N-(3-Chloro-1H-indazol-5-yl)-4-meth-oxy-benzene-sulfonamide.

In the title compound, C14H12ClN3O3S, the fused five- and six-membered rings are folded slightly along the common edge, forming a dihedral angle of 3.2 (1)°. The mean plane through the indazole system makes a dihedral angle of 30.75 (7)° with the distant benzene ring. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules, forming a two-dimensional network parallel to (001).

Related literature

For the pharmacological activity of sulfonamide derivatives, see: Bouissane et al. (2006 ▶); El-Sayed et al. (2011 ▶); Mustafa et al. (2012 ▶). For similar compounds, see: Abbassi et al. (2012 ▶, 2013 ▶); Chicha et al. (2013 ▶).

Experimental

Crystal data

C14H12ClN3O3S

M = 337.78

Monoclinic,

a = 16.1229 (5) Å

b = 10.0562 (3) Å

c = 9.7955 (2) Å

β = 105.388 (1)°

V = 1531.26 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 296 K

0.42 × 0.35 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.693, T max = 0.747

19939 measured reflections

4666 independent reflections

3973 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.117

S = 1.03

4666 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.49 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/S160053681302744X/im2442sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302744X/im2442Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302744X/im2442Isup3.cml

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

C14H12ClN3O3S	F(000) = 696
Mr = 337.78	Dx = 1.465 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4666 reflections
a = 16.1229 (5) Å	θ = 2.4–30.5°
b = 10.0562 (3) Å	µ = 0.40 mm−1
c = 9.7955 (2) Å	T = 296 K
β = 105.388 (1)°	Block, colourless
V = 1531.26 (7) Å3	0.42 × 0.35 × 0.28 mm
Z = 4

Bruker X8 APEX diffractometer	4666 independent reflections
Radiation source: fine-focus sealed tube	3973 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 30.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→20
Tmin = 0.693, Tmax = 0.747	k = −14→14
19939 measured reflections	l = −13→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.5266P] where P = (Fo2 + 2Fc2)/3
4666 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.49 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
C4	0.60822 (8)	0.97963 (12)	−0.02865 (13)	0.0268 (2)
C5	0.56209 (8)	1.06572 (14)	−0.13562 (15)	0.0336 (3)
H5	0.5231	1.0301	−0.2147	0.040*
C6	0.57361 (10)	1.20157 (14)	−0.12547 (17)	0.0386 (3)
H6	0.5432	1.2585	−0.1960	0.046*
C7	0.63294 (9)	1.24992 (12)	−0.00465 (16)	0.0347 (3)
C2	0.67936 (9)	1.16423 (13)	0.10154 (14)	0.0306 (3)
C3	0.66674 (8)	1.02644 (12)	0.09022 (13)	0.0286 (2)
H3	0.6968	0.9690	0.1604	0.034*
C1	0.73489 (11)	1.25131 (14)	0.19788 (17)	0.0400 (3)
C8	0.76161 (9)	0.78982 (13)	−0.03973 (14)	0.0305 (2)
C9	0.80235 (10)	0.71057 (16)	0.07419 (17)	0.0427 (3)
H9	0.7756	0.6340	0.0946	0.051*
C10	0.88322 (11)	0.7460 (2)	0.1577 (2)	0.0533 (5)
H10	0.9112	0.6926	0.2334	0.064*
C11	0.92203 (10)	0.8613 (2)	0.12745 (18)	0.0497 (4)
C12	0.88199 (10)	0.93915 (17)	0.01121 (17)	0.0436 (3)
H12	0.9094	1.0146	−0.0105	0.052*
C13	0.80182 (9)	0.90444 (14)	−0.07167 (15)	0.0348 (3)
H13	0.7745	0.9570	−0.1486	0.042*
C14	1.03882 (16)	0.8432 (4)	0.3356 (3)	0.1044 (12)
H14A	1.0928	0.8853	0.3792	0.157*
H14B	1.0484	0.7512	0.3185	0.157*
H14C	1.0017	0.8498	0.3974	0.157*
N1	0.59374 (7)	0.83818 (10)	−0.04781 (12)	0.0298 (2)
H1	0.5932	0.7982	0.0253	0.036*
N2	0.66110 (10)	1.37511 (12)	0.03591 (17)	0.0486 (3)
H2	0.6490	1.4494	−0.0128	0.058*
N3	0.72483 (10)	1.37633 (13)	0.15800 (16)	0.0497 (3)
O1	0.63534 (8)	0.62011 (10)	−0.11826 (12)	0.0436 (3)
O2	0.63874 (7)	0.81515 (10)	−0.26973 (10)	0.0378 (2)
O3	0.99969 (9)	0.9074 (2)	0.20519 (17)	0.0789 (5)
S1	0.65443 (2)	0.75832 (3)	−0.13090 (3)	0.02874 (9)
Cl1	0.80966 (4)	1.20719 (5)	0.34939 (5)	0.06387 (16)

	U11	U22	U33	U12	U13	U23
C4	0.0299 (5)	0.0219 (5)	0.0284 (5)	−0.0007 (4)	0.0075 (4)	−0.0003 (4)
C5	0.0305 (6)	0.0314 (6)	0.0339 (6)	0.0016 (5)	−0.0001 (5)	0.0017 (5)
C6	0.0366 (7)	0.0296 (6)	0.0441 (8)	0.0063 (5)	0.0011 (6)	0.0087 (5)
C7	0.0370 (7)	0.0217 (5)	0.0443 (7)	0.0024 (5)	0.0087 (6)	0.0009 (5)
C2	0.0354 (6)	0.0242 (5)	0.0311 (6)	−0.0014 (5)	0.0067 (5)	−0.0032 (4)
C3	0.0358 (6)	0.0228 (5)	0.0259 (5)	0.0005 (4)	0.0058 (5)	0.0017 (4)
C1	0.0471 (8)	0.0322 (7)	0.0372 (7)	−0.0059 (6)	0.0049 (6)	−0.0085 (5)
C8	0.0352 (6)	0.0283 (6)	0.0269 (6)	0.0033 (5)	0.0065 (5)	0.0024 (4)
C9	0.0423 (8)	0.0406 (7)	0.0428 (8)	0.0026 (6)	0.0068 (6)	0.0160 (6)
C10	0.0381 (8)	0.0683 (12)	0.0478 (9)	0.0044 (7)	0.0011 (7)	0.0286 (8)
C11	0.0311 (7)	0.0727 (12)	0.0421 (8)	−0.0022 (7)	0.0040 (6)	0.0134 (8)
C12	0.0372 (7)	0.0485 (8)	0.0436 (8)	−0.0060 (6)	0.0080 (6)	0.0109 (7)
C13	0.0381 (7)	0.0336 (6)	0.0313 (6)	0.0015 (5)	0.0066 (5)	0.0073 (5)
C14	0.0523 (12)	0.175 (3)	0.0664 (15)	−0.0201 (16)	−0.0193 (11)	0.0445 (18)
N1	0.0363 (5)	0.0232 (5)	0.0295 (5)	−0.0051 (4)	0.0081 (4)	−0.0004 (4)
N2	0.0575 (8)	0.0211 (5)	0.0617 (9)	0.0005 (5)	0.0065 (7)	0.0009 (5)
N3	0.0595 (9)	0.0294 (6)	0.0568 (9)	−0.0080 (6)	0.0091 (7)	−0.0109 (6)
O1	0.0615 (7)	0.0206 (4)	0.0443 (6)	−0.0064 (4)	0.0063 (5)	−0.0047 (4)
O2	0.0491 (6)	0.0382 (5)	0.0226 (4)	−0.0019 (4)	0.0033 (4)	0.0000 (4)
O3	0.0394 (6)	0.1184 (14)	0.0647 (9)	−0.0214 (8)	−0.0107 (6)	0.0322 (9)
S1	0.03872 (17)	0.02109 (14)	0.02355 (15)	−0.00219 (11)	0.00327 (12)	−0.00259 (10)
Cl1	0.0721 (3)	0.0615 (3)	0.0427 (2)	−0.0113 (2)	−0.0115 (2)	−0.00649 (19)

C4—C3	1.3728 (17)	C9—H9	0.9300
C4—C5	1.4096 (17)	C10—C11	1.387 (3)
C4—N1	1.4456 (15)	C10—H10	0.9300
C5—C6	1.3787 (19)	C11—O3	1.362 (2)
C5—H5	0.9300	C11—C12	1.391 (2)
C6—C7	1.397 (2)	C12—C13	1.377 (2)
C6—H6	0.9300	C12—H12	0.9300
C7—N2	1.3613 (17)	C13—H13	0.9300
C7—C2	1.4041 (19)	C14—O3	1.421 (3)
C2—C3	1.4006 (16)	C14—H14A	0.9600
C2—C1	1.4180 (18)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C1—N3	1.314 (2)	N1—S1	1.6393 (12)
C1—Cl1	1.7038 (17)	N1—H1	0.8235
C8—C9	1.3866 (19)	N2—N3	1.354 (2)
C8—C13	1.3980 (19)	N2—H2	0.8799
C8—S1	1.7507 (14)	O1—S1	1.4359 (10)
C9—C10	1.389 (2)	O2—S1	1.4344 (10)
C3—C4—C5	121.88 (11)	O3—C11—C10	124.39 (15)
C3—C4—N1	119.90 (11)	O3—C11—C12	115.10 (16)
C5—C4—N1	118.21 (11)	C10—C11—C12	120.50 (15)
C6—C5—C4	121.37 (12)	C13—C12—C11	119.94 (14)
C6—C5—H5	119.3	C13—C12—H12	120.0
C4—C5—H5	119.3	C11—C12—H12	120.0
C5—C6—C7	117.05 (12)	C12—C13—C8	119.72 (13)
C5—C6—H6	121.5	C12—C13—H13	120.1
C7—C6—H6	121.5	C8—C13—H13	120.1
N2—C7—C6	132.03 (13)	O3—C14—H14A	109.5
N2—C7—C2	106.28 (13)	O3—C14—H14B	109.5
C6—C7—C2	121.64 (12)	H14A—C14—H14B	109.5
C3—C2—C7	120.72 (12)	O3—C14—H14C	109.5
C3—C2—C1	135.76 (13)	H14A—C14—H14C	109.5
C7—C2—C1	103.44 (12)	H14B—C14—H14C	109.5
C4—C3—C2	117.33 (11)	C4—N1—S1	116.71 (9)
C4—C3—H3	121.3	C4—N1—H1	113.9
C2—C3—H3	121.3	S1—N1—H1	109.7
N3—C1—C2	112.75 (14)	N3—N2—C7	112.47 (13)
N3—C1—Cl1	120.74 (12)	N3—N2—H2	118.6
C2—C1—Cl1	126.50 (12)	C7—N2—H2	128.2
C9—C8—C13	120.34 (13)	C1—N3—N2	105.00 (12)
C9—C8—S1	119.95 (11)	C11—O3—C14	118.12 (18)
C13—C8—S1	119.25 (10)	O2—S1—O1	118.65 (6)
C8—C9—C10	119.78 (15)	O2—S1—N1	107.29 (6)
C8—C9—H9	120.1	O1—S1—N1	105.16 (6)
C10—C9—H9	120.1	O2—S1—C8	108.27 (6)
C11—C10—C9	119.68 (14)	O1—S1—C8	109.65 (7)
C11—C10—H10	120.2	N1—S1—C8	107.25 (6)
C9—C10—H10	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.82	2.26	3.046 (2)	161
N2—H2···O1ii	0.88	1.99	2.862 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.82	2.26	3.046 (2)	161
N2—H2⋯O1ii	0.88	1.99	2.862 (2)	174

Symmetry codes: (i) ; (ii) .