organic compounds
Ethyl 3-[7-(N-acetyl-4-methoxybenzenesulfonamido)-3-chloro-2H-indazol-2-yl]propionate
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: assoman_k@yahoo.fr
In the title compound, C21H22ClN3O6S, the fused five- and six-membered ring rings are almost perpendicular to the planes through the atoms forming the acetyl and the propionic ester groups, as indicated by the dihedral angles of 80.3 (2) and 88.3 (7)°, respectively. The dihedral angle between the indazole system and the 4-methoxybenzenesulfonyl group is 13.76 (6)°. The carbonyl O atom is split over two positions in a 0.60 (5):0.40 (5) ratio. In the crystal, molecules are linked by C—H⋯O and C—H⋯N interactions into a three-dimensional network.
CCDC reference: 986487
Related literature
For the biological activity of et al. (2012); Salerno et al. (2012); Kaltenbach et al. (2003); Thangadurai et al. (2012); Abbassi et al. (2012). For similar compounds, see: Abbassi et al. (2013); Chicha et al. (2013).
see: LohouExperimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell 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: 986487
10.1107/S1600536814003183/tk5294sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003183/tk5294Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814003183/tk5294Isup3.cml
The indazole ring system is recognized to be a highly effective pharmacophore in medicinal chemistry as well as being the core of important nitrogen-containing heterocycles that show a broad range of biological activities, such as nitric oxide syntheses and HIV protease inhibitors, anti-inflammatory and anti-cancer agents, and serotonin 5-HT3 receptor antagonists (Lohou et al., 2012; Salerno et al., 2012; Kaltenbach et al., 2003; Thangadurai et al., 2012; Abbassi et al., 2012). The present work is a continuation of the investigation of the sulfonamide derivatives published recently by our team (Abbassi, et al., 2013; Chicha, et al., 2013).
The molecule of the title compound is built up from fused five- and six-membered rings linked to an acetyl-(4-methoxy-benzenesulfonyl)-amino group and to a propionic ethyl ester as shown in Fig. 1. The indazole ring system makes dihedral angles of 80.3 (2) and 88.3 (7)°, with the two planes through the atoms forming the acetyl (O3C13C14) and the propionic ester (O1O2C3C4C5) groups, respectively. The plane through the 4-methoxy-benzenesulfonyl group is nearly parallel to the indazole ring system, as indicated by the dihedral angle of 13.76 (6)°. In the crystal, the molecules are linked by C—H···O and C—H···N interactions to form a three-dimensional network (Fig. 2 and Table 1).
Ethyl 3-(3-chloro-7-nitro-2H-indazol-2-yl)propanoate (1.48 mmol) was added to a mixture of indium powder (850 mg, 7.43 mmol) and acetic acid (8.35 ml, 150 mmol) in ethanol (5 ml). The reaction mixture was stirred at 333 K for 6 h. After reduction, the starting material disappeared, and the solution was allowed to cool. 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-methoxybenzenesulfonyl 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
(eluted with ethyl acetate: Hexane 2:8). The title compound was recrystallized from ethanol (Yield: 44%; M.pt: 394 K).H atoms were located in a difference map and treated as riding with C–H = 0.96 Å, 0.97 Å and 0.93 Å for methyl-, methylene- and aromatic-H, respectively, and with Uiso(H) = 1.5 Ueq for methyl-H and Uiso(H) = 1.2 Ueq for methylene- and aromatic-H. The ester-O atom was rfined over two positions, O2A and O2B, in a 40:60 ratio.
Data collection: APEX2 (Bruker, 2009); cell
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).Fig. 1. Plot of the molecule of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. Partial crystal packing for the title compound showing hydrogen bonds as dashed lines. |
C21H22ClN3O6S | Z = 2 |
Mr = 479.93 | F(000) = 500 |
Triclinic, P1 | Dx = 1.445 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1442 (3) Å | Cell parameters from 6725 reflections |
b = 9.4376 (4) Å | θ = 2.4–30.5° |
c = 14.0931 (6) Å | µ = 0.31 mm−1 |
α = 108.262 (2)° | T = 296 K |
β = 96.017 (2)° | Block, colourless |
γ = 103.313 (2)° | 0.38 × 0.32 × 0.27 mm |
V = 1103.12 (8) Å3 |
Bruker X8 APEX diffractometer | 6725 independent reflections |
Radiation source: fine-focus sealed tube | 4687 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 30.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→13 |
Tmin = 0.700, Tmax = 0.746 | k = −13→12 |
26786 measured reflections | l = −19→20 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0567P)2 + 0.2297P] where P = (Fo2 + 2Fc2)/3 |
6725 reflections | (Δ/σ)max < 0.001 |
299 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C21H22ClN3O6S | γ = 103.313 (2)° |
Mr = 479.93 | V = 1103.12 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.1442 (3) Å | Mo Kα radiation |
b = 9.4376 (4) Å | µ = 0.31 mm−1 |
c = 14.0931 (6) Å | T = 296 K |
α = 108.262 (2)° | 0.38 × 0.32 × 0.27 mm |
β = 96.017 (2)° |
Bruker X8 APEX diffractometer | 6725 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4687 reflections with I > 2σ(I) |
Tmin = 0.700, Tmax = 0.746 | Rint = 0.030 |
26786 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.30 e Å−3 |
6725 reflections | Δρmin = −0.34 e Å−3 |
299 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 1.0486 (3) | 0.8525 (3) | 0.54237 (17) | 0.0722 (6) | |
H1A | 1.0445 | 0.9308 | 0.6042 | 0.108* | |
H1B | 1.0923 | 0.9013 | 0.4975 | 0.108* | |
H1C | 1.1106 | 0.7903 | 0.5579 | 0.108* | |
C2 | 0.8924 (3) | 0.7528 (3) | 0.49251 (17) | 0.0745 (6) | |
H2A | 0.8474 | 0.7029 | 0.5373 | 0.089* | |
H2B | 0.8285 | 0.8150 | 0.4774 | 0.089* | |
C3 | 0.8483 (2) | 0.4891 (2) | 0.38663 (16) | 0.0538 (4) | |
C4 | 0.8705 (2) | 0.3834 (2) | 0.28825 (15) | 0.0522 (4) | |
H4A | 0.8013 | 0.2809 | 0.2726 | 0.063* | |
H4B | 0.9742 | 0.3743 | 0.2970 | 0.063* | |
C5 | 0.84382 (17) | 0.43617 (19) | 0.19883 (13) | 0.0449 (4) | |
H5A | 0.9164 | 0.5362 | 0.2122 | 0.054* | |
H5B | 0.8617 | 0.3625 | 0.1387 | 0.054* | |
C6 | 0.64292 (16) | 0.56845 (16) | 0.16545 (11) | 0.0358 (3) | |
C7 | 0.48449 (16) | 0.52038 (16) | 0.13433 (11) | 0.0345 (3) | |
C8 | 0.44533 (15) | 0.36588 (15) | 0.13440 (11) | 0.0327 (3) | |
C9 | 0.28989 (16) | 0.27675 (16) | 0.10605 (11) | 0.0355 (3) | |
C10 | 0.18252 (17) | 0.34113 (19) | 0.07555 (13) | 0.0435 (4) | |
H10 | 0.0804 | 0.2829 | 0.0551 | 0.052* | |
C11 | 0.2236 (2) | 0.4947 (2) | 0.07452 (13) | 0.0477 (4) | |
H11 | 0.1477 | 0.5347 | 0.0529 | 0.057* | |
C12 | 0.37178 (19) | 0.58583 (18) | 0.10434 (12) | 0.0429 (3) | |
H12 | 0.3973 | 0.6873 | 0.1048 | 0.051* | |
C13 | 0.25249 (17) | −0.01017 (17) | 0.03603 (12) | 0.0423 (3) | |
C14 | 0.3172 (2) | 0.01302 (19) | −0.05230 (13) | 0.0488 (4) | |
H14A | 0.4034 | 0.1038 | −0.0286 | 0.073* | |
H14B | 0.2405 | 0.0264 | −0.0981 | 0.073* | |
H14C | 0.3494 | −0.0761 | −0.0872 | 0.073* | |
C15 | 0.28344 (17) | 0.00934 (18) | 0.26812 (12) | 0.0426 (3) | |
C16 | 0.4413 (2) | 0.0666 (2) | 0.29788 (16) | 0.0613 (5) | |
H16 | 0.4928 | 0.1571 | 0.2887 | 0.074* | |
C17 | 0.5205 (2) | −0.0119 (3) | 0.34089 (19) | 0.0711 (6) | |
H17 | 0.6266 | 0.0248 | 0.3596 | 0.085* | |
C18 | 0.4447 (2) | −0.1454 (2) | 0.35699 (14) | 0.0516 (4) | |
C19 | 0.2880 (2) | −0.2002 (2) | 0.32867 (15) | 0.0548 (4) | |
H19 | 0.2360 | −0.2887 | 0.3400 | 0.066* | |
C20 | 0.20833 (19) | −0.1236 (2) | 0.28343 (16) | 0.0552 (5) | |
H20 | 0.1025 | −0.1620 | 0.2630 | 0.066* | |
C21 | 0.4639 (3) | −0.3534 (3) | 0.4150 (2) | 0.0850 (7) | |
H21A | 0.3928 | −0.3336 | 0.4597 | 0.127* | |
H21B | 0.5405 | −0.3892 | 0.4452 | 0.127* | |
H21C | 0.4103 | −0.4315 | 0.3510 | 0.127* | |
N1 | 0.68752 (13) | 0.44938 (14) | 0.17929 (9) | 0.0359 (3) | |
N2 | 0.56842 (13) | 0.32172 (13) | 0.16155 (10) | 0.0366 (3) | |
N3 | 0.24731 (14) | 0.12398 (13) | 0.11297 (10) | 0.0388 (3) | |
O1 | 0.90147 (18) | 0.63540 (16) | 0.39826 (10) | 0.0687 (4) | |
O2A | 0.827 (4) | 0.460 (2) | 0.4645 (11) | 0.074 (4) | 0.40 (5) |
O2B | 0.763 (3) | 0.4365 (10) | 0.433 (2) | 0.097 (5) | 0.60 (5) |
O3 | 0.20543 (16) | −0.13637 (13) | 0.04358 (10) | 0.0594 (3) | |
O4 | 0.21707 (17) | 0.26817 (15) | 0.28507 (11) | 0.0632 (4) | |
O5 | 0.02109 (13) | 0.02348 (18) | 0.18811 (13) | 0.0709 (4) | |
O6 | 0.53520 (17) | −0.21420 (19) | 0.39901 (13) | 0.0750 (4) | |
S1 | 0.17842 (4) | 0.11051 (5) | 0.21770 (4) | 0.04718 (12) | |
Cl1 | 0.76852 (5) | 0.74258 (5) | 0.18505 (4) | 0.05352 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0799 (15) | 0.0598 (12) | 0.0636 (13) | 0.0125 (11) | −0.0014 (11) | 0.0131 (10) |
C2 | 0.0808 (15) | 0.0679 (14) | 0.0560 (12) | 0.0081 (11) | 0.0137 (11) | 0.0050 (10) |
C3 | 0.0460 (9) | 0.0567 (11) | 0.0697 (12) | 0.0192 (8) | 0.0124 (8) | 0.0329 (9) |
C4 | 0.0395 (8) | 0.0446 (9) | 0.0715 (12) | 0.0145 (7) | 0.0029 (8) | 0.0193 (8) |
C5 | 0.0288 (7) | 0.0433 (8) | 0.0569 (10) | 0.0070 (6) | 0.0096 (6) | 0.0117 (7) |
C6 | 0.0376 (7) | 0.0283 (7) | 0.0378 (7) | 0.0020 (5) | 0.0082 (6) | 0.0115 (5) |
C7 | 0.0369 (7) | 0.0280 (6) | 0.0366 (7) | 0.0069 (5) | 0.0079 (6) | 0.0099 (5) |
C8 | 0.0319 (7) | 0.0262 (6) | 0.0379 (7) | 0.0070 (5) | 0.0084 (5) | 0.0088 (5) |
C9 | 0.0305 (6) | 0.0278 (6) | 0.0434 (8) | 0.0054 (5) | 0.0076 (6) | 0.0078 (5) |
C10 | 0.0316 (7) | 0.0413 (8) | 0.0528 (9) | 0.0101 (6) | 0.0055 (6) | 0.0106 (7) |
C11 | 0.0443 (9) | 0.0453 (9) | 0.0557 (10) | 0.0208 (7) | 0.0054 (7) | 0.0159 (7) |
C12 | 0.0506 (9) | 0.0329 (7) | 0.0484 (9) | 0.0156 (6) | 0.0094 (7) | 0.0157 (6) |
C13 | 0.0380 (8) | 0.0296 (7) | 0.0484 (9) | 0.0052 (6) | −0.0055 (6) | 0.0063 (6) |
C14 | 0.0582 (10) | 0.0387 (8) | 0.0445 (9) | 0.0178 (7) | 0.0012 (7) | 0.0072 (7) |
C15 | 0.0344 (7) | 0.0408 (8) | 0.0494 (9) | 0.0031 (6) | 0.0109 (6) | 0.0155 (7) |
C16 | 0.0376 (9) | 0.0613 (12) | 0.0818 (14) | −0.0078 (8) | 0.0013 (9) | 0.0393 (10) |
C17 | 0.0359 (9) | 0.0798 (15) | 0.0981 (16) | −0.0058 (9) | −0.0025 (9) | 0.0521 (13) |
C18 | 0.0457 (9) | 0.0578 (11) | 0.0535 (10) | 0.0098 (8) | 0.0101 (7) | 0.0253 (8) |
C19 | 0.0460 (9) | 0.0487 (10) | 0.0719 (12) | 0.0050 (7) | 0.0163 (8) | 0.0282 (9) |
C20 | 0.0339 (8) | 0.0500 (10) | 0.0798 (13) | 0.0009 (7) | 0.0107 (8) | 0.0277 (9) |
C21 | 0.0747 (15) | 0.0906 (18) | 0.117 (2) | 0.0263 (13) | 0.0257 (14) | 0.0693 (16) |
N1 | 0.0290 (6) | 0.0305 (6) | 0.0447 (7) | 0.0029 (4) | 0.0062 (5) | 0.0124 (5) |
N2 | 0.0291 (6) | 0.0274 (6) | 0.0511 (7) | 0.0045 (4) | 0.0076 (5) | 0.0130 (5) |
N3 | 0.0328 (6) | 0.0280 (6) | 0.0501 (7) | 0.0027 (5) | 0.0085 (5) | 0.0102 (5) |
O1 | 0.0901 (11) | 0.0518 (8) | 0.0469 (7) | −0.0014 (7) | 0.0122 (7) | 0.0092 (6) |
O2A | 0.090 (8) | 0.069 (5) | 0.079 (5) | 0.023 (5) | 0.029 (5) | 0.044 (3) |
O2B | 0.106 (9) | 0.078 (3) | 0.117 (9) | 0.013 (4) | 0.069 (8) | 0.041 (4) |
O3 | 0.0734 (9) | 0.0294 (6) | 0.0623 (8) | 0.0020 (5) | −0.0003 (6) | 0.0112 (5) |
O4 | 0.0792 (9) | 0.0511 (7) | 0.0686 (8) | 0.0254 (7) | 0.0410 (7) | 0.0198 (6) |
O5 | 0.0303 (6) | 0.0794 (10) | 0.1197 (12) | 0.0092 (6) | 0.0205 (7) | 0.0597 (9) |
O6 | 0.0554 (8) | 0.0882 (11) | 0.0985 (12) | 0.0154 (7) | 0.0105 (8) | 0.0603 (10) |
S1 | 0.03440 (19) | 0.0441 (2) | 0.0676 (3) | 0.00900 (16) | 0.02084 (18) | 0.02352 (19) |
Cl1 | 0.0495 (2) | 0.0355 (2) | 0.0679 (3) | −0.00609 (16) | 0.00440 (19) | 0.02249 (18) |
C1—C2 | 1.475 (3) | C11—H11 | 0.9300 |
C1—H1A | 0.9600 | C12—H12 | 0.9300 |
C1—H1B | 0.9600 | C13—O3 | 1.2116 (19) |
C1—H1C | 0.9600 | C13—N3 | 1.3996 (19) |
C2—O1 | 1.464 (2) | C13—C14 | 1.488 (2) |
C2—H2A | 0.9700 | C14—H14A | 0.9600 |
C2—H2B | 0.9700 | C14—H14B | 0.9600 |
C3—O2B | 1.193 (6) | C14—H14C | 0.9600 |
C3—O2A | 1.233 (10) | C15—C20 | 1.377 (2) |
C3—O1 | 1.305 (2) | C15—C16 | 1.387 (2) |
C3—C4 | 1.498 (3) | C15—S1 | 1.7446 (18) |
C4—C5 | 1.510 (3) | C16—C17 | 1.370 (3) |
C4—H4A | 0.9700 | C16—H16 | 0.9300 |
C4—H4B | 0.9700 | C17—C18 | 1.389 (3) |
C5—N1 | 1.4680 (19) | C17—H17 | 0.9300 |
C5—H5A | 0.9700 | C18—O6 | 1.357 (2) |
C5—H5B | 0.9700 | C18—C19 | 1.375 (2) |
C6—N1 | 1.3413 (19) | C19—C20 | 1.377 (3) |
C6—C7 | 1.392 (2) | C19—H19 | 0.9300 |
C6—Cl1 | 1.6959 (14) | C20—H20 | 0.9300 |
C7—C12 | 1.410 (2) | C21—O6 | 1.423 (3) |
C7—C8 | 1.4194 (19) | C21—H21A | 0.9600 |
C8—N2 | 1.3464 (18) | C21—H21B | 0.9600 |
C8—C9 | 1.4168 (18) | C21—H21C | 0.9600 |
C9—C10 | 1.367 (2) | N1—N2 | 1.3602 (15) |
C9—N3 | 1.4412 (18) | N3—S1 | 1.6932 (14) |
C10—C11 | 1.416 (2) | O4—S1 | 1.4292 (13) |
C10—H10 | 0.9300 | O5—S1 | 1.4260 (13) |
C11—C12 | 1.367 (2) | ||
C2—C1—H1A | 109.5 | C7—C12—H12 | 121.2 |
C2—C1—H1B | 109.5 | O3—C13—N3 | 120.00 (16) |
H1A—C1—H1B | 109.5 | O3—C13—C14 | 123.63 (15) |
C2—C1—H1C | 109.5 | N3—C13—C14 | 116.37 (13) |
H1A—C1—H1C | 109.5 | C13—C14—H14A | 109.5 |
H1B—C1—H1C | 109.5 | C13—C14—H14B | 109.5 |
O1—C2—C1 | 108.42 (19) | H14A—C14—H14B | 109.5 |
O1—C2—H2A | 110.0 | C13—C14—H14C | 109.5 |
C1—C2—H2A | 110.0 | H14A—C14—H14C | 109.5 |
O1—C2—H2B | 110.0 | H14B—C14—H14C | 109.5 |
C1—C2—H2B | 110.0 | C20—C15—C16 | 119.85 (17) |
H2A—C2—H2B | 108.4 | C20—C15—S1 | 119.72 (13) |
O2B—C3—O2A | 30.9 (5) | C16—C15—S1 | 120.34 (13) |
O2B—C3—O1 | 126.8 (4) | C17—C16—C15 | 119.22 (16) |
O2A—C3—O1 | 116.2 (10) | C17—C16—H16 | 120.4 |
O2B—C3—C4 | 119.1 (8) | C15—C16—H16 | 120.4 |
O2A—C3—C4 | 128.4 (6) | C16—C17—C18 | 120.96 (17) |
O1—C3—C4 | 112.24 (16) | C16—C17—H17 | 119.5 |
C3—C4—C5 | 114.43 (15) | C18—C17—H17 | 119.5 |
C3—C4—H4A | 108.7 | O6—C18—C19 | 124.74 (17) |
C5—C4—H4A | 108.7 | O6—C18—C17 | 115.74 (16) |
C3—C4—H4B | 108.7 | C19—C18—C17 | 119.50 (18) |
C5—C4—H4B | 108.7 | C18—C19—C20 | 119.67 (16) |
H4A—C4—H4B | 107.6 | C18—C19—H19 | 120.2 |
N1—C5—C4 | 111.86 (13) | C20—C19—H19 | 120.2 |
N1—C5—H5A | 109.2 | C19—C20—C15 | 120.77 (15) |
C4—C5—H5A | 109.2 | C19—C20—H20 | 119.6 |
N1—C5—H5B | 109.2 | C15—C20—H20 | 119.6 |
C4—C5—H5B | 109.2 | O6—C21—H21A | 109.5 |
H5A—C5—H5B | 107.9 | O6—C21—H21B | 109.5 |
N1—C6—C7 | 108.02 (12) | H21A—C21—H21B | 109.5 |
N1—C6—Cl1 | 122.44 (11) | O6—C21—H21C | 109.5 |
C7—C6—Cl1 | 129.55 (12) | H21A—C21—H21C | 109.5 |
C6—C7—C12 | 135.94 (14) | H21B—C21—H21C | 109.5 |
C6—C7—C8 | 102.85 (13) | C6—N1—N2 | 112.93 (12) |
C12—C7—C8 | 121.18 (13) | C6—N1—C5 | 128.36 (12) |
N2—C8—C9 | 127.74 (13) | N2—N1—C5 | 118.31 (12) |
N2—C8—C7 | 112.71 (12) | C8—N2—N1 | 103.47 (11) |
C9—C8—C7 | 119.54 (13) | C13—N3—C9 | 123.30 (13) |
C10—C9—C8 | 118.45 (13) | C13—N3—S1 | 120.09 (11) |
C10—C9—N3 | 121.44 (13) | C9—N3—S1 | 116.51 (10) |
C8—C9—N3 | 120.08 (13) | C3—O1—C2 | 118.52 (17) |
C9—C10—C11 | 121.33 (14) | C18—O6—C21 | 118.14 (16) |
C9—C10—H10 | 119.3 | O5—S1—O4 | 118.40 (9) |
C11—C10—H10 | 119.3 | O5—S1—N3 | 109.15 (8) |
C12—C11—C10 | 121.85 (15) | O4—S1—N3 | 103.71 (7) |
C12—C11—H11 | 119.1 | O5—S1—C15 | 109.27 (8) |
C10—C11—H11 | 119.1 | O4—S1—C15 | 109.37 (9) |
C11—C12—C7 | 117.60 (14) | N3—S1—C15 | 106.18 (7) |
C11—C12—H12 | 121.2 | ||
O2B—C3—C4—C5 | 126 (2) | C7—C6—N1—C5 | 171.20 (14) |
O2A—C3—C4—C5 | 161.7 (19) | Cl1—C6—N1—C5 | −8.9 (2) |
O1—C3—C4—C5 | −39.5 (2) | C4—C5—N1—C6 | 130.76 (16) |
C3—C4—C5—N1 | −59.63 (19) | C4—C5—N1—N2 | −57.11 (18) |
N1—C6—C7—C12 | −176.92 (16) | C9—C8—N2—N1 | 179.12 (14) |
Cl1—C6—C7—C12 | 3.2 (3) | C7—C8—N2—N1 | 0.16 (16) |
N1—C6—C7—C8 | 1.25 (15) | C6—N1—N2—C8 | 0.70 (16) |
Cl1—C6—C7—C8 | −178.68 (12) | C5—N1—N2—C8 | −172.61 (13) |
C6—C7—C8—N2 | −0.88 (16) | O3—C13—N3—C9 | −175.04 (14) |
C12—C7—C8—N2 | 177.63 (13) | C14—C13—N3—C9 | 4.8 (2) |
C6—C7—C8—C9 | −179.94 (13) | O3—C13—N3—S1 | 1.2 (2) |
C12—C7—C8—C9 | −1.4 (2) | C14—C13—N3—S1 | −179.00 (11) |
N2—C8—C9—C10 | −176.42 (14) | C10—C9—N3—C13 | 97.10 (18) |
C7—C8—C9—C10 | 2.5 (2) | C8—C9—N3—C13 | −85.05 (18) |
N2—C8—C9—N3 | 5.7 (2) | C10—C9—N3—S1 | −79.22 (17) |
C7—C8—C9—N3 | −175.44 (12) | C8—C9—N3—S1 | 98.63 (14) |
C8—C9—C10—C11 | −1.6 (2) | O2B—C3—O1—C2 | 18 (2) |
N3—C9—C10—C11 | 176.25 (14) | O2A—C3—O1—C2 | −16.5 (14) |
C9—C10—C11—C12 | −0.4 (3) | C4—C3—O1—C2 | −178.05 (17) |
C10—C11—C12—C7 | 1.5 (2) | C1—C2—O1—C3 | 121.8 (2) |
C6—C7—C12—C11 | 177.37 (16) | C19—C18—O6—C21 | 0.2 (3) |
C8—C7—C12—C11 | −0.5 (2) | C17—C18—O6—C21 | −178.6 (2) |
C20—C15—C16—C17 | 1.0 (3) | C13—N3—S1—O5 | −63.19 (14) |
S1—C15—C16—C17 | 177.49 (17) | C9—N3—S1—O5 | 113.25 (12) |
C15—C16—C17—C18 | −1.4 (3) | C13—N3—S1—O4 | 169.72 (12) |
C16—C17—C18—O6 | 179.3 (2) | C9—N3—S1—O4 | −13.83 (13) |
C16—C17—C18—C19 | 0.5 (3) | C13—N3—S1—C15 | 54.49 (13) |
O6—C18—C19—C20 | −177.76 (18) | C9—N3—S1—C15 | −129.06 (11) |
C17—C18—C19—C20 | 0.9 (3) | C20—C15—S1—O5 | −6.70 (18) |
C18—C19—C20—C15 | −1.4 (3) | C16—C15—S1—O5 | 176.77 (16) |
C16—C15—C20—C19 | 0.4 (3) | C20—C15—S1—O4 | 124.38 (15) |
S1—C15—C20—C19 | −176.12 (15) | C16—C15—S1—O4 | −52.16 (17) |
C7—C6—N1—N2 | −1.29 (17) | C20—C15—S1—N3 | −124.30 (15) |
Cl1—C6—N1—N2 | 178.64 (10) | C16—C15—S1—N3 | 59.16 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O4i | 0.97 | 2.58 | 3.438 (3) | 148 |
C21—H21A···O2Bii | 0.96 | 2.44 | 3.273 (7) | 144 |
C21—H21A···O2Aii | 0.96 | 2.60 | 3.43 (2) | 145 |
C2—H2B···O6iii | 0.97 | 2.71 | 3.510 (3) | 140 |
C14—H14C···N2iv | 0.96 | 2.55 | 3.501 (2) | 173 |
C14—H14B···O5v | 0.96 | 2.45 | 3.348 (2) | 155 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x, y+1, z; (iv) −x+1, −y, −z; (v) −x, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O4i | 0.97 | 2.58 | 3.438 (3) | 148 |
C21—H21A···O2Bii | 0.96 | 2.44 | 3.273 (7) | 144 |
C21—H21A···O2Aii | 0.96 | 2.60 | 3.43 (2) | 145 |
C2—H2B···O6iii | 0.97 | 2.71 | 3.510 (3) | 140 |
C14—H14C···N2iv | 0.96 | 2.55 | 3.501 (2) | 173 |
C14—H14B···O5v | 0.96 | 2.45 | 3.348 (2) | 155 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x, y+1, z; (iv) −x+1, −y, −z; (v) −x, −y, −z. |
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
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chicha, H., Kouakou, A., Rakib, E. M., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o1353. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kaltenbach, R. F., Patel, M., Waltermire, R. E., Harris, G. D., Stone, B. R. P., Klabe, R. M., Garber, S., Bacheler, L. T., Cordova, B. C., Logue, K., Wright, M. R., Erickson-Viitanen, S. & Trainor, G. L. (2003). Bioorg. Med. Chem. Lett. 13, 605–686. Web of Science CrossRef PubMed CAS Google Scholar
Lohou, E., Sopkova, J., Schumann, P., Boulouard, M., Stiebing, S., Rault, S. & Collot, V. (2012). Bioorg. Med. Chem. 20, 5296–5304. Web of Science CSD CrossRef CAS PubMed Google Scholar
Salerno, L., Modica, M. N., Romeo, G., Pittala, V., Siracusa, M. A., Amato, M. E., Acquaviva, R., Di Giacomo, C. & Sorrenti, V. (2012). Eur. J. Med. Chem. 49, 118–126. Web of Science CrossRef CAS PubMed 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
Thangadurai, A., Minu, M., Wakode, S., Agrawal, S. & Narasimhan, B. (2012). Med. Chem. Res. 21, 1509–1523. Web of Science CrossRef CAS 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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