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In the mononuclear title complex, [Cu(C18H14Cl2N3O2)2], the CuII atom is coordinated by two N atoms and two O atoms from the Schiff base ligands in a square-planar geometry, with a dihedral angle between the two chelate NCuO planes of 31.57 (3)°. The Cu atom is located on a twofold axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049233/wn2089sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049233/wn2089Isup2.hkl
Contains datablock I

CCDC reference: 630505

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.105
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: APEX2; software used to prepare material for publication: APEX2.

{4,6-Dichloro-2-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4- yl)iminomethyl]phenolato-κ2N,O}copper(II) top
Crystal data top
[Cu(C18H14Cl2N3O2)2]F(000) = 1660
Mr = 813.98Dx = 1.514 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 23.4341 (17) ÅCell parameters from 5244 reflections
b = 6.7434 (5) Åθ = 2.1–25.0°
c = 22.6048 (16) ŵ = 0.96 mm1
β = 91.570 (1)°T = 273 K
V = 3570.8 (4) Å3Prism, blue
Z = 40.34 × 0.16 × 0.13 mm
Data collection top
Bruker APEX-II area-detector
diffractometer
3172 independent reflections
Radiation source: fine-focus sealed tube2660 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
φ and ω scansθmax = 25.2°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2828
Tmin = 0.736, Tmax = 0.885k = 87
10369 measured reflectionsl = 2627
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0692P)2 + 0.3862P]
where P = (Fo2 + 2Fc2)/3
3172 reflections(Δ/σ)max < 0.001
233 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.37 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
Cu10.00000.13084 (6)0.25000.03850 (15)
N10.02757 (7)0.0803 (3)0.17038 (7)0.0385 (4)
N20.08406 (8)0.1200 (3)0.07475 (8)0.0430 (5)
N30.06744 (7)0.0499 (3)0.04327 (7)0.0420 (4)
O10.07314 (6)0.1923 (3)0.28143 (7)0.0490 (4)
O20.00544 (8)0.3147 (3)0.06217 (8)0.0569 (5)
C10.01213 (9)0.0260 (3)0.12484 (9)0.0385 (5)
C20.04701 (10)0.1319 (3)0.12329 (10)0.0421 (5)
C30.02511 (10)0.1510 (3)0.07489 (10)0.0409 (5)
C40.04889 (13)0.3040 (4)0.16436 (12)0.0627 (7)
H4A0.02590.27620.19920.094*
H4B0.03440.41960.14510.094*
H4C0.08760.32740.17530.094*
C50.09640 (11)0.2978 (4)0.03901 (11)0.0548 (6)
H5A0.06280.33640.01860.082*
H5B0.12650.26930.01070.082*
H5C0.10800.40380.06440.082*
C60.10449 (10)0.1333 (3)0.00074 (10)0.0430 (5)
C70.16238 (11)0.0881 (4)0.00231 (11)0.0565 (7)
H70.17760.00690.02650.068*
C80.19710 (13)0.1652 (5)0.04714 (14)0.0707 (9)
H80.23560.13200.04930.085*
C90.17462 (15)0.2918 (5)0.08884 (14)0.0766 (9)
H90.19790.34340.11900.092*
C100.11806 (15)0.3403 (4)0.08529 (13)0.0681 (8)
H100.10350.42950.11240.082*
C110.08193 (12)0.2600 (4)0.04240 (10)0.0535 (6)
H110.04320.29030.04140.064*
C120.11991 (9)0.2175 (3)0.25324 (9)0.0393 (5)
C130.17017 (9)0.2768 (3)0.28486 (10)0.0404 (5)
C140.22127 (9)0.3076 (3)0.25816 (11)0.0452 (6)
H140.25330.34730.28040.054*
C150.22463 (9)0.2788 (3)0.19751 (11)0.0443 (5)
C160.17817 (10)0.2199 (4)0.16449 (11)0.0438 (5)
H160.18130.20000.12400.053*
C170.12514 (9)0.1891 (3)0.19143 (10)0.0389 (5)
C180.07861 (10)0.1245 (3)0.15395 (10)0.0407 (5)
H180.08570.11310.11380.049*
Cl10.16534 (3)0.30613 (10)0.36073 (3)0.05329 (19)
Cl20.28948 (3)0.31602 (11)0.16363 (3)0.0640 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0304 (2)0.0529 (3)0.0319 (2)0.0000.00376 (15)0.000
N10.0334 (9)0.0470 (11)0.0348 (9)0.0017 (8)0.0045 (7)0.0013 (8)
N20.0420 (10)0.0463 (12)0.0403 (10)0.0063 (8)0.0068 (8)0.0002 (8)
N30.0406 (10)0.0453 (11)0.0396 (10)0.0024 (9)0.0082 (8)0.0007 (8)
O10.0348 (8)0.0762 (12)0.0359 (9)0.0084 (8)0.0023 (7)0.0031 (7)
O20.0655 (12)0.0514 (11)0.0531 (11)0.0126 (9)0.0122 (9)0.0078 (8)
C10.0337 (10)0.0470 (14)0.0346 (11)0.0003 (10)0.0026 (8)0.0028 (9)
C20.0390 (12)0.0501 (14)0.0370 (12)0.0027 (10)0.0025 (9)0.0001 (9)
C30.0367 (11)0.0453 (14)0.0404 (12)0.0021 (10)0.0035 (9)0.0034 (10)
C40.0687 (18)0.0607 (18)0.0577 (17)0.0159 (14)0.0152 (13)0.0118 (13)
C50.0568 (15)0.0538 (16)0.0531 (15)0.0106 (12)0.0112 (12)0.0024 (12)
C60.0446 (13)0.0494 (15)0.0344 (12)0.0070 (10)0.0088 (9)0.0067 (10)
C70.0487 (14)0.0694 (18)0.0506 (14)0.0037 (12)0.0119 (11)0.0071 (12)
C80.0554 (17)0.086 (2)0.0689 (19)0.0164 (15)0.0231 (15)0.0112 (16)
C90.085 (2)0.078 (2)0.0644 (19)0.0188 (18)0.0324 (17)0.0016 (16)
C100.092 (2)0.0595 (18)0.0516 (16)0.0049 (15)0.0200 (15)0.0060 (13)
C110.0649 (16)0.0508 (16)0.0442 (14)0.0026 (13)0.0105 (11)0.0042 (11)
C120.0361 (11)0.0409 (13)0.0407 (12)0.0015 (10)0.0050 (9)0.0024 (9)
C130.0375 (11)0.0400 (13)0.0433 (12)0.0007 (10)0.0077 (9)0.0013 (10)
C140.0373 (12)0.0372 (13)0.0605 (16)0.0018 (10)0.0107 (11)0.0016 (10)
C150.0330 (11)0.0369 (13)0.0630 (15)0.0024 (10)0.0039 (10)0.0020 (10)
C160.0410 (12)0.0452 (14)0.0452 (13)0.0009 (11)0.0017 (10)0.0001 (10)
C170.0325 (11)0.0426 (13)0.0413 (12)0.0015 (9)0.0021 (9)0.0003 (9)
C180.0400 (12)0.0467 (14)0.0352 (11)0.0002 (10)0.0015 (9)0.0008 (9)
Cl10.0507 (4)0.0640 (4)0.0444 (4)0.0004 (3)0.0132 (3)0.0078 (3)
Cl20.0387 (3)0.0662 (5)0.0876 (5)0.0094 (3)0.0130 (3)0.0052 (3)
Geometric parameters (Å, º) top
Cu1—O1i1.8835 (15)C6—C71.390 (3)
Cu1—O11.8835 (15)C7—C81.384 (4)
Cu1—N11.9587 (17)C7—H70.9300
Cu1—N1i1.9587 (17)C8—C91.386 (5)
N1—C181.297 (3)C8—H80.9300
N1—C11.417 (3)C9—C101.366 (5)
N2—C21.383 (3)C9—H90.9300
N2—N31.409 (3)C10—C111.380 (4)
N2—C51.470 (3)C10—H100.9300
N3—C31.386 (3)C11—H110.9300
N3—C61.419 (3)C12—C131.418 (3)
O1—C121.294 (2)C12—C171.419 (3)
O2—C31.233 (3)C13—C141.371 (3)
C1—C21.342 (3)C13—Cl11.733 (2)
C1—C31.435 (3)C14—C151.389 (3)
C2—C41.488 (3)C14—H140.9300
C4—H4A0.9600C15—C161.362 (3)
C4—H4B0.9600C15—Cl21.739 (2)
C4—H4C0.9600C16—C171.414 (3)
C5—H5A0.9600C16—H160.9300
C5—H5B0.9600C17—C181.430 (3)
C5—H5C0.9600C18—H180.9300
C6—C111.387 (3)
O1i—Cu1—O1154.58 (11)C11—C6—N3118.9 (2)
O1i—Cu1—N190.65 (7)C7—C6—N3120.6 (2)
O1—Cu1—N193.73 (7)C8—C7—C6119.4 (3)
O1i—Cu1—N1i93.73 (7)C8—C7—H7120.3
O1—Cu1—N1i90.65 (7)C6—C7—H7120.3
N1—Cu1—N1i159.96 (11)C7—C8—C9120.2 (3)
C18—N1—C1116.35 (17)C7—C8—H8119.9
C18—N1—Cu1123.59 (15)C9—C8—H8119.9
C1—N1—Cu1119.08 (13)C10—C9—C8119.6 (3)
C2—N2—N3105.76 (17)C10—C9—H9120.2
C2—N2—C5119.9 (2)C8—C9—H9120.2
N3—N2—C5116.01 (18)C9—C10—C11121.5 (3)
C3—N3—N2110.10 (17)C9—C10—H10119.2
C3—N3—C6125.6 (2)C11—C10—H10119.2
N2—N3—C6120.26 (18)C10—C11—C6118.7 (3)
C12—O1—Cu1128.14 (13)C10—C11—H11120.6
C2—C1—N1127.7 (2)C6—C11—H11120.6
C2—C1—C3109.25 (19)O1—C12—C13119.5 (2)
N1—C1—C3122.7 (2)O1—C12—C17124.35 (19)
C1—C2—N2110.07 (19)C13—C12—C17116.2 (2)
C1—C2—C4129.1 (2)C14—C13—C12122.9 (2)
N2—C2—C4120.8 (2)C14—C13—Cl1119.99 (17)
O2—C3—N3126.0 (2)C12—C13—Cl1117.07 (17)
O2—C3—C1129.5 (2)C13—C14—C15119.2 (2)
N3—C3—C1104.47 (19)C13—C14—H14120.4
C2—C4—H4A109.5C15—C14—H14120.4
C2—C4—H4B109.5C16—C15—C14121.0 (2)
H4A—C4—H4B109.5C16—C15—Cl2119.72 (19)
C2—C4—H4C109.5C14—C15—Cl2119.24 (17)
H4A—C4—H4C109.5C15—C16—C17120.4 (2)
H4B—C4—H4C109.5C15—C16—H16119.8
N2—C5—H5A109.5C17—C16—H16119.8
N2—C5—H5B109.5C16—C17—C12120.3 (2)
H5A—C5—H5B109.5C16—C17—C18117.0 (2)
N2—C5—H5C109.5C12—C17—C18122.6 (2)
H5A—C5—H5C109.5N1—C18—C17126.5 (2)
H5B—C5—H5C109.5N1—C18—H18116.8
C11—C6—C7120.5 (2)C17—C18—H18116.8
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O20.932.492.950 (3)111
C5—H5A···O2ii0.962.463.352 (3)154
Symmetry code: (ii) x, y, z.
 

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