Tetra­kis(μ-naphthalene-1-acetato-κ2O:O′)bis­[(N,N-dimethyl­formamide-κO)copper(II)]

Yin, F.-J.; Gu, Y.; Zhao, H.; Bai, D.-S.

doi:10.1107/S1600536812007064

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page m350

doi:10.1107/S1600536812007064

Open

access

Tetrakis(μ-naphthalene-1-acetato-κ²O:O′)bis[(N,N-dimethylformamide-κO)copper(II)]

Fu-Jun Yin,^a ^* Yu Gu,^b Hong Zhao ^c and Di-Si Bai ^b

^aJiangsu Marine Resources Development, Research Institute, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^bQian'an College, Hebei United University, Tangshan 063009, People's Republic of China, and ^cDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China
^*Correspondence e-mail: yfj1999@126.com

(Received 5 February 2012; accepted 16 February 2012; online 29 February 2012)

The asymmetric unit of the title compound, [Cu₂(C₁₂H₉O₂)₄(C₃H₇NO)₂], contains two independent centrosymmetric dinuclear copper(II) complexes. The central paddle-wheel units are formed by four bridging bidentate naphthalene-1-acetate ligands with two dimethylformamide ligands in the axial positions. The unique Cu^II ions have slightly distorted square-pyramidal coordination geometries. One of the naphthalene rings is disordered over two sets of sites, with refined occpancies of 0.535 (4) and 0.465 (4).

Related literature

For coordination compounds of 1-naphthylacetate, see: Yin et al. (2010 ); Chen et al. (2004 ); Yang et al. (2008 ); Xia et al. (2006 ); Ji et al. (2011 ).

Experimental

Crystal data

[Cu₂(C₁₂H₉O₂)₄(C₃H₇NO)₂]
M_r = 1014.04
Triclinic, $[P \overline 1]$
a = 10.6704 (7) Å
b = 12.3561 (8) Å
c = 20.7734 (14) Å
α = 74.8390 (11)°
β = 84.898 (1)°
γ = 66.848 (1)°
V = 2430.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 298 K
0.10 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.945, T_max = 0.945
18538 measured reflections
8516 independent reflections
7103 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.115
S = 1.04
8516 reflections
630 parameters
16 restraints
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −1.25 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536812007064/lh5416sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007064/lh5416Isup2.hkl

checkCIF report

Comment top

Naphthalene-1-yl-acetate acid is a plant-growth regulator and exhibits remarkable coordination versatility towards metal cations (Yin et al., 2010; Chen et al., 2004; Yang et al., 2008; Xia et al.,2006; Ji et al., 2011). In continuation of the structural studies of metal complexes of this ligands, the crystal structure of the title compound was determined.

The molecular structure of the title compound (I) (see Figs. 1 & 2), contains a centrosymmetric dinuclear copper paddle-wheel unit, in which each Cu^II ion is coordinated by four O atoms from a naphthalen-1-yl-acetate ligand in the basal plane and one O atom of a N,N-dimethylformamide ligand in the axial position to form a square-pyramidal coordination geometry. Both independent molecules lie on crystallographic inversion centers.

Related literature top

For coordination compounds of 1-naphthylacetate, see: Yin et al. (2010); Chen et al. (2004); Yang et al. (2008); Xia et al. (2006); Ji et al. (2011).

Experimental top

The title compound was synthesized by the reaction of Cu(NO₃)₂ × 3 H₂O (72.3 mg, 0.3 mmol), naphthalene-1-yl-acetic acid (93 mg, 0.5 mmol), and NaOH (20 mg, 0.5 mmol) in 10 ml of N,N-dimethylformamide under solvothermal conditions. The mixture was homogenized and transferred into a sealed Teflon-lined solvothermal bomb (volume: 25 ml) and heated to 423K for three days. After cooling green crystals of the title compound were obtained, which were washed with distilled water and absolute ethanol (yield: 48.5% based on Cu(NO₃)₂ × 3 H₂O).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 one of the independent molecules of (I) showing displacement ellipsoids at the 30% probability [symmetry code (A): -x+2, -y+1, -z+1].
	Fig. 2. The molecular structure of the other independent molecule of (I) showing displacement ellipsoids at the 30% probability. [symmetry code (A): -x+1, -y+2, -z].

Tetrakis(µ-naphthalene-1-acetato- κ²O:O')bis[(N,N-dimethylformamide- κO)copper(II)] top

Crystal data top

[Cu₂(C₁₂H₉O₂)₄(C₃H₇NO)₂]	Z = 2
M_r = 1014.04	F(000) = 1052
Triclinic, P1	D_x = 1.386 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6704 (7) Å	Cell parameters from 7990 reflections
b = 12.3561 (8) Å	θ = 2.2–26.9°
c = 20.7734 (14) Å	µ = 0.94 mm⁻¹
α = 74.8390 (11)°	T = 298 K
β = 84.898 (1)°	Block, green
γ = 66.848 (1)°	0.10 × 0.10 × 0.10 mm
V = 2430.3 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	8516 independent reflections
Radiation source: fine-focus sealed tube	7103 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.945, T_max = 0.945	k = −14→14
18538 measured reflections	l = −24→24

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0486P)² + 2.352P] where P = (F_o² + 2F_c²)/3
8516 reflections	(Δ/σ)_max = 0.001
630 parameters	Δρ_max = 0.61 e Å⁻³
16 restraints	Δρ_min = −1.25 e Å⁻³

Crystal data top

[Cu₂(C₁₂H₉O₂)₄(C₃H₇NO)₂]	γ = 66.848 (1)°
M_r = 1014.04	V = 2430.3 (3) Å³
Triclinic, P1	Z = 2
a = 10.6704 (7) Å	Mo Kα radiation
b = 12.3561 (8) Å	µ = 0.94 mm⁻¹
c = 20.7734 (14) Å	T = 298 K
α = 74.8390 (11)°	0.10 × 0.10 × 0.10 mm
β = 84.898 (1)°

Data collection top

Bruker APEXII CCD diffractometer	8516 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	7103 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.945	R_int = 0.019
18538 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	16 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.04	Δρ_max = 0.61 e Å⁻³
8516 reflections	Δρ_min = −1.25 e Å⁻³
630 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	Occ. (<1)
Cu1	0.86554 (3)	0.53893 (3)	0.496213 (16)	0.03371 (10)
O1	0.8617 (2)	0.69486 (17)	0.50264 (11)	0.0474 (5)
O2	0.8686 (2)	0.48613 (19)	0.59443 (10)	0.0488 (5)
O3	1.0954 (2)	0.4191 (2)	0.60003 (10)	0.0505 (5)
O4	1.0886 (2)	0.62875 (17)	0.50813 (11)	0.0478 (5)
O5	0.65309 (19)	0.59391 (19)	0.47337 (11)	0.0481 (5)
N1	0.5038 (2)	0.5742 (2)	0.41095 (13)	0.0501 (6)
C1	0.9708 (3)	0.7076 (2)	0.50813 (14)	0.0396 (6)
C2	0.9582 (3)	0.8313 (3)	0.51355 (18)	0.0518 (8)
H2A	0.9535	0.8829	0.4690	0.062*
H2B	0.8734	0.8676	0.5355	0.062*
C3	1.0737 (3)	0.8278 (3)	0.55139 (17)	0.0491 (7)
C4	1.1703 (3)	0.8671 (3)	0.51830 (19)	0.0573 (8)
H4	1.1640	0.8955	0.4721	0.069*
C5	1.2789 (4)	0.8656 (3)	0.5526 (2)	0.0696 (10)
H5	1.3437	0.8925	0.5290	0.083*
C6	1.2896 (4)	0.8254 (4)	0.6193 (2)	0.0724 (11)
H6	1.3610	0.8263	0.6414	0.087*
C7	1.1946 (4)	0.7819 (3)	0.6562 (2)	0.0652 (9)
C8	1.0849 (3)	0.7827 (3)	0.62141 (19)	0.0558 (8)
C9	0.9902 (4)	0.7392 (4)	0.6595 (2)	0.0755 (11)
H9	0.9184	0.7383	0.6375	0.091*
C10	1.0003 (6)	0.6988 (5)	0.7266 (3)	0.1008 (15)
H10	0.9356	0.6716	0.7502	0.121*
C11	1.1078 (7)	0.6980 (5)	0.7602 (3)	0.1063 (17)
H11	1.1148	0.6701	0.8064	0.128*
C12	1.2028 (5)	0.7377 (5)	0.7261 (3)	0.0910 (14)
H12	1.2746	0.7356	0.7494	0.109*
C13	0.9805 (3)	0.4372 (3)	0.62552 (14)	0.0429 (7)
C14	0.9800 (4)	0.3984 (4)	0.70118 (16)	0.0592 (9)
H14E	1.0662	0.3317	0.7160	0.071*
H14F	0.9765	0.4655	0.7182	0.071*
C15	0.8679 (3)	0.3594 (3)	0.73282 (15)	0.0514 (8)
C16	0.7770 (5)	0.4238 (4)	0.77268 (18)	0.0784 (12)
H16A	0.7809	0.4954	0.7772	0.094*
C17	0.6777 (5)	0.3840 (6)	0.8070 (2)	0.111 (2)
H17A	0.6164	0.4294	0.8339	0.133*
C18	0.6706 (5)	0.2804 (6)	0.8014 (3)	0.106 (2)
H18A	0.6056	0.2541	0.8253	0.127*
C19	0.7591 (4)	0.2122 (4)	0.7603 (2)	0.0781 (13)
C20	0.8604 (3)	0.2511 (3)	0.72557 (16)	0.0559 (8)
C21	0.9501 (4)	0.1789 (3)	0.6852 (2)	0.0743 (11)
H21A	1.0179	0.2020	0.6620	0.089*
C22	0.9383 (7)	0.0752 (4)	0.6798 (3)	0.115 (2)
H22A	0.9979	0.0288	0.6529	0.138*
C23	0.8379 (10)	0.0380 (6)	0.7143 (4)	0.146 (3)
H23A	0.8312	−0.0328	0.7103	0.176*
C24	0.7526 (7)	0.1037 (6)	0.7525 (4)	0.119 (2)
H24A	0.6861	0.0780	0.7750	0.143*
C25	0.6245 (3)	0.5422 (3)	0.43674 (16)	0.0478 (7)
H25A	0.6915	0.4723	0.4233	0.057*
C26	0.3898 (3)	0.6778 (3)	0.4237 (2)	0.0679 (10)
H26A	0.4112	0.7001	0.4610	0.102*
H26B	0.3109	0.6574	0.4336	0.102*
H26C	0.3712	0.7447	0.3850	0.102*
C27	0.4771 (4)	0.5066 (4)	0.3696 (2)	0.0817 (12)
H27A	0.5601	0.4409	0.3641	0.122*
H27B	0.4427	0.5597	0.3267	0.122*
H27C	0.4108	0.4747	0.3908	0.122*
Cu2	0.38926 (5)	0.97711 (5)	0.01857 (2)	0.07018 (17)
O6	0.3889 (3)	1.0570 (3)	0.08925 (12)	0.0702 (7)
O7	0.5200 (3)	0.8234 (3)	0.07183 (12)	0.0721 (7)
O8	0.5772 (3)	1.0939 (3)	0.05852 (13)	0.0949 (11)
O9	0.7071 (3)	0.8613 (3)	0.04101 (13)	0.0897 (10)
O10	0.2111 (3)	0.9402 (3)	0.05243 (13)	0.0763 (8)
N2	0.0108 (3)	0.9822 (3)	0.10633 (17)	0.0696 (8)
C28	0.4779 (4)	1.0960 (4)	0.09576 (17)	0.0685 (10)
C29	0.4625 (5)	1.1507 (4)	0.15480 (17)	0.0715 (10)
H2B1	0.3675	1.2023	0.1582	0.086*
H2B2	0.5151	1.2014	0.1471	0.086*
C30	0.5091 (3)	1.0557 (3)	0.22023 (16)	0.0516 (8)
C31	0.5883 (4)	0.9376 (4)	0.22208 (19)	0.0686 (10)
H4B	0.6157	0.9151	0.1821	0.082*
C32	0.6299 (4)	0.8485 (4)	0.2826 (2)	0.0802 (12)
H5B	0.6840	0.7684	0.2823	0.096*
C33	0.5912 (4)	0.8797 (4)	0.3410 (2)	0.0753 (11)
H6B	0.6193	0.8205	0.3808	0.090*
C34	0.5097 (4)	0.9990 (3)	0.34265 (16)	0.0574 (8)
C35	0.4690 (3)	1.0902 (3)	0.28141 (15)	0.0490 (7)
C36	0.3910 (4)	1.2112 (4)	0.2850 (2)	0.0646 (9)
H9B	0.3647	1.2723	0.2457	0.078*
C37	0.3538 (4)	1.2402 (5)	0.3447 (2)	0.0842 (13)
H10B	0.3037	1.3207	0.3456	0.101*
C38	0.3899 (4)	1.1507 (6)	0.4042 (2)	0.0883 (15)
H11B	0.3622	1.1711	0.4447	0.106*
C39	0.4654 (4)	1.0341 (5)	0.40307 (19)	0.0784 (12)
H12B	0.4889	0.9751	0.4432	0.094*
C40	0.6459 (4)	0.7965 (4)	0.07327 (17)	0.0671 (10)
C41	0.7311 (4)	0.6765 (4)	0.1201 (2)	0.0778 (10)
H14A	0.6651	0.6458	0.1444	0.093*	0.535 (4)
H14B	0.7704	0.6991	0.1523	0.093*	0.535 (4)
H14C	0.6961	0.6687	0.1651	0.093*	0.465 (4)
H14D	0.7984	0.7121	0.1174	0.093*	0.465 (4)
C42	0.8463 (8)	0.5647 (7)	0.1048 (4)	0.0778 (10)	0.535 (4)
C43	0.9800 (8)	0.5434 (7)	0.1138 (4)	0.072 (2)	0.535 (4)
H16B	1.0023	0.5938	0.1329	0.087*	0.535 (4)
C44	1.0858 (10)	0.4438 (8)	0.0940 (6)	0.082 (3)	0.535 (4)
H44	1.1765	0.4304	0.1001	0.098*	0.535 (4)
C45	1.0560 (10)	0.3701 (9)	0.0672 (4)	0.081 (3)	0.535 (4)
H18B	1.1263	0.3054	0.0551	0.097*	0.535 (4)
C46	0.9203 (9)	0.3882 (7)	0.0568 (4)	0.078 (2)	0.535 (4)
C47	0.8127 (8)	0.4873 (6)	0.0759 (3)	0.0697 (19)	0.535 (4)
C48	0.6745 (12)	0.5034 (9)	0.0661 (6)	0.1086 (19)	0.535 (4)
H21B	0.6032	0.5714	0.0745	0.130*	0.535 (4)
C49	0.6473 (13)	0.4207 (10)	0.0449 (7)	0.1086 (19)	0.535 (4)
H22B	0.5592	0.4220	0.0470	0.130*	0.535 (4)
C50	0.7563 (11)	0.3300 (9)	0.0188 (5)	0.1086 (19)	0.535 (4)
H23B	0.7362	0.2840	−0.0047	0.130*	0.535 (4)
C51	0.8885 (11)	0.3115 (9)	0.0284 (5)	0.1086 (19)	0.535 (4)
H24B	0.9583	0.2470	0.0158	0.130*	0.535 (4)
C42'	0.7119 (12)	0.5882 (10)	0.0827 (6)	0.1024 (14)	0.465 (4)
C43'	0.6485 (11)	0.5158 (10)	0.1209 (7)	0.1024 (14)	0.465 (4)
H16'	0.6118	0.5279	0.1620	0.123*	0.465 (4)
C44'	0.6408 (11)	0.4208 (10)	0.0953 (6)	0.1024 (14)	0.465 (4)
H17'	0.6018	0.3688	0.1212	0.123*	0.465 (4)
C45'	0.6911 (13)	0.4048 (14)	0.0316 (7)	0.1024 (14)	0.465 (4)
H18'	0.6783	0.3475	0.0144	0.123*	0.465 (4)
C46'	0.7591 (11)	0.4747 (10)	−0.0045 (6)	0.1024 (14)	0.465 (4)
C47'	0.7665 (11)	0.5695 (10)	0.0209 (6)	0.1024 (14)	0.465 (4)
C48'	0.8347 (11)	0.6422 (10)	−0.0192 (6)	0.1024 (14)	0.465 (4)
H21'	0.8411	0.7054	−0.0051	0.123*	0.465 (4)
C49'	0.8908 (14)	0.6185 (14)	−0.0786 (7)	0.1024 (14)	0.465 (4)
H22'	0.9348	0.6661	−0.1046	0.123*	0.465 (4)
C50'	0.8824 (14)	0.5247 (13)	−0.1000 (8)	0.1024 (14)	0.465 (4)
H23'	0.9236	0.5085	−0.1397	0.123*	0.465 (4)
C51'	0.8184 (11)	0.4587 (10)	−0.0659 (6)	0.1024 (14)	0.465 (4)
H24'	0.8118	0.3986	−0.0829	0.123*	0.465 (4)
C52	0.1214 (4)	1.0013 (4)	0.0845 (2)	0.0746 (12)
H25B	0.1181	1.0735	0.0955	0.090*
C53	−0.0098 (5)	0.8796 (5)	0.0961 (2)	0.0886 (14)
H26D	0.0601	0.8406	0.0678	0.133*
H26E	−0.0974	0.9067	0.0753	0.133*
H26F	−0.0059	0.8230	0.1382	0.133*
C54	−0.0924 (5)	1.0569 (6)	0.1441 (4)	0.143 (3)
H27D	−0.0628	1.1158	0.1530	0.215*
H27E	−0.1064	1.0064	0.1856	0.215*
H27F	−0.1763	1.0981	0.1189	0.215*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02974 (17)	0.03313 (17)	0.04065 (19)	−0.01368 (13)	−0.00106 (13)	−0.01000 (13)
O1	0.0385 (11)	0.0370 (10)	0.0708 (14)	−0.0141 (9)	−0.0009 (10)	−0.0200 (10)
O2	0.0444 (12)	0.0598 (13)	0.0414 (11)	−0.0218 (10)	0.0018 (9)	−0.0085 (10)
O3	0.0453 (12)	0.0674 (14)	0.0395 (11)	−0.0258 (11)	0.0002 (9)	−0.0074 (10)
O4	0.0395 (11)	0.0347 (10)	0.0728 (15)	−0.0128 (9)	−0.0053 (10)	−0.0195 (10)
O5	0.0326 (10)	0.0517 (12)	0.0615 (13)	−0.0155 (9)	−0.0056 (9)	−0.0155 (10)
N1	0.0376 (13)	0.0526 (15)	0.0572 (16)	−0.0145 (12)	−0.0109 (12)	−0.0098 (12)
C1	0.0411 (16)	0.0341 (14)	0.0448 (16)	−0.0141 (12)	−0.0023 (12)	−0.0113 (12)
C2	0.0467 (17)	0.0347 (15)	0.077 (2)	−0.0139 (13)	−0.0058 (16)	−0.0184 (15)
C3	0.0483 (17)	0.0318 (14)	0.071 (2)	−0.0140 (13)	−0.0024 (15)	−0.0193 (14)
C4	0.058 (2)	0.0420 (17)	0.076 (2)	−0.0208 (15)	−0.0008 (17)	−0.0174 (16)
C5	0.055 (2)	0.066 (2)	0.098 (3)	−0.0314 (18)	0.002 (2)	−0.024 (2)
C6	0.052 (2)	0.072 (2)	0.102 (3)	−0.0239 (19)	−0.015 (2)	−0.030 (2)
C7	0.062 (2)	0.059 (2)	0.076 (3)	−0.0163 (18)	−0.0079 (19)	−0.0277 (19)
C8	0.0523 (19)	0.0468 (17)	0.076 (2)	−0.0185 (15)	0.0017 (17)	−0.0286 (17)
C9	0.084 (3)	0.086 (3)	0.074 (3)	−0.046 (2)	0.009 (2)	−0.029 (2)
C10	0.122 (4)	0.119 (4)	0.086 (3)	−0.071 (4)	0.018 (3)	−0.031 (3)
C11	0.134 (5)	0.117 (4)	0.069 (3)	−0.052 (4)	0.002 (3)	−0.020 (3)
C12	0.091 (3)	0.097 (3)	0.089 (3)	−0.030 (3)	−0.020 (3)	−0.032 (3)
C13	0.0501 (18)	0.0445 (16)	0.0413 (16)	−0.0262 (14)	0.0009 (14)	−0.0101 (13)
C14	0.067 (2)	0.079 (2)	0.0399 (17)	−0.0407 (19)	−0.0023 (15)	−0.0066 (16)
C15	0.0529 (18)	0.0597 (19)	0.0338 (15)	−0.0212 (16)	−0.0022 (14)	0.0013 (14)
C16	0.091 (3)	0.087 (3)	0.043 (2)	−0.025 (2)	0.011 (2)	−0.0122 (19)
C17	0.083 (3)	0.146 (5)	0.060 (3)	−0.016 (4)	0.029 (2)	−0.008 (3)
C18	0.063 (3)	0.149 (5)	0.072 (3)	−0.046 (3)	0.004 (2)	0.036 (3)
C19	0.063 (2)	0.090 (3)	0.066 (2)	−0.042 (2)	−0.020 (2)	0.031 (2)
C20	0.0502 (19)	0.058 (2)	0.0472 (18)	−0.0207 (16)	−0.0111 (15)	0.0117 (15)
C21	0.082 (3)	0.052 (2)	0.075 (3)	−0.018 (2)	−0.008 (2)	−0.0012 (19)
C22	0.157 (6)	0.056 (3)	0.116 (4)	−0.025 (3)	−0.029 (4)	−0.010 (3)
C23	0.212 (9)	0.073 (4)	0.160 (7)	−0.081 (5)	−0.068 (6)	0.027 (4)
C24	0.120 (5)	0.106 (5)	0.129 (5)	−0.080 (4)	−0.053 (4)	0.049 (4)
C25	0.0348 (15)	0.0483 (17)	0.0558 (19)	−0.0123 (13)	−0.0044 (14)	−0.0098 (14)
C26	0.0378 (18)	0.063 (2)	0.091 (3)	−0.0095 (16)	−0.0100 (17)	−0.012 (2)
C27	0.069 (3)	0.094 (3)	0.089 (3)	−0.027 (2)	−0.022 (2)	−0.035 (2)
Cu2	0.0715 (3)	0.1253 (4)	0.0355 (2)	−0.0693 (3)	0.00152 (19)	−0.0063 (2)
O6	0.0740 (17)	0.105 (2)	0.0453 (13)	−0.0516 (16)	−0.0009 (12)	−0.0139 (13)
O7	0.0636 (16)	0.099 (2)	0.0579 (15)	−0.0423 (15)	0.0122 (12)	−0.0134 (14)
O8	0.113 (2)	0.173 (3)	0.0461 (15)	−0.106 (2)	0.0112 (15)	−0.0278 (17)
O9	0.0752 (18)	0.150 (3)	0.0545 (15)	−0.072 (2)	−0.0109 (13)	0.0065 (17)
O10	0.0654 (17)	0.114 (2)	0.0606 (16)	−0.0584 (17)	0.0033 (13)	−0.0037 (15)
N2	0.0477 (17)	0.074 (2)	0.081 (2)	−0.0245 (15)	−0.0078 (15)	−0.0046 (17)
C28	0.087 (3)	0.094 (3)	0.0348 (18)	−0.053 (2)	−0.0097 (18)	−0.0002 (17)
C29	0.095 (3)	0.078 (3)	0.046 (2)	−0.041 (2)	−0.0122 (19)	−0.0057 (18)
C30	0.0500 (18)	0.063 (2)	0.0435 (17)	−0.0241 (16)	−0.0039 (14)	−0.0108 (15)
C31	0.065 (2)	0.077 (3)	0.059 (2)	−0.015 (2)	−0.0025 (18)	−0.028 (2)
C32	0.079 (3)	0.060 (2)	0.085 (3)	−0.006 (2)	−0.021 (2)	−0.016 (2)
C33	0.085 (3)	0.072 (3)	0.060 (2)	−0.030 (2)	−0.018 (2)	0.006 (2)
C34	0.055 (2)	0.078 (2)	0.0443 (18)	−0.0350 (18)	−0.0006 (15)	−0.0084 (16)
C35	0.0386 (16)	0.065 (2)	0.0467 (17)	−0.0228 (15)	−0.0004 (13)	−0.0152 (15)
C36	0.051 (2)	0.076 (2)	0.067 (2)	−0.0173 (18)	−0.0099 (17)	−0.0249 (19)
C37	0.048 (2)	0.110 (3)	0.100 (4)	−0.012 (2)	−0.004 (2)	−0.060 (3)
C38	0.055 (2)	0.152 (5)	0.070 (3)	−0.038 (3)	0.014 (2)	−0.055 (3)
C39	0.075 (3)	0.127 (4)	0.046 (2)	−0.057 (3)	0.0077 (19)	−0.017 (2)
C40	0.076 (3)	0.100 (3)	0.0392 (18)	−0.044 (2)	0.0075 (17)	−0.0273 (19)
C41	0.072 (2)	0.073 (2)	0.086 (3)	−0.0228 (19)	0.0066 (19)	−0.026 (2)
C42	0.072 (2)	0.073 (2)	0.086 (3)	−0.0228 (19)	0.0066 (19)	−0.026 (2)
C43	0.074 (5)	0.071 (5)	0.060 (4)	−0.022 (4)	−0.007 (4)	−0.001 (3)
C44	0.075 (6)	0.053 (5)	0.111 (7)	−0.021 (4)	−0.006 (5)	−0.013 (5)
C45	0.080 (7)	0.073 (5)	0.061 (5)	−0.005 (5)	0.015 (5)	−0.013 (4)
C46	0.110 (7)	0.056 (4)	0.051 (4)	−0.018 (4)	−0.006 (4)	−0.004 (3)
C47	0.081 (5)	0.056 (4)	0.054 (4)	−0.013 (4)	0.000 (4)	−0.007 (3)
C48	0.132 (5)	0.081 (3)	0.117 (4)	−0.036 (3)	−0.021 (4)	−0.030 (3)
C49	0.132 (5)	0.081 (3)	0.117 (4)	−0.036 (3)	−0.021 (4)	−0.030 (3)
C50	0.132 (5)	0.081 (3)	0.117 (4)	−0.036 (3)	−0.021 (4)	−0.030 (3)
C51	0.132 (5)	0.081 (3)	0.117 (4)	−0.036 (3)	−0.021 (4)	−0.030 (3)
C42'	0.090 (3)	0.082 (3)	0.114 (3)	−0.0068 (19)	−0.019 (2)	−0.024 (2)
C43'	0.090 (3)	0.082 (3)	0.114 (3)	−0.0068 (19)	−0.019 (2)	−0.024 (2)
C44'	0.090 (3)	0.082 (3)	0.114 (3)	−0.0068 (19)	−0.019 (2)	−0.024 (2)
C45'	0.090 (3)	0.082 (3)	0.114 (3)	−0.0068 (19)	−0.019 (2)	−0.024 (2)
C46'	0.090 (3)	0.082 (3)	0.114 (3)	−0.0068 (19)	−0.019 (2)	−0.024 (2)
C47'	0.090 (3)	0.082 (3)	0.114 (3)	−0.0068 (19)	−0.019 (2)	−0.024 (2)
C48'	0.090 (3)	0.082 (3)	0.114 (3)	−0.0068 (19)	−0.019 (2)	−0.024 (2)
C49'	0.090 (3)	0.082 (3)	0.114 (3)	−0.0068 (19)	−0.019 (2)	−0.024 (2)
C50'	0.090 (3)	0.082 (3)	0.114 (3)	−0.0068 (19)	−0.019 (2)	−0.024 (2)
C51'	0.090 (3)	0.082 (3)	0.114 (3)	−0.0068 (19)	−0.019 (2)	−0.024 (2)
C52	0.059 (2)	0.066 (2)	0.091 (3)	−0.032 (2)	−0.019 (2)	0.011 (2)
C53	0.083 (3)	0.123 (4)	0.080 (3)	−0.069 (3)	−0.002 (2)	−0.011 (3)
C54	0.068 (3)	0.132 (5)	0.221 (8)	−0.018 (3)	0.027 (4)	−0.071 (5)

Geometric parameters (Å, º) top

Cu1—O1	1.9501 (19)	O9—Cu2ⁱⁱ	1.974 (3)
Cu1—O4ⁱ	1.9578 (18)	O10—C52	1.230 (5)
Cu1—O2	1.972 (2)	N2—C52	1.312 (5)
Cu1—O3ⁱ	1.980 (2)	N2—C53	1.439 (5)
Cu1—O5	2.1535 (19)	N2—C54	1.452 (6)
Cu1—Cu1ⁱ	2.6485 (6)	C28—C29	1.516 (5)
O1—C1	1.253 (3)	C29—C30	1.516 (5)
O2—C13	1.254 (4)	C29—H2B1	0.9700
O3—C13	1.251 (4)	C29—H2B2	0.9700
O3—Cu1ⁱ	1.980 (2)	C30—C31	1.361 (5)
O4—C1	1.251 (3)	C30—C35	1.422 (4)
O4—Cu1ⁱ	1.9578 (18)	C31—C32	1.407 (6)
O5—C25	1.236 (4)	C31—H4B	0.9300
N1—C25	1.309 (4)	C32—C33	1.349 (6)
N1—C26	1.444 (4)	C32—H5B	0.9300
N1—C27	1.457 (4)	C33—C34	1.395 (5)
C1—C2	1.514 (4)	C33—H6B	0.9300
C2—C3	1.501 (4)	C34—C39	1.416 (5)
C2—H2A	0.9700	C34—C35	1.428 (5)
C2—H2B	0.9700	C35—C36	1.415 (5)
C3—C4	1.365 (5)	C36—C37	1.362 (5)
C3—C8	1.413 (5)	C36—H9B	0.9300
C4—C5	1.405 (5)	C37—C38	1.391 (7)
C4—H4	0.9300	C37—H10B	0.9300
C5—C6	1.343 (6)	C38—C39	1.352 (7)
C5—H5	0.9300	C38—H11B	0.9300
C6—C7	1.407 (6)	C39—H12B	0.9300
C6—H6	0.9300	C40—C41	1.521 (6)
C7—C12	1.409 (6)	C41—C42	1.532 (8)
C7—C8	1.424 (5)	C41—C42'	1.575 (12)
C8—C9	1.414 (5)	C41—H14A	0.9700
C9—C10	1.351 (6)	C41—H14B	0.9700
C9—H9	0.9300	C41—H14C	0.9700
C10—C11	1.390 (7)	C41—H14D	0.9700
C10—H10	0.9300	C42—C43	1.365 (11)
C11—C12	1.361 (7)	C42—C47	1.418 (10)
C11—H11	0.9300	C43—C44	1.431 (13)
C12—H12	0.9300	C43—H16B	0.9300
C13—C14	1.519 (4)	C44—C45	1.329 (13)
C14—C15	1.498 (4)	C44—H44	0.9300
C14—H14E	0.9700	C45—C46	1.403 (11)
C14—H14F	0.9700	C45—H18B	0.9300
C15—C16	1.361 (5)	C46—C51	1.394 (12)
C15—C20	1.419 (5)	C46—C47	1.429 (10)
C16—C17	1.402 (7)	C47—C48	1.434 (13)
C16—H16A	0.9300	C48—C49	1.348 (15)
C17—C18	1.347 (8)	C48—H21B	0.9300
C17—H17A	0.9300	C49—C50	1.444 (12)
C18—C19	1.393 (7)	C49—H22B	0.9300
C18—H18A	0.9300	C50—C51	1.361 (12)
C19—C20	1.417 (5)	C50—H23B	0.9300
C19—C24	1.420 (8)	C51—H24B	0.9300
C20—C21	1.412 (5)	C42'—C43'	1.377 (16)
C21—C22	1.369 (6)	C42'—C47'	1.399 (16)
C21—H21A	0.9300	C43'—C44'	1.442 (16)
C22—C23	1.396 (10)	C43'—H16'	0.9300
C22—H22A	0.9300	C44'—C45'	1.416 (14)
C23—C24	1.321 (10)	C44'—H17'	0.9300
C23—H23A	0.9300	C45'—C46'	1.375 (18)
C24—H24A	0.9300	C45'—H18'	0.9300
C25—H25A	0.9695	C46'—C51'	1.399 (13)
C26—H26A	0.9600	C46'—C47'	1.437 (15)
C26—H26B	0.9600	C47'—C48'	1.430 (13)
C26—H26C	0.9600	C48'—C49'	1.373 (14)
C27—H27A	0.9600	C48'—H21'	0.9300
C27—H27B	0.9600	C49'—C50'	1.380 (15)
C27—H27C	0.9600	C49'—H22'	0.9300
Cu2—O8ⁱⁱ	1.962 (3)	C50'—C51'	1.297 (14)
Cu2—O7	1.967 (3)	C50'—H23'	0.9300
Cu2—O6	1.970 (3)	C51'—H24'	0.9300
Cu2—O9ⁱⁱ	1.974 (3)	C52—H25B	0.9636
Cu2—O10	2.143 (2)	C53—H26D	0.9600
Cu2—Cu2ⁱⁱ	2.6455 (8)	C53—H26E	0.9600
O6—C28	1.254 (4)	C53—H26F	0.9600
O7—C40	1.252 (5)	C54—H27D	0.9600
O8—C28	1.251 (5)	C54—H27E	0.9600
O8—Cu2ⁱⁱ	1.962 (3)	C54—H27F	0.9600
O9—C40	1.253 (5)

O1—Cu1—O4ⁱ	167.77 (8)	O8—C28—O6	126.3 (4)
O1—Cu1—O2	89.29 (9)	O8—C28—C29	117.5 (3)
O4ⁱ—Cu1—O2	89.56 (9)	O6—C28—C29	116.1 (4)
O1—Cu1—O3ⁱ	89.33 (9)	C28—C29—C30	113.0 (3)
O4ⁱ—Cu1—O3ⁱ	89.23 (9)	C28—C29—H2B1	109.0
O2—Cu1—O3ⁱ	167.86 (8)	C30—C29—H2B1	109.0
O1—Cu1—O5	98.64 (8)	C28—C29—H2B2	109.0
O4ⁱ—Cu1—O5	93.52 (8)	C30—C29—H2B2	109.0
O2—Cu1—O5	101.74 (8)	H2B1—C29—H2B2	107.8
O3ⁱ—Cu1—O5	90.39 (8)	C31—C30—C35	118.9 (3)
O1—Cu1—Cu1ⁱ	86.47 (6)	C31—C30—C29	121.7 (3)
O4ⁱ—Cu1—Cu1ⁱ	81.31 (6)	C35—C30—C29	119.5 (3)
O2—Cu1—Cu1ⁱ	86.99 (6)	C30—C31—C32	122.0 (4)
O3ⁱ—Cu1—Cu1ⁱ	80.89 (6)	C30—C31—H4B	119.0
O5—Cu1—Cu1ⁱ	169.88 (6)	C32—C31—H4B	119.0
C1—O1—Cu1	120.12 (17)	C33—C32—C31	119.7 (4)
C13—O2—Cu1	119.63 (19)	C33—C32—H5B	120.1
C13—O3—Cu1ⁱ	126.54 (19)	C31—C32—H5B	120.1
C1—O4—Cu1ⁱ	125.86 (18)	C32—C33—C34	121.2 (4)
C25—O5—Cu1	117.18 (19)	C32—C33—H6B	119.4
C25—N1—C26	120.9 (3)	C34—C33—H6B	119.4
C25—N1—C27	122.2 (3)	C33—C34—C39	122.5 (4)
C26—N1—C27	116.9 (3)	C33—C34—C35	119.3 (3)
O4—C1—O1	126.2 (2)	C39—C34—C35	118.2 (4)
O4—C1—C2	117.2 (2)	C36—C35—C30	123.3 (3)
O1—C1—C2	116.5 (2)	C36—C35—C34	117.8 (3)
C3—C2—C1	113.8 (2)	C30—C35—C34	118.9 (3)
C3—C2—H2A	108.8	C37—C36—C35	121.4 (4)
C1—C2—H2A	108.8	C37—C36—H9B	119.3
C3—C2—H2B	108.8	C35—C36—H9B	119.3
C1—C2—H2B	108.8	C36—C37—C38	120.7 (4)
H2A—C2—H2B	107.7	C36—C37—H10B	119.6
C4—C3—C8	119.2 (3)	C38—C37—H10B	119.6
C4—C3—C2	120.2 (3)	C39—C38—C37	119.8 (4)
C8—C3—C2	120.6 (3)	C39—C38—H11B	120.1
C3—C4—C5	121.3 (4)	C37—C38—H11B	120.1
C3—C4—H4	119.3	C38—C39—C34	122.0 (4)
C5—C4—H4	119.3	C38—C39—H12B	119.0
C6—C5—C4	120.4 (4)	C34—C39—H12B	119.0
C6—C5—H5	119.8	O7—C40—O9	125.7 (4)
C4—C5—H5	119.8	O7—C40—C41	117.0 (4)
C5—C6—C7	121.0 (3)	O9—C40—C41	117.3 (4)
C5—C6—H6	119.5	C40—C41—C42	130.0 (5)
C7—C6—H6	119.5	C40—C41—C42'	98.4 (5)
C6—C7—C12	122.9 (4)	C42—C41—C42'	55.2 (5)
C6—C7—C8	118.6 (4)	C40—C41—H14A	104.8
C12—C7—C8	118.4 (4)	C42—C41—H14A	104.8
C3—C8—C9	122.8 (3)	C42'—C41—H14A	72.1
C3—C8—C7	119.4 (3)	C40—C41—H14B	104.8
C9—C8—C7	117.7 (4)	C42—C41—H14B	104.8
C10—C9—C8	122.3 (4)	C42'—C41—H14B	156.4
C10—C9—H9	118.9	H14A—C41—H14B	105.8
C8—C9—H9	118.9	C40—C41—H14C	112.0
C9—C10—C11	119.7 (5)	C42—C41—H14C	117.4
C9—C10—H10	120.1	C42'—C41—H14C	113.7
C11—C10—H10	120.1	H14A—C41—H14C	44.3
C12—C11—C10	120.6 (5)	H14B—C41—H14C	61.5
C12—C11—H11	119.7	C40—C41—H14D	85.2
C10—C11—H11	119.7	C42—C41—H14D	87.2
C11—C12—C7	121.3 (4)	C42'—C41—H14D	133.4
C11—C12—H12	119.4	H14A—C41—H14D	151.9
C7—C12—H12	119.4	H14B—C41—H14D	46.2
O3—C13—O2	125.9 (3)	H14C—C41—H14D	107.5
O3—C13—C14	115.4 (3)	C43—C42—C47	119.7 (7)
O2—C13—C14	118.6 (3)	C43—C42—C41	121.4 (7)
C15—C14—C13	117.5 (3)	C47—C42—C41	118.7 (7)
C15—C14—H14E	107.9	C42—C43—C44	120.3 (8)
C13—C14—H14E	107.9	C42—C43—H16B	119.8
C15—C14—H14F	107.9	C44—C43—H16B	119.8
C13—C14—H14F	107.9	C45—C44—C43	120.8 (9)
H14E—C14—H14F	107.2	C45—C44—H44	119.6
C16—C15—C20	119.2 (3)	C43—C44—H44	119.6
C16—C15—C14	120.0 (4)	C44—C45—C46	121.1 (8)
C20—C15—C14	120.7 (3)	C44—C45—H18B	119.4
C15—C16—C17	121.0 (5)	C46—C45—H18B	119.4
C15—C16—H16A	119.5	C45—C46—C51	121.4 (9)
C17—C16—H16A	119.5	C45—C46—C47	119.2 (8)
C18—C17—C16	120.5 (5)	C51—C46—C47	119.5 (9)
C18—C17—H17A	119.8	C42—C47—C48	122.5 (7)
C16—C17—H17A	119.8	C42—C47—C46	119.0 (8)
C17—C18—C19	120.9 (4)	C48—C47—C46	118.6 (8)
C17—C18—H18A	119.5	C49—C48—C47	120.5 (10)
C19—C18—H18A	119.5	C49—C48—H21B	119.8
C18—C19—C20	119.1 (4)	C47—C48—H21B	119.8
C18—C19—C24	122.3 (5)	C48—C49—C50	119.2 (12)
C20—C19—C24	118.6 (5)	C48—C49—H22B	120.4
C21—C20—C19	117.8 (4)	C50—C49—H22B	120.4
C21—C20—C15	123.0 (3)	C51—C50—C49	120.2 (10)
C19—C20—C15	119.2 (4)	C51—C50—H23B	119.9
C22—C21—C20	120.6 (5)	C49—C50—H23B	119.9
C22—C21—H21A	119.7	C50—C51—C46	120.7 (10)
C20—C21—H21A	119.7	C50—C51—H24B	119.6
C21—C22—C23	121.0 (6)	C46—C51—H24B	119.6
C21—C22—H22A	119.5	C43'—C42'—C47'	120.6 (11)
C23—C22—H22A	119.5	C43'—C42'—C41	113.0 (10)
C24—C23—C22	119.7 (6)	C47'—C42'—C41	126.0 (11)
C24—C23—H23A	120.1	C42'—C43'—C44'	118.0 (12)
C22—C23—H23A	120.1	C42'—C43'—H16'	121.0
C23—C24—C19	122.3 (6)	C44'—C43'—H16'	121.0
C23—C24—H24A	118.9	C45'—C44'—C43'	121.5 (12)
C19—C24—H24A	118.9	C45'—C44'—H17'	119.2
O5—C25—N1	125.4 (3)	C43'—C44'—H17'	119.2
O5—C25—H25A	122.7	C46'—C45'—C44'	119.5 (13)
N1—C25—H25A	111.9	C46'—C45'—H18'	120.3
N1—C26—H26A	109.5	C44'—C45'—H18'	120.3
N1—C26—H26B	109.5	C45'—C46'—C51'	122.5 (12)
H26A—C26—H26B	109.5	C45'—C46'—C47'	118.8 (11)
N1—C26—H26C	109.5	C51'—C46'—C47'	118.7 (11)
H26A—C26—H26C	109.5	C42'—C47'—C48'	121.6 (11)
H26B—C26—H26C	109.5	C42'—C47'—C46'	121.4 (11)
N1—C27—H27A	109.5	C48'—C47'—C46'	116.9 (11)
N1—C27—H27B	109.5	C49'—C48'—C47'	119.9 (12)
H27A—C27—H27B	109.5	C49'—C48'—H21'	120.1
N1—C27—H27C	109.5	C47'—C48'—H21'	120.1
H27A—C27—H27C	109.5	C48'—C49'—C50'	120.7 (14)
H27B—C27—H27C	109.5	C48'—C49'—H22'	119.7
O8ⁱⁱ—Cu2—O7	89.67 (14)	C50'—C49'—H22'	119.7
O8ⁱⁱ—Cu2—O6	168.00 (11)	C51'—C50'—C49'	121.4 (16)
O7—Cu2—O6	89.60 (11)	C51'—C50'—H23'	119.3
O8ⁱⁱ—Cu2—O9ⁱⁱ	89.22 (14)	C49'—C50'—H23'	119.3
O7—Cu2—O9ⁱⁱ	167.85 (11)	C50'—C51'—C46'	122.4 (13)
O6—Cu2—O9ⁱⁱ	88.98 (13)	C50'—C51'—H24'	118.8
O8ⁱⁱ—Cu2—O10	96.72 (12)	C46'—C51'—H24'	118.8
O7—Cu2—O10	95.71 (11)	O10—C52—N2	125.3 (4)
O6—Cu2—O10	95.27 (11)	O10—C52—H25B	125.7
O9ⁱⁱ—Cu2—O10	96.44 (11)	N2—C52—H25B	109.0
O8ⁱⁱ—Cu2—Cu2ⁱⁱ	85.27 (8)	N2—C53—H26D	109.5
O7—Cu2—Cu2ⁱⁱ	83.41 (8)	N2—C53—H26E	109.5
O6—Cu2—Cu2ⁱⁱ	82.75 (7)	H26D—C53—H26E	109.5
O9ⁱⁱ—Cu2—Cu2ⁱⁱ	84.44 (8)	N2—C53—H26F	109.5
O10—Cu2—Cu2ⁱⁱ	177.82 (8)	H26D—C53—H26F	109.5
C28—O6—Cu2	124.0 (3)	H26E—C53—H26F	109.5
C40—O7—Cu2	124.0 (3)	N2—C54—H27D	109.5
C28—O8—Cu2ⁱⁱ	121.6 (2)	N2—C54—H27E	109.5
C40—O9—Cu2ⁱⁱ	122.4 (3)	H27D—C54—H27E	109.5
C52—O10—Cu2	123.1 (3)	N2—C54—H27F	109.5
C52—N2—C53	120.1 (4)	H27D—C54—H27F	109.5
C52—N2—C54	123.3 (4)	H27E—C54—H27F	109.5
C53—N2—C54	116.5 (4)

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₂H₉O₂)₄(C₃H₇NO)₂]
M_r	1014.04
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.6704 (7), 12.3561 (8), 20.7734 (14)
α, β, γ (°)	74.8390 (11), 84.898 (1), 66.848 (1)
V (Å³)	2430.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.945, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	18538, 8516, 7103
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.115, 1.04
No. of reflections	8516
No. of parameters	630
No. of restraints	16
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −1.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank Jiangsu Marine Resources Development Research Institute and Huaihai Institute of Technology for support of this work.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, L.-F., Zhang, J., Song, L.-J., Wang, W.-G. & Ju, Z.-F. (2004). Acta Cryst. E60, m1032–m1034. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ji, L.-L., Liu, J.-S. & Song, W.-D. (2011). Acta Cryst. E67, m606. Web of Science CSD CrossRef IUCr Journals 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
Xia, H.-T., Liu, Y.-F. & Li, S.-A. (2006). Acta Cryst. E62, m2653–m2655. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, Y.-Q., Li, C.-H. L. W. & Kuang, Y.-F. (2008). Chin. J. Struct. Chem. 30, 4524–4530. Google Scholar
Yin, F.-J., Zhao, H. & Hu, X.-L. (2010). Synth. React. Inorg. Met. Org. Nano-Met. Chem. 40, 606–612. CAS 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.