N-(7-Eth-oxy-1H-indazol-4-yl)-4-methyl-benzene-sulfonamide.

The mol-ecule of the title heterocyclic compound, C(16)H(17)N(3)O(3)S, is bent at the S atom with an C-SO(2)-NH-C torsion angle of 80.17 (8)°. The phenyl substituent at the S atom is rotated out of the plane of the 1H-indazole ring [inter-planar angle = 46.24 (8)°]. In the crystal, inter-molecular N-H⋯N and N-H⋯O hydrogen bonds build up a ribbon developing parallel to the b-axis direction. C-H⋯O hydrogen bonds link these ribbons, forming a layer parallel to the bc plane.

Related literature

For related structures, see: Shakuntala et al. (2011a ▶,b ▶); Khan et al. (2010 ▶); Gowda et al. (2010 ▶). For the biological activity of similar sulfonamides, see: Soledade et al. (2006 ▶); Lee & Lee, (2002 ▶).

Experimental

Crystal data

C16H17N3O3S

M = 331.39

Monoclinic,

a = 16.2579 (4) Å

b = 5.0291 (1) Å

c = 20.4551 (5) Å

β = 97.269 (1)°

V = 1659.02 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.23 × 0.20 × 0.14 mm

Data collection

Bruker APEXII CCD detector diffractometer

31243 measured reflections

6745 independent reflections

5062 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.158

S = 1.07

6745 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016576/dn2681sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016576/dn2681Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016576/dn2681Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811016576/dn2681Isup4.cml

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

C16H17N3O3S	F(000) = 696
Mr = 331.39	Dx = 1.327 Mg m−3
Monoclinic, P21/c	Melting point: 445 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.2579 (4) Å	Cell parameters from 347 reflections
b = 5.0291 (1) Å	θ = 2.7–27.2°
c = 20.4551 (5) Å	µ = 0.21 mm−1
β = 97.269 (1)°	T = 296 K
V = 1659.02 (7) Å3	Prism, yellow
Z = 4	0.23 × 0.20 × 0.14 mm

Bruker APEXII CCD detector diffractometer	5062 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 34.0°, θmin = 1.3°
ω and φ scans	h = −25→25
31243 measured reflections	k = −7→7
6745 independent reflections	l = −32→31

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0799P)2 + 0.3561P] where P = (Fo2 + 2Fc2)/3
6745 reflections	(Δ/σ)max = 0.011
210 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > σ(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	0.202461 (19)	0.91282 (6)	0.304901 (17)	0.03746 (10)
N1	0.27119 (7)	0.7334 (2)	0.35009 (6)	0.0391 (2)
H14	0.2635	0.5696	0.3412	0.047*
N2	0.43721 (7)	1.2628 (2)	0.50079 (6)	0.0384 (2)
H2A	0.4616	1.3343	0.5362	0.046*
N3	0.45193 (7)	1.3298 (3)	0.43916 (6)	0.0416 (3)
O1	0.19501 (7)	0.8007 (3)	0.24030 (5)	0.0519 (3)
O2	0.22674 (7)	1.1855 (2)	0.31483 (6)	0.0524 (3)
O3	0.37858 (8)	1.0205 (3)	0.61280 (6)	0.0578 (3)
C1	0.08572 (13)	1.0406 (4)	0.38431 (11)	0.0631 (5)
H1	0.1221	1.1725	0.4018	0.076*
C2	0.00971 (15)	1.0085 (5)	0.40702 (13)	0.0794 (7)
H2	−0.0048	1.1212	0.4398	0.095*
C3	−0.04508 (12)	0.8132 (5)	0.38215 (12)	0.0712 (6)
C4	−0.02207 (11)	0.6462 (5)	0.33422 (11)	0.0651 (5)
H4	−0.0581	0.5121	0.3174	0.078*
C5	0.05334 (10)	0.6742 (4)	0.31072 (9)	0.0515 (4)
H5	0.0681	0.5593	0.2785	0.062*
C6	0.10683 (8)	0.8748 (3)	0.33547 (7)	0.0385 (3)
C7	0.29527 (7)	0.8035 (2)	0.41776 (7)	0.0346 (2)
C8	0.26575 (9)	0.6722 (3)	0.46859 (8)	0.0451 (3)
H8	0.2269	0.5376	0.4590	0.054*
C9	0.29232 (10)	0.7346 (3)	0.53502 (8)	0.0501 (4)
H9	0.2716	0.6385	0.5682	0.060*
C10	0.34852 (9)	0.9356 (3)	0.55166 (7)	0.0415 (3)
C11	0.37907 (7)	1.0689 (2)	0.49948 (6)	0.0338 (2)
C12	0.35467 (7)	1.0062 (2)	0.43349 (6)	0.0323 (2)
C13	0.40308 (8)	1.1763 (3)	0.39843 (7)	0.0381 (3)
H13	0.4008	1.1797	0.3528	0.046*
C14	0.36325 (16)	0.8578 (6)	0.66736 (10)	0.0814 (7)
H14A	0.3858	0.6811	0.6630	0.098*
H14B	0.3041	0.8422	0.6691	0.098*
C15	0.4038 (2)	0.9868 (8)	0.72770 (11)	0.1024 (9)
H15A	0.4610	1.0202	0.7232	0.154*
H15B	0.4005	0.8722	0.7648	0.154*
H15C	0.3765	1.1520	0.7344	0.154*
C16	−0.12866 (17)	0.7785 (10)	0.40632 (19)	0.1314 (14)
H16A	−0.1231	0.6624	0.4439	0.197*
H16B	−0.1671	0.7026	0.3718	0.197*
H16C	−0.1489	0.9484	0.4186	0.197*

	U11	U22	U33	U12	U13	U23
S1	0.03566 (15)	0.03045 (15)	0.04463 (19)	−0.00315 (11)	−0.00135 (12)	−0.00309 (12)
N1	0.0377 (5)	0.0267 (4)	0.0501 (6)	−0.0007 (4)	−0.0058 (4)	−0.0085 (4)
N2	0.0355 (5)	0.0403 (5)	0.0385 (5)	−0.0137 (4)	0.0015 (4)	−0.0025 (4)
N3	0.0373 (5)	0.0444 (6)	0.0427 (6)	−0.0155 (5)	0.0038 (4)	0.0018 (5)
O1	0.0506 (6)	0.0608 (7)	0.0429 (6)	−0.0006 (5)	0.0011 (4)	−0.0066 (5)
O2	0.0501 (6)	0.0289 (5)	0.0755 (8)	−0.0068 (4)	−0.0021 (5)	0.0035 (5)
O3	0.0651 (7)	0.0711 (8)	0.0380 (5)	−0.0210 (6)	0.0100 (5)	−0.0019 (5)
C1	0.0635 (10)	0.0507 (9)	0.0779 (13)	−0.0091 (8)	0.0196 (9)	−0.0217 (9)
C2	0.0760 (14)	0.0735 (13)	0.0963 (17)	−0.0007 (12)	0.0407 (13)	−0.0193 (13)
C3	0.0481 (9)	0.0836 (14)	0.0844 (14)	−0.0007 (9)	0.0185 (9)	0.0131 (12)
C4	0.0438 (8)	0.0742 (12)	0.0748 (12)	−0.0200 (8)	−0.0020 (8)	0.0052 (10)
C5	0.0452 (7)	0.0516 (8)	0.0561 (9)	−0.0130 (6)	−0.0006 (6)	−0.0089 (7)
C6	0.0352 (5)	0.0330 (6)	0.0457 (7)	−0.0009 (4)	−0.0012 (5)	−0.0021 (5)
C7	0.0296 (5)	0.0273 (5)	0.0457 (7)	−0.0034 (4)	−0.0001 (4)	−0.0027 (5)
C8	0.0384 (6)	0.0372 (6)	0.0587 (9)	−0.0146 (5)	0.0027 (6)	0.0028 (6)
C9	0.0454 (7)	0.0533 (8)	0.0528 (8)	−0.0178 (6)	0.0110 (6)	0.0081 (7)
C10	0.0382 (6)	0.0464 (7)	0.0404 (6)	−0.0082 (5)	0.0076 (5)	0.0017 (5)
C11	0.0288 (5)	0.0326 (5)	0.0400 (6)	−0.0053 (4)	0.0041 (4)	−0.0007 (5)
C12	0.0278 (4)	0.0299 (5)	0.0387 (6)	−0.0046 (4)	0.0019 (4)	−0.0013 (4)
C13	0.0360 (5)	0.0406 (6)	0.0375 (6)	−0.0094 (5)	0.0040 (4)	0.0004 (5)
C14	0.0892 (15)	0.1092 (19)	0.0474 (10)	−0.0299 (14)	0.0152 (10)	0.0098 (11)
C15	0.118 (2)	0.146 (3)	0.0443 (11)	−0.024 (2)	0.0118 (12)	−0.0018 (14)
C16	0.0683 (16)	0.171 (4)	0.165 (3)	−0.012 (2)	0.058 (2)	0.001 (3)

S1—O1	1.4277 (11)	C5—C6	1.3854 (19)
S1—O2	1.4345 (11)	C5—H5	0.9300
S1—N1	1.6296 (11)	C7—C8	1.369 (2)
S1—C6	1.7581 (14)	C7—C12	1.4133 (16)
N1—C7	1.4340 (17)	C8—C9	1.408 (2)
N1—H14	0.8492	C8—H8	0.9300
N2—N3	1.3550 (16)	C9—C10	1.376 (2)
N2—C11	1.3561 (15)	C9—H9	0.9300
N2—H2A	0.8600	C10—C11	1.4032 (18)
N3—C13	1.3241 (17)	C11—C12	1.3939 (17)
O3—C10	1.3529 (18)	C12—C13	1.4170 (17)
O3—C14	1.431 (2)	C13—H13	0.9300
C1—C6	1.378 (2)	C14—C15	1.474 (3)
C1—C2	1.384 (3)	C14—H14A	0.9700
C1—H1	0.9300	C14—H14B	0.9700
C2—C3	1.379 (3)	C15—H15A	0.9600
C2—H2	0.9300	C15—H15B	0.9600
C3—C4	1.378 (3)	C15—H15C	0.9600
C3—C16	1.514 (3)	C16—H16A	0.9600
C4—C5	1.379 (2)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
O1—S1—O2	119.88 (8)	C7—C8—H8	118.9
O1—S1—N1	106.15 (7)	C9—C8—H8	118.9
O2—S1—N1	107.00 (6)	C10—C9—C8	121.01 (13)
O1—S1—C6	108.12 (7)	C10—C9—H9	119.5
O2—S1—C6	107.07 (7)	C8—C9—H9	119.5
N1—S1—C6	108.17 (7)	O3—C10—C9	127.66 (14)
C7—N1—S1	119.69 (9)	O3—C10—C11	115.56 (12)
C7—N1—H14	117.4	C9—C10—C11	116.78 (13)
S1—N1—H14	110.1	N2—C11—C12	107.09 (11)
N3—N2—C11	111.41 (10)	N2—C11—C10	129.89 (12)
N3—N2—H2A	124.3	C12—C11—C10	122.95 (11)
C11—N2—H2A	124.3	C11—C12—C7	119.09 (11)
C13—N3—N2	106.15 (10)	C11—C12—C13	104.21 (10)
C10—O3—C14	117.55 (15)	C7—C12—C13	136.68 (12)
C6—C1—C2	119.19 (18)	N3—C13—C12	111.14 (12)
C6—C1—H1	120.4	N3—C13—H13	124.4
C2—C1—H1	120.4	C12—C13—H13	124.4
C3—C2—C1	121.5 (2)	O3—C14—C15	107.3 (2)
C3—C2—H2	119.3	O3—C14—H14A	110.3
C1—C2—H2	119.3	C15—C14—H14A	110.3
C4—C3—C2	118.40 (17)	O3—C14—H14B	110.3
C4—C3—C16	119.9 (2)	C15—C14—H14B	110.3
C2—C3—C16	121.7 (3)	H14A—C14—H14B	108.5
C3—C4—C5	121.26 (18)	C14—C15—H15A	109.5
C3—C4—H4	119.4	C14—C15—H15B	109.5
C5—C4—H4	119.4	H15A—C15—H15B	109.5
C4—C5—C6	119.43 (17)	C14—C15—H15C	109.5
C4—C5—H5	120.3	H15A—C15—H15C	109.5
C6—C5—H5	120.3	H15B—C15—H15C	109.5
C1—C6—C5	120.23 (15)	C3—C16—H16A	109.5
C1—C6—S1	120.31 (12)	C3—C16—H16B	109.5
C5—C6—S1	119.45 (12)	H16A—C16—H16B	109.5
C8—C7—C12	118.04 (12)	C3—C16—H16C	109.5
C8—C7—N1	122.39 (11)	H16A—C16—H16C	109.5
C12—C7—N1	119.49 (11)	H16B—C16—H16C	109.5
C7—C8—C9	122.11 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O1i	0.97	2.54	3.373 (3)	144
N1—H14···O2ii	0.85	2.07	2.9159 (15)	172
N2—H2A···N3iii	0.86	2.21	2.8974 (15)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O1i	0.97	2.54	3.373 (3)	144
N1—H14⋯O2ii	0.85	2.07	2.9159 (15)	172
N2—H2A⋯N3iii	0.86	2.21	2.8974 (15)	136

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