3-{2-[(1,3-Benzothia­zol-2-yl)sulfanyl­meth­yl]phen­yl}-4-meth­oxy-5,5-dimethyl­furan-2(5H)-one

Duan, A.; Yang, H.; Zhao, P.; You, W.

doi:10.1107/S1600536812022404

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1854

doi:10.1107/S1600536812022404

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3-{2-[(1,3-Benzothiazol-2-yl)sulfanylmethyl]phenyl}-4-methoxy-5,5-dimethylfuran-2(5H)-one

Anna Duan,^a Haikui Yang,^a Peiliang Zhao ^a and Wenwei You ^a ^*

^aSchool of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, People's Republic of China
^*Correspondence e-mail: youww@smu.edu.cn

(Received 8 May 2012; accepted 17 May 2012; online 23 May 2012)

In the title compound, C₂₁H₁₉NO₃S₂, the dihedral angles formed between the thiazole ring and the adjacent benzene ring and the other benzene ring are 1.58 (3) and 76.48 (6)°, respectively. The crystal structure features a weak C—H⋯O interaction.

Related literature

For the anti-tumor activity of benzothiazole derivatives, see: Brantley et al. (2004 ) and for their anti-tuberculous properties, see: Palmer et al. (1971 ). For fungicidal properties of benzothiazolines and the preparation of the title compound, see: Zhao et al. (2010 ). For general background to furan-2(5H)-ones and their derivatives, see: Iannazzo et al. (2008 ).

Experimental

Crystal data

C₂₁H₁₉NO₃S₂
M_r = 397.49
Triclinic, $[P \overline 1]$
a = 10.4702 (9) Å
b = 10.4851 (9) Å
c = 10.5169 (9) Å
α = 117.567 (1)°
β = 100.398 (1)°
γ = 95.257 (1)°
V = 986.15 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 292 K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2005 ) T_min = 0.944, T_max = 0.972
7206 measured reflections
3804 independent reflections
2713 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.109
S = 0.90
3804 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.56	3.302 (3)	137
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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/S1600536812022404/im2376sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022404/im2376Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022404/im2376Isup3.cml

checkCIF report

Comment top

Benzothiazole derivatives are well known to exhibit a wide spectrum of biological activities, including fungicidal, anticancer and anti-tuberculous properties. (Brantley et al., 2004; Zhao et al., 2010; Palmer et al., 1971). In addition, furan-2(5H)-one derivatives also have good biological activities (Iannazzo et al., 2008). These findings prompted us to synthesize a new series of benzothiazole derivatives by incorporating furan-2(5H)-one at the 2-position, in the hope of finding molecules showing an improved bioactivity. We present here the X-ray crystallographic analysis of the title compound, (I), which was designed and synthesized in our laboratory.

A view of the molecular structure of the title compound is given in Fig.1. The bond lengths and angles are unremarkable.The dihedral angles formed between the triazole ring and the adjacent benzene ring and the other benzene ring system are 1.58 (3)° and 76.48 (6)°, respectively. One intermolecular C—H···O hydrogen bond exists in the crystal structure (Table 1). Atom C2 in the molecule acts as donor, via the H atom H2, towards O1 of an adjacent molecule (Fig.2). No π-π-stacking interactions are observed in the crystal structure.

Related literature top

For the anti-tumor activity of benzothiazole derivatives, see: Brantley et al. (2004) and for their anti-tuberculous properties, see: Palmer et al. (1971). For fungicidal properties of benzothiazolines and the preparation of the title compound, see: Zhao et al. (2010). For general background to furan-2(5H)-ones and their derivatives, see: Iannazzo et al. (2008).

Experimental top

The title compound was synthesized according to a published procedure (Zhao et al., 2010). Crystals appropriate for X-ray data collection were obtained by slow evaporation of a methanolic solution at 292 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. A view of the molecule of (I) showing displacement ellipsoids at the 50% probability level. H atoms are represented by circles of arbitrary size.
	Fig. 2. Hydrogen bonding in the crystal structure of (I). Hydrogen bonds are shown as dashed lines. [Symmetry codes: x - 1, y, z]

3-{2-[(1,3-Benzothiazol-2-yl)sulfanylmethyl]phenyl}-4-methoxy- 5,5-dimethylfuran-2(5H)-one top

Crystal data top

C₂₁H₁₉NO₃S₂	Z = 2
M_r = 397.49	F(000) = 416
Triclinic, P1	D_x = 1.339 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4702 (9) Å	Cell parameters from 2192 reflections
b = 10.4851 (9) Å	θ = 2.3–24.6°
c = 10.5169 (9) Å	µ = 0.29 mm⁻¹
α = 117.567 (1)°	T = 292 K
β = 100.398 (1)°	Block, colorless
γ = 95.257 (1)°	0.20 × 0.20 × 0.10 mm
V = 986.15 (15) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3804 independent reflections
Radiation source: fine-focus sealed tube	2713 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
phi and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2005)	h = −11→12
T_min = 0.944, T_max = 0.972	k = −12→12
7206 measured reflections	l = −12→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0592P)²] where P = (F_o² + 2F_c²)/3
3804 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₁H₁₉NO₃S₂	γ = 95.257 (1)°
M_r = 397.49	V = 986.15 (15) Å³
Triclinic, P1	Z = 2
a = 10.4702 (9) Å	Mo Kα radiation
b = 10.4851 (9) Å	µ = 0.29 mm⁻¹
c = 10.5169 (9) Å	T = 292 K
α = 117.567 (1)°	0.20 × 0.20 × 0.10 mm
β = 100.398 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3804 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2005)	2713 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.972	R_int = 0.040
7206 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 0.90	Δρ_max = 0.25 e Å⁻³
3804 reflections	Δρ_min = −0.22 e Å⁻³
247 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
C1	0.3099 (2)	1.1296 (2)	0.3804 (2)	0.0429 (5)
C2	0.1915 (2)	1.1787 (3)	0.3934 (3)	0.0585 (6)
H2	0.1101	1.1139	0.3439	0.070*
C3	0.1987 (3)	1.3256 (3)	0.4814 (3)	0.0749 (8)
H3	0.1207	1.3609	0.4920	0.090*
C4	0.3186 (3)	1.4226 (3)	0.5548 (3)	0.0720 (8)
H4	0.3199	1.5220	0.6133	0.086*
C5	0.4367 (2)	1.3757 (2)	0.5435 (3)	0.0548 (6)
H5	0.5172	1.4418	0.5944	0.066*
C6	0.4325 (2)	1.2275 (2)	0.4545 (2)	0.0401 (5)
C7	0.5064 (2)	1.0231 (2)	0.3504 (2)	0.0393 (5)
C8	0.7722 (2)	1.0145 (2)	0.3745 (2)	0.0471 (5)
H8A	0.7754	1.0955	0.4713	0.057*
H8B	0.8379	0.9594	0.3878	0.057*
C9	0.80777 (19)	1.0755 (2)	0.2782 (2)	0.0383 (5)
C10	0.82367 (19)	0.9825 (2)	0.1364 (2)	0.0388 (5)
C11	0.8548 (2)	1.0439 (2)	0.0510 (2)	0.0468 (5)
H11	0.8650	0.9830	−0.0432	0.056*
C12	0.8711 (2)	1.1929 (3)	0.1022 (3)	0.0532 (6)
H12	0.8919	1.2318	0.0433	0.064*
C13	0.8561 (2)	1.2839 (2)	0.2417 (3)	0.0547 (6)
H13	0.8674	1.3847	0.2775	0.066*
C14	0.8244 (2)	1.2252 (2)	0.3280 (2)	0.0486 (6)
H14	0.8140	1.2873	0.4217	0.058*
C15	0.8151 (2)	0.8231 (2)	0.0802 (2)	0.0406 (5)
C16	0.7292 (2)	0.7023 (2)	−0.0266 (2)	0.0495 (6)
C17	0.7745 (2)	0.5641 (3)	−0.0455 (3)	0.0630 (7)
C18	0.9225 (2)	0.7703 (3)	0.1412 (3)	0.0514 (6)
C19	0.5531 (2)	0.8016 (3)	−0.1034 (3)	0.0575 (6)
H19A	0.5432	0.8556	−0.0043	0.086*
H19B	0.4677	0.7665	−0.1725	0.086*
H19C	0.6086	0.8647	−0.1235	0.086*
C20	0.6809 (3)	0.4717 (3)	−0.0114 (4)	0.0940 (10)
H20A	0.7197	0.3923	−0.0111	0.141*
H20B	0.5983	0.4328	−0.0856	0.141*
H20C	0.6657	0.5315	0.0841	0.141*
C21	0.8059 (3)	0.4778 (3)	−0.1948 (3)	0.0900 (10)
H21A	0.8612	0.5429	−0.2127	0.135*
H21B	0.7250	0.4334	−0.2718	0.135*
H21C	0.8515	0.4026	−0.1941	0.135*
N1	0.54360 (17)	1.16332 (19)	0.43437 (18)	0.0421 (4)
O1	1.02066 (17)	0.84009 (18)	0.2398 (2)	0.0706 (5)
O2	0.89788 (16)	0.62095 (17)	0.06858 (18)	0.0649 (5)
O3	0.61278 (16)	0.67939 (17)	−0.11829 (18)	0.0677 (5)
S1	0.33515 (6)	0.95239 (6)	0.28478 (6)	0.04817 (18)
S2	0.60881 (6)	0.89569 (6)	0.29888 (6)	0.04876 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0394 (13)	0.0446 (13)	0.0388 (11)	0.0066 (10)	0.0056 (10)	0.0175 (10)
C2	0.0378 (14)	0.0557 (16)	0.0604 (15)	0.0056 (12)	0.0000 (12)	0.0162 (13)
C3	0.0425 (16)	0.0631 (18)	0.091 (2)	0.0176 (14)	0.0086 (15)	0.0167 (16)
C4	0.0551 (18)	0.0436 (15)	0.088 (2)	0.0149 (13)	0.0073 (15)	0.0121 (15)
C5	0.0463 (15)	0.0416 (14)	0.0616 (15)	0.0026 (11)	0.0019 (12)	0.0184 (12)
C6	0.0366 (12)	0.0418 (13)	0.0405 (11)	0.0050 (10)	0.0064 (10)	0.0209 (10)
C7	0.0413 (13)	0.0427 (13)	0.0372 (11)	0.0079 (10)	0.0111 (10)	0.0219 (10)
C8	0.0421 (13)	0.0541 (14)	0.0441 (12)	0.0157 (11)	0.0110 (11)	0.0221 (11)
C9	0.0265 (11)	0.0390 (12)	0.0429 (12)	0.0082 (9)	0.0058 (9)	0.0156 (10)
C10	0.0283 (11)	0.0409 (12)	0.0411 (11)	0.0097 (9)	0.0065 (9)	0.0155 (10)
C11	0.0401 (13)	0.0523 (15)	0.0461 (13)	0.0114 (11)	0.0151 (10)	0.0206 (11)
C12	0.0440 (14)	0.0568 (16)	0.0663 (16)	0.0077 (12)	0.0170 (12)	0.0356 (14)
C13	0.0479 (15)	0.0392 (14)	0.0766 (17)	0.0115 (11)	0.0190 (13)	0.0263 (13)
C14	0.0419 (13)	0.0437 (14)	0.0487 (13)	0.0107 (11)	0.0134 (11)	0.0124 (11)
C15	0.0322 (12)	0.0388 (12)	0.0428 (12)	0.0104 (10)	0.0084 (10)	0.0132 (10)
C16	0.0387 (13)	0.0433 (14)	0.0515 (13)	0.0124 (11)	0.0027 (11)	0.0135 (11)
C17	0.0431 (15)	0.0404 (14)	0.0751 (17)	0.0103 (12)	−0.0045 (13)	0.0104 (13)
C18	0.0405 (14)	0.0442 (15)	0.0562 (14)	0.0145 (11)	0.0076 (12)	0.0146 (12)
C19	0.0451 (15)	0.0602 (16)	0.0596 (15)	0.0165 (12)	0.0001 (12)	0.0269 (13)
C20	0.071 (2)	0.0528 (18)	0.143 (3)	0.0068 (16)	0.003 (2)	0.045 (2)
C21	0.076 (2)	0.0606 (18)	0.078 (2)	0.0289 (16)	−0.0061 (16)	−0.0043 (16)
N1	0.0396 (11)	0.0438 (11)	0.0437 (10)	0.0062 (9)	0.0088 (8)	0.0232 (9)
O1	0.0455 (11)	0.0551 (11)	0.0751 (12)	0.0121 (9)	−0.0145 (9)	0.0129 (10)
O2	0.0498 (11)	0.0427 (10)	0.0749 (11)	0.0169 (8)	−0.0066 (9)	0.0132 (9)
O3	0.0483 (11)	0.0482 (10)	0.0695 (11)	0.0112 (8)	−0.0148 (9)	0.0091 (9)
S1	0.0433 (4)	0.0417 (4)	0.0459 (3)	0.0025 (3)	0.0043 (3)	0.0141 (3)
S2	0.0507 (4)	0.0436 (4)	0.0557 (4)	0.0122 (3)	0.0204 (3)	0.0243 (3)

Geometric parameters (Å, º) top

C1—C2	1.391 (3)	C12—C13	1.379 (3)
C1—C6	1.403 (3)	C12—H12	0.9300
C1—S1	1.729 (2)	C13—C14	1.378 (3)
C2—C3	1.367 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.377 (3)	C15—C16	1.336 (3)
C3—H3	0.9300	C15—C18	1.471 (3)
C4—C5	1.377 (3)	C16—O3	1.334 (3)
C4—H4	0.9300	C16—C17	1.503 (3)
C5—C6	1.385 (3)	C17—O2	1.450 (3)
C5—H5	0.9300	C17—C20	1.517 (4)
C6—N1	1.397 (3)	C17—C21	1.524 (4)
C7—N1	1.289 (2)	C18—O1	1.201 (3)
C7—S2	1.741 (2)	C18—O2	1.360 (3)
C7—S1	1.754 (2)	C19—O3	1.433 (3)
C8—C9	1.504 (3)	C19—H19A	0.9600
C8—S2	1.820 (2)	C19—H19B	0.9600
C8—H8A	0.9700	C19—H19C	0.9600
C8—H8B	0.9700	C20—H20A	0.9600
C9—C14	1.387 (3)	C20—H20B	0.9600
C9—C10	1.406 (3)	C20—H20C	0.9600
C10—C11	1.390 (3)	C21—H21A	0.9600
C10—C15	1.480 (3)	C21—H21B	0.9600
C11—C12	1.378 (3)	C21—H21C	0.9600
C11—H11	0.9300

C2—C1—C6	121.1 (2)	C13—C14—C9	121.5 (2)
C2—C1—S1	129.24 (18)	C13—C14—H14	119.3
C6—C1—S1	109.60 (16)	C9—C14—H14	119.3
C3—C2—C1	117.8 (2)	C16—C15—C18	105.53 (19)
C3—C2—H2	121.1	C16—C15—C10	134.4 (2)
C1—C2—H2	121.1	C18—C15—C10	120.01 (19)
C2—C3—C4	121.6 (2)	O3—C16—C15	133.6 (2)
C2—C3—H3	119.2	O3—C16—C17	114.12 (19)
C4—C3—H3	119.2	C15—C16—C17	112.3 (2)
C3—C4—C5	121.4 (2)	O2—C17—C16	102.18 (18)
C3—C4—H4	119.3	O2—C17—C20	107.9 (2)
C5—C4—H4	119.3	C16—C17—C20	112.3 (2)
C4—C5—C6	118.3 (2)	O2—C17—C21	107.9 (2)
C4—C5—H5	120.8	C16—C17—C21	112.4 (2)
C6—C5—H5	120.8	C20—C17—C21	113.3 (2)
C5—C6—N1	124.9 (2)	O1—C18—O2	120.9 (2)
C5—C6—C1	119.8 (2)	O1—C18—C15	129.0 (2)
N1—C6—C1	115.26 (18)	O2—C18—C15	110.17 (19)
N1—C7—S2	126.65 (17)	O3—C19—H19A	109.5
N1—C7—S1	116.90 (16)	O3—C19—H19B	109.5
S2—C7—S1	116.43 (12)	H19A—C19—H19B	109.5
C9—C8—S2	113.56 (14)	O3—C19—H19C	109.5
C9—C8—H8A	108.9	H19A—C19—H19C	109.5
S2—C8—H8A	108.9	H19B—C19—H19C	109.5
C9—C8—H8B	108.9	C17—C20—H20A	109.5
S2—C8—H8B	108.9	C17—C20—H20B	109.5
H8A—C8—H8B	107.7	H20A—C20—H20B	109.5
C14—C9—C10	118.79 (19)	C17—C20—H20C	109.5
C14—C9—C8	120.27 (18)	H20A—C20—H20C	109.5
C10—C9—C8	120.93 (18)	H20B—C20—H20C	109.5
C11—C10—C9	118.73 (19)	C17—C21—H21A	109.5
C11—C10—C15	119.70 (18)	C17—C21—H21B	109.5
C9—C10—C15	121.48 (18)	H21A—C21—H21B	109.5
C12—C11—C10	121.7 (2)	C17—C21—H21C	109.5
C12—C11—H11	119.2	H21A—C21—H21C	109.5
C10—C11—H11	119.2	H21B—C21—H21C	109.5
C11—C12—C13	119.5 (2)	C7—N1—C6	109.71 (18)
C11—C12—H12	120.3	C18—O2—C17	109.83 (17)
C13—C12—H12	120.3	C16—O3—C19	119.67 (17)
C14—C13—C12	119.9 (2)	C1—S1—C7	88.52 (10)
C14—C13—H13	120.1	C7—S2—C8	101.71 (10)
C12—C13—H13	120.1

C6—C1—C2—C3	−0.3 (3)	C18—C15—C16—C17	−1.3 (3)
S1—C1—C2—C3	177.37 (19)	C10—C15—C16—C17	175.3 (2)
C1—C2—C3—C4	0.2 (4)	O3—C16—C17—O2	−178.22 (19)
C2—C3—C4—C5	−0.4 (4)	C15—C16—C17—O2	1.5 (3)
C3—C4—C5—C6	0.7 (4)	O3—C16—C17—C20	−62.8 (3)
C4—C5—C6—N1	−178.7 (2)	C15—C16—C17—C20	117.0 (3)
C4—C5—C6—C1	−0.8 (3)	O3—C16—C17—C21	66.4 (3)
C2—C1—C6—C5	0.6 (3)	C15—C16—C17—C21	−113.8 (2)
S1—C1—C6—C5	−177.46 (16)	C16—C15—C18—O1	−179.5 (2)
C2—C1—C6—N1	178.74 (18)	C10—C15—C18—O1	3.3 (4)
S1—C1—C6—N1	0.6 (2)	C16—C15—C18—O2	0.5 (2)
S2—C8—C9—C14	114.53 (19)	C10—C15—C18—O2	−176.70 (18)
S2—C8—C9—C10	−64.9 (2)	S2—C7—N1—C6	−177.70 (14)
C14—C9—C10—C11	−0.3 (3)	S1—C7—N1—C6	0.6 (2)
C8—C9—C10—C11	179.14 (18)	C5—C6—N1—C7	177.21 (19)
C14—C9—C10—C15	176.32 (18)	C1—C6—N1—C7	−0.8 (2)
C8—C9—C10—C15	−4.2 (3)	O1—C18—O2—C17	−179.5 (2)
C9—C10—C11—C12	0.4 (3)	C15—C18—O2—C17	0.5 (3)
C15—C10—C11—C12	−176.34 (19)	C16—C17—O2—C18	−1.1 (3)
C10—C11—C12—C13	0.0 (3)	C20—C17—O2—C18	−119.7 (2)
C11—C12—C13—C14	−0.4 (3)	C21—C17—O2—C18	117.5 (2)
C12—C13—C14—C9	0.4 (3)	C15—C16—O3—C19	−4.9 (4)
C10—C9—C14—C13	−0.1 (3)	C17—C16—O3—C19	174.8 (2)
C8—C9—C14—C13	−179.52 (19)	C2—C1—S1—C7	−178.2 (2)
C11—C10—C15—C16	−71.7 (3)	C6—C1—S1—C7	−0.26 (14)
C9—C10—C15—C16	111.7 (3)	N1—C7—S1—C1	−0.19 (15)
C11—C10—C15—C18	104.6 (2)	S2—C7—S1—C1	178.27 (12)
C9—C10—C15—C18	−72.1 (3)	N1—C7—S2—C8	−6.61 (19)
C18—C15—C16—O3	178.4 (2)	S1—C7—S2—C8	175.11 (10)
C10—C15—C16—O3	−5.0 (4)	C9—C8—S2—C7	−80.97 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.56	3.302 (3)	137

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉NO₃S₂
M_r	397.49
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	10.4702 (9), 10.4851 (9), 10.5169 (9)
α, β, γ (°)	117.567 (1), 100.398 (1), 95.257 (1)
V (Å³)	986.15 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2005)
T_min, T_max	0.944, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	7206, 3804, 2713
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.109, 0.90
No. of reflections	3804
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.22

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
C2—H2···O1ⁱ	0.93	2.56	3.302 (3)	137.2

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors acknowledge financial support from the Science Foundation of the Medical Scientific Research Foundation of Guangdong Province (B2010185), and the Natural Science Foundation of Guangdong Province (No. 10451051501004725)

References

Brantley, E., Trapani, V., Alley, M. C., Hose, C. D., Bradshaw, T. D., Stevens, M. F. G., Sausville, E. A. & Stinson, S. F. (2004). Drug Metab. Disp. 32, 1392–1401. Web of Science CrossRef CAS Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Iannazzo, D., Piperno, A., Romeo, G., Romeo, R., Chiacchio, U., Rescifina, A., Balestrieri, E., Macchi, B., Mastino, A. & Cortese, R. (2008). Bioorg. Med. Chem. 16, 9610–9615. Web of Science CrossRef PubMed CAS Google Scholar
Palmer, P. J., Trigg, R. B. & &Warrington, J. V. (1971). J. Med. Chem. 14, 248–251. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2005). 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
Zhao, P. L., Wang, F., Huang, W., Chen, Q. & Liu, Z. M. (2010). Chin. J. Org. Chem. 30, 1567–1573. CAS Google Scholar

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Volume 68| Part 6| June 2012| Page o1854

doi:10.1107/S1600536812022404

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-{2-[(1,3-Benzo­thia­zol-2-yl)sulfanyl­meth­yl]phen­yl}-4-meth­­oxy-5,5-di­methyl­furan-2(5H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

3-{2-[(1,3-Benzothiazol-2-yl)sulfanylmethyl]phenyl}-4-methoxy-5,5-dimethylfuran-2(5H)-one