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In the title compound, [Cu(C16H13ClN3O)(NCS)]·H2O, the CuII atom adopts a distorted square-planar coordination with two N atoms and one O atom of the tridentate phenolate ligand, and one N atom of the thio­cyanate anion. N—H...S, O—H...O and C—H...O hydrogen bonds give rise to a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011913/hb2029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011913/hb2029Isup2.hkl
Contains datablock I

CCDC reference: 608338

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • R factor = 0.042
  • wR factor = 0.101
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

{2-[2-(1H-1,3-Benzimidazol-2-yl)ethyliminomethyl]-4- chlorophenolato}thiocyanatocopper(II) monohydrate top
Crystal data top
[Cu(C16H13ClN3O)(NCS)]·H2OZ = 2
Mr = 438.38F(000) = 446
Triclinic, P1Dx = 1.624 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.685 (3) ÅCell parameters from 1346 reflections
b = 8.946 (3) Åθ = 2.3–22.5°
c = 12.395 (4) ŵ = 1.50 mm1
α = 79.660 (6)°T = 294 K
β = 71.659 (5)°Block, green
γ = 82.709 (5)°0.26 × 0.24 × 0.22 mm
V = 896.7 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3121 independent reflections
Radiation source: fine-focus sealed tube2051 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.704, Tmax = 0.733k = 1010
4372 measured reflectionsl = 1014
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)] = 0.042Hydrogen site location: difmap and geom
wR(F2) = 0.101H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0468P)2]
where P = (Fo2 + 2Fc2)/3
3121 reflections(Δ/σ)max = 0.002
235 parametersΔρmax = 0.44 e Å3
3 restraintsΔρmin = 0.39 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
Cu10.20729 (6)0.18459 (6)0.28076 (5)0.03257 (19)
S10.32531 (14)0.10839 (15)0.52358 (11)0.0508 (4)
Cl10.76408 (15)0.38959 (14)0.00950 (12)0.0583 (4)
O10.2133 (3)0.0191 (3)0.2030 (2)0.0365 (7)
N10.4462 (4)0.1868 (4)0.2368 (3)0.0288 (8)
N20.1742 (4)0.3933 (3)0.3177 (3)0.0315 (8)
N30.2116 (4)0.5891 (4)0.3900 (3)0.0346 (9)
H30.25680.64540.41890.042*
N40.0187 (4)0.1486 (4)0.3676 (3)0.0413 (10)
C10.3401 (5)0.0709 (4)0.1585 (3)0.0295 (10)
C20.3140 (5)0.1987 (5)0.1153 (3)0.0353 (11)
H20.20880.21770.12070.042*
C30.4428 (5)0.2944 (4)0.0656 (3)0.0368 (11)
H3A0.42440.37830.03780.044*
C40.5995 (5)0.2673 (5)0.0563 (4)0.0354 (11)
C50.6297 (5)0.1464 (4)0.0974 (3)0.0354 (11)
H50.73610.13000.09090.043*
C60.5006 (5)0.0463 (4)0.1497 (3)0.0284 (10)
C70.5429 (5)0.0816 (4)0.1877 (3)0.0320 (10)
H70.65320.08880.17510.038*
C80.5248 (5)0.3101 (5)0.2596 (4)0.0385 (11)
H8A0.53760.39270.19560.046*
H8B0.63240.27170.26420.046*
C90.4286 (5)0.3722 (5)0.3702 (4)0.0404 (11)
H9A0.40810.28900.43380.048*
H9B0.49180.44300.38600.048*
C100.2712 (5)0.4512 (5)0.3601 (3)0.0315 (10)
C110.0652 (5)0.6245 (5)0.3660 (3)0.0328 (10)
C120.0439 (6)0.7531 (5)0.3768 (4)0.0439 (12)
H120.02670.83560.40670.053*
C130.1768 (6)0.7520 (5)0.3415 (4)0.0491 (13)
H130.25270.83570.34790.059*
C140.2027 (6)0.6289 (5)0.2957 (4)0.0458 (12)
H140.29580.63240.27310.055*
C150.0939 (5)0.5026 (5)0.2832 (4)0.0416 (11)
H150.11010.42190.25110.050*
C160.0403 (5)0.5009 (4)0.3205 (3)0.0305 (10)
C170.1456 (5)0.1320 (4)0.4314 (4)0.0298 (10)
O20.0522 (4)0.9230 (5)0.8936 (4)0.1088 (16)
H2A0.01680.94180.85610.131*
H2B0.01640.90900.96610.131*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0253 (3)0.0343 (3)0.0393 (3)0.0052 (2)0.0063 (2)0.0124 (2)
S10.0276 (6)0.0644 (9)0.0560 (9)0.0108 (6)0.0026 (6)0.0102 (7)
Cl10.0536 (8)0.0492 (8)0.0678 (9)0.0115 (6)0.0081 (7)0.0267 (7)
O10.0272 (15)0.0409 (18)0.0443 (19)0.0026 (13)0.0084 (14)0.0177 (15)
N10.0236 (18)0.0296 (19)0.033 (2)0.0071 (15)0.0049 (16)0.0075 (16)
N20.0319 (19)0.0289 (19)0.036 (2)0.0026 (16)0.0099 (17)0.0111 (16)
N30.037 (2)0.038 (2)0.036 (2)0.0087 (17)0.0141 (18)0.0156 (17)
N40.027 (2)0.036 (2)0.056 (3)0.0066 (17)0.002 (2)0.0146 (19)
C10.033 (2)0.030 (2)0.024 (2)0.0048 (19)0.007 (2)0.0007 (19)
C20.039 (3)0.037 (3)0.031 (3)0.012 (2)0.008 (2)0.006 (2)
C30.050 (3)0.031 (3)0.031 (3)0.006 (2)0.010 (2)0.009 (2)
C40.039 (3)0.031 (2)0.031 (3)0.006 (2)0.006 (2)0.007 (2)
C50.029 (2)0.035 (3)0.036 (3)0.0026 (19)0.004 (2)0.001 (2)
C60.027 (2)0.030 (2)0.027 (2)0.0015 (18)0.0063 (19)0.0048 (19)
C70.026 (2)0.039 (3)0.029 (3)0.006 (2)0.007 (2)0.002 (2)
C80.026 (2)0.044 (3)0.048 (3)0.010 (2)0.008 (2)0.012 (2)
C90.035 (3)0.048 (3)0.045 (3)0.003 (2)0.016 (2)0.017 (2)
C100.032 (2)0.035 (3)0.029 (2)0.006 (2)0.007 (2)0.009 (2)
C110.036 (2)0.035 (3)0.026 (2)0.005 (2)0.006 (2)0.005 (2)
C120.054 (3)0.033 (3)0.044 (3)0.000 (2)0.013 (3)0.011 (2)
C130.053 (3)0.039 (3)0.050 (3)0.008 (2)0.015 (3)0.001 (2)
C140.045 (3)0.047 (3)0.047 (3)0.003 (2)0.021 (2)0.003 (2)
C150.048 (3)0.034 (3)0.048 (3)0.003 (2)0.020 (2)0.007 (2)
C160.031 (2)0.031 (2)0.031 (3)0.0067 (19)0.009 (2)0.007 (2)
C170.035 (3)0.024 (2)0.037 (3)0.0013 (19)0.019 (2)0.0079 (19)
O20.049 (2)0.206 (5)0.084 (3)0.003 (3)0.033 (2)0.035 (3)
Geometric parameters (Å, º) top
Cu1—O11.893 (3)C5—C61.406 (5)
Cu1—N41.955 (3)C5—H50.9300
Cu1—N21.966 (3)C6—C71.440 (5)
Cu1—N11.974 (3)C7—H70.9300
S1—C171.631 (4)C8—C91.524 (6)
Cl1—C41.759 (4)C8—H8A0.9700
O1—C11.310 (4)C8—H8B0.9700
N1—C71.282 (5)C9—C101.489 (5)
N1—C81.478 (5)C9—H9A0.9700
N2—C101.320 (5)C9—H9B0.9700
N2—C161.408 (5)C11—C121.393 (6)
N3—C101.344 (5)C11—C161.396 (5)
N3—C111.381 (5)C12—C131.358 (6)
N3—H30.8600C12—H120.9300
N4—C171.146 (5)C13—C141.398 (6)
C1—C61.407 (5)C13—H130.9300
C1—C21.416 (5)C14—C151.376 (6)
C2—C31.370 (5)C14—H140.9300
C2—H20.9300C15—C161.379 (6)
C3—C41.378 (6)C15—H150.9300
C3—H3A0.9300O2—H2A0.8514
C4—C51.361 (5)O2—H2B0.8452
O1—Cu1—N488.67 (13)C6—C7—H7116.2
O1—Cu1—N2160.27 (13)N1—C8—C9113.0 (3)
N4—Cu1—N290.64 (13)N1—C8—H8A109.0
O1—Cu1—N194.33 (12)C9—C8—H8A109.0
N4—Cu1—N1162.48 (15)N1—C8—H8B109.0
N2—Cu1—N192.23 (13)C9—C8—H8B109.0
C1—O1—Cu1127.6 (3)H8A—C8—H8B107.8
C7—N1—C8115.8 (3)C10—C9—C8110.6 (3)
C7—N1—Cu1122.4 (3)C10—C9—H9A109.5
C8—N1—Cu1121.8 (2)C8—C9—H9A109.5
C10—N2—C16106.4 (3)C10—C9—H9B109.5
C10—N2—Cu1123.7 (3)C8—C9—H9B109.5
C16—N2—Cu1129.4 (3)H9A—C9—H9B108.1
C10—N3—C11108.0 (3)N2—C10—N3111.8 (4)
C10—N3—H3126.0N2—C10—C9123.0 (4)
C11—N3—H3126.0N3—C10—C9125.2 (4)
C17—N4—Cu1170.4 (4)N3—C11—C12132.0 (4)
O1—C1—C6123.6 (3)N3—C11—C16106.1 (3)
O1—C1—C2118.1 (4)C12—C11—C16121.8 (4)
C6—C1—C2118.3 (3)C13—C12—C11116.6 (4)
C3—C2—C1120.4 (4)C13—C12—H12121.7
C3—C2—H2119.8C11—C12—H12121.7
C1—C2—H2119.8C12—C13—C14122.0 (4)
C2—C3—C4120.5 (4)C12—C13—H13119.0
C2—C3—H3A119.7C14—C13—H13119.0
C4—C3—H3A119.7C15—C14—C13121.5 (4)
C5—C4—C3121.0 (4)C15—C14—H14119.2
C5—C4—Cl1119.0 (3)C13—C14—H14119.2
C3—C4—Cl1120.1 (3)C14—C15—C16117.2 (4)
C4—C5—C6120.2 (4)C14—C15—H15121.4
C4—C5—H5119.9C16—C15—H15121.4
C6—C5—H5119.9C15—C16—C11120.9 (4)
C5—C6—C1119.7 (4)C15—C16—N2131.4 (4)
C5—C6—C7116.9 (4)C11—C16—N2107.6 (4)
C1—C6—C7123.4 (3)N4—C17—S1179.2 (4)
N1—C7—C6127.6 (4)H2A—O2—H2B117.8
N1—C7—H7116.2
N4—Cu1—O1—C1151.6 (3)Cu1—N1—C7—C64.3 (6)
N2—Cu1—O1—C1120.2 (4)C5—C6—C7—N1179.8 (4)
N1—Cu1—O1—C111.1 (3)C1—C6—C7—N12.3 (7)
O1—Cu1—N1—C79.0 (3)C7—N1—C8—C9145.7 (4)
N4—Cu1—N1—C790.4 (5)Cu1—N1—C8—C933.8 (5)
N2—Cu1—N1—C7170.4 (3)N1—C8—C9—C1066.4 (5)
O1—Cu1—N1—C8171.5 (3)C16—N2—C10—N30.3 (5)
N4—Cu1—N1—C889.1 (5)Cu1—N2—C10—N3172.9 (3)
N2—Cu1—N1—C810.1 (3)C16—N2—C10—C9179.1 (4)
O1—Cu1—N2—C10142.4 (4)Cu1—N2—C10—C98.4 (6)
N4—Cu1—N2—C10129.7 (3)C11—N3—C10—N20.2 (5)
N1—Cu1—N2—C1033.0 (3)C11—N3—C10—C9178.9 (4)
O1—Cu1—N2—C1646.8 (6)C8—C9—C10—N245.9 (5)
N4—Cu1—N2—C1641.0 (4)C8—C9—C10—N3132.7 (4)
N1—Cu1—N2—C16156.3 (3)C10—N3—C11—C12178.0 (5)
Cu1—O1—C1—C68.0 (6)C10—N3—C11—C160.1 (4)
Cu1—O1—C1—C2173.0 (3)N3—C11—C12—C13178.1 (4)
O1—C1—C2—C3178.5 (4)C16—C11—C12—C130.4 (6)
C6—C1—C2—C30.5 (6)C11—C12—C13—C140.4 (7)
C1—C2—C3—C40.4 (6)C12—C13—C14—C150.5 (7)
C2—C3—C4—C50.8 (7)C13—C14—C15—C161.5 (7)
C2—C3—C4—Cl1179.1 (3)C14—C15—C16—C111.6 (6)
C3—C4—C5—C60.4 (7)C14—C15—C16—N2178.2 (4)
Cl1—C4—C5—C6179.6 (3)N3—C11—C16—C15177.6 (4)
C4—C5—C6—C10.5 (6)C12—C11—C16—C150.7 (6)
C4—C5—C6—C7178.1 (4)N3—C11—C16—N20.3 (4)
O1—C1—C6—C5178.0 (4)C12—C11—C16—N2178.0 (4)
C2—C1—C6—C50.9 (6)C10—N2—C16—C15177.3 (4)
O1—C1—C6—C70.6 (6)Cu1—N2—C16—C1510.7 (7)
C2—C1—C6—C7178.3 (4)C10—N2—C16—C110.4 (5)
C8—N1—C7—C6176.1 (4)Cu1—N2—C16—C11172.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···S1i0.862.623.440 (3)159
O2—H2A···O1i0.852.032.869 (5)169
O2—H2B···O2ii0.852.393.027 (8)133
C7—H7···O2iii0.932.423.336 (6)167
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+2, z+2; (iii) x+1, y+1, z+1.
 

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