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

The two aromatic rings of the title compound, C(11)H(13)N(3)O(2)S, are inclined at an angle of 47.81 (4)°. The N atom of the amino unit is pyramidally coordinated; one H atom inter-acts with the sulfamyl O atom of an adjacent mol-ecule, forming a centrosymmetric hydrogen-bonded dimer. The dimers are linked by N-H⋯N hydrogen bonds, generating a three-dimensional network.

Related literature

For the synthesis and medicinal properties of the title compound, see: Grueneberg et al. (2002 ▶); Wright et al. (1964 ▶).

Experimental

Crystal data

C11H13N3O2S

M = 251.30

Monoclinic,

a = 7.9649 (1) Å

b = 11.7827 (2) Å

c = 12.2720 (2) Å

β = 91.720 (1)°

V = 1151.18 (3) Å3

Z = 4

Cu Kα radiation

μ = 2.47 mm−1

T = 100 K

0.30 × 0.20 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.525, T max = 0.952

8510 measured reflections

2312 independent reflections

2215 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.07

2312 reflections

164 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.41 e Å−3

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 datablock(s) global, I. DOI: 10.1107/S1600536811032867/bt5610sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032867/bt5610Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032867/bt5610Isup3.cml

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

C11H13N3O2S	F(000) = 528
Mr = 251.30	Dx = 1.450 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 6177 reflections
a = 7.9649 (1) Å	θ = 3.6–74.0°
b = 11.7827 (2) Å	µ = 2.47 mm−1
c = 12.2720 (2) Å	T = 100 K
β = 91.720 (1)°	Plate, orange
V = 1151.18 (3) Å3	0.30 × 0.20 × 0.02 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2312 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2215 reflections with I > 2σ(I)
Mirror	Rint = 0.018
Detector resolution: 10.4041 pixels mm-1	θmax = 74.2°, θmin = 5.2°
ω scans	h = −7→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→14
Tmin = 0.525, Tmax = 0.952	l = −15→15
8510 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.7227P] where P = (Fo2 + 2Fc2)/3
2312 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.35 e Å−3
2 restraints	Δρmin = −0.41 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.60099 (4)	0.32597 (3)	0.50334 (2)	0.01314 (12)
O1	0.44016 (12)	0.37270 (8)	0.52982 (8)	0.0170 (2)
O2	0.65114 (14)	0.21872 (9)	0.54890 (8)	0.0208 (2)
N1	0.61599 (14)	0.27786 (10)	0.02059 (9)	0.0136 (2)
N2	0.55511 (14)	0.18062 (10)	−0.02758 (9)	0.0143 (2)
N3	0.74013 (15)	0.41830 (10)	0.54060 (9)	0.0152 (2)
C1	0.7815 (2)	0.45338 (13)	−0.02125 (12)	0.0232 (3)
H1A	0.8510	0.4777	−0.0815	0.035*
H1B	0.8535	0.4386	0.0434	0.035*
H1C	0.7007	0.5132	−0.0049	0.035*
C2	0.68933 (17)	0.34759 (12)	−0.05284 (11)	0.0161 (3)
C3	0.67052 (18)	0.29522 (12)	−0.15234 (11)	0.0170 (3)
H3	0.7068	0.3228	−0.2205	0.020*
C4	0.58685 (17)	0.19256 (12)	−0.13311 (11)	0.0147 (3)
C5	0.53563 (19)	0.10247 (13)	−0.21321 (11)	0.0196 (3)
H5A	0.4668	0.0456	−0.1771	0.029*
H5B	0.6361	0.0660	−0.2413	0.029*
H5C	0.4705	0.1367	−0.2737	0.029*
C6	0.61070 (16)	0.28964 (12)	0.13566 (11)	0.0136 (3)
C7	0.55663 (18)	0.39093 (12)	0.18128 (11)	0.0183 (3)
H7	0.5220	0.4521	0.1355	0.022*
C8	0.55342 (18)	0.40237 (12)	0.29364 (11)	0.0179 (3)
H8	0.5176	0.4715	0.3253	0.021*
C9	0.60328 (17)	0.31154 (11)	0.35950 (11)	0.0137 (3)
C10	0.65597 (18)	0.21010 (12)	0.31423 (11)	0.0163 (3)
H10	0.6891	0.1485	0.3600	0.020*
C11	0.66000 (18)	0.19918 (12)	0.20165 (11)	0.0163 (3)
H11	0.6963	0.1302	0.1700	0.020*
H1	0.712 (2)	0.4870 (10)	0.5225 (15)	0.029 (5)*
H2	0.8410 (14)	0.3966 (16)	0.5246 (16)	0.029 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01682 (19)	0.01279 (19)	0.00991 (18)	0.00155 (11)	0.00214 (12)	−0.00074 (11)
O1	0.0163 (5)	0.0191 (5)	0.0160 (5)	0.0001 (4)	0.0045 (4)	−0.0025 (4)
O2	0.0332 (6)	0.0157 (5)	0.0138 (5)	0.0049 (4)	0.0028 (4)	0.0018 (4)
N1	0.0153 (6)	0.0143 (6)	0.0110 (5)	−0.0028 (4)	−0.0002 (4)	−0.0017 (4)
N2	0.0142 (5)	0.0159 (6)	0.0128 (6)	−0.0034 (4)	0.0002 (4)	−0.0028 (4)
N3	0.0144 (6)	0.0161 (6)	0.0150 (6)	0.0024 (4)	−0.0003 (4)	−0.0027 (4)
C1	0.0300 (8)	0.0207 (7)	0.0187 (7)	−0.0104 (6)	−0.0052 (6)	0.0036 (6)
C2	0.0169 (6)	0.0165 (7)	0.0149 (6)	−0.0024 (5)	−0.0014 (5)	0.0036 (5)
C3	0.0194 (7)	0.0199 (7)	0.0117 (6)	−0.0022 (5)	−0.0005 (5)	0.0028 (5)
C4	0.0141 (6)	0.0183 (7)	0.0114 (6)	0.0002 (5)	−0.0011 (5)	−0.0011 (5)
C5	0.0248 (7)	0.0209 (7)	0.0130 (6)	−0.0018 (6)	−0.0006 (5)	−0.0039 (5)
C6	0.0123 (6)	0.0173 (7)	0.0113 (6)	−0.0025 (5)	0.0001 (5)	−0.0018 (5)
C7	0.0222 (7)	0.0173 (7)	0.0151 (7)	0.0050 (5)	−0.0033 (5)	0.0003 (5)
C8	0.0219 (7)	0.0160 (7)	0.0157 (7)	0.0048 (5)	−0.0012 (5)	−0.0033 (5)
C9	0.0136 (6)	0.0159 (6)	0.0117 (6)	−0.0005 (5)	0.0012 (5)	−0.0015 (5)
C10	0.0221 (7)	0.0130 (6)	0.0140 (6)	0.0014 (5)	0.0032 (5)	0.0016 (5)
C11	0.0213 (7)	0.0128 (6)	0.0148 (7)	0.0000 (5)	0.0039 (5)	−0.0020 (5)

S1—O2	1.4338 (10)	C3—H3	0.9500
S1—O1	1.4404 (10)	C4—C5	1.4952 (19)
S1—N3	1.6094 (12)	C5—H5A	0.9800
S1—C9	1.7741 (14)	C5—H5B	0.9800
N1—C2	1.3638 (18)	C5—H5C	0.9800
N1—N2	1.3713 (15)	C6—C11	1.3881 (19)
N1—C6	1.4208 (17)	C6—C7	1.392 (2)
N2—C4	1.3344 (18)	C7—C8	1.3864 (19)
N3—H1	0.869 (9)	C7—H7	0.9500
N3—H2	0.871 (9)	C8—C9	1.3918 (19)
C1—C2	1.4920 (19)	C8—H8	0.9500
C1—H1A	0.9800	C9—C10	1.3882 (19)
C1—H1B	0.9800	C10—C11	1.3889 (19)
C1—H1C	0.9800	C10—H10	0.9500
C2—C3	1.372 (2)	C11—H11	0.9500
C3—C4	1.404 (2)
O2—S1—O1	119.22 (6)	N2—C4—C5	120.48 (12)
O2—S1—N3	107.68 (6)	C3—C4—C5	128.50 (13)
O1—S1—N3	106.68 (6)	C4—C5—H5A	109.5
O2—S1—C9	107.00 (6)	C4—C5—H5B	109.5
O1—S1—C9	107.27 (6)	H5A—C5—H5B	109.5
N3—S1—C9	108.66 (6)	C4—C5—H5C	109.5
C2—N1—N2	111.80 (11)	H5A—C5—H5C	109.5
C2—N1—C6	128.61 (11)	H5B—C5—H5C	109.5
N2—N1—C6	119.31 (11)	C11—C6—C7	120.61 (12)
C4—N2—N1	104.80 (11)	C11—C6—N1	119.24 (12)
S1—N3—H1	112.6 (13)	C7—C6—N1	120.15 (12)
S1—N3—H2	111.7 (13)	C8—C7—C6	119.90 (13)
H1—N3—H2	116.9 (18)	C8—C7—H7	120.0
C2—C1—H1A	109.5	C6—C7—H7	120.0
C2—C1—H1B	109.5	C7—C8—C9	119.29 (13)
H1A—C1—H1B	109.5	C7—C8—H8	120.4
C2—C1—H1C	109.5	C9—C8—H8	120.4
H1A—C1—H1C	109.5	C10—C9—C8	120.94 (13)
H1B—C1—H1C	109.5	C10—C9—S1	119.54 (10)
N1—C2—C3	106.24 (12)	C8—C9—S1	119.52 (10)
N1—C2—C1	123.29 (13)	C9—C10—C11	119.61 (13)
C3—C2—C1	130.28 (13)	C9—C10—H10	120.2
C2—C3—C4	106.11 (12)	C11—C10—H10	120.2
C2—C3—H3	126.9	C6—C11—C10	119.64 (13)
C4—C3—H3	126.9	C6—C11—H11	120.2
N2—C4—C3	111.01 (12)	C10—C11—H11	120.2
C2—N1—N2—C4	−1.97 (15)	C11—C6—C7—C8	0.7 (2)
C6—N1—N2—C4	−176.38 (11)	N1—C6—C7—C8	−179.31 (12)
N2—N1—C2—C3	1.89 (15)	C6—C7—C8—C9	−0.5 (2)
C6—N1—C2—C3	175.64 (13)	C7—C8—C9—C10	0.0 (2)
N2—N1—C2—C1	−173.51 (13)	C7—C8—C9—S1	179.52 (11)
C6—N1—C2—C1	0.2 (2)	O2—S1—C9—C10	−2.85 (13)
N1—C2—C3—C4	−1.01 (15)	O1—S1—C9—C10	−131.88 (12)
C1—C2—C3—C4	173.95 (15)	N3—S1—C9—C10	113.15 (12)
N1—N2—C4—C3	1.28 (15)	O2—S1—C9—C8	177.63 (11)
N1—N2—C4—C5	−179.21 (12)	O1—S1—C9—C8	48.60 (13)
C2—C3—C4—N2	−0.18 (16)	N3—S1—C9—C8	−66.37 (13)
C2—C3—C4—C5	−179.65 (14)	C8—C9—C10—C11	0.4 (2)
C2—N1—C6—C11	−128.45 (15)	S1—C9—C10—C11	−179.13 (11)
N2—N1—C6—C11	44.90 (17)	C7—C6—C11—C10	−0.3 (2)
C2—N1—C6—C7	51.5 (2)	N1—C6—C11—C10	179.71 (12)
N2—N1—C6—C7	−135.12 (13)	C9—C10—C11—C6	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O1i	0.87 (1)	2.13 (1)	2.966 (2)	160 (2)
N3—H1···N2ii	0.87 (1)	2.94 (2)	3.501 (2)	124 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O1i	0.87 (1)	2.13 (1)	2.966 (2)	160 (2)
N3—H1⋯N2ii	0.87 (1)	2.94 (2)	3.501 (2)	124 (2)

Symmetry codes: (i) ; (ii) .