supplementary materials
catena-Poly[[[pyridinecopper(II)]-(
-2-oxidonaphthalene-1-carbaldehyde picolinoylhydrazonato)-[pyridinecopper(II)]-
-sulfato] diethyl ether hemisolvate]
The title compound, {[Cu2(C17H11N3O)(SO4)(C5H5N)2]·0.5C4H10O}n, was synthesized by the reaction of 2-hydroxy-1-naphthylaldehyde-2-pyridinecarboxylhydrazone with copper sulfonate. A one-dimensional polymer was obtained via self-assembly. Each Cu ion is located in a distorted square-pyramidal coordination environment, with one Cu ion coordinated by two N and three O atoms, while the other links to two O and three N atoms. In the crystal, weak intermolecular C-H
O interactions connect the chains into a two-dimensional network.
The title compound was synthesizd by mixing
2-hydroxy-1-naphthylaldehyde-2-pyridinecarboxyl-hydrazone (0.0291 g, 0.1 mmol)
and copper sulfonate (0.0319 g, 0.2 mmol) and stirring in 10 ml of pyridine
for 6 h. The product was filtered and then layered with ether. 2 weeks later
brown single crystals were obtained. Anal. Calcd (%) for 2(C27 H21 Cu2 N5 O6
S), C4 H10 O (Mr = 1415.44): C:49.22; H:3.70; N:9.90; Found (%): C: 49.30; H:
3.52; N: 9.76
All H atoms were placed geometrically and treated as riding on their parent
atoms, with C—H 0.97 (methylene), C—H 0.93 (pyridine) C—H 0.93
(naphthalene) Å [Uiso(H) = 1.2Ueq(C)], and with C—H 0.96 Å (methyl) [Uiso(H) = 1.5Ueq(C)].
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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).
catena-Poly[[[pyridinecopper(II)]-(µ-2-oxidonaphthalene-1-carbaldehyde
picolinoylhydrazonato)-[pyridinecopper(II)]-µ-sulfonato] diethyl ether
hemisolvate]
top
Crystal data top
| [Cu2(C17H11N3O)(SO4)(C5H5N)2]·0.5C4H10O | F(000) = 2888 |
| Mr = 707.69 | Dx = 1.586 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 2858 reflections |
| a = 26.484 (2) Å | θ = 2.3–25.3° |
| b = 14.0374 (15) Å | µ = 1.56 mm−1 |
| c = 16.8083 (17) Å | T = 298 K |
| β = 108.404 (2)° | Block, brown |
| V = 5929.2 (10) Å3 | 0.38 × 0.32 × 0.16 mm |
| Z = 8 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 5215 independent reflections |
| Radiation source: fine-focus sealed tube | 3268 reflections with I > 2σ(I) |
| graphite | Rint = 0.055 |
| phi and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −31→31 |
| Tmin = 0.589, Tmax = 0.789 | k = −16→16 |
| 14633 measured reflections | l = −12→19 |
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) = 0.130 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.052P)2 + 19.1978P] where P = (Fo2 + 2Fc2)/3 |
| 5215 reflections | (Δ/σ)max = 0.001 |
| 394 parameters | Δρmax = 0.85 e Å−3 |
| 0 restraints | Δρmin = −0.49 e Å−3 |
Crystal data top
| [Cu2(C17H11N3O)(SO4)(C5H5N)2]·0.5C4H10O | V = 5929.2 (10) Å3 |
| Mr = 707.69 | Z = 8 |
| Monoclinic, C2/c | Mo Kα radiation |
| a = 26.484 (2) Å | µ = 1.56 mm−1 |
| b = 14.0374 (15) Å | T = 298 K |
| c = 16.8083 (17) Å | 0.38 × 0.32 × 0.16 mm |
| β = 108.404 (2)° | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 5215 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3268 reflections with I > 2σ(I) |
| Tmin = 0.589, Tmax = 0.789 | Rint = 0.055 |
| 14633 measured reflections | θmax = 25.0° |
Refinement top
| R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.052P)2 + 19.1978P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.130 | Δρmax = 0.85 e Å−3 |
| S = 1.01 | Δρmin = −0.49 e Å−3 |
| 5215 reflections | Absolute structure: ? |
| 394 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| H-atom parameters constrained | |
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 | 0.19607 (2) | 0.78202 (4) | 0.14330 (4) | 0.0327 (2) | |
| Cu2 | 0.14395 (2) | 1.00409 (4) | −0.08707 (4) | 0.03123 (19) | |
| N1 | 0.16100 (16) | 0.9077 (3) | 0.0066 (2) | 0.0299 (10) | |
| N2 | 0.20801 (16) | 0.8671 (3) | 0.0587 (3) | 0.0297 (10) | |
| N3 | 0.06961 (16) | 0.9731 (3) | −0.0874 (3) | 0.0331 (11) | |
| N4 | 0.17578 (17) | 0.6701 (3) | 0.2012 (3) | 0.0347 (11) | |
| N5 | 0.16690 (18) | 1.1384 (3) | −0.0190 (3) | 0.0368 (11) | |
| O1 | 0.12165 (13) | 0.8167 (3) | 0.0856 (2) | 0.0366 (9) | |
| O2 | 0.26870 (13) | 0.7475 (3) | 0.1794 (2) | 0.0374 (9) | |
| O3 | 0.12067 (13) | 1.0678 (2) | −0.2000 (2) | 0.0355 (9) | |
| O4 | 0.20303 (13) | 0.9942 (2) | −0.1402 (2) | 0.0352 (9) | |
| O5 | 0.19783 (14) | 1.1264 (3) | −0.2360 (2) | 0.0406 (9) | |
| O6 | 0.15828 (16) | 0.9758 (3) | −0.2900 (2) | 0.0449 (10) | |
| O7 | 1.0000 | 0.6854 (6) | 0.2500 | 0.092 (3) | |
| S1 | 0.17080 (5) | 1.04166 (9) | −0.22080 (8) | 0.0293 (3) | |
| C1 | 0.1195 (2) | 0.8746 (4) | 0.0264 (3) | 0.0307 (12) | |
| C2 | 0.0669 (2) | 0.9078 (4) | −0.0292 (3) | 0.0326 (12) | |
| C3 | 0.0197 (2) | 0.8731 (4) | −0.0246 (4) | 0.0456 (15) | |
| H3 | 0.0191 | 0.8286 | 0.0161 | 0.055* | |
| C4 | −0.0273 (2) | 0.9056 (5) | −0.0820 (4) | 0.0550 (17) | |
| H4 | −0.0600 | 0.8828 | −0.0808 | 0.066* | |
| C5 | −0.0247 (2) | 0.9719 (5) | −0.1405 (4) | 0.0532 (17) | |
| H5 | −0.0557 | 0.9948 | −0.1794 | 0.064* | |
| C6 | 0.0243 (2) | 1.0040 (4) | −0.1408 (4) | 0.0442 (15) | |
| H6 | 0.0257 | 1.0494 | −0.1803 | 0.053* | |
| C7 | 0.2514 (2) | 0.8798 (3) | 0.0399 (3) | 0.0313 (12) | |
| H7 | 0.2495 | 0.9184 | −0.0059 | 0.038* | |
| C8 | 0.3020 (2) | 0.8388 (3) | 0.0846 (3) | 0.0297 (12) | |
| C9 | 0.3072 (2) | 0.7729 (4) | 0.1518 (3) | 0.0321 (12) | |
| C10 | 0.3584 (2) | 0.7317 (4) | 0.1922 (4) | 0.0411 (14) | |
| H10 | 0.3616 | 0.6859 | 0.2335 | 0.049* | |
| C11 | 0.4018 (2) | 0.7567 (4) | 0.1727 (4) | 0.0439 (15) | |
| H11 | 0.4345 | 0.7299 | 0.2024 | 0.053* | |
| C12 | 0.3994 (2) | 0.8238 (4) | 0.1071 (4) | 0.0396 (14) | |
| C13 | 0.3491 (2) | 0.8645 (4) | 0.0621 (3) | 0.0332 (13) | |
| C14 | 0.3484 (2) | 0.9312 (4) | −0.0009 (4) | 0.0464 (15) | |
| H14 | 0.3162 | 0.9585 | −0.0319 | 0.056* | |
| C15 | 0.3939 (3) | 0.9568 (5) | −0.0177 (4) | 0.0624 (19) | |
| H15 | 0.3920 | 1.0009 | −0.0598 | 0.075* | |
| C16 | 0.4427 (3) | 0.9177 (5) | 0.0272 (5) | 0.067 (2) | |
| H16 | 0.4734 | 0.9358 | 0.0156 | 0.080* | |
| C17 | 0.4451 (2) | 0.8525 (5) | 0.0886 (4) | 0.0556 (18) | |
| H17 | 0.4779 | 0.8265 | 0.1188 | 0.067* | |
| C18 | 0.1284 (2) | 0.6663 (4) | 0.2132 (4) | 0.0499 (16) | |
| H18 | 0.1068 | 0.7200 | 0.2012 | 0.060* | |
| C19 | 0.1099 (3) | 0.5857 (5) | 0.2430 (4) | 0.0609 (19) | |
| H19 | 0.0768 | 0.5859 | 0.2512 | 0.073* | |
| C20 | 0.1414 (3) | 0.5058 (5) | 0.2601 (4) | 0.0580 (18) | |
| H20 | 0.1294 | 0.4502 | 0.2785 | 0.070* | |
| C21 | 0.1905 (3) | 0.5093 (4) | 0.2498 (4) | 0.0531 (17) | |
| H21 | 0.2129 | 0.4567 | 0.2628 | 0.064* | |
| C22 | 0.2066 (2) | 0.5922 (4) | 0.2198 (3) | 0.0404 (14) | |
| H22 | 0.2399 | 0.5938 | 0.2124 | 0.048* | |
| C23 | 0.1707 (2) | 1.2197 (4) | −0.0595 (4) | 0.0447 (15) | |
| H23 | 0.1622 | 1.2175 | −0.1176 | 0.054* | |
| C24 | 0.1862 (3) | 1.3053 (4) | −0.0203 (4) | 0.0517 (17) | |
| H24 | 0.1877 | 1.3598 | −0.0510 | 0.062* | |
| C25 | 0.1995 (3) | 1.3085 (5) | 0.0656 (4) | 0.0590 (18) | |
| H25 | 0.2109 | 1.3654 | 0.0939 | 0.071* | |
| C26 | 0.1959 (3) | 1.2281 (5) | 0.1093 (4) | 0.0578 (18) | |
| H26 | 0.2042 | 1.2295 | 0.1673 | 0.069* | |
| C27 | 0.1797 (2) | 1.1443 (4) | 0.0646 (4) | 0.0473 (16) | |
| H27 | 0.1776 | 1.0894 | 0.0943 | 0.057* | |
| C28 | 0.9808 (4) | 0.7425 (7) | 0.1773 (8) | 0.109 (4) | |
| H28A | 1.0083 | 0.7862 | 0.1733 | 0.131* | |
| H28B | 0.9504 | 0.7795 | 0.1798 | 0.131* | |
| C29 | 0.9644 (4) | 0.6756 (9) | 0.1002 (7) | 0.136 (4) | |
| H29A | 0.9954 | 0.6439 | 0.0952 | 0.204* | |
| H29B | 0.9481 | 0.7122 | 0.0505 | 0.204* | |
| H29C | 0.9396 | 0.6291 | 0.1072 | 0.204* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| Cu1 | 0.0341 (4) | 0.0334 (4) | 0.0307 (4) | 0.0030 (3) | 0.0104 (3) | 0.0091 (3) |
| Cu2 | 0.0336 (4) | 0.0347 (4) | 0.0247 (3) | 0.0023 (3) | 0.0083 (3) | 0.0051 (3) |
| N1 | 0.028 (2) | 0.034 (2) | 0.024 (2) | 0.005 (2) | 0.002 (2) | 0.007 (2) |
| N2 | 0.032 (2) | 0.028 (2) | 0.026 (2) | 0.002 (2) | 0.004 (2) | 0.0031 (19) |
| N3 | 0.029 (2) | 0.038 (3) | 0.029 (2) | 0.004 (2) | 0.004 (2) | 0.001 (2) |
| N4 | 0.036 (3) | 0.036 (3) | 0.033 (3) | 0.008 (2) | 0.012 (2) | 0.005 (2) |
| N5 | 0.049 (3) | 0.037 (3) | 0.025 (2) | −0.004 (2) | 0.012 (2) | −0.002 (2) |
| O1 | 0.033 (2) | 0.044 (2) | 0.033 (2) | 0.0032 (17) | 0.0119 (18) | 0.0116 (18) |
| O2 | 0.036 (2) | 0.043 (2) | 0.034 (2) | 0.0059 (18) | 0.0127 (18) | 0.0159 (18) |
| O3 | 0.034 (2) | 0.044 (2) | 0.0280 (19) | 0.0051 (17) | 0.0087 (17) | 0.0052 (17) |
| O4 | 0.034 (2) | 0.045 (2) | 0.0258 (19) | 0.0071 (17) | 0.0084 (17) | 0.0092 (17) |
| O5 | 0.050 (2) | 0.039 (2) | 0.033 (2) | −0.0119 (19) | 0.0138 (19) | 0.0061 (18) |
| O6 | 0.061 (3) | 0.044 (2) | 0.034 (2) | −0.006 (2) | 0.020 (2) | −0.0134 (18) |
| O7 | 0.071 (5) | 0.065 (5) | 0.150 (8) | 0.000 | 0.047 (6) | 0.000 |
| S1 | 0.0337 (7) | 0.0319 (7) | 0.0224 (7) | −0.0006 (6) | 0.0089 (6) | 0.0004 (6) |
| C1 | 0.033 (3) | 0.033 (3) | 0.026 (3) | 0.000 (2) | 0.008 (2) | −0.002 (2) |
| C2 | 0.030 (3) | 0.037 (3) | 0.030 (3) | 0.000 (2) | 0.009 (2) | 0.002 (2) |
| C3 | 0.039 (3) | 0.053 (4) | 0.046 (4) | 0.004 (3) | 0.016 (3) | 0.011 (3) |
| C4 | 0.030 (3) | 0.071 (5) | 0.064 (4) | −0.004 (3) | 0.016 (3) | 0.006 (4) |
| C5 | 0.033 (3) | 0.079 (5) | 0.044 (4) | 0.009 (3) | 0.007 (3) | 0.010 (4) |
| C6 | 0.040 (4) | 0.053 (4) | 0.036 (3) | 0.008 (3) | 0.007 (3) | 0.010 (3) |
| C7 | 0.038 (3) | 0.028 (3) | 0.029 (3) | −0.003 (2) | 0.011 (3) | 0.000 (2) |
| C8 | 0.032 (3) | 0.027 (3) | 0.029 (3) | 0.000 (2) | 0.009 (2) | −0.002 (2) |
| C9 | 0.036 (3) | 0.029 (3) | 0.032 (3) | 0.003 (2) | 0.012 (3) | −0.002 (2) |
| C10 | 0.034 (3) | 0.040 (3) | 0.045 (3) | 0.006 (3) | 0.006 (3) | 0.008 (3) |
| C11 | 0.031 (3) | 0.041 (3) | 0.055 (4) | 0.008 (3) | 0.006 (3) | 0.004 (3) |
| C12 | 0.032 (3) | 0.035 (3) | 0.054 (4) | 0.003 (3) | 0.016 (3) | −0.007 (3) |
| C13 | 0.031 (3) | 0.034 (3) | 0.037 (3) | −0.004 (2) | 0.015 (3) | −0.007 (3) |
| C14 | 0.043 (4) | 0.053 (4) | 0.047 (4) | −0.005 (3) | 0.019 (3) | 0.006 (3) |
| C15 | 0.065 (5) | 0.069 (5) | 0.063 (5) | −0.011 (4) | 0.034 (4) | 0.010 (4) |
| C16 | 0.054 (5) | 0.071 (5) | 0.085 (6) | −0.009 (4) | 0.037 (4) | 0.003 (4) |
| C17 | 0.043 (4) | 0.057 (4) | 0.070 (5) | 0.003 (3) | 0.022 (4) | −0.002 (4) |
| C18 | 0.050 (4) | 0.047 (4) | 0.060 (4) | 0.021 (3) | 0.028 (3) | 0.021 (3) |
| C19 | 0.052 (4) | 0.064 (5) | 0.080 (5) | 0.008 (4) | 0.040 (4) | 0.027 (4) |
| C20 | 0.059 (4) | 0.055 (4) | 0.067 (5) | 0.004 (4) | 0.028 (4) | 0.032 (4) |
| C21 | 0.057 (4) | 0.041 (4) | 0.066 (4) | 0.011 (3) | 0.024 (4) | 0.023 (3) |
| C22 | 0.043 (3) | 0.038 (3) | 0.044 (4) | 0.007 (3) | 0.018 (3) | 0.008 (3) |
| C23 | 0.060 (4) | 0.044 (4) | 0.027 (3) | −0.003 (3) | 0.010 (3) | 0.000 (3) |
| C24 | 0.066 (4) | 0.036 (3) | 0.048 (4) | −0.004 (3) | 0.011 (3) | −0.002 (3) |
| C25 | 0.068 (5) | 0.047 (4) | 0.055 (4) | −0.004 (3) | 0.010 (4) | −0.016 (3) |
| C26 | 0.072 (5) | 0.066 (5) | 0.030 (3) | −0.006 (4) | 0.009 (3) | −0.016 (3) |
| C27 | 0.064 (4) | 0.047 (4) | 0.033 (3) | −0.002 (3) | 0.017 (3) | 0.007 (3) |
| C28 | 0.076 (6) | 0.081 (7) | 0.184 (12) | 0.020 (5) | 0.058 (7) | 0.039 (7) |
| C29 | 0.115 (9) | 0.170 (12) | 0.139 (10) | 0.002 (8) | 0.063 (8) | 0.014 (10) |
Geometric parameters (Å, °) top
| Cu1—O2 | 1.888 (3) | C8—C13 | 1.459 (7) |
| Cu1—N2 | 1.957 (4) | C9—C10 | 1.432 (7) |
| Cu1—O1 | 1.964 (3) | C10—C11 | 1.339 (7) |
| Cu1—N4 | 2.008 (4) | C10—H10 | 0.9300 |
| Cu1—O5i | 2.389 (3) | C11—C12 | 1.436 (8) |
| Cu2—O3 | 2.011 (3) | C11—H11 | 0.9300 |
| Cu2—N3 | 2.015 (4) | C12—C17 | 1.402 (8) |
| Cu2—N1 | 2.016 (4) | C12—C13 | 1.426 (7) |
| Cu2—O4 | 2.036 (3) | C13—C14 | 1.409 (8) |
| Cu2—N5 | 2.189 (4) | C14—C15 | 1.368 (8) |
| N1—C1 | 1.328 (6) | C14—H14 | 0.9300 |
| N1—N2 | 1.398 (5) | C15—C16 | 1.388 (9) |
| N2—C7 | 1.296 (6) | C15—H15 | 0.9300 |
| N3—C6 | 1.325 (6) | C16—C17 | 1.365 (9) |
| N3—C2 | 1.359 (6) | C16—H16 | 0.9300 |
| N4—C18 | 1.333 (7) | C17—H17 | 0.9300 |
| N4—C22 | 1.341 (6) | C18—C19 | 1.387 (8) |
| N5—C27 | 1.340 (7) | C18—H18 | 0.9300 |
| N5—C23 | 1.349 (7) | C19—C20 | 1.372 (8) |
| O1—C1 | 1.273 (6) | C19—H19 | 0.9300 |
| O2—C9 | 1.297 (6) | C20—C21 | 1.367 (8) |
| O3—S1 | 1.520 (4) | C20—H20 | 0.9300 |
| O4—S1 | 1.510 (3) | C21—C22 | 1.387 (7) |
| O5—S1 | 1.452 (4) | C21—H21 | 0.9300 |
| O5—Cu1ii | 2.389 (3) | C22—H22 | 0.9300 |
| O6—S1 | 1.440 (4) | C23—C24 | 1.371 (8) |
| O7—C28iii | 1.416 (10) | C23—H23 | 0.9300 |
| O7—C28 | 1.416 (10) | C24—C25 | 1.374 (9) |
| C1—C2 | 1.486 (7) | C24—H24 | 0.9300 |
| C2—C3 | 1.366 (7) | C25—C26 | 1.366 (9) |
| C3—C4 | 1.391 (8) | C25—H25 | 0.9300 |
| C3—H3 | 0.9300 | C26—C27 | 1.389 (8) |
| C4—C5 | 1.371 (8) | C26—H26 | 0.9300 |
| C4—H4 | 0.9300 | C27—H27 | 0.9300 |
| C5—C6 | 1.376 (8) | C28—C29 | 1.547 (13) |
| C5—H5 | 0.9300 | C28—H28A | 0.9700 |
| C6—H6 | 0.9300 | C28—H28B | 0.9700 |
| C7—C8 | 1.434 (7) | C29—H29A | 0.9600 |
| C7—H7 | 0.9300 | C29—H29B | 0.9600 |
| C8—C9 | 1.433 (7) | C29—H29C | 0.9600 |
| | | |
| O2—Cu1—N2 | 90.44 (16) | C7—C8—C13 | 120.0 (5) |
| O2—Cu1—O1 | 169.76 (15) | O2—C9—C10 | 117.0 (5) |
| N2—Cu1—O1 | 81.79 (16) | O2—C9—C8 | 124.6 (5) |
| O2—Cu1—N4 | 92.59 (16) | C10—C9—C8 | 118.5 (5) |
| N2—Cu1—N4 | 163.41 (17) | C11—C10—C9 | 122.4 (5) |
| O1—Cu1—N4 | 93.03 (16) | C11—C10—H10 | 118.8 |
| O2—Cu1—O5i | 96.92 (14) | C9—C10—H10 | 118.8 |
| N2—Cu1—O5i | 108.92 (15) | C10—C11—C12 | 121.8 (5) |
| O1—Cu1—O5i | 91.92 (14) | C10—C11—H11 | 119.1 |
| N4—Cu1—O5i | 86.91 (16) | C12—C11—H11 | 119.1 |
| O3—Cu2—N3 | 94.91 (16) | C17—C12—C13 | 119.7 (6) |
| O3—Cu2—N1 | 164.13 (16) | C17—C12—C11 | 121.7 (5) |
| N3—Cu2—N1 | 80.49 (17) | C13—C12—C11 | 118.6 (5) |
| O3—Cu2—O4 | 70.46 (13) | C14—C13—C12 | 117.0 (5) |
| N3—Cu2—O4 | 150.44 (16) | C14—C13—C8 | 123.3 (5) |
| N1—Cu2—O4 | 106.43 (15) | C12—C13—C8 | 119.7 (5) |
| O3—Cu2—N5 | 93.57 (15) | C15—C14—C13 | 121.7 (6) |
| N3—Cu2—N5 | 107.27 (17) | C15—C14—H14 | 119.1 |
| N1—Cu2—N5 | 102.30 (16) | C13—C14—H14 | 119.1 |
| O4—Cu2—N5 | 99.37 (16) | C14—C15—C16 | 120.9 (6) |
| C1—N1—N2 | 110.1 (4) | C14—C15—H15 | 119.6 |
| C1—N1—Cu2 | 115.5 (3) | C16—C15—H15 | 119.6 |
| N2—N1—Cu2 | 134.3 (3) | C17—C16—C15 | 119.3 (6) |
| C7—N2—N1 | 118.2 (4) | C17—C16—H16 | 120.3 |
| C7—N2—Cu1 | 128.3 (4) | C15—C16—H16 | 120.3 |
| N1—N2—Cu1 | 112.8 (3) | C16—C17—C12 | 121.4 (6) |
| C6—N3—C2 | 117.8 (5) | C16—C17—H17 | 119.3 |
| C6—N3—Cu2 | 127.3 (4) | C12—C17—H17 | 119.3 |
| C2—N3—Cu2 | 114.7 (3) | N4—C18—C19 | 123.0 (5) |
| C18—N4—C22 | 117.6 (5) | N4—C18—H18 | 118.5 |
| C18—N4—Cu1 | 120.9 (4) | C19—C18—H18 | 118.5 |
| C22—N4—Cu1 | 121.0 (4) | C20—C19—C18 | 118.8 (6) |
| C27—N5—C23 | 116.2 (5) | C20—C19—H19 | 120.6 |
| C27—N5—Cu2 | 122.6 (4) | C18—C19—H19 | 120.6 |
| C23—N5—Cu2 | 121.1 (3) | C21—C20—C19 | 118.8 (6) |
| C1—O1—Cu1 | 109.5 (3) | C21—C20—H20 | 120.6 |
| C9—O2—Cu1 | 130.7 (3) | C19—C20—H20 | 120.6 |
| S1—O3—Cu2 | 94.59 (17) | C20—C21—C22 | 119.4 (6) |
| S1—O4—Cu2 | 93.93 (17) | C20—C21—H21 | 120.3 |
| S1—O5—Cu1ii | 135.4 (2) | C22—C21—H21 | 120.3 |
| C28iii—O7—C28 | 110.9 (11) | N4—C22—C21 | 122.3 (5) |
| O6—S1—O5 | 112.6 (2) | N4—C22—H22 | 118.8 |
| O6—S1—O4 | 111.3 (2) | C21—C22—H22 | 118.8 |
| O5—S1—O4 | 110.4 (2) | N5—C23—C24 | 123.9 (5) |
| O6—S1—O3 | 110.2 (2) | N5—C23—H23 | 118.0 |
| O5—S1—O3 | 111.0 (2) | C24—C23—H23 | 118.0 |
| O4—S1—O3 | 100.8 (2) | C23—C24—C25 | 118.2 (6) |
| O1—C1—N1 | 125.7 (5) | C23—C24—H24 | 120.9 |
| O1—C1—C2 | 119.5 (5) | C25—C24—H24 | 120.9 |
| N1—C1—C2 | 114.8 (5) | C26—C25—C24 | 120.0 (6) |
| N3—C2—C3 | 122.6 (5) | C26—C25—H25 | 120.0 |
| N3—C2—C1 | 114.3 (4) | C24—C25—H25 | 120.0 |
| C3—C2—C1 | 123.1 (5) | C25—C26—C27 | 118.1 (6) |
| C2—C3—C4 | 118.6 (6) | C25—C26—H26 | 121.0 |
| C2—C3—H3 | 120.7 | C27—C26—H26 | 121.0 |
| C4—C3—H3 | 120.7 | N5—C27—C26 | 123.6 (6) |
| C5—C4—C3 | 118.9 (6) | N5—C27—H27 | 118.2 |
| C5—C4—H4 | 120.5 | C26—C27—H27 | 118.2 |
| C3—C4—H4 | 120.5 | O7—C28—C29 | 107.9 (8) |
| C4—C5—C6 | 119.1 (6) | O7—C28—H28A | 110.1 |
| C4—C5—H5 | 120.5 | C29—C28—H28A | 110.1 |
| C6—C5—H5 | 120.5 | O7—C28—H28B | 110.1 |
| N3—C6—C5 | 123.0 (6) | C29—C28—H28B | 110.1 |
| N3—C6—H6 | 118.5 | H28A—C28—H28B | 108.4 |
| C5—C6—H6 | 118.5 | C28—C29—H29A | 109.5 |
| N2—C7—C8 | 124.8 (5) | C28—C29—H29B | 109.5 |
| N2—C7—H7 | 117.6 | H29A—C29—H29B | 109.5 |
| C8—C7—H7 | 117.6 | C28—C29—H29C | 109.5 |
| C9—C8—C7 | 120.9 (5) | H29A—C29—H29C | 109.5 |
| C9—C8—C13 | 119.1 (5) | H29B—C29—H29C | 109.5 |
| Symmetry codes: (i) x, −y+2, z+1/2; (ii) x, −y+2, z−1/2; (iii) −x+2, y, −z+1/2. |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C26—H26···O2iv | 0.93 | 2.46 | 3.386 (7) | 174 |
| C5—H5···O3v | 0.93 | 2.43 | 3.340 (7) | 165 |
| C19—H19···O7vi | 0.93 | 2.46 | 3.266 (7) | 145 |
| Symmetry codes: (iv) −x+1/2, y+1/2, −z+1/2; (v) −x, y, −z−1/2; (vi) −x+1, y, −z+1/2. |
Table 1
Selected geometric parameters (Å) top| Cu1—O2 | 1.888 (3) | Cu2—O3 | 2.011 (3) |
| Cu1—N2 | 1.957 (4) | Cu2—N3 | 2.015 (4) |
| Cu1—O1 | 1.964 (3) | Cu2—N1 | 2.016 (4) |
| Cu1—N4 | 2.008 (4) | Cu2—O4 | 2.036 (3) |
| Cu1—O5i | 2.389 (3) | Cu2—N5 | 2.189 (4) |
| Symmetry codes: (i) x, −y+2, z+1/2. |
Table 2
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C26—H26···O2ii | 0.93 | 2.46 | 3.386 (7) | 174 |
| C5—H5···O3iii | 0.93 | 2.43 | 3.340 (7) | 165 |
| C19—H19···O7iv | 0.93 | 2.46 | 3.266 (7) | 145 |
| Symmetry codes: (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x, y, −z−1/2; (iv) −x+1, y, −z+1/2. |
We acknowledge the financial support of the National Natural Science Foundation
of China (grant No. 20671048).
Armstrong, C. M., Bernhardt, P. V., Chin, P. & Richardson, D. R. (2003). Eur. J. Inorg. Chem. pp. 1145–1156.
Bai, Y., Dang, D. B., Cao, X., Duan, C. Y. & Meng, Q. J. (2006). Inorg. Chem. Commun. pp. 86–89.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-Ray Systems, Inc., Madison, Wisconsin, USA.
Hydrazone complexes play an important role in the fields of photoelectric materials and medicines due to their biological and pharmacological activities (Armstrong et al., 2003). The molecular structure of the related salicylaldehyde-2-pyridinecarboxyl-hydrazone has been reported (Bai et al., 2006). To throw further light on the coordination characteristics of 2-pyridinecarboxyl-hydrazone and to explore the properties of their complexes, we report the structure of the title complex (I).
The structure of repeating unit of complex I is shown in Fig. 1 and the one-dimensional polymeric chain structure of the complex is shown in Fig. 2. In the complex, each Cu ion is located in a distorted square pyramidal coordination environment. Cu1 is coordinated to two N and three O atoms, while Cu2 links to two O and three N atoms. The Cu—O (2-naphthol) distance [1.888 (3) Å] is slightly shorter than the previously reported Cu—O (phenol) distance [1.954 (3) Å] (Bai et al., 2006), whereas the Cu—O (carbozone) distance [1.964 (3) Å] is longer than the related Cu—O (carbozone) distance of 1.942 (3) Å in the related complex (Bai et al., 2006). In the crystal, weak intermolecular C—H···O interactions connect the chains into a two-dimensional net structure.