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The title complex, [Cu2(C7H4O3)2(C10H8N2)2]·2C7H6O3, crystallizes as a centrosymmetric dimer containing two CuII atoms bridged by two phenolato O atoms from salicylate ligands. Each CuII atom lies in an approximate square planar environment and is bonded to two N atoms of a 2,2′-bipyridine ligand, the phenolato O and the carboxylato O atoms of a salicylate ligand. The coordination of CuII is completed by bonding to a phenolato O atom in the axial direction, giving square pyramidal geometry. The dimer is stabilized by a strong intermolecular π–π interaction involving pairs of bipyridine ligands and a salicylate ring. The crystal structure is stabilized by π–π interactions and hydrogen bonds.
Supporting information
CCDC reference: 252772
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.044
- wR factor = 0.131
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.35
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O3_a .. 5.96 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalStructure (Rigaku & Rigaku/MSC, 2000-2004); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIF (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Scheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
Crystal data top
[Cu2(C7H4O3)2(C10H8N2)2]·2C7H6O3 | F(000) = 1012.00 |
Mr = 987.91 | Dx = 1.550 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -p_2yab | Cell parameters from 13777 reflections |
a = 10.46 (1) Å | θ = 3.1–27.4° |
b = 17.79 (2) Å | µ = 1.08 mm−1 |
c = 12.04 (1) Å | T = 296 K |
β = 109.25 (4)° | Lath, blue |
V = 2115 (4) Å3 | 0.50 × 0.10 × 0.05 mm |
Z = 2 | |
Data collection top
Rigaku RAXIS-RAPID diffractometer | 2392 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.034 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −13→13 |
Tmin = 0.534, Tmax = 0.948 | k = −23→22 |
20430 measured reflections | l = −15→15 |
4824 independent reflections | |
Refinement top
Refinement on F2 | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0917P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.131 | (Δ/σ)max < 0.001 |
S = 0.85 | Δρmax = 1.08 e Å−3 |
4824 reflections | Δρmin = −0.46 e Å−3 |
304 parameters | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.84570 (4) | 0.03137 (2) | 0.95208 (3) | 0.0443 (1) | |
O1 | 0.7985 (2) | 0.0186 (1) | 1.0908 (2) | 0.0530 (5) | |
O2 | 0.8037 (2) | 0.0326 (1) | 1.2739 (2) | 0.0581 (6) | |
O3 | 1.0062 (2) | 0.0837 (1) | 1.0318 (1) | 0.0468 (5) | |
O4 | 0.3529 (3) | 0.1023 (1) | 0.6149 (2) | 0.0768 (7) | |
O5 | 0.3791 (3) | 0.0649 (1) | 0.7980 (2) | 0.0614 (6) | |
O6 | 0.5186 (3) | 0.1988 (1) | 0.5793 (2) | 0.0898 (9) | |
N1 | 0.6862 (3) | −0.0283 (1) | 0.8569 (2) | 0.0442 (5) | |
N2 | 0.8560 (3) | 0.0546 (1) | 0.7926 (2) | 0.0453 (6) | |
C1 | 0.6662 (3) | −0.0284 (1) | 0.7395 (2) | 0.0440 (6) | |
C2 | 0.5631 (4) | −0.0694 (2) | 0.6623 (3) | 0.0596 (9) | |
C3 | 0.4809 (4) | −0.1116 (2) | 0.7059 (3) | 0.068 (1) | |
C4 | 0.5032 (4) | −0.1135 (2) | 0.8258 (3) | 0.068 (1) | |
C5 | 0.6062 (3) | −0.0703 (2) | 0.8985 (3) | 0.0534 (8) | |
C6 | 0.7632 (3) | 0.0173 (1) | 0.7043 (2) | 0.0460 (7) | |
C7 | 0.7656 (4) | 0.0202 (2) | 0.5901 (3) | 0.067 (1) | |
C8 | 0.8617 (5) | 0.0631 (2) | 0.5671 (3) | 0.086 (1) | |
C9 | 0.9582 (5) | 0.1033 (2) | 0.6572 (3) | 0.079 (1) | |
C10 | 0.9503 (4) | 0.0972 (2) | 0.7694 (3) | 0.0571 (8) | |
C11 | 0.9591 (3) | 0.1046 (1) | 1.2145 (2) | 0.0435 (6) | |
C12 | 1.0291 (3) | 0.1193 (1) | 1.1338 (2) | 0.0413 (6) | |
C13 | 1.1345 (3) | 0.1734 (1) | 1.1634 (3) | 0.0504 (7) | |
C14 | 1.1732 (4) | 0.2096 (2) | 1.2739 (3) | 0.0607 (9) | |
C15 | 1.1048 (4) | 0.1943 (2) | 1.3514 (3) | 0.068 (1) | |
C16 | 0.9997 (4) | 0.1434 (2) | 1.3220 (3) | 0.0574 (8) | |
C17 | 0.8485 (3) | 0.0491 (2) | 1.1916 (2) | 0.0447 (7) | |
C18 | 0.5345 (3) | 0.1519 (1) | 0.7711 (3) | 0.0477 (7) | |
C19 | 0.5812 (4) | 0.1970 (2) | 0.6965 (3) | 0.0637 (9) | |
C20 | 0.6964 (4) | 0.2411 (2) | 0.7420 (4) | 0.078 (1) | |
C21 | 0.7639 (4) | 0.2422 (2) | 0.8640 (4) | 0.078 (1) | |
C22 | 0.7190 (4) | 0.1976 (2) | 0.9403 (3) | 0.0644 (9) | |
C23 | 0.6064 (3) | 0.1538 (2) | 0.8932 (3) | 0.0531 (8) | |
C24 | 0.4139 (3) | 0.1039 (2) | 0.7216 (3) | 0.0525 (7) | |
H1 | 0.5495 | −0.0686 | 0.5820 | 0.072* | |
H2 | 0.4099 | −0.1389 | 0.6550 | 0.082* | |
H3 | 0.4499 | −0.1432 | 0.8566 | 0.082* | |
H4 | 0.6206 | −0.0704 | 0.9789 | 0.064* | |
H5 | 0.7028 | −0.0065 | 0.5303 | 0.081* | |
H6 | 0.8638 | 0.0659 | 0.4906 | 0.103* | |
H7 | 1.0241 | 0.1326 | 0.6420 | 0.095* | |
H8 | 1.0121 | 0.1234 | 0.8306 | 0.068* | |
H9 | 1.1783 | 0.1851 | 1.1098 | 0.060* | |
H10 | 1.2447 | 0.2437 | 1.2942 | 0.073* | |
H11 | 1.1297 | 0.2185 | 1.4239 | 0.082* | |
H12 | 0.9542 | 0.1344 | 1.3752 | 0.069* | |
H13 | 0.7286 | 0.2696 | 0.6921 | 0.094* | |
H14 | 0.8394 | 0.2728 | 0.8948 | 0.093* | |
H15 | 0.7647 | 0.1979 | 1.0209 | 0.077* | |
H16 | 0.5762 | 0.1242 | 0.9433 | 0.064* | |
H17 | 0.4524 | 0.1731 | 0.5650 | 0.078* | |
H18 | 0.309 | 0.038 | 0.777 | 0.102* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0457 (2) | 0.0549 (2) | 0.0323 (2) | −0.0062 (2) | 0.0129 (1) | −0.0049 (1) |
O1 | 0.054 (1) | 0.071 (1) | 0.036 (1) | −0.017 (1) | 0.0174 (9) | −0.0098 (9) |
O2 | 0.059 (1) | 0.083 (2) | 0.037 (1) | −0.018 (1) | 0.022 (1) | −0.008 (1) |
O3 | 0.049 (1) | 0.058 (1) | 0.0353 (9) | −0.010 (1) | 0.0160 (9) | −0.0081 (9) |
O4 | 0.095 (2) | 0.081 (2) | 0.045 (1) | −0.018 (1) | 0.011 (1) | −0.004 (1) |
O5 | 0.059 (2) | 0.076 (2) | 0.052 (1) | −0.019 (1) | 0.023 (1) | −0.003 (1) |
O6 | 0.123 (3) | 0.089 (2) | 0.059 (2) | −0.023 (2) | 0.032 (2) | 0.016 (1) |
N1 | 0.045 (1) | 0.048 (1) | 0.037 (1) | 0.001 (1) | 0.010 (1) | −0.003 (1) |
N2 | 0.055 (2) | 0.046 (1) | 0.034 (1) | −0.002 (1) | 0.014 (1) | −0.004 (1) |
C1 | 0.045 (2) | 0.044 (1) | 0.039 (1) | 0.005 (1) | 0.008 (1) | −0.004 (1) |
C2 | 0.068 (2) | 0.063 (2) | 0.039 (2) | −0.005 (2) | 0.005 (1) | −0.008 (1) |
C3 | 0.062 (2) | 0.072 (2) | 0.062 (2) | −0.022 (2) | 0.008 (2) | −0.018 (2) |
C4 | 0.059 (2) | 0.075 (2) | 0.072 (2) | −0.022 (2) | 0.021 (2) | −0.012 (2) |
C5 | 0.053 (2) | 0.060 (2) | 0.050 (2) | −0.008 (2) | 0.020 (1) | −0.010 (1) |
C6 | 0.052 (2) | 0.049 (2) | 0.033 (1) | 0.005 (1) | 0.009 (1) | −0.002 (1) |
C7 | 0.086 (3) | 0.076 (2) | 0.036 (1) | −0.011 (2) | 0.015 (2) | −0.005 (2) |
C8 | 0.118 (4) | 0.105 (3) | 0.042 (2) | −0.024 (3) | 0.036 (2) | 0.000 (2) |
C9 | 0.107 (3) | 0.084 (3) | 0.052 (2) | −0.022 (2) | 0.034 (2) | −0.001 (2) |
C10 | 0.069 (2) | 0.058 (2) | 0.051 (2) | −0.007 (2) | 0.029 (2) | 0.004 (1) |
C11 | 0.051 (2) | 0.045 (1) | 0.035 (1) | −0.000 (1) | 0.014 (1) | −0.003 (1) |
C12 | 0.042 (2) | 0.042 (1) | 0.039 (1) | 0.001 (1) | 0.012 (1) | −0.002 (1) |
C13 | 0.051 (2) | 0.045 (1) | 0.055 (2) | −0.003 (1) | 0.017 (1) | −0.006 (1) |
C14 | 0.067 (2) | 0.049 (2) | 0.063 (2) | −0.010 (2) | 0.017 (2) | −0.014 (2) |
C15 | 0.095 (3) | 0.062 (2) | 0.047 (2) | −0.015 (2) | 0.022 (2) | −0.022 (2) |
C16 | 0.079 (2) | 0.057 (2) | 0.040 (2) | −0.007 (2) | 0.026 (2) | −0.010 (1) |
C17 | 0.044 (2) | 0.055 (2) | 0.037 (1) | −0.000 (1) | 0.016 (1) | −0.000 (1) |
C18 | 0.053 (2) | 0.045 (1) | 0.051 (2) | 0.004 (1) | 0.026 (1) | 0.000 (1) |
C19 | 0.083 (3) | 0.055 (2) | 0.058 (2) | 0.003 (2) | 0.030 (2) | 0.005 (2) |
C20 | 0.081 (3) | 0.059 (2) | 0.101 (3) | −0.008 (2) | 0.039 (2) | 0.009 (2) |
C21 | 0.066 (3) | 0.065 (2) | 0.102 (3) | −0.007 (2) | 0.026 (2) | −0.003 (2) |
C22 | 0.052 (2) | 0.060 (2) | 0.080 (2) | 0.004 (2) | 0.020 (2) | −0.010 (2) |
C23 | 0.058 (2) | 0.056 (2) | 0.052 (2) | 0.006 (2) | 0.026 (2) | 0.001 (1) |
C24 | 0.060 (2) | 0.050 (2) | 0.049 (2) | 0.004 (1) | 0.022 (2) | −0.003 (1) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.906 (2) | C8—H6 | 0.93 |
Cu1—O3 | 1.882 (2) | C9—C10 | 1.385 (5) |
Cu1—N1 | 1.991 (2) | C9—H7 | 0.93 |
Cu1—N2 | 2.002 (3) | C10—H8 | 0.93 |
Cu1—O3i | 2.536 (3) | C11—C12 | 1.421 (5) |
O1—C17 | 1.275 (3) | C11—C16 | 1.404 (4) |
O2—C17 | 1.263 (4) | C11—C17 | 1.476 (4) |
O3—C12 | 1.332 (3) | C12—C13 | 1.417 (4) |
O4—C24 | 1.232 (3) | C13—C14 | 1.413 (4) |
O5—C24 | 1.298 (4) | C13—H9 | 0.93 |
O5—H18 | 0.84 | C14—C15 | 1.378 (6) |
O6—C19 | 1.347 (4) | C14—H10 | 0.93 |
O6—H17 | 0.80 | C15—C16 | 1.378 (5) |
N1—C1 | 1.359 (4) | C15—H11 | 0.93 |
N1—C5 | 1.336 (4) | C16—C11 | 1.404 (4) |
N2—C6 | 1.354 (3) | C16—C15 | 1.378 (5) |
N2—C10 | 1.345 (5) | C16—H12 | 0.93 |
C1—C2 | 1.379 (4) | C18—C19 | 1.406 (5) |
C1—C6 | 1.467 (5) | C18—C23 | 1.415 (4) |
C2—C3 | 1.369 (6) | C18—C24 | 1.477 (4) |
C2—H1 | 0.93 | C19—C20 | 1.390 (5) |
C3—C4 | 1.385 (5) | C20—C21 | 1.405 (6) |
C3—H2 | 0.93 | C20—H13 | 0.93 |
C4—C5 | 1.377 (4) | C21—C22 | 1.406 (6) |
C4—H3 | 0.93 | C21—H14 | 0.93 |
C5—H4 | 0.93 | C22—C23 | 1.370 (5) |
C6—C7 | 1.386 (5) | C22—H15 | 0.93 |
C7—C8 | 1.361 (7) | C23—H16 | 0.93 |
C7—H5 | 0.93 | H12—C16 | 0.93 |
C8—C9 | 1.409 (5) | | |
| | | |
O1—Cu1—O3 | 93.27 (9) | C10—C9—C8 | 117.0 (4) |
O1—Cu1—N1 | 91.8 (1) | C10—C9—H7 | 121.5 |
O1—Cu1—N2 | 167.8 (1) | H7—C9—C8 | 121.5 |
O3—Cu1—N1 | 174.0 (1) | H8—C10—N2 | 119.0 |
O3—Cu1—N2 | 93.83 (9) | H8—C10—C9 | 119.0 |
N1—Cu1—N2 | 81.8 (1) | C12—C11—C17 | 123.0 (2) |
C17—O1—Cu1 | 129.8 (2) | C12—C11—C16 | 118.2 (3) |
C12—O3—Cu1 | 124.4 (2) | C16—C11—C17 | 118.8 (3) |
C24—O5—H18 | 120.8 | C13—C12—O3 | 116.3 (3) |
C19—O6—H17 | 107.4 | C13—C12—C11 | 119.1 (3) |
C1—N1—Cu1 | 114.3 (2) | C14—C13—C12 | 120.3 (3) |
C1—N1—C5 | 119.3 (2) | C14—C13—H9 | 119.9 |
C5—N1—Cu1 | 126.3 (2) | H9—C13—C12 | 119.8 |
C6—N2—Cu1 | 113.6 (2) | C15—C14—C13 | 119.7 (3) |
C6—N2—C10 | 119.9 (3) | C15—C14—H10 | 120.1 |
C10—N2—Cu1 | 126.2 (2) | H10—C14—C13 | 120.1 |
C2—C1—N1 | 121.3 (3) | C16—C15—C14 | 120.3 (3) |
C2—C1—C6 | 124.1 (3) | C16—C15—H11 | 119.8 |
C6—C1—N1 | 114.6 (2) | H11—C15—C14 | 119.8 |
C3—C2—C1 | 118.8 (3) | C11—C16—H12 | 118.9 |
C3—C2—H1 | 120.6 | C11—C16—C15 | 122.2 (3) |
H1—C2—C1 | 120.6 | C15—C16—H12 | 118.9 |
C4—C3—C2 | 120.1 (3) | C19—C18—C23 | 118.3 (3) |
C4—C3—H2 | 119.9 | C19—C18—C24 | 120.2 (3) |
H2—C3—C2 | 119.9 | C23—C18—C24 | 121.6 (3) |
C5—C4—C3 | 118.5 (4) | C20—C19—O6 | 117.3 (4) |
C5—C4—H3 | 120.8 | C20—C19—C18 | 120.6 (3) |
H3—C4—C3 | 120.8 | C21—C20—C19 | 119.5 (4) |
H4—C5—N1 | 119.0 | C21—C20—H13 | 120.3 |
H4—C5—C4 | 119.0 | H13—C20—C19 | 120.3 |
C7—C6—N2 | 121.2 (3) | C22—C21—C20 | 120.9 (3) |
C7—C6—C1 | 123.3 (3) | C22—C21—H14 | 119.5 |
C8—C7—C6 | 118.7 (3) | H14—C21—C20 | 119.5 |
C8—C7—H5 | 120.6 | C23—C22—H15 | 120.7 |
H5—C7—C6 | 120.7 | C23—C22—C21 | 118.5 (3) |
C9—C8—C7 | 121.2 (4) | H15—C22—C21 | 120.7 |
C9—C8—H6 | 119.4 | H16—C23—C22 | 118.9 |
H6—C8—C7 | 119.4 | H16—C23—C18 | 118.9 |
| | | |
O3—Cu1—O1—C17 | 11.9 (2) | C7—C8—C9—C10 | −0.1 (5) |
O1—Cu1—O3—C12 | −22.0 (2) | C8—C9—C10—N2 | 0.5 (5) |
O1—Cu1—N1—C1 | 172.8 (2) | C16—C11—C12—O3 | 176.2 (2) |
O1—Cu1—N2—C6 | −63.0 (4) | C12—C11—C16—C15 | −0.4 (4) |
Cu1—O1—C17—O2 | −179.3 (2) | C12—C11—C17—O1 | −9.2 (4) |
Cu1—O1—C17—C11 | 0.9 (4) | C12—C11—C17—O2 | 171.0 (3) |
Cu1—O3—C12—C11 | 20.7 (3) | O3—C12—C13—C14 | −174.9 (3) |
Cu1—N1—C1—C2 | 177.5 (2) | C12—C13—C14—C15 | −2.4 (4) |
Cu1—N1—C5—C4 | −175.8 (3) | C13—C14—C15—C16 | 0.6 (5) |
Cu1—N2—C6—C1 | 4.4 (3) | C14—C15—C16—C11 | 0.9 (5) |
Cu1—N2—C10—C9 | 172.6 (3) | C23—C18—C19—O6 | −179.8 (3) |
N1—C1—C2—C3 | −0.9 (5) | C19—C18—C23—C22 | −0.2 (4) |
N1—C1—C6—N2 | −1.8 (4) | C19—C18—C24—O4 | 0.3 (5) |
C1—C2—C3—C4 | −1.0 (5) | C19—C18—C24—O5 | −179.7 (3) |
C2—C3—C4—C5 | 2.2 (5) | O6—C19—C20—C21 | 178.8 (4) |
C3—C4—C5—N1 | −1.5 (5) | C19—C20—C21—C22 | 1.9 (6) |
N2—C6—C7—C8 | −1.6 (5) | C20—C21—C22—C23 | −1.0 (6) |
C6—C7—C8—C9 | 0.6 (6) | C21—C22—C23—C18 | 0.1 (4) |
Symmetry code: (i) −x+2, −y, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H17···O4 | 0.80 | 1.86 | 2.574 (4) | 149 |
O5—H18···O2ii | 0.84 | 1.69 | 2.514 (3) | 165 |
Symmetry code: (ii) −x+1, −y, −z+2. |
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