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

The indazole ring system [maximum deviation = 0.013 (2) Å] of the title compound, C15H15N3O3S, makes a dihedral angle of 50.11 (7)° with the benzene ring. In the crystal, cohesion is provided by C-H⋯O and N-H⋯N hydrogen bonds, which link the molecules into chains propagating along the b-axis direction.

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

C15H15N3O3S

M = 317.36

Monoclinic,

a = 10.1069 (3) Å

b = 13.6178 (3) Å

c = 10.8530 (2) Å

β = 90.777 (2)°

V = 1493.60 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.39 × 0.33 × 0.23 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.651, T max = 0.747

19007 measured reflections

4178 independent reflections

3232 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.125

S = 1.02

4178 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.28 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/S1600536813021624/bt6924sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021624/bt6924Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021624/bt6924Isup3.cml

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

C15H15N3O3S	F(000) = 664
Mr = 317.36	Dx = 1.411 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4178 reflections
a = 10.1069 (3) Å	θ = 2.4–29.6°
b = 13.6178 (3) Å	µ = 0.23 mm−1
c = 10.8530 (2) Å	T = 296 K
β = 90.777 (2)°	Block, colourless
V = 1493.60 (6) Å3	0.39 × 0.33 × 0.23 mm
Z = 4

Bruker X8 APEXII diffractometer	4178 independent reflections
Radiation source: fine-focus sealed tube	3232 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 29.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→13
Tmin = 0.651, Tmax = 0.747	k = −18→18
19007 measured reflections	l = −15→15

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) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0694P)2 + 0.2788P] where P = (Fo2 + 2Fc2)/3
4178 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.28 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	0.35240 (14)	0.12964 (10)	0.31509 (12)	0.0369 (3)
C2	0.32504 (16)	0.16841 (11)	0.19599 (14)	0.0411 (3)
H2	0.3091	0.2353	0.1875	0.049*
C3	0.32149 (15)	0.11009 (11)	0.09337 (13)	0.0395 (3)
H3	0.3025	0.1356	0.0156	0.047*
C4	0.34782 (13)	0.01018 (10)	0.11104 (12)	0.0341 (3)
C5	0.37682 (14)	−0.02927 (10)	0.22857 (13)	0.0364 (3)
C6	0.37813 (15)	0.03159 (10)	0.33265 (13)	0.0379 (3)
H6	0.3958	0.0065	0.4108	0.045*
C7	0.39589 (17)	−0.13088 (11)	0.20596 (14)	0.0452 (4)
H7	0.4174	−0.1766	0.2666	0.054*
C8	0.32417 (16)	−0.06444 (13)	−0.10173 (13)	0.0479 (4)
H8A	0.2402	−0.0949	−0.1185	0.072*
H8B	0.3925	−0.0996	−0.1437	0.072*
H8C	0.3221	0.0023	−0.1301	0.072*
C9	0.53540 (14)	0.33142 (10)	0.36119 (13)	0.0379 (3)
C10	0.46991 (15)	0.42076 (11)	0.35614 (15)	0.0437 (3)
H10	0.4051	0.4347	0.4136	0.052*
C11	0.49956 (17)	0.48930 (11)	0.26688 (15)	0.0472 (4)
H11	0.4541	0.5486	0.2632	0.057*
C12	0.59753 (18)	0.46877 (13)	0.18314 (15)	0.0494 (4)
C13	0.6648 (2)	0.37995 (15)	0.18895 (16)	0.0586 (5)
H13	0.7313	0.3667	0.1329	0.070*
C14	0.63377 (17)	0.31130 (12)	0.27713 (15)	0.0498 (4)
H14	0.6786	0.2517	0.2803	0.060*
C15	0.5734 (3)	0.62492 (16)	0.0850 (2)	0.0806 (7)
H15A	0.6100	0.6615	0.0179	0.121*
H15B	0.5874	0.6603	0.1605	0.121*
H15C	0.4802	0.6159	0.0709	0.121*
N1	0.35058 (13)	0.19331 (9)	0.42115 (11)	0.0409 (3)
H1	0.2838	0.2355	0.4224	0.049*
N2	0.37938 (15)	−0.15242 (9)	0.08822 (12)	0.0469 (3)
N3	0.35107 (12)	−0.06604 (9)	0.03012 (11)	0.0395 (3)
O1	0.45149 (14)	0.29493 (9)	0.58123 (10)	0.0567 (3)
O2	0.58740 (13)	0.16972 (9)	0.47644 (12)	0.0579 (3)
O3	0.63640 (17)	0.53163 (11)	0.09322 (13)	0.0755 (4)
S1	0.48793 (4)	0.24415 (3)	0.47110 (3)	0.04197 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0415 (7)	0.0326 (7)	0.0365 (7)	−0.0015 (5)	−0.0014 (5)	0.0031 (5)
C2	0.0483 (8)	0.0321 (7)	0.0429 (7)	0.0028 (6)	−0.0013 (6)	0.0080 (6)
C3	0.0421 (8)	0.0392 (7)	0.0370 (7)	0.0019 (6)	−0.0040 (6)	0.0099 (6)
C4	0.0306 (6)	0.0362 (7)	0.0356 (6)	−0.0032 (5)	−0.0025 (5)	0.0033 (5)
C5	0.0394 (7)	0.0314 (6)	0.0382 (7)	−0.0036 (5)	−0.0061 (5)	0.0062 (5)
C6	0.0459 (8)	0.0325 (7)	0.0352 (6)	−0.0043 (6)	−0.0044 (5)	0.0061 (5)
C7	0.0576 (10)	0.0321 (7)	0.0455 (8)	−0.0008 (6)	−0.0100 (7)	0.0048 (6)
C8	0.0482 (9)	0.0578 (10)	0.0375 (7)	−0.0042 (7)	−0.0038 (6)	−0.0005 (7)
C9	0.0381 (7)	0.0349 (7)	0.0404 (7)	0.0012 (6)	−0.0068 (5)	−0.0049 (5)
C10	0.0387 (8)	0.0394 (8)	0.0530 (8)	0.0038 (6)	0.0047 (6)	0.0003 (6)
C11	0.0449 (8)	0.0376 (8)	0.0589 (9)	−0.0007 (6)	−0.0006 (7)	0.0026 (7)
C12	0.0552 (10)	0.0494 (9)	0.0438 (8)	−0.0136 (8)	0.0020 (7)	−0.0036 (6)
C13	0.0637 (11)	0.0624 (11)	0.0502 (9)	−0.0011 (9)	0.0174 (8)	−0.0140 (8)
C14	0.0531 (9)	0.0452 (9)	0.0511 (9)	0.0092 (7)	0.0017 (7)	−0.0142 (7)
C15	0.114 (2)	0.0596 (12)	0.0682 (13)	−0.0229 (13)	−0.0051 (12)	0.0189 (10)
N1	0.0482 (7)	0.0341 (6)	0.0403 (6)	0.0021 (5)	0.0011 (5)	−0.0004 (5)
N2	0.0566 (8)	0.0359 (6)	0.0480 (7)	−0.0003 (6)	−0.0074 (6)	−0.0004 (5)
N3	0.0433 (7)	0.0386 (6)	0.0366 (6)	−0.0015 (5)	−0.0047 (5)	0.0004 (5)
O1	0.0813 (9)	0.0532 (7)	0.0355 (5)	0.0041 (6)	−0.0057 (5)	−0.0049 (5)
O2	0.0621 (8)	0.0473 (7)	0.0638 (7)	0.0159 (6)	−0.0164 (6)	0.0051 (6)
O3	0.0955 (11)	0.0686 (9)	0.0631 (8)	−0.0169 (8)	0.0209 (8)	0.0082 (7)
S1	0.0531 (2)	0.0361 (2)	0.03648 (19)	0.00611 (15)	−0.00831 (15)	−0.00026 (13)

C1—C6	1.3731 (19)	C9—S1	1.7553 (15)
C1—C2	1.4199 (19)	C10—C11	1.381 (2)
C1—N1	1.4415 (18)	C10—H10	0.9300
C2—C3	1.368 (2)	C11—C12	1.382 (2)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.3990 (19)	C12—O3	1.360 (2)
C3—H3	0.9300	C12—C13	1.388 (3)
C4—N3	1.3603 (18)	C13—C14	1.377 (3)
C4—C5	1.4111 (18)	C13—H13	0.9300
C5—C6	1.401 (2)	C14—H14	0.9300
C5—C7	1.419 (2)	C15—O3	1.423 (3)
C6—H6	0.9300	C15—H15A	0.9600
C7—N2	1.320 (2)	C15—H15B	0.9600
C7—H7	0.9300	C15—H15C	0.9600
C8—N3	1.4530 (19)	N1—S1	1.6370 (14)
C8—H8A	0.9600	N1—H1	0.8867
C8—H8B	0.9600	N2—N3	1.3633 (18)
C8—H8C	0.9600	O1—S1	1.4332 (12)
C9—C10	1.386 (2)	O2—S1	1.4283 (12)
C9—C14	1.386 (2)
C6—C1—C2	121.47 (13)	C10—C11—C12	119.26 (15)
C6—C1—N1	118.59 (12)	C10—C11—H11	120.4
C2—C1—N1	119.92 (12)	C12—C11—H11	120.4
C3—C2—C1	121.86 (13)	O3—C12—C11	124.13 (17)
C3—C2—H2	119.1	O3—C12—C13	115.78 (16)
C1—C2—H2	119.1	C11—C12—C13	120.08 (15)
C2—C3—C4	116.75 (12)	C14—C13—C12	120.46 (15)
C2—C3—H3	121.6	C14—C13—H13	119.8
C4—C3—H3	121.6	C12—C13—H13	119.8
N3—C4—C3	131.28 (13)	C13—C14—C9	119.70 (15)
N3—C4—C5	106.65 (12)	C13—C14—H14	120.2
C3—C4—C5	122.07 (13)	C9—C14—H14	120.2
C6—C5—C4	120.21 (13)	O3—C15—H15A	109.5
C6—C5—C7	135.76 (13)	O3—C15—H15B	109.5
C4—C5—C7	104.01 (12)	H15A—C15—H15B	109.5
C1—C6—C5	117.62 (12)	O3—C15—H15C	109.5
C1—C6—H6	121.2	H15A—C15—H15C	109.5
C5—C6—H6	121.2	H15B—C15—H15C	109.5
N2—C7—C5	111.63 (13)	C1—N1—S1	119.93 (10)
N2—C7—H7	124.2	C1—N1—H1	114.8
C5—C7—H7	124.2	S1—N1—H1	111.3
N3—C8—H8A	109.5	C7—N2—N3	106.21 (12)
N3—C8—H8B	109.5	C4—N3—N2	111.50 (11)
H8A—C8—H8B	109.5	C4—N3—C8	128.21 (13)
N3—C8—H8C	109.5	N2—N3—C8	120.24 (13)
H8A—C8—H8C	109.5	C12—O3—C15	118.25 (16)
H8B—C8—H8C	109.5	O2—S1—O1	119.82 (7)
C10—C9—C14	119.61 (15)	O2—S1—N1	107.85 (7)
C10—C9—S1	119.11 (12)	O1—S1—N1	104.71 (8)
C14—C9—S1	121.24 (12)	O2—S1—C9	108.02 (8)
C11—C10—C9	120.87 (14)	O1—S1—C9	108.41 (7)
C11—C10—H10	119.6	N1—S1—C9	107.44 (6)
C9—C10—H10	119.6

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.89	2.25	3.1335 (19)	176
C8—H8A···O1ii	0.96	2.49	3.391 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.89	2.25	3.1335 (19)	176
C8—H8A⋯O1ii	0.96	2.49	3.391 (2)	157

Symmetry codes: (i) ; (ii) .