4-(3-Methyl-5-phenyl-1H-pyrazol-1-yl)benzene-sulfonamide.

With respect to the planar five-membered ring of the title compound, C(16)H(15)N(3)O(2)S, the phenyl ring is aligned at 47.0 (1)° and the phenyl-ene ring at 37.6 (1)°. The amino group has the N atom in a pyramidal geometry; the group is a hydrogen-bond donor to the sulfonyl O atom of one mol-ecule and to the pyrazole N atom of another mol-ecule, resulting in the formation of a layer parallel to the bc plane.

Related literature

For the synthesis, see: Gosselin et al. (2006 ▶); Organ & Mayer (2003 ▶).

Experimental

Crystal data

C16H15N3O2S

M = 313.37

Monoclinic,

a = 28.2545 (8) Å

b = 11.9135 (4) Å

c = 9.3739 (3) Å

β = 91.016 (3)°

V = 3154.85 (17) Å3

Z = 8

Cu Kα radiation

μ = 1.91 mm−1

T = 100 K

0.30 × 0.03 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.598, T max = 0.945

6579 measured reflections

3137 independent reflections

2689 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.03

3137 reflections

208 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.51 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/S1600536811032855/bt5609sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032855/bt5609Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032855/bt5609Isup3.cml

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

C16H15N3O2S	F(000) = 1312
Mr = 313.37	Dx = 1.320 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 2773 reflections
a = 28.2545 (8) Å	θ = 3.1–74.2°
b = 11.9135 (4) Å	µ = 1.91 mm−1
c = 9.3739 (3) Å	T = 100 K
β = 91.016 (3)°	Prism, light-yellow
V = 3154.85 (17) Å3	0.30 × 0.03 × 0.03 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	3137 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2689 reflections with I > 2σ(I)
Mirror	Rint = 0.035
Detector resolution: 10.4041 pixels mm-1	θmax = 74.4°, θmin = 3.1°
ω scans	h = −35→31
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→14
Tmin = 0.598, Tmax = 0.945	l = −11→9
6579 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0629P)2 + 1.4812P] where P = (Fo2 + 2Fc2)/3
3137 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.690362 (14)	0.48353 (4)	0.65383 (4)	0.01752 (14)
O1	0.67646 (4)	0.41033 (11)	0.76803 (13)	0.0220 (3)
O2	0.69504 (5)	0.60135 (11)	0.68142 (14)	0.0252 (3)
N1	0.65210 (5)	0.46753 (14)	0.52785 (16)	0.0191 (3)
H1	0.6414 (8)	0.395 (2)	0.516 (2)	0.026 (6)*
H2	0.6583 (8)	0.5054 (18)	0.452 (2)	0.017 (5)*
N2	0.88441 (5)	0.35478 (13)	0.48169 (15)	0.0189 (3)
N3	0.89694 (5)	0.24415 (13)	0.47817 (17)	0.0217 (3)
C1	0.96762 (7)	0.13366 (18)	0.4272 (3)	0.0341 (5)
H1A	0.9686	0.0956	0.5199	0.051*
H1B	1.0000	0.1470	0.3954	0.051*
H1C	0.9508	0.0864	0.3573	0.051*
C2	0.94240 (6)	0.24326 (17)	0.4411 (2)	0.0234 (4)
C3	0.95933 (6)	0.35272 (17)	0.42301 (19)	0.0225 (4)
H3	0.9904	0.3741	0.3974	0.027*
C4	0.92187 (6)	0.42307 (16)	0.44972 (17)	0.0193 (4)
C5	0.91994 (6)	0.54696 (16)	0.44973 (18)	0.0192 (4)
C6	0.89996 (6)	0.60729 (16)	0.5616 (2)	0.0229 (4)
H6	0.8878	0.5683	0.6413	0.028*
C7	0.89779 (7)	0.72353 (17)	0.5573 (2)	0.0284 (4)
H7	0.8840	0.7639	0.6335	0.034*
C8	0.91585 (7)	0.78079 (17)	0.4409 (2)	0.0307 (5)
H8	0.9138	0.8603	0.4365	0.037*
C9	0.93685 (7)	0.72183 (18)	0.3313 (2)	0.0292 (4)
H9	0.9499	0.7612	0.2531	0.035*
C10	0.93889 (6)	0.60550 (17)	0.3355 (2)	0.0235 (4)
H10	0.9533	0.5656	0.2600	0.028*
C11	0.83692 (6)	0.38175 (15)	0.51674 (18)	0.0188 (4)
C12	0.81362 (6)	0.47000 (16)	0.44808 (19)	0.0214 (4)
H12	0.8285	0.5097	0.3733	0.026*
C13	0.76862 (6)	0.49917 (16)	0.48990 (19)	0.0213 (4)
H13	0.7529	0.5611	0.4465	0.026*
C14	0.74629 (6)	0.43750 (15)	0.59607 (18)	0.0183 (4)
C15	0.76849 (6)	0.34505 (15)	0.65805 (18)	0.0193 (4)
H15	0.7523	0.3004	0.7256	0.023*
C16	0.81447 (6)	0.31858 (15)	0.62039 (19)	0.0194 (4)
H16	0.8305	0.2576	0.6652	0.023*

	U11	U22	U33	U12	U13	U23
S1	0.0180 (2)	0.0196 (2)	0.0150 (2)	−0.00041 (15)	0.00220 (16)	−0.00277 (15)
O1	0.0219 (6)	0.0280 (7)	0.0161 (6)	0.0002 (5)	0.0038 (5)	−0.0002 (5)
O2	0.0254 (7)	0.0217 (7)	0.0287 (7)	−0.0010 (5)	0.0032 (5)	−0.0067 (5)
N1	0.0192 (7)	0.0221 (8)	0.0159 (7)	−0.0009 (6)	0.0013 (6)	0.0001 (6)
N2	0.0169 (7)	0.0212 (8)	0.0187 (7)	0.0003 (6)	0.0012 (6)	−0.0010 (6)
N3	0.0201 (7)	0.0195 (8)	0.0256 (8)	0.0009 (6)	0.0010 (6)	−0.0027 (6)
C1	0.0271 (10)	0.0280 (11)	0.0474 (13)	0.0041 (8)	0.0067 (9)	−0.0085 (9)
C2	0.0198 (9)	0.0270 (10)	0.0234 (9)	0.0012 (7)	0.0000 (7)	−0.0044 (7)
C3	0.0179 (8)	0.0283 (10)	0.0212 (9)	−0.0012 (7)	0.0017 (7)	−0.0037 (7)
C4	0.0180 (8)	0.0249 (9)	0.0149 (8)	−0.0034 (7)	0.0001 (6)	−0.0002 (7)
C5	0.0148 (8)	0.0236 (9)	0.0190 (9)	−0.0015 (7)	−0.0018 (6)	0.0007 (7)
C6	0.0207 (9)	0.0264 (10)	0.0218 (9)	−0.0014 (7)	0.0010 (7)	0.0004 (7)
C7	0.0248 (9)	0.0269 (10)	0.0335 (11)	0.0031 (8)	−0.0015 (8)	−0.0050 (8)
C8	0.0288 (10)	0.0219 (10)	0.0410 (12)	0.0007 (8)	−0.0067 (8)	0.0047 (9)
C9	0.0278 (10)	0.0302 (10)	0.0293 (10)	−0.0067 (8)	−0.0037 (8)	0.0098 (8)
C10	0.0206 (9)	0.0289 (10)	0.0211 (9)	−0.0038 (7)	0.0004 (7)	0.0009 (7)
C11	0.0161 (8)	0.0223 (9)	0.0179 (8)	−0.0009 (7)	−0.0001 (6)	−0.0023 (7)
C12	0.0189 (9)	0.0279 (10)	0.0175 (9)	−0.0022 (7)	0.0014 (7)	0.0054 (7)
C13	0.0186 (8)	0.0254 (9)	0.0199 (9)	−0.0003 (7)	−0.0003 (7)	0.0036 (7)
C14	0.0171 (8)	0.0210 (9)	0.0169 (8)	−0.0025 (7)	0.0005 (6)	−0.0031 (7)
C15	0.0220 (9)	0.0189 (9)	0.0171 (8)	−0.0028 (7)	0.0028 (7)	−0.0016 (7)
C16	0.0209 (9)	0.0192 (9)	0.0182 (8)	0.0003 (7)	0.0010 (6)	−0.0004 (7)

S1—O2	1.4330 (13)	C6—C7	1.387 (3)
S1—O1	1.4407 (13)	C6—H6	0.9500
S1—N1	1.5983 (15)	C7—C8	1.391 (3)
S1—C14	1.7666 (18)	C7—H7	0.9500
N1—H1	0.92 (2)	C8—C9	1.387 (3)
N1—H2	0.86 (2)	C8—H8	0.9500
N2—N3	1.365 (2)	C9—C10	1.388 (3)
N2—C4	1.372 (2)	C9—H9	0.9500
N2—C11	1.424 (2)	C10—H10	0.9500
N3—C2	1.337 (2)	C11—C16	1.391 (2)
C1—C2	1.494 (3)	C11—C12	1.392 (3)
C1—H1A	0.9800	C12—C13	1.382 (3)
C1—H1B	0.9800	C12—H12	0.9500
C1—H1C	0.9800	C13—C14	1.397 (2)
C2—C3	1.400 (3)	C13—H13	0.9500
C3—C4	1.376 (3)	C14—C15	1.390 (3)
C3—H3	0.9500	C15—C16	1.389 (2)
C4—C5	1.477 (3)	C15—H15	0.9500
C5—C10	1.393 (3)	C16—H16	0.9500
C5—C6	1.398 (3)
O2—S1—O1	118.97 (8)	C7—C6—H6	119.7
O2—S1—N1	108.01 (8)	C5—C6—H6	119.7
O1—S1—N1	106.68 (8)	C6—C7—C8	119.71 (19)
O2—S1—C14	106.21 (8)	C6—C7—H7	120.1
O1—S1—C14	107.27 (8)	C8—C7—H7	120.1
N1—S1—C14	109.49 (8)	C9—C8—C7	120.03 (19)
S1—N1—H1	114.6 (14)	C9—C8—H8	120.0
S1—N1—H2	113.6 (14)	C7—C8—H8	120.0
H1—N1—H2	117.8 (19)	C8—C9—C10	120.20 (18)
N3—N2—C4	111.46 (14)	C8—C9—H9	119.9
N3—N2—C11	117.98 (14)	C10—C9—H9	119.9
C4—N2—C11	130.56 (16)	C9—C10—C5	120.36 (18)
C2—N3—N2	105.35 (15)	C9—C10—H10	119.8
C2—C1—H1A	109.5	C5—C10—H10	119.8
C2—C1—H1B	109.5	C16—C11—C12	120.91 (16)
H1A—C1—H1B	109.5	C16—C11—N2	118.85 (16)
C2—C1—H1C	109.5	C12—C11—N2	120.24 (16)
H1A—C1—H1C	109.5	C13—C12—C11	119.26 (16)
H1B—C1—H1C	109.5	C13—C12—H12	120.4
N3—C2—C3	110.85 (16)	C11—C12—H12	120.4
N3—C2—C1	119.44 (18)	C12—C13—C14	119.97 (17)
C3—C2—C1	129.70 (17)	C12—C13—H13	120.0
C4—C3—C2	106.24 (16)	C14—C13—H13	120.0
C4—C3—H3	126.9	C15—C14—C13	120.57 (16)
C2—C3—H3	126.9	C15—C14—S1	121.16 (13)
N2—C4—C3	106.09 (16)	C13—C14—S1	118.22 (14)
N2—C4—C5	124.32 (16)	C16—C15—C14	119.42 (16)
C3—C4—C5	129.57 (16)	C16—C15—H15	120.3
C10—C5—C6	119.01 (18)	C14—C15—H15	120.3
C10—C5—C4	119.05 (16)	C15—C16—C11	119.67 (16)
C6—C5—C4	121.94 (16)	C15—C16—H16	120.2
C7—C6—C5	120.64 (18)	C11—C16—H16	120.2
C4—N2—N3—C2	−1.13 (19)	C6—C5—C10—C9	−1.6 (3)
C11—N2—N3—C2	179.13 (15)	C4—C5—C10—C9	178.87 (16)
N2—N3—C2—C3	1.0 (2)	N3—N2—C11—C16	37.9 (2)
N2—N3—C2—C1	179.95 (17)	C4—N2—C11—C16	−141.76 (18)
N3—C2—C3—C4	−0.5 (2)	N3—N2—C11—C12	−142.14 (17)
C1—C2—C3—C4	−179.3 (2)	C4—N2—C11—C12	38.2 (3)
N3—N2—C4—C3	0.86 (19)	C16—C11—C12—C13	3.9 (3)
C11—N2—C4—C3	−179.44 (16)	N2—C11—C12—C13	−176.02 (16)
N3—N2—C4—C5	−177.79 (15)	C11—C12—C13—C14	−2.5 (3)
C11—N2—C4—C5	1.9 (3)	C12—C13—C14—C15	−1.5 (3)
C2—C3—C4—N2	−0.24 (19)	C12—C13—C14—S1	176.01 (14)
C2—C3—C4—C5	178.31 (17)	O2—S1—C14—C15	128.99 (15)
N2—C4—C5—C10	−133.78 (18)	O1—S1—C14—C15	0.77 (17)
C3—C4—C5—C10	47.9 (3)	N1—S1—C14—C15	−114.63 (15)
N2—C4—C5—C6	46.7 (2)	O2—S1—C14—C13	−48.55 (16)
C3—C4—C5—C6	−131.6 (2)	O1—S1—C14—C13	−176.76 (14)
C10—C5—C6—C7	1.8 (3)	N1—S1—C14—C13	67.84 (16)
C4—C5—C6—C7	−178.70 (16)	C13—C14—C15—C16	4.2 (3)
C5—C6—C7—C8	−0.3 (3)	S1—C14—C15—C16	−173.24 (13)
C6—C7—C8—C9	−1.4 (3)	C14—C15—C16—C11	−2.8 (3)
C7—C8—C9—C10	1.6 (3)	C12—C11—C16—C15	−1.2 (3)
C8—C9—C10—C5	−0.1 (3)	N2—C11—C16—C15	178.71 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3i	0.92 (2)	1.98 (2)	2.878 (2)	164 (2)
N1—H2···O1ii	0.86 (2)	2.07 (2)	2.930 (2)	177 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3i	0.92 (2)	1.98 (2)	2.878 (2)	164 (2)
N1—H2⋯O1ii	0.86 (2)	2.07 (2)	2.930 (2)	177 (2)

Symmetry codes: (i) ; (ii) .