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The title compound, [Cu(C13H15BrNO)2], is a mononuclear copper(II) complex. The Cu atom is four-coordinated by two N atoms and two O atoms from two Schiff base ligands in a slightly distorted tetrahedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000280/ob6467sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000280/ob6467Isup2.hkl
Contains datablock I

CCDC reference: 263535

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.117
  • Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.01
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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.

Bis[4-bromo-2-(cyclohexyliminomethyl)phenolato]copper(II) top
Crystal data top
[Cu(C13H15BrNO)2]F(000) = 2520
Mr = 625.88Dx = 1.621 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 10170 reflections
a = 14.996 (1) Åθ = 2.6–22.8°
b = 13.597 (1) ŵ = 3.99 mm1
c = 25.156 (2) ÅT = 298 K
V = 5129.3 (7) Å3Block, blue
Z = 80.22 × 0.21 × 0.18 mm
Data collection top
Bruker APEX area-detector
diffractometer
5866 independent reflections
Radiation source: fine-focus sealed tube4083 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.433, Tmax = 0.487k = 1717
56364 measured reflectionsl = 3232
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0513P)2 + 4.6248P]
where P = (Fo2 + 2Fc2)/3
5866 reflections(Δ/σ)max < 0.001
298 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = 0.36 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
Cu10.14073 (3)0.58035 (3)0.307450 (17)0.04668 (13)
Br10.11579 (4)0.89451 (4)0.48997 (2)0.0925 (2)
Br20.32284 (3)0.25746 (4)0.101200 (18)0.07509 (16)
O10.15852 (17)0.66642 (19)0.36704 (11)0.0614 (7)
O20.21850 (17)0.58901 (17)0.24711 (11)0.0570 (6)
N10.01424 (19)0.6249 (2)0.29250 (11)0.0459 (6)
N20.1724 (2)0.4384 (2)0.32252 (12)0.0487 (7)
C10.0055 (2)0.7203 (2)0.37494 (14)0.0470 (8)
C20.0948 (3)0.7099 (2)0.39320 (14)0.0507 (9)
C30.1138 (3)0.7531 (3)0.44319 (16)0.0601 (10)
H30.17040.74480.45750.072*
C40.0533 (3)0.8060 (3)0.47094 (15)0.0645 (11)
H40.06920.83430.50320.077*
C50.0319 (3)0.8180 (3)0.45154 (14)0.0600 (10)
C60.0558 (3)0.7753 (3)0.40463 (14)0.0548 (9)
H60.11380.78290.39210.066*
C70.0266 (2)0.6806 (3)0.32519 (14)0.0490 (8)
H70.08450.69780.31580.059*
C80.0334 (2)0.5972 (2)0.24355 (14)0.0481 (8)
H80.09700.61160.24830.058*
C90.0232 (3)0.4892 (3)0.23293 (15)0.0550 (9)
H9A0.05010.45200.26160.066*
H9B0.03970.47250.23150.066*
C100.0674 (3)0.4616 (3)0.18054 (16)0.0677 (11)
H10A0.05760.39230.17350.081*
H10B0.13120.47240.18330.081*
C110.0309 (3)0.5213 (4)0.13520 (17)0.0766 (13)
H11A0.03210.50720.13080.092*
H11B0.06130.50320.10260.092*
C120.0435 (4)0.6289 (3)0.14551 (16)0.0788 (13)
H12A0.10670.64380.14740.095*
H12B0.01810.66640.11640.095*
C130.0015 (3)0.6589 (3)0.19768 (15)0.0667 (11)
H13A0.06550.65020.19460.080*
H13B0.01000.72790.20470.080*
C140.2364 (2)0.4137 (2)0.23458 (13)0.0463 (8)
C150.2394 (2)0.5131 (3)0.21718 (15)0.0511 (8)
C160.2703 (3)0.5295 (3)0.16496 (15)0.0598 (10)
H160.27480.59390.15290.072*
C170.2937 (3)0.4556 (3)0.13154 (16)0.0606 (10)
H170.31190.46950.09700.073*
C180.2903 (2)0.3594 (3)0.14933 (14)0.0533 (9)
C190.2636 (2)0.3378 (3)0.19992 (14)0.0506 (8)
H190.26340.27280.21160.061*
C200.2090 (2)0.3838 (3)0.28718 (14)0.0479 (8)
H200.21900.31840.29630.058*
C210.1532 (2)0.3957 (3)0.37550 (15)0.0524 (9)
H210.16240.32440.37390.063*
C220.2179 (3)0.4392 (3)0.41604 (15)0.0623 (10)
H22A0.27830.41960.40710.075*
H22B0.21480.51040.41460.075*
C230.1958 (3)0.4045 (4)0.47222 (17)0.0718 (12)
H23A0.20620.33430.47490.086*
H23B0.23490.43720.49740.086*
C240.1004 (3)0.4265 (3)0.48611 (16)0.0695 (11)
H24A0.09130.49720.48660.083*
H24B0.08740.40140.52140.083*
C250.0368 (3)0.3798 (3)0.44595 (15)0.0632 (10)
H25A0.04280.30880.44720.076*
H25B0.02420.39630.45520.076*
C260.0569 (2)0.4158 (3)0.39027 (15)0.0553 (9)
H26A0.04550.48590.38820.066*
H26B0.01790.38300.36520.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0432 (2)0.0422 (2)0.0546 (3)0.00269 (18)0.00131 (19)0.00353 (18)
Br10.1117 (4)0.1014 (4)0.0645 (3)0.0186 (3)0.0050 (3)0.0281 (3)
Br20.0868 (3)0.0790 (3)0.0595 (3)0.0036 (2)0.0212 (2)0.0054 (2)
O10.0514 (15)0.0595 (16)0.0733 (17)0.0029 (12)0.0118 (13)0.0114 (14)
O20.0548 (15)0.0453 (13)0.0707 (17)0.0006 (11)0.0149 (13)0.0049 (13)
N10.0473 (16)0.0439 (15)0.0466 (16)0.0006 (13)0.0042 (13)0.0016 (13)
N20.0486 (16)0.0473 (16)0.0503 (16)0.0024 (13)0.0085 (13)0.0088 (13)
C10.055 (2)0.0423 (18)0.0437 (18)0.0041 (15)0.0040 (16)0.0006 (14)
C20.058 (2)0.0397 (18)0.054 (2)0.0064 (16)0.0105 (18)0.0054 (16)
C30.063 (2)0.059 (2)0.059 (2)0.009 (2)0.0195 (19)0.0007 (18)
C40.086 (3)0.064 (2)0.044 (2)0.011 (2)0.014 (2)0.0029 (18)
C50.079 (3)0.057 (2)0.044 (2)0.000 (2)0.0040 (19)0.0039 (16)
C60.059 (2)0.057 (2)0.048 (2)0.0005 (18)0.0051 (17)0.0019 (17)
C70.049 (2)0.0474 (19)0.050 (2)0.0013 (16)0.0056 (16)0.0001 (16)
C80.0442 (19)0.052 (2)0.0485 (19)0.0037 (15)0.0070 (15)0.0056 (15)
C90.058 (2)0.050 (2)0.056 (2)0.0034 (17)0.0017 (17)0.0017 (16)
C100.075 (3)0.060 (2)0.068 (3)0.005 (2)0.007 (2)0.021 (2)
C110.075 (3)0.102 (4)0.053 (2)0.003 (3)0.001 (2)0.021 (2)
C120.099 (4)0.084 (3)0.054 (2)0.014 (3)0.013 (2)0.005 (2)
C130.087 (3)0.060 (2)0.053 (2)0.009 (2)0.016 (2)0.0085 (19)
C140.0397 (18)0.0503 (19)0.0489 (19)0.0009 (15)0.0046 (15)0.0061 (15)
C150.0385 (18)0.056 (2)0.059 (2)0.0003 (16)0.0013 (16)0.0106 (17)
C160.063 (2)0.059 (2)0.058 (2)0.0011 (19)0.0075 (19)0.0153 (19)
C170.057 (2)0.075 (3)0.049 (2)0.001 (2)0.0075 (18)0.016 (2)
C180.051 (2)0.062 (2)0.046 (2)0.0010 (18)0.0053 (16)0.0005 (17)
C190.045 (2)0.056 (2)0.051 (2)0.0002 (16)0.0037 (15)0.0067 (17)
C200.0452 (18)0.0463 (18)0.052 (2)0.0003 (15)0.0082 (16)0.0091 (16)
C210.058 (2)0.0463 (19)0.052 (2)0.0029 (16)0.0124 (17)0.0103 (16)
C220.049 (2)0.080 (3)0.058 (2)0.004 (2)0.0031 (18)0.017 (2)
C230.067 (3)0.095 (3)0.053 (2)0.004 (2)0.002 (2)0.013 (2)
C240.080 (3)0.076 (3)0.053 (2)0.003 (2)0.017 (2)0.002 (2)
C250.059 (2)0.070 (2)0.061 (2)0.002 (2)0.0202 (19)0.003 (2)
C260.052 (2)0.057 (2)0.057 (2)0.0049 (17)0.0062 (17)0.0016 (17)
Geometric parameters (Å, º) top
Cu1—O21.918 (3)C11—H11B0.9700
Cu1—O11.920 (3)C12—C131.531 (5)
Cu1—N22.024 (3)C12—H12A0.9700
Cu1—N12.027 (3)C12—H12B0.9700
Br1—C51.898 (4)C13—H13A0.9700
Br2—C181.904 (4)C13—H13B0.9700
O1—C21.302 (4)C14—C191.411 (5)
O2—C151.316 (4)C14—C151.421 (5)
N1—C71.274 (4)C14—C201.444 (5)
N1—C81.473 (4)C15—C161.411 (5)
N2—C201.282 (4)C16—C171.356 (5)
N2—C211.482 (4)C16—H160.9300
C1—C61.401 (5)C17—C181.384 (5)
C1—C21.423 (5)C17—H170.9300
C1—C71.446 (5)C18—C191.366 (5)
C2—C31.417 (5)C19—H190.9300
C3—C41.351 (6)C20—H200.9300
C3—H30.9300C21—C261.515 (5)
C4—C51.377 (6)C21—C221.526 (6)
C4—H40.9300C21—H210.9800
C5—C61.363 (5)C22—C231.526 (5)
C6—H60.9300C22—H22A0.9700
C7—H70.9300C22—H22B0.9700
C8—C91.501 (5)C23—C241.504 (6)
C8—C131.520 (5)C23—H23A0.9700
C8—H80.9800C23—H23B0.9700
C9—C101.522 (5)C24—C251.528 (6)
C9—H9A0.9700C24—H24A0.9700
C9—H9B0.9700C24—H24B0.9700
C10—C111.503 (6)C25—C261.514 (5)
C10—H10A0.9700C25—H25A0.9700
C10—H10B0.9700C25—H25B0.9700
C11—C121.499 (7)C26—H26A0.9700
C11—H11A0.9700C26—H26B0.9700
O2—Cu1—O1119.73 (12)H12A—C12—H12B108.1
O2—Cu1—N293.69 (11)C8—C13—C12110.6 (3)
O1—Cu1—N2113.74 (12)C8—C13—H13A109.5
O2—Cu1—N1113.83 (11)C12—C13—H13A109.5
O1—Cu1—N195.32 (11)C8—C13—H13B109.5
N2—Cu1—N1122.65 (12)C12—C13—H13B109.5
C2—O1—Cu1124.7 (2)H13A—C13—H13B108.1
C15—O2—Cu1123.3 (2)C19—C14—C15119.8 (3)
C7—N1—C8117.3 (3)C19—C14—C20116.2 (3)
C7—N1—Cu1120.5 (2)C15—C14—C20124.0 (3)
C8—N1—Cu1122.2 (2)O2—C15—C16119.1 (3)
C20—N2—C21118.7 (3)O2—C15—C14124.2 (3)
C20—N2—Cu1121.5 (2)C16—C15—C14116.6 (3)
C21—N2—Cu1119.8 (2)C17—C16—C15123.0 (4)
C6—C1—C2119.9 (3)C17—C16—H16118.5
C6—C1—C7116.3 (3)C15—C16—H16118.5
C2—C1—C7123.7 (3)C16—C17—C18119.3 (3)
O1—C2—C3119.3 (3)C16—C17—H17120.3
O1—C2—C1124.9 (3)C18—C17—H17120.3
C3—C2—C1115.7 (4)C19—C18—C17121.1 (4)
C4—C3—C2123.0 (4)C19—C18—Br2120.7 (3)
C4—C3—H3118.5C17—C18—Br2118.2 (3)
C2—C3—H3118.5C18—C19—C14120.2 (3)
C3—C4—C5120.2 (4)C18—C19—H19119.9
C3—C4—H4119.9C14—C19—H19119.9
C5—C4—H4119.9N2—C20—C14126.4 (3)
C6—C5—C4120.1 (4)N2—C20—H20116.8
C6—C5—Br1120.0 (3)C14—C20—H20116.8
C4—C5—Br1120.0 (3)N2—C21—C26109.5 (3)
C5—C6—C1121.1 (4)N2—C21—C22109.1 (3)
C5—C6—H6119.5C26—C21—C22111.8 (3)
C1—C6—H6119.5N2—C21—H21108.8
N1—C7—C1128.4 (3)C26—C21—H21108.8
N1—C7—H7115.8C22—C21—H21108.8
C1—C7—H7115.8C23—C22—C21111.2 (3)
N1—C8—C9110.5 (3)C23—C22—H22A109.4
N1—C8—C13109.0 (3)C21—C22—H22A109.4
C9—C8—C13111.7 (3)C23—C22—H22B109.4
N1—C8—H8108.5C21—C22—H22B109.4
C9—C8—H8108.5H22A—C22—H22B108.0
C13—C8—H8108.5C24—C23—C22111.1 (4)
C8—C9—C10110.5 (3)C24—C23—H23A109.4
C8—C9—H9A109.5C22—C23—H23A109.4
C10—C9—H9A109.5C24—C23—H23B109.4
C8—C9—H9B109.5C22—C23—H23B109.4
C10—C9—H9B109.5H23A—C23—H23B108.0
H9A—C9—H9B108.1C23—C24—C25111.0 (3)
C11—C10—C9111.4 (3)C23—C24—H24A109.4
C11—C10—H10A109.3C25—C24—H24A109.4
C9—C10—H10A109.3C23—C24—H24B109.4
C11—C10—H10B109.3C25—C24—H24B109.4
C9—C10—H10B109.3H24A—C24—H24B108.0
H10A—C10—H10B108.0C26—C25—C24110.6 (3)
C12—C11—C10110.5 (4)C26—C25—H25A109.5
C12—C11—H11A109.5C24—C25—H25A109.5
C10—C11—H11A109.5C26—C25—H25B109.5
C12—C11—H11B109.5C24—C25—H25B109.5
C10—C11—H11B109.5H25A—C25—H25B108.1
H11A—C11—H11B108.1C25—C26—C21111.0 (3)
C11—C12—C13110.7 (4)C25—C26—H26A109.4
C11—C12—H12A109.5C21—C26—H26A109.4
C13—C12—H12A109.5C25—C26—H26B109.4
C11—C12—H12B109.5C21—C26—H26B109.4
C13—C12—H12B109.5H26A—C26—H26B108.0
O2—Cu1—O1—C2138.7 (3)Cu1—N1—C8—C1376.2 (3)
N2—Cu1—O1—C2111.9 (3)N1—C8—C9—C10176.4 (3)
N1—Cu1—O1—C217.3 (3)C13—C8—C9—C1054.9 (4)
O1—Cu1—O2—C15148.6 (3)C8—C9—C10—C1156.3 (5)
N2—Cu1—O2—C1528.5 (3)C9—C10—C11—C1257.9 (5)
N1—Cu1—O2—C1599.8 (3)C10—C11—C12—C1357.5 (5)
O2—Cu1—N1—C7135.4 (3)N1—C8—C13—C12177.4 (3)
O1—Cu1—N1—C79.6 (3)C9—C8—C13—C1255.1 (5)
N2—Cu1—N1—C7113.1 (3)C11—C12—C13—C856.1 (5)
O2—Cu1—N1—C843.0 (3)Cu1—O2—C15—C16158.5 (3)
O1—Cu1—N1—C8168.9 (2)Cu1—O2—C15—C1424.1 (5)
N2—Cu1—N1—C868.5 (3)C19—C14—C15—O2177.5 (3)
O2—Cu1—N2—C2018.3 (3)C20—C14—C15—O20.7 (5)
O1—Cu1—N2—C20143.1 (3)C19—C14—C15—C160.0 (5)
N1—Cu1—N2—C20103.2 (3)C20—C14—C15—C16178.2 (3)
O2—Cu1—N2—C21161.6 (3)O2—C15—C16—C17179.7 (4)
O1—Cu1—N2—C2136.8 (3)C14—C15—C16—C172.0 (6)
N1—Cu1—N2—C2176.9 (3)C15—C16—C17—C182.1 (6)
Cu1—O1—C2—C3165.7 (3)C16—C17—C18—C190.1 (6)
Cu1—O1—C2—C116.0 (5)C16—C17—C18—Br2179.6 (3)
C6—C1—C2—O1174.9 (3)C17—C18—C19—C141.9 (6)
C7—C1—C2—O12.1 (6)Br2—C18—C19—C14177.6 (3)
C6—C1—C2—C33.4 (5)C15—C14—C19—C181.9 (5)
C7—C1—C2—C3179.5 (3)C20—C14—C19—C18179.7 (3)
O1—C2—C3—C4174.8 (4)C21—N2—C20—C14176.8 (3)
C1—C2—C3—C43.7 (5)Cu1—N2—C20—C143.1 (5)
C2—C3—C4—C51.5 (6)C19—C14—C20—N2171.2 (3)
C3—C4—C5—C61.0 (6)C15—C14—C20—N210.5 (6)
C3—C4—C5—Br1178.7 (3)C20—N2—C21—C26129.2 (3)
C4—C5—C6—C11.1 (6)Cu1—N2—C21—C2650.9 (4)
Br1—C5—C6—C1178.6 (3)C20—N2—C21—C22108.1 (4)
C2—C1—C6—C51.2 (5)Cu1—N2—C21—C2271.7 (3)
C7—C1—C6—C5178.5 (3)N2—C21—C22—C23175.0 (3)
C8—N1—C7—C1178.3 (3)C26—C21—C22—C2353.7 (4)
Cu1—N1—C7—C10.3 (5)C21—C22—C23—C2454.7 (5)
C6—C1—C7—N1176.5 (4)C22—C23—C24—C2556.7 (5)
C2—C1—C7—N16.4 (6)C23—C24—C25—C2657.7 (5)
C7—N1—C8—C9134.6 (3)C24—C25—C26—C2156.4 (4)
Cu1—N1—C8—C946.9 (4)N2—C21—C26—C25175.8 (3)
C7—N1—C8—C13102.3 (4)C22—C21—C26—C2554.8 (4)
 

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