3-{2-[(1,3-Benzothia-zol-2-yl)sulfanyl-meth-yl]phen-yl}-4-meth-oxy-5,5-dimethyl-furan-2(5H)-one.

In the title compound, C(21)H(19)NO(3)S(2), the dihedral angles formed between the thia-zole 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 inter-action.

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 = 397.49

Triclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.109

S = 0.90

3804 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022404/im2376sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812022404/im2376Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H19NO3S2	Z = 2
Mr = 397.49	F(000) = 416
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0592P)2] where P = (Fo2 + 2Fc2)/3
3804 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .