catena-Poly[[chlorido(1,10-phenanthro­line)copper(II)]-μ-{2-[(1S,3S)-3-acetyl-2,2-dimethyl­cyclo­but­yl]acetato}]

Ma, S.; Li, Y.

doi:10.1107/S1600536811048586

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1789

https://doi.org/10.1107/S1600536811048586

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catena-Poly[[chlorido(1,10-phenanthroline)copper(II)]-μ-{2-[(1S,3S)-3-acetyl-2,2-dimethylcyclobutyl]acetato}]

Shi-ying Ma ^a ^* and Yan-fei Li ^b

^aDepartment of Chemistry and Environmental Sciences, Taishan University, 271021 Taian, Shandong, People's Republic of China, and ^bDepartment of Materials and Chemistry Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: mashy910@163.com

(Received 27 October 2011; accepted 15 November 2011; online 19 November 2011)

The title compound, [Cu(C₁₀H₁₅O₃)Cl(C₁₂H₈N₂)]_n, is a one-dimensional coordination polymer. The Cu^II atom is coordinated by a chloride ion, two N atoms from the 1,10-phenanthroline ligand, and a monodentate carboxylate O atom from the pinononate anion, forming a CuN₂ClO approximate square plane. A symmetry-generated pinononate O atom completes a square-based pyramidal geometry for the copper ion. The bridging 2-(3-acetyl-2,2-dimethylcyclobutyl)acetate anion leads to chains in the crystal propagating in [001]. Adjacent 1,10-phenanthroline rings form a dihedral angle of 39.4 (2)°.

Related literature

For related structures, see: Che et al. (2006 ); Lalancette et al. (1999 ); Vanderhoff et al. (1986 ).

Experimental

Crystal data

[Cu(C₁₀H₁₅O₃)Cl(C₁₂H₈N₂)]
M_r = 462.41
Monoclinic, P 2₁ /c
a = 14.6143 (11) Å
b = 14.4920 (12) Å
c = 9.8419 (8) Å
β = 98.208 (1)°
V = 2063.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 273 K
0.20 × 0.18 × 0.16 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ) T_min = 0.793, T_max = 0.829
10533 measured reflections
3647 independent reflections
2924 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.097
S = 1.03
3647 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.937 (2)
Cu1—N2	2.030 (2)
Cu1—N1	2.050 (2)
Cu1—Cl1	2.2610 (8)
Cu1—O2ⁱ	2.305 (2)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811048586/hb6482sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048586/hb6482Isup2.hkl

checkCIF report

Comment top

In the structural investigation of pinonate complexes, it has been found that the pinonic acid functions as a monodenate ligand (Lalancette et al., 1999). We sythesized the pinonic acid that obtained from α-pinene oxidated by potassium permangate. In the present paper, we describe the crystal stucture of the title compound.The polymer molecule contains CuN₂O₂Cl square-based pyramids (Fig.1). The Cu(II) atom exists in a distorted square pyramidal enviroment,defined by two carboxyl O atoms from two monodentate pinonate ligand,two N atoms from 1,10-phenanthroline ligand and one Cl^- anion.

Related literature top

For related structures, see: Che et al. (2006); Lalancette et al. (1999); Vanderhoff et al. (1986).

Experimental top

Pinonic acid is synthesized from α-pinene oxidated by potassium permangate.The pinonic acid (0.5 mmol)and NaOH (0.5 mmol) were dissolved in methanol (5 ml). A methanolic solution (5 ml) of CuCl₂.H₂O (0.25 mmol) and 1,10-phenanthroline (0.25 mmol) was slowly droped to the solution of the pinonic acid with stirring.The result solution was flitered and allowed to stand in air at room temperature for seven days,yielding blue blocks of (I).

Structure description top

For related structures, see: Che et al. (2006); Lalancette et al. (1999); Vanderhoff et al. (1986).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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).

Figures top

Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.

catena-Poly[[chlorido(1,10-phenanthroline)copper(II)]-µ- {2-[(1S,3S)-3-acetyl-2,2-dimethylcyclobutyl]acetato}] top

Crystal data top

[Cu(C₁₀H₁₅O₃)Cl(C₁₂H₈N₂)]	F(000) = 956
M_r = 462.41	D_x = 1.489 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3334 reflections
a = 14.6143 (11) Å	θ = 2.5–25.1°
b = 14.4920 (12) Å	µ = 1.21 mm⁻¹
c = 9.8419 (8) Å	T = 273 K
β = 98.208 (1)°	Block, blue
V = 2063.1 (3) Å³	0.20 × 0.18 × 0.16 mm
Z = 4

Data collection top

Siemens SMART CCD diffractometer	3647 independent reflections
Radiation source: fine-focus sealed tube	2924 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
phi and ω scans	θ_max = 25.1°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −15→17
T_min = 0.793, T_max = 0.829	k = −17→14
10533 measured reflections	l = −11→11

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0467P)² + 1.5378P] where P = (F_o² + 2F_c²)/3
3647 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Cu(C₁₀H₁₅O₃)Cl(C₁₂H₈N₂)]	V = 2063.1 (3) Å³
M_r = 462.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.6143 (11) Å	µ = 1.21 mm⁻¹
b = 14.4920 (12) Å	T = 273 K
c = 9.8419 (8) Å	0.20 × 0.18 × 0.16 mm
β = 98.208 (1)°

Data collection top

Siemens SMART CCD diffractometer	3647 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	2924 reflections with I > 2σ(I)
T_min = 0.793, T_max = 0.829	R_int = 0.028
10533 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	Δρ_max = 0.67 e Å⁻³
3647 reflections	Δρ_min = −0.30 e Å⁻³
265 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

	x	y	z	U_iso*/U_eq
Cu1	0.38042 (2)	0.23582 (2)	0.56377 (4)	0.02863 (13)
Cl1	0.34460 (5)	0.08697 (5)	0.51189 (8)	0.0398 (2)
O1	0.26729 (14)	0.25754 (14)	0.6401 (2)	0.0347 (5)
O2	0.33639 (14)	0.21019 (14)	0.8438 (2)	0.0355 (5)
O3	−0.1289 (3)	0.1493 (3)	0.8971 (5)	0.1157 (15)
N1	0.51618 (16)	0.22377 (16)	0.5353 (2)	0.0289 (5)
N2	0.42648 (16)	0.36312 (16)	0.6269 (2)	0.0295 (5)
C1	0.26816 (19)	0.24062 (19)	0.7671 (3)	0.0279 (6)
C2	0.1786 (2)	0.2630 (2)	0.8208 (3)	0.0397 (8)
H2A	0.1808	0.2364	0.9116	0.048*
H2B	0.1739	0.3294	0.8298	0.048*
C3	0.0939 (2)	0.2285 (2)	0.7320 (4)	0.0461 (8)
H3	0.0985	0.2437	0.6362	0.055*
C4	0.0640 (2)	0.1255 (3)	0.7399 (3)	0.0435 (8)
C5	0.0936 (3)	0.0622 (3)	0.6319 (5)	0.0767 (14)
H5A	0.1598	0.0615	0.6401	0.115*
H5B	0.0683	0.0842	0.5423	0.115*
H5C	0.0714	0.0010	0.6447	0.115*
C6	0.0917 (3)	0.0859 (3)	0.8825 (4)	0.0663 (11)
H6A	0.0653	0.0256	0.8872	0.099*
H6B	0.0695	0.1255	0.9489	0.099*
H6C	0.1578	0.0817	0.9016	0.099*
C7	−0.0376 (2)	0.1627 (3)	0.7195 (4)	0.0574 (10)
H7	−0.0622	0.1633	0.6214	0.069*
C8	−0.0020 (3)	0.2584 (3)	0.7638 (5)	0.0651 (11)
H8A	−0.0037	0.2718	0.8600	0.078*
H8B	−0.0299	0.3079	0.7057	0.078*
C9	−0.1054 (3)	0.1142 (3)	0.7988 (5)	0.0697 (12)
C10	−0.1413 (3)	0.0230 (4)	0.7437 (6)	0.0972 (18)
H10A	−0.1668	−0.0102	0.8139	0.146*
H10B	−0.0916	−0.0121	0.7153	0.146*
H10C	−0.1884	0.0326	0.6665	0.146*
C11	0.5589 (2)	0.1529 (2)	0.4869 (3)	0.0375 (7)
H11	0.5255	0.0995	0.4619	0.045*
C12	0.6521 (2)	0.1559 (2)	0.4722 (4)	0.0451 (8)
H12	0.6801	0.1048	0.4383	0.054*
C13	0.7023 (2)	0.2334 (2)	0.5073 (4)	0.0458 (8)
H13	0.7645	0.2358	0.4968	0.055*
C14	0.6600 (2)	0.3100 (2)	0.5596 (3)	0.0357 (7)
C15	0.7052 (2)	0.3956 (2)	0.5989 (3)	0.0435 (8)
H15	0.7678	0.4019	0.5929	0.052*
C16	0.6593 (2)	0.4668 (2)	0.6442 (3)	0.0411 (8)
H16	0.6907	0.5214	0.6695	0.049*
C17	0.5629 (2)	0.4600 (2)	0.6541 (3)	0.0330 (7)
C18	0.5098 (2)	0.5331 (2)	0.6977 (3)	0.0370 (7)
H18	0.5367	0.5901	0.7208	0.044*
C19	0.4190 (2)	0.5183 (2)	0.7050 (3)	0.0406 (8)
H19	0.3831	0.5656	0.7336	0.049*
C20	0.3791 (2)	0.4324 (2)	0.6697 (3)	0.0367 (7)
H20	0.3169	0.4236	0.6765	0.044*
C21	0.51761 (19)	0.37713 (19)	0.6199 (3)	0.0275 (6)
C22	0.56575 (19)	0.3011 (2)	0.5705 (3)	0.0295 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0292 (2)	0.0275 (2)	0.0297 (2)	−0.00360 (15)	0.00622 (14)	−0.00034 (15)
Cl1	0.0446 (5)	0.0285 (4)	0.0455 (5)	−0.0070 (3)	0.0040 (4)	−0.0003 (3)
O1	0.0312 (11)	0.0448 (13)	0.0287 (11)	−0.0034 (9)	0.0060 (9)	0.0014 (9)
O2	0.0377 (12)	0.0373 (12)	0.0309 (12)	0.0077 (9)	0.0032 (9)	−0.0031 (9)
O3	0.109 (3)	0.110 (3)	0.152 (4)	−0.012 (2)	0.098 (3)	−0.022 (3)
N1	0.0325 (13)	0.0249 (13)	0.0299 (13)	−0.0009 (10)	0.0064 (10)	−0.0007 (10)
N2	0.0319 (13)	0.0291 (13)	0.0285 (13)	−0.0023 (11)	0.0074 (10)	−0.0016 (10)
C1	0.0291 (15)	0.0235 (15)	0.0319 (16)	−0.0071 (12)	0.0071 (13)	−0.0064 (12)
C2	0.0345 (17)	0.051 (2)	0.0347 (18)	−0.0008 (15)	0.0101 (13)	−0.0085 (15)
C3	0.0356 (18)	0.060 (2)	0.044 (2)	−0.0002 (16)	0.0080 (15)	0.0042 (17)
C4	0.0289 (17)	0.058 (2)	0.045 (2)	−0.0049 (15)	0.0095 (14)	−0.0051 (17)
C5	0.058 (3)	0.095 (3)	0.082 (3)	−0.023 (2)	0.026 (2)	−0.043 (3)
C6	0.067 (3)	0.061 (3)	0.071 (3)	0.004 (2)	0.012 (2)	0.010 (2)
C7	0.0360 (19)	0.075 (3)	0.061 (2)	−0.0026 (19)	0.0078 (17)	0.004 (2)
C8	0.042 (2)	0.066 (3)	0.088 (3)	0.0026 (19)	0.011 (2)	0.007 (2)
C9	0.039 (2)	0.090 (3)	0.085 (3)	−0.013 (2)	0.026 (2)	−0.003 (3)
C10	0.065 (3)	0.107 (4)	0.122 (5)	−0.044 (3)	0.023 (3)	−0.006 (3)
C11	0.0436 (18)	0.0303 (17)	0.0400 (18)	−0.0009 (14)	0.0106 (14)	−0.0020 (14)
C12	0.0455 (19)	0.0368 (19)	0.057 (2)	0.0080 (16)	0.0200 (17)	−0.0022 (16)
C13	0.0365 (18)	0.045 (2)	0.059 (2)	0.0019 (16)	0.0186 (16)	0.0034 (17)
C14	0.0311 (16)	0.0359 (17)	0.0411 (18)	−0.0034 (14)	0.0089 (13)	0.0024 (14)
C15	0.0353 (18)	0.045 (2)	0.052 (2)	−0.0086 (15)	0.0119 (15)	0.0008 (16)
C16	0.0419 (18)	0.0379 (19)	0.0434 (19)	−0.0153 (15)	0.0062 (15)	−0.0018 (15)
C17	0.0392 (17)	0.0322 (17)	0.0272 (16)	−0.0054 (13)	0.0040 (13)	0.0002 (13)
C18	0.050 (2)	0.0267 (16)	0.0332 (17)	−0.0053 (14)	0.0038 (14)	−0.0042 (13)
C19	0.052 (2)	0.0323 (18)	0.0387 (19)	0.0045 (15)	0.0121 (15)	−0.0070 (14)
C20	0.0362 (17)	0.0362 (18)	0.0396 (18)	0.0023 (14)	0.0118 (14)	−0.0026 (14)
C21	0.0322 (15)	0.0284 (15)	0.0221 (15)	−0.0039 (12)	0.0044 (11)	−0.0008 (12)
C22	0.0325 (15)	0.0269 (15)	0.0289 (15)	−0.0020 (13)	0.0041 (12)	0.0011 (12)

Geometric parameters (Å, º) top

Cu1—O1	1.937 (2)	C7—C9	1.519 (5)
Cu1—N2	2.030 (2)	C7—C8	1.523 (6)
Cu1—N1	2.050 (2)	C7—H7	0.9800
Cu1—Cl1	2.2610 (8)	C8—H8A	0.9700
Cu1—O2ⁱ	2.305 (2)	C8—H8B	0.9700
O1—C1	1.272 (4)	C9—C10	1.496 (7)
O2—C1	1.242 (3)	C10—H10A	0.9600
O2—Cu1ⁱⁱ	2.305 (2)	C10—H10B	0.9600
O3—C9	1.186 (5)	C10—H10C	0.9600
N1—C11	1.326 (4)	C11—C12	1.391 (4)
N1—C22	1.352 (4)	C11—H11	0.9300
N2—C20	1.322 (4)	C12—C13	1.360 (5)
N2—C21	1.359 (3)	C12—H12	0.9300
C1—C2	1.514 (4)	C13—C14	1.403 (4)
C2—C3	1.496 (5)	C13—H13	0.9300
C2—H2A	0.9700	C14—C22	1.403 (4)
C2—H2B	0.9700	C14—C15	1.431 (4)
C3—C8	1.541 (5)	C15—C16	1.342 (5)
C3—C4	1.559 (5)	C15—H15	0.9300
C3—H3	0.9800	C16—C17	1.430 (4)
C4—C5	1.513 (5)	C16—H16	0.9300
C4—C6	1.517 (5)	C17—C21	1.390 (4)
C4—C7	1.566 (5)	C17—C18	1.414 (4)
C5—H5A	0.9600	C18—C19	1.357 (4)
C5—H5B	0.9600	C18—H18	0.9300
C5—H5C	0.9600	C19—C20	1.398 (4)
C6—H6A	0.9600	C19—H19	0.9300
C6—H6B	0.9600	C20—H20	0.9300
C6—H6C	0.9600	C21—C22	1.430 (4)

O1—Cu1—N2	89.87 (9)	C9—C7—H7	109.7
O1—Cu1—N1	164.36 (9)	C8—C7—H7	109.7
N2—Cu1—N1	80.45 (9)	C4—C7—H7	109.7
O1—Cu1—Cl1	93.42 (6)	C7—C8—C3	88.2 (3)
N2—Cu1—Cl1	172.71 (7)	C7—C8—H8A	113.9
N1—Cu1—Cl1	94.89 (7)	C3—C8—H8A	113.9
O1—Cu1—O2ⁱ	99.78 (8)	C7—C8—H8B	113.9
N2—Cu1—O2ⁱ	90.84 (8)	C3—C8—H8B	113.9
N1—Cu1—O2ⁱ	92.67 (8)	H8A—C8—H8B	111.1
Cl1—Cu1—O2ⁱ	95.00 (6)	O3—C9—C10	123.2 (4)
C1—O1—Cu1	117.42 (18)	O3—C9—C7	120.5 (4)
C1—O2—Cu1ⁱⁱ	122.84 (18)	C10—C9—C7	116.3 (4)
C11—N1—C22	118.1 (2)	C9—C10—H10A	109.5
C11—N1—Cu1	129.0 (2)	C9—C10—H10B	109.5
C22—N1—Cu1	112.83 (18)	H10A—C10—H10B	109.5
C20—N2—C21	117.7 (3)	C9—C10—H10C	109.5
C20—N2—Cu1	128.4 (2)	H10A—C10—H10C	109.5
C21—N2—Cu1	113.88 (18)	H10B—C10—H10C	109.5
O2—C1—O1	124.1 (3)	N1—C11—C12	122.1 (3)
O2—C1—C2	121.5 (3)	N1—C11—H11	118.9
O1—C1—C2	114.4 (3)	C12—C11—H11	118.9
C3—C2—C1	114.2 (3)	C13—C12—C11	120.0 (3)
C3—C2—H2A	108.7	C13—C12—H12	120.0
C1—C2—H2A	108.7	C11—C12—H12	120.0
C3—C2—H2B	108.7	C12—C13—C14	119.9 (3)
C1—C2—H2B	108.7	C12—C13—H13	120.1
H2A—C2—H2B	107.6	C14—C13—H13	120.1
C2—C3—C8	119.2 (3)	C22—C14—C13	116.3 (3)
C2—C3—C4	120.3 (3)	C22—C14—C15	118.6 (3)
C8—C3—C4	89.5 (3)	C13—C14—C15	125.0 (3)
C2—C3—H3	108.8	C16—C15—C14	121.6 (3)
C8—C3—H3	108.8	C16—C15—H15	119.2
C4—C3—H3	108.8	C14—C15—H15	119.2
C5—C4—C6	110.8 (4)	C15—C16—C17	120.9 (3)
C5—C4—C3	115.8 (3)	C15—C16—H16	119.6
C6—C4—C3	111.6 (3)	C17—C16—H16	119.6
C5—C4—C7	118.6 (3)	C21—C17—C18	117.2 (3)
C6—C4—C7	111.8 (3)	C21—C17—C16	118.9 (3)
C3—C4—C7	86.1 (3)	C18—C17—C16	123.9 (3)
C4—C5—H5A	109.5	C19—C18—C17	118.8 (3)
C4—C5—H5B	109.5	C19—C18—H18	120.6
H5A—C5—H5B	109.5	C17—C18—H18	120.6
C4—C5—H5C	109.5	C18—C19—C20	120.3 (3)
H5A—C5—H5C	109.5	C18—C19—H19	119.9
H5B—C5—H5C	109.5	C20—C19—H19	119.9
C4—C6—H6A	109.5	N2—C20—C19	122.4 (3)
C4—C6—H6B	109.5	N2—C20—H20	118.8
H6A—C6—H6B	109.5	C19—C20—H20	118.8
C4—C6—H6C	109.5	N2—C21—C17	123.6 (3)
H6A—C6—H6C	109.5	N2—C21—C22	115.8 (2)
H6B—C6—H6C	109.5	C17—C21—C22	120.6 (3)
C9—C7—C8	119.7 (4)	N1—C22—C14	123.6 (3)
C9—C7—C4	116.8 (3)	N1—C22—C21	117.0 (2)
C8—C7—C4	89.8 (3)	C14—C22—C21	119.4 (3)

N2—Cu1—O1—C1	−84.8 (2)	C4—C3—C8—C7	−19.2 (3)
N1—Cu1—O1—C1	−33.3 (4)	C8—C7—C9—O3	−1.9 (7)
Cl1—Cu1—O1—C1	88.70 (19)	C4—C7—C9—O3	104.6 (5)
O2ⁱ—Cu1—O1—C1	−175.62 (19)	C8—C7—C9—C10	176.5 (4)
O1—Cu1—N1—C11	128.7 (3)	C4—C7—C9—C10	−76.9 (5)
N2—Cu1—N1—C11	−178.8 (3)	C22—N1—C11—C12	0.3 (4)
Cl1—Cu1—N1—C11	6.8 (3)	Cu1—N1—C11—C12	179.2 (2)
O2ⁱ—Cu1—N1—C11	−88.4 (3)	N1—C11—C12—C13	−0.4 (5)
O1—Cu1—N1—C22	−52.3 (4)	C11—C12—C13—C14	0.6 (5)
N2—Cu1—N1—C22	0.14 (19)	C12—C13—C14—C22	−0.8 (5)
Cl1—Cu1—N1—C22	−174.20 (18)	C12—C13—C14—C15	−179.4 (3)
O2ⁱ—Cu1—N1—C22	90.55 (19)	C22—C14—C15—C16	−0.6 (5)
O1—Cu1—N2—C20	−13.9 (3)	C13—C14—C15—C16	177.9 (3)
N1—Cu1—N2—C20	178.4 (3)	C14—C15—C16—C17	−0.4 (5)
Cl1—Cu1—N2—C20	−130.9 (5)	C15—C16—C17—C21	1.9 (5)
O2ⁱ—Cu1—N2—C20	85.9 (3)	C15—C16—C17—C18	−178.3 (3)
O1—Cu1—N2—C21	167.71 (19)	C21—C17—C18—C19	0.7 (4)
N1—Cu1—N2—C21	0.05 (19)	C16—C17—C18—C19	−179.1 (3)
Cl1—Cu1—N2—C21	50.7 (6)	C17—C18—C19—C20	−0.1 (5)
O2ⁱ—Cu1—N2—C21	−92.51 (19)	C21—N2—C20—C19	1.1 (4)
Cu1ⁱⁱ—O2—C1—O1	137.8 (2)	Cu1—N2—C20—C19	−177.3 (2)
Cu1ⁱⁱ—O2—C1—C2	−40.6 (3)	C18—C19—C20—N2	−0.8 (5)
Cu1—O1—C1—O2	−0.9 (4)	C20—N2—C21—C17	−0.5 (4)
Cu1—O1—C1—C2	177.59 (19)	Cu1—N2—C21—C17	178.1 (2)
O2—C1—C2—C3	−134.8 (3)	C20—N2—C21—C22	−178.8 (3)
O1—C1—C2—C3	46.7 (4)	Cu1—N2—C21—C22	−0.2 (3)
C1—C2—C3—C8	−171.3 (3)	C18—C17—C21—N2	−0.4 (4)
C1—C2—C3—C4	80.3 (4)	C16—C17—C21—N2	179.4 (3)
C2—C3—C4—C5	−97.2 (4)	C18—C17—C21—C22	177.9 (3)
C8—C3—C4—C5	138.7 (4)	C16—C17—C21—C22	−2.4 (4)
C2—C3—C4—C6	30.8 (4)	C11—N1—C22—C14	−0.6 (4)
C8—C3—C4—C6	−93.2 (3)	Cu1—N1—C22—C14	−179.6 (2)
C2—C3—C4—C7	142.8 (3)	C11—N1—C22—C21	178.8 (3)
C8—C3—C4—C7	18.7 (3)	Cu1—N1—C22—C21	−0.3 (3)
C5—C4—C7—C9	100.1 (5)	C13—C14—C22—N1	0.8 (5)
C6—C4—C7—C9	−30.8 (5)	C15—C14—C22—N1	179.5 (3)
C3—C4—C7—C9	−142.6 (4)	C13—C14—C22—C21	−178.5 (3)
C5—C4—C7—C8	−136.3 (4)	C15—C14—C22—C21	0.2 (4)
C6—C4—C7—C8	92.8 (4)	N2—C21—C22—N1	0.4 (4)
C3—C4—C7—C8	−19.0 (3)	C17—C21—C22—N1	−178.0 (3)
C9—C7—C8—C3	140.3 (4)	N2—C21—C22—C14	179.7 (3)
C4—C7—C8—C3	19.2 (3)	C17—C21—C22—C14	1.4 (4)
C2—C3—C8—C7	−144.2 (3)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₀H₁₅O₃)Cl(C₁₂H₈N₂)]
M_r	462.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	14.6143 (11), 14.4920 (12), 9.8419 (8)
β (°)	98.208 (1)
V (Å³)	2063.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Siemens SMART CCD
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.793, 0.829
No. of measured, independent and observed [I > 2σ(I)] reflections	10533, 3647, 2924
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.03
No. of reflections	3647
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.30

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O1	1.937 (2)	Cu1—Cl1	2.2610 (8)
Cu1—N2	2.030 (2)	Cu1—O2ⁱ	2.305 (2)
Cu1—N1	2.050 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (No·Y07–2-14).

References

Che, G.-B., Xu, Z.-L. & Liu, C.-B. (2006). Acta Cryst. E62, m1695–m1696. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Vanderhoff, P. A., Thompson, H. W. & Lalancette, R. A. (1986). Acta Cryst. C42, 1766–1769. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar

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