metal-organic compounds
The Cu atom in the title compound, [Cu(C17H14N3O)2]·2C5H5N, is chelated by the deprotonated Schiff base in a square-planar geometry; the amine group of the Schiff base forms a hydrogen bond with a pyridine solvent molecule. The Cu atom lies on a center of inversion.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037202/bt2181sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037202/bt2181Isup2.hkl |
CCDC reference: 624006
Computing details top
Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: SHELXL97.
Crystal data top
[Cu(C17H14N3O)2]·2C5H5N | F(000) = 1612 |
Mr = 774.36 | Dx = 1.338 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4184 reflections |
a = 22.552 (2) Å | θ = 2.4–23.8° |
b = 9.076 (1) Å | µ = 0.62 mm−1 |
c = 19.107 (2) Å | T = 293 K |
β = 100.503 (1)° | Fragment, brown |
V = 3845.5 (5) Å3 | 0.36 × 0.23 × 0.17 mm |
Z = 4 |
Data collection top
Bruker APEX-II area-detector diffractometer | 3943 independent reflections |
Radiation source: fine-focus sealed tube | 3103 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −28→28 |
Tmin = 0.783, Tmax = 0.902 | k = −11→11 |
16507 measured reflections | l = −23→23 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0541P)2 + 1.8992P] where P = (Fo2 + 2Fc2)/3 |
3943 reflections | (Δ/σ)max = 0.001 |
255 parameters | Δρmax = 0.21 e Å−3 |
1 restraint | Δρmin = −0.25 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.2500 | 0.7500 | 0.5000 | 0.0434 (1) | |
O1 | 0.3092 (1) | 0.8700 (2) | 0.5580 (1) | 0.0493 (4) | |
N1 | 0.2275 (1) | 0.9414 (2) | 0.6078 (1) | 0.0445 (4) | |
N2 | 0.1973 (1) | 0.8448 (2) | 0.5564 (1) | 0.0427 (4) | |
N3 | 0.0015 (1) | 0.9523 (2) | 0.5997 (1) | 0.0508 (4) | |
N4 | −0.1254 (1) | 0.9620 (3) | 0.6111 (1) | 0.0696 (6) | |
C1 | 0.3258 (1) | 1.0368 (2) | 0.6554 (1) | 0.0431 (5) | |
C2 | 0.3865 (1) | 1.0467 (2) | 0.6511 (1) | 0.0497 (5) | |
C3 | 0.4244 (1) | 1.1372 (3) | 0.6971 (1) | 0.0602 (6) | |
C4 | 0.4028 (1) | 1.2182 (3) | 0.7478 (1) | 0.0598 (6) | |
C5 | 0.3427 (1) | 1.2088 (3) | 0.7530 (1) | 0.0625 (6) | |
C6 | 0.3045 (1) | 1.1189 (3) | 0.7070 (1) | 0.0569 (6) | |
C7 | 0.2851 (1) | 0.9432 (2) | 0.6039 (1) | 0.0426 (5) | |
C8 | 0.1390 (1) | 0.8354 (2) | 0.5468 (1) | 0.0410 (4) | |
C9 | 0.0941 (1) | 0.9144 (2) | 0.5764 (1) | 0.0387 (4) | |
C10 | 0.0360 (1) | 0.8574 (2) | 0.5700 (1) | 0.0422 (4) | |
C11 | 0.0106 (1) | 0.7152 (3) | 0.5393 (1) | 0.0585 (6) | |
C12 | 0.0345 (1) | 1.0751 (2) | 0.6243 (1) | 0.0494 (5) | |
C13 | 0.0159 (1) | 1.2013 (3) | 0.6555 (1) | 0.0674 (7) | |
C14 | 0.0569 (1) | 1.3105 (3) | 0.6737 (2) | 0.0792 (8) | |
C15 | 0.1156 (1) | 1.2972 (3) | 0.6609 (2) | 0.0771 (8) | |
C16 | 0.1339 (1) | 1.1724 (3) | 0.6294 (1) | 0.0602 (6) | |
C17 | 0.0937 (1) | 1.0568 (2) | 0.6111 (1) | 0.0442 (5) | |
C18 | −0.1694 (1) | 0.8940 (3) | 0.5690 (2) | 0.079 (1) | |
C19 | −0.2299 (1) | 0.9151 (4) | 0.5733 (2) | 0.101 (1) | |
C20 | −0.2438 (2) | 1.0103 (5) | 0.6227 (3) | 0.115 (2) | |
C21 | −0.1992 (2) | 1.0812 (4) | 0.6653 (2) | 0.112 (1) | |
C22 | −0.1408 (1) | 1.0528 (4) | 0.6591 (2) | 0.089 (1) | |
H3n | −0.036 (1) | 0.942 (3) | 0.602 (1) | 0.077 (8)* | |
H2 | 0.4017 | 0.9921 | 0.6171 | 0.060* | |
H3 | 0.4649 | 1.1435 | 0.6937 | 0.072* | |
H4 | 0.4287 | 1.2792 | 0.7785 | 0.072* | |
H5 | 0.3279 | 1.2628 | 0.7874 | 0.075* | |
H6 | 0.2640 | 1.1131 | 0.7105 | 0.068* | |
H8 | 0.1230 | 0.7632 | 0.5142 | 0.049* | |
H11a | 0.0261 | 0.6940 | 0.4968 | 0.088* | |
H11b | −0.0326 | 0.7223 | 0.5279 | 0.088* | |
H11c | 0.0218 | 0.6377 | 0.5733 | 0.088* | |
H13 | −0.0234 | 1.2105 | 0.6636 | 0.081* | |
H14 | 0.0457 | 1.3956 | 0.6951 | 0.095* | |
H15 | 0.1429 | 1.3736 | 0.6738 | 0.093* | |
H16 | 0.1730 | 1.1658 | 0.6204 | 0.072* | |
H18 | −0.1600 | 0.8291 | 0.5350 | 0.094* | |
H19 | −0.2601 | 0.8650 | 0.5429 | 0.121* | |
H20 | −0.2838 | 1.0260 | 0.6268 | 0.138* | |
H21 | −0.2078 | 1.1487 | 0.6987 | 0.134* | |
H22 | −0.1102 | 1.0998 | 0.6904 | 0.106* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0317 (2) | 0.0519 (2) | 0.0490 (2) | −0.0007 (2) | 0.0136 (1) | −0.0123 (2) |
O1 | 0.034 (1) | 0.061 (1) | 0.056 (1) | −0.003 (1) | 0.015 (1) | −0.018 (1) |
N1 | 0.033 (1) | 0.055 (1) | 0.046 (1) | 0.000 (1) | 0.010 (1) | −0.012 (1) |
N2 | 0.033 (1) | 0.051 (1) | 0.045 (1) | −0.001 (1) | 0.011 (1) | −0.009 (1) |
N3 | 0.033 (1) | 0.065 (1) | 0.057 (1) | 0.004 (1) | 0.016 (1) | −0.001 (1) |
N4 | 0.050 (1) | 0.085 (2) | 0.079 (2) | 0.013 (1) | 0.025 (1) | 0.015 (1) |
C1 | 0.039 (1) | 0.049 (1) | 0.041 (1) | 0.001 (1) | 0.005 (1) | −0.002 (1) |
C2 | 0.037 (1) | 0.061 (1) | 0.051 (1) | 0.002 (1) | 0.005 (1) | −0.008 (1) |
C3 | 0.041 (1) | 0.078 (2) | 0.058 (1) | −0.006 (1) | 0.000 (1) | −0.005 (1) |
C4 | 0.056 (1) | 0.068 (2) | 0.050 (1) | −0.009 (1) | −0.005 (1) | −0.009 (1) |
C5 | 0.065 (2) | 0.074 (2) | 0.048 (1) | 0.000 (1) | 0.008 (1) | −0.018 (1) |
C6 | 0.046 (1) | 0.076 (2) | 0.049 (1) | −0.003 (1) | 0.012 (1) | −0.016 (1) |
C7 | 0.036 (1) | 0.049 (1) | 0.044 (1) | 0.001 (1) | 0.010 (1) | −0.004 (1) |
C8 | 0.035 (1) | 0.047 (1) | 0.043 (1) | −0.002 (1) | 0.011 (1) | −0.004 (1) |
C9 | 0.033 (1) | 0.047 (1) | 0.038 (1) | 0.001 (1) | 0.009 (1) | 0.000 (1) |
C10 | 0.035 (1) | 0.052 (1) | 0.041 (1) | 0.004 (1) | 0.009 (1) | 0.001 (1) |
C11 | 0.041 (1) | 0.071 (2) | 0.064 (2) | −0.009 (1) | 0.012 (1) | −0.009 (1) |
C12 | 0.044 (1) | 0.056 (1) | 0.052 (1) | 0.006 (1) | 0.018 (1) | −0.001 (1) |
C13 | 0.061 (2) | 0.065 (2) | 0.083 (2) | 0.010 (1) | 0.034 (1) | −0.011 (1) |
C14 | 0.092 (2) | 0.061 (2) | 0.094 (2) | 0.009 (2) | 0.041 (2) | −0.021 (2) |
C15 | 0.078 (2) | 0.059 (2) | 0.101 (2) | −0.012 (1) | 0.032 (2) | −0.025 (2) |
C16 | 0.053 (1) | 0.057 (1) | 0.074 (2) | −0.003 (1) | 0.022 (1) | −0.011 (1) |
C17 | 0.040 (1) | 0.050 (1) | 0.045 (1) | 0.003 (1) | 0.013 (1) | −0.002 (1) |
C18 | 0.069 (2) | 0.084 (2) | 0.086 (2) | 0.004 (2) | 0.022 (2) | 0.0186 (2) |
C19 | 0.060 (2) | 0.108 (3) | 0.131 (3) | −0.009 (2) | 0.007 (2) | 0.047 (2) |
C20 | 0.070 (2) | 0.097 (3) | 0.196 (4) | 0.025 (2) | 0.074 (3) | 0.064 (3) |
C21 | 0.108 (3) | 0.091 (2) | 0.163 (4) | 0.014 (2) | 0.096 (3) | 0.024 (2) |
C22 | 0.078 (2) | 0.099 (2) | 0.099 (2) | −0.002 (2) | 0.043 (2) | 0.007 (2) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.913 (1) | C14—C15 | 1.395 (4) |
Cu1—O1i | 1.913 (1) | C15—C16 | 1.380 (3) |
Cu1—N2 | 1.944 (2) | C16—C17 | 1.390 (3) |
Cu1—N2i | 1.944 (2) | C18—C19 | 1.393 (4) |
O1—C7 | 1.296 (2) | C19—C20 | 1.358 (5) |
N1—C7 | 1.316 (2) | C20—C21 | 1.338 (6) |
N1—N2 | 1.398 (2) | C21—C22 | 1.368 (4) |
N2—C8 | 1.298 (2) | N3—H3n | 0.85 (1) |
N3—C10 | 1.354 (3) | C2—H2 | 0.93 |
N3—C12 | 1.375 (3) | C3—H3 | 0.93 |
N4—C18 | 1.313 (4) | C4—H4 | 0.93 |
N4—C22 | 1.327 (4) | C5—H5 | 0.93 |
C1—C6 | 1.389 (3) | C6—H6 | 0.93 |
C1—C2 | 1.390 (3) | C8—H8 | 0.93 |
C1—C7 | 1.483 (3) | C11—H11a | 0.96 |
C2—C3 | 1.379 (3) | C11—H11b | 0.96 |
C3—C4 | 1.374 (3) | C11—H11c | 0.96 |
C4—C5 | 1.381 (4) | C13—H13 | 0.93 |
C5—C6 | 1.380 (3) | C14—H14 | 0.93 |
C8—C9 | 1.438 (2) | C15—H15 | 0.93 |
C9—C10 | 1.393 (3) | C16—H16 | 0.93 |
C9—C17 | 1.453 (3) | C18—H18 | 0.93 |
C10—C11 | 1.488 (3) | C19—H19 | 0.93 |
C12—C13 | 1.390 (3) | C20—H20 | 0.93 |
C12—C17 | 1.412 (3) | C21—H21 | 0.93 |
C13—C14 | 1.357 (4) | C22—H22 | 0.93 |
O1—Cu1—O1i | 180 | C20—C19—C18 | 118.8 (4) |
O1—Cu1—N2 | 81.96 (6) | C21—C20—C19 | 119.0 (3) |
O1—Cu1—N2i | 98.04 (6) | C20—C21—C22 | 119.1 (4) |
O1i—Cu1—N2 | 98.04 (6) | N4—C22—C21 | 123.7 (4) |
O1i—Cu1—N2i | 81.96 (6) | C10—N3—H3n | 127 (2) |
N2—Cu1—N2i | 180 | C12—N3—H3n | 123 (2) |
C7—O1—Cu1 | 110.4 (1) | C3—C2—H2 | 119.9 |
C7—N1—N2 | 109.1 (2) | C1—C2—H2 | 119.9 |
C8—N2—N1 | 119.5 (2) | C4—C3—H3 | 119.7 |
C8—N2—Cu1 | 126.8 (1) | C2—C3—H3 | 119.7 |
N1—N2—Cu1 | 113.5 (1) | C3—C4—H4 | 120.1 |
C10—N3—C12 | 110.0 (2) | C5—C4—H4 | 120.1 |
C18—N4—C22 | 116.8 (2) | C6—C5—H5 | 120.1 |
C6—C1—C2 | 118.55 (19) | C4—C5—H5 | 120.1 |
C6—C1—C7 | 121.78 (18) | C5—C6—H6 | 119.5 |
C2—C1—C7 | 119.65 (18) | C1—C6—H6 | 119.5 |
C3—C2—C1 | 120.3 (2) | N2—C8—H8 | 113.6 |
C4—C3—C2 | 120.6 (2) | C9—C8—H8 | 113.6 |
C3—C4—C5 | 119.8 (2) | C10—C11—H11a | 109.5 |
C6—C5—C4 | 119.8 (2) | C10—C11—H11b | 109.5 |
C5—C6—C1 | 120.9 (2) | H11a—C11—H11b | 109.5 |
O1—C7—N1 | 124.9 (2) | C10—C11—H11c | 109.5 |
O1—C7—C1 | 117.2 (2) | H11a—C11—H11c | 109.5 |
N1—C7—C1 | 117.8 (2) | H11b—C11—H11c | 109.5 |
N2—C8—C9 | 132.9 (2) | C14—C13—H13 | 121.1 |
C10—C9—C8 | 119.9 (2) | C12—C13—H13 | 121.1 |
C10—C9—C17 | 106.7 (2) | C13—C14—H14 | 119.5 |
C8—C9—C17 | 133.3 (2) | C15—C14—H14 | 119.5 |
N3—C10—C9 | 109.3 (2) | C16—C15—H15 | 119.4 |
N3—C10—C11 | 120.5 (2) | C14—C15—H15 | 119.4 |
C9—C10—C11 | 130.2 (2) | C15—C16—H16 | 120.2 |
N3—C12—C13 | 128.8 (2) | C17—C16—H16 | 120.2 |
N3—C12—C17 | 108.3 (2) | N4—C18—H18 | 118.7 |
C13—C12—C17 | 122.8 (2) | C19—C18—H18 | 118.7 |
C14—C13—C12 | 117.9 (2) | C20—C19—H19 | 120.6 |
C13—C14—C15 | 121.0 (2) | C18—C19—H19 | 120.6 |
C16—C15—C14 | 121.1 (3) | C21—C20—H20 | 120.5 |
C15—C16—C17 | 119.7 (2) | C19—C20—H20 | 120.5 |
C16—C17—C12 | 117.5 (2) | C20—C21—H21 | 120.5 |
C16—C17—C9 | 136.7 (2) | C22—C21—H21 | 120.5 |
C12—C17—C9 | 105.7 (2) | N4—C22—H22 | 118.1 |
N4—C18—C19 | 122.6 (3) | C21—C22—H22 | 118.1 |
C7—O1—Cu1—N2i | −177.6 (1) | C12—N3—C10—C11 | 180.0 (2) |
C7—O1—Cu1—N2 | 2.4 (1) | C8—C9—C10—N3 | −178.1 (2) |
C7—N1—N2—C8 | −174.2 (2) | C17—C9—C10—N3 | −1.7 (2) |
C7—N1—N2—Cu1 | 0.4 (2) | C8—C9—C10—C11 | 4.1 (3) |
O1—Cu1—N2—C8 | 172.5 (2) | C17—C9—C10—C11 | −179.5 (2) |
O1i—Cu1—N2—C8 | −7.5 (2) | C10—N3—C12—C13 | 177.0 (2) |
O1—Cu1—N2—N1 | −1.6 (1) | C10—N3—C12—C17 | −1.3 (2) |
O1i—Cu1—N2—N1 | 178.4 (1) | N3—C12—C13—C14 | −178.1 (3) |
C6—C1—C2—C3 | −0.4 (3) | C17—C12—C13—C14 | −0.1 (4) |
C7—C1—C2—C3 | 177.8 (2) | C12—C13—C14—C15 | 0.7 (5) |
C1—C2—C3—C4 | 0.3 (4) | C13—C14—C15—C16 | −0.1 (5) |
C2—C3—C4—C5 | 0.1 (4) | C14—C15—C16—C17 | −1.1 (5) |
C3—C4—C5—C6 | −0.4 (4) | C15—C16—C17—C12 | 1.6 (4) |
C4—C5—C6—C1 | 0.3 (4) | C15—C16—C17—C9 | 177.6 (3) |
C2—C1—C6—C5 | 0.2 (4) | N3—C12—C17—C16 | 177.3 (2) |
C7—C1—C6—C5 | −178.0 (2) | C13—C12—C17—C16 | −1.1 (3) |
Cu1—O1—C7—N1 | −3.2 (3) | N3—C12—C17—C9 | 0.2 (2) |
Cu1—O1—C7—C1 | 177.2 (1) | C13—C12—C17—C9 | −178.2 (2) |
N2—N1—C7—O1 | 1.9 (3) | C10—C9—C17—C16 | −175.4 (3) |
N2—N1—C7—C1 | −178.6 (2) | C8—C9—C17—C16 | 0.3 (4) |
C6—C1—C7—O1 | −179.6 (2) | C10—C9—C17—C12 | 0.9 (2) |
C2—C1—C7—O1 | 2.3 (3) | C8—C9—C17—C12 | 176.6 (2) |
C6—C1—C7—N1 | 0.8 (3) | C22—N4—C18—C19 | 0.4 (4) |
C2—C1—C7—N1 | −177.3 (2) | N4—C18—C19—C20 | 0.3 (5) |
N1—N2—C8—C9 | 4.7 (3) | C18—C19—C20—C21 | 0.3 (5) |
Cu1—N2—C8—C9 | −169.2 (2) | C19—C20—C21—C22 | −1.7 (5) |
N2—C8—C9—C10 | −163.9 (2) | C18—N4—C22—C21 | −1.9 (5) |
N2—C8—C9—C17 | 20.8 (4) | C20—C21—C22—N4 | 2.6 (5) |
C12—N3—C10—C9 | 1.9 (2) |
Symmetry code: (i) −x+1/2, −y+3/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3n···N4 | 0.85 (1) | 2.07 (1) | 2.910 (3) | 169 (3) |