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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

2

N

,

O

]-(nitrato-

j

2

O

,

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

(2)

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

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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

2

N

,

O

](nitrato-

κ

2

O

,

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 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

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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*

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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)

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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)

(7)

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)

(8)

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)

Figure

Figure 1

References

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