Ethyl 3-[6-(4-meth-oxy-benzene-sulfon-amido)-2H-indazol-2-yl]propano-ate monohydrate.

In the title compound, C(19)H(21)N(3)O(5)S·H(2)O, the central indazole system is essentially planar (r.m.s. deviation = 0.012 Å), while both the benzene ring and the mean plane defined by the non-H atoms of the ethyl propionic ester unit (r.m.s. deviation = 0.087 Å) are nearly perpendicular to the indazole plane, as indicated by the dihedral angles of 82.45 (8) and 75.62 (8)°, respectively. Consequently, the mol-ecule adopts a U-shaped geometry. In the crystal, the water mol-ecule, which is linked to the indazole system by a strong O-H⋯N hydrogen bond, is also involved in two additional N-H⋯O and O-H⋯O inter-actions, which link the organic mol-ecules into chains along the b-axis direction.

Related literature

For the pharmacological activity of sulfonamides, see: Gadad et al. (2000 ▶); Brzozowski et al. (2010 ▶); Drew (2000 ▶); Garaj et al. (2005 ▶). For their anti­proliferative activity see: Abbassi et al. (2012 ▶); Bouissane et al. (2006 ▶).

Experimental

Crystal data

C19H21N3O5S·n class="Chemical">H2O

M = 421.46

Monoclinic,

a = 9.0248 (3) Å

b = 8.7602 (3) Å

c = 13.1792 (4) Å

β = 101.062 (2)°

V = 1022.58 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.42 × 0.37 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer

10050 measured reflections

4021 independent reflections

3887 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.077

S = 1.05

4021 reflections

262 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 1779 Friedel pairs

Flack parameter: 0.03 (6)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: n class="CellLine">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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051975/lr2095sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051975/lr2095Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051975/lr2095Isup3.cml

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

C19H21N3O5S·H2O	F(000) = 444
Mr = 421.46	Dx = 1.369 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2yb	Cell parameters from 4021 reflections
a = 9.0248 (3) Å	θ = 2.3–26.4°
b = 8.7602 (3) Å	µ = 0.20 mm−1
c = 13.1792 (4) Å	T = 296 K
β = 101.062 (2)°	Block, colourless
V = 1022.58 (6) Å3	0.42 × 0.37 × 0.28 mm
Z = 2

Bruker X8 APEX diffractometer	3887 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 26.4°, θmin = 2.3°
φ and ω scans	h = −11→11
10050 measured reflections	k = −10→10
4021 independent reflections	l = −16→16

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.037P)2 + 0.2529P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4021 reflections	Δρmax = 0.28 e Å−3
262 parameters	Δρmin = −0.28 e Å−3
1 restraint	Absolute structure: Flack (1983), 1779 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (6)

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	0.75199 (19)	0.7888 (2)	0.11333 (12)	0.0197 (4)
C2	0.61152 (18)	0.8667 (2)	0.10899 (12)	0.0216 (3)
H2	0.6095	0.9726	0.1039	0.026*
C3	0.4816 (2)	0.7914 (2)	0.11201 (13)	0.0223 (4)
H3	0.3909	0.8438	0.1071	0.027*
C4	0.48733 (19)	0.6302 (2)	0.12290 (12)	0.0202 (3)
C5	0.62772 (18)	0.5536 (2)	0.12955 (12)	0.0191 (3)
C6	0.76182 (19)	0.6328 (2)	0.12325 (13)	0.0214 (4)
H6	0.8528	0.5817	0.1257	0.026*
C7	0.3845 (2)	0.5150 (2)	0.13056 (13)	0.0215 (4)
H7	0.2815	0.5268	0.1283	0.026*
C8	0.4016 (2)	0.2317 (2)	0.15290 (14)	0.0241 (4)
H8A	0.4322	0.1643	0.1022	0.029*
H8B	0.2921	0.2363	0.1386	0.029*
C9	0.4548 (2)	0.1655 (2)	0.25982 (14)	0.0273 (4)
H9A	0.4299	0.0577	0.2586	0.033*
H9B	0.5638	0.1746	0.2782	0.033*
C10	0.3852 (2)	0.2433 (2)	0.34120 (15)	0.0316 (4)
C11	0.3662 (4)	0.2412 (4)	0.5169 (2)	0.0783 (11)
H11A	0.4110	0.3401	0.5363	0.094*
H11B	0.2581	0.2546	0.4950	0.094*
C12	0.3972 (3)	0.1377 (5)	0.6044 (2)	0.0764 (10)
H12A	0.3521	0.1767	0.6594	0.115*
H12B	0.5043	0.1290	0.6277	0.115*
H12C	0.3556	0.0391	0.5839	0.115*
C13	1.07596 (19)	0.8265 (2)	0.27877 (13)	0.0236 (4)
C14	1.1631 (2)	0.7069 (2)	0.32717 (15)	0.0309 (4)
H14	1.2039	0.6351	0.2884	0.037*
C15	1.1882 (2)	0.6960 (3)	0.43361 (15)	0.0355 (5)
H15	1.2487	0.6179	0.4668	0.043*
C16	1.1239 (2)	0.8006 (2)	0.49155 (15)	0.0304 (4)
C17	1.0371 (3)	0.9201 (3)	0.44266 (16)	0.0367 (5)
H17	0.9944	0.9908	0.4812	0.044*
C18	1.0144 (2)	0.9330 (2)	0.33620 (16)	0.0342 (5)
H18	0.9577	1.0136	0.3031	0.041*
C19	1.0760 (3)	0.8738 (3)	0.65678 (15)	0.0430 (6)
H19A	1.0906	0.8351	0.7261	0.065*
H19B	0.9700	0.8764	0.6276	0.065*
H19C	1.1167	0.9751	0.6576	0.065*
N1	0.87396 (16)	0.88540 (16)	0.10220 (11)	0.0222 (3)
H1	0.8609	0.9762	0.1044	0.027*
N2	0.61166 (17)	0.40098 (17)	0.14153 (11)	0.0224 (3)
N3	0.46167 (16)	0.38390 (16)	0.14178 (10)	0.0202 (3)
O1	1.08832 (15)	0.70535 (16)	0.10224 (10)	0.0269 (3)
O2	1.13045 (15)	0.98256 (17)	0.12154 (11)	0.0315 (3)
O3	0.29906 (17)	0.3482 (2)	0.32659 (11)	0.0450 (4)
O4	0.4297 (2)	0.1772 (2)	0.43247 (11)	0.0520 (5)
O5	1.15167 (18)	0.77637 (19)	0.59538 (11)	0.0411 (4)
O6	0.83323 (15)	0.19739 (15)	0.10176 (10)	0.0297 (3)
H6A	0.7633	0.2565	0.1151	0.036*
H6B	0.8488	0.2280	0.0427	0.036*
S1	1.05094 (4)	0.84904 (5)	0.14406 (3)	0.02171 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0167 (9)	0.0247 (8)	0.0181 (8)	0.0017 (7)	0.0040 (7)	−0.0004 (6)
C2	0.0208 (8)	0.0207 (8)	0.0237 (8)	0.0050 (7)	0.0055 (6)	0.0004 (7)
C3	0.0171 (9)	0.0250 (8)	0.0257 (9)	0.0078 (7)	0.0061 (7)	0.0006 (7)
C4	0.0192 (9)	0.0241 (9)	0.0173 (8)	0.0040 (7)	0.0038 (7)	0.0000 (6)
C5	0.0181 (8)	0.0219 (8)	0.0166 (8)	0.0047 (7)	0.0015 (6)	0.0002 (6)
C6	0.0157 (8)	0.0243 (9)	0.0243 (9)	0.0078 (7)	0.0044 (7)	0.0019 (7)
C7	0.0192 (9)	0.0253 (9)	0.0202 (8)	0.0051 (7)	0.0044 (7)	−0.0011 (7)
C8	0.0209 (9)	0.0225 (9)	0.0287 (9)	−0.0006 (7)	0.0043 (7)	−0.0027 (7)
C9	0.0273 (10)	0.0234 (9)	0.0319 (10)	0.0020 (7)	0.0073 (8)	0.0031 (7)
C10	0.0330 (11)	0.0330 (10)	0.0309 (10)	0.0010 (9)	0.0112 (8)	0.0053 (8)
C11	0.110 (3)	0.097 (2)	0.0363 (14)	0.036 (2)	0.0350 (16)	0.0102 (15)
C12	0.0642 (19)	0.129 (3)	0.0388 (14)	−0.015 (2)	0.0174 (13)	0.0096 (17)
C13	0.0187 (8)	0.0259 (9)	0.0256 (8)	−0.0004 (7)	0.0026 (7)	−0.0019 (7)
C14	0.0290 (11)	0.0319 (10)	0.0319 (10)	0.0091 (8)	0.0062 (8)	0.0010 (8)
C15	0.0344 (11)	0.0375 (11)	0.0334 (10)	0.0094 (9)	0.0033 (9)	0.0082 (9)
C16	0.0251 (10)	0.0354 (10)	0.0289 (10)	−0.0046 (7)	0.0010 (8)	0.0003 (7)
C17	0.0404 (12)	0.0377 (11)	0.0321 (10)	0.0088 (9)	0.0072 (9)	−0.0068 (8)
C18	0.0362 (12)	0.0331 (10)	0.0319 (10)	0.0124 (9)	0.0028 (9)	−0.0011 (8)
C19	0.0374 (12)	0.0635 (17)	0.0277 (10)	−0.0016 (11)	0.0051 (8)	−0.0046 (10)
N1	0.0180 (8)	0.0188 (7)	0.0298 (7)	0.0047 (5)	0.0047 (6)	0.0040 (6)
N2	0.0190 (8)	0.0228 (7)	0.0259 (7)	0.0033 (6)	0.0053 (6)	0.0013 (6)
N3	0.0178 (7)	0.0217 (8)	0.0209 (7)	0.0018 (6)	0.0033 (5)	0.0001 (5)
O1	0.0208 (7)	0.0314 (7)	0.0300 (7)	0.0056 (6)	0.0084 (5)	−0.0007 (6)
O2	0.0203 (7)	0.0324 (7)	0.0438 (8)	−0.0005 (6)	0.0114 (6)	0.0073 (6)
O3	0.0536 (9)	0.0433 (8)	0.0434 (8)	0.0182 (9)	0.0227 (7)	0.0073 (8)
O4	0.0646 (11)	0.0640 (11)	0.0303 (8)	0.0236 (9)	0.0165 (8)	0.0126 (7)
O5	0.0444 (9)	0.0506 (9)	0.0262 (8)	0.0047 (7)	0.0020 (6)	0.0013 (6)
O6	0.0334 (8)	0.0249 (7)	0.0335 (7)	0.0082 (6)	0.0133 (6)	0.0030 (5)
S1	0.0152 (2)	0.0246 (2)	0.0263 (2)	0.00303 (17)	0.00648 (15)	0.00187 (18)

C1—C6	1.374 (2)	C12—H12A	0.9600
C1—N1	1.418 (2)	C12—H12B	0.9600
C1—C2	1.431 (2)	C12—H12C	0.9600
C2—C3	1.353 (3)	C13—C18	1.383 (2)
C2—H2	0.9300	C13—C14	1.390 (3)
C3—C4	1.419 (2)	C13—S1	1.7572 (17)
C3—H3	0.9300	C14—C15	1.381 (3)
C4—C7	1.387 (2)	C14—H14	0.9300
C4—C5	1.422 (2)	C15—C16	1.389 (3)
C5—N2	1.357 (2)	C15—H15	0.9300
C5—C6	1.411 (2)	C16—O5	1.360 (2)
C6—H6	0.9300	C16—C17	1.390 (3)
C7—N3	1.337 (2)	C17—C18	1.383 (3)
C7—H7	0.9300	C17—H17	0.9300
C8—N3	1.458 (2)	C18—H18	0.9300
C8—C9	1.514 (3)	C19—O5	1.436 (3)
C8—H8A	0.9700	C19—H19A	0.9600
C8—H8B	0.9700	C19—H19B	0.9600
C9—C10	1.506 (3)	C19—H19C	0.9600
C9—H9A	0.9700	N1—S1	1.6183 (14)
C9—H9B	0.9700	N1—H1	0.8050
C10—O3	1.196 (3)	N2—N3	1.363 (2)
C10—O4	1.326 (2)	O1—S1	1.4399 (14)
C11—C12	1.451 (4)	O2—S1	1.4327 (14)
C11—O4	1.458 (3)	O6—H6A	0.8601
C11—H11A	0.9700	O6—H6B	0.8600
C11—H11B	0.9700
C6—C1—N1	124.49 (16)	H12A—C12—H12B	109.5
C6—C1—C2	121.23 (17)	C11—C12—H12C	109.5
N1—C1—C2	114.23 (15)	H12A—C12—H12C	109.5
C3—C2—C1	122.16 (17)	H12B—C12—H12C	109.5
C3—C2—H2	118.9	C18—C13—C14	120.58 (17)
C1—C2—H2	118.9	C18—C13—S1	119.33 (14)
C2—C3—C4	118.27 (17)	C14—C13—S1	120.01 (14)
C2—C3—H3	120.9	C15—C14—C13	119.13 (18)
C4—C3—H3	120.9	C15—C14—H14	120.4
C7—C4—C3	135.97 (17)	C13—C14—H14	120.4
C7—C4—C5	104.64 (15)	C14—C15—C16	120.55 (19)
C3—C4—C5	119.38 (16)	C14—C15—H15	119.7
N2—C5—C6	127.09 (15)	C16—C15—H15	119.7
N2—C5—C4	111.00 (15)	O5—C16—C15	115.76 (18)
C6—C5—C4	121.91 (16)	O5—C16—C17	124.24 (18)
C1—C6—C5	117.01 (16)	C15—C16—C17	120.01 (18)
C1—C6—H6	121.5	C18—C17—C16	119.51 (18)
C5—C6—H6	121.5	C18—C17—H17	120.2
N3—C7—C4	106.95 (15)	C16—C17—H17	120.2
N3—C7—H7	126.5	C17—C18—C13	120.20 (18)
C4—C7—H7	126.5	C17—C18—H18	119.9
N3—C8—C9	112.72 (15)	C13—C18—H18	119.9
N3—C8—H8A	109.0	O5—C19—H19A	109.5
C9—C8—H8A	109.0	O5—C19—H19B	109.5
N3—C8—H8B	109.0	H19A—C19—H19B	109.5
C9—C8—H8B	109.0	O5—C19—H19C	109.5
H8A—C8—H8B	107.8	H19A—C19—H19C	109.5
C10—C9—C8	112.84 (16)	H19B—C19—H19C	109.5
C10—C9—H9A	109.0	C1—N1—S1	125.60 (12)
C8—C9—H9A	109.0	C1—N1—H1	117.6
C10—C9—H9B	109.0	S1—N1—H1	108.9
C8—C9—H9B	109.0	C5—N2—N3	103.70 (13)
H9A—C9—H9B	107.8	C7—N3—N2	113.70 (14)
O3—C10—O4	123.80 (19)	C7—N3—C8	126.97 (15)
O3—C10—C9	125.49 (18)	N2—N3—C8	119.33 (14)
O4—C10—C9	110.70 (17)	C10—O4—C11	115.4 (2)
C12—C11—O4	108.8 (3)	C16—O5—C19	117.30 (17)
C12—C11—H11A	109.9	H6A—O6—H6B	104.5
O4—C11—H11A	109.9	O2—S1—O1	118.09 (7)
C12—C11—H11B	109.9	O2—S1—N1	105.63 (8)
O4—C11—H11B	109.9	O1—S1—N1	109.27 (8)
H11A—C11—H11B	108.3	O2—S1—C13	109.18 (9)
C11—C12—H12A	109.5	O1—S1—C13	107.13 (8)
C11—C12—H12B	109.5	N1—S1—C13	107.07 (8)
C6—C1—C2—C3	−1.5 (3)	C14—C13—C18—C17	−1.1 (3)
N1—C1—C2—C3	175.96 (15)	S1—C13—C18—C17	−177.88 (17)
C1—C2—C3—C4	1.9 (3)	C6—C1—N1—S1	−26.6 (2)
C2—C3—C4—C7	178.80 (18)	C2—C1—N1—S1	155.99 (12)
C2—C3—C4—C5	−0.4 (3)	C6—C5—N2—N3	−179.35 (15)
C7—C4—C5—N2	−0.54 (19)	C4—C5—N2—N3	0.25 (18)
C3—C4—C5—N2	178.89 (15)	C4—C7—N3—N2	−0.50 (19)
C7—C4—C5—C6	179.08 (15)	C4—C7—N3—C8	179.99 (15)
C3—C4—C5—C6	−1.5 (2)	C5—N2—N3—C7	0.16 (18)
N1—C1—C6—C5	−177.59 (14)	C5—N2—N3—C8	179.70 (14)
C2—C1—C6—C5	−0.4 (2)	C9—C8—N3—C7	−111.10 (19)
N2—C5—C6—C1	−178.61 (17)	C9—C8—N3—N2	69.41 (19)
C4—C5—C6—C1	1.8 (2)	O3—C10—O4—C11	0.0 (4)
C3—C4—C7—N3	−178.7 (2)	C9—C10—O4—C11	−178.6 (2)
C5—C4—C7—N3	0.61 (18)	C12—C11—O4—C10	167.3 (3)
N3—C8—C9—C10	70.9 (2)	C15—C16—O5—C19	−174.48 (19)
C8—C9—C10—O3	−1.3 (3)	C17—C16—O5—C19	5.2 (3)
C8—C9—C10—O4	177.17 (17)	C1—N1—S1—O2	−176.12 (14)
C18—C13—C14—C15	−0.3 (3)	C1—N1—S1—O1	55.87 (16)
S1—C13—C14—C15	176.48 (16)	C1—N1—S1—C13	−59.84 (16)
C13—C14—C15—C16	1.8 (3)	C18—C13—S1—O2	66.47 (17)
C14—C15—C16—O5	177.83 (19)	C14—C13—S1—O2	−110.37 (16)
C14—C15—C16—C17	−1.9 (3)	C18—C13—S1—O1	−164.56 (15)
O5—C16—C17—C18	−179.2 (2)	C14—C13—S1—O1	18.60 (18)
C15—C16—C17—C18	0.5 (3)	C18—C13—S1—N1	−47.44 (18)
C16—C17—C18—C13	1.0 (3)	C14—C13—S1—N1	135.72 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···N2	0.86	1.94	2.8029 (19)	176
N1—H1···O6i	0.81	1.95	2.7575 (19)	177
O6—H6B···O1ii	0.86	2.10	2.9094 (17)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯N2	0.86	1.94	2.8029 (19)	176
N1—H1⋯O6i	0.81	1.95	2.7575 (19)	177
O6—H6B⋯O1ii	0.86	2.10	2.9094 (17)	156

Symmetry codes: (i) ; (ii) .