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The title complex, [Cu(C28H20N4O2)], can be described as a single-stranded helix with the CuII atom having a distorted square-planar coordination. Face-to-face and edge-to-face π–π stacking inter­actions and a C—H...π inter­action between the aromatic rings lead to a three-dimensional network in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025128/is2037sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025128/is2037Isup2.hkl
Contains datablock I

CCDC reference: 618242

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.056
  • wR factor = 0.128
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

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Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.668 0.863 Tmin(prime) and Tmax expected: 0.818 0.863 RR(prime) = 0.816 Please check that your absorption correction is appropriate. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.81 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.38 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT480_ALERT_4_C Long H...A H-Bond Reported H24A .. CG .. 3.05 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 4 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, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

{Benzil bis[(2-oxidobenzylidene)hydrazone]}copper(II) top
Crystal data top
[Cu(C28H20N4O2)]Z = 2
Mr = 508.02F(000) = 522
Triclinic, P1Dx = 1.463 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.223 (2) ÅCell parameters from 993 reflections
b = 10.702 (2) Åθ = 2.5–20.0°
c = 12.720 (3) ŵ = 0.98 mm1
α = 85.132 (5)°T = 293 K
β = 89.749 (5)°Block, green
γ = 67.273 (4)°0.20 × 0.15 × 0.15 mm
V = 1153.3 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3934 independent reflections
Radiation source: fine-focus sealed tube2605 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 910
Tmin = 0.668, Tmax = 0.863k = 1012
5694 measured reflectionsl = 1415
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.03 [exp{2(sinθ/λ}2)]/[σ2(Fo2) + (0.045P)2]
where P = (Fo2 + 2Fc2)/3
3934 reflections(Δ/σ)max < 0.001
316 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. IR data (KBr, cm-1): 3442(m), 1605(s), 1581(s), 1524(s), 1490(m), 1465(s), 1442(s), 1370(s), 1350(m), 1318(s), 1249(m), 1199(s), 1149(s), 1130(m), 1027(m), 1002(m), 963(m), 910(s), 859(m), 805(m), 760(s), 731(m), 687(s), 662(m), 645(m), 605(m), 576(m), 504(m), 474(m), 450(m).

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
Cu10.77899 (6)0.84963 (6)0.33518 (5)0.0375 (2)
O10.6134 (3)0.7995 (3)0.3842 (2)0.0387 (8)
O20.9386 (4)0.6909 (3)0.3968 (3)0.0477 (9)
N10.6501 (4)1.0427 (4)0.3268 (3)0.0341 (9)
N20.7260 (4)1.1346 (4)0.3103 (3)0.0371 (9)
N30.8231 (4)0.9396 (4)0.1216 (3)0.0386 (9)
N40.9060 (4)0.8604 (4)0.2118 (3)0.0339 (9)
C10.4662 (5)0.8791 (5)0.3916 (3)0.0313 (10)
C20.3542 (6)0.8210 (5)0.4114 (4)0.0415 (12)
H2A0.38680.72680.41800.050*
C30.1999 (6)0.8996 (6)0.4210 (4)0.0497 (14)
H3B0.12900.85770.43270.060*
C40.1450 (6)1.0387 (6)0.4140 (4)0.0531 (14)
H4A0.03901.09070.42220.064*
C50.2500 (5)1.0997 (5)0.3945 (4)0.0472 (13)
H5A0.21451.19400.39010.057*
C60.4098 (5)1.0221 (5)0.3810 (3)0.0354 (11)
C70.5086 (6)1.0939 (5)0.3547 (3)0.0378 (11)
H7A0.46501.18760.35840.045*
C80.7804 (5)1.1396 (4)0.2187 (3)0.0306 (10)
C90.8698 (5)1.2289 (4)0.1973 (3)0.0349 (11)
C100.8593 (5)1.3278 (5)0.2636 (4)0.0454 (13)
H10A0.79561.33980.32180.054*
C110.9440 (6)1.4089 (6)0.2429 (5)0.0609 (16)
H11A0.93641.47640.28650.073*
C121.0392 (7)1.3890 (6)0.1574 (6)0.0729 (19)
H12A1.09631.44340.14380.087*
C131.0516 (7)1.2906 (6)0.0921 (5)0.0698 (18)
H13A1.11671.27800.03450.084*
C140.9671 (6)1.2103 (5)0.1119 (4)0.0520 (14)
H14A0.97531.14310.06770.062*
C150.7545 (5)1.0672 (5)0.1292 (3)0.0338 (11)
C160.6410 (5)1.1493 (5)0.0436 (4)0.0362 (11)
C170.5410 (6)1.2805 (5)0.0547 (4)0.0528 (14)
H17A0.55011.32180.11440.063*
C180.4271 (7)1.3520 (6)0.0218 (5)0.0657 (17)
H18A0.35851.44040.01260.079*
C190.4142 (7)1.2946 (7)0.1101 (5)0.0676 (18)
H19A0.33821.34410.16200.081*
C200.5129 (7)1.1639 (7)0.1233 (5)0.0739 (19)
H20A0.50291.12360.18330.089*
C210.6267 (6)1.0926 (6)0.0477 (4)0.0573 (15)
H21A0.69561.00460.05780.069*
C221.0433 (5)0.7717 (5)0.1956 (4)0.0395 (12)
H22A1.08380.77690.12900.047*
C231.1394 (5)0.6651 (4)0.2715 (4)0.0390 (12)
C241.2945 (6)0.5923 (5)0.2449 (5)0.0523 (14)
H24A1.33030.61330.18000.063*
C251.3940 (6)0.4905 (6)0.3135 (5)0.0656 (17)
H25A1.49810.44380.29630.079*
C261.3392 (6)0.4576 (5)0.4084 (5)0.0580 (15)
H26A1.40710.38860.45530.070*
C271.1875 (6)0.5245 (5)0.4342 (4)0.0505 (14)
H27A1.15290.49850.49800.061*
C281.0821 (5)0.6310 (5)0.3683 (4)0.0391 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0362 (3)0.0343 (3)0.0409 (4)0.0136 (3)0.0015 (3)0.0013 (2)
O10.0341 (18)0.0343 (19)0.050 (2)0.0168 (15)0.0055 (15)0.0009 (15)
O20.0393 (19)0.042 (2)0.055 (2)0.0112 (16)0.0034 (17)0.0116 (16)
N10.034 (2)0.027 (2)0.041 (2)0.0121 (17)0.0007 (18)0.0023 (17)
N20.042 (2)0.034 (2)0.040 (2)0.0205 (18)0.0007 (19)0.0023 (18)
N30.045 (2)0.034 (2)0.036 (2)0.0146 (19)0.0027 (19)0.0015 (18)
N40.040 (2)0.032 (2)0.032 (2)0.0159 (18)0.0034 (18)0.0018 (17)
C10.035 (3)0.039 (3)0.024 (2)0.018 (2)0.0006 (19)0.006 (2)
C20.050 (3)0.049 (3)0.034 (3)0.028 (3)0.001 (2)0.008 (2)
C30.044 (3)0.072 (4)0.047 (3)0.037 (3)0.006 (2)0.010 (3)
C40.034 (3)0.067 (4)0.056 (4)0.018 (3)0.005 (2)0.004 (3)
C50.040 (3)0.046 (3)0.048 (3)0.009 (2)0.004 (2)0.001 (2)
C60.036 (3)0.042 (3)0.029 (3)0.016 (2)0.000 (2)0.006 (2)
C70.051 (3)0.031 (3)0.032 (3)0.016 (2)0.003 (2)0.003 (2)
C80.034 (2)0.028 (2)0.028 (3)0.012 (2)0.006 (2)0.0035 (19)
C90.040 (3)0.036 (3)0.032 (3)0.019 (2)0.007 (2)0.005 (2)
C100.044 (3)0.044 (3)0.051 (3)0.020 (2)0.001 (2)0.003 (2)
C110.068 (4)0.051 (4)0.078 (4)0.037 (3)0.004 (3)0.012 (3)
C120.078 (4)0.070 (5)0.093 (5)0.057 (4)0.002 (4)0.006 (4)
C130.081 (4)0.083 (5)0.069 (4)0.057 (4)0.022 (3)0.009 (4)
C140.070 (4)0.054 (3)0.047 (3)0.040 (3)0.006 (3)0.006 (3)
C150.041 (3)0.035 (3)0.029 (3)0.019 (2)0.003 (2)0.001 (2)
C160.040 (3)0.039 (3)0.035 (3)0.023 (2)0.008 (2)0.008 (2)
C170.059 (3)0.052 (4)0.047 (3)0.023 (3)0.016 (3)0.003 (3)
C180.058 (4)0.054 (4)0.074 (5)0.015 (3)0.019 (3)0.018 (3)
C190.060 (4)0.084 (5)0.060 (4)0.035 (4)0.025 (3)0.028 (4)
C200.083 (5)0.098 (6)0.043 (4)0.040 (4)0.025 (3)0.005 (4)
C210.068 (4)0.059 (4)0.044 (3)0.025 (3)0.009 (3)0.001 (3)
C220.042 (3)0.037 (3)0.044 (3)0.020 (2)0.007 (2)0.008 (2)
C230.038 (3)0.027 (3)0.052 (3)0.011 (2)0.005 (2)0.006 (2)
C240.046 (3)0.042 (3)0.068 (4)0.015 (3)0.008 (3)0.012 (3)
C250.038 (3)0.047 (4)0.101 (5)0.003 (3)0.000 (3)0.017 (3)
C260.054 (4)0.039 (3)0.073 (4)0.009 (3)0.016 (3)0.003 (3)
C270.048 (3)0.033 (3)0.065 (4)0.012 (2)0.005 (3)0.007 (3)
C280.036 (3)0.031 (3)0.052 (3)0.015 (2)0.002 (2)0.002 (2)
Geometric parameters (Å, º) top
Cu1—O11.891 (3)C11—H11A0.9300
Cu1—O21.876 (3)C12—C131.367 (8)
Cu1—N11.939 (4)C12—H12A0.9300
Cu1—N41.976 (4)C13—C141.374 (7)
O1—C11.302 (5)C13—H13A0.9300
O2—C281.294 (5)C14—H14A0.9300
N1—C71.268 (5)C15—C161.480 (6)
N1—N21.413 (5)C16—C171.369 (6)
N2—C81.272 (5)C16—C211.384 (7)
N3—C151.276 (5)C17—C181.377 (7)
N3—N41.400 (5)C17—H17A0.9300
N4—C221.284 (5)C18—C191.352 (8)
C1—C21.409 (6)C18—H18A0.9300
C1—C61.407 (6)C19—C201.366 (8)
C2—C31.356 (7)C19—H19A0.9300
C2—H2A0.9300C20—C211.369 (7)
C3—C41.370 (7)C20—H20A0.9300
C3—H3B0.9300C21—H21A0.9300
C4—C51.372 (7)C22—C231.435 (6)
C4—H4A0.9300C22—H22A0.9300
C5—C61.403 (6)C23—C241.395 (6)
C5—H5A0.9300C23—C281.412 (7)
C6—C71.423 (6)C24—C251.365 (7)
C7—H7A0.9300C24—H24A0.9300
C8—C91.493 (6)C25—C261.376 (8)
C8—C151.499 (6)C25—H25A0.9300
C9—C101.382 (6)C26—C271.357 (7)
C9—C141.384 (7)C26—H26A0.9300
C10—C111.384 (7)C27—C281.391 (6)
C10—H10A0.9300C27—H27A0.9300
C11—C121.373 (8)
O1—Cu1—O294.49 (15)C13—C12—H12A119.5
O1—Cu1—N193.45 (15)C11—C12—H12A119.5
O1—Cu1—N4144.66 (14)C14—C13—C12119.6 (6)
O2—Cu1—N1152.98 (16)C14—C13—H13A120.2
O2—Cu1—N492.74 (17)C12—C13—H13A120.2
N1—Cu1—N495.59 (16)C13—C14—C9120.3 (5)
C1—O1—Cu1127.2 (3)C13—C14—H14A119.8
C28—O2—Cu1129.1 (3)C9—C14—H14A119.8
C7—N1—N2115.7 (4)N3—C15—C16117.6 (4)
C7—N1—Cu1124.9 (3)N3—C15—C8124.7 (4)
N2—N1—Cu1118.0 (3)C16—C15—C8117.7 (4)
C8—N2—N1114.7 (4)C17—C16—C21118.0 (5)
C15—N3—N4116.5 (4)C17—C16—C15121.2 (4)
C22—N4—N3115.3 (4)C21—C16—C15120.7 (5)
C22—N4—Cu1124.5 (3)C16—C17—C18120.6 (5)
N3—N4—Cu1116.3 (3)C16—C17—H17A119.7
O1—C1—C2119.1 (4)C18—C17—H17A119.7
O1—C1—C6124.1 (4)C19—C18—C17120.5 (6)
C2—C1—C6116.8 (4)C19—C18—H18A119.7
C3—C2—C1121.3 (5)C17—C18—H18A119.7
C3—C2—H2A119.3C18—C19—C20120.0 (5)
C1—C2—H2A119.3C18—C19—H19A120.0
C2—C3—C4122.1 (5)C20—C19—H19A120.0
C2—C3—H3B118.9C19—C20—C21119.7 (6)
C4—C3—H3B118.9C19—C20—H20A120.2
C3—C4—C5118.5 (5)C21—C20—H20A120.2
C3—C4—H4A120.8C20—C21—C16121.1 (6)
C5—C4—H4A120.8C20—C21—H21A119.4
C4—C5—C6121.1 (5)C16—C21—H21A119.4
C4—C5—H5A119.4N4—C22—C23125.5 (4)
C6—C5—H5A119.4N4—C22—H22A117.3
C5—C6—C1120.1 (4)C23—C22—H22A117.3
C5—C6—C7117.4 (4)C24—C23—C28120.2 (4)
C1—C6—C7122.6 (4)C24—C23—C22116.9 (5)
N1—C7—C6126.4 (4)C28—C23—C22122.8 (4)
N1—C7—H7A116.8C25—C24—C23120.5 (5)
C6—C7—H7A116.8C25—C24—H24A119.8
N2—C8—C9117.7 (4)C23—C24—H24A119.8
N2—C8—C15124.5 (4)C24—C25—C26119.5 (5)
C9—C8—C15117.7 (4)C24—C25—H25A120.3
C10—C9—C14119.7 (4)C26—C25—H25A120.3
C10—C9—C8120.6 (4)C27—C26—C25120.9 (5)
C14—C9—C8119.7 (4)C27—C26—H26A119.6
C11—C10—C9119.7 (5)C25—C26—H26A119.6
C11—C10—H10A120.1C26—C27—C28122.0 (5)
C9—C10—H10A120.1C26—C27—H27A119.0
C12—C11—C10119.6 (5)C28—C27—H27A119.0
C12—C11—H11A120.2O2—C28—C27119.3 (5)
C10—C11—H11A120.2O2—C28—C23123.7 (4)
C13—C12—C11121.1 (5)C27—C28—C23116.9 (4)
O2—Cu1—O1—C1161.7 (4)C15—C8—C9—C1420.7 (6)
N1—Cu1—O1—C17.6 (4)C14—C9—C10—C111.2 (7)
N4—Cu1—O1—C197.1 (4)C8—C9—C10—C11179.5 (4)
O1—Cu1—O2—C28153.3 (4)C9—C10—C11—C120.9 (8)
N1—Cu1—O2—C28100.0 (5)C10—C11—C12—C130.2 (9)
N4—Cu1—O2—C287.9 (4)C11—C12—C13—C140.2 (10)
O2—Cu1—N1—C7103.6 (4)C12—C13—C14—C90.1 (9)
O1—Cu1—N1—C73.3 (4)C10—C9—C14—C130.8 (8)
N4—Cu1—N1—C7149.1 (4)C8—C9—C14—C13179.2 (5)
O2—Cu1—N1—N262.0 (5)N4—N3—C15—C16168.1 (4)
O1—Cu1—N1—N2168.9 (3)N4—N3—C15—C811.7 (6)
N4—Cu1—N1—N245.3 (3)N2—C8—C15—N374.9 (6)
C7—N1—N2—C8122.7 (4)C9—C8—C15—N3108.1 (5)
Cu1—N1—N2—C870.3 (4)N2—C8—C15—C16104.9 (5)
C15—N3—N4—C22134.9 (4)C9—C8—C15—C1672.1 (5)
C15—N3—N4—Cu166.1 (4)N3—C15—C16—C17167.5 (4)
O2—Cu1—N4—C223.4 (4)C8—C15—C16—C1712.3 (6)
O1—Cu1—N4—C2298.4 (4)N3—C15—C16—C218.8 (7)
N1—Cu1—N4—C22157.6 (4)C8—C15—C16—C21171.4 (4)
O2—Cu1—N4—N3160.2 (3)C21—C16—C17—C181.8 (8)
O1—Cu1—N4—N358.5 (4)C15—C16—C17—C18174.5 (5)
N1—Cu1—N4—N345.5 (3)C16—C17—C18—C191.4 (9)
Cu1—O1—C1—C2168.4 (3)C17—C18—C19—C201.1 (9)
Cu1—O1—C1—C611.6 (6)C18—C19—C20—C211.3 (9)
O1—C1—C2—C3179.2 (4)C19—C20—C21—C161.8 (9)
C6—C1—C2—C30.8 (7)C17—C16—C21—C202.0 (8)
C1—C2—C3—C41.2 (8)C15—C16—C21—C20174.3 (5)
C2—C3—C4—C51.3 (8)N3—N4—C22—C23169.4 (4)
C3—C4—C5—C60.5 (8)Cu1—N4—C22—C2312.3 (7)
C4—C5—C6—C12.5 (7)N4—C22—C23—C24170.1 (5)
C4—C5—C6—C7176.3 (4)N4—C22—C23—C2811.4 (8)
O1—C1—C6—C5177.4 (4)C28—C23—C24—C252.3 (8)
C2—C1—C6—C52.6 (6)C22—C23—C24—C25179.2 (5)
O1—C1—C6—C73.9 (7)C23—C24—C25—C261.7 (9)
C2—C1—C6—C7176.1 (4)C24—C25—C26—C270.3 (9)
N2—N1—C7—C6176.7 (4)C25—C26—C27—C281.8 (9)
Cu1—N1—C7—C610.8 (7)Cu1—O2—C28—C27170.9 (3)
C5—C6—C7—N1170.6 (5)Cu1—O2—C28—C2310.6 (7)
C1—C6—C7—N18.2 (7)C26—C27—C28—O2179.7 (5)
N1—N2—C8—C9176.8 (3)C26—C27—C28—C231.2 (8)
N1—N2—C8—C156.2 (6)C24—C23—C28—O2177.7 (5)
N2—C8—C9—C1016.3 (6)C22—C23—C28—O20.8 (8)
C15—C8—C9—C10160.9 (4)C24—C23—C28—C270.8 (7)
N2—C8—C9—C14162.1 (4)C22—C23—C28—C27179.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24—H24A···Cgi0.933.053.93 (2)152
Symmetry code: (i) x+2, y+2, z.
 

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