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The salicylaldehyde semicarbazonate anion O,N,O-chelates to the Cu atom in the title compound, bis­[μ-2-(semicarb­azono­meth­yl)phenolato]-1κ3O3,N1,O:2κO;1κO:2κ3O3,N1,O-bis­[(form­ato-κO)copper(II)] [Cu2(C8H8N3O2)2(CHO2)2], the N and O atoms occupying three sites of the square-planar environment around it. The fourth site is occupied by the negatively charged O atom of the formate anion. Two mol­ecules are bridged through the phen­oxy O atom across a center of symmetry to give a dinuclear compound, so that the Cu atom exists in a square-pyramidal geometry [Cu←Ophen­oxy = 2.546 (1) Å in the apical position]. Hydrogen bonds link the dinuclear mol­ecules into a three-dimensional network architecture.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025845/xu6043sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025845/xu6043Isup2.hkl
Contains datablock I

CCDC reference: 284012

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.033
  • wR factor = 0.090
  • Data-to-parameter ratio = 23.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT411_ALERT_2_B Short Inter H...H Contact H4 .. H4 .. 2.03 Ang.
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1_a .. 5.15 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 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 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 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: 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-2-(semicarbazonomethyl)phenolato]- 1κ3O3,N1,O:2κO;1κO:2κ3O3,N1,O-bis[(formato-κO)copper(II)] top
Crystal data top
[Cu2(C8H8N3O2)2(CHO2)2]F(000) = 580
Mr = 573.46Dx = 1.835 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1754 reflections
a = 7.7562 (5) Åθ = 2.6–32.0°
b = 14.1641 (8) ŵ = 2.11 mm1
c = 9.6837 (6) ÅT = 173 K
β = 102.743 (1)°Prism, green
V = 1037.6 (1) Å30.33 × 0.11 × 0.07 mm
Z = 2
Data collection top
Bruker SMART 1000 area-detector
diffractometer
3551 independent reflections
Radiation source: fine-focus sealed tube2997 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 8.33 pixels mm-1θmax = 32.0°, θmin = 2.6°
φ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2120
Tmin = 0.675, Tmax = 0.866l = 1414
13226 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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.5822P]
where P = (Fo2 + 2Fc2)/3
3551 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.54 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.34785 (3)0.50742 (1)0.35372 (2)0.01738 (7)
O10.3408 (2)0.4413 (1)0.5253 (1)0.0213 (2)
O20.3463 (2)0.5854 (1)0.1843 (1)0.0203 (2)
O30.4146 (2)0.3927 (1)0.2734 (1)0.0214 (3)
O40.5353 (2)0.3125 (1)0.1236 (2)0.0260 (3)
N10.2300 (2)0.6166 (1)0.4066 (2)0.0184 (3)
N20.2159 (2)0.6886 (1)0.3089 (2)0.0216 (3)
N30.2503 (2)0.7260 (1)0.0843 (2)0.0240 (3)
C10.2459 (2)0.4659 (1)0.6179 (2)0.0189 (3)
C20.2351 (2)0.4016 (1)0.7273 (2)0.0237 (3)
C30.1459 (3)0.4247 (2)0.8319 (2)0.0287 (4)
C40.0599 (3)0.5114 (2)0.8307 (2)0.0309 (4)
C50.0667 (2)0.5746 (2)0.7239 (2)0.0254 (4)
C60.1584 (2)0.5540 (1)0.6172 (2)0.0194 (3)
C70.1561 (2)0.6265 (1)0.5128 (2)0.0204 (3)
C80.2728 (2)0.6644 (1)0.1901 (2)0.0181 (3)
C90.4956 (2)0.3882 (1)0.1718 (2)0.0193 (3)
H2n0.17410.74490.32190.026*
H3n10.28710.71230.00690.029*
H3n20.19860.78050.09150.029*
H20.29010.34160.72920.028*
H30.14310.38080.90550.034*
H40.00190.52650.90230.037*
H50.00790.63350.72220.030*
H70.09760.68420.52250.025*
H90.52630.44530.13190.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0206 (1)0.0153 (1)0.0185 (1)0.0030 (1)0.0090 (1)0.0020 (1)
O10.024 (1)0.021 (1)0.023 (1)0.004 (1)0.011 (1)0.005 (1)
O20.024 (1)0.018 (1)0.022 (1)0.005 (1)0.011 (1)0.002 (1)
O30.026 (1)0.016 (1)0.025 (1)0.000 (1)0.013 (1)0.001 (1)
O40.035 (1)0.018 (1)0.031 (1)0.003 (1)0.018 (1)0.005 (1)
N10.022 (1)0.017 (1)0.018 (1)0.002 (1)0.008 (1)0.003 (1)
N20.031 (1)0.016 (1)0.022 (1)0.007 (1)0.014 (1)0.005 (1)
N30.034 (1)0.018 (1)0.024 (1)0.006 (1)0.014 (1)0.005 (1)
C10.016 (1)0.023 (1)0.018 (1)0.002 (1)0.004 (1)0.003 (1)
C20.021 (1)0.027 (1)0.023 (1)0.003 (1)0.005 (1)0.006 (1)
C30.028 (1)0.039 (1)0.021 (1)0.004 (1)0.008 (1)0.009 (1)
C40.031 (1)0.045 (1)0.021 (1)0.002 (1)0.013 (1)0.005 (1)
C50.025 (1)0.035 (1)0.019 (1)0.004 (1)0.010 (1)0.001 (1)
C60.017 (1)0.026 (1)0.016 (1)0.001 (1)0.006 (1)0.002 (1)
C70.022 (1)0.022 (1)0.019 (1)0.004 (1)0.008 (1)0.000 (1)
C80.019 (1)0.018 (1)0.020 (1)0.000 (1)0.008 (1)0.001 (1)
C90.022 (1)0.016 (1)0.021 (8)0.002 (1)0.007 (1)0.000 (1)
Geometric parameters (Å, º) top
Cu1—O11.918 (1)C2—C31.386 (3)
Cu1—O1i2.546 (1)C3—C41.396 (3)
Cu1—O21.976 (1)C4—C51.378 (3)
Cu1—O31.922 (1)C5—C61.408 (2)
Cu1—N11.923 (1)C6—C71.439 (2)
O1—C11.326 (2)N2—H2n0.88
O2—C81.262 (2)N3—H3n10.88
O3—C91.280 (2)N3—H3n20.88
O4—C91.234 (2)C2—H20.95
N1—C71.290 (2)C3—H30.95
N1—N21.380 (2)C4—H40.95
N2—C81.364 (2)C5—H50.95
N3—C81.328 (2)C7—H70.95
C1—C21.413 (2)C9—H90.95
C1—C61.419 (3)
O1—Cu1—O1i86.90 (5)C5—C6—C7116.0 (2)
O1—Cu1—O2174.84 (5)C1—C6—C7124.2 (2)
O1—Cu1—O389.97 (5)N1—C7—C6122.9 (2)
O1—Cu1—N193.19 (6)O2—C8—N3122.1 (2)
O1i—Cu1—O293.10 (5)O2—C8—N2119.6 (2)
O1i—Cu1—O396.57 (5)N3—C8—N2118.3 (2)
O1i—Cu1—N196.11 (5)O4—C9—O3122.7 (2)
O2—Cu1—O395.16 (5)C8—N2—H2n123.2
O2—Cu1—N181.67 (5)N1—N2—H2n123.2
O3—Cu1—N1167.07 (6)C8—N3—H3n1120.0
C1—O1—Cu1125.7 (1)C8—N3—H3n2120.0
C8—O2—Cu1112.3 (1)H3n1—N3—H3n2120.0
C9—O3—Cu1125.1 (1)C3—C2—H2119.4
C7—N1—N2119.0 (1)C1—C2—H2119.4
C7—N1—Cu1128.3 (1)C2—C3—H3119.5
N2—N1—Cu1112.5 (1)C4—C3—H3119.5
C8—N2—N1113.7 (1)C5—C4—H4120.6
O1—C1—C2118.1 (2)C3—C4—H4120.6
O1—C1—C6124.3 (2)C4—C5—H5119.2
C2—C1—C6117.5 (2)C6—C5—H5119.2
C3—C2—C1121.2 (2)N1—C7—H7118.5
C2—C3—C4121.1 (2)C6—C7—H7118.5
C5—C4—C3118.7 (2)O4—C9—H9118.7
C4—C5—C6121.7 (2)O3—C9—H9118.7
C5—C6—C1119.8 (2)
O3—Cu1—O1—C1154.9 (1)Cu1—O1—C1—C611.6 (2)
N1—Cu1—O1—C112.6 (2)O1—C1—C2—C3176.6 (2)
O1i—Cu1—O1—C1108.5 (2)C6—C1—C2—C31.4 (3)
O3—Cu1—O2—C8167.0 (1)C1—C2—C3—C41.5 (3)
N1—Cu1—O2—C80.4 (1)C2—C3—C4—C50.6 (3)
O1i—Cu1—O2—C896.1 (1)C3—C4—C5—C60.4 (3)
O1—Cu1—O3—C9157.2 (2)C4—C5—C6—C10.4 (3)
N1—Cu1—O3—C998.5 (3)C4—C5—C6—C7179.5 (2)
O2—Cu1—O3—C923.4 (2)O1—C1—C6—C5177.5 (2)
O1i—Cu1—O3—C970.3 (2)C2—C1—C6—C50.5 (3)
O1—Cu1—N1—C78.6 (2)O1—C1—C6—C72.4 (3)
O3—Cu1—N1—C795.3 (3)C2—C1—C6—C7179.6 (2)
O2—Cu1—N1—C7171.9 (2)N2—N1—C7—C6177.7 (2)
O1i—Cu1—N1—C795.8 (2)Cu1—N1—C7—C63.1 (3)
O1—Cu1—N1—N2176.5 (1)C5—C6—C7—N1177.9 (2)
O3—Cu1—N1—N279.6 (3)C1—C6—C7—N12.2 (3)
O2—Cu1—N1—N23.0 (1)Cu1—O2—C8—N3176.9 (2)
O1i—Cu1—N1—N289.2 (1)Cu1—O2—C8—N23.9 (2)
C7—N1—N2—C8169.7 (2)N1—N2—C8—O26.6 (2)
Cu1—N1—N2—C85.8 (2)N1—N2—C8—N3174.2 (2)
Cu1—O1—C1—C2170.5 (1)Cu1—O3—C9—O4179.8 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2n···O4ii0.882.052.804 (2)143
N3—H3n1···O4iii0.882.092.931 (2)159
N3—H3n2···O1ii0.882.533.256 (2)140
N3—H3n2···O3ii0.882.353.144 (2)151
Symmetry codes: (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y+1, z.
 

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