Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060096/ci2497sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060096/ci2497Isup2.hkl |
CCDC reference: 672751
Copper nitrate hexahydrate (5 mmol), benzimidazole (10 mmol) and 3-(4-carboxylatophenoxy)propionic acid were dissolved in DMF-water (1:1, v/v) solution, and the pH was adjusted to 7 with 0.1 M sodium hydroxide. The solution was fltered and then set aside for the growth of crystals over a week.
The displacement parameters of the water and N,N-dimethylformamide (DMF) molecules were restrained to be nearly isotropic. The non-H atoms of the DMF molecule were restrained to lie in an approximately flat plane, and the C25—O6, C25—N5 and N5—C26 (= N5—C27) bond distances were restrained to 1.25 (1), 1.35 (1) and 1.45 (1) Å, respectively. C-bound H atoms were placed in calculated positions [C—H = 0.93–0.97 Å and Uiso(H) = 1.2–1.5Ueq(C)], and were included in the refinement in the riding-model approximation. The water H-atoms were placed in chemically sensible positions, however, not all of them form hydrogen bonds. Since the positions of the water H atoms cannot be unambiguously determined, a table of hydrogen bond is not included.
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
[Cu(C7H5N2)2(C10H8O5)]·C3H7NO·5H2O | F(000) = 1404 |
Mr = 671.16 | Dx = 1.438 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 12961 reflections |
a = 12.179 (2) Å | θ = 3.0–27.5° |
b = 15.898 (2) Å | µ = 0.77 mm−1 |
c = 16.420 (2) Å | T = 295 K |
β = 102.834 (4)° | Block, blue |
V = 3099.9 (8) Å3 | 0.38 × 0.25 × 0.17 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 5460 independent reflections |
Radiation source: fine-focus sealed tube | 3293 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 10.000 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
ω scans | h = −14→13 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −18→18 |
Tmin = 0.590, Tmax = 0.880 | l = −19→19 |
23434 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.071 | H-atom parameters constrained |
wR(F2) = 0.247 | w = 1/[σ2(Fo2) + (0.1404P)2 + 1.2497P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
5460 reflections | Δρmax = 0.68 e Å−3 |
399 parameters | Δρmin = −0.51 e Å−3 |
66 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0080 (18) |
[Cu(C7H5N2)2(C10H8O5)]·C3H7NO·5H2O | V = 3099.9 (8) Å3 |
Mr = 671.16 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.179 (2) Å | µ = 0.77 mm−1 |
b = 15.898 (2) Å | T = 295 K |
c = 16.420 (2) Å | 0.38 × 0.25 × 0.17 mm |
β = 102.834 (4)° |
Rigaku R-AXIS RAPID diffractometer | 5460 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3293 reflections with I > 2σ(I) |
Tmin = 0.590, Tmax = 0.880 | Rint = 0.058 |
23434 measured reflections |
R[F2 > 2σ(F2)] = 0.071 | 66 restraints |
wR(F2) = 0.247 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.68 e Å−3 |
5460 reflections | Δρmin = −0.51 e Å−3 |
399 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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.42338 (5) | 0.38523 (4) | 0.21419 (4) | 0.0554 (3) | |
O1 | 0.4755 (3) | 0.2807 (3) | 0.1671 (2) | 0.0630 (10) | |
O2 | 0.5993 (4) | 0.2998 (3) | 0.2855 (3) | 0.0785 (13) | |
O3 | 0.7685 (3) | 0.2409 (3) | 0.1683 (3) | 0.0663 (11) | |
O4 | 1.2319 (4) | 0.3954 (3) | 0.1235 (3) | 0.0865 (15) | |
O5 | 1.2925 (3) | 0.3207 (3) | 0.2359 (3) | 0.0663 (11) | |
O6 | 0.4539 (7) | 0.0029 (5) | 0.2326 (6) | 0.169 (3) | |
O1W | 0.8142 (4) | 0.3305 (3) | 0.5698 (3) | 0.0871 (14) | |
H1W1 | 0.8856 | 0.3333 | 0.5841 | 0.131* | |
H1W2 | 0.7928 | 0.2797 | 0.5711 | 0.131* | |
O2W | 0.6657 (6) | 0.2406 (4) | 0.4455 (4) | 0.124 (2) | |
H2W1 | 0.6472 | 0.2499 | 0.3933 | 0.186* | |
H2W2 | 0.6073 | 0.2235 | 0.4609 | 0.186* | |
O3W | 0.3860 (6) | 0.2179 (5) | 0.3771 (5) | 0.156 (3) | |
H3W1 | 0.4473 | 0.2443 | 0.3950 | 0.233* | |
H3W2 | 0.3542 | 0.2355 | 0.3288 | 0.233* | |
O4W | 0.4405 (7) | 0.0577 (5) | 0.3838 (6) | 0.180 (3) | |
H4W1 | 0.3869 | 0.0384 | 0.3462 | 0.270* | |
H4W2 | 0.4198 | 0.0559 | 0.4299 | 0.270* | |
O5W | 0.6616 (4) | 0.0497 (4) | 0.4591 (3) | 0.1076 (18) | |
H5W1 | 0.6344 | 0.0923 | 0.4303 | 0.161* | |
H5W2 | 0.7053 | 0.0653 | 0.5044 | 0.161* | |
N1 | 0.5139 (4) | 0.4592 (3) | 0.1570 (3) | 0.0579 (12) | |
N2 | 0.6480 (4) | 0.5091 (3) | 0.0992 (3) | 0.0628 (13) | |
H2N | 0.7116 | 0.5125 | 0.0849 | 0.075* | |
N3 | 0.4082 (4) | 0.4714 (3) | 0.2970 (3) | 0.0619 (12) | |
N4 | 0.3327 (4) | 0.5670 (3) | 0.3673 (3) | 0.0685 (14) | |
H4N | 0.2825 | 0.5977 | 0.3824 | 0.082* | |
N5 | 0.5337 (6) | −0.0769 (4) | 0.1470 (5) | 0.119 (2) | |
C1 | 0.5601 (5) | 0.2565 (4) | 0.2215 (4) | 0.0602 (14) | |
C2 | 0.6158 (5) | 0.1738 (4) | 0.2072 (4) | 0.0638 (15) | |
H2A | 0.5943 | 0.1307 | 0.2425 | 0.077* | |
H2B | 0.5892 | 0.1566 | 0.1495 | 0.077* | |
C3 | 0.7430 (5) | 0.1814 (4) | 0.2266 (4) | 0.0646 (16) | |
H3A | 0.7709 | 0.2010 | 0.2834 | 0.078* | |
H3B | 0.7772 | 0.1274 | 0.2202 | 0.078* | |
C4 | 0.8798 (4) | 0.2598 (4) | 0.1730 (4) | 0.0562 (14) | |
C5 | 0.8999 (5) | 0.3188 (4) | 0.1135 (4) | 0.0636 (15) | |
H5 | 0.8399 | 0.3412 | 0.0744 | 0.076* | |
C6 | 1.0065 (5) | 0.3428 (4) | 0.1136 (4) | 0.0622 (15) | |
H6 | 1.0191 | 0.3801 | 0.0731 | 0.075* | |
C7 | 1.0973 (4) | 0.3128 (4) | 0.1728 (3) | 0.0538 (13) | |
C8 | 1.0759 (4) | 0.2543 (4) | 0.2300 (3) | 0.0581 (14) | |
H8 | 1.1361 | 0.2331 | 0.2697 | 0.070* | |
C9 | 0.9696 (4) | 0.2267 (4) | 0.2302 (4) | 0.0595 (14) | |
H9 | 0.9581 | 0.1862 | 0.2683 | 0.071* | |
C10 | 1.2128 (5) | 0.3447 (4) | 0.1763 (4) | 0.0606 (14) | |
C11 | 0.6153 (5) | 0.4466 (4) | 0.1434 (4) | 0.0604 (14) | |
H11 | 0.6592 | 0.3997 | 0.1623 | 0.072* | |
C12 | 0.4764 (5) | 0.5357 (4) | 0.1179 (3) | 0.0552 (13) | |
C13 | 0.3774 (5) | 0.5787 (4) | 0.1105 (3) | 0.0619 (14) | |
H13 | 0.3205 | 0.5588 | 0.1349 | 0.074* | |
C14 | 0.3653 (6) | 0.6521 (4) | 0.0657 (4) | 0.0758 (18) | |
H14 | 0.2991 | 0.6828 | 0.0599 | 0.091* | |
C15 | 0.4500 (7) | 0.6816 (4) | 0.0286 (4) | 0.0807 (19) | |
H15 | 0.4388 | 0.7315 | −0.0016 | 0.097* | |
C16 | 0.5487 (6) | 0.6396 (4) | 0.0355 (4) | 0.0727 (17) | |
H16 | 0.6050 | 0.6595 | 0.0104 | 0.087* | |
C17 | 0.5617 (5) | 0.5667 (4) | 0.0808 (3) | 0.0582 (14) | |
C18 | 0.3140 (5) | 0.5081 (4) | 0.3077 (4) | 0.0694 (16) | |
H18 | 0.2427 | 0.4941 | 0.2770 | 0.083* | |
C19 | 0.4946 (5) | 0.5092 (4) | 0.3561 (3) | 0.0579 (14) | |
C20 | 0.6081 (5) | 0.4948 (4) | 0.3737 (4) | 0.0706 (17) | |
H20 | 0.6400 | 0.4548 | 0.3447 | 0.085* | |
C21 | 0.6737 (6) | 0.5429 (5) | 0.4372 (5) | 0.084 (2) | |
H21 | 0.7512 | 0.5343 | 0.4511 | 0.101* | |
C22 | 0.6276 (7) | 0.6027 (4) | 0.4801 (5) | 0.083 (2) | |
H22 | 0.6747 | 0.6343 | 0.5212 | 0.100* | |
C23 | 0.5131 (7) | 0.6168 (4) | 0.4634 (4) | 0.0771 (19) | |
H23 | 0.4815 | 0.6563 | 0.4933 | 0.093* | |
C24 | 0.4475 (6) | 0.5696 (4) | 0.4002 (4) | 0.0640 (15) | |
C25 | 0.5381 (9) | −0.0393 (5) | 0.2196 (7) | 0.140 (4) | |
H25 | 0.6030 | −0.0435 | 0.2617 | 0.168* | |
C26 | 0.4364 (13) | −0.0725 (14) | 0.0809 (11) | 0.336 (12) | |
H26A | 0.4120 | −0.0151 | 0.0727 | 0.504* | |
H26B | 0.3773 | −0.1058 | 0.0948 | 0.504* | |
H26C | 0.4539 | −0.0937 | 0.0306 | 0.504* | |
C27 | 0.6256 (8) | −0.1250 (6) | 0.1309 (7) | 0.134 (4) | |
H27A | 0.6911 | −0.1156 | 0.1747 | 0.201* | |
H27B | 0.6409 | −0.1081 | 0.0784 | 0.201* | |
H27C | 0.6064 | −0.1837 | 0.1287 | 0.201* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0417 (5) | 0.0649 (5) | 0.0626 (5) | −0.0028 (3) | 0.0181 (3) | 0.0022 (3) |
O1 | 0.046 (2) | 0.073 (3) | 0.069 (2) | −0.0064 (19) | 0.0104 (19) | 0.001 (2) |
O2 | 0.076 (3) | 0.078 (3) | 0.076 (3) | 0.009 (2) | 0.005 (2) | −0.008 (2) |
O3 | 0.039 (2) | 0.079 (3) | 0.082 (3) | −0.0037 (19) | 0.0169 (18) | 0.017 (2) |
O4 | 0.051 (3) | 0.128 (4) | 0.075 (3) | −0.027 (2) | 0.004 (2) | 0.030 (3) |
O5 | 0.047 (2) | 0.079 (3) | 0.074 (3) | −0.002 (2) | 0.015 (2) | 0.008 (2) |
O6 | 0.151 (6) | 0.150 (6) | 0.209 (7) | −0.001 (5) | 0.044 (5) | 0.004 (5) |
O1W | 0.084 (3) | 0.089 (3) | 0.086 (3) | 0.026 (3) | 0.015 (2) | 0.000 (3) |
O2W | 0.154 (5) | 0.127 (5) | 0.087 (3) | 0.010 (4) | 0.018 (3) | 0.001 (3) |
O3W | 0.136 (5) | 0.181 (6) | 0.149 (5) | −0.012 (5) | 0.031 (4) | 0.041 (5) |
O4W | 0.136 (5) | 0.165 (6) | 0.225 (7) | 0.023 (5) | 0.011 (5) | −0.010 (6) |
O5W | 0.078 (3) | 0.148 (5) | 0.102 (3) | 0.019 (3) | 0.032 (3) | −0.020 (3) |
N1 | 0.051 (3) | 0.065 (3) | 0.062 (3) | −0.001 (2) | 0.021 (2) | 0.001 (2) |
N2 | 0.052 (3) | 0.074 (3) | 0.069 (3) | −0.015 (2) | 0.027 (2) | 0.000 (3) |
N3 | 0.043 (3) | 0.073 (3) | 0.073 (3) | 0.001 (2) | 0.020 (2) | 0.007 (3) |
N4 | 0.061 (3) | 0.073 (3) | 0.077 (3) | 0.014 (3) | 0.027 (3) | 0.002 (3) |
N5 | 0.104 (5) | 0.116 (5) | 0.126 (5) | 0.014 (4) | 0.000 (4) | −0.004 (5) |
C1 | 0.047 (3) | 0.065 (4) | 0.072 (4) | −0.005 (3) | 0.021 (3) | 0.002 (3) |
C2 | 0.047 (3) | 0.058 (3) | 0.091 (4) | −0.002 (3) | 0.024 (3) | −0.001 (3) |
C3 | 0.050 (3) | 0.059 (3) | 0.089 (4) | 0.003 (3) | 0.024 (3) | 0.012 (3) |
C4 | 0.041 (3) | 0.063 (3) | 0.068 (3) | −0.007 (2) | 0.018 (3) | −0.001 (3) |
C5 | 0.048 (3) | 0.074 (4) | 0.067 (3) | −0.001 (3) | 0.010 (3) | 0.014 (3) |
C6 | 0.055 (4) | 0.068 (4) | 0.065 (3) | −0.004 (3) | 0.017 (3) | 0.013 (3) |
C7 | 0.043 (3) | 0.063 (3) | 0.058 (3) | −0.003 (2) | 0.015 (3) | 0.004 (3) |
C8 | 0.042 (3) | 0.068 (4) | 0.064 (3) | 0.005 (3) | 0.013 (3) | 0.010 (3) |
C9 | 0.040 (3) | 0.072 (4) | 0.069 (3) | 0.005 (3) | 0.017 (3) | 0.019 (3) |
C10 | 0.046 (3) | 0.072 (4) | 0.066 (4) | −0.004 (3) | 0.016 (3) | 0.006 (3) |
C11 | 0.048 (3) | 0.072 (4) | 0.065 (3) | −0.003 (3) | 0.018 (3) | −0.004 (3) |
C12 | 0.055 (3) | 0.061 (3) | 0.051 (3) | −0.008 (3) | 0.015 (2) | −0.009 (3) |
C13 | 0.062 (4) | 0.066 (4) | 0.058 (3) | 0.000 (3) | 0.016 (3) | −0.003 (3) |
C14 | 0.084 (5) | 0.074 (4) | 0.066 (4) | 0.013 (4) | 0.009 (3) | −0.011 (3) |
C15 | 0.101 (6) | 0.068 (4) | 0.071 (4) | −0.008 (4) | 0.015 (4) | 0.009 (3) |
C16 | 0.083 (5) | 0.072 (4) | 0.065 (4) | −0.016 (4) | 0.021 (3) | −0.001 (3) |
C17 | 0.062 (4) | 0.060 (4) | 0.054 (3) | −0.016 (3) | 0.017 (3) | −0.004 (3) |
C18 | 0.054 (4) | 0.087 (4) | 0.069 (4) | −0.001 (3) | 0.018 (3) | 0.005 (4) |
C19 | 0.051 (3) | 0.062 (3) | 0.064 (3) | 0.000 (3) | 0.019 (3) | 0.007 (3) |
C20 | 0.059 (4) | 0.075 (4) | 0.080 (4) | −0.001 (3) | 0.020 (3) | −0.010 (3) |
C21 | 0.060 (4) | 0.096 (5) | 0.094 (5) | 0.003 (4) | 0.010 (4) | −0.008 (4) |
C22 | 0.085 (5) | 0.081 (5) | 0.079 (5) | −0.006 (4) | 0.012 (4) | −0.008 (4) |
C23 | 0.095 (6) | 0.066 (4) | 0.071 (4) | 0.003 (4) | 0.021 (4) | −0.002 (3) |
C24 | 0.077 (4) | 0.051 (3) | 0.070 (4) | 0.006 (3) | 0.031 (3) | 0.003 (3) |
C25 | 0.142 (7) | 0.128 (7) | 0.150 (7) | 0.002 (6) | 0.034 (6) | 0.000 (6) |
C26 | 0.327 (15) | 0.329 (15) | 0.330 (15) | 0.029 (10) | 0.028 (10) | −0.003 (10) |
C27 | 0.119 (7) | 0.136 (7) | 0.156 (7) | 0.005 (5) | 0.048 (6) | 0.009 (6) |
Cu1—N3 | 1.967 (5) | C4—C9 | 1.378 (8) |
Cu1—N1 | 1.984 (4) | C4—C5 | 1.415 (8) |
Cu1—O5i | 1.993 (4) | C5—C6 | 1.353 (8) |
Cu1—O1 | 1.995 (4) | C5—H5 | 0.93 |
O1—C1 | 1.264 (7) | C6—C7 | 1.385 (8) |
O2—C1 | 1.259 (7) | C6—H6 | 0.93 |
O3—C4 | 1.374 (6) | C7—C8 | 1.386 (7) |
O3—C3 | 1.428 (7) | C7—C10 | 1.485 (7) |
O4—C10 | 1.242 (7) | C8—C9 | 1.369 (7) |
O5—C10 | 1.275 (7) | C8—H8 | 0.93 |
O5—Cu1ii | 1.993 (4) | C9—H9 | 0.93 |
O6—C25 | 1.283 (8) | C11—H11 | 0.93 |
O1W—H1W1 | 0.85 | C12—C13 | 1.366 (8) |
O1W—H1W2 | 0.85 | C12—C17 | 1.405 (7) |
O2W—H2W1 | 0.85 | C13—C14 | 1.370 (9) |
O2W—H2W2 | 0.85 | C13—H13 | 0.93 |
O3W—H3W1 | 0.85 | C14—C15 | 1.390 (9) |
O3W—H3W2 | 0.85 | C14—H14 | 0.93 |
O4W—H4W1 | 0.85 | C15—C16 | 1.358 (9) |
O4W—H4W2 | 0.85 | C15—H15 | 0.93 |
O5W—H5W1 | 0.85 | C16—C17 | 1.368 (9) |
O5W—H5W2 | 0.85 | C16—H16 | 0.93 |
N1—C11 | 1.318 (7) | C18—H18 | 0.93 |
N1—C12 | 1.405 (7) | C19—C20 | 1.367 (8) |
N2—C11 | 1.342 (7) | C19—C24 | 1.401 (8) |
N2—C17 | 1.376 (7) | C20—C21 | 1.394 (9) |
N2—H2N | 0.86 | C20—H20 | 0.93 |
N3—C18 | 1.333 (7) | C21—C22 | 1.375 (10) |
N3—C19 | 1.399 (7) | C21—H21 | 0.93 |
N4—C18 | 1.337 (8) | C22—C23 | 1.379 (10) |
N4—C24 | 1.383 (8) | C22—H22 | 0.93 |
N4—H4N | 0.86 | C23—C24 | 1.383 (9) |
N5—C25 | 1.324 (8) | C23—H23 | 0.93 |
N5—C26 | 1.420 (10) | C25—H25 | 0.93 |
N5—C27 | 1.428 (8) | C26—H26A | 0.96 |
C1—C2 | 1.521 (8) | C26—H26B | 0.96 |
C2—C3 | 1.516 (8) | C26—H26C | 0.96 |
C2—H2A | 0.97 | C27—H27A | 0.96 |
C2—H2B | 0.97 | C27—H27B | 0.96 |
C3—H3A | 0.97 | C27—H27C | 0.96 |
C3—H3B | 0.97 | ||
N3—Cu1—N1 | 93.53 (19) | C4—C9—H9 | 120.5 |
N3—Cu1—O5i | 91.88 (18) | O4—C10—O5 | 120.1 (5) |
N1—Cu1—O5i | 160.05 (19) | O4—C10—C7 | 121.2 (5) |
N3—Cu1—O1 | 159.18 (19) | O5—C10—C7 | 118.7 (5) |
N1—Cu1—O1 | 92.98 (17) | N1—C11—N2 | 112.4 (5) |
O5i—Cu1—O1 | 88.67 (16) | N1—C11—H11 | 123.8 |
C1—O1—Cu1 | 105.0 (4) | N2—C11—H11 | 123.8 |
C4—O3—C3 | 117.7 (4) | C13—C12—N1 | 131.6 (5) |
C10—O5—Cu1ii | 102.2 (3) | C13—C12—C17 | 120.6 (6) |
H1W1—O1W—H1W2 | 110.2 | N1—C12—C17 | 107.7 (5) |
H2W1—O2W—H2W2 | 107.7 | C12—C13—C14 | 117.5 (6) |
H3W1—O3W—H3W2 | 110.2 | C12—C13—H13 | 121.3 |
H4W1—O4W—H4W2 | 107.7 | C14—C13—H13 | 121.3 |
H5W1—O5W—H5W2 | 110.2 | C13—C14—C15 | 121.4 (7) |
C11—N1—C12 | 106.0 (5) | C13—C14—H14 | 119.3 |
C11—N1—Cu1 | 129.1 (4) | C15—C14—H14 | 119.3 |
C12—N1—Cu1 | 124.8 (4) | C16—C15—C14 | 121.8 (6) |
C11—N2—C17 | 107.9 (4) | C16—C15—H15 | 119.1 |
C11—N2—H2N | 126.0 | C14—C15—H15 | 119.1 |
C17—N2—H2N | 126.0 | C15—C16—C17 | 117.1 (6) |
C18—N3—C19 | 104.9 (5) | C15—C16—H16 | 121.4 |
C18—N3—Cu1 | 127.8 (4) | C17—C16—H16 | 121.4 |
C19—N3—Cu1 | 127.3 (4) | C16—C17—N2 | 132.4 (6) |
C18—N4—C24 | 107.4 (5) | C16—C17—C12 | 121.7 (6) |
C18—N4—H4N | 126.3 | N2—C17—C12 | 105.9 (5) |
C24—N4—H4N | 126.3 | N3—C18—N4 | 113.1 (6) |
C25—N5—C26 | 121.7 (13) | N3—C18—H18 | 123.4 |
C25—N5—C27 | 122.2 (9) | N4—C18—H18 | 123.4 |
C26—N5—C27 | 116.1 (12) | C20—C19—N3 | 130.1 (6) |
O2—C1—O1 | 121.5 (6) | C20—C19—C24 | 121.1 (6) |
O2—C1—C2 | 120.1 (6) | N3—C19—C24 | 108.7 (5) |
O1—C1—C2 | 118.4 (6) | C19—C20—C21 | 116.8 (6) |
C3—C2—C1 | 111.6 (5) | C19—C20—H20 | 121.6 |
C3—C2—H2A | 109.3 | C21—C20—H20 | 121.6 |
C1—C2—H2A | 109.3 | C22—C21—C20 | 122.1 (7) |
C3—C2—H2B | 109.3 | C22—C21—H21 | 119.0 |
C1—C2—H2B | 109.3 | C20—C21—H21 | 119.0 |
H2A—C2—H2B | 108.0 | C21—C22—C23 | 121.4 (7) |
O3—C3—C2 | 106.1 (5) | C21—C22—H22 | 119.3 |
O3—C3—H3A | 110.5 | C23—C22—H22 | 119.3 |
C2—C3—H3A | 110.5 | C24—C23—C22 | 116.8 (6) |
O3—C3—H3B | 110.5 | C24—C23—H23 | 121.6 |
C2—C3—H3B | 110.5 | C22—C23—H23 | 121.6 |
H3A—C3—H3B | 108.7 | C23—C24—N4 | 132.5 (6) |
O3—C4—C9 | 125.4 (5) | C23—C24—C19 | 121.7 (6) |
O3—C4—C5 | 115.2 (5) | N4—C24—C19 | 105.8 (5) |
C9—C4—C5 | 119.4 (5) | O6—C25—N5 | 120.8 (11) |
C6—C5—C4 | 120.0 (5) | O6—C25—H25 | 119.6 |
C6—C5—H5 | 120.0 | N5—C25—H25 | 119.6 |
C4—C5—H5 | 120.0 | N5—C26—H26A | 109.5 |
C5—C6—C7 | 121.3 (5) | N5—C26—H26B | 109.5 |
C5—C6—H6 | 119.3 | H26A—C26—H26B | 109.5 |
C7—C6—H6 | 119.3 | N5—C26—H26C | 109.5 |
C6—C7—C8 | 117.8 (5) | H26A—C26—H26C | 109.5 |
C6—C7—C10 | 120.7 (5) | H26B—C26—H26C | 109.5 |
C8—C7—C10 | 121.5 (5) | N5—C27—H27A | 109.5 |
C9—C8—C7 | 122.5 (5) | N5—C27—H27B | 109.5 |
C9—C8—H8 | 118.8 | H27A—C27—H27B | 109.5 |
C7—C8—H8 | 118.8 | N5—C27—H27C | 109.5 |
C8—C9—C4 | 119.0 (5) | H27A—C27—H27C | 109.5 |
C8—C9—H9 | 120.5 | H27B—C27—H27C | 109.5 |
N3—Cu1—O1—C1 | −15.1 (7) | C17—N2—C11—N1 | −1.1 (7) |
N1—Cu1—O1—C1 | 93.0 (4) | C11—N1—C12—C13 | 178.6 (6) |
O5i—Cu1—O1—C1 | −106.9 (4) | Cu1—N1—C12—C13 | 1.9 (8) |
N3—Cu1—N1—C11 | 122.8 (5) | C11—N1—C12—C17 | 0.0 (6) |
O5i—Cu1—N1—C11 | −131.8 (6) | Cu1—N1—C12—C17 | −176.7 (4) |
O1—Cu1—N1—C11 | −37.4 (5) | N1—C12—C13—C14 | −178.3 (6) |
N3—Cu1—N1—C12 | −61.3 (4) | C17—C12—C13—C14 | 0.1 (8) |
O5i—Cu1—N1—C12 | 44.2 (8) | C12—C13—C14—C15 | 0.5 (9) |
O1—Cu1—N1—C12 | 138.5 (4) | C13—C14—C15—C16 | −0.4 (10) |
N1—Cu1—N3—C18 | 116.4 (5) | C14—C15—C16—C17 | −0.2 (10) |
O5i—Cu1—N3—C18 | −44.4 (5) | C15—C16—C17—N2 | 179.0 (6) |
O1—Cu1—N3—C18 | −135.6 (5) | C15—C16—C17—C12 | 0.8 (9) |
N1—Cu1—N3—C19 | −61.8 (5) | C11—N2—C17—C16 | −177.4 (6) |
O5i—Cu1—N3—C19 | 137.4 (5) | C11—N2—C17—C12 | 1.0 (6) |
O1—Cu1—N3—C19 | 46.2 (7) | C13—C12—C17—C16 | −0.8 (9) |
Cu1—O1—C1—O2 | −5.3 (6) | N1—C12—C17—C16 | 177.9 (5) |
Cu1—O1—C1—C2 | 175.8 (4) | C13—C12—C17—N2 | −179.4 (5) |
O2—C1—C2—C3 | −43.4 (8) | N1—C12—C17—N2 | −0.7 (6) |
O1—C1—C2—C3 | 135.4 (6) | C19—N3—C18—N4 | 1.2 (7) |
C4—O3—C3—C2 | 179.5 (5) | Cu1—N3—C18—N4 | −177.3 (4) |
C1—C2—C3—O3 | −63.4 (7) | C24—N4—C18—N3 | −1.0 (7) |
C3—O3—C4—C9 | −0.7 (8) | C18—N3—C19—C20 | 178.8 (6) |
C3—O3—C4—C5 | 179.8 (5) | Cu1—N3—C19—C20 | −2.7 (9) |
O3—C4—C5—C6 | 179.0 (5) | C18—N3—C19—C24 | −0.9 (6) |
C9—C4—C5—C6 | −0.5 (9) | Cu1—N3—C19—C24 | 177.6 (4) |
C4—C5—C6—C7 | −2.2 (9) | N3—C19—C20—C21 | −179.7 (6) |
C5—C6—C7—C8 | 2.8 (9) | C24—C19—C20—C21 | 0.0 (9) |
C5—C6—C7—C10 | −175.1 (6) | C19—C20—C21—C22 | −0.5 (11) |
C6—C7—C8—C9 | −0.8 (9) | C20—C21—C22—C23 | 1.4 (11) |
C10—C7—C8—C9 | 177.1 (5) | C21—C22—C23—C24 | −1.6 (10) |
C7—C8—C9—C4 | −1.9 (9) | C22—C23—C24—N4 | 179.9 (6) |
O3—C4—C9—C8 | −177.0 (5) | C22—C23—C24—C19 | 1.1 (9) |
C5—C4—C9—C8 | 2.5 (9) | C18—N4—C24—C23 | −178.6 (7) |
Cu1ii—O5—C10—O4 | 1.2 (7) | C18—N4—C24—C19 | 0.3 (6) |
Cu1ii—O5—C10—C7 | −177.2 (4) | C20—C19—C24—C23 | −0.3 (9) |
C6—C7—C10—O4 | −4.1 (9) | N3—C19—C24—C23 | 179.5 (5) |
C8—C7—C10—O4 | 178.0 (6) | C20—C19—C24—N4 | −179.4 (5) |
C6—C7—C10—O5 | 174.3 (5) | N3—C19—C24—N4 | 0.4 (6) |
C8—C7—C10—O5 | −3.6 (9) | C26—N5—C25—O6 | −0.2 (3) |
C12—N1—C11—N2 | 0.6 (6) | C27—N5—C25—O6 | −179.4 (3) |
Cu1—N1—C11—N2 | 177.2 (4) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C7H5N2)2(C10H8O5)]·C3H7NO·5H2O |
Mr | 671.16 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 12.179 (2), 15.898 (2), 16.420 (2) |
β (°) | 102.834 (4) |
V (Å3) | 3099.9 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.77 |
Crystal size (mm) | 0.38 × 0.25 × 0.17 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.590, 0.880 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23434, 5460, 3293 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.071, 0.247, 1.11 |
No. of reflections | 5460 |
No. of parameters | 399 |
No. of restraints | 66 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.68, −0.51 |
Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
The present report follows our studies on the transition metal derivatives of 3-(4-carboxylatophenoxy)propionic acid. Previous reports (Kong et al., 2007a,b) describe the crystal structures of isostrutural manganese(II) and cobalt(II) adducts with 2,2'-bipyridine. In the present work, DMF, which was used as a co-solvent, is incorporated into the crystal structure.
The 3-(4-carboxylatophenoxy)propionate dianion links the di(benzimidazole)copper groups into a linear chain running along the a axis of the monoclinic unit cell, with the dianion binding through one O atom each from both carboxylate ends to confer a distorted square-planar environment to the copper center.