N-(1H-Indazol-5-yl)-4-meth-oxy-benzene-sulfonamide.

In the title compound, C14H13N3O3S, the fused ring system is almost planar, the largest deviation from the mean plane being 0.023 (2) Å, and makes a dihedral angle of 47.92 (10)° with the benzene ring of the benzene-sulfonamide moiety. In the crystal, mol-ecules are connected through N-H⋯O hydrogen bonds and weak C-H⋯O contacts, forming a two-dimensional network which is parallel to (010).

Related literature

For the pharmacological activity of selected sulfonamide derivatives, see: El-Sayed et al. (2011 ▶); Smith & Jones (2008 ▶); Scozzafava et al. (2003 ▶). For similar compounds, see: Bouissane et al. (2006 ▶); Abbassi et al. (2012 ▶, 2013 ▶); Chicha et al. (2013 ▶).

Experimental

Crystal data

C14H13N3O3S

M = 303.33

Monoclinic,

a = 8.9996 (4) Å

b = 7.1999 (3) Å

c = 21.3728 (10) Å

β = 91.794 (3)°

V = 1384.20 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.41 × 0.36 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.912, T max = 0.954

14415 measured reflections

3059 independent reflections

2234 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.05

3059 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.26 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/S1600536813028912/im2443sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028912/im2443Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028912/im2443Isup3.cml

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

C14H13N3O3S	F(000) = 632
Mr = 303.33	Dx = 1.456 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3059 reflections
a = 8.9996 (4) Å	θ = 2.3–27.1°
b = 7.1999 (3) Å	µ = 0.25 mm−1
c = 21.3728 (10) Å	T = 296 K
β = 91.794 (3)°	Block, colourless
V = 1384.20 (11) Å3	0.41 × 0.36 × 0.27 mm
Z = 4

Bruker X8 APEX diffractometer	3059 independent reflections
Radiation source: fine-focus sealed tube	2234 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 27.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.912, Tmax = 0.954	k = −9→7
14415 measured reflections	l = −26→27

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)] = 0.042	Hydrogen site location: difference Fourier map
wR(F2) = 0.119	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.3443P] where P = (Fo2 + 2Fc2)/3
3059 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
C1	0.4773 (2)	0.7356 (3)	0.10971 (11)	0.0511 (5)
H1	0.4212	0.8416	0.1167	0.061*
C2	0.4174 (2)	0.5666 (3)	0.08594 (9)	0.0393 (4)
C3	0.2770 (2)	0.5028 (3)	0.06477 (9)	0.0418 (5)
H3	0.1947	0.5810	0.0638	0.050*
C4	0.26542 (19)	0.3211 (3)	0.04565 (9)	0.0375 (4)
C5	0.3905 (2)	0.2042 (3)	0.04520 (10)	0.0432 (5)
H5	0.3786	0.0819	0.0320	0.052*
C6	0.5286 (2)	0.2648 (3)	0.06360 (10)	0.0468 (5)
H6	0.6112	0.1874	0.0624	0.056*
C7	0.5405 (2)	0.4478 (3)	0.08428 (9)	0.0399 (4)
C8	0.0730 (2)	0.0780 (3)	0.13810 (10)	0.0443 (5)
C9	0.0520 (3)	−0.1113 (3)	0.13918 (12)	0.0564 (6)
H9	−0.0086	−0.1682	0.1088	0.068*
C10	0.1216 (3)	−0.2164 (3)	0.18576 (12)	0.0631 (6)
H10	0.1068	−0.3442	0.1872	0.076*
C11	0.2130 (3)	−0.1310 (4)	0.23000 (11)	0.0658 (7)
C12	0.2318 (4)	0.0582 (4)	0.22939 (12)	0.0789 (8)
H12	0.2913	0.1154	0.2601	0.095*
C13	0.1630 (3)	0.1618 (3)	0.18373 (11)	0.0649 (7)
H13	0.1765	0.2899	0.1831	0.078*
C14	0.2942 (4)	−0.4178 (4)	0.27574 (15)	0.0991 (11)
H14A	0.3528	−0.4620	0.3110	0.149*
H14B	0.3375	−0.4594	0.2377	0.149*
H14C	0.1948	−0.4653	0.2779	0.149*
N1	0.65971 (18)	0.5491 (3)	0.10488 (8)	0.0496 (4)
H1N	0.7553	0.5150	0.1082	0.073 (8)*
N2	0.6220 (2)	0.7245 (3)	0.12066 (9)	0.0543 (5)
N3	0.12368 (17)	0.2461 (2)	0.02574 (8)	0.0442 (4)
H3N	0.1279	0.1587	0.0047	0.049 (7)*
O1	−0.03673 (15)	0.3928 (2)	0.10350 (8)	0.0574 (4)
O2	−0.11991 (14)	0.1127 (2)	0.04547 (8)	0.0589 (4)
O3	0.2906 (3)	−0.2221 (3)	0.27662 (9)	0.1019 (8)
S1	−0.00356 (5)	0.21505 (7)	0.07747 (3)	0.04454 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0589 (13)	0.0394 (11)	0.0548 (14)	−0.0011 (10)	−0.0028 (10)	−0.0053 (10)
C2	0.0456 (10)	0.0356 (10)	0.0365 (10)	0.0006 (8)	0.0010 (8)	0.0011 (8)
C3	0.0415 (10)	0.0377 (11)	0.0459 (11)	0.0054 (8)	−0.0026 (8)	0.0007 (9)
C4	0.0389 (9)	0.0398 (11)	0.0339 (10)	−0.0002 (8)	−0.0002 (7)	0.0013 (8)
C5	0.0469 (10)	0.0358 (10)	0.0468 (12)	0.0034 (8)	0.0020 (9)	−0.0047 (9)
C6	0.0400 (10)	0.0464 (12)	0.0542 (13)	0.0079 (9)	0.0020 (9)	−0.0065 (10)
C7	0.0389 (9)	0.0454 (11)	0.0354 (10)	−0.0010 (8)	0.0009 (8)	−0.0005 (8)
C8	0.0443 (10)	0.0438 (12)	0.0451 (12)	0.0001 (9)	0.0055 (9)	−0.0046 (9)
C9	0.0622 (13)	0.0440 (13)	0.0630 (15)	−0.0017 (10)	−0.0010 (11)	−0.0081 (11)
C10	0.0843 (17)	0.0379 (12)	0.0674 (17)	0.0027 (12)	0.0079 (13)	−0.0046 (11)
C11	0.0959 (18)	0.0586 (16)	0.0429 (14)	0.0103 (14)	0.0008 (12)	−0.0005 (11)
C12	0.123 (2)	0.0618 (17)	0.0505 (15)	−0.0090 (16)	−0.0227 (15)	−0.0034 (12)
C13	0.0962 (18)	0.0471 (13)	0.0505 (14)	−0.0087 (13)	−0.0114 (13)	−0.0016 (11)
C14	0.154 (3)	0.0627 (19)	0.080 (2)	0.0185 (19)	−0.006 (2)	0.0124 (16)
N1	0.0429 (9)	0.0535 (11)	0.0522 (11)	−0.0027 (8)	−0.0032 (8)	−0.0073 (8)
N2	0.0598 (11)	0.0472 (11)	0.0554 (11)	−0.0070 (9)	−0.0059 (9)	−0.0075 (9)
N3	0.0425 (9)	0.0444 (10)	0.0452 (10)	−0.0006 (7)	−0.0059 (7)	−0.0074 (8)
O1	0.0471 (8)	0.0472 (9)	0.0780 (11)	0.0083 (7)	0.0036 (7)	−0.0120 (8)
O2	0.0357 (7)	0.0605 (10)	0.0797 (11)	−0.0009 (7)	−0.0091 (7)	−0.0128 (8)
O3	0.179 (2)	0.0620 (12)	0.0623 (13)	0.0153 (13)	−0.0334 (14)	0.0025 (10)
S1	0.0340 (2)	0.0421 (3)	0.0572 (3)	0.0021 (2)	−0.0027 (2)	−0.0070 (2)

C1—N2	1.319 (3)	C9—H9	0.9300
C1—C2	1.418 (3)	C10—C11	1.378 (3)
C1—H1	0.9300	C10—H10	0.9300
C2—C7	1.401 (3)	C11—O3	1.366 (3)
C2—C3	1.406 (3)	C11—C12	1.373 (4)
C3—C4	1.374 (3)	C12—C13	1.362 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.405 (3)	C13—H13	0.9300
C4—N3	1.437 (2)	C14—O3	1.410 (3)
C5—C6	1.364 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.393 (3)	C14—H14C	0.9600
C6—H6	0.9300	N1—N2	1.353 (2)
C7—N1	1.359 (2)	N1—H1N	0.8951
C8—C9	1.376 (3)	N3—S1	1.6319 (18)
C8—C13	1.387 (3)	N3—H3N	0.7745
C8—S1	1.753 (2)	O1—S1	1.4306 (15)
C9—C10	1.385 (3)	O2—S1	1.4361 (14)
N2—C1—C2	111.95 (19)	O3—C11—C12	115.0 (2)
N2—C1—H1	124.0	O3—C11—C10	124.5 (2)
C2—C1—H1	124.0	C12—C11—C10	120.5 (2)
C7—C2—C3	119.72 (17)	C13—C12—C11	119.8 (2)
C7—C2—C1	103.96 (17)	C13—C12—H12	120.1
C3—C2—C1	136.31 (19)	C11—C12—H12	120.1
C4—C3—C2	117.75 (17)	C12—C13—C8	120.5 (2)
C4—C3—H3	121.1	C12—C13—H13	119.7
C2—C3—H3	121.1	C8—C13—H13	119.7
C3—C4—C5	121.28 (17)	O3—C14—H14A	109.5
C3—C4—N3	120.26 (16)	O3—C14—H14B	109.5
C5—C4—N3	118.46 (17)	H14A—C14—H14B	109.5
C6—C5—C4	121.96 (18)	O3—C14—H14C	109.5
C6—C5—H5	119.0	H14A—C14—H14C	109.5
C4—C5—H5	119.0	H14B—C14—H14C	109.5
C5—C6—C7	117.02 (18)	N2—N1—C7	112.33 (17)
C5—C6—H6	121.5	N2—N1—H1N	118.9
C7—C6—H6	121.5	C7—N1—H1N	128.8
N1—C7—C6	131.46 (18)	C1—N2—N1	105.43 (17)
N1—C7—C2	106.32 (17)	C4—N3—S1	119.08 (13)
C6—C7—C2	122.21 (17)	C4—N3—H3N	114.7
C9—C8—C13	119.8 (2)	S1—N3—H3N	109.3
C9—C8—S1	121.26 (17)	C11—O3—C14	118.8 (2)
C13—C8—S1	118.83 (17)	O1—S1—O2	119.10 (9)
C8—C9—C10	119.6 (2)	O1—S1—N3	107.47 (10)
C8—C9—H9	120.2	O2—S1—N3	105.32 (9)
C10—C9—H9	120.2	O1—S1—C8	107.36 (10)
C11—C10—C9	119.7 (2)	O2—S1—C8	109.09 (10)
C11—C10—H10	120.1	N3—S1—C8	108.06 (9)
C9—C10—H10	120.1

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.90	2.07	2.956 (2)	168
N3—H3N···O2ii	0.77	2.23	2.998 (2)	172
C6—H6···O2i	0.93	2.52	3.381 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.90	2.07	2.956 (2)	168
N3—H3N⋯O2ii	0.77	2.23	2.998 (2)	172
C6—H6⋯O2i	0.93	2.52	3.381 (2)	155

Symmetry codes: (i) ; (ii) .