metal-organic papers
Acta Cryst.(2007). E63, m15–m16 doi:10.1107/S1600536806051166 Zhouet al. [Zn(NO
3)(C8H8N2O)2]NO3H2O
m15
Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
Bis[(1
H
-benzimidazol-2-yl)methanol-
j
2N
,
O
]-(nitrato-
j
2O
,
O
000)zinc(II) nitrate monohydrate
Yan-Ling Zhou,aMing-Hua Zenga and Seik Weng Ngb*
a
Department of Chemistry, Guangxi Normal University, Guilin 541000, Guangxi, People’s Republic of China, andbDepartment of
Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 293 K
Mean(C–C) = 0.005 A˚
Rfactor = 0.042
wRfactor = 0.114
Data-to-parameter ratio = 11.0
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 22 November 2006 Accepted 27 November 2006
#2007 International Union of Crystallography All rights reserved
The title compound, [Zn(NO3)(C8H8N2O)2]NO3H2O,
consists of a tris-chelated zinc cation and a nitrate anion, along with an uncoordinated water molecule. These interact
through O—H O and N—H O hydrogen bonds, giving
rise to a three-dimensional network structure. The ZnIIion has an octahedral coordination.
Comment
The benzimidazol-2-ylmethanol ligand has been shown to bind to cobalt(II) as a neutral chelate (Zeng et al., 2006). This feature is also preserved in the present zinc nitrate complex; of the two nitrate anions, only one is involved in coordination. The compound crystallizes as a monohydrate, (I) (Fig. 1), and the metal shows an octahedral coordination. The heterocycle as well as the nitrate group engage in chelation. The structure is consolidated by hydrogen bonds (Table 1) between the cation, anion and the uncoordinated water molecule, leading to a three-dimensional network.
Experimental
(1H-Benzimidazol-2-yl)methanol (0.15 g, 1 mmol), zinc(II) nitrate hexahydrate (0.15 g, 0.5 mmol) and zinc(II) acetate (0.12 g, 0.5 mmol) were dissolved in water (10 ml). Pale-yellow platelets separated from the solution after two weeks.
Crystal data
[Zn(NO3)(C8H8N2O)2]NO3H2O
Mr= 503.73 Triclinic,P1
a= 8.2287 (8) A˚
b= 9.6745 (9) A˚
c= 13.542 (1) A˚ = 81.506 (2) = 80.678 (2) = 69.867 (2)
V= 993.89 (15) A˚3
Z= 2
Dx= 1.683 Mg m 3
MoKradiation = 1.30 mm1
Data collection
Bruker APEX2 area-detector diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)
Tmin= 0.781,Tmax= 0.903
5025 measured reflections 3444 independent reflections 2947 reflections withI> 2(I)
Rint= 0.020 max= 25.0
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.042
wR(F2) = 0.114
S= 1.06 3444 reflections 313 parameters
H atoms treated by a mixture of independent and constrained refinement
w= 1/[2
(Fo2) + (0.0636P)2 + 0.1377P]
whereP= (Fo2+ 2Fc2)/3 (/)max= 0.001
max= 0.42 e A˚ 3
min=0.38 e A˚ 3
Table 1
Selected geometric parameters (A˚ ,).
Zn1—O1 2.246 (3) Zn1—O2 2.173 (3) Zn1—O3 2.195 (2)
Zn1—O4 2.213 (3) Zn1—N1 1.997 (2) Zn1—N3 1.993 (3)
O1—Zn1—O2 117.3 (1) O1—Zn1—O3 96.2 (1) O1—Zn1—O4 154.1 (1) O1—Zn1—N1 76.2 (1) O1—Zn1—N3 85.3 (1) O2—Zn1—O3 145.4 (1) O2—Zn1—O4 88.6 (1) O2—Zn1—N1 96.7 (1)
O2—Zn1—N3 77.1 (1) O3—Zn1—O4 58.1 (1) O3—Zn1—N1 99.5 (1) O3—Zn1—N3 98.8 (1) O4—Zn1—N1 103.1 (1) O4—Zn1—N3 100.8 (1) N1—Zn1—N3 155.2 (1)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O1—H1o O1w 0.85 (1) 1.80 (1) 2.635 (4) 172 (5) O2—H2o O6i 0.84 (1) 2.08 (2) 2.877 (4) 159 (4) O1w—H1w1 O5ii
0.85 (1) 2.07 (2) 2.908 (5) 168 (5) O1w—H1w2 O6iii
0.85 (1) 2.29 (3) 3.038 (5) 148 (5) N2—H2n O6 0.85 (1) 2.14 (2) 2.922 (4) 154 (4) N4—H4n O7iv
0.85 (1) 2.14 (2) 2.959 (4) 163 (3)
Symmetry codes: (i)xþ2;y;zþ1; (ii)xþ1;y;z; (iii)xþ2;yþ1;zþ1; (iv)x;y;zþ1.
The C-bound H atoms were placed in calculated positions (C—H = 0.93–0.97 A˚ ) and included in the refinement in the riding-model approximation, withUiso(H) = 1.2Ueq(C). The amino, hydroxy and
water H atoms were located in a difference Fourier map and refined isotropically with distance restraints of O(N)—H = 0.85 (1) A˚ and H H = 1.39 (1) A˚ .
Data collection:APEX2(Bruker, 2004); cell refinement:SAINT
(Bruker, 2004); data reduction:SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication:SHELXL97.
This work was supported by the Natural Science Founda-tion of Guangxi, Guangxi Normal University and the University of Malaya.
References
Barbour, L. J. (2001).J. Supramol. Chem.1, 189–191.
Bruker (2004).APEX2(Version 6.36A) andSAINT(Version 6.36A). Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of
Go¨ttingen, Germany.
[image:2.610.313.567.72.241.2]Zeng, M.-H., Zhou, Y.-L. & Ng, S. W. (2006).Acta Cryst.E62, m2101–m2102. Figure 1
supporting information
sup-1 Acta Cryst. (2007). E63, m15–m16
supporting information
Acta Cryst. (2007). E63, m15–m16 [https://doi.org/10.1107/S1600536806051166]
Bis[(1
H
-benzimidazol-2-yl)methanol-
κ
2N
,
O
](nitrato-
κ
2O
,
O
′
)zinc(II) nitrate
monohydrate
Yan-Ling Zhou, Ming-Hua Zeng and Seik Weng Ng
Bis[(1H-benzimidazol-2-yl)methanol-κ2N,O](nitrato-κ2O,O′)zinc(II) nitrate monohydrate
Crystal data
[Zn(NO3)(C8H8N2O)2]NO3·H2O
Mr = 503.73
Triclinic, P1 Hall symbol: -P 1 a = 8.2287 (8) Å b = 9.6745 (9) Å c = 13.542 (1) Å α = 81.506 (2)° β = 80.678 (2)° γ = 69.867 (2)° V = 993.89 (15) Å3
Z = 2 F(000) = 516 Dx = 1.683 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1775 reflections θ = 2.6–25.3°
µ = 1.30 mm−1
T = 293 K Plate, pale yellow 0.20 × 0.15 × 0.08 mm
Data collection
Bruker APEX2 area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.781, Tmax = 0.903
5025 measured reflections 3444 independent reflections 2947 reflections with I > 2σ(I) Rint = 0.020
θmax = 25.0°, θmin = 1.5°
h = −8→9 k = −7→11 l = −14→16
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.042
wR(F2) = 0.114
S = 1.06 3444 reflections 313 parameters 6 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0636P)2 + 0.1377P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.42 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
Zn1 0.63068 (5) 0.28762 (4) 0.71867 (3) 0.03887 (16) O1 0.7129 (4) 0.4602 (3) 0.61315 (18) 0.0498 (6) O2 0.8274 (4) 0.1249 (3) 0.80316 (19) 0.0552 (7) O3 0.3507 (3) 0.3877 (3) 0.70619 (18) 0.0528 (6)
O4 0.4400 (4) 0.1801 (3) 0.7952 (2) 0.0597 (7)
O5 0.1635 (4) 0.2852 (4) 0.7842 (2) 0.0794 (9)
O6 1.0456 (4) 0.1810 (3) 0.23550 (19) 0.0685 (8)
O7 0.9411 (4) 0.3797 (3) 0.1372 (2) 0.0639 (8)
O8 1.0147 (4) 0.1678 (3) 0.0834 (2) 0.0733 (9)
O1w 0.9389 (4) 0.5498 (4) 0.6807 (2) 0.0660 (8)
N1 0.7096 (3) 0.1969 (3) 0.58860 (18) 0.0362 (6)
N2 0.8324 (4) 0.1899 (3) 0.4307 (2) 0.0428 (7)
N3 0.6455 (3) 0.3992 (3) 0.82755 (18) 0.0364 (6)
N4 0.7730 (4) 0.4208 (3) 0.9528 (2) 0.0436 (7)
N5 0.3140 (4) 0.2837 (4) 0.7627 (2) 0.0518 (8)
N6 0.9990 (4) 0.2446 (4) 0.1516 (2) 0.0480 (7)
C1 0.7183 (4) 0.0643 (4) 0.5560 (2) 0.0366 (7)
C2 0.6608 (4) −0.0497 (4) 0.6050 (3) 0.0428 (8)
H2 0.6090 −0.0474 0.6714 0.051*
C3 0.6835 (5) −0.1657 (4) 0.5515 (3) 0.0504 (9)
H3 0.6439 −0.2427 0.5821 0.060*
C4 0.7641 (5) −0.1721 (4) 0.4527 (3) 0.0531 (9)
H4 0.7782 −0.2538 0.4195 0.064*
C5 0.8235 (5) −0.0603 (4) 0.4030 (3) 0.0482 (9)
H5 0.8783 −0.0647 0.3373 0.058*
C6 0.7972 (4) 0.0583 (4) 0.4562 (2) 0.0395 (8)
C7 0.7782 (4) 0.2673 (4) 0.5116 (2) 0.0378 (7)
C8 0.7888 (5) 0.4168 (4) 0.5156 (3) 0.0496 (9)
H8A 0.9094 0.4138 0.5039 0.059*
H8B 0.7258 0.4867 0.4645 0.059*
C9 0.5821 (4) 0.5475 (4) 0.8472 (2) 0.0377 (7)
C10 0.4643 (5) 0.6696 (4) 0.8017 (3) 0.0469 (9)
H10 0.4082 0.6612 0.7496 0.056*
C11 0.4330 (5) 0.8044 (4) 0.8362 (3) 0.0564 (10)
H11 0.3544 0.8886 0.8068 0.068*
C12 0.5167 (6) 0.8169 (4) 0.9142 (3) 0.0610 (11)
H12 0.4936 0.9100 0.9349 0.073*
C13 0.6315 (5) 0.6975 (4) 0.9613 (3) 0.0539 (10)
H13 0.6855 0.7069 1.0140 0.065*
C14 0.6637 (4) 0.5609 (4) 0.9267 (2) 0.0417 (8)
C15 0.7580 (4) 0.3290 (4) 0.8921 (2) 0.0389 (7)
C16 0.8541 (5) 0.1691 (4) 0.8933 (2) 0.0460 (8)
H16A 0.9773 0.1497 0.8955 0.055*
H16B 0.8101 0.1154 0.9517 0.055*
supporting information
sup-3 Acta Cryst. (2007). E63, m15–m16
H2O 0.855 (5) 0.0325 (12) 0.808 (3) 0.056 (12)*
H1W1 0.996 (6) 0.478 (4) 0.719 (3) 0.084 (17)*
H1W2 0.900 (6) 0.628 (3) 0.711 (3) 0.090 (19)*
H2N 0.881 (6) 0.218 (5) 0.3748 (19) 0.088 (16)*
H4N 0.837 (4) 0.393 (4) 1.0003 (19) 0.048 (10)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Zn1 0.0469 (3) 0.0401 (3) 0.0314 (2) −0.01608 (18) −0.00224 (16) −0.00750 (16) O1 0.0711 (18) 0.0497 (15) 0.0372 (13) −0.0326 (13) 0.0014 (12) −0.0081 (11) O2 0.0726 (18) 0.0408 (16) 0.0455 (14) −0.0046 (13) −0.0153 (12) −0.0089 (12) O3 0.0508 (15) 0.0615 (17) 0.0481 (15) −0.0217 (13) −0.0064 (11) −0.0033 (13) O4 0.0673 (18) 0.0543 (17) 0.0574 (16) −0.0234 (14) −0.0033 (13) −0.0012 (13) O5 0.0532 (18) 0.113 (3) 0.083 (2) −0.0460 (17) 0.0105 (15) −0.0174 (19) O6 0.0733 (19) 0.079 (2) 0.0406 (15) −0.0107 (16) −0.0144 (13) 0.0078 (14) O7 0.078 (2) 0.0454 (17) 0.0676 (18) −0.0107 (14) −0.0248 (15) −0.0090 (14) O8 0.104 (2) 0.0565 (18) 0.0601 (18) −0.0157 (16) −0.0254 (17) −0.0171 (15) O1w 0.0637 (19) 0.085 (3) 0.0547 (18) −0.0283 (18) −0.0079 (15) −0.0131 (18) N1 0.0441 (15) 0.0366 (15) 0.0299 (13) −0.0161 (12) −0.0013 (11) −0.0057 (11) N2 0.0512 (18) 0.0500 (18) 0.0290 (15) −0.0216 (14) 0.0009 (13) −0.0033 (13) N3 0.0436 (15) 0.0380 (15) 0.0290 (13) −0.0160 (12) −0.0034 (11) −0.0030 (11) N4 0.0504 (17) 0.0532 (19) 0.0312 (15) −0.0209 (14) −0.0100 (13) −0.0013 (13) N5 0.054 (2) 0.062 (2) 0.0448 (17) −0.0233 (17) 0.0010 (15) −0.0197 (16) N6 0.0477 (17) 0.053 (2) 0.0403 (17) −0.0136 (15) −0.0065 (13) −0.0022 (15) C1 0.0376 (17) 0.0366 (18) 0.0356 (17) −0.0096 (14) −0.0075 (13) −0.0066 (14) C2 0.0439 (19) 0.042 (2) 0.0408 (18) −0.0151 (15) −0.0015 (15) −0.0013 (15) C3 0.057 (2) 0.039 (2) 0.058 (2) −0.0174 (17) −0.0152 (18) −0.0019 (17) C4 0.058 (2) 0.043 (2) 0.061 (2) −0.0108 (18) −0.0139 (19) −0.0199 (18) C5 0.049 (2) 0.056 (2) 0.0390 (18) −0.0114 (17) −0.0059 (15) −0.0164 (17) C6 0.0374 (18) 0.047 (2) 0.0337 (17) −0.0108 (15) −0.0065 (14) −0.0079 (15) C7 0.0428 (18) 0.0443 (19) 0.0296 (16) −0.0183 (15) −0.0035 (13) −0.0045 (14) C8 0.071 (2) 0.046 (2) 0.0370 (18) −0.0307 (18) −0.0024 (17) 0.0018 (15) C9 0.0439 (18) 0.0379 (18) 0.0303 (16) −0.0157 (15) 0.0028 (13) −0.0030 (13) C10 0.054 (2) 0.045 (2) 0.0394 (19) −0.0154 (17) −0.0022 (16) −0.0023 (16) C11 0.065 (3) 0.039 (2) 0.055 (2) −0.0111 (18) 0.0071 (19) −0.0027 (17) C12 0.078 (3) 0.044 (2) 0.061 (2) −0.025 (2) 0.014 (2) −0.0158 (19) C13 0.071 (3) 0.062 (3) 0.0393 (19) −0.036 (2) 0.0031 (18) −0.0140 (18) C14 0.049 (2) 0.046 (2) 0.0330 (17) −0.0224 (16) 0.0010 (14) −0.0049 (15) C15 0.0434 (19) 0.044 (2) 0.0297 (16) −0.0176 (15) −0.0012 (14) −0.0016 (14) C16 0.052 (2) 0.047 (2) 0.0350 (18) −0.0115 (16) −0.0077 (15) 0.0005 (15)
Geometric parameters (Å, º)
Zn1—O1 2.246 (3) N4—H4N 0.85 (1)
Zn1—O2 2.173 (3) C1—C2 1.386 (5)
Zn1—O3 2.195 (2) C1—C6 1.403 (4)
Zn1—N1 1.997 (2) C2—H2 0.93
Zn1—N3 1.993 (3) C3—C4 1.394 (5)
O1—C8 1.424 (4) C3—H3 0.93
O1—H1O 0.85 (1) C4—C5 1.380 (5)
O2—C16 1.424 (4) C4—H4 0.93
O2—H2O 0.84 (1) C5—C6 1.380 (5)
O3—N5 1.263 (4) C5—H5 0.93
O4—N5 1.255 (4) C7—C8 1.489 (5)
O5—N5 1.221 (4) C8—H8A 0.97
O6—N6 1.261 (4) C8—H8B 0.97
O7—N6 1.224 (4) C9—C10 1.380 (5)
O8—N6 1.233 (4) C9—C14 1.401 (5)
O1w—H1W1 0.85 (1) C10—C11 1.376 (5)
O1w—H1W2 0.85 (1) C10—H10 0.93
N1—C7 1.316 (4) C11—C12 1.392 (6)
N1—C1 1.393 (4) C11—H11 0.93
N2—C7 1.346 (4) C12—C13 1.363 (6)
N2—C6 1.385 (5) C12—H12 0.93
N2—H2N 0.85 (1) C13—C14 1.392 (5)
N3—C15 1.318 (4) C13—H13 0.93
N3—C9 1.398 (4) C15—C16 1.474 (5)
N4—C15 1.343 (4) C16—H16A 0.97
N4—C14 1.376 (4) C16—H16B 0.97
O1—Zn1—O2 117.3 (1) C2—C3—C4 122.1 (4)
O1—Zn1—O3 96.2 (1) C2—C3—H3 119.0
O1—Zn1—O4 154.1 (1) C4—C3—H3 119.0
O1—Zn1—N1 76.2 (1) C5—C4—C3 121.6 (3)
O1—Zn1—N3 85.3 (1) C5—C4—H4 119.2
O2—Zn1—O3 145.4 (1) C3—C4—H4 119.2
O2—Zn1—O4 88.6 (1) C4—C5—C6 116.4 (3)
O2—Zn1—N1 96.7 (1) C4—C5—H5 121.8
O2—Zn1—N3 77.1 (1) C6—C5—H5 121.8
O3—Zn1—O4 58.1 (1) C5—C6—N2 132.6 (3)
O3—Zn1—N1 99.5 (1) C5—C6—C1 122.2 (3)
O3—Zn1—N3 98.8 (1) N2—C6—C1 105.2 (3)
O4—Zn1—N1 103.1 (1) N1—C7—N2 112.3 (3)
O4—Zn1—N3 100.8 (1) N1—C7—C8 122.5 (3)
N1—Zn1—N3 155.2 (1) N2—C7—C8 125.2 (3)
C8—O1—Zn1 114.9 (2) O1—C8—C7 107.1 (3)
C8—O1—H1O 110 (4) O1—C8—H8A 110.3
Zn1—O1—H1O 108 (4) C7—C8—H8A 110.3
C16—O2—Zn1 115.8 (2) O1—C8—H8B 110.3
C16—O2—H2O 110 (3) C7—C8—H8B 110.3
Zn1—O2—H2O 128 (3) H8A—C8—H8B 108.5
N5—O3—Zn1 93.0 (2) C10—C9—N3 131.3 (3)
N5—O4—Zn1 92.4 (2) C10—C9—C14 120.8 (3)
supporting information
sup-5 Acta Cryst. (2007). E63, m15–m16
C7—N1—C1 106.0 (3) C11—C10—C9 117.5 (3)
C7—N1—Zn1 119.0 (2) C11—C10—H10 121.2
C1—N1—Zn1 134.9 (2) C9—C10—H10 121.2
C7—N2—C6 107.8 (3) C10—C11—C12 121.2 (4)
C7—N2—H2N 125 (3) C10—C11—H11 119.4
C6—N2—H2N 127 (3) C12—C11—H11 119.4
C15—N3—C9 106.4 (3) C13—C12—C11 122.3 (4)
C15—N3—Zn1 117.5 (2) C13—C12—H12 118.8
C9—N3—Zn1 135.2 (2) C11—C12—H12 118.8
C15—N4—C14 108.2 (3) C12—C13—C14 116.7 (4)
C15—N4—H4N 124 (2) C12—C13—H13 121.6
C14—N4—H4N 128 (2) C14—C13—H13 121.6
O5—N5—O4 122.3 (4) N4—C14—C13 132.9 (3)
O5—N5—O3 121.3 (4) N4—C14—C9 105.7 (3)
O4—N5—O3 116.5 (3) C13—C14—C9 121.4 (3)
O7—N6—O8 120.4 (3) N3—C15—N4 111.8 (3)
O7—N6—O6 121.1 (3) N3—C15—C16 122.1 (3)
O8—N6—O6 118.5 (3) N4—C15—C16 126.1 (3)
C2—C1—N1 130.7 (3) O2—C16—C15 106.3 (3)
C2—C1—C6 120.6 (3) O2—C16—H16A 110.5
N1—C1—C6 108.7 (3) C15—C16—H16A 110.5
C3—C2—C1 117.1 (3) O2—C16—H16B 110.5
C3—C2—H2 121.4 C15—C16—H16B 110.5
C1—C2—H2 121.4 H16A—C16—H16B 108.7
N3—Zn1—O1—C8 158.5 (3) N1—C1—C2—C3 178.0 (3)
N1—Zn1—O1—C8 −4.8 (2) C6—C1—C2—C3 −0.4 (5)
O2—Zn1—O1—C8 85.7 (3) C1—C2—C3—C4 1.4 (5)
O3—Zn1—O1—C8 −103.1 (2) C2—C3—C4—C5 −0.9 (6)
O4—Zn1—O1—C8 −96.4 (3) C3—C4—C5—C6 −0.6 (5)
N3—Zn1—O2—C16 6.1 (2) C4—C5—C6—N2 −177.4 (3)
N1—Zn1—O2—C16 161.7 (2) C4—C5—C6—C1 1.5 (5)
O3—Zn1—O2—C16 −80.7 (3) C7—N2—C6—C5 179.5 (3)
O4—Zn1—O2—C16 −95.3 (2) C7—N2—C6—C1 0.4 (4)
O1—Zn1—O2—C16 83.8 (3) C2—C1—C6—C5 −1.0 (5)
N3—Zn1—O3—N5 −96.53 (19) N1—C1—C6—C5 −179.8 (3)
N1—Zn1—O3—N5 100.28 (19) C2—C1—C6—N2 178.1 (3)
O2—Zn1—O3—N5 −16.6 (3) N1—C1—C6—N2 −0.6 (4)
O4—Zn1—O3—N5 0.76 (18) C1—N1—C7—N2 −0.3 (4)
O1—Zn1—O3—N5 177.30 (18) Zn1—N1—C7—N2 177.2 (2)
N3—Zn1—O4—N5 93.0 (2) C1—N1—C7—C8 178.4 (3)
N1—Zn1—O4—N5 −94.0 (2) Zn1—N1—C7—C8 −4.1 (4)
O2—Zn1—O4—N5 169.5 (2) C6—N2—C7—N1 −0.1 (4)
O3—Zn1—O4—N5 −0.76 (18) C6—N2—C7—C8 −178.7 (3)
O1—Zn1—O4—N5 −8.7 (3) Zn1—O1—C8—C7 4.0 (4)
N3—Zn1—N1—C7 −38.4 (4) N1—C7—C8—O1 −0.3 (5)
O2—Zn1—N1—C7 −111.9 (2) N2—C7—C8—O1 178.2 (3)
O4—Zn1—N1—C7 158.0 (2) Zn1—N3—C9—C10 9.7 (5)
O1—Zn1—N1—C7 4.6 (2) C15—N3—C9—C14 0.1 (3)
N3—Zn1—N1—C1 138.2 (3) Zn1—N3—C9—C14 −169.1 (2)
O2—Zn1—N1—C1 64.7 (3) N3—C9—C10—C11 −177.5 (3)
O3—Zn1—N1—C1 −84.7 (3) C14—C9—C10—C11 1.1 (5)
O4—Zn1—N1—C1 −25.4 (3) C9—C10—C11—C12 −0.1 (5)
O1—Zn1—N1—C1 −178.8 (3) C10—C11—C12—C13 −0.9 (6)
N1—Zn1—N3—C15 −77.0 (3) C11—C12—C13—C14 0.9 (6)
O2—Zn1—N3—C15 0.8 (2) C15—N4—C14—C13 −177.4 (4)
O3—Zn1—N3—C15 145.8 (2) C15—N4—C14—C9 0.2 (4)
O4—Zn1—N3—C15 86.8 (2) C12—C13—C14—N4 177.4 (4)
O1—Zn1—N3—C15 −118.6 (2) C12—C13—C14—C9 0.1 (5)
N1—Zn1—N3—C9 91.3 (4) C10—C9—C14—N4 −179.1 (3)
O2—Zn1—N3—C9 169.1 (3) N3—C9—C14—N4 −0.2 (4)
O3—Zn1—N3—C9 −45.9 (3) C10—C9—C14—C13 −1.1 (5)
O4—Zn1—N3—C9 −104.9 (3) N3—C9—C14—C13 177.8 (3)
O1—Zn1—N3—C9 49.6 (3) C9—N3—C15—N4 0.0 (4)
Zn1—O4—N5—O5 −178.5 (3) Zn1—N3—C15—N4 171.4 (2)
Zn1—O4—N5—O3 1.3 (3) C9—N3—C15—C16 −179.2 (3)
Zn1—O3—N5—O5 178.5 (3) Zn1—N3—C15—C16 −7.8 (4)
Zn1—O3—N5—O4 −1.3 (3) C14—N4—C15—N3 −0.1 (4)
C7—N1—C1—C2 −178.0 (3) C14—N4—C15—C16 179.1 (3)
Zn1—N1—C1—C2 5.1 (5) Zn1—O2—C16—C15 −10.5 (3)
C7—N1—C1—C6 0.6 (3) N3—C15—C16—O2 12.1 (4)
Zn1—N1—C1—C6 −176.3 (2) N4—C15—C16—O2 −167.0 (3)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O1—H1O···O1w 0.85 (1) 1.80 (1) 2.635 (4) 172 (5)
O2—H2O···O6i 0.84 (1) 2.08 (2) 2.877 (4) 159 (4)
O1w—H1w1···O5ii 0.85 (1) 2.07 (2) 2.908 (5) 168 (5)
O1w—H1w2···O6iii 0.85 (1) 2.29 (3) 3.038 (5) 148 (5)
N2—H2n···O6 0.85 (1) 2.14 (2) 2.922 (4) 154 (4)
N4—H4n···O7iv 0.85 (1) 2.14 (2) 2.959 (4) 163 (3)