4-(1,3-Benzothia-zol-2-yl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one.

The central five-membered ring of the title compound, C(18)H(15)N(3)OS, is almost planar (r.m.s. deviation = 0.028 Å) and the benzothia-zole fused-ring system is close to coplanar with this ring [dihedral angle = 6.1 (1)°]. The phenyl substituent is twisted by 62.5 (1)°.

Related literature

For the structure of the reactant 4-(2,3-dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, see: Chakibe et al. (2010 ▶).

Experimental

Crystal data

C18H15N3OS

M = 321.39

Monoclinic,

a = 8.7428 (2) Å

b = 25.7551 (5) Å

c = 6.9660 (1) Å

β = 97.460 (1)°

V = 1555.27 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.50 × 0.10 × 0.10 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.900, T max = 0.979

18953 measured reflections

3569 independent reflections

2418 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.131

S = 1.01

3569 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037652/jh2331sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037652/jh2331Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037652/jh2331Isup3.cml

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

C18H15N3OS	F(000) = 672
Mr = 321.39	Dx = 1.373 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3894 reflections
a = 8.7428 (2) Å	θ = 2.5–24.6°
b = 25.7551 (5) Å	µ = 0.22 mm−1
c = 6.9660 (1) Å	T = 293 K
β = 97.460 (1)°	Prism, colorless
V = 1555.27 (5) Å3	0.50 × 0.10 × 0.10 mm
Z = 4

Bruker APEXII diffractometer	3569 independent reflections
Radiation source: fine-focus sealed tube	2418 reflections with I > 2σ(I)
graphite	Rint = 0.053
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.900, Tmax = 0.979	k = −29→33
18953 measured reflections	l = −9→9

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.296P] where P = (Fo2 + 2Fc2)/3
3569 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.92125 (7)	0.46686 (2)	0.19736 (8)	0.04602 (18)
N1	0.8107 (2)	0.43170 (7)	0.5013 (3)	0.0485 (5)
N2	0.6696 (2)	0.60559 (6)	0.3813 (2)	0.0450 (4)
N3	0.6087 (2)	0.58549 (6)	0.5419 (2)	0.0436 (4)
O1	0.80712 (19)	0.57089 (6)	0.1499 (2)	0.0555 (4)
C1	0.9552 (2)	0.40265 (8)	0.2603 (3)	0.0435 (5)
C2	1.0365 (3)	0.36554 (8)	0.1694 (3)	0.0531 (6)
H2	1.0832	0.3740	0.0609	0.064*
C3	1.0459 (3)	0.31630 (9)	0.2442 (4)	0.0611 (7)
H3	1.1003	0.2910	0.1862	0.073*
C4	0.9756 (3)	0.30371 (9)	0.4045 (4)	0.0682 (7)
H4	0.9818	0.2698	0.4510	0.082*
C5	0.8967 (3)	0.34025 (9)	0.4969 (4)	0.0657 (7)
H5	0.8506	0.3313	0.6053	0.079*
C6	0.8869 (2)	0.39090 (8)	0.4253 (3)	0.0462 (5)
C7	0.8201 (2)	0.47347 (7)	0.3978 (3)	0.0399 (5)
C8	0.7531 (2)	0.56620 (8)	0.3030 (3)	0.0417 (5)
C9	0.7516 (2)	0.52318 (7)	0.4329 (3)	0.0387 (5)
C10	0.6676 (2)	0.53751 (7)	0.5781 (3)	0.0398 (5)
C11	0.6421 (3)	0.50940 (9)	0.7570 (3)	0.0514 (6)
H11A	0.5334	0.5064	0.7630	0.077*
H11B	0.6897	0.5282	0.8679	0.077*
H11C	0.6868	0.4754	0.7559	0.077*
C12	0.5534 (3)	0.62109 (9)	0.6788 (3)	0.0527 (6)
H12A	0.5437	0.6031	0.7972	0.079*
H12B	0.4546	0.6346	0.6253	0.079*
H12C	0.6252	0.6492	0.7045	0.079*
C13	0.5892 (3)	0.64466 (7)	0.2625 (3)	0.0414 (5)
C14	0.4314 (3)	0.64253 (9)	0.2115 (3)	0.0532 (6)
H14	0.3732	0.6167	0.2606	0.064*
C15	0.3615 (3)	0.67960 (10)	0.0859 (4)	0.0657 (7)
H15	0.2553	0.6787	0.0497	0.079*
C16	0.4484 (4)	0.71801 (10)	0.0139 (4)	0.0673 (8)
H16	0.4007	0.7428	−0.0705	0.081*
C17	0.6046 (4)	0.71958 (9)	0.0666 (4)	0.0627 (7)
H17	0.6629	0.7454	0.0175	0.075*
C18	0.6759 (3)	0.68310 (8)	0.1916 (3)	0.0508 (5)
H18	0.7820	0.6844	0.2281	0.061*

	U11	U22	U33	U12	U13	U23
S1	0.0543 (3)	0.0407 (3)	0.0427 (3)	0.0044 (2)	0.0050 (2)	0.0038 (2)
N1	0.0525 (11)	0.0414 (10)	0.0524 (11)	0.0046 (8)	0.0100 (9)	0.0068 (8)
N2	0.0576 (11)	0.0379 (9)	0.0397 (9)	0.0063 (8)	0.0079 (8)	0.0048 (7)
N3	0.0568 (11)	0.0403 (10)	0.0334 (9)	0.0041 (8)	0.0047 (8)	−0.0002 (7)
O1	0.0732 (11)	0.0503 (9)	0.0456 (9)	0.0109 (8)	0.0180 (8)	0.0067 (7)
C1	0.0397 (11)	0.0404 (11)	0.0480 (12)	−0.0006 (9)	−0.0033 (9)	0.0008 (9)
C2	0.0500 (13)	0.0493 (13)	0.0590 (14)	0.0057 (11)	0.0036 (11)	−0.0051 (11)
C3	0.0572 (15)	0.0471 (14)	0.0778 (17)	0.0078 (11)	0.0044 (13)	−0.0065 (12)
C4	0.0668 (17)	0.0390 (13)	0.099 (2)	0.0085 (12)	0.0103 (15)	0.0110 (13)
C5	0.0698 (16)	0.0469 (14)	0.0841 (18)	0.0074 (12)	0.0240 (14)	0.0183 (13)
C6	0.0429 (12)	0.0386 (11)	0.0560 (13)	0.0005 (9)	0.0026 (10)	0.0061 (9)
C7	0.0398 (11)	0.0391 (11)	0.0383 (10)	−0.0017 (9)	−0.0043 (8)	0.0018 (8)
C8	0.0485 (12)	0.0376 (11)	0.0381 (11)	0.0028 (9)	0.0016 (9)	−0.0011 (8)
C9	0.0424 (11)	0.0360 (10)	0.0353 (10)	0.0003 (9)	−0.0036 (8)	−0.0004 (8)
C10	0.0433 (11)	0.0389 (11)	0.0342 (10)	−0.0014 (9)	−0.0067 (8)	−0.0005 (8)
C11	0.0613 (14)	0.0524 (13)	0.0392 (11)	0.0003 (11)	0.0020 (10)	0.0049 (10)
C12	0.0629 (15)	0.0518 (13)	0.0438 (12)	0.0052 (11)	0.0077 (11)	−0.0078 (10)
C13	0.0561 (13)	0.0316 (10)	0.0365 (10)	0.0055 (9)	0.0052 (9)	−0.0033 (8)
C14	0.0567 (14)	0.0439 (12)	0.0582 (14)	0.0007 (11)	0.0043 (11)	0.0035 (10)
C15	0.0643 (16)	0.0681 (17)	0.0617 (16)	0.0190 (13)	−0.0025 (13)	0.0022 (13)
C16	0.098 (2)	0.0560 (15)	0.0487 (14)	0.0268 (15)	0.0123 (14)	0.0137 (11)
C17	0.094 (2)	0.0384 (13)	0.0596 (15)	0.0055 (13)	0.0241 (14)	0.0075 (11)
C18	0.0626 (14)	0.0399 (12)	0.0506 (13)	−0.0025 (11)	0.0100 (11)	−0.0024 (10)

S1—C1	1.727 (2)	C8—C9	1.432 (3)
S1—C7	1.755 (2)	C9—C10	1.376 (3)
N1—C7	1.304 (2)	C10—C11	1.483 (3)
N1—C6	1.386 (3)	C11—H11A	0.9600
N2—C8	1.401 (3)	C11—H11B	0.9600
N2—N3	1.399 (2)	C11—H11C	0.9600
N2—C13	1.428 (2)	C12—H12A	0.9600
N3—C10	1.350 (2)	C12—H12B	0.9600
N3—C12	1.451 (3)	C12—H12C	0.9600
O1—C8	1.227 (2)	C13—C18	1.377 (3)
C1—C2	1.392 (3)	C13—C14	1.381 (3)
C1—C6	1.395 (3)	C14—C15	1.382 (3)
C2—C3	1.369 (3)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.381 (4)
C3—C4	1.382 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.368 (4)
C4—C5	1.375 (4)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.374 (3)
C5—C6	1.395 (3)	C17—H17	0.9300
C5—H5	0.9300	C18—H18	0.9300
C7—C9	1.448 (3)
C1—S1—C7	88.78 (10)	C8—C9—C7	122.65 (19)
C7—N1—C6	110.27 (18)	N3—C10—C9	109.58 (17)
C8—N2—N3	108.35 (15)	N3—C10—C11	120.60 (19)
C8—N2—C13	121.79 (16)	C9—C10—C11	129.77 (19)
N3—N2—C13	120.94 (17)	C10—C11—H11A	109.5
C10—N3—N2	108.24 (16)	C10—C11—H11B	109.5
C10—N3—C12	127.40 (17)	H11A—C11—H11B	109.5
N2—N3—C12	119.07 (16)	C10—C11—H11C	109.5
C2—C1—C6	121.6 (2)	H11A—C11—H11C	109.5
C2—C1—S1	128.56 (18)	H11B—C11—H11C	109.5
C6—C1—S1	109.83 (16)	N3—C12—H12A	109.5
C3—C2—C1	118.1 (2)	N3—C12—H12B	109.5
C3—C2—H2	120.9	H12A—C12—H12B	109.5
C1—C2—H2	120.9	N3—C12—H12C	109.5
C2—C3—C4	120.9 (2)	H12A—C12—H12C	109.5
C2—C3—H3	119.5	H12B—C12—H12C	109.5
C4—C3—H3	119.5	C18—C13—C14	121.0 (2)
C5—C4—C3	121.4 (2)	C18—C13—N2	117.5 (2)
C5—C4—H4	119.3	C14—C13—N2	121.43 (19)
C3—C4—H4	119.3	C15—C14—C13	118.7 (2)
C4—C5—C6	119.0 (2)	C15—C14—H14	120.7
C4—C5—H5	120.5	C13—C14—H14	120.7
C6—C5—H5	120.5	C14—C15—C16	120.4 (3)
N1—C6—C5	125.6 (2)	C14—C15—H15	119.8
N1—C6—C1	115.37 (18)	C16—C15—H15	119.8
C5—C6—C1	119.0 (2)	C17—C16—C15	120.1 (2)
N1—C7—C9	125.38 (19)	C17—C16—H16	120.0
N1—C7—S1	115.75 (15)	C15—C16—H16	120.0
C9—C7—S1	118.85 (15)	C16—C17—C18	120.3 (2)
O1—C8—N2	123.08 (18)	C16—C17—H17	119.9
O1—C8—C9	131.43 (19)	C18—C17—H17	119.9
N2—C8—C9	105.45 (17)	C17—C18—C13	119.6 (2)
C10—C9—C8	107.86 (17)	C17—C18—H18	120.2
C10—C9—C7	129.34 (18)	C13—C18—H18	120.2
C8—N2—N3—C10	7.4 (2)	N2—C8—C9—C10	1.0 (2)
C13—N2—N3—C10	155.18 (17)	O1—C8—C9—C7	−0.5 (4)
C8—N2—N3—C12	163.59 (18)	N2—C8—C9—C7	176.98 (18)
C13—N2—N3—C12	−48.6 (3)	N1—C7—C9—C10	1.4 (3)
C7—S1—C1—C2	−179.4 (2)	S1—C7—C9—C10	179.71 (16)
C7—S1—C1—C6	0.61 (15)	N1—C7—C9—C8	−173.65 (19)
C6—C1—C2—C3	1.2 (3)	S1—C7—C9—C8	4.7 (3)
S1—C1—C2—C3	−178.77 (17)	N2—N3—C10—C9	−6.8 (2)
C1—C2—C3—C4	0.4 (4)	C12—N3—C10—C9	−160.4 (2)
C2—C3—C4—C5	−1.3 (4)	N2—N3—C10—C11	171.05 (18)
C3—C4—C5—C6	0.5 (4)	C12—N3—C10—C11	17.4 (3)
C7—N1—C6—C5	−178.3 (2)	C8—C9—C10—N3	3.6 (2)
C7—N1—C6—C1	0.0 (3)	C7—C9—C10—N3	−172.02 (19)
C4—C5—C6—N1	179.4 (2)	C8—C9—C10—C11	−174.0 (2)
C4—C5—C6—C1	1.1 (4)	C7—C9—C10—C11	10.4 (4)
C2—C1—C6—N1	179.51 (19)	C8—N2—C13—C18	−74.5 (2)
S1—C1—C6—N1	−0.5 (2)	N3—N2—C13—C18	142.02 (19)
C2—C1—C6—C5	−2.0 (3)	C8—N2—C13—C14	101.9 (2)
S1—C1—C6—C5	177.98 (18)	N3—N2—C13—C14	−41.5 (3)
C6—N1—C7—C9	178.88 (19)	C18—C13—C14—C15	0.5 (3)
C6—N1—C7—S1	0.5 (2)	N2—C13—C14—C15	−175.8 (2)
C1—S1—C7—N1	−0.67 (16)	C13—C14—C15—C16	−0.2 (4)
C1—S1—C7—C9	−179.16 (17)	C14—C15—C16—C17	0.0 (4)
N3—N2—C8—O1	172.67 (19)	C15—C16—C17—C18	−0.2 (4)
C13—N2—C8—O1	25.2 (3)	C16—C17—C18—C13	0.5 (3)
N3—N2—C8—C9	−5.1 (2)	C14—C13—C18—C17	−0.7 (3)
C13—N2—C8—C9	−152.51 (18)	N2—C13—C18—C17	175.78 (19)
O1—C8—C9—C10	−176.5 (2)