Crystal structure of (E)-2-benzyl­idene-4-[(3-phenyl-4,5-di­hydro­isoxazol-5-yl)meth­yl]-2H-benzo[b][1,4]thia­zin-3(4H)-one

Sebbar, N.K.; Ellouz, M.; Essassi, E.M.; Saadi, M.; El Ammari, L.

doi:10.1107/S2056989015009755

organic compounds

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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages o423-o424

doi:10.1107/S2056989015009755

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Crystal structure of (E)-2-benzylidene-4-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-2H-benzo[b][1,4]thiazin-3(4H)-one

Nada Kheira Sebbar,^a Mohamed Ellouz,^a El Mokhtar Essassi,^a,^b ^* Mohamed Saadi ^c and Lahcen El Ammari ^c

^aLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, ^bMoroccan Foundation for Advanced Science, Innovation and Research (MASCIR), Rabat Design Center, Rue Mohamed Al Jazouli, Madinat El Irfane, 10100 Rabat, Morocco, and ^cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: em_essassi@yahoo.fr

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 19 May 2015; accepted 20 May 2015; online 23 May 2015)

In the title compound, C₂₅H₂₀N₂O₂S, the dihydroisoxazole ring exhibits an envelope conformation with the methine atom being the flap, while the 1,4-thiazine ring displays a screw-boat conformation. The six-membered ring fused to the 1,4-thiazine ring makes dihedral angles of 63.04 (2) and 54.7 (2)° with the mean planes through the five-membered heterocycle and the attached phenyl ring, respectively. The phenyl group connected to the 1,4-thiazine ring is disordered over two sites [major component = 0.57 (2)]. The most prominent interactions in the crystal structure are C—H⋯O hydrogen bonds that link molecules, forming inversion dimers, and C—H⋯N hydrogen bonds that link the dimers into columns parallel to the b axis.

Keywords: crystal structure; benzothiazine; dihydroisoxazole; C—H⋯O,N hydrogen bonding.

CCDC reference: 1402017

1. Related literature

For the biological activity and pharmaceutical properties of benzothiazines and their derivatives, see: Fringuelli et al. (1998 ); Rathore & Kumar (2006 ); Barazarte et al. (2008 ); Bakavoli et al. (2007 ). For related structures, see: Saeed et al. (2010 ); Afrakssou et al. (2011 ); Sebbar et al. (2014a ,b ).

2. Experimental

2.1. Crystal data

C₂₅H₂₀N₂O₂S
M_r = 412.49
Monoclinic, P 2₁ /n
a = 17.4463 (16) Å
b = 5.3024 (4) Å
c = 22.778 (2) Å
β = 106.370 (5)°
V = 2021.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.36 × 0.31 × 0.26 mm

2.2. Data collection

Bruker X8 APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.504, T_max = 0.748
27864 measured reflections
4149 independent reflections
1980 reflections with I > 2σ(I)
R_int = 0.095

2.3. Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.145
S = 1.00
4149 reflections
321 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O1ⁱ	0.93	2.43	3.339 (4)	166
C18—H18B⋯N2ⁱⁱ	0.97	2.56	3.526 (3)	178
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: 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: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1402017

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015009755/tk5368sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015009755/tk5368Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015009755/tk5368Isup3.cml

checkCIF report

Comment top

Recently, a number of pharmacological tests revealed that 2H-1,4- benzothiazine derivatives present various biological activities including antifungal (Fringuelli et al., 1998), antimicrobial (Rathore et al., 2006), antimalarial (Barazarte et al., 2008) and 15-lipoxygenase inhibition properties (Bakavoli et al., 2007). In this work, we aim to prepare new derivatives of 3,4-dihydro-2H- benzo[b]1,4-thiazine for biological evaluation, as in the previous studies (Saeed et al., 2010; Afrakssou et al., 2011; Sebbar et al., 2014a, 2014b. In the reaction, the oxime reacts with (E)-4-allyl-2-benzylidene-2H-benzo[b][1,4]thiazin-3(4H)-one in a biphasic medium (water-chloroform) at 0°C over 4 h to give a unique cycloadduct: (E)-2-benzylidene-4-((3-phenyl-4, 5-dihydroisoxazol-5-yl)methyl)-2H- benzo[b][1,4]thiazin-3(4H)-one (Scheme 1).

The molecule of the title compound is build up from two fused six-membered rings linked, via two –CH₂– groups, on the one hand to a phenyl ring and on the other hand to the 3-phenyl-4,5-dihydroisoxazole system as shown in Fig. 1. The (C1 to C6) benzene cycle form dihedral angles of 63.04 (2)\ and 54.7 (2)° with the mean planes through the five-membered heterocycle and the attached phenyl ring, respectively. In the crystal, the molecules are linked by hydrogen bond (Table 1) in the way to build a dimers as shown in Fig. 2.

Related literature top

For the biological activity and pharmaceutical properties of benzothiazine and their derivatives, see: Fringuelli et al. (1998); Rathore & Kumar (2006); Barazarte et al. (2008); Bakavoli et al. (2007). For related structures, see: Saeed et al. (2010); Afrakssou et al. (2011); Sebbar et al. (2014a,b).

Experimental top

To a solution of (E)-4-allyl-2-benzylidene-3,4-dihydro-2H- benzo[b]1,4-thiazine (1 g, 3.4 mmol) and benzaldoxime (0.81 ml, 6.8 mmol) in chloroform (30 ml) was added dropwise a 24% sodium hypochlorite solution (10 ml) at 273 K. Stirring was continued for 4 h. The organic layer was dried over Na₂SO₄ and the solvent was evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel using a mixture of hexane/ethyl acetate (v/v = 80/20) as eluent. Colourless crystals were isolated when the solvent was allowed to evaporate (yield: 74%).

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: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

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. One phenyl ring is disordered over two positions.

(E)-2-Benzylidene-4-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-2H-benzo[b][1,4]thiazin-3(4H)-one top

Crystal data top

C₂₅H₂₀N₂O₂S	F(000) = 864
M_r = 412.49	D_x = 1.355 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 17.4463 (16) Å	Cell parameters from 4149 reflections
b = 5.3024 (4) Å	θ = 1.7–26.4°
c = 22.778 (2) Å	µ = 0.19 mm⁻¹
β = 106.370 (5)°	T = 296 K
V = 2021.7 (3) Å³	Block, colourless
Z = 4	0.36 × 0.31 × 0.26 mm

Data collection top

Bruker X8 APEX diffractometer	4149 independent reflections
Radiation source: fine-focus sealed tube	1980 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.095
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
T_min = 0.504, T_max = 0.748	k = −6→6
27864 measured reflections	l = −28→25

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.0437P)² + 0.9738P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.008
4149 reflections	Δρ_max = 0.48 e Å⁻³
321 parameters	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₅H₂₀N₂O₂S	V = 2021.7 (3) Å³
M_r = 412.49	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 17.4463 (16) Å	µ = 0.19 mm⁻¹
b = 5.3024 (4) Å	T = 296 K
c = 22.778 (2) Å	0.36 × 0.31 × 0.26 mm
β = 106.370 (5)°

Data collection top

Bruker X8 APEX diffractometer	4149 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1980 reflections with I > 2σ(I)
T_min = 0.504, T_max = 0.748	R_int = 0.095
27864 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.00	Δρ_max = 0.48 e Å⁻³
4149 reflections	Δρ_min = −0.26 e Å⁻³
321 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.17593 (18)	0.5680 (6)	0.36708 (14)	0.0498 (8)
C2	0.1174 (2)	0.6377 (7)	0.31368 (19)	0.0693 (11)
H2	0.0834	0.7719	0.3146	0.083*
C3	0.1096 (2)	0.5102 (9)	0.25999 (18)	0.0784 (12)
H3	0.0717	0.5614	0.2244	0.094*
C4	0.1577 (2)	0.3074 (8)	0.25874 (16)	0.0707 (11)
H4	0.1512	0.2177	0.2226	0.085*
C5	0.21579 (19)	0.2357 (6)	0.31078 (14)	0.0543 (9)
H5	0.2479	0.0968	0.3096	0.065*
C6	0.22670 (17)	0.3703 (5)	0.36516 (14)	0.0418 (7)
C7	0.28231 (19)	0.3227 (6)	0.47719 (16)	0.0529 (8)
C8	0.21687 (19)	0.4767 (6)	0.48721 (15)	0.0542 (9)
C9	0.1957 (2)	0.4326 (7)	0.53875 (16)	0.0659 (10)
H9	0.2239	0.3061	0.5641	0.079*
C10A	0.1328 (11)	0.561 (4)	0.5602 (8)	0.051 (3)	0.57 (2)
C11A	0.1042 (10)	0.781 (3)	0.5504 (5)	0.084 (3)	0.57 (2)
H11A	0.1229	0.8915	0.5258	0.101*	0.57 (2)
C12A	0.0437 (9)	0.861 (3)	0.5768 (6)	0.099 (4)	0.57 (2)
H12A	0.0224	1.0218	0.5680	0.118*	0.57 (2)
C13A	0.0161 (10)	0.713 (5)	0.6139 (12)	0.082 (6)	0.57 (2)
H13A	−0.0329	0.7447	0.6210	0.098*	0.57 (2)
C14A	0.0602 (15)	0.521 (5)	0.6399 (13)	0.094 (6)	0.57 (2)
H14A	0.0499	0.4360	0.6726	0.113*	0.57 (2)
C15A	0.1232 (12)	0.447 (3)	0.6169 (9)	0.090 (5)	0.57 (2)
H15A	0.1593	0.3255	0.6374	0.108*	0.57 (2)
C10B	0.1358 (18)	0.506 (5)	0.5683 (14)	0.060 (8)*	0.43 (2)
C11B	0.0671 (10)	0.674 (4)	0.5314 (8)	0.075 (5)	0.43 (2)
H11B	0.0663	0.7241	0.4920	0.090*	0.43 (2)
C12B	0.0078 (11)	0.752 (4)	0.5551 (8)	0.077 (5)	0.43 (2)
H12B	−0.0347	0.8505	0.5328	0.092*	0.43 (2)
C13B	0.0151 (18)	0.671 (8)	0.6186 (18)	0.108 (14)	0.43 (2)
H13B	−0.0142	0.7420	0.6428	0.129*	0.43 (2)
C14B	0.068 (3)	0.483 (9)	0.6378 (19)	0.17 (2)	0.43 (2)
H14B	0.0702	0.4082	0.6751	0.206*	0.43 (2)
C15B	0.1193 (14)	0.393 (7)	0.6073 (16)	0.142 (14)	0.43 (2)
H15B	0.1421	0.2345	0.6179	0.171*	0.43 (2)
C16	0.36034 (17)	0.1736 (5)	0.41243 (13)	0.0474 (8)
H16A	0.3559	0.1496	0.3694	0.057*
H16B	0.3637	0.0085	0.4313	0.057*
C17	0.43583 (17)	0.3205 (5)	0.44203 (14)	0.0460 (8)
H17	0.4441	0.3324	0.4863	0.055*
C18	0.50908 (17)	0.2106 (5)	0.42840 (14)	0.0468 (8)
H18A	0.5548	0.2102	0.4645	0.056*
H18B	0.4994	0.0405	0.4124	0.056*
C19	0.52051 (17)	0.3901 (5)	0.38119 (13)	0.0419 (7)
C20	0.57826 (18)	0.3586 (5)	0.34590 (14)	0.0464 (8)
C21	0.6339 (2)	0.1683 (7)	0.35988 (16)	0.0677 (10)
H21	0.6341	0.0567	0.3914	0.081*
C22	0.6896 (2)	0.1410 (8)	0.3275 (2)	0.0860 (13)
H22	0.7278	0.0140	0.3380	0.103*
C23	0.6888 (3)	0.2994 (8)	0.2803 (2)	0.0869 (13)
H23	0.7264	0.2807	0.2587	0.104*
C24	0.6332 (3)	0.4842 (8)	0.26472 (19)	0.0900 (13)
H24	0.6323	0.5905	0.2321	0.108*
C25	0.5777 (2)	0.5156 (7)	0.29715 (18)	0.0725 (11)
H25	0.5398	0.6431	0.2862	0.087*
N1	0.28861 (14)	0.3038 (4)	0.41850 (11)	0.0447 (6)
N2	0.47581 (16)	0.5856 (4)	0.37434 (12)	0.0526 (7)
O1	0.33070 (14)	0.2170 (5)	0.51952 (10)	0.0720 (7)
O2	0.42730 (13)	0.5703 (3)	0.41480 (10)	0.0562 (6)
S1	0.18110 (6)	0.72501 (16)	0.43621 (5)	0.0680 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0428 (19)	0.0534 (19)	0.053 (2)	−0.0024 (16)	0.0122 (17)	0.0073 (16)
C2	0.053 (2)	0.078 (2)	0.074 (3)	0.011 (2)	0.013 (2)	0.031 (2)
C3	0.058 (3)	0.117 (3)	0.049 (3)	0.000 (2)	−0.002 (2)	0.031 (2)
C4	0.060 (2)	0.098 (3)	0.047 (2)	−0.008 (2)	0.0034 (19)	0.003 (2)
C5	0.048 (2)	0.062 (2)	0.047 (2)	−0.0018 (16)	0.0042 (17)	−0.0010 (18)
C6	0.0375 (18)	0.0419 (16)	0.044 (2)	−0.0032 (14)	0.0086 (15)	0.0042 (15)
C7	0.043 (2)	0.059 (2)	0.055 (2)	−0.0010 (17)	0.0116 (18)	0.0007 (18)
C8	0.050 (2)	0.063 (2)	0.046 (2)	−0.0028 (17)	0.0077 (17)	−0.0047 (17)
C9	0.056 (2)	0.084 (3)	0.054 (2)	0.007 (2)	0.0101 (19)	−0.002 (2)
C10A	0.056 (7)	0.063 (10)	0.035 (7)	0.004 (6)	0.016 (5)	0.006 (6)
C11A	0.085 (9)	0.094 (8)	0.081 (7)	−0.015 (7)	0.036 (6)	−0.027 (6)
C12A	0.087 (9)	0.114 (8)	0.095 (8)	0.000 (7)	0.025 (7)	−0.043 (7)
C13A	0.060 (9)	0.122 (14)	0.081 (13)	0.024 (9)	0.049 (9)	0.004 (9)
C14A	0.091 (11)	0.102 (9)	0.120 (17)	0.033 (8)	0.080 (11)	0.033 (9)
C15A	0.142 (14)	0.096 (7)	0.059 (9)	0.057 (7)	0.072 (9)	0.032 (6)
C11B	0.055 (9)	0.105 (11)	0.067 (8)	0.009 (8)	0.021 (7)	0.001 (8)
C12B	0.061 (9)	0.105 (11)	0.070 (10)	0.024 (8)	0.027 (7)	0.010 (8)
C13B	0.12 (2)	0.123 (19)	0.08 (2)	−0.070 (18)	0.028 (15)	−0.035 (17)
C14B	0.19 (3)	0.26 (4)	0.08 (2)	0.07 (2)	0.07 (2)	0.03 (2)
C15B	0.058 (12)	0.28 (4)	0.096 (17)	0.007 (15)	0.035 (10)	−0.01 (2)
C16	0.047 (2)	0.0446 (17)	0.046 (2)	0.0058 (15)	0.0060 (16)	−0.0037 (15)
C17	0.0451 (19)	0.0443 (17)	0.0435 (19)	0.0034 (15)	0.0042 (15)	−0.0010 (15)
C18	0.0439 (19)	0.0441 (17)	0.048 (2)	0.0064 (15)	0.0052 (15)	−0.0003 (15)
C19	0.0416 (18)	0.0341 (15)	0.0426 (19)	−0.0021 (14)	−0.0003 (15)	−0.0037 (14)
C20	0.0431 (19)	0.0451 (17)	0.047 (2)	−0.0032 (15)	0.0053 (16)	−0.0015 (16)
C21	0.072 (3)	0.070 (2)	0.066 (3)	0.019 (2)	0.028 (2)	0.0122 (19)
C22	0.082 (3)	0.091 (3)	0.095 (3)	0.030 (2)	0.042 (3)	0.013 (3)
C23	0.084 (3)	0.097 (3)	0.095 (3)	0.007 (3)	0.050 (3)	0.004 (3)
C24	0.097 (3)	0.096 (3)	0.089 (3)	0.005 (3)	0.046 (3)	0.027 (3)
C25	0.069 (3)	0.067 (2)	0.084 (3)	0.010 (2)	0.024 (2)	0.019 (2)
N1	0.0421 (15)	0.0516 (15)	0.0388 (16)	0.0008 (12)	0.0085 (13)	−0.0021 (12)
N2	0.0543 (17)	0.0399 (14)	0.0595 (19)	0.0019 (13)	0.0095 (15)	−0.0023 (13)
O1	0.0622 (16)	0.1030 (19)	0.0471 (15)	0.0177 (14)	0.0093 (13)	0.0139 (14)
O2	0.0586 (14)	0.0385 (12)	0.0724 (16)	0.0094 (11)	0.0200 (13)	−0.0006 (11)
S1	0.0727 (7)	0.0573 (5)	0.0770 (7)	0.0094 (5)	0.0258 (5)	−0.0015 (5)

Geometric parameters (Å, º) top

C1—C6	1.381 (4)	C11B—C12B	1.360 (15)
C1—C2	1.400 (4)	C11B—H11B	0.9300
C1—S1	1.761 (3)	C12B—C13B	1.48 (5)
C2—C3	1.370 (5)	C12B—H12B	0.9300
C2—H2	0.9300	C13B—C14B	1.35 (7)
C3—C4	1.369 (5)	C13B—H13B	0.9300
C3—H3	0.9300	C14B—C15B	1.36 (5)
C4—C5	1.378 (4)	C14B—H14B	0.9300
C4—H4	0.9300	C15B—H15B	0.9300
C5—C6	1.395 (4)	C16—N1	1.469 (3)
C5—H5	0.9300	C16—C17	1.515 (4)
C6—N1	1.424 (3)	C16—H16A	0.9700
C7—O1	1.224 (4)	C16—H16B	0.9700
C7—N1	1.376 (4)	C17—O2	1.453 (3)
C7—C8	1.473 (4)	C17—C18	1.514 (4)
C8—C9	1.347 (4)	C17—H17	0.9800
C8—S1	1.750 (3)	C18—C19	1.491 (4)
C9—C10B	1.45 (3)	C18—H18A	0.9700
C9—C10A	1.49 (2)	C18—H18B	0.9700
C9—H9	0.9300	C19—N2	1.280 (3)
C10A—C11A	1.26 (2)	C19—C20	1.465 (4)
C10A—C15A	1.48 (2)	C20—C21	1.373 (4)
C11A—C12A	1.418 (14)	C20—C25	1.386 (4)
C11A—H11A	0.9300	C21—C22	1.384 (5)
C12A—C13A	1.34 (3)	C21—H21	0.9300
C12A—H12A	0.9300	C22—C23	1.361 (5)
C13A—C14A	1.31 (5)	C22—H22	0.9300
C13A—H13A	0.9300	C23—C24	1.354 (5)
C14A—C15A	1.40 (3)	C23—H23	0.9300
C14A—H14A	0.9300	C24—C25	1.383 (5)
C15A—H15A	0.9300	C24—H24	0.9300
C10B—C15B	1.17 (4)	C25—H25	0.9300
C10B—C11B	1.54 (3)	N2—O2	1.418 (3)

C6—C1—C2	119.4 (3)	C14B—C13B—C12B	113 (3)
C6—C1—S1	121.0 (2)	C14B—C13B—H13B	123.4
C2—C1—S1	119.5 (3)	C12B—C13B—H13B	123.4
C3—C2—C1	120.6 (4)	C13B—C14B—C15B	126 (4)
C3—C2—H2	119.7	C13B—C14B—H14B	117.1
C1—C2—H2	119.7	C15B—C14B—H14B	117.1
C4—C3—C2	119.9 (3)	C10B—C15B—C14B	123 (4)
C4—C3—H3	120.0	C10B—C15B—H15B	118.6
C2—C3—H3	120.0	C14B—C15B—H15B	118.6
C3—C4—C5	120.3 (4)	N1—C16—C17	111.9 (2)
C3—C4—H4	119.8	N1—C16—H16A	109.2
C5—C4—H4	119.8	C17—C16—H16A	109.2
C4—C5—C6	120.4 (3)	N1—C16—H16B	109.2
C4—C5—H5	119.8	C17—C16—H16B	109.2
C6—C5—H5	119.8	H16A—C16—H16B	107.9
C1—C6—C5	119.2 (3)	O2—C17—C18	104.7 (2)
C1—C6—N1	120.0 (3)	O2—C17—C16	107.9 (2)
C5—C6—N1	120.8 (3)	C18—C17—C16	112.9 (2)
O1—C7—N1	120.4 (3)	O2—C17—H17	110.4
O1—C7—C8	121.6 (3)	C18—C17—H17	110.4
N1—C7—C8	118.0 (3)	C16—C17—H17	110.4
C9—C8—C7	117.0 (3)	C19—C18—C17	101.2 (2)
C9—C8—S1	125.1 (3)	C19—C18—H18A	111.5
C7—C8—S1	117.5 (3)	C17—C18—H18A	111.5
C8—C9—C10B	140.4 (11)	C19—C18—H18B	111.5
C8—C9—C10A	128.0 (7)	C17—C18—H18B	111.5
C8—C9—H9	116.0	H18A—C18—H18B	109.3
C10A—C9—H9	116.0	N2—C19—C20	121.0 (3)
C11A—C10A—C15A	113.4 (15)	N2—C19—C18	113.8 (3)
C11A—C10A—C9	131.0 (14)	C20—C19—C18	125.1 (3)
C15A—C10A—C9	112.0 (14)	C21—C20—C25	118.2 (3)
C10A—C11A—C12A	120.2 (12)	C21—C20—C19	120.4 (3)
C10A—C11A—H11A	119.9	C25—C20—C19	121.4 (3)
C12A—C11A—H11A	119.9	C20—C21—C22	120.7 (3)
C13A—C12A—C11A	122.4 (13)	C20—C21—H21	119.7
C13A—C12A—H12A	118.8	C22—C21—H21	119.7
C11A—C12A—H12A	118.8	C23—C22—C21	120.2 (4)
C14A—C13A—C12A	118.2 (14)	C23—C22—H22	119.9
C14A—C13A—H13A	120.9	C21—C22—H22	119.9
C12A—C13A—H13A	120.9	C24—C23—C22	120.1 (4)
C13A—C14A—C15A	118 (2)	C24—C23—H23	120.0
C13A—C14A—H14A	121.0	C22—C23—H23	120.0
C15A—C14A—H14A	121.0	C23—C24—C25	120.3 (4)
C14A—C15A—C10A	120.5 (17)	C23—C24—H24	119.9
C14A—C15A—H15A	119.8	C25—C24—H24	119.9
C10A—C15A—H15A	119.8	C24—C25—C20	120.5 (4)
C15B—C10B—C9	125 (3)	C24—C25—H25	119.7
C15B—C10B—C11B	113 (3)	C20—C25—H25	119.7
C9—C10B—C11B	117 (2)	C7—N1—C6	124.2 (3)
C12B—C11B—C10B	121.4 (16)	C7—N1—C16	115.4 (2)
C12B—C11B—H11B	119.3	C6—N1—C16	119.8 (2)
C10B—C11B—H11B	119.3	C19—N2—O2	109.2 (2)
C11B—C12B—C13B	115.7 (17)	N2—O2—C17	108.8 (2)
C11B—C12B—H12B	122.1	C8—S1—C1	99.02 (15)
C13B—C12B—H12B	122.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1ⁱ	0.93	2.43	3.339 (4)	166
C18—H18B···N2ⁱⁱ	0.97	2.56	3.526 (3)	178

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1ⁱ	0.93	2.43	3.339 (4)	166.1
C18—H18B···N2ⁱⁱ	0.97	2.56	3.526 (3)	178

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y−1, z.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and the University Mohammed V, Rabat, Morocco, for financial support.

References

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Volume 71| Part 6| June 2015| Pages o423-o424

doi:10.1107/S2056989015009755

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

Crystal structure of (E)-2-benzyl­­idene-4-[(3-phenyl-4,5-di­hydro­isoxazol-5-yl)meth­yl]-2H-benzo[b][1,4]thia­zin-3(4H)-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (E)-2-benzylidene-4-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-2H-benzo[b][1,4]thiazin-3(4H)-one