catena-Poly[[(2,2′-bipyridine)copper(II)]-μ-5-tert-butyl­isophthalato]

Li, X.-L.; Huang, M.-L.

doi:10.1107/S1600536808035484

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages m1501-m1502

doi:10.1107/S1600536808035484

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catena-Poly[[(2,2′-bipyridine)copper(II)]-μ-5-tert-butylisophthalato]

Xiao-Ling Li ^a ^* and Miao-Ling Huang ^b

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Quanzhou Normal University, Quanzhou, Fujian 362000, People's Republic of China
^*Correspondence e-mail: zhangwy_hi@126.com

(Received 21 October 2008; accepted 30 October 2008; online 8 November 2008)

In the crystal structure of the title polymeric compound, [Cu(C₁₂H₁₂O₄)(C₁₀H₈N₂)]_n, the asymmetric unit consists of one Cu^II ion, one 5-tert-butylisophthalate (tbip) and one 2,2′-bipyridine (bpy) ligand. The copper(II) ion is four-coordinated by two N atoms from bipy and two O atoms from two tbip ligands, leading to a distorted tetrahedral coordination. Each tbip ligand adopts a bis-monodentate coordination mode to connect two symmetry-related copper(II) ions, so forming a zigzag polymer chain parallel to [001]. The tert-butyl methyl groups are disordered over two positions with occupancies of 0.506 (6)/0.494 (6)

Related literature

For related literature on the synthesis of flexible organic ligands, see: Chang et al. (2005 ); Ma, Chen et al. (2008 ); Xu et al. (2006 ). For related literature on coordination polymers, see: Ma, Wang, Huo et al. (2008 ); Ma, Wang, Wang et al. (2008 ); Pan et al. (2006 ); Yang et al. (2002 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Cu(C₁₂H₁₂O₄)(C₁₀H₈N₂)]
M_r = 439.94
Monoclinic, P 2₁ /c
a = 8.905 (2) Å
b = 20.875 (5) Å
c = 11.564 (3) Å
β = 98.188 (3)°
V = 2127.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 296 (2) K
0.29 × 0.22 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.716, T_max = 0.845
15716 measured reflections
3949 independent reflections
3021 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.130
S = 1.05
3949 reflections
260 parameters
91 restraints
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—O1	1.933 (2)
Cu1—O3ⁱ	1.956 (2)
Cu1—N1	1.985 (3)
Cu1—N2	1.983 (3)

O1—Cu1—O3ⁱ	88.17 (11)
O1—Cu1—N1	94.83 (11)
O3ⁱ—Cu1—N1	172.79 (11)
O1—Cu1—N2	173.34 (11)
O3ⁱ—Cu1—N2	96.69 (11)
N1—Cu1—N2	80.88 (11)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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 I, global. DOI: 10.1107/S1600536808035484/su2072sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035484/su2072Isup2.hkl

checkCIF report

Comment top

It is well known that organic ligands play a crucial role in the design and construction of desirable frameworks. The changes in flexibility, length and symmetry of organic ligands can result in a remarkable class of materials bearing diverse architectures and functions. Thus, the construction of target molecules is a challenge for synthetic chemists (Ma et al., 2008; Chang et al., 2005; Xu et al., 2006). Benzene-1,3-dicarboxylic acid (isophthalic acid, H2isop) and its derivatives, with special conformations such as, an angle of 120° between two carboxylic groups, present versatile coordination modes that can yield predetermined networks. Such ligands have been widely used to construct coordination polymers (Pan et al., 2006; Yang et al., 2002; Ma et al., 2008).

The title compound, (I), was prepared by hydrothermal synthesis using 5-tert-butyl isophthalic acid, 2,2'-bipyridine and copper(II) actate. The asymmetric unit of (I) consists of one copper(II) ion, one tbip and one bipy ligand molecules (Fig. 1). Each copper(II) ion is four-coordinated by two nitrogen atoms from one bipy molecule and two oxygen atoms from two tbip ligands (Table 1). The coordination geometry of the copper(II) ion is distorted tetrahedral. The Cu—O bond lengths [1.933 (2)–1.965 (2) Å] are within the range reported for tetrahedral environments, and the Cu—N bond lengths [1.983 (3)–1.985 (3) Å] are also similar to those found in other tetrahedral copper complexes of bipy (Allen et al., 1987). Each tbip ligand adopts the bis-monodentated coordination mode to connect two symmetry related copper(II) ions so forming a zigzag polymer chain (Fig. 2).

Related literature top

For related literature on the synthesis of flexible organic ligands, see: Chang et al. (2005); Ma, Chen et al. (2008); Xu et al. (2006). For related literature on coordination polymers, see: Ma, Wang, Huo et al. (2008); Ma, Wang, Wang et al.(2008); Pan et al. (2006); Yang et al. (2002). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 5-tert-butyl isophthalic acid (0.1 mmol, 23.1 mg), 2,2'-bipyridine (0.1 mmol, 15.8 mg), Cu(OAc).2.4H₂O (0.05 mmol, 11.5 mg), NaOH (0.1 mmol, 4.0 mg) and H₂O (15 ml) was placed in a Teflon-lined stainless steel vessel, and heated to 160 °C for 4 days. It was then cooled to room temperature over a period of 24 h. Blue block-like crystals of compound (I) were obtained.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. A view of the asymmetric unit of compound (I), with thermal ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity. Atoms with label A are related to those without by symmetry operation (x, -y+1.5, z+0.5).
	Fig. 2. A partial view, along the a axis, of the crystal packing of compound (I) showing the zigzag polymer chain. H atoms have been omitted for clarity.

catena-Poly[[(2,2'-bipyridine)copper(II)]-µ-5-tert-butylisophthalato] top

Crystal data top

[Cu(C₁₂H₁₂O₄)(C₁₀H₈N₂)]	F(000) = 908
M_r = 439.94	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3455 reflections
a = 8.905 (2) Å	θ = 2.5–22.5°
b = 20.875 (5) Å	µ = 1.06 mm⁻¹
c = 11.564 (3) Å	T = 296 K
β = 98.188 (3)°	Block, blue
V = 2127.8 (9) Å³	0.29 × 0.22 × 0.16 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3949 independent reflections
Radiation source: fine-focus sealed tube	3021 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→10
T_min = 0.716, T_max = 0.845	k = −25→25
15716 measured reflections	l = −13→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.065P)² + 1.7017P] where P = (F_o² + 2F_c²)/3
3949 reflections	(Δ/σ)_max = 0.001
260 parameters	Δρ_max = 0.64 e Å⁻³
91 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Cu(C₁₂H₁₂O₄)(C₁₀H₈N₂)]	V = 2127.8 (9) Å³
M_r = 439.94	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.905 (2) Å	µ = 1.06 mm⁻¹
b = 20.875 (5) Å	T = 296 K
c = 11.564 (3) Å	0.29 × 0.22 × 0.16 mm
β = 98.188 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3949 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3021 reflections with I > 2σ(I)
T_min = 0.716, T_max = 0.845	R_int = 0.040
15716 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	91 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.05	Δρ_max = 0.64 e Å⁻³
3949 reflections	Δρ_min = −0.55 e Å⁻³
260 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C10	−0.2988 (8)	0.7849 (4)	0.0801 (8)	0.0991 (17)	0.50
H10A	−0.3808	0.7876	0.1255	0.149*	0.50
H10B	−0.2580	0.7422	0.0851	0.149*	0.50
H10C	−0.3355	0.7948	0.0000	0.149*	0.50
C11	−0.1382 (9)	0.8222 (4)	0.2581 (6)	0.1033 (17)	0.50
H11A	−0.0577	0.8506	0.2893	0.155*	0.50
H11B	−0.1070	0.7786	0.2736	0.155*	0.50
H11C	−0.2266	0.8310	0.2943	0.155*	0.50
C12	−0.2268 (8)	0.9003 (3)	0.1063 (7)	0.1019 (19)	0.50
H12A	−0.3113	0.9085	0.1473	0.153*	0.50
H12B	−0.2570	0.9071	0.0242	0.153*	0.50
H12C	−0.1450	0.9288	0.1341	0.153*	0.50
C10'	−0.2432 (9)	0.7777 (3)	0.1868 (8)	0.0991 (17)	0.50
H10D	−0.2073	0.7791	0.2691	0.149*	0.50
H10E	−0.2138	0.7378	0.1553	0.149*	0.50
H10F	−0.3518	0.7813	0.1743	0.149*	0.50
C11'	−0.1082 (9)	0.8784 (4)	0.2317 (7)	0.1033 (17)	0.50
H11D	−0.0967	0.9208	0.2021	0.155*	0.50
H11E	−0.0112	0.8626	0.2671	0.155*	0.50
H11F	−0.1764	0.8796	0.2890	0.155*	0.50
C12'	−0.2878 (8)	0.8749 (4)	0.0548 (7)	0.1019 (19)	0.50
H12D	−0.3658	0.8871	0.0998	0.153*	0.50
H12E	−0.3324	0.8523	−0.0138	0.153*	0.50
H12F	−0.2371	0.9125	0.0323	0.153*	0.50
Cu1	0.30126 (5)	0.570966 (18)	0.17572 (3)	0.03784 (16)
O1	0.1606 (3)	0.63474 (11)	0.1038 (2)	0.0497 (6)
O2	0.3724 (3)	0.67027 (13)	0.0490 (3)	0.0598 (7)
O3	0.3259 (3)	0.87708 (12)	−0.1821 (2)	0.0507 (6)
O4	0.1347 (3)	0.94173 (12)	−0.1635 (2)	0.0542 (7)
N1	0.2646 (3)	0.50997 (13)	0.0430 (2)	0.0368 (6)
N2	0.4556 (3)	0.50539 (13)	0.2322 (2)	0.0371 (6)
C1	0.2394 (5)	0.67826 (18)	0.0641 (3)	0.0510 (8)
C2	0.1631 (4)	0.74186 (15)	0.0367 (3)	0.0397 (8)
C3	0.2214 (4)	0.78533 (16)	−0.0351 (3)	0.0394 (8)
H3	0.3084	0.7756	−0.0676	0.047*
C4	0.1487 (4)	0.84380 (15)	−0.0584 (3)	0.0378 (8)
C5	0.0213 (4)	0.85804 (16)	−0.0065 (3)	0.0430 (8)
H5	−0.0261	0.8974	−0.0220	0.052*
C6	−0.0377 (4)	0.81567 (17)	0.0678 (3)	0.0460 (9)
C7	0.0343 (4)	0.75671 (16)	0.0860 (3)	0.0448 (9)
H7	−0.0050	0.7264	0.1325	0.054*
C8	0.2057 (4)	0.89150 (16)	−0.1391 (3)	0.0422 (8)
C9	−0.1753 (6)	0.8323 (2)	0.1271 (5)	0.0809 (12)
C13	0.1605 (4)	0.51736 (18)	−0.0526 (3)	0.0469 (9)
H13	0.1031	0.5547	−0.0608	0.056*
C14	0.1365 (4)	0.4717 (2)	−0.1382 (3)	0.0541 (10)
H14	0.0625	0.4775	−0.2026	0.065*
C15	0.2233 (5)	0.4176 (2)	−0.1271 (4)	0.0575 (11)
H15	0.2087	0.3860	−0.1842	0.069*
C16	0.3328 (4)	0.40997 (18)	−0.0308 (3)	0.0485 (9)
H16	0.3938	0.3736	−0.0230	0.058*
C17	0.3503 (4)	0.45690 (16)	0.0533 (3)	0.0352 (7)
C18	0.4614 (4)	0.45458 (16)	0.1610 (3)	0.0353 (7)
C19	0.5640 (4)	0.40508 (18)	0.1901 (3)	0.0478 (9)
H19	0.5675	0.3703	0.1402	0.057*
C20	0.6603 (5)	0.4085 (2)	0.2941 (4)	0.0556 (10)
H20	0.7289	0.3755	0.3156	0.067*
C21	0.6549 (5)	0.4606 (2)	0.3664 (3)	0.0548 (10)
H21	0.7203	0.4638	0.4364	0.066*
C22	0.5505 (4)	0.50766 (18)	0.3323 (3)	0.0475 (9)
H22	0.5457	0.5428	0.3811	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C10	0.081 (4)	0.096 (3)	0.134 (4)	0.009 (3)	0.061 (3)	0.009 (3)
C11	0.101 (4)	0.102 (4)	0.118 (4)	0.020 (3)	0.058 (3)	−0.004 (3)
C12	0.087 (4)	0.084 (3)	0.144 (5)	0.035 (3)	0.048 (3)	0.007 (3)
C10'	0.081 (4)	0.096 (3)	0.134 (4)	0.009 (3)	0.061 (3)	0.009 (3)
C11'	0.101 (4)	0.102 (4)	0.118 (4)	0.020 (3)	0.058 (3)	−0.004 (3)
C12'	0.087 (4)	0.084 (3)	0.144 (5)	0.035 (3)	0.048 (3)	0.007 (3)
Cu1	0.0495 (3)	0.0268 (2)	0.0376 (3)	0.00568 (18)	0.00751 (18)	0.00124 (16)
O1	0.0618 (16)	0.0312 (13)	0.0578 (16)	0.0093 (12)	0.0143 (13)	0.0113 (11)
O2	0.0639 (14)	0.0477 (13)	0.0722 (16)	0.0222 (12)	0.0247 (13)	0.0112 (12)
O3	0.0599 (17)	0.0424 (14)	0.0514 (16)	−0.0017 (12)	0.0132 (13)	0.0113 (12)
O4	0.0725 (18)	0.0373 (14)	0.0517 (16)	0.0066 (13)	0.0042 (13)	0.0124 (12)
N1	0.0414 (16)	0.0347 (15)	0.0340 (15)	0.0035 (12)	0.0042 (12)	0.0052 (12)
N2	0.0448 (16)	0.0336 (15)	0.0322 (14)	−0.0010 (12)	0.0029 (12)	0.0018 (12)
C1	0.0611 (16)	0.0381 (16)	0.0573 (18)	0.0190 (15)	0.0207 (15)	0.0079 (14)
C2	0.051 (2)	0.0288 (17)	0.0407 (19)	0.0085 (15)	0.0102 (16)	0.0041 (14)
C3	0.046 (2)	0.0351 (18)	0.0373 (18)	0.0047 (15)	0.0085 (15)	0.0008 (15)
C4	0.046 (2)	0.0293 (16)	0.0363 (18)	0.0006 (14)	0.0008 (15)	0.0015 (14)
C5	0.046 (2)	0.0299 (18)	0.051 (2)	0.0079 (15)	−0.0001 (16)	0.0030 (15)
C6	0.047 (2)	0.0335 (18)	0.059 (2)	0.0083 (16)	0.0106 (17)	0.0025 (17)
C7	0.051 (2)	0.0324 (18)	0.055 (2)	0.0062 (16)	0.0187 (17)	0.0105 (16)
C8	0.058 (2)	0.0337 (18)	0.0317 (17)	−0.0047 (17)	−0.0048 (16)	0.0022 (14)
C9	0.075 (3)	0.062 (2)	0.118 (3)	0.021 (2)	0.054 (3)	0.011 (2)
C13	0.047 (2)	0.049 (2)	0.043 (2)	0.0062 (17)	0.0025 (16)	0.0034 (17)
C14	0.047 (2)	0.070 (3)	0.043 (2)	−0.009 (2)	−0.0010 (17)	−0.0015 (19)
C15	0.062 (3)	0.060 (3)	0.049 (2)	−0.009 (2)	0.0051 (19)	−0.020 (2)
C16	0.052 (2)	0.042 (2)	0.052 (2)	0.0024 (17)	0.0075 (18)	−0.0099 (17)
C17	0.0374 (18)	0.0351 (17)	0.0343 (17)	−0.0003 (14)	0.0090 (14)	0.0010 (14)
C18	0.0388 (18)	0.0322 (17)	0.0367 (18)	0.0022 (14)	0.0112 (14)	0.0039 (14)
C19	0.053 (2)	0.043 (2)	0.048 (2)	0.0117 (18)	0.0132 (17)	0.0019 (17)
C20	0.055 (2)	0.058 (2)	0.053 (2)	0.020 (2)	0.0061 (19)	0.012 (2)
C21	0.057 (2)	0.061 (3)	0.044 (2)	0.004 (2)	−0.0044 (18)	0.0116 (19)
C22	0.057 (2)	0.043 (2)	0.041 (2)	−0.0016 (18)	0.0012 (17)	0.0005 (16)

Geometric parameters (Å, º) top

C10—C9	1.521 (9)	N1—C17	1.341 (4)
C10—H10A	0.9600	N1—C13	1.347 (4)
C10—H10B	0.9600	N2—C22	1.333 (4)
C10—H10C	0.9600	N2—C18	1.348 (4)
C11—C9	1.519 (9)	C1—C2	1.505 (5)
C11—H11A	0.9600	C2—C3	1.381 (5)
C11—H11B	0.9600	C2—C7	1.386 (5)
C11—H11C	0.9600	C3—C4	1.390 (5)
C12—C9	1.501 (7)	C3—H3	0.9300
C12—H12A	0.9600	C4—C5	1.389 (5)
C12—H12B	0.9600	C4—C8	1.502 (5)
C12—H12C	0.9600	C5—C6	1.387 (5)
C10'—C9	1.504 (8)	C5—H5	0.9300
C10'—H10D	0.9600	C6—C7	1.390 (5)
C10'—H10E	0.9600	C6—C9	1.527 (6)
C10'—H10F	0.9600	C7—H7	0.9300
C11'—C9	1.595 (9)	C8—Cu1ⁱⁱ	2.538 (4)
C11'—H11D	0.9600	C13—C14	1.368 (5)
C11'—H11E	0.9600	C13—H13	0.9300
C11'—H11F	0.9600	C14—C15	1.365 (6)
C12'—C9	1.502 (8)	C14—H14	0.9300
C12'—H12D	0.9600	C15—C16	1.382 (6)
C12'—H12E	0.9600	C15—H15	0.9300
C12'—H12F	0.9600	C16—C17	1.373 (5)
Cu1—O1	1.933 (2)	C16—H16	0.9300
Cu1—O3ⁱ	1.956 (2)	C17—C18	1.477 (5)
Cu1—N1	1.985 (3)	C18—C19	1.388 (5)
Cu1—N2	1.983 (3)	C19—C20	1.376 (5)
Cu1—C8ⁱ	2.538 (4)	C19—H19	0.9300
O1—C1	1.273 (4)	C20—C21	1.377 (6)
O2—C1	1.233 (5)	C20—H20	0.9300
O3—C8	1.279 (5)	C21—C22	1.372 (5)
O3—Cu1ⁱⁱ	1.956 (2)	C21—H21	0.9300
O4—C8	1.236 (4)	C22—H22	0.9300

C9—C10—H10A	109.5	C6—C5—C4	122.4 (3)
C9—C10—H10B	109.5	C6—C5—H5	118.8
H10A—C10—H10B	109.5	C4—C5—H5	118.8
C9—C10—H10C	109.5	C5—C6—C7	116.8 (3)
H10A—C10—H10C	109.5	C5—C6—C9	122.1 (3)
H10B—C10—H10C	109.5	C7—C6—C9	121.0 (4)
C9—C11—H11A	109.5	C2—C7—C6	121.8 (3)
C9—C11—H11B	109.5	C2—C7—H7	119.1
H11A—C11—H11B	109.5	C6—C7—H7	119.1
C9—C11—H11C	109.5	O4—C8—O3	122.7 (3)
H11A—C11—H11C	109.5	O4—C8—C4	119.8 (4)
H11B—C11—H11C	109.5	O3—C8—C4	117.5 (3)
C9—C12—H12A	109.5	O4—C8—Cu1ⁱⁱ	76.6 (2)
C9—C12—H12B	109.5	O3—C8—Cu1ⁱⁱ	49.07 (17)
H12A—C12—H12B	109.5	C4—C8—Cu1ⁱⁱ	155.9 (2)
C9—C12—H12C	109.5	C12—C9—C10'	131.1 (4)
H12A—C12—H12C	109.5	C12'—C9—C10'	115.1 (5)
H12B—C12—H12C	109.5	C12—C9—C11	108.0 (5)
C9—C10'—H10D	109.5	C12'—C9—C11	132.1 (5)
C9—C10'—H10E	109.5	C10'—C9—C11	58.7 (3)
H10D—C10'—H10E	109.5	C12—C9—C10	111.7 (5)
C9—C10'—H10F	109.5	C12'—C9—C10	78.2 (4)
H10D—C10'—H10F	109.5	C10'—C9—C10	49.7 (2)
H10E—C10'—H10F	109.5	C11—C9—C10	108.0 (4)
C9—C11'—H11D	109.5	C12—C9—C6	112.9 (4)
C9—C11'—H11E	109.5	C12'—C9—C6	113.5 (5)
H11D—C11'—H11E	109.5	C10'—C9—C6	115.8 (4)
C9—C11'—H11F	109.5	C11—C9—C6	110.0 (5)
H11D—C11'—H11F	109.5	C10—C9—C6	106.1 (5)
H11E—C11'—H11F	109.5	C12—C9—C11'	67.9 (3)
C9—C12'—H12D	109.5	C12'—C9—C11'	102.3 (4)
C9—C12'—H12E	109.5	C10'—C9—C11'	103.9 (5)
H12D—C12'—H12E	109.5	C11—C9—C11'	47.3 (2)
C9—C12'—H12F	109.5	C10—C9—C11'	146.9 (5)
H12D—C12'—H12F	109.5	C6—C9—C11'	103.9 (5)
H12E—C12'—H12F	109.5	N1—C13—C14	122.2 (4)
O1—Cu1—O3ⁱ	88.17 (11)	N1—C13—H13	118.9
O1—Cu1—N1	94.83 (11)	C14—C13—H13	118.9
O3ⁱ—Cu1—N1	172.79 (11)	C15—C14—C13	118.7 (4)
O1—Cu1—N2	173.34 (11)	C15—C14—H14	120.6
O3ⁱ—Cu1—N2	96.69 (11)	C13—C14—H14	120.6
N1—Cu1—N2	80.88 (11)	C14—C15—C16	119.8 (4)
O1—Cu1—C8ⁱ	82.87 (11)	C14—C15—H15	120.1
O3ⁱ—Cu1—C8ⁱ	29.60 (11)	C16—C15—H15	120.1
N2—Cu1—C8ⁱ	103.60 (11)	C17—C16—C15	119.0 (4)
N1—Cu1—C8ⁱ	144.33 (12)	C17—C16—H16	120.5
C1—O1—Cu1	106.8 (2)	C15—C16—H16	120.5
C8—O3—Cu1ⁱⁱ	101.3 (2)	N1—C17—C16	121.4 (3)
C17—N1—C13	118.9 (3)	N1—C17—C18	114.0 (3)
C17—N1—Cu1	115.6 (2)	C16—C17—C18	124.6 (3)
C13—N1—Cu1	125.4 (2)	N2—C18—C19	121.3 (3)
C22—N2—C18	118.9 (3)	N2—C18—C17	114.2 (3)
C22—N2—Cu1	125.8 (2)	C19—C18—C17	124.5 (3)
C18—N2—Cu1	115.3 (2)	C20—C19—C18	118.7 (4)
O2—C1—O1	123.0 (3)	C20—C19—H19	120.7
O2—C1—C2	120.3 (3)	C18—C19—H19	120.7
O1—C1—C2	116.7 (3)	C19—C20—C21	120.0 (4)
C3—C2—C7	120.3 (3)	C19—C20—H20	120.0
C3—C2—C1	120.6 (3)	C21—C20—H20	120.0
C7—C2—C1	119.1 (3)	C22—C21—C20	118.2 (4)
C2—C3—C4	119.3 (3)	C22—C21—H21	120.9
C2—C3—H3	120.4	C20—C21—H21	120.9
C4—C3—H3	120.4	N2—C22—C21	123.0 (4)
C5—C4—C3	119.4 (3)	N2—C22—H22	118.5
C5—C4—C8	119.7 (3)	C21—C22—H22	118.5
C3—C4—C8	120.9 (3)

O3ⁱ—Cu1—O1—C1	84.9 (3)	C3—C4—C8—Cu1ⁱⁱ	47.6 (8)
N1—Cu1—O1—C1	−101.7 (3)	C5—C6—C9—C12	−6.0 (7)
C8ⁱ—Cu1—O1—C1	114.1 (3)	C7—C6—C9—C12	174.1 (5)
O1—Cu1—N1—C17	176.4 (2)	C5—C6—C9—C12'	32.7 (7)
N2—Cu1—N1—C17	1.5 (2)	C7—C6—C9—C12'	−147.2 (5)
C8ⁱ—Cu1—N1—C17	−99.1 (3)	C5—C6—C9—C10'	169.2 (6)
N2—Cu1—N1—C13	−180.0 (3)	C7—C6—C9—C10'	−10.7 (8)
C8ⁱ—Cu1—N1—C13	79.4 (3)	C5—C6—C9—C11	−126.8 (5)
O3ⁱ—Cu1—N2—C22	−7.2 (3)	C7—C6—C9—C11	53.3 (7)
N1—Cu1—N2—C22	179.6 (3)	C5—C6—C9—C10	116.6 (5)
C8ⁱ—Cu1—N2—C22	−36.5 (3)	C7—C6—C9—C10	−63.3 (6)
O3ⁱ—Cu1—N2—C18	172.5 (2)	C5—C6—C9—C11'	−77.6 (6)
N1—Cu1—N2—C18	−0.6 (2)	C7—C6—C9—C11'	102.6 (5)
C8ⁱ—Cu1—N2—C18	143.3 (2)	C17—N1—C13—C14	1.8 (5)
Cu1—O1—C1—O2	17.2 (5)	Cu1—N1—C13—C14	−176.7 (3)
Cu1—O1—C1—C2	−162.2 (3)	N1—C13—C14—C15	−1.4 (6)
O2—C1—C2—C3	18.7 (6)	C13—C14—C15—C16	−0.1 (6)
O1—C1—C2—C3	−162.0 (3)	C14—C15—C16—C17	1.1 (6)
O2—C1—C2—C7	−160.4 (4)	C13—N1—C17—C16	−0.7 (5)
O1—C1—C2—C7	19.0 (5)	Cu1—N1—C17—C16	178.0 (3)
C7—C2—C3—C4	−0.7 (5)	C13—N1—C17—C18	179.3 (3)
C1—C2—C3—C4	−179.7 (3)	Cu1—N1—C17—C18	−2.1 (4)
C2—C3—C4—C5	1.7 (5)	C15—C16—C17—N1	−0.7 (6)
C2—C3—C4—C8	−178.1 (3)	C15—C16—C17—C18	179.3 (3)
C3—C4—C5—C6	−0.5 (5)	C22—N2—C18—C19	−0.1 (5)
C8—C4—C5—C6	179.3 (3)	Cu1—N2—C18—C19	−179.8 (3)
C4—C5—C6—C7	−1.7 (6)	C22—N2—C18—C17	179.5 (3)
C4—C5—C6—C9	178.4 (4)	Cu1—N2—C18—C17	−0.3 (4)
C3—C2—C7—C6	−1.7 (6)	N1—C17—C18—N2	1.5 (4)
C1—C2—C7—C6	177.4 (4)	C16—C17—C18—N2	−178.5 (3)
C5—C6—C7—C2	2.8 (6)	N1—C17—C18—C19	−178.9 (3)
C9—C6—C7—C2	−177.3 (4)	C16—C17—C18—C19	1.1 (5)
Cu1ⁱⁱ—O3—C8—O4	−22.7 (4)	N2—C18—C19—C20	0.4 (5)
Cu1ⁱⁱ—O3—C8—C4	155.6 (2)	C17—C18—C19—C20	−179.2 (3)
C5—C4—C8—O4	−3.7 (5)	C18—C19—C20—C21	−0.8 (6)
C3—C4—C8—O4	176.1 (3)	C19—C20—C21—C22	0.9 (6)
C5—C4—C8—O3	178.0 (3)	C18—N2—C22—C21	0.2 (5)
C3—C4—C8—O3	−2.2 (5)	Cu1—N2—C22—C21	180.0 (3)
C5—C4—C8—Cu1ⁱⁱ	−132.2 (6)	C20—C21—C22—N2	−0.6 (6)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₂H₁₂O₄)(C₁₀H₈N₂)]
M_r	439.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.905 (2), 20.875 (5), 11.564 (3)
β (°)	98.188 (3)
V (Å³)	2127.8 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.29 × 0.22 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.716, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections	15716, 3949, 3021
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.130, 1.05
No. of reflections	3949
No. of parameters	260
No. of restraints	91
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.55

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—O1	1.933 (2)	Cu1—N1	1.985 (3)
Cu1—O3ⁱ	1.956 (2)	Cu1—N2	1.983 (3)

O1—Cu1—O3ⁱ	88.17 (11)	O1—Cu1—N2	173.34 (11)
O1—Cu1—N1	94.83 (11)	O3ⁱ—Cu1—N2	96.69 (11)
O3ⁱ—Cu1—N1	172.79 (11)	N1—Cu1—N2	80.88 (11)

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

The authors thank Luo Yang Normal University for supporting this work.

References

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