Acta Cryst. (2009). E65, m1272-m1273 [ doi:10.1107/S1600536809039294 ]
-4,4'-bipyridine-
2N:N')(
3-2-nitro-5-sulfonatobenzoato-
3O1:O1':O5)copper(II)] 4,4'-bipyridine hemisolvate]In the title compound, [Cu(C7H3NO7S)(C10H8N2)(H2O)]·0.5C10H8N2, the CuII atom is six-coordinated by two N atoms from two different bipyridine (bipy) ligands, one sulfonate O atom and two carboxylate O atoms from three 2-nitro-5-sulfonatobenzoate ligands and one water O atom in a distorted octahedral geometry. The bipy solvent molecule lies on an inversion center. The CuII atoms are linked by the bipy ligands, forming one-dimensional chains, which are connected by the 2-nitro-5-sulfonatobenzoate ligands into a two-dimensional layer-like network. The two-dimensional structure is extended by O-H
O and O-H
N hydrogen bonds into a three-dimensional supramolecular network.
A mixture of Cu(CH3CO2)2.2H2O (0.040 g, 0.2 mmol), 2-nitro-5-sulfobenzoic acid (0.049 g, 0.2 mmol), 4,4'-bipyridine (0.039 g, 0.2 mmol), and H2O (15 ml) was sealed in a 25 ml Teflon-lined stainless steel reactor, which was heated at 443 K for 72 h and then it was cooled to room temperature. Blue crystals of the title compound were collected.
H atoms on C atoms were positioned geometrically and refined as riding atoms, with C—H= 0.93 Å and Uiso(H)= 1.2Ueq(C). The H atoms of the water molecule were located in a difference Fourier map and refined with a distance restraint of O—H = 0.85 (1) Å and with Uiso(H) = 1.5Ueq(O).
Data collection: SMART (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: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
| [Cu(C7H3NO7S)(C10H8N2)(H2O)]·0.5C10H8N2 | F(000) = 1144 |
| Mr = 561.00 | Dx = 1.725 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 4260 reflections |
| a = 11.4549 (17) Å | θ = 1.8–26.0° |
| b = 11.0447 (16) Å | µ = 1.17 mm−1 |
| c = 17.089 (3) Å | T = 293 K |
| β = 92.738 (3)° | Block, blue |
| V = 2159.5 (5) Å3 | 0.23 × 0.17 × 0.14 mm |
| Z = 4 |
| Bruker SMART APEX CCD diffractometer | 4260 independent reflections |
| Radiation source: fine-focus sealed tube | 2560 reflections with I > 2σ(I) |
| graphite | Rint = 0.088 |
| φ and ω scans | θmax = 26.0°, θmin = 1.8° |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −14→14 |
| Tmin = 0.767, Tmax = 0.850 | k = −13→13 |
| 11892 measured reflections | l = −21→10 |
| 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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.00 | w = 1/[σ2(Fo2) + (0.0455P)2] where P = (Fo2 + 2Fc2)/3 |
| 4260 reflections | (Δ/σ)max = 0.001 |
| 331 parameters | Δρmax = 0.86 e Å−3 |
| 0 restraints | Δρmin = −0.46 e Å−3 |
| [Cu(C7H3NO7S)(C10H8N2)(H2O)]·0.5C10H8N2 | V = 2159.5 (5) Å3 |
| Mr = 561.00 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 11.4549 (17) Å | µ = 1.17 mm−1 |
| b = 11.0447 (16) Å | T = 293 K |
| c = 17.089 (3) Å | 0.23 × 0.17 × 0.14 mm |
| β = 92.738 (3)° |
| Bruker SMART APEX CCD diffractometer | 4260 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2560 reflections with I > 2σ(I) |
| Tmin = 0.767, Tmax = 0.850 | Rint = 0.088 |
| 11892 measured reflections | θmax = 26.0° |
| R[F2 > 2σ(F2)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.135 | Δρmax = 0.86 e Å−3 |
| S = 1.00 | Δρmin = −0.46 e Å−3 |
| 4260 reflections | Absolute structure: ? |
| 331 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.2223 (4) | 0.7923 (4) | 0.6944 (3) | 0.0215 (13) | |
| C2 | 0.2994 (4) | 0.7254 (4) | 0.6511 (3) | 0.0198 (12) | |
| H2 | 0.3565 | 0.7656 | 0.6243 | 0.024* | |
| C3 | 0.2929 (4) | 0.5989 (5) | 0.6472 (3) | 0.0195 (12) | |
| C4 | 0.2051 (5) | 0.5449 (4) | 0.6866 (3) | 0.0224 (13) | |
| C5 | 0.1244 (5) | 0.6090 (5) | 0.7293 (4) | 0.0321 (15) | |
| H5 | 0.0649 | 0.5692 | 0.7542 | 0.039* | |
| C6 | 0.1356 (5) | 0.7338 (5) | 0.7335 (4) | 0.0313 (15) | |
| H6 | 0.0846 | 0.7786 | 0.7627 | 0.038* | |
| C7 | 0.3842 (5) | 0.5338 (4) | 0.6006 (3) | 0.0177 (12) | |
| C8 | 0.5609 (4) | 0.2511 (4) | 0.6504 (3) | 0.0229 (13) | |
| H8 | 0.5129 | 0.2936 | 0.6831 | 0.027* | |
| C9 | 0.5560 (4) | 0.1262 (4) | 0.6501 (3) | 0.0237 (13) | |
| H9 | 0.5067 | 0.0860 | 0.6831 | 0.028* | |
| C10 | 0.6248 (5) | 0.0607 (4) | 0.6005 (3) | 0.0183 (13) | |
| C11 | 0.6982 (4) | 0.1266 (4) | 0.5532 (3) | 0.0205 (13) | |
| H11 | 0.7454 | 0.0869 | 0.5186 | 0.025* | |
| C12 | 0.6997 (4) | 0.2501 (4) | 0.5582 (3) | 0.0208 (13) | |
| H12 | 0.7504 | 0.2924 | 0.5273 | 0.025* | |
| C13 | 0.6233 (4) | −0.0732 (4) | 0.5994 (3) | 0.0191 (13) | |
| C14 | 0.6096 (4) | −0.1390 (4) | 0.6673 (3) | 0.0207 (13) | |
| H14 | 0.5960 | −0.0992 | 0.7140 | 0.025* | |
| C15 | 0.6162 (5) | −0.2632 (4) | 0.6656 (3) | 0.0241 (13) | |
| H15 | 0.6098 | −0.3057 | 0.7122 | 0.029* | |
| C16 | 0.6431 (5) | −0.2628 (4) | 0.5338 (3) | 0.0248 (13) | |
| H16 | 0.6541 | −0.3054 | 0.4878 | 0.030* | |
| C17 | 0.6397 (5) | −0.1375 (4) | 0.5304 (3) | 0.0236 (13) | |
| H17 | 0.6482 | −0.0971 | 0.4833 | 0.028* | |
| C18 | 0.0395 (6) | 0.2255 (6) | 1.0226 (4) | 0.052 (2) | |
| H18 | 0.0316 | 0.1641 | 1.0593 | 0.063* | |
| C19 | 0.0134 (6) | 0.3431 (6) | 1.0445 (4) | 0.0483 (19) | |
| H19 | −0.0057 | 0.3597 | 1.0957 | 0.058* | |
| C20 | 0.0160 (5) | 0.4360 (5) | 0.9900 (4) | 0.0353 (16) | |
| C21 | 0.0488 (5) | 0.4042 (6) | 0.9165 (4) | 0.0408 (17) | |
| H21 | 0.0509 | 0.4629 | 0.8776 | 0.049* | |
| C22 | 0.0790 (5) | 0.2855 (6) | 0.8995 (4) | 0.0421 (17) | |
| H22 | 0.1028 | 0.2677 | 0.8495 | 0.051* | |
| N1 | 0.1916 (4) | 0.4121 (4) | 0.6833 (3) | 0.0327 (13) | |
| N2 | 0.6323 (4) | 0.3136 (3) | 0.6052 (3) | 0.0212 (11) | |
| N3 | 0.6313 (4) | −0.3253 (4) | 0.5997 (3) | 0.0194 (10) | |
| N4 | 0.0754 (4) | 0.1954 (5) | 0.9520 (3) | 0.0406 (14) | |
| O1 | 0.1331 (3) | 0.9957 (3) | 0.7351 (2) | 0.0321 (9) | |
| O2 | 0.3416 (3) | 0.9755 (3) | 0.7461 (2) | 0.0283 (10) | |
| O3 | 0.2451 (4) | 0.9910 (3) | 0.6178 (2) | 0.0373 (10) | |
| O4 | 0.4740 (3) | 0.5046 (3) | 0.6409 (2) | 0.0223 (8) | |
| O5 | 0.3643 (3) | 0.5231 (3) | 0.5297 (2) | 0.0277 (9) | |
| O6 | 0.8116 (3) | 0.4917 (4) | 0.6061 (2) | 0.0259 (9) | |
| O7 | 0.2618 (3) | 0.3519 (3) | 0.6486 (3) | 0.0376 (11) | |
| O8 | 0.1112 (4) | 0.3662 (4) | 0.7165 (3) | 0.0676 (17) | |
| S1 | 0.23675 (13) | 0.95326 (12) | 0.69752 (9) | 0.0243 (4) | |
| Cu1 | 0.63413 (5) | 0.49342 (5) | 0.60435 (4) | 0.0195 (2) | |
| H1A | 0.833 (5) | 0.486 (5) | 0.653 (3) | 0.029* | |
| H1B | 0.843 (5) | 0.543 (5) | 0.576 (3) | 0.029* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.025 (3) | 0.019 (3) | 0.021 (3) | 0.002 (2) | −0.001 (3) | −0.003 (3) |
| C2 | 0.024 (3) | 0.018 (3) | 0.019 (3) | −0.002 (2) | 0.004 (2) | 0.001 (2) |
| C3 | 0.020 (3) | 0.018 (3) | 0.021 (3) | 0.003 (2) | 0.001 (3) | −0.002 (3) |
| C4 | 0.027 (3) | 0.013 (3) | 0.027 (4) | 0.001 (2) | 0.005 (3) | 0.005 (2) |
| C5 | 0.027 (3) | 0.029 (3) | 0.042 (4) | −0.001 (3) | 0.018 (3) | 0.007 (3) |
| C6 | 0.032 (3) | 0.026 (3) | 0.037 (4) | 0.009 (3) | 0.013 (3) | 0.001 (3) |
| C7 | 0.030 (3) | 0.007 (3) | 0.016 (3) | −0.005 (2) | 0.006 (3) | 0.001 (2) |
| C8 | 0.029 (3) | 0.015 (3) | 0.027 (3) | 0.000 (2) | 0.014 (3) | 0.001 (3) |
| C9 | 0.030 (3) | 0.014 (3) | 0.028 (4) | −0.004 (2) | 0.007 (3) | 0.002 (3) |
| C10 | 0.029 (3) | 0.005 (2) | 0.020 (3) | 0.002 (2) | −0.007 (3) | 0.001 (2) |
| C11 | 0.028 (3) | 0.011 (3) | 0.024 (3) | −0.001 (2) | 0.010 (3) | −0.004 (2) |
| C12 | 0.026 (3) | 0.011 (3) | 0.027 (3) | −0.001 (2) | 0.007 (3) | 0.004 (2) |
| C13 | 0.024 (3) | 0.009 (3) | 0.025 (4) | 0.000 (2) | 0.005 (3) | −0.002 (3) |
| C14 | 0.030 (3) | 0.013 (3) | 0.021 (3) | 0.002 (2) | 0.010 (3) | 0.000 (2) |
| C15 | 0.032 (3) | 0.016 (3) | 0.025 (4) | −0.001 (2) | 0.008 (3) | 0.005 (3) |
| C16 | 0.040 (3) | 0.014 (3) | 0.022 (3) | 0.003 (3) | 0.011 (3) | −0.006 (3) |
| C17 | 0.035 (3) | 0.015 (3) | 0.021 (3) | −0.001 (3) | 0.006 (3) | 0.006 (3) |
| C18 | 0.068 (5) | 0.043 (4) | 0.048 (5) | 0.014 (4) | 0.020 (4) | 0.011 (4) |
| C19 | 0.066 (5) | 0.034 (4) | 0.045 (5) | 0.019 (4) | 0.013 (4) | −0.004 (4) |
| C20 | 0.030 (4) | 0.039 (4) | 0.038 (4) | 0.007 (3) | 0.004 (3) | −0.004 (3) |
| C21 | 0.049 (4) | 0.037 (4) | 0.037 (4) | 0.010 (3) | 0.003 (4) | 0.000 (3) |
| C22 | 0.047 (4) | 0.043 (4) | 0.037 (4) | 0.007 (3) | 0.004 (3) | −0.013 (4) |
| N1 | 0.033 (3) | 0.025 (3) | 0.041 (4) | −0.006 (2) | 0.006 (3) | 0.001 (3) |
| N2 | 0.029 (3) | 0.011 (2) | 0.024 (3) | 0.002 (2) | 0.005 (2) | −0.003 (2) |
| N3 | 0.022 (2) | 0.011 (2) | 0.026 (3) | −0.0013 (19) | 0.005 (2) | 0.001 (2) |
| N4 | 0.038 (3) | 0.036 (3) | 0.048 (4) | 0.002 (2) | 0.000 (3) | −0.003 (3) |
| O1 | 0.031 (2) | 0.026 (2) | 0.039 (2) | 0.0052 (19) | 0.0013 (19) | −0.006 (2) |
| O2 | 0.029 (2) | 0.020 (2) | 0.036 (3) | −0.0042 (16) | 0.0006 (19) | −0.0048 (19) |
| O3 | 0.065 (3) | 0.023 (2) | 0.025 (2) | 0.002 (2) | 0.002 (2) | 0.001 (2) |
| O4 | 0.0249 (19) | 0.0142 (18) | 0.028 (2) | 0.0021 (17) | 0.0053 (17) | 0.0024 (19) |
| O5 | 0.045 (2) | 0.017 (2) | 0.021 (2) | 0.0056 (17) | 0.0079 (19) | −0.0030 (18) |
| O6 | 0.030 (2) | 0.021 (2) | 0.027 (2) | −0.0013 (18) | 0.0064 (19) | 0.006 (2) |
| O7 | 0.046 (3) | 0.019 (2) | 0.049 (3) | −0.005 (2) | 0.019 (2) | −0.007 (2) |
| O8 | 0.066 (3) | 0.035 (3) | 0.106 (5) | −0.012 (2) | 0.056 (3) | 0.005 (3) |
| S1 | 0.0298 (8) | 0.0166 (7) | 0.0269 (9) | 0.0041 (6) | 0.0063 (7) | −0.0020 (6) |
| Cu1 | 0.0252 (3) | 0.0066 (3) | 0.0273 (4) | 0.0008 (3) | 0.0082 (3) | −0.0005 (3) |
| C1—C6 | 1.382 (7) | C15—H15 | 0.9300 |
| C1—C2 | 1.391 (7) | C16—N3 | 1.334 (6) |
| C1—S1 | 1.787 (5) | C16—C17 | 1.385 (7) |
| C2—C3 | 1.401 (6) | C16—H16 | 0.9300 |
| C2—H2 | 0.9300 | C17—H17 | 0.9300 |
| C3—C4 | 1.373 (7) | C18—N4 | 1.335 (8) |
| C3—C7 | 1.525 (7) | C18—C19 | 1.389 (9) |
| C4—C5 | 1.398 (7) | C18—H18 | 0.9300 |
| C4—N1 | 1.475 (7) | C19—C20 | 1.386 (9) |
| C5—C6 | 1.386 (7) | C19—H19 | 0.9300 |
| C5—H5 | 0.9300 | C20—C21 | 1.375 (8) |
| C6—H6 | 0.9300 | C20—C20i | 1.505 (11) |
| C7—O5 | 1.227 (6) | C21—C22 | 1.390 (8) |
| C7—O4 | 1.254 (6) | C21—H21 | 0.9300 |
| C8—N2 | 1.341 (6) | C22—N4 | 1.342 (8) |
| C8—C9 | 1.381 (7) | C22—H22 | 0.9300 |
| C8—H8 | 0.9300 | N1—O8 | 1.216 (6) |
| C9—C10 | 1.388 (7) | N1—O7 | 1.219 (6) |
| C9—H9 | 0.9300 | O1—S1 | 1.454 (4) |
| C10—C11 | 1.398 (7) | O2—S1 | 1.448 (4) |
| C10—C13 | 1.479 (6) | O3—S1 | 1.432 (4) |
| C11—C12 | 1.366 (6) | O6—H1A | 0.83 (5) |
| C11—H11 | 0.9300 | O6—H1B | 0.86 (5) |
| C12—N2 | 1.339 (6) | Cu1—N2 | 1.986 (4) |
| C12—H12 | 0.9300 | Cu1—N3ii | 2.004 (4) |
| C13—C14 | 1.384 (7) | Cu1—O2iii | 2.565 (4) |
| C13—C17 | 1.397 (7) | Cu1—O4 | 1.969 (3) |
| C14—C15 | 1.374 (6) | Cu1—O5iv | 2.299 (4) |
| C14—H14 | 0.9300 | Cu1—O6 | 2.032 (4) |
| C15—N3 | 1.337 (6) | ||
| C6—C1—C2 | 119.9 (5) | N4—C18—C19 | 123.8 (7) |
| C6—C1—S1 | 121.2 (4) | N4—C18—H18 | 118.1 |
| C2—C1—S1 | 118.9 (4) | C19—C18—H18 | 118.1 |
| C1—C2—C3 | 121.4 (5) | C20—C19—C18 | 119.9 (7) |
| C1—C2—H2 | 119.3 | C20—C19—H19 | 120.0 |
| C3—C2—H2 | 119.3 | C18—C19—H19 | 120.0 |
| C4—C3—C2 | 116.7 (5) | C21—C20—C19 | 116.2 (6) |
| C4—C3—C7 | 126.0 (5) | C21—C20—C20i | 121.8 (8) |
| C2—C3—C7 | 117.3 (5) | C19—C20—C20i | 122.0 (8) |
| C3—C4—C5 | 123.6 (5) | C20—C21—C22 | 120.9 (6) |
| C3—C4—N1 | 119.4 (5) | C20—C21—H21 | 119.5 |
| C5—C4—N1 | 116.9 (5) | C22—C21—H21 | 119.5 |
| C6—C5—C4 | 117.9 (5) | N4—C22—C21 | 122.9 (6) |
| C6—C5—H5 | 121.0 | N4—C22—H22 | 118.6 |
| C4—C5—H5 | 121.0 | C21—C22—H22 | 118.6 |
| C1—C6—C5 | 120.5 (5) | O8—N1—O7 | 122.2 (5) |
| C1—C6—H6 | 119.8 | O8—N1—C4 | 118.4 (5) |
| C5—C6—H6 | 119.8 | O7—N1—C4 | 119.4 (5) |
| O5—C7—O4 | 128.8 (5) | C12—N2—C8 | 117.4 (4) |
| O5—C7—C3 | 117.5 (5) | C12—N2—Cu1 | 120.8 (4) |
| O4—C7—C3 | 113.6 (5) | C8—N2—Cu1 | 121.7 (4) |
| N2—C8—C9 | 122.5 (5) | C16—N3—C15 | 117.9 (4) |
| N2—C8—H8 | 118.7 | C16—N3—Cu1v | 123.2 (4) |
| C9—C8—H8 | 118.7 | C15—N3—Cu1v | 118.8 (4) |
| C8—C9—C10 | 119.9 (5) | C18—N4—C22 | 116.2 (6) |
| C8—C9—H9 | 120.0 | C7—O4—Cu1 | 126.4 (3) |
| C10—C9—H9 | 120.0 | C7—O5—Cu1iv | 168.9 (4) |
| C9—C10—C11 | 117.2 (4) | Cu1—O6—H1A | 105 (4) |
| C9—C10—C13 | 121.5 (5) | Cu1—O6—H1B | 115 (4) |
| C11—C10—C13 | 121.4 (5) | H1A—O6—H1B | 122 (5) |
| C12—C11—C10 | 119.3 (5) | O3—S1—O2 | 113.9 (2) |
| C12—C11—H11 | 120.4 | O3—S1—O1 | 114.8 (2) |
| C10—C11—H11 | 120.4 | O2—S1—O1 | 111.4 (2) |
| N2—C12—C11 | 123.7 (5) | O3—S1—C1 | 105.8 (3) |
| N2—C12—H12 | 118.1 | O2—S1—C1 | 105.0 (2) |
| C11—C12—H12 | 118.1 | O1—S1—C1 | 104.9 (2) |
| C14—C13—C17 | 117.7 (5) | O4—Cu1—N2 | 92.84 (16) |
| C14—C13—C10 | 121.1 (5) | O4—Cu1—N3ii | 86.36 (16) |
| C17—C13—C10 | 121.1 (5) | N2—Cu1—N3ii | 177.66 (18) |
| C15—C14—C13 | 119.9 (5) | O4—Cu1—O6 | 160.42 (16) |
| C15—C14—H14 | 120.1 | N2—Cu1—O6 | 90.09 (17) |
| C13—C14—H14 | 120.1 | N3ii—Cu1—O6 | 91.39 (17) |
| N3—C15—C14 | 122.6 (5) | O4—Cu1—O5iv | 111.89 (14) |
| N3—C15—H15 | 118.7 | N2—Cu1—O5iv | 85.92 (16) |
| C14—C15—H15 | 118.7 | N3ii—Cu1—O5iv | 92.34 (16) |
| N3—C16—C17 | 123.2 (5) | O6—Cu1—O5iv | 87.62 (15) |
| N3—C16—H16 | 118.4 | O2iii—Cu1—N2 | 85.20 (17) |
| C17—C16—H16 | 118.4 | O2iii—Cu1—N3ii | 96.74 (17) |
| C16—C17—C13 | 118.5 (5) | O2iii—Cu1—O4 | 75.35 (13) |
| C16—C17—H17 | 120.7 | O2iii—Cu1—O5iv | 168.81 (12) |
| C13—C17—H17 | 120.7 | O2iii—Cu1—O6 | 85.63 (13) |
| C6—C1—C2—C3 | −1.2 (8) | C20i—C20—C21—C22 | 179.5 (7) |
| S1—C1—C2—C3 | 179.4 (4) | C20—C21—C22—N4 | 1.7 (10) |
| C1—C2—C3—C4 | 1.4 (8) | C3—C4—N1—O8 | −177.7 (6) |
| C1—C2—C3—C7 | −177.9 (5) | C5—C4—N1—O8 | 0.9 (8) |
| C2—C3—C4—C5 | 0.1 (9) | C3—C4—N1—O7 | 3.5 (8) |
| C7—C3—C4—C5 | 179.2 (5) | C5—C4—N1—O7 | −178.0 (5) |
| C2—C3—C4—N1 | 178.5 (5) | C11—C12—N2—C8 | 1.0 (8) |
| C7—C3—C4—N1 | −2.3 (9) | C11—C12—N2—Cu1 | −176.6 (4) |
| C3—C4—C5—C6 | −1.7 (9) | C9—C8—N2—C12 | 0.5 (8) |
| N1—C4—C5—C6 | 179.8 (5) | C9—C8—N2—Cu1 | 178.1 (4) |
| C2—C1—C6—C5 | −0.5 (9) | C17—C16—N3—C15 | −0.4 (8) |
| S1—C1—C6—C5 | 178.9 (5) | C17—C16—N3—Cu1v | 179.2 (4) |
| C4—C5—C6—C1 | 1.9 (9) | C14—C15—N3—C16 | 1.6 (8) |
| C4—C3—C7—O5 | 95.3 (7) | C14—C15—N3—Cu1v | −178.0 (4) |
| C2—C3—C7—O5 | −85.6 (6) | C19—C18—N4—C22 | −3.8 (10) |
| C4—C3—C7—O4 | −88.7 (7) | C21—C22—N4—C18 | 0.7 (9) |
| C2—C3—C7—O4 | 90.4 (6) | O5—C7—O4—Cu1 | 26.7 (7) |
| N2—C8—C9—C10 | −1.5 (9) | C3—C7—O4—Cu1 | −148.7 (3) |
| C8—C9—C10—C11 | 0.9 (8) | O4—C7—O5—Cu1iv | −29 (2) |
| C8—C9—C10—C13 | 179.0 (5) | C3—C7—O5—Cu1iv | 146.5 (15) |
| C9—C10—C11—C12 | 0.6 (8) | C6—C1—S1—O3 | −130.7 (5) |
| C13—C10—C11—C12 | −177.6 (5) | C2—C1—S1—O3 | 48.7 (5) |
| C10—C11—C12—N2 | −1.6 (8) | C6—C1—S1—O2 | 108.6 (5) |
| C9—C10—C13—C14 | −35.0 (8) | C2—C1—S1—O2 | −72.0 (5) |
| C11—C10—C13—C14 | 143.0 (5) | C6—C1—S1—O1 | −9.0 (5) |
| C9—C10—C13—C17 | 147.2 (5) | C2—C1—S1—O1 | 170.5 (4) |
| C11—C10—C13—C17 | −34.7 (8) | C7—O4—Cu1—N2 | −106.1 (4) |
| C17—C13—C14—C15 | 2.0 (8) | C7—O4—Cu1—N3ii | 71.7 (4) |
| C10—C13—C14—C15 | −175.8 (5) | C7—O4—Cu1—O6 | 155.6 (5) |
| C13—C14—C15—N3 | −2.5 (8) | C7—O4—Cu1—O5iv | −19.4 (4) |
| N3—C16—C17—C13 | 0.1 (8) | C12—N2—Cu1—O4 | 153.9 (4) |
| C14—C13—C17—C16 | −0.9 (8) | C8—N2—Cu1—O4 | −23.6 (4) |
| C10—C13—C17—C16 | 176.9 (5) | C12—N2—Cu1—O6 | −45.4 (4) |
| N4—C18—C19—C20 | 4.6 (11) | C8—N2—Cu1—O6 | 137.1 (4) |
| C18—C19—C20—C21 | −2.0 (10) | C12—N2—Cu1—O5iv | 42.2 (4) |
| C18—C19—C20—C20i | 177.6 (7) | C8—N2—Cu1—O5iv | −135.3 (4) |
| C19—C20—C21—C22 | −0.9 (10) |
| Symmetry codes: (i) −x, −y+1, −z+2; (ii) x, y+1, z; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+1, −y+1, −z+1; (v) x, y−1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O6—H1A···O1iii | 0.83 (5) | 1.94 (5) | 2.758 (5) | 171 (6) |
| O6—H1B···N4vi | 0.86 (5) | 2.00 (5) | 2.801 (6) | 156 (5) |
| Symmetry codes: (iii) −x+1, y−1/2, −z+3/2; (vi) −x+1, y+1/2, −z+3/2. |
| Cu1—N2 | 1.986 (4) | Cu1—O4 | 1.969 (3) |
| Cu1—N3i | 2.004 (4) | Cu1—O5iii | 2.299 (4) |
| Cu1—O2ii | 2.565 (4) | Cu1—O6 | 2.032 (4) |
| Symmetry codes: (i) x, y+1, z; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O6—H1A···O1ii | 0.83 (5) | 1.94 (5) | 2.758 (5) | 171 (6) |
| O6—H1B···N4iv | 0.86 (5) | 2.00 (5) | 2.801 (6) | 156 (5) |
| Symmetry codes: (ii) −x+1, y−1/2, −z+3/2; (iv) −x+1, y+1/2, −z+3/2. |
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dong, H., Bi, W. & Zhu, H. (2009). Asian J. Chem. 21, 5598–5602.
Du, Z., Huang, J., Xie, Y. & Wen, H. (2009). J. Mol. Struct. 919, 112–116.
Li, L., Xu, G. & Zhu, H.-B. (2009). Acta Cryst. E65, m476.
Liu, Y., Bi, Y., He, W., Wang, X., Liao, W. & Zhang, H. (2009). J. Mol. Struct. 919, 235–238.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Sonnauer, A., Feyand, M. & Stock, N. (2009). Cryst. Growth Des. 9, 586–592.
Sonnauer, A. & Stock, N. (2008). Eur. J. Inorg. Chem. pp. 5038–5045.
In recent years, the design and synthesis of copper(II) sulfonates have attracted great attention because of their flexible coordination modes, interesting inorganic-organic lamellar structures, selective and reversible guest inclusion properties, and their ability to intercalate guest molecules (Du et al., 2009; Sonnauer et al., 2009). It is noteworthy that some copper(II) sulfonate complexes with nitrogen-based secondary ligands, exhibiting different bonding modes dependent on the presence of secondary ligands, have been reported (Liu et al., 2009; Sonnauer & Stock, 2008). It has also been demonstrated that the existence and changes of the secondary ligands can have a great effect on the structures of copper(II) sulfonates, often with surprising results (Li et al., 2009). In this paper, we utilized 2-nitro-5-sulfobenzoic acid (H2nsb) as an organic sulfonate ligand and 4,4'-bipyridine (bipy) as an N-donor ligand, providing a coordination compound, [Cu(nsb)(bipy)(H2O)].0.5bipy, which is reported here.
In the title compound, the central CuII ion is six-coordinated by two N atoms from two different bipy ligands, one sulfonate O atom, two carboxylate O atoms from three nsb ligand and one water molecule in a distorted octahedral coordination geometry (Table 1). There are free bipy molecules in the structure, stabilized by hydrogen bonds (Fig. 1). The Cu—O distances are comparable to those found in other crystallographically characterized CuII complexes (Dong et al., 2009). The Cu atoms are linked by the bipy ligands, forming an extended one-dimensional chain. These chains are further connected by the nsb ligands into a two-dimensional layer-like network. In addition, the existence of O—H···O and O—H···N hydrogen bonds (Table 2) extends the two-dimensional layer into a three-dimensional supramolecular architecture (Fig. 2).