1-(4-Methyl-phen-yl)-3-phenyl-1H-pyrazol-5-yl 4-nitro-benzene-sulfonate.

In the title mol-ecule, C(22)H(17)N(3)O(5)S, the pyrazole ring is planar (r.m.s. deviation = 0.018 Å) and forms dihedral angles of 21.45 (10) and 6.96 (10)° with the N- and C-bound benzene rings, respectively. Supra-molecular layers in the bc plane are formed in the crystal via C-H⋯O and π-π inter-actions involving the sulfonamide benzene ring inter-acting with the N- and C-bound benzene rings [centroid-centroid distances = 3.790 (2) and 3.730 (2) Å, respectively]. The crystal studied was found to be a merohedral twin (twin law 1 0 0.678, 0 -1 0, 0 0 -1), the fractional contribution of the minor component being approximately 36%.

Related literature

For related structures and background references to pyrazoles, see: Wardell et al. (2012 ▶); Baddeley et al. (2012 ▶). For the synthesis, see: Galoyan et al. (1969 ▶). For the treatment of twinned diffraction data, see: Spek (2009 ▶).

Experimental

Crystal data

C22H17N3O5S

M = 435.46

Monoclinic,

a = 13.5339 (12) Å

b = 10.4827 (10) Å

c = 14.9303 (13) Å

β = 111.975 (3)°

V = 1964.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 120 K

0.58 × 0.38 × 0.04 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.620, T max = 0.746

4454 measured reflections

4454 independent reflections

3951 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.179

S = 1.19

4454 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.62 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010598/hb6674sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010598/hb6674Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010598/hb6674Isup3.cml

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

C22H17N3O5S	F(000) = 904
Mr = 435.46	Dx = 1.472 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 67707 reflections
a = 13.5339 (12) Å	θ = 2.9–27.5°
b = 10.4827 (10) Å	µ = 0.21 mm−1
c = 14.9303 (13) Å	T = 120 K
β = 111.975 (3)°	Plate, yellow
V = 1964.3 (3) Å3	0.58 × 0.38 × 0.04 mm
Z = 4

Rigaku Saturn724+ diffractometer	4454 independent reflections
Radiation source: Rotating Anode	3951 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.000
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.2°
profile data from ω–scans	h = −17→16
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = 0→13
Tmin = 0.620, Tmax = 0.746	l = 0→19
4454 measured reflections

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0562P)2 + 4.737P] where P = (Fo2 + 2Fc2)/3
4454 reflections	(Δ/σ)max < 0.001
282 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.47829 (6)	0.20331 (9)	0.00726 (6)	0.0203 (2)
O1	0.51909 (18)	0.3508 (3)	0.01445 (17)	0.0203 (5)
O2	0.5619 (2)	0.1219 (3)	0.0044 (2)	0.0268 (6)
O3	0.4369 (2)	0.1938 (3)	0.08223 (19)	0.0315 (7)
O4	0.1490 (2)	0.2303 (3)	−0.4513 (2)	0.0360 (7)
O5	0.0359 (2)	0.2650 (3)	−0.3824 (2)	0.0377 (8)
N1	0.7023 (2)	0.4081 (3)	0.0618 (2)	0.0156 (6)
N2	0.7780 (2)	0.4243 (3)	0.0225 (2)	0.0156 (6)
N3	0.1265 (2)	0.2427 (3)	−0.3796 (2)	0.0254 (7)
C1	0.6074 (2)	0.3760 (3)	−0.0095 (2)	0.0169 (7)
C2	0.7290 (2)	0.4006 (3)	−0.0717 (2)	0.0141 (6)
C3	0.6198 (3)	0.3718 (3)	−0.0957 (2)	0.0183 (7)
H3	0.5673	0.3539	−0.1576	0.022*
C4	0.3726 (3)	0.2062 (3)	−0.1065 (3)	0.0185 (7)
C5	0.2715 (3)	0.2430 (4)	−0.1110 (3)	0.0206 (7)
H5	0.2587	0.2609	−0.0539	0.025*
C6	0.1898 (3)	0.2525 (4)	−0.2022 (3)	0.0222 (7)
H6	0.1196	0.2749	−0.2081	0.027*
C7	0.2126 (3)	0.2292 (3)	−0.2831 (3)	0.0199 (7)
C8	0.3132 (3)	0.1929 (4)	−0.2796 (3)	0.0220 (7)
H8	0.3262	0.1777	−0.3370	0.026*
C9	0.3942 (3)	0.1796 (3)	−0.1886 (3)	0.0189 (7)
H9	0.4633	0.1527	−0.1829	0.023*
C10	0.7302 (3)	0.4228 (3)	0.1639 (2)	0.0152 (6)
C11	0.8359 (3)	0.3992 (3)	0.2245 (3)	0.0181 (7)
H11	0.8871	0.3757	0.1980	0.022*
C12	0.8651 (3)	0.4106 (3)	0.3239 (2)	0.0198 (7)
H12	0.9369	0.3951	0.3651	0.024*
C13	0.7909 (3)	0.4445 (3)	0.3644 (3)	0.0210 (7)
C14	0.6856 (3)	0.4686 (4)	0.3023 (3)	0.0211 (7)
H14	0.6343	0.4919	0.3287	0.025*
C15	0.6551 (3)	0.4590 (3)	0.2020 (3)	0.0197 (7)
H15	0.5838	0.4770	0.1604	0.024*
C16	0.8218 (3)	0.4510 (4)	0.4733 (3)	0.0307 (9)
H16A	0.7642	0.4912	0.4879	0.046*
H16B	0.8871	0.5014	0.5020	0.046*
H16C	0.8341	0.3645	0.5002	0.046*
C17	0.7883 (3)	0.4054 (3)	−0.1369 (2)	0.0157 (6)
C18	0.7359 (3)	0.3973 (3)	−0.2370 (2)	0.0166 (6)
H18	0.6609	0.3851	−0.2640	0.020*
C19	0.7925 (3)	0.4068 (3)	−0.2978 (2)	0.0191 (7)
H19	0.7563	0.4007	−0.3658	0.023*
C20	0.9031 (3)	0.4255 (4)	−0.2584 (3)	0.0210 (7)
H20	0.9417	0.4348	−0.2997	0.025*
C21	0.9563 (3)	0.4303 (3)	−0.1586 (3)	0.0194 (7)
H21	1.0315	0.4409	−0.1319	0.023*
C22	0.8997 (3)	0.4196 (3)	−0.0977 (2)	0.0185 (7)
H22	0.9365	0.4218	−0.0297	0.022*

	U11	U22	U33	U12	U13	U23
S1	0.0124 (4)	0.0288 (5)	0.0195 (4)	−0.0052 (3)	0.0057 (3)	0.0020 (4)
O1	0.0110 (10)	0.0319 (14)	0.0212 (12)	−0.0056 (10)	0.0097 (10)	−0.0077 (10)
O2	0.0167 (12)	0.0245 (14)	0.0359 (15)	0.0004 (10)	0.0058 (11)	0.0053 (12)
O3	0.0206 (12)	0.0545 (19)	0.0206 (13)	−0.0108 (13)	0.0090 (11)	0.0067 (13)
O4	0.0335 (15)	0.0501 (19)	0.0210 (14)	−0.0070 (14)	0.0061 (12)	−0.0007 (13)
O5	0.0202 (13)	0.050 (2)	0.0338 (16)	0.0089 (13)	−0.0002 (12)	−0.0092 (14)
N1	0.0106 (12)	0.0238 (15)	0.0136 (13)	−0.0030 (11)	0.0057 (11)	0.0008 (11)
N2	0.0110 (12)	0.0238 (15)	0.0144 (13)	−0.0021 (11)	0.0075 (11)	0.0014 (11)
N3	0.0230 (15)	0.0232 (16)	0.0244 (17)	−0.0028 (13)	0.0024 (13)	−0.0025 (13)
C1	0.0077 (13)	0.0240 (17)	0.0179 (15)	−0.0046 (12)	0.0034 (12)	−0.0022 (14)
C2	0.0113 (14)	0.0175 (16)	0.0127 (15)	−0.0014 (12)	0.0034 (12)	−0.0004 (12)
C3	0.0126 (14)	0.0237 (18)	0.0171 (16)	−0.0034 (13)	0.0037 (12)	−0.0022 (13)
C4	0.0124 (14)	0.0224 (17)	0.0190 (16)	−0.0046 (13)	0.0040 (12)	−0.0001 (14)
C5	0.0161 (15)	0.0254 (18)	0.0228 (18)	−0.0043 (14)	0.0100 (13)	−0.0032 (14)
C6	0.0139 (15)	0.0242 (18)	0.0274 (19)	−0.0010 (14)	0.0066 (14)	−0.0014 (15)
C7	0.0146 (15)	0.0196 (17)	0.0225 (17)	−0.0042 (13)	0.0035 (13)	−0.0020 (14)
C8	0.0190 (16)	0.0241 (18)	0.0227 (17)	−0.0044 (14)	0.0077 (14)	−0.0029 (14)
C9	0.0137 (14)	0.0210 (17)	0.0240 (18)	−0.0029 (13)	0.0093 (13)	−0.0036 (14)
C10	0.0163 (15)	0.0177 (16)	0.0104 (15)	−0.0014 (12)	0.0036 (12)	−0.0001 (12)
C11	0.0141 (15)	0.0231 (17)	0.0172 (16)	0.0001 (13)	0.0060 (13)	0.0017 (13)
C12	0.0174 (16)	0.0220 (18)	0.0172 (17)	−0.0024 (13)	0.0034 (13)	0.0007 (13)
C13	0.0273 (18)	0.0200 (17)	0.0164 (16)	−0.0054 (14)	0.0090 (14)	−0.0015 (14)
C14	0.0214 (17)	0.0235 (18)	0.0225 (18)	−0.0019 (14)	0.0130 (15)	−0.0020 (14)
C15	0.0170 (15)	0.0209 (16)	0.0218 (17)	−0.0019 (13)	0.0080 (14)	−0.0015 (14)
C16	0.037 (2)	0.039 (2)	0.0143 (17)	−0.0007 (18)	0.0082 (16)	0.0005 (16)
C17	0.0159 (15)	0.0178 (16)	0.0145 (15)	−0.0020 (12)	0.0071 (13)	−0.0001 (12)
C18	0.0159 (15)	0.0189 (16)	0.0137 (15)	−0.0007 (12)	0.0040 (12)	−0.0002 (13)
C19	0.0209 (16)	0.0214 (17)	0.0135 (16)	−0.0014 (13)	0.0050 (13)	−0.0006 (13)
C20	0.0217 (17)	0.0263 (19)	0.0220 (18)	−0.0007 (14)	0.0163 (15)	−0.0008 (14)
C21	0.0134 (15)	0.0246 (18)	0.0207 (17)	−0.0030 (13)	0.0071 (13)	−0.0002 (14)
C22	0.0161 (15)	0.0248 (18)	0.0135 (15)	−0.0007 (13)	0.0045 (13)	−0.0001 (13)

S1—O3	1.430 (3)	C10—C15	1.391 (5)
S1—O2	1.431 (3)	C10—C11	1.399 (4)
S1—O1	1.632 (3)	C11—C12	1.391 (5)
S1—C4	1.765 (3)	C11—H11	0.9500
O1—C1	1.395 (4)	C12—C13	1.397 (5)
O4—N3	1.225 (4)	C12—H12	0.9500
O5—N3	1.233 (4)	C13—C14	1.402 (5)
N1—N2	1.366 (4)	C13—C16	1.522 (5)
N1—C1	1.368 (4)	C14—C15	1.401 (5)
N1—C10	1.435 (4)	C14—H14	0.9500
N2—C2	1.336 (4)	C15—H15	0.9500
N3—C7	1.482 (5)	C16—H16A	0.9800
C1—C3	1.360 (5)	C16—H16B	0.9800
C2—C3	1.417 (4)	C16—H16C	0.9800
C2—C17	1.476 (4)	C17—C18	1.397 (5)
C3—H3	0.9500	C17—C22	1.406 (5)
C4—C9	1.390 (5)	C18—C19	1.393 (5)
C4—C5	1.399 (5)	C18—H18	0.9500
C5—C6	1.399 (5)	C19—C20	1.402 (5)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.376 (5)	C20—C21	1.391 (5)
C6—H6	0.9500	C20—H20	0.9500
C7—C8	1.396 (5)	C21—C22	1.396 (5)
C8—C9	1.397 (5)	C21—H21	0.9500
C8—H8	0.9500	C22—H22	0.9500
C9—H9	0.9500
O3—S1—O2	121.83 (18)	C15—C10—N1	121.5 (3)
O3—S1—O1	103.66 (16)	C11—C10—N1	117.8 (3)
O2—S1—O1	108.38 (14)	C12—C11—C10	119.2 (3)
O3—S1—C4	109.94 (16)	C12—C11—H11	120.4
O2—S1—C4	110.29 (17)	C10—C11—H11	120.4
O1—S1—C4	100.35 (15)	C11—C12—C13	121.4 (3)
C1—O1—S1	117.6 (2)	C11—C12—H12	119.3
N2—N1—C1	109.5 (3)	C13—C12—H12	119.3
N2—N1—C10	120.0 (3)	C12—C13—C14	118.5 (3)
C1—N1—C10	130.5 (3)	C12—C13—C16	121.3 (3)
C2—N2—N1	105.8 (2)	C14—C13—C16	120.2 (3)
O4—N3—O5	124.0 (3)	C15—C14—C13	120.9 (3)
O4—N3—C7	118.5 (3)	C15—C14—H14	119.5
O5—N3—C7	117.4 (3)	C13—C14—H14	119.5
C3—C1—N1	109.4 (3)	C10—C15—C14	119.2 (3)
C3—C1—O1	131.1 (3)	C10—C15—H15	120.4
N1—C1—O1	119.5 (3)	C14—C15—H15	120.4
N2—C2—C3	111.4 (3)	C13—C16—H16A	109.5
N2—C2—C17	120.7 (3)	C13—C16—H16B	109.5
C3—C2—C17	127.9 (3)	H16A—C16—H16B	109.5
C1—C3—C2	103.9 (3)	C13—C16—H16C	109.5
C1—C3—H3	128.0	H16A—C16—H16C	109.5
C2—C3—H3	128.0	H16B—C16—H16C	109.5
C9—C4—C5	122.5 (3)	C18—C17—C22	119.2 (3)
C9—C4—S1	118.9 (3)	C18—C17—C2	121.3 (3)
C5—C4—S1	118.5 (3)	C22—C17—C2	119.5 (3)
C4—C5—C6	118.0 (3)	C19—C18—C17	120.7 (3)
C4—C5—H5	121.0	C19—C18—H18	119.7
C6—C5—H5	121.0	C17—C18—H18	119.7
C7—C6—C5	119.1 (3)	C18—C19—C20	119.8 (3)
C7—C6—H6	120.4	C18—C19—H19	120.1
C5—C6—H6	120.4	C20—C19—H19	120.1
C6—C7—C8	123.5 (3)	C21—C20—C19	119.9 (3)
C6—C7—N3	118.9 (3)	C21—C20—H20	120.1
C8—C7—N3	117.6 (3)	C19—C20—H20	120.1
C7—C8—C9	117.5 (3)	C20—C21—C22	120.3 (3)
C7—C8—H8	121.2	C20—C21—H21	119.9
C9—C8—H8	121.2	C22—C21—H21	119.9
C4—C9—C8	119.4 (3)	C21—C22—C17	120.1 (3)
C4—C9—H9	120.3	C21—C22—H22	119.9
C8—C9—H9	120.3	C17—C22—H22	119.9
C15—C10—C11	120.7 (3)
O3—S1—O1—C1	147.7 (2)	C6—C7—C8—C9	0.2 (6)
O2—S1—O1—C1	17.0 (3)	N3—C7—C8—C9	−179.7 (3)
C4—S1—O1—C1	−98.6 (2)	C5—C4—C9—C8	1.7 (5)
C1—N1—N2—C2	−0.7 (4)	S1—C4—C9—C8	−174.2 (3)
C10—N1—N2—C2	178.1 (3)	C7—C8—C9—C4	−1.8 (5)
N2—N1—C1—C3	−0.5 (4)	N2—N1—C10—C15	153.3 (3)
C10—N1—C1—C3	−179.1 (3)	C1—N1—C10—C15	−28.3 (6)
N2—N1—C1—O1	178.0 (3)	N2—N1—C10—C11	−26.9 (5)
C10—N1—C1—O1	−0.5 (6)	C1—N1—C10—C11	151.6 (4)
S1—O1—C1—C3	69.1 (5)	C15—C10—C11—C12	0.9 (5)
S1—O1—C1—N1	−109.1 (3)	N1—C10—C11—C12	−179.0 (3)
N1—N2—C2—C3	1.5 (4)	C10—C11—C12—C13	0.4 (5)
N1—N2—C2—C17	−178.1 (3)	C11—C12—C13—C14	−0.8 (5)
N1—C1—C3—C2	1.3 (4)	C11—C12—C13—C16	177.2 (4)
O1—C1—C3—C2	−177.0 (4)	C12—C13—C14—C15	0.1 (5)
N2—C2—C3—C1	−1.8 (4)	C16—C13—C14—C15	−177.9 (4)
C17—C2—C3—C1	177.8 (3)	C11—C10—C15—C14	−1.6 (5)
O3—S1—C4—C9	−162.3 (3)	N1—C10—C15—C14	178.2 (3)
O2—S1—C4—C9	−25.3 (3)	C13—C14—C15—C10	1.1 (5)
O1—S1—C4—C9	88.9 (3)	N2—C2—C17—C18	−171.6 (3)
O3—S1—C4—C5	21.6 (4)	C3—C2—C17—C18	8.8 (5)
O2—S1—C4—C5	158.7 (3)	N2—C2—C17—C22	7.8 (5)
O1—S1—C4—C5	−87.2 (3)	C3—C2—C17—C22	−171.8 (3)
C9—C4—C5—C6	0.2 (5)	C22—C17—C18—C19	−1.9 (5)
S1—C4—C5—C6	176.1 (3)	C2—C17—C18—C19	177.5 (3)
C4—C5—C6—C7	−1.8 (5)	C17—C18—C19—C20	−0.4 (5)
C5—C6—C7—C8	1.6 (6)	C18—C19—C20—C21	2.1 (6)
C5—C6—C7—N3	−178.4 (3)	C19—C20—C21—C22	−1.5 (6)
O4—N3—C7—C6	175.1 (4)	C20—C21—C22—C17	−0.8 (5)
O5—N3—C7—C6	−5.4 (5)	C18—C17—C22—C21	2.5 (5)
O4—N3—C7—C8	−5.0 (5)	C2—C17—C22—C21	−177.0 (3)
O5—N3—C7—C8	174.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4i	0.95	2.50	3.387 (5)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4i	0.95	2.50	3.387 (5)	155

Symmetry code: (i) .