1-(1,3-Benzothia-zol-2-yl)-3-benzoyl-thio-urea.

The title compound, C(15)H(11)N(3)OS(2), was synthesized from benzoyl thio-cyanate and 2-amino-benzothia-zole in dry acetone. The thio-urea group is in the thio-amide form. The mol-ecules are stabilized by two inter-molecular C-H⋯S and C-H⋯O hydrogen bonds. Intra-molecular N-H⋯O hydrogen bonding results in a pseudo-S(6) planar ring with dihedral angles of 11.23 and 11.91° with the benzothiazole ring system and the phenyl ring, respectively.

Related literature

For related literature see: Büyükgüngör et al. (2004 ▶); del Campo et al. (2002 ▶); Chen et al. (2003 ▶); D’hooghe et al. (2005 ▶); Koketsu & Ishihara (2006 ▶); Morales et al. (2000 ▶); Rodríguez-Fernández et al. (2005 ▶); Yamin & Hassan (2004 ▶); Yunus et al. (2007 ▶); Zeng et al. (2003 ▶).

Experimental

Crystal data

C15H11N3OS2

M = 313.39

Monoclinic,

a = 12.4402 (8) Å

b = 5.8608 (4) Å

c = 19.7240 (13) Å

β = 90.223 (1)°

V = 1438.06 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 293 (2) K

0.32 × 0.26 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.933, T max = 1.000 (expected range = 0.866–0.928)

8487 measured reflections

3508 independent reflections

2724 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.102

S = 1.04

3508 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706134X/bh2150sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706134X/bh2150Isup2.hkl

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

C15H11N3OS2	F000 = 648
Mr = 313.39	Dx = 1.447 Mg m−3
Monoclinic, P2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 8487 reflections
a = 12.4402 (8) Å	θ = 2.6–28.3º
b = 5.8608 (4) Å	µ = 0.37 mm−1
c = 19.7240 (13) Å	T = 293 (2) K
β = 90.223 (1)º	Block, pale-yellow
V = 1438.06 (16) Å3	0.32 × 0.26 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	3508 independent reflections
Radiation source: fine-focus sealed tube	2724 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 293(2) K	θmax = 28.3º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −16→16
Tmin = 0.933, Tmax = 1.000	k = −7→7
8487 measured reflections	l = −19→26

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.2538P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3508 reflections	Δρmax = 0.31 e Å−3
190 parameters	Δρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
C1	0.21573 (13)	0.0594 (3)	0.53895 (8)	0.0416 (4)
H1A	0.1480	0.0792	0.5197	0.050*
C2	0.23408 (16)	−0.1206 (3)	0.58247 (9)	0.0515 (4)
H2A	0.1785	−0.2203	0.5932	0.062*
C3	0.33485 (18)	−0.1525 (4)	0.61000 (10)	0.0602 (5)
H3A	0.3473	−0.2749	0.6390	0.072*
C4	0.41698 (17)	−0.0051 (4)	0.59497 (11)	0.0646 (5)
H4A	0.4848	−0.0280	0.6137	0.078*
C5	0.39901 (14)	0.1779 (3)	0.55189 (9)	0.0529 (5)
H5A	0.4547	0.2781	0.5419	0.063*
C6	0.29787 (12)	0.2116 (3)	0.52370 (8)	0.0378 (3)
C7	0.28504 (12)	0.4117 (3)	0.47818 (8)	0.0380 (3)
C8	0.14589 (12)	0.6519 (3)	0.42051 (8)	0.0372 (3)
C9	0.22056 (12)	0.9776 (3)	0.35659 (7)	0.0354 (3)
C10	0.29090 (13)	1.2734 (3)	0.30503 (8)	0.0388 (3)
C11	0.36820 (14)	1.4337 (3)	0.28664 (9)	0.0472 (4)
H11A	0.4382	1.4225	0.3030	0.057*
C12	0.33920 (16)	1.6082 (3)	0.24397 (9)	0.0517 (4)
H12A	0.3902	1.7159	0.2313	0.062*
C13	0.23408 (17)	1.6266 (3)	0.21919 (9)	0.0551 (5)
H13A	0.2164	1.7450	0.1898	0.066*
C14	0.15669 (15)	1.4723 (3)	0.23769 (9)	0.0514 (4)
H14A	0.0867	1.4855	0.2214	0.062*
C15	0.18525 (13)	1.2952 (3)	0.28139 (8)	0.0412 (4)
N1	0.18011 (10)	0.4716 (2)	0.46078 (7)	0.0395 (3)
H1B	0.1303	0.3861	0.4770	0.047*
N2	0.22510 (10)	0.7819 (2)	0.39602 (7)	0.0385 (3)
H2B	0.2889	0.7372	0.4064	0.046*
N3	0.30872 (10)	1.0881 (2)	0.34739 (7)	0.0397 (3)
O1	0.36174 (9)	0.5195 (2)	0.45724 (6)	0.0482 (3)
S1	0.10503 (3)	1.08096 (8)	0.31634 (2)	0.04440 (13)
S2	0.01565 (3)	0.69188 (9)	0.40697 (2)	0.05128 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0415 (8)	0.0417 (9)	0.0415 (8)	0.0026 (7)	0.0017 (7)	−0.0018 (7)
C2	0.0636 (11)	0.0424 (10)	0.0486 (10)	−0.0033 (8)	0.0075 (8)	0.0042 (8)
C3	0.0734 (13)	0.0535 (11)	0.0536 (11)	0.0096 (10)	−0.0028 (10)	0.0161 (9)
C4	0.0549 (11)	0.0708 (13)	0.0680 (13)	0.0098 (10)	−0.0134 (9)	0.0184 (11)
C5	0.0423 (9)	0.0610 (12)	0.0553 (11)	0.0008 (8)	−0.0066 (8)	0.0146 (9)
C6	0.0389 (8)	0.0385 (8)	0.0362 (8)	0.0038 (6)	0.0000 (6)	0.0004 (6)
C7	0.0358 (7)	0.0394 (8)	0.0388 (8)	0.0009 (6)	−0.0025 (6)	0.0003 (7)
C8	0.0360 (8)	0.0391 (8)	0.0366 (8)	0.0027 (6)	−0.0012 (6)	−0.0027 (6)
C9	0.0359 (7)	0.0363 (8)	0.0339 (7)	0.0054 (6)	−0.0023 (6)	−0.0005 (6)
C10	0.0422 (8)	0.0398 (8)	0.0343 (8)	0.0048 (7)	0.0034 (6)	0.0000 (6)
C11	0.0471 (9)	0.0494 (10)	0.0451 (9)	−0.0003 (8)	0.0056 (7)	0.0020 (8)
C12	0.0631 (11)	0.0460 (10)	0.0460 (10)	−0.0016 (8)	0.0126 (8)	0.0040 (8)
C13	0.0740 (13)	0.0474 (10)	0.0441 (10)	0.0154 (9)	0.0092 (9)	0.0106 (8)
C14	0.0511 (10)	0.0554 (11)	0.0476 (10)	0.0141 (8)	0.0005 (8)	0.0088 (8)
C15	0.0442 (9)	0.0414 (9)	0.0381 (8)	0.0061 (7)	0.0022 (7)	0.0018 (7)
N1	0.0324 (6)	0.0398 (7)	0.0461 (7)	−0.0007 (5)	−0.0018 (5)	0.0073 (6)
N2	0.0323 (6)	0.0392 (7)	0.0441 (7)	0.0031 (5)	−0.0024 (5)	0.0046 (6)
N3	0.0380 (7)	0.0413 (7)	0.0399 (7)	0.0021 (6)	−0.0018 (5)	0.0030 (6)
O1	0.0351 (6)	0.0515 (7)	0.0581 (7)	−0.0035 (5)	−0.0043 (5)	0.0143 (6)
S1	0.0367 (2)	0.0473 (3)	0.0491 (2)	0.00442 (17)	−0.00595 (17)	0.00779 (18)
S2	0.0328 (2)	0.0624 (3)	0.0586 (3)	0.00376 (19)	−0.00173 (18)	0.0142 (2)

C1—C2	1.379 (2)	C9—N3	1.287 (2)
C1—C6	1.390 (2)	C9—N2	1.387 (2)
C1—H1A	0.9300	C9—S1	1.7476 (15)
C2—C3	1.377 (3)	C10—N3	1.387 (2)
C2—H2A	0.9300	C10—C11	1.393 (2)
C3—C4	1.371 (3)	C10—C15	1.399 (2)
C3—H3A	0.9300	C11—C12	1.372 (2)
C4—C5	1.386 (3)	C11—H11A	0.9300
C4—H4A	0.9300	C12—C13	1.398 (3)
C5—C6	1.388 (2)	C12—H12A	0.9300
C5—H5A	0.9300	C13—C14	1.371 (3)
C6—C7	1.486 (2)	C13—H13A	0.9300
C7—O1	1.2179 (19)	C14—C15	1.395 (2)
C7—N1	1.3933 (19)	C14—H14A	0.9300
C8—N2	1.338 (2)	C15—S1	1.7471 (17)
C8—N1	1.388 (2)	N1—H1B	0.8600
C8—S2	1.6578 (15)	N2—H2B	0.8600
C2—C1—C6	120.37 (16)	N3—C10—C11	125.14 (15)
C2—C1—H1A	119.8	N3—C10—C15	114.84 (14)
C6—C1—H1A	119.8	C11—C10—C15	120.01 (15)
C3—C2—C1	119.85 (18)	C12—C11—C10	118.83 (17)
C3—C2—H2A	120.1	C12—C11—H11A	120.6
C1—C2—H2A	120.1	C10—C11—H11A	120.6
C4—C3—C2	120.47 (18)	C11—C12—C13	121.01 (18)
C4—C3—H3A	119.8	C11—C12—H12A	119.5
C2—C3—H3A	119.8	C13—C12—H12A	119.5
C3—C4—C5	120.11 (18)	C14—C13—C12	120.85 (17)
C3—C4—H4A	119.9	C14—C13—H13A	119.6
C5—C4—H4A	119.9	C12—C13—H13A	119.6
C4—C5—C6	119.95 (18)	C13—C14—C15	118.55 (17)
C4—C5—H5A	120.0	C13—C14—H14A	120.7
C6—C5—H5A	120.0	C15—C14—H14A	120.7
C5—C6—C1	119.24 (15)	C14—C15—C10	120.72 (16)
C5—C6—C7	116.71 (15)	C14—C15—S1	129.37 (14)
C1—C6—C7	124.06 (14)	C10—C15—S1	109.89 (12)
O1—C7—N1	121.35 (14)	C8—N1—C7	128.15 (13)
O1—C7—C6	122.16 (14)	C8—N1—H1B	115.9
N1—C7—C6	116.49 (14)	C7—N1—H1B	115.9
N2—C8—N1	114.57 (13)	C8—N2—C9	130.20 (13)
N2—C8—S2	125.60 (12)	C8—N2—H2B	114.9
N1—C8—S2	119.83 (12)	C9—N2—H2B	114.9
N3—C9—N2	117.53 (13)	C9—N3—C10	110.14 (13)
N3—C9—S1	117.47 (12)	C15—S1—C9	87.62 (7)
N2—C9—S1	124.97 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1	0.86	1.86	2.5878 (17)	142
C1—H1A···S2i	0.93	2.84	3.4017 (17)	120
C5—H5A···O1ii	0.93	2.57	3.470 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1	0.86	1.86	2.5878 (17)	142
C1—H1A⋯S2i	0.93	2.84	3.4017 (17)	120
C5—H5A⋯O1ii	0.93	2.57	3.470 (2)	162

Symmetry codes: (i) ; (ii) .