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The title compound, [Cu(C15H14NO)2], adopts a stepped conformation and displays a square-planar trans-[CuN2O2] coordination geometry. The asymmetric unit contains two independent half mol­ecules and each Cu atom is located on a center of symmetry. For one mol­ecule, the Cu—N and Cu—O bond distances are 2.013 (2) and 1.893 (2) Å, respectively, while for the other mol­ecule, these distances are 2.008 (2) and 1.896 (2) Å. The extended conformation of the phenethyl­imine pendant groups results in crystal packing formed by weakly aggregated planar mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023736/ac6123sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023736/ac6123Isup2.hkl
Contains datablock I

CCDC reference: 255398

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.033
  • wR factor = 0.104
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT156_ALERT_4_C Axial System Input Cell not Standard ........... ? PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
[Cu(C15H14NO)2]Z = 2
Mr = 512.09F(000) = 534.0
Triclinic, P1Dx = 1.354 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 11.943 (4) ÅCell parameters from 25 reflections
b = 11.944 (5) Åθ = 11.0–12.5°
c = 9.102 (3) ŵ = 0.90 mm1
α = 89.81 (3)°T = 298 K
β = 91.89 (3)°Block, brown
γ = 75.43 (3)°0.20 × 0.20 × 0.15 mm
V = 1255.9 (8) Å3
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.028
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 1515
Tmin = 0.835, Tmax = 0.874k = 1515
6444 measured reflectionsl = 114
5773 independent reflections3 standard reflections every 150 reflections
4237 reflections with I > 2σ(I) intensity decay: 0.9%
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.0553P)2 + 0.2726P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.104(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.41 e Å3
4237 reflectionsΔρmin = 0.46 e Å3
320 parameters
Special details top

Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.00000.00000.00000.0410 (1)
Cu20.00000.50000.50000.0418 (1)
O10.1000 (2)0.0348 (2)0.1688 (2)0.0596 (4)
O20.0998 (2)0.5165 (1)0.3307 (2)0.0607 (4)
N10.0450 (1)0.1498 (1)0.0299 (2)0.0402 (3)
N20.0452 (1)0.6718 (1)0.5301 (2)0.0407 (3)
C10.2118 (2)0.1040 (2)0.1410 (2)0.0407 (4)
C20.1893 (2)0.0049 (2)0.2057 (2)0.0419 (4)
C30.2666 (2)0.0519 (2)0.3192 (3)0.0516 (5)
C40.3612 (2)0.0138 (2)0.3629 (3)0.0575 (6)
C50.3841 (2)0.0829 (3)0.2975 (3)0.0645 (6)
C60.3098 (2)0.1408 (2)0.1887 (3)0.0545 (5)
C70.1346 (2)0.1730 (2)0.0313 (2)0.0415 (4)
C80.0256 (2)0.2396 (2)0.1305 (2)0.0433 (4)
C90.1326 (2)0.3066 (2)0.0540 (3)0.0605 (6)
C100.2161 (2)0.3872 (2)0.1586 (2)0.0477 (5)
C110.1926 (2)0.4866 (2)0.2124 (3)0.0580 (5)
C120.2691 (3)0.5575 (2)0.3126 (3)0.0701 (7)
C130.3686 (3)0.5290 (3)0.3583 (3)0.0805 (9)
C140.3928 (3)0.4317 (3)0.3049 (4)0.0852 (9)
C150.3171 (2)0.3612 (2)0.2060 (3)0.0634 (6)
C160.2125 (2)0.7107 (2)0.3596 (2)0.0412 (4)
C170.1900 (2)0.6011 (2)0.2951 (2)0.0437 (4)
C180.2672 (2)0.5829 (2)0.1820 (3)0.0531 (5)
C190.3629 (2)0.6689 (2)0.1405 (3)0.0612 (6)
C200.3863 (2)0.7759 (2)0.2056 (3)0.0668 (7)
C210.3117 (2)0.7968 (2)0.3136 (3)0.0567 (5)
C220.1352 (2)0.7405 (2)0.4689 (2)0.0430 (4)
C230.0250 (2)0.7260 (2)0.6305 (2)0.0442 (4)
C240.1312 (2)0.7415 (2)0.5539 (3)0.0596 (6)
C250.2135 (2)0.7803 (2)0.6587 (2)0.0465 (5)
C260.3144 (2)0.7033 (2)0.7089 (3)0.0608 (6)
C270.3890 (2)0.7348 (3)0.8086 (4)0.0806 (8)
C280.3650 (3)0.8445 (3)0.8608 (3)0.0796 (9)
C290.2663 (3)0.9236 (3)0.8129 (3)0.0717 (8)
C300.1900 (2)0.8919 (2)0.7110 (3)0.0586 (6)
H10.25260.11810.36620.0621*
H20.41200.05430.43910.0694*
H30.45030.10860.32800.0779*
H40.32500.20740.14420.0655*
H50.15200.24290.00130.0501*
H60.04840.20380.21550.0523*
H70.01900.29120.15860.0523*
H80.10950.35070.02250.0729*
H90.17050.25330.01330.0729*
H100.12380.50680.18090.0697*
H110.25210.62570.34950.0844*
H120.42070.57720.42720.0967*
H130.46200.41210.33630.1025*
H140.33520.29350.16920.0760*
H150.25250.51040.13400.0642*
H160.41430.65410.06540.0737*
H170.45340.83450.17610.0804*
H180.32690.87060.35840.0683*
H190.15260.81900.49890.0518*
H200.02020.79930.65950.0535*
H210.04880.67770.71490.0535*
H220.17000.66980.51270.0717*
H230.10730.79780.47780.0717*
H240.33240.62630.67310.0732*
H250.45770.67970.84140.0970*
H260.41680.86610.93040.0955*
H270.24981.00030.84940.0864*
H280.12180.94720.67780.0704*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0358 (2)0.0481 (2)0.0405 (2)0.0149 (1)0.0101 (1)0.0113 (1)
Cu20.0364 (2)0.0447 (2)0.0410 (2)0.0056 (1)0.0094 (1)0.0067 (1)
O10.0580 (9)0.070 (1)0.0582 (9)0.0343 (8)0.0263 (8)0.0270 (8)
O20.0596 (10)0.0521 (9)0.0593 (10)0.0032 (7)0.0271 (8)0.0141 (7)
N10.0376 (8)0.0439 (8)0.0375 (8)0.0080 (6)0.0025 (6)0.0079 (6)
N20.0379 (8)0.0483 (9)0.0374 (8)0.0139 (7)0.0023 (7)0.0067 (7)
C10.0369 (9)0.048 (1)0.0381 (10)0.0120 (8)0.0029 (7)0.0013 (8)
C20.0377 (10)0.049 (1)0.0393 (10)0.0122 (8)0.0076 (8)0.0023 (8)
C30.050 (1)0.056 (1)0.048 (1)0.0140 (10)0.0147 (9)0.0084 (9)
C40.045 (1)0.073 (1)0.051 (1)0.010 (1)0.0168 (10)0.004 (1)
C50.051 (1)0.090 (2)0.058 (1)0.031 (1)0.017 (1)0.005 (1)
C60.051 (1)0.067 (1)0.052 (1)0.028 (1)0.0068 (10)0.003 (1)
C70.042 (1)0.0425 (10)0.0404 (10)0.0119 (8)0.0000 (8)0.0031 (8)
C80.044 (1)0.047 (1)0.0379 (10)0.0085 (8)0.0025 (8)0.0101 (8)
C90.055 (1)0.071 (2)0.042 (1)0.009 (1)0.0042 (10)0.013 (1)
C100.047 (1)0.050 (1)0.038 (1)0.0010 (9)0.0035 (8)0.0052 (8)
C110.061 (1)0.059 (1)0.053 (1)0.014 (1)0.003 (1)0.003 (1)
C120.087 (2)0.052 (1)0.062 (2)0.000 (1)0.016 (1)0.018 (1)
C130.065 (2)0.092 (2)0.064 (2)0.017 (2)0.002 (1)0.025 (1)
C140.053 (2)0.113 (3)0.084 (2)0.012 (2)0.016 (1)0.014 (2)
C150.056 (1)0.063 (1)0.070 (2)0.013 (1)0.001 (1)0.008 (1)
C160.0380 (10)0.046 (1)0.0384 (10)0.0092 (8)0.0029 (8)0.0023 (8)
C170.040 (1)0.048 (1)0.041 (1)0.0096 (8)0.0075 (8)0.0031 (8)
C180.052 (1)0.057 (1)0.049 (1)0.0142 (10)0.0144 (10)0.0005 (9)
C190.049 (1)0.078 (2)0.054 (1)0.015 (1)0.019 (1)0.006 (1)
C200.053 (1)0.074 (2)0.062 (2)0.004 (1)0.018 (1)0.005 (1)
C210.054 (1)0.054 (1)0.054 (1)0.000 (1)0.008 (1)0.0005 (10)
C220.045 (1)0.0433 (10)0.042 (1)0.0121 (8)0.0004 (8)0.0033 (8)
C230.046 (1)0.051 (1)0.0382 (10)0.0171 (9)0.0020 (8)0.0102 (8)
C240.055 (1)0.091 (2)0.042 (1)0.035 (1)0.0020 (10)0.015 (1)
C250.046 (1)0.063 (1)0.0380 (10)0.0260 (10)0.0040 (8)0.0074 (9)
C260.054 (1)0.066 (1)0.064 (1)0.017 (1)0.001 (1)0.008 (1)
C270.051 (1)0.115 (3)0.074 (2)0.018 (2)0.011 (1)0.009 (2)
C280.061 (2)0.133 (3)0.061 (2)0.053 (2)0.000 (1)0.025 (2)
C290.090 (2)0.076 (2)0.065 (2)0.048 (2)0.020 (1)0.027 (1)
C300.061 (1)0.060 (1)0.056 (1)0.018 (1)0.006 (1)0.004 (1)
Geometric parameters (Å, º) top
Cu1—O11.893 (2)C12—C131.369 (5)
Cu1—O1i1.893 (2)C12—H110.950
Cu1—N12.013 (2)C13—C141.359 (5)
Cu1—N1i2.013 (2)C13—H120.950
Cu2—O21.896 (2)C14—C151.376 (4)
Cu2—O2ii1.896 (2)C14—H130.950
Cu2—N22.008 (2)C15—H140.950
Cu2—N2ii2.008 (2)C16—C171.403 (3)
O1—C21.306 (3)C16—C211.410 (3)
O2—C171.308 (2)C16—C221.442 (3)
N1—C71.283 (3)C17—C181.412 (3)
N1—C81.479 (2)C18—C191.372 (3)
N2—C221.286 (2)C18—H150.950
N2—C231.477 (3)C19—C201.378 (4)
C1—C21.409 (3)C19—H160.950
C1—C61.407 (3)C20—C211.370 (4)
C1—C71.441 (3)C20—H170.950
C2—C31.413 (3)C21—H180.950
C3—C41.368 (4)C22—H190.950
C3—H10.950C23—C241.518 (4)
C4—C51.389 (4)C23—H200.950
C4—H20.950C23—H210.950
C5—C61.369 (3)C24—C251.504 (4)
C5—H30.950C24—H220.950
C6—H40.950C24—H230.950
C7—H50.950C25—C261.382 (3)
C8—C91.518 (3)C25—C301.381 (3)
C8—H60.950C26—C271.370 (4)
C8—H70.950C26—H240.950
C9—C101.509 (3)C27—C281.359 (5)
C9—H80.950C27—H250.950
C9—H90.950C28—C291.369 (4)
C10—C111.378 (4)C28—H260.950
C10—C151.376 (4)C29—C301.398 (4)
C11—C121.391 (4)C29—H270.950
C11—H100.950C30—H280.950
O1—Cu1—O1i180.0C13—C12—H11120.0
O1—Cu1—N190.68 (7)C12—C13—C14119.8 (3)
O1—Cu1—N1i89.32 (7)C12—C13—H12120.1
O1i—Cu1—N189.32 (7)C14—C13—H12120.1
O1i—Cu1—N1i90.68 (7)C13—C14—C15120.2 (3)
N1—Cu1—N1i180.0C13—C14—H13119.8
O2—Cu2—O2ii180.0C15—C14—H13119.9
O2—Cu2—N290.66 (7)C10—C15—C14121.2 (3)
O2—Cu2—N2ii89.34 (7)C10—C15—H14119.3
O2ii—Cu2—N289.34 (7)C14—C15—H14119.4
O2ii—Cu2—N2ii90.66 (7)C17—C16—C21119.7 (2)
N2—Cu2—N2ii180.0C17—C16—C22122.2 (2)
Cu1—O1—C2129.1 (1)C21—C16—C22118.1 (2)
Cu2—O2—C17128.8 (1)O2—C17—C16123.7 (2)
Cu1—N1—C7123.9 (1)O2—C17—C18118.5 (2)
Cu1—N1—C8119.9 (1)C16—C17—C18117.8 (2)
C7—N1—C8116.1 (2)C17—C18—C19120.8 (2)
Cu2—N2—C22124.0 (1)C17—C18—H15119.6
Cu2—N2—C23120.1 (1)C19—C18—H15119.6
C22—N2—C23115.9 (2)C18—C19—C20121.5 (2)
C2—C1—C6119.5 (2)C18—C19—H16119.2
C2—C1—C7122.2 (2)C20—C19—H16119.4
C6—C1—C7118.2 (2)C19—C20—C21119.1 (2)
O1—C2—C1123.5 (2)C19—C20—H17120.5
O1—C2—C3118.9 (2)C21—C20—H17120.4
C1—C2—C3117.5 (2)C16—C21—C20121.2 (2)
C2—C3—C4121.4 (2)C16—C21—H18119.3
C2—C3—H1119.3C20—C21—H18119.5
C4—C3—H1119.3N2—C22—C16126.6 (2)
C3—C4—C5120.9 (2)N2—C22—H19116.7
C3—C4—H2119.5C16—C22—H19116.7
C5—C4—H2119.6N2—C23—C24110.1 (2)
C4—C5—C6119.0 (3)N2—C23—H20109.4
C4—C5—H3120.5N2—C23—H21109.2
C6—C5—H3120.5C24—C23—H20109.3
C1—C6—C5121.5 (2)C24—C23—H21109.3
C1—C6—H4119.3H20—C23—H21109.5
C5—C6—H4119.2C23—C24—C25111.7 (2)
N1—C7—C1126.7 (2)C23—C24—H22108.9
N1—C7—H5116.7C23—C24—H23108.9
C1—C7—H5116.7C25—C24—H22108.9
N1—C8—C9109.9 (2)C25—C24—H23109.0
N1—C8—H6109.4H22—C24—H23109.4
N1—C8—H7109.4C24—C25—C26120.4 (2)
C9—C8—H6109.4C24—C25—C30121.7 (2)
C9—C8—H7109.4C26—C25—C30117.9 (2)
H6—C8—H7109.5C25—C26—C27121.8 (2)
C8—C9—C10111.9 (2)C25—C26—H24119.0
C8—C9—H8108.9C27—C26—H24119.2
C8—C9—H9108.9C26—C27—C28120.1 (3)
C10—C9—H8108.8C26—C27—H25119.8
C10—C9—H9108.8C28—C27—H25120.0
H8—C9—H9109.5C27—C28—C29119.8 (3)
C9—C10—C11121.5 (2)C27—C28—H26119.9
C9—C10—C15120.3 (2)C29—C28—H26120.2
C11—C10—C15118.2 (2)C28—C29—C30120.3 (3)
C10—C11—C12120.5 (3)C28—C29—H27119.7
C10—C11—H10119.8C30—C29—H27120.0
C12—C11—H10119.7C25—C30—C29120.1 (2)
C11—C12—C13120.0 (3)C25—C30—H28120.0
C11—C12—H11120.0C29—C30—H28119.9
Cu1—O1—C2—C115.9 (3)C1—C6—C5—C40.6 (4)
Cu1—O1—C2—C3165.9 (1)C1—C7—N1—C8175.1 (2)
Cu1—O1i—C2i—C1i15.9 (3)C2—C1—C6—C50.3 (3)
Cu1—O1i—C2i—C3i165.9 (1)C2—C3—C4—C50.4 (3)
Cu1—N1—C7—C16.5 (3)C3—C2—C1—C61.3 (3)
Cu1—N1—C8—C979.6 (2)C3—C2—C1—C7175.8 (2)
Cu1—N1i—C7i—C1i6.5 (3)C3—C4—C5—C60.6 (4)
Cu1—N1i—C8i—C9i79.6 (2)C5—C6—C1—C7176.9 (2)
Cu2—O2—C17—C1616.9 (3)C7—N1—C8—C9101.9 (2)
Cu2—O2—C17—C18165.3 (2)C8—C9—C10—C1172.1 (3)
Cu2—O2ii—C17ii—C16ii16.9 (3)C8—C9—C10—C15106.1 (3)
Cu2—O2ii—C17ii—C18ii165.3 (2)C9—C10—C11—C12177.8 (2)
Cu2—N2—C22—C166.2 (3)C9—C10—C15—C14178.0 (2)
Cu2—N2—C23—C2480.2 (2)C10—C11—C12—C130.2 (4)
Cu2—N2ii—C22ii—C16ii6.2 (3)C10—C15—C14—C130.2 (5)
Cu2—N2ii—C23ii—C24ii80.2 (2)C11—C10—C15—C140.3 (4)
O1—Cu1—N1—C716.5 (2)C11—C12—C13—C140.3 (4)
O1—Cu1—N1—C8165.2 (1)C12—C11—C10—C150.5 (3)
O1—Cu1—N1i—C7i163.5 (2)C12—C13—C14—C150.5 (5)
O1—Cu1—N1i—C8i14.8 (1)C16—C17—C18—C192.0 (4)
O1—C2—C1—C6179.5 (2)C16—C21—C20—C190.6 (4)
O1—C2—C1—C72.4 (3)C16—C22—N2—C23175.3 (2)
O1—C2—C3—C4179.7 (2)C17—C16—C21—C200.6 (4)
O2—Cu2—N2—C2216.6 (2)C17—C18—C19—C200.9 (4)
O2—Cu2—N2—C23164.9 (1)C18—C17—C16—C211.9 (3)
O2—Cu2—N2ii—C22ii163.4 (2)C18—C17—C16—C22175.9 (2)
O2—Cu2—N2ii—C23ii15.1 (1)C18—C19—C20—C210.4 (4)
O2—C17—C16—C21179.7 (2)C20—C21—C16—C22177.2 (2)
O2—C17—C16—C221.9 (3)C22—N2—C23—C24101.2 (2)
O2—C17—C18—C19180.0 (2)C23—C24—C25—C26104.5 (3)
N1—Cu1—O1—C221.6 (2)C23—C24—C25—C3073.7 (3)
N1—Cu1—O1i—C2i158.4 (2)C24—C25—C26—C27177.5 (3)
N1—C7—C1—C26.6 (3)C24—C25—C30—C29177.4 (2)
N1—C7—C1—C6176.3 (2)C25—C26—C27—C280.2 (5)
N1—C8—C9—C10171.6 (2)C25—C30—C29—C280.3 (4)
N2—Cu2—O2—C1722.4 (2)C26—C25—C30—C290.8 (4)
N2—Cu2—O2ii—C17ii157.6 (2)C26—C27—C28—C290.3 (5)
N2—C22—C16—C176.9 (4)C27—C26—C25—C300.7 (4)
N2—C22—C16—C21175.4 (2)C27—C28—C29—C300.3 (5)
N2—C23—C24—C25171.7 (2)C27—C28—C29—C300.3 (5)
C1—C2—C3—C41.3 (3)
Symmetry codes: (i) x, y, z; (ii) x, y+1, z+1.
 

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