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In the title complex, [Cu(C16H14N2O2)(C7H6N2)]·CH4O, [Cu(L)(1H-benz­imidazole)]·CH3OH, [H2L = 3-methoxy­salicyl­aldehyde (4-methoxy­benzoyl)­hydrazone, C16H16N2O4], the CuII atom is coordinated by two O atoms and one N atom of the fully deprotonated tridentate hydrazone ligand and one N atom from the 1H-benz­imidazole mol­ecule, thus defining a square planar coordination geometry. Adjacent mol­ecules are linked by hydrogen bonds into a chain structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026169/rz6009sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026169/rz6009Isup2.hkl
Contains datablock I

CCDC reference: 255441

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.039
  • wR factor = 0.089
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.65 Ratio PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C H4 O
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 4912 Count of symmetry unique reflns 2637 Completeness (_total/calc) 186.27% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2275 Fraction of Friedel pairs measured 0.863 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 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: 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.

(1H-Benzimidazole-κN3)[3-methoxysalicylaldehyde (4-methoxybenzoyl)hydrazonato-κ3O,N,O']copper(II) methanol solvate top
Crystal data top
[Cu(C16H14N2O4)(C7H6N2)]·CH4OF(000) = 530
Mr = 512.02Dx = 1.483 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 9816 reflections
a = 13.534 (3) Åθ = 3.0–27.5°
b = 5.071 (1) ŵ = 1.00 mm1
c = 21.294 (6) ÅT = 293 K
β = 128.31 (2)°Prism, blue
V = 1146.7 (6) Å30.38 × 0.25 × 0.18 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4912 independent reflections
Radiation source: fine-focus sealed tube4199 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = 1717
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 66
Tmin = 0.703, Tmax = 0.841l = 2727
10067 measured reflections
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)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0569P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4912 reflectionsΔρmax = 0.45 e Å3
316 parametersΔρmin = 0.24 e Å3
4 restraintsAbsolute structure: Flack (1983), 2320 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.015 (11)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.50000 (3)0.46239 (6)0.50000 (2)0.04382 (11)
O10.5901 (2)0.5679 (4)0.61055 (13)0.0507 (5)
O20.9444 (2)0.5329 (5)0.98938 (14)0.0632 (6)
O30.4237 (2)0.3205 (5)0.39809 (12)0.0574 (6)
O40.2912 (3)0.2371 (6)0.24591 (14)0.0816 (9)
O50.9587 (2)0.0253 (6)0.69724 (16)0.0648 (7)
H260.886 (2)0.051 (10)0.684 (3)0.097*
N10.7213 (2)0.2296 (5)0.63356 (15)0.0464 (6)
N20.6375 (2)0.2171 (5)0.55025 (14)0.0442 (6)
N30.3608 (2)0.7152 (5)0.45009 (14)0.0451 (6)
N40.1715 (3)0.8663 (6)0.35051 (16)0.0549 (6)
H250.097 (2)0.892 (10)0.3013 (13)0.082*
C10.6848 (3)0.4195 (6)0.65776 (17)0.0430 (6)
C20.7565 (3)0.4535 (6)0.74521 (17)0.0433 (6)
C30.7241 (3)0.6572 (7)0.77350 (19)0.0527 (7)
H30.66020.77330.73700.063*
C40.7842 (3)0.6909 (7)0.85395 (19)0.0531 (8)
H40.76070.82770.87130.064*
C50.8796 (3)0.5206 (6)0.90877 (18)0.0485 (7)
C60.9135 (3)0.3187 (7)0.88201 (19)0.0522 (7)
H60.97810.20440.91880.063*
C70.8529 (3)0.2844 (6)0.80157 (18)0.0487 (7)
H70.87660.14650.78470.058*
C80.9165 (5)0.7434 (9)1.0201 (2)0.0784 (11)
H8A0.93820.90811.00930.118*
H8B0.96410.72231.07690.118*
H8C0.82820.74210.99500.118*
C90.6549 (3)0.0381 (7)0.5154 (2)0.0498 (8)
H90.72290.07510.54790.060*
C100.5784 (4)0.0026 (7)0.4306 (2)0.0481 (9)
C110.6164 (4)0.1959 (8)0.4016 (2)0.0676 (10)
H110.68930.29290.43740.081*
C120.5472 (4)0.2407 (10)0.3218 (3)0.0823 (12)
H120.57270.36760.30310.099*
C130.4377 (5)0.0959 (10)0.2682 (2)0.0796 (12)
H130.39160.12500.21350.096*
C140.3971 (3)0.0873 (8)0.2942 (2)0.0595 (9)
C150.4678 (3)0.1418 (7)0.37743 (18)0.0487 (7)
C160.2263 (5)0.2256 (14)0.1626 (3)0.111 (2)
H16A0.28350.26440.15150.167*
H16B0.15920.35260.13630.167*
H16C0.19200.05210.14340.167*
C170.2634 (3)0.6995 (7)0.37328 (19)0.0515 (8)
H170.25970.58190.33840.062*
C180.3279 (3)0.9157 (7)0.47966 (19)0.0420 (7)
C190.3970 (4)1.0273 (7)0.5551 (3)0.0488 (9)
H190.47720.96810.59700.059*
C200.3398 (4)1.2324 (7)0.5647 (2)0.0576 (8)
H200.38341.31450.61430.069*
C210.2193 (4)1.3192 (7)0.5025 (2)0.0600 (8)
H210.18371.45480.51200.072*
C220.1513 (3)1.2099 (7)0.4274 (2)0.0561 (8)
H220.07071.26790.38560.067*
C230.2097 (3)1.0083 (6)0.41763 (19)0.0470 (7)
C240.9599 (4)0.2476 (10)0.6869 (3)0.0867 (13)
H24A1.04410.31350.72490.130*
H24B0.93110.28280.63360.130*
H24C0.90530.33340.69490.130*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03522 (15)0.05301 (19)0.03199 (15)0.0032 (3)0.01524 (13)0.0004 (2)
O10.0445 (12)0.0520 (13)0.0378 (11)0.0037 (10)0.0167 (10)0.0023 (10)
O20.0613 (14)0.0805 (16)0.0369 (11)0.0002 (12)0.0251 (12)0.0042 (11)
O30.0461 (12)0.0775 (17)0.0314 (10)0.0164 (12)0.0155 (10)0.0043 (10)
O40.0695 (18)0.116 (2)0.0329 (12)0.0293 (17)0.0188 (13)0.0017 (13)
O50.0379 (13)0.0781 (18)0.0526 (14)0.0004 (11)0.0152 (12)0.0061 (11)
N10.0324 (13)0.0589 (16)0.0319 (12)0.0015 (11)0.0120 (11)0.0002 (11)
N20.0329 (12)0.0559 (15)0.0329 (12)0.0015 (11)0.0150 (11)0.0028 (11)
N30.0397 (13)0.0513 (14)0.0341 (13)0.0003 (11)0.0179 (12)0.0001 (10)
N40.0390 (14)0.0643 (16)0.0382 (14)0.0077 (13)0.0123 (12)0.0011 (12)
C10.0361 (15)0.0473 (16)0.0351 (14)0.0089 (13)0.0168 (13)0.0041 (12)
C20.0384 (14)0.0460 (15)0.0359 (13)0.0091 (13)0.0182 (12)0.0023 (12)
C30.0459 (17)0.0514 (18)0.0390 (16)0.0027 (15)0.0155 (14)0.0001 (13)
C40.0549 (19)0.0533 (19)0.0436 (17)0.0022 (15)0.0267 (16)0.0100 (13)
C50.0429 (15)0.0588 (18)0.0354 (13)0.0121 (14)0.0200 (13)0.0028 (13)
C60.0443 (17)0.0598 (19)0.0403 (16)0.0060 (15)0.0201 (14)0.0070 (14)
C70.0473 (17)0.0503 (17)0.0429 (16)0.0002 (14)0.0252 (14)0.0013 (13)
C80.093 (3)0.086 (3)0.049 (2)0.000 (2)0.041 (2)0.0144 (18)
C90.0375 (16)0.0564 (19)0.0457 (18)0.0063 (16)0.0209 (15)0.0019 (16)
C100.045 (2)0.055 (2)0.0402 (18)0.0008 (15)0.0244 (17)0.0038 (13)
C110.061 (2)0.076 (3)0.062 (2)0.0111 (19)0.036 (2)0.0080 (18)
C120.080 (3)0.098 (3)0.067 (3)0.013 (3)0.045 (2)0.020 (2)
C130.082 (3)0.100 (3)0.049 (2)0.012 (3)0.037 (2)0.016 (2)
C140.0530 (19)0.076 (2)0.0401 (16)0.0026 (17)0.0243 (16)0.0056 (15)
C150.0484 (17)0.0561 (17)0.0403 (15)0.0018 (15)0.0268 (14)0.0037 (13)
C160.099 (4)0.157 (5)0.043 (2)0.036 (4)0.027 (3)0.007 (3)
C170.0428 (17)0.0589 (19)0.0383 (15)0.0047 (14)0.0178 (14)0.0012 (13)
C180.0404 (16)0.0460 (18)0.0375 (15)0.0003 (14)0.0232 (14)0.0045 (14)
C190.045 (2)0.057 (2)0.0409 (18)0.0054 (16)0.0252 (17)0.0085 (15)
C200.073 (2)0.0579 (19)0.0483 (18)0.0027 (18)0.0409 (19)0.0007 (15)
C210.072 (2)0.056 (2)0.069 (2)0.0079 (18)0.052 (2)0.0042 (17)
C220.0478 (18)0.0574 (19)0.0560 (19)0.0092 (15)0.0285 (17)0.0063 (15)
C230.0387 (14)0.0535 (18)0.0440 (15)0.0005 (13)0.0232 (13)0.0017 (12)
C240.062 (3)0.078 (3)0.088 (3)0.006 (2)0.030 (2)0.006 (2)
Geometric parameters (Å, º) top
Cu1—N21.920 (3)C8—H8A0.9600
Cu1—N31.960 (3)C8—H8B0.9600
Cu1—O11.938 (2)C8—H8C0.9600
Cu1—O31.875 (2)C9—C101.435 (6)
N1—C11.323 (4)C9—H90.9300
N1—N21.394 (3)C10—C111.414 (6)
N2—C91.283 (5)C10—C151.400 (5)
O1—C11.274 (4)C11—C121.357 (5)
O3—C151.302 (4)C11—H110.9300
N3—C171.322 (4)C12—C131.393 (6)
N3—C181.405 (4)C12—H120.9300
N4—C171.323 (4)C13—C141.359 (6)
N4—C231.383 (4)C13—H130.9300
N4—H250.91 (2)C14—C151.426 (4)
O2—C51.361 (4)C16—H16A0.9600
O2—C81.421 (5)C16—H16B0.9600
O4—C141.365 (5)C16—H16C0.9600
O4—C161.411 (5)C17—H170.9300
O5—C241.403 (6)C18—C191.383 (6)
O5—H260.85 (5)C18—C231.381 (5)
C1—C21.483 (4)C19—C201.385 (5)
C2—C71.392 (4)C19—H190.9300
C2—C31.396 (5)C20—C211.389 (5)
C3—C41.378 (4)C20—H200.9300
C3—H30.9300C21—C221.374 (5)
C4—C51.381 (5)C21—H210.9300
C4—H40.9300C22—C231.385 (5)
C5—C61.381 (5)C22—H220.9300
C6—C71.377 (4)C24—H24A0.9600
C6—H60.9300C24—H24B0.9600
C7—H70.9300C24—H24C0.9600
N2—Cu1—N3179.2 (1)C10—C9—H9117.2
N2—Cu1—O180.8 (1)C10—C11—H11119.8
O1—Cu1—N398.5 (1)C10—C15—C14117.4 (3)
O3—Cu1—N292.5 (1)C11—C10—C9118.4 (4)
O3—Cu1—N388.2 (1)C11—C12—C13119.8 (4)
O3—Cu1—O1172.9 (1)C11—C12—H12120.1
N1—N2—Cu1115.0 (2)C12—C11—C10120.5 (4)
N1—C1—C2117.5 (3)C12—C11—H11119.8
N2—C9—C10125.6 (3)C12—C13—H13119.4
N2—C9—H9117.2C13—C12—H12120.1
N3—C17—N4113.9 (3)C13—C14—O4125.1 (3)
N3—C17—H17123.0C13—C14—C15120.7 (4)
N4—C17—H17123.0C14—O4—C16117.9 (3)
N4—C23—C22131.1 (3)C14—C13—C12121.3 (4)
O1—C1—N1123.9 (3)C14—C13—H13119.4
O1—C1—C2118.5 (3)C15—O3—Cu1128.3 (2)
O2—C5—C4124.9 (3)C15—C10—C11120.4 (4)
O2—C5—C6115.8 (3)C15—C10—C9121.2 (4)
O2—C8—H8A109.5C17—N3—Cu1121.2 (2)
O2—C8—H8B109.5C17—N3—C18104.4 (3)
O2—C8—H8C109.5C17—N4—C23106.9 (3)
O3—C15—C10125.1 (3)C17—N4—H25129 (3)
O3—C15—C14117.4 (3)C18—N3—Cu1134.0 (2)
O4—C14—C15114.2 (3)C18—C19—C20116.2 (4)
O4—C16—H16A109.5C18—C19—H19121.9
O4—C16—H16B109.5C18—C23—N4106.3 (3)
O4—C16—H16C109.5C18—C23—C22122.6 (3)
O5—C24—H24A109.5C19—C18—N3130.0 (3)
O5—C24—H24B109.5C19—C20—C21122.0 (4)
O5—C24—H24C109.5C19—C20—H20119.0
C1—N1—N2108.9 (2)C20—C19—H19121.9
C1—O1—Cu1111.3 (2)C20—C21—H21119.2
C2—C3—H3119.1C21—C20—H20119.0
C2—C7—H7119.6C21—C22—C23116.1 (3)
C3—C2—C1119.5 (3)C21—C22—H22121.9
C3—C4—C5119.7 (3)C22—C21—C20121.7 (3)
C3—C4—H4120.1C22—C21—H21119.2
C4—C3—C2121.8 (3)C23—N4—H25124 (3)
C4—C3—H3119.1C23—C18—N3108.6 (3)
C4—C5—C6119.4 (3)C23—C18—C19121.3 (3)
C5—O2—C8117.9 (3)C23—C22—H22121.9
C5—C4—H4120.1C24—O5—H26103 (4)
C5—C6—H6119.6H8A—C8—H8B109.5
C6—C7—C2120.8 (3)H8A—C8—H8C109.5
C6—C7—H7119.6H8B—C8—H8C109.5
C7—C2—C1123.0 (3)H16A—C16—H16B109.5
C7—C2—C3117.5 (3)H16A—C16—H16C109.5
C7—C6—C5120.9 (3)H16B—C16—H16C109.5
C7—C6—H6119.6H24A—C24—H24B109.5
C9—N2—Cu1126.7 (2)H24A—C24—H24C109.5
C9—N2—N1118.2 (3)H24B—C24—H24C109.5
Cu1—N2—C9—C104.4 (5)C1—C2—C7—C6177.6 (3)
Cu1—N3—C17—N4173.3 (2)C2—C3—C4—C50.3 (5)
Cu1—N3—C18—C1911.7 (6)C3—C2—C7—C60.1 (5)
Cu1—N3—C18—C23171.9 (2)C3—C4—C5—O2179.2 (3)
Cu1—O1—C1—N14.3 (4)C3—C4—C5—C60.1 (5)
Cu1—O1—C1—C2173.4 (2)C4—C5—C6—C70.4 (5)
Cu1—O3—C15—C107.2 (5)C5—C6—C7—C20.4 (5)
Cu1—O3—C15—C14173.3 (3)C7—C2—C3—C40.3 (5)
N1—N2—C9—C10179.8 (4)C8—O2—C5—C43.2 (5)
N1—C1—C2—C3177.8 (3)C8—O2—C5—C6177.6 (3)
N1—C1—C2—C74.8 (4)C9—C10—C11—C12179.8 (4)
N2—Cu1—O1—C13.7 (2)C9—C10—C15—O30.2 (6)
N2—Cu1—O3—C156.9 (3)C9—C10—C15—C14179.6 (4)
N2—N1—C1—O11.9 (4)C10—C11—C12—C130.2 (7)
N2—N1—C1—C2175.8 (2)C11—C10—C15—O3178.9 (4)
N2—C9—C10—C155.9 (6)C11—C10—C15—C140.5 (6)
N2—C9—C10—C11175.0 (4)C11—C12—C13—C141.2 (8)
N3—Cu1—O1—C1176.4 (2)C12—C13—C14—O4179.9 (4)
N3—Cu1—O3—C15173.0 (3)C12—C13—C14—C151.8 (7)
N3—C18—C19—C20177.1 (3)C13—C14—C15—O3179.6 (4)
N3—C18—C23—N40.6 (4)C13—C14—C15—C100.9 (6)
N3—C18—C23—C22179.1 (3)C15—C10—C11—C121.1 (7)
O1—Cu1—N2—N12.9 (2)C16—O4—C14—C138.0 (7)
O1—Cu1—N2—C9178.7 (3)C16—O4—C14—C15170.4 (4)
O1—Cu1—N3—C17171.8 (3)C17—N3—C18—C19175.8 (4)
O1—Cu1—N3—C180.3 (3)C17—N3—C18—C230.6 (4)
O1—C1—C2—C34.3 (4)C17—N4—C23—C180.3 (4)
O1—C1—C2—C7173.1 (3)C17—N4—C23—C22178.7 (3)
O2—C5—C6—C7178.9 (3)C18—N3—C17—N40.4 (4)
O3—Cu1—N2—N1174.7 (2)C18—C19—C20—C210.8 (5)
O3—Cu1—N2—C91.2 (3)C19—C20—C21—C221.5 (5)
O3—Cu1—N3—C175.8 (3)C19—C18—C23—N4176.2 (3)
O3—Cu1—N3—C18177.3 (3)C19—C18—C23—C222.4 (5)
O4—C14—C15—O31.2 (5)C20—C21—C22—C230.3 (5)
O4—C14—C15—C10179.4 (3)C21—C22—C23—N4176.5 (3)
C1—N1—N2—Cu11.5 (3)C21—C22—C23—C181.6 (5)
C1—N1—N2—C9177.8 (3)C23—N4—C17—N30.1 (4)
C1—C2—C3—C4177.3 (3)C23—C18—C19—C201.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H25···O5i0.91 (2)1.86 (2)2.756 (4)171 (4)
O5—H26···N10.85 (5)1.99 (5)2.800 (4)158 (5)
Symmetry code: (i) x1, y+1, z1/2.
 

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