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

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

doi:10.1107/S1600536814010253

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o653

doi:10.1107/S1600536814010253

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

Hakima Chicha,^a El Mostapha Rakib,^a Latifa Bouissane,^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: l_bouissane@yahoo.fr

Edited by M. Bolte, Goethe-Universität Frankfurt Germany (Received 1 May 2014; accepted 6 May 2014; online 10 May 2014)

In the title compound, C₁₉H₂₀ClN₃O₃S, the benzene ring is inclined to the indazole ring system by 51.23 (8)°. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers which stack in columns parallel to [011]. The atoms in the allyl group are disordered over two sets of sites with an occupancy ratio of 0.624 (8):0.376 (8).

CCDC reference: 1001396

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

C₁₉H₂₀ClN₃O₃S
M_r = 405.89
Triclinic, $[P \overline 1]$
a = 10.0345 (2) Å
b = 10.5208 (2) Å
c = 10.7237 (2) Å
α = 71.561 (1)°
β = 69.601 (1)°
γ = 83.039 (1)°
V = 1006.56 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.42 × 0.35 × 0.30 mm

Data collection

Bruker X8 APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.693, T_max = 0.747
21411 measured reflections
4792 independent reflections
3967 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.126
S = 1.04
4792 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O3ⁱ	0.89	2.22	3.0588 (17)	156
Symmetry code: (i) -x+1, -y, -z+2.

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: 1001396

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814010253/bt6978sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010253/bt6978Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814010253/bt6978Isup3.cml

checkCIF report

Comment 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; Bouissane, et al., 2006). Previously, we identified a series of indazoles bearing a sulfonamide moiety with good antiproliferative activities. Recently, some N-[7(6)-indazolyl]arylsulfonamides prepared by our research group showed important antiproliferative activity against some human and murine cell lines (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 C1 to C7) almost coplanar, with a maximum deviation of -0.036 (2) Å for C5 atom (Fig.1). The indazol system forms a dihedral angle of 51.23 (8)° with the plane through the benzene ring and it is nearly perpendicular to the allyl group as indicated by the torsion angle C18B–C17–N2–N1 of 95.4 (5)°.

The cohesion of the crystal structure is ensured by N3–H3N···O3 hydrogen bonds between molecules forming a dimers, arranged in columns parallel to the [0 1 1] direction as shown in Fig.2 and Table 1.

Related literature top

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 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 ethanol (yield = 40%, m.p. = 373 K).

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. Projection of the crystal structure along a axix, showing molecules linked by hydrogen bonds and forming a dimers columns parallel to the [0 1 1] direction.

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

Crystal data top

C₁₉H₂₀ClN₃O₃S	Z = 2
M_r = 405.89	F(000) = 424
Triclinic, P1	D_x = 1.339 Mg m⁻³
Hall symbol: -P 1	Melting point: 373 K
a = 10.0345 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5208 (2) Å	Cell parameters from 4792 reflections
c = 10.7237 (2) Å	θ = 2.5–27.9°
α = 71.561 (1)°	µ = 0.32 mm⁻¹
β = 69.601 (1)°	T = 296 K
γ = 83.039 (1)°	Block, colourless
V = 1006.56 (3) Å³	0.42 × 0.35 × 0.30 mm

Data collection top

Bruker X8 APEX diffractometer	4792 independent reflections
Radiation source: fine-focus sealed tube	3967 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.693, T_max = 0.747	k = −13→13
21411 measured reflections	l = −14→13

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0687P)² + 0.2408P] where P = (F_o² + 2F_c²)/3
4792 reflections	(Δ/σ)_max = 0.001
263 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₉H₂₀ClN₃O₃S	γ = 83.039 (1)°
M_r = 405.89	V = 1006.56 (3) Å³
Triclinic, P1	Z = 2
a = 10.0345 (2) Å	Mo Kα radiation
b = 10.5208 (2) Å	µ = 0.32 mm⁻¹
c = 10.7237 (2) Å	T = 296 K
α = 71.561 (1)°	0.42 × 0.35 × 0.30 mm
β = 69.601 (1)°

Data collection top

Bruker X8 APEX diffractometer	4792 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3967 reflections with I > 2σ(I)
T_min = 0.693, T_max = 0.747	R_int = 0.027
21411 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	Δρ_max = 0.42 e Å⁻³
4792 reflections	Δρ_min = −0.35 e Å⁻³
263 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	0.8128 (2)	0.5118 (2)	0.42585 (19)	0.0628 (5)
C2	0.69725 (19)	0.46383 (17)	0.55054 (17)	0.0484 (4)
C3	0.6105 (2)	0.57806 (17)	0.55830 (18)	0.0526 (4)
C4	0.4795 (2)	0.57522 (17)	0.6626 (2)	0.0544 (4)
H4	0.4230	0.6519	0.6653	0.065*
C5	0.43792 (18)	0.45479 (17)	0.76086 (18)	0.0481 (4)
H5	0.3495	0.4488	0.8299	0.058*
C6	0.52561 (16)	0.33930 (15)	0.76030 (16)	0.0393 (3)
C7	0.65446 (17)	0.34152 (16)	0.65574 (16)	0.0415 (3)
C8	0.8599 (2)	0.2160 (2)	0.6873 (2)	0.0608 (5)
H8A	0.8369	0.2187	0.7821	0.073*
H8B	0.9213	0.2907	0.6252	0.073*
C9	0.9321 (3)	0.0880 (3)	0.6722 (4)	0.0976 (9)
H9A	0.9546	0.0866	0.5780	0.146*
H9B	0.8705	0.0149	0.7343	0.146*
H9C	1.0181	0.0796	0.6945	0.146*
C10	0.62203 (17)	0.22040 (15)	1.03861 (15)	0.0404 (3)
C11	0.7030 (2)	0.10747 (17)	1.0730 (2)	0.0542 (4)
H11	0.6664	0.0226	1.0973	0.065*
C12	0.8389 (2)	0.1218 (2)	1.0708 (2)	0.0618 (5)
H12	0.8932	0.0457	1.0949	0.074*
C13	0.8960 (2)	0.2475 (2)	1.0333 (2)	0.0570 (4)
C14	0.8130 (2)	0.35895 (19)	0.9984 (2)	0.0586 (5)
H14	0.8502	0.4438	0.9724	0.070*
C15	0.67618 (19)	0.34768 (16)	1.00100 (19)	0.0510 (4)
H15	0.6214	0.4237	0.9781	0.061*
C16	1.0466 (2)	0.2623 (3)	1.0261 (3)	0.0839 (7)
H16A	1.0877	0.1752	1.0543	0.126*
H16B	1.0460	0.3125	1.0870	0.126*
H16C	1.1017	0.3086	0.9323	0.126*
C17	0.6318 (3)	0.8191 (2)	0.4084 (3)	0.0869 (8)
H17A	0.5322	0.8251	0.4162	0.104*	0.376 (8)
H17B	0.6870	0.8653	0.3133	0.104*	0.376 (8)
H17C	0.6737	0.8565	0.3084	0.104*	0.624 (8)
H17D	0.5295	0.8209	0.4297	0.104*	0.624 (8)
C18A	0.657 (2)	0.8881 (16)	0.5179 (15)	0.082 (4)	0.376 (8)
H18A	0.6423	0.8383	0.6103	0.099*	0.376 (8)
C19A	0.6994 (8)	1.0147 (9)	0.4734 (11)	0.105 (4)	0.376 (8)
H19A	0.7144	1.0645	0.3810	0.126*	0.376 (8)
H19B	0.7136	1.0533	0.5346	0.126*	0.376 (8)
C18B	0.6631 (11)	0.9034 (11)	0.4701 (8)	0.076 (2)	0.624 (8)
H18B	0.6512	0.9951	0.4335	0.091*	0.624 (8)
C19B	0.7085 (7)	0.8617 (7)	0.5769 (6)	0.109 (2)	0.624 (8)
H19C	0.7214	0.7705	0.6156	0.131*	0.624 (8)
H19D	0.7279	0.9232	0.6141	0.131*	0.624 (8)
N1	0.8009 (2)	0.6396 (2)	0.36458 (18)	0.0738 (5)
N2	0.6767 (2)	0.68077 (16)	0.44501 (18)	0.0663 (5)
N3	0.47799 (13)	0.21562 (12)	0.86652 (13)	0.0403 (3)
H3N	0.5266	0.1437	0.8473	0.048*
O1	0.73089 (12)	0.22498 (12)	0.65275 (13)	0.0491 (3)
O2	0.36643 (13)	0.31502 (12)	1.06165 (13)	0.0531 (3)
O3	0.40499 (13)	0.07043 (11)	1.10772 (12)	0.0510 (3)
S1	0.45343 (4)	0.20409 (3)	1.03010 (4)	0.04001 (12)
Cl1	0.95478 (8)	0.42370 (8)	0.34929 (7)	0.1012 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0652 (12)	0.0749 (13)	0.0401 (9)	−0.0231 (10)	−0.0109 (8)	−0.0048 (8)
C2	0.0515 (9)	0.0554 (9)	0.0379 (8)	−0.0137 (7)	−0.0157 (7)	−0.0071 (7)
C3	0.0673 (11)	0.0476 (9)	0.0439 (9)	−0.0139 (8)	−0.0265 (8)	−0.0008 (7)
C4	0.0632 (11)	0.0446 (9)	0.0567 (10)	0.0020 (8)	−0.0281 (9)	−0.0083 (7)
C5	0.0456 (8)	0.0487 (9)	0.0488 (9)	−0.0008 (7)	−0.0168 (7)	−0.0110 (7)
C6	0.0407 (7)	0.0400 (7)	0.0384 (7)	−0.0078 (6)	−0.0157 (6)	−0.0073 (6)
C7	0.0425 (8)	0.0457 (8)	0.0391 (8)	−0.0063 (6)	−0.0154 (6)	−0.0119 (6)
C8	0.0471 (9)	0.0792 (13)	0.0574 (11)	0.0035 (9)	−0.0184 (8)	−0.0219 (10)
C9	0.0637 (14)	0.0928 (19)	0.130 (3)	0.0210 (13)	−0.0312 (15)	−0.0325 (17)
C10	0.0447 (8)	0.0391 (7)	0.0360 (7)	−0.0108 (6)	−0.0111 (6)	−0.0079 (6)
C11	0.0628 (11)	0.0399 (8)	0.0589 (10)	−0.0141 (7)	−0.0297 (9)	0.0024 (7)
C12	0.0617 (11)	0.0572 (10)	0.0675 (12)	−0.0071 (9)	−0.0349 (10)	−0.0020 (9)
C13	0.0535 (10)	0.0704 (12)	0.0509 (10)	−0.0184 (9)	−0.0165 (8)	−0.0172 (9)
C14	0.0591 (10)	0.0522 (10)	0.0657 (12)	−0.0222 (8)	−0.0117 (9)	−0.0211 (8)
C15	0.0527 (9)	0.0395 (8)	0.0596 (10)	−0.0088 (7)	−0.0118 (8)	−0.0176 (7)
C16	0.0610 (13)	0.1033 (18)	0.0955 (18)	−0.0223 (12)	−0.0326 (13)	−0.0248 (15)
C17	0.120 (2)	0.0525 (11)	0.0877 (17)	−0.0236 (12)	−0.0575 (16)	0.0148 (11)
C18A	0.134 (10)	0.060 (6)	0.078 (9)	−0.010 (5)	−0.065 (9)	−0.018 (6)
C19A	0.084 (5)	0.107 (7)	0.159 (9)	0.003 (4)	−0.044 (5)	−0.083 (6)
C18B	0.081 (3)	0.071 (3)	0.067 (4)	−0.021 (2)	−0.022 (3)	−0.004 (3)
C19B	0.121 (4)	0.136 (5)	0.081 (4)	−0.061 (4)	−0.011 (3)	−0.048 (3)
N1	0.0861 (13)	0.0787 (12)	0.0463 (9)	−0.0342 (10)	−0.0185 (9)	0.0039 (8)
N2	0.0899 (13)	0.0540 (9)	0.0496 (9)	−0.0224 (8)	−0.0283 (9)	0.0058 (7)
N3	0.0415 (7)	0.0359 (6)	0.0420 (7)	−0.0079 (5)	−0.0112 (5)	−0.0095 (5)
O1	0.0445 (6)	0.0508 (6)	0.0524 (7)	−0.0024 (5)	−0.0131 (5)	−0.0185 (5)
O2	0.0518 (7)	0.0486 (6)	0.0524 (7)	−0.0007 (5)	−0.0070 (5)	−0.0173 (5)
O3	0.0513 (7)	0.0411 (6)	0.0489 (7)	−0.0169 (5)	−0.0053 (5)	−0.0039 (5)
S1	0.0401 (2)	0.0354 (2)	0.0385 (2)	−0.00946 (14)	−0.00577 (15)	−0.00744 (14)
Cl1	0.0849 (4)	0.1221 (6)	0.0606 (4)	−0.0129 (4)	0.0153 (3)	−0.0182 (4)

Geometric parameters (Å, º) top

C1—N1	1.308 (3)	C13—C14	1.383 (3)
C1—C2	1.422 (3)	C13—C16	1.510 (3)
C1—Cl1	1.705 (2)	C14—C15	1.382 (3)
C2—C3	1.403 (3)	C14—H14	0.9300
C2—C7	1.411 (2)	C15—H15	0.9300
C3—N2	1.366 (2)	C16—H16A	0.9600
C3—C4	1.394 (3)	C16—H16B	0.9600
C4—C5	1.366 (2)	C16—H16C	0.9600
C4—H4	0.9300	C17—C18B	1.380 (11)
C5—C6	1.412 (2)	C17—N2	1.442 (3)
C5—H5	0.9300	C17—C18A	1.663 (15)
C6—C7	1.382 (2)	C17—H17A	0.9700
C6—N3	1.4327 (18)	C17—H17B	0.9700
C7—O1	1.3683 (19)	C17—H17C	0.9700
C8—O1	1.450 (2)	C17—H17D	0.9700
C8—C9	1.478 (3)	C18A—C19A	1.331 (19)
C8—H8A	0.9700	C18A—H18A	0.9300
C8—H8B	0.9700	C19A—H19A	0.9300
C9—H9A	0.9600	C19A—H19B	0.9300
C9—H9B	0.9600	C18B—C19B	1.307 (10)
C9—H9C	0.9600	C18B—H18B	0.9300
C10—C11	1.380 (2)	C19B—H19C	0.9300
C10—C15	1.390 (2)	C19B—H19D	0.9300
C10—S1	1.7572 (16)	N1—N2	1.357 (3)
C11—C12	1.382 (3)	N3—S1	1.6504 (13)
C11—H11	0.9300	N3—H3N	0.8896
C12—C13	1.388 (3)	O2—S1	1.4267 (12)
C12—H12	0.9300	O3—S1	1.4317 (11)

N1—C1—C2	112.7 (2)	C13—C16—H16B	109.5
N1—C1—Cl1	118.98 (16)	H16A—C16—H16B	109.5
C2—C1—Cl1	128.32 (17)	C13—C16—H16C	109.5
C3—C2—C7	119.20 (16)	H16A—C16—H16C	109.5
C3—C2—C1	103.15 (16)	H16B—C16—H16C	109.5
C7—C2—C1	137.65 (18)	C18B—C17—N2	118.3 (5)
N2—C3—C4	130.22 (18)	C18B—C17—C18A	14.3 (7)
N2—C3—C2	106.89 (17)	N2—C17—C18A	107.4 (6)
C4—C3—C2	122.81 (15)	C18B—C17—H17A	111.6
C5—C4—C3	117.00 (16)	N2—C17—H17A	110.2
C5—C4—H4	121.5	C18A—C17—H17A	110.2
C3—C4—H4	121.5	C18B—C17—H17B	96.9
C4—C5—C6	121.71 (16)	N2—C17—H17B	110.2
C4—C5—H5	119.1	C18A—C17—H17B	110.2
C6—C5—H5	119.1	H17A—C17—H17B	108.5
C7—C6—C5	121.27 (14)	C18B—C17—H17C	107.7
C7—C6—N3	119.03 (14)	N2—C17—H17C	107.7
C5—C6—N3	119.65 (14)	C18A—C17—H17C	121.4
O1—C7—C6	119.44 (14)	H17A—C17—H17C	99.4
O1—C7—C2	122.54 (14)	H17B—C17—H17C	11.9
C6—C7—C2	117.89 (15)	C18B—C17—H17D	107.7
O1—C8—C9	107.74 (18)	N2—C17—H17D	107.7
O1—C8—H8A	110.2	C18A—C17—H17D	104.8
C9—C8—H8A	110.2	H17A—C17—H17D	7.7
O1—C8—H8B	110.2	H17B—C17—H17D	116.0
C9—C8—H8B	110.2	H17C—C17—H17D	107.1
H8A—C8—H8B	108.5	C19A—C18A—C17	120.0 (9)
C8—C9—H9A	109.5	C19A—C18A—H18A	120.0
C8—C9—H9B	109.5	C17—C18A—H18A	120.0
H9A—C9—H9B	109.5	C18A—C19A—H19A	120.0
C8—C9—H9C	109.5	C18A—C19A—H19B	120.0
H9A—C9—H9C	109.5	H19A—C19A—H19B	120.0
H9B—C9—H9C	109.5	C19B—C18B—C17	123.8 (9)
C11—C10—C15	120.75 (15)	C19B—C18B—H18B	118.1
C11—C10—S1	119.82 (11)	C17—C18B—H18B	118.1
C15—C10—S1	119.27 (13)	C18B—C19B—H19C	120.0
C10—C11—C12	119.32 (15)	C18B—C19B—H19D	120.0
C10—C11—H11	120.3	H19C—C19B—H19D	120.0
C12—C11—H11	120.3	C1—N1—N2	105.77 (17)
C11—C12—C13	121.25 (18)	N1—N2—C3	111.52 (17)
C11—C12—H12	119.4	N1—N2—C17	120.35 (19)
C13—C12—H12	119.4	C3—N2—C17	128.1 (2)
C14—C13—C12	118.22 (17)	C6—N3—S1	119.49 (10)
C14—C13—C16	120.82 (18)	C6—N3—H3N	114.3
C12—C13—C16	120.9 (2)	S1—N3—H3N	108.7
C15—C14—C13	121.79 (16)	C7—O1—C8	114.94 (13)
C15—C14—H14	119.1	O2—S1—O3	119.60 (7)
C13—C14—H14	119.1	O2—S1—N3	107.72 (7)
C14—C15—C10	118.65 (16)	O3—S1—N3	105.18 (7)
C14—C15—H15	120.7	O2—S1—C10	108.63 (7)
C10—C15—H15	120.7	O3—S1—C10	108.69 (7)
C13—C16—H16A	109.5	N3—S1—C10	106.23 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O3ⁱ	0.89	2.22	3.0588 (17)	156

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O3ⁱ	0.89	2.22	3.0588 (17)	156.0

Symmetry code: (i) −x+1, −y, −z+2.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

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
Bouissane, L., El Kazzouli, S., Leonce, S., Pfeifer, P., Rakib, M. E., Khouili, M. & Guillaumet, G. (2006). Bioorg. Med. Chem. 14, 1078–1088. Web of Science CrossRef PubMed CAS 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