organic compounds
H-1-benzothieno[3,2-b]pyran-3-carboxylate
of ethyl 2-amino-4-(4-chlorophenyl)-4aDépartement de Chimie, Faculté des Sciences, Dhar Mehraz, BP 1796 Atlas, 30000 Fes, Morocco, and bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: m.bakhouch@yahoo.fr
The title compound, C20H16ClNO3S, is built up from three fused rings, one five- and two six-membered rings, linked to a 3-ethoxycarbonyl group and to a 4-chlorophenyl ring. The hydropyran ring has a flattened with the C atom substituted by the 4-chlorophenyl ring as the flap (displaced by 0.077 (2) Å from the plane through the other atoms). The fused three-ring system is quasi-planar (r.m.s. deviation = 0.057 Å), with the largest deviation from the mean plane being 0.106 (1) Å for the C atom substituted by the 4-chlorophenyl ring. The 4-chlorophenyl ring is approximately perpendicular to the mean plane of the fused ring system, as indicated by the dihedral angle of 77.32 (6)° between their mean planes. There is an intramolecular N—H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R22(12) ring motif. There are also short intermolecular Cl⋯O interactions present [3.1226 (12) Å] between neighbouring molecules.
Keywords: crystal structure; thioaurones; thiophenones; benzothienopyran; N—H⋯O hydrogen bonds; inversion dimers; Cl⋯O short contact..
CCDC reference: 1415291
1. Related literature
For the reactivity of the thioaurones [(Z)-2-arylidenebenzo[b]thiophen-3(2H)-ones], see: Boughaleb et al. (2010, 2011); Bakhouch et al. (2014, 2015); Cabiddu et al. (2002); Pradhan et al. (2005). For the preparation of the title compound using condensation reactions, see: Daisley et al. (1982).
2. Experimental
2.1. Crystal data
|
2.3. Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013, PLATON and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 1415291
https://doi.org/10.1107/S2056989015014085/su5182sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014085/su5182Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015014085/su5182Isup3.cml
During our studies on the synthesis of
(Boughaleb et al., 2010,2011), we decided to investigate thioaurones [(Z)-2-arylidenebenzo[b]thiophen-3(2H)-ones] as potential starting materials (Cabiddu et al., 2002; Pradhan et al., 2005). In continuation of our previous work (Boughaleb et al., 2011; Bakhouch et al., 2014), we described herein the behaviour of ethyl cyanoacetate with (Z)-2-(4-chlorobenzylidene)benzo[b]thiophen-3(2H)-one. The title compound, was prepared by the action of ethyl cyanoacetate on (Z)-2-(4-chlorobenzylidene)benzo[b]thiophen-3(2H)-one. The reaction was carried out in hot alcohol in the presence of piperidine as a basic catalyst (Daisley et al., 1982). Initially the condensation gave the Michael adducts which undergoes intramolecular to afford an imino-pyran. The subsequent tautomeric transformation gives rise to the title compound, whose we report on herein.The molecule of the title compound, Fig. 1, is formed by three fused rings linked to an ethyl-3-carboxylate group and to a 4-chlorophenyl. The three fused rings (S1/C1—C11/O1) are nearly coplanar, with the maximum deviation from the mean plane being -0.106 (1) Å for atom C9. Its mean plane make a dihedral angle of 77.32 (6)° with the attached 4-chlorophenyl ring. The pyran ring has a flat
with atom C9, substituted by the 4-chlorophenyl ring, as the flap. There is an intramolecular N—H···O hydrogen bond, involving the amine and carboxyl ate group, forming an S(6) ring motif (Fig. 1 and Table 1).In the crystal, molecules are linked by pairs of N—H···O hydrogen bonds forming inversion dimers with an R22(12) ring motif (Table 1 and Fig. 2). There are also short intermolecular Cl1···O1i interactions present between neighbouring molecules [3.1226 (12) Å; symmetry code: (i) x, y+1, z; see Fig. 2].
In a 100 ml flask equipped with a condenser was dissolved 4 mmol of (Z)-2-(4-chlorobenzylidene)-1-benzo[b]thiophen-3(2H)-one and 5 mmol of ethyl cyanoacetate in 30 ml of ethanol. Then, 1 ml of piperidine was added, and the reaction mixture was refluxed for 6 h. Thin layer
revealed the formation of a single product. The organic phase was evaporated under reduce pressure. The resulting residue was recrystallized from ethanol (yield: 67%; m.p.: 405 K). Colourless block-like crystals of the title compound were obtained by slow evaporation of a solution in ethanol.During our studies on the synthesis of
(Boughaleb et al., 2010,2011), we decided to investigate thioaurones [(Z)-2-arylidenebenzo[b]thiophen-3(2H)-ones] as potential starting materials (Cabiddu et al., 2002; Pradhan et al., 2005). In continuation of our previous work (Boughaleb et al., 2011; Bakhouch et al., 2014), we described herein the behaviour of ethyl cyanoacetate with (Z)-2-(4-chlorobenzylidene)benzo[b]thiophen-3(2H)-one. The title compound, was prepared by the action of ethyl cyanoacetate on (Z)-2-(4-chlorobenzylidene)benzo[b]thiophen-3(2H)-one. The reaction was carried out in hot alcohol in the presence of piperidine as a basic catalyst (Daisley et al., 1982). Initially the condensation gave the Michael adducts which undergoes intramolecular to afford an imino-pyran. The subsequent tautomeric transformation gives rise to the title compound, whose we report on herein.The molecule of the title compound, Fig. 1, is formed by three fused rings linked to an ethyl-3-carboxylate group and to a 4-chlorophenyl. The three fused rings (S1/C1—C11/O1) are nearly coplanar, with the maximum deviation from the mean plane being -0.106 (1) Å for atom C9. Its mean plane make a dihedral angle of 77.32 (6)° with the attached 4-chlorophenyl ring. The pyran ring has a flat
with atom C9, substituted by the 4-chlorophenyl ring, as the flap. There is an intramolecular N—H···O hydrogen bond, involving the amine and carboxyl ate group, forming an S(6) ring motif (Fig. 1 and Table 1).In the crystal, molecules are linked by pairs of N—H···O hydrogen bonds forming inversion dimers with an R22(12) ring motif (Table 1 and Fig. 2). There are also short intermolecular Cl1···O1i interactions present between neighbouring molecules [3.1226 (12) Å; symmetry code: (i) x, y+1, z; see Fig. 2].
For the reactivity of thioaurones [(Z)-2-arylidenebenzo[b]thiophen-3(2H)-ones], see: Boughaleb et al. (2010, 2011); Bakhouch et al. (2014, 2015); Cabiddu et al. (2002); Pradhan et al. (2005). For the preparation of the title compound using condensation reactions, see: Daisley et al. (1982).
In a 100 ml flask equipped with a condenser was dissolved 4 mmol of (Z)-2-(4-chlorobenzylidene)-1-benzo[b]thiophen-3(2H)-one and 5 mmol of ethyl cyanoacetate in 30 ml of ethanol. Then, 1 ml of piperidine was added, and the reaction mixture was refluxed for 6 h. Thin layer
revealed the formation of a single product. The organic phase was evaporated under reduce pressure. The resulting residue was recrystallized from ethanol (yield: 67%; m.p.: 405 K). Colourless block-like crystals of the title compound were obtained by slow evaporation of a solution in ethanol. detailsCrystal data, data collection and structure
details are summarized in Table 2. H atoms were located in a difference map and treated as riding: N—H = 0.86 Å, C–H = 0.93 - 0.98Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(N,C) for other H atoms.Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).C20H16ClNO3S | Z = 2 |
Mr = 385.85 | F(000) = 400 |
Triclinic, P1 | Dx = 1.435 Mg m−3 |
a = 8.3606 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.9186 (6) Å | Cell parameters from 3892 reflections |
c = 11.0971 (6) Å | θ = 2.3–27.0° |
α = 104.592 (2)° | µ = 0.35 mm−1 |
β = 106.849 (2)° | T = 296 K |
γ = 102.174 (2)° | Block, colourless |
V = 893.09 (8) Å3 | 0.42 × 0.31 × 0.26 mm |
Bruker X8 APEX diffractometer | 3892 independent reflections |
Radiation source: fine-focus sealed tube | 3422 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 27.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −10→10 |
Tmin = 0.673, Tmax = 0.746 | k = −13→13 |
22918 measured reflections | l = −14→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0548P)2 + 0.2464P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3892 reflections | Δρmax = 0.30 e Å−3 |
235 parameters | Δρmin = −0.24 e Å−3 |
C20H16ClNO3S | γ = 102.174 (2)° |
Mr = 385.85 | V = 893.09 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.3606 (4) Å | Mo Kα radiation |
b = 10.9186 (6) Å | µ = 0.35 mm−1 |
c = 11.0971 (6) Å | T = 296 K |
α = 104.592 (2)° | 0.42 × 0.31 × 0.26 mm |
β = 106.849 (2)° |
Bruker X8 APEX diffractometer | 3892 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3422 reflections with I > 2σ(I) |
Tmin = 0.673, Tmax = 0.746 | Rint = 0.029 |
22918 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.30 e Å−3 |
3892 reflections | Δρmin = −0.24 e Å−3 |
235 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.35626 (19) | 0.05325 (15) | 0.88366 (15) | 0.0351 (3) | |
C2 | 0.2174 (2) | 0.01998 (18) | 0.92720 (18) | 0.0471 (4) | |
H2 | 0.2128 | 0.0769 | 1.0033 | 0.057* | |
C3 | 0.0882 (2) | −0.0988 (2) | 0.85487 (19) | 0.0542 (4) | |
H3 | −0.0054 | −0.1223 | 0.8824 | 0.065* | |
C4 | 0.0936 (2) | −0.1852 (2) | 0.74085 (19) | 0.0539 (4) | |
H4 | 0.0034 | −0.2648 | 0.6931 | 0.065* | |
C5 | 0.2317 (2) | −0.15375 (17) | 0.69832 (16) | 0.0432 (4) | |
H5 | 0.2359 | −0.2120 | 0.6229 | 0.052* | |
C6 | 0.36455 (18) | −0.03341 (14) | 0.77004 (14) | 0.0325 (3) | |
C7 | 0.51995 (18) | 0.02422 (13) | 0.74848 (13) | 0.0296 (3) | |
C8 | 0.62124 (18) | 0.14449 (13) | 0.83590 (13) | 0.0294 (3) | |
C9 | 0.78415 (17) | 0.22422 (13) | 0.82693 (13) | 0.0281 (3) | |
H9 | 0.8804 | 0.2515 | 0.9131 | 0.034* | |
C10 | 0.82868 (17) | 0.13392 (13) | 0.72085 (13) | 0.0298 (3) | |
C11 | 0.71717 (18) | 0.01172 (13) | 0.63660 (13) | 0.0298 (3) | |
C12 | 0.75379 (16) | 0.34879 (13) | 0.79785 (13) | 0.0274 (3) | |
C13 | 0.7782 (2) | 0.46098 (14) | 0.90231 (14) | 0.0354 (3) | |
H13 | 0.8217 | 0.4617 | 0.9898 | 0.042* | |
C14 | 0.7389 (2) | 0.57212 (14) | 0.87879 (15) | 0.0385 (3) | |
H14 | 0.7540 | 0.6462 | 0.9494 | 0.046* | |
C15 | 0.67728 (18) | 0.57080 (13) | 0.74900 (15) | 0.0346 (3) | |
C16 | 0.6569 (2) | 0.46233 (15) | 0.64347 (15) | 0.0396 (3) | |
H16 | 0.6191 | 0.4637 | 0.5564 | 0.047* | |
C17 | 0.69348 (19) | 0.35146 (14) | 0.66880 (14) | 0.0349 (3) | |
H17 | 0.6772 | 0.2774 | 0.5977 | 0.042* | |
C18 | 0.99172 (18) | 0.18273 (14) | 0.70204 (14) | 0.0338 (3) | |
C19 | 1.2395 (2) | 0.37234 (19) | 0.76685 (18) | 0.0508 (4) | |
H19A | 1.2933 | 0.3086 | 0.7312 | 0.061* | |
H19B | 1.3263 | 0.4365 | 0.8501 | 0.061* | |
C20 | 1.1832 (4) | 0.4415 (3) | 0.6705 (3) | 0.1006 (10) | |
H20A | 1.2833 | 0.4864 | 0.6551 | 0.151* | |
H20B | 1.1310 | 0.5052 | 0.7063 | 0.151* | |
H20C | 1.0989 | 0.3777 | 0.5877 | 0.151* | |
N1 | 0.74061 (17) | −0.07170 (12) | 0.53678 (13) | 0.0404 (3) | |
H1A | 0.8348 | −0.0502 | 0.5199 | 0.048* | |
H1B | 0.6615 | −0.1469 | 0.4894 | 0.048* | |
O1 | 0.55816 (13) | −0.04447 (10) | 0.64299 (10) | 0.0341 (2) | |
O2 | 1.09024 (13) | 0.30414 (11) | 0.79199 (11) | 0.0412 (3) | |
O3 | 1.03951 (15) | 0.12634 (12) | 0.61632 (12) | 0.0503 (3) | |
S1 | 0.53387 (5) | 0.19821 (4) | 0.95704 (4) | 0.03808 (12) | |
Cl1 | 0.62208 (6) | 0.70800 (4) | 0.71743 (4) | 0.05029 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0365 (7) | 0.0397 (7) | 0.0395 (7) | 0.0175 (6) | 0.0224 (6) | 0.0158 (6) |
C2 | 0.0454 (9) | 0.0575 (10) | 0.0523 (9) | 0.0213 (8) | 0.0346 (8) | 0.0170 (8) |
C3 | 0.0390 (9) | 0.0698 (12) | 0.0624 (11) | 0.0136 (8) | 0.0341 (8) | 0.0206 (9) |
C4 | 0.0365 (8) | 0.0595 (11) | 0.0591 (11) | 0.0042 (8) | 0.0223 (8) | 0.0119 (9) |
C5 | 0.0378 (8) | 0.0492 (9) | 0.0420 (8) | 0.0101 (7) | 0.0203 (7) | 0.0099 (7) |
C6 | 0.0316 (7) | 0.0393 (7) | 0.0351 (7) | 0.0159 (6) | 0.0179 (6) | 0.0158 (6) |
C7 | 0.0324 (7) | 0.0354 (7) | 0.0311 (6) | 0.0175 (5) | 0.0190 (5) | 0.0131 (5) |
C8 | 0.0348 (7) | 0.0329 (7) | 0.0307 (6) | 0.0173 (5) | 0.0202 (5) | 0.0121 (5) |
C9 | 0.0306 (6) | 0.0313 (6) | 0.0270 (6) | 0.0136 (5) | 0.0150 (5) | 0.0087 (5) |
C10 | 0.0312 (7) | 0.0333 (7) | 0.0335 (7) | 0.0163 (5) | 0.0192 (5) | 0.0116 (5) |
C11 | 0.0336 (7) | 0.0330 (7) | 0.0331 (6) | 0.0172 (5) | 0.0198 (5) | 0.0133 (5) |
C12 | 0.0250 (6) | 0.0296 (6) | 0.0292 (6) | 0.0092 (5) | 0.0134 (5) | 0.0076 (5) |
C13 | 0.0428 (8) | 0.0348 (7) | 0.0273 (6) | 0.0137 (6) | 0.0131 (6) | 0.0063 (5) |
C14 | 0.0444 (8) | 0.0291 (7) | 0.0364 (7) | 0.0118 (6) | 0.0135 (6) | 0.0023 (6) |
C15 | 0.0305 (7) | 0.0283 (7) | 0.0430 (8) | 0.0097 (5) | 0.0104 (6) | 0.0113 (6) |
C16 | 0.0444 (8) | 0.0427 (8) | 0.0309 (7) | 0.0170 (7) | 0.0100 (6) | 0.0123 (6) |
C17 | 0.0405 (8) | 0.0347 (7) | 0.0280 (6) | 0.0148 (6) | 0.0122 (6) | 0.0053 (5) |
C18 | 0.0327 (7) | 0.0387 (7) | 0.0360 (7) | 0.0155 (6) | 0.0183 (6) | 0.0115 (6) |
C19 | 0.0330 (8) | 0.0570 (10) | 0.0541 (10) | 0.0021 (7) | 0.0224 (7) | 0.0070 (8) |
C20 | 0.0660 (15) | 0.115 (2) | 0.130 (2) | 0.0027 (15) | 0.0361 (16) | 0.078 (2) |
N1 | 0.0442 (7) | 0.0356 (6) | 0.0458 (7) | 0.0121 (5) | 0.0308 (6) | 0.0040 (5) |
O1 | 0.0347 (5) | 0.0343 (5) | 0.0358 (5) | 0.0099 (4) | 0.0222 (4) | 0.0054 (4) |
O2 | 0.0327 (5) | 0.0451 (6) | 0.0417 (6) | 0.0059 (4) | 0.0211 (5) | 0.0039 (5) |
O3 | 0.0465 (6) | 0.0504 (7) | 0.0569 (7) | 0.0128 (5) | 0.0373 (6) | 0.0029 (5) |
S1 | 0.0447 (2) | 0.0385 (2) | 0.0392 (2) | 0.01531 (16) | 0.02879 (17) | 0.00859 (15) |
Cl1 | 0.0518 (2) | 0.0325 (2) | 0.0608 (3) | 0.01558 (17) | 0.00947 (19) | 0.01663 (18) |
C1—C2 | 1.396 (2) | C12—C17 | 1.3837 (19) |
C1—C6 | 1.4025 (19) | C12—C13 | 1.3885 (18) |
C1—S1 | 1.7412 (16) | C13—C14 | 1.388 (2) |
C2—C3 | 1.369 (3) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C15 | 1.377 (2) |
C3—C4 | 1.394 (3) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—C16 | 1.380 (2) |
C4—C5 | 1.379 (2) | C15—Cl1 | 1.7441 (14) |
C4—H4 | 0.9300 | C16—C17 | 1.384 (2) |
C5—C6 | 1.393 (2) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—C7 | 1.4327 (18) | C18—O3 | 1.2134 (17) |
C7—C8 | 1.340 (2) | C18—O2 | 1.3521 (18) |
C7—O1 | 1.3821 (15) | C19—O2 | 1.4507 (18) |
C8—C9 | 1.4983 (18) | C19—C20 | 1.484 (3) |
C8—S1 | 1.7428 (13) | C19—H19A | 0.9700 |
C9—C10 | 1.5235 (16) | C19—H19B | 0.9700 |
C9—C12 | 1.5289 (17) | C20—H20A | 0.9600 |
C9—H9 | 0.9800 | C20—H20B | 0.9600 |
C10—C11 | 1.366 (2) | C20—H20C | 0.9600 |
C10—C18 | 1.4492 (19) | N1—H1A | 0.8600 |
C11—N1 | 1.3371 (17) | N1—H1B | 0.8600 |
C11—O1 | 1.3717 (16) | ||
C2—C1—C6 | 120.93 (15) | C13—C12—C9 | 119.77 (12) |
C2—C1—S1 | 126.81 (13) | C14—C13—C12 | 121.31 (13) |
C6—C1—S1 | 112.26 (10) | C14—C13—H13 | 119.3 |
C3—C2—C1 | 118.18 (15) | C12—C13—H13 | 119.3 |
C3—C2—H2 | 120.9 | C15—C14—C13 | 118.84 (13) |
C1—C2—H2 | 120.9 | C15—C14—H14 | 120.6 |
C2—C3—C4 | 121.53 (15) | C13—C14—H14 | 120.6 |
C2—C3—H3 | 119.2 | C14—C15—C16 | 121.13 (13) |
C4—C3—H3 | 119.2 | C14—C15—Cl1 | 119.42 (11) |
C5—C4—C3 | 120.57 (17) | C16—C15—Cl1 | 119.45 (11) |
C5—C4—H4 | 119.7 | C15—C16—C17 | 119.13 (13) |
C3—C4—H4 | 119.7 | C15—C16—H16 | 120.4 |
C4—C5—C6 | 118.99 (15) | C17—C16—H16 | 120.4 |
C4—C5—H5 | 120.5 | C12—C17—C16 | 121.25 (13) |
C6—C5—H5 | 120.5 | C12—C17—H17 | 119.4 |
C5—C6—C1 | 119.78 (13) | C16—C17—H17 | 119.4 |
C5—C6—C7 | 130.77 (13) | O3—C18—O2 | 121.50 (13) |
C1—C6—C7 | 109.45 (13) | O3—C18—C10 | 126.35 (14) |
C8—C7—O1 | 124.03 (12) | O2—C18—C10 | 112.14 (11) |
C8—C7—C6 | 115.98 (12) | O2—C19—C20 | 110.42 (16) |
O1—C7—C6 | 119.99 (12) | O2—C19—H19A | 109.6 |
C7—C8—C9 | 124.22 (11) | C20—C19—H19A | 109.6 |
C7—C8—S1 | 111.10 (10) | O2—C19—H19B | 109.6 |
C9—C8—S1 | 124.64 (10) | C20—C19—H19B | 109.6 |
C8—C9—C10 | 107.59 (11) | H19A—C19—H19B | 108.1 |
C8—C9—C12 | 109.14 (10) | C19—C20—H20A | 109.5 |
C10—C9—C12 | 113.90 (10) | C19—C20—H20B | 109.5 |
C8—C9—H9 | 108.7 | H20A—C20—H20B | 109.5 |
C10—C9—H9 | 108.7 | C19—C20—H20C | 109.5 |
C12—C9—H9 | 108.7 | H20A—C20—H20C | 109.5 |
C11—C10—C18 | 118.03 (12) | H20B—C20—H20C | 109.5 |
C11—C10—C9 | 123.05 (11) | C11—N1—H1A | 120.0 |
C18—C10—C9 | 118.79 (12) | C11—N1—H1B | 120.0 |
N1—C11—C10 | 127.48 (13) | H1A—N1—H1B | 120.0 |
N1—C11—O1 | 108.97 (12) | C11—O1—C7 | 116.36 (11) |
C10—C11—O1 | 123.55 (11) | C18—O2—C19 | 116.32 (11) |
C17—C12—C13 | 118.29 (12) | C1—S1—C8 | 91.21 (7) |
C17—C12—C9 | 121.86 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3 | 0.86 | 2.07 | 2.6796 (18) | 127 |
N1—H1A···O3i | 0.86 | 2.18 | 2.8956 (15) | 141 |
Symmetry code: (i) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3 | 0.86 | 2.07 | 2.6796 (18) | 127 |
N1—H1A···O3i | 0.86 | 2.18 | 2.8956 (15) | 141 |
Symmetry code: (i) −x+2, −y, −z+1. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
References
Bakhouch, M., Al Houari, G., Daoudi, M., Kerbal, A. & El yazidi, M. (2015). Mediterr. J. Chem. 4, 9–17. CrossRef Google Scholar
Bakhouch, M., Al Houari, G., El Yazidi, M., Saadi, M. & El Ammari, L. (2014). Acta Cryst. E70, o587. CSD CrossRef IUCr Journals Google Scholar
Boughaleb, A., Akhazzane, M., Alhouari, G., Bennani, B., Daoudi, M., Garrigues, B., Kerbal, A. & El yazidi, M. (2011). J. Soc. Chim. Tunisie, 13, 117–122. CAS Google Scholar
Boughaleb, A., Al houari, G., Bennani, B., Daoudi, M., Garrigues, B., Kerbal, A. & El yazidi, M. (2010). J. Soc. Chim. Tunisie, 12, 109–115. CAS Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cabiddu, M. G., Cabiddu, S., Cadoni, E., De Montis, S., Fattuoni, C., Melis, S. & Usai, M. (2002). Synthesis, 2002, 875–878. CrossRef Google Scholar
Daisley, R. W., Elagbar, Z. A. & Walker, J. (1982). J. Heterocycl. Chem. 19, 1013–1016. CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Pradhan, T. K., De, A. & Mortier, A. (2005). Tetrahedron, 61, 9007–9017. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef 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.