4-Meth-oxy-N-[6-methyl-2,3-dihydro-1,3-benzothia-zol-2-yl-idene]benzene-sulfonamide.

The title compound, C(15)H(14)N(2)O(3)S(2), is of inter-est with respect to its biological activity. The crystal structure is stabilized by inter-molecular N-H⋯N, C-H⋯O and C-H⋯π hydrogen-bonding inter-actions, as well as offset π-π inter-actions [distance between the centroids of the aryl and thiazole rings of adjacent molecules of 3.954 (2) Å].

Related literature

For related literature, see: Su et al. (2006 ▶); Vicker et al. (2007 ▶); Siddiqui et al. (2007 ▶); Adams et al. (1996 ▶); Bernstein et al. (1995 ▶); Desiraju (1991 ▶); Hanton et al. (1992 ▶); Hunter (1994 ▶).

Experimental

Crystal data

C15H14N2O3S2

M = 334.40

Monoclinic,

a = 12.0173 (15) Å

b = 16.211 (2) Å

c = 7.7377 (10) Å

β = 99.973 (2)°

V = 1484.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 273 (2) K

0.57 × 0.16 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.816, T max = 0.964

12102 measured reflections

2617 independent reflections

2440 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.117

S = 1.15

2617 reflections

205 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus-NT (Bruker, 2000 ▶); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL-NT (Bruker, 2000 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065312/at2516sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065312/at2516Isup2.hkl

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

C15H14N2O3S2	F000 = 696
Mr = 334.40	Dx = 1.496 Mg m−3
Monoclinic, P21/c	Melting point: 534.4 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 12.0173 (15) Å	Cell parameters from 2617 reflections
b = 16.211 (2) Å	θ = 1.7–25.0º
c = 7.7377 (10) Å	µ = 0.37 mm−1
β = 99.973 (2)º	T = 273 (2) K
V = 1484.6 (3) Å3	Rectangular prism, yellow
Z = 4	0.57 × 0.16 × 0.10 mm

Bruker SMART APEX CCD area-detector diffractometer	2617 independent reflections
Radiation source: fine-focus sealed tube	2440 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
Detector resolution: 8.3 pixels mm-1	θmax = 25.0º
T = 273(2) K	θmin = 1.7º
φ and ω scans	h = −14→14
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	k = −19→18
Tmin = 0.816, Tmax = 0.964	l = −9→9
12102 measured reflections

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.9002P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max = 0.001
2617 reflections	Δρmax = 0.41 e Å−3
205 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.1795 (2)	0.78238 (17)	0.4365 (3)	0.0450 (6)
C2	0.0744 (2)	0.80223 (16)	0.4774 (3)	0.0422 (6)
C3	−0.0003 (2)	0.74059 (17)	0.5022 (4)	0.0512 (7)
H3	−0.0704	0.7531	0.5307	0.061*
C4	0.0318 (3)	0.66009 (18)	0.4836 (4)	0.0556 (7)
H4	−0.0185	0.6183	0.4993	0.067*
C5	0.1359 (3)	0.63832 (18)	0.4425 (4)	0.0524 (7)
C6	0.2108 (2)	0.70089 (18)	0.4188 (4)	0.0498 (7)
H6	0.2812	0.6883	0.3913	0.060*
C7	0.1455 (2)	0.93390 (16)	0.4535 (3)	0.0402 (6)
C8	0.3207 (2)	1.09049 (15)	0.6440 (3)	0.0385 (6)
C9	0.4280 (2)	1.05758 (17)	0.6913 (4)	0.0455 (6)
H9	0.4576	1.0234	0.6139	0.055*
C10	0.4905 (2)	1.07537 (17)	0.8519 (4)	0.0469 (6)
H10	0.5630	1.0540	0.8824	0.056*
C11	0.4465 (2)	1.12510 (15)	0.9704 (3)	0.0408 (6)
C12	0.3377 (2)	1.15595 (17)	0.9262 (4)	0.0451 (6)
H12	0.3068	1.1877	1.0061	0.054*
C13	0.2755 (2)	1.13914 (16)	0.7626 (4)	0.0440 (6)
H13	0.2030	1.1605	0.7316	0.053*
C14	0.4823 (3)	1.1987 (2)	1.2418 (4)	0.0591 (8)
H14A	0.4687	1.2510	1.1838	0.089*
H14B	0.5405	1.2046	1.3429	0.089*
H14C	0.4141	1.1798	1.2778	0.089*
C15	0.1682 (3)	0.54964 (19)	0.4239 (4)	0.0669 (9)
H15A	0.1849	0.5246	0.5379	0.100*
H15B	0.2337	0.5469	0.3686	0.100*
H15C	0.1068	0.5208	0.3534	0.100*
H1	−0.003 (2)	0.9100 (16)	0.509 (3)	0.046 (8)*
N1	0.05952 (18)	0.88679 (13)	0.4860 (3)	0.0426 (5)
N2	0.13799 (17)	1.01569 (13)	0.4570 (3)	0.0434 (5)
O1	0.31808 (16)	1.03121 (12)	0.3323 (2)	0.0513 (5)
O2	0.19594 (16)	1.14977 (12)	0.3663 (3)	0.0563 (5)
O3	0.51706 (16)	1.14040 (12)	1.1242 (3)	0.0541 (5)
S1	0.24400 (5)	1.07274 (4)	0.43153 (8)	0.0417 (2)
S2	0.25626 (5)	0.87158 (5)	0.40816 (9)	0.0480 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0430 (14)	0.0497 (16)	0.0401 (14)	0.0028 (12)	0.0015 (11)	−0.0023 (12)
C2	0.0412 (13)	0.0448 (15)	0.0388 (13)	0.0035 (12)	0.0014 (11)	−0.0044 (11)
C3	0.0462 (15)	0.0451 (16)	0.0613 (17)	−0.0012 (13)	0.0062 (13)	−0.0020 (14)
C4	0.0613 (18)	0.0438 (16)	0.0585 (18)	−0.0095 (14)	0.0017 (14)	0.0016 (13)
C5	0.0669 (18)	0.0441 (16)	0.0414 (15)	0.0084 (14)	−0.0041 (13)	−0.0028 (12)
C6	0.0512 (16)	0.0512 (17)	0.0457 (15)	0.0115 (13)	0.0042 (12)	−0.0017 (12)
C7	0.0334 (12)	0.0466 (15)	0.0395 (13)	−0.0003 (11)	0.0039 (10)	−0.0051 (11)
C8	0.0346 (12)	0.0335 (13)	0.0491 (14)	−0.0050 (10)	0.0119 (11)	−0.0019 (11)
C9	0.0432 (14)	0.0447 (15)	0.0512 (15)	0.0082 (12)	0.0150 (12)	−0.0060 (12)
C10	0.0392 (14)	0.0462 (16)	0.0561 (16)	0.0104 (12)	0.0106 (12)	−0.0031 (12)
C11	0.0416 (13)	0.0344 (13)	0.0472 (14)	−0.0011 (11)	0.0097 (11)	0.0001 (11)
C12	0.0418 (14)	0.0442 (15)	0.0526 (16)	0.0034 (12)	0.0173 (12)	−0.0077 (12)
C13	0.0313 (12)	0.0462 (15)	0.0557 (16)	0.0038 (11)	0.0108 (11)	−0.0052 (12)
C14	0.0651 (19)	0.0595 (19)	0.0521 (17)	0.0015 (15)	0.0086 (14)	−0.0137 (14)
C15	0.090 (2)	0.0467 (18)	0.0602 (19)	0.0139 (17)	0.0018 (17)	−0.0001 (15)
N1	0.0339 (11)	0.0405 (13)	0.0538 (13)	0.0021 (10)	0.0084 (10)	−0.0054 (10)
N2	0.0348 (11)	0.0393 (12)	0.0568 (13)	−0.0015 (9)	0.0098 (10)	−0.0064 (10)
O1	0.0471 (10)	0.0587 (13)	0.0518 (11)	−0.0061 (9)	0.0184 (9)	−0.0104 (9)
O2	0.0562 (12)	0.0495 (12)	0.0611 (12)	0.0012 (9)	0.0046 (10)	0.0077 (9)
O3	0.0507 (11)	0.0564 (12)	0.0532 (11)	0.0081 (9)	0.0031 (9)	−0.0098 (9)
S1	0.0377 (3)	0.0418 (4)	0.0469 (4)	−0.0029 (3)	0.0109 (3)	−0.0028 (3)
S2	0.0389 (4)	0.0487 (4)	0.0582 (4)	0.0048 (3)	0.0137 (3)	−0.0031 (3)

C1—C6	1.387 (4)	C9—H9	0.9300
C1—C2	1.391 (4)	C10—C11	1.392 (4)
C1—S2	1.749 (3)	C10—H10	0.9300
C2—C3	1.378 (4)	C11—O3	1.359 (3)
C2—N1	1.385 (3)	C11—C12	1.387 (4)
C3—C4	1.375 (4)	C12—C13	1.381 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.388 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—O3	1.424 (3)
C5—C6	1.389 (4)	C14—H14A	0.9600
C5—C15	1.502 (4)	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—N2	1.330 (3)	C15—H15A	0.9600
C7—N1	1.343 (3)	C15—H15B	0.9600
C7—S2	1.754 (3)	C15—H15C	0.9600
C8—C9	1.385 (4)	N1—H1	0.89 (3)
C8—C13	1.390 (3)	N2—S1	1.614 (2)
C8—S1	1.764 (3)	O1—S1	1.4394 (19)
C9—C10	1.367 (4)	O2—S1	1.431 (2)
C6—C1—C2	121.0 (3)	C12—C11—C10	119.7 (2)
C6—C1—S2	128.1 (2)	C13—C12—C11	119.5 (2)
C2—C1—S2	110.9 (2)	C13—C12—H12	120.2
C3—C2—N1	128.2 (2)	C11—C12—H12	120.2
C3—C2—C1	120.1 (3)	C12—C13—C8	120.4 (2)
N1—C2—C1	111.7 (2)	C12—C13—H13	119.8
C4—C3—C2	118.2 (3)	C8—C13—H13	119.8
C4—C3—H3	120.9	O3—C14—H14A	109.5
C2—C3—H3	120.9	O3—C14—H14B	109.5
C3—C4—C5	123.0 (3)	H14A—C14—H14B	109.5
C3—C4—H4	118.5	O3—C14—H14C	109.5
C5—C4—H4	118.5	H14A—C14—H14C	109.5
C4—C5—C6	118.3 (3)	H14B—C14—H14C	109.5
C4—C5—C15	121.6 (3)	C5—C15—H15A	109.5
C6—C5—C15	120.1 (3)	C5—C15—H15B	109.5
C1—C6—C5	119.3 (3)	H15A—C15—H15B	109.5
C1—C6—H6	120.4	C5—C15—H15C	109.5
C5—C6—H6	120.4	H15A—C15—H15C	109.5
N2—C7—N1	120.4 (2)	H15B—C15—H15C	109.5
N2—C7—S2	129.42 (19)	C7—N1—C2	116.3 (2)
N1—C7—S2	110.18 (19)	C7—N1—H1	120.3 (17)
C9—C8—C13	119.8 (2)	C2—N1—H1	123.4 (17)
C9—C8—S1	119.73 (19)	C7—N2—S1	120.74 (17)
C13—C8—S1	120.45 (19)	C11—O3—C14	118.2 (2)
C10—C9—C8	119.9 (2)	O2—S1—O1	117.99 (12)
C10—C9—H9	120.1	O2—S1—N2	105.33 (12)
C8—C9—H9	120.1	O1—S1—N2	111.79 (11)
C9—C10—C11	120.7 (2)	O2—S1—C8	107.49 (12)
C9—C10—H10	119.7	O1—S1—C8	107.55 (12)
C11—C10—H10	119.7	N2—S1—C8	106.02 (12)
O3—C11—C12	124.7 (2)	C1—S2—C7	90.91 (12)
O3—C11—C10	115.6 (2)
C6—C1—C2—C3	0.4 (4)	S1—C8—C13—C12	−177.1 (2)
S2—C1—C2—C3	178.9 (2)	N2—C7—N1—C2	179.3 (2)
C6—C1—C2—N1	−179.0 (2)	S2—C7—N1—C2	−0.1 (3)
S2—C1—C2—N1	−0.5 (3)	C3—C2—N1—C7	−179.0 (3)
N1—C2—C3—C4	178.7 (3)	C1—C2—N1—C7	0.4 (3)
C1—C2—C3—C4	−0.6 (4)	N1—C7—N2—S1	175.70 (19)
C2—C3—C4—C5	0.5 (4)	S2—C7—N2—S1	−5.1 (3)
C3—C4—C5—C6	−0.1 (4)	C12—C11—O3—C14	−6.8 (4)
C3—C4—C5—C15	179.8 (3)	C10—C11—O3—C14	172.5 (2)
C2—C1—C6—C5	−0.1 (4)	C7—N2—S1—O2	155.3 (2)
S2—C1—C6—C5	−178.3 (2)	C7—N2—S1—O1	25.9 (2)
C4—C5—C6—C1	−0.1 (4)	C7—N2—S1—C8	−91.0 (2)
C15—C5—C6—C1	−180.0 (3)	C9—C8—S1—O2	−134.5 (2)
C13—C8—C9—C10	−2.2 (4)	C13—C8—S1—O2	43.7 (2)
S1—C8—C9—C10	176.0 (2)	C9—C8—S1—O1	−6.5 (2)
C8—C9—C10—C11	1.2 (4)	C13—C8—S1—O1	171.7 (2)
C9—C10—C11—O3	−178.4 (2)	C9—C8—S1—N2	113.2 (2)
C9—C10—C11—C12	1.0 (4)	C13—C8—S1—N2	−68.6 (2)
O3—C11—C12—C13	177.1 (2)	C6—C1—S2—C7	178.7 (3)
C10—C11—C12—C13	−2.1 (4)	C2—C1—S2—C7	0.4 (2)
C11—C12—C13—C8	1.1 (4)	N2—C7—S2—C1	−179.5 (2)
C9—C8—C13—C12	1.1 (4)	N1—C7—S2—C1	−0.15 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.89 (2)	2.07 (2)	2.948 (3)	169 (2)
C3—H3···O2i	0.93	2.41	3.248 (3)	150
C6—H6···O3ii	0.93	2.57	3.485 (3)	169
C9—H9···O1	0.93	2.51	2.894 (3)	105
C14—H14A···Cg3iii	0.93	2.76	3.433 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.89 (2)	2.07 (2)	2.948 (3)	169 (2)
C3—H3⋯O2i	0.93	2.41	3.248 (3)	150
C6—H6⋯O3ii	0.93	2.57	3.485 (3)	169
C9—H9⋯O1	0.93	2.51	2.894 (3)	105
C14—H14A⋯Cg3iii	0.96	2.76	3.433 (3)	128

Symmetry codes: (i) ; (ii) ; (iii) . Cg3 is the centroid of the C8–C13 benzene ring.