Literature DB >> 21202168

Bis[4-(4-methoxy-phen-yl)-4H-1,2,4-triazole-κN]bis-(thio-cyanato-κN)zinc(II).

Ya Zuo1.   

Abstract

In the title complex, [Zn(n class="Chemical">NCS)(2)(C(9)H(9)N(3)O)(2)], the Zn(II) ion is coordinated by two N atoms from the NCS(-) anions and two N atoms from two 4-(4-methoxy-phen-yl)-4H-1,2,4-triazole ligands in a slightly distorted tetra-hedral geometry. Three inter-molecular weak hydrogen-bonding contacts of the types C-H⋯N, C-H⋯S and C-H⋯O are observed in the crystal structure.

Entities:  

Year:  2008        PMID： 21202168      PMCID： PMC2961330          DOI： 10.1107/S1600536808008325

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


Related literature

For related literature, see: Han et al. (2006 ▶); Ling & Zhang (2007 ▶); Thomann et al. (1994 ▶); Yin et al. (2007 ▶); Zhao et al. (2002 ▶); Zhou et al. (2007 ▶).

Experimental

Crystal data

[Zn(NCS)2(C9n class="Species">H9N3O)2] M = 531.91 Monoclinic, a = 7.812 (3) Å b = 17.111 (6) Å c = 18.201 (6) Å β = 99.726 (6)° V = 2398.0 (15) Å3 Z = 4 Mo Kα radiation μ = 1.23 mm−1 T = 293 (2) K 0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.700, T max = 0.884 13731 measured reflections 4932 independent reflections 2127 reflections with I > 2σ(I) R int = 0.121

Refinement

R[F 2 > 2σ(F 2)] = 0.067 wR(F 2) = 0.158 S = 0.97 4932 reflections 300 parameters H-atom parameters constrained Δρmax = 0.39 e Å−3 Δρmin = −0.33 e Å−3 Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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/S1600536808008325/si2077sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008325/si2077Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Zn(NCS)2(C9H9N3O)2]F000 = 1088
Mr = 531.91Dx = 1.473 Mg m−3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
a = 7.812 (3) ÅCell parameters from 713 reflections
b = 17.111 (6) Åθ = 2.6–21.1º
c = 18.201 (6) ŵ = 1.23 mm−1
β = 99.726 (6)ºT = 293 (2) K
V = 2398.0 (15) Å3Block, colorless
Z = 40.16 × 0.12 × 0.10 mm
Bruker SMART CCD area-detector diffractometer4932 independent reflections
Radiation source: fine-focus sealed tube2127 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.121
T = 293(2) Kθmax = 26.5º
φ and O scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.700, Tmax = 0.884k = −21→14
13731 measured reflectionsl = −22→18
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.158  w = 1/[σ2(Fo2) + (0.0555P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
4932 reflectionsΔρmax = 0.39 e Å−3
300 parametersΔρmin = −0.33 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/Ueq
Zn10.36832 (9)1.10583 (5)0.05909 (4)0.0434 (3)
N10.2576 (6)1.0131 (3)0.0996 (3)0.0448 (14)
N20.2447 (7)1.0191 (4)0.1742 (3)0.0506 (15)
N30.1960 (6)0.8971 (4)0.1360 (3)0.0417 (13)
O10.0331 (6)0.5821 (3)0.1525 (2)0.0495 (12)
C10.2292 (7)0.9405 (4)0.0785 (3)0.0393 (16)
H10.23170.92160.03070.047*
C20.2083 (9)0.9483 (5)0.1939 (4)0.055 (2)
H20.19270.93460.24180.066*
C30.1559 (8)0.8147 (4)0.1374 (3)0.0364 (15)
C40.2212 (8)0.7714 (4)0.1995 (3)0.0436 (17)
H40.29490.79430.23910.052*
C50.1762 (8)0.6938 (4)0.2023 (3)0.0429 (17)
H50.21790.66460.24470.051*
C60.0701 (8)0.6587 (4)0.1433 (3)0.0383 (16)
C70.0088 (8)0.7023 (4)0.0807 (3)0.0462 (18)
H7−0.06100.67910.04000.055*
C80.0506 (8)0.7795 (4)0.0784 (3)0.0467 (18)
H80.00730.80890.03640.056*
C9−0.0628 (8)0.5413 (4)0.0903 (4)0.060 (2)
H9A−0.17520.56490.07670.090*
H9B−0.07620.48760.10350.090*
H9C−0.00140.54400.04890.090*
N40.6037 (6)1.1085 (3)0.1237 (3)0.0423 (13)
N50.7566 (7)1.1233 (4)0.0996 (3)0.0586 (18)
N60.8049 (6)1.1152 (3)0.2222 (3)0.0421 (14)
O21.1582 (6)1.1055 (3)0.5135 (2)0.0655 (14)
C100.6367 (8)1.1026 (4)0.1966 (3)0.0464 (16)
H100.55411.09120.22640.056*
C110.8730 (9)1.1266 (5)0.1594 (4)0.065 (2)
H110.99021.13590.15920.078*
C120.8924 (7)1.1139 (4)0.2991 (3)0.0385 (15)
C130.8962 (8)1.1802 (4)0.3406 (3)0.0474 (18)
H130.84101.22530.32020.057*
C140.9835 (8)1.1797 (4)0.4138 (4)0.0509 (18)
H140.98601.22460.44290.061*
C151.0660 (7)1.1130 (4)0.4433 (3)0.0436 (16)
C161.0579 (8)1.0461 (4)0.4010 (4)0.0505 (18)
H161.11141.00070.42140.061*
C170.9708 (8)1.0461 (4)0.3285 (4)0.0462 (18)
H170.96511.00090.29990.055*
C181.1740 (10)1.1722 (5)0.5603 (4)0.080 (3)
H18A1.22791.21380.53720.120*
H18B1.24401.15950.60740.120*
H18C1.06081.18840.56810.120*
S10.1894 (3)1.35631 (13)0.11268 (10)0.0765 (7)
N70.2543 (7)1.2013 (4)0.0874 (3)0.0527 (16)
C190.2283 (9)1.2663 (5)0.0986 (3)0.0445 (18)
S20.3020 (3)1.10216 (14)−0.19983 (10)0.0796 (7)
N80.3645 (7)1.0978 (4)−0.0466 (3)0.0619 (17)
C200.3357 (8)1.1003 (4)−0.1112 (4)0.0500 (17)
U11U22U33U12U13U23
Zn10.0453 (4)0.0419 (5)0.0414 (4)0.0001 (5)0.0025 (3)0.0030 (4)
N10.045 (3)0.045 (4)0.045 (3)−0.001 (3)0.007 (3)−0.003 (3)
N20.070 (4)0.047 (4)0.036 (3)−0.003 (3)0.012 (3)−0.007 (3)
N30.051 (3)0.045 (4)0.029 (3)−0.001 (3)0.008 (2)−0.001 (3)
O10.062 (3)0.040 (3)0.046 (3)−0.008 (2)0.006 (2)0.001 (2)
C10.041 (4)0.043 (5)0.033 (4)0.000 (3)0.006 (3)−0.009 (3)
C20.073 (5)0.055 (6)0.039 (4)−0.002 (4)0.013 (4)−0.005 (4)
C30.041 (4)0.032 (4)0.037 (4)0.005 (3)0.010 (3)0.000 (3)
C40.047 (4)0.051 (5)0.031 (4)−0.007 (4)0.000 (3)−0.009 (3)
C50.044 (4)0.048 (5)0.036 (4)0.000 (3)0.004 (3)0.011 (3)
C60.033 (3)0.043 (5)0.041 (4)−0.002 (3)0.011 (3)−0.002 (3)
C70.052 (4)0.047 (5)0.035 (4)−0.014 (4)−0.007 (3)−0.007 (3)
C80.059 (4)0.043 (5)0.033 (4)−0.009 (4)−0.004 (3)0.012 (3)
C90.061 (5)0.050 (5)0.068 (5)−0.010 (4)0.006 (4)−0.019 (4)
N40.037 (3)0.052 (4)0.039 (3)0.003 (3)0.007 (2)0.008 (3)
N50.046 (3)0.087 (5)0.043 (3)−0.005 (3)0.009 (3)0.009 (3)
N60.037 (3)0.049 (4)0.039 (3)−0.003 (3)0.006 (3)0.000 (3)
O20.071 (3)0.070 (4)0.048 (3)0.003 (3)−0.012 (2)−0.011 (3)
C100.042 (4)0.052 (5)0.045 (4)−0.002 (4)0.007 (3)0.000 (4)
C110.045 (4)0.099 (7)0.052 (5)−0.012 (4)0.012 (4)0.006 (5)
C120.033 (3)0.046 (5)0.039 (4)0.001 (3)0.009 (3)−0.003 (4)
C130.048 (4)0.048 (5)0.046 (4)0.008 (4)0.008 (4)0.008 (4)
C140.058 (5)0.041 (5)0.053 (4)0.003 (4)0.006 (4)−0.009 (4)
C150.039 (3)0.049 (5)0.043 (4)−0.009 (4)0.006 (3)−0.006 (4)
C160.057 (4)0.040 (5)0.050 (4)0.013 (4)−0.004 (4)0.006 (4)
C170.045 (4)0.040 (5)0.053 (5)0.009 (4)0.008 (3)−0.011 (4)
C180.072 (5)0.100 (8)0.059 (5)0.011 (5)−0.010 (4)−0.018 (5)
S10.128 (2)0.0453 (13)0.0492 (12)0.0171 (13)−0.0041 (12)−0.0014 (10)
N70.060 (4)0.050 (4)0.045 (3)0.003 (3)−0.001 (3)−0.001 (3)
C190.053 (4)0.048 (5)0.030 (4)−0.005 (4)0.000 (3)0.005 (4)
S20.1267 (18)0.0637 (15)0.0433 (11)−0.0087 (14)−0.0001 (12)−0.0048 (11)
N80.065 (4)0.070 (5)0.048 (4)0.004 (4)0.003 (3)0.001 (4)
C200.054 (4)0.038 (4)0.055 (5)0.001 (4)0.001 (4)−0.001 (4)
Zn1—N81.923 (6)N4—C101.312 (7)
Zn1—N71.970 (6)N4—N51.365 (6)
Zn1—N12.005 (5)N5—C111.296 (7)
Zn1—N42.009 (5)N6—C101.336 (7)
N1—C11.309 (8)N6—C111.354 (7)
N1—N21.382 (7)N6—C121.450 (7)
N2—C21.308 (8)O2—C151.363 (7)
N3—C11.344 (7)O2—C181.417 (8)
N3—C21.361 (8)C10—H100.9300
N3—C31.445 (8)C11—H110.9300
O1—C61.359 (7)C12—C131.360 (9)
O1—C91.430 (7)C12—C171.377 (8)
C1—H10.9300C13—C141.391 (8)
C2—H20.9300C13—H130.9300
C3—C81.375 (8)C14—C151.374 (9)
C3—C41.376 (8)C14—H140.9300
C4—C51.378 (9)C15—C161.375 (9)
C4—H40.9300C16—C171.379 (8)
C5—C61.379 (8)C16—H160.9300
C5—H50.9300C17—H170.9300
C6—C71.379 (8)C18—H18A0.9600
C7—C81.364 (9)C18—H18B0.9600
C7—H70.9300C18—H18C0.9600
C8—H80.9300S1—C191.598 (8)
C9—H9A0.9600N7—C191.155 (8)
C9—H9B0.9600S2—C201.591 (7)
C9—H9C0.9600N8—C201.160 (7)
N8—Zn1—N7112.9 (2)H9B—C9—H9C109.5
N8—Zn1—N1112.1 (2)C10—N4—N5107.9 (5)
N7—Zn1—N1108.5 (2)C10—N4—Zn1126.4 (4)
N8—Zn1—N4116.4 (2)N5—N4—Zn1125.5 (4)
N7—Zn1—N4103.8 (2)C11—N5—N4105.4 (5)
N1—Zn1—N4102.2 (2)C10—N6—C11103.4 (5)
C1—N1—N2108.8 (5)C10—N6—C12127.6 (5)
C1—N1—Zn1134.9 (5)C11—N6—C12129.0 (5)
N2—N1—Zn1114.2 (4)C15—O2—C18117.8 (6)
C2—N2—N1104.9 (5)N4—C10—N6110.7 (6)
C1—N3—C2104.5 (6)N4—C10—H10124.6
C1—N3—C3128.5 (5)N6—C10—H10124.6
C2—N3—C3127.0 (6)N5—C11—N6112.6 (6)
C6—O1—C9117.9 (5)N5—C11—H11123.7
N1—C1—N3109.9 (6)N6—C11—H11123.7
N1—C1—H1125.0C13—C12—C17121.3 (6)
N3—C1—H1125.0C13—C12—N6119.1 (6)
N2—C2—N3111.9 (6)C17—C12—N6119.7 (6)
N2—C2—H2124.0C12—C13—C14119.3 (6)
N3—C2—H2124.0C12—C13—H13120.4
C8—C3—C4119.7 (6)C14—C13—H13120.4
C8—C3—N3121.1 (6)C15—C14—C13120.0 (6)
C4—C3—N3119.2 (6)C15—C14—H14120.0
C3—C4—C5119.2 (6)C13—C14—H14120.0
C3—C4—H4120.4O2—C15—C14125.7 (7)
C5—C4—H4120.4O2—C15—C16114.3 (7)
C4—C5—C6121.0 (6)C14—C15—C16120.0 (6)
C4—C5—H5119.5C15—C16—C17120.2 (6)
C6—C5—H5119.5C15—C16—H16119.9
O1—C6—C7125.0 (6)C17—C16—H16119.9
O1—C6—C5115.9 (6)C12—C17—C16119.2 (6)
C7—C6—C5119.2 (6)C12—C17—H17120.4
C8—C7—C6119.9 (6)C16—C17—H17120.4
C8—C7—H7120.1O2—C18—H18A109.5
C6—C7—H7120.1O2—C18—H18B109.5
C7—C8—C3121.0 (6)H18A—C18—H18B109.5
C7—C8—H8119.5O2—C18—H18C109.5
C3—C8—H8119.5H18A—C18—H18C109.5
O1—C9—H9A109.5H18B—C18—H18C109.5
O1—C9—H9B109.5C19—N7—Zn1161.0 (6)
H9A—C9—H9B109.5N7—C19—S1178.8 (7)
O1—C9—H9C109.5C20—N8—Zn1168.1 (6)
H9A—C9—H9C109.5N8—C20—S2178.1 (7)
N8—Zn1—N1—C124.0 (7)N7—Zn1—N4—N5−108.5 (5)
N7—Zn1—N1—C1149.4 (6)N1—Zn1—N4—N5138.7 (5)
N4—Zn1—N1—C1−101.4 (6)C10—N4—N5—C11−0.9 (8)
N8—Zn1—N1—N2−175.1 (4)Zn1—N4—N5—C11174.2 (5)
N7—Zn1—N1—N2−49.7 (4)N5—N4—C10—N61.8 (8)
N4—Zn1—N1—N259.5 (4)Zn1—N4—C10—N6−173.2 (4)
C1—N1—N2—C2−0.1 (7)C11—N6—C10—N4−1.9 (8)
Zn1—N1—N2—C2−165.9 (4)C12—N6—C10—N4−180.0 (6)
N2—N1—C1—N30.5 (7)N4—N5—C11—N6−0.3 (9)
Zn1—N1—C1—N3162.2 (4)C10—N6—C11—N51.4 (9)
C2—N3—C1—N1−0.7 (7)C12—N6—C11—N5179.4 (6)
C3—N3—C1—N1179.2 (5)C10—N6—C12—C13−86.6 (8)
N1—N2—C2—N3−0.4 (7)C11—N6—C12—C1395.8 (8)
C1—N3—C2—N20.7 (7)C10—N6—C12—C1793.7 (8)
C3—N3—C2—N2−179.3 (6)C11—N6—C12—C17−83.8 (9)
C1—N3—C3—C8−39.2 (9)C17—C12—C13—C141.1 (10)
C2—N3—C3—C8140.7 (6)N6—C12—C13—C14−178.5 (5)
C1—N3—C3—C4142.3 (6)C12—C13—C14—C150.6 (10)
C2—N3—C3—C4−37.7 (9)C18—O2—C15—C14−1.2 (9)
C8—C3—C4—C5−1.6 (9)C18—O2—C15—C16179.4 (6)
N3—C3—C4—C5176.9 (5)C13—C14—C15—O2178.7 (6)
C3—C4—C5—C61.4 (9)C13—C14—C15—C16−1.9 (10)
C9—O1—C6—C76.3 (9)O2—C15—C16—C17−179.0 (6)
C9—O1—C6—C5−174.3 (5)C14—C15—C16—C171.6 (10)
C4—C5—C6—O1−179.4 (5)C13—C12—C17—C16−1.4 (10)
C4—C5—C6—C70.1 (9)N6—C12—C17—C16178.2 (5)
O1—C6—C7—C8178.2 (6)C15—C16—C17—C120.1 (10)
C5—C6—C7—C8−1.3 (9)N8—Zn1—N7—C19−71.6 (17)
C6—C7—C8—C31.1 (10)N1—Zn1—N7—C19163.5 (16)
C4—C3—C8—C70.4 (10)N4—Zn1—N7—C1955.3 (17)
N3—C3—C8—C7−178.0 (6)Zn1—N7—C19—S1105 (36)
N8—Zn1—N4—C10−169.6 (6)N7—Zn1—N8—C20−29 (3)
N7—Zn1—N4—C1065.7 (6)N1—Zn1—N8—C2093 (3)
N1—Zn1—N4—C10−47.1 (6)N4—Zn1—N8—C20−149 (3)
N8—Zn1—N4—N516.2 (6)Zn1—N8—C20—S2180 (100)
D—H···AD—HH···AD···AD—H···A
C1—H1···N5i0.932.513.438 (8)177
C7—H7···S1ii0.932.863.735 (6)158
C10—H10···O1iii0.932.423.265 (8)151
Zn1—N81.923 (6)
Zn1—N71.970 (6)
Zn1—N12.005 (5)
Zn1—N42.009 (5)
N8—Zn1—N7112.9 (2)
N8—Zn1—N1112.1 (2)
N7—Zn1—N1108.5 (2)
N8—Zn1—N4116.4 (2)
N7—Zn1—N4103.8 (2)
N1—Zn1—N4102.2 (2)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C1—H1⋯N5i0.932.513.438 (8)177
C7—H7⋯S1ii0.932.863.735 (6)158
C10—H10⋯O1iii0.932.423.265 (8)151

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

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