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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Dec 20;65(Pt 1):m121. doi: 10.1107/S1600536808042803

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

Nooraziah Mohd Lair a, Hapipah Mohd Ali a, Seik Weng Ng a,*
PMCID: PMC2968021  PMID: 21581485

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 ▶); Chen & Liu (2004 ▶); Das & Pal (2005 ▶); Fariati et al. (2002 ▶); Lu & Liu (2005 ▶); Lu et al. (2003 ▶).graphic file with name e-65-0m121-scheme1.jpg

Experimental

Crystal data

  • [Cu(C15H11N3O5)(C5H5N)]

  • M r = 455.91

  • Triclinic, Inline graphic

  • 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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: publCIF (Westrip, 2009 ▶).

Supplementary Material

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

e-65-0m121-sup1.cif (19.8KB, cif)

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

e-65-0m121-Isup2.hkl (193.2KB, 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.

Fig. 1.

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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 = 455.91 F(000) = 466
Triclinic, P1 Dx = 1.697 Mg m−3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 6.3529 (1) Å Cell parameters from 3716 reflections
b = 9.8409 (2) Å θ = 2.4–29.2°
c = 15.1303 (3) Å µ = 1.27 mm−1
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
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Data collection

Bruker SMART APEX diffractometer 3942 independent reflections
Radiation source: fine-focus sealed tube 3605 reflections with I > 2σ(I)
graphite Rint = 0.013
ω scans θmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −6→8
Tmin = 0.807, Tmax = 1.000 k = −12→12
6268 measured reflections l = −19→19
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087 H-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 parameters Δρmax = 0.45 e Å−3
0 restraints Δρmin = −0.31 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Cu1 1.14506 (4) 0.70062 (2) 0.728016 (14) 0.01312 (9)
N1 0.9381 (3) 0.64556 (17) 0.62386 (11) 0.0150 (3)
N2 1.0273 (3) 0.68298 (18) 0.54424 (10) 0.0159 (3)
N3 1.7555 (3) 0.93172 (18) 0.27544 (11) 0.0189 (4)
N4 1.3792 (3) 0.78081 (17) 0.82931 (11) 0.0145 (3)
O1 0.9305 (2) 0.61658 (15) 0.80405 (9) 0.0163 (3)
O2 0.2533 (2) 0.39329 (16) 0.90700 (9) 0.0199 (3)
O3 1.3444 (2) 0.77637 (15) 0.64095 (9) 0.0159 (3)
O4 1.6632 (3) 0.91481 (17) 0.20033 (9) 0.0247 (3)
O5 1.9560 (3) 0.9856 (2) 0.29243 (11) 0.0311 (4)
C1 0.7183 (3) 0.5521 (2) 0.78294 (13) 0.0139 (4)
C2 0.5869 (3) 0.5009 (2) 0.85092 (13) 0.0152 (4)
H2 0.6540 0.5120 0.9097 0.018*
C3 0.3615 (3) 0.4346 (2) 0.83442 (13) 0.0149 (4)
C4 0.2562 (3) 0.4147 (2) 0.74829 (13) 0.0151 (4)
H4 0.1016 0.3693 0.7371 0.018*
C5 0.3837 (3) 0.4630 (2) 0.68048 (13) 0.0146 (4)
H5 0.3142 0.4495 0.6219 0.018*
C6 0.6124 (3) 0.5313 (2) 0.69468 (12) 0.0140 (4)
C7 0.7290 (3) 0.5785 (2) 0.61964 (12) 0.0149 (4)
H7 0.6471 0.5592 0.5631 0.018*
C8 0.0219 (3) 0.3204 (3) 0.89270 (15) 0.0247 (5)
H8A −0.0352 0.2939 0.9492 0.037*
H8B −0.0038 0.2333 0.8484 0.037*
H8C −0.0540 0.3840 0.8707 0.037*
C9 1.2393 (3) 0.7493 (2) 0.56222 (12) 0.0140 (4)
C10 1.3714 (3) 0.79538 (19) 0.48671 (12) 0.0142 (4)
C11 1.2684 (3) 0.7902 (2) 0.40223 (13) 0.0162 (4)
H11 1.1119 0.7555 0.3927 0.019*
C12 1.3932 (3) 0.8352 (2) 0.33284 (13) 0.0174 (4)
H12 1.3242 0.8321 0.2755 0.021*
C13 1.6204 (3) 0.8849 (2) 0.34864 (12) 0.0149 (4)
C14 1.7277 (3) 0.8905 (2) 0.43096 (13) 0.0162 (4)
H14 1.8844 0.9243 0.4396 0.019*
C15 1.6016 (3) 0.8457 (2) 0.50049 (12) 0.0146 (4)
H15 1.6720 0.8492 0.5576 0.017*
C16 1.3332 (3) 0.7615 (2) 0.91374 (13) 0.0189 (4)
H16 1.1851 0.7146 0.9246 0.023*
C17 1.4910 (3) 0.8068 (2) 0.98487 (13) 0.0219 (4)
H17 1.4524 0.7913 1.0435 0.026*
C18 1.7074 (3) 0.8753 (2) 0.96950 (14) 0.0210 (4)
H18 1.8197 0.9079 1.0175 0.025*
C19 1.7569 (3) 0.8955 (2) 0.88305 (13) 0.0189 (4)
H19 1.9041 0.9416 0.8707 0.023*
C20 1.5893 (3) 0.8476 (2) 0.81504 (13) 0.0161 (4)
H20 1.6239 0.8625 0.7559 0.019*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Cu1 0.01168 (13) 0.01707 (13) 0.00996 (13) 0.00263 (9) 0.00095 (8) 0.00366 (8)
N1 0.0165 (8) 0.0172 (8) 0.0117 (7) 0.0044 (6) 0.0032 (6) 0.0046 (6)
N2 0.0166 (8) 0.0193 (8) 0.0109 (7) 0.0027 (7) 0.0034 (6) 0.0048 (6)
N3 0.0245 (9) 0.0184 (8) 0.0147 (8) 0.0060 (7) 0.0075 (7) 0.0047 (6)
N4 0.0133 (8) 0.0162 (8) 0.0137 (8) 0.0039 (6) 0.0007 (6) 0.0032 (6)
O1 0.0109 (6) 0.0234 (7) 0.0136 (6) 0.0025 (5) 0.0012 (5) 0.0057 (5)
O2 0.0136 (7) 0.0297 (8) 0.0154 (7) 0.0027 (6) 0.0032 (5) 0.0082 (6)
O3 0.0139 (7) 0.0218 (7) 0.0110 (6) 0.0028 (5) 0.0006 (5) 0.0046 (5)
O4 0.0325 (9) 0.0307 (8) 0.0127 (7) 0.0103 (7) 0.0053 (6) 0.0074 (6)
O5 0.0224 (8) 0.0431 (10) 0.0229 (8) −0.0003 (7) 0.0092 (7) 0.0092 (7)
C1 0.0131 (9) 0.0140 (8) 0.0154 (9) 0.0050 (7) 0.0014 (7) 0.0030 (7)
C2 0.0143 (9) 0.0192 (9) 0.0130 (9) 0.0056 (8) 0.0009 (7) 0.0041 (7)
C3 0.0156 (9) 0.0160 (9) 0.0141 (9) 0.0048 (7) 0.0042 (7) 0.0046 (7)
C4 0.0125 (9) 0.0156 (9) 0.0157 (9) 0.0025 (7) 0.0007 (7) 0.0018 (7)
C5 0.0167 (9) 0.0141 (8) 0.0124 (8) 0.0041 (7) −0.0001 (7) 0.0011 (7)
C6 0.0156 (9) 0.0133 (8) 0.0127 (8) 0.0040 (7) 0.0021 (7) 0.0021 (7)
C7 0.0164 (9) 0.0153 (9) 0.0115 (8) 0.0027 (7) −0.0009 (7) 0.0024 (7)
C8 0.0126 (10) 0.0395 (13) 0.0216 (10) 0.0032 (9) 0.0058 (8) 0.0122 (9)
C9 0.0169 (9) 0.0146 (9) 0.0116 (8) 0.0055 (7) 0.0025 (7) 0.0038 (7)
C10 0.0171 (9) 0.0129 (8) 0.0130 (9) 0.0046 (7) 0.0022 (7) 0.0034 (7)
C11 0.0146 (9) 0.0202 (9) 0.0135 (9) 0.0045 (7) 0.0005 (7) 0.0033 (7)
C12 0.0211 (10) 0.0199 (9) 0.0111 (9) 0.0057 (8) 0.0007 (7) 0.0033 (7)
C13 0.0197 (10) 0.0138 (9) 0.0116 (8) 0.0048 (7) 0.0055 (7) 0.0035 (7)
C14 0.0154 (9) 0.0159 (9) 0.0166 (9) 0.0035 (7) 0.0019 (7) 0.0021 (7)
C15 0.0168 (9) 0.0163 (9) 0.0111 (8) 0.0050 (7) 0.0014 (7) 0.0037 (7)
C16 0.0148 (10) 0.0249 (10) 0.0147 (9) 0.0021 (8) 0.0019 (7) 0.0031 (8)
C17 0.0193 (10) 0.0293 (11) 0.0125 (9) 0.0008 (9) 0.0010 (8) 0.0029 (8)
C18 0.0186 (10) 0.0248 (10) 0.0149 (9) 0.0007 (8) −0.0034 (8) 0.0013 (8)
C19 0.0143 (9) 0.0197 (10) 0.0199 (10) 0.0008 (8) 0.0009 (8) 0.0033 (8)
C20 0.0156 (9) 0.0176 (9) 0.0143 (9) 0.0033 (7) 0.0026 (7) 0.0036 (7)
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Geometric parameters (Å, °)

Cu1—O1 1.8922 (14) C6—C7 1.435 (3)
Cu1—N1 1.9239 (16) C7—H7 0.9500
Cu1—O3 1.9320 (14) C8—H8A 0.9800
Cu1—N4 1.9989 (16) C8—H8B 0.9800
N1—C7 1.293 (3) C8—H8C 0.9800
N1—N2 1.399 (2) C9—C10 1.485 (3)
N2—C9 1.312 (3) C10—C15 1.397 (3)
N3—O5 1.229 (2) C10—C11 1.403 (3)
N3—O4 1.227 (2) C11—C12 1.382 (3)
N3—C13 1.467 (2) C11—H11 0.9500
N4—C20 1.343 (3) C12—C13 1.381 (3)
N4—C16 1.347 (2) C12—H12 0.9500
O1—C1 1.316 (2) C13—C14 1.385 (3)
O2—C3 1.363 (2) C14—C15 1.387 (3)
O2—C8 1.427 (2) C14—H14 0.9500
O3—C9 1.299 (2) C15—H15 0.9500
C1—C2 1.403 (3) C16—C17 1.375 (3)
C1—C6 1.434 (3) C16—H16 0.9500
C2—C3 1.385 (3) C17—C18 1.386 (3)
C2—H2 0.9500 C17—H17 0.9500
C3—C4 1.405 (3) C18—C19 1.384 (3)
C4—C5 1.380 (3) C18—H18 0.9500
C4—H4 0.9500 C19—C20 1.381 (3)
C5—C6 1.404 (3) C19—H19 0.9500
C5—H5 0.9500 C20—H20 0.9500
O1—Cu1—N1 93.57 (6) O2—C8—H8B 109.5
O1—Cu1—O3 174.58 (6) H8A—C8—H8B 109.5
N1—Cu1—O3 81.17 (6) O2—C8—H8C 109.5
O1—Cu1—N4 92.67 (6) H8A—C8—H8C 109.5
N1—Cu1—N4 172.51 (7) H8B—C8—H8C 109.5
O3—Cu1—N4 92.68 (6) O3—C9—N2 125.19 (17)
C7—N1—N2 117.25 (16) O3—C9—C10 117.01 (17)
C7—N1—Cu1 127.41 (13) N2—C9—C10 117.79 (16)
N2—N1—Cu1 115.34 (12) C15—C10—C11 119.71 (17)
C9—N2—N1 108.05 (15) C15—C10—C9 119.31 (16)
O5—N3—O4 123.25 (17) C11—C10—C9 120.98 (18)
O5—N3—C13 118.27 (16) C12—C11—C10 120.41 (18)
O4—N3—C13 118.47 (17) C12—C11—H11 119.8
C20—N4—C16 117.86 (17) C10—C11—H11 119.8
C20—N4—Cu1 121.38 (13) C11—C12—C13 118.53 (17)
C16—N4—Cu1 120.64 (14) C11—C12—H12 120.7
C1—O1—Cu1 127.54 (12) C13—C12—H12 120.7
C3—O2—C8 117.33 (15) C12—C13—C14 122.62 (18)
C9—O3—Cu1 110.23 (12) C12—C13—N3 119.26 (17)
O1—C1—C2 118.11 (17) C14—C13—N3 118.12 (18)
O1—C1—C6 124.11 (17) C15—C14—C13 118.62 (18)
C2—C1—C6 117.78 (17) C15—C14—H14 120.7
C3—C2—C1 121.55 (17) C13—C14—H14 120.7
C3—C2—H2 119.2 C14—C15—C10 120.11 (17)
C1—C2—H2 119.2 C14—C15—H15 119.9
O2—C3—C2 115.33 (17) C10—C15—H15 119.9
O2—C3—C4 123.65 (18) N4—C16—C17 122.91 (19)
C2—C3—C4 121.01 (18) N4—C16—H16 118.5
C5—C4—C3 118.12 (18) C17—C16—H16 118.5
C5—C4—H4 120.9 C16—C17—C18 118.84 (19)
C3—C4—H4 120.9 C16—C17—H17 120.6
C4—C5—C6 122.53 (17) C18—C17—H17 120.6
C4—C5—H5 118.7 C19—C18—C17 118.81 (19)
C6—C5—H5 118.7 C19—C18—H18 120.6
C5—C6—C1 119.00 (17) C17—C18—H18 120.6
C5—C6—C7 117.98 (17) C20—C19—C18 119.05 (19)
C1—C6—C7 123.02 (17) C20—C19—H19 120.5
N1—C7—C6 124.30 (17) C18—C19—H19 120.5
N1—C7—H7 117.9 N4—C20—C19 122.52 (18)
C6—C7—H7 117.9 N4—C20—H20 118.7
O2—C8—H8A 109.5 C19—C20—H20 118.7
O1—Cu1—N1—C7 1.77 (18) C5—C6—C7—N1 178.35 (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—N2 1.5 (2)
O3—Cu1—N1—N2 0.60 (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—C10 178.08 (15)
O1—Cu1—N4—C20 174.53 (15) O3—C9—C10—C15 9.0 (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—C16 179.54 (15) N2—C9—C10—C11 10.4 (3)
N1—Cu1—O1—C1 −2.34 (16) C15—C10—C11—C12 −0.4 (3)
N4—Cu1—O1—C1 173.51 (16) C9—C10—C11—C12 179.15 (17)
N1—Cu1—O3—C9 −1.01 (12) C10—C11—C12—C13 0.1 (3)
N4—Cu1—O3—C9 −176.72 (13) C11—C12—C13—C14 0.4 (3)
Cu1—O1—C1—C2 −178.09 (13) C11—C12—C13—N3 179.37 (17)
Cu1—O1—C1—C6 1.7 (3) O5—N3—C13—C12 174.64 (18)
O1—C1—C2—C3 178.63 (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—C14 173.44 (18)
C8—O2—C3—C4 2.8 (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—C4 0.7 (3) C13—C14—C15—C10 0.4 (3)
O2—C3—C4—C5 179.17 (17) C11—C10—C15—C14 0.1 (3)
C2—C3—C4—C5 0.0 (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—C17 175.93 (16)
C4—C5—C6—C7 −179.44 (17) N4—C16—C17—C18 0.0 (3)
O1—C1—C6—C5 −178.95 (17) C16—C17—C18—C19 −0.1 (3)
C2—C1—C6—C5 0.8 (3) C17—C18—C19—C20 0.4 (3)
O1—C1—C6—C7 0.4 (3) C16—N4—C20—C19 0.4 (3)
C2—C1—C6—C7 −179.86 (17) Cu1—N4—C20—C19 −175.60 (15)
N2—N1—C7—C6 179.34 (16) C18—C19—C20—N4 −0.6 (3)
Cu1—N1—C7—C6 −0.5 (3)
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Footnotes

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

References

  1. Ali, H., Khamis, N. A., Basirun, W. J. & Yamin, B. M. (2004). Acta Cryst. E60, m982–m983.
  2. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  3. Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  4. Chen, W.-H. & Liu, S.-X. (2004). Chin. J. Inorg. Chem.20, 668–670.
  5. Das, S. & Pal, S. (2005). J. Mol. Struct.753, 68–79.
  6. Fariati, F., Caruso, U., Centore, R., Marcolli, W., De Maria, A., Panunzi, B., Roviello, A. & Tuzi, A. (2002). Inorg. Chem.41, 6597–6603. [DOI] [PubMed]
  7. Lu, W.-G., Feng, X.-L., Liu, H.-W. & Wang, S.-L. (2003). Chin. J. Inorg. Chem.19, 206–210.
  8. Lu, W.-G. & Liu, H.-W. (2005). Chin. J. Struct. Chem.24, 1078–1082.
  9. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  10. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  11. Westrip, S. P. (2009). publCIF In preparation.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-65-0m121-sup1.cif (19.8KB, cif)

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

e-65-0m121-Isup2.hkl (193.2KB, hkl)

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

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

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