1-Acetyl-5-isobutyl-2-sulfanylidene­imidazolidin-4-one

Li, K.; Feng, Q.; Lu, Z.-H.

doi:10.1107/S1600536810037256

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2655

doi:10.1107/S1600536810037256

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1-Acetyl-5-isobutyl-2-sulfanylideneimidazolidin-4-one

Kaozhen Li,^a ^* Qiu Feng ^a and Ze-Hua Lu ^b

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, and ^bLiaocheng International Peace Hospital, Shandong 252059, People's Republic of China
^*Correspondence e-mail: lkzlc@163.com

(Received 24 August 2010; accepted 17 September 2010; online 30 September 2010)

There are two independent molecules in the asymmetric unit of the title compound, C₉H₁₄N₂O₂S. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds, forming a chain along the a axis.

Related literature

For biological activity of thiohydantoins, see: Lopez & Trigo (1985 ). For a related structure, see: Sulbaran et al. (2007 ).

Experimental

Crystal data

C₉H₁₄N₂O₂S
M_r = 214.28
Triclinic, $[P \overline 1]$
a = 7.1856 (8) Å
b = 9.7567 (11) Å
c = 16.4226 (15) Å
α = 101.231 (2)°
β = 93.965 (1)°
γ = 90.491 (1)°
V = 1126.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 298 K
0.42 × 0.35 × 0.14 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.897, T_max = 0.964
5877 measured reflections
3916 independent reflections
2199 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.138
S = 1.02
3916 reflections
259 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	1.99	2.834 (3)	167
N4—H4⋯O4ⁱⁱ	0.86	2.01	2.850 (3)	167
Symmetry codes: (i) x-1, y, z; (ii) 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/S1600536810037256/is2592sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037256/is2592Isup2.hkl

checkCIF report

Comment top

Thiohydantoins are known to exhibit a wide range of biological activities, including anticonvulsant, antiarrhythmic, anti-inflammatory, and antidiabetic properties, as well as herbicidal and fungicidal activity (Lopez & Trigo, 1985).

In the title compound (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the reported compound (Sulbaran et al., 2007). In the crystal structure, there exist intermolecular N—H···O hydrogen bonds (Table 1). The supramolecular chain structure along the a axis, which is built by weak intermolecular N—H···O hydrogen bonds.

Related literature top

For biological activity of thiohydantoins, see: Lopez & Trigo (1985). For a related structure, see: Sulbaran et al. (2007).

Experimental top

2-Amino-4-methylpentanoic acid (10 mmol) and NH₄SCN (10 mmol) was dissolved in a 15 ml acetic anhydride and 2 ml acetic acid mixture and transferred in a round-bottom flask. The mixture was warmed, with agitation, to 373 K over a period of 1 h. The resulting solution was cooled in a ice/water mixture and stored in a freezer overnight. Crystal of (I) suitable for X-ray diffraction analysis were obtained by slow evaporation. Elemental analysis: calculated for C₉H₁₄N₂O₂S: C 50.45, H 6.59, N 13.07%; found: C 50.53, H 6.46, N 13.14%.

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 content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids.

1-Acetyl-5-isobutyl-2-sulfanylideneimidazolidin-4-one top

Crystal data top

C₉H₁₄N₂O₂S	Z = 4
M_r = 214.28	F(000) = 456
Triclinic, P1	D_x = 1.264 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1856 (8) Å	Cell parameters from 1409 reflections
b = 9.7567 (11) Å	θ = 2.5–22.5°
c = 16.4226 (15) Å	µ = 0.27 mm⁻¹
α = 101.231 (2)°	T = 298 K
β = 93.965 (1)°	Block, colourless
γ = 90.491 (1)°	0.42 × 0.35 × 0.14 mm
V = 1126.3 (2) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3916 independent reflections
Radiation source: fine-focus sealed tube	2199 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.897, T_max = 0.964	k = −9→11
5877 measured reflections	l = −18→19

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0539P)² + 0.2948P] where P = (F_o² + 2F_c²)/3
3916 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₉H₁₄N₂O₂S	γ = 90.491 (1)°
M_r = 214.28	V = 1126.3 (2) Å³
Triclinic, P1	Z = 4
a = 7.1856 (8) Å	Mo Kα radiation
b = 9.7567 (11) Å	µ = 0.27 mm⁻¹
c = 16.4226 (15) Å	T = 298 K
α = 101.231 (2)°	0.42 × 0.35 × 0.14 mm
β = 93.965 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3916 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2199 reflections with I > 2σ(I)
T_min = 0.897, T_max = 0.964	R_int = 0.023
5877 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.02	Δρ_max = 0.27 e Å⁻³
3916 reflections	Δρ_min = −0.17 e Å⁻³
259 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
N1	0.3760 (3)	0.2881 (3)	0.16750 (16)	0.0404 (7)
N2	0.0770 (3)	0.2612 (3)	0.18054 (17)	0.0523 (8)
H2	−0.0417	0.2710	0.1746	0.063*
N3	0.0219 (3)	0.7835 (3)	0.17203 (16)	0.0429 (7)
N4	0.3235 (4)	0.7558 (3)	0.18537 (17)	0.0518 (8)
H4	0.4406	0.7664	0.1800	0.062*
O1	0.0752 (3)	0.1110 (3)	0.27212 (17)	0.0746 (8)
O2	0.6815 (3)	0.2536 (3)	0.16880 (16)	0.0638 (7)
O3	0.3503 (3)	0.6072 (3)	0.27747 (17)	0.0748 (8)
O4	−0.2837 (3)	0.7469 (3)	0.17042 (16)	0.0649 (7)
S1	0.13550 (12)	0.41653 (10)	0.06933 (6)	0.0563 (3)
S2	0.23535 (13)	0.90538 (11)	0.07109 (6)	0.0626 (3)
C1	0.2002 (4)	0.3238 (3)	0.13812 (19)	0.0403 (8)
C2	0.1575 (4)	0.1820 (4)	0.2329 (2)	0.0520 (9)
C3	0.3646 (4)	0.2041 (4)	0.2328 (2)	0.0466 (9)
H3	0.4243	0.1141	0.2158	0.056*
C4	0.4495 (5)	0.2774 (4)	0.3174 (2)	0.0569 (10)
H4A	0.5733	0.3121	0.3106	0.068*
H4B	0.3747	0.3576	0.3373	0.068*
C5	0.4652 (6)	0.1881 (4)	0.3833 (2)	0.0698 (11)
H5	0.3394	0.1543	0.3900	0.084*
C6	0.5376 (7)	0.2777 (5)	0.4657 (3)	0.1015 (16)
H6A	0.6642	0.3068	0.4621	0.152*
H6B	0.5328	0.2245	0.5089	0.152*
H6C	0.4616	0.3585	0.4782	0.152*
C7	0.5853 (8)	0.0619 (5)	0.3603 (3)	0.121 (2)
H7A	0.7066	0.0916	0.3486	0.182*
H7B	0.5283	0.0007	0.3119	0.182*
H7C	0.5972	0.0131	0.4058	0.182*
C8	0.5509 (4)	0.3120 (3)	0.1399 (2)	0.0453 (8)
C9	0.5730 (5)	0.4020 (4)	0.0785 (2)	0.0639 (11)
H9A	0.7025	0.4090	0.0686	0.096*
H9B	0.5277	0.4934	0.0996	0.096*
H9C	0.5030	0.3621	0.0273	0.096*
C10	0.1898 (4)	0.8166 (3)	0.1424 (2)	0.0427 (8)
C11	0.2580 (5)	0.6769 (4)	0.2376 (2)	0.0502 (9)
C12	0.0504 (4)	0.6996 (3)	0.2371 (2)	0.0461 (9)
H12	−0.0175	0.6099	0.2202	0.055*
C13	−0.0073 (5)	0.7752 (4)	0.3214 (2)	0.0573 (10)
H13A	0.0745	0.8564	0.3406	0.069*
H13B	−0.1329	0.8086	0.3142	0.069*
C14	−0.0024 (6)	0.6886 (4)	0.3882 (2)	0.0724 (12)
H14	0.1255	0.6567	0.3955	0.087*
C15	−0.1284 (9)	0.5618 (6)	0.3658 (3)	0.126 (2)
H15A	−0.1293	0.5155	0.4122	0.190*
H15B	−0.0840	0.4992	0.3189	0.190*
H15C	−0.2526	0.5894	0.3518	0.190*
C16	−0.0487 (7)	0.7818 (6)	0.4705 (3)	0.1089 (17)
H16A	−0.1747	0.8127	0.4655	0.163*
H16B	0.0352	0.8614	0.4831	0.163*
H16C	−0.0355	0.7296	0.5143	0.163*
C17	−0.1606 (4)	0.8094 (4)	0.1444 (2)	0.0471 (9)
C18	−0.2005 (5)	0.9099 (4)	0.0897 (2)	0.0630 (10)
H18A	−0.3330	0.9169	0.0800	0.094*
H18B	−0.1466	0.8784	0.0376	0.094*
H18C	−0.1478	0.9998	0.1157	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0242 (14)	0.0472 (17)	0.0518 (16)	0.0029 (11)	0.0067 (12)	0.0132 (14)
N2	0.0207 (14)	0.067 (2)	0.074 (2)	0.0038 (13)	0.0043 (13)	0.0246 (17)
N3	0.0261 (14)	0.0508 (17)	0.0527 (17)	0.0051 (12)	0.0052 (12)	0.0115 (15)
N4	0.0248 (15)	0.0608 (19)	0.074 (2)	0.0033 (13)	0.0075 (14)	0.0212 (17)
O1	0.0495 (16)	0.092 (2)	0.094 (2)	−0.0114 (14)	0.0122 (14)	0.0441 (18)
O2	0.0275 (13)	0.0854 (19)	0.0865 (18)	0.0089 (12)	0.0085 (12)	0.0342 (16)
O3	0.0490 (16)	0.089 (2)	0.098 (2)	0.0208 (14)	0.0066 (14)	0.0459 (18)
O4	0.0317 (13)	0.0777 (18)	0.0915 (19)	0.0010 (12)	0.0099 (13)	0.0299 (16)
S1	0.0400 (5)	0.0709 (7)	0.0607 (6)	0.0080 (4)	−0.0020 (4)	0.0209 (5)
S2	0.0469 (6)	0.0798 (8)	0.0682 (7)	0.0025 (5)	0.0149 (5)	0.0280 (6)
C1	0.0262 (17)	0.044 (2)	0.048 (2)	0.0048 (14)	0.0041 (14)	0.0028 (17)
C2	0.0330 (19)	0.062 (2)	0.065 (2)	−0.0020 (17)	0.0063 (17)	0.020 (2)
C3	0.0324 (18)	0.051 (2)	0.060 (2)	0.0032 (15)	0.0030 (16)	0.0207 (19)
C4	0.044 (2)	0.064 (2)	0.064 (2)	−0.0014 (18)	0.0012 (18)	0.019 (2)
C5	0.064 (3)	0.085 (3)	0.064 (3)	−0.005 (2)	−0.001 (2)	0.026 (2)
C6	0.104 (4)	0.130 (4)	0.068 (3)	−0.016 (3)	−0.008 (3)	0.021 (3)
C7	0.152 (5)	0.109 (4)	0.106 (4)	0.043 (4)	−0.021 (4)	0.037 (4)
C8	0.0260 (18)	0.051 (2)	0.060 (2)	0.0049 (15)	0.0078 (16)	0.0102 (19)
C9	0.042 (2)	0.073 (3)	0.085 (3)	0.0027 (19)	0.0208 (19)	0.031 (2)
C10	0.0293 (18)	0.045 (2)	0.052 (2)	0.0036 (15)	0.0036 (15)	0.0055 (17)
C11	0.036 (2)	0.055 (2)	0.062 (2)	0.0085 (17)	0.0075 (17)	0.016 (2)
C12	0.0333 (18)	0.049 (2)	0.058 (2)	0.0047 (15)	0.0077 (16)	0.0141 (19)
C13	0.049 (2)	0.064 (2)	0.062 (2)	0.0079 (18)	0.0116 (18)	0.016 (2)
C14	0.067 (3)	0.085 (3)	0.072 (3)	0.008 (2)	0.011 (2)	0.028 (3)
C15	0.173 (6)	0.110 (4)	0.108 (4)	−0.037 (4)	0.031 (4)	0.044 (4)
C16	0.115 (4)	0.143 (5)	0.070 (3)	0.022 (4)	0.023 (3)	0.020 (3)
C17	0.0322 (19)	0.051 (2)	0.058 (2)	0.0043 (16)	0.0054 (16)	0.0091 (19)
C18	0.040 (2)	0.072 (3)	0.079 (3)	0.0074 (18)	−0.0009 (19)	0.023 (2)

Geometric parameters (Å, º) top

N1—C1	1.393 (4)	C6—H6B	0.9600
N1—C8	1.398 (4)	C6—H6C	0.9600
N1—C3	1.478 (4)	C7—H7A	0.9600
N2—C2	1.368 (4)	C7—H7B	0.9600
N2—C1	1.372 (4)	C7—H7C	0.9600
N2—H2	0.8600	C8—C9	1.476 (5)
N3—C10	1.390 (4)	C9—H9A	0.9600
N3—C17	1.399 (4)	C9—H9B	0.9600
N3—C12	1.472 (4)	C9—H9C	0.9600
N4—C10	1.361 (4)	C11—C12	1.510 (4)
N4—C11	1.363 (4)	C12—C13	1.524 (4)
N4—H4	0.8600	C12—H12	0.9800
O1—C2	1.209 (4)	C13—C14	1.508 (5)
O2—C8	1.218 (4)	C13—H13A	0.9700
O3—C11	1.205 (4)	C13—H13B	0.9700
O4—C17	1.217 (4)	C14—C15	1.497 (6)
S1—C1	1.626 (3)	C14—C16	1.534 (5)
S2—C10	1.635 (3)	C14—H14	0.9800
C2—C3	1.502 (4)	C15—H15A	0.9600
C3—C4	1.517 (5)	C15—H15B	0.9600
C3—H3	0.9800	C15—H15C	0.9600
C4—C5	1.515 (5)	C16—H16A	0.9600
C4—H4A	0.9700	C16—H16B	0.9600
C4—H4B	0.9700	C16—H16C	0.9600
C5—C7	1.512 (6)	C17—C18	1.471 (5)
C5—C6	1.517 (5)	C18—H18A	0.9600
C5—H5	0.9800	C18—H18B	0.9600
C6—H6A	0.9600	C18—H18C	0.9600

C1—N1—C8	129.4 (3)	C8—C9—H9A	109.5
C1—N1—C3	111.9 (2)	C8—C9—H9B	109.5
C8—N1—C3	118.6 (3)	H9A—C9—H9B	109.5
C2—N2—C1	114.9 (3)	C8—C9—H9C	109.5
C2—N2—H2	122.6	H9A—C9—H9C	109.5
C1—N2—H2	122.6	H9B—C9—H9C	109.5
C10—N3—C17	129.3 (3)	N4—C10—N3	105.3 (3)
C10—N3—C12	111.7 (2)	N4—C10—S2	123.4 (2)
C17—N3—C12	118.8 (3)	N3—C10—S2	131.3 (3)
C10—N4—C11	115.1 (3)	O3—C11—N4	126.2 (3)
C10—N4—H4	122.5	O3—C11—C12	127.9 (3)
C11—N4—H4	122.5	N4—C11—C12	105.9 (3)
N2—C1—N1	104.9 (3)	N3—C12—C11	101.5 (3)
N2—C1—S1	123.4 (2)	N3—C12—C13	112.7 (3)
N1—C1—S1	131.7 (2)	C11—C12—C13	112.0 (3)
O1—C2—N2	125.9 (3)	N3—C12—H12	110.1
O1—C2—C3	127.8 (3)	C11—C12—H12	110.1
N2—C2—C3	106.3 (3)	C13—C12—H12	110.1
N1—C3—C2	101.6 (2)	C14—C13—C12	115.1 (3)
N1—C3—C4	113.5 (3)	C14—C13—H13A	108.5
C2—C3—C4	111.9 (3)	C12—C13—H13A	108.5
N1—C3—H3	109.9	C14—C13—H13B	108.5
C2—C3—H3	109.9	C12—C13—H13B	108.5
C4—C3—H3	109.9	H13A—C13—H13B	107.5
C5—C4—C3	115.3 (3)	C15—C14—C13	112.9 (4)
C5—C4—H4A	108.5	C15—C14—C16	111.7 (4)
C3—C4—H4A	108.5	C13—C14—C16	108.9 (4)
C5—C4—H4B	108.5	C15—C14—H14	107.7
C3—C4—H4B	108.5	C13—C14—H14	107.7
H4A—C4—H4B	107.5	C16—C14—H14	107.7
C7—C5—C4	113.2 (4)	C14—C15—H15A	109.5
C7—C5—C6	110.9 (4)	C14—C15—H15B	109.5
C4—C5—C6	109.3 (3)	H15A—C15—H15B	109.5
C7—C5—H5	107.7	C14—C15—H15C	109.5
C4—C5—H5	107.7	H15A—C15—H15C	109.5
C6—C5—H5	107.7	H15B—C15—H15C	109.5
C5—C6—H6A	109.5	C14—C16—H16A	109.5
C5—C6—H6B	109.5	C14—C16—H16B	109.5
H6A—C6—H6B	109.5	H16A—C16—H16B	109.5
C5—C6—H6C	109.5	C14—C16—H16C	109.5
H6A—C6—H6C	109.5	H16A—C16—H16C	109.5
H6B—C6—H6C	109.5	H16B—C16—H16C	109.5
C5—C7—H7A	109.5	O4—C17—N3	115.9 (3)
C5—C7—H7B	109.5	O4—C17—C18	122.3 (3)
H7A—C7—H7B	109.5	N3—C17—C18	121.7 (3)
C5—C7—H7C	109.5	C17—C18—H18A	109.5
H7A—C7—H7C	109.5	C17—C18—H18B	109.5
H7B—C7—H7C	109.5	H18A—C18—H18B	109.5
O2—C8—N1	116.2 (3)	C17—C18—H18C	109.5
O2—C8—C9	122.6 (3)	H18A—C18—H18C	109.5
N1—C8—C9	121.1 (3)	H18B—C18—H18C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	1.99	2.834 (3)	167
N4—H4···O4ⁱⁱ	0.86	2.01	2.850 (3)	167

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

Experimental details

Crystal data
Chemical formula	C₉H₁₄N₂O₂S
M_r	214.28
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.1856 (8), 9.7567 (11), 16.4226 (15)
α, β, γ (°)	101.231 (2), 93.965 (1), 90.491 (1)
V (Å³)	1126.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.42 × 0.35 × 0.14

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.897, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	5877, 3916, 2199
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.138, 1.02
No. of reflections	3916
No. of parameters	259
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.17

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
N2—H2···O2ⁱ	0.86	1.99	2.834 (3)	167
N4—H4···O4ⁱⁱ	0.86	2.01	2.850 (3)	167

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

Acknowledgements

The authors acknowledge financial support bythe University Student Science and Technology Culture Foundation of Liaocheng University (No. SRT10056HX2).

References

Lopez, C. A. & Trigo, G. G. (1985). Adv. Heterocycl. Chem. 38, 177–179. CrossRef Web of Science 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
Sulbaran, M. E., Delgado, G. E., Mora, A. J., Bahsas, A., Novoa de Armas, H. & Blaton, N. (2007). Acta Cryst. C63, o543–o545. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar