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

In the centrosymmetric binuclear title complex, [Zn(2)(C(8)H(7)O(2))(4)(C(10)H(14)N(2)O)(2)], the Zn atoms [Zn⋯Zn' = 2.9494 (3) Å] are bridged by four 4-methyl-benzoate (PMB) anions. The four nearest O atoms around each Zn(II) ion form a distorted square-planar arrangement, the octahedral coordin-ation being completed by the pyridine N atom of the N,N-diethyl-nicotinamide (DENA) ligand. Each Zn(II) ion is displaced by 0.3530 (1) Å from the plane of the four O atoms. The dihedral angles between carboxyl-ate groups and their adjacent benzene rings are 5.88 (10) and 11.89 (9)°, while the benzene rings are oriented at a dihedral angle of 75.19 (4)°. The pyridine ring is oriented at dihedral angles of 38.28 (4) and 49.17 (4)° with respect to the benzene rings. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. π-π contacts between parallel benzene rings [centroid-centroid distance = 3.8388 (8) Å] and between parallel pyridine rings [centroid-centroid distance = 3.4855 (7) Å] may further stabilize the crystal structure.

Related literature

For niacin, see: Krishnamachari (1974 ▶) and for the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Hökelek et al. (1995 ▶); Hökelek et al. (2009a ▶,b ▶,c ▶); Necefoğlu et al. (2010 ▶); Speier & Fulop (1989 ▶); Usubaliev et al. (1980 ▶).

Experimental

Crystal data

[Zn2(C8H7O2)4(C10H14N2O)2]

M = 1027.82

Triclinic,

a = 9.8603 (2) Å

b = 10.5272 (2) Å

c = 12.3514 (3) Å

α = 97.346 (3)°

β = 93.525 (3)°

γ = 106.342 (5)°

V = 1213.78 (6) Å3

Z = 1

Mo Kα radiation

μ = 1.05 mm−1

T = 100 K

0.45 × 0.35 × 0.34 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.649, T max = 0.698

22051 measured reflections

6067 independent reflections

5604 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.065

S = 1.06

6067 reflections

311 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.25 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/S1600536810011517/xu2740sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011517/xu2740Isup2.hkl

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

[Zn2(C8H7O2)4(C10H14N2O)2]	Z = 1
Mr = 1027.82	F(000) = 536
Triclinic, P1	Dx = 1.406 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8603 (2) Å	Cell parameters from 9897 reflections
b = 10.5272 (2) Å	θ = 2.4–28.4°
c = 12.3514 (3) Å	µ = 1.05 mm−1
α = 97.346 (3)°	T = 100 K
β = 93.525 (3)°	Block, colourless
γ = 106.342 (5)°	0.45 × 0.35 × 0.34 mm
V = 1213.78 (6) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	6067 independent reflections
Radiation source: fine-focus sealed tube	5604 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 28.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.649, Tmax = 0.698	k = −14→14
22051 measured reflections	l = −16→16

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0311P)2 + 0.5069P] where P = (Fo2 + 2Fc2)/3
6067 reflections	(Δ/σ)max < 0.001
311 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.450815 (15)	0.115632 (13)	0.040631 (11)	0.01383 (5)
O1	0.73414 (10)	0.02215 (9)	0.02905 (8)	0.01896 (19)
O2	0.65938 (9)	0.19668 (9)	0.09519 (8)	0.01795 (18)
O3	0.49245 (10)	−0.10996 (10)	0.12229 (8)	0.0210 (2)
O4	0.41059 (10)	0.05856 (9)	0.18860 (8)	0.01957 (19)
O5	0.30214 (10)	0.44313 (10)	−0.27313 (8)	0.0239 (2)
N1	0.37721 (11)	0.27588 (10)	0.02830 (9)	0.0147 (2)
N2	0.08512 (11)	0.30568 (11)	−0.25343 (9)	0.0175 (2)
C1	0.75162 (13)	0.13428 (12)	0.08691 (10)	0.0154 (2)
C2	0.89284 (13)	0.19728 (12)	0.15322 (10)	0.0158 (2)
C3	0.92011 (14)	0.31934 (13)	0.22226 (11)	0.0184 (2)
H3	0.8532	0.3665	0.2228	0.022*
C4	1.04631 (14)	0.37058 (13)	0.29001 (12)	0.0212 (3)
H4	1.0628	0.4518	0.3359	0.025*
C5	1.14912 (14)	0.30273 (14)	0.29080 (11)	0.0205 (3)
C6	1.12308 (14)	0.18255 (14)	0.21929 (12)	0.0210 (3)
H6	1.1913	0.1369	0.2171	0.025*
C7	0.99677 (14)	0.13047 (13)	0.15144 (11)	0.0193 (3)
H7	0.9812	0.0503	0.1043	0.023*
C8	1.28449 (15)	0.35768 (16)	0.36690 (13)	0.0282 (3)
H8A	1.3353	0.2920	0.3650	0.042*
H8B	1.2620	0.3787	0.4403	0.042*
H8C	1.3424	0.4373	0.3439	0.042*
C9	0.44426 (13)	−0.04751 (13)	0.19693 (10)	0.0165 (2)
C10	0.42490 (13)	−0.10307 (12)	0.30249 (10)	0.0162 (2)
C11	0.34787 (14)	−0.05492 (13)	0.38074 (11)	0.0189 (2)
H11	0.3120	0.0156	0.3692	0.023*
C12	0.32480 (14)	−0.11202 (15)	0.47572 (11)	0.0224 (3)
H12	0.2727	−0.0796	0.5270	0.027*
C13	0.37825 (15)	−0.21695 (14)	0.49557 (11)	0.0235 (3)
C14	0.45906 (15)	−0.26154 (14)	0.41892 (11)	0.0219 (3)
H14	0.4984	−0.3294	0.4320	0.026*
C15	0.48161 (14)	−0.20583 (13)	0.32319 (11)	0.0189 (2)
H15	0.5350	−0.2373	0.2725	0.023*
C16	0.34955 (19)	−0.28015 (19)	0.59785 (13)	0.0360 (4)
H16A	0.3701	−0.3646	0.5892	0.054*
H16B	0.2515	−0.2941	0.6100	0.054*
H16C	0.4088	−0.2220	0.6596	0.054*
C17	0.40194 (13)	0.38549 (13)	0.10388 (10)	0.0160 (2)
H17	0.4491	0.3876	0.1719	0.019*
C18	0.35931 (13)	0.49579 (13)	0.08359 (11)	0.0181 (2)
H18	0.3738	0.5689	0.1384	0.022*
C19	0.29485 (13)	0.49579 (12)	−0.01931 (11)	0.0173 (2)
H19	0.2696	0.5704	−0.0357	0.021*
C20	0.26868 (12)	0.38185 (12)	−0.09764 (10)	0.0152 (2)
C21	0.30915 (13)	0.27380 (12)	−0.06968 (10)	0.0151 (2)
H21	0.2883	0.1964	−0.1209	0.018*
C22	0.21826 (13)	0.37980 (12)	−0.21572 (11)	0.0162 (2)
C23	−0.01970 (14)	0.23617 (13)	−0.18488 (11)	0.0199 (3)
H23A	0.0297	0.2137	−0.1231	0.024*
H23B	−0.0793	0.1532	−0.2275	0.024*
C24	−0.11255 (15)	0.32037 (15)	−0.14258 (13)	0.0270 (3)
H24A	−0.1828	0.2694	−0.1020	0.041*
H24B	−0.1588	0.3458	−0.2034	0.041*
H24C	−0.0549	0.3993	−0.0955	0.041*
C25	0.03872 (15)	0.29558 (14)	−0.37030 (11)	0.0218 (3)
H25A	0.0906	0.3760	−0.3974	0.026*
H25B	−0.0615	0.2891	−0.3790	0.026*
C26	0.06320 (19)	0.17447 (16)	−0.43724 (13)	0.0321 (3)
H26A	0.0298	0.1694	−0.5128	0.048*
H26B	0.0124	0.0948	−0.4102	0.048*
H26C	0.1629	0.1824	−0.4311	0.048*

	U11	U22	U33	U12	U13	U23
Zn1	0.01471 (8)	0.01387 (7)	0.01481 (8)	0.00699 (5)	0.00123 (5)	0.00289 (5)
O1	0.0180 (4)	0.0163 (4)	0.0221 (5)	0.0056 (3)	−0.0003 (4)	0.0008 (4)
O2	0.0162 (4)	0.0170 (4)	0.0215 (5)	0.0064 (3)	0.0004 (4)	0.0035 (3)
O3	0.0231 (5)	0.0281 (5)	0.0161 (4)	0.0131 (4)	0.0043 (4)	0.0052 (4)
O4	0.0229 (5)	0.0208 (4)	0.0177 (4)	0.0093 (4)	0.0027 (4)	0.0058 (4)
O5	0.0200 (5)	0.0275 (5)	0.0235 (5)	0.0030 (4)	0.0020 (4)	0.0110 (4)
N1	0.0133 (5)	0.0147 (5)	0.0172 (5)	0.0053 (4)	0.0026 (4)	0.0034 (4)
N2	0.0164 (5)	0.0186 (5)	0.0176 (5)	0.0053 (4)	0.0009 (4)	0.0031 (4)
C1	0.0160 (6)	0.0156 (5)	0.0155 (6)	0.0045 (4)	0.0029 (5)	0.0061 (4)
C2	0.0150 (5)	0.0159 (6)	0.0173 (6)	0.0045 (4)	0.0025 (5)	0.0047 (5)
C3	0.0180 (6)	0.0174 (6)	0.0215 (6)	0.0070 (5)	0.0038 (5)	0.0046 (5)
C4	0.0215 (6)	0.0177 (6)	0.0223 (6)	0.0038 (5)	0.0015 (5)	0.0002 (5)
C5	0.0167 (6)	0.0226 (6)	0.0211 (6)	0.0029 (5)	0.0010 (5)	0.0057 (5)
C6	0.0166 (6)	0.0239 (6)	0.0249 (7)	0.0087 (5)	0.0026 (5)	0.0051 (5)
C7	0.0180 (6)	0.0179 (6)	0.0225 (6)	0.0068 (5)	0.0022 (5)	0.0017 (5)
C8	0.0199 (7)	0.0332 (8)	0.0278 (7)	0.0037 (6)	−0.0026 (6)	0.0028 (6)
C9	0.0137 (5)	0.0203 (6)	0.0154 (6)	0.0046 (5)	0.0005 (4)	0.0030 (5)
C10	0.0156 (5)	0.0178 (6)	0.0137 (6)	0.0026 (4)	0.0000 (4)	0.0026 (4)
C11	0.0160 (6)	0.0216 (6)	0.0179 (6)	0.0044 (5)	0.0007 (5)	0.0018 (5)
C12	0.0171 (6)	0.0306 (7)	0.0161 (6)	0.0020 (5)	0.0030 (5)	0.0021 (5)
C13	0.0208 (6)	0.0271 (7)	0.0172 (6)	−0.0027 (5)	−0.0018 (5)	0.0071 (5)
C14	0.0242 (7)	0.0197 (6)	0.0198 (6)	0.0031 (5)	−0.0038 (5)	0.0052 (5)
C15	0.0201 (6)	0.0187 (6)	0.0167 (6)	0.0048 (5)	0.0000 (5)	0.0016 (5)
C16	0.0350 (8)	0.0474 (10)	0.0245 (8)	0.0041 (7)	0.0042 (7)	0.0185 (7)
C17	0.0144 (5)	0.0188 (6)	0.0152 (6)	0.0056 (4)	0.0020 (4)	0.0020 (5)
C18	0.0178 (6)	0.0152 (6)	0.0211 (6)	0.0058 (5)	0.0041 (5)	−0.0012 (5)
C19	0.0165 (6)	0.0145 (5)	0.0233 (6)	0.0073 (4)	0.0048 (5)	0.0041 (5)
C20	0.0116 (5)	0.0162 (5)	0.0185 (6)	0.0045 (4)	0.0023 (4)	0.0043 (5)
C21	0.0142 (5)	0.0137 (5)	0.0173 (6)	0.0045 (4)	0.0011 (4)	0.0014 (4)
C22	0.0171 (6)	0.0135 (5)	0.0201 (6)	0.0078 (4)	0.0009 (5)	0.0031 (5)
C23	0.0152 (6)	0.0200 (6)	0.0231 (6)	0.0025 (5)	0.0012 (5)	0.0051 (5)
C24	0.0217 (7)	0.0266 (7)	0.0328 (8)	0.0061 (5)	0.0088 (6)	0.0040 (6)
C25	0.0214 (6)	0.0239 (6)	0.0184 (6)	0.0056 (5)	−0.0026 (5)	0.0019 (5)
C26	0.0409 (9)	0.0295 (8)	0.0242 (7)	0.0105 (7)	0.0035 (7)	−0.0026 (6)

Zn1—Zn1i	2.9494 (3)	C10—C15	1.3934 (18)
Zn1—O1i	2.0420 (9)	C11—H11	0.9300
Zn1—O2	2.0264 (9)	C12—C11	1.3876 (19)
Zn1—O3i	2.1196 (9)	C12—C13	1.393 (2)
Zn1—O4	2.0235 (9)	C12—H12	0.9300
Zn1—N1	2.0340 (10)	C13—C14	1.393 (2)
O1—Zn1i	2.0420 (9)	C13—C16	1.507 (2)
O1—C1	1.2604 (15)	C14—C15	1.3884 (19)
O2—C1	1.2648 (15)	C14—H14	0.9300
O3—Zn1i	2.1196 (9)	C15—H15	0.9300
O3—C9	1.2580 (16)	C16—H16A	0.9600
O4—C9	1.2654 (16)	C16—H16B	0.9600
O5—C22	1.2305 (16)	C16—H16C	0.9600
N1—C17	1.3419 (16)	C17—C18	1.3871 (18)
N1—C21	1.3418 (16)	C17—H17	0.9300
N2—C22	1.3433 (16)	C18—H18	0.9300
N2—C23	1.4700 (17)	C19—C18	1.3857 (19)
N2—C25	1.4685 (17)	C19—H19	0.9300
C1—C2	1.5002 (17)	C20—C19	1.3927 (17)
C2—C7	1.3963 (18)	C20—C21	1.3824 (17)
C3—C2	1.3957 (18)	C20—C22	1.5071 (18)
C3—C4	1.3851 (19)	C21—H21	0.9300
C3—H3	0.9300	C23—C24	1.5146 (19)
C4—H4	0.9300	C23—H23A	0.9700
C5—C4	1.3950 (19)	C23—H23B	0.9700
C5—C6	1.3965 (19)	C24—H24A	0.9600
C5—C8	1.5073 (19)	C24—H24B	0.9600
C6—H6	0.9300	C24—H24C	0.9600
C7—C6	1.3870 (19)	C25—C26	1.515 (2)
C7—H7	0.9300	C25—H25A	0.9700
C8—H8A	0.9600	C25—H25B	0.9700
C8—H8B	0.9600	C26—H26A	0.9600
C8—H8C	0.9600	C26—H26B	0.9600
C9—C10	1.4971 (18)	C26—H26C	0.9600
C10—C11	1.3963 (18)
O1i—Zn1—O3i	84.43 (4)	C13—C12—H12	119.4
O2—Zn1—O1i	159.97 (4)	C12—C13—C14	118.42 (13)
O2—Zn1—O3i	88.67 (4)	C12—C13—C16	120.61 (14)
O2—Zn1—N1	104.57 (4)	C14—C13—C16	120.97 (14)
O4—Zn1—O1i	89.88 (4)	C13—C14—H14	119.6
O4—Zn1—O2	90.22 (4)	C15—C14—C13	120.78 (13)
O4—Zn1—O3i	159.93 (4)	C15—C14—H14	119.6
O4—Zn1—N1	107.92 (4)	C10—C15—H15	119.7
N1—Zn1—O1i	94.43 (4)	C14—C15—C10	120.52 (13)
N1—Zn1—O3i	91.72 (4)	C14—C15—H15	119.7
C1—O1—Zn1i	128.83 (8)	C13—C16—H16A	109.5
C1—O2—Zn1	124.35 (8)	C13—C16—H16B	109.5
C9—O3—Zn1i	145.07 (9)	C13—C16—H16C	109.5
C9—O4—Zn1	110.41 (8)	H16A—C16—H16B	109.5
C17—N1—Zn1	126.21 (9)	H16A—C16—H16C	109.5
C21—N1—Zn1	114.90 (8)	H16B—C16—H16C	109.5
C21—N1—C17	118.59 (11)	N1—C17—C18	122.00 (12)
C22—N2—C23	124.41 (11)	N1—C17—H17	119.0
C22—N2—C25	118.33 (11)	C18—C17—H17	119.0
C25—N2—C23	117.24 (11)	C17—C18—H18	120.4
O1—C1—O2	125.48 (12)	C19—C18—C17	119.26 (12)
O1—C1—C2	117.03 (11)	C19—C18—H18	120.4
O2—C1—C2	117.47 (11)	C18—C19—C20	118.68 (12)
C3—C2—C1	120.98 (11)	C18—C19—H19	120.7
C3—C2—C7	118.75 (12)	C20—C19—H19	120.7
C7—C2—C1	120.17 (11)	C19—C20—C22	122.14 (11)
C2—C3—H3	119.9	C21—C20—C19	118.57 (12)
C4—C3—C2	120.29 (12)	C21—C20—C22	118.65 (11)
C4—C3—H3	119.9	N1—C21—C20	122.78 (11)
C3—C4—C5	121.29 (12)	N1—C21—H21	118.6
C3—C4—H4	119.4	C20—C21—H21	118.6
C5—C4—H4	119.4	O5—C22—N2	123.51 (12)
C4—C5—C6	118.19 (12)	O5—C22—C20	118.39 (11)
C4—C5—C8	120.84 (13)	N2—C22—C20	118.08 (11)
C6—C5—C8	120.97 (13)	N2—C23—C24	112.25 (11)
C5—C6—H6	119.6	N2—C23—H23A	109.2
C7—C6—C5	120.82 (12)	N2—C23—H23B	109.2
C7—C6—H6	119.6	C24—C23—H23A	109.2
C2—C7—H7	119.7	C24—C23—H23B	109.2
C6—C7—C2	120.62 (12)	H23A—C23—H23B	107.9
C6—C7—H7	119.7	C23—C24—H24A	109.5
C5—C8—H8A	109.5	C23—C24—H24B	109.5
C5—C8—H8B	109.5	C23—C24—H24C	109.5
C5—C8—H8C	109.5	H24A—C24—H24B	109.5
H8A—C8—H8B	109.5	H24A—C24—H24C	109.5
H8A—C8—H8C	109.5	H24B—C24—H24C	109.5
H8B—C8—H8C	109.5	N2—C25—C26	111.44 (12)
O3—C9—O4	124.45 (12)	N2—C25—H25A	109.3
O3—C9—C10	117.63 (11)	N2—C25—H25B	109.3
O4—C9—C10	117.92 (11)	C26—C25—H25A	109.3
C11—C10—C9	120.82 (12)	C26—C25—H25B	109.3
C15—C10—C9	120.25 (12)	H25A—C25—H25B	108.0
C15—C10—C11	118.92 (12)	C25—C26—H26A	109.5
C10—C11—H11	119.9	C25—C26—H26B	109.5
C12—C11—C10	120.13 (13)	C25—C26—H26C	109.5
C12—C11—H11	119.9	H26A—C26—H26B	109.5
C11—C12—C13	121.17 (13)	H26A—C26—H26C	109.5
C11—C12—H12	119.4	H26B—C26—H26C	109.5
O1i—Zn1—O2—C1	0.43 (18)	O1—C1—C2—C7	−1.65 (18)
O3i—Zn1—O2—C1	−69.26 (10)	O2—C1—C2—C3	0.75 (18)
O4—Zn1—O2—C1	90.70 (10)	O2—C1—C2—C7	177.09 (12)
N1—Zn1—O2—C1	−160.69 (10)	C1—C2—C7—C6	−174.62 (12)
O1i—Zn1—O4—C9	80.22 (9)	C3—C2—C7—C6	1.8 (2)
O2—Zn1—O4—C9	−79.75 (9)	C4—C3—C2—C1	174.42 (12)
O3i—Zn1—O4—C9	6.98 (16)	C4—C3—C2—C7	−2.0 (2)
N1—Zn1—O4—C9	174.84 (8)	C2—C3—C4—C5	0.3 (2)
O1i—Zn1—N1—C17	139.95 (10)	C6—C5—C4—C3	1.5 (2)
O1i—Zn1—N1—C21	−46.58 (9)	C8—C5—C4—C3	−178.45 (13)
O2—Zn1—N1—C17	−46.43 (11)	C4—C5—C6—C7	−1.6 (2)
O2—Zn1—N1—C21	127.04 (9)	C8—C5—C6—C7	178.28 (13)
O3i—Zn1—N1—C17	−135.50 (10)	C2—C7—C6—C5	0.0 (2)
O3i—Zn1—N1—C21	37.97 (9)	O3—C9—C10—C11	−167.82 (12)
O4—Zn1—N1—C17	48.64 (11)	O3—C9—C10—C15	10.99 (18)
O4—Zn1—N1—C21	−137.89 (8)	O4—C9—C10—C11	11.89 (18)
Zn1i—O1—C1—O2	−15.50 (19)	O4—C9—C10—C15	−169.31 (12)
Zn1i—O1—C1—C2	163.13 (8)	C9—C10—C11—C12	176.76 (11)
Zn1—O2—C1—O1	12.25 (18)	C15—C10—C11—C12	−2.06 (19)
Zn1—O2—C1—C2	−166.37 (8)	C9—C10—C15—C14	−177.34 (12)
Zn1i—O3—C9—O4	−1.2 (2)	C11—C10—C15—C14	1.49 (19)
Zn1i—O3—C9—C10	178.47 (10)	C13—C12—C11—C10	0.5 (2)
Zn1—O4—C9—O3	−1.70 (16)	C11—C12—C13—C14	1.6 (2)
Zn1—O4—C9—C10	178.62 (8)	C11—C12—C13—C16	−178.59 (13)
Zn1—N1—C17—C18	173.27 (9)	C12—C13—C14—C15	−2.2 (2)
C21—N1—C17—C18	0.02 (18)	C16—C13—C14—C15	178.01 (13)
Zn1—N1—C21—C20	−171.23 (9)	C13—C14—C15—C10	0.7 (2)
C17—N1—C21—C20	2.77 (18)	N1—C17—C18—C19	−2.94 (19)
C23—N2—C22—O5	−175.96 (12)	C20—C19—C18—C17	3.09 (19)
C23—N2—C22—C20	5.98 (18)	C21—C20—C19—C18	−0.49 (18)
C25—N2—C22—O5	2.33 (19)	C22—C20—C19—C18	−171.23 (11)
C25—N2—C22—C20	−175.72 (11)	C19—C20—C22—O5	70.73 (16)
C22—N2—C23—C24	92.91 (15)	C19—C20—C22—N2	−111.12 (14)
C25—N2—C23—C24	−85.40 (14)	C21—C20—C22—O5	−100.01 (14)
C22—N2—C25—C26	92.54 (15)	C21—C20—C22—N2	78.14 (15)
C23—N2—C25—C26	−89.04 (15)	C19—C20—C21—N1	−2.52 (18)
O1—C1—C2—C3	−178.00 (12)	C22—C20—C21—N1	168.55 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4ii	0.93	2.55	3.4601 (18)	166
C16—H16C···O4iii	0.96	2.59	3.542 (2)	174
C19—H19···O2iv	0.93	2.57	3.4013 (15)	149

Table 1

Selected bond lengths (Å)

Zn1—O1i	2.0420 (9)
Zn1—O2	2.0264 (9)
Zn1—O3i	2.1196 (9)
Zn1—O4	2.0235 (9)
Zn1—N1	2.0340 (10)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O4ii	0.93	2.55	3.4601 (18)	166
C16—H16C⋯O4iii	0.96	2.59	3.542 (2)	174
C19—H19⋯O2iv	0.93	2.57	3.4013 (15)	149

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