(2,2′-Bipyridine-κ2N,N′)chlorido(2-hy­droxy-2,2-diphenyl­acetato-κ2O1,O1′)copper(II)

Reza, M.Y.; Banu, L.A.; Islam, M.S.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681100729X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page m399

doi:10.1107/S160053681100729X

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(2,2′-Bipyridine-κ²N,N′)chlorido(2-hydroxy-2,2-diphenylacetato-κ²O¹,O^1′)copper(II)

Md. Yeamin Reza,^a Laila Arjuman Banu,^a M. Saidul Islam,^a ‡ Seik Weng Ng ^b and Edward R. T. Tiekink ^b ^*

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

(Received 25 February 2011; accepted 25 February 2011; online 9 March 2011)

The Cu(II) atom in the title complex, [Cu(C₁₄H₁₁O₃)Cl(C₁₀H₈N₂)], exists within a ClN₂O₂ donor set defined by a chloride ion, an asymmetrically chelating carboxylate ligand, and a symmetrically chelating 2,2′-bipyridine molecule. The coordination geometry is square pyramidal with the axial site occupied by the O atom forming the weaker Cu—O interaction. The hydroxy group forms an intramolecular hydrogen bond with the axial O atom, as well as an intermolecular O—H⋯Cl hydrogen bond. The latter leads to the formation of [100] supramolecular chains in the crystal, with the Cu(II) atoms lying in a line.

Related literature

For recent structural studies on metal complexes of anions derived from benzilic acid, see: Yang et al. (2010 ); Reza et al. (2010 ). For additional structural analysis, see: Addison et al. (1984 ); Spek (2009 ).

Experimental

Crystal data

[Cu(C₁₄H₁₁O₃)Cl(C₁₀H₈N₂)]
M_r = 482.40
Monoclinic, P 2₁ /c
a = 7.1537 (9) Å
b = 15.7277 (19) Å
c = 18.601 (4) Å
β = 97.806 (14)°
V = 2073.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 293 K
0.20 × 0.15 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.571, T_max = 1.000
8454 measured reflections
3651 independent reflections
2719 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.238
S = 1.03
3651 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.91 e Å⁻³
Δρ_min = −1.42 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu—Cl1	2.2301 (18)
Cu—O1	1.971 (4)
Cu—O2	2.476 (4)
Cu—N1	2.006 (5)
Cu—N2	1.976 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O2	0.82	2.19	2.622 (6)	113
O3—H3o⋯Cl1ⁱ	0.82	2.62	3.328 (5)	146
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: 10.1107/S160053681100729X/hb5805sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100729X/hb5805Isup2.hkl

checkCIF report

Comment top

Recent structural investigations of benzilate complexes have confirmed that anions derived from benzilic acid can function as multidentate ligands with versatile coordination modes (Reza et al., 2010; Yang et al., 2010). Herein, the crystal and molecular structure of a mononuclear Cu^II complex, (I), is described.

The Cu atom in (I) is coordinated by a Cl, an asymmetrically chelating carboxylate anion, and a symmetrically chelating 2,2'-bipyridine ligand, Table 1. The asymmetric mode of coordination of the carboxylate is reflected in the disparate C—O bond distances with the longer C1—O1 distance [1.285 (8) Å] being associated with the shorter Cu—O1 interaction, and the short C1—O2 distance [1.204 (7) Å] associated with the weaker Cu—O2 contact. The resultant ClN₂O₂ donor set defines a square pyramid. This assignment is based on the value calculated for τ of 0.07 for the Cu atom, which compares to the τ values of 0.0 and 1.0 for ideal square pyramidal and trigonal bi-pyramidal geometries, respectively (Spek, 2009; Addison et al., 1984). In this description, the weakly coordinating O2 atom defines the axial site. While not participating in direct coordination to the Cu atom, the hydroxyl group forms an intramolecular hydrogen bond with the O2 atom as well as an intermolecular O—H···Cl hydrogen bond, Table 2. The latter leads to the generation of supramolecular chains along the a axis, Fig. 2, whereby the Cu atoms lie on a line.

Related literature top

For recent structural studies on metal complexes of anions derived from benzilic acid, see: Yang et al. (2010); Reza et al. (2010). For additional structural analysis, see: Addison et al. (1984); Spek (2009).

Experimental top

A mixture of copper chloride (0.134 g,1 mmol), benzilic acid (0.228 g, 1 mmol), 2,2'-bipyridine (0.196 g, 1 mmol) and Et₃N (0.1 g, 1 mmol) was placed into methanol (40 ml) and the resultant solution was heated to 323 K for 0.5 h. Initial precipitates were filtered off and the filtrate was allowed to stand for several days. Blue blocks of the title compound were collected, washed with methanol and air-dried at room temperature. M. pt. 457 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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. Molecular structure of (I), showing displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular chain along the a axis in (I) mediated by O—H···Cl hydrogen bonds (shown as orange dashed lines).

(2,2'-Bipyridine-κ²N,N')chlorido(2-hydroxy-2,2- diphenylacetato-κ²O¹,O^1')copper(II) top

Crystal data top

[Cu(C₁₄H₁₁O₃)Cl(C₁₀H₈N₂)]	F(000) = 988
M_r = 482.40	D_x = 1.545 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3252 reflections
a = 7.1537 (9) Å	θ = 2.6–29.4°
b = 15.7277 (19) Å	µ = 1.21 mm⁻¹
c = 18.601 (4) Å	T = 293 K
β = 97.806 (14)°	Block, blue
V = 2073.5 (5) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3651 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2719 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.053
Detector resolution: 10.4041 pixels mm^-1	θ_max = 25.0°, θ_min = 2.6°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −18→17
T_min = 0.571, T_max = 1.000	l = −21→22
8454 measured reflections

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.238	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1324P)² + 7.2136P] where P = (F_o² + 2F_c²)/3
3651 reflections	(Δ/σ)_max < 0.001
281 parameters	Δρ_max = 0.91 e Å⁻³
0 restraints	Δρ_min = −1.42 e Å⁻³

Crystal data top

[Cu(C₁₄H₁₁O₃)Cl(C₁₀H₈N₂)]	V = 2073.5 (5) Å³
M_r = 482.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1537 (9) Å	µ = 1.21 mm⁻¹
b = 15.7277 (19) Å	T = 293 K
c = 18.601 (4) Å	0.20 × 0.15 × 0.10 mm
β = 97.806 (14)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3651 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2719 reflections with I > 2σ(I)
T_min = 0.571, T_max = 1.000	R_int = 0.053
8454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.238	H-atom parameters constrained
S = 1.03	Δρ_max = 0.91 e Å⁻³
3651 reflections	Δρ_min = −1.42 e Å⁻³
281 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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

	x	y	z	U_iso*/U_eq
Cu	0.63293 (10)	0.44986 (4)	0.36367 (4)	0.0351 (3)
Cl1	0.4262 (2)	0.34756 (11)	0.32669 (10)	0.0475 (5)
N1	0.7215 (8)	0.5629 (3)	0.4053 (3)	0.0390 (13)
N2	0.6723 (7)	0.4182 (3)	0.4674 (3)	0.0337 (11)
O1	0.6859 (6)	0.4804 (3)	0.2657 (2)	0.0401 (10)
O2	0.9191 (6)	0.3986 (3)	0.3158 (2)	0.0415 (11)
O3	1.0661 (7)	0.3757 (3)	0.1956 (2)	0.0438 (11)
H3o	1.1135	0.3685	0.2378	0.066*
C1	0.8391 (9)	0.4378 (4)	0.2651 (3)	0.0330 (14)
C2	0.9273 (9)	0.4407 (4)	0.1925 (3)	0.0307 (13)
C3	0.7914 (9)	0.4235 (4)	0.1234 (3)	0.0350 (13)
C4	0.6016 (10)	0.4065 (4)	0.1209 (4)	0.0457 (16)
H4	0.5468	0.4054	0.1634	0.055*
C5	0.4940 (11)	0.3911 (5)	0.0554 (5)	0.058 (2)
H5	0.3653	0.3811	0.0536	0.070*
C6	0.5752 (13)	0.3905 (5)	−0.0080 (4)	0.062 (2)
H6	0.5008	0.3794	−0.0520	0.074*
C7	0.7616 (13)	0.4058 (5)	−0.0067 (4)	0.061 (2)
H7	0.8161	0.4044	−0.0493	0.073*
C8	0.8696 (11)	0.4236 (5)	0.0586 (4)	0.0490 (17)
H8	0.9971	0.4358	0.0596	0.059*
C9	1.0175 (8)	0.5291 (4)	0.1890 (3)	0.0342 (13)
C10	0.9071 (10)	0.6006 (4)	0.1767 (4)	0.0414 (15)
H10	0.7765	0.5952	0.1684	0.050*
C11	0.9891 (12)	0.6816 (4)	0.1764 (4)	0.0550 (19)
H11	0.9129	0.7295	0.1691	0.066*
C12	1.1818 (12)	0.6901 (5)	0.1871 (4)	0.057 (2)
H12	1.2369	0.7435	0.1861	0.068*
C13	1.2907 (10)	0.6200 (5)	0.1991 (3)	0.0491 (18)
H13	1.4213	0.6259	0.2060	0.059*
C14	1.2124 (9)	0.5387 (4)	0.2013 (4)	0.0413 (15)
H14	1.2900	0.4915	0.2108	0.050*
C15	0.7393 (9)	0.6339 (4)	0.3682 (4)	0.0448 (16)
H15	0.7052	0.6331	0.3182	0.054*
C16	0.8060 (10)	0.7086 (4)	0.4006 (4)	0.0466 (16)
H16	0.8175	0.7571	0.3730	0.056*
C17	0.8541 (10)	0.7101 (4)	0.4732 (4)	0.0464 (16)
H17	0.8988	0.7599	0.4964	0.056*
C18	0.8367 (9)	0.6366 (4)	0.5133 (4)	0.0410 (15)
H18	0.8700	0.6364	0.5634	0.049*
C19	0.7685 (8)	0.5635 (4)	0.4772 (4)	0.0339 (14)
C20	0.7432 (8)	0.4810 (4)	0.5129 (3)	0.0319 (13)
C21	0.7927 (9)	0.4669 (4)	0.5869 (3)	0.0393 (15)
H21	0.8404	0.5107	0.6177	0.047*
C22	0.7690 (10)	0.3860 (4)	0.6135 (3)	0.0431 (16)
H22	0.8011	0.3748	0.6627	0.052*
C23	0.6981 (10)	0.3219 (4)	0.5670 (4)	0.0484 (17)
H23	0.6828	0.2672	0.5844	0.058*
C24	0.6505 (10)	0.3403 (4)	0.4949 (4)	0.0432 (16)
H24	0.6012	0.2972	0.4637	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0404 (5)	0.0315 (5)	0.0357 (5)	0.0002 (3)	0.0137 (4)	−0.0010 (3)
Cl1	0.0425 (9)	0.0453 (9)	0.0547 (11)	−0.0055 (7)	0.0066 (8)	−0.0046 (8)
N1	0.050 (3)	0.027 (2)	0.045 (3)	0.001 (2)	0.025 (3)	−0.001 (2)
N2	0.034 (3)	0.032 (3)	0.037 (3)	−0.003 (2)	0.009 (2)	−0.003 (2)
O1	0.053 (3)	0.042 (2)	0.029 (2)	0.005 (2)	0.018 (2)	−0.0053 (19)
O2	0.050 (3)	0.043 (2)	0.032 (2)	0.003 (2)	0.009 (2)	0.012 (2)
O3	0.058 (3)	0.033 (2)	0.042 (3)	0.017 (2)	0.012 (2)	−0.002 (2)
C1	0.045 (3)	0.026 (3)	0.029 (3)	−0.007 (3)	0.011 (3)	−0.006 (2)
C2	0.040 (3)	0.032 (3)	0.019 (3)	0.005 (2)	0.002 (2)	−0.001 (2)
C3	0.045 (3)	0.025 (3)	0.035 (3)	0.003 (3)	0.005 (3)	−0.001 (3)
C4	0.046 (4)	0.041 (4)	0.052 (4)	−0.005 (3)	0.010 (3)	−0.010 (3)
C5	0.050 (4)	0.045 (4)	0.075 (6)	−0.004 (3)	−0.009 (4)	−0.010 (4)
C6	0.086 (6)	0.043 (4)	0.046 (5)	−0.002 (4)	−0.025 (4)	−0.004 (3)
C7	0.090 (6)	0.053 (4)	0.041 (4)	−0.008 (4)	0.014 (4)	0.001 (3)
C8	0.063 (4)	0.048 (4)	0.037 (4)	−0.005 (4)	0.012 (3)	−0.003 (3)
C9	0.038 (3)	0.033 (3)	0.034 (3)	−0.001 (3)	0.014 (3)	−0.006 (3)
C10	0.043 (3)	0.038 (3)	0.045 (4)	0.003 (3)	0.011 (3)	0.004 (3)
C11	0.070 (5)	0.030 (3)	0.067 (5)	0.002 (3)	0.019 (4)	0.001 (3)
C12	0.075 (5)	0.038 (4)	0.063 (5)	−0.020 (4)	0.030 (4)	−0.007 (3)
C13	0.052 (4)	0.069 (5)	0.028 (3)	−0.021 (4)	0.012 (3)	−0.007 (3)
C14	0.044 (4)	0.044 (4)	0.038 (4)	0.002 (3)	0.013 (3)	−0.002 (3)
C15	0.040 (4)	0.041 (4)	0.053 (4)	0.000 (3)	0.005 (3)	0.009 (3)
C16	0.050 (4)	0.034 (3)	0.058 (5)	−0.001 (3)	0.016 (3)	0.007 (3)
C17	0.058 (4)	0.033 (3)	0.049 (4)	−0.006 (3)	0.011 (3)	−0.008 (3)
C18	0.040 (3)	0.034 (3)	0.051 (4)	0.000 (3)	0.012 (3)	−0.002 (3)
C19	0.028 (3)	0.033 (3)	0.044 (4)	0.002 (2)	0.016 (3)	0.001 (3)
C20	0.028 (3)	0.035 (3)	0.034 (3)	0.005 (2)	0.010 (2)	0.005 (3)
C21	0.043 (4)	0.044 (3)	0.033 (3)	0.004 (3)	0.011 (3)	−0.006 (3)
C22	0.052 (4)	0.052 (4)	0.026 (3)	0.006 (3)	0.008 (3)	0.007 (3)
C23	0.051 (4)	0.040 (4)	0.058 (5)	0.003 (3)	0.021 (3)	0.011 (3)
C24	0.050 (4)	0.030 (3)	0.053 (4)	−0.004 (3)	0.022 (3)	0.004 (3)

Geometric parameters (Å, º) top

Cu—Cl1	2.2301 (18)	C9—C14	1.390 (9)
Cu—O1	1.971 (4)	C10—C11	1.403 (9)
Cu—O2	2.476 (4)	C10—H10	0.9300
Cu—N1	2.006 (5)	C11—C12	1.372 (11)
Cu—N2	1.976 (5)	C11—H11	0.9300
N1—C15	1.329 (8)	C12—C13	1.351 (11)
N1—C19	1.333 (9)	C12—H12	0.9300
N2—C24	1.345 (8)	C13—C14	1.399 (10)
N2—C20	1.353 (8)	C13—H13	0.9300
O1—C1	1.285 (8)	C14—H14	0.9300
O2—C1	1.204 (7)	C15—C16	1.376 (10)
O3—C2	1.421 (7)	C15—H15	0.9300
O3—H3o	0.8200	C16—C17	1.348 (10)
C1—C2	1.567 (8)	C16—H16	0.9300
C2—C3	1.527 (8)	C17—C18	1.390 (9)
C2—C9	1.537 (8)	C17—H17	0.9300
C3—C4	1.379 (9)	C18—C19	1.387 (9)
C3—C8	1.395 (9)	C18—H18	0.9300
C4—C5	1.371 (10)	C19—C20	1.481 (8)
C4—H4	0.9300	C20—C21	1.391 (9)
C5—C6	1.385 (12)	C21—C22	1.384 (9)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.352 (12)	C22—C23	1.379 (10)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.377 (11)	C23—C24	1.370 (10)
C7—H7	0.9300	C23—H23	0.9300
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.375 (9)

O1—Cu—N2	160.9 (2)	C10—C9—C2	120.8 (5)
O1—Cu—N1	92.9 (2)	C14—C9—C2	120.6 (5)
N2—Cu—N1	81.4 (2)	C9—C10—C11	120.8 (6)
O1—Cu—Cl1	95.35 (14)	C9—C10—H10	119.6
N2—Cu—Cl1	96.91 (15)	C11—C10—H10	119.6
N1—Cu—Cl1	156.84 (16)	C12—C11—C10	120.0 (7)
O1—Cu—O2	58.31 (16)	C12—C11—H11	120.0
N2—Cu—O2	104.72 (18)	C10—C11—H11	120.0
N1—Cu—O2	101.21 (18)	C13—C12—C11	119.3 (6)
Cl1—Cu—O2	101.55 (12)	C13—C12—H12	120.3
C15—N1—C19	119.0 (6)	C11—C12—H12	120.3
C15—N1—Cu	126.3 (5)	C12—C13—C14	121.7 (7)
C19—N1—Cu	114.6 (4)	C12—C13—H13	119.1
C24—N2—C20	118.7 (6)	C14—C13—H13	119.1
C24—N2—Cu	126.3 (4)	C9—C14—C13	119.5 (6)
C20—N2—Cu	114.8 (4)	C9—C14—H14	120.3
C1—O1—Cu	98.7 (4)	C13—C14—H14	120.3
C1—O2—Cu	77.7 (4)	N1—C15—C16	122.9 (7)
C2—O3—H3o	109.5	N1—C15—H15	118.6
O2—C1—O1	125.2 (6)	C16—C15—H15	118.6
O2—C1—C2	119.0 (5)	C17—C16—C15	118.7 (6)
O1—C1—C2	115.8 (5)	C17—C16—H16	120.7
O3—C2—C3	105.5 (4)	C15—C16—H16	120.7
O3—C2—C9	111.0 (5)	C16—C17—C18	119.6 (6)
C3—C2—C9	110.4 (5)	C16—C17—H17	120.2
O3—C2—C1	107.8 (5)	C18—C17—H17	120.2
C3—C2—C1	115.8 (5)	C19—C18—C17	118.7 (6)
C9—C2—C1	106.4 (4)	C19—C18—H18	120.7
C4—C3—C8	118.6 (6)	C17—C18—H18	120.7
C4—C3—C2	125.1 (6)	N1—C19—C18	121.1 (6)
C8—C3—C2	116.3 (6)	N1—C19—C20	114.5 (5)
C3—C4—C5	119.8 (7)	C18—C19—C20	124.4 (6)
C3—C4—H4	120.1	N2—C20—C21	121.8 (6)
C5—C4—H4	120.1	N2—C20—C19	114.6 (5)
C4—C5—C6	120.5 (7)	C21—C20—C19	123.6 (6)
C4—C5—H5	119.7	C22—C21—C20	118.2 (6)
C6—C5—H5	119.7	C22—C21—H21	120.9
C7—C6—C5	120.7 (7)	C20—C21—H21	120.9
C7—C6—H6	119.7	C23—C22—C21	120.1 (6)
C5—C6—H6	119.7	C23—C22—H22	119.9
C6—C7—C8	119.1 (8)	C21—C22—H22	119.9
C6—C7—H7	120.5	C24—C23—C22	118.7 (6)
C8—C7—H7	120.5	C24—C23—H23	120.6
C7—C8—C3	121.3 (7)	C22—C23—H23	120.6
C7—C8—H8	119.4	N2—C24—C23	122.6 (6)
C3—C8—H8	119.4	N2—C24—H24	118.7
C10—C9—C14	118.6 (6)	C23—C24—H24	118.7

O1—Cu—N1—C15	19.3 (6)	C5—C6—C7—C8	−1.1 (12)
N2—Cu—N1—C15	−179.0 (6)	C6—C7—C8—C3	1.9 (12)
Cl1—Cu—N1—C15	−91.6 (6)	C4—C3—C8—C7	−1.0 (10)
O2—Cu—N1—C15	77.6 (5)	C2—C3—C8—C7	177.7 (6)
O1—Cu—N1—C19	−159.5 (4)	O3—C2—C9—C10	171.8 (5)
N2—Cu—N1—C19	2.2 (4)	C3—C2—C9—C10	55.3 (7)
Cl1—Cu—N1—C19	89.6 (6)	C1—C2—C9—C10	−71.2 (7)
O2—Cu—N1—C19	−101.2 (4)	O3—C2—C9—C14	−10.8 (8)
O1—Cu—N2—C24	−103.3 (7)	C3—C2—C9—C14	−127.3 (6)
N1—Cu—N2—C24	−177.1 (5)	C1—C2—C9—C14	106.2 (6)
Cl1—Cu—N2—C24	26.2 (5)	C14—C9—C10—C11	−0.1 (10)
O2—Cu—N2—C24	−77.7 (5)	C2—C9—C10—C11	177.4 (6)
O1—Cu—N2—C20	70.8 (7)	C9—C10—C11—C12	1.4 (11)
N1—Cu—N2—C20	−3.0 (4)	C10—C11—C12—C13	−1.2 (12)
Cl1—Cu—N2—C20	−159.7 (4)	C11—C12—C13—C14	−0.3 (11)
O2—Cu—N2—C20	96.4 (4)	C10—C9—C14—C13	−1.4 (9)
N2—Cu—O1—C1	31.7 (7)	C2—C9—C14—C13	−178.9 (6)
N1—Cu—O1—C1	103.6 (4)	C12—C13—C14—C9	1.6 (10)
Cl1—Cu—O1—C1	−98.1 (3)	C19—N1—C15—C16	0.6 (10)
O2—Cu—O1—C1	2.2 (3)	Cu—N1—C15—C16	−178.2 (5)
O1—Cu—O2—C1	−2.4 (3)	N1—C15—C16—C17	−0.5 (10)
N2—Cu—O2—C1	−172.8 (4)	C15—C16—C17—C18	0.4 (10)
N1—Cu—O2—C1	−88.9 (4)	C16—C17—C18—C19	−0.4 (10)
Cl1—Cu—O2—C1	86.8 (3)	C15—N1—C19—C18	−0.6 (9)
Cu—O2—C1—O1	3.8 (5)	Cu—N1—C19—C18	178.4 (4)
Cu—O2—C1—C2	−177.9 (5)	C15—N1—C19—C20	−179.9 (5)
Cu—O1—C1—O2	−4.7 (7)	Cu—N1—C19—C20	−1.0 (6)
Cu—O1—C1—C2	177.0 (4)	C17—C18—C19—N1	0.5 (9)
O2—C1—C2—O3	15.2 (7)	C17—C18—C19—C20	179.8 (6)
O1—C1—C2—O3	−166.4 (5)	C24—N2—C20—C21	−0.3 (8)
O2—C1—C2—C3	133.0 (6)	Cu—N2—C20—C21	−174.9 (4)
O1—C1—C2—C3	−48.6 (7)	C24—N2—C20—C19	177.8 (5)
O2—C1—C2—C9	−103.9 (6)	Cu—N2—C20—C19	3.3 (6)
O1—C1—C2—C9	74.5 (6)	N1—C19—C20—N2	−1.4 (7)
O3—C2—C3—C4	119.4 (6)	C18—C19—C20—N2	179.2 (5)
C9—C2—C3—C4	−120.7 (6)	N1—C19—C20—C21	176.7 (6)
C1—C2—C3—C4	0.3 (8)	C18—C19—C20—C21	−2.7 (9)
O3—C2—C3—C8	−59.2 (7)	N2—C20—C21—C22	0.5 (9)
C9—C2—C3—C8	60.8 (7)	C19—C20—C21—C22	−177.5 (6)
C1—C2—C3—C8	−178.3 (5)	C20—C21—C22—C23	0.0 (10)
C8—C3—C4—C5	−0.8 (10)	C21—C22—C23—C24	−0.6 (10)
C2—C3—C4—C5	−179.3 (6)	C20—N2—C24—C23	−0.3 (9)
C3—C4—C5—C6	1.6 (11)	Cu—N2—C24—C23	173.6 (5)
C4—C5—C6—C7	−0.7 (12)	C22—C23—C24—N2	0.8 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2	0.82	2.19	2.622 (6)	113
O3—H3o···Cl1ⁱ	0.82	2.62	3.328 (5)	146

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₄H₁₁O₃)Cl(C₁₀H₈N₂)]
M_r	482.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.1537 (9), 15.7277 (19), 18.601 (4)
β (°)	97.806 (14)
V (Å³)	2073.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.571, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8454, 3651, 2719
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.238, 1.03
No. of reflections	3651
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.91, −1.42

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu—Cl1	2.2301 (18)	Cu—N1	2.006 (5)
Cu—O1	1.971 (4)	Cu—N2	1.976 (5)
Cu—O2	2.476 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2	0.82	2.19	2.622 (6)	113
O3—H3o···Cl1ⁱ	0.82	2.62	3.328 (5)	146

Symmetry code: (i) x+1, y, z.

Footnotes

‡Additional correspondence author, e-mail: msjhantu@yahoo.com.

Acknowledgements

MYR, LAB and MSI thank Dr T. G. Roy for special assistance. The authors also thank Rajshahi University for the provision of their central laboratory facilities and the University of Malaya for support of the crystallographic facility.

References

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