Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039669/kp2125sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039669/kp2125Isup2.hkl |
CCDC reference: 660118
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.034
- wR factor = 0.093
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O3 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N3
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.65 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - O3 .. 5.79 su
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.655 Tmax scaled 0.645 Tmin scaled 0.503 PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu (2) 2.28
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
A 10 ml me thanol solution of Cu(NO3)2.3H2O (0.242 g,1 mmol) was dropped into 10 ml me thanol solution of 2, 2'-bipyridine(0.156 g,1 mmol) and 2-hydroxy-1-naphthaldehyde (0.16 g,1 mmol) to be stirred for 5 h at 323 K. By an evaporation of the filtrate for about 10 days green block-shaped crystals were obtained. Analysis, found (%): C, 55.60; H, 3.35; N, 9.21. C21H15CuN3O5 required (%):C, 55.64; H, 3.31; N, 9.27.
H atoms were positioned geometrically with C—H distance of 0.93 Å, and treated as riding atoms, with Uiso(H)=1.2Ueq(C).
In the previously published papers, the crystal structures of 2-hydroxy-1-naphthaldehyde (Maniukiewicz & Bukowska-Strzyzewska, 1992) and its three copper(II) complexes (Yu et al., 2006; Xiu-Jian et al., 2005; Elmali & Elerman, 2002) have been determined. In this paper, we report a new compound containing naphthaldehyde as a ligand (Fig.1). The CuII atom is five-coordinated by two N atoms of bipy and two O atoms of naph in the equatorial plane with an axial nitrate O—Cu bond to form square-pyramidal coordination geometry (Table 1). The Cu atom is shifted from from the least-squares plane N1/N2/O2/O1 by 0.2103 (3)Å towards O3. The presented structure comprises the same cation as [Cu(C10H8N2)(C11H7O2)(ClO4)] (Elmali & Elerman, 2002) but anions are different: nitrate and perchlorate. In the crystal structure of (I), there are two kinds of π-π stacking interactions: strong one between naphthalene rings (symmetry codes: -x + 1, y - 1/2, -z + 1/2; x, -y + 3/2, z + 1/2) and the weak one between naphthalene ring and pyridine ring (symmetry codes: -x + 1, y - 1/2, -z + 1/2; x, y - 1/2, z + 1/2). The dihedral angle, interplanar average distance and ring-centroid separation distance are: 0.000 (1)°, 3.3504 (2) Å, 4.0800 (7)Å for the former ones and 2.505 (1)°, 3.5373 (2) Å, 4.2048 (9)Å for the latter ones, respectively. The title molecules are connected into dimers through the first kind of stacking and further linked into a one-dimensional skeleton via the second π-π stacking along c axis (Fig. 2).
For related literature, see: Elmali & Elerman (2002); Maniukiewicz & Bukowska-Strzyzewska (1992); Xiu-Jian et al. (2005); Yu et al. (2006).
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXTL (Siemens, 1994).
[Cu(C11H7O2)(NO3)(C10H8N2)] | F(000) = 924 |
Mr = 452.90 | Dx = 1.618 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 38 reflections |
a = 12.428 (3) Å | θ = 4.6–15.2° |
b = 9.167 (2) Å | µ = 1.22 mm−1 |
c = 17.245 (6) Å | T = 296 K |
β = 108.85 (1)° | Block, green |
V = 1859.3 (9) Å3 | 0.56 × 0.48 × 0.36 mm |
Z = 4 |
Siemens P4 diffractometer | 2552 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
ω scans | h = 0→14 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = 0→10 |
Tmin = 0.767, Tmax = 0.985 | l = −20→19 |
3797 measured reflections | 3 standard reflections every 97 reflections |
3261 independent reflections | intensity decay: 1.4% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.0639P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3261 reflections | Δρmax = 0.36 e Å−3 |
272 parameters | Δρmin = −0.39 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00014 (4) |
[Cu(C11H7O2)(NO3)(C10H8N2)] | V = 1859.3 (9) Å3 |
Mr = 452.90 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.428 (3) Å | µ = 1.22 mm−1 |
b = 9.167 (2) Å | T = 296 K |
c = 17.245 (6) Å | 0.56 × 0.48 × 0.36 mm |
β = 108.85 (1)° |
Siemens P4 diffractometer | 2552 reflections with I > 2σ(I) |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | Rint = 0.017 |
Tmin = 0.767, Tmax = 0.985 | 3 standard reflections every 97 reflections |
3797 measured reflections | intensity decay: 1.4% |
3261 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.36 e Å−3 |
3261 reflections | Δρmin = −0.39 e Å−3 |
272 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cu | 0.69710 (3) | 0.56548 (4) | 0.01255 (2) | 0.04165 (14) | |
O1 | 0.57130 (15) | 0.6902 (2) | −0.03875 (11) | 0.0465 (5) | |
O2 | 0.64002 (17) | 0.5217 (2) | 0.10181 (12) | 0.0488 (5) | |
O3 | 0.8122 (2) | 0.7602 (3) | 0.05872 (16) | 0.0885 (9) | |
O4 | 0.8697 (3) | 0.6778 (3) | 0.18001 (17) | 0.1045 (10) | |
O5 | 0.9546 (2) | 0.8586 (3) | 0.14903 (16) | 0.0751 (7) | |
N1 | 0.73773 (19) | 0.5505 (3) | −0.08999 (14) | 0.0424 (5) | |
N2 | 0.81823 (18) | 0.4139 (2) | 0.04854 (14) | 0.0412 (5) | |
N3 | 0.8786 (2) | 0.7689 (3) | 0.12895 (18) | 0.0549 (7) | |
C1 | 0.5021 (2) | 0.7470 (3) | −0.00535 (17) | 0.0408 (6) | |
C2 | 0.4219 (2) | 0.8518 (3) | −0.05254 (18) | 0.0473 (7) | |
H2 | 0.4195 | 0.8722 | −0.1059 | 0.057* | |
C3 | 0.3493 (2) | 0.9216 (3) | −0.02088 (19) | 0.0488 (7) | |
H3 | 0.2982 | 0.9886 | −0.0534 | 0.059* | |
C4 | 0.3487 (2) | 0.8958 (3) | 0.06057 (18) | 0.0448 (7) | |
C5 | 0.2758 (3) | 0.9761 (4) | 0.0928 (2) | 0.0590 (9) | |
H5 | 0.2281 | 1.0469 | 0.0609 | 0.071* | |
C6 | 0.2749 (3) | 0.9502 (4) | 0.1705 (2) | 0.0664 (10) | |
H6 | 0.2272 | 1.0038 | 0.1915 | 0.080* | |
C7 | 0.3455 (3) | 0.8437 (4) | 0.2182 (2) | 0.0573 (8) | |
H7 | 0.3438 | 0.8252 | 0.2708 | 0.069* | |
C8 | 0.4175 (2) | 0.7658 (3) | 0.18808 (18) | 0.0492 (7) | |
H8 | 0.4647 | 0.6959 | 0.2212 | 0.059* | |
C9 | 0.4220 (2) | 0.7884 (3) | 0.10894 (17) | 0.0413 (6) | |
C10 | 0.4987 (2) | 0.7101 (3) | 0.07414 (17) | 0.0390 (6) | |
C11 | 0.5631 (2) | 0.5932 (3) | 0.11747 (18) | 0.0445 (7) | |
H11 | 0.5467 | 0.5645 | 0.1642 | 0.053* | |
C12 | 0.6931 (3) | 0.6285 (4) | −0.15859 (19) | 0.0550 (8) | |
H12 | 0.6364 | 0.6959 | −0.1606 | 0.066* | |
C13 | 0.7278 (3) | 0.6129 (4) | −0.2256 (2) | 0.0678 (10) | |
H13 | 0.6947 | 0.6684 | −0.2724 | 0.081* | |
C14 | 0.8112 (3) | 0.5152 (4) | −0.2232 (2) | 0.0660 (10) | |
H14 | 0.8362 | 0.5042 | −0.2682 | 0.079* | |
C15 | 0.8582 (3) | 0.4327 (3) | −0.1540 (2) | 0.0563 (8) | |
H15 | 0.9147 | 0.3647 | −0.1518 | 0.068* | |
C16 | 0.8204 (2) | 0.4523 (3) | −0.08780 (17) | 0.0401 (6) | |
C17 | 0.8641 (2) | 0.3727 (3) | −0.00911 (17) | 0.0418 (6) | |
C18 | 0.9466 (2) | 0.2650 (3) | 0.0066 (2) | 0.0554 (8) | |
H18 | 0.9769 | 0.2364 | −0.0338 | 0.066* | |
C19 | 0.9828 (3) | 0.2011 (4) | 0.0830 (2) | 0.0625 (9) | |
H19 | 1.0378 | 0.1282 | 0.0945 | 0.075* | |
C20 | 0.9380 (3) | 0.2448 (4) | 0.1418 (2) | 0.0585 (8) | |
H20 | 0.9626 | 0.2031 | 0.1937 | 0.070* | |
C21 | 0.8559 (2) | 0.3514 (3) | 0.12283 (18) | 0.0506 (7) | |
H21 | 0.8253 | 0.3814 | 0.1629 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.0377 (2) | 0.0452 (2) | 0.0434 (2) | 0.00772 (16) | 0.01494 (15) | 0.00289 (17) |
O1 | 0.0394 (10) | 0.0579 (12) | 0.0442 (11) | 0.0120 (9) | 0.0163 (9) | 0.0046 (10) |
O2 | 0.0461 (11) | 0.0510 (12) | 0.0537 (12) | 0.0101 (10) | 0.0222 (10) | 0.0094 (10) |
O3 | 0.0918 (19) | 0.0642 (16) | 0.0767 (18) | −0.0083 (15) | −0.0184 (15) | 0.0074 (14) |
O4 | 0.133 (3) | 0.104 (2) | 0.0666 (18) | −0.047 (2) | 0.0194 (18) | −0.0145 (17) |
O5 | 0.0671 (15) | 0.0790 (17) | 0.0836 (17) | −0.0268 (14) | 0.0306 (14) | −0.0271 (15) |
N1 | 0.0400 (12) | 0.0448 (13) | 0.0423 (13) | 0.0051 (11) | 0.0131 (11) | 0.0022 (11) |
N2 | 0.0367 (12) | 0.0435 (14) | 0.0430 (13) | 0.0038 (10) | 0.0122 (10) | 0.0043 (11) |
N3 | 0.0523 (16) | 0.0560 (17) | 0.0592 (18) | 0.0004 (14) | 0.0217 (14) | −0.0173 (15) |
C1 | 0.0320 (13) | 0.0392 (14) | 0.0479 (16) | −0.0014 (12) | 0.0084 (12) | −0.0052 (13) |
C2 | 0.0453 (16) | 0.0486 (17) | 0.0450 (17) | 0.0040 (14) | 0.0104 (14) | −0.0001 (14) |
C3 | 0.0379 (15) | 0.0451 (17) | 0.0575 (19) | 0.0083 (13) | 0.0072 (14) | 0.0026 (15) |
C4 | 0.0382 (15) | 0.0439 (16) | 0.0508 (18) | 0.0013 (12) | 0.0122 (13) | −0.0083 (13) |
C5 | 0.0515 (19) | 0.058 (2) | 0.067 (2) | 0.0163 (15) | 0.0185 (17) | −0.0033 (17) |
C6 | 0.061 (2) | 0.070 (2) | 0.078 (2) | 0.0111 (18) | 0.0358 (19) | −0.013 (2) |
C7 | 0.0594 (19) | 0.064 (2) | 0.0532 (19) | −0.0018 (17) | 0.0253 (16) | −0.0111 (17) |
C8 | 0.0470 (17) | 0.0502 (18) | 0.0515 (18) | 0.0001 (14) | 0.0173 (15) | −0.0072 (15) |
C9 | 0.0349 (14) | 0.0403 (15) | 0.0474 (16) | −0.0061 (12) | 0.0114 (12) | −0.0090 (13) |
C10 | 0.0331 (13) | 0.0406 (15) | 0.0434 (15) | −0.0020 (12) | 0.0127 (12) | −0.0040 (12) |
C11 | 0.0423 (16) | 0.0475 (17) | 0.0467 (17) | 0.0011 (13) | 0.0185 (13) | 0.0009 (13) |
C12 | 0.0528 (18) | 0.0598 (19) | 0.0525 (19) | 0.0175 (16) | 0.0172 (15) | 0.0110 (16) |
C13 | 0.073 (2) | 0.081 (2) | 0.055 (2) | 0.024 (2) | 0.0279 (18) | 0.0241 (18) |
C14 | 0.071 (2) | 0.080 (2) | 0.059 (2) | 0.015 (2) | 0.0382 (19) | 0.0156 (19) |
C15 | 0.0525 (18) | 0.062 (2) | 0.062 (2) | 0.0147 (16) | 0.0302 (16) | 0.0096 (17) |
C16 | 0.0323 (13) | 0.0416 (15) | 0.0449 (16) | 0.0011 (12) | 0.0103 (12) | 0.0019 (13) |
C17 | 0.0328 (14) | 0.0429 (15) | 0.0497 (17) | −0.0019 (12) | 0.0132 (13) | 0.0026 (13) |
C18 | 0.0474 (17) | 0.0566 (19) | 0.067 (2) | 0.0157 (15) | 0.0246 (16) | 0.0078 (17) |
C19 | 0.0501 (19) | 0.063 (2) | 0.074 (2) | 0.0231 (16) | 0.0193 (17) | 0.0189 (18) |
C20 | 0.0518 (18) | 0.063 (2) | 0.0549 (19) | 0.0085 (17) | 0.0093 (16) | 0.0190 (17) |
C21 | 0.0472 (17) | 0.0568 (19) | 0.0474 (18) | 0.0032 (15) | 0.0149 (14) | 0.0057 (15) |
Cu—O1 | 1.9082 (18) | C6—H6 | 0.9300 |
Cu—O2 | 1.934 (2) | C7—C8 | 1.372 (4) |
Cu—N1 | 1.994 (2) | C7—H7 | 0.9300 |
Cu—N2 | 1.995 (2) | C8—C9 | 1.399 (4) |
Cu—O3 | 2.265 (3) | C8—H8 | 0.9300 |
O1—C1 | 1.289 (3) | C9—C10 | 1.468 (4) |
O2—C11 | 1.259 (3) | C10—C11 | 1.400 (4) |
O3—N3 | 1.228 (3) | C11—H11 | 0.9300 |
O4—N3 | 1.244 (4) | C12—C13 | 1.365 (4) |
O5—N3 | 1.215 (3) | C12—H12 | 0.9300 |
N1—C12 | 1.339 (4) | C13—C14 | 1.360 (4) |
N1—C16 | 1.357 (3) | C13—H13 | 0.9300 |
N2—C21 | 1.342 (4) | C14—C15 | 1.374 (4) |
N2—C17 | 1.350 (3) | C14—H14 | 0.9300 |
C1—C10 | 1.426 (4) | C15—C16 | 1.379 (4) |
C1—C2 | 1.434 (4) | C15—H15 | 0.9300 |
C2—C3 | 1.356 (4) | C16—C17 | 1.481 (4) |
C2—H2 | 0.9300 | C17—C18 | 1.385 (4) |
C3—C4 | 1.427 (4) | C18—C19 | 1.378 (4) |
C3—H3 | 0.9300 | C18—H18 | 0.9300 |
C4—C5 | 1.414 (4) | C19—C20 | 1.365 (4) |
C4—C9 | 1.415 (4) | C19—H19 | 0.9300 |
C5—C6 | 1.363 (5) | C20—C21 | 1.375 (4) |
C5—H5 | 0.9300 | C20—H20 | 0.9300 |
C6—C7 | 1.390 (5) | C21—H21 | 0.9300 |
O1—Cu—O2 | 92.12 (8) | C7—C8—C9 | 121.9 (3) |
O1—Cu—N1 | 91.97 (9) | C7—C8—H8 | 119.1 |
O2—Cu—N1 | 162.68 (9) | C9—C8—H8 | 119.1 |
O1—Cu—N2 | 169.98 (9) | C8—C9—C4 | 117.2 (3) |
O2—Cu—N2 | 92.40 (9) | C8—C9—C10 | 124.2 (3) |
N1—Cu—N2 | 81.15 (9) | C4—C9—C10 | 118.6 (3) |
O1—Cu—O3 | 91.16 (9) | C11—C10—C1 | 120.3 (2) |
O2—Cu—O3 | 103.65 (10) | C11—C10—C9 | 119.4 (3) |
N1—Cu—O3 | 93.08 (10) | C1—C10—C9 | 120.2 (2) |
N2—Cu—O3 | 96.45 (10) | O2—C11—C10 | 128.8 (3) |
C1—O1—Cu | 126.84 (18) | O2—C11—H11 | 115.6 |
C11—O2—Cu | 124.22 (19) | C10—C11—H11 | 115.6 |
N3—O3—Cu | 123.0 (2) | N1—C12—C13 | 122.6 (3) |
C12—N1—C16 | 118.2 (2) | N1—C12—H12 | 118.7 |
C12—N1—Cu | 126.5 (2) | C13—C12—H12 | 118.7 |
C16—N1—Cu | 115.28 (18) | C14—C13—C12 | 119.3 (3) |
C21—N2—C17 | 119.0 (2) | C14—C13—H13 | 120.4 |
C21—N2—Cu | 126.1 (2) | C12—C13—H13 | 120.4 |
C17—N2—Cu | 114.94 (18) | C13—C14—C15 | 119.6 (3) |
O5—N3—O3 | 122.5 (3) | C13—C14—H14 | 120.2 |
O5—N3—O4 | 119.4 (3) | C15—C14—H14 | 120.2 |
O3—N3—O4 | 118.0 (3) | C14—C15—C16 | 119.0 (3) |
O1—C1—C10 | 124.4 (2) | C14—C15—H15 | 120.5 |
O1—C1—C2 | 117.3 (3) | C16—C15—H15 | 120.5 |
C10—C1—C2 | 118.2 (2) | N1—C16—C15 | 121.4 (3) |
C3—C2—C1 | 121.3 (3) | N1—C16—C17 | 113.8 (2) |
C3—C2—H2 | 119.4 | C15—C16—C17 | 124.9 (3) |
C1—C2—H2 | 119.4 | N2—C17—C18 | 121.2 (3) |
C2—C3—C4 | 122.3 (3) | N2—C17—C16 | 114.8 (2) |
C2—C3—H3 | 118.9 | C18—C17—C16 | 124.0 (3) |
C4—C3—H3 | 118.9 | C19—C18—C17 | 118.8 (3) |
C5—C4—C9 | 120.2 (3) | C19—C18—H18 | 120.6 |
C5—C4—C3 | 120.6 (3) | C17—C18—H18 | 120.6 |
C9—C4—C3 | 119.2 (3) | C20—C19—C18 | 120.0 (3) |
C6—C5—C4 | 120.4 (3) | C20—C19—H19 | 120.0 |
C6—C5—H5 | 119.8 | C18—C19—H19 | 120.0 |
C4—C5—H5 | 119.8 | C19—C20—C21 | 118.8 (3) |
C5—C6—C7 | 120.0 (3) | C19—C20—H20 | 120.6 |
C5—C6—H6 | 120.0 | C21—C20—H20 | 120.6 |
C7—C6—H6 | 120.0 | N2—C21—C20 | 122.2 (3) |
C8—C7—C6 | 120.4 (3) | N2—C21—H21 | 118.9 |
C8—C7—H7 | 119.8 | C20—C21—H21 | 118.9 |
C6—C7—H7 | 119.8 | ||
O2—Cu—O1—C1 | 17.3 (2) | C7—C8—C9—C10 | 178.9 (3) |
N1—Cu—O1—C1 | −179.5 (2) | C5—C4—C9—C8 | 0.6 (4) |
N2—Cu—O1—C1 | 134.1 (4) | C3—C4—C9—C8 | −179.3 (3) |
O3—Cu—O1—C1 | −86.4 (2) | C5—C4—C9—C10 | −178.3 (3) |
O1—Cu—O2—C11 | −14.7 (2) | C3—C4—C9—C10 | 1.7 (4) |
N1—Cu—O2—C11 | −118.3 (3) | O1—C1—C10—C11 | −8.3 (4) |
N2—Cu—O2—C11 | 174.2 (2) | C2—C1—C10—C11 | 170.3 (2) |
O3—Cu—O2—C11 | 77.0 (2) | O1—C1—C10—C9 | 175.7 (2) |
O1—Cu—O3—N3 | 135.3 (3) | C2—C1—C10—C9 | −5.7 (4) |
O2—Cu—O3—N3 | 42.8 (3) | C8—C9—C10—C11 | 7.8 (4) |
N1—Cu—O3—N3 | −132.7 (3) | C4—C9—C10—C11 | −173.3 (2) |
N2—Cu—O3—N3 | −51.3 (3) | C8—C9—C10—C1 | −176.1 (3) |
O1—Cu—N1—C12 | 9.0 (3) | C4—C9—C10—C1 | 2.7 (4) |
O2—Cu—N1—C12 | 112.6 (3) | Cu—O2—C11—C10 | 3.8 (4) |
N2—Cu—N1—C12 | −178.3 (3) | C1—C10—C11—O2 | 11.0 (4) |
O3—Cu—N1—C12 | −82.3 (3) | C9—C10—C11—O2 | −173.0 (3) |
O1—Cu—N1—C16 | −172.13 (19) | C16—N1—C12—C13 | −0.1 (5) |
O2—Cu—N1—C16 | −68.5 (4) | Cu—N1—C12—C13 | 178.7 (3) |
N2—Cu—N1—C16 | 0.55 (19) | N1—C12—C13—C14 | −0.3 (6) |
O3—Cu—N1—C16 | 96.6 (2) | C12—C13—C14—C15 | 0.7 (6) |
O1—Cu—N2—C21 | −134.5 (4) | C13—C14—C15—C16 | −0.7 (5) |
O2—Cu—N2—C21 | −17.7 (2) | C12—N1—C16—C15 | 0.1 (4) |
N1—Cu—N2—C21 | 178.5 (2) | Cu—N1—C16—C15 | −178.8 (2) |
O3—Cu—N2—C21 | 86.3 (2) | C12—N1—C16—C17 | 179.7 (3) |
O1—Cu—N2—C17 | 45.2 (6) | Cu—N1—C16—C17 | 0.7 (3) |
O2—Cu—N2—C17 | 161.98 (19) | C14—C15—C16—N1 | 0.3 (5) |
N1—Cu—N2—C17 | −1.86 (18) | C14—C15—C16—C17 | −179.2 (3) |
O3—Cu—N2—C17 | −94.0 (2) | C21—N2—C17—C18 | 1.8 (4) |
Cu—O3—N3—O5 | 165.6 (2) | Cu—N2—C17—C18 | −177.9 (2) |
Cu—O3—N3—O4 | −11.3 (4) | C21—N2—C17—C16 | −177.5 (2) |
Cu—O1—C1—C10 | −8.8 (4) | Cu—N2—C17—C16 | 2.8 (3) |
Cu—O1—C1—C2 | 172.60 (18) | N1—C16—C17—N2 | −2.3 (3) |
O1—C1—C2—C3 | −177.1 (3) | C15—C16—C17—N2 | 177.2 (3) |
C10—C1—C2—C3 | 4.3 (4) | N1—C16—C17—C18 | 178.4 (3) |
C1—C2—C3—C4 | 0.2 (4) | C15—C16—C17—C18 | −2.1 (5) |
C2—C3—C4—C5 | 176.8 (3) | N2—C17—C18—C19 | −0.9 (5) |
C2—C3—C4—C9 | −3.3 (4) | C16—C17—C18—C19 | 178.3 (3) |
C9—C4—C5—C6 | −0.4 (5) | C17—C18—C19—C20 | −0.4 (5) |
C3—C4—C5—C6 | 179.5 (3) | C18—C19—C20—C21 | 0.8 (5) |
C4—C5—C6—C7 | −0.5 (5) | C17—N2—C21—C20 | −1.3 (4) |
C5—C6—C7—C8 | 1.1 (5) | Cu—N2—C21—C20 | 178.3 (2) |
C6—C7—C8—C9 | −0.8 (5) | C19—C20—C21—N2 | 0.1 (5) |
C7—C8—C9—C4 | 0.0 (4) |
Experimental details
Crystal data | |
Chemical formula | [Cu(C11H7O2)(NO3)(C10H8N2)] |
Mr | 452.90 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 12.428 (3), 9.167 (2), 17.245 (6) |
β (°) | 108.85 (1) |
V (Å3) | 1859.3 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.22 |
Crystal size (mm) | 0.56 × 0.48 × 0.36 |
Data collection | |
Diffractometer | Siemens P4 |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.767, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3797, 3261, 2552 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.093, 1.05 |
No. of reflections | 3261 |
No. of parameters | 272 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.39 |
Computer programs: XSCANS (Siemens, 1994), SHELXTL (Siemens, 1994), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).
Cu—O1 | 1.9082 (18) | Cu—N2 | 1.995 (2) |
Cu—O2 | 1.934 (2) | Cu—O3 | 2.265 (3) |
Cu—N1 | 1.994 (2) | ||
O1—Cu—O2 | 92.12 (8) | N1—Cu—N2 | 81.15 (9) |
O1—Cu—N1 | 91.97 (9) | O1—Cu—O3 | 91.16 (9) |
O1—Cu—N2 | 169.98 (9) | N2—Cu—O3 | 96.45 (10) |
O2—Cu—N2 | 92.40 (9) |
In the previously published papers, the crystal structures of 2-hydroxy-1-naphthaldehyde (Maniukiewicz & Bukowska-Strzyzewska, 1992) and its three copper(II) complexes (Yu et al., 2006; Xiu-Jian et al., 2005; Elmali & Elerman, 2002) have been determined. In this paper, we report a new compound containing naphthaldehyde as a ligand (Fig.1). The CuII atom is five-coordinated by two N atoms of bipy and two O atoms of naph in the equatorial plane with an axial nitrate O—Cu bond to form square-pyramidal coordination geometry (Table 1). The Cu atom is shifted from from the least-squares plane N1/N2/O2/O1 by 0.2103 (3)Å towards O3. The presented structure comprises the same cation as [Cu(C10H8N2)(C11H7O2)(ClO4)] (Elmali & Elerman, 2002) but anions are different: nitrate and perchlorate. In the crystal structure of (I), there are two kinds of π-π stacking interactions: strong one between naphthalene rings (symmetry codes: -x + 1, y - 1/2, -z + 1/2; x, -y + 3/2, z + 1/2) and the weak one between naphthalene ring and pyridine ring (symmetry codes: -x + 1, y - 1/2, -z + 1/2; x, y - 1/2, z + 1/2). The dihedral angle, interplanar average distance and ring-centroid separation distance are: 0.000 (1)°, 3.3504 (2) Å, 4.0800 (7)Å for the former ones and 2.505 (1)°, 3.5373 (2) Å, 4.2048 (9)Å for the latter ones, respectively. The title molecules are connected into dimers through the first kind of stacking and further linked into a one-dimensional skeleton via the second π-π stacking along c axis (Fig. 2).