1,5-Bis(4-chloro­phen­yl)-3-[4-(dimethyl­amino)phen­yl]pentane-1,5-dione

Lei, X.; Bai, X.

doi:10.1107/S1600536809003894

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o514

doi:10.1107/S1600536809003894

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1,5-Bis(4-chlorophenyl)-3-[4-(dimethylamino)phenyl]pentane-1,5-dione

Xinyou Lei ^a ^* and Xiaohua Bai ^a

^aCollege of Life Sciences and Chemistry, Tianshui Normal University, Tianshui 741000, People's Republic of China
^*Correspondence e-mail: lei_xinyou@163.com

(Received 5 January 2009; accepted 2 February 2009; online 11 February 2009)

In the title molecule, C₂₅H₂₃Cl₂NO₂, the central benzene ring forms dihedral angles of 81.88 (7) and 89.22 (7)° with the two 4-chlorophenyl fragments. The crystal packing exhibits weak intermolecular C—H⋯O hydrogen bonds and π–π interactions [centroid–centroid distance 3.724 (3) Å].

Related literature

For the crystal structures of related compounds, see: Das et al. (1994 ); Huang et al. (2006 ).

Experimental

Crystal data

C₂₅H₂₃Cl₂NO₂
M_r = 440.34
Triclinic, $[P \overline 1]$
a = 6.1059 (11) Å
b = 12.5660 (16) Å
c = 14.731 (2) Å
α = 75.516 (1)°
β = 85.953 (2)°
γ = 87.215 (2)°
V = 1091.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 298 (2) K
0.49 × 0.44 × 0.41 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.859, T_max = 0.880
5699 measured reflections
3783 independent reflections
1846 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.141
S = 0.99
3783 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1ⁱ	0.93	2.58	3.176 (4)	122
Symmetry code: (i) x+1, y, z.

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 I, global. DOI: 10.1107/S1600536809003894/cv2508sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003894/cv2508Isup2.hkl

checkCIF report

Comment top

In this paper, we present the crystal structure of the title compound, (I), obtained with the solvent-free protocol for the synthesis of 1,5-diketones starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH under solvent-free conditions.

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in 1,3,5-triphenyl-pentane-1,5-diketone (Das et al., 1994), 1,5-Diphenyl-3-(2-pyridyl)pentane-1,5-dione (Huang et al., 2006). The dihedral angles between the central benzene ring and the benzene rings C12/C13/C14/C15/C16/C17 and C6/C7/C8/C9/C10/C11 are 89.22 (7) ° and 81.88 (7) °, respectively. The crystal packing exhibits weak intermolecular π–π interactions (Table 1) and C—H···O hydrogen bonds (Table 2).

Related literature top

For the crystal structures of related compounds, see: Das et al. (1994); Huang et al. (2006).

Experimental top

4-(Dimethylamino)benzaldehyde (0.5 mmol) and 4-chloroacetophenone (1.0 mmol), NaOH (1.0 mmol) were mixed in 50 ml flask under sovlent-free condtions. After stirring for 5 min at 293 K, the resulting mixture was washed with water for several times for removing NaOH, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₂₅H₂₃Cl₂NO₂: C 68.19, H 5.26, N 3.18%; found: C 68.23, H 5.35, N 3.15%.

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) showing the atomic numbering scheme and 30% probability displacement ellipsoids. H atoms have been omitted for clarity.

1,5-Bis(4-chlorophenyl)-3-[4-(dimethylamino)phenyl]pentane-1,5-dione top

Crystal data top

C₂₅H₂₃Cl₂NO₂	Z = 2
M_r = 440.34	F(000) = 460
Triclinic, P1	D_x = 1.340 Mg m⁻³
a = 6.1059 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.5660 (16) Å	Cell parameters from 1234 reflections
c = 14.731 (2) Å	θ = 2.5–22.3°
α = 75.516 (1)°	µ = 0.32 mm⁻¹
β = 85.953 (2)°	T = 298 K
γ = 87.215 (2)°	Block, colourless
V = 1091.1 (3) Å³	0.49 × 0.44 × 0.41 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3783 independent reflections
Radiation source: fine-focus sealed tube	1846 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.859, T_max = 0.880	k = −8→14
5699 measured reflections	l = −17→17

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0595P)²] where P = (F_o² + 2F_c²)/3
3783 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₅H₂₃Cl₂NO₂	γ = 87.215 (2)°
M_r = 440.34	V = 1091.1 (3) Å³
Triclinic, P1	Z = 2
a = 6.1059 (11) Å	Mo Kα radiation
b = 12.5660 (16) Å	µ = 0.32 mm⁻¹
c = 14.731 (2) Å	T = 298 K
α = 75.516 (1)°	0.49 × 0.44 × 0.41 mm
β = 85.953 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3783 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1846 reflections with I > 2σ(I)
T_min = 0.859, T_max = 0.880	R_int = 0.024
5699 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 0.99	Δρ_max = 0.18 e Å⁻³
3783 reflections	Δρ_min = −0.28 e Å⁻³
273 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
Cl1	1.1281 (2)	0.35929 (8)	0.70584 (7)	0.1057 (4)
Cl2	0.8066 (2)	1.57712 (9)	0.06677 (8)	0.1334 (5)
N1	0.5447 (5)	0.8356 (3)	0.0253 (2)	0.0836 (9)
O1	0.4561 (4)	0.75133 (19)	0.48581 (16)	0.0838 (8)
O2	0.3440 (4)	1.12960 (19)	0.32504 (17)	0.0811 (7)
C1	0.6537 (6)	0.7566 (3)	0.4892 (2)	0.0550 (8)
C2	0.7662 (5)	0.8611 (2)	0.4432 (2)	0.0560 (8)
H2A	0.8980	0.8441	0.4080	0.067*
H2B	0.8109	0.8943	0.4914	0.067*
C3	0.6236 (5)	0.9442 (2)	0.3771 (2)	0.0551 (8)
H3	0.4755	0.9419	0.4076	0.066*
C4	0.7007 (5)	1.0611 (2)	0.3626 (2)	0.0587 (9)
H4A	0.7239	1.0744	0.4232	0.070*
H4B	0.8403	1.0685	0.3262	0.070*
C5	0.5388 (6)	1.1462 (3)	0.3128 (2)	0.0556 (8)
C6	0.7791 (5)	0.6593 (2)	0.54189 (19)	0.0486 (8)
C7	0.9857 (5)	0.6658 (3)	0.5707 (2)	0.0573 (8)
H7	1.0549	0.7328	0.5548	0.069*
C8	1.0912 (6)	0.5741 (3)	0.6229 (2)	0.0667 (9)
H8	1.2297	0.5793	0.6437	0.080*
C9	0.9908 (7)	0.4750 (3)	0.6441 (2)	0.0650 (9)
C10	0.7867 (7)	0.4664 (3)	0.6155 (2)	0.0744 (10)
H10	0.7202	0.3987	0.6294	0.089*
C11	0.6806 (6)	0.5591 (3)	0.5657 (2)	0.0635 (9)
H11	0.5392	0.5541	0.5476	0.076*
C12	0.6156 (6)	1.2513 (3)	0.2519 (2)	0.0546 (8)
C13	0.8291 (6)	1.2674 (3)	0.2151 (2)	0.0632 (9)
H13	0.9347	1.2109	0.2298	0.076*
C14	0.8859 (6)	1.3673 (3)	0.1565 (2)	0.0779 (11)
H14	1.0288	1.3779	0.1304	0.093*
C15	0.7308 (8)	1.4511 (3)	0.1368 (2)	0.0804 (11)
C16	0.5199 (8)	1.4378 (3)	0.1735 (2)	0.0854 (12)
H16	0.4164	1.4955	0.1604	0.102*
C17	0.4640 (6)	1.3385 (3)	0.2298 (2)	0.0707 (10)
H17	0.3198	1.3286	0.2544	0.085*
C18	0.6048 (5)	0.9143 (2)	0.2842 (2)	0.0490 (8)
C19	0.7708 (5)	0.9307 (2)	0.2150 (2)	0.0572 (8)
H19	0.9003	0.9603	0.2258	0.069*
C20	0.7540 (6)	0.9053 (3)	0.1304 (2)	0.0632 (9)
H20	0.8705	0.9189	0.0853	0.076*
C21	0.5653 (6)	0.8595 (3)	0.1113 (2)	0.0596 (9)
C22	0.3988 (6)	0.8402 (3)	0.1817 (2)	0.0663 (9)
H22	0.2711	0.8079	0.1723	0.080*
C23	0.4195 (5)	0.8681 (2)	0.2655 (2)	0.0597 (9)
H23	0.3035	0.8551	0.3109	0.072*
C24	0.7091 (7)	0.8654 (3)	−0.0499 (3)	0.0939 (13)
H24A	0.7429	0.9413	−0.0588	0.141*
H24B	0.6554	0.8546	−0.1066	0.141*
H24C	0.8393	0.8202	−0.0348	0.141*
C25	0.3520 (7)	0.7852 (4)	0.0080 (3)	0.1137 (16)
H25A	0.3125	0.7267	0.0617	0.171*
H25B	0.3806	0.7559	−0.0461	0.171*
H25C	0.2334	0.8390	−0.0031	0.171*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1403 (11)	0.0722 (7)	0.0954 (8)	0.0259 (6)	−0.0218 (7)	−0.0052 (6)
Cl2	0.1990 (14)	0.0788 (8)	0.0976 (9)	0.0017 (8)	0.0142 (9)	0.0169 (6)
N1	0.092 (3)	0.096 (2)	0.072 (2)	0.0026 (19)	−0.0208 (19)	−0.0359 (19)
O1	0.0554 (16)	0.0829 (18)	0.0964 (19)	−0.0125 (13)	−0.0049 (14)	0.0110 (14)
O2	0.0617 (17)	0.0758 (18)	0.103 (2)	0.0036 (14)	−0.0004 (14)	−0.0203 (14)
C1	0.050 (2)	0.068 (2)	0.0468 (19)	−0.0123 (18)	0.0025 (16)	−0.0132 (17)
C2	0.059 (2)	0.060 (2)	0.0468 (18)	−0.0079 (17)	−0.0023 (16)	−0.0077 (16)
C3	0.054 (2)	0.057 (2)	0.052 (2)	−0.0022 (16)	−0.0017 (16)	−0.0100 (16)
C4	0.069 (2)	0.057 (2)	0.0517 (19)	0.0013 (18)	−0.0075 (17)	−0.0152 (16)
C5	0.059 (2)	0.060 (2)	0.053 (2)	0.0031 (19)	−0.0031 (18)	−0.0243 (18)
C6	0.051 (2)	0.053 (2)	0.0420 (18)	−0.0077 (17)	0.0049 (15)	−0.0128 (15)
C7	0.053 (2)	0.057 (2)	0.061 (2)	−0.0062 (17)	−0.0018 (17)	−0.0117 (17)
C8	0.063 (2)	0.069 (3)	0.067 (2)	−0.001 (2)	−0.0065 (18)	−0.015 (2)
C9	0.088 (3)	0.054 (2)	0.052 (2)	0.007 (2)	−0.0023 (19)	−0.0143 (18)
C10	0.095 (3)	0.054 (2)	0.076 (3)	−0.017 (2)	−0.004 (2)	−0.017 (2)
C11	0.066 (2)	0.058 (2)	0.069 (2)	−0.0129 (19)	−0.0041 (19)	−0.0183 (19)
C12	0.067 (2)	0.055 (2)	0.0439 (19)	0.0068 (18)	−0.0083 (17)	−0.0152 (16)
C13	0.070 (3)	0.063 (2)	0.053 (2)	0.0080 (19)	−0.0059 (18)	−0.0078 (18)
C14	0.083 (3)	0.083 (3)	0.061 (2)	−0.002 (2)	−0.002 (2)	−0.005 (2)
C15	0.112 (4)	0.064 (3)	0.054 (2)	0.009 (2)	−0.002 (2)	0.0012 (19)
C16	0.110 (4)	0.074 (3)	0.061 (2)	0.027 (2)	−0.007 (2)	−0.002 (2)
C17	0.079 (3)	0.075 (3)	0.054 (2)	0.014 (2)	−0.0021 (19)	−0.012 (2)
C18	0.048 (2)	0.0485 (19)	0.0488 (19)	0.0037 (15)	−0.0034 (16)	−0.0098 (15)
C19	0.052 (2)	0.061 (2)	0.061 (2)	−0.0015 (16)	−0.0095 (17)	−0.0180 (17)
C20	0.060 (2)	0.069 (2)	0.059 (2)	0.0039 (18)	0.0010 (17)	−0.0168 (18)
C21	0.071 (2)	0.052 (2)	0.056 (2)	0.0113 (18)	−0.0178 (19)	−0.0124 (17)
C22	0.063 (2)	0.065 (2)	0.073 (3)	−0.0064 (18)	−0.018 (2)	−0.0177 (19)
C23	0.052 (2)	0.064 (2)	0.060 (2)	−0.0028 (17)	−0.0035 (17)	−0.0077 (18)
C24	0.114 (3)	0.109 (3)	0.063 (3)	0.018 (3)	−0.012 (2)	−0.032 (2)
C25	0.107 (4)	0.145 (4)	0.115 (4)	0.007 (3)	−0.039 (3)	−0.074 (3)

Geometric parameters (Å, º) top

Cl1—C9	1.724 (3)	C11—H11	0.9300
Cl2—C15	1.724 (4)	C12—C13	1.380 (4)
N1—C21	1.389 (4)	C12—C17	1.389 (4)
N1—C24	1.430 (4)	C13—C14	1.378 (5)
N1—C25	1.431 (4)	C13—H13	0.9300
O1—C1	1.217 (3)	C14—C15	1.371 (5)
O2—C5	1.211 (3)	C14—H14	0.9300
C1—C6	1.484 (4)	C15—C16	1.362 (5)
C1—C2	1.495 (4)	C16—C17	1.359 (5)
C2—C3	1.523 (4)	C16—H16	0.9300
C2—H2A	0.9700	C17—H17	0.9300
C2—H2B	0.9700	C18—C19	1.371 (4)
C3—C18	1.519 (4)	C18—C23	1.372 (4)
C3—C4	1.523 (4)	C19—C20	1.373 (4)
C3—H3	0.9800	C19—H19	0.9300
C4—C5	1.505 (4)	C20—C21	1.389 (4)
C4—H4A	0.9700	C20—H20	0.9300
C4—H4B	0.9700	C21—C22	1.384 (4)
C5—C12	1.476 (4)	C22—C23	1.381 (4)
C6—C7	1.371 (4)	C22—H22	0.9300
C6—C11	1.376 (4)	C23—H23	0.9300
C7—C8	1.374 (4)	C24—H24A	0.9600
C7—H7	0.9300	C24—H24B	0.9600
C8—C9	1.370 (4)	C24—H24C	0.9600
C8—H8	0.9300	C25—H25A	0.9600
C9—C10	1.361 (4)	C25—H25B	0.9600
C10—C11	1.371 (5)	C25—H25C	0.9600
C10—H10	0.9300

Cg···Cgⁱ	3.724 (3)

C21—N1—C24	121.3 (3)	C17—C12—C5	118.1 (3)
C21—N1—C25	120.5 (3)	C14—C13—C12	120.0 (3)
C24—N1—C25	118.1 (3)	C14—C13—H13	120.0
O1—C1—C6	119.2 (3)	C12—C13—H13	120.0
O1—C1—C2	120.1 (3)	C15—C14—C13	119.7 (4)
C6—C1—C2	120.8 (3)	C15—C14—H14	120.1
C1—C2—C3	113.6 (3)	C13—C14—H14	120.1
C1—C2—H2A	108.9	C16—C15—C14	121.4 (4)
C3—C2—H2A	108.9	C16—C15—Cl2	119.4 (3)
C1—C2—H2B	108.9	C14—C15—Cl2	119.2 (4)
C3—C2—H2B	108.9	C17—C16—C15	118.6 (4)
H2A—C2—H2B	107.7	C17—C16—H16	120.7
C18—C3—C4	111.8 (2)	C15—C16—H16	120.7
C18—C3—C2	112.2 (2)	C16—C17—C12	122.0 (4)
C4—C3—C2	111.8 (2)	C16—C17—H17	119.0
C18—C3—H3	106.9	C12—C17—H17	119.0
C4—C3—H3	106.9	C19—C18—C23	116.2 (3)
C2—C3—H3	106.9	C19—C18—C3	122.4 (3)
C5—C4—C3	112.6 (3)	C23—C18—C3	121.4 (3)
C5—C4—H4A	109.1	C18—C19—C20	122.8 (3)
C3—C4—H4A	109.1	C18—C19—H19	118.6
C5—C4—H4B	109.1	C20—C19—H19	118.6
C3—C4—H4B	109.1	C19—C20—C21	120.9 (3)
H4A—C4—H4B	107.8	C19—C20—H20	119.6
O2—C5—C12	119.8 (3)	C21—C20—H20	119.6
O2—C5—C4	119.8 (3)	C22—C21—C20	116.8 (3)
C12—C5—C4	120.4 (3)	C22—C21—N1	121.9 (3)
C7—C6—C11	118.7 (3)	C20—C21—N1	121.3 (3)
C7—C6—C1	122.8 (3)	C23—C22—C21	121.0 (3)
C11—C6—C1	118.5 (3)	C23—C22—H22	119.5
C6—C7—C8	120.5 (3)	C21—C22—H22	119.5
C6—C7—H7	119.7	C18—C23—C22	122.4 (3)
C8—C7—H7	119.7	C18—C23—H23	118.8
C9—C8—C7	119.5 (3)	C22—C23—H23	118.8
C9—C8—H8	120.2	N1—C24—H24A	109.5
C7—C8—H8	120.2	N1—C24—H24B	109.5
C10—C9—C8	120.9 (3)	H24A—C24—H24B	109.5
C10—C9—Cl1	119.7 (3)	N1—C24—H24C	109.5
C8—C9—Cl1	119.3 (3)	H24A—C24—H24C	109.5
C9—C10—C11	119.0 (3)	H24B—C24—H24C	109.5
C9—C10—H10	120.5	N1—C25—H25A	109.5
C11—C10—H10	120.5	N1—C25—H25B	109.5
C10—C11—C6	121.3 (3)	H25A—C25—H25B	109.5
C10—C11—H11	119.4	N1—C25—H25C	109.5
C6—C11—H11	119.4	H25A—C25—H25C	109.5
C13—C12—C17	118.3 (3)	H25B—C25—H25C	109.5
C13—C12—C5	123.7 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱⁱ	0.93	2.58	3.176 (4)	122

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

Experimental details

Crystal data
Chemical formula	C₂₅H₂₃Cl₂NO₂
M_r	440.34
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.1059 (11), 12.5660 (16), 14.731 (2)
α, β, γ (°)	75.516 (1), 85.953 (2), 87.215 (2)
V (Å³)	1091.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.49 × 0.44 × 0.41

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.859, 0.880
No. of measured, independent and observed [I > 2σ(I)] reflections	5699, 3783, 1846
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.141, 0.99
No. of reflections	3783
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.28

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱ	0.93	2.58	3.176 (4)	122.1

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

Acknowledgements

This project was supported by the Foundation of Tianshui Normal University.

References

Das, G. C., Hursthouse, M. B., Malik, K. M. A., Rahman, M. M., Rahman, M. T. & Olsson, T. (1994). J. Chem. Crystallogr. 24, 511–515. CSD CrossRef CAS Web of Science Google Scholar
Huang, X.-Q., Wang, D.-Q., Dou, J.-M. & Wang, J.-X. (2006). Acta Cryst. E62, o60–o61. 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar