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

In the title compound, C(17)H(13)N(3)OS, the dihedral angle between the ring systems is 2.22 (5)°. The N-H grouping participates in both intra- and intermolecular N-H⋯O hydrogen bonds, the latter leading to dimers related by a twofold rotation axis.

Related literature

For related structures, see: Teo et al. (1993 ▶); Chen (1994 ▶); Sawusch & Schilde (1999 ▶); Chu et al. (2003 ▶); Liu et al. (2004 ▶). For related literature, see: Harnden et al. (1978 ▶); Hatheway et al. (1978 ▶); Londershausen (1996 ▶); Tewari & Mishra (2001 ▶).

Experimental

Crystal data

C17H13N3OS

M = 307.36

Monoclinic,

a = 27.0144 (8) Å

b = 7.4021 (2) Å

c = 14.0523 (4) Å

β = 97.466 (1)°

V = 2786.12 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.40 × 0.28 × 0.20 mm

Data collection

Bruker APEXII with a CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.875, T max = 0.956

57380 measured reflections

3359 independent reflections

2928 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.082

S = 1.05

3359 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.26 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: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013176/fk2016sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013176/fk2016Isup2.hkl

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

C17H13N3OS	F(000) = 1280
Mr = 307.36	Dx = 1.466 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9789 reflections
a = 27.0144 (8) Å	θ = 2.9–30.6°
b = 7.4021 (2) Å	µ = 0.24 mm−1
c = 14.0523 (4) Å	T = 100 K
β = 97.466 (1)°	Prism, red
V = 2786.12 (14) Å3	0.40 × 0.28 × 0.20 mm
Z = 8

Bruker APEXII with a CCD detector diffractometer	3359 independent reflections
Radiation source: fine-focus sealed tube	2928 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 28.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −35→35
Tmin = 0.875, Tmax = 0.956	k = −9→9
57380 measured reflections	l = −18→18

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)] = 0.030	Hydrogen site location: difference Fourier map
wR(F2) = 0.082	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0331P)2 + 3.8168P] where P = (Fo2 + 2Fc2)/3
3359 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	1.059848 (12)	0.17433 (4)	1.08323 (2)	0.01678 (9)
C2	1.02064 (5)	0.21310 (17)	0.97688 (9)	0.0151 (2)
N3	1.04276 (4)	0.16259 (14)	0.90040 (7)	0.0160 (2)
H3	1.0281	0.1754	0.8411	0.0247 (19)*
C4	1.12040 (5)	0.02162 (18)	0.85676 (10)	0.0198 (3)
H4	1.1098	0.0244	0.7896	0.0247 (19)*
C5	1.16636 (5)	−0.04948 (19)	0.89339 (11)	0.0235 (3)
H5	1.1876	−0.0965	0.8506	0.0247 (19)*
C6	1.18205 (5)	−0.05341 (19)	0.99209 (11)	0.0250 (3)
H6	1.2138	−0.1025	1.0152	0.0247 (19)*
C7	1.15201 (5)	0.01318 (19)	1.05696 (10)	0.0222 (3)
H7	1.1626	0.0104	1.1241	0.0247 (19)*
C8	1.10583 (5)	0.08405 (17)	1.02029 (9)	0.0174 (2)
C9	1.09021 (5)	0.08893 (17)	0.92167 (9)	0.0167 (2)
N11	0.89806 (4)	0.38442 (15)	0.90615 (7)	0.0151 (2)
N12	0.90079 (4)	0.40940 (15)	1.00569 (7)	0.0167 (2)
C13	0.94462 (5)	0.34924 (16)	1.04238 (9)	0.0157 (2)
C14	0.97279 (5)	0.28461 (17)	0.96994 (8)	0.0150 (2)
C15	0.94124 (5)	0.30754 (16)	0.87995 (9)	0.0147 (2)
O15	0.94948 (3)	0.26778 (13)	0.79710 (6)	0.01790 (19)
C16	0.95996 (5)	0.35330 (18)	1.14808 (9)	0.0194 (3)
H16A	0.9322	0.3982	1.1800	0.030 (3)*
H16B	0.9888	0.4333	1.1628	0.030 (3)*
H16C	0.9689	0.2310	1.1710	0.030 (3)*
C21	0.85536 (5)	0.45211 (17)	0.84799 (9)	0.0154 (2)
C22	0.81913 (5)	0.54324 (19)	0.89193 (9)	0.0201 (3)
H22	0.8227	0.5545	0.9598	0.027 (2)*
C23	0.77785 (5)	0.61730 (19)	0.83640 (10)	0.0219 (3)
H23	0.7534	0.6799	0.8666	0.027 (2)*
C24	0.77185 (5)	0.60084 (19)	0.73731 (10)	0.0224 (3)
H24	0.7436	0.6522	0.6995	0.027 (2)*
C25	0.80761 (5)	0.50843 (19)	0.69414 (10)	0.0225 (3)
H25	0.8035	0.4960	0.6263	0.027 (2)*
C26	0.84937 (5)	0.43350 (18)	0.74838 (9)	0.0186 (3)
H26	0.8736	0.3703	0.7179	0.027 (2)*

	U11	U22	U33	U12	U13	U23
S1	0.01820 (16)	0.01755 (16)	0.01406 (15)	0.00014 (12)	0.00009 (11)	0.00048 (11)
C2	0.0180 (6)	0.0128 (5)	0.0142 (5)	−0.0027 (4)	0.0010 (4)	0.0002 (4)
N3	0.0175 (5)	0.0166 (5)	0.0138 (5)	0.0006 (4)	0.0019 (4)	0.0002 (4)
C4	0.0221 (6)	0.0161 (6)	0.0222 (6)	−0.0004 (5)	0.0062 (5)	0.0012 (5)
C5	0.0213 (7)	0.0184 (6)	0.0322 (7)	0.0009 (5)	0.0090 (5)	0.0006 (5)
C6	0.0175 (6)	0.0221 (7)	0.0348 (8)	0.0030 (5)	0.0009 (5)	0.0030 (6)
C7	0.0211 (6)	0.0196 (6)	0.0248 (7)	−0.0003 (5)	−0.0013 (5)	0.0025 (5)
C8	0.0175 (6)	0.0142 (6)	0.0206 (6)	−0.0015 (5)	0.0026 (5)	0.0007 (5)
C9	0.0168 (6)	0.0133 (6)	0.0200 (6)	−0.0014 (5)	0.0024 (5)	0.0019 (5)
N11	0.0169 (5)	0.0162 (5)	0.0123 (5)	0.0007 (4)	0.0025 (4)	−0.0001 (4)
N12	0.0204 (5)	0.0177 (5)	0.0122 (5)	0.0000 (4)	0.0026 (4)	−0.0010 (4)
C13	0.0192 (6)	0.0132 (6)	0.0150 (6)	−0.0018 (5)	0.0031 (5)	−0.0006 (4)
C14	0.0177 (6)	0.0138 (6)	0.0135 (5)	−0.0016 (5)	0.0016 (4)	−0.0003 (4)
C15	0.0157 (6)	0.0129 (5)	0.0157 (6)	−0.0021 (4)	0.0024 (4)	0.0004 (4)
O15	0.0188 (4)	0.0220 (5)	0.0132 (4)	0.0011 (4)	0.0034 (3)	−0.0014 (3)
C16	0.0227 (6)	0.0208 (6)	0.0146 (6)	−0.0001 (5)	0.0017 (5)	−0.0014 (5)
C21	0.0153 (6)	0.0131 (5)	0.0176 (6)	−0.0027 (5)	0.0015 (4)	0.0014 (4)
C22	0.0197 (6)	0.0226 (7)	0.0182 (6)	0.0011 (5)	0.0037 (5)	−0.0001 (5)
C23	0.0175 (6)	0.0212 (6)	0.0275 (7)	0.0011 (5)	0.0050 (5)	0.0003 (5)
C24	0.0177 (6)	0.0209 (7)	0.0271 (7)	−0.0007 (5)	−0.0021 (5)	0.0038 (5)
C25	0.0238 (7)	0.0245 (7)	0.0183 (6)	−0.0010 (5)	−0.0008 (5)	0.0009 (5)
C26	0.0195 (6)	0.0186 (6)	0.0178 (6)	−0.0004 (5)	0.0025 (5)	−0.0003 (5)

S1—C2	1.7397 (13)	N12—C13	1.3067 (16)
S1—C8	1.7485 (13)	C13—C14	1.4303 (17)
C2—N3	1.3488 (16)	C13—C16	1.4896 (17)
C2—C14	1.3883 (18)	C14—C15	1.4402 (16)
N3—C9	1.3892 (16)	C15—O15	1.2486 (15)
N3—H3	0.8800	C16—H16A	0.9800
C4—C5	1.3845 (19)	C16—H16B	0.9800
C4—C9	1.3924 (18)	C16—H16C	0.9800
C4—H4	0.9500	C21—C26	1.3949 (17)
C5—C6	1.397 (2)	C21—C22	1.3969 (18)
C5—H5	0.9500	C22—C23	1.3882 (19)
C6—C7	1.387 (2)	C22—H22	0.9500
C6—H6	0.9500	C23—C24	1.3861 (19)
C7—C8	1.3892 (18)	C23—H23	0.9500
C7—H7	0.9500	C24—C25	1.386 (2)
C8—C9	1.3956 (17)	C24—H24	0.9500
N11—C15	1.3896 (16)	C25—C26	1.3921 (18)
N11—N12	1.4034 (14)	C25—H25	0.9500
N11—C21	1.4158 (16)	C26—H26	0.9500
C2—S1—C8	91.25 (6)	C14—C13—C16	127.71 (12)
N3—C2—C14	123.68 (11)	C2—C14—C13	130.85 (12)
N3—C2—S1	110.81 (9)	C2—C14—C15	123.10 (11)
C14—C2—S1	125.50 (10)	C13—C14—C15	106.05 (11)
C2—N3—C9	115.43 (10)	O15—C15—N11	126.94 (11)
C2—N3—H3	122.3	O15—C15—C14	129.34 (12)
C9—N3—H3	122.3	N11—C15—C14	103.72 (10)
C5—C4—C9	117.76 (12)	C13—C16—H16A	109.5
C5—C4—H4	121.1	C13—C16—H16B	109.5
C9—C4—H4	121.1	H16A—C16—H16B	109.5
C4—C5—C6	121.25 (13)	C13—C16—H16C	109.5
C4—C5—H5	119.4	H16A—C16—H16C	109.5
C6—C5—H5	119.4	H16B—C16—H16C	109.5
C7—C6—C5	121.13 (13)	C26—C21—C22	119.65 (12)
C7—C6—H6	119.4	C26—C21—N11	121.59 (11)
C5—C6—H6	119.4	C22—C21—N11	118.74 (11)
C6—C7—C8	117.66 (13)	C23—C22—C21	120.00 (12)
C6—C7—H7	121.2	C23—C22—H22	120.0
C8—C7—H7	121.2	C21—C22—H22	120.0
C7—C8—C9	121.27 (12)	C24—C23—C22	120.70 (13)
C7—C8—S1	128.27 (11)	C24—C23—H23	119.7
C9—C8—S1	110.45 (10)	C22—C23—H23	119.7
N3—C9—C4	127.02 (12)	C23—C24—C25	119.07 (12)
N3—C9—C8	112.04 (11)	C23—C24—H24	120.5
C4—C9—C8	120.93 (12)	C25—C24—H24	120.5
C15—N11—N12	112.38 (10)	C24—C25—C26	121.21 (12)
C15—N11—C21	129.86 (10)	C24—C25—H25	119.4
N12—N11—C21	117.51 (10)	C26—C25—H25	119.4
C13—N12—N11	106.02 (10)	C25—C26—C21	119.36 (12)
N12—C13—C14	111.83 (11)	C25—C26—H26	120.3
N12—C13—C16	120.47 (11)	C21—C26—H26	120.3

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O15	0.88	2.24	2.8483 (14)	126
N3—H3···O15i	0.88	2.22	2.9161 (13)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O15	0.88	2.24	2.8483 (14)	126
N3—H3⋯O15i	0.88	2.22	2.9161 (13)	136

Symmetry code: (i) .