N-(2-Allyl-4-eth-oxy-2H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

The indazole ring system of the title compound, C19H21N3O3S, is almost planar (r.m.s. deviation = 0.0192 Å) and forms dihedral angles of 77.99 (15) and 83.9 (3)° with the benzene ring and allyl group, respectively. In the crystal, centrosymmetrically related mol-ecules are connected by pairs of N-H⋯O hydrogen bonds into dimers, which are further linked by C-H⋯O hydrogen bonds, forming columns parallel to the b axis.

Related literature

For the biological activity of sulfonamides, see: Drews (2000 ▶); Supuran & Scozzafava (2001 ▶); Abbate et al. (2004 ▶); Rostom (2006 ▶); Ghorab et al. (2009 ▶). For similar compounds, see: Bouissane et al. (2006 ▶); Abbassi et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

C19H21N3O3S

M = 371.45

Monoclinic,

a = 26.0808 (5) Å

b = 7.9335 (2) Å

c = 21.1573 (4) Å

β = 122.839 (1)°

V = 3678.13 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.20 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

37135 measured reflections

4059 independent reflections

3100 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.134

S = 1.07

4059 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.36 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/S1600536814009283/rz5122sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009283/rz5122Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814009283/rz5122Isup3.cml

CCDC reference: 999285

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

C19H21N3O3S	F(000) = 1568
Mr = 371.45	Dx = 1.342 Mg m−3
Monoclinic, C2/c	Melting point: 388 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 26.0808 (5) Å	Cell parameters from 4059 reflections
b = 7.9335 (2) Å	θ = 2.3–27.1°
c = 21.1573 (4) Å	µ = 0.20 mm−1
β = 122.839 (1)°	T = 296 K
V = 3678.13 (14) Å3	Block, colourless
Z = 8	0.42 × 0.35 × 0.30 mm

Bruker X8 APEX diffractometer	4059 independent reflections
Radiation source: fine-focus sealed tube	3100 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 27.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −33→33
Tmin = 0.693, Tmax = 0.747	k = −10→10
37135 measured reflections	l = −27→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0616P)2 + 3.2227P] where P = (Fo2 + 2Fc2)/3
4059 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.36 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 > 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	0.18654 (15)	1.1635 (5)	0.01834 (19)	0.0893 (10)
H1A	0.1582	1.1968	0.0297	0.107*
H1B	0.2038	1.2431	0.0030	0.107*
C2	0.20182 (12)	1.0079 (4)	0.02385 (15)	0.0683 (8)
H2	0.2302	0.9786	0.0121	0.082*
C3	0.17730 (12)	0.8734 (4)	0.04754 (16)	0.0724 (8)
H3A	0.1511	0.8016	0.0047	0.087*
H3B	0.1524	0.9234	0.0638	0.087*
C4	0.26062 (10)	0.8146 (3)	0.18156 (14)	0.0550 (6)
H4	0.2592	0.9161	0.2025	0.066*
C5	0.30029 (9)	0.6795 (3)	0.21932 (12)	0.0414 (5)
C6	0.28267 (10)	0.5576 (3)	0.16164 (13)	0.0483 (5)
C7	0.31134 (11)	0.3998 (3)	0.17722 (15)	0.0596 (7)
H7	0.2990	0.3198	0.1395	0.071*
C8	0.35751 (10)	0.3678 (3)	0.24888 (13)	0.0496 (6)
H9	0.3762	0.2625	0.2606	0.060*
C9	0.37814 (9)	0.4902 (2)	0.30660 (11)	0.0356 (4)
C10	0.35000 (9)	0.6438 (3)	0.29332 (11)	0.0363 (4)
C11	0.36304 (15)	0.9237 (3)	0.34341 (16)	0.0712 (8)
H11B	0.3205	0.9536	0.3207	0.085*
H11A	0.3758	0.9615	0.3104	0.085*
C12	0.40124 (14)	1.0063 (4)	0.41880 (16)	0.0715 (8)
H12B	0.3969	1.1264	0.4130	0.107*
H12A	0.4433	0.9761	0.4409	0.107*
H12C	0.3880	0.9692	0.4509	0.107*
C13	0.52408 (8)	0.5771 (2)	0.37746 (10)	0.0329 (4)
C14	0.55443 (10)	0.5564 (3)	0.34089 (12)	0.0428 (5)
H14	0.5586	0.4500	0.3258	0.051*
C15	0.57834 (11)	0.6960 (3)	0.32728 (13)	0.0494 (6)
H15	0.5995	0.6821	0.3036	0.059*
C16	0.57191 (10)	0.8555 (3)	0.34757 (13)	0.0460 (5)
C17	0.54115 (11)	0.8730 (3)	0.38424 (13)	0.0477 (5)
H17	0.5363	0.9797	0.3984	0.057*
C18	0.51797 (10)	0.7357 (3)	0.39973 (12)	0.0421 (5)
H18	0.4982	0.7490	0.4251	0.050*
C19	0.59695 (14)	1.0079 (4)	0.33072 (18)	0.0743 (8)
H19A	0.6303	0.9746	0.3264	0.111*
H19B	0.6110	1.0884	0.3707	0.111*
H19C	0.5654	1.0579	0.2843	0.111*
N1	0.22511 (9)	0.7686 (3)	0.10913 (12)	0.0592 (6)
N2	0.23653 (9)	0.6139 (3)	0.09414 (12)	0.0616 (6)
N3	0.42783 (7)	0.4479 (2)	0.38105 (9)	0.0368 (4)
H3N	0.4322	0.5087	0.4163	0.044*
O1	0.37042 (8)	0.7467 (2)	0.35341 (9)	0.0589 (5)
O2	0.48852 (7)	0.26717 (19)	0.34847 (9)	0.0493 (4)
O3	0.53203 (7)	0.3684 (2)	0.47767 (8)	0.0486 (4)
S1	0.49532 (2)	0.39937 (6)	0.39815 (3)	0.03587 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0645 (19)	0.080 (2)	0.091 (2)	−0.0064 (17)	0.0212 (18)	0.005 (2)
C2	0.0484 (14)	0.096 (2)	0.0516 (15)	0.0093 (15)	0.0215 (12)	0.0095 (16)
C3	0.0416 (13)	0.081 (2)	0.0604 (17)	0.0034 (13)	0.0054 (13)	0.0161 (15)
C4	0.0419 (12)	0.0544 (15)	0.0548 (15)	0.0074 (11)	0.0172 (11)	0.0020 (12)
C5	0.0333 (10)	0.0438 (12)	0.0446 (12)	0.0008 (9)	0.0195 (9)	0.0008 (10)
C6	0.0347 (10)	0.0561 (14)	0.0435 (12)	−0.0049 (10)	0.0144 (10)	−0.0076 (11)
C7	0.0518 (14)	0.0542 (15)	0.0531 (15)	−0.0049 (11)	0.0156 (12)	−0.0207 (12)
C8	0.0480 (12)	0.0370 (12)	0.0566 (14)	−0.0018 (9)	0.0236 (12)	−0.0097 (10)
C9	0.0352 (10)	0.0320 (10)	0.0392 (11)	−0.0016 (8)	0.0200 (9)	0.0006 (9)
C10	0.0370 (10)	0.0355 (11)	0.0380 (11)	−0.0032 (8)	0.0213 (9)	−0.0040 (9)
C11	0.094 (2)	0.0451 (16)	0.0664 (18)	0.0085 (14)	0.0381 (17)	−0.0006 (13)
C12	0.085 (2)	0.0484 (16)	0.080 (2)	−0.0012 (14)	0.0440 (17)	−0.0163 (14)
C13	0.0330 (9)	0.0321 (10)	0.0300 (9)	0.0052 (8)	0.0147 (8)	0.0033 (8)
C14	0.0478 (12)	0.0407 (12)	0.0449 (12)	0.0063 (9)	0.0284 (10)	−0.0007 (10)
C15	0.0514 (13)	0.0562 (15)	0.0532 (13)	0.0016 (11)	0.0365 (12)	0.0031 (11)
C16	0.0424 (11)	0.0458 (13)	0.0473 (13)	−0.0005 (10)	0.0227 (10)	0.0087 (10)
C17	0.0558 (13)	0.0327 (12)	0.0596 (14)	0.0042 (10)	0.0346 (12)	0.0016 (10)
C18	0.0509 (12)	0.0338 (11)	0.0524 (13)	0.0047 (9)	0.0352 (11)	0.0014 (10)
C19	0.0806 (19)	0.0632 (19)	0.095 (2)	−0.0091 (15)	0.0580 (18)	0.0138 (16)
N1	0.0365 (10)	0.0692 (15)	0.0498 (12)	0.0019 (9)	0.0089 (9)	0.0063 (11)
N2	0.0434 (11)	0.0702 (15)	0.0492 (12)	−0.0022 (10)	0.0109 (10)	−0.0057 (11)
N3	0.0419 (9)	0.0324 (9)	0.0389 (9)	0.0019 (7)	0.0238 (8)	0.0019 (7)
O1	0.0722 (11)	0.0430 (9)	0.0508 (10)	0.0097 (8)	0.0264 (9)	−0.0026 (8)
O2	0.0595 (10)	0.0317 (8)	0.0595 (10)	0.0054 (7)	0.0341 (8)	−0.0047 (7)
O3	0.0523 (9)	0.0491 (9)	0.0398 (8)	0.0167 (7)	0.0221 (7)	0.0171 (7)
S1	0.0418 (3)	0.0277 (3)	0.0375 (3)	0.0078 (2)	0.0211 (2)	0.0056 (2)

C1—C2	1.284 (4)	C11—H11A	0.9700
C1—H1A	0.9300	C12—H12B	0.9600
C1—H1B	0.9300	C12—H12A	0.9600
C2—C3	1.465 (4)	C12—H12C	0.9600
C2—H2	0.9300	C13—C18	1.382 (3)
C3—N1	1.477 (3)	C13—C14	1.384 (3)
C3—H3A	0.9700	C13—S1	1.760 (2)
C3—H3B	0.9700	C14—C15	1.376 (3)
C4—N1	1.342 (3)	C14—H14	0.9300
C4—C5	1.400 (3)	C15—C16	1.375 (3)
C4—H4	0.9300	C15—H15	0.9300
C5—C10	1.418 (3)	C16—C17	1.393 (3)
C5—C6	1.424 (3)	C16—C19	1.506 (3)
C6—N2	1.350 (3)	C17—C18	1.369 (3)
C6—C7	1.402 (3)	C17—H17	0.9300
C7—C8	1.354 (3)	C18—H18	0.9300
C7—H7	0.9300	C19—H19A	0.9600
C8—C9	1.418 (3)	C19—H19B	0.9600
C8—H9	0.9300	C19—H19C	0.9600
C9—C10	1.370 (3)	N1—N2	1.341 (3)
C9—N3	1.435 (3)	N3—S1	1.6389 (16)
C10—O1	1.354 (3)	N3—H3N	0.8417
C11—O1	1.418 (3)	O2—S1	1.4261 (15)
C11—C12	1.497 (4)	O3—S1	1.4357 (15)
C11—H11B	0.9700
C2—C1—H1A	120.0	C11—C12—H12C	109.5
C2—C1—H1B	120.0	H12B—C12—H12C	109.5
H1A—C1—H1B	120.0	H12A—C12—H12C	109.5
C1—C2—C3	124.1 (3)	C18—C13—C14	120.33 (19)
C1—C2—H2	118.0	C18—C13—S1	120.05 (15)
C3—C2—H2	118.0	C14—C13—S1	119.59 (16)
C2—C3—N1	113.3 (2)	C15—C14—C13	118.9 (2)
C2—C3—H3A	108.9	C15—C14—H14	120.6
N1—C3—H3A	108.9	C13—C14—H14	120.6
C2—C3—H3B	108.9	C16—C15—C14	122.0 (2)
N1—C3—H3B	108.9	C16—C15—H15	119.0
H3A—C3—H3B	107.7	C14—C15—H15	119.0
N1—C4—C5	106.4 (2)	C15—C16—C17	118.1 (2)
N1—C4—H4	126.8	C15—C16—C19	121.5 (2)
C5—C4—H4	126.8	C17—C16—C19	120.4 (2)
C4—C5—C10	137.2 (2)	C18—C17—C16	121.1 (2)
C4—C5—C6	103.6 (2)	C18—C17—H17	119.5
C10—C5—C6	119.2 (2)	C16—C17—H17	119.5
N2—C6—C7	126.8 (2)	C17—C18—C13	119.67 (19)
N2—C6—C5	111.7 (2)	C17—C18—H18	120.2
C7—C6—C5	121.4 (2)	C13—C18—H18	120.2
C8—C7—C6	117.9 (2)	C16—C19—H19A	109.5
C8—C7—H7	121.0	C16—C19—H19B	109.5
C6—C7—H7	121.0	H19A—C19—H19B	109.5
C7—C8—C9	121.8 (2)	C16—C19—H19C	109.5
C7—C8—H9	119.1	H19A—C19—H19C	109.5
C9—C8—H9	119.1	H19B—C19—H19C	109.5
C10—C9—C8	121.43 (19)	N2—N1—C4	114.5 (2)
C10—C9—N3	119.84 (17)	N2—N1—C3	119.7 (2)
C8—C9—N3	118.68 (18)	C4—N1—C3	125.8 (2)
O1—C10—C9	116.71 (18)	N1—N2—C6	103.7 (2)
O1—C10—C5	125.09 (19)	C9—N3—S1	121.32 (13)
C9—C10—C5	118.13 (18)	C9—N3—H3N	116.5
O1—C11—C12	108.4 (2)	S1—N3—H3N	108.9
O1—C11—H11B	110.0	C10—O1—C11	120.3 (2)
C12—C11—H11B	110.0	O2—S1—O3	118.36 (10)
O1—C11—H11A	110.0	O2—S1—N3	108.69 (9)
C12—C11—H11A	110.0	O3—S1—N3	104.65 (9)
H11B—C11—H11A	108.4	O2—S1—C13	107.78 (9)
C11—C12—H12B	109.5	O3—S1—C13	108.99 (10)
C11—C12—H12A	109.5	N3—S1—C13	107.96 (9)
H12B—C12—H12A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C8—H9···O2	0.93	2.48	2.991 (3)	115
N3—H3N···O3i	0.84	2.14	2.960 (2)	164
C17—H17···O2ii	0.93	2.54	3.333 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O3i	0.84	2.14	2.960 (2)	164
C17—H17⋯O2ii	0.93	2.54	3.333 (3)	144

Symmetry codes: (i) ; (ii) .