Literature DB >> 21202451

Bis[2-(1H-1,2,3-benzotriazol-1-yl)acetic acid-κN]dichloridozinc(II).

Tian Hang1, Qiong Ye.   

Abstract

In the title complex, [ZnCl(2)(C(8)H(7)N(3)O(2))(2)], the Zn(II) atom is coordinated by two chloride ions and two N atoms in a distorted tetra-hedral coordination environment. In the crystal structure, mol-ecules are linked by inter-molecular C-H⋯O and O-H⋯O hydrogen bonds, forming a three-dimensional network.

Entities:  

Year:  2008        PMID： 21202451      PMCID： PMC2961613          DOI： 10.1107/S1600536808006399

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


Related literature

For synthesis of the organic ligand, see: Danan et al. (1997 ▶); Xu & Ye (2007 ▶).

Experimental

Crystal data

[ZnCl2(C8H7N3O2)2] M = 490.60 Triclinic, a = 8.0896 (16) Å b = 9.6898 (19) Å c = 12.703 (3) Å α = 87.48 (3)° β = 84.25 (3)° γ = 83.95 (3)° V = 984.7 (4) Å3 Z = 2 Mo Kα radiation μ = 1.55 mm−1 T = 293 (2) K 0.3 × 0.2 × 0.1 mm

Data collection

Rigaku Mercury2 CCD diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.720, T max = 0.860 10222 measured reflections 4512 independent reflections 4022 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.099 S = 1.09 4512 reflections 275 parameters 2 restraints H-atom parameters constrained Δρmax = 0.63 e Å−3 Δρmin = −0.54 e Å−3 Data collection: CrystalClear (Rigaku, 2005 ▶); 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: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006399/pk2083sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006399/pk2083Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[ZnCl2(C8H7N3O2)2]Z = 2
Mr = 490.60F000 = 496
Triclinic, P1Dx = 1.655 Mg m−3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.0896 (16) ÅCell parameters from 10272 reflections
b = 9.6898 (19) Åθ = 3.1–28.7º
c = 12.703 (3) ŵ = 1.56 mm−1
α = 87.48 (3)ºT = 293 (2) K
β = 84.25 (3)ºBlock, colorless
γ = 83.95 (3)º0.3 × 0.2 × 0.1 mm
V = 984.7 (4) Å3
Mercury2 CCD (2x2 bin mode) diffractometer4512 independent reflections
Radiation source: fine-focus sealed tube4022 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
Detector resolution: 13.6612 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.1º
CCD_Profile_fitting scansh = −10→10
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −12→12
Tmin = 0.720, Tmax = 0.860l = −16→16
10222 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.099  w = 1/[σ2(Fo2) + (0.0423P)2 + 0.762P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
4512 reflectionsΔρmax = 0.63 e Å−3
275 parametersΔρmin = −0.54 e Å−3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
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 > 2σ(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.
xyzUiso*/Ueq
Zn1−0.24666 (3)0.21707 (3)0.28538 (2)0.03130 (10)
Cl1−0.49995 (9)0.21702 (8)0.23354 (6)0.04842 (18)
Cl2−0.17619 (9)0.06835 (7)0.41738 (5)0.04511 (17)
O10.4086 (3)0.4222 (3)−0.1108 (2)0.0764 (8)
H1C0.48840.4518−0.08740.115*
O2−0.5545 (3)0.9218 (2)0.3737 (2)0.0627 (6)
H2B−0.58590.98460.32010.061 (11)*
O3−0.3617 (3)0.7988 (2)0.26399 (16)0.0555 (6)
O40.2761 (3)0.4739 (3)0.05103 (16)0.0546 (6)
N1−0.2805 (3)0.6045 (2)0.41091 (17)0.0327 (4)
N2−0.0410 (3)0.2952 (2)0.09576 (17)0.0350 (5)
N30.0805 (3)0.2522 (2)0.02244 (16)0.0338 (4)
N4−0.3401 (3)0.4916 (2)0.37794 (17)0.0350 (5)
N5−0.0605 (3)0.1913 (2)0.16490 (16)0.0334 (4)
N6−0.2121 (3)0.4090 (2)0.33810 (17)0.0330 (4)
C10.2918 (4)−0.1020 (3)0.0338 (2)0.0470 (7)
H1A0.3714−0.16600.00040.048 (9)*
C20.1680 (4)0.6422 (3)0.3786 (2)0.0465 (7)
H2A0.25060.69850.38930.061 (10)*
C30.1993 (4)−0.1432 (3)0.1290 (2)0.0504 (7)
H3A0.2219−0.23300.15650.056 (10)*
C40.0791 (4)−0.0547 (3)0.1816 (2)0.0434 (6)
H4A0.0190−0.08200.24390.048 (9)*
C50.0517 (3)0.0791 (3)0.13594 (19)0.0329 (5)
C60.1357 (3)0.3460 (3)−0.0639 (2)0.0380 (6)
H6A0.04390.4144−0.07890.050 (9)*
H6B0.16980.2937−0.12720.051 (9)*
C70.0055 (4)0.6881 (3)0.4093 (2)0.0404 (6)
H7A−0.02560.77370.43970.042 (8)*
C80.2157 (3)0.5130 (3)0.3319 (2)0.0456 (7)
H8A0.32820.48760.31210.054 (9)*
C9−0.3956 (3)0.7224 (3)0.4457 (2)0.0375 (6)
H9A−0.34640.77270.49700.056 (10)*
H9B−0.49790.69000.47970.057 (10)*
C100.2827 (4)0.4195 (3)−0.0345 (2)0.0391 (6)
C110.1012 (3)0.4239 (3)0.3143 (2)0.0391 (6)
H11A0.13250.33810.28440.042 (8)*
C120.1438 (3)0.1188 (3)0.0429 (2)0.0323 (5)
C130.2670 (3)0.0281 (3)−0.0107 (2)0.0415 (6)
H13A0.32820.0552−0.07270.044 (8)*
C14−0.4354 (3)0.8186 (3)0.3517 (2)0.0360 (5)
C15−0.0664 (3)0.4692 (2)0.34439 (19)0.0313 (5)
C16−0.1116 (3)0.5972 (2)0.39085 (19)0.0311 (5)
U11U22U33U12U13U23
Zn10.03324 (16)0.02833 (16)0.03146 (16)−0.00575 (11)0.00609 (11)−0.00602 (11)
Cl10.0373 (3)0.0458 (4)0.0624 (5)−0.0034 (3)−0.0060 (3)−0.0035 (3)
Cl20.0551 (4)0.0419 (4)0.0363 (3)−0.0022 (3)0.0009 (3)0.0019 (3)
O10.0671 (16)0.100 (2)0.0642 (16)−0.0331 (15)0.0161 (12)−0.0134 (15)
O20.0577 (14)0.0495 (13)0.0762 (17)0.0028 (10)0.0081 (12)−0.0038 (12)
O30.0670 (14)0.0550 (13)0.0375 (11)0.0109 (11)0.0131 (10)−0.0053 (9)
O40.0568 (13)0.0696 (15)0.0398 (11)−0.0209 (11)0.0038 (10)−0.0117 (10)
N10.0334 (10)0.0284 (10)0.0360 (11)−0.0040 (8)0.0012 (8)−0.0081 (8)
N20.0393 (11)0.0324 (11)0.0317 (11)−0.0044 (9)0.0075 (9)−0.0042 (8)
N30.0337 (11)0.0345 (11)0.0318 (11)−0.0055 (8)0.0071 (8)−0.0037 (8)
N40.0323 (11)0.0330 (11)0.0400 (12)−0.0074 (8)0.0028 (9)−0.0100 (9)
N50.0383 (11)0.0279 (10)0.0321 (11)−0.0036 (8)0.0067 (9)−0.0025 (8)
N60.0320 (10)0.0291 (10)0.0384 (11)−0.0068 (8)0.0014 (9)−0.0074 (8)
C10.0420 (15)0.0468 (16)0.0484 (16)0.0110 (12)0.0016 (12)−0.0103 (13)
C20.0382 (14)0.0512 (17)0.0539 (17)−0.0206 (12)−0.0079 (13)0.0027 (13)
C30.0575 (18)0.0400 (16)0.0492 (17)0.0097 (13)0.0000 (14)0.0012 (13)
C40.0512 (16)0.0376 (14)0.0386 (14)−0.0014 (12)0.0051 (12)0.0023 (11)
C50.0348 (12)0.0324 (12)0.0306 (12)−0.0029 (10)0.0031 (10)−0.0053 (10)
C60.0429 (14)0.0397 (14)0.0303 (12)−0.0063 (11)0.0039 (10)0.0002 (10)
C70.0463 (15)0.0324 (13)0.0450 (15)−0.0125 (11)−0.0068 (12)−0.0032 (11)
C80.0297 (13)0.0563 (18)0.0498 (16)−0.0046 (12)0.0004 (12)0.0011 (13)
C90.0386 (14)0.0369 (13)0.0352 (13)0.0004 (11)0.0051 (11)−0.0115 (11)
C100.0445 (14)0.0359 (13)0.0364 (14)−0.0084 (11)0.0013 (10)0.0022 (11)
C110.0335 (13)0.0417 (14)0.0411 (14)−0.0010 (11)−0.0007 (11)−0.0055 (11)
C120.0304 (12)0.0343 (13)0.0319 (12)−0.0045 (10)0.0013 (9)−0.0044 (10)
C130.0337 (13)0.0514 (16)0.0367 (14)0.0003 (11)0.0069 (11)−0.0062 (12)
C140.0353 (13)0.0332 (12)0.0393 (14)−0.0078 (9)0.0051 (10)−0.0086 (10)
C150.0325 (12)0.0299 (12)0.0318 (12)−0.0064 (9)−0.0015 (9)−0.0019 (9)
C160.0326 (12)0.0301 (12)0.0310 (12)−0.0061 (9)−0.0014 (9)−0.0015 (9)
Zn1—N52.041 (2)C2—C71.367 (4)
Zn1—N62.059 (2)C2—C81.410 (4)
Zn1—Cl12.2142 (9)C2—H2A0.9295
Zn1—Cl22.2403 (10)C3—C41.369 (4)
O1—C101.336 (4)C3—H3A0.9301
O1—H1C0.8200C4—C51.402 (4)
O2—C141.332 (3)C4—H4A0.9297
O2—H2B0.9295C5—C121.394 (3)
O3—C141.223 (3)C6—C101.533 (4)
O4—C101.222 (3)C6—H6A0.9698
N1—N41.340 (3)C6—H6B0.9703
N1—C161.360 (3)C7—C161.402 (3)
N1—C91.451 (3)C7—H7A0.9301
N2—N51.318 (3)C8—C111.372 (4)
N2—N31.331 (3)C8—H8A0.9298
N3—C121.363 (3)C9—C141.521 (4)
N3—C61.459 (3)C9—H9A0.9703
N4—N61.314 (3)C9—H9B0.9702
N5—C51.379 (3)C11—C151.400 (4)
N6—C151.380 (3)C11—H11A0.9294
C1—C131.363 (4)C12—C131.401 (4)
C1—C31.422 (4)C13—H13A0.9300
C1—H1A0.9292C15—C161.395 (3)
N5—Zn1—N6101.73 (9)N3—C6—H6A109.6
N5—Zn1—Cl1113.50 (7)C10—C6—H6A109.7
N6—Zn1—Cl1110.90 (7)N3—C6—H6B109.5
N5—Zn1—Cl2107.14 (7)C10—C6—H6B109.4
N6—Zn1—Cl2104.41 (7)H6A—C6—H6B108.2
Cl1—Zn1—Cl2117.63 (4)C2—C7—C16115.2 (3)
C10—O1—H1C109.5C2—C7—H7A122.6
C14—O2—H2B119.5C16—C7—H7A122.3
N4—N1—C16111.2 (2)C11—C8—C2122.0 (3)
N4—N1—C9119.7 (2)C11—C8—H8A119.0
C16—N1—C9128.3 (2)C2—C8—H8A119.0
N5—N2—N3107.4 (2)N1—C9—C14110.2 (2)
N2—N3—C12111.6 (2)N1—C9—H9A109.7
N2—N3—C6120.6 (2)C14—C9—H9A109.7
C12—N3—C6127.7 (2)N1—C9—H9B109.6
N6—N4—N1107.55 (19)C14—C9—H9B109.5
N2—N5—C5109.6 (2)H9A—C9—H9B108.2
N2—N5—Zn1118.20 (16)O4—C10—O1125.3 (3)
C5—N5—Zn1132.12 (17)O4—C10—C6120.4 (2)
N4—N6—C15109.65 (19)O1—C10—C6114.2 (2)
N4—N6—Zn1120.39 (16)C8—C11—C15116.2 (3)
C15—N6—Zn1129.87 (17)C8—C11—H11A122.1
C13—C1—C3122.2 (3)C15—C11—H11A121.6
C13—C1—H1A118.7N3—C12—C5104.5 (2)
C3—C1—H1A119.1N3—C12—C13133.1 (2)
C7—C2—C8122.8 (3)C5—C12—C13122.4 (2)
C7—C2—H2A118.6C1—C13—C12115.8 (3)
C8—C2—H2A118.6C1—C13—H13A122.1
C4—C3—C1122.1 (3)C12—C13—H13A122.1
C4—C3—H3A119.1O3—C14—O2124.5 (3)
C1—C3—H3A118.8O3—C14—C9120.8 (2)
C3—C4—C5116.1 (3)O2—C14—C9114.6 (2)
C3—C4—H4A121.8N6—C15—C16106.8 (2)
C5—C4—H4A122.1N6—C15—C11132.0 (2)
N5—C5—C12106.9 (2)C16—C15—C11121.1 (2)
N5—C5—C4131.7 (2)N1—C16—C15104.7 (2)
C12—C5—C4121.4 (2)N1—C16—C7132.6 (2)
N3—C6—C10110.5 (2)C15—C16—C7122.7 (2)
N5—N2—N3—C12−0.4 (3)C16—N1—C9—C1481.9 (3)
N5—N2—N3—C6−177.9 (2)N3—C6—C10—O4−48.2 (4)
C16—N1—N4—N61.1 (3)N3—C6—C10—O1134.4 (3)
C9—N1—N4—N6171.8 (2)C2—C8—C11—C150.6 (4)
N3—N2—N5—C50.4 (3)N2—N3—C12—C50.3 (3)
N3—N2—N5—Zn1−176.82 (16)C6—N3—C12—C5177.6 (2)
N6—Zn1—N5—N2−47.2 (2)N2—N3—C12—C13178.1 (3)
Cl1—Zn1—N5—N272.01 (19)C6—N3—C12—C13−4.6 (5)
Cl2—Zn1—N5—N2−156.44 (17)N5—C5—C12—N30.0 (3)
N6—Zn1—N5—C5136.3 (2)C4—C5—C12—N3178.8 (2)
Cl1—Zn1—N5—C5−104.5 (2)N5—C5—C12—C13−178.2 (2)
Cl2—Zn1—N5—C527.1 (2)C4—C5—C12—C130.7 (4)
N1—N4—N6—C15−0.4 (3)C3—C1—C13—C12−0.4 (4)
N1—N4—N6—Zn1176.54 (15)N3—C12—C13—C1−177.6 (3)
N5—Zn1—N6—N4148.39 (19)C5—C12—C13—C1−0.1 (4)
Cl1—Zn1—N6—N427.4 (2)N1—C9—C14—O3−6.9 (4)
Cl2—Zn1—N6—N4−100.26 (19)N1—C9—C14—O2172.8 (2)
N5—Zn1—N6—C15−35.3 (2)N4—N6—C15—C16−0.4 (3)
Cl1—Zn1—N6—C15−156.3 (2)Zn1—N6—C15—C16−176.95 (17)
Cl2—Zn1—N6—C1576.0 (2)N4—N6—C15—C11179.4 (3)
C13—C1—C3—C40.3 (5)Zn1—N6—C15—C112.8 (4)
C1—C3—C4—C50.3 (5)C8—C11—C15—N6179.5 (3)
N2—N5—C5—C12−0.2 (3)C8—C11—C15—C16−0.8 (4)
Zn1—N5—C5—C12176.47 (18)N4—N1—C16—C15−1.3 (3)
N2—N5—C5—C4−178.9 (3)C9—N1—C16—C15−170.9 (2)
Zn1—N5—C5—C4−2.2 (4)N4—N1—C16—C7179.4 (3)
C3—C4—C5—N5177.8 (3)C9—N1—C16—C79.7 (5)
C3—C4—C5—C12−0.7 (4)N6—C15—C16—N11.0 (3)
N2—N3—C6—C1092.5 (3)C11—C15—C16—N1−178.8 (2)
C12—N3—C6—C10−84.5 (3)N6—C15—C16—C7−179.6 (2)
C8—C2—C7—C16−0.1 (4)C11—C15—C16—C70.6 (4)
C7—C2—C8—C11−0.1 (5)C2—C7—C16—N1179.1 (3)
N4—N1—C9—C14−87.0 (3)C2—C7—C16—C15−0.1 (4)
D—H···AD—HH···AD···AD—H···A
O1—H1C···O4i0.822.203.015 (4)171
O2—H2B···Cl1ii0.932.593.348 (3)139
C6—H6A···O4iii0.972.693.586 (4)153
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1C⋯O4i0.822.203.015 (4)171
O2—H2B⋯Cl1ii0.932.593.348 (3)139
C6—H6A⋯O4iii0.972.693.586 (4)153

Symmetry codes: (i) ; (ii) ; (iii) .

  2 in total

1.  A short history of SHELX.

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

2.  Synthesis and antiparasitic activities of amidinic azolated derivatives.

Authors:  A Danan; D Charon; S Kirkiacharian; C Bories; P M Loiseau
Journal:  Farmaco       Date:  1997-04
  2 in total
  2 in total

1.  Bis[2-(1H-benzotriazol-1-yl)acetonitrile-κN]dibromidocopper(II).

Authors:  Wei Wang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-07-05

2.  (1H-1,2,3-Benzotriazol-1-yl)methyl 2,2-dimethyl-propano-ate.

Authors:  Sen Xu; Yingzhong Shen
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-14
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.