Crystal structure of N-(1-allyl-3-chloro-4-eth-oxy-1H-indazol-5-yl)-4-meth-oxybenzene-sulfonamide.

In the title compound, C19H20ClN3O4S, the benzene ring is inclined to the indazole ring system (r.m.s. deviation = 0.014 Å) by 65.07 (8)°. The allyl and eth-oxy groups are almost normal to the indazole ring, as indicated by the respective torsion angles [N-N-C-C = 111.6 (2) and C-C-O-C = -88.1 (2)°]. In the crystal, mol-ecules are connected by N-H⋯N hydrogen bonds, forming helical chains propagating along [010]. The chains are linked by 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 ▶); Bouissane et al. (2006 ▶); Ghorab et al. (2009 ▶). For similar compounds, see: Abbassi et al. (2012 ▶, 2013 ▶); Chicha et al. (2014 ▶).

Experimental

Crystal data

C19H20ClN3O4S

M = 421.89

Monoclinic,

a = 8.2699 (7) Å

b = 13.1235 (12) Å

c = 10.0026 (9) Å

β = 110.379 (5)°

V = 1017.64 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.42 × 0.32 × 0.28 mm

Data collection

Bruker X8 APEX Diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.670, T max = 0.746

12792 measured reflections

5605 independent reflections

4754 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.03

5605 reflections

253 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack & Bernardinelli (2000 ▶)

Absolute structure parameter: −0.04 (4)

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/S1600536814018492/su2771sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018492/su2771Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018492/su2771Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018492/su2771fig1.tif

A view of the mol­ecular structure of the title mol­ecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814018492/su2771fig2.tif

A partial view of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1019238

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

C19H20ClN3O4S	F(000) = 440
Mr = 421.89	Dx = 1.377 Mg m−3
Monoclinic, P21	Melting point: 397 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 8.2699 (7) Å	Cell parameters from 5605 reflections
b = 13.1235 (12) Å	θ = 2.6–29.6°
c = 10.0026 (9) Å	µ = 0.32 mm−1
β = 110.379 (5)°	T = 296 K
V = 1017.64 (16) Å3	Prism, colourless
Z = 2	0.42 × 0.32 × 0.28 mm

Bruker X8 APEX Diffractometer	5605 independent reflections
Radiation source: fine-focus sealed tube	4754 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 29.6°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −11→11
Tmin = 0.670, Tmax = 0.746	k = −18→18
12792 measured reflections	l = −12→13

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.0481P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
5605 reflections	Δρmax = 0.18 e Å−3
253 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: Flack & Bernardinelli (2000)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (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
C1	0.5375 (4)	0.8680 (4)	0.9417 (3)	0.1124 (13)
H1A	0.6182	0.8159	0.9577	0.135*
H1B	0.5344	0.9084	1.0173	0.135*
C2	0.4301 (3)	0.8844 (2)	0.8151 (3)	0.0706 (7)
H2	0.3506	0.9370	0.8018	0.085*
C3	0.4268 (2)	0.82350 (16)	0.6893 (2)	0.0519 (4)
H3A	0.4629	0.8663	0.6257	0.062*
H3B	0.5089	0.7680	0.7206	0.062*
C4	0.0173 (2)	0.76621 (13)	0.43723 (18)	0.0438 (4)
C5	0.0066 (2)	0.69652 (13)	0.54239 (16)	0.0396 (3)
C6	0.1670 (2)	0.70913 (13)	0.65413 (18)	0.0411 (4)
C7	0.2124 (2)	0.65003 (15)	0.77993 (19)	0.0472 (4)
H7	0.3187	0.6575	0.8526	0.057*
C8	0.0936 (2)	0.58180 (14)	0.78968 (19)	0.0455 (4)
H8	0.1200	0.5420	0.8714	0.055*
C9	−0.0697 (2)	0.56870 (13)	0.68005 (17)	0.0387 (3)
C10	−0.1141 (2)	0.62525 (13)	0.55548 (17)	0.0389 (3)
C11	−0.4058 (3)	0.67175 (17)	0.4348 (2)	0.0595 (5)
H11A	−0.3680	0.7422	0.4467	0.071*
H11B	−0.4498	0.6548	0.5102	0.071*
C12	−0.5450 (3)	0.6575 (2)	0.2914 (3)	0.0826 (8)
H12A	−0.6410	0.7009	0.2846	0.124*
H12B	−0.5821	0.5877	0.2807	0.124*
H12C	−0.5006	0.6748	0.2176	0.124*
C13	−0.1432 (2)	0.47263 (13)	0.97527 (17)	0.0372 (3)
C14	−0.0709 (2)	0.37584 (14)	1.00480 (19)	0.0445 (4)
H14	−0.0998	0.3261	0.9342	0.053*
C15	0.0440 (2)	0.35386 (14)	1.1395 (2)	0.0472 (4)
H15	0.0936	0.2895	1.1594	0.057*
C16	0.0854 (2)	0.42823 (14)	1.24556 (18)	0.0412 (4)
C17	0.0108 (3)	0.52403 (15)	1.21696 (19)	0.0509 (5)
H17	0.0365	0.5732	1.2882	0.061*
C18	−0.1031 (2)	0.54584 (15)	1.08055 (19)	0.0472 (4)
H18	−0.1525	0.6103	1.0603	0.057*
C19	0.2358 (3)	0.4703 (2)	1.4897 (2)	0.0654 (6)
H19A	0.3188	0.4414	1.5739	0.098*
H19B	0.1310	0.4845	1.5071	0.098*
H19C	0.2808	0.5323	1.4656	0.098*
N1	0.25612 (19)	0.78146 (13)	0.61078 (16)	0.0475 (3)
H1N	−0.1966	0.4399	0.6454	0.057*
N2	0.1641 (2)	0.81619 (12)	0.47747 (17)	0.0487 (4)
N3	−0.18652 (19)	0.49314 (12)	0.69400 (14)	0.0450 (3)
O1	−0.26451 (16)	0.60654 (10)	0.44257 (13)	0.0492 (3)
O2	−0.3468 (2)	0.60356 (12)	0.80661 (15)	0.0631 (4)
O3	−0.41372 (18)	0.41918 (13)	0.76263 (15)	0.0663 (4)
O4	0.20127 (17)	0.39973 (12)	1.37445 (14)	0.0575 (4)
S1	−0.29029 (5)	0.50045 (3)	0.80328 (4)	0.04255 (11)
Cl1	−0.13391 (7)	0.78969 (4)	0.27168 (5)	0.06011 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0692 (16)	0.197 (4)	0.0710 (18)	−0.008 (2)	0.0241 (14)	−0.035 (2)
C2	0.0470 (11)	0.0776 (16)	0.0869 (16)	−0.0028 (11)	0.0230 (11)	−0.0236 (13)
C3	0.0415 (9)	0.0562 (11)	0.0615 (11)	−0.0034 (8)	0.0223 (8)	0.0045 (9)
C4	0.0545 (10)	0.0401 (10)	0.0375 (8)	0.0026 (8)	0.0168 (7)	0.0043 (7)
C5	0.0474 (9)	0.0380 (8)	0.0345 (7)	0.0047 (7)	0.0155 (6)	0.0034 (6)
C6	0.0436 (8)	0.0399 (9)	0.0415 (8)	0.0019 (7)	0.0169 (7)	0.0041 (7)
C7	0.0441 (9)	0.0529 (11)	0.0404 (8)	0.0016 (8)	0.0096 (7)	0.0075 (7)
C8	0.0517 (10)	0.0480 (10)	0.0367 (8)	0.0037 (8)	0.0154 (7)	0.0096 (7)
C9	0.0471 (9)	0.0340 (8)	0.0377 (8)	−0.0011 (7)	0.0184 (7)	−0.0012 (6)
C10	0.0460 (8)	0.0355 (8)	0.0343 (7)	0.0020 (7)	0.0129 (6)	−0.0020 (6)
C11	0.0527 (10)	0.0579 (12)	0.0599 (11)	0.0003 (10)	0.0097 (9)	−0.0046 (10)
C12	0.0651 (14)	0.0873 (19)	0.0745 (15)	−0.0002 (13)	−0.0023 (12)	0.0097 (14)
C13	0.0374 (7)	0.0407 (9)	0.0341 (7)	0.0006 (6)	0.0129 (6)	0.0056 (6)
C14	0.0526 (9)	0.0398 (9)	0.0398 (8)	0.0039 (8)	0.0145 (7)	−0.0014 (7)
C15	0.0530 (10)	0.0396 (9)	0.0487 (9)	0.0108 (8)	0.0171 (8)	0.0061 (7)
C16	0.0353 (7)	0.0475 (10)	0.0390 (8)	0.0030 (7)	0.0108 (6)	0.0053 (7)
C17	0.0548 (10)	0.0466 (11)	0.0424 (9)	0.0043 (8)	0.0057 (7)	−0.0067 (7)
C18	0.0532 (10)	0.0382 (9)	0.0447 (9)	0.0072 (7)	0.0100 (8)	0.0024 (7)
C19	0.0630 (12)	0.0784 (16)	0.0416 (10)	−0.0014 (11)	0.0013 (8)	0.0019 (10)
N1	0.0483 (7)	0.0480 (8)	0.0464 (8)	−0.0015 (7)	0.0169 (6)	0.0078 (7)
N2	0.0601 (9)	0.0433 (8)	0.0465 (8)	0.0024 (7)	0.0234 (7)	0.0091 (6)
N3	0.0608 (8)	0.0372 (7)	0.0419 (7)	−0.0087 (7)	0.0241 (6)	−0.0053 (6)
O1	0.0551 (7)	0.0475 (7)	0.0390 (6)	−0.0016 (6)	0.0089 (5)	−0.0066 (5)
O2	0.0731 (9)	0.0687 (10)	0.0497 (8)	0.0340 (8)	0.0242 (7)	0.0146 (7)
O3	0.0477 (7)	0.0917 (12)	0.0499 (8)	−0.0213 (8)	0.0049 (6)	0.0132 (8)
O4	0.0520 (7)	0.0689 (9)	0.0419 (6)	0.0142 (7)	0.0041 (5)	0.0047 (6)
S1	0.03950 (19)	0.0505 (2)	0.03584 (18)	0.00353 (19)	0.01090 (14)	0.00789 (17)
Cl1	0.0752 (3)	0.0580 (3)	0.0390 (2)	−0.0010 (2)	0.0097 (2)	0.0121 (2)

C1—C2	1.287 (4)	C11—H11B	0.9700
C1—H1A	0.9300	C12—H12A	0.9600
C1—H1B	0.9300	C12—H12B	0.9600
C2—C3	1.483 (3)	C12—H12C	0.9600
C2—H2	0.9300	C13—C18	1.378 (3)
C3—N1	1.463 (2)	C13—C14	1.391 (2)
C3—H3A	0.9700	C13—S1	1.7650 (16)
C3—H3B	0.9700	C14—C15	1.382 (2)
C4—N2	1.313 (2)	C14—H14	0.9300
C4—C5	1.420 (2)	C15—C16	1.393 (3)
C4—Cl1	1.7201 (17)	C15—H15	0.9300
C5—C10	1.407 (2)	C16—O4	1.3636 (19)
C5—C6	1.416 (2)	C16—C17	1.386 (3)
C6—N1	1.362 (2)	C17—C18	1.391 (2)
C6—C7	1.413 (2)	C17—H17	0.9300
C7—C8	1.358 (3)	C18—H18	0.9300
C7—H7	0.9300	C19—O4	1.428 (3)
C8—C9	1.423 (2)	C19—H19A	0.9600
C8—H8	0.9300	C19—H19B	0.9600
C9—C10	1.385 (2)	C19—H19C	0.9600
C9—N3	1.425 (2)	N1—N2	1.363 (2)
C10—O1	1.3801 (19)	N3—S1	1.6106 (14)
C11—O1	1.428 (2)	N3—H1N	0.8390
C11—C12	1.506 (3)	O2—S1	1.4358 (15)
C11—H11A	0.9700	O3—S1	1.4338 (15)
C2—C1—H1A	120.0	C11—C12—H12C	109.5
C2—C1—H1B	120.0	H12A—C12—H12C	109.5
H1A—C1—H1B	120.0	H12B—C12—H12C	109.5
C1—C2—C3	123.2 (3)	C18—C13—C14	120.21 (15)
C1—C2—H2	118.4	C18—C13—S1	120.10 (13)
C3—C2—H2	118.4	C14—C13—S1	119.68 (13)
N1—C3—C2	112.82 (16)	C15—C14—C13	119.75 (16)
N1—C3—H3A	109.0	C15—C14—H14	120.1
C2—C3—H3A	109.0	C13—C14—H14	120.1
N1—C3—H3B	109.0	C14—C15—C16	119.95 (16)
C2—C3—H3B	109.0	C14—C15—H15	120.0
H3A—C3—H3B	107.8	C16—C15—H15	120.0
N2—C4—C5	112.59 (15)	O4—C16—C17	124.04 (16)
N2—C4—Cl1	119.34 (13)	O4—C16—C15	115.67 (16)
C5—C4—Cl1	128.07 (14)	C17—C16—C15	120.29 (15)
C10—C5—C6	120.30 (15)	C16—C17—C18	119.33 (17)
C10—C5—C4	136.61 (15)	C16—C17—H17	120.3
C6—C5—C4	103.08 (15)	C18—C17—H17	120.3
N1—C6—C7	131.36 (16)	C13—C18—C17	120.43 (17)
N1—C6—C5	107.00 (15)	C13—C18—H18	119.8
C7—C6—C5	121.61 (16)	C17—C18—H18	119.8
C8—C7—C6	116.83 (15)	O4—C19—H19A	109.5
C8—C7—H7	121.6	O4—C19—H19B	109.5
C6—C7—H7	121.6	H19A—C19—H19B	109.5
C7—C8—C9	122.74 (16)	O4—C19—H19C	109.5
C7—C8—H8	118.6	H19A—C19—H19C	109.5
C9—C8—H8	118.6	H19B—C19—H19C	109.5
C10—C9—C8	120.76 (16)	C6—N1—N2	111.39 (14)
C10—C9—N3	119.00 (15)	C6—N1—C3	128.29 (16)
C8—C9—N3	120.16 (14)	N2—N1—C3	120.30 (16)
O1—C10—C9	121.44 (16)	C4—N2—N1	105.93 (14)
O1—C10—C5	120.56 (15)	C9—N3—S1	124.38 (12)
C9—C10—C5	117.75 (15)	C9—N3—H1N	117.2
O1—C11—C12	108.46 (19)	S1—N3—H1N	118.3
O1—C11—H11A	110.0	C10—O1—C11	115.14 (13)
C12—C11—H11A	110.0	C16—O4—C19	117.56 (16)
O1—C11—H11B	110.0	O3—S1—O2	120.14 (10)
C12—C11—H11B	110.0	O3—S1—N3	104.96 (9)
H11A—C11—H11B	108.4	O2—S1—N3	109.07 (8)
C11—C12—H12A	109.5	O3—S1—C13	107.67 (8)
C11—C12—H12B	109.5	O2—S1—C13	106.96 (8)
H12A—C12—H12B	109.5	N3—S1—C13	107.45 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N···N2i	0.84	2.11	2.931 (2)	166
C19—H19A···O3ii	0.96	2.37	3.285 (2)	159
C3—H3B···O2iii	0.97	2.47	3.418 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N⋯N2i	0.84	2.11	2.931 (2)	166
C19—H19A⋯O3ii	0.96	2.37	3.285 (2)	159
C3—H3B⋯O2iii	0.97	2.47	3.418 (3)	165

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