2-[3-(1,3-Benzothia-zol-2-yl)-2,2-di-methyl-prop-yl]-2-methyl-2,3-di-hydro-1,3-benzothia-zole.

In the title compound, C(20)H(22)N(2)S(2), the five-membered thia-zole ring of the 2-methyl-2,3-dihydro-1,3-benzothia-zole unit has an envelope conformation. The dihedral angle between the planar [maximum deviation of 0.014 (1) Å for the S atom] benzothia-zole ring system and the benzene ring is 78.37 (12)°. Two intra-molecular C-H⋯S hydrogen bonds are observed, forming rings of graph-set motif S(6). In the crystal, the molecules are consolidated in pairs through N-H⋯N hydrogen bonds and are arranged parallel to the b axis.

Related literature

For the biological activity of benzothia­zoles, see: Prabhu et al. (2011 ▶); Chaudhary et al. (2010 ▶): Kaur et al. (2010 ▶). For the crystal structures of closely related compounds see: Ghalib et al. (2011 ▶); Chen et al. (2009 ▶); Brandenburg et al. (1987 ▶).

Experimental

Crystal data

C20H22N2S2

M = 354.52

Triclinic,

a = 9.8472 (8) Å

b = 9.9039 (8) Å

c = 11.7974 (9) Å

α = 88.490 (2)°

β = 67.006 (2)°

γ = 60.764 (2)°

V = 904.64 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 273 K

0.49 × 0.13 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.868, T max = 0.985

10184 measured reflections

3354 independent reflections

2667 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 0.91

3354 reflections

224 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029297/rz2780sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029297/rz2780Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029297/rz2780Isup3.cml

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

C20H22N2S2	Z = 2
Mr = 354.52	F(000) = 376
Triclinic, P1	Dx = 1.301 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8472 (8) Å	Cell parameters from 2480 reflections
b = 9.9039 (8) Å	θ = 1.9–25.5°
c = 11.7974 (9) Å	µ = 0.30 mm−1
α = 88.490 (2)°	T = 273 K
β = 67.006 (2)°	Plate, yellow
γ = 60.764 (2)°	0.49 × 0.13 × 0.05 mm
V = 904.64 (12) Å3

Bruker SMART APEX CCD area-detector diffractometer	3354 independent reflections
Radiation source: fine-focus sealed tube	2667 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scan	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.868, Tmax = 0.985	k = −11→11
10184 measured reflections	l = −14→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.3605P] where P = (Fo2 + 2Fc2)/3
3354 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.39 e Å−3
2 restraints	Δρmin = −0.16 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
S1	0.32354 (9)	0.83415 (8)	0.06044 (6)	0.0508 (2)
S2	0.60463 (8)	0.61184 (7)	0.35113 (6)	0.0445 (2)
N1	0.0246 (3)	0.9353 (3)	0.2519 (2)	0.0436 (5)
N2	0.3465 (2)	0.8013 (2)	0.55742 (18)	0.0379 (5)
C1	0.0589 (3)	0.8023 (3)	0.1830 (2)	0.0385 (6)
C2	−0.0418 (3)	0.7350 (3)	0.2115 (2)	0.0501 (7)
H2B	−0.1497	0.7839	0.2801	0.060*
C3	0.0203 (4)	0.5937 (4)	0.1367 (3)	0.0580 (8)
H3A	−0.0469	0.5479	0.1558	0.070*
C4	0.1790 (4)	0.5200 (4)	0.0346 (3)	0.0558 (7)
H4A	0.2189	0.4245	−0.0138	0.067*
C5	0.2793 (3)	0.5872 (3)	0.0039 (2)	0.0460 (6)
H5A	0.3863	0.5382	−0.0657	0.055*
C6	0.2192 (3)	0.7280 (3)	0.0774 (2)	0.0386 (6)
C7	0.1258 (3)	1.0049 (3)	0.1824 (2)	0.0428 (6)
C8	0.1569 (3)	1.0844 (3)	0.2717 (2)	0.0421 (6)
H8A	0.0463	1.1468	0.3440	0.051*
H8C	0.1845	1.1590	0.2293	0.051*
C9	0.2906 (3)	0.9950 (3)	0.3245 (2)	0.0375 (6)
C10	0.2804 (3)	0.8512 (3)	0.3731 (2)	0.0383 (6)
H10A	0.1617	0.8876	0.4310	0.046*
H10B	0.3125	0.7766	0.3024	0.046*
C11	0.3927 (3)	0.7671 (3)	0.4378 (2)	0.0348 (5)
C12	0.4823 (3)	0.7044 (3)	0.5878 (2)	0.0363 (5)
C13	0.4762 (3)	0.7113 (3)	0.7076 (2)	0.0469 (6)
H13A	0.3756	0.7846	0.7761	0.056*
C14	0.6216 (4)	0.6076 (3)	0.7226 (3)	0.0532 (7)
H14A	0.6184	0.6107	0.8024	0.064*
C15	0.7724 (4)	0.4990 (3)	0.6216 (3)	0.0554 (7)
H15A	0.8689	0.4303	0.6345	0.067*
C16	0.7823 (3)	0.4906 (3)	0.5024 (3)	0.0502 (7)
H16A	0.8843	0.4181	0.4344	0.060*
C17	0.6351 (3)	0.5939 (3)	0.4866 (2)	0.0381 (6)
C18	0.0321 (4)	1.1296 (4)	0.1175 (3)	0.0687 (9)
H18A	−0.0691	1.2194	0.1799	0.103*
H18B	−0.0010	1.0853	0.0691	0.103*
H18C	0.1077	1.1621	0.0628	0.103*
C19	0.2421 (4)	1.1127 (3)	0.4357 (3)	0.0502 (7)
H19A	0.2371	1.2064	0.4081	0.075*
H19B	0.3275	1.0654	0.4676	0.075*
H19C	0.1315	1.1399	0.5009	0.075*
C20	0.4729 (3)	0.9444 (3)	0.2260 (3)	0.0509 (7)
H20A	0.4713	1.0324	0.1890	0.076*
H20B	0.5120	0.8594	0.1617	0.076*
H20C	0.5497	0.9098	0.2656	0.076*
H1N2	−0.074 (4)	0.996 (3)	0.297 (2)	0.041 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0468 (4)	0.0560 (4)	0.0375 (4)	−0.0280 (3)	−0.0046 (3)	−0.0051 (3)
S2	0.0395 (4)	0.0391 (4)	0.0376 (4)	−0.0113 (3)	−0.0126 (3)	−0.0002 (3)
N1	0.0316 (12)	0.0483 (13)	0.0363 (12)	−0.0134 (10)	−0.0105 (10)	−0.0029 (10)
N2	0.0327 (10)	0.0388 (11)	0.0364 (11)	−0.0153 (9)	−0.0139 (9)	0.0063 (9)
C1	0.0348 (13)	0.0469 (14)	0.0313 (12)	−0.0162 (11)	−0.0185 (10)	0.0057 (11)
C2	0.0387 (14)	0.0693 (19)	0.0419 (15)	−0.0270 (14)	−0.0184 (12)	0.0059 (14)
C3	0.0574 (18)	0.074 (2)	0.0569 (18)	−0.0425 (16)	−0.0260 (15)	0.0090 (16)
C4	0.0627 (18)	0.0535 (17)	0.0560 (18)	−0.0304 (15)	−0.0293 (15)	0.0023 (14)
C5	0.0430 (14)	0.0469 (15)	0.0384 (14)	−0.0177 (12)	−0.0156 (12)	0.0000 (12)
C6	0.0358 (13)	0.0453 (14)	0.0308 (12)	−0.0165 (11)	−0.0170 (10)	0.0064 (11)
C7	0.0432 (14)	0.0409 (14)	0.0364 (13)	−0.0159 (12)	−0.0178 (11)	0.0052 (11)
C8	0.0445 (14)	0.0331 (13)	0.0408 (14)	−0.0154 (11)	−0.0174 (12)	0.0044 (11)
C9	0.0398 (13)	0.0372 (13)	0.0390 (13)	−0.0204 (11)	−0.0197 (11)	0.0088 (10)
C10	0.0369 (13)	0.0393 (13)	0.0418 (14)	−0.0210 (11)	−0.0184 (11)	0.0087 (11)
C11	0.0326 (12)	0.0320 (12)	0.0383 (13)	−0.0172 (10)	−0.0133 (10)	0.0072 (10)
C12	0.0349 (12)	0.0353 (13)	0.0413 (13)	−0.0195 (11)	−0.0174 (11)	0.0110 (10)
C13	0.0477 (15)	0.0553 (17)	0.0391 (14)	−0.0284 (13)	−0.0179 (12)	0.0103 (12)
C14	0.0640 (18)	0.0623 (18)	0.0543 (17)	−0.0386 (16)	−0.0378 (15)	0.0260 (15)
C15	0.0553 (17)	0.0438 (16)	0.078 (2)	−0.0231 (14)	−0.0432 (17)	0.0252 (15)
C16	0.0408 (14)	0.0344 (14)	0.0639 (18)	−0.0099 (11)	−0.0245 (13)	0.0071 (12)
C17	0.0394 (13)	0.0317 (12)	0.0418 (14)	−0.0178 (11)	−0.0173 (11)	0.0071 (10)
C18	0.084 (2)	0.062 (2)	0.068 (2)	−0.0288 (17)	−0.0527 (19)	0.0217 (16)
C19	0.0645 (18)	0.0451 (15)	0.0504 (16)	−0.0318 (14)	−0.0289 (14)	0.0102 (12)
C20	0.0461 (15)	0.0541 (17)	0.0544 (17)	−0.0305 (14)	−0.0179 (13)	0.0146 (13)

S1—C6	1.756 (3)	C9—C19	1.535 (3)
S1—C7	1.856 (2)	C9—C10	1.555 (3)
S2—C17	1.728 (3)	C10—C11	1.491 (3)
S2—C11	1.746 (2)	C10—H10A	0.9700
N1—C1	1.384 (3)	C10—H10B	0.9700
N1—C7	1.464 (3)	C12—C13	1.394 (3)
N1—H1N2	0.79 (3)	C12—C17	1.394 (3)
N2—C11	1.299 (3)	C13—C14	1.374 (4)
N2—C12	1.392 (3)	C13—H13A	0.9300
C1—C2	1.384 (4)	C14—C15	1.381 (4)
C1—C6	1.400 (3)	C14—H14A	0.9300
C2—C3	1.385 (4)	C15—C16	1.372 (4)
C2—H2B	0.9300	C15—H15A	0.9300
C3—C4	1.374 (4)	C16—C17	1.391 (4)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.378 (4)	C18—H18A	0.9600
C4—H4A	0.9300	C18—H18B	0.9600
C5—C6	1.380 (3)	C18—H18C	0.9600
C5—H5A	0.9300	C19—H19A	0.9600
C7—C18	1.534 (4)	C19—H19B	0.9600
C7—C8	1.534 (3)	C19—H19C	0.9600
C8—C9	1.542 (3)	C20—H20A	0.9600
C8—H8A	0.9700	C20—H20B	0.9600
C8—H8C	0.9700	C20—H20C	0.9600
C9—C20	1.532 (3)
C6—S1—C7	91.74 (12)	C9—C10—H10A	108.6
C17—S2—C11	89.66 (11)	C11—C10—H10B	108.6
C1—N1—C7	114.6 (2)	C9—C10—H10B	108.6
C1—N1—H1N2	115.9 (19)	H10A—C10—H10B	107.6
C7—N1—H1N2	115.8 (19)	N2—C11—C10	125.0 (2)
C11—N2—C12	111.0 (2)	N2—C11—S2	115.04 (18)
C2—C1—N1	127.2 (2)	C10—C11—S2	119.97 (18)
C2—C1—C6	119.2 (2)	N2—C12—C13	125.6 (2)
N1—C1—C6	113.5 (2)	N2—C12—C17	115.1 (2)
C1—C2—C3	119.2 (2)	C13—C12—C17	119.4 (2)
C1—C2—H2B	120.4	C14—C13—C12	118.8 (3)
C3—C2—H2B	120.4	C14—C13—H13A	120.6
C4—C3—C2	121.3 (3)	C12—C13—H13A	120.6
C4—C3—H3A	119.4	C13—C14—C15	121.3 (3)
C2—C3—H3A	119.4	C13—C14—H14A	119.3
C3—C4—C5	120.2 (3)	C15—C14—H14A	119.3
C3—C4—H4A	119.9	C16—C15—C14	121.1 (3)
C5—C4—H4A	119.9	C16—C15—H15A	119.4
C4—C5—C6	119.2 (2)	C14—C15—H15A	119.4
C4—C5—H5A	120.4	C15—C16—C17	117.9 (3)
C6—C5—H5A	120.4	C15—C16—H16A	121.0
C5—C6—C1	120.9 (2)	C17—C16—H16A	121.0
C5—C6—S1	128.0 (2)	C16—C17—C12	121.5 (2)
C1—C6—S1	111.07 (18)	C16—C17—S2	129.3 (2)
N1—C7—C18	111.0 (2)	C12—C17—S2	109.22 (18)
N1—C7—C8	110.4 (2)	C7—C18—H18A	109.5
C18—C7—C8	108.3 (2)	C7—C18—H18B	109.5
N1—C7—S1	103.03 (17)	H18A—C18—H18B	109.5
C18—C7—S1	108.93 (19)	C7—C18—H18C	109.5
C8—C7—S1	115.00 (18)	H18A—C18—H18C	109.5
C7—C8—C9	124.5 (2)	H18B—C18—H18C	109.5
C7—C8—H8A	106.2	C9—C19—H19A	109.5
C9—C8—H8A	106.2	C9—C19—H19B	109.5
C7—C8—H8C	106.2	H19A—C19—H19B	109.5
C9—C8—H8C	106.2	C9—C19—H19C	109.5
H8A—C8—H8C	106.4	H19A—C19—H19C	109.5
C20—C9—C19	108.4 (2)	H19B—C19—H19C	109.5
C20—C9—C8	110.9 (2)	C9—C20—H20A	109.5
C19—C9—C8	106.2 (2)	C9—C20—H20B	109.5
C20—C9—C10	111.5 (2)	H20A—C20—H20B	109.5
C19—C9—C10	109.0 (2)	C9—C20—H20C	109.5
C8—C9—C10	110.70 (19)	H20A—C20—H20C	109.5
C11—C10—C9	114.51 (19)	H20B—C20—H20C	109.5
C11—C10—H10A	108.6
C7—N1—C1—C2	−163.1 (2)	C7—C8—C9—C10	−46.0 (3)
C7—N1—C1—C6	20.5 (3)	C20—C9—C10—C11	61.9 (3)
N1—C1—C2—C3	−174.7 (2)	C19—C9—C10—C11	−57.7 (3)
C6—C1—C2—C3	1.5 (4)	C8—C9—C10—C11	−174.1 (2)
C1—C2—C3—C4	−0.3 (4)	C12—N2—C11—C10	−178.0 (2)
C2—C3—C4—C5	−0.8 (4)	C12—N2—C11—S2	0.9 (3)
C3—C4—C5—C6	0.7 (4)	C9—C10—C11—N2	89.5 (3)
C4—C5—C6—C1	0.5 (4)	C9—C10—C11—S2	−89.4 (2)
C4—C5—C6—S1	178.4 (2)	C17—S2—C11—N2	−1.15 (19)
C2—C1—C6—C5	−1.6 (4)	C17—S2—C11—C10	177.85 (19)
N1—C1—C6—C5	175.1 (2)	C11—N2—C12—C13	179.4 (2)
C2—C1—C6—S1	−179.83 (19)	C11—N2—C12—C17	−0.1 (3)
N1—C1—C6—S1	−3.1 (3)	N2—C12—C13—C14	−179.8 (2)
C7—S1—C6—C5	171.4 (2)	C17—C12—C13—C14	−0.4 (4)
C7—S1—C6—C1	−10.53 (19)	C12—C13—C14—C15	0.6 (4)
C1—N1—C7—C18	90.3 (3)	C13—C14—C15—C16	0.0 (4)
C1—N1—C7—C8	−149.5 (2)	C14—C15—C16—C17	−0.7 (4)
C1—N1—C7—S1	−26.2 (2)	C15—C16—C17—C12	0.9 (4)
C6—S1—C7—N1	19.83 (17)	C15—C16—C17—S2	−179.3 (2)
C6—S1—C7—C18	−98.1 (2)	N2—C12—C17—C16	179.1 (2)
C6—S1—C7—C8	140.07 (19)	C13—C12—C17—C16	−0.4 (4)
N1—C7—C8—C9	77.0 (3)	N2—C12—C17—S2	−0.8 (3)
C18—C7—C8—C9	−161.2 (2)	C13—C12—C17—S2	179.76 (19)
S1—C7—C8—C9	−39.1 (3)	C11—S2—C17—C16	−178.8 (3)
C7—C8—C9—C20	78.3 (3)	C11—S2—C17—C12	1.02 (18)
C7—C8—C9—C19	−164.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N2···N2i	0.79 (3)	2.35 (3)	3.130 (3)	170 (4)
C10—H10B···S1	0.97	2.87	3.543 (2)	128
C20—H20B···S1	0.96	2.67	3.331 (4)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N2⋯N2i	0.79 (3)	2.35 (3)	3.130 (3)	170 (4)
C10—H10B⋯S1	0.97	2.87	3.543 (2)	128
C20—H20B⋯S1	0.96	2.67	3.331 (4)	126

Symmetry code: (i) .