4-(3,4-Diacetyl-5-methyl-1H-pyrazol-1-yl)benzene-sulfonamide.

In the title mol-ecule, C(14)H(15)N(3)O(4)S, the pyrazole ring is aligned at a dihedral angle of 55.5 (1)° with respect to the benzene ring; the mean planes of the acetyl substituents are twisted by 13.4 (3) and 30.1 (3)° with respect to the pyrazole ring. Inter-molecular classical N-H⋯O and weak C-H⋯O hydrogen bonding links the mol-ecules, forming a three-dimensional network architecture in the crystal structure.

Related literature

For background to the biological properties of aryl-substituted pyrazoles, see: Abdel-Aziz et al. (2010 ▶).

Experimental

Crystal data

C14H15N3O4S

M = 321.35

Orthorhombic,

a = 8.3716 (3) Å

b = 21.7722 (8) Å

c = 7.8915 (3) Å

V = 1438.37 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 100 K

0.20 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.952, T max = 0.988

10477 measured reflections

3087 independent reflections

2634 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.095

S = 1.05

3087 reflections

210 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.39 e Å−3

Absolute structure: Flack (1983 ▶), 1337 Friedel pairs

Flack parameter: 0.08 (8)

Data collection: CrysAlis PRO (Agilent, 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005733/xu5161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005733/xu5161Isup2.hkl

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

C14H15N3O4S	F(000) = 672
Mr = 321.35	Dx = 1.484 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3291 reflections
a = 8.3716 (3) Å	θ = 2.4–29.2°
b = 21.7722 (8) Å	µ = 0.25 mm−1
c = 7.8915 (3) Å	T = 100 K
V = 1438.37 (9) Å3	Prism, colorless
Z = 4	0.20 × 0.15 × 0.05 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	3087 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2634 reflections with I > 2σ(I)
Mirror	Rint = 0.056
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.6°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −28→27
Tmin = 0.952, Tmax = 0.988	l = −10→9
10477 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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0422P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3087 reflections	Δρmax = 0.31 e Å−3
210 parameters	Δρmin = −0.39 e Å−3
3 restraints	Absolute structure: Flack (1983), 1337 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (8)

	x	y	z	Uiso*/Ueq
S1	0.69022 (7)	0.29885 (3)	0.49994 (9)	0.01726 (16)
O1	1.5767 (2)	0.55022 (9)	0.1918 (3)	0.0278 (5)
O2	1.3205 (2)	0.68881 (8)	0.5594 (3)	0.0229 (5)
O3	0.7216 (2)	0.27511 (9)	0.6664 (3)	0.0234 (5)
O4	0.5323 (2)	0.31899 (7)	0.4576 (3)	0.0226 (5)
N1	1.0863 (2)	0.56565 (9)	0.4491 (3)	0.0164 (5)
N2	1.1261 (2)	0.50985 (9)	0.3847 (3)	0.0160 (5)
N3	0.7369 (3)	0.24582 (10)	0.3684 (3)	0.0182 (5)
H31	0.726 (3)	0.2569 (13)	0.2624 (17)	0.017 (8)*
H32	0.8310 (18)	0.2289 (11)	0.385 (4)	0.021 (8)*
C1	1.5821 (3)	0.64151 (12)	0.3508 (4)	0.0235 (7)
H1A	1.6916	0.6438	0.3072	0.035*
H1B	1.5845	0.6411	0.4750	0.035*
H1C	1.5215	0.6773	0.3115	0.035*
C2	1.5041 (3)	0.58395 (12)	0.2877 (4)	0.0196 (6)
C3	1.3404 (3)	0.56637 (11)	0.3441 (3)	0.0149 (6)
C4	1.2165 (3)	0.60007 (11)	0.4274 (3)	0.0157 (6)
C5	1.2032 (3)	0.66253 (11)	0.5028 (4)	0.0179 (5)
C6	1.0404 (3)	0.68993 (11)	0.5136 (5)	0.0252 (6)
H6A	1.0466	0.7299	0.5704	0.038*
H6B	0.9704	0.6625	0.5783	0.038*
H6C	0.9972	0.6954	0.3992	0.038*
C7	1.2751 (3)	0.50868 (12)	0.3166 (3)	0.0170 (6)
C8	1.3336 (3)	0.45309 (12)	0.2257 (4)	0.0236 (7)
H8A	1.2448	0.4339	0.1646	0.035*
H8B	1.3777	0.4238	0.3077	0.035*
H8C	1.4170	0.4650	0.1449	0.035*
C9	1.0197 (3)	0.45957 (11)	0.4118 (4)	0.0160 (6)
C10	0.8629 (3)	0.46375 (12)	0.3568 (3)	0.0176 (6)
H10	0.8261	0.4996	0.3002	0.021*
C11	0.7607 (3)	0.41477 (12)	0.3856 (4)	0.0196 (6)
H11	0.6525	0.4168	0.3498	0.024*
C12	0.8176 (3)	0.36269 (11)	0.4670 (3)	0.0172 (6)
C13	0.9744 (3)	0.35924 (11)	0.5236 (4)	0.0178 (6)
H13	1.0112	0.3236	0.5810	0.021*
C14	1.0763 (3)	0.40801 (11)	0.4958 (4)	0.0190 (6)
H14	1.1839	0.4063	0.5338	0.023*

	U11	U22	U33	U12	U13	U23
S1	0.0148 (3)	0.0163 (3)	0.0207 (4)	−0.0022 (2)	0.0012 (3)	0.0006 (3)
O1	0.0200 (10)	0.0241 (10)	0.0392 (13)	0.0012 (8)	0.0106 (10)	−0.0016 (10)
O2	0.0238 (11)	0.0223 (10)	0.0226 (12)	−0.0058 (8)	0.0029 (8)	−0.0047 (9)
O3	0.0263 (10)	0.0229 (10)	0.0211 (12)	−0.0025 (9)	0.0023 (9)	0.0001 (9)
O4	0.0157 (9)	0.0188 (9)	0.0334 (14)	−0.0020 (7)	0.0016 (8)	0.0017 (9)
N1	0.0164 (11)	0.0135 (10)	0.0192 (13)	0.0009 (8)	0.0006 (9)	−0.0009 (9)
N2	0.0147 (11)	0.0159 (10)	0.0175 (12)	0.0008 (9)	−0.0015 (9)	−0.0025 (10)
N3	0.0192 (12)	0.0160 (11)	0.0192 (14)	−0.0004 (9)	−0.0017 (10)	0.0022 (11)
C1	0.0171 (13)	0.0244 (14)	0.0289 (18)	−0.0047 (11)	0.0023 (12)	−0.0023 (14)
C2	0.0170 (13)	0.0203 (14)	0.0215 (16)	0.0011 (11)	−0.0017 (12)	0.0043 (14)
C3	0.0143 (12)	0.0174 (13)	0.0132 (15)	−0.0004 (10)	−0.0010 (10)	0.0031 (11)
C4	0.0165 (12)	0.0173 (12)	0.0134 (14)	−0.0015 (10)	−0.0011 (11)	0.0011 (12)
C5	0.0242 (13)	0.0162 (12)	0.0134 (13)	−0.0016 (10)	0.0032 (13)	0.0016 (14)
C6	0.0255 (14)	0.0191 (13)	0.0312 (18)	0.0020 (11)	0.0024 (15)	−0.0052 (14)
C7	0.0155 (13)	0.0180 (13)	0.0176 (15)	−0.0002 (10)	−0.0017 (11)	0.0026 (12)
C8	0.0190 (13)	0.0197 (14)	0.0321 (19)	−0.0007 (11)	0.0051 (12)	−0.0050 (13)
C9	0.0163 (12)	0.0147 (12)	0.0170 (15)	−0.0027 (10)	0.0032 (11)	−0.0048 (11)
C10	0.0173 (13)	0.0151 (12)	0.0204 (16)	0.0021 (10)	0.0002 (11)	−0.0003 (12)
C11	0.0118 (12)	0.0241 (13)	0.0229 (16)	0.0013 (11)	−0.0031 (11)	−0.0012 (14)
C12	0.0165 (12)	0.0158 (12)	0.0193 (17)	0.0001 (10)	0.0031 (11)	−0.0017 (12)
C13	0.0179 (12)	0.0150 (12)	0.0207 (16)	0.0032 (10)	−0.0021 (11)	0.0007 (12)
C14	0.0157 (12)	0.0189 (12)	0.0224 (15)	0.0016 (10)	−0.0001 (13)	−0.0040 (13)

S1—O4	1.4325 (18)	C4—C5	1.489 (3)
S1—O3	1.436 (2)	C5—C6	1.490 (3)
S1—N3	1.601 (3)	C6—H6A	0.9800
S1—C12	1.771 (2)	C6—H6B	0.9800
O1—C2	1.218 (3)	C6—H6C	0.9800
O2—C5	1.221 (3)	C7—C8	1.490 (4)
N1—C4	1.334 (3)	C8—H8A	0.9800
N1—N2	1.358 (3)	C8—H8B	0.9800
N2—C7	1.358 (3)	C8—H8C	0.9800
N2—C9	1.427 (3)	C9—C10	1.385 (3)
N3—H31	0.875 (10)	C9—C14	1.387 (4)
N3—H32	0.879 (10)	C10—C11	1.386 (4)
C1—C2	1.498 (4)	C10—H10	0.9500
C1—H1A	0.9800	C11—C12	1.388 (4)
C1—H1B	0.9800	C11—H11	0.9500
C1—H1C	0.9800	C12—C13	1.388 (3)
C2—C3	1.491 (4)	C13—C14	1.380 (3)
C3—C7	1.387 (3)	C13—H13	0.9500
C3—C4	1.430 (4)	C14—H14	0.9500
O4—S1—O3	119.48 (11)	C5—C6—H6B	109.5
O4—S1—N3	107.16 (12)	H6A—C6—H6B	109.5
O3—S1—N3	106.79 (13)	C5—C6—H6C	109.5
O4—S1—C12	106.35 (11)	H6A—C6—H6C	109.5
O3—S1—C12	107.84 (12)	H6B—C6—H6C	109.5
N3—S1—C12	108.90 (12)	N2—C7—C3	106.5 (2)
C4—N1—N2	104.7 (2)	N2—C7—C8	120.5 (2)
N1—N2—C7	112.94 (19)	C3—C7—C8	132.9 (2)
N1—N2—C9	118.5 (2)	C7—C8—H8A	109.5
C7—N2—C9	128.2 (2)	C7—C8—H8B	109.5
S1—N3—H31	113 (2)	H8A—C8—H8B	109.5
S1—N3—H32	115.2 (19)	C7—C8—H8C	109.5
H31—N3—H32	110 (3)	H8A—C8—H8C	109.5
C2—C1—H1A	109.5	H8B—C8—H8C	109.5
C2—C1—H1B	109.5	C10—C9—C14	121.8 (2)
H1A—C1—H1B	109.5	C10—C9—N2	119.6 (2)
C2—C1—H1C	109.5	C14—C9—N2	118.6 (2)
H1A—C1—H1C	109.5	C9—C10—C11	118.9 (2)
H1B—C1—H1C	109.5	C9—C10—H10	120.6
O1—C2—C3	119.3 (2)	C11—C10—H10	120.6
O1—C2—C1	119.6 (2)	C10—C11—C12	119.5 (2)
C3—C2—C1	121.1 (2)	C10—C11—H11	120.2
C7—C3—C4	104.5 (2)	C12—C11—H11	120.2
C7—C3—C2	123.3 (2)	C11—C12—C13	121.2 (2)
C4—C3—C2	132.2 (2)	C11—C12—S1	120.17 (19)
N1—C4—C3	111.3 (2)	C13—C12—S1	118.66 (19)
N1—C4—C5	113.6 (2)	C14—C13—C12	119.5 (2)
C3—C4—C5	135.0 (2)	C14—C13—H13	120.3
O2—C5—C4	120.9 (2)	C12—C13—H13	120.3
O2—C5—C6	121.8 (2)	C13—C14—C9	119.2 (2)
C4—C5—C6	117.2 (2)	C13—C14—H14	120.4
C5—C6—H6A	109.5	C9—C14—H14	120.4
C4—N1—N2—C7	−2.5 (3)	C4—C3—C7—C8	174.8 (3)
C4—N1—N2—C9	170.7 (2)	C2—C3—C7—C8	−3.5 (5)
O1—C2—C3—C7	11.2 (4)	N1—N2—C9—C10	57.7 (3)
C1—C2—C3—C7	−167.1 (3)	C7—N2—C9—C10	−130.3 (3)
O1—C2—C3—C4	−166.6 (3)	N1—N2—C9—C14	−121.2 (3)
C1—C2—C3—C4	15.0 (5)	C7—N2—C9—C14	50.9 (4)
N2—N1—C4—C3	1.4 (3)	C14—C9—C10—C11	−0.5 (4)
N2—N1—C4—C5	−175.3 (2)	N2—C9—C10—C11	−179.4 (2)
C7—C3—C4—N1	0.1 (3)	C9—C10—C11—C12	−0.6 (4)
C2—C3—C4—N1	178.3 (3)	C10—C11—C12—C13	1.4 (4)
C7—C3—C4—C5	175.9 (3)	C10—C11—C12—S1	−178.3 (2)
C2—C3—C4—C5	−6.0 (5)	O4—S1—C12—C11	−10.3 (3)
N1—C4—C5—O2	148.1 (3)	O3—S1—C12—C11	−139.6 (2)
C3—C4—C5—O2	−27.6 (5)	N3—S1—C12—C11	104.9 (2)
N1—C4—C5—C6	−29.0 (4)	O4—S1—C12—C13	169.9 (2)
C3—C4—C5—C6	155.3 (3)	O3—S1—C12—C13	40.7 (3)
N1—N2—C7—C3	2.7 (3)	N3—S1—C12—C13	−74.9 (2)
C9—N2—C7—C3	−169.8 (2)	C11—C12—C13—C14	−1.1 (4)
N1—N2—C7—C8	−174.3 (2)	S1—C12—C13—C14	178.6 (2)
C9—N2—C7—C8	13.2 (4)	C12—C13—C14—C9	0.0 (4)
C4—C3—C7—N2	−1.6 (3)	C10—C9—C14—C13	0.8 (4)
C2—C3—C7—N2	−179.9 (2)	N2—C9—C14—C13	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···O2i	0.88 (1)	2.03 (1)	2.864 (3)	159 (3)
N3—H32···O4ii	0.88 (1)	2.06 (1)	2.933 (3)	170 (3)
C1—H1C···O3i	0.98	2.55	3.446 (3)	151
C10—H10···O1iii	0.95	2.51	3.314 (3)	142
C14—H14···O1iv	0.95	2.54	3.414 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯O2i	0.88 (1)	2.03 (1)	2.864 (3)	159 (3)
N3—H32⋯O4ii	0.88 (1)	2.06 (1)	2.933 (3)	170 (3)
C1—H1C⋯O3i	0.98	2.55	3.446 (3)	151
C10—H10⋯O1iii	0.95	2.51	3.314 (3)	142
C14—H14⋯O1iv	0.95	2.54	3.414 (3)	153

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