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

The title compound, C(20)H(15)N(3)OS, is a 1H-pyrazol-3(2H)-one having aromatic 4-(1,3-benzothia-zol-2-yl) and 2-phenyl substit-uents. The five-membered ring and the fused-ring system are close to planar, the r.m.s. deviations being 0.025 and 0.005 Å, respectively. The five-membered ring is aligned at 67.5 (1)° with respect to the phenyl ring and at 4.7 (1)° with respect to the fused-ring system. In the crystal, adjacent mol-ecules are linked through the acetyl-enic H atom by a C-H⋯O hydrogen bond into C(8) chains propagating in [010].

Related literature

For the structure of a similar compound, 4-(benzo[d]thia­zol-2-yl)-2-allyl-3-methyl-1-phenyl-1,2-dihydro­pyrazol-5-one, see: Chakibe et al. (2010 ▶). 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: Chakib et al. (2010 ▶).

Experimental

Crystal data

C20H15N3OS

M = 345.41

Orthorhombic,

a = 4.8221 (1) Å

b = 9.3698 (2) Å

c = 37.6990 (9) Å

V = 1703.32 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.923, T max = 0.961

10502 measured reflections

3699 independent reflections

3008 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.105

S = 0.99

3699 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1483 Friedel pairs

Flack parameter: 0.00 (9)

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/S1600536810040328/xu5048sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040328/xu5048Isup2.hkl

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

C20H15N3OS	F(000) = 720
Mr = 345.41	Dx = 1.347 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2503 reflections
a = 4.8221 (1) Å	θ = 2.4–22.9°
b = 9.3698 (2) Å	µ = 0.20 mm−1
c = 37.6990 (9) Å	T = 293 K
V = 1703.32 (6) Å3	Prism, yellow
Z = 4	0.40 × 0.20 × 0.20 mm

Bruker X8 APEXII diffractometer	3699 independent reflections
Radiation source: fine-focus sealed tube	3008 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 27.1°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→6
Tmin = 0.923, Tmax = 0.961	k = −11→11
10502 measured reflections	l = −47→46

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0613P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
3699 reflections	Δρmax = 0.20 e Å−3
227 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), 1483 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (9)

	x	y	z	Uiso*/Ueq
S1	0.55911 (13)	0.45298 (6)	0.105599 (16)	0.04655 (17)
O1	0.9129 (4)	0.52382 (15)	0.16533 (4)	0.0487 (4)
N1	0.5947 (4)	0.6723 (2)	0.06358 (5)	0.0445 (4)
N2	1.1641 (4)	0.85264 (18)	0.14034 (5)	0.0422 (4)
N3	1.1570 (4)	0.73580 (18)	0.16370 (5)	0.0408 (4)
C1	0.3603 (5)	0.4536 (3)	0.06743 (6)	0.0469 (5)
C2	0.1735 (6)	0.3514 (3)	0.05524 (7)	0.0599 (7)
H2	0.1422	0.2680	0.0680	0.072*
C3	0.0366 (6)	0.3767 (3)	0.02398 (8)	0.0681 (8)
H3	−0.0894	0.3097	0.0155	0.082*
C4	0.0833 (6)	0.4998 (3)	0.00504 (8)	0.0683 (8)
H4	−0.0121	0.5142	−0.0161	0.082*
C5	0.2662 (5)	0.6015 (3)	0.01643 (7)	0.0593 (7)
H5	0.2961	0.6841	0.0033	0.071*
C6	0.4073 (5)	0.5783 (3)	0.04845 (6)	0.0446 (5)
C7	0.6919 (5)	0.6195 (2)	0.09303 (6)	0.0376 (5)
C8	0.9769 (5)	0.6346 (2)	0.14978 (5)	0.0386 (5)
C9	0.8913 (4)	0.6897 (2)	0.11590 (5)	0.0351 (4)
C10	1.0182 (4)	0.8196 (2)	0.11109 (5)	0.0386 (5)
C11	1.0201 (6)	0.9159 (3)	0.07987 (6)	0.0558 (7)
H11A	0.9830	1.0119	0.0874	0.084*
H11B	0.8800	0.8861	0.0634	0.084*
H11C	1.1985	0.9120	0.0686	0.084*
C12	1.3789 (5)	0.9610 (2)	0.14413 (7)	0.0479 (6)
H12A	1.4965	0.9371	0.1641	0.057*
H12B	1.4934	0.9620	0.1230	0.057*
C13	1.2600 (5)	1.1024 (3)	0.14956 (6)	0.0494 (6)
C14	1.1643 (7)	1.2142 (3)	0.15376 (8)	0.0657 (8)
H14	1.0873	1.3042	0.1571	0.079*
C15	1.2100 (5)	0.7561 (2)	0.20074 (5)	0.0383 (5)
C16	1.0709 (5)	0.8595 (3)	0.21937 (7)	0.0534 (6)
H16	0.9444	0.9189	0.2080	0.064*
C17	1.1218 (6)	0.8741 (3)	0.25519 (7)	0.0625 (7)
H17	1.0293	0.9440	0.2681	0.075*
C18	1.3064 (6)	0.7867 (3)	0.27184 (7)	0.0588 (7)
H18	1.3389	0.7973	0.2960	0.071*
C19	1.4434 (6)	0.6842 (3)	0.25322 (7)	0.0629 (7)
H19	1.5693	0.6248	0.2647	0.075*
C20	1.3951 (5)	0.6682 (3)	0.21707 (6)	0.0505 (6)
H20	1.4880	0.5983	0.2042	0.061*

	U11	U22	U33	U12	U13	U23
S1	0.0594 (3)	0.0375 (3)	0.0427 (3)	−0.0076 (3)	0.0002 (3)	0.0022 (2)
O1	0.0764 (10)	0.0299 (8)	0.0397 (9)	−0.0053 (8)	−0.0008 (9)	0.0053 (6)
N1	0.0509 (11)	0.0449 (11)	0.0376 (10)	−0.0009 (9)	0.0005 (9)	0.0036 (8)
N2	0.0573 (11)	0.0309 (9)	0.0386 (11)	−0.0056 (8)	0.0001 (9)	0.0042 (8)
N3	0.0598 (12)	0.0303 (9)	0.0323 (10)	−0.0002 (8)	−0.0029 (9)	0.0021 (8)
C1	0.0480 (12)	0.0497 (13)	0.0431 (13)	0.0012 (11)	0.0078 (10)	−0.0093 (11)
C2	0.0620 (15)	0.0589 (17)	0.0587 (17)	−0.0136 (13)	0.0045 (13)	−0.0111 (13)
C3	0.0521 (14)	0.086 (2)	0.0662 (19)	−0.0125 (15)	0.0019 (14)	−0.0292 (17)
C4	0.0551 (15)	0.096 (2)	0.0535 (17)	0.0027 (16)	−0.0097 (13)	−0.0122 (15)
C5	0.0586 (15)	0.0776 (19)	0.0418 (15)	−0.0006 (14)	−0.0034 (12)	0.0016 (13)
C6	0.0435 (12)	0.0544 (14)	0.0358 (12)	0.0030 (11)	0.0021 (10)	−0.0053 (10)
C7	0.0442 (11)	0.0346 (11)	0.0340 (12)	0.0014 (9)	0.0085 (9)	−0.0004 (9)
C8	0.0528 (13)	0.0297 (10)	0.0334 (12)	0.0042 (9)	0.0042 (9)	−0.0043 (8)
C9	0.0456 (11)	0.0301 (10)	0.0297 (10)	0.0026 (9)	0.0057 (9)	0.0008 (8)
C10	0.0488 (12)	0.0333 (10)	0.0336 (12)	0.0023 (8)	0.0052 (9)	0.0002 (9)
C11	0.0780 (17)	0.0472 (14)	0.0422 (14)	−0.0119 (12)	0.0012 (12)	0.0132 (10)
C12	0.0470 (12)	0.0391 (12)	0.0577 (15)	−0.0027 (10)	0.0044 (11)	0.0016 (11)
C13	0.0636 (15)	0.0378 (13)	0.0467 (15)	−0.0098 (12)	0.0002 (12)	0.0017 (10)
C14	0.093 (2)	0.0388 (14)	0.0652 (18)	0.0028 (14)	0.0063 (16)	0.0001 (12)
C15	0.0451 (12)	0.0360 (12)	0.0339 (12)	−0.0026 (9)	−0.0016 (9)	−0.0021 (9)
C16	0.0570 (13)	0.0545 (15)	0.0487 (14)	0.0157 (12)	−0.0105 (12)	−0.0128 (11)
C17	0.0676 (16)	0.0679 (18)	0.0519 (16)	0.0054 (14)	−0.0002 (14)	−0.0231 (13)
C18	0.0733 (17)	0.0678 (18)	0.0353 (14)	−0.0125 (15)	−0.0049 (13)	−0.0038 (12)
C19	0.0728 (17)	0.0678 (17)	0.0479 (15)	0.0121 (15)	−0.0133 (14)	0.0063 (13)
C20	0.0628 (15)	0.0459 (13)	0.0428 (13)	0.0117 (12)	−0.0012 (12)	−0.0030 (11)

S1—C1	1.729 (2)	C9—C10	1.374 (3)
S1—C7	1.752 (2)	C10—C11	1.483 (3)
O1—C8	1.232 (2)	C11—H11A	0.9600
N1—C7	1.303 (3)	C11—H11B	0.9600
N1—C6	1.385 (3)	C11—H11C	0.9600
N2—C10	1.344 (3)	C12—C13	1.458 (3)
N2—N3	1.405 (2)	C12—H12A	0.9700
N2—C12	1.458 (3)	C12—H12B	0.9700
N3—C8	1.389 (3)	C13—C14	1.156 (4)
N3—C15	1.433 (3)	C14—H14	0.9300
C1—C6	1.389 (3)	C15—C20	1.362 (3)
C1—C2	1.393 (3)	C15—C16	1.372 (3)
C2—C3	1.371 (4)	C16—C17	1.379 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.375 (4)	C17—C18	1.362 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.368 (4)	C18—C19	1.361 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.403 (3)	C19—C20	1.391 (3)
C5—H5	0.9300	C19—H19	0.9300
C7—C9	1.449 (3)	C20—H20	0.9300
C8—C9	1.438 (3)
C1—S1—C7	88.55 (12)	N2—C10—C9	109.20 (18)
C7—N1—C6	110.14 (19)	N2—C10—C11	120.51 (19)
C10—N2—N3	108.77 (17)	C9—C10—C11	130.3 (2)
C10—N2—C12	127.79 (18)	C10—C11—H11A	109.5
N3—N2—C12	119.92 (19)	C10—C11—H11B	109.5
C8—N3—N2	108.09 (17)	H11A—C11—H11B	109.5
C8—N3—C15	124.80 (18)	C10—C11—H11C	109.5
N2—N3—C15	120.19 (17)	H11A—C11—H11C	109.5
C6—C1—C2	120.9 (2)	H11B—C11—H11C	109.5
C6—C1—S1	109.94 (18)	C13—C12—N2	111.6 (2)
C2—C1—S1	129.1 (2)	C13—C12—H12A	109.3
C3—C2—C1	118.5 (3)	N2—C12—H12A	109.3
C3—C2—H2	120.8	C13—C12—H12B	109.3
C1—C2—H2	120.8	N2—C12—H12B	109.3
C2—C3—C4	120.8 (3)	H12A—C12—H12B	108.0
C2—C3—H3	119.6	C14—C13—C12	179.6 (3)
C4—C3—H3	119.6	C13—C14—H14	180.0
C5—C4—C3	121.9 (3)	C20—C15—C16	121.1 (2)
C5—C4—H4	119.1	C20—C15—N3	118.5 (2)
C3—C4—H4	119.1	C16—C15—N3	120.4 (2)
C4—C5—C6	118.3 (3)	C15—C16—C17	118.9 (2)
C4—C5—H5	120.8	C15—C16—H16	120.5
C6—C5—H5	120.8	C17—C16—H16	120.5
N1—C6—C1	115.4 (2)	C18—C17—C16	120.5 (3)
N1—C6—C5	124.9 (2)	C18—C17—H17	119.7
C1—C6—C5	119.7 (2)	C16—C17—H17	119.7
N1—C7—C9	125.0 (2)	C19—C18—C17	120.2 (2)
N1—C7—S1	115.93 (17)	C19—C18—H18	119.9
C9—C7—S1	119.08 (16)	C17—C18—H18	119.9
O1—C8—N3	123.5 (2)	C18—C19—C20	120.0 (3)
O1—C8—C9	130.8 (2)	C18—C19—H19	120.0
N3—C8—C9	105.66 (18)	C20—C19—H19	120.0
C10—C9—C8	107.89 (19)	C15—C20—C19	119.2 (2)
C10—C9—C7	128.25 (19)	C15—C20—H20	120.4
C8—C9—C7	123.76 (19)	C19—C20—H20	120.4
C10—N2—N3—C8	−6.4 (2)	O1—C8—C9—C7	2.1 (4)
C12—N2—N3—C8	−166.84 (19)	N3—C8—C9—C7	−177.20 (19)
C10—N2—N3—C15	−158.63 (19)	N1—C7—C9—C10	−1.5 (4)
C12—N2—N3—C15	41.0 (3)	S1—C7—C9—C10	−179.60 (17)
C7—S1—C1—C6	−0.38 (17)	N1—C7—C9—C8	174.4 (2)
C7—S1—C1—C2	−179.8 (2)	S1—C7—C9—C8	−3.7 (3)
C6—C1—C2—C3	0.0 (4)	N3—N2—C10—C9	6.0 (2)
S1—C1—C2—C3	179.4 (2)	C12—N2—C10—C9	164.5 (2)
C1—C2—C3—C4	0.2 (4)	N3—N2—C10—C11	−172.1 (2)
C2—C3—C4—C5	−0.1 (4)	C12—N2—C10—C11	−13.7 (3)
C3—C4—C5—C6	−0.3 (4)	C8—C9—C10—N2	−3.4 (2)
C7—N1—C6—C1	1.1 (3)	C7—C9—C10—N2	173.0 (2)
C7—N1—C6—C5	−179.4 (2)	C8—C9—C10—C11	174.5 (2)
C2—C1—C6—N1	179.1 (2)	C7—C9—C10—C11	−9.1 (4)
S1—C1—C6—N1	−0.3 (2)	C10—N2—C12—C13	81.7 (3)
C2—C1—C6—C5	−0.4 (3)	N3—N2—C12—C13	−122.0 (2)
S1—C1—C6—C5	−179.83 (18)	C8—N3—C15—C20	81.6 (3)
C4—C5—C6—N1	−178.9 (2)	N2—N3—C15—C20	−131.0 (2)
C4—C5—C6—C1	0.5 (4)	C8—N3—C15—C16	−96.6 (3)
C6—N1—C7—C9	−179.6 (2)	N2—N3—C15—C16	50.7 (3)
C6—N1—C7—S1	−1.4 (2)	C20—C15—C16—C17	0.2 (4)
C1—S1—C7—N1	1.08 (18)	N3—C15—C16—C17	178.4 (2)
C1—S1—C7—C9	179.36 (17)	C15—C16—C17—C18	−0.3 (4)
N2—N3—C8—O1	−175.2 (2)	C16—C17—C18—C19	0.1 (4)
C15—N3—C8—O1	−24.6 (3)	C17—C18—C19—C20	0.0 (4)
N2—N3—C8—C9	4.2 (2)	C16—C15—C20—C19	−0.1 (4)
C15—N3—C8—C9	154.8 (2)	N3—C15—C20—C19	−178.3 (2)
O1—C8—C9—C10	178.7 (2)	C18—C19—C20—C15	0.0 (4)
N3—C8—C9—C10	−0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1i	0.93	2.24	3.174 (3)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1i	0.93	2.24	3.174 (3)	179

Symmetry code: (i) .