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In the title complex, [Cu2(C11H11N3O2)2(C5H5N)2]·CH4O, the two CuII atoms are bridged by two oxime O atoms of di­acetyl monoxime benzoyl­hydrazone ligands, with a Cu...Cu distance of 3.644 (2) Å. The center of the dimer corresponds to a crystallographic center of symmetry. Each CuII atom shows a square-pyramidal geometry defined by two N and two O atoms of hydrazone ligands and one pyridine N atom. The methanol solvent mol­ecules lie on special positions with twofold rotation symmetry and form intramolecular O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024523/sj6009sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024523/sj6009Isup2.hkl
Contains datablock I

CCDC reference: 255418

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in solvent or counterion
  • R factor = 0.051
  • wR factor = 0.122
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

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Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 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: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis[µ-3-(hydroxyimino)butan-2-one benzoylhydrazonato]bis[pyridinecopper(II)] methanol solvate top
Crystal data top
C32H32Cu2N8O4·CH4OF(000) = 1552
Mr = 751.78Dx = 1.477 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7270 reflections
a = 17.617 (4) Åθ = 3.2–27.5°
b = 8.363 (3) ŵ = 1.31 mm1
c = 23.099 (4) ÅT = 293 K
β = 96.695 (11)°Prism, dark blue
V = 3380.0 (16) Å30.28 × 0.22 × 0.12 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3865 independent reflections
Radiation source: fine-focus sealed tube2569 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 2022
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1010
Tmin = 0.710, Tmax = 0.859l = 2929
16098 measured reflections
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0629P)2 + 1.2139P]
where P = (Fo2 + 2Fc2)/3
3865 reflections(Δ/σ)max < 0.001
230 parametersΔρmax = 0.40 e Å3
1 restraintΔρmin = 0.25 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.92540 (2)0.03169 (5)0.547199 (17)0.04586 (15)
O10.97494 (13)0.1215 (3)0.43731 (10)0.0536 (6)
O20.88797 (13)0.1480 (3)0.61548 (10)0.0541 (6)
O31.0134 (5)0.1661 (10)0.7117 (3)0.099 (2)0.50
N10.91798 (15)0.0623 (3)0.46478 (12)0.0459 (6)
N20.81645 (15)0.0191 (3)0.52814 (12)0.0466 (6)
N30.76989 (16)0.0861 (3)0.56525 (12)0.0492 (7)
N40.95372 (17)0.2046 (3)0.59067 (13)0.0549 (7)
C10.8294 (2)0.1947 (5)0.38962 (15)0.0595 (9)
C20.84838 (19)0.0989 (4)0.44363 (14)0.0447 (7)
C30.78946 (19)0.0388 (4)0.47834 (15)0.0466 (7)
C40.7065 (2)0.0457 (5)0.45723 (18)0.0633 (10)
C50.81457 (19)0.1495 (4)0.60965 (15)0.0473 (8)
C60.7745 (2)0.2320 (4)0.65464 (15)0.0484 (8)
C70.6960 (2)0.2433 (5)0.64894 (19)0.0682 (11)
C80.6590 (3)0.3214 (6)0.6899 (2)0.0841 (14)
C90.7010 (3)0.3900 (5)0.7375 (2)0.0768 (13)
C100.7788 (3)0.3818 (5)0.74363 (18)0.0707 (11)
C110.8159 (2)0.3030 (4)0.70246 (16)0.0597 (9)
C120.9927 (2)0.3192 (5)0.5671 (2)0.0696 (11)
C131.0094 (3)0.4633 (5)0.5933 (3)0.0909 (15)
C140.9858 (4)0.4922 (6)0.6458 (3)0.1033 (19)
C150.9462 (3)0.3770 (6)0.6712 (2)0.0919 (15)
C160.9309 (2)0.2351 (5)0.64225 (17)0.0673 (11)
C170.9940 (17)0.0717 (11)0.7604 (6)0.074 (4)0.50
H1A0.87290.19820.36820.089*
H1B0.78710.14620.36600.089*
H1C0.81590.30140.39980.089*
H4A0.67820.01010.48410.095*
H4B0.69020.15530.45450.095*
H4C0.69740.00360.41950.095*
H70.66750.19730.61680.082*
H80.60590.32780.68560.101*
H90.67630.44200.76560.092*
H100.80700.42930.77560.085*
H110.86900.29770.70690.072*
H121.00940.30020.53100.083*
H131.03670.54020.57530.109*
H140.99630.58980.66430.124*
H150.92990.39410.70760.110*
H160.90330.15720.65950.081*
H17A1.03400.08080.79230.111*0.50
H17B0.98830.03830.74890.111*0.50
H17C0.94690.10990.77250.111*0.50
H180.97910.15880.68460.149*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0390 (2)0.0538 (2)0.0440 (2)0.00290 (19)0.00185 (16)0.00842 (19)
O10.0426 (13)0.0663 (15)0.0522 (14)0.0098 (11)0.0071 (11)0.0166 (12)
O20.0412 (13)0.0644 (14)0.0559 (14)0.0022 (11)0.0028 (11)0.0128 (11)
O30.090 (5)0.108 (5)0.091 (5)0.028 (5)0.023 (4)0.039 (4)
N10.0424 (15)0.0471 (15)0.0477 (15)0.0055 (12)0.0033 (12)0.0049 (12)
N20.0393 (14)0.0546 (15)0.0452 (15)0.0042 (12)0.0025 (12)0.0029 (13)
N30.0408 (15)0.0574 (15)0.0497 (17)0.0004 (12)0.0067 (13)0.0018 (13)
N40.0525 (18)0.0552 (17)0.0549 (18)0.0064 (14)0.0034 (14)0.0021 (14)
C10.057 (2)0.071 (2)0.049 (2)0.0130 (18)0.0030 (17)0.0119 (18)
C20.0439 (18)0.0486 (17)0.0400 (17)0.0068 (14)0.0023 (14)0.0003 (14)
C30.0428 (17)0.0465 (17)0.0493 (19)0.0049 (15)0.0006 (14)0.0049 (15)
C40.044 (2)0.082 (3)0.062 (2)0.0034 (19)0.0017 (17)0.001 (2)
C50.0485 (19)0.0442 (17)0.0499 (19)0.0010 (15)0.0089 (16)0.0027 (14)
C60.051 (2)0.0460 (17)0.050 (2)0.0007 (15)0.0147 (16)0.0043 (15)
C70.057 (2)0.072 (2)0.078 (3)0.0052 (19)0.017 (2)0.016 (2)
C80.058 (3)0.098 (3)0.102 (4)0.004 (2)0.032 (3)0.028 (3)
C90.086 (3)0.076 (3)0.076 (3)0.001 (2)0.039 (3)0.011 (2)
C100.090 (3)0.069 (3)0.055 (2)0.002 (2)0.018 (2)0.013 (2)
C110.063 (2)0.061 (2)0.056 (2)0.0011 (19)0.0104 (19)0.0048 (18)
C120.062 (3)0.068 (3)0.076 (3)0.009 (2)0.001 (2)0.004 (2)
C130.087 (4)0.062 (3)0.121 (5)0.009 (2)0.002 (3)0.004 (3)
C140.109 (4)0.069 (3)0.124 (5)0.001 (3)0.017 (4)0.034 (3)
C150.110 (4)0.091 (4)0.073 (3)0.024 (3)0.004 (3)0.024 (3)
C160.078 (3)0.066 (2)0.057 (2)0.015 (2)0.005 (2)0.001 (2)
C170.091 (11)0.079 (5)0.051 (12)0.017 (8)0.001 (10)0.007 (5)
Geometric parameters (Å, º) top
Cu1—O1i1.905 (2)C5—C61.492 (4)
Cu1—O22.028 (2)C6—C71.377 (5)
Cu1—N12.050 (3)C6—C111.385 (5)
Cu1—N21.922 (3)C7—C81.376 (5)
Cu1—N42.246 (3)C7—H70.9300
O2—C51.285 (4)C8—C91.377 (6)
N3—C51.328 (4)C8—H80.9300
N2—N31.373 (4)C9—C101.363 (6)
N2—C31.287 (4)C9—H90.9300
C2—C31.472 (5)C10—C111.382 (5)
C2—N11.303 (4)C10—H100.9300
O1—N11.343 (3)C11—H110.9300
O1—Cu1i1.905 (2)C12—C131.365 (6)
O3—C171.448 (8)C12—H120.9300
O3—H180.8200C13—C141.347 (8)
N4—C161.326 (5)C13—H130.9300
N4—C121.332 (5)C14—C151.363 (8)
C1—C21.487 (4)C14—H140.9300
C1—H1A0.9600C15—C161.374 (6)
C1—H1B0.9600C15—H150.9300
C1—H1C0.9600C16—H160.9300
C3—C41.488 (5)C17—H17A0.9600
C4—H4A0.9600C17—H17B0.9600
C4—H4B0.9600C17—H17C0.9600
C4—H4C0.9600
O1i—Cu1—N2159.9 (1)C6—C7—H7119.4
O1i—Cu1—O292.35 (9)C6—C11—H11119.8
O1i—Cu1—N1106.5 (1)C7—C8—C9119.5 (4)
O1i—Cu1—N496.4 (1)C7—C8—H8120.2
O2—Cu1—N1156.2 (1)C7—C6—C11118.5 (3)
O2—Cu1—N498.6 (1)C7—C6—C5121.1 (3)
N2—Cu1—O278.3 (1)C8—C7—C6121.2 (4)
N2—Cu1—N179.2 (1)C8—C7—H7119.4
N2—Cu1—N4102.6 (1)C8—C9—H9119.9
N1—Cu1—N493.7 (1)C9—C10—C11120.2 (4)
O1—N1—Cu1127.6 (2)C9—C10—H10119.9
N1—O1—Cu1i119.3 (2)C9—C8—H8120.2
O2—C5—N3125.2 (3)C10—C9—C8120.2 (4)
O2—C5—C6118.9 (3)C10—C9—H9119.9
N1—C2—C3114.1 (3)C10—C11—C6120.4 (4)
N1—C2—C1123.5 (3)C10—C11—H11119.8
N2—C3—C2113.9 (3)C11—C6—C5120.4 (3)
N2—C3—C4123.6 (3)C11—C10—H10119.9
N3—N2—Cu1119.2 (2)C12—N4—Cu1123.3 (3)
N3—C5—C6115.9 (3)C12—C13—H13120.5
N4—C12—C13123.3 (5)C13—C14—C15119.2 (5)
N4—C12—H12118.4C13—C14—H14120.4
N4—C16—C15122.8 (4)C13—C12—H12118.4
N4—C16—H16118.6C14—C13—C12119.0 (5)
C2—N1—O1117.3 (3)C14—C13—H13120.5
C2—N1—Cu1113.2 (2)C14—C15—C16118.8 (5)
C2—C1—H1A109.5C14—C15—H15120.6
C2—C1—H1B109.5C15—C14—H14120.4
C2—C1—H1C109.5C15—C16—H16118.6
C2—C3—C4122.5 (3)C16—N4—C12117.0 (3)
C3—C4—H4A109.5C16—N4—Cu1119.8 (3)
C3—C4—H4B109.5C16—C15—H15120.6
C3—N2—N3121.8 (3)H1A—C1—H1B109.5
C3—N2—Cu1118.7 (2)H1A—C1—H1C109.5
C3—C2—C1122.5 (3)H1B—C1—H1C109.5
C3—C4—H4C109.5H4A—C4—H4B109.5
C5—O2—Cu1109.7 (2)H4A—C4—H4C109.5
C5—N3—N2107.6 (3)H4B—C4—H4C109.5
Cu1i—O1—N1—C2164.2 (2)N1—C2—C3—C4170.4 (3)
Cu1i—O1—N1—Cu132.7 (3)N2—N3—C5—O20.6 (5)
Cu1—N2—N3—C50.1 (3)N2—N3—C5—C6178.8 (3)
Cu1—N1—C2—C310.6 (3)N2—Cu1—O2—C50.5 (2)
Cu1—N1—C2—C1168.7 (3)N2—Cu1—N4—C1668.3 (3)
Cu1—N2—C3—C24.0 (4)N2—Cu1—N1—C26.8 (2)
Cu1—O2—C5—N30.8 (4)N2—Cu1—N1—O1170.5 (3)
Cu1—O2—C5—C6178.9 (2)N2—Cu1—N4—C12111.3 (3)
Cu1—N4—C12—C13179.5 (4)N3—N2—C3—C2177.4 (3)
Cu1—N4—C16—C15180.0 (3)N3—N2—C3—C42.7 (5)
O1—N1—C2—C13.3 (5)N3—C5—C6—C71.3 (5)
Cu1—N2—C3—C4176.2 (3)N3—C5—C6—C11179.5 (3)
O1i—Cu1—O2—C5162.5 (2)N4—Cu1—N1—O168.3 (3)
O1i—Cu1—N1—C2166.9 (2)N4—Cu1—O2—C5100.7 (2)
O1i—Cu1—N1—O129.4 (3)N4—Cu1—N1—C295.3 (2)
O1i—Cu1—N2—C3109.7 (3)N4—Cu1—N2—C390.2 (3)
O1i—Cu1—N2—N364.0 (4)N4—Cu1—N2—N396.1 (2)
O1i—Cu1—N4—C16104.9 (3)N4—C12—C13—C140.2 (8)
O1i—Cu1—N4—C1275.5 (3)C1—C2—C3—N2169.5 (3)
O1—N1—C2—C3176.0 (3)C1—C2—C3—C410.3 (5)
O2—Cu1—N4—C12168.8 (3)C3—N2—N3—C5173.6 (3)
O2—Cu1—N2—N30.2 (2)C5—C6—C7—C8179.0 (4)
O2—Cu1—N4—C1611.5 (3)C5—C6—C11—C10178.9 (3)
O2—Cu1—N2—C3173.4 (3)C6—C7—C8—C90.2 (7)
O2—C5—C6—C7176.9 (3)C7—C8—C9—C100.6 (7)
O2—Cu1—N1—C226.0 (4)C7—C6—C11—C100.7 (5)
O2—Cu1—N1—O1170.3 (2)C8—C9—C10—C110.7 (7)
O2—C5—C6—C111.3 (5)C9—C10—C11—C60.1 (6)
N1—C2—C3—N29.8 (4)C11—C6—C7—C80.8 (6)
N1—Cu1—O2—C519.7 (4)C12—C13—C14—C150.3 (9)
N1—Cu1—N2—N3172.4 (2)C13—C14—C15—C160.7 (9)
N1—Cu1—N2—C31.2 (2)C12—N4—C16—C150.3 (6)
N1—Cu1—N4—C16148.1 (3)C14—C15—C16—N40.8 (8)
N1—Cu1—N4—C1231.6 (3)C16—N4—C12—C130.2 (6)
Symmetry code: (i) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H18···O20.822.132.950 (8)178
 

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