Dibenzoato-κO;κO,O'-(6,6'-dimethyl-2,2'-bipyridine-κN,N')zinc(II)-benzoic acid (1/1).

In the crystal structure of the title compound, [Zn(C(6)H(5)COO)(2)(C(12)H(12)N(2))]·C(6)H(5)COOH, the Zn atom is penta-coordinated in distorted square-pyramidal geometry by two O atoms of a benzoate anion and two N atoms of a 6,6'-dimethyl-2,2'-bipyridine ligand occupying the basal plane and an O atom of another benzoate anion located at the apical site. In the crystal structure, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds and C-H⋯π inter-actions are present.

Related literature

For related structures, see: Alizadeh et al. (2009 ▶); Cui et al. (2005 ▶); Hökelek et al. (2009a ▶,b ▶); Klausmeyer et al. (2007 ▶); Phatchimkun et al. (2009 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

[Zn(C7H5O2)2(C12H12N2)]·C7H6O2

M = 613.96

Triclinic,

a = 9.974 (6) Å

b = 12.546 (7) Å

c = 12.798 (8) Å

α = 96.631 (11)°

β = 97.016 (12)°

γ = 105.060 (12)°

V = 1516.7 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.86 mm−1

T = 296 K

0.16 × 0.14 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.875, T max = 0.904

8123 measured reflections

5295 independent reflections

2785 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.136

S = 1.04

5295 reflections

370 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.64 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, global. DOI: 10.1107/S1600536809042093/rk2173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042093/rk2173Isup2.hkl

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

[Zn(C7H5O2)2(C12H12N2)]·C7H6O2	Z = 2
Mr = 613.96	F(000) = 636
Triclinic, P1	Dx = 1.344 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.974 (6) Å	Cell parameters from 1683 reflections
b = 12.546 (7) Å	θ = 2.5–27.8°
c = 12.798 (8) Å	µ = 0.86 mm−1
α = 96.631 (11)°	T = 296 K
β = 97.016 (12)°	Block, colourless
γ = 105.060 (12)°	0.16 × 0.14 × 0.12 mm
V = 1516.7 (16) Å3

Bruker APEXII CCD area-detector diffractometer	5295 independent reflections
Radiation source: fine-focus sealed tube	2785 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ– and ω–scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→11
Tmin = 0.875, Tmax = 0.904	k = −14→13
8123 measured reflections	l = −15→15

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0455P)2] where P = (Fo2 + 2Fc2)/3
5295 reflections	(Δ/σ)max < 0.001
370 parameters	Δρmax = 0.64 e Å−3
14 restraints	Δρmin = −0.64 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.41555 (6)	0.22239 (5)	0.15235 (4)	0.0561 (2)
N1	0.2722 (4)	0.0734 (3)	0.0835 (3)	0.0509 (10)
N2	0.4792 (4)	0.2028 (3)	0.0057 (3)	0.0461 (10)
O1	0.6236 (4)	0.2621 (4)	0.2360 (3)	0.1060 (12)
O2	0.4751 (4)	0.1472 (3)	0.2994 (3)	0.0945 (13)
O3	0.3506 (4)	0.3454 (3)	0.2070 (3)	0.0708 (10)
O4	0.2026 (4)	0.3185 (3)	0.0566 (2)	0.0672 (10)
O5	0.1962 (4)	0.1688 (3)	0.8042 (3)	0.0760 (11)
O6	0.2806 (4)	0.3497 (3)	0.8688 (3)	0.0717 (10)
H6	0.2520	0.3287	0.9225	0.108*
C1	0.5999 (8)	0.1987 (7)	0.3044 (5)	0.1025 (12)
C2	0.7122 (5)	0.1859 (4)	0.3773 (3)	0.0997 (13)
C3	0.8523 (6)	0.2392 (4)	0.3750 (4)	0.128 (3)
H3	0.8755	0.2882	0.3265	0.153*
C4	0.9579 (4)	0.2192 (5)	0.4450 (5)	0.164 (4)
H4	1.0517	0.2549	0.4434	0.196*
C5	0.9232 (6)	0.1460 (5)	0.5174 (4)	0.172 (5)
H5	0.9938	0.1326	0.5642	0.206*
C6	0.7831 (7)	0.0926 (4)	0.5197 (4)	0.153 (4)
H6A	0.7599	0.0436	0.5681	0.183*
C7	0.6775 (5)	0.1126 (4)	0.4497 (4)	0.111 (3)
H7	0.5837	0.0769	0.4513	0.134*
C8	0.2506 (6)	0.3676 (4)	0.1480 (4)	0.0535 (13)
C9	0.1893 (5)	0.4536 (4)	0.1966 (4)	0.0537 (13)
C10	0.2524 (7)	0.5206 (5)	0.2920 (4)	0.0894 (19)
H10	0.3346	0.5114	0.3277	0.107*
C11	0.1952 (9)	0.6015 (6)	0.3357 (5)	0.116 (2)
H11	0.2383	0.6463	0.4003	0.139*
C12	0.0740 (9)	0.6148 (6)	0.2822 (7)	0.125 (3)
H12	0.0324	0.6668	0.3120	0.150*
C13	0.0151 (7)	0.5522 (6)	0.1864 (7)	0.117 (3)
H13	−0.0654	0.5631	0.1496	0.140*
C14	0.0726 (6)	0.4730 (4)	0.1430 (5)	0.0780 (17)
H14	0.0320	0.4318	0.0763	0.094*
C15	0.2525 (5)	0.2627 (5)	0.7920 (4)	0.0529 (13)
C16	0.2973 (5)	0.2925 (5)	0.6902 (4)	0.0538 (13)
C17	0.3171 (6)	0.3999 (5)	0.6671 (4)	0.0758 (16)
H17	0.3070	0.4564	0.7167	0.091*
C18	0.3528 (7)	0.4224 (6)	0.5677 (5)	0.097 (2)
H18	0.3660	0.4941	0.5508	0.116*
C19	0.3684 (7)	0.3383 (7)	0.4953 (5)	0.098 (2)
H19	0.3910	0.3533	0.4291	0.118*
C20	0.3510 (6)	0.2331 (6)	0.5199 (5)	0.0866 (19)
H20	0.3653	0.1771	0.4720	0.104*
C21	0.3122 (5)	0.2107 (5)	0.6159 (4)	0.0689 (15)
H21	0.2955	0.1380	0.6308	0.083*
C22	0.1317 (6)	0.0689 (5)	0.2271 (4)	0.0847 (18)
H22A	0.2067	0.0747	0.2840	0.127*
H22B	0.0452	0.0241	0.2431	0.127*
H22C	0.1232	0.1421	0.2192	0.127*
C23	0.1631 (6)	0.0156 (5)	0.1256 (4)	0.0633 (15)
C24	0.0820 (6)	−0.0880 (5)	0.0732 (6)	0.0798 (18)
H24	0.0049	−0.1267	0.1009	0.096*
C25	0.1145 (7)	−0.1335 (5)	−0.0189 (6)	0.087 (2)
H25	0.0622	−0.2045	−0.0524	0.105*
C26	0.2243 (6)	−0.0747 (4)	−0.0621 (4)	0.0719 (16)
H26	0.2461	−0.1040	−0.1259	0.086*
C27	0.3021 (5)	0.0296 (4)	−0.0087 (4)	0.0482 (12)
C28	0.4195 (5)	0.1021 (4)	−0.0519 (4)	0.0471 (12)
C29	0.4627 (6)	0.0693 (5)	−0.1451 (4)	0.0648 (15)
H29	0.4218	−0.0020	−0.1832	0.078*
C30	0.5682 (7)	0.1441 (6)	−0.1813 (4)	0.0785 (17)
H30	0.5997	0.1236	−0.2440	0.094*
C31	0.6250 (6)	0.2471 (5)	−0.1248 (5)	0.0753 (16)
H31	0.6951	0.2982	−0.1492	0.090*
C32	0.5798 (6)	0.2774 (4)	−0.0311 (4)	0.0601 (14)
C33	0.6386 (6)	0.3902 (4)	0.0338 (5)	0.095 (2)
H33A	0.5630	0.4200	0.0507	0.142*
H33B	0.6962	0.4388	−0.0060	0.142*
H33C	0.6944	0.3846	0.0985	0.142*

	U11	U22	U33	U12	U13	U23
Zn1	0.0556 (4)	0.0578 (4)	0.0511 (4)	0.0185 (3)	−0.0002 (3)	−0.0035 (3)
N1	0.040 (2)	0.057 (3)	0.053 (3)	0.013 (2)	−0.002 (2)	0.013 (2)
N2	0.038 (2)	0.046 (3)	0.054 (2)	0.016 (2)	0.005 (2)	0.002 (2)
O1	0.0884 (18)	0.162 (3)	0.069 (2)	0.063 (2)	−0.0244 (18)	−0.003 (2)
O2	0.093 (3)	0.124 (3)	0.066 (2)	0.061 (3)	−0.034 (2)	−0.0054 (18)
O3	0.081 (3)	0.074 (2)	0.056 (2)	0.037 (2)	−0.008 (2)	−0.0079 (18)
O4	0.078 (3)	0.075 (2)	0.044 (2)	0.0216 (19)	0.0045 (19)	−0.0047 (18)
O5	0.092 (3)	0.073 (3)	0.065 (2)	0.021 (2)	0.019 (2)	0.014 (2)
O6	0.100 (3)	0.068 (2)	0.051 (2)	0.030 (2)	0.016 (2)	0.0073 (19)
C1	0.086 (2)	0.158 (3)	0.066 (2)	0.065 (2)	−0.0219 (19)	−0.006 (2)
C2	0.084 (2)	0.155 (4)	0.064 (2)	0.066 (2)	−0.021 (2)	−0.007 (2)
C3	0.075 (5)	0.201 (8)	0.097 (5)	0.050 (5)	0.003 (4)	−0.027 (5)
C4	0.096 (6)	0.256 (12)	0.121 (7)	0.078 (7)	−0.032 (6)	−0.055 (7)
C5	0.135 (9)	0.205 (11)	0.155 (9)	0.101 (8)	−0.086 (7)	−0.069 (8)
C6	0.211 (10)	0.094 (6)	0.134 (7)	0.068 (6)	−0.083 (7)	−0.003 (5)
C7	0.117 (6)	0.095 (5)	0.100 (5)	0.043 (4)	−0.057 (5)	−0.030 (4)
C8	0.068 (4)	0.049 (3)	0.042 (3)	0.014 (3)	0.014 (3)	0.003 (3)
C9	0.059 (3)	0.053 (3)	0.047 (3)	0.019 (3)	0.006 (3)	−0.002 (3)
C10	0.120 (5)	0.095 (5)	0.063 (4)	0.058 (4)	0.004 (4)	−0.005 (3)
C11	0.160 (8)	0.120 (6)	0.075 (5)	0.071 (6)	0.012 (5)	−0.024 (4)
C12	0.114 (7)	0.120 (6)	0.147 (7)	0.064 (5)	0.025 (6)	−0.030 (6)
C13	0.071 (5)	0.101 (6)	0.166 (8)	0.039 (4)	−0.012 (5)	−0.033 (5)
C14	0.060 (4)	0.068 (4)	0.096 (4)	0.021 (3)	−0.003 (4)	−0.016 (3)
C15	0.048 (3)	0.059 (4)	0.055 (3)	0.022 (3)	0.005 (3)	0.011 (3)
C16	0.049 (3)	0.066 (4)	0.045 (3)	0.016 (3)	0.002 (3)	0.009 (3)
C17	0.075 (4)	0.082 (5)	0.065 (4)	0.012 (3)	0.011 (3)	0.013 (3)
C18	0.103 (5)	0.101 (5)	0.074 (4)	−0.001 (4)	0.018 (4)	0.028 (4)
C19	0.090 (5)	0.141 (7)	0.055 (4)	0.014 (5)	0.017 (4)	0.018 (5)
C20	0.084 (5)	0.117 (6)	0.060 (4)	0.031 (4)	0.015 (3)	0.002 (4)
C21	0.072 (4)	0.082 (4)	0.054 (3)	0.026 (3)	0.009 (3)	0.006 (3)
C22	0.063 (4)	0.116 (5)	0.078 (4)	0.021 (4)	0.014 (3)	0.026 (4)
C23	0.052 (4)	0.069 (4)	0.069 (4)	0.018 (3)	−0.006 (3)	0.025 (3)
C24	0.058 (4)	0.065 (5)	0.110 (5)	0.003 (3)	0.001 (4)	0.034 (4)
C25	0.075 (5)	0.056 (4)	0.114 (6)	0.004 (4)	−0.017 (4)	0.008 (4)
C26	0.069 (4)	0.054 (4)	0.079 (4)	0.011 (3)	−0.012 (3)	−0.004 (3)
C27	0.046 (3)	0.043 (3)	0.051 (3)	0.015 (3)	−0.012 (3)	0.002 (3)
C28	0.047 (3)	0.046 (3)	0.051 (3)	0.025 (3)	−0.003 (3)	0.000 (3)
C29	0.076 (4)	0.061 (4)	0.060 (4)	0.032 (3)	0.005 (3)	−0.008 (3)
C30	0.096 (5)	0.104 (5)	0.055 (4)	0.053 (4)	0.030 (4)	0.016 (4)
C31	0.073 (4)	0.086 (5)	0.074 (4)	0.030 (4)	0.019 (3)	0.017 (4)
C32	0.060 (4)	0.056 (4)	0.064 (4)	0.019 (3)	0.005 (3)	0.009 (3)
C33	0.099 (5)	0.066 (4)	0.099 (4)	−0.012 (3)	0.023 (4)	0.005 (4)

Zn1—O3	1.917 (3)	C13—H13	0.9300
Zn1—N1	2.059 (4)	C14—H14	0.9300
Zn1—N2	2.062 (4)	C15—C16	1.484 (7)
Zn1—O1	2.120 (4)	C16—C21	1.368 (6)
Zn1—O2	2.283 (4)	C16—C17	1.381 (7)
N1—C27	1.344 (6)	C17—C18	1.402 (7)
N1—C23	1.350 (6)	C17—H17	0.9300
N2—C28	1.335 (5)	C18—C19	1.375 (8)
N2—C32	1.353 (6)	C18—H18	0.9300
O1—C1	1.252 (8)	C19—C20	1.365 (8)
O2—C1	1.235 (8)	C19—H19	0.9300
O3—C8	1.285 (5)	C20—C21	1.369 (7)
O4—C8	1.233 (5)	C20—H20	0.9300
O5—C15	1.204 (5)	C21—H21	0.9300
O6—C15	1.327 (5)	C22—C23	1.496 (7)
O6—H6	0.8200	C22—H22A	0.9600
C1—C2	1.423 (7)	C22—H22B	0.9600
C2—C3	1.3900	C22—H22C	0.9600
C2—C7	1.3900	C23—C24	1.384 (7)
C3—C4	1.3900	C24—C25	1.362 (8)
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.3900	C25—C26	1.368 (8)
C4—H4	0.9300	C25—H25	0.9300
C5—C6	1.3900	C26—C27	1.384 (6)
C5—H5	0.9300	C26—H26	0.9300
C6—C7	1.3900	C27—C28	1.492 (6)
C6—H6A	0.9300	C28—C29	1.372 (6)
C7—H7	0.9300	C29—C30	1.382 (7)
C8—C9	1.485 (7)	C29—H29	0.9300
C9—C14	1.369 (6)	C30—C31	1.349 (7)
C9—C10	1.377 (6)	C30—H30	0.9300
C10—C11	1.384 (8)	C31—C32	1.379 (7)
C10—H10	0.9300	C31—H31	0.9300
C11—C12	1.374 (9)	C32—C33	1.488 (7)
C11—H11	0.9300	C33—H33A	0.9600
C12—C13	1.352 (8)	C33—H33B	0.9600
C12—H12	0.9300	C33—H33C	0.9600
C13—C14	1.369 (8)
O3—Zn1—N1	119.74 (16)	O5—C15—C16	123.5 (5)
O3—Zn1—N2	124.65 (15)	O6—C15—C16	113.6 (5)
N1—Zn1—N2	80.07 (17)	C21—C16—C17	119.5 (5)
O3—Zn1—O1	102.78 (16)	C21—C16—C15	119.1 (5)
N1—Zn1—O1	132.61 (16)	C17—C16—C15	121.3 (5)
N2—Zn1—O1	93.04 (16)	C16—C17—C18	119.0 (6)
O3—Zn1—O2	104.33 (15)	C16—C17—H17	120.5
N1—Zn1—O2	91.25 (15)	C18—C17—H17	120.5
N2—Zn1—O2	127.89 (14)	C19—C18—C17	120.0 (6)
O1—Zn1—O2	56.64 (17)	C19—C18—H18	120.0
C27—N1—C23	119.8 (4)	C17—C18—H18	120.0
C27—N1—Zn1	113.4 (3)	C20—C19—C18	120.4 (6)
C23—N1—Zn1	126.6 (4)	C20—C19—H19	119.8
C28—N2—C32	119.6 (4)	C18—C19—H19	119.8
C28—N2—Zn1	113.8 (3)	C19—C20—C21	119.4 (6)
C32—N2—Zn1	126.4 (3)	C19—C20—H20	120.3
C1—O1—Zn1	98.0 (4)	C21—C20—H20	120.3
C1—O2—Zn1	90.6 (4)	C20—C21—C16	121.6 (6)
C8—O3—Zn1	117.4 (3)	C20—C21—H21	119.2
C15—O6—H6	109.5	C16—C21—H21	119.2
O2—C1—O1	114.7 (6)	C23—C22—H22A	109.5
O2—C1—C2	124.5 (7)	C23—C22—H22B	109.5
O1—C1—C2	120.8 (7)	H22A—C22—H22B	109.5
C3—C2—C7	120.0	C23—C22—H22C	109.5
C3—C2—C1	122.6 (5)	H22A—C22—H22C	109.5
C7—C2—C1	117.3 (5)	H22B—C22—H22C	109.5
C4—C3—C2	120.0	N1—C23—C24	119.8 (5)
C4—C3—H3	120.0	N1—C23—C22	117.9 (5)
C2—C3—H3	120.0	C24—C23—C22	122.2 (6)
C3—C4—C5	120.0	C25—C24—C23	120.2 (6)
C3—C4—H4	120.0	C25—C24—H24	119.9
C5—C4—H4	120.0	C23—C24—H24	119.9
C4—C5—C6	120.0	C24—C25—C26	120.0 (6)
C4—C5—H5	120.0	C24—C25—H25	120.0
C6—C5—H5	120.0	C26—C25—H25	120.0
C7—C6—C5	120.0	C25—C26—C27	118.4 (6)
C7—C6—H6A	120.0	C25—C26—H26	120.8
C5—C6—H6A	120.0	C27—C26—H26	120.8
C6—C7—C2	120.0	N1—C27—C26	121.7 (5)
C6—C7—H7	120.0	N1—C27—C28	115.9 (4)
C2—C7—H7	120.0	C26—C27—C28	122.4 (5)
O4—C8—O3	123.0 (5)	N2—C28—C29	121.7 (5)
O4—C8—C9	120.3 (5)	N2—C28—C27	115.4 (4)
O3—C8—C9	116.7 (4)	C29—C28—C27	122.9 (5)
C14—C9—C10	118.3 (5)	C28—C29—C30	118.8 (5)
C14—C9—C8	120.0 (5)	C28—C29—H29	120.6
C10—C9—C8	121.6 (5)	C30—C29—H29	120.6
C9—C10—C11	121.0 (6)	C31—C30—C29	119.3 (5)
C9—C10—H10	119.5	C31—C30—H30	120.4
C11—C10—H10	119.5	C29—C30—H30	120.4
C12—C11—C10	119.1 (6)	C30—C31—C32	120.5 (6)
C12—C11—H11	120.5	C30—C31—H31	119.7
C10—C11—H11	120.5	C32—C31—H31	119.7
C13—C12—C11	120.0 (7)	N2—C32—C31	120.0 (5)
C13—C12—H12	120.0	N2—C32—C33	117.5 (5)
C11—C12—H12	120.0	C31—C32—C33	122.5 (5)
C12—C13—C14	120.8 (7)	C32—C33—H33A	109.5
C12—C13—H13	119.6	C32—C33—H33B	109.5
C14—C13—H13	119.6	H33A—C33—H33B	109.5
C9—C14—C13	120.8 (6)	C32—C33—H33C	109.5
C9—C14—H14	119.6	H33A—C33—H33C	109.5
C13—C14—H14	119.6	H33B—C33—H33C	109.5
O5—C15—O6	122.9 (5)
O3—Zn1—N1—C27	134.4 (3)	C8—C9—C10—C11	179.1 (6)
N2—Zn1—N1—C27	10.0 (3)	C9—C10—C11—C12	−0.2 (11)
O1—Zn1—N1—C27	−74.9 (4)	C10—C11—C12—C13	−2.5 (13)
O2—Zn1—N1—C27	−118.3 (3)	C11—C12—C13—C14	1.9 (13)
O3—Zn1—N1—C23	−50.8 (4)	C10—C9—C14—C13	−4.0 (9)
N2—Zn1—N1—C23	−175.2 (4)	C8—C9—C14—C13	−179.8 (6)
O1—Zn1—N1—C23	99.9 (4)	C12—C13—C14—C9	1.4 (11)
O2—Zn1—N1—C23	56.5 (4)	O5—C15—C16—C21	−18.5 (7)
O3—Zn1—N2—C28	−130.2 (3)	O6—C15—C16—C21	161.4 (4)
N1—Zn1—N2—C28	−10.8 (3)	O5—C15—C16—C17	158.1 (5)
O1—Zn1—N2—C28	122.0 (3)	O6—C15—C16—C17	−22.0 (6)
O2—Zn1—N2—C28	73.0 (3)	C21—C16—C17—C18	−0.3 (8)
O3—Zn1—N2—C32	55.2 (4)	C15—C16—C17—C18	−176.9 (5)
N1—Zn1—N2—C32	174.6 (4)	C16—C17—C18—C19	−0.4 (9)
O1—Zn1—N2—C32	−52.6 (4)	C17—C18—C19—C20	−0.8 (10)
O2—Zn1—N2—C32	−101.6 (4)	C18—C19—C20—C21	2.6 (10)
O3—Zn1—O1—C1	100.7 (4)	C19—C20—C21—C16	−3.4 (9)
N1—Zn1—O1—C1	−53.5 (5)	C17—C16—C21—C20	2.2 (8)
N2—Zn1—O1—C1	−132.8 (4)	C15—C16—C21—C20	178.9 (5)
O2—Zn1—O1—C1	1.8 (4)	C27—N1—C23—C24	−0.5 (7)
O3—Zn1—O2—C1	−97.8 (4)	Zn1—N1—C23—C24	−175.0 (4)
N1—Zn1—O2—C1	141.0 (4)	C27—N1—C23—C22	−178.6 (4)
N2—Zn1—O2—C1	62.6 (4)	Zn1—N1—C23—C22	6.9 (6)
O1—Zn1—O2—C1	−1.8 (4)	N1—C23—C24—C25	2.1 (8)
N1—Zn1—O3—C8	−45.9 (4)	C22—C23—C24—C25	−179.9 (5)
N2—Zn1—O3—C8	52.9 (4)	C23—C24—C25—C26	−2.7 (9)
O1—Zn1—O3—C8	155.8 (3)	C24—C25—C26—C27	1.6 (8)
O2—Zn1—O3—C8	−145.8 (3)	C23—N1—C27—C26	−0.6 (6)
Zn1—O2—C1—O1	2.8 (6)	Zn1—N1—C27—C26	174.6 (3)
Zn1—O2—C1—C2	−174.3 (6)	C23—N1—C27—C28	176.8 (4)
Zn1—O1—C1—O2	−3.0 (7)	Zn1—N1—C27—C28	−7.9 (5)
Zn1—O1—C1—C2	174.2 (5)	C25—C26—C27—N1	0.1 (7)
O2—C1—C2—C3	175.0 (5)	C25—C26—C27—C28	−177.2 (5)
O1—C1—C2—C3	−1.9 (8)	C32—N2—C28—C29	3.7 (6)
O2—C1—C2—C7	−2.0 (8)	Zn1—N2—C28—C29	−171.4 (3)
O1—C1—C2—C7	−178.9 (5)	C32—N2—C28—C27	−175.3 (4)
C7—C2—C3—C4	0.0	Zn1—N2—C28—C27	9.7 (4)
C1—C2—C3—C4	−176.9 (5)	N1—C27—C28—N2	−1.2 (5)
C2—C3—C4—C5	0.0	C26—C27—C28—N2	176.3 (4)
C3—C4—C5—C6	0.0	N1—C27—C28—C29	179.9 (4)
C4—C5—C6—C7	0.0	C26—C27—C28—C29	−2.7 (7)
C5—C6—C7—C2	0.0	N2—C28—C29—C30	−1.8 (7)
C3—C2—C7—C6	0.0	C27—C28—C29—C30	177.1 (4)
C1—C2—C7—C6	177.1 (4)	C28—C29—C30—C31	−0.5 (8)
Zn1—O3—C8—O4	−5.0 (6)	C29—C30—C31—C32	0.8 (8)
Zn1—O3—C8—C9	172.6 (3)	C28—N2—C32—C31	−3.3 (7)
O4—C8—C9—C14	4.8 (7)	Zn1—N2—C32—C31	171.1 (3)
O3—C8—C9—C14	−172.9 (5)	C28—N2—C32—C33	177.4 (4)
O4—C8—C9—C10	−170.8 (5)	Zn1—N2—C32—C33	−8.2 (6)
O3—C8—C9—C10	11.5 (7)	C30—C31—C32—N2	1.0 (8)
C14—C9—C10—C11	3.4 (9)	C30—C31—C32—C33	−179.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···O5i	0.93	2.44	3.340 (8)	162
C33—H33C···O1	0.96	2.52	3.199 (8)	128
C22—H22A···O2	0.96	2.57	3.289 (7)	132
O6—H6···O4ii	0.82	1.85	2.655 (5)	166
C31—H31···Cg1iii	0.93	2.79	3.708 (7)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24⋯O5i	0.93	2.44	3.340 (8)	162
C33—H33C⋯O1	0.96	2.52	3.199 (8)	128
C22—H22A⋯O2	0.96	2.57	3.289 (7)	132
O6—H6⋯O4ii	0.82	1.85	2.655 (5)	166
C31—H31⋯Cg1iii	0.93	2.79	3.708 (7)	170

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C9–C14 ring.