metal-organic papers
m992
Yang, Zeng and Ng [Zn(C12H8N3)2(H2O)] doi:10.1107/S1600536805012614 Acta Cryst.(2005). E61, m992–m993 Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Aquabis[2-(2-pyridyl)-1
H
-benzimidazolato]zinc(II)
Jian-Kui Yang,a,bMing-Hua Zenga* and Seik Weng Ngc
a
Department of Chemistry, Guangxi Normal University, Guilin 541000, Guangxi, People’s Republic of China,bDepartment of Applied Chemistry, Hunan Agricultural University, Changsha 410128, Hunan, People’s Republic of China, andcDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: zmhzsu@163.com
Key indicators
Single-crystal X-ray study
T= 295 K
Mean(C–C) = 0.005 A˚
Rfactor = 0.048
wRfactor = 0.131
Data-to-parameter ratio = 16.2
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 compound, [Zn(C12H8N3)2(H2O)], the Zn atom is
chelated by two heterocycles, and the coordinating N atoms comprise the basal plane of the square-pyramidal environ-ment. The apical position is occupied by an aqua ligand. The complexes are linked by O—H O hydrogen bonds into a ribbon structure along theaaxis.
Comment
2-(2-Pyridyl)-1H-benzimidazole (Hpybim) is an organic heterocycle that possesses luminescence properties, and the present study was initiated in an investigation of this property in the zinc complex. The crystal structure of [Zn(pybim)2] as
well as its electronic structure have been studied (Yueet al., 2002); it is a planar compound. A search through the Cambridge Structural Database (Version 5.26; Allen, 2002) found only two metal complexes containing this ligand,viz.a copper(II) isothiocyanate adduct of the neutral Hpybim molecule (Battagliaet al., 1976) and an yttrium(III) complex (Mu¨ller-Buschbaum & Quitmann, 2003).
The Zn atom in the present complex, (I), is chelated by the two pybimligands. The four coordinating N atoms comprise a square plane; the coordinated water molecule occupies the apical position of the square-pyramidal geometry. The aqua ligands link adjacent complexes into a ribbon structure along theaaxis (Fig. 2).
Experimental
Zinc nitrate hexahydrate (0.149 g, 0.5 mmol) and 2-carboxy-phenoxyacetic acid (0.196 g, 1 mmol) were dissolved in ethanol (3 ml) and water (15 ml). The solution was placed in a 23 ml Teflon-lined stainless steel Parr bomb. The bomb was heated at 433 K for 120 h. The cool mixture yielded colourless crystals of (I); these were washed with water and then dried in air (yieldca70%).
Crystal data
[Zn(C12H8N3)2(H2O)]
Mr= 471.81
Monoclinic,P21=c
a= 12.5448 (8) A˚
b= 13.0525 (8) A˚
c= 13.3493 (9) A˚
= 102.731 (1)
V= 2132.1 (2) A˚3
Z= 4
Dx= 1.470 Mg m
3 MoKradiation Cell parameters from 3351
reflections
= 3.0–25.4
= 1.18 mm1
T= 295 (2) K Block, colourless 0.360.180.11 mm
Data collection
Bruker SMART APEX area-detector diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Bruker, 2001)
Tmin= 0.676,Tmax= 0.881 12 542 measured reflections
4812 independent reflections 3727 reflections withI> 2(I)
Rint= 0.025
max= 27.5
h=16!16
k=10!16
l=16!17
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.048
wR(F2) = 0.131
S= 1.01 4812 reflections 297 parameters
H atoms treated by a mixture of independent and constrained refinement
w= 1/[2(F
o2) + (0.0743P)2
+ 0.521P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 0.58 e A˚
3
min=0.21 e A˚
[image:2.610.50.555.75.501.2]3
Table 1
Selected geometric parameters (A˚ ,).
Zn1—O1w 2.001 (2)
Zn1—N1 1.989 (2)
Zn1—N3 2.239 (2)
Zn1—N4 2.002 (2)
Zn1—N6 2.245 (2)
O1w—Zn1—N1 117.5 (1) O1w—Zn1—N3 89.1 (1) O1w—Zn1—N4 115.5 (1) O1w—Zn1—N6 85.8 (1)
N1—Zn1—N3 78.7 (1)
N1—Zn1—N4 126.9 (1)
N1—Zn1—N6 108.3 (1)
N3—Zn1—N4 99.1 (1)
N3—Zn1—N6 172.7 (1)
N4—Zn1—N6 78.5 (1)
N1—C7—C8—N3 3.1 (4) N4—C19—C20—N6 3.2 (3)
Table 2
Hydrogen-bonding geometry (A˚ ,).
D—H A D—H H A D A D—H A
O1w—H1w1 N2i
0.85 (1) 1.90 (2) 2.713 (3) 160 (3) O1w—H1w2 N5ii
0.84 (1) 1.88 (1) 2.713 (3) 170 (3)
Symmetry codes: (i) 2x;1y;1z; (ii) 1x;1y;1z.
The carbon-bound H atoms were positioned geometrically (C—H = 0.93 A˚ ) and were included in the refinement in the riding-model approximation, withUiso(H) values set at 1.2 timesUeq(C). The water
H atoms were located in difference Fourier maps and refined isotropically with O—H distances restrained to 0.85 (1) A˚ .
Data collection:SMART(Bruker, 2001); cell refinement:SAINT
(Bruker, 2001); data reduction: SAINT; 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.
We thank the Guangxi Normal University and the Univer-sity of Malaya for supporting this study.
References
Allen, F. H. (2002).Acta Cryst.B58, 380–388.
Battaglia, L. P., Ferrari, M. B., Corradi, A. B., Fava, G. G., Pelizzi, C. & Tani, M. E. V. (1976).J. Chem. Soc. Dalton Trans.pp. 2197–2202.
Bruker (2001).SADABS(Version 6.45),SAINT(Version 6.45) andSMART
(Version 5.0). Bruker AXS Inc., Madison, Wisconsin, USA.
Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Mu¨ller-Buschbaum, K. & Quitmann, C. C. (2003).Inorg. Chem.42, 2742–2750. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
Go¨ttingen, Germany.
Yue, S.-M., Su, Z.-M., Ma, J.-F., Liao, Y., Kan, Y.-H. & Zhang, H.-J. (2002).
Chin. J. Struct. Chem.22, 174–178.
Figure 1
The molecular structure of (I), showing displacement ellipsoids at the 50% probability level.
Figure 2
[image:2.610.317.564.368.530.2]supporting information
sup-1 Acta Cryst. (2005). E61, m992–m993
supporting information
Acta Cryst. (2005). E61, m992–m993 [https://doi.org/10.1107/S1600536805012614]
Aquabis[2-(2-pyridyl)-1
H
-benzimidazolato]zinc(II)
Jian-Kui Yang, Ming-Hua Zeng and Seik Weng Ng
Aquabis[2-(2-pyridyl)-1H-benzimidazolato]zinc(II)
Crystal data
[Zn(C12H8N3)2(H2O)]
Mr = 471.81 Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 12.5448 (8) Å
b = 13.0525 (8) Å
c = 13.3493 (9) Å
β = 102.731 (1)°
V = 2132.1 (2) Å3
Z = 4
F(000) = 968
Dx = 1.470 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 3351 reflections
θ = 3.0–25.4°
µ = 1.18 mm−1
T = 295 K Block, colorless 0.36 × 0.18 × 0.11 mm
Data collection
Bruker APEX area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2002)
Tmin = 0.676, Tmax = 0.881
12542 measured reflections 4812 independent reflections 3727 reflections with I > 2σ(I)
Rint = 0.025
θmax = 27.5°, θmin = 2.2°
h = −16→16
k = −10→16
l = −16→17
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.048
wR(F2) = 0.131
S = 1.01 4812 reflections 297 parameters 2 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: difference Fourier map H atoms treated by a mixture of independent
and constrained refinement
w = 1/[σ2(F
o2) + (0.0743P)2 + 0.521P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.58 e Å−3
Δρmin = −0.21 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
H1w2 0.6750 (13) 0.399 (2) 0.441 (2) 0.068 (10)* N1 0.92465 (17) 0.55839 (17) 0.63461 (18) 0.0435 (5) N2 1.09546 (17) 0.61715 (19) 0.6356 (2) 0.0521 (6) N3 0.84516 (18) 0.62390 (18) 0.44168 (19) 0.0495 (6) N4 0.64527 (16) 0.63475 (16) 0.55799 (17) 0.0410 (5) N5 0.47012 (17) 0.64655 (17) 0.57787 (17) 0.0426 (5) N6 0.67943 (19) 0.45294 (17) 0.65498 (19) 0.0455 (5) C1 0.9918 (2) 0.5314 (2) 0.7278 (2) 0.0481 (7) C2 0.9705 (3) 0.4805 (3) 0.8120 (3) 0.0639 (9)
H2 0.9007 0.4573 0.8132 0.077*
C3 1.0581 (4) 0.4655 (3) 0.8948 (3) 0.0815 (12)
H3 1.0472 0.4296 0.9519 0.098*
C4 1.1617 (3) 0.5033 (4) 0.8941 (3) 0.0867 (12)
H4 1.2182 0.4935 0.9514 0.104*
C5 1.1822 (3) 0.5543 (3) 0.8112 (3) 0.0750 (11)
H5 1.2518 0.5789 0.8113 0.090*
C6 1.0967 (2) 0.5686 (2) 0.7270 (3) 0.0543 (7) C7 0.9922 (2) 0.60767 (19) 0.5855 (2) 0.0424 (6) C8 0.9496 (2) 0.6464 (2) 0.4811 (2) 0.0456 (6) C9 1.0120 (3) 0.7003 (2) 0.4242 (3) 0.0644 (9)
H9 1.0848 0.7158 0.4521 0.077*
C10 0.9632 (3) 0.7301 (3) 0.3256 (3) 0.0733 (10)
H10 1.0032 0.7658 0.2861 0.088*
C11 0.8567 (3) 0.7072 (3) 0.2865 (3) 0.0718 (10)
H11 0.8225 0.7274 0.2204 0.086*
C12 0.8009 (3) 0.6538 (3) 0.3467 (3) 0.0607 (8)
H12 0.7280 0.6375 0.3195 0.073*
C13 0.6018 (2) 0.7241 (2) 0.5122 (2) 0.0408 (6) C14 0.6474 (2) 0.8013 (2) 0.4628 (2) 0.0533 (7)
H14 0.7197 0.7981 0.4565 0.064*
C15 0.5811 (3) 0.8824 (2) 0.4237 (3) 0.0602 (8)
H15 0.6088 0.9343 0.3891 0.072*
C16 0.4734 (3) 0.8886 (2) 0.4347 (3) 0.0601 (8)
H16 0.4313 0.9448 0.4075 0.072*
C17 0.4282 (2) 0.8149 (2) 0.4841 (2) 0.0529 (7)
H17 0.3563 0.8201 0.4912 0.063*
C18 0.4931 (2) 0.7312 (2) 0.52396 (19) 0.0416 (6) C19 0.56288 (19) 0.5934 (2) 0.59504 (18) 0.0375 (5) C20 0.5814 (2) 0.4952 (2) 0.65080 (19) 0.0393 (5) C21 0.5037 (2) 0.4494 (2) 0.6954 (2) 0.0504 (7)
H21 0.4359 0.4801 0.6910 0.061*
C22 0.5281 (3) 0.3581 (3) 0.7462 (2) 0.0599 (8)
H22 0.4773 0.3262 0.7770 0.072*
C23 0.6281 (3) 0.3148 (2) 0.7509 (2) 0.0596 (8)
H23 0.6468 0.2533 0.7855 0.072*
C24 0.7009 (3) 0.3635 (2) 0.7036 (2) 0.0575 (8)
supporting information
sup-3 Acta Cryst. (2005). E61, m992–m993
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Zn1 0.02878 (18) 0.0487 (2) 0.0573 (2) −0.00007 (12) 0.01280 (14) 0.00078 (14) O1w 0.0341 (11) 0.0767 (15) 0.0863 (16) −0.0156 (10) 0.0281 (11) −0.0329 (12) N1 0.0319 (11) 0.0458 (13) 0.0540 (13) 0.0021 (9) 0.0121 (10) −0.0006 (10) N2 0.0316 (12) 0.0559 (15) 0.0706 (17) −0.0001 (10) 0.0150 (11) −0.0044 (12) N3 0.0399 (12) 0.0536 (15) 0.0572 (14) 0.0018 (10) 0.0155 (11) 0.0057 (11) N4 0.0321 (11) 0.0406 (12) 0.0515 (13) −0.0010 (9) 0.0120 (9) 0.0015 (9) N5 0.0331 (11) 0.0502 (13) 0.0459 (12) −0.0006 (9) 0.0119 (9) −0.0080 (10) N6 0.0393 (12) 0.0449 (13) 0.0531 (14) −0.0005 (9) 0.0117 (10) 0.0037 (10) C1 0.0426 (15) 0.0495 (17) 0.0512 (16) 0.0086 (12) 0.0082 (13) −0.0055 (12) C2 0.061 (2) 0.071 (2) 0.060 (2) 0.0024 (16) 0.0132 (16) 0.0000 (16) C3 0.094 (3) 0.090 (3) 0.056 (2) 0.014 (2) 0.006 (2) 0.0064 (18) C4 0.065 (2) 0.109 (3) 0.073 (3) 0.013 (2) −0.015 (2) −0.004 (2) C5 0.0451 (19) 0.090 (3) 0.083 (3) 0.0081 (17) −0.0020 (18) −0.006 (2) C6 0.0358 (14) 0.0576 (18) 0.068 (2) 0.0066 (12) 0.0086 (13) −0.0121 (15) C7 0.0315 (13) 0.0376 (14) 0.0614 (17) 0.0013 (10) 0.0175 (12) −0.0056 (12) C8 0.0397 (14) 0.0345 (14) 0.0676 (18) 0.0037 (11) 0.0230 (13) 0.0020 (12) C9 0.0495 (18) 0.0541 (19) 0.095 (3) −0.0024 (14) 0.0272 (17) 0.0137 (17) C10 0.077 (2) 0.057 (2) 0.095 (3) 0.0049 (17) 0.040 (2) 0.0304 (19) C11 0.081 (3) 0.065 (2) 0.073 (2) 0.0146 (18) 0.0258 (19) 0.0233 (18) C12 0.0540 (18) 0.064 (2) 0.064 (2) 0.0040 (15) 0.0120 (15) 0.0121 (16) C13 0.0340 (12) 0.0411 (14) 0.0459 (14) −0.0011 (10) 0.0054 (10) −0.0043 (11) C14 0.0425 (15) 0.0461 (17) 0.0704 (19) −0.0042 (12) 0.0106 (13) 0.0059 (14) C15 0.0625 (19) 0.0402 (16) 0.073 (2) −0.0057 (14) 0.0034 (16) 0.0069 (14) C16 0.0585 (19) 0.0424 (17) 0.070 (2) 0.0067 (14) −0.0063 (16) −0.0028 (14) C17 0.0430 (15) 0.0536 (18) 0.0581 (17) 0.0105 (13) 0.0027 (13) −0.0068 (14) C18 0.0376 (13) 0.0443 (15) 0.0417 (14) −0.0008 (11) 0.0063 (11) −0.0102 (11) C19 0.0297 (12) 0.0447 (15) 0.0384 (13) −0.0034 (10) 0.0082 (10) −0.0074 (11) C20 0.0394 (14) 0.0429 (14) 0.0360 (13) −0.0071 (11) 0.0090 (10) −0.0057 (11) C21 0.0435 (16) 0.065 (2) 0.0441 (15) −0.0072 (13) 0.0133 (12) 0.0017 (13) C22 0.0596 (19) 0.073 (2) 0.0477 (16) −0.0175 (16) 0.0128 (14) 0.0112 (15) C23 0.073 (2) 0.0514 (19) 0.0517 (17) −0.0072 (15) 0.0067 (15) 0.0115 (14) C24 0.0568 (18) 0.0515 (18) 0.0632 (19) 0.0039 (14) 0.0108 (15) 0.0056 (14)
Geometric parameters (Å, º)
Zn1—O1w 2.001 (2) C7—C8 1.467 (4)
Zn1—N1 1.989 (2) C8—C9 1.395 (4)
Zn1—N3 2.239 (2) C9—C10 1.379 (5)
Zn1—N4 2.002 (2) C9—H9 0.9300
Zn1—N6 2.245 (2) C10—C11 1.356 (5)
O1w—H1w1 0.85 (1) C10—H10 0.9300
O1w—H1w2 0.84 (1) C11—C12 1.368 (4)
N1—C7 1.345 (3) C11—H11 0.9300
N1—C1 1.385 (4) C12—H12 0.9300
N2—C6 1.372 (4) C13—C18 1.410 (3)
N3—C12 1.326 (4) C14—C15 1.377 (4)
N3—C8 1.333 (3) C14—H14 0.9300
N4—C19 1.353 (3) C15—C16 1.392 (4)
N4—C13 1.373 (3) C15—H15 0.9300
N5—C19 1.331 (3) C16—C17 1.360 (4)
N5—C18 1.383 (3) C16—H16 0.9300
N6—C24 1.334 (4) C17—C18 1.396 (4)
N6—C20 1.338 (3) C17—H17 0.9300
C1—C2 1.382 (5) C19—C20 1.474 (4)
C1—C6 1.404 (4) C20—C21 1.385 (4)
C2—C3 1.390 (5) C21—C22 1.372 (4)
C2—H2 0.9300 C21—H21 0.9300
C3—C4 1.393 (6) C22—C23 1.365 (4)
C3—H3 0.9300 C22—H22 0.9300
C4—C5 1.362 (6) C23—C24 1.375 (4)
C4—H4 0.9300 C23—H23 0.9300
C5—C6 1.386 (5) C24—H24 0.9300
C5—H5 0.9300
O1w—Zn1—N1 117.5 (1) C9—C8—C7 124.1 (3)
O1w—Zn1—N3 89.1 (1) C10—C9—C8 118.5 (3)
O1w—Zn1—N4 115.5 (1) C10—C9—H9 120.7
O1w—Zn1—N6 85.8 (1) C8—C9—H9 120.7
N1—Zn1—N3 78.7 (1) C11—C10—C9 119.9 (3)
N1—Zn1—N4 126.9 (1) C11—C10—H10 120.1
N1—Zn1—N6 108.3 (1) C9—C10—H10 120.1
N3—Zn1—N4 99.1 (1) C10—C11—C12 118.3 (3)
N3—Zn1—N6 172.7 (1) C10—C11—H11 120.8
N4—Zn1—N6 78.5 (1) C12—C11—H11 120.8
Zn1—O1w—H1w1 126 (2) N3—C12—C11 123.4 (3)
Zn1—O1w—H1w2 121 (2) N3—C12—H12 118.3
H1w1—O1w—H1w2 112 (3) C11—C12—H12 118.3
C7—N1—C1 103.6 (2) N4—C13—C14 131.3 (2)
C7—N1—Zn1 116.13 (19) N4—C13—C18 107.8 (2)
C1—N1—Zn1 140.2 (2) C14—C13—C18 120.9 (2)
C7—N2—C6 102.9 (2) C15—C14—C13 117.3 (3)
C12—N3—C8 118.8 (3) C15—C14—H14 121.4
C12—N3—Zn1 130.4 (2) C13—C14—H14 121.4
C8—N3—Zn1 110.84 (18) C14—C15—C16 121.6 (3)
C19—N4—C13 104.0 (2) C14—C15—H15 119.2
C19—N4—Zn1 115.32 (17) C16—C15—H15 119.2
C13—N4—Zn1 138.76 (17) C17—C16—C15 121.9 (3)
C19—N5—C18 103.4 (2) C17—C16—H16 119.1
C24—N6—C20 117.8 (2) C15—C16—H16 119.1
C24—N6—Zn1 131.1 (2) C16—C17—C18 117.9 (3)
C20—N6—Zn1 110.47 (17) C16—C17—H17 121.0
supporting information
sup-5 Acta Cryst. (2005). E61, m992–m993
C2—C1—C6 121.5 (3) N5—C18—C17 130.8 (2)
N1—C1—C6 106.9 (3) N5—C18—C13 108.9 (2)
C1—C2—C3 117.0 (3) C17—C18—C13 120.4 (3)
C1—C2—H2 121.5 N5—C19—N4 116.0 (2)
C3—C2—H2 121.5 N5—C19—C20 125.1 (2)
C2—C3—C4 121.4 (4) N4—C19—C20 118.9 (2)
C2—C3—H3 119.3 N6—C20—C21 122.1 (3)
C4—C3—H3 119.3 N6—C20—C19 114.9 (2)
C5—C4—C3 121.5 (4) C21—C20—C19 123.0 (2)
C5—C4—H4 119.3 C22—C21—C20 119.1 (3)
C3—C4—H4 119.3 C22—C21—H21 120.5
C4—C5—C6 118.3 (4) C20—C21—H21 120.5
C4—C5—H5 120.9 C23—C22—C21 119.0 (3)
C6—C5—H5 120.9 C23—C22—H22 120.5
N2—C6—C5 129.7 (3) C21—C22—H22 120.5
N2—C6—C1 109.9 (3) C22—C23—C24 119.0 (3)
C5—C6—C1 120.4 (3) C22—C23—H23 120.5
N2—C7—N1 116.7 (3) C24—C23—H23 120.5
N2—C7—C8 123.9 (2) N6—C24—C23 123.0 (3)
N1—C7—C8 119.4 (2) N6—C24—H24 118.5
N3—C8—C9 121.1 (3) C23—C24—H24 118.5
N3—C8—C7 114.8 (2)
N1—Zn1—N6—C20 135.97 (18) C16—C17—C18—N5 179.3 (3) O1w—Zn1—N6—C20 −106.39 (19) C16—C17—C18—C13 −0.3 (4) N4—Zn1—N6—C20 10.70 (18) N4—C13—C18—N5 0.5 (3) C7—N1—C1—C2 179.1 (3) C14—C13—C18—N5 −178.2 (2) Zn1—N1—C1—C2 −4.4 (5) N4—C13—C18—C17 −179.8 (2) C7—N1—C1—C6 0.5 (3) C14—C13—C18—C17 1.5 (4) Zn1—N1—C1—C6 177.0 (2) C18—N5—C19—N4 0.2 (3) N1—C1—C2—C3 180.0 (3) C18—N5—C19—C20 179.9 (2) C6—C1—C2—C3 −1.5 (5) C13—N4—C19—N5 0.1 (3) C1—C2—C3—C4 2.1 (6) Zn1—N4—C19—N5 −167.05 (17) C2—C3—C4—C5 −1.6 (7) C13—N4—C19—C20 −179.6 (2) C3—C4—C5—C6 0.4 (7) Zn1—N4—C19—C20 13.3 (3) C7—N2—C6—C5 −179.5 (3) C24—N6—C20—C21 0.4 (4) C7—N2—C6—C1 −0.1 (3) Zn1—N6—C20—C21 172.7 (2) C4—C5—C6—N2 179.5 (4) C24—N6—C20—C19 −179.4 (2) C4—C5—C6—C1 0.2 (5) Zn1—N6—C20—C19 −7.1 (3) C2—C1—C6—N2 −179.1 (3) N5—C19—C20—N6 177.1 (2) N1—C1—C6—N2 −0.2 (3) N4—C19—C20—N6 −3.2 (3) C2—C1—C6—C5 0.4 (5) N5—C19—C20—C21 −2.7 (4) N1—C1—C6—C5 179.2 (3) N4—C19—C20—C21 177.0 (2) C6—N2—C7—N1 0.5 (3) N6—C20—C21—C22 0.5 (4) C6—N2—C7—C8 −178.8 (3) C19—C20—C21—C22 −179.7 (3) C1—N1—C7—N2 −0.6 (3) C20—C21—C22—C23 −0.3 (5) Zn1—N1—C7—N2 −178.13 (18) C21—C22—C23—C24 −0.6 (5) C1—N1—C7—C8 178.7 (2) C20—N6—C24—C23 −1.4 (4) Zn1—N1—C7—C8 1.2 (3) Zn1—N6—C24—C23 −171.9 (2) C12—N3—C8—C9 0.0 (4) C22—C23—C24—N6 1.6 (5)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O1w—H1w1···N2i 0.85 (1) 1.90 (2) 2.713 (3) 160 (3)
O1w—H1w2···N5ii 0.84 (1) 1.88 (1) 2.713 (3) 170 (3)
