Literature DB >> 22346839

Bis{1-[(1H-benzimidazol-2-yl)meth-yl]-1H-imidazole-κN}-bis-(3,5-dicarb-oxy-benzoato-κO)zinc octa-hydrate.

Lei Zhao, Bingtao Liu, Ting Li, Xiangru Meng.

Abstract

In the title complex, [Zn(C(9)H(5)O(6))(2)(C(11)n class="Species">H(10)N(4))(2)]·8H(2)O, the Zn(II) ion exhibits site symmetry 2. It shows a distorted tetra-hedral coordination defined by two N atoms from two symmetry-related 1-[(1H-benzimidazol-2-yl)meth-yl]-1H-imid-azole ligands and by two O atoms from two symmetry-related monodeprotonated 3,5-dicarb-oxy-benzoate anions. In the crystal, complex mol-ecules and solvent water mol-ecules are linked through inter-molecular O-H⋯O, O-H⋯N, and N-H⋯O hydrogen bonds into a three-dimensional network.

Entities: Chemical Disease Species

Year: 2012 PMID： 22346839 PMCID： PMC3274892 DOI： 10.1107/S160053681200147X

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background information on ZnII complexes constructed from both aromatic carboxylates and n class="Disease">N-heterocyclic ligands, see: Lin et al. (2008 ▶); Tian et al. (2010 ▶).

Experimental

Crystal data

[Zn(C9H5O6)2(C11n class="Species">H10N4)2]·8H2O M = 1024.22 Monoclinic, a = 20.870 (4) Å b = 15.008 (3) Å c = 15.472 (3) Å β = 109.51 (3)° V = 4567.9 (16) Å3 Z = 4 Mo Kα radiation μ = 0.63 mm−1 T = 293 K 0.18 × 0.15 × 0.14 mm

Data collection

Rigaku Saturn diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004 ▶) T min = 0.896, T max = 0.917 15325 measured reflections 4127 independent reflections 3898 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.054 wR(F 2) = 0.158 S = 1.07 4127 reflections 314 parameters H-atom parameters constrained Δρmax = 1.08 e Å−3 Δρmin = −0.45 e Å−3 Data collection: CrystalClear (Rigaku/MSC, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200147X/ff2052sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200147X/ff2052Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn(C₉H₅O₆)₂(C₁₁H₁₀N₄)₂]·8H₂O	F(000) = 2128
M_r = 1024.22	D_x = 1.489 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6831 reflections
a = 20.870 (4) Å	θ = 1.7–27.9°
b = 15.008 (3) Å	µ = 0.63 mm⁻¹
c = 15.472 (3) Å	T = 293 K
β = 109.51 (3)°	Prism, colourless
V = 4567.9 (16) Å³	0.18 × 0.15 × 0.14 mm
Z = 4

Rigaku Saturn diffractometer	4127 independent reflections
Radiation source: fine-focus sealed tube	3898 reflections with I > 2σ(I)
graphite	R_int = 0.031
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.3°, θ_min = 2.0°
ω scans	h = −25→25
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	k = −17→18
T_min = 0.896, T_max = 0.917	l = −18→18
15325 measured reflections

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0953P)² + 7.0031P] where P = (F_o² + 2F_c²)/3
4127 reflections	(Δ/σ)_max < 0.001
314 parameters	Δρ_max = 1.08 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	U_iso*/U_eq
Zn1	1.0000	0.47361 (3)	0.7500	0.02673 (18)
N1	1.00685 (12)	0.54973 (17)	0.85945 (17)	0.0303 (5)
N2	1.04718 (12)	0.60129 (16)	0.99936 (16)	0.0295 (5)
N3	1.20973 (13)	0.63838 (16)	1.09909 (17)	0.0323 (6)
N4	1.15439 (13)	0.75634 (17)	1.11874 (19)	0.0368 (6)
H4	1.1219	0.7891	1.1235	0.044*
O1	0.91112 (10)	0.41744 (14)	0.70946 (15)	0.0353 (5)
O2	0.95138 (12)	0.31291 (17)	0.64061 (18)	0.0486 (6)
O3	0.67237 (16)	0.42512 (17)	0.6806 (3)	0.0685 (9)
H3	0.6539	0.4603	0.6391	0.082*
O4	0.60726 (13)	0.3058 (2)	0.6317 (3)	0.0730 (10)
O5	0.70841 (13)	0.02986 (15)	0.5653 (3)	0.0604 (8)
H5	0.7129	−0.0244	0.5703	0.073*
O6	0.81799 (15)	0.02479 (16)	0.5819 (3)	0.0655 (9)
O7	0.03572 (17)	0.8297 (2)	0.1368 (3)	0.0841 (11)
H7A	0.0096	0.7939	0.1517	0.101*
H7B	0.0500	0.8761	0.1688	0.101*
O8	0.5834 (2)	0.5183 (3)	0.7433 (3)	0.1037 (14)
H8A	0.5724	0.4636	0.7401	0.124*
H8B	0.6017	0.5138	0.8011	0.124*
O9	0.4962 (3)	0.3677 (5)	0.6555 (6)	0.214 (4)
H9A	0.5130	0.3746	0.6129	0.256*
H9B	0.4592	0.3966	0.6428	0.256*
O10	0.4214 (6)	0.4833 (11)	0.5182 (7)	0.417 (11)
H10A	0.4442	0.4475	0.5597	0.501*
H10B	0.3822	0.4733	0.5214	0.501*
C1	1.05420 (15)	0.53995 (19)	0.9405 (2)	0.0303 (6)
H1A	1.0878	0.4964	0.9546	0.036*
C2	0.96815 (16)	0.6220 (2)	0.8680 (2)	0.0381 (7)
H2A	0.9311	0.6451	0.8215	0.046*
C3	0.99263 (16)	0.6536 (2)	0.9542 (2)	0.0396 (8)
H3A	0.9758	0.7015	0.9782	0.048*
C4	1.09106 (16)	0.6115 (2)	1.0948 (2)	0.0344 (7)
H4A	1.1063	0.5531	1.1204	0.041*
H4B	1.0650	0.6377	1.1298	0.041*
C5	1.15158 (15)	0.6686 (2)	1.10402 (19)	0.0302 (6)
C6	1.21887 (16)	0.7856 (2)	1.1250 (2)	0.0347 (7)
C7	1.24868 (19)	0.8692 (2)	1.1402 (3)	0.0483 (9)
H7C	1.2251	0.9194	1.1480	0.058*
C8	1.3160 (2)	0.8734 (3)	1.1431 (3)	0.0519 (9)
H8C	1.3381	0.9282	1.1529	0.062*
C9	1.35128 (18)	0.7980 (3)	1.1318 (3)	0.0506 (9)
H9C	1.3964	0.8037	1.1353	0.061*
C10	1.32114 (17)	0.7154 (2)	1.1157 (2)	0.0419 (8)
H10C	1.3446	0.6653	1.1074	0.050*
C11	1.25365 (15)	0.7105 (2)	1.1124 (2)	0.0327 (7)
C12	0.90560 (15)	0.3445 (2)	0.6650 (2)	0.0314 (6)
C13	0.83856 (15)	0.2976 (2)	0.64489 (19)	0.0297 (6)
C14	0.78386 (15)	0.3418 (2)	0.6558 (2)	0.0332 (7)
H14A	0.7884	0.4009	0.6749	0.040*
C15	0.72163 (16)	0.2984 (2)	0.6385 (2)	0.0357 (7)
C16	0.71589 (16)	0.2091 (2)	0.6120 (2)	0.0363 (7)
H16A	0.6747	0.1797	0.6007	0.044*
C17	0.77091 (16)	0.1639 (2)	0.6024 (2)	0.0346 (7)
C18	0.83224 (16)	0.2091 (2)	0.6178 (2)	0.0344 (7)
H18A	0.8691	0.1796	0.6098	0.041*
C19	0.66265 (17)	0.3463 (2)	0.6498 (3)	0.0439 (8)
C20	0.76632 (18)	0.0659 (2)	0.5806 (3)	0.0435 (8)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0215 (3)	0.0258 (3)	0.0320 (3)	0.000	0.0078 (2)	0.000
N1	0.0237 (12)	0.0282 (12)	0.0380 (14)	−0.0005 (10)	0.0089 (10)	−0.0032 (11)
N2	0.0276 (12)	0.0287 (12)	0.0324 (13)	−0.0035 (10)	0.0104 (10)	−0.0038 (10)
N3	0.0291 (13)	0.0262 (12)	0.0383 (14)	−0.0012 (10)	0.0070 (11)	0.0028 (11)
N4	0.0317 (14)	0.0321 (14)	0.0479 (16)	−0.0030 (11)	0.0152 (12)	−0.0087 (12)
O1	0.0294 (11)	0.0326 (11)	0.0417 (12)	−0.0077 (9)	0.0090 (9)	−0.0042 (9)
O2	0.0372 (13)	0.0513 (15)	0.0651 (16)	−0.0110 (11)	0.0276 (12)	−0.0135 (12)
O3	0.0585 (18)	0.0375 (15)	0.119 (3)	−0.0020 (13)	0.0428 (18)	−0.0142 (16)
O4	0.0347 (14)	0.0558 (17)	0.129 (3)	−0.0097 (13)	0.0275 (16)	−0.0182 (18)
O5	0.0418 (15)	0.0241 (12)	0.111 (3)	−0.0081 (10)	0.0193 (15)	−0.0041 (13)
O6	0.0515 (17)	0.0367 (15)	0.115 (3)	−0.0043 (12)	0.0364 (17)	−0.0187 (14)
O7	0.078 (2)	0.065 (2)	0.129 (3)	−0.0150 (17)	0.060 (2)	−0.018 (2)
O8	0.100 (3)	0.089 (3)	0.111 (3)	0.001 (2)	0.020 (3)	0.001 (2)
O9	0.117 (5)	0.204 (7)	0.321 (10)	0.020 (5)	0.074 (6)	−0.060 (7)
O10	0.317 (14)	0.76 (3)	0.254 (12)	0.332 (17)	0.204 (12)	0.243 (16)
C1	0.0241 (14)	0.0280 (15)	0.0376 (16)	−0.0019 (11)	0.0087 (12)	−0.0011 (12)
C2	0.0307 (16)	0.0373 (17)	0.0415 (18)	0.0074 (13)	0.0055 (13)	−0.0038 (14)
C3	0.0378 (17)	0.0364 (17)	0.0443 (18)	0.0087 (14)	0.0135 (15)	−0.0062 (14)
C4	0.0345 (16)	0.0372 (16)	0.0318 (15)	−0.0090 (13)	0.0113 (13)	−0.0024 (13)
C5	0.0302 (15)	0.0292 (15)	0.0298 (15)	−0.0035 (12)	0.0083 (12)	−0.0002 (12)
C6	0.0341 (16)	0.0323 (16)	0.0349 (16)	−0.0050 (13)	0.0077 (13)	−0.0040 (13)
C7	0.053 (2)	0.0324 (18)	0.060 (2)	−0.0087 (16)	0.0192 (18)	−0.0079 (16)
C8	0.051 (2)	0.043 (2)	0.058 (2)	−0.0209 (18)	0.0141 (18)	−0.0030 (17)
C9	0.0346 (18)	0.061 (2)	0.053 (2)	−0.0129 (17)	0.0102 (16)	0.0041 (18)
C10	0.0336 (17)	0.0413 (19)	0.049 (2)	0.0004 (14)	0.0110 (15)	0.0042 (15)
C11	0.0312 (15)	0.0283 (15)	0.0347 (16)	−0.0033 (12)	0.0059 (12)	0.0020 (12)
C12	0.0313 (15)	0.0315 (15)	0.0306 (15)	−0.0058 (12)	0.0092 (12)	0.0026 (12)
C13	0.0292 (15)	0.0295 (15)	0.0282 (14)	−0.0068 (12)	0.0065 (12)	0.0010 (12)
C14	0.0341 (16)	0.0243 (14)	0.0388 (17)	−0.0066 (12)	0.0092 (13)	−0.0024 (12)
C15	0.0303 (16)	0.0310 (16)	0.0436 (18)	−0.0041 (13)	0.0093 (13)	−0.0014 (13)
C16	0.0304 (16)	0.0294 (16)	0.0460 (18)	−0.0070 (13)	0.0084 (13)	0.0007 (13)
C17	0.0315 (16)	0.0273 (15)	0.0429 (18)	−0.0067 (12)	0.0097 (13)	−0.0013 (13)
C18	0.0309 (16)	0.0330 (16)	0.0405 (17)	−0.0047 (13)	0.0137 (13)	−0.0020 (13)
C19	0.0345 (18)	0.0325 (17)	0.063 (2)	−0.0033 (14)	0.0139 (16)	−0.0040 (16)
C20	0.0409 (19)	0.0302 (17)	0.058 (2)	−0.0065 (15)	0.0153 (16)	−0.0036 (15)

Zn1—O1	1.941 (2)	C1—H1A	0.9300
Zn1—O1ⁱ	1.941 (2)	C2—C3	1.344 (5)
Zn1—N1	2.008 (2)	C2—H2A	0.9300
Zn1—N1ⁱ	2.008 (2)	C3—H3A	0.9300
N1—C1	1.320 (4)	C4—C5	1.493 (4)
N1—C2	1.385 (4)	C4—H4A	0.9700
N2—C1	1.338 (4)	C4—H4B	0.9700
N2—C3	1.367 (4)	C6—C7	1.384 (5)
N2—C4	1.463 (4)	C6—C11	1.390 (4)
N3—C5	1.322 (4)	C7—C8	1.392 (5)
N3—C11	1.388 (4)	C7—H7C	0.9300
N4—C5	1.334 (4)	C8—C9	1.392 (6)
N4—C6	1.388 (4)	C8—H8C	0.9300
N4—H4	0.8600	C9—C10	1.375 (5)
O1—C12	1.278 (4)	C9—H9C	0.9300
O2—C12	1.233 (4)	C10—C11	1.394 (5)
O3—C19	1.266 (4)	C10—H10C	0.9300
O3—H3	0.8200	C12—C13	1.503 (4)
O4—C19	1.253 (4)	C13—C14	1.378 (4)
O5—C20	1.272 (4)	C13—C18	1.386 (4)
O5—H5	0.8200	C14—C15	1.396 (4)
O6—C20	1.236 (4)	C14—H14A	0.9300
O7—H7A	0.8500	C15—C16	1.395 (4)
O7—H7B	0.8492	C15—C19	1.485 (5)
O8—H8A	0.8501	C16—C17	1.384 (5)
O8—H8B	0.8502	C16—H16A	0.9300
O9—H9A	0.8500	C17—C18	1.397 (4)
O9—H9B	0.8501	C17—C20	1.505 (4)
O10—H10A	0.8502	C18—H18A	0.9300
O10—H10B	0.8498

O1—Zn1—O1ⁱ	128.52 (13)	N4—C6—C11	105.8 (3)
O1—Zn1—N1	108.11 (10)	C6—C7—C8	116.0 (3)
O1ⁱ—Zn1—N1	100.57 (10)	C6—C7—H7C	122.0
O1—Zn1—N1ⁱ	100.57 (10)	C8—C7—H7C	122.0
O1ⁱ—Zn1—N1ⁱ	108.11 (10)	C7—C8—C9	121.9 (3)
N1—Zn1—N1ⁱ	110.65 (15)	C7—C8—H8C	119.0
C1—N1—C2	105.8 (3)	C9—C8—H8C	119.0
C1—N1—Zn1	123.9 (2)	C10—C9—C8	121.8 (3)
C2—N1—Zn1	130.3 (2)	C10—C9—H9C	119.1
C1—N2—C3	108.0 (2)	C8—C9—H9C	119.1
C1—N2—C4	125.9 (3)	C9—C10—C11	116.7 (3)
C3—N2—C4	126.2 (3)	C9—C10—H10C	121.6
C5—N3—C11	107.3 (3)	C11—C10—H10C	121.6
C5—N4—C6	108.1 (3)	N3—C11—C6	107.7 (3)
C5—N4—H4	125.9	N3—C11—C10	131.0 (3)
C6—N4—H4	125.9	C6—C11—C10	121.3 (3)
C12—O1—Zn1	116.8 (2)	O2—C12—O1	123.7 (3)
C19—O3—H3	109.5	O2—C12—C13	121.3 (3)
C20—O5—H5	109.5	O1—C12—C13	115.0 (3)
H7A—O7—H7B	119.4	C14—C13—C18	119.9 (3)
H8A—O8—H8B	90.1	C14—C13—C12	120.1 (3)
H9A—O9—H9B	109.5	C18—C13—C12	119.9 (3)
H10A—O10—H10B	98.7	C13—C14—C15	120.5 (3)
N1—C1—N2	110.7 (3)	C13—C14—H14A	119.7
N1—C1—H1A	124.7	C15—C14—H14A	119.7
N2—C1—H1A	124.7	C16—C15—C14	119.2 (3)
C3—C2—N1	109.3 (3)	C16—C15—C19	120.4 (3)
C3—C2—H2A	125.4	C14—C15—C19	120.4 (3)
N1—C2—H2A	125.4	C17—C16—C15	120.6 (3)
C2—C3—N2	106.3 (3)	C17—C16—H16A	119.7
C2—C3—H3A	126.9	C15—C16—H16A	119.7
N2—C3—H3A	126.9	C16—C17—C18	119.3 (3)
N2—C4—C5	112.4 (2)	C16—C17—C20	120.7 (3)
N2—C4—H4A	109.1	C18—C17—C20	119.9 (3)
C5—C4—H4A	109.1	C13—C18—C17	120.4 (3)
N2—C4—H4B	109.1	C13—C18—H18A	119.8
C5—C4—H4B	109.1	C17—C18—H18A	119.8
H4A—C4—H4B	107.9	O4—C19—O3	123.9 (3)
N3—C5—N4	111.1 (3)	O4—C19—C15	118.6 (3)
N3—C5—C4	124.1 (3)	O3—C19—C15	117.5 (3)
N4—C5—C4	124.8 (3)	O6—C20—O5	124.1 (3)
C7—C6—N4	132.0 (3)	O6—C20—C17	119.6 (3)
C7—C6—C11	122.2 (3)	O5—C20—C17	116.3 (3)

O1—Zn1—N1—C1	121.9 (2)	C5—N3—C11—C10	178.6 (3)
O1ⁱ—Zn1—N1—C1	−14.8 (3)	C7—C6—C11—N3	179.9 (3)
N1ⁱ—Zn1—N1—C1	−128.9 (3)	N4—C6—C11—N3	0.0 (3)
O1—Zn1—N1—C2	−60.7 (3)	C7—C6—C11—C10	0.8 (5)
O1ⁱ—Zn1—N1—C2	162.6 (3)	N4—C6—C11—C10	−179.1 (3)
N1ⁱ—Zn1—N1—C2	48.5 (3)	C9—C10—C11—N3	−178.9 (3)
O1ⁱ—Zn1—O1—C12	−34.72 (19)	C9—C10—C11—C6	−0.1 (5)
N1—Zn1—O1—C12	−155.2 (2)	Zn1—O1—C12—O2	−6.1 (4)
N1ⁱ—Zn1—O1—C12	88.8 (2)	Zn1—O1—C12—C13	172.90 (18)
C2—N1—C1—N2	0.5 (3)	O2—C12—C13—C14	−166.9 (3)
Zn1—N1—C1—N2	178.40 (19)	O1—C12—C13—C14	14.1 (4)
C3—N2—C1—N1	−0.2 (3)	O2—C12—C13—C18	14.9 (4)
C4—N2—C1—N1	−179.1 (3)	O1—C12—C13—C18	−164.2 (3)
C1—N1—C2—C3	−0.6 (4)	C18—C13—C14—C15	−0.9 (5)
Zn1—N1—C2—C3	−178.3 (2)	C12—C13—C14—C15	−179.2 (3)
N1—C2—C3—N2	0.5 (4)	C13—C14—C15—C16	1.5 (5)
C1—N2—C3—C2	−0.2 (4)	C13—C14—C15—C19	−179.6 (3)
C4—N2—C3—C2	178.7 (3)	C14—C15—C16—C17	−0.4 (5)
C1—N2—C4—C5	86.6 (4)	C19—C15—C16—C17	−179.3 (3)
C3—N2—C4—C5	−92.1 (4)	C15—C16—C17—C18	−1.2 (5)
C11—N3—C5—N4	0.7 (3)	C15—C16—C17—C20	175.5 (3)
C11—N3—C5—C4	−178.9 (3)	C14—C13—C18—C17	−0.7 (5)
C6—N4—C5—N3	−0.8 (4)	C12—C13—C18—C17	177.5 (3)
C6—N4—C5—C4	178.9 (3)	C16—C17—C18—C13	1.8 (5)
N2—C4—C5—N3	−87.7 (4)	C20—C17—C18—C13	−175.0 (3)
N2—C4—C5—N4	92.7 (4)	C16—C15—C19—O4	−2.6 (5)
C5—N4—C6—C7	−179.5 (4)	C14—C15—C19—O4	178.5 (3)
C5—N4—C6—C11	0.5 (3)	C16—C15—C19—O3	174.8 (4)
N4—C6—C7—C8	179.3 (3)	C14—C15—C19—O3	−4.1 (5)
C11—C6—C7—C8	−0.6 (5)	C16—C17—C20—O6	−172.3 (4)
C6—C7—C8—C9	−0.3 (6)	C18—C17—C20—O6	4.4 (5)
C7—C8—C9—C10	1.0 (6)	C16—C17—C20—O5	4.9 (5)
C8—C9—C10—C11	−0.8 (5)	C18—C17—C20—O5	−178.4 (3)
C5—N3—C11—C6	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···O9	0.85	2.22	2.936 (8)	142.
O9—H9A···O4	0.85	2.15	2.634 (7)	115.
O9—H9B···O10	0.85	2.24	2.783 (12)	122.
O10—H10A···O9	0.85	1.93	2.783 (12)	179.
N4—H4···O7ⁱⁱ	0.86	1.97	2.808 (4)	163.
O3—H3···O10ⁱⁱⁱ	0.82	2.56	3.341 (10)	159.
O5—H5···N3^iv	0.82	1.77	2.577 (3)	165.
O7—H7A···O2^v	0.85	1.98	2.784 (4)	156.
O7—H7B···O8^vi	0.85	1.95	2.796 (5)	179.
O8—H8B···O6^vii	0.85	2.02	2.799 (6)	152.
O10—H10B···O6^viii	0.85	2.03	2.728 (9)	139.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8A⋯O9	0.85	2.22	2.936 (8)	142
O9—H9A⋯O4	0.85	2.15	2.634 (7)	115
O9—H9B⋯O10	0.85	2.24	2.783 (12)	122
O10—H10A⋯O9	0.85	1.93	2.783 (12)	179
N4—H4⋯O7ⁱ	0.86	1.97	2.808 (4)	163
O3—H3⋯O10ⁱⁱ	0.82	2.56	3.341 (10)	159
O5—H5⋯N3ⁱⁱⁱ	0.82	1.77	2.577 (3)	165
O7—H7A⋯O2^iv	0.85	1.98	2.784 (4)	156
O7—H7B⋯O8^v	0.85	1.95	2.796 (5)	179
O8—H8B⋯O6^vi	0.85	2.02	2.799 (6)	152
O10—H10B⋯O6^vii	0.85	2.03	2.728 (9)	139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

1 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

1 in total

2 in total

1. Bis{1-[(1H-benzotriazol-1-yl)meth-yl]-2-methyl-1H-imidazole-κN(3)}dichlorido-cobalt(II).

Authors: Haiyan Yang; Yinghua Li; Yaomin Zhao; Wenzhuo Li; Fang He
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-06-20

2. Bis{1-[(1H-benzotriazol-1-yl)meth-yl]-2-methyl-1H-imdazole-κN(3)}dichlorido-zinc.

Authors: Haiyan Yang; Yinghua Li
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-05-26

2 in total