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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o116
doi:10.1107/S1600536813034697

Ethyl 2-{5-[(3-oxo-3,4-di­hydro-2H-1,4-benzo­thia­zin-4-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate

Nada Kheira Sebbar,a* Abdelfettah Zerzouf,b El Mokhtar Essassi,a Mohamed Saadic and Lahcen El Ammaric

aLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V-Agdal, Rabat, Morocco, bLaboratoire de Chimie Organique et Etudes Physico-chimique, ENS Takaddoum, Rabat, Morocco, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: nk_sebbar@yahoo.fr

(Received 24 December 2013; accepted 27 December 2013; online 8 January 2014)

In the title compound, C15H16N4O3S, the six-membered heterocycle of the benzo­thia­zine fragment exhibits a screw boat conformation. The dihedral angle between the planes through the triazole ring and the benzene ring fused to the 1,4-thia­zine ring is 62.98 (11)°. The mean plane formed by the atoms belonging to the acetate group is nearly perpendicular to the triazole ring [dihedral angle = 74.65 (12)°]. In the crystal, mol­ecules are linked by pairs of C—H⋯O inter­actions, forming dimeric aggregates.

CCDC reference: 978857

Related literature

For the pharmacological activity of benzo­thia­zine derivatives, see: Fringuelli et al. (1998[Fringuelli, R., Schiaffella, F., Bistoni, F., Pitzurra, L. & Vecchiarelli, A. (1998). Bioorg. Med. Chem. 6, 103-108.]); Lopatina et al. (1982[Lopatina, K. I., Artemenko, G. N., Sokolova, T. V., Avdulov, N. A. & Zagorevskii, V. A. (1982). Pharm. Chem. J. 16, 110-113.]); Rathore & Kumar (2006[Rathore, B. S. & Kumar, M. (2006). Bioorg. Med. Chem. 14, 5678-5682.]). For related structures, see: Keita et al. (2000[Keita, A., Ahabchane, N., Essassi, E. M. & Pierrot, M. (2000). Acta Cryst. C56, e227.]); Zerzouf et al. (2001[Zerzouf, A., Salem, M., Essassi, E. M. & Pierrot, M. (2001). Acta Cryst. E57, o498-o499.]); Barryala et al. (2011[Barryala, Y., Massip, S., Lazar, S., Essassi, E. M. & Zouihri, H. (2011). Acta Cryst. E67, o724.]). For puckering calculation see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C15H16N4O3S

  • Mr = 332.38

  • Triclinic, [P \overline 1]

  • a = 5.6414 (2) Å

  • b = 11.1604 (4) Å

  • c = 13.3724 (5) Å

  • α = 73.823 (2)°

  • β = 87.226 (2)°

  • γ = 88.566 (2)°

  • V = 807.59 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 296 K

  • 0.37 × 0.34 × 0.28 mm
Data collection

  • Bruker X8 APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.692, Tmax = 0.747

  • 16305 measured reflections

  • 3560 independent reflections

  • 2963 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.124

  • S = 1.05

  • 3560 reflections

  • 208 parameters

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C4—H4⋯O2i 0.93 2.59 3.445 (3) 154
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 978857

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813034697/tk5283sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813034697/tk5283Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813034697/tk5283Isup3.cml

checkCIF report


Experimental top

Synthesis and crystallization top

To a solution of 4-(prop-2-yn-1-yl)-2H-1, 4-benzo­thia­zin-3-one (0.2 g, 0.7 mmol) in ethanol (15 ml) was added azide ethyl acetate (0.20 ml, 1.89 mmol). The mixture was stirred under reflux for 24 h. After completion of reaction (monitored by TLC), the solution was concentrated and the residue was purified by column chromatography on silica gel by using a mixture (hexane/ethyl acetate 2/1). Crystals were obtained when the solvent was allowed to evaporate. The solid product was purified by recrystallization from ethanol to afford yellow crystals in 75% yield.

Refinement top

The H atoms were located in a difference map and treated as riding with C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methyl­ene) and C—H = 0.96 Å, (methyl), and with Uiso(H) = 1.2 Ueq (methyl­ene and ammonium) and Uiso(H) = 1.5 Ueq for the methyl. Owing to poor aggreement, three reflections, i.e. (0 1 1), (0 1 0) and (0 0 1), were omitted from the final cycles of refinement.

Results and discussion top

Several derivatives of benzo­thia­zines form an important class of bioactive molecules in the field of drugs and pharmaceuticals. Applications in various therapeutic areas, include their use as anti-depressants (Lopatina et al., 1982); anti-fungals (Fringuelli et al., 1998) and anti-microbials (Rathore & Kumar, 2006). The present work is a continuation of the investigation of the benzo­thia­zine derivatives published recently by our team (Keita et al., 2000; Zerzouf et al., 2001; Barryala et al., 2011). The aim of the present paper was to study the recently synthesized ethyl2-{5-[(3-oxo-2H-1,4-benzo­thia­zin-4-yl)methyl]- 1,2,3-triazol-1-yl}acetate crystal structure by X-ray crystallography at room temperature.

The molecule of the title compound is build up from two fused six-membered rings linked to a triazole ring which is attached to an ethyl­acetate group as shown in Fig.1. The 1,4-thia­zine ring adopts a screw boat conformation as indicated by the puckering amplitude Q = 0.6536 (17) Å, and spherical polar angle θ = 112.04 (16)°, with φ = 152.14 (18)° (Cremer & Pople, 1975). The benzene ring (C1 to C6) makes a dihedral angle of 62.98 (11)° with the triazole ring (N2N3N4C10C11) which is nearly perpendicular to the mean plane through the acetate atoms (C12C13O2O3) as indicated by the dihedral angle between them of 74.65 (12)°. In the crystal, the molecules are linked by weak inter­molecular C4–H4···O2 inter­actions to form dimers (see Fig.2 and Table 1).

Related literature top

For the pharmacological activity of benzothiazine derivatives, see: Fringuelli et al. (1998); Lopatina et al. (1982); Rathore & Kumar (2006). For related structures, see: Keita et al. (2000); Zerzouf et al. (2001); Barryala et al. (2011). For puckering calculation see: Cremer & Pople (1975).

Structure description top

Several derivatives of benzo­thia­zines form an important class of bioactive molecules in the field of drugs and pharmaceuticals. Applications in various therapeutic areas, include their use as anti-depressants (Lopatina et al., 1982); anti-fungals (Fringuelli et al., 1998) and anti-microbials (Rathore & Kumar, 2006). The present work is a continuation of the investigation of the benzo­thia­zine derivatives published recently by our team (Keita et al., 2000; Zerzouf et al., 2001; Barryala et al., 2011). The aim of the present paper was to study the recently synthesized ethyl2-{5-[(3-oxo-2H-1,4-benzo­thia­zin-4-yl)methyl]- 1,2,3-triazol-1-yl}acetate crystal structure by X-ray crystallography at room temperature.

The molecule of the title compound is build up from two fused six-membered rings linked to a triazole ring which is attached to an ethyl­acetate group as shown in Fig.1. The 1,4-thia­zine ring adopts a screw boat conformation as indicated by the puckering amplitude Q = 0.6536 (17) Å, and spherical polar angle θ = 112.04 (16)°, with φ = 152.14 (18)° (Cremer & Pople, 1975). The benzene ring (C1 to C6) makes a dihedral angle of 62.98 (11)° with the triazole ring (N2N3N4C10C11) which is nearly perpendicular to the mean plane through the acetate atoms (C12C13O2O3) as indicated by the dihedral angle between them of 74.65 (12)°. In the crystal, the molecules are linked by weak inter­molecular C4–H4···O2 inter­actions to form dimers (see Fig.2 and Table 1).

For the pharmacological activity of benzothiazine derivatives, see: Fringuelli et al. (1998); Lopatina et al. (1982); Rathore & Kumar (2006). For related structures, see: Keita et al. (2000); Zerzouf et al. (2001); Barryala et al. (2011). For puckering calculation see: Cremer & Pople (1975).

Synthesis and crystallization top

To a solution of 4-(prop-2-yn-1-yl)-2H-1, 4-benzo­thia­zin-3-one (0.2 g, 0.7 mmol) in ethanol (15 ml) was added azide ethyl acetate (0.20 ml, 1.89 mmol). The mixture was stirred under reflux for 24 h. After completion of reaction (monitored by TLC), the solution was concentrated and the residue was purified by column chromatography on silica gel by using a mixture (hexane/ethyl acetate 2/1). Crystals were obtained when the solvent was allowed to evaporate. The solid product was purified by recrystallization from ethanol to afford yellow crystals in 75% yield.

Refinement details top

The H atoms were located in a difference map and treated as riding with C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methyl­ene) and C—H = 0.96 Å, (methyl), and with Uiso(H) = 1.2 Ueq (methyl­ene and ammonium) and Uiso(H) = 1.5 Ueq for the methyl. Owing to poor aggreement, three reflections, i.e. (0 1 1), (0 1 0) and (0 0 1), were omitted from the final cycles of refinement.

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
[Figure 1] 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.
[Figure 2] Fig. 2. Three dimensional plot of the title compound, showing molecules linked through C4–H4···O2 hydrogen bonds (dashed lines).
Ethyl 2-{5-[(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl)methyl]-1H-1,2,3-triazol-1-yl}acetate top
Crystal data top
C15H16N4O3SZ = 2
Mr = 332.38F(000) = 348
Triclinic, P1Dx = 1.367 Mg m−3
a = 5.6414 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1604 (4) ÅCell parameters from 3560 reflections
c = 13.3724 (5) Åθ = 2.8–27.1°
α = 73.823 (2)°µ = 0.22 mm−1
β = 87.226 (2)°T = 296 K
γ = 88.566 (2)°Block, yellow
V = 807.59 (5) Å30.37 × 0.34 × 0.28 mm
Data collection top
Bruker X8 APEX
diffractometer		3560 independent reflections
Radiation source: fine-focus sealed tube2963 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 27.1°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −7→7
Tmin = 0.692, Tmax = 0.747k = −14→14
16305 measured reflectionsl = −17→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.3602P]
where P = (Fo2 + 2Fc2)/3
3560 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Crystal data top
C15H16N4O3Sγ = 88.566 (2)°
Mr = 332.38V = 807.59 (5) Å3
Triclinic, P1Z = 2
a = 5.6414 (2) ÅMo Kα radiation
b = 11.1604 (4) ŵ = 0.22 mm−1
c = 13.3724 (5) ÅT = 296 K
α = 73.823 (2)°0.37 × 0.34 × 0.28 mm
β = 87.226 (2)°
Data collection top
Bruker X8 APEX
diffractometer		3560 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2963 reflections with I > 2σ(I)
Tmin = 0.692, Tmax = 0.747Rint = 0.028
16305 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.05Δρmax = 0.39 e Å−3
3560 reflectionsΔρmin = −0.32 e Å−3
208 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
xyzUiso*/Ueq
C10.0414 (3)0.32734 (16)0.35494 (13)0.0404 (4)
C2−0.1005 (4)0.43140 (19)0.35277 (16)0.0584 (5)
H2−0.10860.49600.29160.070*
C3−0.2296 (5)0.4392 (3)0.4410 (2)0.0816 (8)
H3−0.32260.50970.43910.098*
C4−0.2224 (5)0.3437 (3)0.5320 (2)0.0848 (8)
H4−0.31300.34880.59070.102*
C5−0.0814 (4)0.2415 (3)0.53555 (16)0.0681 (6)
H5−0.07550.17750.59720.082*
C60.0537 (3)0.23176 (18)0.44807 (14)0.0469 (4)
C70.4681 (3)0.1852 (2)0.36729 (17)0.0589 (5)
H7A0.53600.24440.39860.071*
H7B0.59270.12720.35810.071*
C80.3767 (3)0.25404 (16)0.26244 (15)0.0435 (4)
C90.0720 (3)0.38039 (16)0.16053 (13)0.0386 (4)
H9A−0.09990.37670.16590.046*
H9B0.12680.33620.11060.046*
C100.1439 (3)0.51384 (15)0.12016 (12)0.0351 (3)
C110.3619 (3)0.56739 (15)0.10351 (14)0.0399 (4)
H110.50900.52740.11390.048*
C120.4837 (3)0.79233 (16)0.04712 (13)0.0422 (4)
H12A0.40780.86770.00590.051*
H12B0.61990.77370.00660.051*
C130.5656 (4)0.81404 (19)0.14565 (15)0.0498 (4)
C140.8094 (7)0.9430 (4)0.2083 (2)0.1208 (14)
H14A0.69530.97960.24820.145*
H14B0.86690.86530.25410.145*
C150.9975 (6)1.0233 (3)0.1746 (3)0.1089 (12)
H15A1.06931.03800.23370.163*
H15B0.94121.10100.13030.163*
H15C1.11280.98670.13640.163*
N10.1656 (2)0.31606 (12)0.26288 (10)0.0359 (3)
N2−0.0215 (3)0.60571 (14)0.09455 (13)0.0471 (4)
N30.0854 (3)0.71393 (14)0.06368 (13)0.0486 (4)
N40.3184 (2)0.69022 (13)0.06899 (11)0.0380 (3)
O10.4877 (3)0.25525 (15)0.18177 (12)0.0619 (4)
O20.5302 (4)0.7457 (2)0.23075 (13)0.1013 (8)
O30.6924 (3)0.91691 (13)0.12300 (11)0.0560 (4)
S10.23551 (10)0.10089 (5)0.45316 (4)0.06117 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0407 (9)0.0437 (9)0.0341 (8)−0.0073 (7)0.0014 (7)−0.0060 (7)
C20.0686 (13)0.0517 (11)0.0476 (11)0.0061 (10)0.0149 (10)−0.0052 (9)
C30.097 (2)0.0739 (16)0.0688 (16)0.0123 (14)0.0299 (14)−0.0176 (13)
C40.098 (2)0.104 (2)0.0478 (13)0.0025 (17)0.0262 (13)−0.0187 (13)
C50.0732 (15)0.0872 (17)0.0330 (10)−0.0082 (13)0.0021 (10)0.0015 (10)
C60.0438 (9)0.0539 (10)0.0369 (9)−0.0068 (8)−0.0049 (7)−0.0015 (8)
C70.0386 (10)0.0640 (13)0.0608 (13)0.0032 (9)−0.0069 (9)0.0052 (10)
C80.0369 (9)0.0409 (9)0.0481 (10)−0.0043 (7)−0.0002 (7)−0.0046 (7)
C90.0370 (8)0.0419 (9)0.0338 (8)−0.0049 (7)−0.0042 (6)−0.0049 (7)
C100.0326 (8)0.0403 (8)0.0291 (8)0.0007 (6)−0.0027 (6)−0.0039 (6)
C110.0327 (8)0.0367 (8)0.0453 (9)0.0027 (6)−0.0022 (7)−0.0031 (7)
C120.0479 (10)0.0376 (8)0.0360 (9)−0.0069 (7)−0.0020 (7)−0.0014 (7)
C130.0559 (11)0.0526 (11)0.0380 (10)−0.0085 (9)−0.0009 (8)−0.0073 (8)
C140.153 (3)0.155 (3)0.0655 (18)−0.077 (3)−0.0210 (19)−0.039 (2)
C150.117 (3)0.116 (3)0.096 (2)−0.047 (2)−0.038 (2)−0.0240 (19)
N10.0348 (7)0.0363 (7)0.0326 (7)−0.0022 (5)−0.0014 (5)−0.0028 (5)
N20.0332 (7)0.0468 (8)0.0536 (9)0.0020 (6)−0.0060 (6)−0.0009 (7)
N30.0394 (8)0.0432 (8)0.0555 (10)0.0059 (6)−0.0070 (7)−0.0008 (7)
N40.0358 (7)0.0362 (7)0.0368 (7)−0.0004 (5)−0.0022 (5)−0.0018 (6)
O10.0508 (8)0.0707 (10)0.0586 (9)0.0096 (7)0.0109 (7)−0.0119 (7)
O20.1505 (19)0.1102 (15)0.0355 (9)−0.0617 (14)−0.0002 (10)−0.0028 (9)
O30.0673 (9)0.0560 (8)0.0456 (8)−0.0148 (7)−0.0102 (6)−0.0131 (6)
S10.0544 (3)0.0533 (3)0.0578 (3)−0.0006 (2)−0.0062 (2)0.0150 (2)
Geometric parameters (Å, º) top
C1—C21.388 (3)C9—H9B0.9700
C1—C61.399 (2)C10—N21.351 (2)
C1—N11.421 (2)C10—C111.362 (2)
C2—C31.379 (3)C11—N41.339 (2)
C2—H20.9300C11—H110.9300
C3—C41.378 (4)C12—N41.448 (2)
C3—H30.9300C12—C131.500 (3)
C4—C51.365 (4)C12—H12A0.9700
C4—H40.9300C12—H12B0.9700
C5—C61.394 (3)C13—O21.191 (2)
C5—H50.9300C13—O31.322 (2)
C6—S11.751 (2)C14—C151.381 (4)
C7—C81.507 (3)C14—O31.446 (3)
C7—S11.800 (2)C14—H14A0.9700
C7—H7A0.9700C14—H14B0.9700
C7—H7B0.9700C15—H15A0.9600
C8—O11.217 (2)C15—H15B0.9600
C8—N11.363 (2)C15—H15C0.9600
C9—N11.473 (2)N2—N31.314 (2)
C9—C101.495 (2)N3—N41.335 (2)
C9—H9A0.9700
C2—C1—C6119.07 (17)C11—C10—C9131.21 (15)
C2—C1—N1120.41 (15)N4—C11—C10104.97 (14)
C6—C1—N1120.48 (17)N4—C11—H11127.5
C3—C2—C1120.2 (2)C10—C11—H11127.5
C3—C2—H2119.9N4—C12—C13111.39 (14)
C1—C2—H2119.9N4—C12—H12A109.4
C4—C3—C2120.8 (2)C13—C12—H12A109.4
C4—C3—H3119.6N4—C12—H12B109.4
C2—C3—H3119.6C13—C12—H12B109.4
C5—C4—C3119.6 (2)H12A—C12—H12B108.0
C5—C4—H4120.2O2—C13—O3125.37 (19)
C3—C4—H4120.2O2—C13—C12124.90 (19)
C4—C5—C6120.9 (2)O3—C13—C12109.65 (15)
C4—C5—H5119.5C15—C14—O3112.4 (3)
C6—C5—H5119.5C15—C14—H14A109.1
C5—C6—C1119.4 (2)O3—C14—H14A109.1
C5—C6—S1120.78 (16)C15—C14—H14B109.1
C1—C6—S1119.84 (15)O3—C14—H14B109.1
C8—C7—S1111.53 (13)H14A—C14—H14B107.8
C8—C7—H7A109.3C14—C15—H15A109.5
S1—C7—H7A109.3C14—C15—H15B109.5
C8—C7—H7B109.3H15A—C15—H15B109.5
S1—C7—H7B109.3C14—C15—H15C109.5
H7A—C7—H7B108.0H15A—C15—H15C109.5
O1—C8—N1121.92 (17)H15B—C15—H15C109.5
O1—C8—C7121.56 (17)C8—N1—C1123.85 (14)
N1—C8—C7116.51 (16)C8—N1—C9116.72 (14)
N1—C9—C10113.91 (13)C1—N1—C9119.33 (14)
N1—C9—H9A108.8N3—N2—C10109.05 (14)
C10—C9—H9A108.8N2—N3—N4106.88 (14)
N1—C9—H9B108.8N3—N4—C11111.00 (14)
C10—C9—H9B108.8N3—N4—C12119.89 (14)
H9A—C9—H9B107.7C11—N4—C12128.89 (14)
N2—C10—C11108.10 (14)C13—O3—C14116.59 (19)
N2—C10—C9120.68 (14)C6—S1—C795.49 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.932.593.445 (3)154
Symmetry code: (i) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.932.593.445 (3)154
Symmetry code: (i) −x, −y+1, −z+1.
 

Acknowledgements

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

References

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ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o116
doi:10.1107/S1600536813034697
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