Download citation
Download citation
link to html
The title complex, [Cu(C13H16NO2)2], is a mononuclear copper(II) complex. The Cu atom is located on a crystallographic inversion centre and is coordinated by two O and two N atoms from two Schiff base ligands, forming a square-planar geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023860/gk2077sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023860/gk2077Isup2.hkl
Contains datablock I

CCDC reference: 650575

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.108
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.14
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

The interesting Cu(II) complexes with Schiff base ligands have been widely reported previously (Xu et al., 2005; Hebbachi & Benali-Cherif, 2005; Liu et al., 2004; Zhang, 2004; Wang, 2007; Usha et al., 2004). We report herein the title new copper(II) complex, (I), derived from the Schiff base ligand, 2-(cyclopentyliminomethyl)-6-methoxyphenol.

(I) is a mononuclear copper(II) complex (Fig. 1).

Related literature top

For related literature, see: Hebbachi & Benali-Cherif (2005); Liu et al. (2004); Usha et al. (2004); Wang (2007); Xu et al. (2005); Zhang (2004).

Experimental top

3-Methoxy-2-hydroxybenzaldehyde (0.2 mmol, 30.5 mg), cyclopentylamine (0.2 mmol, 17.2 mg), and Cu(CH3COO)2.H2O (0.1 mmol, 20.0 mg) were dissolved in methanol. The mixture was stirred at 325 K for 30 min to give a transparent blue solution. Blue crystals were obtained by slow evaporation of the solution in air.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C–H distances in the range 0.93–0.97 Å and Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(methyl C).

Structure description top

The interesting Cu(II) complexes with Schiff base ligands have been widely reported previously (Xu et al., 2005; Hebbachi & Benali-Cherif, 2005; Liu et al., 2004; Zhang, 2004; Wang, 2007; Usha et al., 2004). We report herein the title new copper(II) complex, (I), derived from the Schiff base ligand, 2-(cyclopentyliminomethyl)-6-methoxyphenol.

(I) is a mononuclear copper(II) complex (Fig. 1).

For related literature, see: Hebbachi & Benali-Cherif (2005); Liu et al. (2004); Usha et al. (2004); Wang (2007); Xu et al. (2005); Zhang (2004).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with anisotropic displacement ellipsoids drawn at the 30% probability level.
bis{2-[(E)-cyclopentyliminomethyl]-6-methoxyphenolato}copper(II) top
Crystal data top
[Cu(C13H16NO2)2]F(000) = 1052
Mr = 500.08Dx = 1.427 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3071 reflections
a = 12.060 (2) Åθ = 2.3–25.4°
b = 10.8025 (18) ŵ = 0.97 mm1
c = 17.863 (3) ÅT = 293 K
V = 2327.1 (7) Å3Block, blue
Z = 40.33 × 0.27 × 0.25 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2662 independent reflections
Radiation source: fine-focus sealed tube1921 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1515
Tmin = 0.739, Tmax = 0.793k = 1313
18677 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0539P)2 + 0.5523P]
where P = (Fo2 + 2Fc2)/3
2662 reflections(Δ/σ)max < 0.001
152 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.52 e Å3
Crystal data top
[Cu(C13H16NO2)2]V = 2327.1 (7) Å3
Mr = 500.08Z = 4
Orthorhombic, PbcaMo Kα radiation
a = 12.060 (2) ŵ = 0.97 mm1
b = 10.8025 (18) ÅT = 293 K
c = 17.863 (3) Å0.33 × 0.27 × 0.25 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2662 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
1921 reflections with I > 2σ(I)
Tmin = 0.739, Tmax = 0.793Rint = 0.048
18677 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.03Δρmax = 0.29 e Å3
2662 reflectionsΔρmin = 0.52 e Å3
152 parameters
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
xyzUiso*/Ueq
Cu10.50001.00000.50000.03149 (14)
O10.48094 (13)1.06065 (17)0.59762 (9)0.0476 (4)
O20.47911 (14)1.21263 (17)0.71126 (10)0.0532 (5)
N10.37204 (14)0.88125 (16)0.51335 (9)0.0309 (4)
C10.30127 (18)0.98086 (19)0.62636 (12)0.0349 (5)
C20.39230 (17)1.05894 (19)0.63916 (11)0.0339 (5)
C30.38780 (18)1.13863 (19)0.70281 (11)0.0385 (5)
C40.2975 (2)1.1376 (2)0.74929 (13)0.0484 (6)
H40.29631.18930.79090.058*
C50.2074 (2)1.0602 (2)0.73515 (14)0.0524 (6)
H50.14611.06150.76670.063*
C60.2092 (2)0.9832 (2)0.67549 (14)0.0474 (6)
H60.14920.93120.66660.057*
C70.30020 (17)0.8935 (2)0.56588 (11)0.0353 (5)
H70.24040.83920.56460.042*
C80.35710 (16)0.77989 (18)0.45869 (11)0.0326 (5)
H80.37010.81500.40890.039*
C90.24757 (18)0.7099 (2)0.45507 (13)0.0416 (5)
H9A0.22490.68090.50410.050*
H9B0.18910.76060.43380.050*
C100.27792 (19)0.6031 (2)0.40378 (13)0.0447 (6)
H10A0.22620.53500.40950.054*
H10B0.27820.62920.35180.054*
C110.3933 (2)0.5656 (2)0.42889 (18)0.0623 (8)
H11A0.43890.54430.38600.075*
H11B0.38970.49470.46210.075*
C120.4416 (2)0.6771 (2)0.46972 (16)0.0532 (7)
H12A0.45140.65910.52250.064*
H12B0.51270.70020.44850.064*
C130.4917 (2)1.2773 (3)0.77932 (19)0.0682 (9)
H13A0.43251.33600.78470.102*
H13B0.56141.32010.77930.102*
H13C0.48981.21980.82030.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0323 (2)0.0320 (2)0.0301 (2)0.00396 (14)0.00267 (14)0.00402 (15)
O10.0444 (9)0.0600 (11)0.0385 (9)0.0173 (8)0.0109 (7)0.0169 (8)
O20.0556 (10)0.0581 (11)0.0457 (10)0.0085 (8)0.0009 (8)0.0213 (9)
N10.0349 (10)0.0284 (9)0.0295 (9)0.0007 (7)0.0007 (7)0.0003 (7)
C10.0372 (12)0.0350 (12)0.0325 (11)0.0033 (9)0.0021 (9)0.0017 (9)
C20.0377 (12)0.0354 (11)0.0286 (10)0.0031 (9)0.0031 (9)0.0014 (9)
C30.0459 (13)0.0366 (11)0.0331 (11)0.0052 (10)0.0029 (10)0.0028 (9)
C40.0575 (15)0.0490 (14)0.0387 (13)0.0116 (12)0.0063 (11)0.0088 (11)
C50.0502 (15)0.0618 (16)0.0452 (14)0.0093 (13)0.0164 (11)0.0045 (12)
C60.0403 (14)0.0551 (15)0.0469 (14)0.0010 (11)0.0074 (11)0.0003 (11)
C70.0326 (11)0.0360 (12)0.0372 (12)0.0038 (9)0.0007 (9)0.0031 (9)
C80.0348 (11)0.0288 (10)0.0342 (11)0.0037 (8)0.0020 (9)0.0001 (9)
C90.0411 (12)0.0405 (13)0.0430 (13)0.0061 (10)0.0021 (10)0.0025 (10)
C100.0533 (15)0.0346 (12)0.0461 (13)0.0109 (10)0.0034 (11)0.0016 (10)
C110.0654 (18)0.0343 (13)0.087 (2)0.0071 (12)0.0115 (16)0.0115 (13)
C120.0479 (15)0.0426 (14)0.0691 (17)0.0101 (11)0.0195 (13)0.0094 (13)
C130.076 (2)0.071 (2)0.0575 (17)0.0026 (15)0.0138 (14)0.0303 (16)
Geometric parameters (Å, º) top
Cu1—O11.8770 (16)C7—H70.9300
Cu1—O1i1.8770 (16)C8—C121.520 (3)
Cu1—N12.0208 (17)C8—C91.523 (3)
Cu1—N1i2.0208 (17)C8—H80.9800
O1—C21.301 (2)C9—C101.518 (3)
O2—C31.369 (3)C9—H9A0.9700
O2—C131.410 (4)C9—H9B0.9700
N1—C71.284 (3)C10—C111.517 (3)
N1—C81.478 (3)C10—H10A0.9700
C1—C21.403 (3)C10—H10B0.9700
C1—C61.416 (3)C11—C121.523 (3)
C1—C71.435 (3)C11—H11A0.9700
C2—C31.427 (3)C11—H11B0.9700
C3—C41.369 (3)C12—H12A0.9700
C4—C51.395 (4)C12—H12B0.9700
C4—H40.9300C13—H13A0.9600
C5—C61.352 (3)C13—H13B0.9600
C5—H50.9300C13—H13C0.9600
C6—H60.9300
O1—Cu1—O1i180.00 (4)C12—C8—C9102.97 (17)
O1—Cu1—N191.06 (7)N1—C8—H8107.0
O1i—Cu1—N188.94 (7)C12—C8—H8107.0
O1—Cu1—N1i88.94 (7)C9—C8—H8107.0
O1i—Cu1—N1i91.06 (7)C10—C9—C8101.17 (17)
N1—Cu1—N1i180.0C10—C9—H9A111.5
C2—O1—Cu1128.71 (14)C8—C9—H9A111.5
C3—O2—C13118.1 (2)C10—C9—H9B111.5
C7—N1—C8118.47 (18)C8—C9—H9B111.5
C7—N1—Cu1122.43 (14)H9A—C9—H9B109.4
C8—N1—Cu1119.04 (12)C11—C10—C9104.20 (19)
C2—C1—C6120.1 (2)C11—C10—H10A110.9
C2—C1—C7121.69 (19)C9—C10—H10A110.9
C6—C1—C7118.1 (2)C11—C10—H10B110.9
O1—C2—C1123.93 (19)C9—C10—H10B110.9
O1—C2—C3118.5 (2)H10A—C10—H10B108.9
C1—C2—C3117.56 (19)C10—C11—C12106.4 (2)
O2—C3—C4125.3 (2)C10—C11—H11A110.5
O2—C3—C2114.17 (19)C12—C11—H11A110.5
C4—C3—C2120.6 (2)C10—C11—H11B110.5
C3—C4—C5121.0 (2)C12—C11—H11B110.5
C3—C4—H4119.5H11A—C11—H11B108.7
C5—C4—H4119.5C8—C12—C11105.01 (18)
C6—C5—C4119.9 (2)C8—C12—H12A110.7
C6—C5—H5120.0C11—C12—H12A110.7
C4—C5—H5120.0C8—C12—H12B110.7
C5—C6—C1120.8 (2)C11—C12—H12B110.7
C5—C6—H6119.6H12A—C12—H12B108.8
C1—C6—H6119.6O2—C13—H13A109.5
N1—C7—C1127.7 (2)O2—C13—H13B109.5
N1—C7—H7116.1H13A—C13—H13B109.5
C1—C7—H7116.1O2—C13—H13C109.5
N1—C8—C12111.95 (17)H13A—C13—H13C109.5
N1—C8—C9120.09 (17)H13B—C13—H13C109.5
Symmetry code: (i) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formula[Cu(C13H16NO2)2]
Mr500.08
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)12.060 (2), 10.8025 (18), 17.863 (3)
V3)2327.1 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.97
Crystal size (mm)0.33 × 0.27 × 0.25
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.739, 0.793
No. of measured, independent and
observed [I > 2σ(I)] reflections
18677, 2662, 1921
Rint0.048
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.108, 1.03
No. of reflections2662
No. of parameters152
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.52

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Bruker, 2000), SHELXTL.

 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds