A new ZnII coordination polymer based on 4-(pyridin-4-yl)benzoic and formic acids: in-situ synthesis, crystal structure and luminescence properties

Luo, F.; Tang, G.; Zhang, J.

doi:10.1107/S205322961801269X

A new Zn^II coordination polymer based on 4-(pyridin-4-yl)benzoic and formic acids: in-situ synthesis, crystal structure and luminescence properties

The title compound, poly[(μ₂-formato-κ³O,O′:O)[μ₂-4-(pyridin-4-yl)benzoato-κ³N:O,O′]zinc(II)], [Zn(C₁₂H₈NO₂)(HCOO)]_n, has been synthesized in situ and characterized by thermogravimetric analysis (TGA) and single-crystal and powder X-ray diffraction analyses. The polymer contains two independent structural units in the asymmetric unit. These are constructed from Zn²⁺ ions, 4-(pyridin-4-yl)benzoate (4-pbc) bridges and in-situ-generated formate ligands, forming two similar two-dimensional (2D) layer structures. These similar 2D layers are arranged alternately and are linked with each other by dense C—H

O hydrogen bonds to generate a three-dimensional (3D) supramolecular framework. The crystal is pseudomerohedrally twinned about [201]. Compared with free 4-Hpbc, the polymer exhibits a red shift and significantly enhanced solid-state luminescence properties.

Keywords: two-dimensional coordination polymer; zinc(II); crystal structure; PXRD; luminescence; in-situ synthesis; Z′ > 1.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961801269X/sk3707sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961801269X/sk3707Isup2.hkl Contains datablock I

CCDC reference: 1864567

Computing details top

Data collection: APEX2 (Bruker, 2015); cell refinement: APEX2 (Bruker, 2015); data reduction: APEX2 (Bruker, 2015); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: SHELXL2016 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015).

Poly[(µ₂-formato-κ³O,O':O)[µ₂-4-(pyridin-4-yl)benzoato-κ³N:O,O']zinc(II)] top

Crystal data top

[Zn(C₁₂H₈NO₂)(CHO₂)]	F(000) = 1248
M_r = 308.58	D_x = 1.737 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.8902 (8) Å	Cell parameters from 7847 reflections
b = 21.9049 (13) Å	θ = 3.1–26.1°
c = 8.8786 (5) Å	µ = 2.09 mm⁻¹
β = 109.699 (3)°	T = 150 K
V = 2360.2 (2) Å³	Block, colorless
Z = 8	0.24 × 0.17 × 0.13 mm

Data collection top

Bruker APEXII CCD diffractometer	3581 reflections with I > 2σ(I)
ω scans	R_int = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2015)	θ_max = 26.1°, θ_min = 3.1°
T_min = 0.655, T_max = 0.745	h = −15→13
7683 measured reflections	k = −27→24
4661 independent reflections	l = −10→10

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + 0.7028P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
4661 reflections	Δρ_max = 0.32 e Å⁻³
344 parameters	Δρ_min = −0.37 e Å⁻³

Special details top

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. Refined as a 2-component twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1A	0.29437 (3)	0.25250 (2)	0.45181 (6)	0.01722 (13)
O1A	0.4444 (2)	0.26094 (12)	0.4332 (4)	0.0262 (7)
O2A	0.3340 (2)	0.24687 (11)	0.1889 (3)	0.0202 (6)
O3A	0.1578 (2)	0.20268 (11)	0.3747 (4)	0.0266 (7)
O4A	0.3009 (2)	0.14101 (12)	0.4436 (4)	0.0298 (7)
N1A	−0.2178 (2)	−0.16365 (13)	0.1039 (4)	0.0184 (7)
C1A	0.2009 (3)	0.14956 (16)	0.3893 (5)	0.0200 (8)
C2A	0.1238 (3)	0.09661 (16)	0.3392 (5)	0.0213 (9)
C3A	0.0136 (3)	0.10108 (16)	0.3249 (5)	0.0256 (9)
H3A	−0.014723	0.138808	0.346907	0.031*
C4A	−0.0560 (3)	0.05076 (16)	0.2786 (5)	0.0249 (9)
H4A	−0.131035	0.053987	0.271469	0.030*
C5A	−0.0150 (3)	−0.00510 (16)	0.2421 (5)	0.0220 (9)
C6A	0.0943 (3)	−0.00846 (16)	0.2537 (5)	0.0229 (9)
H6A	0.122624	−0.045442	0.227248	0.027*
C7A	0.1633 (3)	0.04161 (16)	0.3038 (5)	0.0230 (9)
H7A	0.238831	0.038113	0.313886	0.028*
C8A	−0.0873 (3)	−0.05875 (16)	0.1904 (5)	0.0194 (8)
C9A	−0.1735 (3)	−0.07036 (16)	0.2483 (5)	0.0223 (9)
H9A	−0.189647	−0.042272	0.318888	0.027*
C10A	−0.2358 (3)	−0.12355 (16)	0.2018 (5)	0.0230 (9)
H10A	−0.293785	−0.130985	0.242929	0.028*
C11A	−0.1361 (3)	−0.15237 (16)	0.0447 (5)	0.0229 (9)
H11A	−0.123609	−0.180828	−0.028095	0.027*
C12A	−0.0700 (3)	−0.10138 (16)	0.0853 (5)	0.0218 (9)
H12A	−0.012827	−0.095373	0.041626	0.026*
C13A	0.4285 (3)	0.25442 (16)	0.2881 (6)	0.0205 (8)
H13A	0.489800	0.255196	0.251526	0.025*
Zn1B	0.79699 (3)	0.25029 (2)	0.34564 (6)	0.01667 (12)
O1B	0.9470 (2)	0.24106 (12)	0.5070 (4)	0.0250 (6)
O2B	0.8355 (2)	0.24882 (11)	0.6455 (4)	0.0212 (6)
O3B	0.6696 (2)	0.30528 (11)	0.2951 (3)	0.0244 (7)
O4B	0.8143 (2)	0.36496 (12)	0.3842 (4)	0.0319 (7)
N1B	0.2855 (3)	0.66856 (13)	0.1826 (4)	0.0198 (7)
C1B	0.7131 (3)	0.35771 (16)	0.3307 (5)	0.0212 (9)
C2B	0.6369 (3)	0.41115 (16)	0.3048 (5)	0.0192 (8)
C3B	0.5293 (3)	0.40782 (15)	0.2027 (5)	0.0208 (8)
H3B	0.502311	0.370641	0.148656	0.025*
C4B	0.4609 (3)	0.45747 (16)	0.1783 (5)	0.0207 (8)
H4B	0.387704	0.454446	0.105330	0.025*
C5B	0.4968 (3)	0.51215 (16)	0.2583 (5)	0.0199 (8)
C6B	0.6056 (3)	0.51592 (16)	0.3628 (5)	0.0224 (9)
H6B	0.632030	0.552881	0.418552	0.027*
C7B	0.6745 (3)	0.46614 (16)	0.3852 (5)	0.0246 (9)
H7B	0.748440	0.469152	0.455850	0.030*
C8B	0.4224 (3)	0.56611 (16)	0.2331 (5)	0.0197 (8)
C9B	0.3397 (3)	0.57604 (17)	0.0880 (5)	0.0246 (9)
H9B	0.328115	0.547521	0.003325	0.030*
C10B	0.2743 (3)	0.62731 (17)	0.0665 (5)	0.0248 (9)
H10B	0.218931	0.633672	−0.034637	0.030*
C11B	0.3654 (3)	0.65913 (17)	0.3236 (5)	0.0224 (9)
H11B	0.375014	0.688267	0.406412	0.027*
C12B	0.4337 (3)	0.60935 (17)	0.3533 (5)	0.0236 (9)
H12B	0.488538	0.604242	0.455423	0.028*
C13B	0.9303 (3)	0.24473 (15)	0.6376 (6)	0.0218 (9)
H13B	0.991645	0.244389	0.733979	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1A	0.0162 (2)	0.0135 (2)	0.0199 (3)	−0.00069 (17)	0.0034 (2)	0.00040 (18)
O1A	0.0208 (13)	0.0370 (16)	0.0196 (17)	−0.0073 (12)	0.0053 (13)	−0.0037 (13)
O2A	0.0186 (13)	0.0239 (13)	0.0180 (16)	−0.0018 (11)	0.0060 (12)	0.0006 (11)
O3A	0.0226 (13)	0.0150 (12)	0.0380 (19)	−0.0032 (11)	0.0049 (13)	−0.0014 (12)
O4A	0.0205 (14)	0.0239 (14)	0.0400 (19)	−0.0030 (12)	0.0034 (14)	−0.0027 (13)
N1A	0.0197 (15)	0.0129 (14)	0.0213 (19)	0.0009 (13)	0.0050 (14)	0.0027 (13)
C1A	0.024 (2)	0.0174 (17)	0.016 (2)	0.0006 (16)	0.0030 (17)	0.0045 (15)
C2A	0.024 (2)	0.0153 (17)	0.023 (2)	0.0025 (15)	0.0052 (17)	0.0021 (15)
C3A	0.0246 (19)	0.0153 (17)	0.037 (3)	0.0027 (16)	0.0111 (19)	−0.0028 (18)
C4A	0.0222 (19)	0.0188 (18)	0.034 (3)	−0.0004 (16)	0.0094 (18)	−0.0025 (17)
C5A	0.027 (2)	0.0156 (17)	0.023 (2)	0.0005 (17)	0.0074 (18)	0.0016 (16)
C6A	0.0234 (19)	0.0147 (17)	0.029 (2)	0.0049 (16)	0.0061 (18)	−0.0018 (16)
C7A	0.0209 (18)	0.0196 (18)	0.028 (2)	0.0009 (16)	0.0072 (17)	0.0012 (16)
C8A	0.0213 (19)	0.0146 (16)	0.020 (2)	0.0015 (16)	0.0045 (16)	0.0019 (15)
C9A	0.029 (2)	0.0164 (18)	0.023 (2)	−0.0008 (16)	0.0108 (18)	−0.0035 (16)
C10A	0.0249 (19)	0.0158 (17)	0.029 (2)	0.0009 (16)	0.0098 (19)	0.0017 (16)
C11A	0.029 (2)	0.0161 (17)	0.023 (2)	0.0018 (16)	0.0073 (18)	−0.0019 (16)
C12A	0.0210 (18)	0.0211 (18)	0.025 (2)	0.0008 (16)	0.0103 (17)	0.0005 (16)
C13A	0.0200 (18)	0.0203 (18)	0.023 (2)	−0.0007 (16)	0.0100 (18)	0.0011 (16)
Zn1B	0.0161 (2)	0.0124 (2)	0.0218 (3)	0.00131 (17)	0.0068 (2)	0.00129 (17)
O1B	0.0210 (13)	0.0333 (15)	0.0210 (17)	−0.0001 (12)	0.0076 (13)	−0.0008 (12)
O2B	0.0169 (13)	0.0230 (13)	0.0231 (16)	0.0003 (11)	0.0058 (12)	−0.0007 (11)
O3B	0.0205 (13)	0.0162 (13)	0.0355 (18)	0.0042 (11)	0.0081 (12)	0.0016 (12)
O4B	0.0218 (15)	0.0203 (13)	0.050 (2)	0.0047 (12)	0.0077 (14)	0.0027 (13)
N1B	0.0228 (16)	0.0140 (14)	0.0225 (19)	0.0001 (13)	0.0076 (15)	−0.0008 (13)
C1B	0.023 (2)	0.0182 (18)	0.024 (2)	0.0011 (16)	0.0104 (18)	0.0043 (16)
C2B	0.0232 (19)	0.0149 (17)	0.022 (2)	−0.0016 (16)	0.0103 (17)	0.0029 (16)
C3B	0.0271 (19)	0.0100 (16)	0.027 (2)	−0.0009 (16)	0.0109 (18)	−0.0005 (15)
C4B	0.0140 (17)	0.0191 (17)	0.027 (2)	0.0011 (16)	0.0043 (16)	0.0031 (16)
C5B	0.0257 (19)	0.0153 (16)	0.021 (2)	0.0001 (16)	0.0106 (17)	0.0024 (16)
C6B	0.0215 (19)	0.0172 (17)	0.027 (2)	−0.0007 (16)	0.0063 (17)	−0.0024 (16)
C7B	0.0221 (19)	0.0192 (18)	0.030 (2)	−0.0015 (16)	0.0055 (17)	−0.0008 (16)
C8B	0.0218 (18)	0.0133 (16)	0.025 (2)	−0.0020 (15)	0.0092 (17)	0.0020 (16)
C9B	0.031 (2)	0.0166 (18)	0.025 (2)	0.0020 (17)	0.0075 (18)	−0.0031 (16)
C10B	0.029 (2)	0.0189 (17)	0.023 (2)	0.0039 (17)	0.0041 (18)	−0.0010 (16)
C11B	0.0239 (19)	0.0204 (18)	0.023 (2)	0.0012 (16)	0.0078 (17)	−0.0050 (16)
C12B	0.0242 (19)	0.0198 (18)	0.023 (2)	−0.0003 (16)	0.0028 (17)	−0.0034 (16)
C13B	0.0203 (18)	0.0193 (18)	0.021 (2)	−0.0025 (15)	0.0012 (18)	0.0019 (16)

Geometric parameters (Å, º) top

Zn1A—O3A	1.986 (3)	Zn1B—O3B	1.962 (2)
Zn1A—O2A	2.555 (3)	Zn1B—O1B	1.991 (3)
Zn1A—O2Aⁱ	1.992 (3)	Zn1B—O2B	2.539 (2)
Zn1A—O1A	2.005 (3)	Zn1B—O2Bⁱⁱⁱ	2.000 (3)
Zn1A—N1Aⁱⁱ	2.065 (3)	Zn1B—N1B^iv	2.054 (3)
Zn1A—O4A	2.446 (3)	Zn1B—C1B	2.574 (4)
Zn1A—C1A	2.529 (4)	Zn1B—C13B	2.585 (4)
O1A—C13A	1.243 (6)	O1B—C13B	1.251 (6)
O2A—C13A	1.251 (5)	O2B—C13B	1.250 (5)
O3A—C1A	1.277 (4)	O3B—C1B	1.270 (4)
O4A—C1A	1.229 (4)	O4B—C1B	1.238 (5)
N1A—C10A	1.310 (5)	N1B—C10B	1.341 (5)
N1A—C11A	1.349 (5)	N1B—C11B	1.342 (5)
C1A—C2A	1.494 (5)	C1B—C2B	1.495 (5)
C2A—C7A	1.385 (5)	C2B—C3B	1.379 (5)
C2A—C3A	1.386 (5)	C2B—C7B	1.401 (5)
C3A—C4A	1.393 (5)	C3B—C4B	1.370 (5)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.413 (5)	C4B—C5B	1.390 (5)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.379 (5)	C5B—C6B	1.400 (5)
C5A—C8A	1.474 (5)	C5B—C8B	1.491 (5)
C6A—C7A	1.388 (5)	C6B—C7B	1.378 (5)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—H7A	0.9500	C7B—H7B	0.9500
C8A—C12A	1.390 (5)	C8B—C9B	1.384 (5)
C8A—C9A	1.397 (5)	C8B—C12B	1.397 (5)
C9A—C10A	1.396 (5)	C9B—C10B	1.379 (5)
C9A—H9A	0.9499	C9B—H9B	0.9501
C10A—H10A	0.9499	C10B—H10B	0.9500
C11A—C12A	1.377 (5)	C11B—C12B	1.370 (5)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
Zn1B—O4B	2.535 (3)

O3A—Zn1A—O2Aⁱ	104.48 (12)	O3B—Zn1B—O2Bⁱⁱⁱ	103.31 (11)
O3A—Zn1A—O1A	142.16 (12)	O1B—Zn1B—O2Bⁱⁱⁱ	99.69 (12)
O2Aⁱ—Zn1A—O1A	100.11 (12)	O3B—Zn1B—N1B^iv	98.51 (11)
O3A—Zn1A—N1Aⁱⁱ	96.31 (11)	O1B—Zn1B—N1B^iv	109.67 (12)
O2Aⁱ—Zn1A—N1Aⁱⁱ	100.28 (12)	O2Bⁱⁱⁱ—Zn1B—N1B^iv	100.00 (11)
O1A—Zn1A—N1Aⁱⁱ	107.14 (12)	O3B—Zn1B—C1B	28.68 (11)
O3A—Zn1A—O4A	58.43 (9)	O1B—Zn1B—C1B	114.77 (12)
O2Aⁱ—Zn1A—O4A	92.25 (10)	O2Bⁱⁱⁱ—Zn1B—C1B	99.86 (11)
O1A—Zn1A—O4A	92.63 (10)	N1B^iv—Zn1B—C1B	126.81 (12)
N1Aⁱⁱ—Zn1A—O4A	154.13 (10)	O3B—Zn1B—C13B	118.69 (12)
O3A—Zn1A—C1A	29.89 (11)	O1B—Zn1B—C13B	28.10 (14)
O2Aⁱ—Zn1A—C1A	99.88 (12)	O2Bⁱⁱⁱ—Zn1B—C13B	127.68 (13)
O1A—Zn1A—C1A	117.77 (12)	N1B^iv—Zn1B—C13B	102.88 (12)
N1Aⁱⁱ—Zn1A—C1A	125.94 (12)	C1B—Zn1B—C13B	102.73 (12)
O4A—Zn1A—C1A	28.55 (10)	C13B—O1B—Zn1B	103.3 (3)
C13A—O1A—Zn1A	104.4 (3)	C13B—O2B—Zn1Bⁱ	126.2 (3)
C13A—O2A—Zn1Aⁱⁱⁱ	125.8 (3)	C1B—O3B—Zn1B	103.5 (2)
C1A—O3A—Zn1A	99.3 (2)	C10B—N1B—C11B	117.6 (3)
C1A—O4A—Zn1A	79.5 (2)	C10B—N1B—Zn1B^vi	125.2 (3)
C10A—N1A—C11A	118.1 (3)	C11B—N1B—Zn1B^vi	116.8 (2)
C10A—N1A—Zn1A^v	125.3 (3)	O4B—C1B—O3B	122.1 (4)
C11A—N1A—Zn1A^v	116.3 (2)	O4B—C1B—C2B	120.7 (3)
O4A—C1A—O3A	122.8 (3)	O3B—C1B—C2B	117.2 (3)
O4A—C1A—C2A	120.2 (3)	O4B—C1B—Zn1B	74.2 (2)
O3A—C1A—C2A	117.0 (3)	O3B—C1B—Zn1B	47.85 (17)
O4A—C1A—Zn1A	72.0 (2)	C2B—C1B—Zn1B	165.1 (3)
O3A—C1A—Zn1A	50.82 (17)	C3B—C2B—C7B	118.6 (3)
C2A—C1A—Zn1A	167.8 (3)	C3B—C2B—C1B	121.5 (3)
C7A—C2A—C3A	119.0 (4)	C7B—C2B—C1B	119.9 (3)
C7A—C2A—C1A	118.9 (3)	C4B—C3B—C2B	120.9 (3)
C3A—C2A—C1A	122.1 (3)	C4B—C3B—H3B	119.6
C2A—C3A—C4A	120.6 (3)	C2B—C3B—H3B	119.6
C2A—C3A—H3A	119.7	C3B—C4B—C5B	121.2 (4)
C4A—C3A—H3A	119.7	C3B—C4B—H4B	119.4
C3A—C4A—C5A	119.9 (4)	C5B—C4B—H4B	119.4
C3A—C4A—H4A	120.0	C4B—C5B—C6B	118.4 (3)
C5A—C4A—H4A	120.0	C4B—C5B—C8B	121.4 (4)
C6A—C5A—C4A	118.7 (3)	C6B—C5B—C8B	120.2 (3)
C6A—C5A—C8A	120.2 (3)	C7B—C6B—C5B	120.1 (4)
C4A—C5A—C8A	121.0 (3)	C7B—C6B—H6B	119.9
C5A—C6A—C7A	120.7 (3)	C5B—C6B—H6B	119.9
C5A—C6A—H6A	119.7	C6B—C7B—C2B	120.7 (4)
C7A—C6A—H6A	119.7	C6B—C7B—H7B	119.6
C2A—C7A—C6A	121.0 (4)	C2B—C7B—H7B	119.6
C2A—C7A—H7A	119.5	C9B—C8B—C12B	117.0 (3)
C6A—C7A—H7A	119.5	C9B—C8B—C5B	121.2 (4)
C12A—C8A—C9A	116.9 (3)	C12B—C8B—C5B	121.8 (4)
C12A—C8A—C5A	121.2 (3)	C10B—C9B—C8B	120.0 (4)
C9A—C8A—C5A	121.9 (3)	C10B—C9B—H9B	120.0
C10A—C9A—C8A	119.5 (4)	C8B—C9B—H9B	120.0
C10A—C9A—H9A	120.2	N1B—C10B—C9B	122.6 (4)
C8A—C9A—H9A	120.2	N1B—C10B—H10B	118.7
N1A—C10A—C9A	122.9 (4)	C9B—C10B—H10B	118.7
N1A—C10A—H10A	118.6	N1B—C11B—C12B	122.9 (4)
C9A—C10A—H10A	118.6	N1B—C11B—H11B	118.5
N1A—C11A—C12A	122.9 (4)	C12B—C11B—H11B	118.5
N1A—C11A—H11A	118.6	C11B—C12B—C8B	119.8 (4)
C12A—C11A—H11A	118.6	C11B—C12B—H12B	120.1
C11A—C12A—C8A	119.7 (4)	C8B—C12B—H12B	120.1
C11A—C12A—H12A	120.2	O2B—C13B—O1B	122.3 (4)
C8A—C12A—H12A	120.2	O2B—C13B—Zn1B	73.8 (2)
O1A—C13A—O2A	121.7 (4)	O1B—C13B—Zn1B	48.6 (2)
O1A—C13A—H13A	119.1	O2B—C13B—H13B	118.9
O2A—C13A—H13A	119.1	O1B—C13B—H13B	118.9
O3B—Zn1B—O1B	139.61 (11)	Zn1B—C13B—H13B	166.9

Zn1A—O4A—C1A—O3A	−1.6 (4)	Zn1B—O3B—C1B—O4B	−0.1 (5)
Zn1A—O4A—C1A—C2A	179.2 (4)	Zn1B—O3B—C1B—C2B	179.6 (3)
Zn1A—O3A—C1A—O4A	2.0 (5)	O4B—C1B—C2B—C3B	159.6 (4)
Zn1A—O3A—C1A—C2A	−178.8 (3)	O3B—C1B—C2B—C3B	−20.1 (6)
O4A—C1A—C2A—C7A	−21.3 (6)	Zn1B—C1B—C2B—C3B	−19.0 (14)
O3A—C1A—C2A—C7A	159.5 (4)	O4B—C1B—C2B—C7B	−20.3 (6)
Zn1A—C1A—C2A—C7A	155.2 (12)	O3B—C1B—C2B—C7B	160.0 (4)
O4A—C1A—C2A—C3A	159.6 (4)	Zn1B—C1B—C2B—C7B	161.1 (9)
O3A—C1A—C2A—C3A	−19.6 (6)	C7B—C2B—C3B—C4B	0.9 (6)
Zn1A—C1A—C2A—C3A	−23.9 (16)	C1B—C2B—C3B—C4B	−179.0 (4)
C7A—C2A—C3A—C4A	1.2 (7)	C2B—C3B—C4B—C5B	−1.6 (6)
C1A—C2A—C3A—C4A	−179.7 (4)	C3B—C4B—C5B—C6B	1.2 (6)
C2A—C3A—C4A—C5A	−1.5 (7)	C3B—C4B—C5B—C8B	−179.5 (4)
C3A—C4A—C5A—C6A	0.1 (6)	C4B—C5B—C6B—C7B	−0.2 (6)
C3A—C4A—C5A—C8A	−179.0 (4)	C8B—C5B—C6B—C7B	−179.5 (4)
C4A—C5A—C6A—C7A	1.4 (6)	C5B—C6B—C7B—C2B	−0.4 (6)
C8A—C5A—C6A—C7A	−179.4 (4)	C3B—C2B—C7B—C6B	0.0 (6)
C3A—C2A—C7A—C6A	0.4 (6)	C1B—C2B—C7B—C6B	180.0 (4)
C1A—C2A—C7A—C6A	−178.8 (4)	C4B—C5B—C8B—C9B	−30.5 (6)
C5A—C6A—C7A—C2A	−1.7 (6)	C6B—C5B—C8B—C9B	148.8 (4)
C6A—C5A—C8A—C12A	−30.6 (6)	C4B—C5B—C8B—C12B	150.5 (4)
C4A—C5A—C8A—C12A	148.6 (4)	C6B—C5B—C8B—C12B	−30.3 (6)
C6A—C5A—C8A—C9A	147.2 (4)	C12B—C8B—C9B—C10B	1.1 (6)
C4A—C5A—C8A—C9A	−33.7 (6)	C5B—C8B—C9B—C10B	−178.0 (4)
C12A—C8A—C9A—C10A	1.2 (5)	C11B—N1B—C10B—C9B	1.1 (6)
C5A—C8A—C9A—C10A	−176.6 (4)	Zn1B^vi—N1B—C10B—C9B	173.3 (3)
C11A—N1A—C10A—C9A	−0.7 (6)	C8B—C9B—C10B—N1B	−1.2 (6)
Zn1A^v—N1A—C10A—C9A	173.0 (3)	C10B—N1B—C11B—C12B	−0.9 (6)
C8A—C9A—C10A—N1A	−0.5 (6)	Zn1B^vi—N1B—C11B—C12B	−173.8 (3)
C10A—N1A—C11A—C12A	1.3 (5)	N1B—C11B—C12B—C8B	0.8 (6)
Zn1A^v—N1A—C11A—C12A	−173.0 (3)	C9B—C8B—C12B—C11B	−0.9 (6)
N1A—C11A—C12A—C8A	−0.6 (6)	C5B—C8B—C12B—C11B	178.2 (4)
C9A—C8A—C12A—C11A	−0.6 (5)	Zn1Bⁱ—O2B—C13B—O1B	175.9 (2)
C5A—C8A—C12A—C11A	177.2 (4)	Zn1Bⁱ—O2B—C13B—Zn1B	179.3 (2)
Zn1A—O1A—C13A—O2A	2.3 (4)	Zn1B—O1B—C13B—O2B	4.3 (4)
Zn1Aⁱⁱⁱ—O2A—C13A—O1A	170.9 (3)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) −x, y−1/2, −z+1/2; (vi) −x+1, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4B—H4B···O4Aⁱⁱⁱ	0.95	2.57	3.217 (5)	126
C6A—H6A···O4B^iv	0.95	2.46	3.398 (5)	171
C11B—H11B···O1A^vii	0.95	2.54	3.189 (5)	126
C12A—H12A···O4B^iv	0.95	2.57	3.298 (5)	134
C13A—H13A···O3B	0.95	2.47	3.282 (5)	143
C13B—H13B···O3A^viii	0.95	2.39	3.194 (5)	143

Symmetry codes: (iii) x, −y+1/2, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (vii) −x+1, −y+1, −z+1; (viii) x+1, −y+1/2, z+1/2.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page