1-(4-Methyl-phenyl-sulfon-yl)-5-phenyl-4,5-dihydro-1H-pyrazole.

The title compound, C(16)H(16)N(2)O(2)S, was synthesized by the reaction of 5-phenyl-4,5-dihydro-1H-pyrazole and 4-methyl-benzene-1-sulfonyl chloride. The five-membered pyrazoline ring is nearly planar, with a miximum deviation of 0.078 (2) Å.

Related literature

For the pharmacological properties of pyrazoline derivatives, see: Goodell et al. (2006 ▶); Park et al. (2005 ▶); Shaharyar et al. (2006 ▶); Suresh et al. (2009 ▶).

Experimental

Crystal data

C16H16N2O2S

M = 300.37

Orthorhombic,

a = 19.2938 (7) Å

b = 6.0438 (2) Å

c = 12.9812 (5) Å

V = 1513.71 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.32 × 0.28 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.933, T max = 0.947

5286 measured reflections

2168 independent reflections

1870 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.081

S = 1.05

2168 reflections

191 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 711 Friedel pairs

Flack parameter: 0.00 (8)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025001/bv2186sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025001/bv2186Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025001/bv2186Isup3.cml

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

C16H16N2O2S	F(000) = 632
Mr = 300.37	Dx = 1.318 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2341 reflections
a = 19.2938 (7) Å	θ = 3.1–29.4°
b = 6.0438 (2) Å	µ = 0.22 mm−1
c = 12.9812 (5) Å	T = 293 K
V = 1513.71 (10) Å3	Block, colorless
Z = 4	0.32 × 0.28 × 0.25 mm

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	2168 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 10.3592 pixels mm-1	θmax = 25.4°, θmin = 3.1°
ω scans	h = −17→23
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→7
Tmin = 0.933, Tmax = 0.947	l = −15→10
5286 measured reflections

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.0462P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2168 reflections	Δρmax = 0.15 e Å−3
191 parameters	Δρmin = −0.26 e Å−3
1 restraint	Absolute structure: Flack (1983), 711 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (8)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.36119 (3)	0.55535 (9)	0.53950 (5)	0.0517 (2)
O1	0.37103 (10)	0.7881 (3)	0.5338 (2)	0.0737 (6)
O2	0.34854 (11)	0.4301 (3)	0.44842 (16)	0.0680 (6)
N1	0.29819 (12)	0.6172 (4)	0.7097 (2)	0.0680 (7)
N2	0.29200 (10)	0.5148 (3)	0.61190 (18)	0.0511 (6)
C1	0.43222 (13)	0.4394 (4)	0.6042 (2)	0.0452 (6)
C2	0.45625 (14)	0.2327 (4)	0.5752 (2)	0.0555 (7)
H2	0.4349	0.1557	0.5218	0.067*
C3	0.51202 (15)	0.1425 (4)	0.6261 (3)	0.0581 (7)
H3	0.5285	0.0046	0.6058	0.070*
C4	0.54427 (13)	0.2507 (4)	0.7066 (2)	0.0547 (7)
C5	0.60491 (17)	0.1474 (5)	0.7611 (3)	0.0828 (10)
H5C	0.6114	0.2183	0.8266	0.124*
H5B	0.6459	0.1653	0.7201	0.124*
H5A	0.5961	−0.0073	0.7715	0.124*
C6	0.51950 (14)	0.4589 (4)	0.7345 (2)	0.0530 (7)
H6	0.5409	0.5358	0.7878	0.064*
C7	0.46389 (13)	0.5524 (4)	0.6845 (2)	0.0500 (7)
H7	0.4476	0.6908	0.7044	0.060*
C8	0.26877 (16)	0.4944 (7)	0.7745 (3)	0.0833 (11)
H8	0.2666	0.5317	0.8440	0.100*
C9	0.23803 (18)	0.2892 (6)	0.7349 (3)	0.0839 (11)
H9A	0.1878	0.2940	0.7383	0.101*
H9B	0.2545	0.1614	0.7729	0.101*
C10	0.26345 (13)	0.2845 (4)	0.6227 (2)	0.0523 (7)
H10	0.3006	0.1753	0.6148	0.063*
C11	0.20658 (11)	0.2411 (3)	0.5454 (2)	0.0428 (5)
C12	0.15381 (12)	0.3928 (4)	0.5298 (3)	0.0516 (6)
H12	0.1543	0.5262	0.5654	0.062*
C13	0.10086 (14)	0.3487 (5)	0.4626 (2)	0.0619 (8)
H13	0.0661	0.4530	0.4525	0.074*
C14	0.09883 (16)	0.1535 (5)	0.4104 (3)	0.0705 (9)
H14	0.0627	0.1240	0.3651	0.085*
C15	0.15027 (17)	0.0006 (5)	0.4250 (3)	0.0694 (9)
H15	0.1490	−0.1331	0.3895	0.083*
C16	0.20389 (14)	0.0445 (4)	0.4922 (2)	0.0576 (7)
H16	0.2387	−0.0601	0.5017	0.069*

	U11	U22	U33	U12	U13	U23
S1	0.0487 (4)	0.0551 (3)	0.0513 (4)	−0.0086 (3)	−0.0036 (4)	0.0102 (4)
O1	0.0702 (12)	0.0549 (9)	0.0961 (16)	−0.0138 (8)	−0.0086 (14)	0.0230 (14)
O2	0.0698 (14)	0.0891 (13)	0.0451 (12)	−0.0115 (10)	−0.0081 (10)	0.0042 (11)
N1	0.0476 (14)	0.0842 (16)	0.072 (2)	−0.0022 (12)	0.0035 (14)	−0.0205 (16)
N2	0.0439 (12)	0.0530 (10)	0.0564 (15)	−0.0063 (9)	−0.0051 (11)	0.0041 (11)
C1	0.0434 (14)	0.0462 (12)	0.0460 (16)	−0.0091 (10)	0.0061 (12)	−0.0001 (12)
C2	0.0560 (17)	0.0538 (13)	0.0567 (18)	−0.0112 (12)	0.0010 (14)	−0.0077 (14)
C3	0.0597 (17)	0.0482 (13)	0.0663 (19)	0.0048 (12)	0.0084 (16)	−0.0035 (15)
C4	0.0438 (15)	0.0616 (15)	0.0585 (18)	0.0016 (13)	0.0070 (14)	−0.0004 (16)
C5	0.068 (2)	0.091 (2)	0.089 (3)	0.0186 (18)	−0.0106 (19)	−0.003 (2)
C6	0.0498 (16)	0.0601 (15)	0.0491 (16)	−0.0071 (12)	−0.0003 (14)	−0.0072 (15)
C7	0.0482 (15)	0.0467 (12)	0.0551 (18)	−0.0020 (11)	0.0042 (13)	−0.0080 (13)
C8	0.051 (2)	0.143 (3)	0.056 (2)	−0.020 (2)	−0.0031 (17)	−0.010 (2)
C9	0.076 (2)	0.123 (3)	0.0524 (19)	−0.037 (2)	−0.0169 (18)	0.029 (2)
C10	0.0441 (14)	0.0538 (13)	0.0589 (18)	−0.0075 (11)	−0.0118 (15)	0.0135 (14)
C11	0.0375 (12)	0.0484 (11)	0.0424 (14)	−0.0041 (9)	0.0018 (14)	0.0101 (13)
C12	0.0450 (14)	0.0557 (12)	0.0540 (17)	0.0044 (10)	−0.0020 (16)	−0.0027 (15)
C13	0.0484 (16)	0.0702 (16)	0.067 (2)	0.0055 (14)	−0.0098 (16)	0.0054 (16)
C14	0.063 (2)	0.085 (2)	0.064 (2)	−0.0111 (16)	−0.0217 (16)	0.0068 (18)
C15	0.083 (2)	0.0592 (15)	0.066 (2)	−0.0050 (15)	−0.0100 (19)	−0.0082 (17)
C16	0.0557 (17)	0.0519 (14)	0.0653 (19)	0.0081 (12)	−0.0054 (15)	0.0044 (14)

S1—O1	1.4213 (16)	C7—H7	0.9300
S1—O2	1.425 (2)	C8—C9	1.468 (5)
S1—N2	1.651 (2)	C8—H8	0.9300
S1—C1	1.754 (3)	C9—C10	1.537 (5)
N1—C8	1.257 (4)	C9—H9A	0.9700
N1—N2	1.417 (3)	C9—H9B	0.9700
N2—C10	1.504 (3)	C10—C11	1.510 (4)
C1—C2	1.385 (3)	C10—H10	0.9800
C1—C7	1.387 (4)	C11—C16	1.375 (4)
C2—C3	1.376 (4)	C11—C12	1.385 (3)
C2—H2	0.9300	C12—C13	1.370 (4)
C3—C4	1.380 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.361 (4)
C4—C6	1.394 (3)	C13—H13	0.9300
C4—C5	1.503 (4)	C14—C15	1.369 (4)
C5—H5C	0.9600	C14—H14	0.9300
C5—H5B	0.9600	C15—C16	1.379 (4)
C5—H5A	0.9600	C15—H15	0.9300
C6—C7	1.376 (4)	C16—H16	0.9300
C6—H6	0.9300
O1—S1—O2	120.35 (16)	N1—C8—C9	116.5 (3)
O1—S1—N2	106.53 (13)	N1—C8—H8	121.7
O2—S1—N2	104.77 (12)	C9—C8—H8	121.7
O1—S1—C1	108.43 (12)	C8—C9—C10	102.6 (3)
O2—S1—C1	108.62 (12)	C8—C9—H9A	111.2
N2—S1—C1	107.45 (11)	C10—C9—H9A	111.2
C8—N1—N2	107.7 (3)	C8—C9—H9B	111.2
N1—N2—C10	110.6 (2)	C10—C9—H9B	111.2
N1—N2—S1	112.15 (17)	H9A—C9—H9B	109.2
C10—N2—S1	119.12 (17)	N2—C10—C11	111.4 (2)
C2—C1—C7	120.1 (2)	N2—C10—C9	100.8 (2)
C2—C1—S1	119.4 (2)	C11—C10—C9	113.7 (2)
C7—C1—S1	120.48 (18)	N2—C10—H10	110.2
C3—C2—C1	119.2 (3)	C11—C10—H10	110.2
C3—C2—H2	120.4	C9—C10—H10	110.2
C1—C2—H2	120.4	C16—C11—C12	118.1 (2)
C2—C3—C4	121.9 (2)	C16—C11—C10	120.7 (2)
C2—C3—H3	119.0	C12—C11—C10	121.1 (2)
C4—C3—H3	119.0	C13—C12—C11	120.9 (2)
C3—C4—C6	118.0 (3)	C13—C12—H12	119.6
C3—C4—C5	120.7 (2)	C11—C12—H12	119.6
C6—C4—C5	121.3 (3)	C14—C13—C12	120.4 (3)
C4—C5—H5C	109.5	C14—C13—H13	119.8
C4—C5—H5B	109.5	C12—C13—H13	119.8
H5C—C5—H5B	109.5	C13—C14—C15	119.7 (3)
C4—C5—H5A	109.5	C13—C14—H14	120.1
H5C—C5—H5A	109.5	C15—C14—H14	120.1
H5B—C5—H5A	109.5	C14—C15—C16	120.1 (3)
C7—C6—C4	121.0 (3)	C14—C15—H15	120.0
C7—C6—H6	119.5	C16—C15—H15	120.0
C4—C6—H6	119.5	C11—C16—C15	120.8 (3)
C6—C7—C1	119.7 (2)	C11—C16—H16	119.6
C6—C7—H7	120.1	C15—C16—H16	119.6
C1—C7—H7	120.1