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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| Pages o160-o161
doi:10.1107/S1600536814000786

4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth­yl]-2H-1,4-benzo­thia­zin-3(4H)-one

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, Avenue 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 11 January 2014; accepted 13 January 2014; online 18 January 2014)

In the title compound, C18H16N4OS, the six-membered heterocycle of the benzo­thia­zine fragment exhibits a screw-boat conformation. The dihedral angles between the plane through the triazole ring and those through the fused and terminal benzene rings are 76.68 (11) and 71.0 (1)°, respectively; the benzene rings are nearly perpendicular [dihedral angle = 79.6 (1)°]. In the crystal, mol­ecules are linked by C—H⋯N and C—H⋯O inter­actions, forming a three-dimensional network.

CCDC reference: 981245

Related literature

For the biological activity of 1,4-benzo­thia­zin-3-one derivatives, see: Rathore & Kumar (2006[Rathore, B. S. & Kumar, M. (2006). Bioorg. Med. Chem. 14, 5678-5682.]); Baraza­rte et al. (2008[Barazarte, A., Camacho, J., Dominguez, J., Lobo, G., Gamboa, N., Rodrigues, J., Capparelli, M. V., Alvarez-Larena, A., Andujar, S., Enriz, D. & Charris, J. (2008). Bioorg. Med. Chem. 16, 3661-3674.]); Chia et al. (2008[Chia, E. W., Pearce, A. N., Berridge, M. V., Larsen, L., Perry, N. B., Sansom, C. E., Godfrey, C. A., Hanton, L. R., Lu, G. L., Walton, M., Denny, W. A., Webb, V. L., Copp, B. R. & Harper, J. L. (2008). Bioorg. Med. Chem. 16, 9432-9442.]). For related structures, see: Ouzidan et al. (2011[Ouzidan, Y., Kandri Rodi, Y., Fronczek, F. R., Venkatraman, R., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o890-o891.]); Sebbar et al. (2014[Sebbar, N. K., Zerzouf, A., Essassi, E. M., Saadi, M. & El Ammari, L. (2014). Acta Cryst. E70, o116.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C18H16N4OS

  • Mr = 336.41

  • Monoclinic, P 21 /c

  • a = 13.283 (2) Å

  • b = 5.3661 (10) Å

  • c = 23.281 (4) Å

  • β = 96.633 (10)°

  • V = 1648.3 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 296 K

  • 0.39 × 0.35 × 0.28 mm
Data collection

  • Bruker X8 APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.649, Tmax = 0.747

  • 15366 measured reflections

  • 3526 independent reflections

  • 2540 reflections with I > 2σ(I)

  • Rint = 0.044
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.149

  • S = 1.03

  • 3526 reflections

  • 217 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C8—H8⋯N2i 0.93 2.44 3.344 (3) 165
C8—H8⋯N3i 0.93 2.44 3.339 (3) 164
C5—H5⋯O1ii 0.93 2.58 3.477 (2) 163
Symmetry codes: (i) x, y+1, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: 981245

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814000786/tk5287sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814000786/tk5287Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814000786/tk5287Isup3.cml

checkCIF report


Experimental top

Synthesis and crystallization top

A mixture of 4-(prop-2-yn-1-yl)-3,4-di­hydro-2H-1,4-benzo­thia­zin-3-one (0.27 g, 0.35 mmol) and benzyl­azide (1.34 ml, 0.35 mmol) in ethanol (5 ml) was stirred at room temperature for 24 h. After cooling, the solid obtained was purified by column chromatography on silica gel with ethyl acetate-hexane (1/2) as eluent. Crystals were isolated when the solvent was allowed to evaporate.

Refinement top

The H atoms were located in a difference map and treated as riding with C—H = 0.93 Å (aromatic) and C—H = 0.97 Å (methyl­ene), and with Uiso(H) = 1.2 Ueq(C).

Results and discussion top

1,4-Benzo­thia­zine derivatives have a wide spectrum of pharmaceutical and biological activities, such as anti-microbial (Rathore & Kumar, 2006); anti-malarial (Baraza­rte et al., 2008) and anti-inflammatory (Chia et al., 2008). The present work is a continuation of the investigation of the benzo­thia­zine derivatives published recently by our team (Ouzidan et al., 2011; Sebbar et al., 2014). The aim of the present paper was to study the crystal structure of the recently synthesized 4-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-3,4-di­hydro-2H-1,4-benzo­thia­zin-3-one compound.

The molecule of the title compound is built up from two fused six-membered rings linked to a triazole ring, via the heterocyclic, which in turn is attached to benzene ring as shown in Fig. 1. The 1,4-thia­zine ring adopts a screw boat conformation as indicated by the puckering amplitude Q = 0.6197 (17) Å, spherical polar angle θ = 64.42 (16)° and with φ = 329.6 (2)° (Cremer & Pople, 1975). The triazole ring (N1N2N3C8C9) makes dihedral angles of 76.68 (11) and 71.0 (1)° with the benzene fused to the 1,4-thia­zine ring (C11 to C16) and the other benzene ring (C1 to C6), respectively. Moreover, the two benzene rings are nearly perpendicular as indicated by the dihedral angle between them of 79.6 (1)°.

In the crystal, the molecules are linked together by a weak inter­molecular C8–H8···N2, C8–H8···N3 and C5–H5···O1 inter­actions, to form a three-dimensional network (see Fig. 2 and Table 1).

Related literature top

For the biological activity of 1,4-benzothiazin-3-one derivatives, see: Rathore & Kumar (2006); Barazarte et al. (2008); Chia et al. (2008). For related structures, see: Ouzidan et al. (2011); Sebbar et al. (2014). For puckering parameters, see: Cremer & Pople (1975).

Structure description top

1,4-Benzo­thia­zine derivatives have a wide spectrum of pharmaceutical and biological activities, such as anti-microbial (Rathore & Kumar, 2006); anti-malarial (Baraza­rte et al., 2008) and anti-inflammatory (Chia et al., 2008). The present work is a continuation of the investigation of the benzo­thia­zine derivatives published recently by our team (Ouzidan et al., 2011; Sebbar et al., 2014). The aim of the present paper was to study the crystal structure of the recently synthesized 4-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-3,4-di­hydro-2H-1,4-benzo­thia­zin-3-one compound.

The molecule of the title compound is built up from two fused six-membered rings linked to a triazole ring, via the heterocyclic, which in turn is attached to benzene ring as shown in Fig. 1. The 1,4-thia­zine ring adopts a screw boat conformation as indicated by the puckering amplitude Q = 0.6197 (17) Å, spherical polar angle θ = 64.42 (16)° and with φ = 329.6 (2)° (Cremer & Pople, 1975). The triazole ring (N1N2N3C8C9) makes dihedral angles of 76.68 (11) and 71.0 (1)° with the benzene fused to the 1,4-thia­zine ring (C11 to C16) and the other benzene ring (C1 to C6), respectively. Moreover, the two benzene rings are nearly perpendicular as indicated by the dihedral angle between them of 79.6 (1)°.

In the crystal, the molecules are linked together by a weak inter­molecular C8–H8···N2, C8–H8···N3 and C5–H5···O1 inter­actions, to form a three-dimensional network (see Fig. 2 and Table 1).

For the biological activity of 1,4-benzothiazin-3-one derivatives, see: Rathore & Kumar (2006); Barazarte et al. (2008); Chia et al. (2008). For related structures, see: Ouzidan et al. (2011); Sebbar et al. (2014). For puckering parameters, see: Cremer & Pople (1975).

Synthesis and crystallization top

A mixture of 4-(prop-2-yn-1-yl)-3,4-di­hydro-2H-1,4-benzo­thia­zin-3-one (0.27 g, 0.35 mmol) and benzyl­azide (1.34 ml, 0.35 mmol) in ethanol (5 ml) was stirred at room temperature for 24 h. After cooling, the solid obtained was purified by column chromatography on silica gel with ethyl acetate-hexane (1/2) as eluent. Crystals were isolated when the solvent was allowed to evaporate.

Refinement details top

The H atoms were located in a difference map and treated as riding with C—H = 0.93 Å (aromatic) and C—H = 0.97 Å (methyl­ene), and with Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (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. Partial three dimensional plot of the title compound, showing molecules linked through C8–H8···N2, C8–H8···N3 and C5–H5···O1 hydrogen bonds (dashed lines).
4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-2H-1,4-benzothiazin-3(4H)-one top
Crystal data top
C18H16N4OSF(000) = 704
Mr = 336.41Dx = 1.356 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3526 reflections
a = 13.283 (2) Åθ = 1.8–27.1°
b = 5.3661 (10) ŵ = 0.21 mm−1
c = 23.281 (4) ÅT = 296 K
β = 96.633 (10)°Block, colourless
V = 1648.3 (5) Å30.39 × 0.35 × 0.28 mm
Z = 4
Data collection top
Bruker X8 APEX
diffractometer		3526 independent reflections
Radiation source: fine-focus sealed tube2540 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
φ and ω scansθmax = 27.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −16→17
Tmin = 0.649, Tmax = 0.747k = −6→5
15366 measured reflectionsl = −29→29
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.087P)2 + 0.1602P]
where P = (Fo2 + 2Fc2)/3
3526 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Crystal data top
C18H16N4OSV = 1648.3 (5) Å3
Mr = 336.41Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.283 (2) ŵ = 0.21 mm−1
b = 5.3661 (10) ÅT = 296 K
c = 23.281 (4) Å0.39 × 0.35 × 0.28 mm
β = 96.633 (10)°
Data collection top
Bruker X8 APEX
diffractometer		3526 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2540 reflections with I > 2σ(I)
Tmin = 0.649, Tmax = 0.747Rint = 0.044
15366 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.03Δρmax = 0.22 e Å−3
3526 reflectionsΔρmin = −0.33 e Å−3
217 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.22144 (17)1.2104 (4)0.32721 (9)0.0608 (6)
H10.27031.33280.33610.073*
C20.13131 (19)1.2201 (4)0.35176 (10)0.0663 (6)
H20.12071.34710.37760.080*
C30.05772 (18)1.0436 (4)0.33828 (10)0.0620 (6)
H3−0.00281.05010.35470.074*
C40.07467 (19)0.8572 (5)0.30010 (9)0.0675 (7)
H40.02460.73870.29010.081*
C50.16506 (19)0.8438 (4)0.27650 (8)0.0577 (6)
H50.17590.71400.25150.069*
C60.23928 (15)1.0199 (4)0.28950 (7)0.0457 (4)
C70.33713 (17)1.0077 (4)0.26263 (8)0.0597 (6)
H7A0.33090.88290.23230.072*
H7B0.34901.16730.24500.072*
C80.48825 (17)1.0970 (4)0.33613 (9)0.0545 (5)
H80.48851.27030.33540.065*
C90.55342 (15)0.9457 (3)0.36961 (7)0.0424 (4)
C100.64140 (18)1.0099 (4)0.41219 (9)0.0555 (5)
H10A0.67111.16460.40060.067*
H10B0.61811.03630.44970.067*
C110.72308 (14)0.6346 (4)0.46251 (7)0.0438 (4)
C120.64100 (17)0.6069 (5)0.49446 (8)0.0581 (6)
H120.58230.69940.48470.070*
C130.6465 (2)0.4417 (5)0.54082 (8)0.0727 (8)
H130.59230.42960.56270.087*
C140.7301 (2)0.2979 (6)0.55454 (8)0.0780 (8)
H140.73270.18730.58540.094*
C150.81136 (19)0.3164 (5)0.52239 (8)0.0683 (7)
H150.86800.21540.53110.082*
C160.80820 (15)0.4867 (4)0.47686 (7)0.0499 (5)
C170.84430 (15)0.5783 (4)0.36944 (7)0.0526 (5)
H17A0.89100.60670.34100.063*
H17B0.80320.43410.35720.063*
C180.77735 (15)0.8007 (4)0.37190 (7)0.0480 (5)
N10.42420 (12)0.9464 (3)0.30471 (6)0.0442 (4)
N20.44742 (13)0.7078 (3)0.31697 (6)0.0482 (4)
N30.52629 (12)0.7072 (3)0.35664 (6)0.0461 (4)
N40.71926 (12)0.8149 (3)0.41721 (6)0.0451 (4)
O10.77092 (14)0.9600 (3)0.33403 (6)0.0689 (5)
S10.91484 (4)0.51598 (14)0.43858 (2)0.0692 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0529 (13)0.0505 (13)0.0794 (14)−0.0036 (10)0.0088 (11)−0.0073 (10)
C20.0640 (15)0.0553 (13)0.0817 (14)0.0067 (11)0.0168 (12)−0.0186 (11)
C30.0530 (13)0.0659 (14)0.0694 (13)0.0021 (11)0.0169 (11)0.0023 (11)
C40.0738 (16)0.0651 (15)0.0658 (12)−0.0245 (12)0.0177 (12)−0.0075 (11)
C50.0784 (16)0.0501 (12)0.0461 (9)−0.0030 (11)0.0137 (10)−0.0047 (9)
C60.0480 (11)0.0503 (11)0.0385 (8)0.0108 (9)0.0041 (7)0.0125 (8)
C70.0553 (13)0.0785 (16)0.0465 (10)0.0182 (11)0.0108 (9)0.0225 (10)
C80.0598 (13)0.0292 (9)0.0759 (13)0.0004 (9)0.0141 (11)0.0046 (9)
C90.0480 (11)0.0325 (9)0.0483 (9)−0.0044 (8)0.0125 (8)−0.0029 (7)
C100.0621 (13)0.0426 (11)0.0615 (11)−0.0112 (10)0.0064 (10)−0.0110 (9)
C110.0433 (10)0.0563 (11)0.0312 (7)−0.0180 (9)0.0015 (7)−0.0067 (7)
C120.0483 (12)0.0824 (15)0.0449 (10)−0.0193 (11)0.0101 (9)−0.0094 (10)
C130.0673 (16)0.114 (2)0.0379 (9)−0.0397 (15)0.0129 (10)−0.0035 (11)
C140.0828 (19)0.110 (2)0.0378 (9)−0.0344 (16)−0.0084 (10)0.0178 (11)
C150.0655 (15)0.0909 (18)0.0437 (10)−0.0127 (13)−0.0145 (9)0.0138 (11)
C160.0410 (10)0.0736 (14)0.0332 (8)−0.0165 (10)−0.0039 (7)−0.0012 (8)
C170.0461 (11)0.0736 (14)0.0391 (8)−0.0139 (10)0.0094 (8)−0.0017 (9)
C180.0469 (11)0.0581 (12)0.0387 (8)−0.0221 (9)0.0036 (7)−0.0004 (8)
N10.0450 (9)0.0419 (9)0.0469 (8)0.0054 (7)0.0102 (7)0.0093 (6)
N20.0531 (10)0.0375 (9)0.0513 (8)0.0015 (7)−0.0049 (7)0.0012 (7)
N30.0538 (10)0.0318 (8)0.0503 (8)−0.0042 (7)−0.0035 (7)−0.0009 (6)
N40.0435 (9)0.0497 (9)0.0419 (7)−0.0123 (7)0.0044 (6)−0.0033 (7)
O10.0803 (12)0.0684 (10)0.0588 (8)−0.0190 (8)0.0122 (8)0.0172 (7)
S10.0364 (3)0.1170 (6)0.0528 (3)−0.0050 (3)−0.0005 (2)0.0036 (3)
Geometric parameters (Å, º) top
C1—C61.385 (3)C10—H10B0.9700
C1—C21.386 (3)C11—C161.390 (3)
C1—H10.9300C11—C121.397 (3)
C2—C31.371 (3)C11—N41.428 (2)
C2—H20.9300C12—C131.392 (3)
C3—C41.374 (3)C12—H120.9300
C3—H30.9300C13—C141.360 (4)
C4—C51.379 (3)C13—H130.9300
C4—H40.9300C14—C151.387 (4)
C5—C61.374 (3)C14—H140.9300
C5—H50.9300C15—C161.396 (3)
C6—C71.508 (3)C15—H150.9300
C7—N11.464 (3)C16—S11.766 (2)
C7—H7A0.9700C17—C181.493 (3)
C7—H7B0.9700C17—S11.798 (2)
C8—N11.330 (3)C17—H17A0.9700
C8—C91.364 (3)C17—H17B0.9700
C8—H80.9300C18—O11.224 (2)
C9—N31.354 (2)C18—N41.379 (2)
C9—C101.483 (3)N1—N21.340 (2)
C10—N41.466 (3)N2—N31.314 (2)
C10—H10A0.9700
C6—C1—C2120.5 (2)C16—C11—C12118.32 (18)
C6—C1—H1119.7C16—C11—N4121.53 (16)
C2—C1—H1119.7C12—C11—N4120.14 (19)
C3—C2—C1120.5 (2)C13—C12—C11120.4 (2)
C3—C2—H2119.8C13—C12—H12119.8
C1—C2—H2119.8C11—C12—H12119.8
C2—C3—C4119.0 (2)C14—C13—C12120.8 (2)
C2—C3—H3120.5C14—C13—H13119.6
C4—C3—H3120.5C12—C13—H13119.6
C3—C4—C5120.7 (2)C13—C14—C15119.9 (2)
C3—C4—H4119.6C13—C14—H14120.1
C5—C4—H4119.6C15—C14—H14120.1
C6—C5—C4120.80 (19)C14—C15—C16120.0 (2)
C6—C5—H5119.6C14—C15—H15120.0
C4—C5—H5119.6C16—C15—H15120.0
C5—C6—C1118.43 (18)C11—C16—C15120.55 (19)
C5—C6—C7120.64 (18)C11—C16—S1120.37 (14)
C1—C6—C7120.92 (19)C15—C16—S1119.07 (18)
N1—C7—C6112.60 (14)C18—C17—S1111.42 (13)
N1—C7—H7A109.1C18—C17—H17A109.3
C6—C7—H7A109.1S1—C17—H17A109.3
N1—C7—H7B109.1C18—C17—H17B109.3
C6—C7—H7B109.1S1—C17—H17B109.3
H7A—C7—H7B107.8H17A—C17—H17B108.0
N1—C8—C9106.02 (17)O1—C18—N4120.9 (2)
N1—C8—H8127.0O1—C18—C17121.52 (17)
C9—C8—H8127.0N4—C18—C17117.51 (16)
N3—C9—C8107.47 (18)C8—N1—N2110.29 (16)
N3—C9—C10122.51 (17)C8—N1—C7129.57 (18)
C8—C9—C10130.00 (18)N2—N1—C7120.13 (17)
N4—C10—C9112.43 (15)N3—N2—N1107.31 (15)
N4—C10—H10A109.1N2—N3—C9108.92 (15)
C9—C10—H10A109.1C18—N4—C11123.52 (17)
N4—C10—H10B109.1C18—N4—C10115.48 (16)
C9—C10—H10B109.1C11—N4—C10120.46 (15)
H10A—C10—H10B107.8C16—S1—C1795.91 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···N2i0.932.443.344 (3)165
C8—H8···N3i0.932.443.339 (3)164
C5—H5···O1ii0.932.583.477 (2)163
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···N2i0.932.443.344 (3)164.8
C8—H8···N3i0.932.443.339 (3)163.7
C5—H5···O1ii0.932.583.477 (2)162.9
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y−1/2, −z+1/2.
 

Acknowledgements

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

References

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ISSN: 2056-9890
Volume 70| Part 2| February 2014| Pages o160-o161
doi:10.1107/S1600536814000786
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