N-(1-Allyl-1H-indazol-5-yl)-4-meth-oxy-benzene-sulfonamide hemihydrate.

In the title compound, C17H17N3O3 (.)0.5H2O, the indazole system makes a dihedral angle of 46.19 (8)° with the plane through the benzene ring and is nearly perpendicular to the allyl group, as indicated by the dihedral angle of 81.2 (3)°. In the crystal, the water mol-ecule, disordered over two sites related by an inversion center, forms O-H⋯N bridges between indazole N atoms of two sulfonamide mol-ecules. It is also connected via N-H⋯O inter-action to the third sulfonamide mol-ecule; however, due to the water mol-ecule disorder, only every second mol-ecule of sulfonamide participates in this inter-action. This missing inter-action results in a slight disorder of the sulfonamide S,O and N atoms which are split over two sites with half occupancy. With the help of C-H⋯O hydrogen bonds, the mol-ecules are further connected into a three-dimensional network.

Related literature

For the pharmacological activity of sulfonamides, see: Bouissane et al. (2006 ▶); Supuran & Scozzafava (2003 ▶); Smith & Jones (2008 ▶); Scozzafava et al. (2003 ▶). For their anti­proliferative activity, see: Abbassi et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

2C17H17N3O3S·H2O

M = 704.81

Monoclinic,

a = 8.2099 (7) Å

b = 13.8928 (12) Å

c = 15.0495 (14) Å

β = 92.327 (3)°

V = 1715.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.38 × 0.36 × 0.25 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.693, T max = 0.747

19356 measured reflections

4088 independent reflections

2737 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.01

4088 reflections

266 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 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/S1600536813025543/gk2590sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025543/gk2590Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025543/gk2590Isup3.cml

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

2C17H17N3O3S·H2O	F(000) = 740
Mr = 704.81	Dx = 1.365 Mg m−3
Monoclinic, P21/n	Melting point: 370 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.2099 (7) Å	Cell parameters from 4088 reflections
b = 13.8928 (12) Å	θ = 2.7–27.9°
c = 15.0495 (14) Å	µ = 0.21 mm−1
β = 92.327 (3)°	T = 296 K
V = 1715.1 (3) Å3	Block, colourless
Z = 2	0.38 × 0.36 × 0.25 mm

Bruker X8 APEX diffractometer	4088 independent reflections
Radiation source: fine-focus sealed tube	2737 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 27.9°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
Tmin = 0.693, Tmax = 0.747	k = −17→18
19356 measured reflections	l = −19→19

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.3501P] where P = (Fo2 + 2Fc2)/3
4088 reflections	(Δ/σ)max < 0.001
266 parameters	Δρmax = 0.15 e Å−3
2 restraints	Δρmin = −0.17 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 > 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	0.4495 (2)	−0.11076 (14)	0.23403 (11)	0.0607 (5)
C2	0.3084 (2)	−0.06191 (13)	0.20204 (12)	0.0602 (4)
H2	0.2989	0.0038	0.2126	0.072*
C3	0.18511 (19)	−0.10864 (12)	0.15581 (12)	0.0560 (4)
H3	0.0918	−0.0764	0.1351	0.067*
C4	0.20595 (18)	−0.20712 (11)	0.14118 (10)	0.0469 (4)
C5	0.34564 (19)	−0.25681 (12)	0.17146 (11)	0.0514 (4)
C6	0.4694 (2)	−0.20697 (14)	0.21927 (11)	0.0618 (5)
H6	0.5628	−0.2388	0.2404	0.074*
C7	0.3185 (2)	−0.35243 (13)	0.14334 (14)	0.0680 (5)
H7	0.3916	−0.4026	0.1542	0.082*
C8	−0.0440 (2)	−0.25522 (14)	0.04742 (13)	0.0656 (5)
H8A	−0.1088	−0.2084	0.0781	0.079*
H8B	−0.1062	−0.3145	0.0425	0.079*
C9	−0.0116 (3)	−0.21878 (16)	−0.04337 (13)	0.0753 (6)
H9	0.0561	−0.2554	−0.0781	0.090*
C10	−0.0701 (3)	−0.14065 (18)	−0.07713 (17)	0.0909 (7)
H10A	−0.1382	−0.1021	−0.0443	0.109*
H10B	−0.0443	−0.1225	−0.1344	0.109*
C11	0.64190 (18)	0.08820 (13)	0.17142 (11)	0.0528 (4)
C12	0.6036 (2)	0.07706 (13)	0.08101 (11)	0.0572 (4)
H12	0.6267	0.0194	0.0528	0.069*
C13	0.5320 (2)	0.15075 (13)	0.03369 (11)	0.0574 (4)
H13	0.5056	0.1426	−0.0265	0.069*
C14	0.49834 (19)	0.23733 (12)	0.07447 (12)	0.0536 (4)
C15	0.5389 (2)	0.24981 (15)	0.16372 (13)	0.0670 (5)
H15	0.5187	0.3082	0.1914	0.080*
C16	0.6095 (2)	0.17525 (16)	0.21134 (12)	0.0676 (5)
H16	0.6358	0.1836	0.2715	0.081*
C17	0.3917 (3)	0.39644 (15)	0.0586 (2)	0.1045 (9)
H17A	0.3408	0.4371	0.0140	0.157*
H17B	0.4915	0.4255	0.0805	0.157*
H17C	0.3197	0.3884	0.1068	0.157*
N1	0.5992 (6)	−0.0729 (4)	0.2783 (4)	0.0542 (11)	0.50
H1	0.5661	−0.0447	0.3275	0.065*	0.50
S1	0.7087 (4)	0.0029 (3)	0.2443 (3)	0.0586 (6)	0.50
O1	0.7780 (11)	−0.0690 (6)	0.1876 (6)	0.0787 (17)	0.50
O2	0.8022 (7)	0.0461 (5)	0.3174 (4)	0.0836 (15)	0.50
N1'	0.5494 (6)	−0.0450 (4)	0.2905 (4)	0.0524 (11)	0.50
H1'	0.5163	−0.0168	0.3397	0.063*	0.50
S1'	0.7382 (4)	−0.0190 (3)	0.2239 (2)	0.0574 (7)	0.50
O1'	0.7928 (11)	−0.0869 (6)	0.1587 (5)	0.0736 (12)	0.50
O2'	0.8508 (7)	0.0180 (5)	0.2899 (4)	0.0801 (15)	0.50
N2	0.1771 (2)	−0.36215 (11)	0.09978 (11)	0.0683 (4)
N3	0.10705 (17)	−0.27305 (10)	0.09919 (9)	0.0558 (4)
O3	0.42555 (16)	0.30521 (9)	0.02113 (9)	0.0731 (4)
O4	0.5283 (4)	−0.0107 (2)	0.44955 (19)	0.0927 (10)	0.50
H4	0.4728	0.0403	0.4598	0.111*	0.50
H4'	0.5735	−0.0261	0.5001	0.111*	0.50

	U11	U22	U33	U12	U13	U23
C1	0.0617 (10)	0.0779 (12)	0.0414 (9)	−0.0260 (9)	−0.0095 (7)	0.0098 (8)
C2	0.0597 (10)	0.0590 (10)	0.0623 (11)	−0.0108 (8)	0.0071 (8)	−0.0109 (9)
C3	0.0428 (8)	0.0562 (10)	0.0689 (11)	0.0012 (7)	0.0005 (7)	−0.0025 (8)
C4	0.0431 (8)	0.0524 (9)	0.0447 (8)	−0.0025 (6)	−0.0032 (6)	0.0017 (7)
C5	0.0479 (8)	0.0552 (10)	0.0507 (9)	0.0003 (7)	−0.0046 (7)	0.0098 (7)
C6	0.0507 (9)	0.0754 (12)	0.0581 (10)	−0.0083 (8)	−0.0146 (8)	0.0235 (9)
C7	0.0651 (11)	0.0545 (11)	0.0831 (13)	0.0084 (9)	−0.0107 (10)	0.0057 (9)
C8	0.0545 (10)	0.0683 (12)	0.0723 (12)	−0.0088 (8)	−0.0198 (9)	0.0031 (9)
C9	0.0764 (13)	0.0858 (14)	0.0621 (12)	0.0144 (11)	−0.0179 (10)	−0.0080 (11)
C10	0.0900 (16)	0.0918 (17)	0.0903 (16)	0.0097 (13)	−0.0014 (13)	0.0144 (13)
C11	0.0391 (8)	0.0661 (10)	0.0526 (9)	−0.0119 (7)	−0.0045 (7)	−0.0006 (8)
C12	0.0607 (10)	0.0550 (10)	0.0557 (10)	−0.0045 (8)	−0.0002 (8)	−0.0104 (8)
C13	0.0674 (10)	0.0614 (11)	0.0430 (9)	−0.0061 (8)	−0.0028 (8)	−0.0060 (8)
C14	0.0465 (8)	0.0547 (10)	0.0595 (10)	−0.0072 (7)	−0.0009 (7)	−0.0052 (8)
C15	0.0658 (11)	0.0704 (12)	0.0643 (12)	0.0015 (9)	−0.0020 (9)	−0.0259 (10)
C16	0.0607 (11)	0.0954 (15)	0.0461 (10)	−0.0057 (10)	−0.0061 (8)	−0.0158 (10)
C17	0.1018 (18)	0.0579 (13)	0.151 (2)	0.0092 (12)	−0.0287 (17)	−0.0145 (14)
N1	0.051 (3)	0.064 (3)	0.048 (2)	−0.0047 (19)	−0.009 (2)	−0.0044 (19)
S1	0.0382 (11)	0.0669 (15)	0.0694 (16)	−0.0012 (8)	−0.0146 (9)	0.0034 (9)
O1	0.059 (2)	0.056 (3)	0.122 (6)	0.028 (2)	0.020 (3)	−0.019 (3)
O2	0.069 (3)	0.091 (4)	0.087 (4)	−0.013 (2)	−0.045 (3)	0.003 (2)
N1'	0.050 (3)	0.065 (3)	0.042 (2)	−0.0058 (19)	−0.0044 (18)	−0.0026 (19)
S1'	0.0353 (12)	0.0652 (18)	0.0704 (18)	−0.0059 (9)	−0.0121 (9)	0.0045 (11)
O1'	0.046 (2)	0.064 (3)	0.112 (5)	0.016 (2)	0.014 (3)	−0.017 (2)
O2'	0.056 (3)	0.082 (3)	0.099 (4)	−0.014 (2)	−0.036 (2)	0.007 (2)
N2	0.0745 (10)	0.0528 (9)	0.0764 (11)	0.0032 (7)	−0.0109 (8)	−0.0062 (8)
N3	0.0533 (8)	0.0537 (8)	0.0590 (8)	−0.0026 (6)	−0.0133 (6)	−0.0004 (7)
O3	0.0735 (9)	0.0590 (8)	0.0856 (9)	−0.0007 (6)	−0.0104 (7)	0.0020 (7)
O4	0.133 (3)	0.0734 (18)	0.0708 (17)	0.0370 (18)	−0.0081 (18)	−0.0020 (15)

C1—C6	1.366 (3)	C11—S1'	1.848 (4)
C1—C2	1.411 (3)	C12—C13	1.366 (2)
C1—N1	1.471 (6)	C12—H12	0.9300
C1—N1'	1.474 (6)	C13—C14	1.383 (2)
C2—C3	1.369 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—O3	1.361 (2)
C3—C4	1.397 (2)	C14—C15	1.382 (3)
C3—H3	0.9300	C15—C16	1.374 (3)
C4—N3	1.3623 (19)	C15—H15	0.9300
C4—C5	1.399 (2)	C16—H16	0.9300
C5—C6	1.403 (2)	C17—O3	1.419 (3)
C5—C7	1.409 (2)	C17—H17A	0.9600
C6—H6	0.9300	C17—H17B	0.9600
C7—N2	1.317 (2)	C17—H17C	0.9600
C7—H7	0.9300	N1—S1	1.489 (8)
C8—N3	1.459 (2)	N1—H1	0.8898
C8—C9	1.491 (3)	S1—O2	1.445 (7)
C8—H8A	0.9700	S1—O1	1.4463 (10)
C8—H8B	0.9700	N1'—S1'	1.914 (7)
C9—C10	1.283 (3)	N1'—H1'	0.8898
C9—H9	0.9300	S1'—O2'	1.425 (7)
C10—H10A	0.9300	S1'—O1'	1.4460 (10)
C10—H10B	0.9300	N2—N3	1.365 (2)
C11—C16	1.381 (3)	O4—O4i	1.633 (6)
C11—C12	1.393 (2)	O4—H4	0.8600
C11—S1	1.691 (5)	O4—H4'	0.8600
C6—C1—C2	121.13 (15)	C12—C13—H13	119.7
C6—C1—N1	108.7 (2)	C14—C13—H13	119.7
C2—C1—N1	129.9 (3)	O3—C14—C15	124.71 (16)
C6—C1—N1'	129.3 (2)	O3—C14—C13	115.57 (15)
C2—C1—N1'	109.2 (2)	C15—C14—C13	119.73 (17)
C3—C2—C1	121.71 (17)	C16—C15—C14	119.50 (17)
C3—C2—H2	119.1	C16—C15—H15	120.3
C1—C2—H2	119.1	C14—C15—H15	120.3
C2—C3—C4	116.86 (16)	C15—C16—C11	121.18 (16)
C2—C3—H3	121.6	C15—C16—H16	119.4
C4—C3—H3	121.6	C11—C16—H16	119.4
N3—C4—C3	131.06 (14)	O3—C17—H17A	109.5
N3—C4—C5	106.54 (14)	O3—C17—H17B	109.5
C3—C4—C5	122.40 (14)	H17A—C17—H17B	109.5
C4—C5—C6	119.36 (16)	O3—C17—H17C	109.5
C4—C5—C7	104.47 (14)	H17A—C17—H17C	109.5
C6—C5—C7	136.17 (16)	H17B—C17—H17C	109.5
C1—C6—C5	118.54 (16)	C1—N1—S1	127.0 (5)
C1—C6—H6	120.7	C1—N1—H1	104.9
C5—C6—H6	120.7	S1—N1—H1	100.6
N2—C7—C5	111.81 (15)	O2—S1—O1	121.8 (5)
N2—C7—H7	124.1	O2—S1—N1	110.0 (5)
C5—C7—H7	124.1	O1—S1—N1	88.4 (5)
N3—C8—C9	111.58 (16)	O2—S1—C11	110.6 (4)
N3—C8—H8A	109.3	O1—S1—C11	103.1 (5)
C9—C8—H8A	109.3	N1—S1—C11	122.3 (3)
N3—C8—H8B	109.3	C1—N1'—S1'	104.9 (3)
C9—C8—H8B	109.3	C1—N1'—H1	132.6
H8A—C8—H8B	108.0	S1'—N1'—H1	110.1
C10—C9—C8	124.9 (2)	C1—N1'—H1'	124.8
C10—C9—H9	117.6	S1'—N1'—H1'	129.3
C8—C9—H9	117.6	O2'—S1'—O1'	119.8 (4)
C9—C10—H10A	120.0	O2'—S1'—C11	105.2 (3)
C9—C10—H10B	120.0	O1'—S1'—C11	112.0 (5)
H10A—C10—H10B	120.0	O2'—S1'—N1'	102.7 (4)
C16—C11—C12	118.85 (17)	O1'—S1'—N1'	120.8 (4)
C16—C11—S1	113.23 (17)	C11—S1'—N1'	92.0 (2)
C12—C11—S1	127.62 (18)	C7—N2—N3	105.84 (14)
C16—C11—S1'	127.33 (16)	C4—N3—N2	111.33 (13)
C12—C11—S1'	113.81 (17)	C4—N3—C8	127.69 (14)
C13—C12—C11	120.08 (16)	N2—N3—C8	120.42 (14)
C13—C12—H12	120.0	C14—O3—C17	118.21 (17)
C11—C12—H12	120.0	H4—O4—H4'	104.9
C12—C13—C14	120.64 (16)
C6—C1—C2—C3	0.6 (3)	C16—C11—S1—O2	−32.4 (4)
N1—C1—C2—C3	174.6 (3)	C12—C11—S1—O2	154.1 (3)
N1'—C1—C2—C3	−172.7 (3)	S1'—C11—S1—O2	124.8 (11)
C1—C2—C3—C4	−0.4 (3)	C16—C11—S1—O1	−164.0 (4)
C2—C3—C4—N3	179.20 (17)	C12—C11—S1—O1	22.4 (5)
C2—C3—C4—C5	−0.3 (3)	S1'—C11—S1—O1	−6.8 (9)
N3—C4—C5—C6	−178.82 (15)	C16—C11—S1—N1	99.6 (3)
C3—C4—C5—C6	0.8 (3)	C12—C11—S1—N1	−74.0 (3)
N3—C4—C5—C7	0.46 (18)	S1'—C11—S1—N1	−103.2 (11)
C3—C4—C5—C7	−179.94 (17)	C6—C1—N1'—S1'	77.0 (4)
C2—C1—C6—C5	−0.1 (3)	C2—C1—N1'—S1'	−110.3 (2)
N1—C1—C6—C5	−175.3 (3)	N1—C1—N1'—S1'	44.8 (10)
N1'—C1—C6—C5	171.8 (3)	C16—C11—S1'—O2'	−32.7 (4)
C4—C5—C6—C1	−0.6 (3)	C12—C11—S1'—O2'	145.7 (3)
C7—C5—C6—C1	−179.5 (2)	S1—C11—S1'—O2'	−59.3 (9)
C4—C5—C7—N2	0.1 (2)	C16—C11—S1'—O1'	−164.4 (4)
C6—C5—C7—N2	179.2 (2)	C12—C11—S1'—O1'	14.0 (5)
N3—C8—C9—C10	−125.3 (2)	S1—C11—S1'—O1'	169.0 (11)
C16—C11—C12—C13	−1.4 (3)	C16—C11—S1'—N1'	71.0 (3)
S1—C11—C12—C13	171.9 (2)	C12—C11—S1'—N1'	−110.6 (2)
S1'—C11—C12—C13	−179.90 (18)	S1—C11—S1'—N1'	44.4 (9)
C11—C12—C13—C14	0.7 (3)	C1—N1'—S1'—O2'	−162.4 (4)
C12—C13—C14—O3	−179.39 (15)	C1—N1'—S1'—O1'	−25.8 (6)
C12—C13—C14—C15	0.6 (3)	C1—N1'—S1'—C11	91.5 (3)
O3—C14—C15—C16	178.76 (17)	C5—C7—N2—N3	−0.7 (2)
C13—C14—C15—C16	−1.3 (3)	C3—C4—N3—N2	179.53 (18)
C14—C15—C16—C11	0.6 (3)	C5—C4—N3—N2	−0.92 (18)
C12—C11—C16—C15	0.7 (3)	C3—C4—N3—C8	8.2 (3)
S1—C11—C16—C15	−173.5 (2)	C5—C4—N3—C8	−172.26 (17)
S1'—C11—C16—C15	179.0 (2)	C7—N2—N3—C4	1.0 (2)
C6—C1—N1—S1	118.9 (3)	C7—N2—N3—C8	173.05 (17)
C2—C1—N1—S1	−55.7 (5)	C9—C8—N3—C4	78.0 (2)
N1'—C1—N1—S1	−86.9 (12)	C9—C8—N3—N2	−92.6 (2)
C1—N1—S1—O2	157.9 (4)	C15—C14—O3—C17	1.5 (3)
C1—N1—S1—O1	−78.7 (5)	C13—C14—O3—C17	−178.45 (18)
C1—N1—S1—C11	25.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.89	1.93	2.802 (6)	165
C3—H3···O1′ii	0.93	2.50	3.237 (9)	136
C8—H8A···O1′ii	0.97	2.25	3.202 (4)	168
C7—H7···O2iii	0.93	2.63	3.447 (7)	147
O4—H4···N2iv	0.86	2.02	2.748 (3)	142
O4—H4′···N2v	0.86	2.29	3.082 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.89	1.93	2.802 (6)	165
C3—H3⋯O1′i	0.93	2.50	3.237 (9)	136
C8—H8A⋯O1′i	0.97	2.25	3.202 (4)	168
C7—H7⋯O2ii	0.93	2.63	3.447 (7)	147
O4—H4⋯N2iii	0.86	2.02	2.748 (3)	142
O4—H4′⋯N2iv	0.86	2.29	3.082 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .