Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807067517/si2057sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807067517/si2057Isup2.hkl |
CCDC reference: 677392
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- R factor = 0.063
- wR factor = 0.122
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent N Ueq(max)/Ueq(min) ... 4.03 Ratio PLAT420_ALERT_2_B D-H Without Acceptor O16 - H16B ... ? PLAT420_ALERT_2_B D-H Without Acceptor O17 - H17D ... ?
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.32 Ratio PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C8 - C9 ... 1.53 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C20 - C21 ... 1.53 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 7
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
2-(Oxaloamino)benzoic acid (0.232 g, 1 mmol; Zang et al., 2003) and ? (0.12 g, 3 mmol) were dissolved in water (20 ml). To this solution, CuCl2.2H2O (0.17 g, 1 mmol) and imidazole (0.068 g, 1 mmol) were added. After stirring for an hour, CaCl2 (0.111 g, 1 mmol) was added. The solution was filtered after stirring for another hour. Evaporation of the filtrate gave green single crystals of the title compound after one week. Elemental analysis found (calculatedd) for C24H36CaCu2N6O20 (%): C 32.26 (32.18); H, 3.92 (4.05); N 9.52 (9.38); Ca 4.45 (4.47); Cu 14.14 (14.19). The analyses were performed on a Perkin–Elmer 240 C elemental analyzer. The abundance of Cu is determined by spectrophotometry while the abundance of Ca is obtained from edta titration.
The structure was solved by direct methods. All the H atoms were fixed geometrically and constrained with a riding model. d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic 0.97 Å, Uiso = 1.2Ueq (C) for CH2 and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms; 0.85 Å, Uiso = 1.5Ueq (O) for H2O atoms.
Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: publCIF (Westrip, 2008).
Fig. 1. Asymmetric unit of the title compound. Hydrogen atoms are omitted for clarity. Displacement ellipsoids are drawn at the 50% probability level. |
[CaCu2(C9H4NO5)2(C3H4N2)2(H2O)3]·7H2O | F(000) = 1840 |
Mr = 895.75 | Dx = 1.701 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1959 reflections |
a = 6.8988 (9) Å | θ = 2.7–20.5° |
b = 24.011 (3) Å | µ = 1.45 mm−1 |
c = 21.161 (3) Å | T = 293 K |
β = 93.511 (3)° | Block, green |
V = 3498.7 (8) Å3 | 0.2 × 0.2 × 0.2 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 6119 independent reflections |
Radiation source: fine-focus sealed tube | 3486 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.093 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −8→8 |
Tmin = 0.75, Tmax = 0.76 | k = −28→28 |
17203 measured reflections | l = −15→25 |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3 |
6119 reflections | (Δ/σ)max = 0.018 |
478 parameters | Δρmax = 0.59 e Å−3 |
7 restraints | Δρmin = −0.48 e Å−3 |
[CaCu2(C9H4NO5)2(C3H4N2)2(H2O)3]·7H2O | V = 3498.7 (8) Å3 |
Mr = 895.75 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.8988 (9) Å | µ = 1.45 mm−1 |
b = 24.011 (3) Å | T = 293 K |
c = 21.161 (3) Å | 0.2 × 0.2 × 0.2 mm |
β = 93.511 (3)° |
Bruker SMART CCD area-detector diffractometer | 6119 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 3486 reflections with I > 2σ(I) |
Tmin = 0.75, Tmax = 0.76 | Rint = 0.093 |
17203 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 7 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.59 e Å−3 |
6119 reflections | Δρmin = −0.48 e Å−3 |
478 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 | ||
Ca1 | 0.57052 (19) | 0.21723 (5) | 0.36790 (5) | 0.0305 (3) | |
Cu1 | 0.42034 (12) | 0.15913 (3) | 0.10945 (3) | 0.0365 (2) | |
Cu2 | 0.40057 (12) | 0.12870 (3) | 0.60805 (3) | 0.0303 (2) | |
N1 | 0.4528 (7) | 0.20197 (17) | 0.57516 (19) | 0.0223 (12) | |
N2 | 0.4559 (7) | 0.22668 (18) | 0.1570 (2) | 0.0275 (12) | |
C1 | 0.4976 (10) | 0.2460 (3) | 0.0207 (3) | 0.0400 (17) | |
C2 | 0.4626 (8) | 0.2899 (2) | 0.0672 (3) | 0.0273 (15) | |
C3 | 0.4444 (9) | 0.3438 (3) | 0.0446 (3) | 0.0405 (17) | |
H3 | 0.4611 | 0.3502 | 0.0019 | 0.049* | |
C4 | 0.4034 (10) | 0.3877 (3) | 0.0816 (3) | 0.0460 (19) | |
H4 | 0.3903 | 0.4232 | 0.0645 | 0.055* | |
C5 | 0.3812 (10) | 0.3788 (3) | 0.1455 (3) | 0.0422 (18) | |
H5 | 0.3532 | 0.4085 | 0.1716 | 0.051* | |
C6 | 0.4004 (9) | 0.3262 (2) | 0.1701 (3) | 0.0326 (16) | |
H6 | 0.3856 | 0.3206 | 0.2131 | 0.039* | |
C7 | 0.4416 (8) | 0.2810 (2) | 0.1321 (2) | 0.0260 (14) | |
C8 | 0.4955 (9) | 0.2169 (2) | 0.2188 (3) | 0.0278 (15) | |
C9 | 0.4692 (9) | 0.1558 (2) | 0.2362 (3) | 0.0294 (15) | |
N3 | 0.3548 (9) | 0.0899 (2) | 0.0656 (3) | 0.0497 (16) | |
C10 | 0.3866 (13) | 0.0390 (3) | 0.0854 (4) | 0.070 (3) | |
H10 | 0.4524 | 0.0299 | 0.1236 | 0.084* | |
N4 | 0.3135 (12) | 0.0024 (3) | 0.0442 (4) | 0.091 (3) | |
H4A | 0.3211 | −0.0332 | 0.0478 | 0.109* | |
C11 | 0.2251 (14) | 0.0305 (4) | −0.0043 (4) | 0.083 (3) | |
H11 | 0.1579 | 0.0154 | −0.0397 | 0.099* | |
C12 | 0.2529 (12) | 0.0841 (4) | 0.0084 (4) | 0.070 (2) | |
H12 | 0.2098 | 0.1133 | −0.0177 | 0.084* | |
C13 | 0.4628 (9) | 0.1977 (3) | 0.7176 (3) | 0.0309 (16) | |
C14 | 0.4633 (8) | 0.2491 (2) | 0.6780 (3) | 0.0268 (15) | |
C15 | 0.4633 (9) | 0.2996 (3) | 0.7113 (3) | 0.0417 (18) | |
H15 | 0.4738 | 0.2986 | 0.7553 | 0.050* | |
C16 | 0.4481 (10) | 0.3508 (3) | 0.6814 (3) | 0.0451 (19) | |
H16 | 0.4443 | 0.3836 | 0.7046 | 0.054* | |
C17 | 0.4390 (10) | 0.3517 (2) | 0.6165 (3) | 0.0422 (18) | |
H17 | 0.4291 | 0.3857 | 0.5954 | 0.051* | |
C18 | 0.4441 (9) | 0.3035 (2) | 0.5821 (3) | 0.0352 (17) | |
H18 | 0.4390 | 0.3057 | 0.5382 | 0.042* | |
C19 | 0.4568 (8) | 0.2516 (2) | 0.6106 (3) | 0.0258 (15) | |
C20 | 0.4908 (8) | 0.2006 (2) | 0.5142 (3) | 0.0247 (14) | |
C21 | 0.4483 (9) | 0.1434 (2) | 0.4842 (3) | 0.0305 (16) | |
N5 | 0.3638 (8) | 0.05199 (19) | 0.6339 (2) | 0.0339 (14) | |
C22 | 0.2829 (10) | 0.0326 (3) | 0.6870 (3) | 0.0466 (19) | |
H22 | 0.2244 | 0.0544 | 0.7169 | 0.056* | |
C23 | 0.3020 (12) | −0.0230 (3) | 0.6888 (4) | 0.061 (2) | |
H23 | 0.2597 | −0.0466 | 0.7199 | 0.074* | |
N6 | 0.3947 (9) | −0.0383 (2) | 0.6367 (3) | 0.0591 (18) | |
H6A | 0.4251 | −0.0716 | 0.6261 | 0.071* | |
C24 | 0.4289 (10) | 0.0077 (3) | 0.6058 (3) | 0.0468 (19) | |
H24 | 0.4919 | 0.0088 | 0.5682 | 0.056* | |
O1 | 0.5537 (7) | 0.26049 (18) | −0.03227 (19) | 0.0528 (13) | |
O2 | 0.4690 (7) | 0.19479 (18) | 0.03125 (17) | 0.0415 (12) | |
O3 | 0.4352 (7) | 0.12114 (15) | 0.19170 (18) | 0.0423 (12) | |
O4 | 0.4854 (7) | 0.14343 (15) | 0.29325 (19) | 0.0436 (13) | |
O5 | 0.5407 (6) | 0.24986 (15) | 0.26216 (17) | 0.0347 (11) | |
O6 | 0.5085 (6) | 0.20180 (16) | 0.77547 (17) | 0.0420 (12) | |
O7 | 0.4140 (7) | 0.15086 (16) | 0.69376 (17) | 0.0418 (12) | |
O8 | 0.5517 (6) | 0.23713 (15) | 0.47962 (17) | 0.0315 (10) | |
O9 | 0.4621 (7) | 0.13889 (15) | 0.42624 (17) | 0.0401 (12) | |
O10 | 0.4020 (6) | 0.10426 (15) | 0.51994 (17) | 0.0372 (12) | |
O11 | 0.8768 (6) | 0.17246 (16) | 0.37391 (18) | 0.0466 (12) | |
H11A | 0.9524 | 0.1891 | 0.4009 | 0.070* | |
H11C | 0.8666 | 0.1385 | 0.3846 | 0.070* | |
O12 | 0.2690 (6) | 0.26068 (18) | 0.36776 (18) | 0.0590 (14) | |
H12A | 0.1876 | 0.2723 | 0.3390 | 0.089* | |
H12B | 0.2011 | 0.2541 | 0.3991 | 0.089* | |
O13 | 0.7663 (6) | 0.29991 (15) | 0.37573 (18) | 0.0492 (13) | |
H13A | 0.8576 | 0.2976 | 0.3507 | 0.074* | |
H13B | 0.6965 | 0.3282 | 0.3663 | 0.074* | |
O14 | 0.2004 (10) | 0.0229 (2) | 0.2365 (3) | 0.117 (2) | |
H14C | 0.2560 | 0.0500 | 0.2192 | 0.175* | |
H14D | 0.1710 | 0.0263 | 0.2747 | 0.175* | |
O15 | 0.1196 (7) | 0.08557 (18) | 0.3431 (2) | 0.0766 (17) | |
H15A | 0.2257 | 0.1036 | 0.3467 | 0.115* | |
H15D | 0.1356 | 0.0662 | 0.3767 | 0.115* | |
O16 | 0.1226 (8) | 0.02987 (18) | 0.4619 (2) | 0.0818 (18) | |
H16A | 0.1659 | 0.0551 | 0.4871 | 0.123* | |
H16B | 0.2171 | 0.0074 | 0.4592 | 0.123* | |
O17 | 0.1399 (16) | 0.0127 (4) | 0.8469 (4) | 0.252 (5) | |
H17C | 0.0609 | −0.0057 | 0.8226 | 0.378* | |
H17D | 0.2441 | 0.0153 | 0.8276 | 0.378* | |
O18 | 0.6065 (16) | 0.0784 (2) | 0.7980 (4) | 0.265 (7) | |
H18C | 0.6615 | 0.0481 | 0.7884 | 0.397* | |
H18D | 0.5511 | 0.0987 | 0.7693 | 0.397* | |
O19 | 0.9605 (13) | 0.1133 (3) | 0.8665 (4) | 0.198 (4) | |
H19C | 1.0155 | 0.0822 | 0.8607 | 0.296* | |
H19D | 0.9021 | 0.1202 | 0.8308 | 0.296* | |
O20 | 0.6630 (11) | 0.1175 (2) | 0.9470 (3) | 0.149 (3) | |
H20C | 0.7636 | 0.1334 | 0.9343 | 0.224* | |
H20D | 0.5978 | 0.1372 | 0.9715 | 0.224* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ca1 | 0.0384 (9) | 0.0344 (7) | 0.0194 (7) | −0.0010 (7) | 0.0075 (6) | 0.0025 (6) |
Cu1 | 0.0455 (6) | 0.0401 (5) | 0.0245 (4) | −0.0008 (4) | 0.0074 (4) | −0.0051 (4) |
Cu2 | 0.0427 (5) | 0.0282 (4) | 0.0208 (4) | −0.0017 (4) | 0.0095 (4) | 0.0012 (4) |
N1 | 0.028 (3) | 0.025 (3) | 0.015 (3) | −0.007 (2) | 0.004 (2) | −0.004 (2) |
N2 | 0.035 (3) | 0.028 (3) | 0.020 (3) | 0.000 (3) | 0.007 (2) | 0.004 (2) |
C1 | 0.035 (5) | 0.059 (5) | 0.026 (4) | 0.007 (4) | 0.003 (3) | 0.012 (4) |
C2 | 0.021 (4) | 0.039 (4) | 0.022 (3) | −0.002 (3) | 0.003 (3) | 0.011 (3) |
C3 | 0.038 (5) | 0.055 (5) | 0.030 (4) | −0.006 (4) | 0.009 (3) | 0.007 (4) |
C4 | 0.050 (5) | 0.033 (4) | 0.055 (5) | −0.015 (4) | 0.001 (4) | 0.020 (4) |
C5 | 0.053 (5) | 0.029 (4) | 0.046 (4) | −0.013 (4) | 0.009 (4) | 0.001 (3) |
C6 | 0.033 (4) | 0.036 (4) | 0.029 (4) | −0.004 (3) | 0.006 (3) | 0.007 (3) |
C7 | 0.025 (4) | 0.037 (4) | 0.016 (3) | −0.008 (3) | 0.005 (3) | 0.006 (3) |
C8 | 0.026 (4) | 0.037 (4) | 0.022 (4) | 0.006 (3) | 0.008 (3) | 0.003 (3) |
C9 | 0.030 (4) | 0.029 (4) | 0.031 (4) | 0.003 (3) | 0.009 (3) | 0.004 (3) |
N3 | 0.074 (5) | 0.041 (4) | 0.035 (3) | −0.012 (4) | 0.010 (3) | −0.009 (3) |
C10 | 0.101 (8) | 0.063 (6) | 0.049 (5) | −0.011 (6) | 0.022 (5) | −0.025 (5) |
N4 | 0.126 (8) | 0.059 (5) | 0.092 (6) | −0.026 (5) | 0.052 (6) | −0.033 (5) |
C11 | 0.088 (8) | 0.096 (8) | 0.065 (6) | −0.028 (6) | 0.015 (6) | −0.036 (6) |
C12 | 0.067 (6) | 0.086 (6) | 0.057 (5) | −0.005 (5) | 0.001 (4) | −0.022 (5) |
C13 | 0.015 (4) | 0.054 (5) | 0.024 (4) | 0.001 (3) | 0.003 (3) | −0.005 (3) |
C14 | 0.025 (4) | 0.031 (4) | 0.026 (3) | 0.005 (3) | 0.009 (3) | −0.003 (3) |
C15 | 0.039 (5) | 0.053 (5) | 0.034 (4) | −0.002 (4) | 0.013 (3) | −0.018 (4) |
C16 | 0.048 (5) | 0.028 (4) | 0.061 (5) | −0.006 (4) | 0.018 (4) | −0.026 (4) |
C17 | 0.052 (5) | 0.021 (3) | 0.056 (5) | −0.005 (3) | 0.023 (4) | 0.006 (3) |
C18 | 0.049 (5) | 0.030 (4) | 0.029 (4) | −0.005 (3) | 0.022 (3) | −0.004 (3) |
C19 | 0.019 (4) | 0.030 (3) | 0.029 (3) | −0.002 (3) | 0.008 (3) | −0.001 (3) |
C20 | 0.020 (4) | 0.028 (4) | 0.027 (4) | 0.002 (3) | 0.005 (3) | −0.002 (3) |
C21 | 0.032 (4) | 0.027 (4) | 0.033 (4) | −0.001 (3) | 0.003 (3) | −0.002 (3) |
N5 | 0.047 (4) | 0.026 (3) | 0.029 (3) | 0.002 (3) | 0.010 (3) | 0.005 (2) |
C22 | 0.063 (6) | 0.034 (4) | 0.044 (5) | 0.000 (4) | 0.023 (4) | 0.003 (4) |
C23 | 0.069 (6) | 0.060 (6) | 0.057 (5) | −0.012 (5) | 0.015 (5) | 0.025 (4) |
N6 | 0.075 (5) | 0.030 (3) | 0.072 (5) | 0.002 (3) | 0.000 (4) | 0.009 (3) |
C24 | 0.070 (6) | 0.030 (4) | 0.042 (4) | 0.006 (4) | 0.012 (4) | 0.006 (4) |
O1 | 0.059 (3) | 0.071 (3) | 0.031 (2) | 0.014 (2) | 0.025 (2) | 0.010 (2) |
O2 | 0.056 (3) | 0.049 (3) | 0.020 (2) | 0.004 (3) | 0.014 (2) | −0.003 (2) |
O3 | 0.073 (4) | 0.029 (2) | 0.026 (2) | −0.004 (2) | 0.008 (2) | −0.003 (2) |
O4 | 0.075 (4) | 0.031 (3) | 0.026 (2) | −0.006 (2) | 0.004 (2) | 0.009 (2) |
O5 | 0.054 (3) | 0.033 (2) | 0.017 (2) | −0.005 (2) | 0.004 (2) | 0.002 (2) |
O6 | 0.042 (3) | 0.066 (3) | 0.018 (2) | −0.003 (2) | −0.001 (2) | −0.002 (2) |
O7 | 0.066 (4) | 0.038 (3) | 0.022 (2) | −0.007 (3) | 0.007 (2) | −0.002 (2) |
O8 | 0.043 (3) | 0.029 (2) | 0.024 (2) | −0.003 (2) | 0.012 (2) | 0.0015 (19) |
O9 | 0.069 (4) | 0.034 (3) | 0.018 (2) | −0.009 (2) | 0.014 (2) | −0.0050 (19) |
O10 | 0.065 (3) | 0.027 (2) | 0.022 (2) | −0.013 (2) | 0.017 (2) | 0.0012 (19) |
O11 | 0.046 (3) | 0.049 (3) | 0.043 (3) | 0.000 (2) | −0.005 (2) | −0.003 (2) |
O12 | 0.046 (3) | 0.100 (4) | 0.032 (3) | 0.019 (3) | 0.009 (2) | 0.023 (3) |
O13 | 0.050 (3) | 0.046 (3) | 0.053 (3) | 0.003 (2) | 0.016 (2) | −0.005 (2) |
O14 | 0.143 (7) | 0.134 (5) | 0.076 (4) | 0.021 (5) | 0.033 (4) | 0.015 (4) |
O15 | 0.054 (4) | 0.061 (3) | 0.114 (5) | −0.002 (3) | 0.003 (3) | −0.003 (3) |
O16 | 0.085 (5) | 0.069 (3) | 0.092 (4) | −0.007 (3) | 0.014 (3) | −0.041 (3) |
O17 | 0.297 (13) | 0.352 (13) | 0.105 (6) | 0.155 (11) | 0.000 (7) | −0.011 (8) |
O18 | 0.451 (18) | 0.077 (5) | 0.236 (10) | 0.052 (7) | −0.226 (11) | −0.008 (6) |
O19 | 0.199 (10) | 0.115 (6) | 0.277 (12) | −0.027 (7) | 0.002 (8) | 0.010 (7) |
O20 | 0.194 (8) | 0.105 (5) | 0.160 (7) | −0.032 (5) | 0.098 (6) | −0.042 (5) |
Ca1—O12 | 2.327 (4) | C13—O6 | 1.250 (6) |
Ca1—O11 | 2.367 (4) | C13—O7 | 1.269 (6) |
Ca1—O5 | 2.368 (4) | C13—C14 | 1.492 (8) |
Ca1—O9 | 2.395 (4) | C14—C15 | 1.403 (7) |
Ca1—O13 | 2.401 (4) | C14—C19 | 1.425 (7) |
Ca1—O4 | 2.422 (4) | C15—C16 | 1.384 (8) |
Ca1—O8 | 2.423 (4) | C15—H15 | 0.93 |
Ca1—H11A | 2.7672 | C16—C17 | 1.372 (8) |
Ca1—H11C | 2.7894 | C16—H16 | 0.93 |
Cu1—O2 | 1.911 (4) | C17—C18 | 1.368 (7) |
Cu1—N2 | 1.917 (4) | C17—H17 | 0.93 |
Cu1—N3 | 1.943 (5) | C18—C19 | 1.384 (7) |
Cu1—O3 | 1.962 (4) | C18—H18 | 0.93 |
Cu2—O7 | 1.887 (4) | C20—O8 | 1.234 (6) |
Cu2—N1 | 1.934 (4) | C20—C21 | 1.533 (7) |
Cu2—N5 | 1.943 (5) | C21—O9 | 1.240 (6) |
Cu2—O10 | 1.955 (4) | C21—O10 | 1.260 (6) |
N1—C20 | 1.332 (6) | N5—C24 | 1.311 (7) |
N1—C19 | 1.409 (6) | N5—C22 | 1.367 (7) |
N2—C8 | 1.340 (6) | C22—C23 | 1.342 (8) |
N2—C7 | 1.409 (6) | C22—H22 | 0.93 |
C1—O1 | 1.257 (7) | C23—N6 | 1.358 (8) |
C1—O2 | 1.266 (7) | C23—H23 | 0.93 |
C1—C2 | 1.473 (8) | N6—C24 | 1.313 (7) |
C2—C3 | 1.383 (7) | N6—H6A | 0.86 |
C2—C7 | 1.406 (7) | C24—H24 | 0.93 |
C3—C4 | 1.352 (8) | O11—H11A | 0.85 |
C3—H3 | 0.93 | O11—H11C | 0.85 |
C4—C5 | 1.385 (8) | O12—H12A | 0.85 |
C4—H4 | 0.93 | O12—H12B | 0.85 |
C5—C6 | 1.369 (7) | O13—H13A | 0.85 |
C5—H5 | 0.93 | O13—H13B | 0.85 |
C6—C7 | 1.390 (7) | O14—H14C | 0.85 |
C6—H6 | 0.93 | O14—H14D | 0.85 |
C8—O5 | 1.237 (6) | O15—H15A | 0.85 |
C8—C9 | 1.526 (7) | O15—H15D | 0.85 |
C9—O4 | 1.241 (6) | O16—H16A | 0.85 |
C9—O3 | 1.268 (6) | O16—H16B | 0.85 |
N3—C10 | 1.305 (8) | O17—H17C | 0.85 |
N3—C12 | 1.371 (8) | O17—H17D | 0.85 |
C10—N4 | 1.316 (8) | O18—H18C | 0.85 |
C10—H10 | 0.93 | O18—H18D | 0.85 |
N4—C11 | 1.344 (10) | O19—H19C | 0.85 |
N4—H4A | 0.86 | O19—H19D | 0.85 |
C11—C12 | 1.326 (10) | O20—H20C | 0.85 |
C11—H11 | 0.93 | O20—H20D | 0.85 |
C12—H12 | 0.93 | ||
O12—Ca1—O11 | 176.97 (14) | C10—N3—C12 | 104.7 (6) |
O12—Ca1—O5 | 79.88 (14) | C10—N3—Cu1 | 128.2 (5) |
O11—Ca1—O5 | 103.11 (15) | C12—N3—Cu1 | 127.0 (6) |
O12—Ca1—O9 | 92.60 (16) | N3—C10—N4 | 111.3 (8) |
O11—Ca1—O9 | 85.50 (15) | N3—C10—H10 | 124.3 |
O5—Ca1—O9 | 137.32 (14) | N4—C10—H10 | 124.3 |
O12—Ca1—O13 | 97.38 (15) | C10—N4—C11 | 107.9 (7) |
O11—Ca1—O13 | 82.84 (14) | C10—N4—H4A | 126.0 |
O5—Ca1—O13 | 78.91 (14) | C11—N4—H4A | 126.0 |
O9—Ca1—O13 | 143.71 (14) | C12—C11—N4 | 106.2 (8) |
O12—Ca1—O4 | 98.41 (16) | C12—C11—H11 | 126.9 |
O11—Ca1—O4 | 83.26 (14) | N4—C11—H11 | 126.9 |
O5—Ca1—O4 | 67.80 (13) | C11—C12—N3 | 109.8 (8) |
O9—Ca1—O4 | 71.98 (13) | C11—C12—H12 | 125.1 |
O13—Ca1—O4 | 139.70 (15) | N3—C12—H12 | 125.1 |
O12—Ca1—O8 | 79.15 (14) | O6—C13—O7 | 120.3 (6) |
O11—Ca1—O8 | 97.93 (14) | O6—C13—C14 | 118.4 (6) |
O5—Ca1—O8 | 148.21 (13) | O7—C13—C14 | 121.3 (5) |
O9—Ca1—O8 | 67.35 (12) | C15—C14—C19 | 117.6 (5) |
O13—Ca1—O8 | 80.40 (13) | C15—C14—C13 | 115.7 (5) |
O4—Ca1—O8 | 139.05 (14) | C19—C14—C13 | 126.7 (5) |
O12—Ca1—H11A | 161.2 | C16—C15—C14 | 122.7 (6) |
O11—Ca1—H11A | 16.8 | C16—C15—H15 | 118.6 |
O5—Ca1—H11A | 110.2 | C14—C15—H15 | 118.6 |
O9—Ca1—H11A | 90.1 | C17—C16—C15 | 118.1 (6) |
O13—Ca1—H11A | 70.2 | C17—C16—H16 | 121.0 |
O4—Ca1—H11A | 100.1 | C15—C16—H16 | 121.0 |
O8—Ca1—H11A | 84.8 | C18—C17—C16 | 121.1 (6) |
O12—Ca1—H11C | 162.1 | C18—C17—H17 | 119.5 |
O11—Ca1—H11C | 16.5 | C16—C17—H17 | 119.5 |
O5—Ca1—H11C | 111.4 | C17—C18—C19 | 122.3 (6) |
O9—Ca1—H11C | 69.6 | C17—C18—H18 | 118.9 |
O13—Ca1—H11C | 98.5 | C19—C18—H18 | 118.9 |
O4—Ca1—H11C | 74.5 | C18—C19—N1 | 122.1 (5) |
O8—Ca1—H11C | 95.3 | C18—C19—C14 | 118.1 (5) |
H11A—Ca1—H11C | 28.9 | N1—C19—C14 | 119.6 (5) |
O2—Cu1—N2 | 92.99 (18) | O8—C20—N1 | 130.6 (5) |
O2—Cu1—N3 | 91.0 (2) | O8—C20—C21 | 117.1 (5) |
N2—Cu1—N3 | 173.2 (2) | N1—C20—C21 | 112.3 (5) |
O2—Cu1—O3 | 166.89 (19) | O9—C21—O10 | 124.5 (5) |
N2—Cu1—O3 | 85.94 (17) | O9—C21—C20 | 117.6 (5) |
N3—Cu1—O3 | 91.3 (2) | O10—C21—C20 | 117.9 (5) |
O7—Cu2—N1 | 95.17 (17) | C24—N5—C22 | 105.5 (5) |
O7—Cu2—N5 | 89.76 (18) | C24—N5—Cu2 | 125.9 (4) |
N1—Cu2—N5 | 173.9 (2) | C22—N5—Cu2 | 128.4 (4) |
O7—Cu2—O10 | 176.73 (19) | C23—C22—N5 | 108.5 (6) |
N1—Cu2—O10 | 85.29 (16) | C23—C22—H22 | 125.8 |
N5—Cu2—O10 | 89.59 (18) | N5—C22—H22 | 125.8 |
C20—N1—C19 | 122.6 (5) | C22—C23—N6 | 107.3 (6) |
C20—N1—Cu2 | 112.2 (4) | C22—C23—H23 | 126.4 |
C19—N1—Cu2 | 125.2 (3) | N6—C23—H23 | 126.4 |
C8—N2—C7 | 122.2 (5) | C24—N6—C23 | 106.6 (6) |
C8—N2—Cu1 | 112.1 (4) | C24—N6—H6A | 126.7 |
C7—N2—Cu1 | 125.7 (4) | C23—N6—H6A | 126.7 |
O1—C1—O2 | 119.1 (6) | N5—C24—N6 | 112.2 (6) |
O1—C1—C2 | 118.0 (6) | N5—C24—H24 | 123.9 |
O2—C1—C2 | 122.9 (5) | N6—C24—H24 | 123.9 |
C3—C2—C7 | 117.9 (6) | C1—O2—Cu1 | 128.7 (4) |
C3—C2—C1 | 117.0 (5) | C9—O3—Cu1 | 110.6 (3) |
C7—C2—C1 | 125.1 (5) | C9—O4—Ca1 | 117.6 (4) |
C4—C3—C2 | 123.1 (6) | C8—O5—Ca1 | 119.5 (3) |
C4—C3—H3 | 118.5 | C13—O7—Cu2 | 128.9 (4) |
C2—C3—H3 | 118.5 | C20—O8—Ca1 | 118.6 (3) |
C3—C4—C5 | 119.0 (6) | C21—O9—Ca1 | 119.1 (4) |
C3—C4—H4 | 120.5 | C21—O10—Cu2 | 111.4 (3) |
C5—C4—H4 | 120.5 | Ca1—O11—H11A | 109.4 |
C6—C5—C4 | 120.0 (6) | Ca1—O11—H11C | 111.2 |
C6—C5—H5 | 120.0 | H11A—O11—H11C | 109.3 |
C4—C5—H5 | 120.0 | Ca1—O12—H12A | 134.4 |
C5—C6—C7 | 121.1 (6) | Ca1—O12—H12B | 116.8 |
C5—C6—H6 | 119.4 | H12A—O12—H12B | 104.4 |
C7—C6—H6 | 119.4 | Ca1—O13—H13A | 109.8 |
C6—C7—C2 | 118.9 (5) | Ca1—O13—H13B | 109.7 |
C6—C7—N2 | 121.2 (5) | H13A—O13—H13B | 109.7 |
C2—C7—N2 | 119.8 (5) | H14C—O14—H14D | 118.3 |
O5—C8—N2 | 129.7 (5) | H15A—O15—H15D | 97.9 |
O5—C8—C9 | 117.7 (5) | H16A—O16—H16B | 104.7 |
N2—C8—C9 | 112.6 (5) | H17C—O17—H17D | 106.1 |
O4—C9—O3 | 124.6 (5) | H18C—O18—H18D | 120.4 |
O4—C9—C8 | 117.4 (5) | H19C—O19—H19D | 103.5 |
O3—C9—C8 | 118.1 (5) | H20C—O20—H20D | 114.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O20—H20D···O2i | 0.85 | 2.11 | 2.950 (7) | 172 |
O20—H20C···O19 | 0.85 | 2.09 | 2.749 (11) | 134 |
O19—H19D···O18 | 0.85 | 2.34 | 2.887 (12) | 123 |
O19—H19C···O17ii | 0.85 | 1.91 | 2.758 (11) | 180 |
O18—H18D···O6 | 0.85 | 2.50 | 3.070 (7) | 125 |
O18—H18D···O7 | 0.85 | 2.20 | 3.049 (7) | 179 |
O18—H18C···O14iii | 0.85 | 2.04 | 2.887 (10) | 178 |
O17—H17C···O14iv | 0.85 | 2.17 | 2.974 (12) | 158 |
O16—H16A···O10 | 0.85 | 2.10 | 2.850 (6) | 148 |
O15—H15D···O16 | 0.85 | 2.01 | 2.845 (7) | 167 |
O15—H15A···O9 | 0.85 | 2.42 | 3.131 (6) | 141 |
O15—H15A···O4 | 0.85 | 2.38 | 3.121 (7) | 146 |
O14—H14D···O15 | 0.85 | 2.08 | 2.798 (7) | 142 |
O14—H14C···O3 | 0.85 | 2.21 | 3.045 (7) | 169 |
O13—H13B···O19v | 0.85 | 2.15 | 2.963 (9) | 160 |
O13—H13A···O6vi | 0.85 | 1.95 | 2.780 (6) | 164 |
O12—H12B···O1vii | 0.85 | 1.86 | 2.706 (6) | 180 |
O12—H12A···O6v | 0.85 | 1.87 | 2.725 (5) | 180 |
O11—H11C···O15ii | 0.85 | 2.37 | 2.778 (6) | 110 |
O11—H11A···O1viii | 0.85 | 1.96 | 2.780 (6) | 163 |
N6—H6A···O9iii | 0.86 | 2.13 | 2.958 (7) | 161 |
N6—H6A···O4iii | 0.86 | 2.48 | 3.018 (6) | 122 |
N4—H4A···O20iii | 0.86 | 2.03 | 2.888 (9) | 178 |
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) −x, −y, −z+1; (v) x−1/2, −y+1/2, z−1/2; (vi) x+1/2, −y+1/2, z−1/2; (vii) x−1/2, −y+1/2, z+1/2; (viii) x+1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [CaCu2(C9H4NO5)2(C3H4N2)2(H2O)3]·7H2O |
Mr | 895.75 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 6.8988 (9), 24.011 (3), 21.161 (3) |
β (°) | 93.511 (3) |
V (Å3) | 3498.7 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.45 |
Crystal size (mm) | 0.2 × 0.2 × 0.2 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.75, 0.76 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17203, 6119, 3486 |
Rint | 0.093 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.122, 1.00 |
No. of reflections | 6119 |
No. of parameters | 478 |
No. of restraints | 7 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −0.48 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), publCIF (Westrip, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O20—H20D···O2i | 0.85 | 2.11 | 2.950 (7) | 172 |
O20—H20C···O19 | 0.85 | 2.09 | 2.749 (11) | 134 |
O19—H19D···O18 | 0.85 | 2.34 | 2.887 (12) | 123 |
O19—H19C···O17ii | 0.85 | 1.91 | 2.758 (11) | 180 |
O18—H18D···O6 | 0.85 | 2.50 | 3.070 (7) | 125 |
O18—H18D···O7 | 0.85 | 2.20 | 3.049 (7) | 179 |
O18—H18C···O14iii | 0.85 | 2.04 | 2.887 (10) | 178 |
O17—H17C···O14iv | 0.85 | 2.17 | 2.974 (12) | 158 |
O16—H16A···O10 | 0.85 | 2.10 | 2.850 (6) | 148 |
O15—H15D···O16 | 0.85 | 2.01 | 2.845 (7) | 167 |
O15—H15A···O9 | 0.85 | 2.42 | 3.131 (6) | 141 |
O15—H15A···O4 | 0.85 | 2.38 | 3.121 (7) | 146 |
O14—H14D···O15 | 0.85 | 2.08 | 2.798 (7) | 142 |
O14—H14C···O3 | 0.85 | 2.21 | 3.045 (7) | 169 |
O13—H13B···O19v | 0.85 | 2.15 | 2.963 (9) | 160 |
O13—H13A···O6vi | 0.85 | 1.95 | 2.780 (6) | 164 |
O12—H12B···O1vii | 0.85 | 1.86 | 2.706 (6) | 180 |
O12—H12A···O6v | 0.85 | 1.87 | 2.725 (5) | 180 |
O11—H11C···O15ii | 0.85 | 2.37 | 2.778 (6) | 110 |
O11—H11A···O1viii | 0.85 | 1.96 | 2.780 (6) | 163 |
N6—H6A···O9iii | 0.86 | 2.13 | 2.958 (7) | 161 |
N6—H6A···O4iii | 0.86 | 2.48 | 3.018 (6) | 122 |
N4—H4A···O20iii | 0.86 | 2.03 | 2.888 (9) | 178 |
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) −x, −y, −z+1; (v) x−1/2, −y+1/2, z−1/2; (vi) x+1/2, −y+1/2, z−1/2; (vii) x−1/2, −y+1/2, z+1/2; (viii) x+1/2, −y+1/2, z+1/2. |
The "complex as ligand" approach, i.e. using metal cations to link reactively stable coordination compounds that contain potential bridging blocks, is particularly suitable for designing heteropolymetallic compounds.
In the title compound, CuII adopts square planar geometry, coordinating to the oxamato-N-benzoate and the imidazole ligand to afford a Cu-containing "ligand". CaII then bridges two Cu-ligands together.
The molecule has a local (non-crystallographic) mirror plane containing Ca and three aqueous ligands O11, O12 and O13. In addition, 23 classic hydrogen bonds are found in the structure (Table 1).