Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040366/hb2508sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040366/hb2508Isup2.hkl |
CCDC reference: 660130
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- R factor = 0.049
- wR factor = 0.148
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O6 - H6B ... ?
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C5 - C7 ... 1.53 Ang. PLAT731_ALERT_1_C Bond Calc 0.82(7), Rep 0.83(3) ...... 2.33 su-Ra O6 -H6B 1.555 1.555
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.31 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 8
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
2,2'-biimidazole was synthesized according to the literature procedure (Xiao & Shreeve, 2005). A mixture of Cu(NO3)2·4H2O, pyridine-2,6-dicarboxylic acid, 2,2'-biimidazole and water in a molar ratio of 1:1:1:555 was sealed in a 23 ml polyfluoroethylene-lined stainless steel bomb and heated to 423 K under autogenous pressure for 72 h. After slowly cooling to room temperature and opening the bomb, blue plates of (I) were formed, collected by filtration, washed in deionized water, and finally dried.
The N– and O-bound H atoms were located in difference maps and refined with distance restraints [N–H = 0.86 (3) Å, O–H = 0.85 (3) Å, H···H = 1.39 (3) Å] and the constraints Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O).
The C-bound H atoms were geometrically placed (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
Biimidazole (H2biim) is a bidentate chelating ligand with multiple proton-donor sites which can coordinate to a transition metal in its neutral (H2biim), singly-deprotonated (Hbiim-) and doubly-deprotonated (biim2-) forms. Coordinated H2biim usually forms hydrogen bonds with counteranions or solvent molecules (Whitesides et al., (1991); Rebek,1990).
Here, we report the synthesis and sructure of the the title compound, (I), which contains Cu(II) ions, neutral H2biim and pyridine-2,6-dicarboxylate (pda) dianions. The CuII ion in (I) exhibits a distorted mer-CuN3O3 octahedral geometry (Table 1), arising from N1, N2, N4 and O5 as equatorial atoms and O1 and O3 as axial atoms.
The packing for (I) is mainly governed by a combination of O(or N, C)–H···O hydrogen bonds (Table 2, Fig. 2) linking the constituent species together.
For related literature, see: Whitesides et al. (1991); Rebek (1990); Xiao & Shreeve (2005).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
[Cu(C7H3NO4)(C6H6N4)(H2O)]·H2O | Z = 2 |
Mr = 398.82 | F(000) = 406 |
Triclinic, P1 | Dx = 1.711 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.5951 (4) Å | Cell parameters from 3382 reflections |
b = 10.6971 (7) Å | θ = 2.5–27.8° |
c = 11.6112 (7) Å | µ = 1.46 mm−1 |
α = 97.210 (1)° | T = 296 K |
β = 94.384 (1)° | Plate, blue |
γ = 106.411 (1)° | 0.35 × 0.10 × 0.06 mm |
V = 774.16 (8) Å3 |
Bruker SMART CCD diffractometer | 2978 independent reflections |
Radiation source: fine-focus sealed tube | 2595 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 26.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −8→8 |
Tmin = 0.630, Tmax = 0.918 | k = −13→13 |
7976 measured reflections | l = −14→12 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0837P)2 + 1.1035P] where P = (Fo2 + 2Fc2)/3 |
2978 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.82 e Å−3 |
8 restraints | Δρmin = −0.52 e Å−3 |
[Cu(C7H3NO4)(C6H6N4)(H2O)]·H2O | γ = 106.411 (1)° |
Mr = 398.82 | V = 774.16 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.5951 (4) Å | Mo Kα radiation |
b = 10.6971 (7) Å | µ = 1.46 mm−1 |
c = 11.6112 (7) Å | T = 296 K |
α = 97.210 (1)° | 0.35 × 0.10 × 0.06 mm |
β = 94.384 (1)° |
Bruker SMART CCD diffractometer | 2978 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2595 reflections with I > 2σ(I) |
Tmin = 0.630, Tmax = 0.918 | Rint = 0.029 |
7976 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 8 restraints |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.82 e Å−3 |
2978 reflections | Δρmin = −0.52 e Å−3 |
244 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 | ||
Cu1 | 0.72700 (7) | 0.86989 (4) | 0.73050 (4) | 0.0290 (2) | |
C1 | 0.6942 (6) | 0.5957 (3) | 0.7217 (3) | 0.0269 (8) | |
C2 | 0.5990 (7) | 0.4613 (4) | 0.6989 (4) | 0.0376 (10) | |
H2 | 0.6697 | 0.4032 | 0.7225 | 0.045* | |
C3 | 0.3954 (7) | 0.4149 (4) | 0.6399 (4) | 0.0411 (10) | |
H3 | 0.3290 | 0.3245 | 0.6229 | 0.049* | |
C4 | 0.2892 (6) | 0.5014 (4) | 0.6059 (4) | 0.0345 (9) | |
H4 | 0.1518 | 0.4711 | 0.5670 | 0.041* | |
C5 | 0.3952 (6) | 0.6344 (3) | 0.6320 (3) | 0.0261 (8) | |
C6 | 0.9129 (6) | 0.6668 (4) | 0.7889 (3) | 0.0277 (8) | |
C7 | 0.3065 (6) | 0.7458 (4) | 0.6035 (3) | 0.0281 (8) | |
C8 | 0.5874 (6) | 0.7965 (4) | 0.9848 (4) | 0.0348 (9) | |
H8 | 0.5183 | 0.7064 | 0.9679 | 0.042* | |
C9 | 0.6372 (6) | 0.8679 (4) | 1.0932 (4) | 0.0341 (9) | |
H9 | 0.6103 | 0.8369 | 1.1635 | 0.041* | |
C10 | 0.7441 (5) | 0.9956 (3) | 0.9642 (3) | 0.0252 (8) | |
C11 | 0.8339 (5) | 1.1019 (3) | 0.9001 (3) | 0.0266 (8) | |
C12 | 0.9225 (6) | 1.1865 (4) | 0.7462 (4) | 0.0348 (9) | |
H12 | 0.9476 | 1.1949 | 0.6694 | 0.042* | |
C13 | 0.9615 (7) | 1.2875 (4) | 0.8357 (4) | 0.0379 (10) | |
H13 | 1.0156 | 1.3769 | 0.8315 | 0.046* | |
N1 | 0.5914 (5) | 0.6780 (3) | 0.6882 (3) | 0.0240 (6) | |
N2 | 0.6540 (5) | 0.8769 (3) | 0.9036 (3) | 0.0286 (7) | |
N4 | 0.8402 (5) | 1.0698 (3) | 0.7868 (3) | 0.0292 (7) | |
N3 | 0.7358 (5) | 0.9956 (3) | 1.0784 (3) | 0.0301 (7) | |
H3A | 0.789 (7) | 1.059 (3) | 1.131 (3) | 0.036* | |
N5 | 0.9061 (5) | 1.2329 (3) | 0.9335 (3) | 0.0296 (7) | |
H5C | 0.908 (7) | 1.274 (4) | 1.000 (3) | 0.036* | |
O1 | 0.9727 (4) | 0.7904 (2) | 0.7902 (2) | 0.0286 (6) | |
O2 | 1.0086 (5) | 0.6037 (3) | 0.8420 (3) | 0.0425 (8) | |
O3 | 0.4277 (4) | 0.8609 (3) | 0.6434 (3) | 0.0380 (7) | |
O4 | 0.1318 (5) | 0.7184 (3) | 0.5452 (3) | 0.0406 (7) | |
O5 | 0.8806 (5) | 0.8899 (3) | 0.5814 (3) | 0.0366 (7) | |
H5A | 0.957 (7) | 0.844 (5) | 0.569 (4) | 0.055* | |
H5B | 0.808 (7) | 0.895 (5) | 0.520 (3) | 0.055* | |
O6 | 0.3788 (10) | 0.0955 (4) | 0.6068 (4) | 0.0869 (16) | |
H6A | 0.378 (13) | 0.025 (4) | 0.632 (7) | 0.130* | |
H6B | 0.480 (10) | 0.158 (5) | 0.639 (7) | 0.130* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0276 (3) | 0.0193 (3) | 0.0376 (3) | 0.00591 (19) | −0.0040 (2) | 0.0020 (2) |
C1 | 0.031 (2) | 0.0192 (16) | 0.0275 (19) | 0.0061 (14) | −0.0043 (15) | 0.0013 (14) |
C2 | 0.038 (2) | 0.0214 (18) | 0.053 (3) | 0.0122 (17) | −0.0073 (19) | 0.0037 (18) |
C3 | 0.039 (2) | 0.0196 (18) | 0.057 (3) | 0.0010 (17) | −0.007 (2) | 0.0006 (18) |
C4 | 0.029 (2) | 0.0236 (18) | 0.042 (2) | 0.0003 (15) | −0.0056 (17) | −0.0038 (17) |
C5 | 0.0279 (19) | 0.0209 (17) | 0.0274 (19) | 0.0065 (14) | −0.0038 (15) | 0.0015 (14) |
C6 | 0.0250 (18) | 0.0266 (18) | 0.031 (2) | 0.0103 (15) | −0.0012 (15) | −0.0026 (15) |
C7 | 0.0277 (19) | 0.0259 (18) | 0.033 (2) | 0.0121 (15) | 0.0000 (16) | 0.0039 (15) |
C8 | 0.029 (2) | 0.0257 (19) | 0.049 (3) | 0.0062 (16) | 0.0053 (18) | 0.0071 (18) |
C9 | 0.027 (2) | 0.037 (2) | 0.041 (2) | 0.0114 (17) | 0.0029 (17) | 0.0113 (18) |
C10 | 0.0174 (16) | 0.0228 (17) | 0.036 (2) | 0.0088 (13) | −0.0022 (14) | 0.0036 (15) |
C11 | 0.0197 (17) | 0.0188 (16) | 0.039 (2) | 0.0060 (13) | −0.0024 (15) | −0.0001 (15) |
C12 | 0.033 (2) | 0.0236 (18) | 0.046 (2) | 0.0059 (16) | −0.0005 (18) | 0.0088 (17) |
C13 | 0.035 (2) | 0.0228 (19) | 0.052 (3) | 0.0047 (16) | −0.0067 (19) | 0.0087 (18) |
N1 | 0.0237 (15) | 0.0190 (14) | 0.0272 (16) | 0.0061 (12) | −0.0032 (12) | 0.0000 (12) |
N2 | 0.0235 (15) | 0.0214 (15) | 0.0389 (19) | 0.0056 (12) | 0.0017 (13) | 0.0009 (13) |
N4 | 0.0273 (16) | 0.0180 (14) | 0.041 (2) | 0.0069 (12) | −0.0018 (14) | 0.0026 (13) |
N3 | 0.0222 (16) | 0.0287 (16) | 0.037 (2) | 0.0071 (13) | −0.0029 (13) | −0.0002 (14) |
N5 | 0.0276 (16) | 0.0180 (15) | 0.041 (2) | 0.0076 (12) | −0.0036 (14) | −0.0019 (13) |
O1 | 0.0271 (13) | 0.0215 (12) | 0.0340 (15) | 0.0065 (10) | −0.0060 (11) | −0.0003 (11) |
O2 | 0.0399 (17) | 0.0316 (15) | 0.055 (2) | 0.0174 (13) | −0.0175 (14) | 0.0022 (14) |
O3 | 0.0305 (15) | 0.0226 (13) | 0.0584 (19) | 0.0087 (11) | −0.0122 (13) | 0.0053 (13) |
O4 | 0.0340 (16) | 0.0369 (16) | 0.0474 (18) | 0.0156 (13) | −0.0170 (13) | −0.0050 (14) |
O5 | 0.0457 (18) | 0.0357 (16) | 0.0323 (16) | 0.0185 (13) | 0.0007 (13) | 0.0065 (13) |
O6 | 0.147 (5) | 0.045 (2) | 0.069 (3) | 0.048 (3) | −0.043 (3) | −0.004 (2) |
Cu1—N1 | 1.974 (3) | C8—C9 | 1.353 (6) |
Cu1—N4 | 2.056 (3) | C8—N2 | 1.369 (5) |
Cu1—O5 | 2.076 (3) | C8—H8 | 0.9300 |
Cu1—N2 | 2.100 (3) | C9—N3 | 1.376 (5) |
Cu1—O3 | 2.120 (3) | C9—H9 | 0.9300 |
Cu1—O1 | 2.141 (3) | C10—N2 | 1.321 (5) |
C1—N1 | 1.330 (5) | C10—N3 | 1.331 (5) |
C1—C2 | 1.378 (5) | C10—C11 | 1.449 (5) |
C1—C6 | 1.525 (5) | C11—N4 | 1.324 (5) |
C2—C3 | 1.384 (6) | C11—N5 | 1.341 (5) |
C2—H2 | 0.9300 | C12—C13 | 1.354 (6) |
C3—C4 | 1.385 (6) | C12—N4 | 1.371 (5) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.379 (5) | C13—N5 | 1.369 (6) |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—N1 | 1.331 (5) | N3—H3A | 0.83 (3) |
C5—C7 | 1.529 (5) | N5—H5C | 0.83 (3) |
C6—O2 | 1.233 (5) | O5—H5A | 0.80 (3) |
C6—O1 | 1.267 (4) | O5—H5B | 0.84 (3) |
C7—O4 | 1.229 (5) | O6—H6A | 0.84 (3) |
C7—O3 | 1.270 (5) | O6—H6B | 0.83 (3) |
N1—Cu1—N4 | 173.29 (12) | N2—C8—H8 | 125.2 |
N1—Cu1—O5 | 95.10 (12) | C8—C9—N3 | 106.1 (4) |
N4—Cu1—O5 | 91.07 (13) | C8—C9—H9 | 127.0 |
N1—Cu1—N2 | 94.58 (12) | N3—C9—H9 | 127.0 |
N4—Cu1—N2 | 79.94 (12) | N2—C10—N3 | 111.8 (3) |
O5—Cu1—N2 | 164.58 (13) | N2—C10—C11 | 117.7 (3) |
N1—Cu1—O3 | 77.85 (11) | N3—C10—C11 | 130.6 (3) |
N4—Cu1—O3 | 99.15 (11) | N4—C11—N5 | 111.4 (3) |
O5—Cu1—O3 | 93.90 (13) | N4—C11—C10 | 117.1 (3) |
N2—Cu1—O3 | 99.86 (13) | N5—C11—C10 | 131.4 (4) |
N1—Cu1—O1 | 77.50 (11) | C13—C12—N4 | 109.2 (4) |
N4—Cu1—O1 | 105.69 (11) | C13—C12—H12 | 125.4 |
O5—Cu1—O1 | 85.31 (11) | N4—C12—H12 | 125.4 |
N2—Cu1—O1 | 85.10 (11) | C12—C13—N5 | 106.8 (3) |
O3—Cu1—O1 | 155.16 (10) | C12—C13—H13 | 126.6 |
N1—C1—C2 | 120.4 (4) | N5—C13—H13 | 126.6 |
N1—C1—C6 | 112.9 (3) | C1—N1—C5 | 121.7 (3) |
C2—C1—C6 | 126.6 (4) | C1—N1—Cu1 | 119.1 (2) |
C1—C2—C3 | 118.3 (4) | C5—N1—Cu1 | 119.0 (2) |
C1—C2—H2 | 120.8 | C10—N2—C8 | 105.5 (3) |
C3—C2—H2 | 120.8 | C10—N2—Cu1 | 110.9 (2) |
C2—C3—C4 | 120.8 (4) | C8—N2—Cu1 | 141.3 (3) |
C2—C3—H3 | 119.6 | C11—N4—C12 | 105.8 (3) |
C4—C3—H3 | 119.6 | C11—N4—Cu1 | 113.0 (2) |
C5—C4—C3 | 117.4 (4) | C12—N4—Cu1 | 141.3 (3) |
C5—C4—H4 | 121.3 | C10—N3—C9 | 107.0 (3) |
C3—C4—H4 | 121.3 | C10—N3—H3A | 127 (3) |
N1—C5—C4 | 121.3 (3) | C9—N3—H3A | 126 (3) |
N1—C5—C7 | 112.9 (3) | C11—N5—C13 | 106.8 (3) |
C4—C5—C7 | 125.7 (3) | C11—N5—H5C | 127 (3) |
O2—C6—O1 | 125.9 (4) | C13—N5—H5C | 126 (3) |
O2—C6—C1 | 119.3 (3) | C6—O1—Cu1 | 114.4 (2) |
O1—C6—C1 | 114.7 (3) | C7—O3—Cu1 | 115.6 (2) |
O4—C7—O3 | 126.3 (3) | Cu1—O5—H5A | 116 (4) |
O4—C7—C5 | 119.2 (3) | Cu1—O5—H5B | 117 (4) |
O3—C7—C5 | 114.4 (3) | H5A—O5—H5B | 113 (4) |
C9—C8—N2 | 109.7 (3) | H6A—O6—H6B | 112 (5) |
C9—C8—H8 | 125.2 | ||
N1—C1—C2—C3 | 0.3 (6) | N4—Cu1—N2—C10 | −10.2 (2) |
C6—C1—C2—C3 | 177.6 (4) | O5—Cu1—N2—C10 | 44.9 (6) |
C1—C2—C3—C4 | −0.7 (7) | O3—Cu1—N2—C10 | −107.9 (2) |
C2—C3—C4—C5 | 0.7 (7) | O1—Cu1—N2—C10 | 96.7 (3) |
C3—C4—C5—N1 | −0.3 (6) | N1—Cu1—N2—C8 | 14.6 (4) |
C3—C4—C5—C7 | −179.4 (4) | N4—Cu1—N2—C8 | −169.3 (4) |
N1—C1—C6—O2 | 167.6 (3) | O5—Cu1—N2—C8 | −114.1 (5) |
C2—C1—C6—O2 | −9.9 (6) | O3—Cu1—N2—C8 | 93.1 (4) |
N1—C1—C6—O1 | −8.0 (5) | O1—Cu1—N2—C8 | −62.4 (4) |
C2—C1—C6—O1 | 174.5 (4) | N5—C11—N4—C12 | 0.5 (4) |
N1—C5—C7—O4 | 175.4 (4) | C10—C11—N4—C12 | 177.6 (3) |
C4—C5—C7—O4 | −5.4 (6) | N5—C11—N4—Cu1 | −179.2 (2) |
N1—C5—C7—O3 | −3.9 (5) | C10—C11—N4—Cu1 | −2.1 (4) |
C4—C5—C7—O3 | 175.3 (4) | C13—C12—N4—C11 | −0.9 (4) |
N2—C8—C9—N3 | 0.4 (5) | C13—C12—N4—Cu1 | 178.6 (3) |
N2—C10—C11—N4 | −7.3 (5) | O5—Cu1—N4—C11 | −160.8 (3) |
N3—C10—C11—N4 | 172.6 (4) | N2—Cu1—N4—C11 | 6.6 (3) |
N2—C10—C11—N5 | 169.0 (4) | O3—Cu1—N4—C11 | 105.0 (3) |
N3—C10—C11—N5 | −11.1 (7) | O1—Cu1—N4—C11 | −75.4 (3) |
N4—C12—C13—N5 | 1.0 (5) | O5—Cu1—N4—C12 | 19.6 (4) |
C2—C1—N1—C5 | 0.0 (6) | N2—Cu1—N4—C12 | −173.0 (4) |
C6—C1—N1—C5 | −177.6 (3) | O3—Cu1—N4—C12 | −74.5 (4) |
C2—C1—N1—Cu1 | 176.5 (3) | O1—Cu1—N4—C12 | 105.1 (4) |
C6—C1—N1—Cu1 | −1.1 (4) | N2—C10—N3—C9 | 1.2 (4) |
C4—C5—N1—C1 | −0.1 (6) | C11—C10—N3—C9 | −178.7 (4) |
C7—C5—N1—C1 | 179.1 (3) | C8—C9—N3—C10 | −0.9 (4) |
C4—C5—N1—Cu1 | −176.5 (3) | N4—C11—N5—C13 | 0.1 (4) |
C7—C5—N1—Cu1 | 2.6 (4) | C10—C11—N5—C13 | −176.4 (4) |
O5—Cu1—N1—C1 | 89.7 (3) | C12—C13—N5—C11 | −0.6 (4) |
N2—Cu1—N1—C1 | −78.3 (3) | O2—C6—O1—Cu1 | −162.8 (3) |
O3—Cu1—N1—C1 | −177.4 (3) | C1—C6—O1—Cu1 | 12.5 (4) |
O1—Cu1—N1—C1 | 5.7 (3) | N1—Cu1—O1—C6 | −10.3 (3) |
O5—Cu1—N1—C5 | −93.7 (3) | N4—Cu1—O1—C6 | 163.6 (3) |
N2—Cu1—N1—C5 | 98.3 (3) | O5—Cu1—O1—C6 | −106.6 (3) |
O3—Cu1—N1—C5 | −0.8 (3) | N2—Cu1—O1—C6 | 85.5 (3) |
O1—Cu1—N1—C5 | −177.8 (3) | O3—Cu1—O1—C6 | −17.4 (4) |
N3—C10—N2—C8 | −0.9 (4) | O4—C7—O3—Cu1 | −176.0 (3) |
C11—C10—N2—C8 | 179.0 (3) | C5—C7—O3—Cu1 | 3.2 (4) |
N3—C10—N2—Cu1 | −167.5 (2) | N1—Cu1—O3—C7 | −1.5 (3) |
C11—C10—N2—Cu1 | 12.4 (4) | N4—Cu1—O3—C7 | −175.4 (3) |
C9—C8—N2—C10 | 0.3 (4) | O5—Cu1—O3—C7 | 92.9 (3) |
C9—C8—N2—Cu1 | 160.1 (3) | N2—Cu1—O3—C7 | −94.1 (3) |
N1—Cu1—N2—C10 | 173.7 (3) | O1—Cu1—O3—C7 | 5.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O3i | 0.84 (3) | 1.90 (4) | 2.700 (5) | 160 (9) |
O5—H5B···O6ii | 0.84 (3) | 1.88 (3) | 2.719 (5) | 174 (5) |
O5—H5A···O4iii | 0.80 (3) | 2.01 (3) | 2.813 (4) | 175 (5) |
N5—H5C···O2iv | 0.83 (3) | 2.05 (3) | 2.871 (5) | 166 (4) |
N3—H3A···O1iv | 0.83 (3) | 1.97 (3) | 2.729 (4) | 152 (4) |
C3—H3···O6 | 0.93 | 2.55 | 3.359 (6) | 146 |
C13—H13···O2v | 0.93 | 2.43 | 3.298 (5) | 156 |
C4—H4···O4vi | 0.93 | 2.48 | 3.294 (5) | 147 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+2, −z+2; (v) x, y+1, z; (vi) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C7H3NO4)(C6H6N4)(H2O)]·H2O |
Mr | 398.82 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 6.5951 (4), 10.6971 (7), 11.6112 (7) |
α, β, γ (°) | 97.210 (1), 94.384 (1), 106.411 (1) |
V (Å3) | 774.16 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.46 |
Crystal size (mm) | 0.35 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.630, 0.918 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7976, 2978, 2595 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.148, 1.10 |
No. of reflections | 2978 |
No. of parameters | 244 |
No. of restraints | 8 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.82, −0.52 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).
Cu1—N1 | 1.974 (3) | Cu1—N2 | 2.100 (3) |
Cu1—N4 | 2.056 (3) | Cu1—O3 | 2.120 (3) |
Cu1—O5 | 2.076 (3) | Cu1—O1 | 2.141 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···O3i | 0.84 (3) | 1.90 (4) | 2.700 (5) | 160 (9) |
O5—H5B···O6ii | 0.84 (3) | 1.88 (3) | 2.719 (5) | 174 (5) |
O5—H5A···O4iii | 0.80 (3) | 2.01 (3) | 2.813 (4) | 175 (5) |
N5—H5C···O2iv | 0.83 (3) | 2.05 (3) | 2.871 (5) | 166 (4) |
N3—H3A···O1iv | 0.83 (3) | 1.97 (3) | 2.729 (4) | 152 (4) |
C3—H3···O6 | 0.93 | 2.55 | 3.359 (6) | 146 |
C13—H13···O2v | 0.93 | 2.43 | 3.298 (5) | 156 |
C4—H4···O4vi | 0.93 | 2.48 | 3.294 (5) | 147 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+2, −z+2; (v) x, y+1, z; (vi) −x, −y+1, −z+1. |
Biimidazole (H2biim) is a bidentate chelating ligand with multiple proton-donor sites which can coordinate to a transition metal in its neutral (H2biim), singly-deprotonated (Hbiim-) and doubly-deprotonated (biim2-) forms. Coordinated H2biim usually forms hydrogen bonds with counteranions or solvent molecules (Whitesides et al., (1991); Rebek,1990).
Here, we report the synthesis and sructure of the the title compound, (I), which contains Cu(II) ions, neutral H2biim and pyridine-2,6-dicarboxylate (pda) dianions. The CuII ion in (I) exhibits a distorted mer-CuN3O3 octahedral geometry (Table 1), arising from N1, N2, N4 and O5 as equatorial atoms and O1 and O3 as axial atoms.
The packing for (I) is mainly governed by a combination of O(or N, C)–H···O hydrogen bonds (Table 2, Fig. 2) linking the constituent species together.