3-(1,3-Dithio­lan-2-yl­idene)-1-phenyl­pyridine-2,4(1H,3H)-dione

Li, L.-J.; Li, Y.; Hao, X.-Y.; Sun, X.-Y.

doi:10.1107/S1600536809021862

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1602

doi:10.1107/S1600536809021862

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3-(1,3-Dithiolan-2-ylidene)-1-phenylpyridine-2,4(1H,3H)-dione

Lei-Jiao Li,^a Yan Li,^a Xi-Yun Hao ^a and Xiu-Yun Sun ^a ^*

^aSchool of Chemical and Pharmaceutical Engineering, Jilin Institute of Chemical Technology, Jilin 132022, People's Republic of China
^*Correspondence e-mail: xiuyuns@sina.com

(Received 7 May 2009; accepted 9 June 2009; online 17 June 2009)

The title compound, C₁₄H₁₁NO₂S₂, was synthesized by reaction of 2-(1,3-dithiolan-2-ylidene)-3-oxo-N-phenylbutanamide with N,N′-dimethylformamide dimethyl acetal in N,N′-dimethylformamide. The molecule exhibits a V-shaped conformation in the crystal, with a dihedral angle of 65.9 (2)° between the benzene and pyridine rings. In the crystal. C—H⋯O and C—H⋯S interactions are observed. Two C atoms of the dithiolane ring are disordered with occupancies in the ratio 0.541 (13)/0.459 (13).

Related literature

For the synthesis, see Li et al., (2008 ).

Experimental

Crystal data

C₁₄H₁₁NO₂S₂
M_r = 289.36
Monoclinic, P 2₁
a = 5.7708 (17) Å
b = 12.033 (4) Å
c = 9.624 (3) Å
β = 101.094 (3)°
V = 655.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 292 K
0.35 × 0.29 × 0.28 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.870, T_max = 0.894
5598 measured reflections
2543 independent reflections
2361 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.071
S = 1.04
2543 reflections
191 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1181 Friedel pairs
Flack parameter: −0.05 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1′—H1′A⋯O1ⁱ	0.97	2.43	3.300 (17)	148
C2—H2B⋯O1ⁱ	0.97	2.69	3.388 (8)	129
C7—H7⋯O2ⁱⁱ	0.93	2.36	3.259 (3)	163
C14—H14⋯O2ⁱⁱⁱ	0.93	2.46	3.293 (3)	149
C11—H11⋯S1^iv	0.93	2.90	3.756 (3)	153
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+2]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+1]$ .

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 global, I. DOI: 10.1107/S1600536809021862/rk2145sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021862/rk2145Isup2.hkl

checkCIF report

Comment top

N-Substituted pyridone compounds have versatile physiological activity. For instance, they can sterilize, ease pain, resist tumour and cure parkinsonism and so forth. These compounds can cure β-thalassemia beyond compare, beacuse they have powerful ability to form coordination compounds. In the molecule of the title compound, (Fig. 1), C1 and C2 are disordered in ratio 0.541 (13)/0.459 (13). The molecule exhibits a V-shaped conformation in the crystal with a dihedral angle of 65.9 (2)° between the benzene ring and the pyridine ring. The dihedral angle between the pyridine ring and the dithiolane ring is 2.6 (8)°.

Related literature top

For the synthesis, see Li et al., (2008).

Experimental top

The title compound, with M.P. 497 K, was synthesized according to the literature (Li et al., 2008). It was dissolved in ethyl acetate at room temperature and hexane was added. The solution was kept at room temperature in a sealed flask for a few days to give single crystals suitable for single crystal X-ray analysis.

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. Molecular structure of the title compound with atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius. Only major fragment of disordered cycle is presented.

3-(1,3-Dithiolan-2-ylidene)-1-phenylpyridine-2,4(1H,3H)-dione top

Crystal data top

C₁₄H₁₁NO₂S₂	F(000) = 300
M_r = 289.36	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁	Melting point: 497 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 5.7708 (17) Å	Cell parameters from 3388 reflections
b = 12.033 (4) Å	θ = 2.7–26.1°
c = 9.624 (3) Å	µ = 0.40 mm⁻¹
β = 101.094 (3)°	T = 292 K
V = 655.8 (4) Å³	Block, yellow
Z = 2	0.35 × 0.29 × 0.28 mm

Data collection top

Bruker APEXII CCD diffractometer	2543 independent reflections
Radiation source: fine-focus sealed tube	2361 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 26.1°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→7
T_min = 0.870, T_max = 0.894	k = −14→14
5598 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.071	w = 1/[σ²(F_o²) + (0.035P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2543 reflections	Δρ_max = 0.17 e Å⁻³
191 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1181 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (5)

Crystal data top

C₁₄H₁₁NO₂S₂	V = 655.8 (4) Å³
M_r = 289.36	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.7708 (17) Å	µ = 0.40 mm⁻¹
b = 12.033 (4) Å	T = 292 K
c = 9.624 (3) Å	0.35 × 0.29 × 0.28 mm
β = 101.094 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2543 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2361 reflections with I > 2σ(I)
T_min = 0.870, T_max = 0.894	R_int = 0.050
5598 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.071	Δρ_max = 0.17 e Å⁻³
S = 1.04	Δρ_min = −0.21 e Å⁻³
2543 reflections	Absolute structure: Flack (1983), 1181 Friedel pairs
191 parameters	Absolute structure parameter: −0.05 (5)
1 restraint

Special details top

Geometry. All s.u.'s (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
S1	0.64100 (9)	0.15466 (4)	0.63757 (5)	0.04732 (14)
S2	0.47667 (10)	−0.01817 (4)	0.80937 (6)	0.05463 (16)
C1	0.775 (3)	0.0231 (13)	0.6391 (16)	0.063 (3)	0.541 (13)
H1A	0.8165	0.0099	0.5476	0.076*	0.541 (13)
H1B	0.9197	0.0230	0.7097	0.076*	0.541 (13)
C2	0.6217 (17)	−0.0684 (4)	0.6704 (9)	0.0580 (18)	0.541 (13)
H2A	0.7152	−0.1339	0.7017	0.070*	0.541 (13)
H2B	0.5059	−0.0874	0.5866	0.070*	0.541 (13)
C1'	0.742 (3)	0.0127 (13)	0.6019 (19)	0.064 (4)	0.459 (13)
H1'A	0.6365	−0.0202	0.5217	0.076*	0.459 (13)
H1'B	0.9000	0.0149	0.5818	0.076*	0.459 (13)
C2'	0.7381 (17)	−0.0516 (5)	0.7321 (11)	0.057 (2)	0.459 (13)
H2'A	0.8802	−0.0357	0.8011	0.069*	0.459 (13)
H2'B	0.7374	−0.1303	0.7104	0.069*	0.459 (13)
C3	0.4657 (3)	0.12007 (16)	0.75830 (19)	0.0385 (4)
C4	0.3248 (3)	0.19662 (16)	0.8105 (2)	0.0384 (4)
C5	0.1840 (3)	0.16281 (18)	0.91489 (18)	0.0419 (4)
C6	0.0463 (4)	0.24818 (18)	0.9638 (2)	0.0495 (5)
H6	−0.0410	0.2314	1.0328	0.059*
C7	0.0409 (3)	0.35039 (17)	0.9126 (2)	0.0477 (5)
H7	−0.0534	0.4027	0.9462	0.057*
C8	0.3154 (3)	0.31026 (17)	0.7579 (2)	0.0422 (4)
C9	0.1463 (3)	0.49614 (15)	0.7608 (2)	0.0402 (4)
C10	−0.0659 (3)	0.53405 (19)	0.6854 (2)	0.0517 (5)
H10	−0.1967	0.4874	0.6672	0.062*
C11	−0.0823 (4)	0.6429 (2)	0.6368 (2)	0.0613 (6)
H11	−0.2248	0.6693	0.5854	0.074*
C12	0.1097 (5)	0.71177 (19)	0.6640 (3)	0.0646 (6)
H12	0.0981	0.7844	0.6301	0.078*
C13	0.3191 (4)	0.67360 (19)	0.7411 (3)	0.0604 (6)
H13	0.4486	0.7209	0.7608	0.072*
C14	0.3393 (3)	0.56575 (17)	0.7898 (2)	0.0494 (5)
H14	0.4820	0.5401	0.8419	0.059*
N1	0.1675 (3)	0.38340 (13)	0.81222 (16)	0.0422 (4)
O1	0.4251 (3)	0.34287 (12)	0.66800 (17)	0.0611 (4)
O2	0.1866 (2)	0.06549 (12)	0.95739 (17)	0.0562 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0552 (3)	0.0452 (3)	0.0482 (3)	0.0055 (2)	0.0264 (2)	0.0024 (2)
S2	0.0693 (3)	0.0355 (2)	0.0669 (3)	0.0066 (2)	0.0325 (3)	0.0060 (3)
C1	0.071 (4)	0.066 (6)	0.064 (7)	0.005 (3)	0.039 (4)	−0.022 (4)
C2	0.067 (4)	0.040 (2)	0.074 (4)	0.004 (2)	0.030 (3)	−0.007 (2)
C1'	0.111 (10)	0.034 (4)	0.059 (8)	0.014 (4)	0.048 (6)	−0.012 (4)
C2'	0.059 (4)	0.035 (3)	0.081 (5)	0.005 (3)	0.022 (4)	0.001 (3)
C3	0.0437 (10)	0.0379 (10)	0.0358 (9)	−0.0007 (8)	0.0123 (7)	0.0000 (7)
C4	0.0437 (9)	0.0369 (9)	0.0381 (9)	−0.0002 (7)	0.0167 (7)	0.0008 (8)
C5	0.0482 (10)	0.0415 (10)	0.0387 (9)	−0.0055 (9)	0.0154 (7)	0.0024 (9)
C6	0.0597 (12)	0.0503 (12)	0.0469 (11)	0.0006 (10)	0.0313 (9)	0.0002 (9)
C7	0.0556 (11)	0.0459 (12)	0.0484 (11)	0.0022 (9)	0.0272 (9)	−0.0053 (9)
C8	0.0501 (11)	0.0399 (10)	0.0412 (10)	0.0042 (8)	0.0199 (8)	0.0025 (8)
C9	0.0458 (9)	0.0376 (10)	0.0417 (9)	0.0042 (8)	0.0194 (7)	0.0006 (8)
C10	0.0436 (10)	0.0543 (12)	0.0589 (13)	0.0057 (9)	0.0144 (9)	−0.0045 (10)
C11	0.0611 (12)	0.0638 (15)	0.0593 (12)	0.0260 (12)	0.0127 (10)	0.0049 (12)
C12	0.0907 (17)	0.0430 (11)	0.0712 (14)	0.0188 (12)	0.0433 (13)	0.0104 (11)
C13	0.0627 (13)	0.0433 (12)	0.0831 (15)	−0.0024 (10)	0.0341 (11)	−0.0004 (11)
C14	0.0463 (10)	0.0441 (11)	0.0600 (14)	0.0013 (9)	0.0153 (9)	0.0000 (9)
N1	0.0508 (9)	0.0347 (8)	0.0465 (9)	0.0038 (7)	0.0227 (7)	−0.0003 (7)
O1	0.0833 (10)	0.0434 (8)	0.0717 (10)	0.0140 (8)	0.0525 (8)	0.0151 (7)
O2	0.0678 (9)	0.0442 (8)	0.0644 (9)	−0.0033 (7)	0.0323 (7)	0.0112 (7)

Geometric parameters (Å, º) top

S1—C3	1.732 (2)	C5—C6	1.432 (3)
S1—C1	1.761 (15)	C6—C7	1.323 (3)
S1—C1'	1.857 (16)	C6—H6	0.9300
S2—C3	1.732 (2)	C7—N1	1.377 (2)
S2—C2	1.813 (5)	C7—H7	0.9300
S2—C2'	1.850 (6)	C8—O1	1.231 (2)
C1—C2	1.479 (19)	C8—N1	1.396 (2)
C1—H1A	0.9700	C9—C10	1.376 (3)
C1—H1B	0.9700	C9—C14	1.379 (3)
C2—H2A	0.9700	C9—N1	1.441 (2)
C2—H2B	0.9700	C10—C11	1.388 (3)
C1'—C2'	1.48 (2)	C10—H10	0.9300
C1'—H1'A	0.9700	C11—C12	1.367 (4)
C1'—H1'B	0.9700	C11—H11	0.9300
C2'—H2'A	0.9700	C12—C13	1.370 (3)
C2'—H2'B	0.9700	C12—H12	0.9300
C3—C4	1.385 (3)	C13—C14	1.377 (3)
C4—C8	1.455 (3)	C13—H13	0.9300
C4—C5	1.466 (2)	C14—H14	0.9300
C5—O2	1.240 (2)

C3—S1—C1	95.2 (5)	C8—C4—C5	120.70 (16)
C3—S1—C1'	98.4 (7)	O2—C5—C6	122.80 (17)
C1—S1—C1'	12.1 (9)	O2—C5—C4	121.01 (18)
C3—S2—C2	96.19 (18)	C6—C5—C4	116.20 (18)
C3—S2—C2'	94.75 (19)	C7—C6—C5	121.31 (18)
C2—S2—C2'	26.22 (19)	C7—C6—H6	119.3
C2—C1—S1	113.1 (9)	C5—C6—H6	119.3
C2—C1—H1A	109.0	C6—C7—N1	123.46 (17)
S1—C1—H1A	109.0	C6—C7—H7	118.3
C2—C1—H1B	109.0	N1—C7—H7	118.3
S1—C1—H1B	109.0	O1—C8—N1	119.78 (18)
H1A—C1—H1B	107.8	O1—C8—C4	123.65 (17)
C1—C2—S2	106.3 (7)	N1—C8—C4	116.55 (16)
C1—C2—H2A	110.5	C10—C9—C14	120.52 (19)
S2—C2—H2A	110.5	C10—C9—N1	120.09 (17)
C1—C2—H2B	110.5	C14—C9—N1	119.38 (17)
S2—C2—H2B	110.5	C9—C10—C11	119.1 (2)
H2A—C2—H2B	108.7	C9—C10—H10	120.4
C2'—C1'—S1	105.6 (11)	C11—C10—H10	120.4
C2'—C1'—H1'A	110.6	C12—C11—C10	120.5 (2)
S1—C1'—H1'A	110.6	C12—C11—H11	119.8
C2'—C1'—H1'B	110.6	C10—C11—H11	119.8
S1—C1'—H1'B	110.6	C11—C12—C13	119.9 (2)
H1'A—C1'—H1'B	108.7	C11—C12—H12	120.1
C1'—C2'—S2	111.9 (9)	C13—C12—H12	120.1
C1'—C2'—H2'A	109.2	C12—C13—C14	120.6 (2)
S2—C2'—H2'A	109.2	C12—C13—H13	119.7
C1'—C2'—H2'B	109.2	C14—C13—H13	119.7
S2—C2'—H2'B	109.2	C13—C14—C9	119.4 (2)
H2'A—C2'—H2'B	107.9	C13—C14—H14	120.3
C4—C3—S1	122.87 (14)	C9—C14—H14	120.3
C4—C3—S2	121.84 (15)	C7—N1—C8	121.74 (16)
S1—C3—S2	115.28 (11)	C7—N1—C9	119.40 (15)
C3—C4—C8	118.94 (16)	C8—N1—C9	118.86 (15)
C3—C4—C5	120.35 (18)

C3—S1—C1—C2	29.1 (11)	O2—C5—C6—C7	−177.6 (2)
C1'—S1—C1—C2	−77 (5)	C4—C5—C6—C7	2.6 (3)
S1—C1—C2—S2	−40.8 (12)	C5—C6—C7—N1	−1.2 (3)
C3—S2—C2—C1	31.6 (9)	C3—C4—C8—O1	0.5 (3)
C2'—S2—C2—C1	−56.5 (9)	C5—C4—C8—O1	−178.25 (19)
C3—S1—C1'—C2'	−28.1 (12)	C3—C4—C8—N1	178.91 (17)
C1—S1—C1'—C2'	47 (5)	C5—C4—C8—N1	0.1 (3)
S1—C1'—C2'—S2	40.1 (13)	C14—C9—C10—C11	1.1 (3)
C3—S2—C2'—C1'	−33.7 (10)	N1—C9—C10—C11	−179.94 (18)
C2—S2—C2'—C1'	60.7 (11)	C9—C10—C11—C12	−0.3 (3)
C1—S1—C3—C4	175.0 (5)	C10—C11—C12—C13	−0.8 (4)
C1'—S1—C3—C4	−173.3 (6)	C11—C12—C13—C14	1.0 (4)
C1—S1—C3—S2	−5.4 (5)	C12—C13—C14—C9	−0.3 (3)
C1'—S1—C3—S2	6.3 (6)	C10—C9—C14—C13	−0.8 (3)
C2—S2—C3—C4	165.9 (4)	N1—C9—C14—C13	−179.81 (18)
C2'—S2—C3—C4	−167.8 (4)	C6—C7—N1—C8	−0.9 (3)
C2—S2—C3—S1	−13.8 (4)	C6—C7—N1—C9	178.73 (18)
C2'—S2—C3—S1	12.5 (4)	O1—C8—N1—C7	179.79 (18)
S1—C3—C4—C8	2.5 (3)	C4—C8—N1—C7	1.4 (3)
S2—C3—C4—C8	−177.09 (14)	O1—C8—N1—C9	0.2 (3)
S1—C3—C4—C5	−178.70 (14)	C4—C8—N1—C9	−178.25 (16)
S2—C3—C4—C5	1.7 (2)	C10—C9—N1—C7	−65.0 (2)
C3—C4—C5—O2	−0.6 (3)	C14—C9—N1—C7	114.0 (2)
C8—C4—C5—O2	178.16 (18)	C10—C9—N1—C8	114.7 (2)
C3—C4—C5—C6	179.24 (18)	C14—C9—N1—C8	−66.3 (2)
C8—C4—C5—C6	−2.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1′—H1′A···O1ⁱ	0.97	2.43	3.300 (17)	148
C2—H2B···O1ⁱ	0.97	2.69	3.388 (8)	129
C7—H7···O2ⁱⁱ	0.93	2.36	3.259 (3)	163
C14—H14···O2ⁱⁱⁱ	0.93	2.46	3.293 (3)	149
C11—H11···S1^iv	0.93	2.90	3.756 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁NO₂S₂
M_r	289.36
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	292
a, b, c (Å)	5.7708 (17), 12.033 (4), 9.624 (3)
β (°)	101.094 (3)
V (Å³)	655.8 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.35 × 0.29 × 0.28

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.870, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	5598, 2543, 2361
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.071, 1.04
No. of reflections	2543
No. of parameters	191
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.21
Absolute structure	Flack (1983), 1181 Friedel pairs
Absolute structure parameter	−0.05 (5)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SAINT (Bruker, 2007, 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
C1'—H1'A···O1ⁱ	0.97	2.43	3.300 (17)	148
C2—H2B···O1ⁱ	0.97	2.69	3.388 (8)	129
C7—H7···O2ⁱⁱ	0.93	2.36	3.259 (3)	163
C14—H14···O2ⁱⁱⁱ	0.93	2.46	3.293 (3)	149
C11—H11···S1^iv	0.93	2.90	3.756 (3)	153

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

Acknowledgements

The authors thank the Jilin Institute of Chemical Technology for support of this work.

References

Bruker (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2, and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, Y.-H., Li, W.-L., Zhang, R., Zhou, Y. & Dong, D.-W. (2008). Synthesis, 21, 3411–3414. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar