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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): m427–m428.
Published online 2009 March 25. doi:  10.1107/S1600536809007995
PMCID: PMC2969059

trans,trans,trans-Diaqua­bis(nicotin­amide-κN)bis­(2-nitro­benzoato-κO)copper(II)

Abstract

The water-coordinated metal atom in the title compound, [Cu(C7H4NO4)2(C6H6N2O)2(H2O)2], lies on a center of inversion in an all-trans octa­hedral environment with slight distortions. The mol­ecule inter­acts with adjacent mol­ecules through O—H(...)O and N—H(...)O hydrogen bonds, forming a layered network parallel to (010).

Related literature

There are recent examples of diaquadi(aryl­carboxyl­ato)di(nicotinamide)metal(II) compounds, see: Hökelek & Necefoğlu (2007a [triangle],b [triangle]); Hökelek et al. (2007 [triangle]); Koksharova et al. (2006 [triangle]); Şahin et al. (2007a [triangle], 2007b [triangle]); Stachova et al. (2006 [triangle]); Çaylak et al. (2007 [triangle]); Zhang et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m427-scheme1.jpg

Experimental

Crystal data

  • [Cu(C7H4NO4)2(C6H6N2O)2(H2O)2]
  • M r = 676.05
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m427-efi1.jpg
  • a = 7.9582 (3) Å
  • b = 18.7044 (6) Å
  • c = 9.8573 (2) Å
  • β = 104.012 (2)°
  • V = 1423.63 (8) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.84 mm−1
  • T = 295 K
  • 0.45 × 0.20 × 0.16 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.557, T max = 0.877
  • 7295 measured reflections
  • 2507 independent reflections
  • 2069 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.111
  • S = 1.12
  • 2507 reflections
  • 229 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.46 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [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]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007995/bt2894sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007995/bt2894Isup2.hkl

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

Acknowledgments

We thank the Foundation of Jiangsu Provincial Key Program of Physical Chemistry in Yangzhou University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

A water/methanol (1:1 v/v) solution (3 ml) of copper nitrate trihydrate (0.174 g, 0.6 mmol) was added to a water/methanol (1:1 v/v) solution (3 ml) of 2-nitrobenzoic acid (0.100 g, 0.6 mmol), sodium hydroxide (0.024 g 0.6 mmol) and nicotinamide (0.073 g, 0.6 mmol). Blue block were obtained after several days (yield: 40%). CH&N elemental analysis: calc. for C26H24CuN6O12: C 46.19, H 3.59,N 12.43%; found: C 46.37, H 3.41, N 12.60%.

Refinement

Carbon-bound H atoms were placed in calculated positions and were allowed to ride on the parent atoms. The oxygen-bound ones were located in a difference Fourier map, and were refined with distance restraints N–H, O–H = 0.85±0.01 Å; an additional H···H 1.39 + 0.01 Å restraint was used. Their displacement parameters were freely refined.

Figures

Fig. 1.
Thermal ellipsoid plot of Cu(H2O)2(C7H4NO4)2(C6H6N2O)2; displacement ellipsoids are drawn at the 50% probabability level, and H atoms as spheres of arbitrary radii.

Crystal data

[Cu(C7H4NO4)2(C6H6N2O)2(H2O)2]F(000) = 694
Mr = 676.05Dx = 1.577 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3858 reflections
a = 7.9582 (3) Åθ = 2.2–25.0°
b = 18.7044 (6) ŵ = 0.84 mm1
c = 9.8573 (2) ÅT = 295 K
β = 104.012 (2)°Block, blue
V = 1423.63 (8) Å30.45 × 0.20 × 0.16 mm
Z = 2

Data collection

Bruker SMART area-detector diffractometer2507 independent reflections
Radiation source: medium-focus sealed tube2069 reflections with I > 2σ(I)
graphiteRint = 0.036
[var phi] and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.557, Tmax = 0.877k = −14→22
7295 measured reflectionsl = −11→11

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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.12w = 1/[σ2(Fo2) + (0.0395P)2 + 1.8061P] where P = (Fo2 + 2Fc2)/3
2507 reflections(Δ/σ)max = 0.001
229 parametersΔρmax = 0.31 e Å3
4 restraintsΔρmin = −0.46 e Å3

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

xyzUiso*/Ueq
Cu10.50000.50000.50000.02960 (19)
O10.6141 (3)0.41263 (12)0.4483 (2)0.0329 (5)
O20.3896 (3)0.37179 (15)0.2856 (3)0.0531 (7)
O30.3215 (5)0.2416 (3)0.0916 (5)0.1123 (16)
O40.3942 (5)0.2153 (2)0.3108 (5)0.1137 (16)
O50.0632 (4)0.49124 (18)0.8331 (3)0.0642 (9)
O1W0.8082 (4)0.54476 (16)0.5876 (3)0.0493 (7)
H110.772 (6)0.5753 (19)0.637 (4)0.067 (15)*
H120.883 (5)0.522 (2)0.647 (4)0.073 (16)*
N10.4256 (5)0.2375 (2)0.2043 (5)0.0624 (10)
N20.4917 (3)0.45491 (14)0.6829 (3)0.0290 (6)
N30.1614 (5)0.4274 (2)1.0283 (3)0.0539 (9)
H310.081 (4)0.442 (2)1.065 (4)0.069 (14)*
H320.241 (4)0.403 (2)1.082 (4)0.075 (16)*
C10.6639 (4)0.32322 (17)0.2924 (3)0.0297 (7)
C20.6033 (5)0.26281 (19)0.2137 (4)0.0372 (8)
C30.7038 (6)0.2231 (2)0.1461 (4)0.0496 (10)
H30.65780.18350.09290.057 (12)*
C40.8740 (6)0.2428 (2)0.1585 (4)0.0552 (11)
H40.94330.21700.11250.065 (13)*
C50.9406 (5)0.3009 (2)0.2392 (4)0.0503 (10)
H51.05610.31350.24950.067 (14)*
C60.8366 (4)0.3409 (2)0.3053 (4)0.0395 (8)
H60.88340.38010.35910.038 (10)*
C70.5449 (4)0.37176 (17)0.3480 (3)0.0289 (7)
C80.3508 (4)0.46333 (17)0.7327 (3)0.0306 (7)
H80.25710.48820.67850.029 (9)*
C90.3378 (4)0.43678 (18)0.8613 (3)0.0304 (7)
C100.4781 (5)0.3999 (2)0.9403 (4)0.0434 (9)
H100.47470.38191.02760.048 (11)*
C110.6240 (5)0.3899 (2)0.8889 (4)0.0461 (10)
H11A0.71860.36440.94020.062 (13)*
C120.6259 (4)0.41833 (19)0.7608 (4)0.0364 (8)
H12A0.72410.41200.72680.032 (9)*
C130.1760 (5)0.4530 (2)0.9067 (4)0.0419 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.0375 (3)0.0296 (3)0.0256 (3)0.0041 (3)0.0153 (2)0.0014 (2)
O10.0378 (13)0.0332 (12)0.0292 (12)0.0057 (10)0.0110 (10)−0.0034 (10)
O20.0318 (14)0.0677 (19)0.0557 (17)0.0093 (13)0.0028 (12)−0.0203 (14)
O30.061 (2)0.178 (5)0.091 (3)−0.027 (3)0.006 (2)−0.071 (3)
O40.094 (3)0.118 (4)0.140 (4)−0.030 (3)0.049 (3)0.048 (3)
O50.0489 (16)0.107 (3)0.0436 (15)0.0375 (17)0.0254 (13)0.0285 (16)
O1W0.0454 (16)0.0586 (19)0.0407 (16)0.0032 (14)0.0045 (13)−0.0056 (14)
N10.060 (2)0.051 (2)0.079 (3)−0.0141 (19)0.023 (2)−0.022 (2)
N20.0302 (14)0.0338 (15)0.0250 (14)0.0037 (12)0.0104 (11)−0.0004 (12)
N30.046 (2)0.084 (3)0.039 (2)0.020 (2)0.0237 (17)0.0225 (18)
C10.0332 (18)0.0310 (17)0.0259 (17)0.0033 (14)0.0089 (14)0.0021 (14)
C20.040 (2)0.0354 (19)0.037 (2)0.0021 (16)0.0110 (16)0.0003 (16)
C30.066 (3)0.037 (2)0.046 (2)0.007 (2)0.014 (2)−0.0094 (18)
C40.069 (3)0.054 (3)0.050 (3)0.025 (2)0.027 (2)0.003 (2)
C50.041 (2)0.052 (2)0.062 (3)0.0077 (19)0.0224 (19)0.005 (2)
C60.036 (2)0.037 (2)0.045 (2)0.0019 (16)0.0094 (16)−0.0030 (17)
C70.0341 (18)0.0287 (17)0.0254 (17)0.0025 (14)0.0104 (14)0.0028 (14)
C80.0326 (18)0.0327 (18)0.0270 (17)0.0055 (15)0.0082 (14)0.0006 (14)
C90.0335 (18)0.0333 (18)0.0269 (17)0.0033 (14)0.0123 (14)0.0022 (14)
C100.050 (2)0.054 (2)0.0303 (18)0.0127 (19)0.0168 (17)0.0124 (17)
C110.043 (2)0.056 (2)0.042 (2)0.0189 (19)0.0159 (18)0.0153 (18)
C120.0342 (19)0.041 (2)0.038 (2)0.0087 (16)0.0168 (16)0.0057 (16)
C130.042 (2)0.053 (2)0.0347 (19)0.0079 (18)0.0167 (17)0.0081 (17)

Geometric parameters (Å, °)

Cu1—O1i1.995 (2)C1—C61.389 (5)
Cu1—O11.995 (2)C1—C71.507 (4)
Cu1—N2i2.006 (3)C2—C31.377 (5)
Cu1—N22.006 (3)C3—C41.380 (6)
Cu1—O1w2.537 (3)C3—H30.9300
O1—C71.266 (4)C4—C51.375 (6)
O2—C71.240 (4)C4—H40.9300
O3—N11.216 (5)C5—C61.389 (5)
O4—N11.210 (5)C5—H50.9300
O5—C131.237 (4)C6—H60.9300
O1W—H110.85 (4)C8—C91.389 (4)
O1W—H120.85 (4)C8—H80.9300
N1—C21.472 (5)C9—C101.381 (5)
N2—C81.337 (4)C9—C131.493 (5)
N2—C121.342 (4)C10—C111.387 (5)
N3—C131.322 (5)C10—H100.9300
N3—H310.85 (4)C11—C121.374 (5)
N3—H320.85 (4)C11—H11A0.9300
C1—C21.389 (5)C12—H12A0.9300
O1i—Cu1—O1180.000 (1)C4—C3—H3120.5
O1i—Cu1—N2i90.07 (10)C5—C4—C3119.7 (4)
O1—Cu1—N2i89.93 (10)C5—C4—H4120.1
O1i—Cu1—N289.93 (10)C3—C4—H4120.1
O1—Cu1—N290.07 (10)C4—C5—C6120.4 (4)
N2i—Cu1—N2180.00 (14)C4—C5—H5119.8
O1i—Cu1—O1W96.04 (9)C6—C5—H5119.8
O1—Cu1—O1W83.96 (9)C5—C6—C1121.2 (4)
N2i—Cu1—O1W85.84 (10)C5—C6—H6119.4
N2—Cu1—O1W94.16 (10)C1—C6—H6119.4
C7—O1—Cu1123.7 (2)O2—C7—O1125.5 (3)
Cu1—O1W—H1189 (3)O2—C7—C1117.3 (3)
Cu1—O1W—H12122 (3)O1—C7—C1117.1 (3)
H11—O1W—H12103 (4)N2—C8—C9123.2 (3)
O4—N1—O3125.1 (4)N2—C8—H8118.4
O4—N1—C2116.9 (4)C9—C8—H8118.4
O3—N1—C2117.9 (4)C10—C9—C8117.7 (3)
C8—N2—C12118.1 (3)C10—C9—C13124.8 (3)
C8—N2—Cu1119.6 (2)C8—C9—C13117.5 (3)
C12—N2—Cu1122.3 (2)C9—C10—C11119.7 (3)
C13—N3—H31120 (3)C9—C10—H10120.2
C13—N3—H32123 (3)C11—C10—H10120.2
H31—N3—H32115 (4)C12—C11—C10118.7 (3)
C2—C1—C6116.5 (3)C12—C11—H11A120.7
C2—C1—C7122.0 (3)C10—C11—H11A120.7
C6—C1—C7121.2 (3)N2—C12—C11122.6 (3)
C3—C2—C1123.1 (3)N2—C12—H12A118.7
C3—C2—N1117.2 (3)C11—C12—H12A118.7
C1—C2—N1119.7 (3)O5—C13—N3122.1 (3)
C2—C3—C4119.0 (4)O5—C13—C9119.9 (3)
C2—C3—H3120.5N3—C13—C9118.0 (3)
N2i—Cu1—O1—C7−65.5 (2)C2—C1—C6—C51.7 (5)
N2—Cu1—O1—C7114.5 (2)C7—C1—C6—C5−171.9 (3)
O1W—Cu1—O1—C7−151.3 (2)Cu1—O1—C7—O2−14.1 (5)
O1i—Cu1—N2—C840.3 (2)Cu1—O1—C7—C1160.6 (2)
O1—Cu1—N2—C8−139.7 (2)C2—C1—C7—O2−24.1 (5)
O1W—Cu1—N2—C8136.3 (2)C6—C1—C7—O2149.2 (3)
O1i—Cu1—N2—C12−137.2 (3)C2—C1—C7—O1160.7 (3)
O1—Cu1—N2—C1242.8 (3)C6—C1—C7—O1−26.0 (4)
O1W—Cu1—N2—C12−41.1 (3)C12—N2—C8—C90.7 (5)
C6—C1—C2—C3−2.6 (5)Cu1—N2—C8—C9−176.9 (2)
C7—C1—C2—C3171.0 (3)N2—C8—C9—C10−0.1 (5)
C6—C1—C2—N1175.3 (3)N2—C8—C9—C13177.3 (3)
C7—C1—C2—N1−11.1 (5)C8—C9—C10—C11−0.8 (6)
O4—N1—C2—C3111.8 (5)C13—C9—C10—C11−178.0 (4)
O3—N1—C2—C3−69.5 (5)C9—C10—C11—C121.2 (6)
O4—N1—C2—C1−66.2 (5)C8—N2—C12—C11−0.4 (5)
O3—N1—C2—C1112.5 (4)Cu1—N2—C12—C11177.2 (3)
C1—C2—C3—C41.3 (6)C10—C11—C12—N2−0.6 (6)
N1—C2—C3—C4−176.6 (4)C10—C9—C13—O5174.3 (4)
C2—C3—C4—C50.9 (6)C8—C9—C13—O5−2.9 (5)
C3—C4—C5—C6−1.6 (6)C10—C9—C13—N3−3.5 (6)
C4—C5—C6—C10.3 (6)C8—C9—C13—N3179.3 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1w—H11···O2i0.85 (4)1.92 (2)2.726 (4)159 (4)
O1w—H12···O5ii0.85 (4)2.11 (2)2.934 (2)165 (3)
N3—H32···O2iii0.85 (4)2.15 (2)2.929 (4)152 (4)
N3—H31···O5iv0.85 (4)2.11 (2)2.926 (4)161 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x, y, z+1; (iv) −x, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2894).

References

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