

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810025481/sj5030sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810025481/sj5030Isup2.hkl |
CCDC reference: 788190
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.057
- wR factor = 0.163
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 20 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 9
Alert level G PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c ....... P21/n
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
4-Methoxysalicylaldehyde (0.1 mmol, 15.2 mg) and cyclopentylamine (0.1 mmol, 8.5 mg) were mixed and stirred in methanol (10 ml) for 30 min. Then a methanol solution (5 ml) of copper acetate (0.1 mmol, 19.9 mg) was added to the mixture. The final mixture was stirred for another 30 min to give a blue solution. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of the solution at room temperature.
H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined using a riding model, with with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmetyl). Rotating group models were used for the methyl groups.
Schiff bases are known to be versatile ligands in coordination chemistry (Hamaker et al., 2010; Wang et al., 2010; Mirkhani et al., 2010; Liu & Yang, 2009). A large number of complexes with Schiff bases have been reported because of their interesting structures and potential applications (Keypour et al., 2009; Adhikary et al., 2009; Peng et al., 2009). We report here the crystal structure of the title new copper complex with the Schiff base ligand 2-(cyclopentyliminomethyl)-5-methoxyphenol.
The Cu atom in the complex is four-coordinated by two phenolate O atoms and two imine N atoms from two Schiff base ligands, forming a distorted square planar geometry (Fig. 1). The dihedral angle between the C1-C6 and C14-C19 benzene rings is 55.8 (3)°. The bond lengths (Table 1) involving the Cu atom are comparable to those observed in similar copper complexes (Friščić et al., 2002; Marsh & Spek, 2001; Han et al., 2001; Akitsu & Einaga, 2004; Dhar et al., 2003).
For background to complexes with Schiff bases, see: Hamaker et al. (2010); Wang et al. (2010); Mirkhani et al. (2010); Liu & Yang (2009); Keypour et al. (2009); Adhikary et al. (2009); Peng et al. (2009). For similar copper complexes, see: Friščić et al. (2002); Marsh & Spek (2001); Han et al. (2001); Akitsu & Einaga, 2004; Dhar et al. (2003).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).
![]() | Fig. 1. The molecular structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
[Cu(C13H16NO2)2] | F(000) = 1052 |
Mr = 500.08 | Dx = 1.383 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3695 reflections |
a = 8.496 (1) Å | θ = 2.5–25.1° |
b = 14.054 (2) Å | µ = 0.94 mm−1 |
c = 20.442 (2) Å | T = 298 K |
β = 100.236 (3)° | Block, blue |
V = 2402.0 (5) Å3 | 0.23 × 0.21 × 0.21 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 4333 independent reflections |
Radiation source: fine-focus sealed tube | 3131 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
ω scans | θmax = 25.3°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −9→10 |
Tmin = 0.812, Tmax = 0.826 | k = −16→16 |
12222 measured reflections | l = −24→17 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0973P)2] where P = (Fo2 + 2Fc2)/3 |
4333 reflections | (Δ/σ)max = 0.001 |
300 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −1.16 e Å−3 |
[Cu(C13H16NO2)2] | V = 2402.0 (5) Å3 |
Mr = 500.08 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.496 (1) Å | µ = 0.94 mm−1 |
b = 14.054 (2) Å | T = 298 K |
c = 20.442 (2) Å | 0.23 × 0.21 × 0.21 mm |
β = 100.236 (3)° |
Bruker APEXII CCD area-detector diffractometer | 4333 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 3131 reflections with I > 2σ(I) |
Tmin = 0.812, Tmax = 0.826 | Rint = 0.081 |
12222 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.69 e Å−3 |
4333 reflections | Δρmin = −1.16 e Å−3 |
300 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
Cu1 | −0.00311 (5) | 0.84349 (3) | 0.75910 (2) | 0.0392 (2) | |
N1 | −0.0266 (3) | 0.8673 (2) | 0.85224 (14) | 0.0387 (7) | |
N2 | 0.0215 (3) | 0.8950 (2) | 0.67202 (13) | 0.0367 (7) | |
O1 | 0.2109 (3) | 0.80068 (19) | 0.77995 (11) | 0.0460 (6) | |
O2 | 0.6781 (3) | 0.6732 (2) | 0.91142 (15) | 0.0597 (8) | |
O3 | −0.2181 (3) | 0.8050 (2) | 0.73199 (11) | 0.0487 (7) | |
O4 | −0.6953 (3) | 0.7268 (2) | 0.58341 (13) | 0.0608 (8) | |
C1 | 0.2376 (4) | 0.8058 (3) | 0.89943 (16) | 0.0387 (8) | |
C2 | 0.2940 (4) | 0.7847 (2) | 0.83963 (16) | 0.0376 (8) | |
C3 | 0.4436 (4) | 0.7414 (2) | 0.84350 (17) | 0.0408 (8) | |
H3 | 0.4817 | 0.7276 | 0.8047 | 0.049* | |
C4 | 0.5355 (4) | 0.7190 (3) | 0.90438 (18) | 0.0438 (9) | |
C5 | 0.4826 (5) | 0.7423 (3) | 0.96339 (18) | 0.0510 (10) | |
H5 | 0.5457 | 0.7289 | 1.0044 | 0.061* | |
C6 | 0.3390 (4) | 0.7843 (3) | 0.96003 (18) | 0.0481 (10) | |
H6 | 0.3051 | 0.7999 | 0.9995 | 0.058* | |
C7 | 0.7322 (5) | 0.6397 (3) | 0.8541 (2) | 0.0614 (12) | |
H7A | 0.6525 | 0.5990 | 0.8293 | 0.092* | |
H7B | 0.8297 | 0.6046 | 0.8671 | 0.092* | |
H7C | 0.7513 | 0.6928 | 0.8270 | 0.092* | |
C8 | 0.0844 (4) | 0.8467 (2) | 0.90186 (18) | 0.0404 (9) | |
H8 | 0.0625 | 0.8599 | 0.9439 | 0.049* | |
C9 | −0.1767 (4) | 0.9093 (3) | 0.86370 (17) | 0.0414 (8) | |
H9 | −0.2630 | 0.8665 | 0.8436 | 0.050* | |
C10 | −0.2091 (5) | 1.0059 (3) | 0.8299 (2) | 0.0653 (12) | |
H10A | −0.1117 | 1.0433 | 0.8349 | 0.078* | |
H10B | −0.2508 | 0.9980 | 0.7828 | 0.078* | |
C11 | −0.3317 (6) | 1.0539 (4) | 0.8645 (3) | 0.0819 (16) | |
H11A | −0.2954 | 1.1169 | 0.8796 | 0.098* | |
H11B | −0.4332 | 1.0599 | 0.8344 | 0.098* | |
C12 | −0.3499 (5) | 0.9915 (3) | 0.9232 (2) | 0.0670 (13) | |
H12A | −0.4458 | 0.9529 | 0.9131 | 0.080* | |
H12B | −0.3555 | 1.0298 | 0.9622 | 0.080* | |
C13 | −0.2011 (5) | 0.9294 (3) | 0.9345 (2) | 0.0563 (11) | |
H13A | −0.2186 | 0.8711 | 0.9575 | 0.068* | |
H13B | −0.1102 | 0.9629 | 0.9596 | 0.068* | |
C14 | −0.2496 (4) | 0.8557 (2) | 0.61796 (17) | 0.0393 (9) | |
C15 | −0.3019 (4) | 0.8089 (3) | 0.67175 (17) | 0.0390 (8) | |
C16 | −0.4528 (4) | 0.7646 (3) | 0.66019 (17) | 0.0432 (9) | |
H16 | −0.4880 | 0.7324 | 0.6947 | 0.052* | |
C17 | −0.5492 (4) | 0.7683 (3) | 0.59848 (18) | 0.0448 (9) | |
C18 | −0.4993 (5) | 0.8175 (3) | 0.54602 (19) | 0.0540 (11) | |
H18 | −0.5656 | 0.8213 | 0.5047 | 0.065* | |
C19 | −0.3540 (4) | 0.8592 (3) | 0.55627 (18) | 0.0497 (10) | |
H19 | −0.3216 | 0.8916 | 0.5213 | 0.060* | |
C20 | −0.7465 (6) | 0.6658 (3) | 0.6315 (3) | 0.0699 (14) | |
H20A | −0.6642 | 0.6202 | 0.6469 | 0.105* | |
H20B | −0.8423 | 0.6332 | 0.6115 | 0.105* | |
H20C | −0.7675 | 0.7032 | 0.6683 | 0.105* | |
C21 | −0.0928 (4) | 0.8941 (2) | 0.62103 (17) | 0.0400 (8) | |
H21 | −0.0707 | 0.9215 | 0.5822 | 0.048* | |
C22 | 0.1781 (4) | 0.9340 (2) | 0.66504 (17) | 0.0386 (8) | |
H22 | 0.2540 | 0.8808 | 0.6702 | 0.046* | |
C23 | 0.1945 (4) | 0.9857 (3) | 0.60076 (18) | 0.0472 (9) | |
H23A | 0.1985 | 0.9408 | 0.5651 | 0.057* | |
H23B | 0.1057 | 1.0290 | 0.5873 | 0.057* | |
C24 | 0.3521 (5) | 1.0401 (3) | 0.6185 (2) | 0.0557 (11) | |
H24A | 0.3421 | 1.1032 | 0.5989 | 0.067* | |
H24B | 0.4372 | 1.0065 | 0.6022 | 0.067* | |
C25 | 0.3882 (5) | 1.0467 (3) | 0.6946 (2) | 0.0631 (12) | |
H25A | 0.4823 | 1.0096 | 0.7124 | 0.076* | |
H25B | 0.4067 | 1.1123 | 0.7087 | 0.076* | |
C26 | 0.2415 (5) | 1.0072 (3) | 0.71846 (19) | 0.0493 (10) | |
H26A | 0.1632 | 1.0567 | 0.7208 | 0.059* | |
H26B | 0.2703 | 0.9774 | 0.7617 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0408 (3) | 0.0561 (3) | 0.0189 (3) | 0.00078 (18) | 0.00073 (19) | 0.00373 (18) |
N1 | 0.0382 (17) | 0.0517 (17) | 0.0256 (16) | −0.0011 (13) | 0.0040 (13) | 0.0007 (13) |
N2 | 0.0390 (16) | 0.0482 (17) | 0.0227 (15) | 0.0050 (13) | 0.0045 (12) | 0.0025 (13) |
O1 | 0.0477 (15) | 0.0664 (16) | 0.0218 (13) | 0.0132 (13) | 0.0001 (11) | 0.0091 (12) |
O2 | 0.0506 (17) | 0.082 (2) | 0.0432 (17) | 0.0161 (14) | −0.0017 (14) | 0.0044 (15) |
O3 | 0.0483 (15) | 0.0762 (17) | 0.0189 (13) | −0.0110 (13) | −0.0013 (11) | 0.0067 (12) |
O4 | 0.0481 (17) | 0.093 (2) | 0.0370 (16) | −0.0184 (15) | −0.0033 (13) | −0.0022 (15) |
C1 | 0.044 (2) | 0.049 (2) | 0.0206 (18) | 0.0027 (16) | −0.0030 (15) | −0.0013 (16) |
C2 | 0.047 (2) | 0.0435 (19) | 0.0215 (17) | −0.0014 (16) | 0.0030 (15) | 0.0049 (15) |
C3 | 0.045 (2) | 0.052 (2) | 0.0262 (18) | 0.0029 (17) | 0.0067 (16) | 0.0036 (16) |
C4 | 0.042 (2) | 0.050 (2) | 0.036 (2) | 0.0022 (16) | −0.0022 (16) | 0.0066 (17) |
C5 | 0.051 (2) | 0.070 (3) | 0.027 (2) | 0.0025 (19) | −0.0074 (17) | 0.0035 (19) |
C6 | 0.055 (2) | 0.067 (3) | 0.0202 (18) | 0.0014 (19) | 0.0018 (17) | −0.0019 (18) |
C7 | 0.053 (3) | 0.071 (3) | 0.061 (3) | 0.019 (2) | 0.012 (2) | 0.009 (2) |
C8 | 0.044 (2) | 0.055 (2) | 0.0227 (18) | −0.0036 (16) | 0.0081 (16) | −0.0031 (16) |
C9 | 0.040 (2) | 0.055 (2) | 0.0281 (19) | −0.0057 (16) | 0.0050 (15) | −0.0045 (17) |
C10 | 0.062 (3) | 0.073 (3) | 0.064 (3) | 0.018 (2) | 0.021 (2) | 0.018 (2) |
C11 | 0.092 (4) | 0.082 (3) | 0.076 (4) | 0.032 (3) | 0.028 (3) | 0.010 (3) |
C12 | 0.070 (3) | 0.073 (3) | 0.063 (3) | 0.009 (2) | 0.024 (2) | −0.017 (2) |
C13 | 0.061 (3) | 0.072 (3) | 0.038 (2) | 0.005 (2) | 0.017 (2) | −0.005 (2) |
C14 | 0.042 (2) | 0.056 (2) | 0.0185 (18) | 0.0033 (16) | 0.0012 (15) | 0.0013 (15) |
C15 | 0.043 (2) | 0.051 (2) | 0.0215 (18) | 0.0045 (16) | 0.0028 (15) | −0.0023 (16) |
C16 | 0.044 (2) | 0.061 (2) | 0.0234 (18) | −0.0042 (17) | 0.0024 (16) | 0.0031 (17) |
C17 | 0.044 (2) | 0.060 (2) | 0.0279 (19) | −0.0007 (17) | 0.0004 (16) | −0.0064 (18) |
C18 | 0.049 (2) | 0.086 (3) | 0.023 (2) | −0.002 (2) | −0.0044 (17) | 0.001 (2) |
C19 | 0.048 (2) | 0.077 (3) | 0.023 (2) | −0.0010 (19) | 0.0031 (17) | 0.0059 (18) |
C20 | 0.061 (3) | 0.087 (3) | 0.060 (3) | −0.026 (2) | 0.005 (2) | 0.003 (3) |
C21 | 0.044 (2) | 0.054 (2) | 0.0228 (18) | 0.0017 (17) | 0.0071 (15) | 0.0070 (16) |
C22 | 0.038 (2) | 0.045 (2) | 0.0319 (19) | 0.0040 (15) | 0.0053 (15) | 0.0026 (16) |
C23 | 0.053 (2) | 0.056 (2) | 0.034 (2) | −0.0034 (18) | 0.0110 (18) | 0.0057 (18) |
C24 | 0.059 (3) | 0.058 (2) | 0.053 (3) | −0.013 (2) | 0.020 (2) | −0.002 (2) |
C25 | 0.065 (3) | 0.068 (3) | 0.053 (3) | −0.018 (2) | 0.000 (2) | 0.005 (2) |
C26 | 0.057 (2) | 0.056 (2) | 0.034 (2) | −0.0040 (18) | 0.0031 (18) | −0.0020 (18) |
Cu1—O1 | 1.890 (2) | C11—H11A | 0.9700 |
Cu1—O3 | 1.891 (2) | C11—H11B | 0.9700 |
Cu1—N2 | 1.967 (3) | C12—C13 | 1.520 (6) |
Cu1—N1 | 1.978 (3) | C12—H12A | 0.9700 |
N1—C8 | 1.289 (4) | C12—H12B | 0.9700 |
N1—C9 | 1.462 (4) | C13—H13A | 0.9700 |
N2—C21 | 1.292 (4) | C13—H13B | 0.9700 |
N2—C22 | 1.469 (4) | C14—C19 | 1.408 (5) |
O1—C2 | 1.316 (4) | C14—C15 | 1.419 (5) |
O2—C4 | 1.356 (4) | C14—C21 | 1.428 (5) |
O2—C7 | 1.414 (5) | C15—C16 | 1.407 (5) |
O3—C15 | 1.309 (4) | C16—C17 | 1.378 (5) |
O4—C17 | 1.356 (4) | C16—H16 | 0.9300 |
O4—C20 | 1.429 (5) | C17—C18 | 1.403 (5) |
C1—C6 | 1.410 (5) | C18—C19 | 1.349 (5) |
C1—C2 | 1.421 (5) | C18—H18 | 0.9300 |
C1—C8 | 1.432 (5) | C19—H19 | 0.9300 |
C2—C3 | 1.398 (5) | C20—H20A | 0.9600 |
C3—C4 | 1.383 (5) | C20—H20B | 0.9600 |
C3—H3 | 0.9300 | C20—H20C | 0.9600 |
C4—C5 | 1.399 (5) | C21—H21 | 0.9300 |
C5—C6 | 1.346 (5) | C22—C26 | 1.527 (5) |
C5—H5 | 0.9300 | C22—C23 | 1.529 (5) |
C6—H6 | 0.9300 | C22—H22 | 0.9800 |
C7—H7A | 0.9600 | C23—C24 | 1.529 (5) |
C7—H7B | 0.9600 | C23—H23A | 0.9700 |
C7—H7C | 0.9600 | C23—H23B | 0.9700 |
C8—H8 | 0.9300 | C24—C25 | 1.535 (6) |
C9—C13 | 1.524 (5) | C24—H24A | 0.9700 |
C9—C10 | 1.527 (5) | C24—H24B | 0.9700 |
C9—H9 | 0.9800 | C25—C26 | 1.522 (5) |
C10—C11 | 1.518 (6) | C25—H25A | 0.9700 |
C10—H10A | 0.9700 | C25—H25B | 0.9700 |
C10—H10B | 0.9700 | C26—H26A | 0.9700 |
C11—C12 | 1.516 (6) | C26—H26B | 0.9700 |
O1—Cu1—O3 | 144.60 (13) | C13—C12—H12B | 110.8 |
O1—Cu1—N2 | 93.93 (11) | H12A—C12—H12B | 108.9 |
O3—Cu1—N2 | 95.32 (11) | C12—C13—C9 | 102.3 (3) |
O1—Cu1—N1 | 95.40 (11) | C12—C13—H13A | 111.3 |
O3—Cu1—N1 | 94.20 (11) | C9—C13—H13A | 111.3 |
N2—Cu1—N1 | 148.66 (12) | C12—C13—H13B | 111.3 |
C8—N1—C9 | 120.1 (3) | C9—C13—H13B | 111.3 |
C8—N1—Cu1 | 122.4 (2) | H13A—C13—H13B | 109.2 |
C9—N1—Cu1 | 117.6 (2) | C19—C14—C15 | 118.5 (3) |
C21—N2—C22 | 119.3 (3) | C19—C14—C21 | 117.4 (3) |
C21—N2—Cu1 | 122.7 (2) | C15—C14—C21 | 124.0 (3) |
C22—N2—Cu1 | 118.0 (2) | O3—C15—C16 | 117.8 (3) |
C2—O1—Cu1 | 126.8 (2) | O3—C15—C14 | 123.7 (3) |
C4—O2—C7 | 119.1 (3) | C16—C15—C14 | 118.5 (3) |
C15—O3—Cu1 | 126.8 (2) | C17—C16—C15 | 120.8 (3) |
C17—O4—C20 | 118.7 (3) | C17—C16—H16 | 119.6 |
C6—C1—C2 | 117.6 (3) | C15—C16—H16 | 119.6 |
C6—C1—C8 | 118.2 (3) | O4—C17—C16 | 124.2 (3) |
C2—C1—C8 | 124.1 (3) | O4—C17—C18 | 115.3 (3) |
O1—C2—C3 | 117.4 (3) | C16—C17—C18 | 120.5 (3) |
O1—C2—C1 | 123.7 (3) | C19—C18—C17 | 119.2 (3) |
C3—C2—C1 | 118.9 (3) | C19—C18—H18 | 120.4 |
C4—C3—C2 | 120.8 (3) | C17—C18—H18 | 120.4 |
C4—C3—H3 | 119.6 | C18—C19—C14 | 122.5 (4) |
C2—C3—H3 | 119.6 | C18—C19—H19 | 118.8 |
O2—C4—C3 | 123.7 (4) | C14—C19—H19 | 118.8 |
O2—C4—C5 | 115.9 (3) | O4—C20—H20A | 109.5 |
C3—C4—C5 | 120.4 (3) | O4—C20—H20B | 109.5 |
C6—C5—C4 | 119.1 (3) | H20A—C20—H20B | 109.5 |
C6—C5—H5 | 120.5 | O4—C20—H20C | 109.5 |
C4—C5—H5 | 120.5 | H20A—C20—H20C | 109.5 |
C5—C6—C1 | 123.1 (4) | H20B—C20—H20C | 109.5 |
C5—C6—H6 | 118.5 | N2—C21—C14 | 126.9 (3) |
C1—C6—H6 | 118.5 | N2—C21—H21 | 116.5 |
O2—C7—H7A | 109.5 | C14—C21—H21 | 116.5 |
O2—C7—H7B | 109.5 | N2—C22—C26 | 113.1 (3) |
H7A—C7—H7B | 109.5 | N2—C22—C23 | 118.9 (3) |
O2—C7—H7C | 109.5 | C26—C22—C23 | 102.7 (3) |
H7A—C7—H7C | 109.5 | N2—C22—H22 | 107.2 |
H7B—C7—H7C | 109.5 | C26—C22—H22 | 107.2 |
N1—C8—C1 | 127.2 (3) | C23—C22—H22 | 107.2 |
N1—C8—H8 | 116.4 | C24—C23—C22 | 104.1 (3) |
C1—C8—H8 | 116.4 | C24—C23—H23A | 110.9 |
N1—C9—C13 | 119.8 (3) | C22—C23—H23A | 110.9 |
N1—C9—C10 | 112.2 (3) | C24—C23—H23B | 110.9 |
C13—C9—C10 | 102.8 (3) | C22—C23—H23B | 110.9 |
N1—C9—H9 | 107.1 | H23A—C23—H23B | 109.0 |
C13—C9—H9 | 107.1 | C23—C24—C25 | 106.2 (3) |
C10—C9—H9 | 107.1 | C23—C24—H24A | 110.5 |
C11—C10—C9 | 105.5 (3) | C25—C24—H24A | 110.5 |
C11—C10—H10A | 110.6 | C23—C24—H24B | 110.5 |
C9—C10—H10A | 110.6 | C25—C24—H24B | 110.5 |
C11—C10—H10B | 110.6 | H24A—C24—H24B | 108.7 |
C9—C10—H10B | 110.6 | C26—C25—C24 | 106.0 (3) |
H10A—C10—H10B | 108.8 | C26—C25—H25A | 110.5 |
C12—C11—C10 | 106.7 (4) | C24—C25—H25A | 110.5 |
C12—C11—H11A | 110.4 | C26—C25—H25B | 110.5 |
C10—C11—H11A | 110.4 | C24—C25—H25B | 110.5 |
C12—C11—H11B | 110.4 | H25A—C25—H25B | 108.7 |
C10—C11—H11B | 110.4 | C25—C26—C22 | 102.8 (3) |
H11A—C11—H11B | 108.6 | C25—C26—H26A | 111.2 |
C11—C12—C13 | 104.6 (3) | C22—C26—H26A | 111.2 |
C11—C12—H12A | 110.8 | C25—C26—H26B | 111.2 |
C13—C12—H12A | 110.8 | C22—C26—H26B | 111.2 |
C11—C12—H12B | 110.8 | H26A—C26—H26B | 109.1 |
Experimental details
Crystal data | |
Chemical formula | [Cu(C13H16NO2)2] |
Mr | 500.08 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 8.496 (1), 14.054 (2), 20.442 (2) |
β (°) | 100.236 (3) |
V (Å3) | 2402.0 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.94 |
Crystal size (mm) | 0.23 × 0.21 × 0.21 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.812, 0.826 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12222, 4333, 3131 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.163, 1.00 |
No. of reflections | 4333 |
No. of parameters | 300 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.69, −1.16 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Cu1—O1 | 1.890 (2) | Cu1—N2 | 1.967 (3) |
Cu1—O3 | 1.891 (2) | Cu1—N1 | 1.978 (3) |
O1—Cu1—O3 | 144.60 (13) | O1—Cu1—N1 | 95.40 (11) |
O1—Cu1—N2 | 93.93 (11) | O3—Cu1—N1 | 94.20 (11) |
O3—Cu1—N2 | 95.32 (11) | N2—Cu1—N1 | 148.66 (12) |
Schiff bases are known to be versatile ligands in coordination chemistry (Hamaker et al., 2010; Wang et al., 2010; Mirkhani et al., 2010; Liu & Yang, 2009). A large number of complexes with Schiff bases have been reported because of their interesting structures and potential applications (Keypour et al., 2009; Adhikary et al., 2009; Peng et al., 2009). We report here the crystal structure of the title new copper complex with the Schiff base ligand 2-(cyclopentyliminomethyl)-5-methoxyphenol.
The Cu atom in the complex is four-coordinated by two phenolate O atoms and two imine N atoms from two Schiff base ligands, forming a distorted square planar geometry (Fig. 1). The dihedral angle between the C1-C6 and C14-C19 benzene rings is 55.8 (3)°. The bond lengths (Table 1) involving the Cu atom are comparable to those observed in similar copper complexes (Friščić et al., 2002; Marsh & Spek, 2001; Han et al., 2001; Akitsu & Einaga, 2004; Dhar et al., 2003).