4-Chloro-2-{3-chloro-2-[(3,5-dimethyl­piperidin-1-yl)meth­yl]phenyl­sulfan­yl}-6-methoxy­pyrimidine

Zou, G.; Zhu, M.

doi:10.1107/S1600536810004599

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o650

doi:10.1107/S1600536810004599

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4-Chloro-2-{3-chloro-2-[(3,5-dimethylpiperidin-1-yl)methyl]phenylsulfanyl}-6-methoxypyrimidine

Guanglong Zou ^a and Mei Zhu ^b ^*

^aSchool of Chemistry and Environmental Science, Guizhou University for Nationalities, Guiyang 550025, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China
^*Correspondence e-mail: zhumei@iccas.ac.cn

(Received 1 January 2010; accepted 5 February 2010; online 17 February 2010)

In the title compound, C₁₉H₂₃Cl₂N₃OS, the dihedral angle between the benzene ring and the pyrimidine ring is 86.6 (9)°. The piperidine ring adopts a chair conformation.

Related literature

For the biological activity of pyrimidine derivatives, see: Joffe et al. (1989 ); Petersen & Schmidt (2003 ); Blum (2001 ); Gompper et al. (2004 ); Michael (2005 ); Nadal & Olavarria (2004 ).

Experimental

Crystal data

C₁₉H₂₃Cl₂N₃OS
M_r = 412.36
Triclinic, $[P \overline 1]$
a = 8.000 (4) Å
b = 11.454 (6) Å
c = 12.001 (7) Å
α = 87.820 (7)°
β = 76.084 (6)°
γ = 77.700 (6)°
V = 1042.9 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 296 K
0.39 × 0.37 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.852, T_max = 0.901
7861 measured reflections
3848 independent reflections
2553 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.119
S = 1.03
3848 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004599/pb2021sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004599/pb2021Isup2.hkl

checkCIF report

Comment top

Pyrimidine derivatives are widespread in medicinal and natural products chemistry. A number of natural products, pharmaceuticals, and functional materials incorporate this heterocycle (Michael, 2005. Several examples of pharmaceutically important compounds include trimethoprim (Joffe et al., 1989), sulfadiazine (Petersen & Schmidt, 2003),Gleevec (imatinib mesilate) (Nadal & Olavarria, 2004), and Xeloda (capecitabine) (Blum, 2001). Natural and unnatural polymers also contain pyrimidine derivatives (Gompper et al., 2004). The potent physiological properties of these pyrimidine derivatives led to vast research of their use as medicines in the field of pharmaceutical chemistry. So in the recent decades, many chemists have been attracted by the synthesis of pyrimidines. In this context, we report the synthesis ofthe title compound.

The molecular structure is shown in Fig. 1. The bond lengths and angles are within normal ranges. The pyrimidine ring makes dihedral angles of 86.6 (9)° with the benzene ring. In the crystal structure,The cyclohexyl groups display chair-type conformation.

Related literature top

For the biological activity of pyrimidine derivatives, see: Joffe et al. (1989); Petersen & Schmidt (2003); Blum (2001); Gompper et al. (2004); Michael (2005); Nadal & Olavarria (2004).

Experimental top

To a solution of 2,4-dichloro-6-methoxypyrimidine (0.5 mmol) and 3-chloro-2-((3,5-dimethylpiperidin-1-yl)methyl)benzenethiol (0.5 mmol) in dry methylbenzene was added NaH (0.6 mmol). The mixture was stirred for 12 h at room temperature. After evaporation of the solvent, the residue was purified by column chromatography on silica gel to afford the title compound as a colorless solid (yield 78%). The title compound was recrystallized from CH₂Cl₂ at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the molecular structure of (I) with atom numbering scheme and 30% probability displacement ellipsoids.

4-Chloro-2-{3-chloro-2-[(3,5-dimethylpiperidin-1-yl)methyl]phenylsulfanyl}- 6-methoxypyrimidine top

Crystal data top

C₁₉H₂₃Cl₂N₃OS	Z = 2
M_r = 412.36	F(000) = 432
Triclinic, P1	D_x = 1.313 Mg m⁻³
a = 8.000 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.454 (6) Å	Cell parameters from 2557 reflections
c = 12.001 (7) Å	θ = 2.5–25.9°
α = 87.820 (7)°	µ = 0.42 mm⁻¹
β = 76.084 (6)°	T = 296 K
γ = 77.700 (6)°	Block, colourless
V = 1042.9 (10) Å³	0.39 × 0.37 × 0.25 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3848 independent reflections
Radiation source: fine-focus sealed tube	2553 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
phi and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.852, T_max = 0.901	k = −13→13
7861 measured reflections	l = −14→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0498P)² + 0.3748P] where P = (F_o² + 2F_c²)/3
3848 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₉H₂₃Cl₂N₃OS	γ = 77.700 (6)°
M_r = 412.36	V = 1042.9 (10) Å³
Triclinic, P1	Z = 2
a = 8.000 (4) Å	Mo Kα radiation
b = 11.454 (6) Å	µ = 0.42 mm⁻¹
c = 12.001 (7) Å	T = 296 K
α = 87.820 (7)°	0.39 × 0.37 × 0.25 mm
β = 76.084 (6)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3848 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2553 reflections with I > 2σ(I)
T_min = 0.852, T_max = 0.901	R_int = 0.019
7861 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
3848 reflections	Δρ_min = −0.31 e Å⁻³
238 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
C1	0.8993 (3)	0.4679 (2)	0.3790 (2)	0.0511 (6)
C2	0.7914 (4)	0.5783 (3)	0.4072 (2)	0.0639 (7)
H2	0.8031	0.6417	0.3572	0.077*
C3	0.6657 (4)	0.5951 (3)	0.5096 (3)	0.0772 (10)
H3	0.5913	0.6695	0.5281	0.093*
C4	0.6503 (4)	0.5026 (4)	0.5841 (3)	0.0765 (10)
H4	0.5657	0.5136	0.6533	0.092*
C5	0.7618 (4)	0.3926 (3)	0.5555 (2)	0.0649 (8)
C6	0.8897 (3)	0.3706 (2)	0.4527 (2)	0.0517 (6)
C7	1.0146 (4)	0.2522 (3)	0.4215 (2)	0.0613 (7)
H7A	1.1342	0.2648	0.3977	0.074*
H7B	1.0071	0.2019	0.4886	0.074*
C8	1.1282 (4)	0.1048 (3)	0.2685 (3)	0.0722 (8)
H8A	1.1601	0.0419	0.3206	0.087*
H8B	1.2269	0.1439	0.2432	0.087*
C9	1.0929 (4)	0.0498 (3)	0.1644 (3)	0.0773 (9)
H9	1.0612	0.1145	0.1126	0.093*
C10	0.9343 (4)	−0.0090 (3)	0.2069 (3)	0.0838 (10)
H10A	0.9048	−0.0403	0.1418	0.101*
H10B	0.9647	−0.0753	0.2562	0.101*
C11	0.7761 (4)	0.0801 (3)	0.2730 (3)	0.0867 (10)
H11	0.7438	0.1436	0.2202	0.104*
C12	0.8245 (4)	0.1367 (3)	0.3699 (3)	0.0757 (9)
H12A	0.7247	0.1972	0.4083	0.091*
H12B	0.8503	0.0761	0.4256	0.091*
C13	1.2537 (5)	−0.0357 (3)	0.1000 (3)	0.1102 (13)
H13A	1.3485	0.0055	0.0749	0.165*
H13B	1.2284	−0.0676	0.0345	0.165*
H13C	1.2871	−0.0998	0.1494	0.165*
C14	0.6166 (5)	0.0238 (4)	0.3187 (5)	0.151 (2)
H14A	0.6428	−0.0360	0.3738	0.226*
H14B	0.5894	−0.0124	0.2562	0.226*
H14C	0.5174	0.0844	0.3547	0.226*
C15	0.9754 (3)	0.4023 (2)	0.14901 (19)	0.0466 (6)
C16	1.0372 (3)	0.3253 (2)	−0.0292 (2)	0.0483 (6)
C17	0.8596 (3)	0.3280 (2)	−0.0188 (2)	0.0528 (6)
H17	0.8179	0.3030	−0.0778	0.063*
C18	0.7513 (3)	0.3697 (2)	0.0833 (2)	0.0500 (6)
C19	1.3329 (4)	0.2760 (3)	−0.1362 (3)	0.0729 (8)
H19A	1.3525	0.3554	−0.1317	0.109*
H19B	1.3998	0.2398	−0.2085	0.109*
H19C	1.3695	0.2292	−0.0749	0.109*
Cl1	0.73889 (14)	0.27940 (11)	0.65587 (8)	0.1117 (4)
Cl2	0.52759 (9)	0.37327 (8)	0.10766 (6)	0.0780 (3)
N1	0.9758 (3)	0.19101 (19)	0.32894 (19)	0.0585 (6)
N2	0.8031 (3)	0.40866 (18)	0.16994 (16)	0.0497 (5)
N3	1.0978 (3)	0.36245 (17)	0.05379 (16)	0.0480 (5)
O1	1.1505 (2)	0.28158 (17)	−0.12653 (14)	0.0651 (5)
S1	1.06955 (9)	0.45367 (7)	0.25092 (6)	0.0613 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0428 (14)	0.0719 (18)	0.0443 (13)	−0.0167 (13)	−0.0152 (11)	−0.0130 (13)
C2	0.0580 (18)	0.0735 (19)	0.0658 (18)	−0.0100 (15)	−0.0263 (15)	−0.0174 (15)
C3	0.0500 (18)	0.095 (2)	0.088 (2)	−0.0002 (16)	−0.0258 (17)	−0.043 (2)
C4	0.0440 (17)	0.127 (3)	0.0581 (18)	−0.0211 (19)	−0.0025 (13)	−0.0381 (19)
C5	0.0497 (16)	0.102 (2)	0.0489 (15)	−0.0256 (16)	−0.0123 (12)	−0.0129 (15)
C6	0.0387 (14)	0.0765 (18)	0.0458 (14)	−0.0172 (13)	−0.0144 (11)	−0.0118 (13)
C7	0.0502 (16)	0.0762 (19)	0.0630 (17)	−0.0127 (14)	−0.0235 (13)	−0.0044 (14)
C8	0.0544 (18)	0.075 (2)	0.086 (2)	−0.0077 (15)	−0.0158 (15)	−0.0109 (16)
C9	0.088 (2)	0.0613 (19)	0.084 (2)	−0.0076 (17)	−0.0285 (18)	−0.0092 (16)
C10	0.090 (2)	0.063 (2)	0.104 (3)	−0.0093 (18)	−0.038 (2)	−0.0161 (18)
C11	0.069 (2)	0.078 (2)	0.126 (3)	−0.0152 (17)	−0.044 (2)	−0.019 (2)
C12	0.0523 (18)	0.080 (2)	0.096 (2)	−0.0149 (15)	−0.0165 (16)	−0.0183 (17)
C13	0.120 (3)	0.099 (3)	0.097 (3)	−0.015 (2)	−0.003 (2)	−0.023 (2)
C14	0.081 (3)	0.149 (4)	0.234 (6)	−0.048 (3)	−0.028 (3)	−0.070 (4)
C15	0.0469 (15)	0.0525 (15)	0.0424 (13)	−0.0118 (12)	−0.0128 (11)	−0.0016 (11)
C16	0.0533 (16)	0.0477 (14)	0.0413 (13)	−0.0097 (11)	−0.0065 (11)	−0.0045 (11)
C17	0.0575 (16)	0.0600 (16)	0.0461 (14)	−0.0163 (13)	−0.0179 (12)	−0.0061 (12)
C18	0.0462 (15)	0.0567 (15)	0.0498 (14)	−0.0110 (12)	−0.0159 (12)	−0.0012 (12)
C19	0.0481 (17)	0.087 (2)	0.0704 (19)	−0.0035 (15)	0.0056 (14)	−0.0227 (16)
Cl1	0.1161 (8)	0.1555 (10)	0.0669 (5)	−0.0582 (7)	−0.0048 (5)	0.0201 (6)
Cl2	0.0450 (4)	0.1197 (7)	0.0740 (5)	−0.0198 (4)	−0.0189 (3)	−0.0135 (4)
N1	0.0447 (13)	0.0622 (14)	0.0712 (14)	−0.0079 (11)	−0.0197 (11)	−0.0128 (11)
N2	0.0428 (12)	0.0640 (13)	0.0436 (11)	−0.0108 (10)	−0.0120 (9)	−0.0063 (9)
N3	0.0459 (12)	0.0536 (12)	0.0436 (11)	−0.0111 (9)	−0.0076 (9)	−0.0041 (9)
O1	0.0607 (12)	0.0770 (13)	0.0517 (11)	−0.0109 (10)	−0.0021 (9)	−0.0198 (9)
S1	0.0499 (4)	0.0947 (6)	0.0468 (4)	−0.0301 (4)	−0.0108 (3)	−0.0118 (3)

Geometric parameters (Å, º) top

C1—C2	1.374 (4)	C11—C14	1.527 (5)
C1—C6	1.400 (4)	C11—H11	0.9800
C1—S1	1.778 (3)	C12—N1	1.451 (3)
C2—C3	1.378 (4)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C3—C4	1.367 (5)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.381 (4)	C13—H13C	0.9600
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.392 (4)	C14—H14B	0.9600
C5—Cl1	1.744 (3)	C14—H14C	0.9600
C6—C7	1.504 (4)	C15—N2	1.327 (3)
C7—N1	1.462 (3)	C15—N3	1.336 (3)
C7—H7A	0.9700	C15—S1	1.759 (2)
C7—H7B	0.9700	C16—N3	1.327 (3)
C8—N1	1.450 (3)	C16—O1	1.334 (3)
C8—C9	1.531 (4)	C16—C17	1.390 (3)
C8—H8A	0.9700	C17—C18	1.356 (3)
C8—H8B	0.9700	C17—H17	0.9300
C9—C13	1.501 (5)	C18—N2	1.331 (3)
C9—C10	1.533 (4)	C18—Cl2	1.735 (3)
C9—H9	0.9800	C19—O1	1.423 (3)
C10—C11	1.517 (4)	C19—H19A	0.9600
C10—H10A	0.9700	C19—H19B	0.9600
C10—H10B	0.9700	C19—H19C	0.9600
C11—C12	1.518 (4)

C2—C1—C6	122.1 (2)	C10—C11—H11	107.8
C2—C1—S1	118.1 (2)	C14—C11—H11	107.8
C6—C1—S1	119.5 (2)	N1—C12—C11	112.1 (3)
C1—C2—C3	120.0 (3)	N1—C12—H12A	109.2
C1—C2—H2	120.0	C11—C12—H12A	109.2
C3—C2—H2	120.0	N1—C12—H12B	109.2
C4—C3—C2	120.1 (3)	C11—C12—H12B	109.2
C4—C3—H3	119.9	H12A—C12—H12B	107.9
C2—C3—H3	119.9	C9—C13—H13A	109.5
C3—C4—C5	119.2 (3)	C9—C13—H13B	109.5
C3—C4—H4	120.4	H13A—C13—H13B	109.5
C5—C4—H4	120.4	C9—C13—H13C	109.5
C4—C5—C6	122.9 (3)	H13A—C13—H13C	109.5
C4—C5—Cl1	116.9 (2)	H13B—C13—H13C	109.5
C6—C5—Cl1	120.1 (2)	C11—C14—H14A	109.5
C5—C6—C1	115.7 (3)	C11—C14—H14B	109.5
C5—C6—C7	123.5 (3)	H14A—C14—H14B	109.5
C1—C6—C7	120.8 (2)	C11—C14—H14C	109.5
N1—C7—C6	112.1 (2)	H14A—C14—H14C	109.5
N1—C7—H7A	109.2	H14B—C14—H14C	109.5
C6—C7—H7A	109.2	N2—C15—N3	127.9 (2)
N1—C7—H7B	109.2	N2—C15—S1	120.94 (18)
C6—C7—H7B	109.2	N3—C15—S1	111.10 (18)
H7A—C7—H7B	107.9	N3—C16—O1	119.2 (2)
N1—C8—C9	111.9 (2)	N3—C16—C17	122.8 (2)
N1—C8—H8A	109.2	O1—C16—C17	118.0 (2)
C9—C8—H8A	109.2	C18—C17—C16	115.4 (2)
N1—C8—H8B	109.2	C18—C17—H17	122.3
C9—C8—H8B	109.2	C16—C17—H17	122.3
H8A—C8—H8B	107.9	N2—C18—C17	124.9 (2)
C13—C9—C8	111.4 (3)	N2—C18—Cl2	115.60 (19)
C13—C9—C10	112.8 (3)	C17—C18—Cl2	119.48 (19)
C8—C9—C10	107.9 (3)	O1—C19—H19A	109.5
C13—C9—H9	108.2	O1—C19—H19B	109.5
C8—C9—H9	108.2	H19A—C19—H19B	109.5
C10—C9—H9	108.2	O1—C19—H19C	109.5
C11—C10—C9	111.0 (3)	H19A—C19—H19C	109.5
C11—C10—H10A	109.4	H19B—C19—H19C	109.5
C9—C10—H10A	109.4	C8—N1—C12	111.5 (2)
C11—C10—H10B	109.4	C8—N1—C7	111.9 (2)
C9—C10—H10B	109.4	C12—N1—C7	111.8 (2)
H10A—C10—H10B	108.0	C15—N2—C18	113.9 (2)
C12—C11—C10	110.0 (3)	C16—N3—C15	115.1 (2)
C12—C11—C14	110.9 (3)	C16—O1—C19	118.0 (2)
C10—C11—C14	112.3 (3)	C15—S1—C1	103.40 (12)
C12—C11—H11	107.8

C6—C1—C2—C3	−1.7 (4)	N3—C16—C17—C18	−1.0 (4)
S1—C1—C2—C3	−175.51 (19)	O1—C16—C17—C18	178.0 (2)
C1—C2—C3—C4	1.2 (4)	C16—C17—C18—N2	1.2 (4)
C2—C3—C4—C5	0.0 (4)	C16—C17—C18—Cl2	−178.17 (19)
C3—C4—C5—C6	−0.7 (4)	C9—C8—N1—C12	59.6 (3)
C3—C4—C5—Cl1	178.5 (2)	C9—C8—N1—C7	−174.4 (2)
C4—C5—C6—C1	0.1 (4)	C11—C12—N1—C8	−57.7 (3)
Cl1—C5—C6—C1	−178.95 (17)	C11—C12—N1—C7	176.2 (2)
C4—C5—C6—C7	178.6 (2)	C6—C7—N1—C8	157.2 (2)
Cl1—C5—C6—C7	−0.5 (3)	C6—C7—N1—C12	−76.9 (3)
C2—C1—C6—C5	1.0 (3)	N3—C15—N2—C18	−0.1 (4)
S1—C1—C6—C5	174.74 (17)	S1—C15—N2—C18	178.03 (18)
C2—C1—C6—C7	−177.5 (2)	C17—C18—N2—C15	−0.7 (4)
S1—C1—C6—C7	−3.8 (3)	Cl2—C18—N2—C15	178.70 (18)
C5—C6—C7—N1	109.8 (3)	O1—C16—N3—C15	−178.6 (2)
C1—C6—C7—N1	−71.8 (3)	C17—C16—N3—C15	0.4 (3)
N1—C8—C9—C13	177.8 (3)	N2—C15—N3—C16	0.2 (4)
N1—C8—C9—C10	−57.8 (3)	S1—C15—N3—C16	−178.04 (17)
C13—C9—C10—C11	179.1 (3)	N3—C16—O1—C19	0.5 (3)
C8—C9—C10—C11	55.6 (4)	C17—C16—O1—C19	−178.5 (2)
C9—C10—C11—C12	−54.9 (4)	N2—C15—S1—C1	15.0 (2)
C9—C10—C11—C14	−178.9 (3)	N3—C15—S1—C1	−166.64 (18)
C10—C11—C12—N1	55.2 (4)	C2—C1—S1—C15	−95.9 (2)
C14—C11—C12—N1	180.0 (3)	C6—C1—S1—C15	90.2 (2)

Experimental details

Crystal data
Chemical formula	C₁₉H₂₃Cl₂N₃OS
M_r	412.36
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.000 (4), 11.454 (6), 12.001 (7)
α, β, γ (°)	87.820 (7), 76.084 (6), 77.700 (6)
V (Å³)	1042.9 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.39 × 0.37 × 0.25

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.852, 0.901
No. of measured, independent and observed [I > 2σ(I)] reflections	7861, 3848, 2553
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.119, 1.03
No. of reflections	3848
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.31

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

This work was supported by the Doctoral Foundation of Luoyang Normal University.

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