metal-organic compounds
In the title compound, [Cu(C17H11NO2)(C5H5N)(H2O)], the anionic naphthalen-2-olate group chelates to the Cu atom through its O, O' and N atoms, and the N atom of the heterocycle completes the square-planar coordination of the Cu atom. The apical site of the square-pyramidal environment is occupied by the water ligand. Adjacent molecules are linked by hydrogen bonds into a linear chain running along the b axis of the monoclinic unit cell.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302631X/na6270sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680302631X/na6270Isup2.hkl |
CCDC reference: 227763
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Aqua{1-[(2-oxidophenyl)iminomethyl]naphthalen-2-olato}pyridinecopper(II) top
Crystal data top
[Cu(C17H11NO2)(C5H5N)(H2O)] | F(000) = 868 |
Mr = 421.92 | Dx = 1.535 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 16.947 (1) Å | Cell parameters from 2530 reflections |
b = 5.5645 (4) Å | θ = 2.4–24.1° |
c = 19.462 (2) Å | µ = 1.22 mm−1 |
β = 95.803 (1)° | T = 298 K |
V = 1825.9 (2) Å3 | Plate, green |
Z = 4 | 0.24 × 0.17 × 0.03 mm |
Data collection top
Bruker APEX area-detector diffractometer | 4087 independent reflections |
Radiation source: fine-focus sealed tube | 2683 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scan | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −17→21 |
Tmin = 0.651, Tmax = 0.888 | k = −6→7 |
10709 measured reflections | l = −25→25 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0671P)2] where P = (Fo2 + 2Fc2)/3 |
4087 reflections | (Δ/σ)max = 0.001 |
273 parameters | Δρmax = 0.43 e Å−3 |
21 restraints | Δρmin = −0.43 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu1 | 0.58284 (2) | 0.51153 (6) | 0.71574 (2) | 0.0361 (1) | |
O1 | 0.5184 (1) | 0.7577 (4) | 0.6699 (1) | 0.0440 (5) | |
O2 | 0.6387 (1) | 0.2489 (4) | 0.7664 (1) | 0.0398 (5) | |
O1w | 0.6929 (2) | 0.7807 (4) | 0.7328 (2) | 0.0543 (6) | |
N1 | 0.5462 (1) | 0.5926 (5) | 0.8042 (1) | 0.0348 (6) | |
N2 | 0.6133 (1) | 0.3985 (5) | 0.6229 (1) | 0.0405 (6) | |
C1 | 0.4743 (2) | 0.9171 (6) | 0.6973 (2) | 0.0379 (7) | |
C2 | 0.4385 (2) | 1.0959 (6) | 0.6512 (2) | 0.0453 (8) | |
C3 | 0.3912 (2) | 1.2689 (6) | 0.6733 (2) | 0.0493 (8) | |
C4 | 0.3738 (2) | 1.2831 (5) | 0.7429 (2) | 0.0395 (7) | |
C5 | 0.3231 (2) | 1.4631 (6) | 0.7645 (2) | 0.0496 (9) | |
C6 | 0.3071 (2) | 1.4786 (6) | 0.8309 (2) | 0.0566 (9) | |
C7 | 0.3407 (2) | 1.3134 (7) | 0.8781 (2) | 0.060 (1) | |
C8 | 0.3903 (2) | 1.1352 (7) | 0.8586 (2) | 0.0533 (9) | |
C9 | 0.4088 (2) | 1.1129 (6) | 0.7902 (2) | 0.0376 (7) | |
C10 | 0.4610 (2) | 0.9285 (5) | 0.7673 (2) | 0.0358 (7) | |
C11 | 0.4976 (2) | 0.7638 (6) | 0.8162 (2) | 0.0385 (7) | |
C12 | 0.5799 (2) | 0.4385 (5) | 0.8571 (2) | 0.0374 (7) | |
C13 | 0.5701 (2) | 0.4555 (6) | 0.9271 (2) | 0.0519 (9) | |
C14 | 0.6050 (2) | 0.2877 (7) | 0.9730 (2) | 0.060 (1) | |
C15 | 0.6493 (2) | 0.1049 (7) | 0.9492 (2) | 0.0564 (9) | |
C16 | 0.6612 (2) | 0.0880 (6) | 0.8807 (2) | 0.0495 (8) | |
C17 | 0.6276 (2) | 0.2565 (5) | 0.8333 (2) | 0.0369 (7) | |
C18 | 0.6741 (3) | 0.240 (1) | 0.6165 (3) | 0.052 (2) | 0.50 |
C19 | 0.6972 (4) | 0.161 (1) | 0.5538 (3) | 0.063 (2) | 0.50 |
C20 | 0.6563 (2) | 0.2585 (7) | 0.4951 (2) | 0.071 (1) | |
C21 | 0.5868 (4) | 0.389 (2) | 0.4967 (3) | 0.062 (2) | 0.50 |
C22 | 0.5704 (4) | 0.467 (1) | 0.5614 (2) | 0.051 (1) | 0.50 |
C18' | 0.6365 (5) | 0.1677 (8) | 0.6124 (3) | 0.052 (2) | 0.50 |
C19' | 0.6628 (5) | 0.102 (1) | 0.5500 (3) | 0.063 (2) | 0.50 |
C21' | 0.6428 (4) | 0.5054 (9) | 0.5096 (3) | 0.062 (2) | 0.50 |
C22' | 0.6207 (4) | 0.5727 (9) | 0.5739 (3) | 0.051 (1) | 0.50 |
H1w1 | 0.674 (2) | 0.913 (4) | 0.744 (2) | 0.10 (2)* | |
H1w2 | 0.742 (1) | 0.792 (6) | 0.731 (2) | 0.08 (1)* | |
H2 | 0.4480 | 1.0928 | 0.6049 | 0.054* | |
H3 | 0.3693 | 1.3823 | 0.6418 | 0.059* | |
H5 | 0.3003 | 1.5730 | 0.7324 | 0.060* | |
H6 | 0.2740 | 1.5988 | 0.8446 | 0.068* | |
H7 | 0.3295 | 1.3225 | 0.9238 | 0.072* | |
H8 | 0.4120 | 1.0268 | 0.8917 | 0.064* | |
H11 | 0.4855 | 0.7804 | 0.8615 | 0.046* | |
H13 | 0.5401 | 0.5798 | 0.9431 | 0.062* | |
H14 | 0.5985 | 0.2987 | 1.0197 | 0.072* | |
H15 | 0.6716 | −0.0097 | 0.9801 | 0.068* | |
H16 | 0.6919 | −0.0363 | 0.8657 | 0.059* | |
H18 | 0.7017 | 0.1820 | 0.6568 | 0.062* | 0.50 |
H19 | 0.7377 | 0.0491 | 0.5514 | 0.076* | 0.50 |
H20 | 0.6764 | 0.2357 | 0.4529 | 0.085* | |
H21 | 0.5534 | 0.4212 | 0.4569 | 0.074* | 0.50 |
H22 | 0.5281 | 0.5720 | 0.5638 | 0.061* | 0.50 |
H18' | 0.6348 | 0.0543 | 0.6473 | 0.062* | 0.50 |
H19' | 0.6849 | −0.0493 | 0.5452 | 0.076* | 0.50 |
H21' | 0.6486 | 0.6215 | 0.4761 | 0.074* | 0.50 |
H22' | 0.6111 | 0.7331 | 0.5835 | 0.061* | 0.50 |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0391 (2) | 0.0379 (2) | 0.0319 (2) | 0.0026 (2) | 0.0069 (1) | 0.0011 (2) |
O1 | 0.048 (1) | 0.049 (1) | 0.036 (1) | 0.011 (1) | 0.007 (1) | 0.005 (1) |
O2 | 0.048 (1) | 0.038 (1) | 0.035 (1) | 0.009 (1) | 0.009 (1) | 0.001 (1) |
O1w | 0.045 (2) | 0.041 (2) | 0.080 (2) | −0.005 (1) | 0.017 (1) | −0.013 (1) |
N1 | 0.033 (1) | 0.039 (1) | 0.033 (1) | 0.004 (1) | 0.005 (1) | 0.003 (1) |
N2 | 0.042 (2) | 0.044 (2) | 0.036 (1) | −0.005 (1) | 0.006 (1) | 0.000 (1) |
C1 | 0.033 (2) | 0.038 (2) | 0.042 (2) | −0.004 (1) | 0.003 (1) | 0.004 (1) |
C2 | 0.046 (2) | 0.050 (2) | 0.039 (2) | 0.002 (2) | 0.001 (2) | 0.008 (2) |
C3 | 0.046 (2) | 0.049 (2) | 0.052 (2) | 0.003 (2) | −0.002 (2) | 0.016 (2) |
C4 | 0.031 (2) | 0.036 (2) | 0.051 (2) | −0.002 (1) | 0.001 (1) | 0.005 (1) |
C5 | 0.043 (2) | 0.037 (2) | 0.067 (2) | 0.007 (2) | 0.000 (2) | 0.009 (2) |
C6 | 0.053 (2) | 0.047 (2) | 0.071 (3) | 0.013 (2) | 0.009 (2) | −0.001 (2) |
C7 | 0.068 (3) | 0.060 (2) | 0.055 (2) | 0.020 (2) | 0.017 (2) | 0.000 (2) |
C8 | 0.061 (2) | 0.052 (2) | 0.048 (2) | 0.016 (2) | 0.012 (2) | 0.006 (2) |
C9 | 0.033 (2) | 0.034 (2) | 0.047 (2) | −0.003 (1) | 0.004 (1) | 0.002 (1) |
C10 | 0.030 (2) | 0.038 (2) | 0.040 (2) | −0.001 (1) | 0.004 (1) | 0.005 (1) |
C11 | 0.039 (2) | 0.044 (2) | 0.034 (2) | 0.003 (1) | 0.008 (1) | 0.001 (1) |
C12 | 0.038 (2) | 0.040 (2) | 0.035 (2) | 0.003 (1) | 0.007 (1) | 0.004 (1) |
C13 | 0.058 (2) | 0.059 (2) | 0.041 (2) | 0.022 (2) | 0.015 (2) | 0.008 (2) |
C14 | 0.072 (3) | 0.074 (3) | 0.035 (2) | 0.021 (2) | 0.012 (2) | 0.012 (2) |
C15 | 0.067 (2) | 0.058 (2) | 0.044 (2) | 0.018 (2) | 0.005 (2) | 0.015 (2) |
C16 | 0.058 (2) | 0.045 (2) | 0.047 (2) | 0.016 (2) | 0.010 (2) | 0.006 (2) |
C17 | 0.036 (2) | 0.037 (2) | 0.038 (2) | −0.002 (1) | 0.006 (1) | 0.003 (1) |
C18 | 0.073 (5) | 0.039 (3) | 0.046 (2) | −0.005 (3) | 0.018 (3) | −0.002 (2) |
C19 | 0.081 (6) | 0.040 (4) | 0.074 (3) | −0.011 (4) | 0.035 (4) | −0.012 (3) |
C20 | 0.079 (3) | 0.092 (3) | 0.043 (2) | 0.000 (2) | 0.017 (2) | −0.014 (2) |
C21 | 0.059 (3) | 0.093 (5) | 0.035 (2) | 0.009 (3) | 0.009 (3) | 0.001 (3) |
C22 | 0.057 (3) | 0.055 (4) | 0.040 (3) | 0.004 (2) | 0.008 (3) | 0.002 (2) |
C18' | 0.073 (5) | 0.039 (3) | 0.046 (2) | −0.005 (3) | 0.018 (3) | −0.002 (2) |
C19' | 0.081 (6) | 0.040 (4) | 0.074 (3) | −0.011 (4) | 0.035 (4) | −0.012 (3) |
C21' | 0.059 (3) | 0.093 (5) | 0.035 (2) | 0.009 (3) | 0.009 (3) | 0.001 (3) |
C22' | 0.057 (3) | 0.055 (4) | 0.040 (3) | 0.004 (2) | 0.008 (3) | 0.002 (2) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.915 (2) | C18—C19 | 1.392 (4) |
Cu1—O2 | 1.953 (2) | C19—C20 | 1.385 (4) |
Cu1—O1w | 2.389 (2) | C20—C21 | 1.385 (4) |
Cu1—N1 | 1.941 (2) | C21—C22 | 1.388 (4) |
Cu1—N2 | 2.030 (2) | C18'—C19' | 1.384 (4) |
O1—C1 | 1.308 (4) | C21'—C22' | 1.393 (4) |
O2—C17 | 1.335 (3) | O1w—H1w1 | 0.84 (1) |
N1—C11 | 1.296 (4) | O1w—H1w2 | 0.84 (1) |
N1—C12 | 1.415 (4) | C2—H2 | 0.93 |
N2—C18 | 1.370 (4) | C3—H3 | 0.93 |
N2—C22 | 1.389 (4) | C5—H5 | 0.93 |
C1—C10 | 1.404 (4) | C6—H6 | 0.93 |
C1—C2 | 1.434 (4) | C7—H7 | 0.93 |
C2—C3 | 1.351 (5) | C8—H8 | 0.93 |
C3—C4 | 1.418 (4) | C11—H11 | 0.93 |
C4—C9 | 1.409 (4) | C13—H13 | 0.93 |
C4—C5 | 1.412 (4) | C14—H14 | 0.93 |
C5—C6 | 1.348 (5) | C15—H15 | 0.93 |
C6—C7 | 1.381 (5) | C16—H16 | 0.93 |
C7—C8 | 1.378 (5) | C18—H18 | 0.93 |
C8—C9 | 1.405 (4) | C19—H19 | 0.93 |
C9—C10 | 1.453 (4) | C20—H20 | 0.93 |
C10—C11 | 1.418 (4) | C21—H21 | 0.93 |
C12—C13 | 1.392 (4) | C22—H22 | 0.93 |
C12—C17 | 1.404 (4) | C18'—H18' | 0.93 |
C13—C14 | 1.382 (4) | C19'—H19' | 0.93 |
C15—C16 | 1.373 (4) | C21'—H21' | 0.93 |
C16—C17 | 1.396 (4) | C22'—H22' | 0.93 |
O1—Cu1—O2 | 174.1 (1) | O2—C17—C12 | 119.2 (3) |
O1—Cu1—O1w | 91.0 (1) | C16—C17—C12 | 118.5 (3) |
O1—Cu1—N2 | 89.5 (1) | N2—C18—C19 | 124.3 (5) |
O1—Cu1—N1 | 91.7 (1) | C20—C19—C18 | 115.9 (5) |
O2—Cu1—N1 | 84.7 (1) | C21—C20—C19 | 122.8 (4) |
O2—Cu1—N2 | 93.6 (1) | C21—C22—N2 | 124.0 (5) |
O2—Cu1—O1w | 93.9 (1) | Cu1—O1w—H1w1 | 105 (2) |
O1w—Cu1—N1 | 92.7 (1) | Cu1—O1w—H1w2 | 144 (2) |
O1w—Cu1—N2 | 93.0 (1) | H1w1—O1w—H1w2 | 111 (2) |
N1—Cu1—N2 | 174.2 (1) | C3—C2—H2 | 119.3 |
C1—O1—Cu1 | 128.1 (2) | C1—C2—H2 | 119.3 |
C17—O2—Cu1 | 111.1 (2) | C2—C3—H3 | 118.9 |
C11—N1—C12 | 122.1 (3) | C4—C3—H3 | 118.9 |
C11—N1—Cu1 | 126.6 (2) | C6—C5—H5 | 119.4 |
C12—N1—Cu1 | 111.3 (2) | C4—C5—H5 | 119.4 |
C18—N2—C22 | 115.6 (4) | C5—C6—H6 | 120.5 |
C18—N2—Cu1 | 122.7 (3) | C7—C6—H6 | 120.5 |
C22—N2—Cu1 | 121.5 (3) | C8—C7—H7 | 119.4 |
O1—C1—C10 | 125.5 (3) | C6—C7—H7 | 119.4 |
O1—C1—C2 | 116.0 (3) | C7—C8—H8 | 119.2 |
C10—C1—C2 | 118.5 (3) | C9—C8—H8 | 119.2 |
C3—C2—C1 | 121.5 (3) | N1—C11—H11 | 116.7 |
C2—C3—C4 | 122.1 (3) | C10—C11—H11 | 116.7 |
C9—C4—C5 | 120.8 (3) | C14—C13—H13 | 120.0 |
C9—C4—C3 | 118.2 (3) | C12—C13—H13 | 120.0 |
C5—C4—C3 | 121.0 (3) | C15—C14—H14 | 120.1 |
C6—C5—C4 | 121.2 (3) | C13—C14—H14 | 120.1 |
C5—C6—C7 | 119.0 (3) | C14—C15—H15 | 119.4 |
C8—C7—C6 | 121.2 (3) | C16—C15—H15 | 119.4 |
C7—C8—C9 | 121.7 (3) | C15—C16—H16 | 119.8 |
C8—C9—C4 | 116.1 (3) | C17—C16—H16 | 119.8 |
C8—C9—C10 | 123.7 (3) | N2—C18—H18 | 117.8 |
C4—C9—C10 | 120.2 (3) | C19—C18—H18 | 117.8 |
C1—C10—C11 | 121.3 (3) | C20—C19—H19 | 122.1 |
C1—C10—C9 | 119.4 (3) | C18—C19—H19 | 122.1 |
C11—C10—C9 | 119.3 (3) | C21—C20—H20 | 118.6 |
N1—C11—C10 | 126.7 (3) | C19—C20—H20 | 118.6 |
C13—C12—C17 | 120.1 (3) | C20—C21—H21 | 122.1 |
C13—C12—N1 | 126.3 (3) | C22—C21—H21 | 122.1 |
C17—C12—N1 | 113.5 (3) | C21—C22—H22 | 118.0 |
C14—C13—C12 | 120.0 (3) | N2—C22—H22 | 118.0 |
C15—C14—C13 | 119.8 (3) | C19'—C18'—H18' | 119.9 |
C14—C15—C16 | 121.2 (3) | C18'—C19'—H19' | 119.8 |
C15—C16—C17 | 120.4 (3) | C22'—C21'—H21' | 120.0 |
O2—C17—C16 | 122.3 (3) | C21'—C22'—H22' | 120.5 |
N1—Cu1—O1—C1 | 4.3 (3) | C2—C1—C10—C11 | −177.0 (3) |
N2—Cu1—O1—C1 | 178.6 (3) | O1—C1—C10—C9 | −178.5 (3) |
O1w—Cu1—O1—C1 | −88.4 (3) | C2—C1—C10—C9 | 2.8 (4) |
N1—Cu1—O2—C17 | −2.0 (2) | C8—C9—C10—C1 | 178.3 (3) |
N2—Cu1—O2—C17 | −176.4 (2) | C4—C9—C10—C1 | −1.9 (4) |
O1w—Cu1—O2—C17 | 90.4 (2) | C8—C9—C10—C11 | −1.8 (5) |
O1—Cu1—N1—C11 | −1.9 (3) | C4—C9—C10—C11 | 178.0 (3) |
O2—Cu1—N1—C11 | −177.2 (3) | C12—N1—C11—C10 | 179.7 (3) |
O1w—Cu1—N1—C11 | 89.1 (3) | Cu1—N1—C11—C10 | −0.1 (5) |
O1—Cu1—N1—C12 | 178.3 (2) | C1—C10—C11—N1 | 0.9 (5) |
O2—Cu1—N1—C12 | 3.0 (2) | C9—C10—C11—N1 | −178.9 (3) |
O1w—Cu1—N1—C12 | −90.7 (2) | C11—N1—C12—C13 | −3.9 (5) |
O1—Cu1—N2—C18 | 167.4 (4) | Cu1—N1—C12—C13 | 175.9 (3) |
O2—Cu1—N2—C18 | −17.6 (4) | C11—N1—C12—C17 | 176.7 (3) |
O1w—Cu1—N2—C18 | 76.5 (4) | Cu1—N1—C12—C17 | −3.5 (3) |
O1—Cu1—N2—C22 | −16.4 (4) | C17—C12—C13—C14 | −2.4 (5) |
O2—Cu1—N2—C22 | 158.6 (4) | N1—C12—C13—C14 | 178.3 (3) |
O1w—Cu1—N2—C22 | −107.3 (4) | C12—C13—C14—C15 | 0.1 (6) |
Cu1—O1—C1—C10 | −4.8 (4) | C13—C14—C15—C16 | 1.5 (6) |
Cu1—O1—C1—C2 | 173.9 (2) | C14—C15—C16—C17 | −0.7 (6) |
O1—C1—C2—C3 | 179.5 (3) | Cu1—O2—C17—C16 | 179.9 (3) |
C10—C1—C2—C3 | −1.8 (5) | Cu1—O2—C17—C12 | 0.5 (3) |
C1—C2—C3—C4 | −0.3 (5) | C15—C16—C17—O2 | 179.0 (3) |
C2—C3—C4—C9 | 1.3 (5) | C15—C16—C17—C12 | −1.6 (5) |
C2—C3—C4—C5 | −178.9 (3) | C13—C12—C17—O2 | −177.4 (3) |
C9—C4—C5—C6 | 0.5 (5) | N1—C12—C17—O2 | 2.0 (4) |
C3—C4—C5—C6 | −179.3 (3) | C13—C12—C17—C16 | 3.2 (5) |
C4—C5—C6—C7 | −0.6 (5) | N1—C12—C17—C16 | −177.5 (3) |
C5—C6—C7—C8 | 0.4 (6) | C22—N2—C18—C19 | 4.3 (9) |
C6—C7—C8—C9 | −0.2 (6) | Cu1—N2—C18—C19 | −179.3 (5) |
C7—C8—C9—C4 | 0.0 (5) | N2—C18—C19—C20 | 2 (1) |
C7—C8—C9—C10 | 179.8 (3) | C18—C19—C20—C21 | −13 (1) |
C5—C4—C9—C8 | −0.2 (4) | C19—C20—C21—C22 | 15 (1) |
C3—C4—C9—C8 | 179.6 (3) | C20—C21—C22—N2 | −8 (1) |
C5—C4—C9—C10 | −180.0 (3) | C18—N2—C22—C21 | −1.2 (9) |
C3—C4—C9—C10 | −0.2 (4) | Cu1—N2—C22—C21 | −177.6 (6) |
O1—C1—C10—C11 | 1.6 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O2i | 0.84 (3) | 2.02 (2) | 2.860 (3) | 173 (4) |
O1w—H1w2···O2ii | 0.84 (3) | 2.03 (2) | 2.858 (3) | 168 (3) |
Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, y+1/2, −z+3/2. |