metal-organic compounds
Bis(2,2′-bipyridine-κ2N,N′)(4-methylbenzoato-κ2O,O′)copper(II) iodide hemihydrate
aCollege of Chemistry, South China University of Technology, Guangzhou 510640, People's Republic of China
*Correspondence e-mail: ghdeng@126.com
The title compound, [Cu(C8H7O2)(C10H8N2)2]I·0.5H2O, was obtained by the hydrothermal reaction of copper(I) iodide, 4-methylbenzoic acid and 2,2′-bipyridine. The initial reactant of CuI was oxidized to CuII. The contains two independent complex molecules, two I− ions and one water molecule. Each CuII atom is coordinated by two O atoms from a 4-methylbenzoate ligand and four N atoms from two 2,2′-bipyridine ligands, displaying a distorted octahedral geometry. The structure involves O—H⋯I hydrogen bonds between the water molecule and iodide ions and π–π stacking interactions between the benzene and pyridyl rings [centroid–centroid distance = 3.79 (1) Å] and between the pyridyl rings [centroid–centroid distance = 3.87 (1) Å].
Related literature
For related literature, see: Ma & Deng (2008); Mao et al. (2001); Song et al. (2008a,b,c,d).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808024252/hy2148sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808024252/hy2148Isup2.hkl
A mixture of CuI (0.1 g, 0.5 mmol), 4-methylbenzoic acid (0.068 g, 0.5 mmol), 2,2'-bipyridine (0.078 g, 0.5 mmol) and H2O (10 ml) was placed in a 23 ml Teflon-lined reactor, which was heated to 433 K for 3 d and then cooled to room temperature at a rate of 10 K h-1. Block colorless crystals were obtained.
C-bound H atoms were positioned geometrically and refined as riding, with C—H = 0.93 (CH) and 0.96 (CH3) Å, and with Uiso(H) = 1.2Ueq(C) for CH group or 1.5Ueq(C) for CH3 group. H atoms of water molecule were tentatively located in difference Fourier maps and refined with distance restraints of O–H = 0.84 (1) and H···H = 1.35 (1) Å, and with Uiso(H) = 1.5Ueq(O). The highest residual electron density was 1.14 Å from atom I1 and the deepest hole 0.81 Å from atom I1.
Data collection: APEX2 (Bruker, 2007); cell
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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Cu(C8H7O2)(C10H8N2)2]I·0.5H2O | Z = 4 |
Mr = 646.96 | F(000) = 1288 |
Triclinic, P1 | Dx = 1.603 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 14.6698 (4) Å | Cell parameters from 5300 reflections |
b = 15.3588 (4) Å | θ = 1.3–28.0° |
c = 15.4224 (7) Å | µ = 2.00 mm−1 |
α = 100.943 (2)° | T = 296 K |
β = 114.345 (2)° | Block, blue |
γ = 111.996 (2)° | 0.37 × 0.30 × 0.26 mm |
V = 2680.64 (19) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 9564 independent reflections |
Radiation source: fine-focus sealed tube | 6740 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ϕ and ω scans | θmax = 25.2°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.525, Tmax = 0.624 | k = −18→18 |
29909 measured reflections | l = −17→18 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0774P)2 + 2.4876P] where P = (Fo2 + 2Fc2)/3 |
9564 reflections | (Δ/σ)max < 0.001 |
660 parameters | Δρmax = 1.56 e Å−3 |
3 restraints | Δρmin = −1.53 e Å−3 |
[Cu(C8H7O2)(C10H8N2)2]I·0.5H2O | γ = 111.996 (2)° |
Mr = 646.96 | V = 2680.64 (19) Å3 |
Triclinic, P1 | Z = 4 |
a = 14.6698 (4) Å | Mo Kα radiation |
b = 15.3588 (4) Å | µ = 2.00 mm−1 |
c = 15.4224 (7) Å | T = 296 K |
α = 100.943 (2)° | 0.37 × 0.30 × 0.26 mm |
β = 114.345 (2)° |
Bruker SMART APEXII CCD area-detector diffractometer | 9564 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6740 reflections with I > 2σ(I) |
Tmin = 0.525, Tmax = 0.624 | Rint = 0.037 |
29909 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 3 restraints |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.03 | Δρmax = 1.56 e Å−3 |
9564 reflections | Δρmin = −1.53 e Å−3 |
660 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5583 (5) | −0.0992 (4) | 0.8879 (4) | 0.0588 (14) | |
H1 | 0.6232 | −0.0884 | 0.8844 | 0.071* | |
C2 | 0.5284 (6) | −0.1583 (5) | 0.9396 (5) | 0.0685 (16) | |
H2 | 0.5726 | −0.1862 | 0.9707 | 0.082* | |
C3 | 0.4332 (6) | −0.1746 (5) | 0.9441 (5) | 0.0787 (19) | |
H3 | 0.4115 | −0.2137 | 0.9787 | 0.094* | |
C4 | 0.3693 (5) | −0.1328 (5) | 0.8973 (5) | 0.0698 (17) | |
H4 | 0.3035 | −0.1439 | 0.8992 | 0.084* | |
C5 | 0.4036 (4) | −0.0738 (4) | 0.8470 (4) | 0.0515 (12) | |
C6 | 0.3422 (4) | −0.0237 (4) | 0.7958 (4) | 0.0543 (13) | |
C7 | 0.2355 (6) | −0.0438 (5) | 0.7799 (6) | 0.083 (2) | |
H7 | 0.1976 | −0.0916 | 0.7998 | 0.099* | |
C8 | 0.1861 (6) | 0.0083 (7) | 0.7338 (7) | 0.100 (3) | |
H8 | 0.1139 | −0.0047 | 0.7221 | 0.121* | |
C9 | 0.2416 (7) | 0.0782 (7) | 0.7056 (6) | 0.091 (2) | |
H9 | 0.2095 | 0.1151 | 0.6767 | 0.110* | |
C10 | 0.3481 (5) | 0.0941 (5) | 0.7206 (5) | 0.0719 (17) | |
H10 | 0.3862 | 0.1408 | 0.6997 | 0.086* | |
C11 | 0.3340 (4) | −0.0838 (4) | 0.5409 (4) | 0.0536 (13) | |
H11 | 0.2900 | −0.0645 | 0.5605 | 0.064* | |
C12 | 0.2824 (5) | −0.1491 (4) | 0.4398 (4) | 0.0617 (15) | |
H12 | 0.2052 | −0.1726 | 0.3913 | 0.074* | |
C13 | 0.3469 (5) | −0.1793 (4) | 0.4111 (4) | 0.0632 (15) | |
H13 | 0.3130 | −0.2250 | 0.3433 | 0.076* | |
C14 | 0.4609 (5) | −0.1414 (4) | 0.4830 (4) | 0.0573 (13) | |
H14 | 0.5056 | −0.1600 | 0.4640 | 0.069* | |
C15 | 0.5095 (4) | −0.0754 (3) | 0.5840 (4) | 0.0441 (11) | |
C16 | 0.6312 (4) | −0.0306 (3) | 0.6684 (4) | 0.0443 (11) | |
C17 | 0.7116 (5) | −0.0489 (4) | 0.6564 (5) | 0.0617 (14) | |
H17 | 0.6910 | −0.0899 | 0.5912 | 0.074* | |
C18 | 0.8221 (5) | −0.0065 (5) | 0.7407 (5) | 0.0733 (17) | |
H18 | 0.8765 | −0.0189 | 0.7334 | 0.088* | |
C19 | 0.8507 (5) | 0.0547 (5) | 0.8365 (5) | 0.0703 (16) | |
H19 | 0.9242 | 0.0830 | 0.8950 | 0.084* | |
C20 | 0.7693 (4) | 0.0734 (4) | 0.8442 (4) | 0.0595 (14) | |
H20 | 0.7894 | 0.1163 | 0.9083 | 0.071* | |
C21 | 0.6656 (4) | 0.2547 (4) | 0.8568 (4) | 0.0494 (12) | |
C22 | 0.7626 (4) | 0.3594 (4) | 0.9370 (4) | 0.0472 (12) | |
C23 | 0.8244 (5) | 0.3793 (5) | 1.0407 (4) | 0.0666 (16) | |
H23 | 0.8066 | 0.3261 | 1.0623 | 0.080* | |
C24 | 0.9126 (5) | 0.4775 (5) | 1.1130 (5) | 0.0778 (18) | |
H24 | 0.9520 | 0.4891 | 1.1829 | 0.093* | |
C25 | 0.9441 (5) | 0.5588 (4) | 1.0854 (5) | 0.0642 (16) | |
C26 | 0.8836 (5) | 0.5382 (4) | 0.9817 (5) | 0.0664 (16) | |
H26 | 0.9037 | 0.5911 | 0.9600 | 0.080* | |
C27 | 0.7936 (5) | 0.4407 (4) | 0.9084 (4) | 0.0577 (13) | |
H27 | 0.7531 | 0.4297 | 0.8387 | 0.069* | |
C28 | 1.0395 (6) | 0.6647 (5) | 1.1648 (6) | 0.099 (2) | |
H28A | 1.0074 | 0.7023 | 1.1859 | 0.148* | |
H28B | 1.0801 | 0.6992 | 1.1353 | 0.148* | |
H28C | 1.0924 | 0.6605 | 1.2243 | 0.148* | |
C36 | 1.0037 (6) | 0.3445 (7) | 0.4202 (7) | 0.105 (3) | |
H36A | 0.9998 | 0.3090 | 0.3592 | 0.158* | |
H36B | 1.0105 | 0.3080 | 0.4644 | 0.158* | |
H36C | 1.0701 | 0.4127 | 0.4573 | 0.158* | |
C30 | 0.8952 (5) | 0.3506 (5) | 0.3882 (5) | 0.0709 (17) | |
C31 | 0.8731 (6) | 0.4128 (7) | 0.3403 (6) | 0.098 (3) | |
H31 | 0.9283 | 0.4540 | 0.3288 | 0.118* | |
C32 | 0.7725 (5) | 0.4176 (5) | 0.3080 (5) | 0.0744 (18) | |
H32 | 0.7607 | 0.4606 | 0.2751 | 0.089* | |
C33 | 0.6900 (4) | 0.3575 (4) | 0.3255 (4) | 0.0432 (11) | |
C34 | 0.7122 (4) | 0.2956 (4) | 0.3758 (4) | 0.0521 (12) | |
H34 | 0.6580 | 0.2551 | 0.3886 | 0.063* | |
C35 | 0.5819 (4) | 0.3622 (4) | 0.2935 (4) | 0.0461 (11) | |
C37 | 0.6852 (4) | 0.6225 (4) | 0.4203 (5) | 0.0648 (15) | |
H37 | 0.7121 | 0.6057 | 0.3783 | 0.078* | |
C38 | 0.7636 (5) | 0.6975 (4) | 0.5194 (5) | 0.0746 (18) | |
H38 | 0.8424 | 0.7318 | 0.5438 | 0.090* | |
C39 | 0.7249 (5) | 0.7213 (4) | 0.5815 (5) | 0.0669 (16) | |
H39 | 0.7775 | 0.7697 | 0.6501 | 0.080* | |
C40 | 0.6076 (5) | 0.6734 (4) | 0.5428 (4) | 0.0562 (13) | |
H40 | 0.5798 | 0.6901 | 0.5840 | 0.067* | |
C41 | 0.5320 (4) | 0.6000 (3) | 0.4412 (4) | 0.0441 (11) | |
C42 | 0.4036 (4) | 0.5452 (3) | 0.3899 (3) | 0.0417 (11) | |
C43 | 0.3480 (5) | 0.5727 (4) | 0.4316 (4) | 0.0569 (13) | |
H43 | 0.3898 | 0.6275 | 0.4960 | 0.068* | |
C44 | 0.2272 (5) | 0.5173 (5) | 0.3759 (5) | 0.0681 (16) | |
H44 | 0.1867 | 0.5358 | 0.4015 | 0.082* | |
C45 | 0.1691 (5) | 0.4352 (4) | 0.2830 (5) | 0.0627 (15) | |
H45 | 0.0886 | 0.3955 | 0.2457 | 0.075* | |
C46 | 0.2306 (4) | 0.4124 (4) | 0.2458 (4) | 0.0506 (12) | |
H46 | 0.1902 | 0.3567 | 0.1824 | 0.061* | |
C47 | 0.2668 (5) | 0.2356 (4) | 0.1058 (5) | 0.0598 (14) | |
H47 | 0.2849 | 0.2271 | 0.1678 | 0.072* | |
C48 | 0.1841 (5) | 0.1508 (4) | 0.0136 (6) | 0.0715 (17) | |
H48 | 0.1474 | 0.0861 | 0.0126 | 0.086* | |
C49 | 0.1574 (5) | 0.1646 (5) | −0.0771 (6) | 0.082 (2) | |
H49 | 0.1013 | 0.1087 | −0.1408 | 0.098* | |
C50 | 0.2138 (5) | 0.2621 (5) | −0.0742 (4) | 0.0706 (17) | |
H50 | 0.1966 | 0.2717 | −0.1356 | 0.085* | |
C51 | 0.2964 (4) | 0.3448 (4) | 0.0223 (4) | 0.0499 (12) | |
C52 | 0.3624 (4) | 0.4512 (4) | 0.0340 (4) | 0.0481 (12) | |
C29 | 0.8130 (5) | 0.2930 (4) | 0.4069 (5) | 0.0606 (14) | |
H29 | 0.8261 | 0.2514 | 0.4414 | 0.073* | |
C53 | 0.3479 (5) | 0.4781 (5) | −0.0497 (4) | 0.0609 (14) | |
H53 | 0.2921 | 0.4294 | −0.1177 | 0.073* | |
C54 | 0.4170 (6) | 0.5774 (5) | −0.0305 (5) | 0.0700 (17) | |
H54 | 0.4096 | 0.5968 | −0.0856 | 0.084* | |
C55 | 0.4974 (5) | 0.6486 (5) | 0.0704 (5) | 0.0643 (15) | |
H55 | 0.5449 | 0.7165 | 0.0847 | 0.077* | |
C56 | 0.5062 (5) | 0.6173 (4) | 0.1499 (4) | 0.0533 (13) | |
H56 | 0.5604 | 0.6655 | 0.2183 | 0.064* | |
Cu2 | 0.44994 (5) | 0.45165 (4) | 0.24535 (4) | 0.04330 (16) | |
Cu1 | 0.53604 (5) | 0.04754 (4) | 0.76873 (5) | 0.04622 (17) | |
I1 | 0.04839 (6) | 0.20792 (5) | 0.62512 (4) | 0.1112 (2) | |
I2 | 0.98058 (3) | 0.14574 (3) | 0.13668 (3) | 0.07583 (16) | |
N1 | 0.4398 (3) | 0.5204 (3) | 0.1327 (3) | 0.0449 (9) | |
N2 | 0.3228 (3) | 0.3298 (3) | 0.1110 (3) | 0.0483 (10) | |
N3 | 0.3964 (4) | 0.0430 (3) | 0.7649 (3) | 0.0544 (11) | |
N4 | 0.4981 (3) | −0.0577 (3) | 0.8433 (3) | 0.0498 (10) | |
N5 | 0.4459 (3) | −0.0467 (3) | 0.6130 (3) | 0.0440 (9) | |
N6 | 0.6613 (3) | 0.0313 (3) | 0.7616 (3) | 0.0479 (10) | |
N7 | 0.3464 (3) | 0.4665 (3) | 0.2964 (3) | 0.0416 (9) | |
N8 | 0.5707 (3) | 0.5723 (3) | 0.3818 (3) | 0.0478 (10) | |
O1 | 0.6478 (3) | 0.1823 (3) | 0.8889 (3) | 0.0568 (9) | |
O2 | 0.6079 (3) | 0.2405 (3) | 0.7651 (3) | 0.0674 (10) | |
O3 | 0.5675 (3) | 0.4192 (3) | 0.2437 (3) | 0.0522 (8) | |
O4 | 0.5122 (3) | 0.3137 (3) | 0.3162 (3) | 0.0597 (9) | |
O1W | 0.8745 (9) | 0.9386 (6) | 0.5468 (7) | 0.201 (4) | |
H2W | 0.9082 | 1.0013 | 0.5663 | 0.301* | |
H1W | 0.8900 | 0.9191 | 0.5042 | 0.301* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.063 (3) | 0.062 (3) | 0.066 (4) | 0.034 (3) | 0.041 (3) | 0.030 (3) |
C2 | 0.075 (4) | 0.066 (4) | 0.066 (4) | 0.034 (3) | 0.039 (3) | 0.031 (3) |
C3 | 0.093 (5) | 0.070 (4) | 0.078 (4) | 0.029 (4) | 0.062 (4) | 0.028 (3) |
C4 | 0.069 (4) | 0.064 (4) | 0.067 (4) | 0.018 (3) | 0.050 (3) | 0.011 (3) |
C5 | 0.049 (3) | 0.045 (3) | 0.048 (3) | 0.015 (2) | 0.031 (3) | 0.004 (2) |
C6 | 0.042 (3) | 0.056 (3) | 0.049 (3) | 0.017 (2) | 0.027 (3) | 0.001 (2) |
C7 | 0.058 (4) | 0.090 (5) | 0.097 (5) | 0.035 (4) | 0.049 (4) | 0.020 (4) |
C8 | 0.060 (4) | 0.124 (7) | 0.101 (6) | 0.050 (5) | 0.041 (4) | 0.011 (5) |
C9 | 0.079 (5) | 0.106 (6) | 0.091 (5) | 0.071 (5) | 0.034 (4) | 0.023 (4) |
C10 | 0.067 (4) | 0.069 (4) | 0.076 (4) | 0.046 (3) | 0.032 (3) | 0.013 (3) |
C11 | 0.049 (3) | 0.054 (3) | 0.048 (3) | 0.023 (2) | 0.022 (3) | 0.018 (2) |
C12 | 0.051 (3) | 0.065 (4) | 0.045 (3) | 0.021 (3) | 0.016 (3) | 0.017 (3) |
C13 | 0.068 (4) | 0.068 (4) | 0.043 (3) | 0.028 (3) | 0.029 (3) | 0.015 (3) |
C14 | 0.065 (4) | 0.055 (3) | 0.056 (3) | 0.030 (3) | 0.037 (3) | 0.017 (3) |
C15 | 0.047 (3) | 0.040 (2) | 0.050 (3) | 0.021 (2) | 0.029 (2) | 0.022 (2) |
C16 | 0.048 (3) | 0.043 (3) | 0.053 (3) | 0.027 (2) | 0.032 (2) | 0.022 (2) |
C17 | 0.059 (3) | 0.062 (3) | 0.070 (4) | 0.034 (3) | 0.038 (3) | 0.019 (3) |
C18 | 0.059 (4) | 0.083 (4) | 0.087 (5) | 0.043 (3) | 0.042 (4) | 0.029 (4) |
C19 | 0.042 (3) | 0.085 (4) | 0.070 (4) | 0.030 (3) | 0.025 (3) | 0.021 (3) |
C20 | 0.041 (3) | 0.065 (3) | 0.055 (3) | 0.022 (3) | 0.022 (3) | 0.015 (3) |
C21 | 0.044 (3) | 0.054 (3) | 0.048 (3) | 0.022 (2) | 0.031 (3) | 0.009 (2) |
C22 | 0.039 (3) | 0.043 (3) | 0.049 (3) | 0.016 (2) | 0.023 (2) | 0.008 (2) |
C23 | 0.060 (4) | 0.069 (4) | 0.052 (3) | 0.019 (3) | 0.027 (3) | 0.023 (3) |
C24 | 0.056 (4) | 0.084 (5) | 0.047 (3) | 0.017 (3) | 0.014 (3) | 0.010 (3) |
C25 | 0.041 (3) | 0.056 (3) | 0.067 (4) | 0.015 (3) | 0.026 (3) | 0.000 (3) |
C26 | 0.054 (3) | 0.049 (3) | 0.083 (5) | 0.021 (3) | 0.034 (3) | 0.019 (3) |
C27 | 0.055 (3) | 0.054 (3) | 0.056 (3) | 0.027 (3) | 0.026 (3) | 0.016 (3) |
C28 | 0.057 (4) | 0.075 (4) | 0.098 (5) | 0.013 (3) | 0.026 (4) | −0.008 (4) |
C36 | 0.064 (4) | 0.188 (8) | 0.124 (6) | 0.083 (5) | 0.063 (5) | 0.107 (7) |
C30 | 0.055 (3) | 0.109 (5) | 0.072 (4) | 0.048 (3) | 0.039 (3) | 0.053 (4) |
C31 | 0.059 (4) | 0.168 (7) | 0.121 (6) | 0.064 (5) | 0.062 (4) | 0.109 (6) |
C32 | 0.057 (4) | 0.097 (5) | 0.088 (5) | 0.041 (3) | 0.041 (3) | 0.061 (4) |
C33 | 0.038 (3) | 0.052 (3) | 0.039 (3) | 0.022 (2) | 0.021 (2) | 0.016 (2) |
C34 | 0.050 (3) | 0.056 (3) | 0.060 (3) | 0.027 (2) | 0.037 (3) | 0.025 (3) |
C35 | 0.042 (3) | 0.055 (3) | 0.031 (2) | 0.025 (2) | 0.015 (2) | 0.006 (2) |
C37 | 0.041 (3) | 0.061 (3) | 0.071 (4) | 0.022 (3) | 0.025 (3) | 0.007 (3) |
C38 | 0.036 (3) | 0.057 (3) | 0.088 (5) | 0.020 (3) | 0.015 (3) | 0.000 (3) |
C39 | 0.051 (3) | 0.053 (3) | 0.058 (3) | 0.023 (3) | 0.009 (3) | 0.003 (3) |
C40 | 0.053 (3) | 0.055 (3) | 0.044 (3) | 0.024 (3) | 0.019 (3) | 0.010 (2) |
C41 | 0.042 (3) | 0.039 (2) | 0.039 (3) | 0.017 (2) | 0.015 (2) | 0.015 (2) |
C42 | 0.042 (3) | 0.039 (2) | 0.039 (3) | 0.018 (2) | 0.020 (2) | 0.017 (2) |
C43 | 0.056 (3) | 0.053 (3) | 0.054 (3) | 0.021 (3) | 0.033 (3) | 0.014 (2) |
C44 | 0.070 (4) | 0.066 (4) | 0.080 (4) | 0.032 (3) | 0.054 (4) | 0.023 (3) |
C45 | 0.048 (3) | 0.060 (3) | 0.075 (4) | 0.021 (3) | 0.038 (3) | 0.018 (3) |
C46 | 0.042 (3) | 0.045 (3) | 0.053 (3) | 0.015 (2) | 0.023 (2) | 0.014 (2) |
C47 | 0.051 (3) | 0.051 (3) | 0.067 (4) | 0.026 (3) | 0.029 (3) | 0.013 (3) |
C48 | 0.051 (3) | 0.050 (3) | 0.084 (5) | 0.015 (3) | 0.032 (3) | 0.005 (3) |
C49 | 0.044 (3) | 0.067 (4) | 0.077 (5) | 0.011 (3) | 0.020 (3) | −0.015 (3) |
C50 | 0.049 (3) | 0.087 (5) | 0.045 (3) | 0.026 (3) | 0.019 (3) | 0.003 (3) |
C51 | 0.040 (3) | 0.061 (3) | 0.041 (3) | 0.027 (2) | 0.020 (2) | 0.007 (2) |
C52 | 0.044 (3) | 0.064 (3) | 0.043 (3) | 0.035 (2) | 0.025 (2) | 0.016 (2) |
C29 | 0.062 (3) | 0.076 (4) | 0.070 (4) | 0.045 (3) | 0.041 (3) | 0.043 (3) |
C53 | 0.067 (4) | 0.084 (4) | 0.044 (3) | 0.049 (3) | 0.029 (3) | 0.026 (3) |
C54 | 0.092 (5) | 0.094 (5) | 0.062 (4) | 0.066 (4) | 0.048 (4) | 0.046 (4) |
C55 | 0.081 (4) | 0.067 (4) | 0.075 (4) | 0.046 (3) | 0.052 (4) | 0.041 (3) |
C56 | 0.062 (3) | 0.053 (3) | 0.053 (3) | 0.034 (3) | 0.032 (3) | 0.025 (3) |
Cu2 | 0.0401 (3) | 0.0434 (3) | 0.0389 (3) | 0.0195 (3) | 0.0192 (3) | 0.0103 (2) |
Cu1 | 0.0409 (3) | 0.0460 (3) | 0.0491 (4) | 0.0218 (3) | 0.0244 (3) | 0.0136 (3) |
I1 | 0.1320 (5) | 0.1664 (6) | 0.0966 (4) | 0.1121 (5) | 0.0670 (4) | 0.0762 (4) |
I2 | 0.0619 (3) | 0.0608 (3) | 0.0672 (3) | 0.01033 (19) | 0.0296 (2) | 0.0105 (2) |
N1 | 0.045 (2) | 0.053 (2) | 0.040 (2) | 0.029 (2) | 0.0223 (19) | 0.0163 (18) |
N2 | 0.042 (2) | 0.043 (2) | 0.046 (2) | 0.0190 (18) | 0.0195 (19) | 0.0059 (18) |
N3 | 0.046 (2) | 0.055 (3) | 0.054 (3) | 0.028 (2) | 0.024 (2) | 0.009 (2) |
N4 | 0.046 (2) | 0.051 (2) | 0.051 (2) | 0.021 (2) | 0.031 (2) | 0.015 (2) |
N5 | 0.044 (2) | 0.039 (2) | 0.045 (2) | 0.0182 (18) | 0.023 (2) | 0.0153 (17) |
N6 | 0.042 (2) | 0.046 (2) | 0.053 (3) | 0.0201 (19) | 0.027 (2) | 0.017 (2) |
N7 | 0.040 (2) | 0.043 (2) | 0.039 (2) | 0.0192 (18) | 0.0207 (18) | 0.0167 (17) |
N8 | 0.040 (2) | 0.049 (2) | 0.049 (2) | 0.0215 (19) | 0.023 (2) | 0.0126 (19) |
O1 | 0.058 (2) | 0.046 (2) | 0.059 (2) | 0.0213 (17) | 0.0337 (19) | 0.0136 (17) |
O2 | 0.068 (2) | 0.065 (2) | 0.048 (2) | 0.022 (2) | 0.029 (2) | 0.0106 (18) |
O3 | 0.053 (2) | 0.060 (2) | 0.051 (2) | 0.0343 (17) | 0.0282 (17) | 0.0239 (17) |
O4 | 0.048 (2) | 0.084 (3) | 0.058 (2) | 0.0359 (19) | 0.0337 (19) | 0.031 (2) |
O1W | 0.325 (12) | 0.176 (7) | 0.233 (9) | 0.142 (8) | 0.225 (10) | 0.116 (7) |
C1—N4 | 1.322 (6) | C31—H31 | 0.9300 |
C1—C2 | 1.384 (8) | C32—C33 | 1.385 (7) |
C1—H1 | 0.9300 | C32—H32 | 0.9300 |
C2—C3 | 1.357 (9) | C33—C34 | 1.384 (7) |
C2—H2 | 0.9300 | C33—C35 | 1.489 (6) |
C3—C4 | 1.372 (9) | C34—C29 | 1.372 (7) |
C3—H3 | 0.9300 | C34—H34 | 0.9300 |
C4—C5 | 1.387 (8) | C35—O4 | 1.243 (6) |
C4—H4 | 0.9300 | C35—O3 | 1.289 (6) |
C5—N4 | 1.341 (6) | C37—N8 | 1.342 (6) |
C5—C6 | 1.480 (8) | C37—C38 | 1.370 (8) |
C6—N3 | 1.340 (7) | C37—H37 | 0.9300 |
C6—C7 | 1.377 (8) | C38—C39 | 1.358 (9) |
C7—C8 | 1.377 (11) | C38—H38 | 0.9300 |
C7—H7 | 0.9300 | C39—C40 | 1.377 (8) |
C8—C9 | 1.348 (11) | C39—H39 | 0.9300 |
C8—H8 | 0.9300 | C40—C41 | 1.384 (7) |
C9—C10 | 1.395 (9) | C40—H40 | 0.9300 |
C9—H9 | 0.9300 | C41—N8 | 1.344 (6) |
C10—N3 | 1.344 (7) | C41—C42 | 1.487 (6) |
C10—H10 | 0.9300 | C42—N7 | 1.351 (6) |
C11—N5 | 1.346 (6) | C42—C43 | 1.358 (7) |
C11—C12 | 1.369 (7) | C43—C44 | 1.393 (8) |
C11—H11 | 0.9300 | C43—H43 | 0.9300 |
C12—C13 | 1.380 (8) | C44—C45 | 1.368 (8) |
C12—H12 | 0.9300 | C44—H44 | 0.9300 |
C13—C14 | 1.364 (8) | C45—C46 | 1.360 (7) |
C13—H13 | 0.9300 | C45—H45 | 0.9300 |
C14—C15 | 1.380 (7) | C46—N7 | 1.338 (6) |
C14—H14 | 0.9300 | C46—H46 | 0.9300 |
C15—N5 | 1.357 (6) | C47—N2 | 1.336 (7) |
C15—C16 | 1.476 (7) | C47—C48 | 1.371 (8) |
C16—N6 | 1.345 (6) | C47—H47 | 0.9300 |
C16—C17 | 1.384 (7) | C48—C49 | 1.370 (10) |
C17—C18 | 1.375 (8) | C48—H48 | 0.9300 |
C17—H17 | 0.9300 | C49—C50 | 1.394 (9) |
C18—C19 | 1.382 (9) | C49—H49 | 0.9300 |
C18—H18 | 0.9300 | C50—C51 | 1.393 (7) |
C19—C20 | 1.372 (8) | C50—H50 | 0.9300 |
C19—H19 | 0.9300 | C51—N2 | 1.349 (6) |
C20—N6 | 1.344 (6) | C51—C52 | 1.484 (7) |
C20—H20 | 0.9300 | C52—N1 | 1.339 (6) |
C21—O2 | 1.233 (6) | C52—C53 | 1.387 (7) |
C21—O1 | 1.284 (6) | C29—H29 | 0.9300 |
C21—C22 | 1.490 (7) | C53—C54 | 1.366 (8) |
C22—C23 | 1.373 (7) | C53—H53 | 0.9300 |
C22—C27 | 1.381 (7) | C54—C55 | 1.372 (8) |
C23—C24 | 1.380 (8) | C54—H54 | 0.9300 |
C23—H23 | 0.9300 | C55—C56 | 1.375 (7) |
C24—C25 | 1.373 (9) | C55—H55 | 0.9300 |
C24—H24 | 0.9300 | C56—N1 | 1.336 (6) |
C25—C26 | 1.369 (8) | C56—H56 | 0.9300 |
C25—C28 | 1.492 (8) | Cu1—O1 | 1.976 (4) |
C26—C27 | 1.381 (8) | Cu1—O2 | 2.769 (4) |
C26—H26 | 0.9300 | Cu1—N6 | 1.987 (4) |
C27—H27 | 0.9300 | Cu1—N3 | 2.000 (4) |
C28—H28A | 0.9600 | Cu1—N5 | 2.060 (4) |
C28—H28B | 0.9600 | Cu1—N4 | 2.192 (4) |
C28—H28C | 0.9600 | Cu2—O3 | 1.974 (3) |
C36—C30 | 1.506 (8) | Cu2—O4 | 2.832 (3) |
C36—H36A | 0.9600 | Cu2—N8 | 1.997 (4) |
C36—H36B | 0.9600 | Cu2—N2 | 2.001 (4) |
C36—H36C | 0.9600 | Cu2—N7 | 2.038 (4) |
C30—C31 | 1.367 (8) | Cu2—N1 | 2.181 (4) |
C30—C29 | 1.379 (8) | O1W—H2W | 0.8200 |
C31—C32 | 1.385 (8) | O1W—H1W | 0.8200 |
N4—C1—C2 | 122.5 (5) | C37—C38—H38 | 120.4 |
N4—C1—H1 | 118.7 | C38—C39—C40 | 119.8 (5) |
C2—C1—H1 | 118.7 | C38—C39—H39 | 120.1 |
C3—C2—C1 | 118.7 (6) | C40—C39—H39 | 120.1 |
C3—C2—H2 | 120.6 | C39—C40—C41 | 118.5 (5) |
C1—C2—H2 | 120.6 | C39—C40—H40 | 120.7 |
C2—C3—C4 | 119.3 (6) | C41—C40—H40 | 120.7 |
C2—C3—H3 | 120.3 | N8—C41—C40 | 121.6 (5) |
C4—C3—H3 | 120.3 | N8—C41—C42 | 115.0 (4) |
C3—C4—C5 | 119.5 (6) | C40—C41—C42 | 123.5 (5) |
C3—C4—H4 | 120.2 | N7—C42—C43 | 122.7 (4) |
C5—C4—H4 | 120.2 | N7—C42—C41 | 113.9 (4) |
N4—C5—C4 | 120.7 (5) | C43—C42—C41 | 123.4 (4) |
N4—C5—C6 | 115.5 (4) | C42—C43—C44 | 118.7 (5) |
C4—C5—C6 | 123.8 (5) | C42—C43—H43 | 120.7 |
N3—C6—C7 | 121.3 (6) | C44—C43—H43 | 120.7 |
N3—C6—C5 | 116.0 (4) | C45—C44—C43 | 118.8 (5) |
C7—C6—C5 | 122.8 (6) | C45—C44—H44 | 120.6 |
C6—C7—C8 | 118.7 (7) | C43—C44—H44 | 120.6 |
C6—C7—H7 | 120.7 | C46—C45—C44 | 119.2 (5) |
C8—C7—H7 | 120.7 | C46—C45—H45 | 120.4 |
C9—C8—C7 | 120.6 (7) | C44—C45—H45 | 120.4 |
C9—C8—H8 | 119.7 | N7—C46—C45 | 123.0 (5) |
C7—C8—H8 | 119.7 | N7—C46—H46 | 118.5 |
C8—C9—C10 | 118.8 (7) | C45—C46—H46 | 118.5 |
C8—C9—H9 | 120.6 | N2—C47—C48 | 123.2 (6) |
C10—C9—H9 | 120.6 | N2—C47—H47 | 118.4 |
N3—C10—C9 | 120.8 (7) | C48—C47—H47 | 118.4 |
N3—C10—H10 | 119.6 | C49—C48—C47 | 117.8 (6) |
C9—C10—H10 | 119.6 | C49—C48—H48 | 121.1 |
N5—C11—C12 | 122.4 (5) | C47—C48—H48 | 121.1 |
N5—C11—H11 | 118.8 | C48—C49—C50 | 120.3 (6) |
C12—C11—H11 | 118.8 | C48—C49—H49 | 119.8 |
C11—C12—C13 | 118.8 (5) | C50—C49—H49 | 119.8 |
C11—C12—H12 | 120.6 | C51—C50—C49 | 118.7 (6) |
C13—C12—H12 | 120.6 | C51—C50—H50 | 120.6 |
C14—C13—C12 | 119.5 (5) | C49—C50—H50 | 120.6 |
C14—C13—H13 | 120.3 | N2—C51—C50 | 120.2 (5) |
C12—C13—H13 | 120.3 | N2—C51—C52 | 116.7 (4) |
C13—C14—C15 | 119.7 (5) | C50—C51—C52 | 123.0 (5) |
C13—C14—H14 | 120.1 | N1—C52—C53 | 121.9 (5) |
C15—C14—H14 | 120.1 | N1—C52—C51 | 114.6 (4) |
N5—C15—C14 | 121.0 (5) | C53—C52—C51 | 123.5 (5) |
N5—C15—C16 | 114.4 (4) | C34—C29—C30 | 121.6 (5) |
C14—C15—C16 | 124.6 (5) | C34—C29—H29 | 119.2 |
N6—C16—C17 | 120.4 (5) | C30—C29—H29 | 119.2 |
N6—C16—C15 | 115.3 (4) | C54—C53—C52 | 118.8 (5) |
C17—C16—C15 | 124.3 (5) | C54—C53—H53 | 120.6 |
C18—C17—C16 | 120.1 (6) | C52—C53—H53 | 120.6 |
C18—C17—H17 | 119.9 | C53—C54—C55 | 119.7 (5) |
C16—C17—H17 | 119.9 | C53—C54—H54 | 120.1 |
C17—C18—C19 | 118.7 (6) | C55—C54—H54 | 120.1 |
C17—C18—H18 | 120.7 | C54—C55—C56 | 118.6 (6) |
C19—C18—H18 | 120.7 | C54—C55—H55 | 120.7 |
C20—C19—C18 | 119.3 (6) | C56—C55—H55 | 120.7 |
C20—C19—H19 | 120.4 | N1—C56—C55 | 122.6 (5) |
C18—C19—H19 | 120.4 | N1—C56—H56 | 118.7 |
N6—C20—C19 | 121.7 (5) | C55—C56—H56 | 118.7 |
N6—C20—H20 | 119.1 | O1—Cu1—O2 | 52.46 (16) |
C19—C20—H20 | 119.1 | O1—Cu1—N6 | 92.58 (16) |
O2—C21—O1 | 123.2 (5) | O1—Cu1—N3 | 94.78 (16) |
O2—C21—C22 | 120.5 (5) | O2—Cu1—N6 | 96.13 (16) |
O1—C21—C22 | 116.3 (5) | O2—Cu1—N3 | 90.52 (16) |
C23—C22—C27 | 117.5 (5) | N6—Cu1—N3 | 172.15 (16) |
C23—C22—C21 | 122.2 (5) | O1—Cu1—N5 | 152.67 (15) |
C27—C22—C21 | 120.3 (5) | O2—Cu1—N5 | 101.75 (16) |
C22—C23—C24 | 120.7 (6) | N6—Cu1—N5 | 80.38 (16) |
C22—C23—H23 | 119.7 | N3—Cu1—N5 | 94.23 (16) |
C24—C23—H23 | 119.7 | O1—Cu1—N4 | 102.51 (15) |
C25—C24—C23 | 122.3 (6) | O2—Cu1—N4 | 152.05 (16) |
C25—C24—H24 | 118.9 | N6—Cu1—N4 | 97.40 (16) |
C23—C24—H24 | 118.9 | N3—Cu1—N4 | 78.34 (17) |
C26—C25—C24 | 116.8 (5) | N5—Cu1—N4 | 104.56 (15) |
C26—C25—C28 | 121.7 (6) | O3—Cu2—O4 | 51.67 (15) |
C24—C25—C28 | 121.6 (6) | O3—Cu2—N8 | 90.84 (15) |
C25—C26—C27 | 121.7 (6) | O3—Cu2—N2 | 91.78 (15) |
C25—C26—H26 | 119.1 | O4—Cu2—N8 | 93.70 (15) |
C27—C26—H26 | 119.1 | O4—Cu2—N2 | 86.63 (15) |
C26—C27—C22 | 121.0 (5) | N8—Cu2—N2 | 176.92 (16) |
C26—C27—H27 | 119.5 | O3—Cu2—N7 | 156.24 (15) |
C22—C27—H27 | 119.5 | O4—Cu2—N7 | 106.46 (15) |
C25—C28—H28A | 109.5 | N8—Cu2—N7 | 80.59 (16) |
C25—C28—H28B | 109.5 | N2—Cu2—N7 | 96.37 (16) |
H28A—C28—H28B | 109.5 | O3—Cu2—N1 | 94.97 (14) |
C25—C28—H28C | 109.5 | O4—Cu2—N1 | 143.21 (15) |
H28A—C28—H28C | 109.5 | N8—Cu2—N1 | 102.89 (16) |
H28B—C28—H28C | 109.5 | N2—Cu2—N1 | 78.49 (16) |
C30—C36—H36A | 109.5 | N7—Cu2—N1 | 108.50 (14) |
C30—C36—H36B | 109.5 | C56—N1—C52 | 118.4 (4) |
H36A—C36—H36B | 109.5 | C56—N1—Cu2 | 128.6 (3) |
C30—C36—H36C | 109.5 | C52—N1—Cu2 | 112.8 (3) |
H36A—C36—H36C | 109.5 | C47—N2—C51 | 119.7 (4) |
H36B—C36—H36C | 109.5 | C47—N2—Cu2 | 123.0 (4) |
C31—C30—C29 | 116.7 (5) | C51—N2—Cu2 | 117.3 (3) |
C31—C30—C36 | 122.4 (6) | C6—N3—C10 | 119.8 (5) |
C29—C30—C36 | 120.9 (6) | C6—N3—Cu1 | 117.7 (3) |
C30—C31—C32 | 123.3 (6) | C10—N3—Cu1 | 122.0 (4) |
C30—C31—H31 | 118.4 | C1—N4—C5 | 119.2 (5) |
C32—C31—H31 | 118.4 | C1—N4—Cu1 | 129.0 (3) |
C33—C32—C31 | 119.1 (5) | C5—N4—Cu1 | 111.7 (3) |
C33—C32—H32 | 120.5 | C11—N5—C15 | 118.6 (4) |
C31—C32—H32 | 120.5 | C11—N5—Cu1 | 127.7 (3) |
C34—C33—C32 | 118.3 (5) | C15—N5—Cu1 | 113.7 (3) |
C34—C33—C35 | 121.2 (4) | C20—N6—C16 | 119.8 (4) |
C32—C33—C35 | 120.5 (5) | C20—N6—Cu1 | 124.0 (4) |
C29—C34—C33 | 121.1 (5) | C16—N6—Cu1 | 116.1 (3) |
C29—C34—H34 | 119.5 | C46—N7—C42 | 117.5 (4) |
C33—C34—H34 | 119.5 | C46—N7—Cu2 | 127.8 (3) |
O4—C35—O3 | 123.7 (4) | C42—N7—Cu2 | 114.5 (3) |
O4—C35—C33 | 120.0 (4) | C37—N8—C41 | 118.6 (4) |
O3—C35—C33 | 116.3 (4) | C37—N8—Cu2 | 125.8 (4) |
N8—C37—C38 | 122.2 (6) | C41—N8—Cu2 | 115.5 (3) |
N8—C37—H37 | 118.9 | C21—O1—Cu1 | 110.0 (3) |
C38—C37—H37 | 118.9 | C35—O3—Cu2 | 111.0 (3) |
C39—C38—C37 | 119.2 (5) | H2W—O1W—H1W | 103.5 |
C39—C38—H38 | 120.4 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···I1i | 0.82 | 3.15 | 3.935 (8) | 161 |
O1W—H2W···I1ii | 0.82 | 2.76 | 3.568 (8) | 170 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C8H7O2)(C10H8N2)2]I·0.5H2O |
Mr | 646.96 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 14.6698 (4), 15.3588 (4), 15.4224 (7) |
α, β, γ (°) | 100.943 (2), 114.345 (2), 111.996 (2) |
V (Å3) | 2680.64 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.00 |
Crystal size (mm) | 0.37 × 0.30 × 0.26 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.525, 0.624 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29909, 9564, 6740 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.149, 1.03 |
No. of reflections | 9564 |
No. of parameters | 660 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.56, −1.53 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Cu1—O1 | 1.976 (4) | Cu2—O3 | 1.974 (3) |
Cu1—O2 | 2.769 (4) | Cu2—O4 | 2.832 (3) |
Cu1—N6 | 1.987 (4) | Cu2—N8 | 1.997 (4) |
Cu1—N3 | 2.000 (4) | Cu2—N2 | 2.001 (4) |
Cu1—N5 | 2.060 (4) | Cu2—N7 | 2.038 (4) |
Cu1—N4 | 2.192 (4) | Cu2—N1 | 2.181 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···I1i | 0.82 | 3.15 | 3.935 (8) | 161 |
O1W—H2W···I1ii | 0.82 | 2.76 | 3.568 (8) | 170 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y+1, z. |
Acknowledgements
The authors acknowledge South China University of Technology for supporting this work.
References
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Song, W.-D., Yan, J.-B. & Hao, X.-M. (2008d). Acta Cryst. E64, m919–m920. Web of Science CSD CrossRef IUCr Journals Google Scholar
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As a building block, 4-methylbenzoate ligand is an excellent candidate for the construction of supramolecular complexes (Ma & Deng, 2008; Song et al., 2008a,b,c,d). Recently, we obtained the title mononuclear complex by the hydrothermal reaction of CuI, 4-methylbenzoic acid and 2,2'-bipyridine.
As illustrated in Fig. 1, the asymmetric unit of the title compound contains two independent complex molecules, two I ions and one lattice water molecule. Each CuII atom has a distorted octahedral coordination geometry, involving two carboxylate O atoms from one 4-methylbenzoate ligand, and four N atoms from two 2,2'-bipyridine ligands. One Cu—O distance is distinctly longer than the others for each CuII atom (Table 1), but still within the range of a significant interaction (Mao et al. 2001). Judged from the blue crystals, the initial reactant of CuI was thus oxidated to CuII in the hydrothermal reaction. The structure involves O—H···I hydrogen bonds between the water molecule and I ions (Table 2) and π–π stacking interactions (Fig. 2). The centroid–centroid distances are 3.79 (1)Å between the adjacent phenyl and pyridyl rings, and 3.87 (1)Å between the adjacent pyridyl rings.