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The title complex, [Cu(C21H14NO)2], possesses a crystallographically imposed center of symmetry. The CuII atom is coordinated by the two bidentate ligands in a trans arrangement, forming a CuN2O2 square-planar configuration, with Cu—O and Cu—N bond lengths of 1.871 (3) and 1.981 (3) Å, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701152X/cv2211sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701152X/cv2211Isup2.hkl
Contains datablock I

CCDC reference: 642963

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.061
  • wR factor = 0.212
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 3 N1 -CU1 -N1 -C1 4.00 0.00 3.567 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6 N1 -CU1 -N1 -C12 15.00 0.00 3.567 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 7 O1 -CU1 -O1 -C3 0.00 0.00 3.567 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); 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.

Bis[1-(1-naphthyliminomethyl)2-naphtholato-κ2N,O)copper(II) top
Crystal data top
[Cu(C21H14NO)2]F(000) = 678
Mr = 656.20Dx = 1.421 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.958 (4) ÅCell parameters from 1552 reflections
b = 14.5062 (17) Åθ = 2.2–20.8°
c = 12.515 (9) ŵ = 0.75 mm1
β = 109.405 (19)°T = 298 K
V = 1534.0 (12) Å3Prism, blue
Z = 20.27 × 0.21 × 0.12 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3581 independent reflections
Radiation source: fine-focus sealed tube1635 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
φ and ω scansθmax = 28.2°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.822, Tmax = 0.915k = 1916
9233 measured reflectionsl = 1616
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.212H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.1038P)2]
where P = (Fo2 + 2Fc2)/3
3581 reflections(Δ/σ)max < 0.001
214 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.54 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
Cu10.00000.50001.00000.0475 (3)
N10.1476 (5)0.3945 (3)1.0218 (3)0.0510 (10)
O10.0347 (4)0.4994 (2)0.8441 (3)0.0551 (9)
C10.1721 (6)0.3471 (3)0.9409 (4)0.0517 (13)
H10.24100.29740.96280.062*
C20.1040 (5)0.3636 (3)0.8219 (3)0.0403 (10)
C30.0045 (5)0.4394 (3)0.7813 (4)0.0457 (11)
C40.0578 (6)0.4551 (4)0.6610 (4)0.0536 (13)
H40.12210.50600.63330.064*
C50.0245 (6)0.3974 (4)0.5884 (4)0.0554 (13)
H50.06890.40860.51110.067*
C60.0759 (6)0.3202 (3)0.6253 (4)0.0478 (12)
C70.1392 (6)0.3010 (3)0.7431 (4)0.0457 (11)
C80.2369 (6)0.2230 (4)0.7754 (4)0.0580 (14)
H80.27930.20830.85190.070*
C90.2715 (8)0.1682 (4)0.6984 (5)0.0734 (17)
H90.33570.11680.72330.088*
C100.2125 (8)0.1880 (4)0.5830 (5)0.0730 (17)
H100.23960.15180.53080.088*
C110.1139 (7)0.2617 (4)0.5487 (4)0.0649 (16)
H110.07010.27380.47160.078*
C120.2285 (6)0.3617 (3)1.1354 (4)0.0487 (12)
C130.1791 (7)0.2869 (4)1.1766 (4)0.0601 (14)
H130.09850.25141.12780.072*
C140.2435 (7)0.2597 (4)1.2902 (4)0.0639 (15)
H140.20640.20701.31560.077*
C150.3607 (7)0.3109 (5)1.3628 (4)0.0710 (17)
H150.40130.29471.43890.085*
C160.4219 (6)0.3903 (4)1.3219 (4)0.0558 (13)
C170.3519 (5)0.4133 (3)1.2059 (4)0.0491 (12)
C180.4170 (7)0.4927 (4)1.1643 (6)0.0712 (16)
H180.37820.50931.08820.085*
C190.5368 (8)0.5422 (5)1.2399 (7)0.088 (2)
H190.57670.59391.21480.106*
C200.5993 (9)0.5168 (6)1.3527 (8)0.105 (3)
H200.68280.55041.40140.126*
C210.5412 (7)0.4447 (6)1.3925 (6)0.090 (2)
H210.58170.43081.46930.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0449 (5)0.0629 (6)0.0340 (4)0.0123 (4)0.0121 (3)0.0014 (4)
N10.049 (2)0.070 (3)0.033 (2)0.009 (2)0.0125 (18)0.0016 (19)
O10.065 (2)0.066 (2)0.0357 (17)0.0211 (18)0.0182 (16)0.0030 (17)
C10.049 (3)0.065 (3)0.041 (3)0.012 (2)0.015 (2)0.004 (2)
C20.032 (2)0.056 (3)0.033 (2)0.005 (2)0.0115 (19)0.003 (2)
C30.043 (3)0.055 (3)0.039 (2)0.003 (2)0.013 (2)0.002 (2)
C40.056 (3)0.065 (3)0.040 (3)0.015 (3)0.015 (2)0.007 (2)
C50.060 (3)0.067 (3)0.033 (2)0.000 (3)0.007 (2)0.000 (2)
C60.049 (3)0.054 (3)0.040 (2)0.004 (2)0.014 (2)0.004 (2)
C70.045 (3)0.050 (3)0.043 (2)0.001 (2)0.017 (2)0.004 (2)
C80.062 (3)0.066 (4)0.049 (3)0.013 (3)0.024 (3)0.005 (3)
C90.087 (4)0.061 (4)0.077 (4)0.018 (3)0.035 (4)0.004 (3)
C100.086 (4)0.073 (4)0.063 (4)0.003 (3)0.029 (3)0.021 (3)
C110.069 (4)0.079 (4)0.047 (3)0.004 (3)0.021 (3)0.012 (3)
C120.047 (3)0.057 (3)0.045 (3)0.007 (2)0.018 (2)0.006 (2)
C130.066 (4)0.063 (3)0.049 (3)0.003 (3)0.017 (3)0.004 (3)
C140.070 (4)0.071 (4)0.052 (3)0.009 (3)0.022 (3)0.019 (3)
C150.067 (4)0.099 (5)0.045 (3)0.026 (3)0.015 (3)0.007 (3)
C160.041 (3)0.082 (4)0.043 (3)0.013 (3)0.012 (2)0.008 (3)
C170.037 (3)0.061 (3)0.047 (3)0.008 (2)0.010 (2)0.006 (2)
C180.053 (3)0.073 (4)0.086 (4)0.006 (3)0.021 (3)0.008 (3)
C190.060 (4)0.077 (4)0.133 (7)0.019 (4)0.038 (4)0.009 (5)
C200.063 (5)0.125 (7)0.109 (7)0.013 (4)0.005 (5)0.033 (5)
C210.055 (4)0.131 (7)0.073 (4)0.001 (4)0.005 (3)0.033 (4)
Geometric parameters (Å, º) top
Cu1—O1i1.871 (3)C9—H90.9300
Cu1—O11.871 (3)C10—C111.363 (7)
Cu1—N1i1.981 (4)C10—H100.9300
Cu1—N11.981 (4)C11—H110.9300
N1—C11.301 (6)C12—C131.339 (7)
N1—C121.445 (6)C12—C171.382 (6)
O1—C31.297 (5)C13—C141.401 (7)
C1—C21.430 (6)C13—H130.9300
C1—H10.9300C14—C151.358 (7)
C2—C31.400 (6)C14—H140.9300
C2—C71.451 (6)C15—C161.441 (8)
C3—C41.439 (6)C15—H150.9300
C4—C51.339 (7)C16—C211.385 (8)
C4—H40.9300C16—C171.417 (6)
C5—C61.415 (7)C17—C181.463 (7)
C5—H50.9300C18—C191.374 (8)
C6—C111.404 (6)C18—H180.9300
C6—C71.420 (6)C19—C201.385 (10)
C7—C81.405 (7)C19—H190.9300
C8—C91.362 (7)C20—C211.336 (10)
C8—H80.9300C20—H200.9300
C9—C101.393 (7)C21—H210.9300
O1i—Cu1—O1180.000 (1)C11—C10—C9118.1 (5)
O1i—Cu1—N1i90.69 (14)C11—C10—H10121.0
O1—Cu1—N190.69 (14)C9—C10—H10121.0
O1—Cu1—N1i89.31 (14)C10—C11—C6122.6 (5)
O1i—Cu1—N189.31 (14)C10—C11—H11118.7
N1i—Cu1—N1180.000 (2)C6—C11—H11118.7
C1—N1—C12115.6 (4)C13—C12—C17119.3 (5)
C1—N1—Cu1125.3 (3)C13—C12—N1121.6 (5)
C12—N1—Cu1118.9 (3)C17—C12—N1118.9 (4)
C3—O1—Cu1130.6 (3)C12—C13—C14122.8 (5)
N1—C1—C2126.8 (4)C12—C13—H13118.6
N1—C1—H1116.6C14—C13—H13118.6
C2—C1—H1116.6C15—C14—C13119.4 (5)
C3—C2—C1120.6 (4)C15—C14—H14120.3
C3—C2—C7120.1 (4)C13—C14—H14120.3
C1—C2—C7119.3 (4)C14—C15—C16120.0 (5)
O1—C3—C2125.1 (4)C14—C15—H15120.0
O1—C3—C4116.0 (4)C16—C15—H15120.0
C2—C3—C4118.9 (4)C21—C16—C17120.3 (6)
C5—C4—C3121.0 (5)C21—C16—C15122.2 (6)
C5—C4—H4119.5C17—C16—C15117.5 (5)
C3—C4—H4119.5C12—C17—C16120.9 (5)
C4—C5—C6122.3 (4)C12—C17—C18121.9 (5)
C4—C5—H5118.9C16—C17—C18117.2 (5)
C6—C5—H5118.9C19—C18—C17118.6 (6)
C11—C6—C5121.9 (4)C19—C18—H18120.7
C11—C6—C7119.1 (5)C17—C18—H18120.7
C5—C6—C7119.0 (4)C18—C19—C20121.5 (7)
C8—C7—C6116.9 (4)C18—C19—H19119.3
C8—C7—C2124.3 (4)C20—C19—H19119.3
C6—C7—C2118.7 (4)C21—C20—C19120.8 (7)
C9—C8—C7122.2 (5)C21—C20—H20119.6
C9—C8—H8118.9C19—C20—H20119.6
C7—C8—H8118.9C20—C21—C16121.5 (7)
C8—C9—C10121.1 (5)C20—C21—H21119.2
C8—C9—H9119.4C16—C21—H21119.2
C10—C9—H9119.4
O1i—Cu1—N1—C1172.2 (4)C6—C7—C8—C90.6 (8)
O1—Cu1—N1—C17.8 (4)C2—C7—C8—C9177.3 (5)
N1i—Cu1—N1—C140 (100)C7—C8—C9—C100.8 (9)
O1i—Cu1—N1—C123.3 (4)C8—C9—C10—C112.5 (9)
O1—Cu1—N1—C12176.7 (4)C9—C10—C11—C62.9 (9)
N1i—Cu1—N1—C12145 (100)C5—C6—C11—C10178.9 (5)
O1i—Cu1—O1—C30 (100)C7—C6—C11—C101.5 (8)
N1i—Cu1—O1—C3169.0 (4)C1—N1—C12—C1375.5 (6)
N1—Cu1—O1—C311.0 (4)Cu1—N1—C12—C13100.5 (5)
C12—N1—C1—C2178.6 (4)C1—N1—C12—C17109.8 (5)
Cu1—N1—C1—C22.9 (8)Cu1—N1—C12—C1774.3 (5)
N1—C1—C2—C32.9 (8)C17—C12—C13—C142.3 (8)
N1—C1—C2—C7177.2 (5)N1—C12—C13—C14172.4 (5)
Cu1—O1—C3—C28.9 (7)C12—C13—C14—C150.3 (9)
Cu1—O1—C3—C4172.7 (3)C13—C14—C15—C162.5 (8)
C1—C2—C3—O10.2 (7)C14—C15—C16—C21180.0 (5)
C7—C2—C3—O1179.9 (4)C14—C15—C16—C172.0 (8)
C1—C2—C3—C4178.2 (4)C13—C12—C17—C162.7 (7)
C7—C2—C3—C41.8 (7)N1—C12—C17—C16172.1 (4)
O1—C3—C4—C5179.9 (5)C13—C12—C17—C18176.5 (5)
C2—C3—C4—C51.4 (8)N1—C12—C17—C188.7 (7)
C3—C4—C5—C61.7 (8)C21—C16—C17—C12177.4 (5)
C4—C5—C6—C11178.1 (5)C15—C16—C17—C120.6 (7)
C4—C5—C6—C72.4 (8)C21—C16—C17—C183.4 (7)
C11—C6—C7—C80.2 (7)C15—C16—C17—C18178.6 (5)
C5—C6—C7—C8179.3 (5)C12—C17—C18—C19178.2 (5)
C11—C6—C7—C2177.8 (5)C16—C17—C18—C192.6 (8)
C5—C6—C7—C22.7 (7)C17—C18—C19—C202.0 (10)
C3—C2—C7—C8179.7 (5)C18—C19—C20—C212.2 (12)
C1—C2—C7—C80.3 (7)C19—C20—C21—C163.0 (12)
C3—C2—C7—C62.4 (7)C17—C16—C21—C203.7 (10)
C1—C2—C7—C6177.5 (4)C15—C16—C21—C20178.4 (7)
Symmetry code: (i) x, y+1, z+2.
 

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