{μ(2)-[1-(carb-oxylato-meth-yl)cyclo-hex-yl]methanaminium}bis(μ(3)-hydroxido)bis(nitrato-κO,O')tetrazinc(II).

As the title gabapentin complex, [Zn(4)(OH)(2)(NO(3))(2)(C(9)H(17)NO(2))(4)(H(2)O)(4)](NO(3))(4) is located about a centre of inversion, the asymmetric unit contains two disordered nitrate ions and half a complex mol-ecule. The two zinc ions have different coordination environments: one is slightly distorted octa-hedral and the other is trigonal-pyramidal. The conformation of the gabapentin mol-ecule is defined by the formation of two intra-molecular O-H⋯O hydrogen bonds. Furthermore, the ammonium H atoms are involved in numerous hydrogen bonds with the disordered nitrate anions.

Related literature

For related transition metal complexes with gabapentin, see: Braga et al. (2008 ▶). For structures with hexa- and tetra-coordinated zinc atoms, see: Clegg et al. (1991 ▶); Karmakar & Baruah (2008 ▶). For the structure of a gabapentin nitrate salt, see: de Vries et al. (2011 ▶).

Experimental

Crystal data

[Zn4(OH)2(NO3)2(C9H17NO2)4(H2O)4](NO3)4

M = 1424.64

Triclinic,

a = 10.0160 (2) Å

b = 11.3524 (2) Å

c = 14.2480 (2) Å

α = 88.740 (1)°

β = 74.021 (1)°

γ = 67.295 (1)°

V = 1430.28 (4) Å3

Z = 1

Mo Kα radiation

μ = 1.76 mm−1

T = 173 K

0.51 × 0.30 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.468, T max = 0.698

21157 measured reflections

6238 independent reflections

5401 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.128

S = 1.05

6238 reflections

363 parameters

6 restraints

H-atom parameters constrained

Δρmax = 1.54 e Å−3

Δρmin = −1.42 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-NT (Bruker, 2005 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) ▶; molecular graphics: X-SEED (Barbour, 2001 ▶; Atwood & Barbour, 2003 ▶); software used to prepare material for publication: X-SEED.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011020/ez2233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011020/ez2233Isup2.hkl

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

[Zn4(OH)2(NO3)2(C9H17NO2)4(H2O)4](NO3)4	Z = 1
Mr = 1424.64	F(000) = 740
Triclinic, P1	Dx = 1.654 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0160 (2) Å	Cell parameters from 9598 reflections
b = 11.3524 (2) Å	θ = 2.3–28.3°
c = 14.2480 (2) Å	µ = 1.76 mm−1
α = 88.740 (1)°	T = 173 K
β = 74.021 (1)°	Plate, colourless
γ = 67.295 (1)°	0.51 × 0.30 × 0.22 mm
V = 1430.28 (4) Å3

Bruker APEXII CCD diffractometer	6238 independent reflections
Radiation source: fine-focus sealed tube	5401 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.468, Tmax = 0.698	k = −14→14
21157 measured reflections	l = −18→18

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0613P)2 + 3.8991P] where P = (Fo2 + 2Fc2)/3
6238 reflections	(Δ/σ)max = 0.013
363 parameters	Δρmax = 1.54 e Å−3
6 restraints	Δρmin = −1.42 e Å−3

Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 2004)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	−0.08278 (4)	0.62842 (3)	0.46097 (3)	0.01972 (11)
O1	−0.0166 (3)	0.7519 (2)	0.3682 (2)	0.0336 (6)
N1	−0.2171 (4)	1.0031 (3)	0.3320 (3)	0.0435 (8)
H1D	−0.3130	1.0069	0.3452	0.065*
H1E	−0.2199	1.0839	0.3362	0.065*
H1C	−0.1728	0.9571	0.3763	0.065*
C1	0.0355 (4)	0.9276 (3)	0.2009 (3)	0.0281 (7)
Zn2	0.22789 (4)	0.47355 (4)	0.30465 (3)	0.02482 (12)
H6D	−0.3494	0.7287	0.5512	0.15 (4)*
H7C	−0.1625	0.8249	0.5891	0.058 (15)*
H7D	−0.0066	0.7513	0.5868	0.08 (2)*
H5C	0.1996	0.5382	0.4626	0.062 (16)*
H6C	−0.3895	0.8254	0.4791	0.13 (3)*
O2	0.2232 (3)	0.6464 (2)	0.2767 (2)	0.0358 (6)
N2	−0.4080 (3)	0.6146 (3)	0.3453 (2)	0.0302 (6)
H2C	−0.4994	0.6262	0.3879	0.045*
H2D	−0.4041	0.6923	0.3327	0.045*
H2E	−0.3333	0.5686	0.3722	0.045*
C2	0.0420 (5)	1.0591 (3)	0.1794 (3)	0.0394 (9)
H2A	−0.0225	1.0997	0.1364	0.047*
H2B	−0.0004	1.1148	0.2418	0.047*
O3	−0.1127 (3)	0.5294 (2)	0.34852 (18)	0.0287 (5)
C3	0.2008 (6)	1.0517 (4)	0.1306 (4)	0.0465 (11)
H3A	0.2631	1.0204	0.1762	0.056*
H3B	0.1962	1.1385	0.1156	0.056*
O4	0.1073 (3)	0.4364 (3)	0.23377 (19)	0.0341 (6)
C4	0.2743 (6)	0.9621 (4)	0.0362 (3)	0.0498 (11)
H4A	0.3799	0.9542	0.0083	0.060*
H4B	0.2189	0.9987	−0.0124	0.060*
O5	0.1376 (2)	0.5004 (2)	0.44675 (17)	0.0212 (4)
C5	0.2734 (5)	0.8296 (4)	0.0554 (3)	0.0411 (9)
H5A	0.3152	0.7751	−0.0076	0.049*
H5B	0.3391	0.7888	0.0976	0.049*
O6	−0.3136 (3)	0.7413 (2)	0.48426 (19)	0.0302 (5)
C6	0.1145 (5)	0.8373 (4)	0.1050 (3)	0.0334 (8)
H6A	0.1199	0.7502	0.1198	0.040*
H6B	0.0527	0.8677	0.0590	0.040*
O7	−0.0932 (3)	0.7376 (2)	0.5826 (2)	0.0321 (6)
C7	0.1148 (4)	0.8735 (3)	0.2808 (3)	0.0295 (7)
H7A	0.2222	0.8614	0.2559	0.035*
H7B	0.0671	0.9370	0.3391	0.035*
C8	0.1070 (4)	0.7472 (3)	0.3114 (3)	0.0278 (7)
C9	−0.1283 (4)	0.9397 (3)	0.2312 (3)	0.0353 (8)
H9A	−0.1791	0.9893	0.1840	0.042*
H9B	−0.1286	0.8529	0.2270	0.042*
C10	−0.2366 (4)	0.5177 (3)	0.1742 (2)	0.0237 (6)
C11	−0.2081 (4)	0.6402 (3)	0.1505 (3)	0.0290 (7)
H11A	−0.2157	0.6844	0.2121	0.035*
H11B	−0.1040	0.6161	0.1069	0.035*
C12	−0.3194 (5)	0.7331 (4)	0.1010 (3)	0.0396 (9)
H12A	−0.4226	0.7653	0.1473	0.048*
H12B	−0.2919	0.8075	0.0842	0.048*
C13	−0.3179 (5)	0.6677 (4)	0.0082 (3)	0.0435 (10)
H13A	−0.3944	0.7285	−0.0203	0.052*
H13B	−0.2175	0.6432	−0.0406	0.052*
C14	−0.3516 (5)	0.5490 (4)	0.0299 (3)	0.0389 (9)
H14A	−0.3427	0.5051	−0.0322	0.047*
H14B	−0.4568	0.5746	0.0724	0.047*
C15	−0.2431 (4)	0.4568 (4)	0.0807 (3)	0.0326 (8)
H15A	−0.1404	0.4218	0.0339	0.039*
H15B	−0.2736	0.3841	0.0982	0.039*
C16	−0.1039 (4)	0.4168 (3)	0.2054 (3)	0.0312 (8)
H16A	−0.1408	0.3548	0.2418	0.037*
H16B	−0.0240	0.3689	0.1451	0.037*
C17	−0.0319 (4)	0.4651 (3)	0.2677 (2)	0.0256 (7)
C18	−0.3875 (4)	0.5441 (4)	0.2524 (3)	0.0297 (7)
H18A	−0.4709	0.5941	0.2248	0.036*
H18B	−0.3957	0.4611	0.2675	0.036*
O1A	0.3312 (7)	0.6003 (6)	0.5027 (5)	0.0231 (14)*	0.487 (10)
O2A	0.1479 (8)	0.7922 (7)	0.5821 (6)	0.0357 (16)*	0.487 (10)
O3A	0.3675 (8)	0.7772 (7)	0.5194 (5)	0.053 (2)*	0.487 (10)
N3A	0.2773 (8)	0.7269 (8)	0.5350 (6)	0.0244 (17)*	0.487 (10)
O1D	0.3120 (7)	0.6272 (7)	0.4840 (5)	0.0316 (16)*	0.513 (10)
O2D	0.1653 (7)	0.7624 (6)	0.6064 (5)	0.0304 (14)*	0.513 (10)
O3D	0.3889 (8)	0.7207 (7)	0.5785 (6)	0.060 (2)*	0.513 (10)
N3D	0.2932 (8)	0.7002 (7)	0.5536 (6)	0.0251 (17)*	0.513 (10)
O1B	0.6378 (5)	0.2233 (5)	0.2221 (4)	0.0333 (13)*	0.537 (7)
O2B	0.4562 (6)	0.3503 (6)	0.1739 (4)	0.0597 (19)*	0.537 (7)
O3B	0.4324 (6)	0.3401 (6)	0.3257 (3)	0.0548 (19)*	0.537 (7)
N5B	0.5111 (8)	0.2971 (7)	0.2415 (5)	0.0284 (15)*	0.537 (7)
O1E	0.6232 (7)	0.1961 (7)	0.1990 (6)	0.0391 (17)*	0.463 (7)
O2E	0.4354 (7)	0.3790 (6)	0.2182 (5)	0.0358 (16)*	0.463 (7)
O3E	0.4128 (8)	0.2302 (7)	0.3050 (6)	0.052 (2)*	0.463 (7)
N5E	0.4917 (9)	0.2665 (9)	0.2375 (6)	0.0333 (19)*	0.463 (7)
O1C	0.5177 (11)	−0.1170 (9)	0.3201 (7)	0.072 (2)*	0.548 (7)
O2C	0.4870 (8)	−0.0027 (6)	0.4501 (5)	0.0575 (19)*	0.548 (7)
O3C	0.2965 (9)	0.0137 (9)	0.3980 (6)	0.072 (2)*	0.548 (7)
N4C	0.4311 (8)	−0.0360 (6)	0.3883 (6)	0.0334 (15)*	0.548 (7)
O1F	0.5650 (7)	−0.1201 (6)	0.3312 (5)	0.0359 (16)*	0.452 (7)
O2F	0.3302 (8)	−0.0551 (10)	0.4016 (8)	0.090*	0.452 (7)
O3F	0.4270 (10)	0.0782 (5)	0.3488 (8)	0.090*	0.452 (7)
N4F	0.4427 (11)	−0.0271 (10)	0.3500 (9)	0.048 (2)*	0.452 (7)

	U11	U22	U33	U12	U13	U23
Zn1	0.01629 (18)	0.01734 (18)	0.0228 (2)	−0.00489 (14)	−0.00405 (14)	0.00329 (13)
O1	0.0291 (13)	0.0243 (12)	0.0391 (15)	−0.0072 (10)	−0.0029 (11)	0.0110 (11)
N1	0.0398 (19)	0.0292 (17)	0.046 (2)	−0.0079 (15)	0.0030 (16)	−0.0007 (15)
C1	0.0355 (19)	0.0163 (15)	0.0281 (17)	−0.0071 (14)	−0.0070 (15)	0.0030 (13)
Zn2	0.01772 (19)	0.0238 (2)	0.0265 (2)	−0.00436 (15)	−0.00230 (15)	0.00454 (15)
O2	0.0307 (13)	0.0254 (13)	0.0400 (15)	−0.0058 (11)	−0.0013 (11)	0.0105 (11)
N2	0.0205 (14)	0.0341 (16)	0.0308 (16)	−0.0091 (12)	−0.0016 (12)	−0.0033 (12)
C2	0.053 (2)	0.0182 (16)	0.036 (2)	−0.0098 (16)	−0.0021 (18)	0.0067 (14)
O3	0.0200 (11)	0.0299 (13)	0.0305 (13)	−0.0043 (10)	−0.0061 (10)	−0.0058 (10)
C3	0.060 (3)	0.0240 (19)	0.051 (3)	−0.0201 (19)	−0.003 (2)	0.0099 (17)
O4	0.0217 (12)	0.0445 (15)	0.0274 (13)	−0.0060 (11)	−0.0035 (10)	−0.0036 (11)
C4	0.055 (3)	0.043 (2)	0.039 (2)	−0.018 (2)	0.002 (2)	0.0120 (19)
O5	0.0187 (10)	0.0199 (10)	0.0265 (12)	−0.0089 (9)	−0.0071 (9)	0.0052 (9)
C5	0.046 (2)	0.033 (2)	0.032 (2)	−0.0099 (18)	0.0000 (17)	−0.0019 (16)
O6	0.0212 (12)	0.0278 (13)	0.0323 (14)	−0.0002 (10)	−0.0071 (10)	−0.0027 (10)
C6	0.040 (2)	0.0271 (17)	0.0289 (18)	−0.0081 (15)	−0.0104 (16)	−0.0003 (14)
O7	0.0291 (13)	0.0258 (12)	0.0380 (14)	−0.0072 (10)	−0.0093 (11)	−0.0040 (10)
C7	0.0379 (19)	0.0247 (16)	0.0286 (18)	−0.0152 (15)	−0.0099 (15)	0.0066 (13)
C8	0.0304 (18)	0.0249 (16)	0.0272 (17)	−0.0104 (14)	−0.0080 (14)	0.0087 (13)
C9	0.0336 (19)	0.0225 (17)	0.042 (2)	−0.0030 (15)	−0.0105 (17)	0.0019 (15)
C10	0.0219 (15)	0.0231 (15)	0.0271 (16)	−0.0104 (13)	−0.0058 (13)	−0.0022 (12)
C11	0.0295 (17)	0.0307 (18)	0.0304 (18)	−0.0179 (15)	−0.0054 (14)	0.0019 (14)
C12	0.051 (2)	0.033 (2)	0.040 (2)	−0.0197 (18)	−0.0175 (19)	0.0102 (16)
C13	0.051 (3)	0.050 (2)	0.032 (2)	−0.022 (2)	−0.0153 (19)	0.0107 (18)
C14	0.041 (2)	0.049 (2)	0.034 (2)	−0.0224 (19)	−0.0156 (17)	0.0004 (17)
C15	0.0343 (19)	0.0344 (19)	0.0306 (18)	−0.0160 (16)	−0.0073 (15)	−0.0064 (15)
C16	0.0285 (18)	0.0251 (17)	0.0325 (19)	−0.0025 (14)	−0.0084 (15)	−0.0083 (14)
C17	0.0217 (16)	0.0234 (16)	0.0250 (16)	−0.0023 (13)	−0.0060 (13)	0.0014 (13)
C18	0.0262 (17)	0.0346 (18)	0.0312 (18)	−0.0165 (15)	−0.0056 (14)	−0.0015 (14)

Zn1—O1	2.075 (2)	O7—H7C	0.9540
Zn1—O5i	2.075 (2)	O7—H7D	0.9559
Zn1—O5	2.077 (2)	C7—C8	1.513 (5)
Zn1—O6	2.099 (2)	C7—H7A	0.9900
Zn1—O7	2.109 (3)	C7—H7B	0.9900
Zn1—O3	2.127 (2)	C9—H9A	0.9900
Zn1—Zn1i	3.1029 (7)	C9—H9B	0.9900
Zn1—Zn2	3.1412 (5)	C10—C18	1.534 (5)
O1—C8	1.262 (4)	C10—C11	1.537 (5)
N1—C9	1.490 (5)	C10—C15	1.542 (5)
N1—H1D	0.9100	C10—C16	1.550 (5)
N1—H1E	0.9100	C11—C12	1.531 (5)
N1—H1C	0.9100	C11—H11A	0.9900
C1—C9	1.528 (5)	C11—H11B	0.9900
C1—C2	1.540 (5)	C12—C13	1.525 (6)
C1—C6	1.544 (5)	C12—H12A	0.9900
C1—C7	1.548 (5)	C12—H12B	0.9900
Zn2—O4	1.933 (3)	C13—C14	1.516 (6)
Zn2—O5	1.954 (2)	C13—H13A	0.9900
Zn2—O2	1.979 (3)	C13—H13B	0.9900
Zn2—O2E	1.979 (7)	C14—C15	1.524 (6)
Zn2—O3B	2.122 (5)	C14—H14A	0.9900
Zn2—O2B	2.440 (6)	C14—H14B	0.9900
O2—C8	1.260 (4)	C15—H15A	0.9900
N2—C18	1.485 (4)	C15—H15B	0.9900
N2—H2C	0.9100	C16—C17	1.513 (5)
N2—H2D	0.9100	C16—H16A	0.9900
N2—H2E	0.9100	C16—H16B	0.9900
C2—C3	1.520 (6)	C18—H18A	0.9900
C2—H2A	0.9900	C18—H18B	0.9900
C2—H2B	0.9900	O1A—N3A	1.365 (10)
O3—C17	1.258 (4)	O2A—N3A	1.217 (10)
C3—C4	1.524 (6)	O3A—N3A	1.214 (10)
C3—H3A	0.9900	O1D—N3D	1.233 (9)
C3—H3B	0.9900	O2D—N3D	1.224 (9)
O4—C17	1.253 (4)	O3D—N3D	1.210 (10)
C4—C5	1.526 (6)	O1B—N5B	1.177 (7)
C4—H4A	0.9900	O2B—N5B	1.266 (7)
C4—H4B	0.9900	O3B—N5B	1.228 (7)
O5—Zn1i	2.075 (2)	O1E—N5E	1.218 (10)
O5—H5C	0.9537	O2E—N5E	1.240 (11)
C5—C6	1.522 (6)	O3E—N5E	1.239 (11)
C5—H5A	0.9900	O1C—N4C	1.225 (11)
C5—H5B	0.9900	O2C—N4C	1.297 (9)
O6—H6D	0.9503	O3C—N4C	1.212 (10)
O6—H6C	0.9812	O1F—N4F	1.233 (12)
C6—H6A	0.9900	O2F—N4F	1.312 (12)
C6—H6B	0.9900	O3F—N4F	1.144 (12)
O1—Zn1—O5i	177.11 (9)	H5A—C5—H5B	108.0
O1—Zn1—O5	93.85 (9)	Zn1—O6—H6D	98.6
O5i—Zn1—O5	83.28 (9)	Zn1—O6—H6C	146.2
O1—Zn1—O6	92.92 (10)	H6D—O6—H6C	102.2
O5i—Zn1—O6	89.95 (10)	C5—C6—C1	113.2 (3)
O5—Zn1—O6	173.15 (10)	C5—C6—H6A	108.9
O1—Zn1—O7	89.88 (11)	C1—C6—H6A	108.9
O5i—Zn1—O7	89.98 (10)	C5—C6—H6B	108.9
O5—Zn1—O7	93.55 (9)	C1—C6—H6B	108.9
O6—Zn1—O7	87.50 (10)	H6A—C6—H6B	107.8
O1—Zn1—O3	93.96 (11)	Zn1—O7—H7C	113.3
O5i—Zn1—O3	86.62 (10)	Zn1—O7—H7D	120.8
O5—Zn1—O3	95.10 (9)	H7C—O7—H7D	98.9
O6—Zn1—O3	83.38 (9)	C8—C7—C1	113.2 (3)
O7—Zn1—O3	170.27 (10)	C8—C7—H7A	108.9
O1—Zn1—Zn1i	135.46 (7)	C1—C7—H7A	108.9
O5i—Zn1—Zn1i	41.67 (6)	C8—C7—H7B	108.9
O5—Zn1—Zn1i	41.61 (6)	C1—C7—H7B	108.9
O6—Zn1—Zn1i	131.61 (8)	H7A—C7—H7B	107.8
O7—Zn1—Zn1i	92.37 (7)	O2—C8—O1	125.5 (3)
O3—Zn1—Zn1i	91.15 (7)	O2—C8—C7	117.5 (3)
O1—Zn1—Zn2	70.09 (7)	O1—C8—C7	117.0 (3)
O5i—Zn1—Zn2	107.55 (6)	N1—C9—C1	114.2 (3)
O5—Zn1—Zn2	37.41 (6)	N1—C9—H9A	108.7
O6—Zn1—Zn2	145.77 (7)	C1—C9—H9A	108.7
O7—Zn1—Zn2	120.73 (7)	N1—C9—H9B	108.7
O3—Zn1—Zn2	69.00 (6)	C1—C9—H9B	108.7
Zn1i—Zn1—Zn2	70.725 (14)	H9A—C9—H9B	107.6
C8—O1—Zn1	135.0 (2)	C18—C10—C11	112.7 (3)
C9—N1—H1D	109.5	C18—C10—C15	106.9 (3)
C9—N1—H1E	109.5	C11—C10—C15	109.1 (3)
H1D—N1—H1E	109.5	C18—C10—C16	110.6 (3)
C9—N1—H1C	109.5	C11—C10—C16	110.7 (3)
H1D—N1—H1C	109.5	C15—C10—C16	106.5 (3)
H1E—N1—H1C	109.5	C12—C11—C10	113.1 (3)
C9—C1—C2	110.3 (3)	C12—C11—H11A	109.0
C9—C1—C6	105.8 (3)	C10—C11—H11A	109.0
C2—C1—C6	108.6 (3)	C12—C11—H11B	109.0
C9—C1—C7	112.0 (3)	C10—C11—H11B	109.0
C2—C1—C7	109.0 (3)	H11A—C11—H11B	107.8
C6—C1—C7	111.0 (3)	C13—C12—C11	111.1 (3)
O4—Zn2—O5	113.77 (10)	C13—C12—H12A	109.4
O4—Zn2—O2	107.78 (12)	C11—C12—H12A	109.4
O5—Zn2—O2	100.42 (10)	C13—C12—H12B	109.4
O4—Zn2—O2E	101.9 (2)	C11—C12—H12B	109.4
O5—Zn2—O2E	133.7 (2)	H12A—C12—H12B	108.0
O2—Zn2—O2E	95.5 (2)	C14—C13—C12	111.1 (3)
O4—Zn2—O3B	125.86 (18)	C14—C13—H13A	109.4
O5—Zn2—O3B	89.12 (13)	C12—C13—H13A	109.4
O2—Zn2—O3B	115.6 (2)	C14—C13—H13B	109.4
O2E—Zn2—O3B	45.1 (2)	C12—C13—H13B	109.4
O4—Zn2—O2B	89.76 (16)	H13A—C13—H13B	108.0
O5—Zn2—O2B	143.75 (11)	C13—C14—C15	111.2 (3)
O2—Zn2—O2B	97.72 (18)	C13—C14—H14A	109.4
O2E—Zn2—O2B	12.2 (2)	C15—C14—H14A	109.4
O3B—Zn2—O2B	54.68 (10)	C13—C14—H14B	109.4
O4—Zn2—Zn1	85.10 (7)	C15—C14—H14B	109.4
O5—Zn2—Zn1	40.23 (6)	H14A—C14—H14B	108.0
O2—Zn2—Zn1	83.40 (8)	C14—C15—C10	114.3 (3)
O2E—Zn2—Zn1	172.9 (2)	C14—C15—H15A	108.7
O3B—Zn2—Zn1	129.32 (11)	C10—C15—H15A	108.7
O2B—Zn2—Zn1	174.83 (13)	C14—C15—H15B	108.7
C8—O2—Zn2	122.3 (2)	C10—C15—H15B	108.7
C18—N2—H2C	109.5	H15A—C15—H15B	107.6
C18—N2—H2D	109.5	C17—C16—C10	117.5 (3)
H2C—N2—H2D	109.5	C17—C16—H16A	107.9
C18—N2—H2E	109.5	C10—C16—H16A	107.9
H2C—N2—H2E	109.5	C17—C16—H16B	107.9
H2D—N2—H2E	109.5	C10—C16—H16B	107.9
C3—C2—C1	113.6 (3)	H16A—C16—H16B	107.2
C3—C2—H2A	108.8	O4—C17—O3	124.6 (3)
C1—C2—H2A	108.8	O4—C17—C16	116.2 (3)
C3—C2—H2B	108.8	O3—C17—C16	119.2 (3)
C1—C2—H2B	108.8	N2—C18—C10	114.6 (3)
H2A—C2—H2B	107.7	N2—C18—H18A	108.6
C17—O3—Zn1	136.7 (2)	C10—C18—H18A	108.6
C2—C3—C4	111.1 (4)	N2—C18—H18B	108.6
C2—C3—H3A	109.4	C10—C18—H18B	108.6
C4—C3—H3A	109.4	H18A—C18—H18B	107.6
C2—C3—H3B	109.4	O3A—N3A—O2A	117.1 (8)
C4—C3—H3B	109.4	O3A—N3A—O1A	117.3 (7)
H3A—C3—H3B	108.0	O2A—N3A—O1A	125.5 (7)
C17—O4—Zn2	123.8 (2)	O3D—N3D—O2D	112.5 (7)
C3—C4—C5	110.9 (3)	O3D—N3D—O1D	127.6 (7)
C3—C4—H4A	109.5	O2D—N3D—O1D	119.9 (7)
C5—C4—H4A	109.5	N5B—O2B—Zn2	86.3 (4)
C3—C4—H4B	109.5	N5B—O3B—Zn2	102.7 (4)
C5—C4—H4B	109.5	O1B—N5B—O3B	123.3 (6)
H4A—C4—H4B	108.1	O1B—N5B—O2B	120.0 (6)
Zn2—O5—Zn1i	127.54 (11)	O3B—N5B—O2B	115.9 (6)
Zn2—O5—Zn1	102.36 (10)	N5E—O2E—Zn2	112.5 (6)
Zn1i—O5—Zn1	96.72 (9)	O1E—N5E—O2E	122.7 (9)
Zn2—O5—H5C	98.0	O1E—N5E—O3E	119.7 (8)
Zn1i—O5—H5C	117.7	O2E—N5E—O3E	117.3 (8)
Zn1—O5—H5C	114.2	O3C—N4C—O1C	121.6 (9)
C6—C5—C4	111.6 (4)	O3C—N4C—O2C	120.0 (8)
C6—C5—H5A	109.3	O1C—N4C—O2C	118.4 (8)
C4—C5—H5A	109.3	O3F—N4F—O1F	125.7 (10)
C6—C5—H5B	109.3	O3F—N4F—O2F	118.7 (10)
C4—C5—H5B	109.3	O1F—N4F—O2F	112.4 (9)
O5—Zn1—O1—C8	9.3 (4)	O7—Zn1—O5—Zn2	−139.60 (11)
O6—Zn1—O1—C8	−169.7 (4)	O3—Zn1—O5—Zn2	44.86 (11)
O7—Zn1—O1—C8	102.8 (4)	Zn1i—Zn1—O5—Zn2	130.84 (13)
O3—Zn1—O1—C8	−86.1 (4)	O1—Zn1—O5—Zn1i	179.69 (10)
Zn1i—Zn1—O1—C8	9.6 (4)	O5i—Zn1—O5—Zn1i	0.0
Zn2—Zn1—O1—C8	−20.1 (3)	O7—Zn1—O5—Zn1i	89.57 (10)
O1—Zn1—Zn2—O4	−97.08 (12)	O3—Zn1—O5—Zn1i	−85.98 (10)
O5i—Zn1—Zn2—O4	84.68 (11)	Zn2—Zn1—O5—Zn1i	−130.84 (13)
O5—Zn1—Zn2—O4	136.68 (13)	C3—C4—C5—C6	55.1 (5)
O6—Zn1—Zn2—O4	−32.92 (16)	C4—C5—C6—C1	−55.2 (5)
O7—Zn1—Zn2—O4	−174.51 (12)	C9—C1—C6—C5	171.4 (3)
O3—Zn1—Zn2—O4	5.49 (11)	C2—C1—C6—C5	52.9 (4)
Zn1i—Zn1—Zn2—O4	104.53 (9)	C7—C1—C6—C5	−66.9 (4)
O1—Zn1—Zn2—O5	126.23 (13)	C9—C1—C7—C8	54.5 (4)
O5i—Zn1—Zn2—O5	−52.01 (14)	C2—C1—C7—C8	176.8 (3)
O6—Zn1—Zn2—O5	−169.60 (16)	C6—C1—C7—C8	−63.5 (4)
O7—Zn1—Zn2—O5	48.81 (13)	Zn2—O2—C8—O1	1.5 (5)
O3—Zn1—Zn2—O5	−131.19 (12)	Zn2—O2—C8—C7	−177.1 (2)
Zn1i—Zn1—Zn2—O5	−32.16 (10)	Zn1—O1—C8—O2	19.9 (6)
O1—Zn1—Zn2—O2	11.49 (12)	Zn1—O1—C8—C7	−161.4 (3)
O5i—Zn1—Zn2—O2	−166.75 (11)	C1—C7—C8—O2	101.5 (4)
O5—Zn1—Zn2—O2	−114.75 (13)	C1—C7—C8—O1	−77.2 (4)
O6—Zn1—Zn2—O2	75.65 (16)	C2—C1—C9—N1	−73.7 (4)
O7—Zn1—Zn2—O2	−65.94 (12)	C6—C1—C9—N1	169.0 (3)
O3—Zn1—Zn2—O2	114.06 (12)	C7—C1—C9—N1	47.9 (4)
Zn1i—Zn1—Zn2—O2	−146.91 (9)	C18—C10—C11—C12	−66.4 (4)
O1—Zn1—Zn2—O3B	129.3 (2)	C15—C10—C11—C12	52.2 (4)
O5i—Zn1—Zn2—O3B	−48.9 (2)	C16—C10—C11—C12	169.1 (3)
O5—Zn1—Zn2—O3B	3.1 (2)	C10—C11—C12—C13	−55.9 (4)
O6—Zn1—Zn2—O3B	−166.5 (3)	C11—C12—C13—C14	56.2 (5)
O7—Zn1—Zn2—O3B	51.9 (2)	C12—C13—C14—C15	−55.0 (5)
O3—Zn1—Zn2—O3B	−128.1 (2)	C13—C14—C15—C10	54.1 (5)
Zn1i—Zn1—Zn2—O3B	−29.1 (2)	C18—C10—C15—C14	70.5 (4)
O4—Zn2—O2—C8	72.0 (3)	C11—C10—C15—C14	−51.7 (4)
O5—Zn2—O2—C8	−47.3 (3)	C16—C10—C15—C14	−171.2 (3)
O2E—Zn2—O2—C8	176.3 (3)	C18—C10—C16—C17	−87.8 (4)
O3B—Zn2—O2—C8	−141.4 (3)	C11—C10—C16—C17	37.9 (4)
O2B—Zn2—O2—C8	164.2 (3)	C15—C10—C16—C17	156.4 (3)
Zn1—Zn2—O2—C8	−10.7 (3)	Zn2—O4—C17—O3	5.5 (5)
C9—C1—C2—C3	−169.1 (4)	Zn2—O4—C17—C16	−174.2 (2)
C6—C1—C2—C3	−53.6 (5)	Zn1—O3—C17—O4	4.3 (6)
C7—C1—C2—C3	67.5 (4)	Zn1—O3—C17—C16	−176.0 (2)
O1—Zn1—O3—C17	59.8 (3)	C10—C16—C17—O4	−122.7 (4)
O5i—Zn1—O3—C17	−117.4 (3)	C10—C16—C17—O3	57.6 (5)
O5—Zn1—O3—C17	−34.5 (3)	C11—C10—C18—N2	−54.5 (4)
O6—Zn1—O3—C17	152.2 (3)	C15—C10—C18—N2	−174.4 (3)
Zn1i—Zn1—O3—C17	−76.0 (3)	C16—C10—C18—N2	70.0 (4)
Zn2—Zn1—O3—C17	−7.2 (3)	O4—Zn2—O2B—N5B	−132.7 (5)
C1—C2—C3—C4	56.0 (5)	O5—Zn2—O2B—N5B	−0.2 (7)
O5—Zn2—O4—C17	21.5 (3)	O2—Zn2—O2B—N5B	119.4 (5)
O2—Zn2—O4—C17	−88.9 (3)	O2E—Zn2—O2B—N5B	39.1 (11)
O2E—Zn2—O4—C17	171.3 (3)	O3B—Zn2—O2B—N5B	3.5 (5)
O3B—Zn2—O4—C17	128.8 (3)	O4—Zn2—O3B—N5B	55.1 (6)
O2B—Zn2—O4—C17	173.0 (3)	O5—Zn2—O3B—N5B	174.2 (5)
Zn1—Zn2—O4—C17	−7.5 (3)	O2—Zn2—O3B—N5B	−84.6 (5)
C2—C3—C4—C5	−55.2 (5)	O2E—Zn2—O3B—N5B	−13.7 (5)
O4—Zn2—O5—Zn1i	60.31 (17)	O2B—Zn2—O3B—N5B	−3.6 (5)
O2—Zn2—O5—Zn1i	175.16 (14)	Zn1—Zn2—O3B—N5B	172.2 (4)
O2E—Zn2—O5—Zn1i	−76.7 (3)	Zn2—O3B—N5B—O1B	176.3 (7)
O3B—Zn2—O5—Zn1i	−69.0 (2)	Zn2—O3B—N5B—O2B	6.4 (9)
O2B—Zn2—O5—Zn1i	−66.0 (4)	Zn2—O2B—N5B—O1B	−175.7 (8)
Zn1—Zn2—O5—Zn1i	108.63 (16)	Zn2—O2B—N5B—O3B	−5.4 (8)
O4—Zn2—O5—Zn1	−48.32 (13)	O4—Zn2—O2E—N5E	−88.7 (7)
O2—Zn2—O5—Zn1	66.53 (12)	O5—Zn2—O2E—N5E	51.7 (7)
O2E—Zn2—O5—Zn1	174.6 (3)	O2—Zn2—O2E—N5E	161.8 (7)
O3B—Zn2—O5—Zn1	−177.62 (19)	O3B—Zn2—O2E—N5E	40.8 (6)
O2B—Zn2—O5—Zn1	−174.7 (3)	O2B—Zn2—O2E—N5E	−97.1 (14)
O1—Zn1—O5—Zn2	−49.48 (12)	Zn2—O2E—N5E—O1E	−172.9 (7)
O5i—Zn1—O5—Zn2	130.84 (13)	Zn2—O2E—N5E—O3E	0.5 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1	0.91	2.23	2.918 (4)	132
N1—H1D···O2Cii	0.91	2.18	3.003 (9)	149
N1—H1E···O1Bii	0.91	2.57	3.015 (6)	111
N1—H1E···O2Diii	0.91	2.25	3.090 (8)	153
N1—H1E···O3Diii	0.91	2.31	3.037 (8)	136
N2—H2C···O1Div	0.91	2.00	2.906 (8)	172
N2—H2D···O1Cii	0.91	2.02	2.884 (9)	158
N2—H2E···O3	0.91	2.01	2.748 (5)	138
O5—H5C···O1D	0.95	1.86	2.809 (8)	173
O6—H6C···O2Cii	0.98	1.97	2.944 (7)	170
O6—H6C···O2Ci	0.98	2.01	2.819 (7)	138
O6—H6D···O3Div	0.95	2.58	3.010 (9)	108
O6—H6D···O3Bi	0.95	2.00	2.927 (5)	163
O7—H7C···O3Ci	0.95	1.78	2.735 (9)	178
O7—H7D···O2D	0.96	1.87	2.819 (8)	173

Table 1

Selected bond lengths (Å)

Zn1—O1	2.075 (2)
Zn1—O5i	2.075 (2)
Zn1—O5	2.077 (2)
Zn1—O6	2.099 (2)
Zn1—O7	2.109 (3)
Zn1—O3	2.127 (2)
Zn2—O4	1.933 (3)
Zn2—O5	1.954 (2)
Zn2—O2	1.979 (3)
Zn2—O2E	1.979 (7)
Zn2—O3B	2.122 (5)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O1	0.91	2.23	2.918 (4)	132
N1—H1D⋯O2Cii	0.91	2.18	3.003 (9)	149
N1—H1E⋯O1Bii	0.91	2.57	3.015 (6)	111
N1—H1E⋯O2Diii	0.91	2.25	3.090 (8)	153
N1—H1E⋯O3Diii	0.91	2.31	3.037 (8)	136
N2—H2C⋯O1Div	0.91	2.00	2.906 (8)	172
N2—H2D⋯O1Cii	0.91	2.02	2.884 (9)	158
N2—H2E⋯O3	0.91	2.01	2.748 (5)	138
O5—H5C⋯O1D	0.95	1.86	2.809 (8)	173
O6—H6C⋯O2Cii	0.98	1.97	2.944 (7)	170
O6—H6C⋯O2Ci	0.98	2.01	2.819 (7)	138
O6—H6D⋯O3Div	0.95	2.58	3.010 (9)	108
O6—H6D⋯O3Bi	0.95	2.00	2.927 (5)	163
O7—H7C⋯O3Ci	0.95	1.78	2.735 (9)	178
O7—H7D⋯O2D	0.96	1.87	2.819 (8)	173

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