metal-organic papers
m494
Gao, Huo, Liu and Gu [Zn(C9H6O5)(C7H6N2)2] doi:10.1107/S1600536805003661 Acta Cryst.(2005). E61, m494–m495 Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
catena
-Poly[[bis(1
H
-benzimidazole-
j
N
3)zinc(II)]-l
-3-carboxyphenoxyacetato-
j
2O
:
O
000]
Shan Gao,a* Li-Hua Huo,aJi-Wei
Liua,band Chang-Sheng Gua
a
School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People’s Republic of China, andbCollege of
Chemistry and Chemical Technology, Da Qing Petroleum Institute, Da Qing 163318, People’s Republic of China
Correspondence e-mail: shangao67@yahoo.com
Key indicators
Single-crystal X-ray study
T= 295 K
Mean(C–C) = 0.008 A˚
Rfactor = 0.060
wRfactor = 0.151
Data-to-parameter ratio = 17.0
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
In the title one-dimensional polymer, [Zn(C9H6O5
)-(C7H6N2)2]n, the Zn II
center exhibits a deformed tetrahedral coordination geometry defined by two N atoms from two benzimidazole molecules and two carboxyl O atoms from two different 4-carboxyphenoxyacetate groups. Each 4-carboxy-phenoxyacetate ligand acts in a bis-monodentate mode to connect two adjacent ZnII ions, forming a chain structure. Hydrogen bonds serve to connect the chains into a two-dimensional supramolecular network.
Comment
Carboxyphenoxyacetic acids (CPOAH2) can be regarded as a
family of excellent bridging ligands with both rigid and flexible parts, and hence they can be used to form coordination polymers because of their versatile coordination modes and high structural stability. Recently, we have reported the structures of three zincII polymers constructed by 3- or 4-CPOA2 ligands (3- and 4-carboxyphenoxyacetate, respec-tively), namely [Zn(4-CPOA)(2,20-bipy)(H
2O)]n, (II) (Gaoet
al., 2004), [Zn(4-CPOA)(H2O)2]n, (III) (Zhao, Gao et al.,
2005), in which the octahedrally coordinated ZnIIatoms are bridged by 4-CPOA2 ligands, forming a chain structure, as well as {[Zn(4,40-bipy)(H
2O)4](3-CPOA)}n (4,40-bipy is 4,40
-bipyridine), (IV), in which the octahedrally coordinated ZnII atoms are linked by 4,40-bipy ligands into infinite cationic
polymeric chains (Zhao, Gu et al., 2005). In our efforts to investigate the bonding nature of carboxylate-bridged ZnII polymers, we have now synthesized [Zn(3-CPOA)(1H -benz-imidazole)2]n, (I).
As depicted in Fig. 1, the ZnII atom exists in a distorted tetrahedral coordination that is defined by two N atoms from two benzimidazole molecules and two carboxyl O atoms from two different 3-CPOA2 groups. The oxyacetate group is twisted out of the benzene ring plane. Each 3-CPOA2ligand links two adjacent ZnIIatoms, utilizing its two monodentate
carboxyl groups to form a one-dimensional infinite chain structure (Fig. 2). The chains are connected through inter-molecular hydrogen bonds, forming a two-dimensional supramolecular network (Table 2).
Experimental
The title complex was prepared by the addition of stoichiometric amounts of zinc diacetate dihydrate (0.44 g, 5 mmol) and benz-imidazole (0.68 g, 10 mmol) to an aqueous solution of 3-CPOAH2 (0.39 g, 5 mmol), and adjusting the pH to 7 with 0.1MNaOH. The mixture was sealed in a 50 ml Teflon-lined stainless steel bomb and held at 423 K for 3 d. The bomb was cooled slowly to room temperature and colorless prismatic crystals were obtained over several days. Analysis calculated for C23H18N4O5Zn: C 55.72, H 3.66, N 11.30%; found: C 55.86, H 3.62, N 11.33%.
Crystal data
[Zn(C9H6O5)(C7H6N2)2]
Mr= 495.80 Triclinic,P1
a= 10.580 (3) A˚
b= 11.356 (3) A˚
c= 11.492 (3) A˚ = 116.06 (2)
= 100.32 (2)
= 104.936 (14) V= 1128.4 (6) A˚3
Z= 2
Dx= 1.459 Mg m
3
MoKradiation Cell parameters from 8851
reflections = 3.4–27.5
= 1.13 mm1
T= 295 (2) K Prism, colorless 0.370.260.18 mm
Data collection
Rigaku R-AXIS RAPID diffractometer !scans
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)
Tmin= 0.679,Tmax= 0.822 10127 measured reflections
5055 independent reflections 3129 reflections withI> 2(I)
Rint= 0.045 max= 27.5
h=13!13
k=14!14
l=14!14
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.060
wR(F2) = 0.151
S= 1.03 5055 reflections 298 parameters
H-atom parameters constrained
w= 1/[2
(Fo2) + (0.0715P)2 + 0.3509P]
whereP= (Fo2+ 2Fc2)/3 (/)max= 0.001
max= 0.43 e A˚ 3
[image:2.610.312.568.70.142.2]min=0.26 e A˚ 3
Table 1
Selected geometric parameters (A˚ ,).
Zn1—O1 1.942 (3) Zn1—O4i
1.986 (3) Zn1—N1 2.027 (3) Zn1—N3 2.011 (3)
O1—C15 1.266 (4) O2—C15 1.231 (5) O4—C23 1.277 (5) O5—C23 1.232 (5)
O1—Zn1—O4i
110.49 (12) O1—Zn1—N1 105.98 (13) O1—Zn1—N3 119.11 (13)
O4i
—Zn1—N1 100.62 (12) O4i
—Zn1—N3 111.56 (12) N3—Zn1—N1 107.20 (14)
Symmetry code: (i)x;1þy;z.
Table 2
Hydrogen-bonding geometry (A˚ ,).
D—H A D—H H A D A D—H A
N2—H24 O2ii
0.86 1.93 2.747 (5) 158 N4—H25 O5iii
0.86 1.93 2.688 (4) 146
Symmetry codes: (ii) 1x;1y;1z; (iii) 2x;1y;1z.
H atoms were placed in calculated positions, with C—H = 0.93 or 0.97 A˚ , N—H = 0.86 A˚ andUiso(H) = 1.2Ueq(C,N), and were refined in the riding-model approximation.
Data collection:RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics:ORTEPII(Johnson, 1976); software used to prepare material for publication:SHELXL97.
The authors thank the National Natural Science Foundation of China (No. 20101003), the Scientific Fund of Remarkable Teachers of Heilongjiang Province (No. 1054G036) and Heilongjiang University for supporting this work.
References
Gao, S., Gu, C.-S., Huo, L.-H., Liu, J.-W. & Zhao, J.-G. (2004).Acta Cryst.E60, m1906–m1908.
Higashi, T. (1995).ABSCOR.Rigaku Corporation, Tokyo, Japan.
Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Rigaku (1998).RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., 9009 New Trails
Drive, The Woodlands, TX 77381-5209, USA.
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Go¨ttingen, Germany.
Zhao, J.-G., Gao, S., Huo, L.-H. & Ng, S. W. (2005).Acta Cryst.E61, m115– m116.
[image:2.610.46.293.71.232.2]Zhao, J.-G., Gu, C.-S., Huo, L.-H., Liu, J.-W. & Gao, S. (2005).Acta Cryst.E61,
Figure 1
ORTEPIIplot (Johnson, 1976) of the title complex, with displacement ellipsoids drawn at the 30% probability level. See Table 1 for symmetry codes.
Figure 2
[image:2.610.313.566.221.299.2]supporting information
sup-1 Acta Cryst. (2005). E61, m494–m495
supporting information
Acta Cryst. (2005). E61, m494–m495 [https://doi.org/10.1107/S1600536805003661]
catena
-Poly[[bis(1
H
-benzimidazole-
κ
N
3)zinc(II)]-
µ
-3-carboxyphenoxyacetato-κ
2O
:
O
′
]
Shan Gao, Li-Hua Huo, Ji-Wei Liu and Chang-Sheng Gu
catena-Poly[[bis(1H-benzimidazole-κN3)zinc(II)]-µ-3-carboxyphenoxyacetato- κ2O:O′]
Crystal data
[Zn(C9H6O5)(C7H6N2)2]
Mr = 495.80 Triclinic, P1 Hall symbol: -P 1
a = 10.580 (3) Å
b = 11.356 (3) Å
c = 11.492 (3) Å
α = 116.06 (2)°
β = 100.32 (2)°
γ = 104.936 (14)°
V = 1128.4 (6) Å3
Z = 2
F(000) = 508
Dx = 1.459 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 8851 reflections
θ = 3.4–27.5°
µ = 1.13 mm−1
T = 295 K Prism, colorless 0.37 × 0.26 × 0.18 mm
Data collection
Rigaku R-AXIS RAPID diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
Detector resolution: 10 pixels mm-1
ω scans
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)
Tmin = 0.679, Tmax = 0.822
10127 measured reflections 5055 independent reflections 3129 reflections with I > 2σ(I)′
Rint = 0.045
θmax = 27.5°, θmin = 3.1°
h = −13→13
k = −14→14
l = −14→14
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.060
wR(F2) = 0.151
S = 1.03 5055 reflections 298 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0715P)2 + 0.3509P] where P = (Fo2 + 2Fc2)/3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
Zn1 0.74550 (5) 0.89735 (5) 0.68338 (5) 0.05213 (19)
O1 0.8747 (3) 0.8960 (3) 0.8255 (3) 0.0618 (8)
O2 0.8601 (3) 0.6840 (3) 0.6722 (3) 0.0648 (8)
O3 0.9940 (3) 0.6508 (3) 0.8778 (3) 0.0633 (8)
O4 0.7018 (3) 0.0702 (3) 0.7632 (3) 0.0621 (8)
O5 0.9159 (3) 0.1644 (3) 0.7723 (3) 0.0596 (7)
N1 0.5598 (3) 0.7461 (3) 0.6316 (3) 0.0532 (8)
N2 0.3532 (4) 0.5726 (4) 0.5123 (4) 0.0736 (11)
N3 0.7845 (3) 0.8594 (3) 0.5080 (3) 0.0534 (8)
N4 0.9021 (4) 0.8260 (4) 0.3624 (4) 0.0598 (9)
C1 0.4721 (5) 0.6476 (5) 0.5084 (5) 0.0641 (11)
C2 0.4941 (4) 0.7354 (4) 0.7238 (4) 0.0535 (10)
C3 0.5368 (5) 0.8156 (5) 0.8656 (5) 0.0701 (12)
C4 0.4463 (6) 0.7845 (7) 0.9298 (6) 0.0977 (19)
C5 0.3156 (7) 0.6766 (7) 0.8547 (7) 0.0983 (18)
C6 0.2712 (6) 0.5965 (6) 0.7155 (7) 0.0877 (16)
C7 0.3644 (5) 0.6274 (4) 0.6507 (5) 0.0614 (11)
C8 0.8739 (5) 0.8060 (4) 0.4632 (4) 0.0571 (10)
C9 0.7527 (4) 0.9218 (4) 0.4316 (4) 0.0531 (10)
C10 0.6675 (5) 0.9974 (5) 0.4371 (5) 0.0660 (12)
C11 0.6634 (5) 1.0514 (6) 0.3517 (6) 0.0813 (15)
C12 0.7383 (5) 1.0324 (5) 0.2624 (6) 0.0766 (14)
C13 0.8208 (5) 0.9568 (5) 0.2539 (5) 0.0678 (12)
C14 0.8274 (4) 0.9014 (4) 0.3399 (4) 0.0546 (10)
C15 0.8993 (4) 0.7841 (4) 0.7909 (4) 0.0528 (10)
C16 0.9893 (5) 0.7856 (4) 0.9107 (5) 0.0645 (12)
C17 0.8795 (4) 0.5500 (4) 0.8631 (4) 0.0523 (10)
C18 0.7565 (5) 0.5656 (4) 0.8766 (5) 0.0616 (11)
C19 0.6478 (5) 0.4537 (5) 0.8582 (5) 0.0671 (12)
C20 0.6589 (5) 0.3245 (5) 0.8251 (5) 0.0597 (11)
C21 0.7840 (4) 0.3102 (4) 0.8158 (4) 0.0497 (9)
C22 0.8927 (4) 0.4221 (4) 0.8339 (4) 0.0505 (9)
C23 0.8044 (5) 0.1736 (4) 0.7828 (4) 0.0509 (9)
H1 0.4901 0.6314 0.4276 0.077*
H3 0.6240 0.8883 0.9161 0.084*
H4 0.4732 0.8366 1.0253 0.117*
H5 0.2568 0.6588 0.9013 0.118*
H6 0.1834 0.5247 0.6656 0.105*
H8 0.9138 0.7590 0.4978 0.068*
H10 0.6157 1.0106 0.4959 0.079*
H11 0.6078 1.1032 0.3537 0.098*
H12 0.7322 1.0721 0.2071 0.092*
H13 0.8705 0.9430 0.1932 0.081*
H16A 1.0831 0.8531 0.9411 0.077*
supporting information
sup-3 Acta Cryst. (2005). E61, m494–m495
H18 0.7471 0.6513 0.8982 0.074*
H19 0.5657 0.4651 0.8680 0.081*
H20 0.5839 0.2486 0.8094 0.072*
H22 0.9758 0.4118 0.8266 0.061*
H24 0.2833 0.5037 0.4425 0.088*
H25 0.9567 0.7971 0.3197 0.072*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Zn1 0.0602 (3) 0.0454 (3) 0.0551 (3) 0.0173 (2) 0.0207 (2) 0.0301 (2)
O1 0.0742 (19) 0.0387 (14) 0.0608 (19) 0.0150 (14) 0.0068 (15) 0.0256 (13)
O2 0.077 (2) 0.0463 (15) 0.0521 (18) 0.0101 (15) 0.0121 (15) 0.0208 (15)
O3 0.0659 (18) 0.0432 (15) 0.082 (2) 0.0182 (14) 0.0167 (16) 0.0371 (15)
O4 0.0697 (18) 0.0461 (15) 0.078 (2) 0.0186 (14) 0.0332 (16) 0.0366 (15)
O5 0.0656 (19) 0.0557 (16) 0.075 (2) 0.0312 (15) 0.0324 (16) 0.0401 (15)
N1 0.059 (2) 0.0433 (17) 0.051 (2) 0.0153 (16) 0.0148 (17) 0.0232 (17)
N2 0.070 (2) 0.049 (2) 0.067 (3) 0.0058 (19) 0.010 (2) 0.0161 (19)
N3 0.063 (2) 0.0500 (18) 0.057 (2) 0.0218 (17) 0.0222 (18) 0.0335 (17)
N4 0.068 (2) 0.063 (2) 0.065 (2) 0.0335 (19) 0.0318 (19) 0.0383 (19)
C1 0.076 (3) 0.054 (2) 0.057 (3) 0.024 (2) 0.023 (2) 0.023 (2)
C2 0.060 (3) 0.046 (2) 0.054 (3) 0.015 (2) 0.019 (2) 0.029 (2)
C3 0.067 (3) 0.078 (3) 0.057 (3) 0.009 (2) 0.015 (2) 0.039 (3)
C4 0.097 (4) 0.116 (5) 0.063 (3) 0.011 (4) 0.025 (3) 0.049 (3)
C5 0.091 (4) 0.117 (5) 0.094 (5) 0.020 (4) 0.042 (4) 0.065 (4)
C6 0.072 (3) 0.072 (3) 0.100 (5) −0.001 (3) 0.023 (3) 0.048 (3)
C7 0.067 (3) 0.048 (2) 0.061 (3) 0.013 (2) 0.019 (2) 0.028 (2)
C8 0.067 (3) 0.048 (2) 0.062 (3) 0.023 (2) 0.024 (2) 0.031 (2)
C9 0.050 (2) 0.052 (2) 0.052 (2) 0.0112 (19) 0.0133 (19) 0.029 (2)
C10 0.061 (3) 0.080 (3) 0.074 (3) 0.034 (3) 0.027 (2) 0.048 (3)
C11 0.079 (3) 0.093 (4) 0.092 (4) 0.047 (3) 0.026 (3) 0.057 (3)
C12 0.086 (4) 0.082 (3) 0.078 (3) 0.035 (3) 0.023 (3) 0.055 (3)
C13 0.079 (3) 0.069 (3) 0.056 (3) 0.017 (3) 0.024 (2) 0.039 (2)
C14 0.056 (2) 0.052 (2) 0.052 (2) 0.011 (2) 0.018 (2) 0.028 (2)
C15 0.052 (2) 0.039 (2) 0.055 (3) 0.0032 (18) 0.010 (2) 0.025 (2)
C16 0.081 (3) 0.038 (2) 0.062 (3) 0.016 (2) 0.004 (2) 0.027 (2)
C17 0.063 (3) 0.043 (2) 0.050 (2) 0.017 (2) 0.014 (2) 0.0272 (19)
C18 0.079 (3) 0.052 (2) 0.071 (3) 0.037 (2) 0.031 (2) 0.037 (2)
C19 0.072 (3) 0.074 (3) 0.086 (3) 0.041 (3) 0.041 (3) 0.053 (3)
C20 0.065 (3) 0.059 (2) 0.069 (3) 0.023 (2) 0.029 (2) 0.041 (2)
C21 0.063 (3) 0.045 (2) 0.047 (2) 0.021 (2) 0.0184 (19) 0.0273 (18)
C22 0.057 (2) 0.046 (2) 0.054 (2) 0.0228 (19) 0.0167 (19) 0.0286 (19)
C23 0.067 (3) 0.047 (2) 0.048 (2) 0.023 (2) 0.021 (2) 0.0319 (19)
Geometric parameters (Å, º)
Zn1—O1 1.942 (3) C5—H5 0.9300
Zn1—N1 2.027 (3) C6—H6 0.9300
Zn1—N3 2.011 (3) C8—H8 0.9300
O1—C15 1.266 (4) C9—C10 1.388 (6)
O2—C15 1.231 (5) C9—C14 1.402 (6)
O4—C23 1.277 (5) C10—C11 1.367 (7)
O5—C23 1.232 (5) C10—H10 0.9300
O3—C16 1.424 (4) C11—C12 1.383 (7)
O3—C17 1.360 (5) C11—H11 0.9300
O4—Zn1ii 1.986 (3) C12—C13 1.361 (7)
N1—C1 1.311 (5) C12—H12 0.9300
N1—C2 1.398 (5) C13—C14 1.386 (6)
N2—C1 1.346 (6) C13—H13 0.9300
N2—C7 1.399 (6) C15—C16 1.518 (6)
N2—H24 0.8600 C16—H16A 0.9700
N3—C8 1.313 (5) C16—H16B 0.9700
N3—C9 1.397 (5) C17—C18 1.384 (6)
N4—C8 1.343 (5) C17—C22 1.391 (5)
N4—C14 1.377 (5) C18—C19 1.379 (6)
N4—H25 0.8600 C18—H18 0.9300
C1—H1 0.9300 C19—C20 1.389 (6)
C2—C7 1.381 (6) C19—H19 0.9300
C2—C3 1.381 (6) C20—C21 1.391 (6)
C3—C4 1.377 (7) C20—H20 0.9300
C3—H3 0.9300 C21—C22 1.382 (5)
C4—C5 1.388 (8) C21—C23 1.511 (5)
C4—H4 0.9300 C22—H22 0.9300
C5—C6 1.356 (8)
O1—Zn1—O4i 110.49 (12) C7—C2—C3 120.1 (4)
O1—Zn1—N1 105.98 (13) C7—C2—N1 109.1 (4)
O1—Zn1—N3 119.11 (13) C7—C6—H6 121.7
O4i—Zn1—N1 100.62 (12) C8—N3—Zn1 127.4 (3)
O4i—Zn1—N3 111.56 (12) C8—N3—C9 105.0 (3)
N3—Zn1—N1 107.20 (14) C8—N4—C14 107.3 (3)
O1—C15—C16 113.4 (4) C8—N4—H25 126.4
O2—C15—O1 125.0 (4) C9—N3—Zn1 125.2 (3)
O2—C15—C16 121.5 (4) C9—C10—H10 121.7
O3—C16—C15 113.4 (3) C10—C9—N3 130.8 (4)
O3—C16—H16A 108.9 C10—C9—C14 120.3 (4)
O3—C16—H16B 108.9 C10—C11—C12 122.9 (5)
O3—C17—C18 126.0 (3) C10—C11—H11 118.5
O3—C17—C22 114.8 (4) C11—C10—C9 116.6 (4)
O4—C23—C21 117.5 (4) C11—C10—H10 121.7
O5—C23—O4 122.8 (3) C11—C12—H12 119.3
O5—C23—C21 119.8 (4) C12—C11—H11 118.5
N1—C1—N2 112.4 (4) C12—C13—C14 116.9 (4)
N1—C1—H1 123.8 C12—C13—H13 121.6
supporting information
sup-5 Acta Cryst. (2005). E61, m494–m495
N2—C7—C6 132.5 (5) C13—C12—H12 119.3
N3—C8—N4 113.4 (4) C13—C14—C9 121.9 (4)
N3—C8—H8 123.3 C14—N4—H25 126.4
N3—C9—C14 108.8 (4) C14—C13—H13 121.6
N4—C8—H8 123.3 C15—O1—Zn1 116.7 (3)
N4—C14—C9 105.5 (3) C15—C16—H16A 108.9
N4—C14—C13 132.6 (4) C15—C16—H16B 108.9
C1—N1—Zn1 128.4 (3) C17—O3—C16 118.0 (3)
C1—N1—C2 105.9 (4) C17—C18—H18 120.1
C1—N2—C7 107.3 (4) C17—C22—H22 119.5
C1—N2—H24 126.3 C18—C17—C22 119.3 (4)
C2—N1—Zn1 125.4 (3) C18—C19—C20 121.2 (4)
C2—C3—H3 121.0 C18—C19—H19 119.4
C2—C7—N2 105.2 (4) C19—C18—C17 119.9 (4)
C2—C7—C6 122.1 (5) C19—C18—H18 120.1
C3—C2—N1 130.7 (4) C19—C20—C21 119.0 (4)
C3—C4—C5 121.1 (5) C19—C20—H20 120.5
C3—C4—H4 119.4 C20—C19—H19 119.4
C4—C3—C2 118.0 (5) C20—C21—C23 121.9 (4)
C4—C3—H3 121.0 C21—C20—H20 120.5
C4—C5—H5 119.0 C21—C22—C17 120.9 (4)
C5—C4—H4 119.4 C21—C22—H22 119.5
C5—C6—C7 116.6 (5) C22—C21—C20 119.8 (3)
C5—C6—H6 121.7 C22—C21—C23 118.3 (4)
C6—C5—C4 122.0 (5) C23—O4—Zn1ii 107.7 (2)
C6—C5—H5 119.0 H16A—C16—H16B 107.7
C7—N2—H24 126.3
Zn1—O1—C15—O2 8.5 (5) C2—N1—C1—N2 0.0 (5)
Zn1—O1—C15—C16 −174.1 (3) C2—C3—C4—C5 −0.5 (9)
Zn1ii—O4—C23—O5 −10.1 (5) C3—C2—C7—N2 178.0 (4)
Zn1ii—O4—C23—C21 167.9 (3) C3—C2—C7—C6 1.2 (7)
Zn1—N1—C1—N2 −174.6 (3) C3—C4—C5—C6 0.5 (10)
Zn1—N1—C2—C3 −2.8 (6) C4—C5—C6—C7 0.4 (9)
Zn1—N1—C2—C7 174.7 (3) C5—C6—C7—N2 −177.0 (5)
Zn1—N3—C8—N4 −164.1 (3) C5—C6—C7—C2 −1.2 (8)
Zn1—N3—C9—C10 −14.3 (6) C7—N2—C1—N1 0.1 (5)
Zn1—N3—C9—C14 164.0 (3) C7—C2—C3—C4 −0.3 (7)
O1—Zn1—N1—C2 52.6 (3) C8—N3—C9—C10 −178.0 (5)
O1—Zn1—N1—C1 −133.8 (4) C8—N3—C9—C14 0.3 (4)
O1—Zn1—N3—C8 14.4 (4) C8—N4—C14—C9 −0.9 (4)
O1—Zn1—N3—C9 −145.6 (3) C8—N4—C14—C13 176.6 (5)
O1—C15—C16—O3 168.1 (4) C9—N3—C8—N4 −1.0 (5)
O2—C15—C16—O3 −14.4 (6) C9—C10—C11—C12 0.5 (8)
O3—C17—C18—C19 179.6 (4) C10—C9—C14—N4 178.9 (4)
O3—C17—C22—C21 −179.7 (4) C10—C9—C14—C13 1.0 (6)
O4i—Zn1—N1—C1 111.1 (4) C10—C11—C12—C13 0.5 (9)
O4i—Zn1—O1—C15 172.5 (3) C12—C13—C14—N4 −177.2 (5)
O4i—Zn1—N3—C8 145.0 (3) C12—C13—C14—C9 0.0 (7)
O4i—Zn1—N3—C9 −15.0 (4) C14—N4—C8—N3 1.2 (5)
N1—Zn1—N3—C8 −105.7 (3) C14—C9—C10—C11 −1.2 (7)
N1—Zn1—N3—C9 94.3 (3) C16—O3—C17—C18 0.3 (6)
N1—Zn1—O1—C15 64.4 (3) C16—O3—C17—C22 −178.7 (3)
N1—C2—C3—C4 177.0 (5) C17—O3—C16—C15 −73.2 (5)
N1—C2—C7—N2 0.2 (5) C17—C18—C19—C20 −0.4 (7)
N1—C2—C7—C6 −176.6 (4) C18—C17—C22—C21 1.3 (6)
N3—Zn1—N1—C1 −5.6 (4) C18—C19—C20—C21 2.4 (7)
N3—Zn1—N1—C2 −179.2 (3) C19—C20—C21—C22 −2.6 (6)
N3—Zn1—O1—C15 −56.4 (3) C19—C20—C21—C23 178.9 (4)
N3—C9—C10—C11 176.9 (4) C20—C21—C22—C17 0.7 (6)
N3—C9—C14—N4 0.4 (4) C20—C21—C23—O4 0.2 (6)
N3—C9—C14—C13 −177.5 (4) C20—C21—C23—O5 178.3 (4)
C1—N1—C2—C3 −177.6 (5) C22—C17—C18—C19 −1.5 (6)
C1—N1—C2—C7 −0.1 (5) C22—C21—C23—O4 −178.4 (4)
C1—N2—C7—C2 −0.2 (5) C22—C21—C23—O5 −0.3 (6)
C1—N2—C7—C6 176.2 (5) C23—C21—C22—C17 179.4 (4)
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N2—H24···O2iii 0.86 1.93 2.747 (5) 158
N4—H25···O5iv 0.86 1.93 2.688 (4) 146