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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page m894
https://doi.org/10.1107/S1600536812025081

Bis{N-[meth­oxy(4-methylbenzamido)methyl]-2,4-di­methylanilinido-κ2N,O}copper(II)

M. Sukeri M. Yusof,a* Maisara A. Kadira and Bohari M. Yaminb

aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Mengabang Telipot, 21030 Kuala Terengganu, Terengganu, Malaysia, and bSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia
*Correspondence e-mail: mohdsukeri@umt.edu.my

(Received 20 May 2012; accepted 1 June 2012; online 13 June 2012)

In the centrosymmetric mononuclear title complex, [Cu(C18H20N2O2)2], the CuII atom is four-coordinated in a trans-CuN2O2 square-planar geometry with the N—Cu—O chelate angle being 89.97 (11)°. The dihedral angles made by the planes defined by the aromatic ring carbons of the 4-methyl­benzene and 2,4-dimethyl­benzene fragments with the plane defined by the chelate ring are 13.43 (15) and 82.69 (13)° respectively. The angle between the planes defined by the aromatic carbons of the two rings is 89.40 (16)°. A a weak intra­molecular C—H⋯N hydrogen bond occurs.

Related literature

For applications of related compounds, see: Moro et al. (2009[Moro, A. C., Mauro, A. E., Netto, A. V. G., Ananias, S. R., Quilles, M. B., Carlos, I. Z., Pavan, F. R., Leite, C. Q. F. & Hörner, M. (2009). Eur. J. Med. Chem. 44, 4611-4615.]); Rauf et al. (2009[Rauf, M. K., ud-Din, I., Badshah, A., Gielen, M., Ebihara, M., de Vos, D. & Ahmed, S. (2009). J. Inorg. Biochem. 103, 1135-1144.]); D'Cruz et al. (2003[D'Cruz, O. J., Dong, Y. & Uckun, F. M. (2003). Biochem. Biophys. Res. Commun. 302, 253-264.]). For a related structure, see: Shen et al. (1999[Shen, X., Shi, X., Kang, B., Tong, Y., Liu, Y., Gu, L., Liu, Q. & Huang, Y. (1999). Polyhedron, 18, 33-37.]). For C—N bond lengths, see: Arslan et al. (2007[Arslan, H., Flörke, U., Külcü, N. & Binzet, G. (2007). Spectrochim. Acta Part A, 68, 1347-1355.]).

[Scheme 1]

Experimental

Crystal data

  • [Cu(C18H20N2O2)2]

  • Mr = 656.26

  • Triclinic, [P \overline 1]

  • a = 7.949 (2) Å

  • b = 10.191 (3) Å

  • c = 10.844 (4) Å

  • α = 80.784 (6)°

  • β = 74.302 (6)°

  • γ = 79.772 (6)°

  • V = 826.4 (4) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.71 mm−1

  • T = 298 K

  • 0.40 × 0.24 × 0.18 mm
Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS , SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.766, Tmax = 0.884

  • 10650 measured reflections

  • 3792 independent reflections

  • 2609 reflections with I > 2/s(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.198

  • S = 1.01

  • 3792 reflections

  • 205 parameters

  • H-atom parameters constrained

  • Δρmax = 1.10 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C18—H18A⋯N1 0.96 2.27 2.783 (7) 112

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS , SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS , SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I, 265R. DOI: https://doi.org/10.1107/S1600536812025081/qm2070sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025081/qm2070Isup2.hkl

checkCIF report


Comment top

The interest in the synthesis and properties of transition metal complexes containing thiourea derivatives has received a significant level of attention. This is due to their significant biological activity and variation in the mode of binding. Thiourea derivatives have shown great potential in medicinal applications especially as anticancer, antifungal, antibacterial and most interestingly as anti-HIV agents (Moro et al., 2009; Rauf et al., 2009; D'Cruz et al., 2003). In this work, the title compound derived from the desulfurization of N-(4-methylbenzoyl)-N'-(2,4-dimethylphenyl)thiourea has been successfully synthesised. The molecular structure shows that the ligand acts as a bidentate chelating ligand through nitrogen and oxygen atoms (Fig. 1). The molecule is discrete and centrosymmeric about the Cu1 atom. The two ligands coordinate to the metal centre with the N1-Cu1-O1 bond angles of 89.97 (11)°. This is typical square planar geometry for a four coordinate complex. The Cu1-N1 and Cu1-O1 bond lengths are 1.963 (2) and 1.892 (2)Å, respectively, which is in agreement with a related complex (Shen et al., 1999). The bond length O1-C8 is 1.263 (3)Å, which is slightly shorter than the other bonds. This indicates the presence of partial double bond character in the this bond due to resonance effects. The C-N bond lengths of the [C9-N2 = 1.310 (4)Å, C9-N1= 1.325 (4)Å and C8-N1 = 1.313 (4)Å] groups lie in the range expected for C-N bonds with partial double bond character. This is shorter than the bond lengths for normal C-N bonds (about 1.48Å) reported in the literature (Arslan et al., 2007). The presence of strong delocalization in the chelate ring N2, C9, N1, C8 and O1 atoms, suggested the presence of a conjugated π-system along N2-C9-N1-C8-O1 which is similar to other reported carbonylthiourea derivatives (Shen et al., 1999).

The six-membered ring Cu1-N2-C9-N1-C8-O1-Cu1, 4-methylphenyl (C1-C7), and 2,4-dimethylphenyl (C10-C15/C16/C17) groups are essentially planar with maximum deviation of 0.016 (2)Å for atom N2 from the least-squares planes. The chelating ring makes dihedral angles with the 4-methylphenyl and 2,4-dimethylphenyl fragments of 13.43 (15) and 82.69 (13)°, respectively. The plane of the 4-methyphenyl and 2,4-dimethyphenyl fragments are inclined to each other at an angle of 89.40 (16)°. There is a weak intramolecular hydrogen bond C18-H18A···N1 resulting a pseudo five-membered ring, C11-C16-C18-H18A···N1 (Table 1).

Related literature top

For applications of related compounds, see: Moro et al. (2009); Rauf et al. (2009); D'Cruz et al. (2003). For a related structure, see: Shen et al. (1999). For C—N bond lengths, see: Arslan et al. (2007).

Experimental top

A solution of N-(4-methylbenzoyl)-N'-(2,4-dimethylphenyl)thiourea (0.51 g, 2 mmol) in DCM (30 ml) was added dropwise to a solution of copper(II) acetate monohydrate (0.17 g, 1 mmol) in MeOH (50 ml) at about 15 minutes rate in 100 ml two-necked round bottom flask with constant stirring at room temperature. The reaction was slowly put under reflux for ca. 3 hours. Reaction progress was monitored by TLC (hexane: ethyl acetate; 7:3). When the reaction had completed, the solvent was removed in-vacuo and followed by recrystallisation from DCM: MeOH (1:3) to afford dark green solid crystals. The crude product was purified by preparative TLC (hexane: acetone; 7:3) and the dark green band was collected and recrystallised from MeOH to afford the title compound (0.16 g, 24°).

Refinement top

All H atoms attached to C and N atoms were fixed geometrically and treated as riding with C-H= 0.93-0.97 Å(aromatic and methylene) and N—H= 0.86 Å(amino) with Uiso(H)=1.2Ueq(C or N). There are highest peak 1.26Å and deepest hole 0.93Å for Br1 atom.

Structure description top

The interest in the synthesis and properties of transition metal complexes containing thiourea derivatives has received a significant level of attention. This is due to their significant biological activity and variation in the mode of binding. Thiourea derivatives have shown great potential in medicinal applications especially as anticancer, antifungal, antibacterial and most interestingly as anti-HIV agents (Moro et al., 2009; Rauf et al., 2009; D'Cruz et al., 2003). In this work, the title compound derived from the desulfurization of N-(4-methylbenzoyl)-N'-(2,4-dimethylphenyl)thiourea has been successfully synthesised. The molecular structure shows that the ligand acts as a bidentate chelating ligand through nitrogen and oxygen atoms (Fig. 1). The molecule is discrete and centrosymmeric about the Cu1 atom. The two ligands coordinate to the metal centre with the N1-Cu1-O1 bond angles of 89.97 (11)°. This is typical square planar geometry for a four coordinate complex. The Cu1-N1 and Cu1-O1 bond lengths are 1.963 (2) and 1.892 (2)Å, respectively, which is in agreement with a related complex (Shen et al., 1999). The bond length O1-C8 is 1.263 (3)Å, which is slightly shorter than the other bonds. This indicates the presence of partial double bond character in the this bond due to resonance effects. The C-N bond lengths of the [C9-N2 = 1.310 (4)Å, C9-N1= 1.325 (4)Å and C8-N1 = 1.313 (4)Å] groups lie in the range expected for C-N bonds with partial double bond character. This is shorter than the bond lengths for normal C-N bonds (about 1.48Å) reported in the literature (Arslan et al., 2007). The presence of strong delocalization in the chelate ring N2, C9, N1, C8 and O1 atoms, suggested the presence of a conjugated π-system along N2-C9-N1-C8-O1 which is similar to other reported carbonylthiourea derivatives (Shen et al., 1999).

The six-membered ring Cu1-N2-C9-N1-C8-O1-Cu1, 4-methylphenyl (C1-C7), and 2,4-dimethylphenyl (C10-C15/C16/C17) groups are essentially planar with maximum deviation of 0.016 (2)Å for atom N2 from the least-squares planes. The chelating ring makes dihedral angles with the 4-methylphenyl and 2,4-dimethylphenyl fragments of 13.43 (15) and 82.69 (13)°, respectively. The plane of the 4-methyphenyl and 2,4-dimethyphenyl fragments are inclined to each other at an angle of 89.40 (16)°. There is a weak intramolecular hydrogen bond C18-H18A···N1 resulting a pseudo five-membered ring, C11-C16-C18-H18A···N1 (Table 1).

For applications of related compounds, see: Moro et al. (2009); Rauf et al. (2009); D'Cruz et al. (2003). For a related structure, see: Shen et al. (1999). For C—N bond lengths, see: Arslan et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with the atom labeling scheme. Displacement ellipsods are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
Bis{N-[methoxy(4-methylbenzamido)methyl]-2,4-dimethylanilinido- κ2N,O}copper(II) top
Crystal data top
[Cu(C18H20N2O2)2]V = 826.4 (4) Å3
Mr = 656.26Z = 1
Triclinic, P1F(000) = 345
Hall symbol: -P 1Dx = 1.319 Mg m−3
a = 7.949 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.191 (3) Åθ = 2.0–27.5°
c = 10.844 (4) ŵ = 0.71 mm−1
α = 80.784 (6)°T = 298 K
β = 74.302 (6)°Slab, dark green
γ = 79.772 (6)°0.40 × 0.24 × 0.18 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3792 independent reflections
Radiation source: fine-focus sealed tube2609 reflections with I > 2/s(I)
Graphite monochromatorRint = 0.029
Detector resolution: 83.66 pixels mm-1θmax = 27.5°, θmin = 2.0°
ω scanh = −10→10
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		k = −13→13
Tmin = 0.766, Tmax = 0.884l = −14→14
10650 measured reflections
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1258P)2 + 0.1796P]
where P = (Fo2 + 2Fc2)/3
3792 reflections(Δ/σ)max < 0.001
205 parametersΔρmax = 1.10 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
[Cu(C18H20N2O2)2]γ = 79.772 (6)°
Mr = 656.26V = 826.4 (4) Å3
Triclinic, P1Z = 1
a = 7.949 (2) ÅMo Kα radiation
b = 10.191 (3) ŵ = 0.71 mm−1
c = 10.844 (4) ÅT = 298 K
α = 80.784 (6)°0.40 × 0.24 × 0.18 mm
β = 74.302 (6)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3792 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		2609 reflections with I > 2/s(I)
Tmin = 0.766, Tmax = 0.884Rint = 0.029
10650 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.198H-atom parameters constrained
S = 1.01Δρmax = 1.10 e Å−3
3792 reflectionsΔρmin = −0.43 e Å−3
205 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.00000.50000.00000.0627 (3)
O1−0.1657 (4)0.3971 (2)0.1152 (3)0.0901 (10)
N2−0.0057 (4)0.1849 (3)0.1172 (3)0.0681 (8)
H2B−0.00590.10330.15310.082*
N10.1674 (4)0.3356 (3)−0.0332 (3)0.0656 (8)
C1−0.3153 (5)0.0812 (4)0.2570 (4)0.0821 (13)
H1A−0.21250.02150.23320.098*
C2−0.4700 (6)0.0327 (4)0.3219 (5)0.1020 (17)
H2A−0.4695−0.05950.34290.122*
C3−0.6273 (5)0.1185 (4)0.3570 (4)0.0756 (11)
C4−0.6217 (5)0.2527 (4)0.3283 (4)0.0815 (12)
H4A−0.72400.31240.35350.098*
C5−0.4678 (5)0.3015 (4)0.2629 (4)0.0791 (12)
H5A−0.46890.39380.24230.095*
C6−0.3110 (4)0.2167 (3)0.2269 (3)0.0592 (8)
C7−0.7988 (6)0.0625 (6)0.4239 (6)0.1115 (19)
H7A−0.89350.13530.44120.167*
H7B−0.78730.00960.50350.167*
H7C−0.82390.00730.36900.167*
C8−0.1487 (4)0.2717 (3)0.1485 (3)0.0589 (9)
C90.1395 (4)0.2185 (3)0.0320 (4)0.0630 (9)
O30.2725 (3)0.1187 (2)0.0036 (3)0.0813 (9)
C100.2530 (6)−0.0141 (4)0.0702 (5)0.0887 (14)
H10A0.3583−0.07460.04000.133*
H10B0.1542−0.04410.05370.133*
H10C0.2335−0.01200.16120.133*
C110.3306 (4)0.3394 (3)−0.1320 (4)0.0662 (10)
C120.4865 (5)0.3460 (4)−0.1022 (5)0.0841 (13)
H12A0.49050.3481−0.01760.101*
C130.6398 (5)0.3496 (4)−0.2046 (6)0.0915 (15)
H13A0.74660.3515−0.18560.110*
C140.6383 (6)0.3502 (4)−0.3302 (6)0.0976 (17)
C150.4796 (6)0.3439 (4)−0.3572 (5)0.0901 (14)
H15A0.47550.3433−0.44200.108*
C160.3248 (5)0.3384 (4)−0.2577 (5)0.0763 (12)
C170.8026 (7)0.3562 (6)−0.4423 (6)0.129 (2)
H17A0.90240.3606−0.41000.193*
H17B0.78440.4346−0.50210.193*
H17C0.82410.2774−0.48540.193*
C180.1646 (7)0.3292 (7)−0.2882 (6)0.1151 (18)
H18A0.07110.3267−0.21060.173*
H18B0.17780.2489−0.32760.173*
H18C0.13660.4060−0.34690.173*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0487 (4)0.0292 (3)0.0850 (5)−0.0033 (2)0.0177 (3)0.0044 (2)
O10.0619 (15)0.0325 (11)0.133 (2)−0.0030 (10)0.0375 (15)0.0051 (13)
N20.0540 (16)0.0318 (13)0.093 (2)−0.0040 (11)0.0103 (14)0.0142 (13)
N10.0492 (15)0.0347 (13)0.087 (2)−0.0020 (11)0.0173 (13)0.0042 (12)
C10.067 (2)0.0387 (17)0.110 (3)−0.0080 (16)0.022 (2)0.0062 (18)
C20.083 (3)0.045 (2)0.142 (4)−0.021 (2)0.034 (3)−0.001 (2)
C30.067 (2)0.064 (2)0.079 (3)−0.0243 (18)0.0207 (18)−0.0087 (19)
C40.061 (2)0.060 (2)0.096 (3)−0.0054 (17)0.0249 (19)−0.008 (2)
C50.067 (2)0.0414 (18)0.102 (3)−0.0108 (16)0.022 (2)−0.0004 (18)
C60.0580 (19)0.0388 (16)0.064 (2)−0.0093 (13)0.0105 (15)0.0010 (14)
C70.076 (3)0.104 (4)0.132 (4)−0.044 (3)0.034 (3)−0.018 (3)
C80.0538 (18)0.0326 (14)0.072 (2)−0.0066 (13)0.0112 (15)0.0001 (13)
C90.0490 (17)0.0349 (15)0.086 (2)−0.0020 (13)0.0062 (16)0.0032 (15)
O30.0555 (14)0.0312 (11)0.123 (2)0.0030 (10)0.0185 (14)0.0111 (12)
C100.075 (3)0.0341 (17)0.125 (4)0.0045 (16)0.007 (2)0.0141 (19)
C110.0522 (19)0.0314 (14)0.087 (3)−0.0001 (13)0.0195 (16)0.0035 (15)
C120.048 (2)0.048 (2)0.128 (4)−0.0017 (15)0.008 (2)0.014 (2)
C130.049 (2)0.057 (2)0.136 (4)−0.0009 (17)0.012 (2)0.014 (2)
C140.066 (3)0.048 (2)0.134 (4)0.0010 (18)0.036 (3)0.005 (2)
C150.086 (3)0.058 (2)0.098 (3)−0.014 (2)0.024 (2)−0.004 (2)
C160.057 (2)0.049 (2)0.106 (3)−0.0094 (16)0.011 (2)−0.0074 (19)
C170.074 (3)0.103 (4)0.154 (5)−0.006 (3)0.053 (3)0.001 (3)
C180.100 (4)0.120 (5)0.123 (4)−0.028 (4)−0.015 (3)−0.014 (4)
Geometric parameters (Å, º) top
Cu1—O11.891 (2)C7—H7C0.9600
Cu1—O1i1.891 (2)C9—O31.338 (4)
Cu1—N1i1.962 (3)O3—C101.442 (4)
Cu1—N11.962 (3)C10—H10A0.9600
O1—C81.264 (4)C10—H10B0.9600
N2—C81.312 (4)C10—H10C0.9600
N2—C91.328 (4)C11—C121.377 (6)
N2—H2B0.8600C11—C161.378 (6)
N1—C91.309 (4)C12—C131.411 (6)
N1—C111.444 (4)C12—H12A0.9300
C1—C61.371 (5)C13—C141.364 (8)
C1—C21.374 (5)C13—H13A0.9300
C1—H1A0.9300C14—C151.385 (7)
C2—C31.391 (6)C14—C171.527 (6)
C2—H2A0.9300C15—C161.403 (5)
C3—C41.359 (6)C15—H15A0.9300
C3—C71.523 (5)C16—C181.421 (7)
C4—C51.371 (5)C17—H17A0.9600
C4—H4A0.9300C17—H17B0.9600
C5—C61.384 (5)C17—H17C0.9600
C5—H5A0.9300C18—H18A0.9600
C6—C81.487 (4)C18—H18B0.9600
C7—H7A0.9600C18—H18C0.9600
C7—H7B0.9600
O1—Cu1—O1i180.00 (13)N1—C9—N2128.6 (3)
O1—Cu1—N1i90.03 (11)N1—C9—O3115.1 (3)
O1i—Cu1—N1i89.97 (11)N2—C9—O3116.3 (3)
O1—Cu1—N189.97 (11)C9—O3—C10118.9 (3)
O1i—Cu1—N190.03 (11)O3—C10—H10A109.5
N1i—Cu1—N1180.0O3—C10—H10B109.5
C8—O1—Cu1128.5 (2)H10A—C10—H10B109.5
C8—N2—C9122.4 (3)O3—C10—H10C109.5
C8—N2—H2B118.8H10A—C10—H10C109.5
C9—N2—H2B118.8H10B—C10—H10C109.5
C9—N1—C11116.6 (3)C12—C11—C16121.0 (3)
C9—N1—Cu1122.7 (2)C12—C11—N1121.2 (4)
C11—N1—Cu1120.7 (2)C16—C11—N1117.7 (3)
C6—C1—C2120.7 (4)C11—C12—C13117.6 (5)
C6—C1—H1A119.6C11—C12—H12A121.2
C2—C1—H1A119.6C13—C12—H12A121.2
C1—C2—C3121.4 (4)C14—C13—C12122.9 (5)
C1—C2—H2A119.3C14—C13—H13A118.5
C3—C2—H2A119.3C12—C13—H13A118.5
C4—C3—C2117.6 (3)C13—C14—C15118.2 (4)
C4—C3—C7121.9 (4)C13—C14—C17123.5 (5)
C2—C3—C7120.6 (4)C15—C14—C17118.3 (6)
C3—C4—C5121.2 (4)C14—C15—C16120.5 (5)
C3—C4—H4A119.4C14—C15—H15A119.7
C5—C4—H4A119.4C16—C15—H15A119.7
C4—C5—C6121.5 (4)C11—C16—C15119.8 (4)
C4—C5—H5A119.2C11—C16—C18121.0 (4)
C6—C5—H5A119.2C15—C16—C18119.2 (5)
C1—C6—C5117.5 (3)C14—C17—H17A109.5
C1—C6—C8121.9 (3)C14—C17—H17B109.5
C5—C6—C8120.4 (3)H17A—C17—H17B109.5
C3—C7—H7A109.5C14—C17—H17C109.5
C3—C7—H7B109.5H17A—C17—H17C109.5
H7A—C7—H7B109.5H17B—C17—H17C109.5
C3—C7—H7C109.5C16—C18—H18A109.5
H7A—C7—H7C109.5C16—C18—H18B109.5
H7B—C7—H7C109.5H18A—C18—H18B109.5
O1—C8—N2127.0 (3)C16—C18—H18C109.5
O1—C8—C6116.1 (3)H18A—C18—H18C109.5
N2—C8—C6116.8 (3)H18B—C18—H18C109.5
O1i—Cu1—O1—C8104 (100)C5—C6—C8—N2−179.4 (4)
N1i—Cu1—O1—C8−178.2 (4)C11—N1—C9—N2−172.2 (4)
N1—Cu1—O1—C81.8 (4)Cu1—N1—C9—N28.3 (6)
O1—Cu1—N1—C9−7.7 (4)C11—N1—C9—O34.2 (6)
O1i—Cu1—N1—C9172.3 (4)Cu1—N1—C9—O3−175.3 (3)
N1i—Cu1—N1—C9−128 (100)C8—N2—C9—N1−0.1 (7)
O1—Cu1—N1—C11172.8 (3)C8—N2—C9—O3−176.4 (4)
O1i—Cu1—N1—C11−7.2 (3)N1—C9—O3—C10−179.6 (4)
N1i—Cu1—N1—C1153 (100)N2—C9—O3—C10−2.8 (6)
C6—C1—C2—C31.3 (8)C9—N1—C11—C12−82.1 (5)
C1—C2—C3—C4−2.0 (8)Cu1—N1—C11—C1297.4 (4)
C1—C2—C3—C7177.4 (5)C9—N1—C11—C1699.0 (4)
C2—C3—C4—C52.4 (8)Cu1—N1—C11—C16−81.5 (4)
C7—C3—C4—C5−177.0 (5)C16—C11—C12—C13−1.0 (5)
C3—C4—C5—C6−2.0 (8)N1—C11—C12—C13−179.9 (3)
C2—C1—C6—C5−0.8 (7)C11—C12—C13—C141.8 (6)
C2—C1—C6—C8−175.5 (4)C12—C13—C14—C15−1.6 (6)
C4—C5—C6—C11.1 (7)C12—C13—C14—C17179.0 (4)
C4—C5—C6—C8175.9 (4)C13—C14—C15—C160.6 (6)
Cu1—O1—C8—N25.3 (7)C17—C14—C15—C16−179.9 (4)
Cu1—O1—C8—C6−171.8 (3)C12—C11—C16—C150.2 (5)
C9—N2—C8—O1−7.5 (7)N1—C11—C16—C15179.1 (3)
C9—N2—C8—C6169.6 (4)C12—C11—C16—C18178.9 (4)
C1—C6—C8—O1172.6 (4)N1—C11—C16—C18−2.2 (6)
C5—C6—C8—O1−2.0 (6)C14—C15—C16—C110.1 (6)
C1—C6—C8—N2−4.9 (6)C14—C15—C16—C18−178.8 (5)
Symmetry code: (i) −x, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···N10.962.272.783 (7)112

Experimental details

Crystal data
Chemical formula[Cu(C18H20N2O2)2]
Mr656.26
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.949 (2), 10.191 (3), 10.844 (4)
α, β, γ (°)80.784 (6), 74.302 (6), 79.772 (6)
V (Å3)826.4 (4)
Z1
Radiation typeMo Kα
µ (mm−1)0.71
Crystal size (mm)0.40 × 0.24 × 0.18
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.766, 0.884
No. of measured, independent and
observed [I > 2/s(I)] reflections		10650, 3792, 2609
Rint0.029
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.198, 1.01
No. of reflections3792
No. of parameters205
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.10, −0.43

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···N10.962.272.783 (7)112
 

Acknowledgements

The authors thank the Ministry of Higher Education of Malaysia and both Universiti Kebangsaan Malaysia and Universiti Malaysia Terengganu for the research grant FRGS 59001.

References

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page m894
https://doi.org/10.1107/S1600536812025081
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