N-(1-Allyl-3-chloro-4-eth-oxy-1H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

In the title compound, C19H20ClN3O3S, the benzene ring is inclined to the indazole ring system by 51.23 (8)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers which stack in columns parallel to [011]. The atoms in the allyl group are disordered over two sets of sites with an occupancy ratio of 0.624 (8):0.376 (8).

Related literature

For the biological activity of sulfonamides, see: El-Sayed et al. (2011 ▶); Mustafa et al. (2012 ▶); Scozzafava et al. (2003 ▶); Bouissane et al. (2006 ▶). For similar compounds, see: Abbassi et al. (2012 ▶, 2013 ▶); Chicha et al. (2014 ▶).

Experimental

Crystal data

C19H20ClN3O3S

M = 405.89

Triclinic,

a = 10.0345 (2) Å

b = 10.5208 (2) Å

c = 10.7237 (2) Å

α = 71.561 (1)°

β = 69.601 (1)°

γ = 83.039 (1)°

V = 1006.56 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.42 × 0.35 × 0.30 mm

Data collection

Bruker X8 APEX diffractometer

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

21411 measured reflections

4792 independent reflections

3967 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.126

S = 1.04

4792 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.35 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/S1600536814010253/bt6978sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010253/bt6978Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010253/bt6978Isup3.cml

CCDC reference: 1001396

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H20ClN3O3S	Z = 2
Mr = 405.89	F(000) = 424
Triclinic, P1	Dx = 1.339 Mg m−3
Hall symbol: -P 1	Melting point: 373 K
a = 10.0345 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5208 (2) Å	Cell parameters from 4792 reflections
c = 10.7237 (2) Å	θ = 2.5–27.9°
α = 71.561 (1)°	µ = 0.32 mm−1
β = 69.601 (1)°	T = 296 K
γ = 83.039 (1)°	Block, colourless
V = 1006.56 (3) Å3	0.42 × 0.35 × 0.30 mm

Bruker X8 APEX diffractometer	4792 independent reflections
Radiation source: fine-focus sealed tube	3967 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 27.9°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.693, Tmax = 0.747	k = −13→13
21411 measured reflections	l = −14→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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0687P)2 + 0.2408P] where P = (Fo2 + 2Fc2)/3
4792 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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	Occ. (<1)
C1	0.8128 (2)	0.5118 (2)	0.42585 (19)	0.0628 (5)
C2	0.69725 (19)	0.46383 (17)	0.55054 (17)	0.0484 (4)
C3	0.6105 (2)	0.57806 (17)	0.55830 (18)	0.0526 (4)
C4	0.4795 (2)	0.57522 (17)	0.6626 (2)	0.0544 (4)
H4	0.4230	0.6519	0.6653	0.065*
C5	0.43792 (18)	0.45479 (17)	0.76086 (18)	0.0481 (4)
H5	0.3495	0.4488	0.8299	0.058*
C6	0.52561 (16)	0.33930 (15)	0.76030 (16)	0.0393 (3)
C7	0.65446 (17)	0.34152 (16)	0.65574 (16)	0.0415 (3)
C8	0.8599 (2)	0.2160 (2)	0.6873 (2)	0.0608 (5)
H8A	0.8369	0.2187	0.7821	0.073*
H8B	0.9213	0.2907	0.6252	0.073*
C9	0.9321 (3)	0.0880 (3)	0.6722 (4)	0.0976 (9)
H9A	0.9546	0.0866	0.5780	0.146*
H9B	0.8705	0.0149	0.7343	0.146*
H9C	1.0181	0.0796	0.6945	0.146*
C10	0.62203 (17)	0.22040 (15)	1.03861 (15)	0.0404 (3)
C11	0.7030 (2)	0.10747 (17)	1.0730 (2)	0.0542 (4)
H11	0.6664	0.0226	1.0973	0.065*
C12	0.8389 (2)	0.1218 (2)	1.0708 (2)	0.0618 (5)
H12	0.8932	0.0457	1.0949	0.074*
C13	0.8960 (2)	0.2475 (2)	1.0333 (2)	0.0570 (4)
C14	0.8130 (2)	0.35895 (19)	0.9984 (2)	0.0586 (5)
H14	0.8502	0.4438	0.9724	0.070*
C15	0.67618 (19)	0.34768 (16)	1.00100 (19)	0.0510 (4)
H15	0.6214	0.4237	0.9781	0.061*
C16	1.0466 (2)	0.2623 (3)	1.0261 (3)	0.0839 (7)
H16A	1.0877	0.1752	1.0543	0.126*
H16B	1.0460	0.3125	1.0870	0.126*
H16C	1.1017	0.3086	0.9323	0.126*
C17	0.6318 (3)	0.8191 (2)	0.4084 (3)	0.0869 (8)
H17A	0.5322	0.8251	0.4162	0.104*	0.376 (8)
H17B	0.6870	0.8653	0.3133	0.104*	0.376 (8)
H17C	0.6737	0.8565	0.3084	0.104*	0.624 (8)
H17D	0.5295	0.8209	0.4297	0.104*	0.624 (8)
C18A	0.657 (2)	0.8881 (16)	0.5179 (15)	0.082 (4)	0.376 (8)
H18A	0.6423	0.8383	0.6103	0.099*	0.376 (8)
C19A	0.6994 (8)	1.0147 (9)	0.4734 (11)	0.105 (4)	0.376 (8)
H19A	0.7144	1.0645	0.3810	0.126*	0.376 (8)
H19B	0.7136	1.0533	0.5346	0.126*	0.376 (8)
C18B	0.6631 (11)	0.9034 (11)	0.4701 (8)	0.076 (2)	0.624 (8)
H18B	0.6512	0.9951	0.4335	0.091*	0.624 (8)
C19B	0.7085 (7)	0.8617 (7)	0.5769 (6)	0.109 (2)	0.624 (8)
H19C	0.7214	0.7705	0.6156	0.131*	0.624 (8)
H19D	0.7279	0.9232	0.6141	0.131*	0.624 (8)
N1	0.8009 (2)	0.6396 (2)	0.36458 (18)	0.0738 (5)
N2	0.6767 (2)	0.68077 (16)	0.44501 (18)	0.0663 (5)
N3	0.47799 (13)	0.21562 (12)	0.86652 (13)	0.0403 (3)
H3N	0.5266	0.1437	0.8473	0.048*
O1	0.73089 (12)	0.22498 (12)	0.65275 (13)	0.0491 (3)
O2	0.36643 (13)	0.31502 (12)	1.06165 (13)	0.0531 (3)
O3	0.40499 (13)	0.07043 (11)	1.10772 (12)	0.0510 (3)
S1	0.45343 (4)	0.20409 (3)	1.03010 (4)	0.04001 (12)
Cl1	0.95478 (8)	0.42370 (8)	0.34929 (7)	0.1012 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0652 (12)	0.0749 (13)	0.0401 (9)	−0.0231 (10)	−0.0109 (8)	−0.0048 (8)
C2	0.0515 (9)	0.0554 (9)	0.0379 (8)	−0.0137 (7)	−0.0157 (7)	−0.0071 (7)
C3	0.0673 (11)	0.0476 (9)	0.0439 (9)	−0.0139 (8)	−0.0265 (8)	−0.0008 (7)
C4	0.0632 (11)	0.0446 (9)	0.0567 (10)	0.0020 (8)	−0.0281 (9)	−0.0083 (7)
C5	0.0456 (8)	0.0487 (9)	0.0488 (9)	−0.0008 (7)	−0.0168 (7)	−0.0110 (7)
C6	0.0407 (7)	0.0400 (7)	0.0384 (7)	−0.0078 (6)	−0.0157 (6)	−0.0073 (6)
C7	0.0425 (8)	0.0457 (8)	0.0391 (8)	−0.0063 (6)	−0.0154 (6)	−0.0119 (6)
C8	0.0471 (9)	0.0792 (13)	0.0574 (11)	0.0035 (9)	−0.0184 (8)	−0.0219 (10)
C9	0.0637 (14)	0.0928 (19)	0.130 (3)	0.0210 (13)	−0.0312 (15)	−0.0325 (17)
C10	0.0447 (8)	0.0391 (7)	0.0360 (7)	−0.0108 (6)	−0.0111 (6)	−0.0079 (6)
C11	0.0628 (11)	0.0399 (8)	0.0589 (10)	−0.0141 (7)	−0.0297 (9)	0.0024 (7)
C12	0.0617 (11)	0.0572 (10)	0.0675 (12)	−0.0071 (9)	−0.0349 (10)	−0.0020 (9)
C13	0.0535 (10)	0.0704 (12)	0.0509 (10)	−0.0184 (9)	−0.0165 (8)	−0.0172 (9)
C14	0.0591 (10)	0.0522 (10)	0.0657 (12)	−0.0222 (8)	−0.0117 (9)	−0.0211 (8)
C15	0.0527 (9)	0.0395 (8)	0.0596 (10)	−0.0088 (7)	−0.0118 (8)	−0.0176 (7)
C16	0.0610 (13)	0.1033 (18)	0.0955 (18)	−0.0223 (12)	−0.0326 (13)	−0.0248 (15)
C17	0.120 (2)	0.0525 (11)	0.0877 (17)	−0.0236 (12)	−0.0575 (16)	0.0148 (11)
C18A	0.134 (10)	0.060 (6)	0.078 (9)	−0.010 (5)	−0.065 (9)	−0.018 (6)
C19A	0.084 (5)	0.107 (7)	0.159 (9)	0.003 (4)	−0.044 (5)	−0.083 (6)
C18B	0.081 (3)	0.071 (3)	0.067 (4)	−0.021 (2)	−0.022 (3)	−0.004 (3)
C19B	0.121 (4)	0.136 (5)	0.081 (4)	−0.061 (4)	−0.011 (3)	−0.048 (3)
N1	0.0861 (13)	0.0787 (12)	0.0463 (9)	−0.0342 (10)	−0.0185 (9)	0.0039 (8)
N2	0.0899 (13)	0.0540 (9)	0.0496 (9)	−0.0224 (8)	−0.0283 (9)	0.0058 (7)
N3	0.0415 (7)	0.0359 (6)	0.0420 (7)	−0.0079 (5)	−0.0112 (5)	−0.0095 (5)
O1	0.0445 (6)	0.0508 (6)	0.0524 (7)	−0.0024 (5)	−0.0131 (5)	−0.0185 (5)
O2	0.0518 (7)	0.0486 (6)	0.0524 (7)	−0.0007 (5)	−0.0070 (5)	−0.0173 (5)
O3	0.0513 (7)	0.0411 (6)	0.0489 (7)	−0.0169 (5)	−0.0053 (5)	−0.0039 (5)
S1	0.0401 (2)	0.0354 (2)	0.0385 (2)	−0.00946 (14)	−0.00577 (15)	−0.00744 (14)
Cl1	0.0849 (4)	0.1221 (6)	0.0606 (4)	−0.0129 (4)	0.0153 (3)	−0.0182 (4)

C1—N1	1.308 (3)	C13—C14	1.383 (3)
C1—C2	1.422 (3)	C13—C16	1.510 (3)
C1—Cl1	1.705 (2)	C14—C15	1.382 (3)
C2—C3	1.403 (3)	C14—H14	0.9300
C2—C7	1.411 (2)	C15—H15	0.9300
C3—N2	1.366 (2)	C16—H16A	0.9600
C3—C4	1.394 (3)	C16—H16B	0.9600
C4—C5	1.366 (2)	C16—H16C	0.9600
C4—H4	0.9300	C17—C18B	1.380 (11)
C5—C6	1.412 (2)	C17—N2	1.442 (3)
C5—H5	0.9300	C17—C18A	1.663 (15)
C6—C7	1.382 (2)	C17—H17A	0.9700
C6—N3	1.4327 (18)	C17—H17B	0.9700
C7—O1	1.3683 (19)	C17—H17C	0.9700
C8—O1	1.450 (2)	C17—H17D	0.9700
C8—C9	1.478 (3)	C18A—C19A	1.331 (19)
C8—H8A	0.9700	C18A—H18A	0.9300
C8—H8B	0.9700	C19A—H19A	0.9300
C9—H9A	0.9600	C19A—H19B	0.9300
C9—H9B	0.9600	C18B—C19B	1.307 (10)
C9—H9C	0.9600	C18B—H18B	0.9300
C10—C11	1.380 (2)	C19B—H19C	0.9300
C10—C15	1.390 (2)	C19B—H19D	0.9300
C10—S1	1.7572 (16)	N1—N2	1.357 (3)
C11—C12	1.382 (3)	N3—S1	1.6504 (13)
C11—H11	0.9300	N3—H3N	0.8896
C12—C13	1.388 (3)	O2—S1	1.4267 (12)
C12—H12	0.9300	O3—S1	1.4317 (11)
N1—C1—C2	112.7 (2)	C13—C16—H16B	109.5
N1—C1—Cl1	118.98 (16)	H16A—C16—H16B	109.5
C2—C1—Cl1	128.32 (17)	C13—C16—H16C	109.5
C3—C2—C7	119.20 (16)	H16A—C16—H16C	109.5
C3—C2—C1	103.15 (16)	H16B—C16—H16C	109.5
C7—C2—C1	137.65 (18)	C18B—C17—N2	118.3 (5)
N2—C3—C4	130.22 (18)	C18B—C17—C18A	14.3 (7)
N2—C3—C2	106.89 (17)	N2—C17—C18A	107.4 (6)
C4—C3—C2	122.81 (15)	C18B—C17—H17A	111.6
C5—C4—C3	117.00 (16)	N2—C17—H17A	110.2
C5—C4—H4	121.5	C18A—C17—H17A	110.2
C3—C4—H4	121.5	C18B—C17—H17B	96.9
C4—C5—C6	121.71 (16)	N2—C17—H17B	110.2
C4—C5—H5	119.1	C18A—C17—H17B	110.2
C6—C5—H5	119.1	H17A—C17—H17B	108.5
C7—C6—C5	121.27 (14)	C18B—C17—H17C	107.7
C7—C6—N3	119.03 (14)	N2—C17—H17C	107.7
C5—C6—N3	119.65 (14)	C18A—C17—H17C	121.4
O1—C7—C6	119.44 (14)	H17A—C17—H17C	99.4
O1—C7—C2	122.54 (14)	H17B—C17—H17C	11.9
C6—C7—C2	117.89 (15)	C18B—C17—H17D	107.7
O1—C8—C9	107.74 (18)	N2—C17—H17D	107.7
O1—C8—H8A	110.2	C18A—C17—H17D	104.8
C9—C8—H8A	110.2	H17A—C17—H17D	7.7
O1—C8—H8B	110.2	H17B—C17—H17D	116.0
C9—C8—H8B	110.2	H17C—C17—H17D	107.1
H8A—C8—H8B	108.5	C19A—C18A—C17	120.0 (9)
C8—C9—H9A	109.5	C19A—C18A—H18A	120.0
C8—C9—H9B	109.5	C17—C18A—H18A	120.0
H9A—C9—H9B	109.5	C18A—C19A—H19A	120.0
C8—C9—H9C	109.5	C18A—C19A—H19B	120.0
H9A—C9—H9C	109.5	H19A—C19A—H19B	120.0
H9B—C9—H9C	109.5	C19B—C18B—C17	123.8 (9)
C11—C10—C15	120.75 (15)	C19B—C18B—H18B	118.1
C11—C10—S1	119.82 (11)	C17—C18B—H18B	118.1
C15—C10—S1	119.27 (13)	C18B—C19B—H19C	120.0
C10—C11—C12	119.32 (15)	C18B—C19B—H19D	120.0
C10—C11—H11	120.3	H19C—C19B—H19D	120.0
C12—C11—H11	120.3	C1—N1—N2	105.77 (17)
C11—C12—C13	121.25 (18)	N1—N2—C3	111.52 (17)
C11—C12—H12	119.4	N1—N2—C17	120.35 (19)
C13—C12—H12	119.4	C3—N2—C17	128.1 (2)
C14—C13—C12	118.22 (17)	C6—N3—S1	119.49 (10)
C14—C13—C16	120.82 (18)	C6—N3—H3N	114.3
C12—C13—C16	120.9 (2)	S1—N3—H3N	108.7
C15—C14—C13	121.79 (16)	C7—O1—C8	114.94 (13)
C15—C14—H14	119.1	O2—S1—O3	119.60 (7)
C13—C14—H14	119.1	O2—S1—N3	107.72 (7)
C14—C15—C10	118.65 (16)	O3—S1—N3	105.18 (7)
C14—C15—H15	120.7	O2—S1—C10	108.63 (7)
C10—C15—H15	120.7	O3—S1—C10	108.69 (7)
C13—C16—H16A	109.5	N3—S1—C10	106.23 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O3i	0.89	2.22	3.0588 (17)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O3i	0.89	2.22	3.0588 (17)	156

Symmetry code: (i) .