Tetra-μ-acetato-κ8O:O′-bis­{[N-(4-chloro­phen­yl)-4-methyl­pyridin-2-amine-κN1]copper(II)}

Fairuz, Z.A.; Aiyub, Z.; Abdullah, Z.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536810030187

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages m1049-m1050

https://doi.org/10.1107/S1600536810030187

Open

access

Tetra-μ-acetato-κ⁸O:O′-bis{[N-(4-chlorophenyl)-4-methylpyridin-2-amine-κN¹]copper(II)}

Zainal A. Fairuz,^a Zaharah Aiyub,^a Zanariah Abdullah,^a ‡ Seik Weng Ng ^a and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 29 July 2010; accepted 29 July 2010; online 4 August 2010)

In the crystal structure of the title complex, [Cu₂(CH₃COO)₄(C₁₂H₁₁ClN₂)₂], the complete binuclear molecule is generated by a crystallographic centre of inversion; the four acetate groups each bridge a pair of Cu^II atoms. The coordination of the metal atom is distorted octahedral within a donor set defined by four O atoms, the heterocyclic N atom and the second Cu atom. The pyridine ring is twisted with respect to the benzene ring, forming a dihedral angle of 33.9 (2)°. An intramolecular N—H⋯O hydrogen bond is present between the amino group and a carboxyl O atom. Intermolecular interactions of the C—H⋯π type link molecules in the crystal structure.

Related literature

For examples of tetrakisacetatobis[(substituted 2-aminopyridyl)copper] complexes, see: Barquín et al. (2004 ); Seco et al. (2004 ); Sieroń (2004 ); Fairuz et al. (2009 ).

Experimental

Crystal data

[Cu₂(C₂H₃O₂)₄(C₁₂H₁₁ClN₂)₂]
M_r = 800.61
Monoclinic, P 2₁ /c
a = 11.7430 (17) Å
b = 15.619 (2) Å
c = 9.9866 (14) Å
β = 109.901 (2)°
V = 1722.3 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.45 mm⁻¹
T = 296 K
0.35 × 0.25 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.632, T_max = 0.931
11432 measured reflections
3951 independent reflections
2460 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.151
S = 1.04
3951 reflections
224 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O3ⁱ	1.967 (3)
Cu1—O1ⁱ	1.975 (3)
Cu1—O2	1.983 (3)
Cu1—O4	1.984 (3)
Cu1—N1	2.220 (3)
Cu1—Cu1ⁱ	2.6431 (10)
Symmetry code: (i) -x+2, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C5–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4	0.85 (4)	2.30 (2)	3.101 (5)	156 (4)
C4—H4a⋯Cg1ⁱⁱ	0.96	2.83	3.650 (5)	144
Symmetry code: (ii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810030187/hb5589sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030187/hb5589Isup2.hkl

checkCIF report

Comment top

The binuclear title complex, (I), was studied in connection with the structural characterization of tetrakisacetatobis[(substituted 2-aminopyridyl)copper] complexes, see: Barquín et al., 2004; Seco et al., 2004; Sieroń, 2004; Fairuz et al., 2009). The binuclear copper(II) complex, Fig. 1, is situated about a centre of inversion and features two Cu atoms bridged by four acetate groups. The Cu–O bond distances lie in the experimentally equivalent range 1.967 (3) to 1.984 (3) Å, Table 1. The coordination environment for each Cu atom is completed by a N atom derived from the N-4-chloroanilino-4-picoline ligand and the second Cu atom [Cu···Cuⁱ = 2.6431 (10) Å]. The resulting hexa-coordinated geometry is based on an octahedron. An intramolecular N1–H···O4 interaction is noted, Table 2. The N-heterocycle is non-planar with the dihedral angle formed between the pyridine and benzene rings being 33.9 (2) °. The major twist in the molecule occurs around the amine group as seen in the value of the C9–N2–C11–C12 torsion angle of 24.1 (8) °. The most obvious intermolecular contact operating in the crystal structure is of the type C–H···π and occurs between methyl-H and pyridine rings, Table 2. These link complex molecules that stack in columns along the a axis, Fig. 2.

Related literature top

For examples of tetrakisacetatobis[(substituted 2-aminopyridyl)copper] complexes, see: Barquín et al. (2004); Seco et al. (2004); Sieroń (2004); Fairuz et al. (2009).

Experimental top

A mixture of N-(4-chlorophenyl)-4-methylpyridin-2-amine (0.2408 g, 1.1 mmol) in acetonitrile (15 ml) and trimethyl orthoformate (10 ml) was heated to 328 K. Copper acetate (0.1 g, 0.5 mmol) dissolved in acetonitrile (15 ml) was added drop wise to the ligand solution. The green solution was left at room temperature and green plates of (I) were collected after a few days.

Structure description top

For examples of tetrakisacetatobis[(substituted 2-aminopyridyl)copper] complexes, see: Barquín et al. (2004); Seco et al. (2004); Sieroń (2004); Fairuz et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level. Symmetry code: (i) 2–x, 1–y, 1–z.
	Fig. 2. Unit-cell contents shown in projection down the a axis in (I). The C–H···π contacts are shown as purple dashed lines.

Tetra-µ-acetato-κ⁸O:O'-bis{[N-(4-chlorophenyl)-4- methylpyridin-2-amine-κN¹]copper(II)} top

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₂H₁₁ClN₂)₂]	F(000) = 820
M_r = 800.61	D_x = 1.544 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2098 reflections
a = 11.7430 (17) Å	θ = 2.5–23.4°
b = 15.619 (2) Å	µ = 1.45 mm⁻¹
c = 9.9866 (14) Å	T = 296 K
β = 109.901 (2)°	Plate, green
V = 1722.3 (4) Å³	0.35 × 0.25 × 0.05 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	3951 independent reflections
Radiation source: fine-focus sealed tube	2460 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ω scan	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→13
T_min = 0.632, T_max = 0.931	k = −19→20
11432 measured reflections	l = −11→12

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.064P)² + 1.063P] where P = (F_o² + 2F_c²)/3
3951 reflections	(Δ/σ)_max = 0.001
224 parameters	Δρ_max = 0.49 e Å⁻³
1 restraint	Δρ_min = −0.77 e Å⁻³

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₂H₁₁ClN₂)₂]	V = 1722.3 (4) Å³
M_r = 800.61	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7430 (17) Å	µ = 1.45 mm⁻¹
b = 15.619 (2) Å	T = 296 K
c = 9.9866 (14) Å	0.35 × 0.25 × 0.05 mm
β = 109.901 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3951 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2460 reflections with I > 2σ(I)
T_min = 0.632, T_max = 0.931	R_int = 0.065
11432 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.49 e Å⁻³
3951 reflections	Δρ_min = −0.77 e Å⁻³
224 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.92999 (4)	0.47727 (4)	0.57325 (5)	0.03790 (19)
Cl1	0.17644 (11)	0.30281 (12)	0.10013 (15)	0.0756 (5)
N1	0.8173 (3)	0.4410 (2)	0.7033 (3)	0.0359 (8)
N2	0.6604 (3)	0.3905 (3)	0.5143 (4)	0.0514 (11)
H2	0.712 (3)	0.386 (3)	0.472 (4)	0.054 (14)*
O1	0.9185 (3)	0.5697 (2)	0.2909 (3)	0.0520 (8)
O2	0.7991 (2)	0.5312 (2)	0.4143 (3)	0.0526 (9)
O3	1.0247 (3)	0.4097 (2)	0.3375 (3)	0.0502 (8)
O4	0.9027 (3)	0.3711 (2)	0.4573 (4)	0.0539 (9)
C1	0.8177 (4)	0.5643 (3)	0.3087 (5)	0.0424 (10)
C2	0.7092 (4)	0.6009 (4)	0.1941 (5)	0.0656 (15)
H2A	0.6375	0.5713	0.1939	0.098*
H2B	0.7191	0.5942	0.1032	0.098*
H2C	0.7018	0.6607	0.2122	0.098*
C3	0.9545 (3)	0.3572 (3)	0.3661 (4)	0.0408 (10)
C4	0.9312 (4)	0.2732 (3)	0.2895 (5)	0.0569 (13)
H4A	0.8869	0.2365	0.3312	0.085*
H4B	1.0070	0.2468	0.2971	0.085*
H4C	0.8849	0.2825	0.1909	0.085*
C5	0.8690 (4)	0.4552 (3)	0.8442 (5)	0.0490 (12)
H5	0.9457	0.4798	0.8764	0.059*
C6	0.8160 (4)	0.4360 (4)	0.9428 (5)	0.0531 (13)
H6	0.8555	0.4474	1.0388	0.064*
C7	0.7010 (4)	0.3986 (3)	0.8961 (4)	0.0456 (11)
C8	0.6464 (3)	0.3833 (3)	0.7531 (4)	0.0417 (11)
H8	0.5700	0.3584	0.7193	0.050*
C9	0.7059 (3)	0.4054 (3)	0.6584 (4)	0.0350 (9)
C10	0.6402 (5)	0.3728 (4)	1.0011 (5)	0.0710 (17)
H10A	0.5833	0.4162	1.0044	0.107*
H10B	0.7002	0.3662	1.0939	0.107*
H10C	0.5984	0.3195	0.9718	0.107*
C11	0.5429 (3)	0.3694 (3)	0.4227 (4)	0.0375 (10)
C12	0.4356 (4)	0.3881 (3)	0.4500 (4)	0.0414 (10)
H12	0.4400	0.4149	0.5347	0.050*
C13	0.3230 (4)	0.3668 (3)	0.3517 (5)	0.0447 (11)
H13	0.2526	0.3776	0.3717	0.054*
C14	0.3172 (4)	0.3294 (3)	0.2243 (5)	0.0436 (11)
C15	0.4220 (4)	0.3123 (3)	0.1936 (5)	0.0500 (12)
H15	0.4171	0.2877	0.1070	0.060*
C16	0.5334 (4)	0.3321 (3)	0.2928 (5)	0.0474 (12)
H16	0.6034	0.3202	0.2725	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0227 (2)	0.0514 (4)	0.0388 (3)	−0.0041 (2)	0.00946 (19)	0.0002 (3)
Cl1	0.0348 (6)	0.1143 (13)	0.0618 (8)	−0.0131 (7)	−0.0044 (5)	−0.0148 (8)
N1	0.0246 (15)	0.050 (2)	0.0316 (17)	−0.0048 (15)	0.0081 (13)	−0.0007 (16)
N2	0.0275 (17)	0.091 (3)	0.037 (2)	−0.021 (2)	0.0132 (15)	−0.011 (2)
O1	0.0338 (15)	0.075 (2)	0.0466 (18)	0.0082 (16)	0.0124 (14)	0.0134 (17)
O2	0.0260 (14)	0.080 (3)	0.0495 (18)	0.0036 (15)	0.0100 (13)	0.0128 (17)
O3	0.0449 (17)	0.058 (2)	0.0533 (19)	−0.0118 (16)	0.0234 (15)	−0.0082 (16)
O4	0.0485 (18)	0.058 (2)	0.064 (2)	−0.0131 (16)	0.0299 (17)	−0.0089 (17)
C1	0.031 (2)	0.049 (3)	0.043 (2)	0.001 (2)	0.0071 (18)	−0.005 (2)
C2	0.043 (3)	0.085 (4)	0.056 (3)	0.023 (3)	0.002 (2)	0.010 (3)
C3	0.0264 (18)	0.050 (3)	0.041 (2)	−0.0003 (19)	0.0048 (17)	−0.003 (2)
C4	0.053 (3)	0.052 (3)	0.061 (3)	−0.012 (2)	0.013 (2)	−0.008 (3)
C5	0.033 (2)	0.074 (4)	0.039 (2)	−0.017 (2)	0.0113 (18)	−0.007 (2)
C6	0.042 (2)	0.081 (4)	0.036 (2)	−0.017 (3)	0.0125 (19)	−0.011 (2)
C7	0.033 (2)	0.069 (3)	0.036 (2)	−0.004 (2)	0.0133 (17)	0.005 (2)
C8	0.0242 (18)	0.059 (3)	0.041 (2)	−0.0074 (19)	0.0093 (17)	0.006 (2)
C9	0.0247 (17)	0.043 (3)	0.033 (2)	−0.0035 (17)	0.0049 (15)	0.0015 (18)
C10	0.051 (3)	0.121 (5)	0.045 (3)	−0.016 (3)	0.021 (2)	0.005 (3)
C11	0.0256 (18)	0.049 (3)	0.035 (2)	−0.0080 (18)	0.0068 (16)	0.0046 (19)
C12	0.033 (2)	0.054 (3)	0.037 (2)	−0.002 (2)	0.0110 (18)	−0.004 (2)
C13	0.0257 (19)	0.056 (3)	0.050 (3)	0.005 (2)	0.0102 (18)	0.003 (2)
C14	0.030 (2)	0.051 (3)	0.044 (2)	−0.004 (2)	0.0039 (17)	−0.001 (2)
C15	0.039 (2)	0.065 (3)	0.041 (2)	0.000 (2)	0.0069 (19)	−0.006 (2)
C16	0.030 (2)	0.073 (4)	0.040 (2)	−0.004 (2)	0.0140 (18)	−0.001 (2)

Geometric parameters (Å, º) top

Cu1—O3ⁱ	1.967 (3)	C4—H4B	0.9600
Cu1—O1ⁱ	1.975 (3)	C4—H4C	0.9600
Cu1—O2	1.983 (3)	C5—C6	1.366 (6)
Cu1—O4	1.984 (3)	C5—H5	0.9300
Cu1—N1	2.220 (3)	C6—C7	1.397 (6)
Cu1—Cu1ⁱ	2.6431 (10)	C6—H6	0.9300
Cl1—C14	1.745 (4)	C7—C8	1.373 (6)
N1—C9	1.350 (5)	C7—C10	1.511 (6)
N1—C5	1.348 (5)	C8—C9	1.397 (5)
N2—C9	1.373 (5)	C8—H8	0.9300
N2—C11	1.411 (5)	C10—H10A	0.9600
N2—H2	0.85 (4)	C10—H10B	0.9600
O1—C1	1.258 (5)	C10—H10C	0.9600
O1—Cu1ⁱ	1.975 (3)	C11—C16	1.392 (6)
O2—C1	1.259 (5)	C11—C12	1.407 (6)
O3—C3	1.262 (5)	C12—C13	1.393 (5)
O3—Cu1ⁱ	1.967 (3)	C12—H12	0.9300
O4—C3	1.274 (5)	C13—C14	1.380 (6)
C1—C2	1.506 (6)	C13—H13	0.9300
C2—H2A	0.9600	C14—C15	1.392 (6)
C2—H2B	0.9600	C15—C16	1.381 (6)
C2—H2C	0.9600	C15—H15	0.9300
C3—C4	1.497 (6)	C16—H16	0.9300
C4—H4A	0.9600

O3ⁱ—Cu1—O1ⁱ	88.89 (14)	H4A—C4—H4C	109.5
O3ⁱ—Cu1—O2	89.88 (14)	H4B—C4—H4C	109.5
O1ⁱ—Cu1—O2	168.34 (12)	N1—C5—C6	124.2 (4)
O3ⁱ—Cu1—O4	168.17 (12)	N1—C5—H5	117.9
O1ⁱ—Cu1—O4	91.08 (15)	C6—C5—H5	117.9
O2—Cu1—O4	87.76 (14)	C5—C6—C7	118.5 (4)
O3ⁱ—Cu1—N1	95.02 (13)	C5—C6—H6	120.7
O1ⁱ—Cu1—N1	94.59 (12)	C7—C6—H6	120.7
O2—Cu1—N1	97.06 (12)	C8—C7—C6	118.4 (4)
O4—Cu1—N1	96.77 (13)	C8—C7—C10	120.8 (4)
O3ⁱ—Cu1—Cu1ⁱ	83.47 (9)	C6—C7—C10	120.8 (4)
O1ⁱ—Cu1—Cu1ⁱ	84.00 (9)	C7—C8—C9	119.8 (4)
O2—Cu1—Cu1ⁱ	84.35 (9)	C7—C8—H8	120.1
O4—Cu1—Cu1ⁱ	84.76 (9)	C9—C8—H8	120.1
N1—Cu1—Cu1ⁱ	177.94 (9)	N1—C9—N2	113.9 (3)
C9—N1—C5	117.2 (3)	N1—C9—C8	121.9 (3)
C9—N1—Cu1	127.9 (3)	N2—C9—C8	124.2 (4)
C5—N1—Cu1	115.0 (3)	C7—C10—H10A	109.5
C9—N2—C11	131.6 (3)	C7—C10—H10B	109.5
C9—N2—H2	116 (3)	H10A—C10—H10B	109.5
C11—N2—H2	111 (3)	C7—C10—H10C	109.5
C1—O1—Cu1ⁱ	123.3 (3)	H10A—C10—H10C	109.5
C1—O2—Cu1	122.5 (3)	H10B—C10—H10C	109.5
C3—O3—Cu1ⁱ	125.2 (3)	C16—C11—N2	116.9 (4)
C3—O4—Cu1	122.5 (3)	C16—C11—C12	118.3 (4)
O1—C1—O2	125.9 (4)	N2—C11—C12	124.6 (4)
O1—C1—C2	117.4 (4)	C13—C12—C11	120.8 (4)
O2—C1—C2	116.7 (4)	C13—C12—H12	119.6
C1—C2—H2A	109.5	C11—C12—H12	119.6
C1—C2—H2B	109.5	C14—C13—C12	119.2 (4)
H2A—C2—H2B	109.5	C14—C13—H13	120.4
C1—C2—H2C	109.5	C12—C13—H13	120.4
H2A—C2—H2C	109.5	C13—C14—C15	120.9 (4)
H2B—C2—H2C	109.5	C13—C14—Cl1	119.6 (3)
O3—C3—O4	123.9 (4)	C15—C14—Cl1	119.5 (3)
O3—C3—C4	118.2 (4)	C16—C15—C14	119.5 (4)
O4—C3—C4	117.8 (4)	C16—C15—H15	120.3
C3—C4—H4A	109.5	C14—C15—H15	120.3
C3—C4—H4B	109.5	C15—C16—C11	121.2 (4)
H4A—C4—H4B	109.5	C15—C16—H16	119.4
C3—C4—H4C	109.5	C11—C16—H16	119.4

O3ⁱ—Cu1—N1—C9	134.2 (4)	Cu1—N1—C5—C6	−178.7 (4)
O1ⁱ—Cu1—N1—C9	−136.5 (4)	N1—C5—C6—C7	0.3 (8)
O2—Cu1—N1—C9	43.7 (4)	C5—C6—C7—C8	−0.3 (8)
O4—Cu1—N1—C9	−44.9 (4)	C5—C6—C7—C10	177.6 (5)
O3ⁱ—Cu1—N1—C5	−47.1 (3)	C6—C7—C8—C9	−0.2 (7)
O1ⁱ—Cu1—N1—C5	42.2 (3)	C10—C7—C8—C9	−178.1 (5)
O2—Cu1—N1—C5	−137.6 (3)	C5—N1—C9—N2	−178.3 (4)
O4—Cu1—N1—C5	133.8 (3)	Cu1—N1—C9—N2	0.4 (6)
O3ⁱ—Cu1—O2—C1	84.2 (4)	C5—N1—C9—C8	−0.6 (6)
O1ⁱ—Cu1—O2—C1	0.3 (9)	Cu1—N1—C9—C8	178.0 (3)
O4—Cu1—O2—C1	−84.2 (4)	C11—N2—C9—N1	−167.2 (5)
N1—Cu1—O2—C1	179.2 (4)	C11—N2—C9—C8	15.3 (8)
Cu1ⁱ—Cu1—O2—C1	0.8 (4)	C7—C8—C9—N1	0.7 (7)
O3ⁱ—Cu1—O4—C3	7.9 (9)	C7—C8—C9—N2	178.1 (5)
O1ⁱ—Cu1—O4—C3	−81.8 (3)	C9—N2—C11—C16	−159.9 (5)
O2—Cu1—O4—C3	86.6 (3)	C9—N2—C11—C12	24.1 (8)
N1—Cu1—O4—C3	−176.6 (3)	C16—C11—C12—C13	2.3 (7)
Cu1ⁱ—Cu1—O4—C3	2.0 (3)	N2—C11—C12—C13	178.3 (4)
Cu1ⁱ—O1—C1—O2	2.0 (7)	C11—C12—C13—C14	−2.1 (7)
Cu1ⁱ—O1—C1—C2	−178.3 (3)	C12—C13—C14—C15	0.5 (7)
Cu1—O2—C1—O1	−1.8 (7)	C12—C13—C14—Cl1	−179.8 (4)
Cu1—O2—C1—C2	178.5 (3)	C13—C14—C15—C16	0.8 (8)
Cu1ⁱ—O3—C3—O4	0.4 (6)	Cl1—C14—C15—C16	−178.9 (4)
Cu1ⁱ—O3—C3—C4	−179.1 (3)	C14—C15—C16—C11	−0.5 (8)
Cu1—O4—C3—O3	−2.1 (6)	N2—C11—C16—C15	−177.3 (4)
Cu1—O4—C3—C4	177.4 (3)	C12—C11—C16—C15	−1.0 (7)
C9—N1—C5—C6	0.1 (7)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1,C5–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4	0.85 (4)	2.30 (2)	3.101 (5)	156 (4)
C4—H4a···Cg1ⁱⁱ	0.96	2.83	3.650 (5)	144

Symmetry code: (ii) x, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂H₃O₂)₄(C₁₂H₁₁ClN₂)₂]
M_r	800.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.7430 (17), 15.619 (2), 9.9866 (14)
β (°)	109.901 (2)
V (Å³)	1722.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.45
Crystal size (mm)	0.35 × 0.25 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.632, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	11432, 3951, 2460
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.151, 1.04
No. of reflections	3951
No. of parameters	224
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.77

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu1—O3ⁱ	1.967 (3)	Cu1—O4	1.984 (3)
Cu1—O1ⁱ	1.975 (3)	Cu1—N1	2.220 (3)
Cu1—O2	1.983 (3)	Cu1—Cu1ⁱ	2.6431 (10)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1,C5–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4	0.85 (4)	2.30 (2)	3.101 (5)	156 (4)
C4—H4a···Cg1ⁱⁱ	0.96	2.83	3.650 (5)	144

Symmetry code: (ii) x, −y−1/2, z−3/2.

Footnotes

‡Additional correspondence author, e-mail: zana@um.edu.my.

Acknowledgements

Z. Abullulah thanks the Ministry of Higher Education, Malaysia, for research grants (RG027/09AFR and PS374/2009B). The authors are also grateful to the University of Malaya for support of the crystallographic facility.

References

Barquín, M., González Garmendia, M. J., Pacheco, S., Pinilla, E., Quintela, S., Seco, J. M. & Torres, M. R. (2004). Inorg. Chim. Acta, 357, 3230–3236. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fairuz, Z. A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, m1690. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Seco, J. M., González Garmendia, M. J., Pinilla, E. & Torres, M. R. (2004). Polyhedron, 21, 457–464. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sieroń, L. (2004). Acta Cryst. E60, m577–m578. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages m1049-m1050

https://doi.org/10.1107/S1600536810030187

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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