Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107047142/fa3124sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270107047142/fa3124Isup2.hkl |
CCDC reference: 669161
The preparation of p-hydroxybenzoate complexes was carried out as follows. First, sodium 3-hydroxybenzoate was prepared according to the equation 2(3-hba) + 2NaHCO3 → 2Na(3-hba) + 2CO2 + 2H2O (3-hba is 3-hydroxybenzoic acid). In the second step, CuII-3-hba salts were synthesized from the Na(3-hba) salt by the substitution reaction 2Na(3-hba) + CuSO4·5H2O → Cu(3-hba)2.nH2O + Na2SO4. The Cu(3-hba)2.nH2O salts were prepared in aqueous media. The synthesis of the mixed-ligand complexes was carried out as follows. A solution of na (nicotinamide) (2 mmol) in distilled water (30 ml) was added dropwise with stirring to a solution of Cu(3-hba)2.nH2O (1 mmol) in hot distilled water (50 ml). The solution was heated to 323 K in a temperature-controlled bath and stirred for 4 h, then cooled to room temperature and left for 10–12 d for crystallization. The crystals formed were filtered, washed with cold water and acetone, and dried in vacuo. The mixed-ligand complexes were prepared according to the equation Cu(3-hba)2.nH2O + 2na → Cu(3-hba)2(na)2(H2O)2
H atoms bonded to C and N were included in their expected positions and allowed to ride, with C—H and N—H distances restrained to 0.93 and 0.86 Å, respectively. Water H atoms were located in difference maps and refined subject to a restraint of O—H = 0.83 (2) Å. H atoms were assigned a Uiso(H) value of 1.2Ueq of the parent atom. The H atoms of hydroxyl O atoms were refined with fixed O—H = 0.82 Å [Uiso(H) = 1.5Ueq of the parent atom].
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Cu(C7H5O3)2(C6H6N2O)2(H2O)2] | F(000) = 638 |
Mr = 618.05 | Dx = 1.602 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 8248 reflections |
a = 7.2667 (7) Å | θ = 2.1–28.0° |
b = 17.8020 (14) Å | µ = 0.92 mm−1 |
c = 10.8166 (10) Å | T = 296 K |
β = 113.706 (7)° | Prism, blue |
V = 1281.2 (2) Å3 | 0.74 × 0.52 × 0.40 mm |
Z = 2 |
Stoe IPDS2 diffractometer | 2562 independent reflections |
Radiation source: fine-focus sealed tube | 2296 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.3°, θmin = 2.3° |
ω scans | h = −7→8 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −20→22 |
Tmin = 0.413, Tmax = 0.563 | l = −13→13 |
8248 measured reflections |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0457P)2 + 0.5351P] where P = (Fo2 + 2Fc2)/3 |
2562 reflections | (Δ/σ)max < 0.001 |
193 parameters | Δρmax = 0.35 e Å−3 |
4 restraints | Δρmin = −0.41 e Å−3 |
[Cu(C7H5O3)2(C6H6N2O)2(H2O)2] | V = 1281.2 (2) Å3 |
Mr = 618.05 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.2667 (7) Å | µ = 0.92 mm−1 |
b = 17.8020 (14) Å | T = 296 K |
c = 10.8166 (10) Å | 0.74 × 0.52 × 0.40 mm |
β = 113.706 (7)° |
Stoe IPDS2 diffractometer | 2562 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2296 reflections with I > 2σ(I) |
Tmin = 0.413, Tmax = 0.563 | Rint = 0.026 |
8248 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 4 restraints |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.35 e Å−3 |
2562 reflections | Δρmin = −0.41 e Å−3 |
193 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5924 (3) | 0.40542 (11) | 0.74090 (18) | 0.0358 (4) | |
H1 | 0.4558 | 0.3945 | 0.7005 | 0.043* | |
C2 | 0.7072 (3) | 0.37191 (12) | 0.8620 (2) | 0.0430 (5) | |
H2 | 0.6484 | 0.3396 | 0.9032 | 0.052* | |
C3 | 0.9093 (3) | 0.38669 (12) | 0.92141 (18) | 0.0391 (4) | |
H3 | 0.9897 | 0.3638 | 1.0025 | 0.047* | |
C4 | 0.9920 (3) | 0.43616 (10) | 0.85896 (16) | 0.0305 (4) | |
C5 | 0.8654 (3) | 0.46828 (10) | 0.73849 (16) | 0.0291 (3) | |
H5 | 0.9195 | 0.5022 | 0.6968 | 0.035* | |
C6 | 1.2084 (3) | 0.45897 (12) | 0.91378 (18) | 0.0376 (4) | |
C7 | 0.6147 (3) | 0.63826 (9) | 0.64905 (16) | 0.0289 (4) | |
C8 | 0.7823 (3) | 0.69129 (9) | 0.72717 (16) | 0.0275 (3) | |
C9 | 0.9748 (3) | 0.68005 (10) | 0.73330 (16) | 0.0300 (4) | |
H9 | 0.9991 | 0.6419 | 0.6830 | 0.036* | |
C10 | 1.1307 (3) | 0.72583 (11) | 0.81471 (18) | 0.0333 (4) | |
C11 | 1.0937 (3) | 0.78369 (11) | 0.88709 (19) | 0.0373 (4) | |
H11 | 1.1982 | 0.8147 | 0.9409 | 0.045* | |
C12 | 0.9030 (3) | 0.79530 (11) | 0.8795 (2) | 0.0386 (4) | |
H12 | 0.8784 | 0.8347 | 0.9273 | 0.046* | |
C13 | 0.7467 (3) | 0.74893 (10) | 0.80145 (19) | 0.0346 (4) | |
H13 | 0.6184 | 0.7563 | 0.7986 | 0.042* | |
N1 | 0.6697 (2) | 0.45309 (8) | 0.67899 (14) | 0.0287 (3) | |
N2 | 1.3346 (3) | 0.42477 (13) | 1.02307 (19) | 0.0574 (5) | |
H2A | 1.4592 | 0.4375 | 1.0578 | 0.069* | |
H2B | 1.2923 | 0.3897 | 1.0597 | 0.069* | |
O1 | 1.2629 (2) | 0.50901 (11) | 0.85896 (18) | 0.0649 (6) | |
O2 | 0.64485 (19) | 0.59518 (7) | 0.56628 (12) | 0.0335 (3) | |
O3 | 0.4597 (2) | 0.63788 (9) | 0.67152 (16) | 0.0497 (4) | |
O4 | 1.3251 (2) | 0.71641 (10) | 0.83315 (17) | 0.0528 (4) | |
H4 | 1.3335 | 0.6812 | 0.7869 | 0.079* | |
O5 | 0.2080 (3) | 0.52026 (12) | 0.57284 (19) | 0.0622 (5) | |
H5A | 0.264 (5) | 0.5607 (13) | 0.605 (3) | 0.093* | |
H5B | 0.115 (4) | 0.5071 (18) | 0.585 (4) | 0.093* | |
Cu1 | 0.5000 | 0.5000 | 0.5000 | 0.03004 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0255 (9) | 0.0402 (10) | 0.0360 (9) | −0.0069 (7) | 0.0065 (7) | 0.0033 (7) |
C2 | 0.0363 (11) | 0.0494 (11) | 0.0389 (10) | −0.0089 (9) | 0.0105 (8) | 0.0127 (8) |
C3 | 0.0343 (10) | 0.0472 (11) | 0.0285 (9) | −0.0011 (8) | 0.0050 (7) | 0.0111 (8) |
C4 | 0.0240 (9) | 0.0374 (9) | 0.0252 (8) | −0.0009 (7) | 0.0049 (6) | 0.0001 (7) |
C5 | 0.0247 (9) | 0.0329 (8) | 0.0262 (8) | −0.0024 (7) | 0.0066 (6) | 0.0024 (6) |
C6 | 0.0250 (9) | 0.0526 (12) | 0.0289 (9) | −0.0008 (8) | 0.0044 (7) | 0.0046 (8) |
C7 | 0.0244 (9) | 0.0270 (8) | 0.0270 (8) | 0.0005 (6) | 0.0019 (6) | 0.0021 (6) |
C8 | 0.0260 (9) | 0.0269 (8) | 0.0240 (7) | −0.0017 (6) | 0.0042 (6) | 0.0010 (6) |
C9 | 0.0316 (9) | 0.0295 (8) | 0.0289 (8) | −0.0007 (7) | 0.0122 (7) | −0.0017 (6) |
C10 | 0.0255 (9) | 0.0385 (9) | 0.0357 (9) | −0.0030 (7) | 0.0120 (7) | 0.0024 (7) |
C11 | 0.0324 (10) | 0.0351 (9) | 0.0386 (9) | −0.0095 (8) | 0.0083 (8) | −0.0065 (7) |
C12 | 0.0375 (11) | 0.0327 (9) | 0.0428 (10) | −0.0011 (8) | 0.0132 (8) | −0.0107 (8) |
C13 | 0.0265 (9) | 0.0334 (9) | 0.0418 (10) | 0.0016 (7) | 0.0114 (8) | −0.0036 (7) |
N1 | 0.0232 (7) | 0.0309 (7) | 0.0262 (7) | −0.0032 (6) | 0.0039 (5) | 0.0005 (5) |
N2 | 0.0266 (9) | 0.0773 (14) | 0.0505 (11) | −0.0048 (9) | −0.0031 (7) | 0.0273 (10) |
O1 | 0.0293 (8) | 0.0973 (14) | 0.0505 (9) | −0.0191 (8) | −0.0023 (7) | 0.0326 (9) |
O2 | 0.0334 (7) | 0.0311 (6) | 0.0290 (6) | −0.0062 (5) | 0.0053 (5) | −0.0051 (5) |
O3 | 0.0321 (8) | 0.0540 (9) | 0.0633 (9) | −0.0120 (6) | 0.0194 (7) | −0.0183 (7) |
O4 | 0.0293 (8) | 0.0626 (10) | 0.0691 (10) | −0.0082 (7) | 0.0224 (7) | −0.0167 (8) |
O5 | 0.0484 (10) | 0.0794 (13) | 0.0534 (10) | −0.0183 (9) | 0.0150 (8) | −0.0084 (9) |
Cu1 | 0.02809 (18) | 0.02744 (17) | 0.02281 (16) | −0.00376 (11) | −0.00204 (12) | −0.00015 (10) |
C1—N1 | 1.337 (2) | C9—C10 | 1.386 (3) |
C1—C2 | 1.374 (3) | C9—H9 | 0.9300 |
C1—H1 | 0.9300 | C10—O4 | 1.356 (2) |
C2—C3 | 1.371 (3) | C10—C11 | 1.384 (3) |
C2—H2 | 0.9300 | C11—C12 | 1.371 (3) |
C3—C4 | 1.385 (3) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.383 (3) |
C4—C5 | 1.381 (2) | C12—H12 | 0.9300 |
C4—C6 | 1.497 (3) | C13—H13 | 0.9300 |
C5—N1 | 1.332 (2) | N1—Cu1 | 2.0117 (14) |
C5—H5 | 0.9300 | N2—H2A | 0.8600 |
C6—O1 | 1.221 (3) | N2—H2B | 0.8600 |
C6—N2 | 1.318 (2) | O2—Cu1 | 1.9714 (12) |
C7—O3 | 1.245 (2) | O4—H4 | 0.8200 |
C7—O2 | 1.263 (2) | O5—Cu1 | 2.569 (2) |
C7—C8 | 1.503 (2) | O5—H5A | 0.831 (17) |
C8—C9 | 1.389 (3) | O5—H5B | 0.775 (17) |
C8—C13 | 1.390 (2) | ||
N1—C1—C2 | 122.46 (17) | O4—C10—C9 | 123.92 (17) |
N1—C1—H1 | 118.8 | C11—C10—C9 | 120.13 (17) |
C2—C1—H1 | 118.8 | C12—C11—C10 | 120.03 (17) |
C3—C2—C1 | 119.26 (18) | C12—C11—H11 | 120.0 |
C3—C2—H2 | 120.4 | C10—C11—H11 | 120.0 |
C1—C2—H2 | 120.4 | C11—C12—C13 | 120.56 (17) |
C2—C3—C4 | 119.10 (17) | C11—C12—H12 | 119.7 |
C2—C3—H3 | 120.5 | C13—C12—H12 | 119.7 |
C4—C3—H3 | 120.5 | C12—C13—C8 | 119.73 (17) |
C5—C4—C3 | 117.93 (16) | C12—C13—H13 | 120.1 |
C5—C4—C6 | 117.16 (16) | C8—C13—H13 | 120.1 |
C3—C4—C6 | 124.89 (16) | C5—N1—C1 | 117.98 (15) |
N1—C5—C4 | 123.26 (16) | C5—N1—Cu1 | 120.20 (11) |
N1—C5—H5 | 118.4 | C1—N1—Cu1 | 121.82 (12) |
C4—C5—H5 | 118.4 | C6—N2—H2A | 120.0 |
O1—C6—N2 | 121.90 (18) | C6—N2—H2B | 120.0 |
O1—C6—C4 | 119.98 (16) | H2A—N2—H2B | 120.0 |
N2—C6—C4 | 118.11 (18) | C7—O2—Cu1 | 124.08 (12) |
O3—C7—O2 | 124.31 (16) | C10—O4—H4 | 109.5 |
O3—C7—C8 | 119.06 (16) | Cu1—O5—H5A | 85 (2) |
O2—C7—C8 | 116.60 (16) | Cu1—O5—H5B | 153 (2) |
C9—C8—C13 | 119.78 (16) | H5A—O5—H5B | 121 (3) |
C9—C8—C7 | 120.61 (15) | O2—Cu1—N1i | 91.39 (5) |
C13—C8—C7 | 119.46 (16) | O2—Cu1—N1 | 88.61 (5) |
C10—C9—C8 | 119.74 (16) | O2—Cu1—O5 | 98.86 (6) |
C10—C9—H9 | 120.1 | O2i—Cu1—O5 | 81.14 (6) |
C8—C9—H9 | 120.1 | N1i—Cu1—O5 | 88.54 (6) |
O4—C10—C11 | 115.92 (17) | N1—Cu1—O5 | 91.46 (6) |
N1—C1—C2—C3 | −1.0 (3) | C10—C11—C12—C13 | 0.9 (3) |
C1—C2—C3—C4 | 1.2 (3) | C11—C12—C13—C8 | −1.7 (3) |
C2—C3—C4—C5 | −0.2 (3) | C9—C8—C13—C12 | 0.9 (3) |
C2—C3—C4—C6 | 178.4 (2) | C7—C8—C13—C12 | 176.39 (17) |
C3—C4—C5—N1 | −1.1 (3) | C4—C5—N1—C1 | 1.3 (3) |
C6—C4—C5—N1 | −179.77 (17) | C4—C5—N1—Cu1 | −177.76 (14) |
C5—C4—C6—O1 | 6.5 (3) | C2—C1—N1—C5 | −0.2 (3) |
C3—C4—C6—O1 | −172.0 (2) | C2—C1—N1—Cu1 | 178.81 (16) |
C5—C4—C6—N2 | −174.9 (2) | O3—C7—O2—Cu1 | −20.1 (2) |
C3—C4—C6—N2 | 6.5 (3) | C8—C7—O2—Cu1 | 157.98 (11) |
O3—C7—C8—C9 | 162.30 (17) | C7—O2—Cu1—N1i | 104.17 (13) |
O2—C7—C8—C9 | −15.9 (2) | C7—O2—Cu1—N1 | −75.83 (13) |
O3—C7—C8—C13 | −13.2 (2) | C7—O2—Cu1—O5 | 15.43 (14) |
O2—C7—C8—C13 | 168.61 (16) | C5—N1—Cu1—O2 | −41.38 (14) |
C13—C8—C9—C10 | 0.8 (3) | C1—N1—Cu1—O2 | 139.58 (15) |
C7—C8—C9—C10 | −174.72 (16) | C5—N1—Cu1—O2i | 138.62 (14) |
C8—C9—C10—O4 | 176.05 (17) | C1—N1—Cu1—O2i | −40.42 (15) |
C8—C9—C10—C11 | −1.6 (3) | C5—N1—Cu1—O5 | −140.20 (14) |
O4—C10—C11—C12 | −177.07 (18) | C1—N1—Cu1—O5 | 40.76 (15) |
C9—C10—C11—C12 | 0.7 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1ii | 0.86 | 2.08 | 2.928 (2) | 168 |
O4—H4···O3iii | 0.82 | 1.98 | 2.709 (2) | 148 |
O5—H5A···O3 | 0.83 (2) | 1.90 (2) | 2.702 (2) | 162 (3) |
O5—H5B···O5iv | 0.78 (2) | 2.33 (3) | 2.883 (4) | 129 (3) |
Symmetry codes: (ii) −x+3, −y+1, −z+2; (iii) x+1, y, z; (iv) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C7H5O3)2(C6H6N2O)2(H2O)2] |
Mr | 618.05 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 7.2667 (7), 17.8020 (14), 10.8166 (10) |
β (°) | 113.706 (7) |
V (Å3) | 1281.2 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.92 |
Crystal size (mm) | 0.74 × 0.52 × 0.40 |
Data collection | |
Diffractometer | Stoe IPDS2 diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.413, 0.563 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8248, 2562, 2296 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.622 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.081, 1.03 |
No. of reflections | 2562 |
No. of parameters | 193 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.35, −0.41 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
N1—Cu1 | 2.0117 (14) | O5—Cu1 | 2.569 (2) |
O2—Cu1 | 1.9714 (12) | ||
C7—O2—Cu1 | 124.08 (12) | O2—Cu1—O5 | 98.86 (6) |
O2—Cu1—N1 | 88.61 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.86 | 2.08 | 2.928 (2) | 168.0 |
O4—H4···O3ii | 0.82 | 1.98 | 2.709 (2) | 148.2 |
O5—H5A···O3 | 0.831 (17) | 1.898 (18) | 2.702 (2) | 162 (3) |
O5—H5B···O5iii | 0.775 (17) | 2.33 (3) | 2.883 (4) | 129 (3) |
Symmetry codes: (i) −x+3, −y+1, −z+2; (ii) x+1, y, z; (iii) −x, −y+1, −z+1. |
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Investigation of coordination polymers has attracted increasing interest over the past decade (Moulton & Zaworotko, 2001) because of the intriguing structural motifs of these compounds and their potential applications in catalysis, host–guest chemistry and magnetism (Leininger et al., 2000; Feng & Xu, 2001; Yuan et al., 2002). The rational design and synthesis of coordination polymers have focused on the use of benzene di- and polycarboxylates as rigid bridging spacers (Li et al., 1999; Chui et al., 1999). The utilization of aliphatic α,ω-dicarboxylates to construct supramolecular aggregates is also of growing interest (Rao et al., 2004; Kitagawa et al., 2004). Recent research has concentrated on the construction of coordination polymers with specific topologies based on co-bridging of rigid 4,4'-bipyridine and α,ω-dicarboxylates (Zheng et al., 2004; Zheng & Ying, 2005). Some interesting coordination polymers assembled with 4,4'-bipyridine (bipy) have been reported, showing various structural motifs, including two-dimensional layers (Carlucci et al., 1997; Tong et al., 1998) and three-dimensional nets (Lu et al., 1998; Hagrman et al., 1998; Kondo et al., 1999; Zhang et al., 1999; Greve et al. 2003; Şahin et al., 2007). We report here the structure of the title compound, (I), in which hydrogen bonds and C—H···π interactions lead to a two-dimensional supramolecular network.
The molecular structure of (I) and the atom-labelling scheme are shown in Fig. 1. The compound crystallizes in the space group P21/c with Z' = 1/2. The CuII atom is located on a centre of symmetry and is coordinated by two O atoms from two equivalent carboxylate groups, two O atoms from aqua ligands and two pyridyl N atoms. The geometry around the CuII ion (Table 1) is that of a distorted octahedron, the equatorial plane of which (O2/O5/O2iv/O5iv) is formed by two carboxylate O atoms (O2 and O2iv) and two aqua O atoms (O5 and O5iv) [symmetry code: (iv) 1 − x, 1 − y, 1 − z]. The axial positions are occupied by two pyridyl N atoms (N1 and N1iv). The significant difference between the Cu—L bond distances in the equatorial plane [Cu—O2/O2iv = 1.9714 (12) Å and Cu—O5/O5iv = 2.569 (2) Å] and those in the axial positions [Cu—N1/N1iv = 2.0117 (14) Å] has also been observed in other copper complexes (Uçar et al., 2005). The Cu—O5 distance is longer than corresponding values in related structures (Wen et al., 2004; Lu et al., 2006). This elongation can be attributed to the static Jahn–Teller effect. Carboxylate atom O3 is pendant, with a longer Cu1···O3 distance [3.161 (2) Å] and larger Cu1—O2—C7 angle, consistent with the absence of bonding between atoms Cu1 and O3. The carboxylate group is not coplanar with the attached benzene ring, the dihedral angle between the planes being 15.8 (2)°.
Molecules are linked by intermolecular hydrogen bonding, and we employ graph-set notation (Bernstein et al., 1995) to describe the patterns formed. Molecules of (I) are linked into sheets by a combination of O—H···O and N—H···O hydrogen bonds (Table 2). Thus, the O5—H5A···O3 hydrogen bond produces an S(6) motif (Fig. 1). Amino atom N2 in the reference molecule at (x, y, z) acts as a hydrogen-bond donor, via atom H2A, to atom O1 in the molecule at (−x + 3, −y + 1, −z + 2), so forming a C(12)[R22(8)] chain of rings running parallel to the [201] direction and a centrosymmetric R22(8) ring centred at (−1/2, 1/2, 0) (Fig. 2). Fig. 3 shows the way in which hydroxyl atom O4, a water ligand and carboxylate atom O3 are involved in intermolecular hydrogen-bonding interactions. Water atom O5 in the reference molecule at (x, y, z) acts as a hydrogen-bond donor, via atom H5B, to atom O5 in the molecule at (−x, −y + 1, −z + 1), so forming a C(4)[R22(4)] chain of rings running parallel to the [100] direction and centrosymmetric R22(4) rings centred at (0, 1/2, 1/2). At the same time, atom O4 in the reference molecule at (x, y, z) acts as a hydrogen-bond donor, via atom H4, to atom O3 of the molecule at (x + 1, y, z), so forming a C(7) chain running parallel to the [100] direction. The combination of the C(4) and C(7) chains along [100] generates a chain of edge-fused R22(15) rings (Fig. 3).
In the structure of (I), there is also a strong C—H···Cgv interaction between C3—H3 (of a pyridine ring) and the centroid Cg of a phenyl ring. Interlinked C3—H3···Cgv and C3v—H3v···Cg [symmetry code: (v) 2 − x, 1 − y, 2 − z] interactions define an R22(20) ring pattern (Fig. 4). The C—H···Cgv contact distance between the centroid of a pyridine [Should this be phenyl?] ring and the H atoms nearest that phenyl ring is 2.63 Å. The perpendicular distance between atom H3 and the centre of the phenyl ring is 2.616 Å and the C—H···Cgv angle is 153°. This C—H···π interaction produces a chain running parallel to the [101] direction.
These intermolecular interactions, namely an extensive network of hydrogen bonds and π-ring interactions, play a key role in assembling the supramolecular structure of (I).