N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-[4-(methyl-sulfan-yl)phen-yl]acetamide.

In the title compound, C(20)H(21)N(3)O(2)S, the 2,3-dihydro-1H-pyrazole ring is nearly planar (r.m.s. deviation = 0.023 Å) and forms dihedral angles of 16.96 (6) and 38.93 (6)° with the benzene and phenyl rings, respectively. The dihedral angle between the benzene and phenyl rings is 55.54 (6)°. The mol-ecular conformation is consolidated by an intra-molecular C-H⋯O hydrogen bond, which forms an S(6) ring. In the crystal, inversion dimers linked by pairs of N-H⋯O(p) (p = pyrazole) hydrogen bonds generate R(2) (2)(10) loops. The dimers are linked by C-H⋯O hydrogen bonds into sheets lying parallel to (100).

Related literature

For general background to the title compound and for related structures, see: Fun et al. (2011a ▶,b ▶, 2012a ▶,b ▶). For the stability of the temperature controller used in the the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H21N3O2S

M = 367.46

Monoclinic,

a = 14.9176 (8) Å

b = 6.6527 (4) Å

c = 19.5792 (10) Å

β = 110.689 (1)°

V = 1817.78 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.37 × 0.18 × 0.07 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.931, T max = 0.987

19714 measured reflections

5302 independent reflections

4231 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.03

5302 reflections

242 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034605/hb6925sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034605/hb6925Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034605/hb6925Isup3.cml

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

C20H21N3O2S	F(000) = 776
Mr = 367.46	Dx = 1.343 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5722 reflections
a = 14.9176 (8) Å	θ = 2.9–30.0°
b = 6.6527 (4) Å	µ = 0.20 mm−1
c = 19.5792 (10) Å	T = 100 K
β = 110.689 (1)°	Plate, yellow
V = 1817.78 (17) Å3	0.37 × 0.18 × 0.07 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	5302 independent reflections
Radiation source: fine-focus sealed tube	4231 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 30.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→21
Tmin = 0.931, Tmax = 0.987	k = −9→9
19714 measured reflections	l = −27→27

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.058P)2 + 0.594P] where P = (Fo2 + 2Fc2)/3
5302 reflections	(Δ/σ)max = 0.001
242 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 2sigma(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	0.90518 (2)	1.11552 (8)	0.26045 (2)	0.03908 (13)
O1	0.48783 (6)	0.70169 (15)	0.28728 (5)	0.0201 (2)
O2	0.37745 (6)	0.49368 (14)	0.45147 (5)	0.01838 (19)
N1	0.54078 (7)	0.67806 (17)	0.41084 (6)	0.0162 (2)
N2	0.35044 (7)	1.00817 (16)	0.41536 (5)	0.0153 (2)
N3	0.31713 (7)	0.81906 (16)	0.42879 (5)	0.0155 (2)
C1	0.67740 (8)	0.8798 (2)	0.29532 (7)	0.0182 (2)
H1A	0.6135	0.9222	0.2866	0.022*
C2	0.73958 (9)	1.0064 (2)	0.27714 (7)	0.0201 (3)
H2A	0.7178	1.1344	0.2564	0.024*
C3	0.83366 (8)	0.9474 (2)	0.28906 (6)	0.0210 (3)
C4	0.86425 (8)	0.7580 (2)	0.31933 (6)	0.0215 (3)
H4A	0.9278	0.7148	0.3271	0.026*
C5	0.80202 (8)	0.6324 (2)	0.33817 (7)	0.0189 (3)
H5A	0.8240	0.5050	0.3594	0.023*
C6	0.70736 (8)	0.6908 (2)	0.32626 (6)	0.0162 (2)
C7	0.64106 (8)	0.5462 (2)	0.34610 (7)	0.0184 (2)
H7A	0.6251	0.4323	0.3113	0.022*
H7B	0.6750	0.4914	0.3956	0.022*
C8	0.54900 (8)	0.64688 (19)	0.34457 (6)	0.0155 (2)
C9	0.45856 (8)	0.7725 (2)	0.41579 (6)	0.0153 (2)
C10	0.43573 (8)	0.9695 (2)	0.40415 (6)	0.0154 (2)
C11	0.38429 (8)	0.6706 (2)	0.43345 (6)	0.0154 (2)
C12	0.24277 (8)	0.8087 (2)	0.45811 (6)	0.0158 (2)
C13	0.18356 (9)	0.6400 (2)	0.44282 (7)	0.0200 (3)
H13A	0.1934	0.5340	0.4137	0.024*
C14	0.10982 (10)	0.6290 (2)	0.47079 (8)	0.0251 (3)
H14A	0.0696	0.5138	0.4613	0.030*
C15	0.09484 (9)	0.7850 (2)	0.51241 (7)	0.0261 (3)
H15A	0.0439	0.7774	0.5308	0.031*
C16	0.15406 (9)	0.9525 (2)	0.52726 (7)	0.0233 (3)
H16A	0.1435	1.0593	0.5557	0.028*
C17	0.22911 (9)	0.9648 (2)	0.50060 (6)	0.0194 (3)
H17A	0.2704	1.0784	0.5114	0.023*
C18	1.02279 (10)	1.0805 (3)	0.32583 (8)	0.0324 (3)
H18A	1.0649	1.1877	0.3205	0.049*
H18B	1.0478	0.9499	0.3177	0.049*
H18C	1.0203	1.0846	0.3752	0.049*
C19	0.48791 (9)	1.1329 (2)	0.38237 (7)	0.0186 (2)
H19A	0.5565	1.1016	0.3998	0.028*
H19B	0.4779	1.2601	0.4039	0.028*
H19C	0.4638	1.1450	0.3291	0.028*
C20	0.27706 (9)	1.1291 (2)	0.36089 (7)	0.0188 (2)
H20A	0.3065	1.2511	0.3502	0.028*
H20B	0.2270	1.1663	0.3801	0.028*
H20C	0.2488	1.0506	0.3160	0.028*
H1N1	0.5810 (13)	0.620 (3)	0.4501 (10)	0.031 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.02042 (17)	0.0570 (3)	0.0355 (2)	−0.00826 (17)	0.00457 (14)	0.0233 (2)
O1	0.0176 (4)	0.0252 (5)	0.0164 (4)	0.0004 (4)	0.0046 (3)	−0.0015 (4)
O2	0.0222 (4)	0.0140 (4)	0.0196 (4)	0.0002 (4)	0.0083 (3)	0.0024 (4)
N1	0.0167 (4)	0.0162 (5)	0.0159 (4)	0.0036 (4)	0.0061 (4)	0.0030 (4)
N2	0.0169 (4)	0.0120 (5)	0.0180 (4)	0.0002 (4)	0.0074 (4)	0.0023 (4)
N3	0.0175 (4)	0.0124 (5)	0.0193 (5)	−0.0008 (4)	0.0098 (4)	0.0018 (4)
C1	0.0162 (5)	0.0194 (6)	0.0187 (5)	0.0012 (5)	0.0058 (4)	−0.0004 (5)
C2	0.0193 (5)	0.0208 (7)	0.0190 (5)	−0.0003 (5)	0.0054 (4)	0.0011 (5)
C3	0.0164 (5)	0.0305 (8)	0.0156 (5)	−0.0043 (5)	0.0049 (4)	0.0005 (5)
C4	0.0148 (5)	0.0324 (8)	0.0169 (5)	0.0016 (5)	0.0051 (4)	0.0004 (5)
C5	0.0181 (5)	0.0220 (7)	0.0163 (5)	0.0031 (5)	0.0056 (4)	−0.0004 (5)
C6	0.0166 (5)	0.0173 (6)	0.0155 (5)	−0.0002 (5)	0.0067 (4)	−0.0020 (5)
C7	0.0181 (5)	0.0166 (6)	0.0232 (6)	0.0017 (5)	0.0104 (4)	0.0003 (5)
C8	0.0155 (5)	0.0132 (6)	0.0188 (5)	−0.0020 (4)	0.0071 (4)	−0.0012 (5)
C9	0.0166 (5)	0.0157 (6)	0.0147 (5)	0.0007 (4)	0.0068 (4)	0.0007 (5)
C10	0.0161 (5)	0.0168 (6)	0.0138 (5)	−0.0003 (4)	0.0058 (4)	−0.0001 (5)
C11	0.0167 (5)	0.0155 (6)	0.0135 (5)	0.0004 (4)	0.0050 (4)	−0.0002 (4)
C12	0.0153 (5)	0.0188 (6)	0.0140 (5)	0.0006 (5)	0.0060 (4)	0.0021 (5)
C13	0.0210 (5)	0.0186 (6)	0.0218 (6)	−0.0016 (5)	0.0092 (4)	−0.0007 (5)
C14	0.0227 (6)	0.0248 (7)	0.0309 (7)	−0.0054 (5)	0.0133 (5)	0.0023 (6)
C15	0.0232 (6)	0.0341 (8)	0.0258 (6)	−0.0004 (6)	0.0147 (5)	0.0036 (6)
C16	0.0245 (6)	0.0299 (8)	0.0180 (5)	0.0018 (6)	0.0108 (5)	−0.0033 (5)
C17	0.0193 (5)	0.0220 (7)	0.0167 (5)	−0.0014 (5)	0.0060 (4)	−0.0024 (5)
C18	0.0195 (6)	0.0420 (10)	0.0339 (7)	−0.0062 (6)	0.0071 (5)	0.0014 (7)
C19	0.0197 (5)	0.0159 (6)	0.0227 (6)	−0.0010 (5)	0.0105 (4)	0.0020 (5)
C20	0.0191 (5)	0.0170 (6)	0.0199 (5)	0.0021 (5)	0.0063 (4)	0.0036 (5)

S1—C3	1.7679 (14)	C7—H7B	0.9900
S1—C18	1.7844 (14)	C9—C10	1.3534 (18)
O1—C8	1.2251 (14)	C9—C11	1.4413 (16)
O2—C11	1.2432 (15)	C10—C19	1.4843 (17)
N1—C8	1.3617 (15)	C12—C17	1.3898 (18)
N1—C9	1.4115 (15)	C12—C13	1.3936 (18)
N1—H1N1	0.878 (19)	C13—C14	1.3933 (17)
N2—C10	1.3893 (14)	C13—H13A	0.9500
N2—N3	1.4112 (14)	C14—C15	1.386 (2)
N2—C20	1.4690 (15)	C14—H14A	0.9500
N3—C11	1.3867 (16)	C15—C16	1.387 (2)
N3—C12	1.4194 (14)	C15—H15A	0.9500
C1—C2	1.3892 (18)	C16—C17	1.3946 (17)
C1—C6	1.3985 (18)	C16—H16A	0.9500
C1—H1A	0.9500	C17—H17A	0.9500
C2—C3	1.3952 (17)	C18—H18A	0.9800
C2—H2A	0.9500	C18—H18B	0.9800
C3—C4	1.399 (2)	C18—H18C	0.9800
C4—C5	1.3919 (18)	C19—H19A	0.9800
C4—H4A	0.9500	C19—H19B	0.9800
C5—C6	1.4024 (16)	C19—H19C	0.9800
C5—H5A	0.9500	C20—H20A	0.9800
C6—C7	1.5252 (17)	C20—H20B	0.9800
C7—C8	1.5187 (16)	C20—H20C	0.9800
C7—H7A	0.9900
C3—S1—C18	103.92 (7)	C9—C10—C19	129.15 (11)
C8—N1—C9	120.41 (10)	N2—C10—C19	120.82 (11)
C8—N1—H1N1	120.2 (12)	O2—C11—N3	124.27 (11)
C9—N1—H1N1	118.4 (12)	O2—C11—C9	131.34 (11)
C10—N2—N3	105.49 (10)	N3—C11—C9	104.36 (10)
C10—N2—C20	118.41 (10)	C17—C12—C13	120.95 (11)
N3—N2—C20	113.73 (9)	C17—C12—N3	120.44 (11)
C11—N3—N2	110.70 (9)	C13—C12—N3	118.60 (11)
C11—N3—C12	126.05 (11)	C14—C13—C12	119.11 (13)
N2—N3—C12	119.72 (10)	C14—C13—H13A	120.4
C2—C1—C6	121.05 (11)	C12—C13—H13A	120.4
C2—C1—H1A	119.5	C15—C14—C13	120.34 (13)
C6—C1—H1A	119.5	C15—C14—H14A	119.8
C1—C2—C3	120.65 (13)	C13—C14—H14A	119.8
C1—C2—H2A	119.7	C14—C15—C16	120.13 (12)
C3—C2—H2A	119.7	C14—C15—H15A	119.9
C2—C3—C4	118.86 (12)	C16—C15—H15A	119.9
C2—C3—S1	116.94 (11)	C15—C16—C17	120.30 (13)
C4—C3—S1	124.14 (9)	C15—C16—H16A	119.8
C5—C4—C3	120.31 (11)	C17—C16—H16A	119.8
C5—C4—H4A	119.8	C12—C17—C16	119.15 (13)
C3—C4—H4A	119.8	C12—C17—H17A	120.4
C4—C5—C6	121.08 (13)	C16—C17—H17A	120.4
C4—C5—H5A	119.5	S1—C18—H18A	109.5
C6—C5—H5A	119.5	S1—C18—H18B	109.5
C1—C6—C5	118.04 (11)	H18A—C18—H18B	109.5
C1—C6—C7	122.72 (10)	S1—C18—H18C	109.5
C5—C6—C7	119.23 (12)	H18A—C18—H18C	109.5
C8—C7—C6	112.33 (11)	H18B—C18—H18C	109.5
C8—C7—H7A	109.1	C10—C19—H19A	109.5
C6—C7—H7A	109.1	C10—C19—H19B	109.5
C8—C7—H7B	109.1	H19A—C19—H19B	109.5
C6—C7—H7B	109.1	C10—C19—H19C	109.5
H7A—C7—H7B	107.9	H19A—C19—H19C	109.5
O1—C8—N1	122.58 (11)	H19B—C19—H19C	109.5
O1—C8—C7	121.68 (11)	N2—C20—H20A	109.5
N1—C8—C7	115.70 (10)	N2—C20—H20B	109.5
C10—C9—N1	126.34 (11)	H20A—C20—H20B	109.5
C10—C9—C11	109.09 (10)	N2—C20—H20C	109.5
N1—C9—C11	124.57 (11)	H20A—C20—H20C	109.5
C9—C10—N2	110.03 (11)	H20B—C20—H20C	109.5
C10—N2—N3—C11	6.12 (12)	N1—C9—C10—C19	1.3 (2)
C20—N2—N3—C11	137.50 (10)	C11—C9—C10—C19	−177.91 (11)
C10—N2—N3—C12	166.16 (10)	N3—N2—C10—C9	−4.81 (12)
C20—N2—N3—C12	−62.45 (13)	C20—N2—C10—C9	−133.47 (11)
C6—C1—C2—C3	0.30 (19)	N3—N2—C10—C19	175.01 (10)
C1—C2—C3—C4	0.31 (19)	C20—N2—C10—C19	46.35 (16)
C1—C2—C3—S1	177.43 (10)	N2—N3—C11—O2	173.15 (11)
C18—S1—C3—C2	146.76 (11)	C12—N3—C11—O2	14.66 (19)
C18—S1—C3—C4	−36.29 (13)	N2—N3—C11—C9	−4.94 (12)
C2—C3—C4—C5	−0.98 (19)	C12—N3—C11—C9	−163.44 (11)
S1—C3—C4—C5	−177.88 (10)	C10—C9—C11—O2	−176.02 (12)
C3—C4—C5—C6	1.06 (19)	N1—C9—C11—O2	4.7 (2)
C2—C1—C6—C5	−0.24 (18)	C10—C9—C11—N3	1.88 (13)
C2—C1—C6—C7	−179.19 (11)	N1—C9—C11—N3	−177.38 (10)
C4—C5—C6—C1	−0.43 (18)	C11—N3—C12—C17	130.20 (13)
C4—C5—C6—C7	178.55 (11)	N2—N3—C12—C17	−26.55 (16)
C1—C6—C7—C8	−12.81 (16)	C11—N3—C12—C13	−50.36 (17)
C5—C6—C7—C8	168.25 (11)	N2—N3—C12—C13	152.89 (11)
C9—N1—C8—O1	1.55 (19)	C17—C12—C13—C14	−0.03 (19)
C9—N1—C8—C7	179.33 (11)	N3—C12—C13—C14	−179.46 (11)
C6—C7—C8—O1	69.15 (15)	C12—C13—C14—C15	0.9 (2)
C6—C7—C8—N1	−108.66 (12)	C13—C14—C15—C16	−0.8 (2)
C8—N1—C9—C10	−72.32 (17)	C14—C15—C16—C17	−0.1 (2)
C8—N1—C9—C11	106.81 (14)	C13—C12—C17—C16	−0.90 (18)
N1—C9—C10—N2	−178.87 (10)	N3—C12—C17—C16	178.52 (11)
C11—C9—C10—N2	1.88 (13)	C15—C16—C17—C12	0.99 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2i	0.880 (19)	1.956 (19)	2.7816 (14)	155.7 (19)
C1—H1A···O1	0.95	2.38	3.0185 (16)	124
C1—H1A···O1ii	0.95	2.51	3.2342 (16)	133
C7—H7A···O1iii	0.99	2.57	3.4960 (16)	155
C19—H19B···O2iv	0.98	2.55	3.4470 (17)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.880 (19)	1.956 (19)	2.7816 (14)	155.7 (19)
C1—H1A⋯O1	0.95	2.38	3.0185 (16)	124
C1—H1A⋯O1ii	0.95	2.51	3.2342 (16)	133
C7—H7A⋯O1iii	0.99	2.57	3.4960 (16)	155
C19—H19B⋯O2iv	0.98	2.55	3.4470 (17)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .