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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m121.
Published online 2008 December 20. doi:  10.1107/S1600536808042803
PMCID: PMC2968021

[N′-(4-Meth­oxy-2-oxidobenzyl­idene)4-nitro­benzohydrazidato-κ3 O,N,O′](pyridine-κN)copper(II)

Abstract

The pyridine-coordinated CuII atom in the title Schiff base complex, [Cu(C15H11N3O5)(C5H5N)], is O,N,O′-chelated by the doubly deprotonated Schiff base ligand. The metal centre is in a square-planar coordination geometry.

Related literature

For the pyridine adducts of copper derivatives of similar ligands, see: Ali et al. (2004 [triangle]); Chen & Liu (2004 [triangle]); Das & Pal (2005 [triangle]); Fariati et al. (2002 [triangle]); Lu & Liu (2005 [triangle]); Lu et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m121-scheme1.jpg

Experimental

Crystal data

  • [Cu(C15H11N3O5)(C5H5N)]
  • M r = 455.91
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m121-efi1.jpg
  • a = 6.3529 (1) Å
  • b = 9.8409 (2) Å
  • c = 15.1303 (3) Å
  • α = 98.063 (1)°
  • β = 92.011 (1)°
  • γ = 107.088 (1)°
  • V = 892.31 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.27 mm−1
  • T = 100 (2) K
  • 0.40 × 0.10 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.807, T max = 1.000 (expected range = 0.757–0.939)
  • 6268 measured reflections
  • 3942 independent reflections
  • 3605 reflections with I > 2σ(I)
  • R int = 0.013

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.087
  • S = 1.09
  • 3942 reflections
  • 272 parameters
  • H-atom parameters constrained
  • Δρmax = 0.45 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042803/bt2838sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042803/bt2838Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031, 12–02-03–2051).

supplementary crystallographic information

Experimental

N'-2-Hydroxy-3-methoxybenzylidene)-nitrobenzohydrazide (0.30 g, 1 mmol) and copper acetate (0.20 g, 1 mmol) were heated in a ethanol (50 ml) for 2 hours. The solvent was removed and the resulting compound recrystallized from pyridine.

Refinement

Hydrogen atoms were placed at calculated positions (Caromatic–H 0.95 Å, Cmethyl–H 0.98 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2Ueq(Caromatic) or 1.5Ueq(Cmethyl).

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of Cu(C5H5N)(C15H11N3O5) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Cu(C15H11N3O5)(C5H5N)]Z = 2
Mr = 455.91F(000) = 466
Triclinic, P1Dx = 1.697 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3529 (1) ÅCell parameters from 3716 reflections
b = 9.8409 (2) Åθ = 2.4–29.2°
c = 15.1303 (3) ŵ = 1.27 mm1
α = 98.063 (1)°T = 100 K
β = 92.011 (1)°Block, brown
γ = 107.088 (1)°0.40 × 0.10 × 0.05 mm
V = 892.31 (3) Å3

Data collection

Bruker SMART APEX diffractometer3942 independent reflections
Radiation source: fine-focus sealed tube3605 reflections with I > 2σ(I)
graphiteRint = 0.013
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −6→8
Tmin = 0.807, Tmax = 1.000k = −12→12
6268 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0494P)2 + 0.535P] where P = (Fo2 + 2Fc2)/3
3942 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = −0.31 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cu11.14506 (4)0.70062 (2)0.728016 (14)0.01312 (9)
N10.9381 (3)0.64556 (17)0.62386 (11)0.0150 (3)
N21.0273 (3)0.68298 (18)0.54424 (10)0.0159 (3)
N31.7555 (3)0.93172 (18)0.27544 (11)0.0189 (4)
N41.3792 (3)0.78081 (17)0.82931 (11)0.0145 (3)
O10.9305 (2)0.61658 (15)0.80405 (9)0.0163 (3)
O20.2533 (2)0.39329 (16)0.90700 (9)0.0199 (3)
O31.3444 (2)0.77637 (15)0.64095 (9)0.0159 (3)
O41.6632 (3)0.91481 (17)0.20033 (9)0.0247 (3)
O51.9560 (3)0.9856 (2)0.29243 (11)0.0311 (4)
C10.7183 (3)0.5521 (2)0.78294 (13)0.0139 (4)
C20.5869 (3)0.5009 (2)0.85092 (13)0.0152 (4)
H20.65400.51200.90970.018*
C30.3615 (3)0.4346 (2)0.83442 (13)0.0149 (4)
C40.2562 (3)0.4147 (2)0.74829 (13)0.0151 (4)
H40.10160.36930.73710.018*
C50.3837 (3)0.4630 (2)0.68048 (13)0.0146 (4)
H50.31420.44950.62190.018*
C60.6124 (3)0.5313 (2)0.69468 (12)0.0140 (4)
C70.7290 (3)0.5785 (2)0.61964 (12)0.0149 (4)
H70.64710.55920.56310.018*
C80.0219 (3)0.3204 (3)0.89270 (15)0.0247 (5)
H8A−0.03520.29390.94920.037*
H8B−0.00380.23330.84840.037*
H8C−0.05400.38400.87070.037*
C91.2393 (3)0.7493 (2)0.56222 (12)0.0140 (4)
C101.3714 (3)0.79538 (19)0.48671 (12)0.0142 (4)
C111.2684 (3)0.7902 (2)0.40223 (13)0.0162 (4)
H111.11190.75550.39270.019*
C121.3932 (3)0.8352 (2)0.33284 (13)0.0174 (4)
H121.32420.83210.27550.021*
C131.6204 (3)0.8849 (2)0.34864 (12)0.0149 (4)
C141.7277 (3)0.8905 (2)0.43096 (13)0.0162 (4)
H141.88440.92430.43960.019*
C151.6016 (3)0.8457 (2)0.50049 (12)0.0146 (4)
H151.67200.84920.55760.017*
C161.3332 (3)0.7615 (2)0.91374 (13)0.0189 (4)
H161.18510.71460.92460.023*
C171.4910 (3)0.8068 (2)0.98487 (13)0.0219 (4)
H171.45240.79131.04350.026*
C181.7074 (3)0.8753 (2)0.96950 (14)0.0210 (4)
H181.81970.90791.01750.025*
C191.7569 (3)0.8955 (2)0.88305 (13)0.0189 (4)
H191.90410.94160.87070.023*
C201.5893 (3)0.8476 (2)0.81504 (13)0.0161 (4)
H201.62390.86250.75590.019*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.01168 (13)0.01707 (13)0.00996 (13)0.00263 (9)0.00095 (8)0.00366 (8)
N10.0165 (8)0.0172 (8)0.0117 (7)0.0044 (6)0.0032 (6)0.0046 (6)
N20.0166 (8)0.0193 (8)0.0109 (7)0.0027 (7)0.0034 (6)0.0048 (6)
N30.0245 (9)0.0184 (8)0.0147 (8)0.0060 (7)0.0075 (7)0.0047 (6)
N40.0133 (8)0.0162 (8)0.0137 (8)0.0039 (6)0.0007 (6)0.0032 (6)
O10.0109 (6)0.0234 (7)0.0136 (6)0.0025 (5)0.0012 (5)0.0057 (5)
O20.0136 (7)0.0297 (8)0.0154 (7)0.0027 (6)0.0032 (5)0.0082 (6)
O30.0139 (7)0.0218 (7)0.0110 (6)0.0028 (5)0.0006 (5)0.0046 (5)
O40.0325 (9)0.0307 (8)0.0127 (7)0.0103 (7)0.0053 (6)0.0074 (6)
O50.0224 (8)0.0431 (10)0.0229 (8)−0.0003 (7)0.0092 (7)0.0092 (7)
C10.0131 (9)0.0140 (8)0.0154 (9)0.0050 (7)0.0014 (7)0.0030 (7)
C20.0143 (9)0.0192 (9)0.0130 (9)0.0056 (8)0.0009 (7)0.0041 (7)
C30.0156 (9)0.0160 (9)0.0141 (9)0.0048 (7)0.0042 (7)0.0046 (7)
C40.0125 (9)0.0156 (9)0.0157 (9)0.0025 (7)0.0007 (7)0.0018 (7)
C50.0167 (9)0.0141 (8)0.0124 (8)0.0041 (7)−0.0001 (7)0.0011 (7)
C60.0156 (9)0.0133 (8)0.0127 (8)0.0040 (7)0.0021 (7)0.0021 (7)
C70.0164 (9)0.0153 (9)0.0115 (8)0.0027 (7)−0.0009 (7)0.0024 (7)
C80.0126 (10)0.0395 (13)0.0216 (10)0.0032 (9)0.0058 (8)0.0122 (9)
C90.0169 (9)0.0146 (9)0.0116 (8)0.0055 (7)0.0025 (7)0.0038 (7)
C100.0171 (9)0.0129 (8)0.0130 (9)0.0046 (7)0.0022 (7)0.0034 (7)
C110.0146 (9)0.0202 (9)0.0135 (9)0.0045 (7)0.0005 (7)0.0033 (7)
C120.0211 (10)0.0199 (9)0.0111 (9)0.0057 (8)0.0007 (7)0.0033 (7)
C130.0197 (10)0.0138 (9)0.0116 (8)0.0048 (7)0.0055 (7)0.0035 (7)
C140.0154 (9)0.0159 (9)0.0166 (9)0.0035 (7)0.0019 (7)0.0021 (7)
C150.0168 (9)0.0163 (9)0.0111 (8)0.0050 (7)0.0014 (7)0.0037 (7)
C160.0148 (10)0.0249 (10)0.0147 (9)0.0021 (8)0.0019 (7)0.0031 (8)
C170.0193 (10)0.0293 (11)0.0125 (9)0.0008 (9)0.0010 (8)0.0029 (8)
C180.0186 (10)0.0248 (10)0.0149 (9)0.0007 (8)−0.0034 (8)0.0013 (8)
C190.0143 (9)0.0197 (10)0.0199 (10)0.0008 (8)0.0009 (8)0.0033 (8)
C200.0156 (9)0.0176 (9)0.0143 (9)0.0033 (7)0.0026 (7)0.0036 (7)

Geometric parameters (Å, °)

Cu1—O11.8922 (14)C6—C71.435 (3)
Cu1—N11.9239 (16)C7—H70.9500
Cu1—O31.9320 (14)C8—H8A0.9800
Cu1—N41.9989 (16)C8—H8B0.9800
N1—C71.293 (3)C8—H8C0.9800
N1—N21.399 (2)C9—C101.485 (3)
N2—C91.312 (3)C10—C151.397 (3)
N3—O51.229 (2)C10—C111.403 (3)
N3—O41.227 (2)C11—C121.382 (3)
N3—C131.467 (2)C11—H110.9500
N4—C201.343 (3)C12—C131.381 (3)
N4—C161.347 (2)C12—H120.9500
O1—C11.316 (2)C13—C141.385 (3)
O2—C31.363 (2)C14—C151.387 (3)
O2—C81.427 (2)C14—H140.9500
O3—C91.299 (2)C15—H150.9500
C1—C21.403 (3)C16—C171.375 (3)
C1—C61.434 (3)C16—H160.9500
C2—C31.385 (3)C17—C181.386 (3)
C2—H20.9500C17—H170.9500
C3—C41.405 (3)C18—C191.384 (3)
C4—C51.380 (3)C18—H180.9500
C4—H40.9500C19—C201.381 (3)
C5—C61.404 (3)C19—H190.9500
C5—H50.9500C20—H200.9500
O1—Cu1—N193.57 (6)O2—C8—H8B109.5
O1—Cu1—O3174.58 (6)H8A—C8—H8B109.5
N1—Cu1—O381.17 (6)O2—C8—H8C109.5
O1—Cu1—N492.67 (6)H8A—C8—H8C109.5
N1—Cu1—N4172.51 (7)H8B—C8—H8C109.5
O3—Cu1—N492.68 (6)O3—C9—N2125.19 (17)
C7—N1—N2117.25 (16)O3—C9—C10117.01 (17)
C7—N1—Cu1127.41 (13)N2—C9—C10117.79 (16)
N2—N1—Cu1115.34 (12)C15—C10—C11119.71 (17)
C9—N2—N1108.05 (15)C15—C10—C9119.31 (16)
O5—N3—O4123.25 (17)C11—C10—C9120.98 (18)
O5—N3—C13118.27 (16)C12—C11—C10120.41 (18)
O4—N3—C13118.47 (17)C12—C11—H11119.8
C20—N4—C16117.86 (17)C10—C11—H11119.8
C20—N4—Cu1121.38 (13)C11—C12—C13118.53 (17)
C16—N4—Cu1120.64 (14)C11—C12—H12120.7
C1—O1—Cu1127.54 (12)C13—C12—H12120.7
C3—O2—C8117.33 (15)C12—C13—C14122.62 (18)
C9—O3—Cu1110.23 (12)C12—C13—N3119.26 (17)
O1—C1—C2118.11 (17)C14—C13—N3118.12 (18)
O1—C1—C6124.11 (17)C15—C14—C13118.62 (18)
C2—C1—C6117.78 (17)C15—C14—H14120.7
C3—C2—C1121.55 (17)C13—C14—H14120.7
C3—C2—H2119.2C14—C15—C10120.11 (17)
C1—C2—H2119.2C14—C15—H15119.9
O2—C3—C2115.33 (17)C10—C15—H15119.9
O2—C3—C4123.65 (18)N4—C16—C17122.91 (19)
C2—C3—C4121.01 (18)N4—C16—H16118.5
C5—C4—C3118.12 (18)C17—C16—H16118.5
C5—C4—H4120.9C16—C17—C18118.84 (19)
C3—C4—H4120.9C16—C17—H17120.6
C4—C5—C6122.53 (17)C18—C17—H17120.6
C4—C5—H5118.7C19—C18—C17118.81 (19)
C6—C5—H5118.7C19—C18—H18120.6
C5—C6—C1119.00 (17)C17—C18—H18120.6
C5—C6—C7117.98 (17)C20—C19—C18119.05 (19)
C1—C6—C7123.02 (17)C20—C19—H19120.5
N1—C7—C6124.30 (17)C18—C19—H19120.5
N1—C7—H7117.9N4—C20—C19122.52 (18)
C6—C7—H7117.9N4—C20—H20118.7
O2—C8—H8A109.5C19—C20—H20118.7
O1—Cu1—N1—C71.77 (18)C5—C6—C7—N1178.35 (18)
O3—Cu1—N1—C7−179.56 (18)C1—C6—C7—N1−1.0 (3)
O1—Cu1—N1—N2−178.07 (13)Cu1—O3—C9—N21.5 (2)
O3—Cu1—N1—N20.60 (12)Cu1—O3—C9—C10−177.59 (12)
C7—N1—N2—C9−179.91 (17)N1—N2—C9—O3−1.0 (3)
Cu1—N1—N2—C9−0.05 (19)N1—N2—C9—C10178.08 (15)
O1—Cu1—N4—C20174.53 (15)O3—C9—C10—C159.0 (3)
O3—Cu1—N4—C20−4.54 (15)N2—C9—C10—C15−170.09 (17)
O1—Cu1—N4—C16−1.39 (16)O3—C9—C10—C11−170.48 (17)
O3—Cu1—N4—C16179.54 (15)N2—C9—C10—C1110.4 (3)
N1—Cu1—O1—C1−2.34 (16)C15—C10—C11—C12−0.4 (3)
N4—Cu1—O1—C1173.51 (16)C9—C10—C11—C12179.15 (17)
N1—Cu1—O3—C9−1.01 (12)C10—C11—C12—C130.1 (3)
N4—Cu1—O3—C9−176.72 (13)C11—C12—C13—C140.4 (3)
Cu1—O1—C1—C2−178.09 (13)C11—C12—C13—N3179.37 (17)
Cu1—O1—C1—C61.7 (3)O5—N3—C13—C12174.64 (18)
O1—C1—C2—C3178.63 (17)O4—N3—C13—C12−5.6 (3)
C6—C1—C2—C3−1.1 (3)O5—N3—C13—C14−6.3 (3)
C8—O2—C3—C2−178.07 (18)O4—N3—C13—C14173.44 (18)
C8—O2—C3—C42.8 (3)C12—C13—C14—C15−0.6 (3)
C1—C2—C3—O2−178.47 (17)N3—C13—C14—C15−179.62 (16)
C1—C2—C3—C40.7 (3)C13—C14—C15—C100.4 (3)
O2—C3—C4—C5179.17 (17)C11—C10—C15—C140.1 (3)
C2—C3—C4—C50.0 (3)C9—C10—C15—C14−179.40 (17)
C3—C4—C5—C6−0.4 (3)C20—N4—C16—C17−0.1 (3)
C4—C5—C6—C1−0.1 (3)Cu1—N4—C16—C17175.93 (16)
C4—C5—C6—C7−179.44 (17)N4—C16—C17—C180.0 (3)
O1—C1—C6—C5−178.95 (17)C16—C17—C18—C19−0.1 (3)
C2—C1—C6—C50.8 (3)C17—C18—C19—C200.4 (3)
O1—C1—C6—C70.4 (3)C16—N4—C20—C190.4 (3)
C2—C1—C6—C7−179.86 (17)Cu1—N4—C20—C19−175.60 (15)
N2—N1—C7—C6179.34 (16)C18—C19—C20—N4−0.6 (3)
Cu1—N1—C7—C6−0.5 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2838).

References

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  • Das, S. & Pal, S. (2005). J. Mol. Struct.753, 68–79.
  • Fariati, F., Caruso, U., Centore, R., Marcolli, W., De Maria, A., Panunzi, B., Roviello, A. & Tuzi, A. (2002). Inorg. Chem.41, 6597–6603. [PubMed]
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  • Westrip, S. P. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography