Related literature
For a related structure, see: Yang et al. (2009
).
Experimental
Crystal data
[Cu(C8H7O2)2(C6H6N4)2] Mr = 602.11 Monoclinic, P 21 /n a = 12.2839 (9) Å b = 7.3150 (5) Å c = 14.9755 (11) Å β = 93.673 (1)° V = 1342.89 (17) Å3 Z = 2 Mo Kα radiation μ = 0.87 mm−1 T = 296 K 0.25 × 0.18 × 0.15 mm
|
Data collection
Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2001 ) Tmin = 0.813, Tmax = 0.881 6459 measured reflections 2611 independent reflections 1807 reflections with I > 2σ(I) Rint = 0.043
|
Cu1—N3 | 2.012 (2) | Cu1—N1 | 2.021 (2) | Cu1—O2 | 2.685 (2) | | |
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | N4—H4A⋯O1i | 0.890 (10) | 1.755 (11) | 2.644 (3) | 178 (3) | N2—H2A⋯O2i | 0.894 (10) | 1.755 (11) | 2.647 (3) | 176 (3) | Symmetry code: (i) x, y-1, z. | |
Data collection: SMART (Bruker, 2001
); cell refinement: SAINT (Bruker, 2001
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: PLATON (Spek, 2009
); software used to prepare material for publication: PLATON.
Supporting information
CuCl2.2H2O (0.17 g, 1.0 mmol) was added into an aqueous solution (15 ml) of 4-methyl-benzenecarboxylic acid (0.14 g, 1.0 mmol) and NaOH (0.04 g, 1.0 mmol) and refluxed for 30 min. Then an ethanol solution (10 ml) containing 2,2'-biimidazole (0.13 g, 1.0 mmol) was slowly added with continuous stirring. The resulting solution was refluxed for 3 h, filtered and kept for crystallization. After nine days, blue blocks of (I) were obtained.
H atoms bonded to N are located in a difference maps and refined isotropically 0.89 (1) for N—H using DFIX commands. All the remaining H atoms were positioned geometrically with C—H = 0.93 Å (aromatic) and 0.96 Å (methyl) and were refined as riding with Uiso(H) =1.2Ueq(C) (aromatic) and 1.5Ueq(C) (methyl).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).
Bis(2,2'-bi-1
H-imidazole-
κ2N3,
N3')bis(4- methylbenzoato-
κO)copper(II)
top Crystal data top [Cu(C8H7O2)2(C6H6N4)2] | F(000) = 622 |
Mr = 602.11 | Dx = 1.489 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1035 reflections |
a = 12.2839 (9) Å | θ = 2.7–22.3° |
b = 7.3150 (5) Å | µ = 0.87 mm−1 |
c = 14.9755 (11) Å | T = 296 K |
β = 93.673 (1)° | Block, blue |
V = 1342.89 (17) Å3 | 0.25 × 0.18 × 0.15 mm |
Z = 2 | |
Data collection top Bruker SMART APEX CCD diffractometer | 2611 independent reflections |
Radiation source: fine-focus sealed tube | 1807 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
0.3° wide ω exposures scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −13→15 |
Tmin = 0.813, Tmax = 0.881 | k = −8→9 |
6459 measured reflections | l = −18→10 |
Refinement top 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0405P)2 + 0.305P] where P = (Fo2 + 2Fc2)/3 |
2611 reflections | (Δ/σ)max < 0.001 |
196 parameters | Δρmax = 0.26 e Å−3 |
2 restraints | Δρmin = −0.29 e Å−3 |
Crystal data top [Cu(C8H7O2)2(C6H6N4)2] | V = 1342.89 (17) Å3 |
Mr = 602.11 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.2839 (9) Å | µ = 0.87 mm−1 |
b = 7.3150 (5) Å | T = 296 K |
c = 14.9755 (11) Å | 0.25 × 0.18 × 0.15 mm |
β = 93.673 (1)° | |
Data collection top Bruker SMART APEX CCD diffractometer | 2611 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1807 reflections with I > 2σ(I) |
Tmin = 0.813, Tmax = 0.881 | Rint = 0.043 |
6459 measured reflections | |
Refinement top R[F2 > 2σ(F2)] = 0.045 | 2 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.26 e Å−3 |
2611 reflections | Δρmin = −0.29 e Å−3 |
196 parameters | |
Special details top 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 1.0000 | 1.0000 | 0.0000 | 0.03766 (19) | |
N1 | 0.89630 (18) | 0.7883 (3) | 0.01223 (16) | 0.0349 (6) | |
N2 | 0.8736 (2) | 0.5161 (3) | 0.07173 (18) | 0.0397 (6) | |
H2A | 0.895 (3) | 0.410 (3) | 0.096 (2) | 0.067 (11)* | |
N3 | 1.09622 (18) | 0.8469 (3) | 0.08419 (16) | 0.0347 (6) | |
N4 | 1.1064 (2) | 0.5980 (4) | 0.16805 (17) | 0.0408 (6) | |
H4A | 1.087 (2) | 0.494 (3) | 0.193 (2) | 0.053 (10)* | |
C9 | 0.7954 (2) | 0.7212 (4) | −0.0174 (2) | 0.0417 (8) | |
H9 | 0.7454 | 0.7807 | −0.0565 | 0.050* | |
C10 | 0.7809 (2) | 0.5549 (4) | 0.0195 (2) | 0.0450 (8) | |
H10 | 0.7195 | 0.4809 | 0.0110 | 0.054* | |
C11 | 0.9395 (2) | 0.6593 (4) | 0.06569 (19) | 0.0333 (7) | |
C12 | 1.0464 (2) | 0.6939 (4) | 0.10720 (19) | 0.0342 (7) | |
C13 | 1.2008 (2) | 0.6939 (4) | 0.1851 (2) | 0.0478 (8) | |
H13 | 1.2587 | 0.6610 | 0.2249 | 0.057* | |
C14 | 1.1944 (2) | 0.8452 (4) | 0.1337 (2) | 0.0420 (8) | |
H14 | 1.2481 | 0.9346 | 0.1320 | 0.050* | |
O1 | 1.05155 (19) | 1.2894 (3) | 0.24540 (17) | 0.0673 (8) | |
O2 | 0.93115 (18) | 1.1925 (3) | 0.13825 (16) | 0.0527 (6) | |
C1 | 0.9823 (3) | 1.1777 (4) | 0.2138 (2) | 0.0444 (8) | |
C2 | 0.9573 (2) | 1.0140 (4) | 0.2697 (2) | 0.0379 (7) | |
C3 | 0.8761 (2) | 0.8939 (4) | 0.2408 (2) | 0.0415 (8) | |
H3 | 0.8384 | 0.9127 | 0.1857 | 0.050* | |
C4 | 0.8499 (3) | 0.7468 (5) | 0.2923 (2) | 0.0500 (9) | |
H4 | 0.7947 | 0.6676 | 0.2715 | 0.060* | |
C5 | 0.9039 (3) | 0.7145 (5) | 0.3741 (2) | 0.0506 (9) | |
C6 | 0.9860 (3) | 0.8328 (5) | 0.4026 (2) | 0.0566 (10) | |
H6 | 1.0242 | 0.8122 | 0.4573 | 0.068* | |
C7 | 1.0128 (3) | 0.9816 (4) | 0.3515 (2) | 0.0507 (9) | |
H7 | 1.0683 | 1.0602 | 0.3722 | 0.061* | |
C8 | 0.8718 (3) | 0.5549 (6) | 0.4308 (3) | 0.0838 (14) | |
H8A | 0.8992 | 0.4436 | 0.4067 | 0.126* | |
H8B | 0.7937 | 0.5485 | 0.4307 | 0.126* | |
H8C | 0.9021 | 0.5710 | 0.4910 | 0.126* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0373 (3) | 0.0273 (3) | 0.0474 (4) | −0.0028 (2) | −0.0042 (2) | 0.0112 (2) |
N1 | 0.0373 (13) | 0.0266 (13) | 0.0404 (15) | 0.0007 (11) | −0.0007 (11) | 0.0035 (11) |
N2 | 0.0399 (14) | 0.0276 (15) | 0.0512 (16) | −0.0012 (12) | −0.0003 (13) | 0.0073 (12) |
N3 | 0.0383 (13) | 0.0242 (13) | 0.0411 (15) | −0.0033 (11) | −0.0010 (12) | 0.0036 (11) |
N4 | 0.0411 (15) | 0.0313 (15) | 0.0488 (17) | −0.0016 (12) | −0.0071 (13) | 0.0134 (13) |
C9 | 0.0405 (17) | 0.0315 (17) | 0.052 (2) | 0.0030 (14) | −0.0065 (15) | 0.0054 (14) |
C10 | 0.0370 (17) | 0.0360 (18) | 0.061 (2) | −0.0050 (14) | −0.0052 (16) | 0.0028 (16) |
C11 | 0.0381 (16) | 0.0254 (16) | 0.0364 (17) | −0.0013 (13) | 0.0039 (14) | 0.0040 (13) |
C12 | 0.0375 (16) | 0.0270 (16) | 0.0378 (18) | 0.0013 (13) | 0.0007 (14) | 0.0005 (13) |
C13 | 0.0412 (18) | 0.046 (2) | 0.054 (2) | −0.0018 (15) | −0.0124 (16) | 0.0117 (17) |
C14 | 0.0429 (18) | 0.0359 (18) | 0.046 (2) | −0.0071 (14) | −0.0050 (16) | 0.0042 (15) |
O1 | 0.0665 (16) | 0.0519 (16) | 0.0802 (19) | −0.0196 (13) | −0.0211 (14) | 0.0323 (14) |
O2 | 0.0590 (14) | 0.0433 (14) | 0.0549 (15) | −0.0006 (11) | −0.0050 (12) | 0.0187 (11) |
C1 | 0.0415 (18) | 0.0378 (19) | 0.054 (2) | 0.0051 (15) | 0.0002 (17) | 0.0120 (16) |
C2 | 0.0374 (16) | 0.0327 (17) | 0.0437 (19) | 0.0052 (14) | 0.0023 (14) | 0.0073 (14) |
C3 | 0.0453 (18) | 0.0395 (19) | 0.0392 (19) | 0.0028 (15) | −0.0010 (15) | 0.0092 (15) |
C4 | 0.0507 (19) | 0.0427 (19) | 0.056 (2) | −0.0127 (16) | −0.0030 (17) | 0.0077 (17) |
C5 | 0.0470 (19) | 0.044 (2) | 0.060 (2) | −0.0069 (16) | 0.0045 (17) | 0.0199 (17) |
C6 | 0.057 (2) | 0.058 (2) | 0.053 (2) | −0.0043 (18) | −0.0108 (18) | 0.0261 (18) |
C7 | 0.0451 (18) | 0.050 (2) | 0.055 (2) | −0.0119 (16) | −0.0118 (16) | 0.0160 (17) |
C8 | 0.085 (3) | 0.078 (3) | 0.086 (3) | −0.029 (2) | −0.010 (2) | 0.045 (3) |
Geometric parameters (Å, º) top Cu1—N3i | 2.012 (2) | C13—C14 | 1.347 (4) |
Cu1—N3 | 2.012 (2) | C13—H13 | 0.9300 |
Cu1—N1i | 2.021 (2) | C14—H14 | 0.9300 |
Cu1—N1 | 2.021 (2) | O1—C1 | 1.251 (4) |
Cu1—O2 | 2.685 (2) | O2—C1 | 1.263 (4) |
Cu1—O2i | 2.685 (2) | C1—C2 | 1.504 (4) |
N1—C11 | 1.326 (3) | C2—C3 | 1.378 (4) |
N1—C9 | 1.380 (3) | C2—C7 | 1.384 (4) |
N2—C11 | 1.331 (3) | C3—C4 | 1.374 (4) |
N2—C10 | 1.370 (4) | C3—H3 | 0.9300 |
N2—H2A | 0.894 (10) | C4—C5 | 1.375 (4) |
N3—C12 | 1.332 (3) | C4—H4 | 0.9300 |
N3—C14 | 1.375 (4) | C5—C6 | 1.376 (5) |
N4—C12 | 1.334 (3) | C5—C8 | 1.510 (4) |
N4—C13 | 1.365 (4) | C6—C7 | 1.382 (4) |
N4—H4A | 0.890 (10) | C6—H6 | 0.9300 |
C9—C10 | 1.353 (4) | C7—H7 | 0.9300 |
C9—H9 | 0.9300 | C8—H8A | 0.9600 |
C10—H10 | 0.9300 | C8—H8B | 0.9600 |
C11—C12 | 1.439 (4) | C8—H8C | 0.9600 |
| | | |
N3i—Cu1—N3 | 180.0 | N4—C13—H13 | 126.3 |
N3i—Cu1—N1i | 82.25 (9) | C13—C14—N3 | 109.4 (3) |
N3—Cu1—N1i | 97.75 (9) | C13—C14—H14 | 125.3 |
N3i—Cu1—N1 | 97.75 (9) | N3—C14—H14 | 125.3 |
N3—Cu1—N1 | 82.25 (9) | O1—C1—O2 | 124.8 (3) |
N1i—Cu1—N1 | 180.0 | O1—C1—C2 | 117.9 (3) |
C11—N1—C9 | 104.9 (2) | O2—C1—C2 | 117.3 (3) |
C11—N1—Cu1 | 111.68 (18) | C3—C2—C7 | 118.3 (3) |
C9—N1—Cu1 | 143.3 (2) | C3—C2—C1 | 120.1 (3) |
C11—N2—C10 | 106.6 (3) | C7—C2—C1 | 121.5 (3) |
C11—N2—H2A | 123 (2) | C4—C3—C2 | 120.9 (3) |
C10—N2—H2A | 129 (2) | C4—C3—H3 | 119.5 |
C12—N3—C14 | 104.7 (2) | C2—C3—H3 | 119.5 |
C12—N3—Cu1 | 111.65 (18) | C3—C4—C5 | 121.2 (3) |
C14—N3—Cu1 | 143.40 (19) | C3—C4—H4 | 119.4 |
C12—N4—C13 | 106.5 (2) | C5—C4—H4 | 119.4 |
C12—N4—H4A | 126 (2) | C4—C5—C6 | 118.0 (3) |
C13—N4—H4A | 128 (2) | C4—C5—C8 | 120.3 (3) |
C10—C9—N1 | 109.2 (3) | C6—C5—C8 | 121.6 (3) |
C10—C9—H9 | 125.4 | C5—C6—C7 | 121.3 (3) |
N1—C9—H9 | 125.4 | C5—C6—H6 | 119.4 |
C9—C10—N2 | 107.0 (3) | C7—C6—H6 | 119.4 |
C9—C10—H10 | 126.5 | C6—C7—C2 | 120.2 (3) |
N2—C10—H10 | 126.5 | C6—C7—H7 | 119.9 |
N1—C11—N2 | 112.3 (3) | C2—C7—H7 | 119.9 |
N1—C11—C12 | 117.1 (2) | C5—C8—H8A | 109.5 |
N2—C11—C12 | 130.6 (3) | C5—C8—H8B | 109.5 |
N3—C12—N4 | 112.1 (2) | H8A—C8—H8B | 109.5 |
N3—C12—C11 | 117.2 (3) | C5—C8—H8C | 109.5 |
N4—C12—C11 | 130.7 (3) | H8A—C8—H8C | 109.5 |
C14—C13—N4 | 107.3 (3) | H8B—C8—H8C | 109.5 |
C14—C13—H13 | 126.3 | | |
Symmetry code: (i) −x+2, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···O1ii | 0.89 (1) | 1.76 (1) | 2.644 (3) | 178 (3) |
N2—H2A···O2ii | 0.89 (1) | 1.76 (1) | 2.647 (3) | 176 (3) |
Symmetry code: (ii) x, y−1, z. |
Experimental details
Crystal data |
Chemical formula | [Cu(C8H7O2)2(C6H6N4)2] |
Mr | 602.11 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 12.2839 (9), 7.3150 (5), 14.9755 (11) |
β (°) | 93.673 (1) |
V (Å3) | 1342.89 (17) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.87 |
Crystal size (mm) | 0.25 × 0.18 × 0.15 |
|
Data collection |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.813, 0.881 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6459, 2611, 1807 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.104, 1.02 |
No. of reflections | 2611 |
No. of parameters | 196 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.29 |
Selected bond lengths (Å) topCu1—N3 | 2.012 (2) | Cu1—O2 | 2.685 (2) |
Cu1—N1 | 2.021 (2) | | |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···O1i | 0.890 (10) | 1.755 (11) | 2.644 (3) | 178 (3) |
N2—H2A···O2i | 0.894 (10) | 1.755 (11) | 2.647 (3) | 176 (3) |
Symmetry code: (i) x, y−1, z. |
References
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, L. F., Cao, M. L., Mo, H. J., Hao, H. G., Wu, J. J., Zhang, J. P. & Ye, B. H. (2009). CrystEngComm, 11, 1114–1121. Web of Science CSD CrossRef CAS Google Scholar
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2,2'-Biimidazole is an interesting ligand because it has two N atoms and two –NH donors. Both N-donors having the stronger coordination ability and flexible coordination modes. Additionally, two –NH donors can interact with other hydrogen bonding acceptors via hydrogen bonds (Yang et al., 2009). Herein, we report the title compound of bis(4-methyl-benzenecarboxylate-kN)bis(2,2'-biimidazole-N,N') copper, (I).
In the symmetric unit of (I), Cu2+ having an inversion centre was chelated by two 2,2'-biimidazole ligands through and weakly interacts with two 4-methyl benzenecarboxylate ligands acting as monodentate, which results in a elongated octahedron (Cu1—N1 2.021 (2) Å; Cu1—N3 2.012 (2) Å; Cu1—O2 2.685 (2) Å). Adjacent two Cu(C8H7O2)(C6H3N4) units are linked together by two pairs of N—H···O hydrogen bonds forming two R22(9) motifs, which are further arranged into a one-dimensional chain along the [010] direction.