Crystal structure of N-(1-acetyl-3-chloro-1H-indazol-6-yl)-4-meth-oxy-benzene-sulfonamide.

In the title compound, C16H14ClN3O4S, the six-membered ring of the indazole group is connected to a sulfonamide group. The indazole system is essentially planar, with the greatest deviation from the mean plane being 0.007 (2) Å. The dihedral angle between the two six-membered rings is 74.99 (9)°. The crystal structure exhibits inversion dimers in which mol-ecules are linked by pairs of N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For biological activities of indazole derivatives, see: Gaikwad et al. (2015 ▸); Jennings & Tennant (2007 ▸). For related derivatives, see: Abbassi et al. (2012 ▸, 2014 ▸); Bouissane et al. (2006 ▸).

Experimental

Crystal data

C16H14ClN3O4S

M = 379.81

Monoclinic,

a = 13.9664 (6) Å

b = 6.4300 (3) Å

c = 19.6155 (9) Å

β = 107.227 (1)°

V = 1682.52 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 296 K

0.31 × 0.27 × 0.21 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.654, T max = 0.747

33806 measured reflections

4461 independent reflections

3423 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.130

S = 1.09

4461 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.35 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: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▸) and ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015020605/tk5402sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020605/tk5402Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020605/tk5402Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015020605/tk5402fig1.tif

Plot of the mol­ecule of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

Click here for additional data file.

C . DOI: 10.1107/S2056989015020605/tk5402fig2.tif

Partial plot of the mol­ecular packing in the title compound, showing inversion dimers of mol­ecules linked through N1—H1⋯O1 (dashed lines) and C15—H15C⋯O2 hydrogen bonds.

CCDC reference: 1434410

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

C16H14ClN3O4S	Dx = 1.499 Mg m−3
Mr = 379.81	Melting point: 388 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.9664 (6) Å	Cell parameters from 4461 reflections
b = 6.4300 (3) Å	θ = 3.0–29.0°
c = 19.6155 (9) Å	µ = 0.38 mm−1
β = 107.227 (1)°	T = 296 K
V = 1682.52 (13) Å3	Block, colourless
Z = 4	0.31 × 0.27 × 0.21 mm
F(000) = 784

Bruker X8 APEX diffractometer	4461 independent reflections
Radiation source: fine-focus sealed tube	3423 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 29.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→19
Tmin = 0.654, Tmax = 0.747	k = −8→8
33806 measured reflections	l = −26→26

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0695P)2 + 0.2697P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
4461 reflections	Δρmax = 0.34 e Å−3
227 parameters	Δρmin = −0.35 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.

	x	y	z	Uiso*/Ueq
C1	0.91669 (11)	0.2704 (2)	0.37321 (8)	0.0452 (3)
C2	0.89374 (16)	0.1193 (3)	0.41556 (10)	0.0617 (5)
H2	0.9006	−0.0205	0.4058	0.074*
C3	0.86020 (16)	0.1769 (3)	0.47309 (10)	0.0602 (5)
H3	0.8448	0.0755	0.5020	0.072*
C4	0.85003 (11)	0.3830 (2)	0.48700 (8)	0.0408 (3)
C5	0.87624 (15)	0.5333 (3)	0.44499 (10)	0.0550 (4)
H5	0.8712	0.6734	0.4551	0.066*
C6	0.90957 (15)	0.4760 (3)	0.38864 (10)	0.0557 (4)
H6	0.9274	0.5773	0.3608	0.067*
C7	0.61586 (12)	0.4460 (3)	0.47134 (9)	0.0473 (4)
C8	0.53586 (11)	0.3118 (3)	0.44493 (8)	0.0441 (3)
H8	0.5300	0.1886	0.4682	0.053*
C9	0.46477 (11)	0.3708 (2)	0.38180 (8)	0.0446 (3)
C10	0.47468 (13)	0.5525 (3)	0.34520 (9)	0.0516 (4)
C11	0.55490 (14)	0.6856 (3)	0.37318 (12)	0.0617 (5)
H11	0.5613	0.8077	0.3495	0.074*
C12	0.62455 (14)	0.6340 (3)	0.43640 (11)	0.0601 (4)
H12	0.6779	0.7234	0.4564	0.072*
C13	0.39023 (14)	0.5496 (3)	0.28361 (10)	0.0573 (4)
C14	0.32896 (13)	0.0995 (3)	0.35643 (9)	0.0507 (4)
C15	0.22920 (16)	0.0485 (3)	0.30602 (11)	0.0669 (5)
H15A	0.2340	0.0443	0.2582	0.100*
H15B	0.1816	0.1529	0.3092	0.100*
H15C	0.2076	−0.0846	0.3181	0.100*
C16	0.95084 (18)	0.0198 (3)	0.29354 (11)	0.0681 (5)
H16A	0.9737	0.0148	0.2520	0.102*
H16B	0.9962	−0.0572	0.3315	0.102*
H16C	0.8851	−0.0402	0.2826	0.102*
N1	0.68799 (10)	0.3907 (3)	0.53612 (7)	0.0528 (3)
H1	0.6685	0.3165	0.5660	0.063*
N2	0.37631 (11)	0.2767 (2)	0.34114 (7)	0.0500 (3)
N3	0.33132 (12)	0.3908 (3)	0.27965 (8)	0.0582 (4)
O1	0.37051 (10)	−0.0002 (2)	0.40987 (7)	0.0588 (3)
O2	0.85332 (9)	0.3360 (2)	0.61953 (6)	0.0641 (4)
O3	0.81333 (11)	0.6802 (2)	0.56320 (8)	0.0681 (4)
O4	0.94732 (10)	0.2289 (2)	0.31491 (7)	0.0593 (3)
S1	0.80653 (3)	0.45883 (7)	0.55819 (2)	0.04892 (14)
Cl1	0.36508 (5)	0.72884 (10)	0.21588 (3)	0.0859 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0407 (8)	0.0515 (8)	0.0423 (8)	−0.0026 (6)	0.0104 (6)	0.0070 (6)
C2	0.0916 (14)	0.0368 (8)	0.0669 (11)	0.0011 (8)	0.0390 (10)	0.0044 (7)
C3	0.0858 (14)	0.0418 (8)	0.0645 (11)	−0.0039 (8)	0.0400 (10)	0.0088 (7)
C4	0.0355 (7)	0.0432 (7)	0.0427 (7)	−0.0029 (6)	0.0101 (6)	0.0004 (6)
C5	0.0692 (11)	0.0384 (8)	0.0621 (10)	−0.0086 (7)	0.0265 (9)	0.0016 (7)
C6	0.0703 (11)	0.0455 (8)	0.0564 (10)	−0.0113 (8)	0.0268 (9)	0.0078 (7)
C7	0.0397 (8)	0.0540 (9)	0.0529 (9)	0.0037 (6)	0.0209 (7)	−0.0007 (7)
C8	0.0424 (8)	0.0491 (8)	0.0444 (8)	0.0034 (6)	0.0183 (6)	0.0020 (6)
C9	0.0413 (8)	0.0500 (8)	0.0473 (8)	0.0052 (6)	0.0203 (6)	0.0007 (6)
C10	0.0481 (9)	0.0563 (9)	0.0561 (9)	0.0108 (7)	0.0242 (8)	0.0105 (7)
C11	0.0542 (10)	0.0554 (10)	0.0804 (13)	0.0032 (8)	0.0271 (9)	0.0182 (9)
C12	0.0471 (9)	0.0587 (10)	0.0758 (12)	−0.0038 (8)	0.0202 (9)	0.0073 (9)
C13	0.0558 (10)	0.0662 (11)	0.0544 (9)	0.0142 (8)	0.0231 (8)	0.0173 (8)
C14	0.0497 (9)	0.0546 (9)	0.0463 (8)	0.0004 (7)	0.0118 (7)	−0.0034 (7)
C15	0.0639 (12)	0.0710 (12)	0.0545 (10)	−0.0106 (9)	0.0002 (9)	−0.0021 (9)
C16	0.0777 (13)	0.0725 (12)	0.0595 (11)	0.0117 (10)	0.0288 (10)	−0.0048 (9)
N1	0.0420 (7)	0.0696 (9)	0.0487 (7)	−0.0057 (6)	0.0165 (6)	0.0042 (6)
N2	0.0498 (7)	0.0563 (8)	0.0420 (7)	0.0026 (6)	0.0107 (6)	0.0055 (6)
N3	0.0568 (9)	0.0696 (10)	0.0468 (8)	0.0097 (7)	0.0132 (7)	0.0115 (7)
O1	0.0532 (7)	0.0599 (7)	0.0572 (7)	−0.0037 (6)	0.0068 (6)	0.0094 (6)
O2	0.0522 (7)	0.0939 (10)	0.0416 (6)	−0.0115 (7)	0.0070 (5)	0.0031 (6)
O3	0.0687 (8)	0.0608 (8)	0.0779 (9)	−0.0131 (6)	0.0264 (7)	−0.0248 (7)
O4	0.0719 (8)	0.0625 (7)	0.0502 (7)	−0.0038 (6)	0.0286 (6)	0.0018 (5)
S1	0.0440 (2)	0.0576 (3)	0.0458 (2)	−0.00842 (17)	0.01419 (17)	−0.00832 (17)
Cl1	0.0821 (4)	0.0971 (4)	0.0790 (4)	0.0150 (3)	0.0247 (3)	0.0444 (3)

C1—O4	1.361 (2)	C11—C12	1.371 (3)
C1—C6	1.366 (2)	C11—H11	0.9300
C1—C2	1.376 (2)	C12—H12	0.9300
C2—C3	1.394 (3)	C13—N3	1.299 (3)
C2—H2	0.9300	C13—Cl1	1.7146 (18)
C3—C4	1.369 (2)	C14—O1	1.219 (2)
C3—H3	0.9300	C14—N2	1.394 (2)
C4—C5	1.388 (2)	C14—C15	1.487 (2)
C4—S1	1.7490 (16)	C15—H15A	0.9600
C5—C6	1.371 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300	C16—O4	1.414 (2)
C7—C8	1.385 (2)	C16—H16A	0.9600
C7—C12	1.413 (2)	C16—H16B	0.9600
C7—N1	1.413 (2)	C16—H16C	0.9600
C8—C9	1.391 (2)	N1—S1	1.6419 (14)
C8—H8	0.9300	N1—H1	0.8600
C9—N2	1.395 (2)	N2—N3	1.3924 (19)
C9—C10	1.399 (2)	O2—S1	1.4257 (14)
C10—C11	1.388 (3)	O3—S1	1.4279 (14)
C10—C13	1.417 (3)
O4—C1—C6	115.95 (14)	C11—C12—H12	119.8
O4—C1—C2	123.80 (16)	C7—C12—H12	119.8
C6—C1—C2	120.25 (16)	N3—C13—C10	114.44 (15)
C1—C2—C3	119.71 (16)	N3—C13—Cl1	120.08 (15)
C1—C2—H2	120.1	C10—C13—Cl1	125.44 (15)
C3—C2—H2	120.1	O1—C14—N2	118.65 (15)
C4—C3—C2	119.87 (15)	O1—C14—C15	124.73 (17)
C4—C3—H3	120.1	N2—C14—C15	116.61 (15)
C2—C3—H3	120.1	C14—C15—H15A	109.5
C3—C4—C5	119.64 (15)	C14—C15—H15B	109.5
C3—C4—S1	120.68 (12)	H15A—C15—H15B	109.5
C5—C4—S1	119.68 (13)	C14—C15—H15C	109.5
C6—C5—C4	120.27 (16)	H15A—C15—H15C	109.5
C6—C5—H5	119.9	H15B—C15—H15C	109.5
C4—C5—H5	119.9	O4—C16—H16A	109.5
C1—C6—C5	120.20 (15)	O4—C16—H16B	109.5
C1—C6—H6	119.9	H16A—C16—H16B	109.5
C5—C6—H6	119.9	O4—C16—H16C	109.5
C8—C7—C12	121.82 (16)	H16A—C16—H16C	109.5
C8—C7—N1	117.46 (15)	H16B—C16—H16C	109.5
C12—C7—N1	120.70 (16)	C7—N1—S1	124.38 (12)
C7—C8—C9	116.57 (15)	C7—N1—H1	117.8
C7—C8—H8	121.7	S1—N1—H1	117.8
C9—C8—H8	121.7	N3—N2—C14	119.73 (14)
C8—C9—N2	131.97 (15)	N3—N2—C9	111.28 (14)
C8—C9—C10	122.10 (16)	C14—N2—C9	128.90 (13)
N2—C9—C10	105.92 (14)	C13—N3—N2	104.30 (15)
C11—C10—C9	120.21 (16)	C1—O4—C16	118.88 (14)
C11—C10—C13	135.73 (17)	O2—S1—O3	119.31 (9)
C9—C10—C13	104.05 (16)	O2—S1—N1	104.43 (8)
C12—C11—C10	118.81 (17)	O3—S1—N1	108.98 (9)
C12—C11—H11	120.6	O2—S1—C4	109.79 (8)
C10—C11—H11	120.6	O3—S1—C4	107.52 (8)
C11—C12—C7	120.40 (17)	N1—S1—C4	106.07 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.19	2.934 (2)	144
C15—H15C···O2i	0.96	2.33	3.251 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.19	2.934 (2)	144
C15—H15C⋯O2i	0.96	2.33	3.251 (3)	159

Symmetry code: (i) .