Crystal structure of N-(1-allyl-3-chloro-1H-indazol-5-yl)-4-methyl­benzene­sulfonamide

Chicha, H.; Rakib, E.M.; Chigr, M.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536814018194

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1041-o1042

doi:10.1107/S1600536814018194

Open

access

Crystal structure of N-(1-allyl-3-chloro-1H-indazol-5-yl)-4-methylbenzenesulfonamide

Hakima Chicha,^a El Mostapha Rakib,^a Mohamed Chigr,^a ^* Mohamed Saadi ^b and Lahcen El Ammari ^b

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: m_chigr@yahoo.fr

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 6 August 2014; accepted 7 August 2014; online 23 August 2014)

The 3-chloro-1H-indazole system in the title molecule, C₁₇H₁₆ClN₃O₂S, is almost planar, with the largest deviation from the mean plane being 0.029 (2) Å for one of the N atoms. This system is nearly perpendicular to the allyl chain, as indicated by the C—C—N—N torsion angle of −90.1 (6)° between them. The allyl group is split into two fragments, the major component has a site occupancy of 0.579 (7). The indazole system makes a dihedral angle of 47.53 (10)° with the plane through the benzene ring. In the crystal, molecules are connected by N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network.

Keywords: crystal structure; benzenesulfonamides; biological activity; hydrogen bonding.

CCDC reference: 1018456

1. Related literature

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

2. Experimental

2.1. Crystal data

C₁₇H₁₆ClN₃O₂S
M_r = 361.84
Orthorhombic, P b c n
a = 8.1736 (12) Å
b = 22.504 (4) Å
c = 19.279 (3) Å
V = 3546.2 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.40 × 0.36 × 0.31 mm

2.2. Data collection

Bruker X8 APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.693, T_max = 0.747
18362 measured reflections
3621 independent reflections
2327 reflections with I > 2σ(I)
R_int = 0.051

2.3. Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.123
S = 1.02
3621 reflections
225 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1ⁱ	0.81	2.39	3.140 (3)	155
C4—H4⋯O2ⁱⁱ	0.93	2.44	3.364 (3)	171
C5—H5⋯O1ⁱ	0.93	2.58	3.282 (3)	132
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) x+1, y, z.

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 ).

Supporting information

CCDC reference: 1018456

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814018194/tk5336sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018194/tk5336Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018194/tk5336Isup3.cml

checkCIF report

Structural commentary top

Sulfonamides are an important class of compounds which are widely used in the design of diverse classes of drug candidates (El-Sayed et al., 2011; Mustafa et al., 2012; Scozzafava et al., 2003). Previously, we identified a series of indazoles bearing a sulfonamide moiety with good antiproliferative activities (Abbassi et al., 2012; Abbassi, et al. 2013; Chicha et al., 2014).

The molecule of the title compound is built up from two fused five- and six-membered rings (N1 N2 C2 to C8) almost coplanar, with a maximum deviation of 0.029 (2) Å for N1 atom (Fig. 1). The dihedral angle between the indazol system and the plane through the benzene ring (C9 to C14) is of 47.53 (10)°. The allyl chain is perpendicular to the fused rings system as indicated by the C(16A)—C(15)—N(1)—N(2) torsion angle of -90.1 (6)°.

The cohesion of the crystal structure is ensured by N3–H3N···O1, C5–H5···O1 and C4–H4···O2 hydrogen bonds between molecules to form a three-dimensional network as shown in Fig. 2 and Table 1.

Synthesis and crystallization top

A mixture of 1-allyl-3-chloro-5-nitroindazole (1.22 mmol) and anhydrous SnCl₂ (1.1 g, 6.1 mmol) in 25 ml of absolute ethanol was heated at 333 K for 6 h. After reduction, the starting material disappeared, and the solution was allowed to cool down. The pH was made slightly basic (pH 7–8) by addition of 5% aqueous potassium bicarbonate before extraction with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate. The solvent was removed to afford the amine, which was immediately dissolved in pyridine (5 ml) and then reacted with 4-methylbenzenesulfonyl chloride (1.25 mmol) at room temperature for 24 h. After the reaction mixture was concentrated in vacuo, the resulting residue was purified by flash chromatography (eluted with ethyl acetate:hexane 2:8). The title compound was recrystallized from its ethanol solution. Yield: 65%, M.pt: 394 K.

Refinement top

The reflections (002), (110), (021) and (020), probably affected by the beam stop, were removed from the final refinement. The refinement of the model, i.e. disordered allyl group, required constraints on the distance C15—C16—C17 and atomic displacements of allyl group. The H atoms were located in a difference map and treated as riding with C—H = 0.96 Å, C—H = 0.97 Å, C—H = 0.93 Å, and N—H = 0.81 Å for methyl, methylene, aromatic CH and NH, respectively, and with U_iso(H) = 1.2 U_eq (methylene, aromatic, NH) and U_iso(H) = 1.5 U_eq for methyl.

Related literature top

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

	Fig. 1. Molecular structure 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.
	Fig. 2. Crystal structure of the title compound, showing molecules linked by N3–H3N···O1, C5–H5···O1 and C4–H4···O2 hydrogen bonds between molecules.

N-(1-Allyl-3-chloro-1H-indazol-5-yl)-4-methylbenzenesulfonamide top

Crystal data top

C₁₇H₁₆ClN₃O₂S	D_x = 1.355 Mg m⁻³
M_r = 361.84	Melting point: 394 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3621 reflections
a = 8.1736 (12) Å	θ = 2.8–26.4°
b = 22.504 (4) Å	µ = 0.35 mm⁻¹
c = 19.279 (3) Å	T = 296 K
V = 3546.2 (10) Å³	Block, colourless
Z = 8	0.40 × 0.36 × 0.31 mm
F(000) = 1504

Data collection top

Bruker X8 APEX diffractometer	3621 independent reflections
Radiation source: fine-focus sealed tube	2327 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −9→10
T_min = 0.693, T_max = 0.747	k = −28→26
18362 measured reflections	l = −22→24

Refinement top

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0557P)² + 0.7269P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3621 reflections	Δρ_max = 0.26 e Å⁻³
225 parameters	Δρ_min = −0.26 e Å⁻³
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0026 (4)

Crystal data top

C₁₇H₁₆ClN₃O₂S	V = 3546.2 (10) Å³
M_r = 361.84	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 8.1736 (12) Å	µ = 0.35 mm⁻¹
b = 22.504 (4) Å	T = 296 K
c = 19.279 (3) Å	0.40 × 0.36 × 0.31 mm

Data collection top

Bruker X8 APEX diffractometer	3621 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	2327 reflections with I > 2σ(I)
T_min = 0.693, T_max = 0.747	R_int = 0.051
18362 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	4 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.02	Δρ_max = 0.26 e Å⁻³
3621 reflections	Δρ_min = −0.26 e Å⁻³
225 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.8260 (3)	−0.03622 (11)	0.08181 (12)	0.0516 (6)
C2	0.8328 (3)	0.02554 (10)	0.06992 (11)	0.0427 (5)
C3	0.9964 (3)	0.04008 (11)	0.08496 (12)	0.0481 (6)
C4	1.0542 (3)	0.09849 (12)	0.07951 (13)	0.0570 (7)
H4	1.1624	0.1081	0.0892	0.068*
C5	0.9446 (3)	0.14053 (11)	0.05939 (13)	0.0532 (6)
H5	0.9793	0.1798	0.0558	0.064*
C6	0.7806 (3)	0.12692 (10)	0.04380 (11)	0.0444 (5)
C7	0.7233 (3)	0.06945 (10)	0.04817 (11)	0.0445 (6)
H7	0.6156	0.0602	0.0370	0.053*
C8	0.6222 (3)	0.22836 (11)	0.14802 (13)	0.0503 (6)
C9	0.6865 (3)	0.19241 (12)	0.19974 (14)	0.0628 (7)
H9	0.6795	0.1513	0.1961	0.075*
C10	0.7609 (4)	0.21805 (15)	0.25663 (15)	0.0741 (8)
H10	0.8063	0.1939	0.2907	0.089*
C11	0.7691 (4)	0.27915 (16)	0.26378 (16)	0.0756 (9)
C12	0.7046 (4)	0.31338 (14)	0.21193 (19)	0.0830 (10)
H12	0.7097	0.3545	0.2162	0.100*
C13	0.6321 (3)	0.28965 (12)	0.15350 (16)	0.0669 (8)
H13	0.5911	0.3141	0.1187	0.080*
C14	0.8448 (5)	0.3061 (2)	0.32849 (19)	0.1179 (15)
H14A	0.8818	0.2750	0.3586	0.177*
H14B	0.7645	0.3298	0.3521	0.177*
H14C	0.9358	0.3307	0.3156	0.177*
C15	1.2392 (3)	−0.01960 (14)	0.12649 (15)	0.0755 (9)
H15A	1.3111	0.0081	0.1029	0.091*
H15B	1.2767	−0.0597	0.1172	0.091*
C16A	1.2386 (8)	−0.0080 (6)	0.2012 (2)	0.0902 (19)	0.579 (7)
H16A	1.1739	−0.0334	0.2276	0.108*	0.579 (7)
C17A	1.3154 (12)	0.0324 (4)	0.2354 (5)	0.120 (2)	0.579 (7)
H17A	1.3823	0.0593	0.2122	0.144*	0.579 (7)
H17B	1.3039	0.0348	0.2833	0.144*	0.579 (7)
C16B	1.2961 (13)	−0.0101 (9)	0.1975 (3)	0.0902 (19)	0.421 (7)
H16B	1.3979	−0.0238	0.2119	0.108*	0.421 (7)
C17B	1.2008 (15)	0.0178 (6)	0.2393 (6)	0.120 (2)	0.421 (7)
H17C	1.0994	0.0312	0.2241	0.144*	0.421 (7)
H17D	1.2333	0.0246	0.2849	0.144*	0.421 (7)
N1	1.0722 (2)	−0.01207 (10)	0.10293 (11)	0.0576 (6)
N2	0.9665 (3)	−0.05905 (9)	0.10217 (11)	0.0593 (6)
N3	0.6711 (2)	0.17352 (9)	0.02206 (10)	0.0510 (5)
H3N	0.7140	0.2027	0.0059	0.061*
O1	0.4373 (2)	0.24036 (8)	0.03876 (10)	0.0743 (6)
O2	0.44423 (19)	0.14312 (8)	0.09892 (10)	0.0613 (5)
S1	0.52632 (7)	0.19552 (3)	0.07563 (3)	0.0508 (2)
Cl1	0.65782 (9)	−0.08137 (3)	0.07145 (5)	0.0776 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0444 (14)	0.0511 (15)	0.0591 (16)	0.0037 (11)	−0.0066 (12)	−0.0015 (11)
C2	0.0360 (12)	0.0497 (14)	0.0424 (12)	0.0002 (10)	−0.0015 (10)	−0.0025 (10)
C3	0.0361 (13)	0.0595 (15)	0.0486 (14)	0.0021 (11)	−0.0009 (10)	−0.0027 (11)
C4	0.0324 (13)	0.0728 (18)	0.0659 (17)	−0.0071 (12)	−0.0022 (12)	−0.0017 (13)
C5	0.0449 (14)	0.0543 (15)	0.0605 (15)	−0.0097 (12)	0.0030 (12)	0.0020 (11)
C6	0.0380 (13)	0.0514 (14)	0.0437 (13)	−0.0018 (11)	0.0008 (10)	0.0035 (10)
C7	0.0326 (12)	0.0537 (15)	0.0471 (13)	−0.0013 (10)	−0.0013 (10)	−0.0012 (10)
C8	0.0372 (13)	0.0534 (16)	0.0603 (16)	−0.0031 (11)	0.0080 (11)	0.0041 (11)
C9	0.0652 (18)	0.0606 (17)	0.0625 (17)	−0.0024 (14)	0.0008 (14)	0.0087 (13)
C10	0.0681 (19)	0.099 (2)	0.0556 (17)	−0.0019 (18)	0.0005 (15)	0.0061 (16)
C11	0.0620 (18)	0.102 (3)	0.0632 (19)	−0.0170 (18)	0.0130 (16)	−0.0167 (17)
C12	0.094 (2)	0.064 (2)	0.090 (2)	−0.0176 (18)	0.006 (2)	−0.0170 (17)
C13	0.0691 (18)	0.0497 (16)	0.082 (2)	−0.0021 (14)	0.0029 (16)	0.0027 (13)
C14	0.113 (3)	0.162 (4)	0.078 (2)	−0.028 (3)	0.007 (2)	−0.041 (2)
C15	0.0471 (15)	0.094 (2)	0.086 (2)	0.0195 (15)	−0.0203 (15)	−0.0028 (16)
C16A	0.051 (5)	0.108 (3)	0.112 (3)	0.026 (6)	−0.053 (3)	−0.003 (3)
C17A	0.125 (7)	0.150 (6)	0.085 (4)	−0.008 (6)	−0.019 (5)	−0.002 (4)
C16B	0.051 (5)	0.108 (3)	0.112 (3)	0.026 (6)	−0.053 (3)	−0.003 (3)
C17B	0.125 (7)	0.150 (6)	0.085 (4)	−0.008 (6)	−0.019 (5)	−0.002 (4)
N1	0.0400 (11)	0.0674 (15)	0.0655 (14)	0.0090 (11)	−0.0081 (10)	−0.0028 (11)
N2	0.0556 (13)	0.0575 (13)	0.0649 (14)	0.0090 (12)	−0.0079 (11)	−0.0014 (10)
N3	0.0487 (12)	0.0504 (12)	0.0540 (12)	−0.0004 (9)	0.0008 (10)	0.0125 (9)
O1	0.0602 (12)	0.0682 (12)	0.0945 (14)	0.0180 (10)	−0.0207 (11)	0.0137 (10)
O2	0.0408 (9)	0.0583 (11)	0.0848 (12)	−0.0107 (8)	0.0069 (9)	0.0003 (9)
S1	0.0372 (3)	0.0478 (4)	0.0673 (4)	0.0015 (3)	−0.0050 (3)	0.0078 (3)
Cl1	0.0639 (5)	0.0553 (4)	0.1137 (7)	−0.0094 (3)	−0.0186 (4)	0.0066 (4)

Geometric parameters (Å, º) top

C1—N2	1.318 (3)	C12—H12	0.9300
C1—C2	1.410 (3)	C13—H13	0.9300
C1—Cl1	1.721 (3)	C14—H14A	0.9600
C2—C7	1.398 (3)	C14—H14B	0.9600
C2—C3	1.407 (3)	C14—H14C	0.9600
C3—N1	1.371 (3)	C15—N1	1.448 (3)
C3—C4	1.400 (3)	C15—C16B	1.461 (2)
C4—C5	1.359 (3)	C15—C16A	1.464 (2)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.407 (3)	C15—H15B	0.9700
C5—H5	0.9300	C16A—C17A	1.286 (2)
C6—C7	1.378 (3)	C16A—H16A	0.9300
C6—N3	1.441 (3)	C17A—H17A	0.9300
C7—H7	0.9300	C17A—H17B	0.9300
C8—C13	1.386 (3)	C16B—C17B	1.286 (2)
C8—C9	1.387 (3)	C16B—H16B	0.9300
C8—S1	1.763 (3)	C17B—H17C	0.9300
C9—C10	1.381 (4)	C17B—H17D	0.9300
C9—H9	0.9300	N1—N2	1.366 (3)
C10—C11	1.384 (4)	N3—S1	1.647 (2)
C10—H10	0.9300	N3—H3N	0.8060
C11—C12	1.368 (5)	O1—S1	1.4329 (18)
C11—C14	1.519 (4)	O2—S1	1.4291 (17)
C12—C13	1.380 (4)

N2—C1—C2	113.4 (2)	C11—C14—H14B	109.5
N2—C1—Cl1	120.0 (2)	H14A—C14—H14B	109.5
C2—C1—Cl1	126.52 (19)	C11—C14—H14C	109.5
C7—C2—C3	120.4 (2)	H14A—C14—H14C	109.5
C7—C2—C1	136.1 (2)	H14B—C14—H14C	109.5
C3—C2—C1	103.5 (2)	N1—C15—C16B	125.2 (5)
N1—C3—C4	132.1 (2)	N1—C15—C16A	106.5 (3)
N1—C3—C2	106.4 (2)	C16B—C15—C16A	18.8 (5)
C4—C3—C2	121.5 (2)	N1—C15—H15A	110.4
C5—C4—C3	116.9 (2)	C16B—C15—H15A	98.8
C5—C4—H4	121.5	C16A—C15—H15A	110.4
C3—C4—H4	121.5	N1—C15—H15B	110.4
C4—C5—C6	122.5 (2)	C16B—C15—H15B	102.0
C4—C5—H5	118.8	C16A—C15—H15B	110.4
C6—C5—H5	118.8	H15A—C15—H15B	108.6
C7—C6—C5	121.0 (2)	C17A—C16A—C15	128.9 (8)
C7—C6—N3	119.3 (2)	C17A—C16A—H16A	115.5
C5—C6—N3	119.7 (2)	C15—C16A—H16A	115.5
C6—C7—C2	117.6 (2)	C16A—C17A—H17A	120.0
C6—C7—H7	121.2	C16A—C17A—H17B	120.0
C2—C7—H7	121.2	H17A—C17A—H17B	120.0
C13—C8—C9	120.2 (3)	C17B—C16B—C15	117.8 (10)
C13—C8—S1	120.3 (2)	C17B—C16B—H16B	121.1
C9—C8—S1	119.5 (2)	C15—C16B—H16B	121.1
C10—C9—C8	119.6 (3)	C16B—C17B—H17C	120.0
C10—C9—H9	120.2	C16B—C17B—H17D	120.0
C8—C9—H9	120.2	H17C—C17B—H17D	120.0
C9—C10—C11	121.1 (3)	N2—N1—C3	111.97 (18)
C9—C10—H10	119.5	N2—N1—C15	120.6 (2)
C11—C10—H10	119.5	C3—N1—C15	127.2 (2)
C12—C11—C10	117.9 (3)	C1—N2—N1	104.6 (2)
C12—C11—C14	122.2 (3)	C6—N3—S1	118.87 (15)
C10—C11—C14	119.9 (3)	C6—N3—H3N	115.8
C11—C12—C13	123.0 (3)	S1—N3—H3N	108.1
C11—C12—H12	118.5	O2—S1—O1	119.90 (11)
C13—C12—H12	118.5	O2—S1—N3	106.65 (10)
C12—C13—C8	118.2 (3)	O1—S1—N3	105.41 (11)
C12—C13—H13	120.9	O2—S1—C8	107.81 (11)
C8—C13—H13	120.9	O1—S1—C8	108.85 (12)
C11—C14—H14A	109.5	N3—S1—C8	107.64 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.81	2.39	3.140 (3)	155
C4—H4···O2ⁱⁱ	0.93	2.44	3.364 (3)	171
C5—H5···O1ⁱ	0.93	2.58	3.282 (3)	132

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.81	2.39	3.140 (3)	155.1
C4—H4···O2ⁱⁱ	0.93	2.44	3.364 (3)	171.1
C5—H5···O1ⁱ	0.93	2.58	3.282 (3)	132.3

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x+1, y, z.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements, and the University Sultan Moulay Slimane, Beni-Mellal, Morocco, for financial support.

References

Abbassi, N., Chicha, H., Rakib, E. M., Hannioui, A., Alaoui, M., Hajjaji, A., Geffken, D., Aiello, C., Gangemi, R., Rosano, C. & Viale, M. (2012). Eur. J. Med. Chem. 57, 240–249. Web of Science CrossRef CAS PubMed Google Scholar
Abbassi, N., Rakib, E. M., Hannioui, A., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o190–o191. CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chicha, H., Rakib, E. M., Amiri, O., Saadi, M. & El Ammari, L. (2014). Acta Cryst. E70, o181. CSD CrossRef IUCr Journals Google Scholar
El-Sayed, N. S., El-Bendary, E. R., El-Ashry, S. M. & El-Kerdawy, M. M. (2011). Eur. J. Med. Chem. 46, 3714–3720. Web of Science CAS PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mustafa, G., Khan, I. U., Ashraf, M., Afzal, I., Shahzad, S. A. & Shafiq, M. (2012). Bioorg. Med. Chem. 20, 2535–2539. Web of Science CrossRef CAS PubMed Google Scholar
Scozzafava, A., Owa, T., Mastrolorenzo, A. & Supuran, C. T. (2003). Curr. Med. Chem. 10, 925–953. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1041-o1042

doi:10.1107/S1600536814018194

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of N-(1-allyl-3-chloro-1H-indazol-5-yl)-4-methyl­benzene­sulfonamide

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of N-(1-allyl-3-chloro-1H-indazol-5-yl)-4-methylbenzenesulfonamide