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[N′-(4-Meth­­oxy-2-oxido­benzyl­­idene)4-nitro­benzohydrazidato-κ3O,N,O′](pyridine-κN)copper(II)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 15 December 2008; accepted 16 December 2008; online 20 December 2008)

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[Ali, H., Khamis, N. A., Basirun, W. J. & Yamin, B. M. (2004). Acta Cryst. E60, m982-m983.]); Chen & Liu (2004[Chen, W.-H. & Liu, S.-X. (2004). Chin. J. Inorg. Chem. 20, 668-670.]); Das & Pal (2005[Das, S. & Pal, S. (2005). J. Mol. Struct. 753, 68-79.]); Fariati et al. (2002[Fariati, F., Caruso, U., Centore, R., Marcolli, W., De Maria, A., Panunzi, B., Roviello, A. & Tuzi, A. (2002). Inorg. Chem. 41, 6597-6603.]); Lu & Liu (2005[Lu, W.-G. & Liu, H.-W. (2005). Chin. J. Struct. Chem. 24, 1078-1082.]); Lu et al. (2003[Lu, W.-G., Feng, X.-L., Liu, H.-W. & Wang, S.-L. (2003). Chin. J. Inorg. Chem. 19, 206-210.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C15H11N3O5)(C5H5N)]

  • Mr = 455.91

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.807, Tmax = 1.000 (expected range = 0.757–0.939)

  • 6268 measured reflections

  • 3942 independent reflections

  • 3605 reflections with I > 2σ(I)

  • Rint = 0.013

Refinement
  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] 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.
[N'-(4-Methoxy-2-oxidobenzylidene)-4-nitrobenzohydrazidato- κ3O,N,O'](pyridine-κN)copper(II) top
Crystal data top
[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 top
Bruker SMART APEX
diffractometer
3942 independent reflections
Radiation source: fine-focus sealed tube3605 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 68
Tmin = 0.807, Tmax = 1.000k = 1212
6268 measured reflectionsl = 1919
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.09 w = 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 = 0.32 e Å3
Crystal data top
[Cu(C15H11N3O5)(C5H5N)]γ = 107.088 (1)°
Mr = 455.91V = 892.31 (3) Å3
Triclinic, P1Z = 2
a = 6.3529 (1) ÅMo Kα radiation
b = 9.8409 (2) ŵ = 1.27 mm1
c = 15.1303 (3) ÅT = 100 K
α = 98.063 (1)°0.40 × 0.10 × 0.05 mm
β = 92.011 (1)°
Data collection top
Bruker SMART APEX
diffractometer
3942 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3605 reflections with I > 2σ(I)
Tmin = 0.807, Tmax = 1.000Rint = 0.013
6268 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 1.09Δρmax = 0.45 e Å3
3942 reflectionsΔρmin = 0.32 e Å3
272 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H8A0.03520.29390.94920.037*
H8B0.00380.23330.84840.037*
H8C0.05400.38400.87070.037*
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) top
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, º) top
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—C7179.56 (18)C1—C6—C7—N11.0 (3)
O1—Cu1—N1—N2178.07 (13)Cu1—O3—C9—N21.5 (2)
O3—Cu1—N1—N20.60 (12)Cu1—O3—C9—C10177.59 (12)
C7—N1—N2—C9179.91 (17)N1—N2—C9—O31.0 (3)
Cu1—N1—N2—C90.05 (19)N1—N2—C9—C10178.08 (15)
O1—Cu1—N4—C20174.53 (15)O3—C9—C10—C159.0 (3)
O3—Cu1—N4—C204.54 (15)N2—C9—C10—C15170.09 (17)
O1—Cu1—N4—C161.39 (16)O3—C9—C10—C11170.48 (17)
O3—Cu1—N4—C16179.54 (15)N2—C9—C10—C1110.4 (3)
N1—Cu1—O1—C12.34 (16)C15—C10—C11—C120.4 (3)
N4—Cu1—O1—C1173.51 (16)C9—C10—C11—C12179.15 (17)
N1—Cu1—O3—C91.01 (12)C10—C11—C12—C130.1 (3)
N4—Cu1—O3—C9176.72 (13)C11—C12—C13—C140.4 (3)
Cu1—O1—C1—C2178.09 (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—C125.6 (3)
C6—C1—C2—C31.1 (3)O5—N3—C13—C146.3 (3)
C8—O2—C3—C2178.07 (18)O4—N3—C13—C14173.44 (18)
C8—O2—C3—C42.8 (3)C12—C13—C14—C150.6 (3)
C1—C2—C3—O2178.47 (17)N3—C13—C14—C15179.62 (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—C14179.40 (17)
C3—C4—C5—C60.4 (3)C20—N4—C16—C170.1 (3)
C4—C5—C6—C10.1 (3)Cu1—N4—C16—C17175.93 (16)
C4—C5—C6—C7179.44 (17)N4—C16—C17—C180.0 (3)
O1—C1—C6—C5178.95 (17)C16—C17—C18—C190.1 (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—C7179.86 (17)Cu1—N4—C20—C19175.60 (15)
N2—N1—C7—C6179.34 (16)C18—C19—C20—N40.6 (3)
Cu1—N1—C7—C60.5 (3)

Experimental details

Crystal data
Chemical formula[Cu(C15H11N3O5)(C5H5N)]
Mr455.91
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)6.3529 (1), 9.8409 (2), 15.1303 (3)
α, β, γ (°)98.063 (1), 92.011 (1), 107.088 (1)
V3)892.31 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.27
Crystal size (mm)0.40 × 0.10 × 0.05
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.807, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
6268, 3942, 3605
Rint0.013
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.087, 1.09
No. of reflections3942
No. of parameters272
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.45, 0.32

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2009).

 

Acknowledgements

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

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