1-Allyl-4-(1,3-benzothia-zol-2-yl)-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one.

The title compound, C(20)H(17)N(3)OS, is a 1H-pyrazol-3(2H)-one having aromatic 4-(1,3-benzothia-zol-2-yl)- and 2-phenyl substituents. The five-membered ring and fused ring system are planar, the r.m.s. deviations being 0.021 and 0.005 Å, respectively. The five-membered ring is aligned at 7.9 (2)° with respect to the fused-ring system. The allyl and phenyl parts of the mol-ecule are both disordered over two positions in a 1:1 ratio. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the structure of a related compound (E)-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

C20H17N3OS

M = 347.43

Orthorhombic,

a = 17.8734 (5) Å

b = 10.4297 (2) Å

c = 18.9578 (4) Å

V = 3534.00 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.30 × 0.30 × 0.25 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.944, T max = 0.953

18349 measured reflections

3678 independent reflections

2341 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.172

S = 1.00

3678 reflections

227 parameters

17 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536810040316/xu5047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040316/xu5047Isup2.hkl

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

C20H17N3OS	F(000) = 1456
Mr = 347.43	Dx = 1.306 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3745 reflections
a = 17.8734 (5) Å	θ = 2.3–22.5°
b = 10.4297 (2) Å	µ = 0.20 mm−1
c = 18.9578 (4) Å	T = 293 K
V = 3534.00 (14) Å3	Prism, colorless
Z = 8	0.30 × 0.30 × 0.25 mm

Bruker X8 APEXII diffractometer	3678 independent reflections
Radiation source: fine-focus sealed tube	2341 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 26.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→21
Tmin = 0.944, Tmax = 0.953	k = −13→12
18349 measured reflections	l = −23→23

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.096P)2 + 0.8646P] where P = (Fo2 + 2Fc2)/3
3678 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.32 e Å−3
17 restraints	Δρmin = −0.25 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.54022 (4)	0.59623 (7)	0.57529 (3)	0.0590 (2)
O1	0.63189 (12)	0.5096 (2)	0.45761 (10)	0.0808 (6)
N1	0.61613 (12)	0.7853 (2)	0.62953 (11)	0.0590 (6)
N2	0.79529 (13)	0.6762 (2)	0.48741 (11)	0.0593 (6)
N3	0.75432 (13)	0.5809 (2)	0.45335 (11)	0.0627 (6)
C1	0.50073 (15)	0.6812 (2)	0.64448 (12)	0.0531 (6)
C2	0.43115 (17)	0.6640 (3)	0.67650 (14)	0.0669 (7)
H2	0.3989	0.5995	0.6617	0.080*
C3	0.41164 (19)	0.7448 (3)	0.73035 (15)	0.0762 (9)
H3	0.3654	0.7349	0.7522	0.091*
C4	0.4595 (2)	0.8412 (3)	0.75287 (16)	0.0798 (9)
H4	0.4454	0.8943	0.7900	0.096*
C5	0.52717 (19)	0.8589 (3)	0.72110 (15)	0.0743 (8)
H5	0.5587	0.9242	0.7362	0.089*
C6	0.54904 (16)	0.7785 (2)	0.66569 (12)	0.0566 (6)
C7	0.61898 (14)	0.6956 (2)	0.58142 (11)	0.0495 (6)
C8	0.68208 (17)	0.5800 (3)	0.48056 (13)	0.0603 (7)
C9	0.68293 (15)	0.6721 (2)	0.53608 (12)	0.0518 (6)
C10	0.75276 (15)	0.7255 (2)	0.53898 (12)	0.0548 (6)
C11	0.78327 (19)	0.8222 (3)	0.58934 (16)	0.0760 (8)
H11A	0.8269	0.8617	0.5693	0.114*
H11B	0.7965	0.7806	0.6327	0.114*
H11C	0.7461	0.8865	0.5984	0.114*
C12	0.87637 (17)	0.6862 (3)	0.48056 (16)	0.0746 (8)
H12A	0.8914	0.7755	0.4806	0.090*	0.50
H12B	0.8926	0.6475	0.4366	0.090*	0.50
H12C	0.8825	0.7782	0.4852	0.090*	0.50
H12D	0.8812	0.6708	0.4303	0.090*	0.50
C13	0.9121 (11)	0.6151 (15)	0.5440 (7)	0.101 (3)	0.50
H13	0.8915	0.5398	0.5616	0.121*	0.50
C14	0.9722 (11)	0.6652 (18)	0.5718 (9)	0.139 (4)	0.50
H14A	0.9920	0.7407	0.5535	0.166*	0.50
H14B	0.9953	0.6254	0.6099	0.166*	0.50
C13'	0.9175 (11)	0.5938 (15)	0.5294 (7)	0.101 (3)	0.50
H13'	0.9148	0.5076	0.5171	0.121*	0.50
C14'	0.9555 (11)	0.6196 (18)	0.5854 (8)	0.139 (4)	0.50
H14C	0.9603	0.7041	0.6004	0.166*	0.50
H14D	0.9781	0.5538	0.6107	0.166*	0.50
C15	0.7691 (10)	0.5140 (10)	0.3885 (4)	0.0510 (18)	0.50
C16	0.8277 (10)	0.4304 (14)	0.3741 (5)	0.0863 (18)	0.50
H16	0.8561	0.3969	0.4108	0.104*	0.50
C17	0.8437 (10)	0.3967 (13)	0.3048 (5)	0.105 (3)	0.50
H17	0.8829	0.3407	0.2951	0.126*	0.50
C18	0.8012 (11)	0.4466 (10)	0.2499 (4)	0.110 (4)	0.50
H18	0.8119	0.4241	0.2035	0.132*	0.50
C19	0.7426 (10)	0.5303 (12)	0.2643 (6)	0.102 (3)	0.50
H19	0.7142	0.5637	0.2275	0.123*	0.50
C20	0.7265 (9)	0.5640 (12)	0.3336 (7)	0.0714 (19)	0.50
H20	0.6874	0.6199	0.3432	0.086*	0.50
C15'	0.7791 (10)	0.5424 (10)	0.3848 (5)	0.0510 (18)	0.50
C16'	0.8326 (10)	0.4458 (14)	0.3884 (4)	0.0863 (18)	0.50
H16'	0.8571	0.4294	0.4308	0.104*	0.50
C17'	0.8494 (11)	0.3738 (12)	0.3288 (5)	0.105 (3)	0.50
H17'	0.8852	0.3092	0.3312	0.126*	0.50
C18'	0.8127 (11)	0.3984 (9)	0.2656 (4)	0.110 (4)	0.50
H18'	0.8240	0.3502	0.2257	0.132*	0.50
C19'	0.7593 (10)	0.4949 (13)	0.2620 (5)	0.102 (3)	0.50
H19'	0.7347	0.5113	0.2197	0.123*	0.50
C20'	0.7425 (9)	0.5669 (11)	0.3216 (7)	0.0714 (19)	0.50
H20'	0.7067	0.6315	0.3192	0.086*	0.50

	U11	U22	U33	U12	U13	U23
S1	0.0542 (4)	0.0698 (4)	0.0528 (4)	−0.0033 (3)	0.0062 (3)	−0.0106 (3)
O1	0.0647 (13)	0.1020 (15)	0.0756 (13)	−0.0228 (12)	0.0166 (10)	−0.0337 (12)
N1	0.0559 (14)	0.0630 (12)	0.0580 (12)	0.0042 (10)	0.0020 (10)	−0.0066 (10)
N2	0.0529 (14)	0.0655 (12)	0.0594 (12)	−0.0072 (11)	0.0080 (10)	−0.0040 (10)
N3	0.0568 (14)	0.0740 (13)	0.0573 (12)	−0.0097 (11)	0.0118 (11)	−0.0143 (10)
C1	0.0521 (16)	0.0634 (14)	0.0438 (12)	0.0102 (12)	−0.0007 (11)	0.0048 (10)
C2	0.0615 (18)	0.0812 (18)	0.0581 (15)	0.0026 (15)	0.0106 (13)	0.0007 (13)
C3	0.067 (2)	0.100 (2)	0.0611 (16)	0.0151 (18)	0.0163 (15)	0.0006 (15)
C4	0.084 (2)	0.090 (2)	0.0657 (17)	0.0216 (19)	0.0131 (17)	−0.0169 (16)
C5	0.075 (2)	0.0803 (18)	0.0677 (17)	0.0077 (16)	0.0047 (16)	−0.0213 (15)
C6	0.0589 (17)	0.0610 (14)	0.0500 (13)	0.0111 (13)	−0.0020 (12)	−0.0043 (11)
C7	0.0514 (15)	0.0534 (12)	0.0438 (11)	0.0041 (11)	−0.0018 (10)	0.0018 (10)
C8	0.0599 (17)	0.0689 (15)	0.0521 (13)	−0.0055 (14)	0.0088 (13)	−0.0060 (12)
C9	0.0538 (16)	0.0566 (13)	0.0450 (12)	0.0004 (12)	0.0022 (11)	−0.0006 (10)
C10	0.0558 (16)	0.0580 (13)	0.0507 (13)	−0.0014 (12)	0.0024 (12)	−0.0003 (11)
C11	0.070 (2)	0.0852 (19)	0.0725 (17)	−0.0151 (16)	0.0033 (15)	−0.0177 (15)
C12	0.0580 (19)	0.090 (2)	0.0763 (19)	−0.0105 (16)	0.0148 (15)	−0.0134 (16)
C13	0.072 (3)	0.124 (5)	0.108 (6)	0.039 (3)	−0.021 (4)	−0.065 (4)
C14	0.136 (8)	0.165 (9)	0.115 (6)	0.033 (7)	0.001 (5)	0.023 (6)
C13'	0.072 (3)	0.124 (5)	0.108 (6)	0.039 (3)	−0.021 (4)	−0.065 (4)
C14'	0.136 (8)	0.165 (9)	0.115 (6)	0.033 (7)	0.001 (5)	0.023 (6)
C15	0.059 (4)	0.031 (4)	0.0631 (17)	−0.024 (4)	0.0240 (16)	−0.001 (2)
C16	0.087 (3)	0.067 (3)	0.105 (4)	0.001 (3)	0.026 (4)	−0.022 (3)
C17	0.122 (5)	0.085 (5)	0.108 (8)	0.000 (4)	0.058 (7)	−0.028 (5)
C18	0.133 (8)	0.098 (8)	0.098 (5)	−0.045 (8)	0.057 (6)	−0.038 (5)
C19	0.100 (7)	0.149 (8)	0.0579 (19)	−0.034 (6)	0.029 (3)	−0.017 (3)
C20	0.069 (6)	0.102 (2)	0.043 (4)	−0.020 (3)	0.028 (3)	0.007 (2)
C15'	0.059 (4)	0.031 (4)	0.0631 (17)	−0.024 (4)	0.0240 (16)	−0.001 (2)
C16'	0.087 (3)	0.067 (3)	0.105 (4)	0.001 (3)	0.026 (4)	−0.022 (3)
C17'	0.122 (5)	0.085 (5)	0.108 (8)	0.000 (4)	0.058 (7)	−0.028 (5)
C18'	0.133 (8)	0.098 (8)	0.098 (5)	−0.045 (8)	0.057 (6)	−0.038 (5)
C19'	0.100 (7)	0.149 (8)	0.0579 (19)	−0.034 (6)	0.029 (3)	−0.017 (3)
C20'	0.069 (6)	0.102 (2)	0.043 (4)	−0.020 (3)	0.028 (3)	0.007 (2)

S1—C1	1.733 (2)	C12—H12C	0.9701
S1—C7	1.752 (3)	C12—H12D	0.9701
O1—C8	1.238 (3)	C13—C14	1.305 (10)
N1—C7	1.307 (3)	C13—H13	0.9300
N1—C6	1.383 (3)	C14—H14A	0.9300
N2—C10	1.341 (3)	C14—H14B	0.9300
N2—N3	1.393 (3)	C13'—C14'	1.289 (9)
N2—C12	1.459 (3)	C13'—H13'	0.9300
N3—C8	1.391 (4)	C14'—H14C	0.9300
N3—C15'	1.430 (6)	C14'—H14D	0.9300
N3—C15	1.438 (6)	C15—C16	1.3900
C1—C6	1.392 (4)	C15—C20	1.3900
C1—C2	1.395 (4)	C16—C17	1.3900
C2—C3	1.369 (4)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.3900
C3—C4	1.388 (5)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.3900
C4—C5	1.363 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.3900
C5—C6	1.399 (4)	C19—H19	0.9300
C5—H5	0.9300	C20—H20	0.9300
C7—C9	1.451 (3)	C15'—C16'	1.3900
C8—C9	1.425 (3)	C15'—C20'	1.3900
C9—C10	1.368 (4)	C16'—C17'	1.3900
C10—C11	1.492 (4)	C16'—H16'	0.9300
C11—H11A	0.9600	C17'—C18'	1.3900
C11—H11B	0.9600	C17'—H17'	0.9300
C11—H11C	0.9600	C18'—C19'	1.3900
C12—C13'	1.525 (9)	C18'—H18'	0.9300
C12—C13	1.551 (8)	C19'—C20'	1.3900
C12—H12A	0.9700	C19'—H19'	0.9300
C12—H12B	0.9700	C20'—H20'	0.9300
C1—S1—C7	88.53 (12)	H12A—C12—H12B	108.5
C7—N1—C6	110.1 (2)	C13'—C12—H12C	121.0
C10—N2—N3	108.3 (2)	C13—C12—H12C	110.8
C10—N2—C12	126.9 (2)	C13'—C12—H12D	116.7
N3—N2—C12	122.1 (2)	H12C—C12—H12D	104.1
C8—N3—N2	108.7 (2)	C14—C13—C12	117.5 (15)
C8—N3—C15'	128.5 (7)	C14—C13—H13	121.3
N2—N3—C15'	117.3 (6)	C12—C13—H13	121.3
C8—N3—C15	118.9 (7)	C13—C14—H14A	120.0
N2—N3—C15	130.3 (6)	C13—C14—H14B	120.0
C6—C1—C2	121.4 (2)	H14A—C14—H14B	120.0
C6—C1—S1	109.81 (19)	C14'—C13'—C12	128.4 (15)
C2—C1—S1	128.8 (2)	C14'—C13'—H13'	115.8
C3—C2—C1	118.2 (3)	C12—C13'—H13'	115.8
C3—C2—H2	120.9	C13'—C14'—H14C	120.0
C1—C2—H2	120.9	C13'—C14'—H14D	120.0
C2—C3—C4	121.2 (3)	H14C—C14'—H14D	120.0
C2—C3—H3	119.4	C16—C15—C20	120.0
C4—C3—H3	119.4	C16—C15—N3	127.6 (11)
C5—C4—C3	120.6 (3)	C20—C15—N3	111.0 (10)
C5—C4—H4	119.7	C15—C16—C17	120.0
C3—C4—H4	119.7	C15—C16—H16	120.0
C4—C5—C6	119.9 (3)	C17—C16—H16	120.0
C4—C5—H5	120.0	C18—C17—C16	120.0
C6—C5—H5	120.0	C18—C17—H17	120.0
N1—C6—C1	115.6 (2)	C16—C17—H17	120.0
N1—C6—C5	125.7 (3)	C17—C18—C19	120.0
C1—C6—C5	118.7 (3)	C17—C18—H18	120.0
N1—C7—C9	124.4 (2)	C19—C18—H18	120.0
N1—C7—S1	115.99 (19)	C20—C19—C18	120.0
C9—C7—S1	119.57 (17)	C20—C19—H19	120.0
O1—C8—N3	123.1 (2)	C18—C19—H19	120.0
O1—C8—C9	131.8 (3)	C19—C20—C15	120.0
N3—C8—C9	105.0 (2)	C19—C20—H20	120.0
C10—C9—C8	108.3 (2)	C15—C20—H20	120.0
C10—C9—C7	128.8 (2)	C16'—C15'—C20'	120.0
C8—C9—C7	122.9 (2)	C16'—C15'—N3	111.8 (10)
N2—C10—C9	109.4 (2)	C20'—C15'—N3	125.8 (11)
N2—C10—C11	121.2 (3)	C15'—C16'—C17'	120.0
C9—C10—C11	129.4 (2)	C15'—C16'—H16'	120.0
C10—C11—H11A	109.5	C17'—C16'—H16'	120.0
C10—C11—H11B	109.5	C18'—C17'—C16'	120.0
H11A—C11—H11B	109.5	C18'—C17'—H17'	120.0
C10—C11—H11C	109.5	C16'—C17'—H17'	120.0
H11A—C11—H11C	109.5	C19'—C18'—C17'	120.0
H11B—C11—H11C	109.5	C19'—C18'—H18'	120.0
N2—C12—C13'	112.3 (9)	C17'—C18'—H18'	120.0
N2—C12—C13	107.8 (9)	C18'—C19'—C20'	120.0
N2—C12—H12A	110.1	C18'—C19'—H19'	120.0
C13'—C12—H12A	118.2	C20'—C19'—H19'	120.0
C13—C12—H12A	110.1	C19'—C20'—C15'	120.0
N2—C12—H12B	110.1	C19'—C20'—H20'	120.0
C13—C12—H12B	110.1	C15'—C20'—H20'	120.0
C10—N2—N3—C8	5.6 (3)	C12—N2—C10—C11	13.0 (4)
C12—N2—N3—C8	168.3 (2)	C8—C9—C10—N2	2.0 (3)
C10—N2—N3—C15'	161.9 (8)	C7—C9—C10—N2	179.5 (2)
C12—N2—N3—C15'	−35.5 (8)	C8—C9—C10—C11	−177.2 (3)
C10—N2—N3—C15	168.7 (9)	C7—C9—C10—C11	0.3 (5)
C12—N2—N3—C15	−28.7 (9)	C10—N2—C12—C13'	77.9 (7)
C7—S1—C1—C6	1.10 (18)	N3—N2—C12—C13'	−81.3 (7)
C7—S1—C1—C2	179.7 (2)	C10—N2—C12—C13	64.1 (7)
C6—C1—C2—C3	−0.8 (4)	N3—N2—C12—C13	−95.2 (7)
S1—C1—C2—C3	−179.3 (2)	N2—C12—C13—C14	−142.4 (14)
C1—C2—C3—C4	−0.1 (4)	C13'—C12—C13—C14	106 (7)
C2—C3—C4—C5	0.8 (5)	N2—C12—C13'—C14'	−108 (2)
C3—C4—C5—C6	−0.6 (5)	C13—C12—C13'—C14'	−35 (6)
C7—N1—C6—C1	0.3 (3)	C8—N3—C15—C16	−133.0 (8)
C7—N1—C6—C5	179.4 (3)	N2—N3—C15—C16	65.4 (10)
C2—C1—C6—N1	−179.8 (2)	C15'—N3—C15—C16	91 (6)
S1—C1—C6—N1	−1.1 (3)	C8—N3—C15—C20	60.6 (8)
C2—C1—C6—C5	1.0 (4)	N2—N3—C15—C20	−101.0 (10)
S1—C1—C6—C5	179.8 (2)	C15'—N3—C15—C20	−75 (6)
C4—C5—C6—N1	−179.4 (3)	C20—C15—C16—C17	0.0
C4—C5—C6—C1	−0.3 (4)	N3—C15—C16—C17	−165.3 (9)
C6—N1—C7—C9	−177.2 (2)	C15—C16—C17—C18	0.0
C6—N1—C7—S1	0.6 (3)	C16—C17—C18—C19	0.0
C1—S1—C7—N1	−1.01 (19)	C17—C18—C19—C20	0.0
C1—S1—C7—C9	176.89 (19)	C18—C19—C20—C15	0.0
N2—N3—C8—O1	176.1 (3)	C16—C15—C20—C19	0.0
C15'—N3—C8—O1	23.3 (8)	N3—C15—C20—C19	167.6 (9)
C15—N3—C8—O1	10.8 (7)	C8—N3—C15'—C16'	−121.9 (9)
N2—N3—C8—C9	−4.3 (3)	N2—N3—C15'—C16'	87.4 (7)
C15'—N3—C8—C9	−157.0 (7)	C15—N3—C15'—C16'	−71 (6)
C15—N3—C8—C9	−169.5 (7)	C8—N3—C15'—C20'	40.7 (11)
O1—C8—C9—C10	−178.9 (3)	N2—N3—C15'—C20'	−110.1 (9)
N3—C8—C9—C10	1.4 (3)	C15—N3—C15'—C20'	92 (6)
O1—C8—C9—C7	3.4 (5)	C20'—C15'—C16'—C17'	0.0
N3—C8—C9—C7	−176.2 (2)	N3—C15'—C16'—C17'	163.7 (10)
N1—C7—C9—C10	7.8 (4)	C15'—C16'—C17'—C18'	0.0
S1—C7—C9—C10	−169.9 (2)	C16'—C17'—C18'—C19'	0.0
N1—C7—C9—C8	−175.0 (2)	C17'—C18'—C19'—C20'	0.0
S1—C7—C9—C8	7.2 (3)	C18'—C19'—C20'—C15'	0.0
N3—N2—C10—C9	−4.7 (3)	C16'—C15'—C20'—C19'	0.0
C12—N2—C10—C9	−166.3 (3)	N3—C15'—C20'—C19'	−161.3 (9)
N3—N2—C10—C11	174.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.59	3.318 (3)	135
C12—H12A···O1ii	0.97	2.51	3.404 (4)	152
C12—H12C···O1ii	0.97	2.48	3.404 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.59	3.318 (3)	135
C12—H12A⋯O1ii	0.97	2.51	3.404 (4)	152
C12—H12C⋯O1ii	0.97	2.48	3.404 (4)	159

Symmetry codes: (i) ; (ii) .