Crystal structure of (Z)-2-benzyl­idene-4-methyl-2H-benzo[b][1,4]thia­zin-3(4H)-one

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

doi:10.1107/S2056989015019295

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 11| November 2015| Pages o862-o863

https://doi.org/10.1107/S2056989015019295

Open

access

Crystal structure of (Z)-2-benzylidene-4-methyl-2H-benzo[b][1,4]thiazin-3(4H)-one

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

^aLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: mellouz05@gmail.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 7 October 2015; accepted 12 October 2015; online 17 October 2015)

In the title compound, C₁₆H₁₃NOS, the 1,4-thiazine ring displays a screw-boat conformation. The conformation about the ethene bond [1.344 (2) Å] is Z. The plane of the fused benzene ring makes a dihedral angle of 58.95 (9)° with the pendent phenyl ring, indicating a twisted conformation in the molecule. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers.

Keywords: crystal structure; thiomorpholin-3-one derivative; benzothiazine derivative; hydrogen bonding.

CCDC reference: 1430755

1. Related literature

For background to the pharmacological activity and potential applications of benzothiazines, see: Schiaffella et al. (2006 ); Gupta et al. (2009 ); Armenise et al. (2000 ); Bansode et al. (2009 ); Dixit et al. (2009 ); Dixit et al. (2008 ); Thomas et al. (2003 ). For medicinal applications; see: Warren et al. (1987 ); Armenise et al. (2012 ); Sabatini et al. (2008 ); Jacquot et al. (2001 ); Kalluraya et al. (2005 ); Munirajasekar et al. (2011 ). For similar compounds, see: Sebbar et al. (2014a ,b ); Zerzouf et al. (2001 ).

2. Experimental

2.1. Crystal data

C₁₆H₁₃NOS
M_r = 267.33
Monoclinic, P 2₁ /c
a = 9.1497 (3) Å
b = 14.7052 (5) Å
c = 10.0037 (3) Å
β = 97.051 (1)°
V = 1335.80 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.23 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 = 0.670, T_max = 0.746
25334 measured reflections
4082 independent reflections
3071 reflections with I > 2σ(I)
R_int = 0.031

2.3. Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.153
S = 1.12
4082 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.50	3.404 (2)	164
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; 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: 1430755

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019295/tk5394sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019295/tk5394Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015019295/tk5394Isup3.cml

checkCIF report

Comment top

Over the years, 4H-1,4-benzothiazines have constituted an important class of heterocycles which, even when part of a complex molecule, possess a wide spectrum of biological activities (Schiaffella et al., 2006; Gupta et al., 2009; Armenise et al., 2000). Due to the presence of a fold along the nitrogen—sulfur axis, the biological activity of some 1,4-benzothiazines is similar to that of phenothiazines, featuring the same structural specificity (Bansode et al., 2009; Dixit et al., 2009; Dixit et al., 2008; Thomas et al., 2003). Generally, benzothiazine and derivatives have found widespread application as analgesic (Warren et al., 1987), antibacterial (Armenise et al., 2012; Sabatini et al., 2008), anticancer (Jacquot et al., 2001), anticonvulsant (Kalluraya et al., 2005) and anthelmintic (Munirajasekar et al., 2011) agents. As a continuation of our research work devoted to the development of N-substituted benzothiazine and evaluating their potential pharmacological activities, we have checked the action of iodomethane towards (E)-2-benzylidene-2H-benzo[b][1,4]thiazin-3(4H)-one under phase-transfer catalysis conditions using tetra n-butylammonium bromide (TBAB) as catalyst and potassium carbonate as base (Sebbar et al., 2014a, Sebbar et al., 2014b; Zerzouf et al., 2001). This led to the characterization of the title compound, Scheme 1.

The molecule of the title compound is build up from two fused six-membered rings linked as shown in Fig.1. The dihedral angle between the (C1 to C6) and (C11 to C16) benzene rings is 58.95 (9)°.

In the crystal, the molecules are linked together by a hydrogen bond (C12–H12···O1) in a way to build a dimer, as shown in Fig. 2 and Table 1.

Related literature top

For background to the pharmacological activity and potential applications of benzothiazines, see: Schiaffella et al. (2006); Gupta et al. (2009); Armenise et al. (2000); Bansode et al. (2009); Dixit et al. (2009); Dixit et al. (2008); Thomas et al. (2003). For medicinal applications; see: Warren et al. (1987); Armenise et al. (2012); Sabatini et al. (2008); Jacquot et al. (2001); Kalluraya et al. (2005); Munirajasekar et al. (2011). For similar compounds, see: Sebbar et al. (2014a,b); Zerzouf et al. (2001).

Experimental top

To a solution of 2-(benzylidene)-3,4-dihydro-2H-1,4-benzothiazin-3-one (0.5 g, 2 mmol), potassium carbonate (0.55 g, 4 mmol) and tetra n-butyl ammonium bromide (0.064 g, 0.2 mmol) in DMF (15 ml) was added iodomethane (0.25 ml, 4 mmol). Stirring was continued at room temperature for 12 h. The mixture was filtered and the solvent removed. The residue was extracted with water. The organic compound was chromatographed on a column of silica gel with ethyl acetate-hexane (9/1) as eluent. Brown crystals were isolated when the solvent was allowed to evaporate (yield: 53%; m.p. = 342 K).

Structure description top

The molecule of the title compound is build up from two fused six-membered rings linked as shown in Fig.1. The dihedral angle between the (C1 to C6) and (C11 to C16) benzene rings is 58.95 (9)°.

In the crystal, the molecules are linked together by a hydrogen bond (C12–H12···O1) in a way to build a dimer, as shown in Fig. 2 and Table 1.

For background to the pharmacological activity and potential applications of benzothiazines, see: Schiaffella et al. (2006); Gupta et al. (2009); Armenise et al. (2000); Bansode et al. (2009); Dixit et al. (2009); Dixit et al. (2008); Thomas et al. (2003). For medicinal applications; see: Warren et al. (1987); Armenise et al. (2012); Sabatini et al. (2008); Jacquot et al. (2001); Kalluraya et al. (2005); Munirajasekar et al. (2011). For similar compounds, see: Sebbar et al. (2014a,b); Zerzouf et al. (2001).

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

	Fig. 1. Molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. Supramolecular association in the title compound, showing inversion dimers of molecules linked through C12—H12···O1 hydrogen bond (dashed lines).

(Z)-2-Benzylidene-4-methyl-2H-benzo[b][1,4]thiazin-3(4H)-one top

Crystal data top

C₁₆H₁₃NOS	D_x = 1.329 Mg m⁻³
M_r = 267.33	Melting point: 342 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.1497 (3) Å	Cell parameters from 4082 reflections
b = 14.7052 (5) Å	θ = 2.2–30.5°
c = 10.0037 (3) Å	µ = 0.23 mm⁻¹
β = 97.051 (1)°	T = 296 K
V = 1335.80 (7) Å³	Prism, brown
Z = 4	0.36 × 0.31 × 0.26 mm
F(000) = 560

Data collection top

Bruker X8 APEX diffractometer	4082 independent reflections
Radiation source: fine-focus sealed tube	3071 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
φ and ω scans	θ_max = 30.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→13
T_min = 0.670, T_max = 0.746	k = −20→21
25334 measured reflections	l = −14→14

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0757P)² + 0.2379P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
4082 reflections	Δρ_max = 0.37 e Å⁻³
172 parameters	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₆H₁₃NOS	V = 1335.80 (7) Å³
M_r = 267.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1497 (3) Å	µ = 0.23 mm⁻¹
b = 14.7052 (5) Å	T = 296 K
c = 10.0037 (3) Å	0.36 × 0.31 × 0.26 mm
β = 97.051 (1)°

Data collection top

Bruker X8 APEX diffractometer	4082 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3071 reflections with I > 2σ(I)
T_min = 0.670, T_max = 0.746	R_int = 0.031
25334 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.12	Δρ_max = 0.37 e Å⁻³
4082 reflections	Δρ_min = −0.21 e Å⁻³
172 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
C1	0.73318 (17)	0.52736 (10)	0.43834 (14)	0.0426 (3)
C2	0.6952 (2)	0.48778 (12)	0.55605 (16)	0.0513 (4)
H2	0.6186	0.4459	0.5516	0.062*
C3	0.7715 (2)	0.51089 (13)	0.67964 (16)	0.0579 (5)
H3	0.7445	0.4862	0.7586	0.070*
C4	0.8872 (2)	0.57054 (13)	0.68451 (17)	0.0596 (4)
H4	0.9383	0.5863	0.7675	0.071*
C5	0.9292 (2)	0.60761 (12)	0.56848 (17)	0.0549 (4)
H5	1.0100	0.6464	0.5737	0.066*
C6	0.85101 (17)	0.58725 (10)	0.44272 (14)	0.0425 (3)
C7	0.86549 (16)	0.58789 (10)	0.19776 (14)	0.0435 (3)
C8	0.75763 (16)	0.51143 (10)	0.17601 (14)	0.0408 (3)
C9	0.9905 (3)	0.70539 (13)	0.3367 (2)	0.0689 (5)
H9A	1.0003	0.7272	0.4278	0.103*
H9B	1.0853	0.6874	0.3142	0.103*
H9C	0.9512	0.7528	0.2768	0.103*
C10	0.75953 (16)	0.45936 (11)	0.06583 (14)	0.0430 (3)
H10	0.8336	0.4735	0.0133	0.052*
C11	0.66396 (17)	0.38420 (10)	0.01526 (14)	0.0432 (3)
C12	0.7201 (2)	0.32215 (12)	−0.07117 (18)	0.0563 (4)
H12	0.8150	0.3299	−0.0935	0.068*
C13	0.6368 (3)	0.24967 (15)	−0.1236 (3)	0.0770 (6)
H13	0.6763	0.2088	−0.1804	0.092*
C14	0.4954 (3)	0.23710 (15)	−0.0928 (2)	0.0744 (6)
H14	0.4397	0.1879	−0.1283	0.089*
C15	0.4378 (2)	0.29778 (15)	−0.0094 (2)	0.0663 (5)
H15	0.3427	0.2893	0.0121	0.080*
C16	0.51940 (18)	0.37157 (13)	0.04339 (17)	0.0550 (4)
H16	0.4778	0.4130	0.0979	0.066*
N1	0.89082 (15)	0.62709 (9)	0.32356 (13)	0.0466 (3)
O1	0.92759 (14)	0.61644 (9)	0.10488 (12)	0.0591 (3)
S1	0.62428 (4)	0.50183 (3)	0.28662 (4)	0.05206 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0506 (8)	0.0451 (7)	0.0335 (6)	0.0048 (6)	0.0115 (6)	0.0010 (5)
C2	0.0614 (10)	0.0554 (9)	0.0395 (7)	0.0038 (7)	0.0162 (7)	0.0053 (6)
C3	0.0759 (12)	0.0629 (10)	0.0359 (8)	0.0138 (8)	0.0103 (8)	0.0093 (7)
C4	0.0735 (11)	0.0637 (10)	0.0390 (7)	0.0134 (9)	−0.0027 (7)	−0.0030 (7)
C5	0.0626 (10)	0.0528 (9)	0.0479 (8)	0.0018 (7)	0.0014 (7)	−0.0070 (7)
C6	0.0537 (8)	0.0380 (7)	0.0367 (7)	0.0064 (6)	0.0090 (6)	−0.0005 (5)
C7	0.0451 (7)	0.0476 (8)	0.0390 (7)	−0.0009 (6)	0.0101 (6)	0.0039 (6)
C8	0.0405 (7)	0.0504 (8)	0.0322 (6)	−0.0003 (6)	0.0079 (5)	0.0045 (5)
C9	0.0953 (15)	0.0483 (9)	0.0663 (11)	−0.0214 (9)	0.0228 (10)	−0.0069 (8)
C10	0.0425 (7)	0.0545 (8)	0.0327 (6)	−0.0003 (6)	0.0077 (5)	0.0038 (6)
C11	0.0459 (7)	0.0500 (8)	0.0328 (6)	−0.0006 (6)	0.0019 (5)	0.0059 (5)
C12	0.0566 (9)	0.0543 (9)	0.0589 (10)	−0.0009 (7)	0.0107 (8)	−0.0052 (7)
C13	0.0818 (14)	0.0585 (11)	0.0914 (16)	−0.0055 (10)	0.0138 (12)	−0.0195 (10)
C14	0.0754 (13)	0.0584 (11)	0.0862 (14)	−0.0158 (10)	−0.0033 (11)	−0.0036 (10)
C15	0.0503 (9)	0.0789 (13)	0.0677 (11)	−0.0139 (9)	−0.0012 (8)	0.0097 (10)
C16	0.0465 (8)	0.0704 (11)	0.0474 (8)	−0.0025 (7)	0.0033 (6)	−0.0006 (8)
N1	0.0583 (8)	0.0404 (6)	0.0429 (6)	−0.0045 (5)	0.0130 (5)	0.0001 (5)
O1	0.0633 (7)	0.0710 (8)	0.0461 (6)	−0.0177 (6)	0.0191 (5)	0.0037 (5)
S1	0.0473 (2)	0.0749 (3)	0.0361 (2)	−0.01066 (18)	0.01376 (16)	−0.00324 (16)

Geometric parameters (Å, º) top

C1—C6	1.389 (2)	C9—N1	1.465 (2)
C1—C2	1.395 (2)	C9—H9A	0.9600
C1—S1	1.7510 (15)	C9—H9B	0.9600
C2—C3	1.386 (3)	C9—H9C	0.9600
C2—H2	0.9300	C10—C11	1.461 (2)
C3—C4	1.371 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.398 (2)
C4—C5	1.379 (3)	C11—C16	1.398 (2)
C4—H4	0.9300	C12—C13	1.376 (3)
C5—C6	1.401 (2)	C12—H12	0.9300
C5—H5	0.9300	C13—C14	1.379 (3)
C6—N1	1.4154 (19)	C13—H13	0.9300
C7—O1	1.2215 (18)	C14—C15	1.371 (3)
C7—N1	1.3777 (19)	C14—H14	0.9300
C7—C8	1.494 (2)	C15—C16	1.385 (3)
C8—C10	1.344 (2)	C15—H15	0.9300
C8—S1	1.7505 (15)	C16—H16	0.9300

C6—C1—C2	120.73 (14)	H9A—C9—H9C	109.5
C6—C1—S1	121.35 (11)	H9B—C9—H9C	109.5
C2—C1—S1	117.89 (13)	C8—C10—C11	130.37 (14)
C3—C2—C1	120.00 (17)	C8—C10—H10	114.8
C3—C2—H2	120.0	C11—C10—H10	114.8
C1—C2—H2	120.0	C12—C11—C16	117.82 (15)
C4—C3—C2	119.42 (16)	C12—C11—C10	117.27 (14)
C4—C3—H3	120.3	C16—C11—C10	124.87 (15)
C2—C3—H3	120.3	C13—C12—C11	120.86 (18)
C3—C4—C5	121.10 (16)	C13—C12—H12	119.6
C3—C4—H4	119.5	C11—C12—H12	119.6
C5—C4—H4	119.5	C12—C13—C14	120.6 (2)
C4—C5—C6	120.48 (17)	C12—C13—H13	119.7
C4—C5—H5	119.8	C14—C13—H13	119.7
C6—C5—H5	119.8	C15—C14—C13	119.39 (19)
C1—C6—C5	118.21 (14)	C15—C14—H14	120.3
C1—C6—N1	121.00 (13)	C13—C14—H14	120.3
C5—C6—N1	120.79 (15)	C14—C15—C16	120.82 (19)
O1—C7—N1	120.60 (14)	C14—C15—H15	119.6
O1—C7—C8	120.56 (14)	C16—C15—H15	119.6
N1—C7—C8	118.81 (12)	C15—C16—C11	120.45 (18)
C10—C8—C7	118.25 (13)	C15—C16—H16	119.8
C10—C8—S1	123.55 (12)	C11—C16—H16	119.8
C7—C8—S1	117.89 (11)	C7—N1—C6	124.35 (12)
N1—C9—H9A	109.5	C7—N1—C9	116.37 (13)
N1—C9—H9B	109.5	C6—N1—C9	118.12 (13)
H9A—C9—H9B	109.5	C8—S1—C1	99.44 (7)
N1—C9—H9C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.50	3.404 (2)	164

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.50	3.404 (2)	164

Symmetry code: (i) −x+2, −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

Armenise, D., Muraglia, M., Florio, M. A., De Laurentis, N., Rosato, A., Carrieri, A., Corbo, F. & Franchini, C. (2012). Arch. Pharm. Pharm. Med. Chem. 345, 407–416. Web of Science CrossRef CAS Google Scholar
Armenise, D., Trapani, G., Arrivo, V., Laraspata, E. & Morlacchi, F. (2000). J. Heterocycl. Chem. 37, 1611–1616. CrossRef CAS Google Scholar
Bansode, T. N., Shelke, J. V. & Dongre, V. G. (2009). Eur. J. Med. Chem. 44, 5094–5098. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dixit, Y., Dixit, R., Gautam, N. & Gautam, D. C. (2008). E-J. Chem. 5, 1063–1068. CrossRef CAS Google Scholar
Dixit, Y., Dixit, R., Gautam, N. & Gautam, D. C. (2009). Nucleosides Nucleotides Nucleic Acids, 28, 998–1006. Web of Science CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gupta, S., Ajmera, N., Meena, P., Gautam, N., Kumar, A. & Gautam, D. C. (2009). Jordan. J. Chem. 4, 209–221. CAS Google Scholar
Jacquot, Y., Bermont, L., Giorgi, H., Refouvelet, B. L., Adessi, G., Daubrosse, E. & Xicluna, A. (2001). Eur. J. Med. Chem. 36, 127–136. Web of Science CrossRef PubMed CAS Google Scholar
Kalluraya, B., Chimbalkar, R. M. & Hegde, J. C. (2005). Indian J. Heterocycl. Chem. 15, 15–18. CAS Google Scholar
Munirajasekar, D., Himaja, M. & Sunil, M. (2011). Int. Res. J. Pharm. 2, 114–117. Google Scholar
Sabatini, S., Kaatz, G. W., Rossolini, G. M., Brandini, D. & Fravolini, A. (2008). J. Med. Chem. 51, 4321–4330. Web of Science CrossRef PubMed CAS Google Scholar
Schiaffella, F., Macchiarulo, A., Milanese, L., Vecchiarelli, A. & Fringuelli, R. (2006). Bioorg. Med. Chem. 14, 5196–5203. Web of Science CrossRef PubMed CAS Google Scholar
Sebbar, N. K., El Fal, M., Essassi, E. M., Saadi, M. & El Ammari, L. (2014b). Acta Cryst. E70, o686. CSD CrossRef IUCr Journals Google Scholar
Sebbar, N. K., Zerzouf, A., Essassi, E. M., Saadi, M. & El Ammari, L. (2014a). Acta Cryst. E70, o614. CSD CrossRef IUCr Journals 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
Thomas, L., Gupta, A. & Gupta, V. (2003). J. Fluor. Chem. 122, 207–213. Web of Science CrossRef CAS Google Scholar
Warren, B. K. & Knaus, E. E. (1987). Eur. J. Med. Chem. 22, 411–415. CrossRef CAS Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zerzouf, A., Salem, M., Essassi, E. M. & Pierrot, M. (2001). Acta Cryst. E57, o498–o499. Web of Science CSD 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 11| November 2015| Pages o862-o863

https://doi.org/10.1107/S2056989015019295

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Crystal structure of (Z)-2-benzyl­­idene-4-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 (Z)-2-benzylidene-4-methyl-2H-benzo[b][1,4]thiazin-3(4H)-one