Tetra-kis[μ-4-(diethyl-amino)benzoato-κO:O']bis-[(N,N-diethyl-nicotinamide-κN)zinc(II)].

In the centrosymmetric binuclear title complex, [Zn(2)(C(11)H(14)NO(2))(4)(C(10)H(14)N(2)O)(2)], the two Zn(II) ions [Zn⋯Zn = 2.8874 (3) Å] are bridged by four 4-(diethyl-amino)benzoate (DEAB) ligands. The four nearest O atoms around each Zn(II) ion form a distorted square-planar arrangement, the distorted square-pyramidal coordination being completed by the pyridine N atom of an N,N-diethyl-nicotinamide (DENA) ligand at a distance of 2.0484 (12) Å. The dihedral angle between the benzene ring and the carboxyl-ate group is 4.89 (6)° in one of the independent DEAB ligands and 7.13 (7)° in the other. The benzene rings of the two independent DEAB ligands are oriented at a dihedral angle of 86.58 (5)°. The pyridine ring is oriented at dihedral angles of 31.17 (4) and 58.38 (4)° with respect to the two benzene rings. In the crystal, weak inter-molecular C-H⋯O inter-actions link the mol-ecules into a three-dimensional network. Two weak C-H⋯π inter-actions are also present. The two ethyl groups of one of the DEAB ligands are disordered over two orientations, with occupancy ratios of 0.798 (5):0.202 (5) and 0.890 (5):0.110 (5).

Related literature

For general background to transition metal complexes of nicotinamide, one form of niacin, and/or the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶); Krishnamachari (1974 ▶). For related structures, see: Hökelek et al. (1995 ▶); Speier & Fulop (1989 ▶); Usubaliev et al. (1980 ▶).

Experimental

Crystal data

[Zn2(C11H14NO2)4(C10H14N2O)2]

M = 1256.13

Monoclinic,

a = 10.3758 (2) Å

b = 13.4107 (2) Å

c = 22.4458 (3) Å

β = 93.837 (3)°

V = 3116.26 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.83 mm−1

T = 100 K

0.54 × 0.31 × 0.27 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.778, T max = 0.798

28538 measured reflections

7635 independent reflections

6141 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.077

S = 1.04

7635 reflections

417 parameters

30 restraints

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.50 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027986/ci2853sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027986/ci2853Isup2.hkl

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

[Zn2(C11H14NO2)4(C10H14N2O)2]	F(000) = 1328
Mr = 1256.13	Dx = 1.339 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9966 reflections
a = 10.3758 (2) Å	θ = 2.4–28.2°
b = 13.4107 (2) Å	µ = 0.83 mm−1
c = 22.4458 (3) Å	T = 100 K
β = 93.837 (3)°	Block, colourless
V = 3116.26 (9) Å3	0.54 × 0.31 × 0.27 mm
Z = 2

Bruker Kappa APEXII CCD area-detector diffractometer	7635 independent reflections
Radiation source: fine-focus sealed tube	6141 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.778, Tmax = 0.798	k = −17→14
28538 measured reflections	l = −29→29

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0361P)2 + 1.1231P] where P = (Fo2 + 2Fc2)/3
7635 reflections	(Δ/σ)max = 0.001
417 parameters	Δρmax = 0.34 e Å−3
30 restraints	Δρmin = −0.50 e Å−3

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	0.590282 (14)	−0.001300 (11)	0.051808 (7)	0.01207 (5)
O1	0.71173 (9)	0.04299 (8)	−0.01063 (5)	0.0211 (2)
O2	0.62210 (10)	−0.14522 (8)	0.02975 (5)	0.0224 (2)
O3	0.51994 (10)	0.14132 (8)	0.04988 (5)	0.0224 (2)
O4	0.42848 (9)	−0.04493 (9)	0.09108 (5)	0.0233 (2)
O5	0.89856 (10)	0.27621 (8)	0.22536 (5)	0.0239 (2)
N1	0.70525 (11)	0.01702 (9)	0.12883 (5)	0.0141 (2)
N2	1.04716 (11)	0.21838 (9)	0.16475 (5)	0.0165 (3)
N3	1.07197 (11)	0.22316 (9)	−0.20302 (5)	0.0168 (3)
N4	0.69189 (18)	−0.58476 (12)	−0.07155 (8)	0.0523 (5)
C1	0.68215 (13)	0.05780 (11)	−0.06557 (7)	0.0171 (3)
C2	0.78619 (13)	0.09438 (10)	−0.10265 (6)	0.0153 (3)
C3	0.90883 (13)	0.11536 (11)	−0.07684 (6)	0.0167 (3)
H3A	0.9277	0.1008	−0.0358	0.020*
C4	1.00401 (13)	0.15681 (11)	−0.10930 (6)	0.0163 (3)
H4A	1.0862	0.1713	−0.0901	0.020*
C5	0.98026 (13)	0.17780 (11)	−0.17073 (6)	0.0156 (3)
C6	0.85852 (13)	0.14974 (11)	−0.19736 (6)	0.0189 (3)
H6A	0.8412	0.1582	−0.2392	0.023*
C7	0.76393 (13)	0.11015 (11)	−0.16366 (6)	0.0178 (3)
H7A	0.6822	0.0934	−0.1826	0.021*
C8	1.04919 (14)	0.23897 (12)	−0.26731 (6)	0.0209 (3)
H8A	1.0051	0.1793	−0.2848	0.025*
H8B	1.1339	0.2444	−0.2849	0.025*
C9	0.96903 (15)	0.33067 (13)	−0.28572 (7)	0.0267 (4)
H9A	0.9590	0.3346	−0.3294	0.040*
H9B	1.0129	0.3908	−0.2699	0.040*
H9C	0.8837	0.3256	−0.2697	0.040*
C10	1.18098 (13)	0.27590 (11)	−0.17287 (6)	0.0178 (3)
H10A	1.2477	0.2868	−0.2017	0.021*
H10B	1.2193	0.2333	−0.1403	0.021*
C11	1.14461 (15)	0.37612 (12)	−0.14676 (7)	0.0241 (3)
H11A	1.2217	0.4073	−0.1272	0.036*
H11B	1.0800	0.3659	−0.1174	0.036*
H11C	1.1088	0.4196	−0.1788	0.036*
C12	0.56282 (13)	−0.18488 (11)	−0.01543 (6)	0.0178 (3)
C13	0.59362 (14)	−0.29028 (11)	−0.02924 (6)	0.0185 (3)
C14	0.68952 (15)	−0.34159 (12)	0.00421 (7)	0.0231 (3)
H14A	0.7339	−0.3092	0.0372	0.028*
C15	0.72204 (16)	−0.43823 (12)	−0.00909 (7)	0.0281 (4)
H15A	0.7886	−0.4709	0.0146	0.034*
C16	0.65822 (19)	−0.48938 (12)	−0.05719 (8)	0.0314 (4)
C17	0.55900 (16)	−0.43734 (12)	−0.09041 (7)	0.0281 (4)
H17A	0.5123	−0.4697	−0.1227	0.034*
C18	0.52914 (15)	−0.34049 (12)	−0.07659 (7)	0.0215 (3)
H18A	0.4628	−0.3070	−0.1000	0.026*
C19	0.6089 (3)	−0.6454 (2)	−0.11435 (12)	0.0390 (8)	0.798 (5)
H19A	0.5177	−0.6240	−0.1135	0.047*	0.798 (5)
H19B	0.6145	−0.7167	−0.1032	0.047*	0.798 (5)
C19A	0.6650 (8)	−0.6238 (6)	−0.1345 (3)	0.021 (2)	0.202 (5)
H19C	0.6501	−0.5692	−0.1638	0.025*	0.202 (5)
H19D	0.7350	−0.6677	−0.1469	0.025*	0.202 (5)
C20	0.6553 (3)	−0.6304 (2)	−0.17580 (13)	0.0488 (9)	0.798 (5)
H20A	0.6016	−0.6697	−0.2047	0.073*	0.798 (5)
H20B	0.7454	−0.6522	−0.1762	0.073*	0.798 (5)
H20C	0.6491	−0.5596	−0.1865	0.073*	0.798 (5)
C20A	0.5425 (8)	−0.6813 (7)	−0.1250 (4)	0.025 (2)	0.202 (5)
H20D	0.5104	−0.7120	−0.1628	0.038*	0.202 (5)
H20E	0.4770	−0.6358	−0.1111	0.038*	0.202 (5)
H20F	0.5609	−0.7335	−0.0951	0.038*	0.202 (5)
C21	0.8083 (2)	−0.63245 (14)	−0.04326 (9)	0.0270 (5)	0.890 (5)
H21A	0.8758	−0.5814	−0.0346	0.032*	0.890 (5)
H21B	0.8421	−0.6818	−0.0710	0.032*	0.890 (5)
C21A	0.7424 (11)	−0.6515 (9)	−0.0200 (5)	0.014 (3)	0.110 (5)
H21C	0.7204	−0.6266	0.0196	0.017*	0.110 (5)
H21D	0.7165	−0.7222	−0.0252	0.017*	0.110 (5)
C22	0.77785 (19)	−0.68377 (15)	0.01393 (10)	0.0317 (6)	0.890 (5)
H22A	0.8564	−0.7150	0.0321	0.048*	0.890 (5)
H22B	0.7119	−0.7350	0.0052	0.048*	0.890 (5)
H22C	0.7455	−0.6347	0.0416	0.048*	0.890 (5)
C22A	0.8816 (13)	−0.6323 (12)	−0.0329 (7)	0.023 (4)	0.110 (5)
H22D	0.9389	−0.6677	−0.0036	0.035*	0.110 (5)
H22E	0.8993	−0.5606	−0.0304	0.035*	0.110 (5)
H22F	0.8966	−0.6562	−0.0731	0.035*	0.110 (5)
C23	0.78856 (12)	0.09373 (11)	0.13414 (6)	0.0151 (3)
H23A	0.7982	0.1353	0.1005	0.018*
C24	0.86084 (12)	0.11458 (11)	0.18662 (6)	0.0146 (3)
C25	0.84666 (13)	0.05239 (11)	0.23546 (6)	0.0176 (3)
H25A	0.8948	0.0646	0.2722	0.021*
C26	0.76207 (14)	−0.02724 (11)	0.23011 (7)	0.0177 (3)
H26A	0.7523	−0.0710	0.2628	0.021*
C27	0.69193 (13)	−0.04194 (11)	0.17624 (6)	0.0156 (3)
H27A	0.6322	−0.0957	0.1727	0.019*
C28	0.93872 (13)	0.20938 (11)	0.19367 (6)	0.0162 (3)
C29	1.10610 (13)	0.13687 (11)	0.13207 (6)	0.0184 (3)
H29A	1.0595	0.0740	0.1392	0.022*
H29B	1.1970	0.1283	0.1476	0.022*
C30	1.10256 (16)	0.15648 (13)	0.06565 (7)	0.0272 (4)
H30A	1.1425	0.1005	0.0457	0.041*
H30B	1.1502	0.2179	0.0583	0.041*
H30C	1.0127	0.1638	0.0499	0.041*
C31	1.11704 (14)	0.31346 (11)	0.17016 (7)	0.0218 (3)
H31A	1.2063	0.3033	0.1584	0.026*
H31B	1.1222	0.3347	0.2125	0.026*
C32	1.05431 (16)	0.39602 (12)	0.13212 (8)	0.0309 (4)
H32A	1.1052	0.4573	0.1376	0.046*
H32B	0.9665	0.4077	0.1442	0.046*
H32C	1.0507	0.3763	0.0900	0.046*

	U11	U22	U33	U12	U13	U23
Zn1	0.01304 (8)	0.01106 (9)	0.01221 (9)	0.00028 (6)	0.00165 (6)	−0.00082 (6)
O1	0.0216 (5)	0.0223 (6)	0.0204 (5)	−0.0014 (5)	0.0085 (4)	0.0013 (5)
O2	0.0304 (6)	0.0132 (5)	0.0238 (6)	0.0017 (5)	0.0019 (4)	−0.0040 (5)
O3	0.0274 (6)	0.0142 (5)	0.0257 (6)	0.0067 (4)	0.0026 (4)	0.0000 (5)
O4	0.0168 (5)	0.0281 (6)	0.0256 (6)	−0.0040 (5)	0.0057 (4)	0.0017 (5)
O5	0.0239 (5)	0.0195 (6)	0.0292 (6)	−0.0031 (5)	0.0091 (4)	−0.0091 (5)
N1	0.0142 (5)	0.0124 (6)	0.0160 (6)	0.0015 (4)	0.0030 (4)	−0.0008 (5)
N2	0.0143 (5)	0.0152 (6)	0.0199 (6)	−0.0008 (5)	0.0010 (5)	−0.0042 (5)
N3	0.0159 (5)	0.0193 (7)	0.0157 (6)	−0.0015 (5)	0.0039 (4)	0.0010 (5)
N4	0.0780 (12)	0.0235 (8)	0.0499 (10)	0.0278 (9)	−0.0370 (9)	−0.0196 (8)
C1	0.0198 (7)	0.0104 (7)	0.0219 (8)	0.0016 (6)	0.0075 (6)	−0.0015 (6)
C2	0.0169 (6)	0.0110 (7)	0.0186 (7)	0.0010 (5)	0.0052 (5)	0.0002 (6)
C3	0.0204 (7)	0.0141 (7)	0.0157 (7)	0.0011 (6)	0.0033 (5)	−0.0005 (6)
C4	0.0159 (6)	0.0158 (7)	0.0173 (7)	−0.0001 (6)	0.0014 (5)	−0.0003 (6)
C5	0.0161 (6)	0.0128 (7)	0.0184 (7)	0.0013 (6)	0.0053 (5)	0.0000 (6)
C6	0.0189 (7)	0.0219 (8)	0.0158 (7)	0.0000 (6)	0.0017 (5)	0.0021 (6)
C7	0.0149 (6)	0.0177 (7)	0.0210 (7)	−0.0007 (6)	0.0015 (5)	0.0005 (6)
C8	0.0193 (7)	0.0275 (8)	0.0165 (7)	−0.0014 (6)	0.0055 (6)	0.0027 (7)
C9	0.0261 (8)	0.0297 (9)	0.0240 (8)	−0.0027 (7)	−0.0007 (6)	0.0073 (7)
C10	0.0161 (6)	0.0188 (8)	0.0190 (7)	−0.0021 (6)	0.0039 (5)	0.0004 (6)
C11	0.0305 (8)	0.0205 (8)	0.0215 (8)	0.0008 (7)	0.0022 (6)	0.0001 (7)
C12	0.0207 (7)	0.0141 (7)	0.0195 (7)	0.0015 (6)	0.0080 (6)	0.0015 (6)
C13	0.0240 (7)	0.0127 (7)	0.0191 (7)	0.0027 (6)	0.0040 (6)	−0.0002 (6)
C14	0.0318 (8)	0.0168 (8)	0.0200 (8)	0.0033 (7)	−0.0039 (6)	−0.0032 (7)
C15	0.0370 (9)	0.0191 (8)	0.0266 (9)	0.0099 (7)	−0.0102 (7)	−0.0026 (7)
C16	0.0457 (10)	0.0163 (8)	0.0304 (9)	0.0118 (7)	−0.0102 (8)	−0.0068 (7)
C17	0.0375 (9)	0.0196 (8)	0.0256 (8)	0.0074 (7)	−0.0111 (7)	−0.0078 (7)
C18	0.0258 (7)	0.0172 (8)	0.0211 (8)	0.0057 (6)	−0.0022 (6)	0.0006 (6)
C19	0.048 (2)	0.0193 (14)	0.0468 (17)	0.0109 (14)	−0.0154 (15)	−0.0123 (13)
C19A	0.029 (4)	0.011 (3)	0.024 (4)	0.000 (3)	0.008 (3)	0.000 (3)
C20	0.0493 (15)	0.0474 (17)	0.0470 (19)	0.0233 (13)	−0.0163 (12)	−0.0227 (14)
C20A	0.022 (4)	0.019 (5)	0.035 (5)	−0.004 (4)	−0.005 (4)	0.004 (4)
C21	0.0295 (12)	0.0161 (9)	0.0355 (11)	0.0056 (8)	0.0039 (9)	−0.0024 (8)
C21A	0.021 (5)	0.011 (5)	0.010 (5)	0.005 (4)	−0.003 (4)	0.000 (4)
C22	0.0302 (10)	0.0230 (10)	0.0419 (13)	0.0001 (8)	0.0021 (9)	0.0014 (9)
C22A	0.017 (5)	0.022 (5)	0.030 (5)	0.000 (4)	0.001 (4)	−0.002 (4)
C23	0.0147 (6)	0.0136 (7)	0.0173 (7)	0.0009 (5)	0.0041 (5)	0.0000 (6)
C24	0.0130 (6)	0.0135 (7)	0.0176 (7)	0.0016 (5)	0.0029 (5)	−0.0032 (6)
C25	0.0183 (7)	0.0184 (8)	0.0157 (7)	0.0032 (6)	−0.0010 (5)	−0.0022 (6)
C26	0.0205 (7)	0.0163 (7)	0.0166 (7)	0.0030 (6)	0.0024 (6)	0.0027 (6)
C27	0.0161 (6)	0.0119 (7)	0.0192 (7)	0.0012 (6)	0.0033 (5)	−0.0001 (6)
C28	0.0152 (6)	0.0164 (7)	0.0168 (7)	0.0002 (6)	−0.0010 (5)	−0.0011 (6)
C29	0.0146 (6)	0.0174 (8)	0.0234 (8)	0.0015 (6)	0.0028 (5)	−0.0038 (6)
C30	0.0322 (8)	0.0264 (9)	0.0235 (8)	0.0083 (7)	0.0062 (6)	−0.0033 (7)
C31	0.0188 (7)	0.0198 (8)	0.0271 (8)	−0.0049 (6)	0.0037 (6)	−0.0067 (7)
C32	0.0342 (9)	0.0162 (8)	0.0427 (10)	−0.0041 (7)	0.0059 (8)	−0.0002 (8)

Zn1—Zn1i	2.8874 (3)	C14—H14A	0.95
Zn1—O1	2.0349 (10)	C15—C16	1.407 (2)
Zn1—O2	2.0251 (10)	C15—H15A	0.95
Zn1—O3	2.0465 (10)	C16—C17	1.414 (2)
Zn1—O4	2.0337 (10)	C17—C18	1.376 (2)
Zn1—N1	2.0484 (12)	C17—H17A	0.95
O1—C1	1.2664 (18)	C18—H18A	0.95
O2—C12	1.2673 (18)	C19—C20	1.504 (4)
O3—C12i	1.2599 (18)	C19—H19A	0.99
O4—C1i	1.2599 (17)	C19—H19B	0.99
O5—C28	1.2339 (17)	C19A—C20A	1.514 (7)
N1—C23	1.3439 (18)	C19A—H19C	0.99
N1—C27	1.3403 (19)	C19A—H19D	0.99
N2—C28	1.3415 (17)	C20—H20A	0.98
N2—C29	1.4721 (18)	C20—H20B	0.98
N2—C31	1.4678 (19)	C20—H20C	0.98
N3—C5	1.3760 (17)	C20A—H20D	0.98
N3—C8	1.4620 (18)	C20A—H20E	0.98
N3—C10	1.4612 (18)	C20A—H20F	0.98
N4—C16	1.370 (2)	C21—C22	1.508 (3)
N4—C19	1.488 (3)	C21—H21A	0.99
N4—C19A	1.515 (6)	C21—H21B	0.99
N4—C21	1.472 (2)	C21A—C22A	1.514 (8)
N4—C21A	1.527 (8)	C21A—H21C	0.99
C1—O4i	1.2599 (17)	C21A—H21D	0.99
C1—C2	1.4896 (19)	C22—H22A	0.98
C2—C3	1.391 (2)	C22—H22B	0.98
C2—C7	1.390 (2)	C22—H22C	0.98
C3—C4	1.3826 (19)	C22A—H22D	0.98
C3—H3A	0.95	C22A—H22E	0.98
C4—C5	1.413 (2)	C22A—H22F	0.98
C4—H4A	0.95	C23—C24	1.382 (2)
C5—C6	1.412 (2)	C23—H23A	0.95
C6—C7	1.3845 (19)	C24—C25	1.393 (2)
C6—H6A	0.95	C24—C28	1.509 (2)
C7—H7A	0.95	C25—C26	1.382 (2)
C8—C9	1.526 (2)	C25—H25A	0.95
C8—H8A	0.99	C26—C27	1.383 (2)
C8—H8B	0.99	C26—H26A	0.95
C9—H9A	0.98	C27—H27A	0.95
C9—H9B	0.98	C29—C30	1.512 (2)
C9—H9C	0.98	C29—H29A	0.99
C10—C11	1.524 (2)	C29—H29B	0.99
C10—H10A	0.99	C30—H30A	0.98
C10—H10B	0.99	C30—H30B	0.98
C11—H11A	0.98	C30—H30C	0.98
C11—H11B	0.98	C31—C32	1.518 (2)
C11—H11C	0.98	C31—H31A	0.99
C12—O3i	1.2599 (18)	C31—H31B	0.99
C12—C13	1.486 (2)	C32—H32A	0.98
C13—C14	1.388 (2)	C32—H32B	0.98
C13—C18	1.391 (2)	C32—H32C	0.98
C14—C15	1.377 (2)
O2—Zn1—O4	89.12 (4)	C18—C17—C16	120.93 (15)
O2—Zn1—O1	89.50 (4)	C18—C17—H17A	119.5
O4—Zn1—O1	161.75 (4)	C16—C17—H17A	119.5
O2—Zn1—O3	161.66 (4)	C17—C18—C13	121.68 (14)
O4—Zn1—O3	88.54 (4)	C17—C18—H18A	119.2
O1—Zn1—O3	87.08 (4)	C13—C18—H18A	119.2
O2—Zn1—N1	103.03 (4)	N4—C19—C20	108.2 (3)
O4—Zn1—N1	96.87 (4)	N4—C19—H19A	110.1
O1—Zn1—N1	101.17 (4)	C20—C19—H19A	110.1
O3—Zn1—N1	95.31 (4)	N4—C19—H19B	110.1
O2—Zn1—Zn1i	85.53 (3)	C20—C19—H19B	110.1
O4—Zn1—Zn1i	80.95 (3)	H19A—C19—H19B	108.4
O1—Zn1—Zn1i	80.80 (3)	C19—C20—H20A	109.5
O3—Zn1—Zn1i	76.14 (3)	C19—C20—H20B	109.5
N1—Zn1—Zn1i	171.18 (3)	H20A—C20—H20B	109.5
C1—O1—Zn1	126.55 (9)	C19—C20—H20C	109.5
C12—O2—Zn1	121.15 (9)	H20A—C20—H20C	109.5
C12i—O3—Zn1	132.36 (10)	H20B—C20—H20C	109.5
C1i—O4—Zn1	126.57 (10)	C20A—C19A—N4	98.6 (6)
C27—N1—C23	118.75 (12)	C20A—C19A—H19C	112.0
C27—N1—Zn1	120.95 (9)	N4—C19A—H19C	112.0
C23—N1—Zn1	120.09 (10)	C20A—C19A—H19D	112.0
C28—N2—C31	117.63 (12)	N4—C19A—H19D	112.0
C28—N2—C29	124.34 (12)	H19C—C19A—H19D	109.7
C31—N2—C29	117.84 (11)	C19A—C20A—H20D	109.5
C5—N3—C10	120.74 (12)	C19A—C20A—H20E	109.5
C5—N3—C8	120.81 (12)	H20D—C20A—H20E	109.5
C10—N3—C8	117.13 (11)	C19A—C20A—H20F	109.5
C16—N4—C21	121.25 (15)	H20D—C20A—H20F	109.5
C16—N4—C19	121.07 (16)	H20E—C20A—H20F	109.5
C21—N4—C19	117.63 (16)	N4—C21—C22	110.67 (18)
C16—N4—C19A	120.6 (4)	N4—C21—H21A	109.5
C21—N4—C19A	110.3 (4)	C22—C21—H21A	109.5
C16—N4—C21A	116.7 (5)	N4—C21—H21B	109.5
C19—N4—C21A	108.9 (5)	C22—C21—H21B	109.5
C19A—N4—C21A	122.4 (6)	H21A—C21—H21B	108.1
O4i—C1—O1	125.11 (13)	C21—C22—H22A	109.5
O4i—C1—C2	117.60 (13)	C21—C22—H22B	109.5
O1—C1—C2	117.28 (12)	H22A—C22—H22B	109.5
C7—C2—C3	117.82 (12)	C21—C22—H22C	109.5
C7—C2—C1	121.46 (13)	H22A—C22—H22C	109.5
C3—C2—C1	120.71 (13)	H22B—C22—H22C	109.5
C4—C3—C2	121.84 (13)	C22A—C21A—N4	92.2 (9)
C4—C3—H3A	119.1	C22A—C21A—H21C	113.2
C2—C3—H3A	119.1	N4—C21A—H21C	113.2
C3—C4—C5	120.69 (13)	C22A—C21A—H21D	113.2
C3—C4—H4A	119.7	N4—C21A—H21D	113.2
C5—C4—H4A	119.7	H21C—C21A—H21D	110.6
N3—C5—C6	121.70 (13)	C21A—C22A—H22D	109.5
N3—C5—C4	121.37 (13)	C21A—C22A—H22E	109.5
C6—C5—C4	116.93 (12)	H22D—C22A—H22E	109.5
C7—C6—C5	121.17 (13)	C21A—C22A—H22F	109.5
C7—C6—H6A	119.4	H22D—C22A—H22F	109.5
C5—C6—H6A	119.4	H22E—C22A—H22F	109.5
C6—C7—C2	121.32 (13)	N1—C23—C24	122.65 (13)
C6—C7—H7A	119.3	N1—C23—H23A	118.7
C2—C7—H7A	119.3	C24—C23—H23A	118.7
N3—C8—C9	115.68 (13)	C23—C24—C25	118.02 (13)
N3—C8—H8A	108.4	C23—C24—C28	121.06 (13)
C9—C8—H8A	108.4	C25—C24—C28	120.39 (13)
N3—C8—H8B	108.4	C26—C25—C24	119.61 (13)
C9—C8—H8B	108.4	C26—C25—H25A	120.2
H8A—C8—H8B	107.4	C24—C25—H25A	120.2
C8—C9—H9A	109.5	C25—C26—C27	118.67 (14)
C8—C9—H9B	109.5	C25—C26—H26A	120.7
H9A—C9—H9B	109.5	C27—C26—H26A	120.7
C8—C9—H9C	109.5	N1—C27—C26	122.28 (13)
H9A—C9—H9C	109.5	N1—C27—H27A	118.9
H9B—C9—H9C	109.5	C26—C27—H27A	118.9
N3—C10—C11	113.65 (12)	O5—C28—N2	122.70 (13)
N3—C10—H10A	108.8	O5—C28—C24	118.24 (12)
C11—C10—H10A	108.8	N2—C28—C24	119.05 (12)
N3—C10—H10B	108.8	N2—C29—C30	112.26 (12)
C11—C10—H10B	108.8	N2—C29—H29A	109.2
H10A—C10—H10B	107.7	C30—C29—H29A	109.2
C10—C11—H11A	109.5	N2—C29—H29B	109.2
C10—C11—H11B	109.5	C30—C29—H29B	109.2
H11A—C11—H11B	109.5	H29A—C29—H29B	107.9
C10—C11—H11C	109.5	C29—C30—H30A	109.5
H11A—C11—H11C	109.5	C29—C30—H30B	109.5
H11B—C11—H11C	109.5	H30A—C30—H30B	109.5
O3i—C12—O2	124.80 (14)	C29—C30—H30C	109.5
O3i—C12—C13	117.40 (13)	H30A—C30—H30C	109.5
O2—C12—C13	117.79 (13)	H30B—C30—H30C	109.5
C14—C13—C18	117.65 (14)	N2—C31—C32	113.34 (13)
C14—C13—C12	120.99 (13)	N2—C31—H31A	108.9
C18—C13—C12	121.36 (13)	C32—C31—H31A	108.9
C15—C14—C13	121.76 (15)	N2—C31—H31B	108.9
C15—C14—H14A	119.1	C32—C31—H31B	108.9
C13—C14—H14A	119.1	H31A—C31—H31B	107.7
C14—C15—C16	121.05 (15)	C31—C32—H32A	109.5
C14—C15—H15A	119.5	C31—C32—H32B	109.5
C16—C15—H15A	119.5	H32A—C32—H32B	109.5
N4—C16—C15	121.43 (15)	C31—C32—H32C	109.5
N4—C16—C17	121.65 (15)	H32A—C32—H32C	109.5
C15—C16—C17	116.92 (14)	H32B—C32—H32C	109.5
O2—Zn1—O1—C1	86.39 (12)	O2—C12—C13—C18	177.38 (13)
O4—Zn1—O1—C1	0.7 (2)	C18—C13—C14—C15	1.0 (2)
O3—Zn1—O1—C1	−75.59 (12)	C12—C13—C14—C15	−177.97 (15)
N1—Zn1—O1—C1	−170.43 (12)	C13—C14—C15—C16	−0.5 (3)
Zn1i—Zn1—O1—C1	0.84 (11)	C21—N4—C16—C15	−9.2 (3)
O4—Zn1—O2—C12	80.83 (11)	C19—N4—C16—C15	168.0 (2)
O1—Zn1—O2—C12	−80.97 (11)	C19A—N4—C16—C15	−155.2 (4)
O3—Zn1—O2—C12	−1.8 (2)	C21A—N4—C16—C15	31.6 (6)
N1—Zn1—O2—C12	177.68 (10)	C21—N4—C16—C17	169.95 (19)
Zn1i—Zn1—O2—C12	−0.16 (10)	C19—N4—C16—C17	−12.8 (3)
O2—Zn1—O3—C12i	3.0 (2)	C19A—N4—C16—C17	24.0 (5)
O4—Zn1—O3—C12i	−79.71 (13)	C21A—N4—C16—C17	−149.3 (5)
O1—Zn1—O3—C12i	82.56 (13)	C14—C15—C16—N4	178.53 (19)
N1—Zn1—O3—C12i	−176.48 (13)	C14—C15—C16—C17	−0.7 (3)
Zn1i—Zn1—O3—C12i	1.32 (12)	N4—C16—C17—C18	−177.90 (19)
O2—Zn1—O4—C1i	−84.71 (12)	C15—C16—C17—C18	1.3 (3)
O1—Zn1—O4—C1i	1.0 (2)	C16—C17—C18—C13	−0.8 (3)
O3—Zn1—O4—C1i	77.11 (12)	C14—C13—C18—C17	−0.4 (2)
N1—Zn1—O4—C1i	172.28 (12)	C12—C13—C18—C17	178.60 (15)
Zn1i—Zn1—O4—C1i	0.91 (12)	C16—N4—C19—C20	92.3 (3)
O2—Zn1—N1—C27	−56.86 (11)	C21—N4—C19—C20	−90.3 (2)
O4—Zn1—N1—C27	33.82 (11)	C19A—N4—C19—C20	−6.4 (7)
O1—Zn1—N1—C27	−148.95 (10)	C21A—N4—C19—C20	−128.3 (5)
O3—Zn1—N1—C27	122.98 (10)	C16—N4—C19A—C20A	−99.3 (6)
O2—Zn1—N1—C23	128.42 (10)	C21—N4—C19A—C20A	111.4 (5)
O4—Zn1—N1—C23	−140.90 (10)	C19—N4—C19A—C20A	1.3 (4)
O1—Zn1—N1—C23	36.33 (11)	C21A—N4—C19A—C20A	73.6 (8)
O3—Zn1—N1—C23	−51.73 (10)	C16—N4—C21—C22	88.0 (2)
Zn1—O1—C1—O4i	−1.8 (2)	C19—N4—C21—C22	−89.4 (3)
Zn1—O1—C1—C2	177.44 (9)	C19A—N4—C21—C22	−123.0 (4)
O4i—C1—C2—C7	−2.5 (2)	C21A—N4—C21—C22	−5.3 (8)
O1—C1—C2—C7	178.20 (13)	C16—N4—C21A—C22A	−98.4 (8)
O4i—C1—C2—C3	176.53 (13)	C21—N4—C21A—C22A	8.8 (6)
O1—C1—C2—C3	−2.8 (2)	C19—N4—C21A—C22A	120.2 (8)
C7—C2—C3—C4	4.3 (2)	C19A—N4—C21A—C22A	88.5 (9)
C1—C2—C3—C4	−174.77 (13)	C27—N1—C23—C24	−0.2 (2)
C2—C3—C4—C5	−1.2 (2)	Zn1—N1—C23—C24	174.59 (10)
C10—N3—C5—C6	163.01 (13)	N1—C23—C24—C25	0.6 (2)
C8—N3—C5—C6	−3.5 (2)	N1—C23—C24—C28	−171.13 (12)
C10—N3—C5—C4	−17.2 (2)	C23—C24—C25—C26	0.1 (2)
C8—N3—C5—C4	176.24 (13)	C28—C24—C25—C26	171.85 (13)
C3—C4—C5—N3	177.03 (13)	C24—C25—C26—C27	−1.0 (2)
C3—C4—C5—C6	−3.2 (2)	C23—N1—C27—C26	−0.8 (2)
N3—C5—C6—C7	−175.71 (14)	Zn1—N1—C27—C26	−175.60 (10)
C4—C5—C6—C7	4.5 (2)	C25—C26—C27—N1	1.5 (2)
C5—C6—C7—C2	−1.5 (2)	C31—N2—C28—O5	−2.0 (2)
C3—C2—C7—C6	−2.9 (2)	C29—N2—C28—O5	172.87 (13)
C1—C2—C7—C6	176.11 (14)	C31—N2—C28—C24	176.98 (12)
C5—N3—C8—C9	82.09 (17)	C29—N2—C28—C24	−8.2 (2)
C10—N3—C8—C9	−84.90 (15)	C23—C24—C28—O5	106.09 (16)
C5—N3—C10—C11	−74.11 (17)	C25—C24—C28—O5	−65.45 (18)
C8—N3—C10—C11	92.88 (15)	C23—C24—C28—N2	−72.92 (18)
Zn1—O2—C12—O3i	−0.69 (19)	C25—C24—C28—N2	115.54 (15)
Zn1—O2—C12—C13	178.81 (9)	C28—N2—C29—C30	114.21 (15)
O3i—C12—C13—C14	175.86 (14)	C31—N2—C29—C30	−70.95 (16)
O2—C12—C13—C14	−3.7 (2)	C28—N2—C31—C32	−76.65 (17)
O3i—C12—C13—C18	−3.1 (2)	C29—N2—C31—C32	108.16 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O5ii	0.99	2.49	3.390 (2)	151
C21—H21B···Cg1iii	0.99	2.94	3.879 (3)	163
C29—H29A···Cg1iv	0.99	2.87	3.637 (2)	137

Table 1

Selected bond lengths (Å)

Zn1—O1	2.0349 (10)
Zn1—O2	2.0251 (10)
Zn1—O3	2.0465 (10)
Zn1—O4	2.0337 (10)
Zn1—N1	2.0484 (12)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O5ii	0.99	2.49	3.390 (2)	151
C21—H21B⋯Cg1iii	0.99	2.94	3.879 (3)	163
C29—H29A⋯Cg1iv	0.99	2.87	3.637 (2)	137

Symmetry codes: (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C2–C7 ring.