Download citation
Download citation
link to html
The title compound, [Cu(C11H12Cl2N2O)(NCS)], is a mononuclear Schiff base copper(II) complex. The CuII atom is coordinated by one O and two N atoms of the Schiff base ligand, and by one N atom of the thio­cyanate ligand, forming a square-planar coordination. The mol­ecule possesses crystallographic mirror symmetry, with one disordered CH2 group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031107/ci6642sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031107/ci6642Isup2.hkl
Contains datablock I

CCDC reference: 289692

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.048
  • wR factor = 0.115
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.81 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.07 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.13 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT412_ALERT_2_C Short Intra XH3 .. XHn H9A .. H10B .. 1.82 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

{2,4-Dichloro-6-[2- (dimethylamino)ethyliminomethyl]phenolato}thiocyanatocopper(II) top
Crystal data top
[Cu(C11H12Cl2N2O)(NCS)]F(000) = 772
Mr = 381.75Dx = 1.692 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 1964 reflections
a = 19.301 (2) Åθ = 2.8–21.2°
b = 6.950 (1) ŵ = 1.95 mm1
c = 11.173 (1) ÅT = 298 K
V = 1498.8 (3) Å3Block, blue
Z = 40.23 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1960 independent reflections
Radiation source: fine-focus sealed tube1486 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2524
Tmin = 0.663, Tmax = 0.720k = 99
12536 measured reflectionsl = 1414
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.054P)2 + 1.0678P]
where P = (Fo2 + 2Fc2)/3
1960 reflections(Δ/σ)max = 0.001
121 parametersΔρmax = 0.43 e Å3
6 restraintsΔρmin = 0.63 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*/UeqOcc. (<1)
Cu10.17718 (3)0.25000.35621 (5)0.03688 (19)
Cl10.15807 (7)0.25000.64774 (12)0.0621 (4)
Cl20.11021 (7)0.25000.76824 (12)0.0696 (5)
S10.41022 (7)0.25000.46467 (14)0.0673 (5)
O10.13481 (15)0.25000.5109 (3)0.0426 (8)
N10.08885 (18)0.25000.2757 (3)0.0391 (9)
N20.2176 (2)0.25000.1866 (3)0.0499 (11)
N30.2689 (2)0.25000.4250 (4)0.0616 (13)
C10.0153 (2)0.25000.4503 (4)0.0334 (9)
C20.0695 (2)0.25000.5370 (4)0.0326 (9)
C30.0473 (2)0.25000.6579 (4)0.0381 (10)
C40.0202 (2)0.25000.6908 (4)0.0385 (10)
H40.03220.25000.77140.046*
C50.0713 (2)0.25000.6035 (4)0.0413 (11)
C60.0541 (2)0.25000.4868 (4)0.0388 (10)
H60.08900.25000.42940.047*
C70.0288 (2)0.25000.3243 (4)0.0378 (10)
H70.00930.25000.27340.045*
C80.0941 (3)0.25000.1450 (4)0.0669 (18)
H8A0.05500.19720.10690.080*0.50
H8B0.09440.39430.12120.080*0.50
C90.1595 (3)0.1659 (12)0.1090 (6)0.054 (2)0.50
H9A0.15490.02750.11670.064*0.50
H9B0.16940.19520.02580.064*0.50
C100.2603 (3)0.0826 (7)0.1630 (4)0.0922 (17)
H10A0.26900.07300.07860.138*
H10B0.23660.03100.18990.138*
H10C0.30350.09490.20490.138*
C120.3274 (2)0.25000.4415 (4)0.0488 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0276 (3)0.0524 (4)0.0307 (3)0.0000.0030 (2)0.000
Cl10.0363 (6)0.0947 (11)0.0553 (8)0.0000.0164 (6)0.000
Cl20.0494 (8)0.1243 (14)0.0351 (7)0.0000.0052 (6)0.000
S10.0334 (7)0.1052 (13)0.0633 (9)0.0000.0025 (6)0.000
O10.0285 (15)0.070 (2)0.0290 (16)0.0000.0020 (12)0.000
N10.0321 (19)0.057 (2)0.0285 (19)0.0000.0019 (15)0.000
N20.032 (2)0.085 (3)0.032 (2)0.0000.0061 (17)0.000
N30.036 (2)0.107 (4)0.042 (3)0.0000.002 (2)0.000
C10.031 (2)0.036 (2)0.033 (2)0.0000.0068 (17)0.000
C20.033 (2)0.035 (2)0.030 (2)0.0000.0008 (17)0.000
C30.039 (3)0.044 (3)0.031 (2)0.0000.0019 (18)0.000
C40.044 (3)0.044 (3)0.028 (2)0.0000.010 (2)0.000
C50.032 (2)0.047 (3)0.045 (3)0.0000.012 (2)0.000
C60.033 (2)0.046 (3)0.037 (2)0.0000.0002 (19)0.000
C70.031 (2)0.049 (3)0.033 (2)0.0000.0030 (18)0.000
C80.043 (3)0.126 (6)0.031 (3)0.0000.003 (2)0.000
C90.041 (4)0.087 (6)0.033 (3)0.001 (3)0.004 (3)0.006 (3)
C100.136 (4)0.063 (3)0.077 (3)0.006 (3)0.058 (3)0.009 (2)
C120.038 (3)0.076 (4)0.033 (2)0.0000.006 (2)0.000
Geometric parameters (Å, º) top
Cu1—O11.912 (3)C2—C31.417 (6)
Cu1—N11.927 (4)C3—C41.354 (6)
Cu1—N31.930 (4)C4—C51.387 (7)
Cu1—N22.050 (4)C4—H40.93
Cl1—C51.746 (4)C5—C61.345 (7)
Cl2—C31.730 (5)C6—H60.93
S1—C121.619 (5)C7—H70.93
O1—C21.294 (5)C8—C91.449 (8)
N1—C71.280 (5)C8—C9i1.449 (8)
N1—C81.464 (6)C8—H8A0.94
N2—C10i1.450 (5)C8—H8B1.04
N2—C101.450 (5)C9—C9i1.169 (16)
N2—C91.533 (8)C9—H9A0.97
N2—C9i1.533 (8)C9—H9B0.97
N3—C121.144 (6)C10—H10A0.96
C1—C61.401 (6)C10—H10B0.96
C1—C21.425 (6)C10—H10C0.96
C1—C71.431 (6)
O1—Cu1—N192.49 (14)C5—C4—H4120.2
O1—Cu1—N391.85 (16)C6—C5—C4120.4 (4)
N1—Cu1—N3175.66 (16)C6—C5—Cl1120.7 (4)
O1—Cu1—N2177.06 (14)C4—C5—Cl1118.8 (4)
N1—Cu1—N284.56 (15)C5—C6—C1121.2 (4)
N3—Cu1—N291.10 (17)C5—C6—H6119.4
C2—O1—Cu1128.3 (3)C1—C6—H6119.4
C7—N1—C8119.1 (4)N1—C7—C1125.6 (4)
C7—N1—Cu1127.1 (3)N1—C7—H7117.2
C8—N1—Cu1113.8 (3)C1—C7—H7117.2
C10i—N2—C10106.8 (5)C9—C8—N1109.7 (4)
C10i—N2—C9128.2 (5)C9i—C8—N1109.7 (4)
C10—N2—C990.4 (4)C9—C8—H8A114.6
C10i—N2—C9i90.4 (4)N1—C8—H8A113.3
C10—N2—C9i128.2 (5)C9—C8—H8B108.3
C10i—N2—Cu1112.6 (2)N1—C8—H8B104.8
C10—N2—Cu1112.6 (2)H8A—C8—H8B105.4
C9—N2—Cu1104.2 (3)C8—C9—N2109.0 (5)
C9i—N2—Cu1104.2 (3)C8—C9—H9A107.1
C12—N3—Cu1165.8 (4)N2—C9—H9A113.3
C6—C1—C2120.3 (4)C8—C9—H9B110.6
C6—C1—C7117.4 (4)N2—C9—H9B108.6
C2—C1—C7122.3 (4)H9A—C9—H9B108.1
O1—C2—C3120.6 (4)N2—C10—H10A109.5
O1—C2—C1124.2 (4)N2—C10—H10B109.5
C3—C2—C1115.2 (4)H10A—C10—H10B109.5
C4—C3—C2123.3 (4)N2—C10—H10C109.5
C4—C3—Cl2118.8 (3)H10A—C10—H10C109.5
C2—C3—Cl2117.9 (3)H10B—C10—H10C109.5
C3—C4—C5119.5 (4)N3—C12—S1179.9 (5)
C3—C4—H4120.2
N1—Cu1—O1—C20.0C2—C3—C4—C50.0
N3—Cu1—O1—C2180.0Cl2—C3—C4—C5180.0
O1—Cu1—N1—C70.0C3—C4—C5—C60.0
N2—Cu1—N1—C7180.0C3—C4—C5—Cl1180.0
O1—Cu1—N1—C8180.0C4—C5—C6—C10.0
N2—Cu1—N1—C80.0Cl1—C5—C6—C1180.0
N1—Cu1—N2—C10i119.6 (3)C2—C1—C6—C50.0
N3—Cu1—N2—C10i60.4 (3)C7—C1—C6—C5180.0
N1—Cu1—N2—C10119.6 (3)C8—N1—C7—C1180.0
N3—Cu1—N2—C1060.4 (3)Cu1—N1—C7—C10.0
N1—Cu1—N2—C923.2 (3)C6—C1—C7—N1180.0
N3—Cu1—N2—C9156.8 (3)C2—C1—C7—N10.0
N1—Cu1—N2—C9i23.2 (3)C7—N1—C8—C9154.6 (4)
N3—Cu1—N2—C9i156.8 (3)Cu1—N1—C8—C925.4 (4)
O1—Cu1—N3—C12180.000 (2)C7—N1—C8—C9i154.6 (4)
N2—Cu1—N3—C120.000 (2)Cu1—N1—C8—C9i25.4 (4)
Cu1—O1—C2—C3180.0N1—C8—C9—C9i99.1 (3)
Cu1—O1—C2—C10.0C9i—C8—C9—N253.6 (5)
C6—C1—C2—O1180.0N1—C8—C9—N245.5 (6)
C7—C1—C2—O10.0C10i—N2—C9—C9i38.7 (3)
C6—C1—C2—C30.0C10—N2—C9—C9i150.6 (3)
C7—C1—C2—C3180.0Cu1—N2—C9—C9i95.98 (15)
O1—C2—C3—C4180.0C10i—N2—C9—C891.5 (6)
C1—C2—C3—C40.0C10—N2—C9—C8156.6 (5)
O1—C2—C3—Cl20.0C9i—N2—C9—C852.8 (5)
C1—C2—C3—Cl2180.0Cu1—N2—C9—C843.1 (5)
Symmetry code: (i) x, y+1/2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds