N-(2-Allyl-4-chloro-2H-indazol-5-yl)-4-meth-oxy-benzene-sulfonamide hemi-hydrate.

The fused five- and six-membered rings in the title compound, C17H16ClN3O3S·0.5H2O, are practically coplanar, with the maximum deviation from the mean plane being 0.057 (3) Å for the C atom bound to the exocyclic N atom. The indazole system makes a dihedral angle of 66.18 (12)° with the plane through the benzene ring, and it is nearly perpendicular to the allyl group, as indicated by the N-N-C-C torsion angle of 79.2 (3)°. In the crystal, the water mol-ecule, lying on a twofold axis, forms O-H⋯N and accepts N-H⋯O hydrogen bonds. Additional C-H⋯O hydrogen bonds contribute to the formation of a chain along the b-axis direction.

Related literature

For the pharmacological activity of sulfonamides, see: Brzozowski et al. (2010 ▶); Drew (2000 ▶); Garaj et al. (2005 ▶); Lopez et al. (2010 ▶). For similar compounds, see: Abbassi et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

C17H16ClN3O3S·0.5H2O

M = 386.86

Monoclinic,

a = 23.5515 (9) Å

b = 8.9081 (3) Å

c = 20.8278 (8) Å

β = 122.628 (2)°

V = 3680.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.35 mm−1

T = 296 K

0.41 × 0.38 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer

20391 measured reflections

4389 independent reflections

2740 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.122

S = 1.02

4389 reflections

231 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.33 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/S1600536813020606/tk5244sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020606/tk5244Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020606/tk5244Isup3.cml

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

C17H16ClN3O3S·0.5H2O	F(000) = 1608
Mr = 386.86	Dx = 1.396 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4389 reflections
a = 23.5515 (9) Å	θ = 2.5–27.9°
b = 8.9081 (3) Å	µ = 0.35 mm−1
c = 20.8278 (8) Å	T = 296 K
β = 122.628 (2)°	Block, colourless
V = 3680.1 (2) Å3	0.41 × 0.38 × 0.27 mm
Z = 8

Bruker X8 APEX diffractometer	2740 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 27.9°, θmin = 2.5°
φ and ω scans	h = −30→29
20391 measured reflections	k = −11→11
4389 independent reflections	l = −25→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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0457P)2 + 2.416P] where P = (Fo2 + 2Fc2)/3
4389 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.33 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	0.07686 (11)	0.1101 (2)	0.24133 (13)	0.0363 (5)
C2	0.06759 (12)	−0.0223 (3)	0.19808 (14)	0.0434 (6)
H2	0.0569	−0.0121	0.1483	0.052*
C3	0.07383 (13)	−0.1630 (3)	0.22687 (14)	0.0457 (6)
H3	0.0688	−0.2476	0.1981	0.055*
C4	0.08816 (12)	−0.1761 (3)	0.30157 (13)	0.0402 (5)
C5	0.09891 (11)	−0.0468 (2)	0.34607 (13)	0.0369 (5)
C6	0.09541 (11)	0.0968 (2)	0.31577 (13)	0.0361 (5)
C7	0.10847 (12)	−0.1007 (3)	0.41405 (14)	0.0458 (6)
H7	0.1169	−0.0441	0.4558	0.055*
C8	0.11049 (16)	−0.3571 (3)	0.46422 (16)	0.0612 (8)
H8A	0.0770	−0.4358	0.4394	0.073*
H8B	0.1028	−0.3065	0.5001	0.073*
C9	0.1797 (2)	−0.4252 (4)	0.5063 (2)	0.0854 (11)
H9	0.1947	−0.4679	0.4773	0.103*
C10	0.2188 (2)	−0.4290 (6)	0.5770 (3)	0.1285 (17)
H10A	0.2056	−0.3874	0.6080	0.154*
H10B	0.2610	−0.4734	0.5987	0.154*
C11	0.19083 (12)	0.3430 (3)	0.25760 (13)	0.0404 (5)
C12	0.23937 (14)	0.2387 (3)	0.27121 (15)	0.0517 (7)
H12	0.2288	0.1607	0.2369	0.062*
C13	0.30364 (14)	0.2495 (3)	0.33557 (15)	0.0521 (7)
H13	0.3364	0.1796	0.3443	0.062*
C14	0.31891 (13)	0.3638 (3)	0.38665 (14)	0.0448 (6)
C15	0.26970 (14)	0.4682 (3)	0.37284 (15)	0.0555 (7)
H15	0.2802	0.5461	0.4072	0.067*
C16	0.20606 (13)	0.4575 (3)	0.30924 (15)	0.0514 (7)
H16	0.1732	0.5269	0.3008	0.062*
C17	0.43186 (15)	0.2760 (4)	0.47218 (17)	0.0706 (9)
H17A	0.4722	0.3057	0.5189	0.106*
H17B	0.4409	0.2688	0.4325	0.106*
H17C	0.4171	0.1802	0.4790	0.106*
N1	0.06279 (10)	0.2526 (2)	0.20483 (11)	0.0415 (5)
H1	0.0473	0.3177	0.2200	0.050*
N2	0.09126 (11)	−0.3021 (2)	0.33985 (12)	0.0491 (5)
N3	0.10311 (11)	−0.2499 (2)	0.40710 (12)	0.0481 (5)
O1	0.08137 (9)	0.47240 (19)	0.14958 (10)	0.0602 (5)
O2	0.11154 (9)	0.2212 (2)	0.12606 (10)	0.0550 (5)
O3	0.38047 (10)	0.3849 (2)	0.45159 (10)	0.0651 (6)
O4	0.0000	−0.5316 (2)	0.2500	0.0455 (6)
H4	0.0324	−0.4800	0.2868	0.055*
S1	0.10886 (3)	0.32522 (7)	0.17658 (3)	0.04380 (18)
Cl1	0.11387 (4)	0.25023 (7)	0.37487 (4)	0.0539 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0325 (12)	0.0362 (11)	0.0432 (14)	−0.0015 (9)	0.0224 (10)	−0.0012 (10)
C2	0.0502 (15)	0.0461 (13)	0.0395 (14)	−0.0016 (11)	0.0279 (12)	−0.0045 (11)
C3	0.0548 (15)	0.0385 (13)	0.0473 (15)	−0.0058 (11)	0.0299 (13)	−0.0112 (11)
C4	0.0418 (13)	0.0355 (12)	0.0426 (13)	−0.0036 (10)	0.0223 (11)	−0.0035 (10)
C5	0.0334 (12)	0.0374 (12)	0.0354 (12)	−0.0021 (10)	0.0156 (10)	−0.0031 (10)
C6	0.0328 (12)	0.0341 (11)	0.0399 (13)	−0.0014 (9)	0.0186 (10)	−0.0063 (10)
C7	0.0488 (15)	0.0420 (13)	0.0425 (14)	−0.0026 (11)	0.0220 (12)	−0.0046 (11)
C8	0.078 (2)	0.0522 (15)	0.0503 (16)	−0.0095 (15)	0.0324 (15)	0.0060 (13)
C9	0.113 (3)	0.069 (2)	0.060 (2)	0.022 (2)	0.038 (2)	0.0236 (18)
C10	0.090 (3)	0.168 (5)	0.130 (4)	0.029 (3)	0.061 (3)	0.046 (4)
C11	0.0413 (13)	0.0437 (13)	0.0389 (13)	−0.0031 (11)	0.0233 (11)	0.0003 (11)
C12	0.0509 (16)	0.0530 (15)	0.0490 (16)	−0.0001 (12)	0.0255 (13)	−0.0111 (12)
C13	0.0469 (15)	0.0546 (15)	0.0521 (16)	0.0088 (12)	0.0250 (13)	−0.0044 (13)
C14	0.0446 (14)	0.0488 (14)	0.0360 (13)	−0.0008 (11)	0.0185 (11)	0.0006 (11)
C15	0.0555 (17)	0.0510 (15)	0.0479 (16)	0.0041 (13)	0.0200 (13)	−0.0123 (12)
C16	0.0516 (16)	0.0462 (14)	0.0530 (16)	0.0083 (12)	0.0259 (13)	−0.0020 (12)
C17	0.0550 (18)	0.085 (2)	0.0531 (18)	0.0131 (16)	0.0170 (15)	0.0047 (16)
N1	0.0426 (11)	0.0384 (10)	0.0480 (12)	0.0044 (9)	0.0272 (10)	0.0030 (9)
N2	0.0621 (14)	0.0374 (10)	0.0467 (13)	−0.0070 (10)	0.0285 (11)	−0.0033 (10)
N3	0.0580 (14)	0.0422 (11)	0.0400 (12)	−0.0039 (10)	0.0238 (11)	0.0007 (10)
O1	0.0570 (11)	0.0533 (11)	0.0583 (12)	0.0038 (9)	0.0232 (10)	0.0218 (9)
O2	0.0580 (12)	0.0709 (12)	0.0423 (10)	−0.0083 (9)	0.0311 (9)	−0.0085 (9)
O3	0.0547 (12)	0.0710 (12)	0.0449 (11)	0.0067 (10)	0.0106 (9)	−0.0085 (9)
O4	0.0490 (14)	0.0278 (11)	0.0537 (15)	0.000	0.0238 (12)	0.000
S1	0.0435 (3)	0.0467 (3)	0.0391 (3)	−0.0030 (3)	0.0210 (3)	0.0045 (3)
Cl1	0.0702 (5)	0.0371 (3)	0.0480 (4)	0.0009 (3)	0.0275 (3)	−0.0084 (3)

C1—C6	1.371 (3)	C11—C12	1.379 (3)
C1—N1	1.423 (3)	C11—C16	1.382 (3)
C1—C2	1.428 (3)	C11—S1	1.757 (2)
C2—C3	1.363 (3)	C12—C13	1.382 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.408 (3)	C13—C14	1.373 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—N2	1.356 (3)	C14—O3	1.361 (3)
C4—C5	1.413 (3)	C14—C15	1.390 (4)
C5—C7	1.393 (3)	C15—C16	1.367 (3)
C5—C6	1.409 (3)	C15—H15	0.9300
C6—Cl1	1.731 (2)	C16—H16	0.9300
C7—N3	1.336 (3)	C17—O3	1.425 (3)
C7—H7	0.9300	C17—H17A	0.9600
C8—N3	1.461 (3)	C17—H17B	0.9600
C8—C9	1.501 (5)	C17—H17C	0.9600
C8—H8A	0.9700	N1—S1	1.622 (2)
C8—H8B	0.9700	N1—H1	0.8338
C9—C10	1.247 (5)	N2—N3	1.355 (3)
C9—H9	0.9300	O1—S1	1.4359 (18)
C10—H10A	0.9300	O2—S1	1.4286 (18)
C10—H10B	0.9300	O4—H4	0.8662
C6—C1—N1	121.5 (2)	C11—C12—C13	120.4 (2)
C6—C1—C2	119.3 (2)	C11—C12—H12	119.8
N1—C1—C2	119.2 (2)	C13—C12—H12	119.8
C3—C2—C1	122.6 (2)	C14—C13—C12	119.7 (2)
C3—C2—H2	118.7	C14—C13—H13	120.2
C1—C2—H2	118.7	C12—C13—H13	120.2
C2—C3—C4	117.9 (2)	O3—C14—C13	124.5 (2)
C2—C3—H3	121.1	O3—C14—C15	115.9 (2)
C4—C3—H3	121.1	C13—C14—C15	119.7 (2)
N2—C4—C3	128.5 (2)	C16—C15—C14	120.7 (2)
N2—C4—C5	110.8 (2)	C16—C15—H15	119.7
C3—C4—C5	120.6 (2)	C14—C15—H15	119.7
C7—C5—C6	134.9 (2)	C15—C16—C11	119.6 (2)
C7—C5—C4	105.0 (2)	C15—C16—H16	120.2
C6—C5—C4	120.0 (2)	C11—C16—H16	120.2
C1—C6—C5	119.4 (2)	O3—C17—H17A	109.5
C1—C6—Cl1	122.73 (17)	O3—C17—H17B	109.5
C5—C6—Cl1	117.83 (18)	H17A—C17—H17B	109.5
N3—C7—C5	106.2 (2)	O3—C17—H17C	109.5
N3—C7—H7	126.9	H17A—C17—H17C	109.5
C5—C7—H7	126.9	H17B—C17—H17C	109.5
N3—C8—C9	110.7 (3)	C1—N1—S1	122.73 (16)
N3—C8—H8A	109.5	C1—N1—H1	116.2
C9—C8—H8A	109.5	S1—N1—H1	112.1
N3—C8—H8B	109.5	N3—N2—C4	103.84 (18)
C9—C8—H8B	109.5	C7—N3—N2	114.1 (2)
H8A—C8—H8B	108.1	C7—N3—C8	126.8 (2)
C10—C9—C8	125.3 (4)	N2—N3—C8	119.0 (2)
C10—C9—H9	117.4	C14—O3—C17	118.8 (2)
C8—C9—H9	117.4	O2—S1—O1	119.55 (12)
C9—C10—H10A	120.0	O2—S1—N1	108.20 (11)
C9—C10—H10B	120.0	O1—S1—N1	104.94 (11)
H10A—C10—H10B	120.0	O2—S1—C11	107.69 (12)
C12—C11—C16	119.9 (2)	O1—S1—C11	108.89 (11)
C12—C11—S1	119.78 (19)	N1—S1—C11	106.92 (11)
C16—C11—S1	120.25 (19)
C6—C1—C2—C3	2.7 (4)	C13—C14—C15—C16	0.6 (4)
N1—C1—C2—C3	−173.7 (2)	C14—C15—C16—C11	−1.0 (4)
C1—C2—C3—C4	1.8 (4)	C12—C11—C16—C15	1.3 (4)
C2—C3—C4—N2	174.2 (2)	S1—C11—C16—C15	178.7 (2)
C2—C3—C4—C5	−3.0 (4)	C6—C1—N1—S1	114.3 (2)
N2—C4—C5—C7	−0.3 (3)	C2—C1—N1—S1	−69.4 (3)
C3—C4—C5—C7	177.4 (2)	C3—C4—N2—N3	−176.8 (2)
N2—C4—C5—C6	−177.8 (2)	C5—C4—N2—N3	0.6 (3)
C3—C4—C5—C6	−0.1 (3)	C5—C7—N3—N2	0.6 (3)
N1—C1—C6—C5	170.4 (2)	C5—C7—N3—C8	178.8 (2)
C2—C1—C6—C5	−5.8 (3)	C4—N2—N3—C7	−0.8 (3)
N1—C1—C6—Cl1	−8.6 (3)	C4—N2—N3—C8	−179.2 (2)
C2—C1—C6—Cl1	175.13 (17)	C9—C8—N3—C7	−99.0 (3)
C7—C5—C6—C1	−171.9 (3)	C9—C8—N3—N2	79.2 (3)
C4—C5—C6—C1	4.6 (3)	C13—C14—O3—C17	−5.1 (4)
C7—C5—C6—Cl1	7.2 (4)	C15—C14—O3—C17	175.5 (3)
C4—C5—C6—Cl1	−176.30 (18)	C1—N1—S1—O2	56.3 (2)
C6—C5—C7—N3	176.7 (3)	C1—N1—S1—O1	−175.03 (18)
C4—C5—C7—N3	−0.2 (3)	C1—N1—S1—C11	−59.5 (2)
N3—C8—C9—C10	127.3 (4)	C12—C11—S1—O2	−15.3 (2)
C16—C11—C12—C13	−1.2 (4)	C16—C11—S1—O2	167.2 (2)
S1—C11—C12—C13	−178.6 (2)	C12—C11—S1—O1	−146.4 (2)
C11—C12—C13—C14	0.7 (4)	C16—C11—S1—O1	36.2 (2)
C12—C13—C14—O3	−179.9 (3)	C12—C11—S1—N1	100.7 (2)
C12—C13—C14—C15	−0.4 (4)	C16—C11—S1—N1	−76.7 (2)
O3—C14—C15—C16	−180.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.83	2.04	2.875 (2)	174
O4—H4···N2	0.87	2.00	2.822 (2)	158
C7—H7···O3ii	0.93	2.37	3.288 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.83	2.04	2.875 (2)	174
O4—H4⋯N2	0.87	2.00	2.822 (2)	158
C7—H7⋯O3ii	0.93	2.37	3.288 (3)	170

Symmetry codes: (i) ; (ii) .