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In the title compound, [CuCl2(C11H8N2O)2], the CuII atom is coordinated by two N and two Cl atoms in a centrosymmetric square-planar geometry. Intermolecular N—H...Cl hydrogen bonds link the mol­ecules into a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031009/cv6420sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031009/cv6420Isup2.hkl
Contains datablock I

CCDC reference: 262261

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.023
  • wR factor = 0.068
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.554 0.693 Tmin' and Tmax expected: 0.625 0.693 RR' = 0.887 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.87 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C1 .. 5.19 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C8 .. 6.24 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - N1 .. 6.43 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT and SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Dichloro[2-(2-furyl)-1H-benzimidazole-κN3]copper(II) top
Crystal data top
[CuCl2(C11H8N2O)2]F(000) = 510
Mr = 502.83Dx = 1.576 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.8112 (9) ÅCell parameters from 2608 reflections
b = 14.1852 (14) Åθ = 2.5–29.0°
c = 9.1367 (9) ŵ = 1.31 mm1
β = 111.867 (1)°T = 273 K
V = 1059.82 (18) Å3Block, green
Z = 20.35 × 0.30 × 0.28 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1912 independent reflections
Radiation source: fine-focus sealed tube1728 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
φ and ω scansθmax = 25.3°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.554, Tmax = 0.693k = 1714
5326 measured reflectionsl = 109
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0381P)2 + 0.1747P]
where P = (Fo2 + 2Fc2)/3
1912 reflections(Δ/σ)max = 0.001
142 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.17 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu0.00001.00001.00000.04497 (12)
Cl0.17015 (6)0.95564 (3)1.24718 (5)0.05952 (15)
O10.16336 (17)0.81562 (9)0.99049 (17)0.0650 (4)
C10.2518 (2)0.82294 (14)0.8030 (2)0.0578 (5)
C80.0605 (2)0.76069 (14)0.9476 (2)0.0540 (4)
C60.2140 (2)0.91002 (14)0.8476 (2)0.0556 (4)
C20.3679 (3)0.81227 (19)0.7362 (3)0.0763 (6)
H20.39170.75380.70400.092*
C100.2216 (3)0.66513 (16)1.0162 (3)0.0741 (6)
H100.27060.61121.03630.089*
C110.2613 (3)0.75435 (17)1.0325 (3)0.0716 (6)
H110.34350.77251.06740.086*
C50.2927 (3)0.98971 (16)0.8302 (3)0.0734 (6)
H50.26771.04850.86040.088*
C90.0912 (3)0.66884 (15)0.9625 (3)0.0683 (5)
H90.03670.61760.94140.082*
C30.4458 (3)0.8927 (2)0.7202 (3)0.0862 (7)
H30.52550.88850.67650.103*
C40.4105 (3)0.9795 (2)0.7662 (3)0.0847 (7)
H40.46731.03230.75390.102*
N20.1511 (2)0.75893 (11)0.83701 (18)0.0594 (4)
H2A0.14820.69910.82140.071*
N10.09043 (19)0.89823 (10)0.90904 (17)0.0538 (4)
C70.0587 (2)0.80751 (12)0.8990 (2)0.0507 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0546 (2)0.03282 (18)0.0553 (2)0.00195 (11)0.02955 (15)0.00068 (11)
Cl0.0749 (3)0.0437 (3)0.0594 (3)0.0019 (2)0.0244 (2)0.00298 (19)
O10.0711 (9)0.0490 (8)0.0801 (10)0.0024 (6)0.0341 (8)0.0011 (6)
C10.0574 (11)0.0614 (12)0.0527 (11)0.0060 (9)0.0183 (9)0.0008 (8)
C80.0629 (11)0.0522 (11)0.0462 (9)0.0027 (9)0.0196 (8)0.0020 (8)
C60.0543 (10)0.0611 (11)0.0563 (10)0.0038 (9)0.0264 (8)0.0004 (9)
C20.0715 (14)0.0877 (17)0.0743 (14)0.0183 (13)0.0326 (12)0.0050 (12)
C100.0928 (16)0.0619 (13)0.0702 (14)0.0155 (12)0.0334 (12)0.0091 (10)
C110.0720 (13)0.0759 (15)0.0745 (14)0.0057 (11)0.0361 (11)0.0048 (11)
C50.0777 (15)0.0629 (14)0.0914 (17)0.0029 (10)0.0453 (13)0.0041 (11)
C90.0896 (16)0.0523 (12)0.0671 (13)0.0033 (11)0.0341 (12)0.0032 (9)
C30.0710 (15)0.112 (2)0.0906 (17)0.0083 (14)0.0474 (14)0.0068 (15)
C40.0747 (16)0.0891 (17)0.1044 (19)0.0047 (13)0.0497 (15)0.0085 (14)
N20.0732 (10)0.0454 (8)0.0595 (9)0.0101 (8)0.0247 (8)0.0047 (7)
N10.0620 (9)0.0448 (8)0.0600 (9)0.0022 (7)0.0289 (7)0.0028 (7)
C70.0615 (11)0.0418 (9)0.0463 (10)0.0059 (8)0.0171 (8)0.0016 (7)
Geometric parameters (Å, º) top
Cu—N11.9756 (14)C2—H20.9300
Cu—N1i1.9756 (14)C10—C111.336 (3)
Cu—Cli2.2852 (5)C10—C91.408 (3)
Cu—Cl2.2852 (5)C10—H100.9300
O1—C81.359 (2)C11—H110.9300
O1—C111.376 (3)C5—C41.375 (3)
C1—C21.380 (3)C5—H50.9300
C1—C61.380 (3)C9—H90.9300
C1—N21.384 (3)C3—C41.374 (4)
C8—C91.348 (3)C3—H30.9300
C8—C71.445 (3)C4—H40.9300
C6—C51.366 (3)N2—C71.342 (2)
C6—N11.409 (2)N2—H2A0.8600
C2—C31.367 (4)N1—C71.313 (2)
N1—Cu—N1i180.000 (1)C10—C11—H11124.8
N1—Cu—Cli90.25 (5)O1—C11—H11124.8
N1i—Cu—Cli89.75 (5)C6—C5—C4117.3 (2)
N1—Cu—Cl89.75 (5)C6—C5—H5121.4
N1i—Cu—Cl90.25 (5)C4—C5—H5121.4
Cli—Cu—Cl180.0C8—C9—C10107.0 (2)
C8—O1—C11105.86 (16)C8—C9—H9126.5
C2—C1—C6121.9 (2)C10—C9—H9126.5
C2—C1—N2132.1 (2)C2—C3—C4122.4 (2)
C6—C1—N2105.97 (16)C2—C3—H3118.8
C9—C8—O1110.12 (17)C4—C3—H3118.8
C9—C8—C7132.20 (19)C3—C4—C5121.1 (2)
O1—C8—C7117.67 (16)C3—C4—H4119.4
C5—C6—C1121.16 (18)C5—C4—H4119.4
C5—C6—N1130.24 (18)C7—N2—C1107.36 (16)
C1—C6—N1108.60 (17)C7—N2—H2A126.3
C3—C2—C1116.1 (2)C1—N2—H2A126.3
C3—C2—H2121.9C7—N1—C6105.33 (15)
C1—C2—H2121.9C7—N1—Cu129.59 (13)
C11—C10—C9106.54 (19)C6—N1—Cu125.00 (12)
C11—C10—H10126.7N1—C7—N2112.73 (17)
C9—C10—H10126.7N1—C7—C8126.07 (17)
C10—C11—O1110.5 (2)N2—C7—C8121.20 (17)
Symmetry code: (i) x, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Clii0.862.333.1731 (17)168
Symmetry code: (ii) x, y+3/2, z1/2.
 

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