4-Meth­oxy-N-(1-methyl-1H-indazol-7-yl)benzene­sulfonamide hemihydrate

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

doi:10.1107/S2414314617006459

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 5| May 2017| x170645

https://doi.org/10.1107/S2414314617006459

Open

access

4-Methoxy-N-(1-methyl-1H-indazol-7-yl)benzenesulfonamide hemihydrate

Latifa Bouissane,^a ^* Souad Mojahidi,^a El Mostapha Rakib,^a Hakima Chicha,^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, Faculty of Sciences, Mohammed V University in Rabat, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: l_bouissane@yahoo.com

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 15 April 2017; accepted 29 April 2017; online 5 May 2017)

The asymmetric unit of the title compound, 2C₁₅H₁₅N₃O₃S·H₂O, comprises two crystallographically independent organic molecules and one water molecule, all in general positions. Each organic molecule comprises an indazolyl system linked through a sulfonamide group to a methoxybenzene ring. The most important difference between the two organic molecules is the dihedral angle between the fused-ring system and the methoxybenzene ring, which is 56.32 (7)° in one molecule and 35.35 (8)° in the other. In the crystal, the organic and water molecules are connected into supramolecular chains along the c axis through O—H⋯N, O—H⋯O, N—H⋯O and N—-H⋯N hydrogen bonds; in addition, a π–π interaction between pyrazolyl rings [inter-centroid separation = 3.7547 (12) Å] is noted.

Keywords: indazolyl; benzenesulfonamide; heterocyclic compounds; hydrogen-bonds; crystal structure.

CCDC reference: 1547025

Structure description

Sulfonamides and their derivatives constitute an important class of therapeutic agents that exhibit a broad spectrum of pharmacological profiles, such as anti-bacterial, diuretic, hypoglycaemic, anti-thyroid, anti-viral, anti-inflammatory and anti-parasitic activities among others (Ranjith et al., 2014 ; Shah et al., 2013 ; Scozzafava et al., 2013 ; Greig et al., 2013 ). In our previous work, we have found that indazoles bearing arylsulfonamide groups showed anti-proliferative activity against human (colon and prostate) and murine (leukaemia) cell lines (Abbassi et al., 2012 , 2014 ; Bouissane, et al., 2006 ).

The asymmetric unit of the title compound contains two independent organic molecules and one water molecule, as shown in Fig. 1. The fused five- and six-membered rings of each molecule are almost coplanar, with the maximum deviation from the mean plane being 0.020 (2) Å for the C12 atom and 0.022 (2) Å for the C27 atom in the first and second molecules, respectively. The dihedral angles between the indazolyl system and the methoxybenzene ring are 56.32 (7) and 35.35 (8)° in the first and second molecules, respectively.

Figure 1
Plot of the molecules comprising the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, the organic molecules are connected through the water molecule by O7—H7A⋯N6, O7—H7B⋯O2, N1—HN1⋯O7 and N4—HN4⋯N3 hydrogen bonds (Table 1), in addition to π–π interactions between pyrazole rings as shown in Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯N6ⁱ	0.83	2.03	2.828 (2)	160
O7—H7B⋯O2ⁱⁱ	0.83	2.08	2.8831 (18)	162
N1—HN1⋯O7	0.86	1.92	2.7745 (18)	177
N4—HN4⋯N3	0.83	2.26	3.060 (2)	163
Symmetry codes: (i) x, y, z+1; (ii) -x+2, -y, -z+2.

Figure 2
Crystal packing for the title compound showing hydrogen bonds as blue dashed lines and π–π interactions between pyrazole rings as green dashed lines.

Synthesis and crystallization

A mixture of 1-methyl-7-nitroindazole (1.22 mmol) and anhydrous SnCl₂ (1.1 g, 6.1 mmol) in ethanethiol (25 ml) was heated at 308 K for 4 h. After reduction, the starting material had been consumed and the solution was allowed to cool. The pH of the solution was made slightly basic (pH = 7–8) by addition of 5% aqueous potassium bicarbonate. Extraction with EtOAc followed. 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-methoxybenzenesulfonyl chloride (0.26 g, 1.25 mmol) at room temperature for 24 h. After the reaction mixture had been concentrated in vacuo, the resulting residue was purified by flash chromatography (elution was with EtOAc/hexane 1:9). The title compound was recrystallized from acetone solution, yield 62%; m.p. 439 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Three reflections, i.e. (010), (0 $[\overline{1}]$ 1) and (001), were omitted from the final cycles of refinement owing to poor agreement.

Table 2
Experimental details

Crystal data
Chemical formula	2C₁₅H₁₅N₃O₃S·H₂O
M_r	652.73
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	8.3013 (5), 13.1934 (8), 15.3583 (9)
α, β, γ (°)	103.241 (3), 105.470 (3), 93.046 (3)
V (Å³)	1566.30 (16)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.23
Crystal size (mm)	0.33 × 0.26 × 0.22

Data collection
Diffractometer	Bruker X8 APEX
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.663, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	52678, 8793, 6373
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.694

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.126, 1.01
No. of reflections	8793
No. of parameters	410
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.27
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXTL2014/7 (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1547025

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617006459/tk4031sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617006459/tk4031Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL2014/7 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

4-Methoxy-N-(1-methyl-1H-indazol-7-yl)benzenesulfonamide hemihydrate top

Crystal data top

2C₁₅H₁₅N₃O₃S·H₂O	Z = 2
M_r = 652.73	F(000) = 684
Triclinic, P1	D_x = 1.384 Mg m⁻³
a = 8.3013 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.1934 (8) Å	Cell parameters from 8793 reflections
c = 15.3583 (9) Å	θ = 2.4–29.6°
α = 103.241 (3)°	µ = 0.23 mm⁻¹
β = 105.470 (3)°	T = 296 K
γ = 93.046 (3)°	Block, colourless
V = 1566.30 (16) Å³	0.33 × 0.26 × 0.22 mm

Data collection top

Bruker X8 APEX diffractometer	8793 independent reflections
Radiation source: fine-focus sealed tube	6373 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 29.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −11→11
T_min = 0.663, T_max = 0.746	k = −18→18
52678 measured reflections	l = −21→21

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0597P)² + 0.3677P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
8793 reflections	Δρ_max = 0.36 e Å⁻³
410 parameters	Δρ_min = −0.27 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C1	0.7955 (3)	0.5081 (2)	1.36936 (15)	0.0819 (7)
H1A	0.7711	0.5670	1.4116	0.123*
H1B	0.9031	0.4886	1.3978	0.123*
H1C	0.7100	0.4500	1.3553	0.123*
C2	0.8330 (2)	0.46149 (14)	1.21830 (12)	0.0519 (4)
C3	0.8606 (2)	0.35988 (14)	1.22437 (12)	0.0523 (4)
H3	0.8550	0.3382	1.2771	0.063*
C4	0.8961 (2)	0.29174 (13)	1.15114 (11)	0.0475 (4)
H4	0.9146	0.2236	1.1545	0.057*
C5	0.90435 (18)	0.32425 (12)	1.07256 (11)	0.0413 (3)
C6	0.8740 (2)	0.42508 (13)	1.06623 (13)	0.0506 (4)
H6	0.8771	0.4465	1.0130	0.061*
C7	0.8392 (2)	0.49298 (14)	1.13927 (14)	0.0590 (4)
H7	0.8197	0.5608	1.1356	0.071*
C8	0.63751 (17)	0.16629 (12)	0.88692 (10)	0.0384 (3)
C9	0.5267 (2)	0.20653 (14)	0.93452 (12)	0.0490 (4)
H9	0.5570	0.2172	0.9991	0.059*
C10	0.3695 (2)	0.23200 (16)	0.88899 (13)	0.0581 (5)
H10	0.2985	0.2591	0.9239	0.070*
C11	0.3193 (2)	0.21774 (15)	0.79473 (13)	0.0555 (4)
H11	0.2160	0.2359	0.7649	0.067*
C12	0.42742 (19)	0.17504 (14)	0.74370 (11)	0.0471 (4)
C13	0.58508 (17)	0.14913 (11)	0.78936 (10)	0.0384 (3)
C14	0.4189 (2)	0.14518 (17)	0.64821 (12)	0.0588 (5)
H14	0.3280	0.1526	0.6003	0.071*
C15	0.8160 (2)	0.06416 (15)	0.72874 (13)	0.0546 (4)
H15A	0.8191	0.0273	0.6677	0.082*
H15B	0.8260	0.0165	0.7682	0.082*
H15C	0.9076	0.1198	0.7550	0.082*
C16	0.6073 (3)	0.5679 (2)	0.86652 (16)	0.0869 (7)
H16A	0.5583	0.6269	0.8937	0.130*
H16B	0.7230	0.5724	0.9018	0.130*
H16C	0.5469	0.5042	0.8674	0.130*
C17	0.6649 (2)	0.49176 (14)	0.72376 (13)	0.0549 (4)
C18	0.7408 (2)	0.41260 (14)	0.75749 (12)	0.0543 (4)
H18	0.7482	0.4088	0.8181	0.065*
C19	0.8056 (2)	0.33912 (14)	0.70115 (11)	0.0521 (4)
H19	0.8576	0.2861	0.7242	0.063*
C20	0.7939 (2)	0.34356 (13)	0.61088 (11)	0.0470 (4)
C21	0.7174 (2)	0.42338 (15)	0.57673 (13)	0.0586 (4)
H21	0.7093	0.4270	0.5160	0.070*
C22	0.6541 (3)	0.49656 (16)	0.63312 (15)	0.0650 (5)
H22	0.6033	0.5501	0.6104	0.078*
C23	0.57109 (19)	0.17150 (12)	0.41223 (11)	0.0419 (3)
C24	0.4319 (2)	0.21437 (14)	0.42935 (13)	0.0530 (4)
H24	0.4268	0.2339	0.4906	0.064*
C25	0.2974 (2)	0.22982 (16)	0.35798 (17)	0.0661 (5)
H25	0.2048	0.2580	0.3727	0.079*
C26	0.3001 (2)	0.20434 (16)	0.26802 (16)	0.0675 (5)
H26	0.2119	0.2163	0.2210	0.081*
C27	0.4389 (2)	0.15954 (14)	0.24732 (12)	0.0544 (4)
C28	0.57333 (19)	0.14280 (12)	0.31873 (11)	0.0425 (3)
C29	0.4819 (3)	0.11994 (18)	0.16507 (13)	0.0704 (6)
H29	0.4157	0.1199	0.1058	0.085*
C30	0.8443 (2)	0.06187 (16)	0.31512 (15)	0.0652 (5)
H30A	0.8662	0.0060	0.2690	0.098*
H30B	0.8409	0.0372	0.3688	0.098*
H30C	0.9321	0.1194	0.3331	0.098*
N1	0.79869 (15)	0.14195 (10)	0.93399 (9)	0.0409 (3)
HN1	0.8019	0.1000	0.9697	0.049*
N2	0.65791 (16)	0.10768 (11)	0.72168 (9)	0.0458 (3)
N3	0.55537 (19)	0.10556 (14)	0.63529 (10)	0.0578 (4)
N4	0.70516 (16)	0.15252 (11)	0.48502 (9)	0.0456 (3)
HN4	0.6730	0.1276	0.5232	0.055*
N5	0.68470 (18)	0.09626 (12)	0.27673 (10)	0.0515 (3)
N6	0.6269 (3)	0.08297 (14)	0.18201 (11)	0.0690 (5)
O1	0.7990 (2)	0.53534 (11)	1.28620 (10)	0.0743 (4)
O2	1.09600 (13)	0.18909 (10)	1.02068 (8)	0.0530 (3)
O3	0.96160 (15)	0.29187 (10)	0.91188 (8)	0.0534 (3)
O4	0.5979 (2)	0.56814 (12)	0.77337 (11)	0.0761 (4)
O5	0.98772 (16)	0.19783 (11)	0.59488 (9)	0.0679 (4)
O6	0.90416 (17)	0.28627 (11)	0.46690 (9)	0.0658 (4)
O7	0.8147 (2)	0.01367 (11)	1.05542 (10)	0.0801 (5)
H7A	0.7595	0.0187	1.0937	0.120*
H7B	0.8402	−0.0470	1.0451	0.120*
S1	0.95253 (4)	0.23680 (3)	0.98091 (3)	0.04128 (10)
S2	0.86491 (5)	0.24489 (4)	0.53781 (3)	0.05034 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0833 (15)	0.0967 (17)	0.0597 (13)	0.0026 (13)	0.0285 (11)	0.0002 (12)
C2	0.0429 (8)	0.0515 (9)	0.0548 (10)	−0.0010 (7)	0.0146 (7)	0.0015 (8)
C3	0.0503 (9)	0.0619 (10)	0.0455 (9)	0.0055 (8)	0.0141 (7)	0.0148 (8)
C4	0.0465 (8)	0.0496 (9)	0.0477 (9)	0.0107 (7)	0.0115 (7)	0.0161 (7)
C5	0.0319 (7)	0.0465 (8)	0.0444 (8)	0.0041 (6)	0.0086 (6)	0.0124 (6)
C6	0.0512 (9)	0.0494 (9)	0.0564 (10)	0.0037 (7)	0.0180 (8)	0.0212 (8)
C7	0.0639 (11)	0.0436 (9)	0.0728 (12)	0.0073 (8)	0.0240 (9)	0.0159 (8)
C8	0.0340 (7)	0.0427 (7)	0.0395 (7)	0.0028 (6)	0.0114 (6)	0.0120 (6)
C9	0.0442 (8)	0.0609 (10)	0.0425 (8)	0.0045 (7)	0.0171 (7)	0.0090 (7)
C10	0.0388 (8)	0.0741 (12)	0.0627 (11)	0.0111 (8)	0.0225 (8)	0.0095 (9)
C11	0.0333 (7)	0.0688 (11)	0.0637 (11)	0.0078 (7)	0.0118 (7)	0.0175 (9)
C12	0.0350 (7)	0.0586 (9)	0.0465 (8)	0.0006 (7)	0.0081 (6)	0.0167 (7)
C13	0.0346 (7)	0.0420 (7)	0.0394 (7)	0.0013 (6)	0.0119 (6)	0.0112 (6)
C14	0.0418 (9)	0.0862 (13)	0.0460 (9)	−0.0006 (9)	0.0045 (7)	0.0232 (9)
C15	0.0563 (10)	0.0571 (10)	0.0557 (10)	0.0161 (8)	0.0254 (8)	0.0119 (8)
C16	0.0716 (14)	0.1005 (18)	0.0711 (14)	0.0149 (13)	0.0200 (11)	−0.0130 (13)
C17	0.0530 (9)	0.0466 (9)	0.0579 (10)	0.0013 (7)	0.0119 (8)	0.0047 (8)
C18	0.0607 (10)	0.0539 (10)	0.0411 (8)	0.0004 (8)	0.0087 (7)	0.0061 (7)
C19	0.0582 (10)	0.0487 (9)	0.0421 (8)	0.0054 (8)	0.0037 (7)	0.0100 (7)
C20	0.0454 (8)	0.0475 (9)	0.0418 (8)	−0.0002 (7)	0.0062 (6)	0.0075 (7)
C21	0.0665 (11)	0.0605 (11)	0.0521 (10)	0.0080 (9)	0.0149 (8)	0.0231 (8)
C22	0.0736 (13)	0.0541 (10)	0.0705 (12)	0.0168 (9)	0.0172 (10)	0.0242 (9)
C23	0.0410 (7)	0.0429 (8)	0.0404 (8)	0.0030 (6)	0.0108 (6)	0.0092 (6)
C24	0.0499 (9)	0.0535 (10)	0.0587 (10)	0.0091 (7)	0.0222 (8)	0.0116 (8)
C25	0.0444 (9)	0.0633 (11)	0.0949 (16)	0.0151 (8)	0.0205 (10)	0.0261 (11)
C26	0.0470 (10)	0.0710 (12)	0.0803 (14)	0.0057 (9)	−0.0016 (9)	0.0346 (11)
C27	0.0530 (10)	0.0577 (10)	0.0474 (9)	−0.0054 (8)	0.0028 (7)	0.0199 (8)
C28	0.0409 (7)	0.0442 (8)	0.0404 (8)	−0.0002 (6)	0.0106 (6)	0.0091 (6)
C29	0.0777 (14)	0.0827 (14)	0.0419 (10)	−0.0124 (12)	0.0044 (9)	0.0180 (9)
C30	0.0521 (10)	0.0683 (12)	0.0724 (13)	0.0089 (9)	0.0279 (9)	0.0002 (10)
N1	0.0403 (6)	0.0462 (7)	0.0392 (6)	0.0078 (5)	0.0107 (5)	0.0173 (5)
N2	0.0427 (7)	0.0572 (8)	0.0379 (7)	0.0051 (6)	0.0134 (5)	0.0105 (6)
N3	0.0528 (8)	0.0804 (11)	0.0369 (7)	−0.0020 (7)	0.0103 (6)	0.0137 (7)
N4	0.0461 (7)	0.0519 (7)	0.0365 (6)	0.0035 (6)	0.0084 (5)	0.0110 (6)
N5	0.0542 (8)	0.0567 (8)	0.0421 (7)	0.0012 (6)	0.0191 (6)	0.0044 (6)
N6	0.0888 (13)	0.0728 (11)	0.0403 (8)	−0.0145 (10)	0.0256 (8)	0.0013 (7)
O1	0.0868 (10)	0.0645 (8)	0.0705 (9)	0.0059 (8)	0.0361 (8)	−0.0005 (7)
O2	0.0393 (6)	0.0674 (7)	0.0522 (7)	0.0187 (5)	0.0100 (5)	0.0160 (6)
O3	0.0507 (6)	0.0659 (7)	0.0529 (7)	0.0045 (6)	0.0208 (5)	0.0266 (6)
O4	0.0813 (10)	0.0655 (9)	0.0754 (10)	0.0197 (8)	0.0236 (8)	0.0019 (7)
O5	0.0500 (7)	0.0782 (9)	0.0602 (8)	0.0173 (6)	−0.0015 (6)	0.0052 (7)
O6	0.0613 (8)	0.0764 (9)	0.0588 (8)	−0.0076 (7)	0.0245 (6)	0.0107 (7)
O7	0.1307 (14)	0.0656 (9)	0.0751 (9)	0.0411 (9)	0.0604 (10)	0.0357 (7)
S1	0.03386 (17)	0.0517 (2)	0.0421 (2)	0.00845 (15)	0.01207 (14)	0.01725 (16)
S2	0.0423 (2)	0.0591 (3)	0.0438 (2)	0.00319 (18)	0.00828 (16)	0.00708 (18)

Geometric parameters (Å, º) top

C1—O1	1.411 (3)	C17—C22	1.387 (3)
C1—H1A	0.9600	C18—C19	1.377 (2)
C1—H1B	0.9600	C18—H18	0.9300
C1—H1C	0.9600	C19—C20	1.379 (2)
C2—O1	1.356 (2)	C19—H19	0.9300
C2—C7	1.382 (3)	C20—C21	1.391 (2)
C2—C3	1.392 (3)	C20—S2	1.7512 (17)
C3—C4	1.379 (2)	C21—C22	1.368 (3)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.387 (2)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.374 (2)
C5—C6	1.387 (2)	C23—C28	1.404 (2)
C5—S1	1.7544 (16)	C23—N4	1.4301 (19)
C6—C7	1.372 (3)	C24—C25	1.402 (3)
C6—H6	0.9300	C24—H24	0.9300
C7—H7	0.9300	C25—C26	1.352 (3)
C8—C9	1.376 (2)	C25—H25	0.9300
C8—C13	1.404 (2)	C26—C27	1.400 (3)
C8—N1	1.4324 (18)	C26—H26	0.9300
C9—C10	1.404 (2)	C27—C29	1.398 (3)
C9—H9	0.9300	C27—C28	1.408 (2)
C10—C11	1.360 (3)	C28—N5	1.358 (2)
C10—H10	0.9300	C29—N6	1.307 (3)
C11—C12	1.401 (2)	C29—H29	0.9300
C11—H11	0.9300	C30—N5	1.442 (2)
C12—C14	1.410 (2)	C30—H30A	0.9600
C12—C13	1.410 (2)	C30—H30B	0.9600
C13—N2	1.3619 (19)	C30—H30C	0.9600
C14—N3	1.316 (2)	N1—S1	1.6256 (13)
C14—H14	0.9300	N1—HN1	0.8600
C15—N2	1.448 (2)	N2—N3	1.3651 (19)
C15—H15A	0.9600	N4—S2	1.6441 (14)
C15—H15B	0.9600	N4—HN4	0.8284
C15—H15C	0.9600	N5—N6	1.371 (2)
C16—O4	1.413 (3)	O2—S1	1.4337 (11)
C16—H16A	0.9600	O3—S1	1.4307 (12)
C16—H16B	0.9600	O5—S2	1.4259 (13)
C16—H16C	0.9600	O6—S2	1.4259 (14)
C17—O4	1.356 (2)	O7—H7A	0.8299
C17—C18	1.378 (3)	O7—H7B	0.8299

O1—C1—H1A	109.5	C19—C20—C21	119.72 (16)
O1—C1—H1B	109.5	C19—C20—S2	119.93 (13)
H1A—C1—H1B	109.5	C21—C20—S2	120.25 (13)
O1—C1—H1C	109.5	C22—C21—C20	119.56 (17)
H1A—C1—H1C	109.5	C22—C21—H21	120.2
H1B—C1—H1C	109.5	C20—C21—H21	120.2
O1—C2—C7	115.49 (17)	C21—C22—C17	120.74 (18)
O1—C2—C3	124.28 (17)	C21—C22—H22	119.6
C7—C2—C3	120.23 (16)	C17—C22—H22	119.6
C4—C3—C2	119.14 (16)	C24—C23—C28	116.88 (15)
C4—C3—H3	120.4	C24—C23—N4	122.16 (15)
C2—C3—H3	120.4	C28—C23—N4	120.92 (14)
C3—C4—C5	120.33 (16)	C23—C24—C25	122.49 (18)
C3—C4—H4	119.8	C23—C24—H24	118.8
C5—C4—H4	119.8	C25—C24—H24	118.8
C4—C5—C6	120.26 (15)	C26—C25—C24	120.99 (18)
C4—C5—S1	119.56 (12)	C26—C25—H25	119.5
C6—C5—S1	120.19 (12)	C24—C25—H25	119.5
C7—C6—C5	119.37 (16)	C25—C26—C27	118.40 (17)
C7—C6—H6	120.3	C25—C26—H26	120.8
C5—C6—H6	120.3	C27—C26—H26	120.8
C6—C7—C2	120.64 (16)	C29—C27—C26	134.62 (19)
C6—C7—H7	119.7	C29—C27—C28	104.63 (17)
C2—C7—H7	119.7	C26—C27—C28	120.72 (17)
C9—C8—C13	116.97 (14)	N5—C28—C23	132.75 (15)
C9—C8—N1	121.96 (13)	N5—C28—C27	106.74 (14)
C13—C8—N1	121.07 (13)	C23—C28—C27	120.50 (15)
C8—C9—C10	122.28 (15)	N6—C29—C27	111.51 (17)
C8—C9—H9	118.9	N6—C29—H29	124.2
C10—C9—H9	118.9	C27—C29—H29	124.2
C11—C10—C9	121.10 (15)	N5—C30—H30A	109.5
C11—C10—H10	119.4	N5—C30—H30B	109.5
C9—C10—H10	119.4	H30A—C30—H30B	109.5
C10—C11—C12	118.25 (15)	N5—C30—H30C	109.5
C10—C11—H11	120.9	H30A—C30—H30C	109.5
C12—C11—H11	120.9	H30B—C30—H30C	109.5
C11—C12—C14	135.14 (16)	C8—N1—S1	118.27 (10)
C11—C12—C13	120.65 (15)	C8—N1—HN1	118.1
C14—C12—C13	104.18 (14)	S1—N1—HN1	110.3
N2—C13—C8	132.50 (14)	C13—N2—N3	110.83 (13)
N2—C13—C12	106.78 (13)	C13—N2—C15	130.26 (14)
C8—C13—C12	120.72 (13)	N3—N2—C15	118.85 (14)
N3—C14—C12	111.63 (15)	C14—N3—N2	106.58 (14)
N3—C14—H14	124.2	C23—N4—S2	118.47 (11)
C12—C14—H14	124.2	C23—N4—HN4	113.9
N2—C15—H15A	109.5	S2—N4—HN4	111.1
N2—C15—H15B	109.5	C28—N5—N6	110.14 (15)
H15A—C15—H15B	109.5	C28—N5—C30	131.09 (14)
N2—C15—H15C	109.5	N6—N5—C30	118.77 (15)
H15A—C15—H15C	109.5	C29—N6—N5	106.98 (16)
H15B—C15—H15C	109.5	C2—O1—C1	117.75 (17)
O4—C16—H16A	109.5	C17—O4—C16	118.23 (17)
O4—C16—H16B	109.5	H7A—O7—H7B	107.4
H16A—C16—H16B	109.5	O3—S1—O2	118.81 (7)
O4—C16—H16C	109.5	O3—S1—N1	107.97 (7)
H16A—C16—H16C	109.5	O2—S1—N1	105.66 (7)
H16B—C16—H16C	109.5	O3—S1—C5	107.83 (8)
O4—C17—C18	124.60 (18)	O2—S1—C5	107.82 (7)
O4—C17—C22	115.79 (17)	N1—S1—C5	108.38 (7)
C18—C17—C22	119.62 (17)	O6—S2—O5	120.27 (9)
C19—C18—C17	119.84 (17)	O6—S2—N4	106.67 (7)
C19—C18—H18	120.1	O5—S2—N4	105.43 (8)
C17—C18—H18	120.1	O6—S2—C20	108.53 (8)
C18—C19—C20	120.52 (16)	O5—S2—C20	108.31 (8)
C18—C19—H19	119.7	N4—S2—C20	106.89 (7)
C20—C19—H19	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···N6ⁱ	0.83	2.03	2.828 (2)	160
O7—H7B···O2ⁱⁱ	0.83	2.08	2.8831 (18)	162
N1—HN1···O7	0.86	1.92	2.7745 (18)	177
N4—HN4···N3	0.83	2.26	3.060 (2)	163

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

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, el 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., Chicha, H., Bouissane, L., Hannioui, A., Aiello, C., Gangemi, R., Castagnola, P., Rosano, C. & Viale, M. (2014). Arch. Pharm. Chem. Life Sci. 347, 423–431. Web of Science CrossRef CAS Google Scholar
Bouissane, L., El Kazzouli, S., Léonce, S., Pfeiffer, B., 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 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Greig, I. R., Coste, E., Ralston, S. H. & van 't Hof, R. J. (2013). Bioorg. Med. Chem. Lett. 23, 816–820. Web of Science CrossRef CAS PubMed Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ranjith, P. K., Pakkath, R., Haridas, K. R. & Kumari, S. N. (2014). Eur. J. Med. Chem. 71, 354–365. Web of Science CrossRef CAS PubMed Google Scholar
Scozzafava, A., Carta, F. & Supuran, C. T. (2013). Expert Opin. Ther. Pat. 23, 203–213. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shoaib Ahmad Shah, S., Rivera, G. & Ashfaq, M. (2013). Mini Rev. Med. Chem. 13, 70–86. CrossRef PubMed 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.