N-(3-Chloro-4-eth-oxy-1-methyl-1H-indazol-5-yl)-4-meth-oxy-benzene-sulfonamide.

The indazole ring system of the title compound, C17H18ClN3O4S, is almost planar (r.m.s. deviation = 0.0113 Å) and forms dihedral angles of 32.22 (8) and 57.5 (3)° with the benzene ring and the mean plane through the 4-eth-oxy group, respectively. In the crystal, mol-ecules are connected by pairs of N-H⋯O hydrogen bonds into inversion dimers, which are further linked by π-π inter-actions between the diazole rings [inter-centroid distance = 3.4946 (11) Å], forming chains parallel to [101].

Related literature

For the biological activity of sulfonamides, see: El-Sayed et al. (2011 ▶); Mustafa et al. (2012 ▶); Scozzafava et al. (2003 ▶); Bouissane et al. (2006 ▶). For similar compounds see: Abbassi et al. (2012 ▶, 2013 ▶); Chicha et al. (2014 ▶).

Experimental

Crystal data

C17H18ClN3O4S

M = 395.85

Triclinic,

a = 8.5296 (9) Å

b = 8.6165 (9) Å

c = 12.9821 (14) Å

α = 91.810 (6)°

β = 102.566 (5)°

γ = 100.514 (5)°

V = 913.10 (17) Å3

Z = 2

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; Bruker, 2009 ▶) T min = 0.693, T max = 0.747

20149 measured reflections

4353 independent reflections

3825 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.128

S = 1.04

4353 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.62 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/S1600536814010800/rz5125sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010800/rz5125Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010800/rz5125Isup3.cml

CCDC reference: 1002205

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

C17H18ClN3O4S	Z = 2
Mr = 395.85	F(000) = 412
Triclinic, P1	Dx = 1.440 Mg m−3
Hall symbol: -P 1	Melting point: 382 K
a = 8.5296 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6165 (9) Å	Cell parameters from 4353 reflections
c = 12.9821 (14) Å	θ = 2.5–27.9°
α = 91.810 (6)°	µ = 0.35 mm−1
β = 102.566 (5)°	T = 296 K
γ = 100.514 (5)°	Block, colourless
V = 913.10 (17) Å3	0.40 × 0.36 × 0.31 mm

Bruker X8 APEX Diffractometer	4353 independent reflections
Radiation source: fine-focus sealed tube	3825 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 27.9°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.693, Tmax = 0.747	k = −11→11
20149 measured reflections	l = −17→17

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.4317P] where P = (Fo2 + 2Fc2)/3
4353 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.62 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 > 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
C1	0.5956 (2)	1.2540 (2)	0.53435 (14)	0.0465 (4)
C2	0.6304 (2)	1.16538 (19)	0.62328 (12)	0.0362 (3)
C3	0.4744 (2)	1.0918 (2)	0.63444 (13)	0.0398 (4)
C4	0.4514 (2)	0.9921 (2)	0.71502 (15)	0.0442 (4)
H4	0.3477	0.9433	0.7215	0.053*
C5	0.5905 (2)	0.9706 (2)	0.78353 (14)	0.0415 (4)
H5	0.5805	0.9040	0.8377	0.050*
C6	0.7494 (2)	1.04510 (19)	0.77578 (12)	0.0360 (3)
C7	0.77174 (19)	1.14377 (19)	0.69596 (12)	0.0345 (3)
C8	0.1867 (2)	1.0920 (3)	0.53266 (18)	0.0650 (6)
H8A	0.1396	1.1448	0.4730	0.098*
H8B	0.1465	1.1199	0.5929	0.098*
H8C	0.1567	0.9795	0.5164	0.098*
C9	1.0146 (4)	1.3349 (4)	0.7609 (3)	0.1024 (13)
H9A	1.0714	1.2835	0.8190	0.123*
H9B	0.9409	1.3902	0.7881	0.123*
C10	1.1304 (4)	1.4471 (4)	0.7272 (3)	0.0911 (10)
H10A	1.1881	1.5222	0.7854	0.137*
H10B	1.0757	1.5013	0.6710	0.137*
H10C	1.2066	1.3947	0.7023	0.137*
C11	0.8443 (2)	0.6987 (2)	0.84226 (13)	0.0404 (4)
C12	0.7169 (2)	0.6368 (2)	0.75581 (14)	0.0463 (4)
H12	0.7098	0.6828	0.6915	0.056*
C13	0.6019 (3)	0.5074 (2)	0.76605 (16)	0.0497 (4)
H13	0.5163	0.4665	0.7087	0.060*
C14	0.6129 (2)	0.4373 (2)	0.86199 (16)	0.0468 (4)
C15	0.7421 (3)	0.4963 (2)	0.94719 (15)	0.0517 (5)
H15	0.7518	0.4475	1.0106	0.062*
C16	0.8564 (2)	0.6281 (2)	0.93729 (14)	0.0477 (4)
H16	0.9417	0.6694	0.9947	0.057*
C17	0.4980 (3)	0.2324 (3)	0.9591 (2)	0.0686 (6)
H17A	0.4045	0.1478	0.9498	0.103*
H17B	0.4982	0.3051	1.0167	0.103*
H17C	0.5963	0.1898	0.9744	0.103*
N1	0.36396 (19)	1.1398 (2)	0.55635 (13)	0.0501 (4)
N2	0.4375 (2)	1.2384 (2)	0.49460 (13)	0.0539 (4)
N3	0.89007 (18)	1.02121 (17)	0.85304 (11)	0.0404 (3)
H3N	0.8863	1.0326	0.9184	0.048*
O1	0.92080 (15)	1.21799 (16)	0.68322 (10)	0.0452 (3)
O2	1.01006 (18)	0.87771 (18)	0.73054 (11)	0.0539 (3)
O3	1.11721 (16)	0.89209 (18)	0.92468 (11)	0.0527 (3)
O4	0.4905 (2)	0.31318 (18)	0.86454 (14)	0.0643 (4)
S1	0.98089 (5)	0.87464 (5)	0.83452 (3)	0.04091 (13)
Cl1	0.73113 (8)	1.37072 (8)	0.47676 (5)	0.0764 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0518 (10)	0.0536 (10)	0.0352 (8)	0.0137 (8)	0.0083 (7)	0.0118 (7)
C2	0.0383 (8)	0.0405 (8)	0.0305 (7)	0.0087 (6)	0.0077 (6)	0.0051 (6)
C3	0.0344 (8)	0.0495 (9)	0.0344 (8)	0.0085 (7)	0.0054 (6)	−0.0009 (7)
C4	0.0357 (8)	0.0528 (10)	0.0435 (9)	0.0017 (7)	0.0138 (7)	0.0030 (7)
C5	0.0444 (9)	0.0443 (9)	0.0377 (8)	0.0052 (7)	0.0150 (7)	0.0100 (7)
C6	0.0370 (8)	0.0391 (8)	0.0317 (7)	0.0079 (6)	0.0062 (6)	0.0061 (6)
C7	0.0335 (7)	0.0380 (8)	0.0317 (7)	0.0048 (6)	0.0086 (6)	0.0046 (6)
C8	0.0363 (10)	0.1031 (18)	0.0536 (12)	0.0190 (11)	0.0023 (8)	−0.0030 (12)
C9	0.098 (2)	0.100 (2)	0.093 (2)	−0.0537 (18)	0.0542 (18)	−0.0367 (17)
C10	0.0769 (18)	0.090 (2)	0.093 (2)	−0.0280 (15)	0.0291 (16)	0.0033 (16)
C11	0.0454 (9)	0.0436 (9)	0.0341 (8)	0.0157 (7)	0.0066 (7)	0.0074 (7)
C12	0.0552 (10)	0.0470 (9)	0.0354 (8)	0.0141 (8)	0.0034 (7)	0.0070 (7)
C13	0.0547 (11)	0.0460 (10)	0.0440 (10)	0.0123 (8)	0.0002 (8)	0.0001 (8)
C14	0.0537 (10)	0.0386 (9)	0.0518 (10)	0.0150 (8)	0.0144 (8)	0.0051 (7)
C15	0.0646 (12)	0.0528 (11)	0.0407 (9)	0.0172 (9)	0.0118 (8)	0.0139 (8)
C16	0.0540 (10)	0.0529 (10)	0.0344 (8)	0.0141 (8)	0.0023 (7)	0.0088 (7)
C17	0.0824 (16)	0.0540 (12)	0.0782 (16)	0.0135 (11)	0.0346 (13)	0.0184 (11)
N1	0.0383 (8)	0.0712 (11)	0.0393 (8)	0.0152 (7)	0.0021 (6)	0.0049 (7)
N2	0.0538 (9)	0.0712 (11)	0.0379 (8)	0.0222 (8)	0.0034 (7)	0.0104 (7)
N3	0.0430 (8)	0.0459 (8)	0.0309 (7)	0.0105 (6)	0.0034 (6)	0.0074 (6)
O1	0.0373 (6)	0.0556 (7)	0.0418 (7)	0.0006 (5)	0.0133 (5)	0.0069 (5)
O2	0.0551 (8)	0.0700 (9)	0.0422 (7)	0.0175 (7)	0.0175 (6)	0.0119 (6)
O3	0.0402 (7)	0.0672 (9)	0.0472 (7)	0.0139 (6)	−0.0014 (6)	0.0099 (6)
O4	0.0689 (10)	0.0500 (8)	0.0710 (10)	0.0045 (7)	0.0145 (8)	0.0114 (7)
S1	0.0376 (2)	0.0510 (3)	0.0343 (2)	0.01182 (17)	0.00498 (16)	0.00904 (17)
Cl1	0.0761 (4)	0.0903 (4)	0.0633 (4)	0.0073 (3)	0.0187 (3)	0.0442 (3)

C1—N2	1.315 (3)	C10—H10B	0.9600
C1—C2	1.412 (2)	C10—H10C	0.9600
C1—Cl1	1.705 (2)	C11—C16	1.385 (2)
C2—C3	1.406 (2)	C11—C12	1.395 (3)
C2—C7	1.406 (2)	C11—S1	1.7552 (19)
C3—N1	1.356 (2)	C12—C13	1.374 (3)
C3—C4	1.399 (3)	C12—H12	0.9300
C4—C5	1.366 (3)	C13—C14	1.394 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.416 (2)	C14—O4	1.358 (3)
C5—H5	0.9300	C14—C15	1.388 (3)
C6—C7	1.384 (2)	C15—C16	1.384 (3)
C6—N3	1.438 (2)	C15—H15	0.9300
C7—O1	1.3618 (19)	C16—H16	0.9300
C8—N1	1.454 (3)	C17—O4	1.425 (3)
C8—H8A	0.9600	C17—H17A	0.9600
C8—H8B	0.9600	C17—H17B	0.9600
C8—H8C	0.9600	C17—H17C	0.9600
C9—O1	1.401 (3)	N1—N2	1.351 (2)
C9—C10	1.403 (3)	N3—S1	1.6346 (15)
C9—H9A	0.9700	N3—H3N	0.8599
C9—H9B	0.9700	O2—S1	1.4249 (14)
C10—H10A	0.9600	O3—S1	1.4414 (13)
N2—C1—C2	112.46 (17)	C16—C11—C12	120.00 (18)
N2—C1—Cl1	119.64 (14)	C16—C11—S1	119.51 (14)
C2—C1—Cl1	127.89 (15)	C12—C11—S1	120.31 (13)
C3—C2—C7	120.42 (15)	C13—C12—C11	119.71 (17)
C3—C2—C1	103.30 (15)	C13—C12—H12	120.1
C7—C2—C1	136.23 (16)	C11—C12—H12	120.1
N1—C3—C4	130.62 (17)	C12—C13—C14	120.31 (18)
N1—C3—C2	106.77 (16)	C12—C13—H13	119.8
C4—C3—C2	122.60 (16)	C14—C13—H13	119.8
C5—C4—C3	115.92 (16)	O4—C14—C15	124.41 (18)
C5—C4—H4	122.0	O4—C14—C13	115.58 (18)
C3—C4—H4	122.0	C15—C14—C13	120.01 (18)
C4—C5—C6	122.96 (16)	C16—C15—C14	119.60 (17)
C4—C5—H5	118.5	C16—C15—H15	120.2
C6—C5—H5	118.5	C14—C15—H15	120.2
C7—C6—C5	120.98 (15)	C15—C16—C11	120.33 (18)
C7—C6—N3	119.18 (15)	C15—C16—H16	119.8
C5—C6—N3	119.83 (14)	C11—C16—H16	119.8
O1—C7—C6	124.09 (15)	O4—C17—H17A	109.5
O1—C7—C2	118.80 (14)	O4—C17—H17B	109.5
C6—C7—C2	117.09 (14)	H17A—C17—H17B	109.5
N1—C8—H8A	109.5	O4—C17—H17C	109.5
N1—C8—H8B	109.5	H17A—C17—H17C	109.5
H8A—C8—H8B	109.5	H17B—C17—H17C	109.5
N1—C8—H8C	109.5	N2—N1—C3	111.91 (15)
H8A—C8—H8C	109.5	N2—N1—C8	120.44 (17)
H8B—C8—H8C	109.5	C3—N1—C8	127.59 (19)
O1—C9—C10	115.4 (3)	C1—N2—N1	105.56 (15)
O1—C9—H9A	108.4	C6—N3—S1	120.30 (12)
C10—C9—H9A	108.4	C6—N3—H3N	116.8
O1—C9—H9B	108.4	S1—N3—H3N	110.2
C10—C9—H9B	108.4	C7—O1—C9	118.21 (16)
H9A—C9—H9B	107.5	C14—O4—C17	118.35 (19)
C9—C10—H10A	109.5	O2—S1—O3	119.64 (9)
C9—C10—H10B	109.5	O2—S1—N3	108.12 (8)
H10A—C10—H10B	109.5	O3—S1—N3	104.44 (8)
C9—C10—H10C	109.5	O2—S1—C11	108.74 (9)
H10A—C10—H10C	109.5	O3—S1—C11	108.06 (8)
H10B—C10—H10C	109.5	N3—S1—C11	107.20 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O3i	0.86	2.13	2.974 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O3i	0.86	2.13	2.974 (2)	169

Symmetry code: (i) .