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Acta Cryst. (2009). E65, m427-m428    [ doi:10.1107/S1600536809007995 ]

trans,trans,trans-Diaquabis(nicotinamide-[kappa]N)bis(2-nitrobenzoato-[kappa]O)copper(II)

K.-L. Zhang, Q.-L. Xie and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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).

Figures top
[Figure 1] 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.
trans,trans,trans-Diaquabis(nicotinamide- κN)bis(2-nitrobenzoato-κO)copper(II) top
Crystal data top
[Cu(C7H4NO4)2(C6H6N2O)2(H2O)2]F(000) = 694
Mr = 676.05Dx = 1.577 Mg m−3
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 mm−1
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 top
Bruker SMART area-detector
diffractometer		2507 independent reflections
Radiation source: medium-focus sealed tube2069 reflections with I > 2σ(I)
graphiteRint = 0.036
φ 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 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 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 Å−3
4 restraintsΔρmin = −0.46 e Å−3
Crystal data top
[Cu(C7H4NO4)2(C6H6N2O)2(H2O)2]V = 1423.63 (8) Å3
Mr = 676.05Z = 2
Monoclinic, P21/nMo Kα radiation
a = 7.9582 (3) ŵ = 0.84 mm−1
b = 18.7044 (6) ÅT = 295 K
c = 9.8573 (2) Å0.45 × 0.20 × 0.16 mm
β = 104.012 (2)°
Data collection top
Bruker SMART area-detector
diffractometer		2507 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2069 reflections with I > 2σ(I)
Tmin = 0.557, Tmax = 0.877Rint = 0.036
7295 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111Δρmax = 0.31 e Å−3
S = 1.12Δρmin = −0.46 e Å−3
2507 reflectionsAbsolute structure: ?
229 parametersFlack parameter: ?
4 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Selected geometric parameters (Å) top
Cu1—O11.995 (2)Cu1—O1w2.537 (3)
Cu1—N22.006 (3)
Table 2
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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

references
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