organic compounds
4-Methoxy-N-(1-methyl-1H-indazol-7-yl)benzenesulfonamide hemihydrate
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
The 15H15N3O3S·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.
of the title compound, 2CKeywords: indazolyl; benzenesulfonamide; heterocyclic compounds; hydrogen-bonds; crystal structure.
CCDC reference: 1547025
Structure description
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).
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 (RanjithThe . 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.
of the title compound contains two independent organic molecules and one water molecule, as shown in Fig. 1In 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.
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 (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 . Three reflections, i.e. (010), (01) and (001), were omitted from the final cycles of owing to poor agreement.
details are summarized in Table 2Structural data
CCDC reference: 1547025
https://doi.org/10.1107/S2414314617006459/tk4031sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617006459/tk4031Isup2.hkl
Data collection: APEX2 (Bruker, 2009); cell
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).2C15H15N3O3S·H2O | Z = 2 |
Mr = 652.73 | F(000) = 684 |
Triclinic, P1 | Dx = 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 |
Bruker X8 APEX diffractometer | 8793 independent reflections |
Radiation source: fine-focus sealed tube | 6373 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 29.6°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −11→11 |
Tmin = 0.663, Tmax = 0.746 | k = −18→18 |
52678 measured reflections | l = −21→21 |
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(Fo2) + (0.0597P)2 + 0.3677P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
8793 reflections | Δρmax = 0.36 e Å−3 |
410 parameters | Δρmin = −0.27 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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 |
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
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