Crystal structure of N-(1-allyl-3-chloro-1H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

The 3-chloro-1H-indazole system in the title mol-ecule, C17H16ClN3O2S, is almost planar, with the largest deviation from the mean plane being 0.029 (2) Å for one of the N atoms. This system is nearly perpendicular to the allyl chain, as indicated by the C-C-N-N torsion angle of -90.1 (6)° between them. The allyl group is split into two fragments, the major component has a site occupancy of 0.579 (7). The indazole system makes a dihedral angle of 47.53 (10)° with the plane through the benzene ring. In the crystal, mol-ecules are connected by N-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

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

Experimental

Crystal data

C17H16ClN3O2S

M = 361.84

Orthorhombic,

a = 8.1736 (12) Å

b = 22.504 (4) Å

c = 19.279 (3) Å

V = 3546.2 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.35 mm−1

T = 296 K

0.40 × 0.36 × 0.31 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.693, T max = 0.747

18362 measured reflections

3621 independent reflections

2327 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.02

3621 reflections

225 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.26 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/S1600536814018194/tk5336sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018194/tk5336Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018194/tk5336Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018194/tk5336fig1.tif

Mol­ecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

Click here for additional data file.

N . DOI: 10.1107/S1600536814018194/tk5336fig2.tif

Crystal structure of the title compound, showing mol­ecules linked by N3–H3N⋯O1, C5–H5⋯O1 and C4–H4⋯O2 hydrogen bonds between mol­ecules.

CCDC reference: 1018456

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

C17H16ClN3O2S	Dx = 1.355 Mg m−3
Mr = 361.84	Melting point: 394 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3621 reflections
a = 8.1736 (12) Å	θ = 2.8–26.4°
b = 22.504 (4) Å	µ = 0.35 mm−1
c = 19.279 (3) Å	T = 296 K
V = 3546.2 (10) Å3	Block, colourless
Z = 8	0.40 × 0.36 × 0.31 mm
F(000) = 1504

Bruker X8 APEX diffractometer	3621 independent reflections
Radiation source: fine-focus sealed tube	2327 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −9→10
Tmin = 0.693, Tmax = 0.747	k = −28→26
18362 measured reflections	l = −22→24

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0557P)2 + 0.7269P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3621 reflections	Δρmax = 0.26 e Å−3
225 parameters	Δρmin = −0.26 e Å−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0026 (4)

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	0.8260 (3)	−0.03622 (11)	0.08181 (12)	0.0516 (6)
C2	0.8328 (3)	0.02554 (10)	0.06992 (11)	0.0427 (5)
C3	0.9964 (3)	0.04008 (11)	0.08496 (12)	0.0481 (6)
C4	1.0542 (3)	0.09849 (12)	0.07951 (13)	0.0570 (7)
H4	1.1624	0.1081	0.0892	0.068*
C5	0.9446 (3)	0.14053 (11)	0.05939 (13)	0.0532 (6)
H5	0.9793	0.1798	0.0558	0.064*
C6	0.7806 (3)	0.12692 (10)	0.04380 (11)	0.0444 (5)
C7	0.7233 (3)	0.06945 (10)	0.04817 (11)	0.0445 (6)
H7	0.6156	0.0602	0.0370	0.053*
C8	0.6222 (3)	0.22836 (11)	0.14802 (13)	0.0503 (6)
C9	0.6865 (3)	0.19241 (12)	0.19974 (14)	0.0628 (7)
H9	0.6795	0.1513	0.1961	0.075*
C10	0.7609 (4)	0.21805 (15)	0.25663 (15)	0.0741 (8)
H10	0.8063	0.1939	0.2907	0.089*
C11	0.7691 (4)	0.27915 (16)	0.26378 (16)	0.0756 (9)
C12	0.7046 (4)	0.31338 (14)	0.21193 (19)	0.0830 (10)
H12	0.7097	0.3545	0.2162	0.100*
C13	0.6321 (3)	0.28965 (12)	0.15350 (16)	0.0669 (8)
H13	0.5911	0.3141	0.1187	0.080*
C14	0.8448 (5)	0.3061 (2)	0.32849 (19)	0.1179 (15)
H14A	0.8818	0.2750	0.3586	0.177*
H14B	0.7645	0.3298	0.3521	0.177*
H14C	0.9358	0.3307	0.3156	0.177*
C15	1.2392 (3)	−0.01960 (14)	0.12649 (15)	0.0755 (9)
H15A	1.3111	0.0081	0.1029	0.091*
H15B	1.2767	−0.0597	0.1172	0.091*
C16A	1.2386 (8)	−0.0080 (6)	0.2012 (2)	0.0902 (19)	0.579 (7)
H16A	1.1739	−0.0334	0.2276	0.108*	0.579 (7)
C17A	1.3154 (12)	0.0324 (4)	0.2354 (5)	0.120 (2)	0.579 (7)
H17A	1.3823	0.0593	0.2122	0.144*	0.579 (7)
H17B	1.3039	0.0348	0.2833	0.144*	0.579 (7)
C16B	1.2961 (13)	−0.0101 (9)	0.1975 (3)	0.0902 (19)	0.421 (7)
H16B	1.3979	−0.0238	0.2119	0.108*	0.421 (7)
C17B	1.2008 (15)	0.0178 (6)	0.2393 (6)	0.120 (2)	0.421 (7)
H17C	1.0994	0.0312	0.2241	0.144*	0.421 (7)
H17D	1.2333	0.0246	0.2849	0.144*	0.421 (7)
N1	1.0722 (2)	−0.01207 (10)	0.10293 (11)	0.0576 (6)
N2	0.9665 (3)	−0.05905 (9)	0.10217 (11)	0.0593 (6)
N3	0.6711 (2)	0.17352 (9)	0.02206 (10)	0.0510 (5)
H3N	0.7140	0.2027	0.0059	0.061*
O1	0.4373 (2)	0.24036 (8)	0.03876 (10)	0.0743 (6)
O2	0.44423 (19)	0.14312 (8)	0.09892 (10)	0.0613 (5)
S1	0.52632 (7)	0.19552 (3)	0.07563 (3)	0.0508 (2)
Cl1	0.65782 (9)	−0.08137 (3)	0.07145 (5)	0.0776 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0444 (14)	0.0511 (15)	0.0591 (16)	0.0037 (11)	−0.0066 (12)	−0.0015 (11)
C2	0.0360 (12)	0.0497 (14)	0.0424 (12)	0.0002 (10)	−0.0015 (10)	−0.0025 (10)
C3	0.0361 (13)	0.0595 (15)	0.0486 (14)	0.0021 (11)	−0.0009 (10)	−0.0027 (11)
C4	0.0324 (13)	0.0728 (18)	0.0659 (17)	−0.0071 (12)	−0.0022 (12)	−0.0017 (13)
C5	0.0449 (14)	0.0543 (15)	0.0605 (15)	−0.0097 (12)	0.0030 (12)	0.0020 (11)
C6	0.0380 (13)	0.0514 (14)	0.0437 (13)	−0.0018 (11)	0.0008 (10)	0.0035 (10)
C7	0.0326 (12)	0.0537 (15)	0.0471 (13)	−0.0013 (10)	−0.0013 (10)	−0.0012 (10)
C8	0.0372 (13)	0.0534 (16)	0.0603 (16)	−0.0031 (11)	0.0080 (11)	0.0041 (11)
C9	0.0652 (18)	0.0606 (17)	0.0625 (17)	−0.0024 (14)	0.0008 (14)	0.0087 (13)
C10	0.0681 (19)	0.099 (2)	0.0556 (17)	−0.0019 (18)	0.0005 (15)	0.0061 (16)
C11	0.0620 (18)	0.102 (3)	0.0632 (19)	−0.0170 (18)	0.0130 (16)	−0.0167 (17)
C12	0.094 (2)	0.064 (2)	0.090 (2)	−0.0176 (18)	0.006 (2)	−0.0170 (17)
C13	0.0691 (18)	0.0497 (16)	0.082 (2)	−0.0021 (14)	0.0029 (16)	0.0027 (13)
C14	0.113 (3)	0.162 (4)	0.078 (2)	−0.028 (3)	0.007 (2)	−0.041 (2)
C15	0.0471 (15)	0.094 (2)	0.086 (2)	0.0195 (15)	−0.0203 (15)	−0.0028 (16)
C16A	0.051 (5)	0.108 (3)	0.112 (3)	0.026 (6)	−0.053 (3)	−0.003 (3)
C17A	0.125 (7)	0.150 (6)	0.085 (4)	−0.008 (6)	−0.019 (5)	−0.002 (4)
C16B	0.051 (5)	0.108 (3)	0.112 (3)	0.026 (6)	−0.053 (3)	−0.003 (3)
C17B	0.125 (7)	0.150 (6)	0.085 (4)	−0.008 (6)	−0.019 (5)	−0.002 (4)
N1	0.0400 (11)	0.0674 (15)	0.0655 (14)	0.0090 (11)	−0.0081 (10)	−0.0028 (11)
N2	0.0556 (13)	0.0575 (13)	0.0649 (14)	0.0090 (12)	−0.0079 (11)	−0.0014 (10)
N3	0.0487 (12)	0.0504 (12)	0.0540 (12)	−0.0004 (9)	0.0008 (10)	0.0125 (9)
O1	0.0602 (12)	0.0682 (12)	0.0945 (14)	0.0180 (10)	−0.0207 (11)	0.0137 (10)
O2	0.0408 (9)	0.0583 (11)	0.0848 (12)	−0.0107 (8)	0.0069 (9)	0.0003 (9)
S1	0.0372 (3)	0.0478 (4)	0.0673 (4)	0.0015 (3)	−0.0050 (3)	0.0078 (3)
Cl1	0.0639 (5)	0.0553 (4)	0.1137 (7)	−0.0094 (3)	−0.0186 (4)	0.0066 (4)

C1—N2	1.318 (3)	C12—H12	0.9300
C1—C2	1.410 (3)	C13—H13	0.9300
C1—Cl1	1.721 (3)	C14—H14A	0.9600
C2—C7	1.398 (3)	C14—H14B	0.9600
C2—C3	1.407 (3)	C14—H14C	0.9600
C3—N1	1.371 (3)	C15—N1	1.448 (3)
C3—C4	1.400 (3)	C15—C16B	1.461 (2)
C4—C5	1.359 (3)	C15—C16A	1.464 (2)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.407 (3)	C15—H15B	0.9700
C5—H5	0.9300	C16A—C17A	1.286 (2)
C6—C7	1.378 (3)	C16A—H16A	0.9300
C6—N3	1.441 (3)	C17A—H17A	0.9300
C7—H7	0.9300	C17A—H17B	0.9300
C8—C13	1.386 (3)	C16B—C17B	1.286 (2)
C8—C9	1.387 (3)	C16B—H16B	0.9300
C8—S1	1.763 (3)	C17B—H17C	0.9300
C9—C10	1.381 (4)	C17B—H17D	0.9300
C9—H9	0.9300	N1—N2	1.366 (3)
C10—C11	1.384 (4)	N3—S1	1.647 (2)
C10—H10	0.9300	N3—H3N	0.8060
C11—C12	1.368 (5)	O1—S1	1.4329 (18)
C11—C14	1.519 (4)	O2—S1	1.4291 (17)
C12—C13	1.380 (4)
N2—C1—C2	113.4 (2)	C11—C14—H14B	109.5
N2—C1—Cl1	120.0 (2)	H14A—C14—H14B	109.5
C2—C1—Cl1	126.52 (19)	C11—C14—H14C	109.5
C7—C2—C3	120.4 (2)	H14A—C14—H14C	109.5
C7—C2—C1	136.1 (2)	H14B—C14—H14C	109.5
C3—C2—C1	103.5 (2)	N1—C15—C16B	125.2 (5)
N1—C3—C4	132.1 (2)	N1—C15—C16A	106.5 (3)
N1—C3—C2	106.4 (2)	C16B—C15—C16A	18.8 (5)
C4—C3—C2	121.5 (2)	N1—C15—H15A	110.4
C5—C4—C3	116.9 (2)	C16B—C15—H15A	98.8
C5—C4—H4	121.5	C16A—C15—H15A	110.4
C3—C4—H4	121.5	N1—C15—H15B	110.4
C4—C5—C6	122.5 (2)	C16B—C15—H15B	102.0
C4—C5—H5	118.8	C16A—C15—H15B	110.4
C6—C5—H5	118.8	H15A—C15—H15B	108.6
C7—C6—C5	121.0 (2)	C17A—C16A—C15	128.9 (8)
C7—C6—N3	119.3 (2)	C17A—C16A—H16A	115.5
C5—C6—N3	119.7 (2)	C15—C16A—H16A	115.5
C6—C7—C2	117.6 (2)	C16A—C17A—H17A	120.0
C6—C7—H7	121.2	C16A—C17A—H17B	120.0
C2—C7—H7	121.2	H17A—C17A—H17B	120.0
C13—C8—C9	120.2 (3)	C17B—C16B—C15	117.8 (10)
C13—C8—S1	120.3 (2)	C17B—C16B—H16B	121.1
C9—C8—S1	119.5 (2)	C15—C16B—H16B	121.1
C10—C9—C8	119.6 (3)	C16B—C17B—H17C	120.0
C10—C9—H9	120.2	C16B—C17B—H17D	120.0
C8—C9—H9	120.2	H17C—C17B—H17D	120.0
C9—C10—C11	121.1 (3)	N2—N1—C3	111.97 (18)
C9—C10—H10	119.5	N2—N1—C15	120.6 (2)
C11—C10—H10	119.5	C3—N1—C15	127.2 (2)
C12—C11—C10	117.9 (3)	C1—N2—N1	104.6 (2)
C12—C11—C14	122.2 (3)	C6—N3—S1	118.87 (15)
C10—C11—C14	119.9 (3)	C6—N3—H3N	115.8
C11—C12—C13	123.0 (3)	S1—N3—H3N	108.1
C11—C12—H12	118.5	O2—S1—O1	119.90 (11)
C13—C12—H12	118.5	O2—S1—N3	106.65 (10)
C12—C13—C8	118.2 (3)	O1—S1—N3	105.41 (11)
C12—C13—H13	120.9	O2—S1—C8	107.81 (11)
C8—C13—H13	120.9	O1—S1—C8	108.85 (12)
C11—C14—H14A	109.5	N3—S1—C8	107.64 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1i	0.81	2.39	3.140 (3)	155
C4—H4···O2ii	0.93	2.44	3.364 (3)	171
C5—H5···O1i	0.93	2.58	3.282 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1i	0.81	2.39	3.140 (3)	155
C4—H4⋯O2ii	0.93	2.44	3.364 (3)	171
C5—H5⋯O1i	0.93	2.58	3.282 (3)	132

Symmetry codes: (i) ; (ii) .