N-[7-Eth-oxy-2-(prop-2-en-1-yl)-2H-indazol-6-yl]-4-methyl-benzene-sulfonamide.

In the title compound, C(19)H(21)N(3)O(3)S, the C-SO(2)-NH-C torsion angle is 66.20 (9)°. The dihedral angle between the benzene ring and the essentially planar indazole ring system [r.m.s. deviation = 0.0361 (1) Å] is 72.97 (6)°. The S atom has a distorted tetra-hedral geometry [maximum deviation = O-S-O = 119.30 (6)°]. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds. In addition, weak C-H⋯O inter-actions may stabilize the crystal packing.

Related literature

For related structures, see: Abbassi et al. (2011a ▶,b ▶). For the biological activity of sulfonamides, see: Soledade et al. (2006 ▶); Lee & Lee (2002 ▶). For the synthesis of 7-eth­oxy-N-alkyl­indazole derivatives, see: Abbassi et al. (2011c ▶).

Experimental

Crystal data

C19H21N3O3S

M = 371.45

Monoclinic,

a = 10.1459 (7) Å

b = 9.9506 (7) Å

c = 18.3720 (13) Å

β = 95.097 (3)°

V = 1847.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.32 × 0.31 × 0.24 mm

Data collection

Bruker APEXII CCD detector diffractometer

20488 measured reflections

4034 independent reflections

3693 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.06

4034 reflections

238 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.39 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 datablock(s) I, global. DOI: 10.1107/S1600536811045855/bt5700sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045855/bt5700Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045855/bt5700Isup3.cml

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

C19H21N3O3S	F(000) = 784
Mr = 371.45	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 243 reflections
a = 10.1459 (7) Å	θ = 2.3–27.2°
b = 9.9506 (7) Å	µ = 0.20 mm−1
c = 18.3720 (13) Å	T = 296 K
β = 95.097 (3)°	Prism, colourless
V = 1847.5 (2) Å3	0.32 × 0.31 × 0.24 mm
Z = 4

Bruker APEXII CCD detector diffractometer	3693 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 27.0°, θmin = 2.0°
ω and φ scans	h = −12→12
20488 measured reflections	k = −12→12
4034 independent reflections	l = −22→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0522P)2 + 0.8814P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4034 reflections	Δρmax = 0.69 e Å−3
238 parameters	Δρmin = −0.39 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0206 (15)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
C1	0.76485 (15)	0.66788 (16)	0.17902 (8)	0.0312 (3)
C10	0.93118 (13)	0.91852 (15)	−0.08185 (7)	0.0252 (3)
C11	0.79381 (13)	0.94222 (14)	−0.07596 (7)	0.0216 (3)
C12	0.71089 (12)	0.83505 (13)	−0.05612 (7)	0.0207 (3)
C13	0.98070 (14)	1.04447 (16)	−0.09800 (8)	0.0296 (3)
C14	0.5674 (2)	0.8996 (2)	0.29302 (10)	0.0556 (6)
C15	0.50380 (15)	0.94048 (18)	−0.09413 (10)	0.0373 (4)
C16	0.36049 (15)	0.90887 (17)	−0.09383 (10)	0.0354 (4)
C17	0.88027 (17)	1.27272 (16)	−0.11789 (10)	0.0375 (4)
C18	0.86633 (18)	1.2985 (2)	−0.19860 (12)	0.0523 (5)
C19	0.8539 (2)	1.2068 (3)	−0.24945 (12)	0.0708 (7)
C2	0.73094 (17)	0.75204 (19)	0.23458 (9)	0.0389 (4)
C3	0.60421 (17)	0.80532 (16)	0.23408 (8)	0.0335 (3)
C4	0.51129 (15)	0.77163 (14)	0.17715 (8)	0.0283 (3)
C5	0.54257 (13)	0.68865 (14)	0.12097 (8)	0.0244 (3)
C6	0.67012 (13)	0.63684 (13)	0.12255 (7)	0.0211 (3)
C7	0.76898 (13)	0.71167 (13)	−0.04258 (7)	0.0208 (3)
C8	0.90547 (13)	0.68843 (14)	−0.05067 (8)	0.0256 (3)
C9	0.98638 (14)	0.78904 (15)	−0.06954 (8)	0.0284 (3)
H1	0.8499	0.6328	0.1797	0.037*
H13	1.0678	1.0651	−0.1057	0.036*
H14A	0.5216	0.9759	0.2711	0.083*
H14B	0.6461	0.9291	0.3214	0.083*
H14C	0.5109	0.8538	0.3242	0.083*
H15A	0.5298	0.9353	−0.1436	0.045*
H15B	0.5208	1.0310	−0.0761	0.045*
H16A	0.3429	0.8224	−0.1158	0.053*
H16B	0.3094	0.9761	−0.1211	0.053*
H16C	0.3368	0.9077	−0.0444	0.053*
H17A	0.9628	1.3116	−0.0969	0.045*
H17B	0.8085	1.3171	−0.0958	0.045*
H18	0.8666	1.3877	−0.2137	0.063*
H19A	0.8532	1.1163	−0.2367	0.085*
H19B	0.8458	1.2318	−0.2984	0.085*
H1N	0.6049	0.6137	−0.0394	0.026*
H2	0.7940	0.7731	0.2728	0.047*
H4	0.4259	0.8057	0.1768	0.034*
H5	0.4795	0.6678	0.0828	0.029*
H8	0.9400	0.6025	−0.0429	0.031*
H9	1.0756	0.7732	−0.0742	0.034*
N1	0.68677 (11)	0.60110 (11)	−0.02548 (6)	0.0216 (2)
N2	0.76199 (11)	1.07276 (12)	−0.08760 (7)	0.0254 (3)
N3	0.87862 (12)	1.13021 (12)	−0.10026 (7)	0.0275 (3)
O1	0.57901 (9)	0.84573 (10)	−0.04824 (5)	0.0253 (2)
O2	0.84526 (10)	0.49024 (11)	0.06679 (6)	0.0292 (2)
O3	0.61092 (10)	0.41953 (10)	0.04911 (6)	0.0286 (2)
S1	0.70831 (3)	0.52451 (3)	0.053468 (17)	0.02072 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0241 (7)	0.0381 (8)	0.0310 (7)	0.0053 (6)	−0.0010 (6)	−0.0003 (6)
C10	0.0198 (6)	0.0297 (7)	0.0264 (6)	−0.0003 (5)	0.0042 (5)	0.0030 (5)
C11	0.0198 (6)	0.0234 (6)	0.0218 (6)	0.0011 (5)	0.0027 (5)	0.0019 (5)
C12	0.0169 (6)	0.0233 (6)	0.0221 (6)	0.0018 (5)	0.0038 (5)	0.0004 (5)
C13	0.0210 (7)	0.0338 (8)	0.0343 (7)	−0.0038 (6)	0.0038 (5)	0.0060 (6)
C14	0.0765 (14)	0.0595 (12)	0.0305 (8)	0.0257 (11)	0.0018 (9)	−0.0124 (8)
C15	0.0246 (7)	0.0411 (9)	0.0460 (9)	0.0066 (6)	0.0024 (6)	0.0175 (7)
C16	0.0217 (7)	0.0376 (8)	0.0463 (9)	0.0036 (6)	−0.0010 (6)	0.0049 (7)
C17	0.0338 (8)	0.0267 (8)	0.0519 (10)	−0.0066 (6)	0.0024 (7)	0.0104 (7)
C18	0.0383 (10)	0.0547 (12)	0.0637 (13)	−0.0004 (8)	0.0034 (9)	0.0353 (10)
C19	0.0733 (16)	0.099 (2)	0.0401 (11)	0.0078 (14)	0.0022 (10)	0.0231 (12)
C2	0.0410 (9)	0.0466 (10)	0.0272 (7)	0.0060 (7)	−0.0072 (6)	−0.0061 (7)
C3	0.0465 (9)	0.0310 (8)	0.0236 (7)	0.0083 (7)	0.0064 (6)	0.0012 (6)
C4	0.0294 (7)	0.0253 (7)	0.0312 (7)	0.0078 (6)	0.0079 (6)	0.0042 (6)
C5	0.0220 (6)	0.0225 (6)	0.0284 (7)	0.0020 (5)	0.0016 (5)	0.0012 (5)
C6	0.0222 (6)	0.0191 (6)	0.0225 (6)	0.0017 (5)	0.0044 (5)	0.0023 (5)
C7	0.0204 (6)	0.0214 (6)	0.0210 (6)	0.0013 (5)	0.0044 (5)	0.0006 (5)
C8	0.0223 (7)	0.0264 (7)	0.0287 (7)	0.0071 (5)	0.0064 (5)	0.0026 (5)
C9	0.0189 (6)	0.0338 (8)	0.0333 (7)	0.0045 (5)	0.0071 (5)	0.0046 (6)
N1	0.0201 (5)	0.0204 (5)	0.0242 (5)	0.0014 (4)	0.0022 (4)	0.0021 (4)
N2	0.0225 (6)	0.0233 (6)	0.0306 (6)	−0.0027 (4)	0.0036 (4)	0.0047 (5)
N3	0.0249 (6)	0.0261 (6)	0.0317 (6)	−0.0052 (5)	0.0024 (5)	0.0063 (5)
O1	0.0169 (5)	0.0249 (5)	0.0346 (5)	0.0035 (4)	0.0052 (4)	0.0079 (4)
O2	0.0237 (5)	0.0299 (5)	0.0345 (5)	0.0111 (4)	0.0053 (4)	0.0055 (4)
O3	0.0317 (5)	0.0183 (5)	0.0362 (5)	−0.0026 (4)	0.0045 (4)	0.0027 (4)
S1	0.02049 (18)	0.01647 (17)	0.02557 (18)	0.00367 (11)	0.00417 (12)	0.00238 (11)

C1—H1	0.9300	C19—H19B	0.9300
C1—C2	1.387 (2)	C19—H19A	0.9300
C10—C9	1.415 (2)	C19—C18	1.304 (4)
C10—C13	1.392 (2)	C2—H2	0.9300
C11—C10	1.4271 (18)	C3—C14	1.505 (2)
C11—C12	1.4257 (18)	C3—C2	1.390 (2)
C11—N2	1.3509 (18)	C4—H4	0.9300
C12—O1	1.3626 (15)	C4—C3	1.386 (2)
C13—H13	0.9300	C5—H5	0.9300
C13—N3	1.340 (2)	C5—C4	1.381 (2)
C14—H14C	0.9600	C6—C5	1.3910 (18)
C14—H14B	0.9600	C6—C1	1.385 (2)
C14—H14A	0.9600	C7—N1	1.4323 (17)
C15—H15B	0.9700	C7—C8	1.4247 (18)
C15—H15A	0.9700	C7—C12	1.3749 (18)
C15—C16	1.488 (2)	C8—H8	0.9300
C15—O1	1.4380 (17)	C8—C9	1.359 (2)
C16—H16C	0.9600	C9—H9	0.9300
C16—H16B	0.9600	N1—H1N	0.8562
C16—H16A	0.9600	N2—N3	1.3528 (16)
C17—H17B	0.9700	S1—C6	1.7600 (13)
C17—H17A	0.9700	S1—N1	1.6358 (11)
C17—C18	1.499 (3)	S1—O3	1.4352 (10)
C17—N3	1.4549 (19)	S1—O2	1.4305 (10)
C18—H18	0.9300
C2—C1—H1	120.5	H19A—C19—H19B	120.0
C6—C1—H1	120.5	C18—C19—H19B	120.0
C6—C1—C2	119.01 (14)	C18—C19—H19A	120.0
C9—C10—C11	120.91 (13)	C3—C2—H2	119.5
C13—C10—C11	103.93 (12)	C1—C2—H2	119.5
C13—C10—C9	135.12 (13)	C1—C2—C3	121.00 (14)
C12—C11—C10	119.89 (12)	C2—C3—C14	121.45 (16)
N2—C11—C10	111.60 (12)	C4—C3—C14	119.87 (15)
N2—C11—C12	128.43 (12)	C4—C3—C2	118.67 (14)
C7—C12—C11	117.44 (12)	C3—C4—H4	119.2
O1—C12—C11	125.18 (12)	C5—C4—H4	119.2
O1—C12—C7	117.36 (12)	C5—C4—C3	121.52 (13)
C10—C13—H13	126.6	C6—C5—H5	120.6
N3—C13—H13	126.6	C4—C5—H5	120.6
N3—C13—C10	106.70 (12)	C4—C5—C6	118.77 (13)
H14B—C14—H14C	109.5	C5—C6—S1	118.97 (10)
H14A—C14—H14C	109.5	C1—C6—S1	119.95 (11)
C3—C14—H14C	109.5	C1—C6—C5	121.02 (13)
H14A—C14—H14B	109.5	C8—C7—N1	119.24 (12)
C3—C14—H14B	109.5	C12—C7—N1	118.49 (11)
C3—C14—H14A	109.5	C12—C7—C8	122.08 (12)
H15A—C15—H15B	108.3	C7—C8—H8	119.3
C16—C15—H15B	109.9	C9—C8—H8	119.3
O1—C15—H15B	109.9	C9—C8—C7	121.45 (13)
C16—C15—H15A	109.9	C10—C9—H9	120.9
O1—C15—H15A	109.9	C8—C9—H9	120.9
O1—C15—C16	109.09 (13)	C8—C9—C10	118.16 (12)
H16B—C16—H16C	109.5	S1—N1—H1N	112.5
H16A—C16—H16C	109.5	C7—N1—H1N	112.9
C15—C16—H16C	109.5	C7—N1—S1	121.19 (9)
H16A—C16—H16B	109.5	C11—N2—N3	103.48 (11)
C15—C16—H16B	109.5	N2—N3—C17	118.53 (12)
C15—C16—H16A	109.5	C13—N3—C17	127.12 (13)
H17A—C17—H17B	107.8	C13—N3—N2	114.27 (12)
C18—C17—H17B	109.1	C12—O1—C15	117.63 (11)
N3—C17—H17B	109.1	N1—S1—C6	108.84 (6)
C18—C17—H17A	109.1	O3—S1—C6	107.93 (6)
N3—C17—H17A	109.1	O2—S1—C6	107.50 (6)
N3—C17—C18	112.65 (15)	O3—S1—N1	104.63 (6)
C17—C18—H18	117.2	O2—S1—N1	108.30 (6)
C19—C18—H18	117.2	O2—S1—O3	119.30 (6)
C19—C18—C17	125.68 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.86	2.21	3.0199 (15)	159.
C8—H8···O2ii	0.93	2.44	3.1270 (17)	131.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.86	2.21	3.0199 (15)	159
C8—H8⋯O2ii	0.93	2.44	3.1270 (17)	131

Symmetry codes: (i) ; (ii) .