In the title compound, [CuCl
2(C
11H
8N
2O)
2], the Cu
II 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
CCDC reference: 262261
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (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
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)-1
H-benzimidazole-
κN3]copper(II)
top
Crystal data top
[CuCl2(C11H8N2O)2] | F(000) = 510 |
Mr = 502.83 | Dx = 1.576 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8112 (9) Å | Cell parameters from 2608 reflections |
b = 14.1852 (14) Å | θ = 2.5–29.0° |
c = 9.1367 (9) Å | µ = 1.31 mm−1 |
β = 111.867 (1)° | T = 273 K |
V = 1059.82 (18) Å3 | Block, green |
Z = 2 | 0.35 × 0.30 × 0.28 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1912 independent reflections |
Radiation source: fine-focus sealed tube | 1728 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
φ and ω scans | θmax = 25.3°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.554, Tmax = 0.693 | k = −17→14 |
5326 measured reflections | l = −10→9 |
Refinement top
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)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.069 | H-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 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cu | 0.0000 | 1.0000 | 1.0000 | 0.04497 (12) | |
Cl | 0.17015 (6) | 0.95564 (3) | 1.24718 (5) | 0.05952 (15) | |
O1 | −0.16336 (17) | 0.81562 (9) | 0.99049 (17) | 0.0650 (4) | |
C1 | 0.2518 (2) | 0.82294 (14) | 0.8030 (2) | 0.0578 (5) | |
C8 | −0.0605 (2) | 0.76069 (14) | 0.9476 (2) | 0.0540 (4) | |
C6 | 0.2140 (2) | 0.91002 (14) | 0.8476 (2) | 0.0556 (4) | |
C2 | 0.3679 (3) | 0.81227 (19) | 0.7362 (3) | 0.0763 (6) | |
H2 | 0.3917 | 0.7538 | 0.7040 | 0.092* | |
C10 | −0.2216 (3) | 0.66513 (16) | 1.0162 (3) | 0.0741 (6) | |
H10 | −0.2706 | 0.6112 | 1.0363 | 0.089* | |
C11 | −0.2613 (3) | 0.75435 (17) | 1.0325 (3) | 0.0716 (6) | |
H11 | −0.3435 | 0.7725 | 1.0674 | 0.086* | |
C5 | 0.2927 (3) | 0.98971 (16) | 0.8302 (3) | 0.0734 (6) | |
H5 | 0.2677 | 1.0485 | 0.8604 | 0.088* | |
C9 | −0.0912 (3) | 0.66884 (15) | 0.9625 (3) | 0.0683 (5) | |
H9 | −0.0367 | 0.6176 | 0.9414 | 0.082* | |
C3 | 0.4458 (3) | 0.8927 (2) | 0.7202 (3) | 0.0862 (7) | |
H3 | 0.5255 | 0.8885 | 0.6765 | 0.103* | |
C4 | 0.4105 (3) | 0.9795 (2) | 0.7662 (3) | 0.0847 (7) | |
H4 | 0.4673 | 1.0323 | 0.7539 | 0.102* | |
N2 | 0.1511 (2) | 0.75893 (11) | 0.83701 (18) | 0.0594 (4) | |
H2A | 0.1482 | 0.6991 | 0.8214 | 0.071* | |
N1 | 0.09043 (19) | 0.89823 (10) | 0.90904 (17) | 0.0538 (4) | |
C7 | 0.0587 (2) | 0.80751 (12) | 0.8990 (2) | 0.0507 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.0546 (2) | 0.03282 (18) | 0.0553 (2) | −0.00195 (11) | 0.02955 (15) | −0.00068 (11) |
Cl | 0.0749 (3) | 0.0437 (3) | 0.0594 (3) | −0.0019 (2) | 0.0244 (2) | 0.00298 (19) |
O1 | 0.0711 (9) | 0.0490 (8) | 0.0801 (10) | −0.0024 (6) | 0.0341 (8) | 0.0011 (6) |
C1 | 0.0574 (11) | 0.0614 (12) | 0.0527 (11) | 0.0060 (9) | 0.0183 (9) | 0.0008 (8) |
C8 | 0.0629 (11) | 0.0522 (11) | 0.0462 (9) | −0.0027 (9) | 0.0196 (8) | 0.0020 (8) |
C6 | 0.0543 (10) | 0.0611 (11) | 0.0563 (10) | 0.0038 (9) | 0.0264 (8) | 0.0004 (9) |
C2 | 0.0715 (14) | 0.0877 (17) | 0.0743 (14) | 0.0183 (13) | 0.0326 (12) | −0.0050 (12) |
C10 | 0.0928 (16) | 0.0619 (13) | 0.0702 (14) | −0.0155 (12) | 0.0334 (12) | 0.0091 (10) |
C11 | 0.0720 (13) | 0.0759 (15) | 0.0745 (14) | −0.0057 (11) | 0.0361 (11) | 0.0048 (11) |
C5 | 0.0777 (15) | 0.0629 (14) | 0.0914 (17) | −0.0029 (10) | 0.0453 (13) | −0.0041 (11) |
C9 | 0.0896 (16) | 0.0523 (12) | 0.0671 (13) | 0.0033 (11) | 0.0341 (12) | 0.0032 (9) |
C3 | 0.0710 (15) | 0.112 (2) | 0.0906 (17) | 0.0083 (14) | 0.0474 (14) | 0.0068 (15) |
C4 | 0.0747 (16) | 0.0891 (17) | 0.1044 (19) | −0.0047 (13) | 0.0497 (15) | 0.0085 (14) |
N2 | 0.0732 (10) | 0.0454 (8) | 0.0595 (9) | 0.0101 (8) | 0.0247 (8) | −0.0047 (7) |
N1 | 0.0620 (9) | 0.0448 (8) | 0.0600 (9) | 0.0022 (7) | 0.0289 (7) | −0.0028 (7) |
C7 | 0.0615 (11) | 0.0418 (9) | 0.0463 (10) | 0.0059 (8) | 0.0171 (8) | −0.0016 (7) |
Geometric parameters (Å, º) top
Cu—N1 | 1.9756 (14) | C2—H2 | 0.9300 |
Cu—N1i | 1.9756 (14) | C10—C11 | 1.336 (3) |
Cu—Cli | 2.2852 (5) | C10—C9 | 1.408 (3) |
Cu—Cl | 2.2852 (5) | C10—H10 | 0.9300 |
O1—C8 | 1.359 (2) | C11—H11 | 0.9300 |
O1—C11 | 1.376 (3) | C5—C4 | 1.375 (3) |
C1—C2 | 1.380 (3) | C5—H5 | 0.9300 |
C1—C6 | 1.380 (3) | C9—H9 | 0.9300 |
C1—N2 | 1.384 (3) | C3—C4 | 1.374 (4) |
C8—C9 | 1.348 (3) | C3—H3 | 0.9300 |
C8—C7 | 1.445 (3) | C4—H4 | 0.9300 |
C6—C5 | 1.366 (3) | N2—C7 | 1.342 (2) |
C6—N1 | 1.409 (2) | N2—H2A | 0.8600 |
C2—C3 | 1.367 (4) | N1—C7 | 1.313 (2) |
| | | |
N1—Cu—N1i | 180.000 (1) | C10—C11—H11 | 124.8 |
N1—Cu—Cli | 90.25 (5) | O1—C11—H11 | 124.8 |
N1i—Cu—Cli | 89.75 (5) | C6—C5—C4 | 117.3 (2) |
N1—Cu—Cl | 89.75 (5) | C6—C5—H5 | 121.4 |
N1i—Cu—Cl | 90.25 (5) | C4—C5—H5 | 121.4 |
Cli—Cu—Cl | 180.0 | C8—C9—C10 | 107.0 (2) |
C8—O1—C11 | 105.86 (16) | C8—C9—H9 | 126.5 |
C2—C1—C6 | 121.9 (2) | C10—C9—H9 | 126.5 |
C2—C1—N2 | 132.1 (2) | C2—C3—C4 | 122.4 (2) |
C6—C1—N2 | 105.97 (16) | C2—C3—H3 | 118.8 |
C9—C8—O1 | 110.12 (17) | C4—C3—H3 | 118.8 |
C9—C8—C7 | 132.20 (19) | C3—C4—C5 | 121.1 (2) |
O1—C8—C7 | 117.67 (16) | C3—C4—H4 | 119.4 |
C5—C6—C1 | 121.16 (18) | C5—C4—H4 | 119.4 |
C5—C6—N1 | 130.24 (18) | C7—N2—C1 | 107.36 (16) |
C1—C6—N1 | 108.60 (17) | C7—N2—H2A | 126.3 |
C3—C2—C1 | 116.1 (2) | C1—N2—H2A | 126.3 |
C3—C2—H2 | 121.9 | C7—N1—C6 | 105.33 (15) |
C1—C2—H2 | 121.9 | C7—N1—Cu | 129.59 (13) |
C11—C10—C9 | 106.54 (19) | C6—N1—Cu | 125.00 (12) |
C11—C10—H10 | 126.7 | N1—C7—N2 | 112.73 (17) |
C9—C10—H10 | 126.7 | N1—C7—C8 | 126.07 (17) |
C10—C11—O1 | 110.5 (2) | N2—C7—C8 | 121.20 (17) |
Symmetry code: (i) −x, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Clii | 0.86 | 2.33 | 3.1731 (17) | 168 |
Symmetry code: (ii) x, −y+3/2, z−1/2. |