Literature DB >> 23476484

Bis[2-(1H-benzotriazol-1-yl)-1H-benz-imidazol-1-ido]diethano-lcadmium.

Ping Cao1, Jia-Cheng Liu, Dong-Cheng Hu.   

Abstract

In the title complex, [Cd(C13H8N5)2(C2H5OH)2], the Cd(II) cation is located on an inversion center and coordinated by two deprotonated 2-(1H-benzotriazol-1-yl)-1H-benzimid-azol-1-ide (L) ligands and two ethanol mol-ecules in a distorted N4O2 octa-hedral geometry. In the L ligand, the dihedral angle between benzoimidazole and benzotriazole ring systems is 10.8 (3)°. In the crystal, the complex mol-ecules are connected by O-H⋯N hydrogen bonds; inter-molecular π-π stacking is also observed [centroid-centroid distances of 3.668 (5) Å between triazole and benzene rings and 3.780 (5) Å between imidazole rings].

Entities:  

Year:  2013        PMID： 23476484      PMCID： PMC3588456          DOI： 10.1107/S1600536813001827

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


Related literature

For applications of metal comlexes with heterocyclic ligands, see: Zhou et al. (2006 ▶); Batten & Robson (1998 ▶); Zaworotko (1994 ▶). For a related structure, see: Wu et al. (2009 ▶).

Experimental

Crystal data

[Cd(C13H8N5)2(C2H6O)2] M = 673.03 Monoclinic, a = 8.7544 (4) Å b = 8.0112 (2) Å c = 20.9382 (9) Å β = 101.352 (5)° V = 1439.74 (10) Å3 Z = 2 Mo Kα radiation μ = 0.81 mm−1 T = 293 K 0.32 × 0.28 × 0.25 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.773, T max = 0.818 7375 measured reflections 3636 independent reflections 2781 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.089 wR(F 2) = 0.221 S = 1.20 3636 reflections 200 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 2.99 e Å−3 Δρmin = −0.97 e Å−3 Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001827/xu5670sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001827/xu5670Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Cd(C13H8N5)2(C2H6O)2]F(000) = 684
Mr = 673.03Dx = 1.552 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3469 reflections
a = 8.7544 (4) Åθ = 3.4–28.4°
b = 8.0112 (2) ŵ = 0.81 mm−1
c = 20.9382 (9) ÅT = 293 K
β = 101.352 (5)°Block, yellow
V = 1439.74 (10) Å30.32 × 0.28 × 0.25 mm
Z = 2
Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer3636 independent reflections
Radiation source: fine-focus sealed tube2781 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 16.0733 pixels mm-1θmax = 28.5°, θmin = 3.4°
ω scansh = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)k = −9→10
Tmin = 0.773, Tmax = 0.818l = −26→28
7375 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.089Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221H atoms treated by a mixture of independent and constrained refinement
S = 1.20w = 1/[σ2(Fo2) + (0.0356P)2 + 19.0636P] where P = (Fo2 + 2Fc2)/3
3636 reflections(Δ/σ)max = 0.001
200 parametersΔρmax = 2.99 e Å−3
1 restraintΔρmin = −0.97 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.
xyzUiso*/Ueq
Cd10.00000.50000.50000.0382 (3)
N50.0518 (8)0.2674 (8)0.4545 (3)0.0345 (15)
N40.1590 (8)0.0074 (9)0.4596 (3)0.0371 (15)
C70.1439 (9)0.1508 (9)0.4883 (4)0.0303 (15)
N20.1878 (9)0.3336 (8)0.5803 (3)0.0397 (16)
C40.5416 (12)−0.0727 (12)0.6419 (5)0.049 (2)
H40.6007−0.16890.64130.059*
C60.3410 (9)0.1084 (10)0.5935 (4)0.0341 (17)
C50.4252 (11)−0.0382 (11)0.5883 (5)0.047 (2)
H50.4046−0.10680.55180.057*
C30.5740 (11)0.0307 (12)0.6967 (5)0.050 (2)
H30.65560.00320.73070.060*
C13−0.0046 (9)0.1884 (9)0.3956 (4)0.0320 (16)
O1−0.2074 (8)0.3361 (7)0.5291 (4)0.0470 (16)
H1−0.199 (14)0.233 (3)0.522 (6)0.071*
N30.2245 (8)0.1886 (8)0.5512 (3)0.0317 (14)
C90.0275 (11)−0.0769 (11)0.3455 (4)0.0404 (19)
H90.0686−0.18420.34750.048*
C14−0.3409 (15)0.3597 (16)0.5541 (8)0.081 (4)
H14A−0.36280.25860.57620.098*
H14B−0.42810.38000.51850.098*
C20.4898 (11)0.1690 (12)0.7015 (5)0.046 (2)
H20.50960.23520.73870.055*
C12−0.1048 (11)0.2473 (11)0.3394 (4)0.042 (2)
H12−0.14830.35360.33720.050*
C10−0.0704 (12)−0.0196 (14)0.2903 (5)0.052 (2)
H10−0.0937−0.08850.25390.063*
C11−0.1348 (12)0.1384 (12)0.2877 (5)0.049 (2)
H11−0.20100.17230.24960.059*
C80.0624 (9)0.0309 (9)0.3979 (4)0.0326 (17)
C10.3704 (10)0.2104 (10)0.6481 (4)0.0361 (17)
N10.2753 (9)0.3473 (9)0.6380 (4)0.0430 (17)
C15−0.3265 (19)0.5020 (19)0.6007 (8)0.096 (5)
H15A−0.32350.60490.57740.144*
H15B−0.23240.49030.63280.144*
H15C−0.41450.50270.62180.144*
U11U22U33U12U13U23
Cd10.0529 (5)0.0192 (4)0.0413 (5)0.0066 (4)0.0064 (4)−0.0031 (4)
N50.046 (4)0.017 (3)0.039 (4)0.004 (3)0.004 (3)0.001 (3)
N40.045 (4)0.026 (3)0.041 (4)0.006 (3)0.008 (3)0.007 (3)
C70.035 (4)0.018 (3)0.038 (4)0.000 (3)0.008 (3)0.004 (3)
N20.057 (4)0.022 (3)0.039 (4)0.010 (3)0.006 (3)−0.003 (3)
C40.058 (6)0.030 (4)0.053 (6)0.013 (4)−0.005 (4)0.003 (4)
C60.041 (4)0.020 (3)0.041 (4)0.000 (3)0.010 (3)0.002 (3)
C50.055 (5)0.032 (5)0.053 (5)0.009 (4)0.005 (4)0.001 (4)
C30.049 (5)0.043 (6)0.052 (5)0.001 (4)−0.006 (4)0.004 (4)
C130.043 (4)0.020 (3)0.033 (4)0.005 (3)0.007 (3)0.004 (3)
O10.064 (4)0.019 (3)0.064 (4)0.007 (3)0.027 (3)−0.001 (3)
N30.044 (4)0.019 (3)0.032 (3)0.003 (3)0.008 (3)0.000 (3)
C90.057 (5)0.027 (4)0.035 (4)0.009 (4)0.004 (4)−0.007 (3)
C140.070 (8)0.053 (7)0.130 (12)0.010 (6)0.042 (8)−0.007 (8)
C20.054 (5)0.039 (5)0.040 (5)−0.004 (4)−0.003 (4)−0.002 (4)
C120.059 (5)0.029 (4)0.035 (4)0.013 (4)0.005 (4)0.004 (3)
C100.066 (6)0.049 (6)0.038 (5)−0.003 (5)0.001 (4)−0.008 (5)
C110.061 (6)0.045 (5)0.036 (5)0.003 (5)−0.001 (4)−0.001 (4)
C80.037 (4)0.024 (4)0.037 (4)0.001 (3)0.008 (3)−0.005 (3)
C10.046 (4)0.028 (4)0.033 (4)−0.001 (3)0.005 (3)0.000 (3)
N10.056 (4)0.032 (4)0.035 (4)0.007 (3)−0.004 (3)−0.007 (3)
C150.122 (12)0.065 (8)0.120 (12)−0.018 (9)0.074 (10)−0.029 (9)
Cd1—O1i2.414 (7)C13—C81.388 (10)
Cd1—O12.414 (7)C13—C121.404 (11)
Cd1—N22.494 (7)O1—C141.384 (13)
Cd1—N2i2.494 (7)O1—H10.848 (10)
Cd1—N5i2.180 (6)C9—C101.375 (13)
Cd1—N52.180 (6)C9—C81.382 (11)
N5—C71.341 (10)C9—H90.9300
N5—C131.388 (10)C14—C151.489 (18)
N4—C71.316 (10)C14—H14A0.9700
N4—C81.411 (10)C14—H14B0.9700
C7—N31.399 (10)C2—C11.411 (12)
N2—N11.301 (10)C2—H20.9300
N2—N31.380 (9)C12—C111.374 (13)
C4—C51.387 (13)C12—H120.9300
C4—C31.398 (14)C10—C111.383 (14)
C4—H40.9300C10—H100.9300
C6—N31.371 (10)C11—H110.9300
C6—C11.388 (11)C1—N11.368 (11)
C6—C51.402 (11)C15—H15A0.9600
C5—H50.9300C15—H15B0.9600
C3—C21.346 (13)C15—H15C0.9600
C3—H30.9300
N5i—Cd1—N5180.000 (1)C8—C13—N5108.1 (7)
N5i—Cd1—O1i82.9 (2)C8—C13—C12121.6 (8)
N5—Cd1—O1i97.1 (2)N5—C13—C12130.2 (7)
N5i—Cd1—O197.1 (2)C14—O1—Cd1138.9 (7)
N5—Cd1—O182.9 (2)C14—O1—H1108 (8)
O1i—Cd1—O1180.0 (2)Cd1—O1—H1113 (8)
N5i—Cd1—N2109.2 (2)C6—N3—N2108.5 (6)
N5—Cd1—N270.8 (2)C6—N3—C7132.8 (7)
O1i—Cd1—N291.8 (2)N2—N3—C7118.7 (6)
O1—Cd1—N288.2 (2)C10—C9—C8117.5 (8)
N5i—Cd1—N2i70.8 (2)C10—C9—H9121.2
N5—Cd1—N2i109.2 (2)C8—C9—H9121.2
O1i—Cd1—N2i88.2 (2)O1—C14—C15112.6 (11)
O1—Cd1—N2i91.8 (2)O1—C14—H14A109.1
N2—Cd1—N2i180.0 (3)C15—C14—H14A109.1
C7—N5—C13102.9 (6)O1—C14—H14B109.1
C7—N5—Cd1121.3 (5)C15—C14—H14B109.1
C13—N5—Cd1135.2 (5)H14A—C14—H14B107.8
C7—N4—C8101.9 (6)C3—C2—C1117.8 (9)
N4—C7—N5118.1 (7)C3—C2—H2121.1
N4—C7—N3122.8 (7)C1—C2—H2121.1
N5—C7—N3119.1 (7)C11—C12—C13115.9 (8)
N1—N2—N3109.6 (6)C11—C12—H12122.0
N1—N2—Cd1140.4 (5)C13—C12—H12122.0
N3—N2—Cd1109.4 (5)C9—C10—C11121.4 (9)
C5—C4—C3123.0 (9)C9—C10—H10119.3
C5—C4—H4118.5C11—C10—H10119.3
C3—C4—H4118.5C12—C11—C10122.5 (9)
N3—C6—C1104.5 (7)C12—C11—H11118.7
N3—C6—C5132.7 (8)C10—C11—H11118.7
C1—C6—C5122.8 (8)C9—C8—C13121.0 (8)
C4—C5—C6114.7 (9)C9—C8—N4130.0 (7)
C4—C5—H5122.7C13—C8—N4109.0 (7)
C6—C5—H5122.7N1—C1—C6109.6 (7)
C2—C3—C4121.5 (9)N1—C1—C2130.1 (8)
C2—C3—H3119.2C6—C1—C2120.2 (8)
C4—C3—H3119.2N2—N1—C1107.8 (7)
N5i—Cd1—N5—C732 (100)N2i—Cd1—O1—C14−59.3 (13)
O1i—Cd1—N5—C793.0 (6)C1—C6—N3—N20.3 (9)
O1—Cd1—N5—C7−87.0 (6)C5—C6—N3—N2−177.3 (9)
N2—Cd1—N5—C73.5 (6)C1—C6—N3—C7180.0 (8)
N2i—Cd1—N5—C7−176.5 (6)C5—C6—N3—C72.4 (15)
N5i—Cd1—N5—C13−158 (100)N1—N2—N3—C60.1 (9)
O1i—Cd1—N5—C13−97.4 (8)Cd1—N2—N3—C6173.1 (5)
O1—Cd1—N5—C1382.6 (8)N1—N2—N3—C7−179.6 (7)
N2—Cd1—N5—C13173.2 (8)Cd1—N2—N3—C7−6.6 (8)
N2i—Cd1—N5—C13−6.8 (8)N4—C7—N3—C67.9 (13)
C8—N4—C7—N5−0.4 (9)N5—C7—N3—C6−169.3 (8)
C8—N4—C7—N3−177.7 (7)N4—C7—N3—N2−172.5 (7)
C13—N5—C7—N41.5 (10)N5—C7—N3—N210.3 (11)
Cd1—N5—C7—N4174.0 (5)Cd1—O1—C14—C15−33 (2)
C13—N5—C7—N3178.8 (7)C4—C3—C2—C1−2.2 (15)
Cd1—N5—C7—N3−8.6 (10)C8—C13—C12—C111.5 (13)
N5i—Cd1—N2—N1−8.7 (10)N5—C13—C12—C11178.0 (9)
N5—Cd1—N2—N1171.3 (10)C8—C9—C10—C11−1.7 (15)
O1i—Cd1—N2—N174.5 (10)C13—C12—C11—C10−0.3 (15)
O1—Cd1—N2—N1−105.5 (10)C9—C10—C11—C120.4 (17)
N2i—Cd1—N2—N1130 (100)C10—C9—C8—C132.8 (13)
N5i—Cd1—N2—N3−178.2 (5)C10—C9—C8—N4−179.3 (9)
N5—Cd1—N2—N31.8 (5)N5—C13—C8—C9180.0 (8)
O1i—Cd1—N2—N3−95.1 (5)C12—C13—C8—C9−2.8 (13)
O1—Cd1—N2—N384.9 (5)N5—C13—C8—N41.7 (9)
N2i—Cd1—N2—N3−39 (100)C12—C13—C8—N4178.9 (8)
C3—C4—C5—C6−0.5 (15)C7—N4—C8—C9−178.9 (9)
N3—C6—C5—C4176.7 (9)C7—N4—C8—C13−0.8 (9)
C1—C6—C5—C4−0.6 (13)N3—C6—C1—N1−0.7 (9)
C5—C4—C3—C22.1 (17)C5—C6—C1—N1177.3 (8)
C7—N5—C13—C8−1.9 (9)N3—C6—C1—C2−177.6 (8)
Cd1—N5—C13—C8−172.8 (6)C5—C6—C1—C20.4 (13)
C7—N5—C13—C12−178.7 (9)C3—C2—C1—N1−175.1 (9)
Cd1—N5—C13—C1210.3 (14)C3—C2—C1—C61.1 (14)
N5i—Cd1—O1—C1411.6 (13)N3—N2—N1—C1−0.5 (10)
N5—Cd1—O1—C14−168.4 (13)Cd1—N2—N1—C1−170.1 (7)
O1i—Cd1—O1—C14−110 (100)C6—C1—N1—N20.7 (10)
N2—Cd1—O1—C14120.7 (13)C2—C1—N1—N2177.2 (9)
D—H···AD—HH···AD···AD—H···A
O1—H1···N4ii0.85 (1)1.98 (5)2.787 (9)159 (12)
Table 1

Selected bond lengths (Å)

Cd1—O12.414 (7)
Cd1—N22.494 (7)
Cd1—N52.180 (6)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O1—H1⋯N4i 0.85 (1)1.98 (5)2.787 (9)159 (12)

Symmetry code: (i) .

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1.  A short history of SHELX.

Authors:  George M Sheldrick
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