organic compounds
Z)-2-benzylidene-4-methyl-2H-benzo[b][1,4]thiazin-3(4H)-one
of (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
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
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2.3. Refinement
|
Data collection: APEX2 (Bruker, 2009); cell 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
https://doi.org/10.1107/S2056989015019295/tk5394sup1.cif
contains datablock I. DOI: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
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
Brown crystals were isolated when the solvent was allowed to evaporate (yield: 53%; m.p. = 342 K).The H atoms were located in a difference map and treated as riding with C—H = 0.93 Å (aromatic) and C—H = 0.96 Å (methyl), and with Uiso(H) = 1.2 Ueq (aromatic) and Uiso(H) = 1.5 Ueq (methyl).
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
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.
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).
Data collection: APEX2 (Bruker, 2009); cell
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).C16H13NOS | Dx = 1.329 Mg m−3 |
Mr = 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 |
Bruker X8 APEX diffractometer | 4082 independent reflections |
Radiation source: fine-focus sealed tube | 3071 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 30.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −7→13 |
Tmin = 0.670, Tmax = 0.746 | k = −20→21 |
25334 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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.0757P)2 + 0.2379P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
4082 reflections | Δρmax = 0.37 e Å−3 |
172 parameters | Δρmin = −0.21 e Å−3 |
C16H13NOS | V = 1335.80 (7) Å3 |
Mr = 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)° |
Bruker X8 APEX diffractometer | 4082 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3071 reflections with I > 2σ(I) |
Tmin = 0.670, Tmax = 0.746 | Rint = 0.031 |
25334 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.37 e Å−3 |
4082 reflections | Δρmin = −0.21 e Å−3 |
172 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 | 0.73318 (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) |
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) |
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 |
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. |
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
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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.