4-Methyl-N-(1-methyl-1H-indazol-5-yl)benzene-sulfonamide.

In the title compound, C15H15N3O2S, the fused ring system is close to planar, the largest deviation from the mean plane being 0.030 (2) Å, and makes a dihedral angle of 48.84 (9)° with the benzene ring belonging to the methyl-benzene-sulfonamide moiety. In the crystal, mol-ecules are -connected through N-H⋯N hydrogen bonds and weak C-H⋯O contacts, forming a two-dimensional network parallel to (001).

Related literature

For the pharmacological activity of sulfonamide derivatives, see: Bouissane et al. (2006 ▶); Mustafa et al. (2012 ▶); Lopez et al. (2010 ▶). For similar compounds, see: Abbassi et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

C15H15N3O2S

M = 301.36

Monoclinic,

a = 8.0026 (3) Å

b = 12.8195 (4) Å

c = 14.1321 (4) Å

β = 91.602 (2)°

V = 1449.24 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.43 × 0.36 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.992

17896 measured reflections

4048 independent reflections

2703 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.134

S = 1.02

4048 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813023398/bh2482sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023398/bh2482Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023398/bh2482Isup3.cml

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

C15H15N3O2S	F(000) = 632
Mr = 301.36	Dx = 1.381 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4048 reflections
a = 8.0026 (3) Å	θ = 2.9–29.6°
b = 12.8195 (4) Å	µ = 0.23 mm−1
c = 14.1321 (4) Å	T = 296 K
β = 91.602 (2)°	Block, colourless
V = 1449.24 (8) Å3	0.43 × 0.36 × 0.28 mm
Z = 4

Bruker X8 APEX diffractometer	4048 independent reflections
Radiation source: fine-focus sealed tube	2703 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 29.6°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.960, Tmax = 0.992	k = −17→17
17896 measured reflections	l = −19→19

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0633P)2 + 0.2552P] where P = (Fo2 + 2Fc2)/3
4048 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.32 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.31920 (19)	0.13913 (14)	0.21183 (12)	0.0348 (4)
C2	0.4588 (2)	0.18535 (14)	0.16945 (13)	0.0386 (4)
H2	0.4693	0.2576	0.1706	0.046*
C3	0.5789 (2)	0.12762 (14)	0.12688 (13)	0.0381 (4)
H3	0.6709	0.1587	0.0997	0.046*
C4	0.55641 (19)	0.01961 (13)	0.12629 (12)	0.0336 (4)
C5	0.4161 (2)	−0.02812 (13)	0.16553 (12)	0.0352 (4)
C6	0.2952 (2)	0.03317 (13)	0.20985 (13)	0.0361 (4)
H6	0.2022	0.0029	0.2368	0.043*
C7	0.4424 (2)	−0.13606 (15)	0.15117 (14)	0.0448 (4)
H7	0.3685	−0.1880	0.1690	0.054*
C8	0.8127 (2)	−0.04980 (17)	0.04713 (14)	0.0486 (5)
H8A	0.8953	−0.0912	0.0803	0.073*
H8B	0.8477	0.0218	0.0470	0.073*
H8C	0.8000	−0.0743	−0.0169	0.073*
C9	0.1242 (2)	0.36208 (14)	0.13664 (13)	0.0392 (4)
C10	0.1538 (3)	0.35014 (17)	0.04145 (16)	0.0561 (5)
H10	0.1315	0.2868	0.0116	0.067*
C11	0.2163 (3)	0.43217 (19)	−0.00880 (16)	0.0616 (6)
H11	0.2356	0.4234	−0.0729	0.074*
C12	0.2515 (3)	0.52718 (17)	0.03268 (16)	0.0523 (5)
C13	0.2195 (3)	0.53815 (18)	0.12835 (17)	0.0617 (6)
H13	0.2415	0.6016	0.1580	0.074*
C14	0.1560 (3)	0.45732 (16)	0.17998 (15)	0.0518 (5)
H14	0.1345	0.4664	0.2438	0.062*
C15	0.3195 (3)	0.6169 (2)	−0.0239 (2)	0.0802 (8)
H15A	0.3339	0.5951	−0.0881	0.120*
H15B	0.4253	0.6383	0.0032	0.120*
H15C	0.2425	0.6742	−0.0227	0.120*
N1	0.20248 (17)	0.20314 (12)	0.26172 (11)	0.0393 (3)
H1	0.2468	0.2458	0.3038	0.047*
N2	0.5857 (2)	−0.15374 (12)	0.10917 (12)	0.0471 (4)
N3	0.65480 (18)	−0.05848 (12)	0.09380 (11)	0.0391 (3)
O1	−0.05599 (17)	0.30214 (12)	0.27498 (12)	0.0624 (4)
O2	−0.02085 (16)	0.18164 (11)	0.13971 (11)	0.0572 (4)
S1	0.04597 (5)	0.25800 (4)	0.20396 (4)	0.04273 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0324 (7)	0.0340 (9)	0.0381 (9)	0.0007 (6)	0.0028 (6)	0.0028 (7)
C2	0.0387 (8)	0.0284 (9)	0.0491 (11)	−0.0039 (7)	0.0045 (7)	0.0023 (8)
C3	0.0336 (8)	0.0340 (10)	0.0469 (10)	−0.0041 (7)	0.0073 (7)	0.0040 (8)
C4	0.0314 (7)	0.0335 (9)	0.0358 (9)	0.0026 (6)	−0.0003 (6)	0.0017 (7)
C5	0.0345 (8)	0.0307 (9)	0.0404 (10)	−0.0014 (6)	−0.0010 (7)	0.0040 (7)
C6	0.0312 (7)	0.0330 (9)	0.0441 (10)	−0.0039 (6)	0.0041 (7)	0.0060 (8)
C7	0.0462 (10)	0.0309 (10)	0.0574 (12)	−0.0021 (7)	0.0041 (8)	0.0041 (9)
C8	0.0448 (10)	0.0532 (13)	0.0483 (11)	0.0088 (8)	0.0113 (8)	−0.0031 (10)
C9	0.0359 (8)	0.0353 (10)	0.0461 (10)	0.0035 (7)	−0.0006 (7)	−0.0016 (8)
C10	0.0714 (13)	0.0429 (12)	0.0544 (13)	−0.0043 (10)	0.0093 (10)	−0.0120 (10)
C11	0.0802 (16)	0.0564 (15)	0.0488 (13)	−0.0019 (12)	0.0119 (11)	0.0001 (11)
C12	0.0515 (11)	0.0466 (13)	0.0586 (14)	−0.0009 (9)	−0.0033 (9)	0.0106 (10)
C13	0.0813 (16)	0.0415 (13)	0.0619 (15)	−0.0138 (11)	−0.0080 (12)	−0.0026 (11)
C14	0.0674 (13)	0.0420 (12)	0.0456 (11)	−0.0050 (9)	−0.0026 (9)	−0.0027 (9)
C15	0.0803 (17)	0.0709 (18)	0.0893 (19)	−0.0147 (14)	−0.0032 (14)	0.0316 (16)
N1	0.0382 (7)	0.0352 (8)	0.0448 (9)	0.0009 (6)	0.0081 (6)	−0.0017 (7)
N2	0.0510 (9)	0.0323 (9)	0.0582 (10)	0.0030 (7)	0.0029 (7)	−0.0006 (8)
N3	0.0386 (7)	0.0352 (9)	0.0436 (9)	0.0038 (6)	0.0033 (6)	−0.0012 (7)
O1	0.0494 (8)	0.0546 (10)	0.0848 (11)	0.0102 (6)	0.0318 (8)	0.0029 (8)
O2	0.0403 (7)	0.0446 (8)	0.0862 (11)	−0.0080 (6)	−0.0079 (7)	−0.0064 (8)
S1	0.0311 (2)	0.0361 (3)	0.0614 (3)	0.00089 (16)	0.00821 (18)	−0.0010 (2)

C1—C6	1.372 (2)	C9—C14	1.387 (3)
C1—C2	1.412 (2)	C9—S1	1.7635 (19)
C1—N1	1.442 (2)	C10—C11	1.371 (3)
C2—C3	1.366 (2)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.377 (3)
C3—C4	1.396 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.390 (3)
C4—N3	1.361 (2)	C12—C15	1.510 (3)
C4—C5	1.406 (2)	C13—C14	1.373 (3)
C5—C6	1.407 (2)	C13—H13	0.9300
C5—C7	1.415 (3)	C14—H14	0.9300
C6—H6	0.9300	C15—H15A	0.9600
C7—N2	1.325 (2)	C15—H15B	0.9600
C7—H7	0.9300	C15—H15C	0.9600
C8—N3	1.446 (2)	N1—S1	1.6348 (15)
C8—H8A	0.9600	N1—H1	0.8759
C8—H8B	0.9600	N2—N3	1.361 (2)
C8—H8C	0.9600	O1—S1	1.4280 (14)
C9—C10	1.381 (3)	O2—S1	1.4288 (15)
C6—C1—C2	121.25 (15)	C9—C10—H10	120.2
C6—C1—N1	118.75 (14)	C10—C11—C12	122.1 (2)
C2—C1—N1	119.96 (15)	C10—C11—H11	119.0
C3—C2—C1	122.27 (16)	C12—C11—H11	119.0
C3—C2—H2	118.9	C11—C12—C13	117.5 (2)
C1—C2—H2	118.9	C11—C12—C15	121.4 (2)
C2—C3—C4	116.61 (15)	C13—C12—C15	121.1 (2)
C2—C3—H3	121.7	C14—C13—C12	121.4 (2)
C4—C3—H3	121.7	C14—C13—H13	119.3
N3—C4—C3	130.97 (16)	C12—C13—H13	119.3
N3—C4—C5	106.78 (15)	C13—C14—C9	119.7 (2)
C3—C4—C5	122.23 (15)	C13—C14—H14	120.1
C4—C5—C6	119.96 (16)	C9—C14—H14	120.1
C4—C5—C7	104.22 (15)	C12—C15—H15A	109.5
C6—C5—C7	135.76 (16)	C12—C15—H15B	109.5
C1—C6—C5	117.65 (15)	H15A—C15—H15B	109.5
C1—C6—H6	121.2	C12—C15—H15C	109.5
C5—C6—H6	121.2	H15A—C15—H15C	109.5
N2—C7—C5	111.41 (16)	H15B—C15—H15C	109.5
N2—C7—H7	124.3	C1—N1—S1	119.89 (12)
C5—C7—H7	124.3	C1—N1—H1	115.6
N3—C8—H8A	109.5	S1—N1—H1	111.2
N3—C8—H8B	109.5	C7—N2—N3	106.19 (15)
H8A—C8—H8B	109.5	N2—N3—C4	111.38 (14)
N3—C8—H8C	109.5	N2—N3—C8	120.41 (15)
H8A—C8—H8C	109.5	C4—N3—C8	128.20 (16)
H8B—C8—H8C	109.5	O1—S1—O2	120.46 (9)
C10—C9—C14	119.56 (19)	O1—S1—N1	105.33 (9)
C10—C9—S1	120.99 (15)	O2—S1—N1	106.88 (8)
C14—C9—S1	119.44 (15)	O1—S1—C9	107.32 (9)
C11—C10—C9	119.6 (2)	O2—S1—C9	107.92 (9)
C11—C10—H10	120.2	N1—S1—C9	108.45 (8)
C6—C1—C2—C3	−1.9 (3)	C12—C13—C14—C9	0.6 (4)
N1—C1—C2—C3	175.55 (16)	C10—C9—C14—C13	−1.2 (3)
C1—C2—C3—C4	0.6 (3)	S1—C9—C14—C13	178.93 (17)
C2—C3—C4—N3	−176.89 (18)	C6—C1—N1—S1	−95.37 (17)
C2—C3—C4—C5	1.3 (3)	C2—C1—N1—S1	87.17 (18)
N3—C4—C5—C6	176.56 (15)	C5—C7—N2—N3	−0.9 (2)
C3—C4—C5—C6	−2.0 (3)	C7—N2—N3—C4	0.3 (2)
N3—C4—C5—C7	−0.94 (19)	C7—N2—N3—C8	−179.02 (17)
C3—C4—C5—C7	−179.50 (16)	C3—C4—N3—N2	178.82 (18)
C2—C1—C6—C5	1.1 (3)	C5—C4—N3—N2	0.4 (2)
N1—C1—C6—C5	−176.33 (15)	C3—C4—N3—C8	−1.9 (3)
C4—C5—C6—C1	0.7 (3)	C5—C4—N3—C8	179.70 (17)
C7—C5—C6—C1	177.3 (2)	C1—N1—S1—O1	171.99 (13)
C4—C5—C7—N2	1.2 (2)	C1—N1—S1—O2	42.75 (15)
C6—C5—C7—N2	−175.7 (2)	C1—N1—S1—C9	−73.37 (14)
C14—C9—C10—C11	0.8 (3)	C10—C9—S1—O1	−147.78 (17)
S1—C9—C10—C11	−179.30 (18)	C14—C9—S1—O1	32.12 (18)
C9—C10—C11—C12	0.2 (4)	C10—C9—S1—O2	−16.55 (18)
C10—C11—C12—C13	−0.8 (4)	C14—C9—S1—O2	163.35 (15)
C10—C11—C12—C15	−179.7 (2)	C10—C9—S1—N1	98.89 (17)
C11—C12—C13—C14	0.4 (4)	C14—C9—S1—N1	−81.21 (17)
C15—C12—C13—C14	179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.88	2.21	3.065 (2)	166
C3—H3···O2ii	0.93	2.53	3.277 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.88	2.21	3.065 (2)	166
C3—H3⋯O2ii	0.93	2.53	3.277 (2)	137

Symmetry codes: (i) ; (ii) .