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The title compound, [Cu(C20H14N2O2)], is a mononuclear copper(II) compound, the Cu atom of which is coordinated by two N and two O atoms from the o-phenyl­ene­bis(salicylideneamine) ligand in a square-planar geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019975/ng6151sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019975/ng6151Isup2.hkl
Contains datablock I

CCDC reference: 277733

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.076
  • wR factor = 0.171
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 4.88 Cell volume su given = 7.00 PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit P 2ac ab PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 1574.10 Ang-3 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 3487 Count of symmetry unique reflns 2102 Completeness (_total/calc) 165.89% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1385 Fraction of Friedel pairs measured 0.659 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 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 1 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: SMART; data reduction: SAINT (Bruker, 1998); 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.

[o-Phenylenebis(salicylideneaminato)]copper(II) top
Crystal data top
[Cu(C20H14N2O2)]F(000) = 772
Mr = 377.87Dx = 1.594 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac abCell parameters from 880 reflections
a = 5.470 (1) Åθ = 2.0–21.3°
b = 16.618 (3) ŵ = 1.40 mm1
c = 17.322 (3) ÅT = 298 K
V = 1574.1 (7) Å3Block, blue
Z = 40.23 × 0.18 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3487 independent reflections
Radiation source: fine-focus sealed tube2138 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.096
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 67
Tmin = 0.739, Tmax = 0.817k = 2120
9949 measured reflectionsl = 2214
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.076H-atom parameters constrained
wR(F2) = 0.171 w = 1/[σ2(Fo2) + (0.067P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3487 reflectionsΔρmax = 0.54 e Å3
226 parametersΔρmin = 0.47 e Å3
0 restraintsAbsolute structure: Flack (1983), with 1385 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (4)
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
Cu10.85100 (16)0.72327 (5)0.18951 (5)0.0390 (3)
O10.8497 (10)0.6265 (3)0.1375 (3)0.0489 (13)
O20.5748 (9)0.6824 (3)0.2367 (3)0.0403 (13)
N11.1285 (11)0.7616 (3)0.1400 (3)0.0314 (13)
N20.8482 (12)0.8204 (3)0.2440 (3)0.0330 (13)
C11.0159 (14)0.5965 (4)0.0907 (4)0.0339 (17)
C20.9898 (15)0.5191 (4)0.0624 (4)0.046 (2)
H20.85500.48870.07720.055*
C31.1576 (18)0.4867 (5)0.0134 (4)0.051 (2)
H31.13430.43470.00500.062*
C41.3623 (17)0.5295 (5)0.0096 (5)0.057 (2)
H41.47690.50650.04260.068*
C51.3915 (16)0.6045 (5)0.0167 (5)0.054 (2)
H51.53060.63250.00150.065*
C61.2232 (13)0.6440 (4)0.0663 (4)0.0362 (18)
C71.2656 (13)0.7232 (5)0.0926 (4)0.0389 (17)
H71.40370.74960.07410.047*
C81.1913 (14)0.8409 (4)0.1632 (4)0.0335 (17)
C91.3801 (15)0.8895 (5)0.1356 (4)0.047 (2)
H91.48190.87050.09660.056*
C101.4163 (15)0.9639 (5)0.1649 (5)0.052 (2)
H101.54810.99430.14750.063*
C111.2630 (17)0.9958 (5)0.2199 (5)0.052 (2)
H111.29011.04730.23910.063*
C121.0679 (16)0.9505 (4)0.2465 (5)0.048 (2)
H120.96050.97220.28250.057*
C131.0327 (14)0.8730 (5)0.2195 (4)0.0406 (19)
C140.7091 (13)0.8360 (4)0.3024 (4)0.0367 (18)
H140.73820.88400.32830.044*
C150.5160 (13)0.7870 (5)0.3310 (4)0.0399 (18)
C160.3757 (17)0.8167 (5)0.3955 (5)0.052 (2)
H160.40990.86630.41790.063*
C170.1870 (15)0.7682 (6)0.4227 (5)0.053 (2)
H170.10230.78400.46670.064*
C180.1224 (17)0.6983 (6)0.3871 (5)0.060 (3)
H180.01150.66910.40470.072*
C190.2542 (15)0.6711 (4)0.3255 (5)0.046 (2)
H190.21060.62260.30250.056*
C200.4552 (14)0.7147 (5)0.2957 (4)0.044 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0416 (5)0.0369 (5)0.0385 (5)0.0036 (4)0.0013 (5)0.0006 (5)
O10.037 (3)0.060 (3)0.050 (3)0.007 (3)0.008 (3)0.011 (3)
O20.034 (3)0.030 (3)0.057 (3)0.005 (2)0.007 (3)0.005 (3)
N10.036 (3)0.029 (3)0.029 (3)0.002 (3)0.007 (3)0.005 (2)
N20.041 (4)0.026 (3)0.033 (3)0.008 (3)0.003 (4)0.002 (3)
C10.044 (5)0.030 (4)0.028 (4)0.007 (3)0.001 (4)0.001 (3)
C20.058 (5)0.036 (4)0.044 (5)0.005 (4)0.006 (5)0.003 (4)
C30.070 (6)0.043 (4)0.041 (5)0.001 (5)0.008 (5)0.001 (4)
C40.056 (6)0.061 (5)0.053 (5)0.010 (5)0.011 (5)0.007 (4)
C50.052 (6)0.064 (6)0.045 (5)0.000 (5)0.002 (5)0.005 (5)
C60.033 (4)0.041 (4)0.035 (4)0.008 (3)0.002 (4)0.001 (4)
C70.038 (4)0.047 (4)0.031 (4)0.002 (4)0.004 (3)0.002 (4)
C80.043 (5)0.027 (3)0.031 (4)0.005 (3)0.003 (3)0.007 (3)
C90.051 (5)0.063 (5)0.026 (4)0.004 (4)0.002 (4)0.012 (4)
C100.044 (5)0.064 (6)0.050 (5)0.009 (4)0.001 (4)0.001 (5)
C110.074 (6)0.029 (4)0.054 (6)0.004 (4)0.004 (5)0.004 (4)
C120.066 (7)0.033 (4)0.045 (5)0.002 (4)0.002 (4)0.002 (4)
C130.031 (4)0.060 (5)0.031 (4)0.002 (4)0.014 (4)0.000 (4)
C140.052 (5)0.023 (3)0.035 (4)0.011 (3)0.008 (4)0.005 (3)
C150.037 (4)0.054 (5)0.029 (4)0.014 (4)0.001 (3)0.002 (4)
C160.063 (6)0.043 (4)0.052 (5)0.012 (5)0.006 (5)0.002 (4)
C170.049 (5)0.072 (6)0.039 (5)0.013 (5)0.012 (4)0.001 (5)
C180.040 (5)0.091 (7)0.049 (5)0.013 (5)0.009 (5)0.028 (5)
C190.048 (5)0.032 (4)0.059 (6)0.003 (3)0.000 (4)0.011 (4)
C200.036 (4)0.053 (5)0.044 (5)0.020 (4)0.002 (4)0.013 (4)
Geometric parameters (Å, º) top
Cu1—O11.844 (5)C8—C91.396 (10)
Cu1—O21.847 (5)C8—C131.410 (10)
Cu1—N11.856 (6)C9—C101.352 (10)
Cu1—N21.869 (5)C9—H90.9300
O1—C11.315 (8)C10—C111.375 (11)
O2—C201.326 (8)C10—H100.9300
N1—C71.282 (8)C11—C121.385 (11)
N1—C81.420 (8)C11—H110.9300
N2—C141.292 (9)C12—C131.383 (10)
N2—C131.401 (9)C12—H120.9300
C1—C21.384 (9)C14—C151.422 (10)
C1—C61.445 (10)C14—H140.9300
C2—C31.362 (10)C15—C201.390 (10)
C2—H20.9300C15—C161.442 (10)
C3—C41.385 (11)C16—C171.392 (11)
C3—H30.9300C16—H160.9300
C4—C51.337 (10)C17—C181.362 (12)
C4—H40.9300C17—H170.9300
C5—C61.420 (10)C18—C191.364 (11)
C5—H50.9300C18—H180.9300
C6—C71.412 (10)C19—C201.414 (10)
C7—H70.9300C19—H190.9300
O1—Cu1—O283.8 (2)C13—C8—N1113.4 (6)
O1—Cu1—N194.4 (2)C10—C9—C8120.6 (7)
O2—Cu1—N1178.2 (2)C10—C9—H9119.7
O1—Cu1—N2178.7 (3)C8—C9—H9119.7
O2—Cu1—N295.0 (2)C9—C10—C11121.6 (8)
N1—Cu1—N286.8 (3)C9—C10—H10119.2
C1—O1—Cu1129.0 (5)C11—C10—H10119.2
C20—O2—Cu1126.6 (5)C10—C11—C12119.4 (7)
C7—N1—C8120.1 (6)C10—C11—H11120.3
C7—N1—Cu1127.1 (5)C12—C11—H11120.3
C8—N1—Cu1112.7 (5)C13—C12—C11120.1 (8)
C14—N2—C13122.4 (6)C13—C12—H12120.0
C14—N2—Cu1125.0 (5)C11—C12—H12120.0
C13—N2—Cu1112.4 (5)C12—C13—N2125.4 (7)
O1—C1—C2119.9 (7)C12—C13—C8120.0 (7)
O1—C1—C6121.0 (6)N2—C13—C8114.6 (7)
C2—C1—C6119.0 (7)N2—C14—C15126.5 (7)
C3—C2—C1121.3 (8)N2—C14—H14116.7
C3—C2—H2119.4C15—C14—H14116.7
C1—C2—H2119.4C20—C15—C14121.3 (7)
C2—C3—C4121.4 (7)C20—C15—C16120.6 (7)
C2—C3—H3119.3C14—C15—C16118.0 (7)
C4—C3—H3119.3C17—C16—C15117.3 (8)
C5—C4—C3118.6 (8)C17—C16—H16121.4
C5—C4—H4120.7C15—C16—H16121.4
C3—C4—H4120.7C18—C17—C16122.2 (8)
C4—C5—C6124.0 (8)C18—C17—H17118.9
C4—C5—H5118.0C16—C17—H17118.9
C6—C5—H5118.0C17—C18—C19119.9 (9)
C7—C6—C5121.3 (7)C17—C18—H18120.0
C7—C6—C1122.9 (6)C19—C18—H18120.0
C5—C6—C1115.7 (7)C18—C19—C20121.8 (8)
N1—C7—C6125.1 (7)C18—C19—H19119.1
N1—C7—H7117.5C20—C19—H19119.1
C6—C7—H7117.5O2—C20—C15124.8 (7)
C9—C8—C13118.3 (7)O2—C20—C19117.3 (8)
C9—C8—N1128.3 (7)C15—C20—C19117.9 (7)
O2—Cu1—O1—C1172.2 (6)C13—C8—C9—C103.1 (11)
N1—Cu1—O1—C18.0 (6)N1—C8—C9—C10179.2 (7)
O1—Cu1—O2—C20172.3 (6)C8—C9—C10—C113.1 (13)
N2—Cu1—O2—C207.3 (6)C9—C10—C11—C120.6 (13)
O1—Cu1—N1—C75.6 (6)C10—C11—C12—C131.9 (12)
N2—Cu1—N1—C7174.0 (6)C11—C12—C13—N2177.6 (7)
O1—Cu1—N1—C8177.9 (4)C11—C12—C13—C81.9 (11)
N2—Cu1—N1—C82.6 (4)C14—N2—C13—C129.2 (11)
O2—Cu1—N2—C149.8 (6)Cu1—N2—C13—C12176.6 (6)
N1—Cu1—N2—C14170.4 (6)C14—N2—C13—C8170.3 (6)
O2—Cu1—N2—C13176.2 (5)Cu1—N2—C13—C83.9 (7)
N1—Cu1—N2—C133.6 (5)C9—C8—C13—C120.6 (10)
Cu1—O1—C1—C2174.4 (5)N1—C8—C13—C12178.6 (6)
Cu1—O1—C1—C67.4 (10)C9—C8—C13—N2179.9 (6)
O1—C1—C2—C3179.4 (7)N1—C8—C13—N21.9 (9)
C6—C1—C2—C31.3 (11)C13—N2—C14—C15179.3 (6)
C1—C2—C3—C40.6 (12)Cu1—N2—C14—C157.3 (10)
C2—C3—C4—C50.8 (13)N2—C14—C15—C201.0 (11)
C3—C4—C5—C60.9 (13)N2—C14—C15—C16177.7 (6)
C4—C5—C6—C7179.4 (8)C20—C15—C16—C173.1 (11)
C4—C5—C6—C12.6 (12)C14—C15—C16—C17179.9 (7)
O1—C1—C6—C72.3 (11)C15—C16—C17—C185.0 (12)
C2—C1—C6—C7179.5 (7)C16—C17—C18—C194.3 (13)
O1—C1—C6—C5179.1 (6)C17—C18—C19—C201.6 (12)
C2—C1—C6—C52.7 (10)Cu1—O2—C20—C151.8 (10)
C8—N1—C7—C6179.2 (6)Cu1—O2—C20—C19176.9 (5)
Cu1—N1—C7—C62.9 (10)C14—C15—C20—O24.0 (11)
C5—C6—C7—N1176.8 (7)C16—C15—C20—O2179.4 (6)
C1—C6—C7—N10.1 (11)C14—C15—C20—C19177.3 (6)
C7—N1—C8—C96.5 (11)C16—C15—C20—C190.6 (10)
Cu1—N1—C8—C9176.7 (6)C18—C19—C20—O2178.6 (7)
C7—N1—C8—C13175.8 (6)C18—C19—C20—C150.2 (11)
Cu1—N1—C8—C131.0 (7)
 

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