Literature DB >> 26594566

Crystal structure of (Z)-2-benzyl-idene-4-methyl-2H-benzo[b][1,4]thia-zin-3(4H)-one.

Mohamed Ellouz¹, Nada Kheira Sebbar¹, El Mokhtar Essassi¹, Mohamed Saadi², Lahcen El Ammari².

Abstract

In the title compound, C16H13NOS, the 1,4-thia-zine 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 mol-ecule. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds, forming inversion dimers.

Entities: Chemical Disease Species

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

Year: 2015 PMID： 26594566 PMCID： PMC4645059 DOI： 10.1107/S2056989015019295

Source DB: PubMed Journal: Acta Crystallogr E Crystallogr Commun

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 ▸).

Experimental

Crystal data

C16H13NOS M = 267.33 Monoclinic, 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

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

Refinement

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

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 ▸). Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015019295/tk5394sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015019295/tk5394Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015019295/tk5394Isup3.cml Click here for additional data file. . DOI: 10.1107/S2056989015019295/tk5394fig1.tif 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. Click here for additional data file. . DOI: 10.1107/S2056989015019295/tk5394fig2.tif Supramolecular association in the title compound, showing inversion dimers of molecules linked through C12—H12⋯O1 hydrogen bond (dashed lines). CCDC reference: 1430755 Additional supporting information: crystallographic information; 3D view; checkCIF report

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

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 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

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	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)

	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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C12H12O1ⁱ	0.93	2.50	3.404(2)	164

Symmetry code: (i) .

10 in total

1. 4H-1,4-benzothiazine, dihydro-1,4-benzothiazinones and 2-amino-5-fluorobenzenethiol derivatives: design, synthesis and in vitro antimicrobial screening.

Authors: Domenico Armenise; Marilena Muraglia; Marco Antonio Florio; Nicolino De Laurentis; Antonio Rosato; Antonio Carrieri; Filomena Corbo; Carlo Franchini
Journal: Arch Pharm (Weinheim) Date: 2011-12-07 Impact factor: 3.751

2. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

3. Substituted benzopyranobenzothiazinones. Synthesis and estrogenic activity on MCF-7 breast carcinoma cells.

Authors: Y Jacquot; L Bermont; H Giorgi; B Refouvelet; G L Adessi; E Daubrosse; A Xicluna
Journal: Eur J Med Chem Date: 2001-02 Impact factor: 6.514

4. Synthesis and antimicrobial activities of novel biologically active heterocycles: 10h-phenothiazines, their ribofuranosides, and sulfone derivatives.

Authors: Yogesh Dixit; Rahul Dixit; Naveen Gautam; D C Gautam
Journal: Nucleosides Nucleotides Nucleic Acids Date: 2009-11 Impact factor: 1.381

5. Novel ketoconazole analogues based on the replacement of 2,4-dichlorophenyl group with 1,4-benzothiazine moiety: design, synthesis, and microbiological evaluation.

Authors: Fausto Schiaffella; Antonio Macchiarulo; Lara Milanese; Anna Vecchiarelli; Renata Fringuelli
Journal: Bioorg Med Chem Date: 2006-05-02 Impact factor: 3.641

6. From phenothiazine to 3-phenyl-1,4-benzothiazine derivatives as inhibitors of the Staphylococcus aureus NorA multidrug efflux pump.

Authors: Stefano Sabatini; Glenn W Kaatz; Gian Maria Rossolini; David Brandini; Arnaldo Fravolini
Journal: J Med Chem Date: 2008-06-25 Impact factor: 7.446