organic compounds
3-Chloro-4-[2-(4-chlorobenzylidene)hydrazinylidene]-1-methyl-3,4-dihydro-1H-2λ6,1-benzothiazine-2,2-dione
aDepartment of Chemistry, Gomal University, Dera Ismail Khan, NWFP, Pakistan, bDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan, cDepartment of Physics, University of Sargodha, Sargodha, Pakistan, dDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, and eMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan
*Correspondence e-mail: hafizshafique@hotmail.com
In the title compound, C16H13Cl2N3O2S, the dihedral angle between the aromatic rings is 6.62 (2)° and the C=N—N=C torsion angle is 176.2 (4)°. The thiazine ring shows an with the S atom displaced by 0.633 (6) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.037 Å). The Cl atom is an an axial conformation and is displaced by 2.015 (6) Å from the thiazine ring plane. In the crystal, molecules are linked by C—H⋯O interactions, generating a three-dimensional network. Very weak aromatic π–π stacking interactions [centroid–centroid separations = 3.928 (2) Å] are also observed.
Related literature
For background to benzothiazines, see: Misu & Togo (2003); Harmata et al. (2006). For the synthesis and biological activity of the title compound and related materials, see: Ahmad et al. (2010a); Shafiq et al. (2011a). For further synthetic details, see: Shafiq et al. (2011b). For related structures, see: Ahmad et al. (2010b); Shafiq et al. (2011c, 2013).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; 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: SHELXL97.
Supporting information
10.1107/S1600536813004443/im2417sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813004443/im2417Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813004443/im2417Isup3.cml
The Schiff base derivative of (4Z)-4-hydrazinylidene-1-methyl-3,4-dihydro -1H-2,1-benzothiazine 2,2-dioxide (Shafiq et al., 2011c) and para-chlorobenzaldehyde was prepared using the method reported previously (Shafiq et al., 2011a). Chlorination of the Schiff base was undertaken using N-chloro succinimide and dibenzoylperoxide (Shafiq et al., 2011b). The crude product was re-crystallized from ethyl acetate and dichloromethane solution (1:1 v/v) to obtain yellow blocks of the title compound.
H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and refined as riding. The methyl group was allowed to rotate, but not to tip, to best fit the electron density. The constraint Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C) was applied.
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXL97 (Sheldrick, 2008).C16H13Cl2N3O2S | F(000) = 784 |
Mr = 382.25 | Dx = 1.497 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 225 reflections |
a = 12.309 (2) Å | θ = 3.7–22.3° |
b = 17.189 (3) Å | µ = 0.52 mm−1 |
c = 8.1837 (13) Å | T = 296 K |
β = 101.632 (8)° | Block, yellow |
V = 1695.9 (5) Å3 | 0.28 × 0.16 × 0.14 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 3319 independent reflections |
Radiation source: fine-focus sealed tube | 1736 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.076 |
ω scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −15→15 |
Tmin = 0.868, Tmax = 0.931 | k = −21→21 |
13580 measured reflections | l = −10→9 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.047P)2 + 0.7016P] where P = (Fo2 + 2Fc2)/3 |
3319 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C16H13Cl2N3O2S | V = 1695.9 (5) Å3 |
Mr = 382.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.309 (2) Å | µ = 0.52 mm−1 |
b = 17.189 (3) Å | T = 296 K |
c = 8.1837 (13) Å | 0.28 × 0.16 × 0.14 mm |
β = 101.632 (8)° |
Bruker APEXII CCD diffractometer | 3319 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 1736 reflections with I > 2σ(I) |
Tmin = 0.868, Tmax = 0.931 | Rint = 0.076 |
13580 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.42 e Å−3 |
3319 reflections | Δρmin = −0.33 e Å−3 |
218 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. |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2793 (4) | 0.0825 (2) | 0.2790 (5) | 0.0443 (10) | |
C2 | 0.3546 (4) | 0.0531 (2) | 0.4159 (5) | 0.0562 (12) | |
H2 | 0.4291 | 0.0496 | 0.4103 | 0.067* | |
C3 | 0.3216 (5) | 0.0291 (3) | 0.5591 (6) | 0.0754 (16) | |
H3 | 0.3733 | 0.0100 | 0.6489 | 0.090* | |
C4 | 0.2111 (6) | 0.0339 (3) | 0.5677 (6) | 0.0820 (18) | |
H4 | 0.1879 | 0.0176 | 0.6635 | 0.098* | |
C5 | 0.1353 (5) | 0.0624 (3) | 0.4352 (7) | 0.0736 (15) | |
H5 | 0.0609 | 0.0652 | 0.4421 | 0.088* | |
C6 | 0.1678 (4) | 0.0875 (2) | 0.2903 (5) | 0.0534 (11) | |
C7 | −0.0133 (4) | 0.1564 (3) | 0.1866 (7) | 0.0877 (17) | |
H7A | −0.0670 | 0.1177 | 0.2001 | 0.132* | |
H7B | −0.0435 | 0.1892 | 0.0936 | 0.132* | |
H7C | 0.0046 | 0.1874 | 0.2861 | 0.132* | |
C8 | 0.2436 (3) | 0.1500 (2) | −0.0046 (5) | 0.0456 (10) | |
H8 | 0.2703 | 0.1445 | −0.1090 | 0.055* | |
C9 | 0.3205 (3) | 0.1070 (2) | 0.1305 (4) | 0.0402 (9) | |
C10 | 0.5527 (3) | 0.1066 (2) | −0.0255 (5) | 0.0460 (10) | |
H10 | 0.5968 | 0.0836 | 0.0677 | 0.055* | |
C11 | 0.6032 (3) | 0.1273 (2) | −0.1647 (5) | 0.0404 (9) | |
C12 | 0.7137 (3) | 0.1108 (2) | −0.1598 (5) | 0.0511 (11) | |
H12 | 0.7557 | 0.0875 | −0.0653 | 0.061* | |
C13 | 0.7630 (3) | 0.1285 (2) | −0.2933 (6) | 0.0551 (12) | |
H13 | 0.8374 | 0.1172 | −0.2886 | 0.066* | |
C14 | 0.7011 (4) | 0.1626 (2) | −0.4315 (5) | 0.0508 (11) | |
C15 | 0.5919 (4) | 0.1809 (2) | −0.4393 (5) | 0.0550 (11) | |
H15 | 0.5509 | 0.2047 | −0.5341 | 0.066* | |
C16 | 0.5430 (3) | 0.1640 (2) | −0.3062 (5) | 0.0498 (11) | |
H16 | 0.4691 | 0.1772 | −0.3108 | 0.060* | |
S1 | 0.10908 (9) | 0.10838 (7) | −0.03153 (14) | 0.0548 (3) | |
N1 | 0.0871 (3) | 0.1183 (2) | 0.1564 (5) | 0.0598 (10) | |
N2 | 0.4212 (3) | 0.09167 (19) | 0.1225 (4) | 0.0493 (9) | |
N3 | 0.4512 (3) | 0.11839 (19) | −0.0247 (4) | 0.0504 (9) | |
O1 | 0.0296 (2) | 0.1538 (2) | −0.1431 (4) | 0.0787 (10) | |
O2 | 0.1256 (2) | 0.02920 (17) | −0.0680 (3) | 0.0573 (8) | |
Cl1 | 0.23868 (10) | 0.25052 (6) | 0.04375 (17) | 0.0757 (4) | |
Cl2 | 0.76214 (12) | 0.18282 (8) | −0.60081 (17) | 0.0859 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.059 (3) | 0.038 (2) | 0.039 (2) | −0.009 (2) | 0.015 (2) | −0.0026 (18) |
C2 | 0.076 (3) | 0.053 (3) | 0.040 (2) | −0.012 (2) | 0.013 (2) | −0.004 (2) |
C3 | 0.120 (5) | 0.067 (3) | 0.039 (3) | −0.023 (3) | 0.016 (3) | 0.000 (2) |
C4 | 0.151 (6) | 0.056 (3) | 0.051 (3) | −0.026 (4) | 0.050 (4) | −0.009 (3) |
C5 | 0.100 (4) | 0.058 (3) | 0.080 (4) | −0.017 (3) | 0.057 (3) | −0.011 (3) |
C6 | 0.072 (3) | 0.038 (2) | 0.057 (3) | −0.012 (2) | 0.030 (3) | −0.011 (2) |
C7 | 0.062 (3) | 0.093 (4) | 0.115 (4) | 0.006 (3) | 0.036 (3) | −0.032 (3) |
C8 | 0.045 (3) | 0.046 (2) | 0.047 (2) | −0.0027 (19) | 0.012 (2) | 0.0048 (19) |
C9 | 0.048 (3) | 0.035 (2) | 0.039 (2) | −0.006 (2) | 0.0107 (19) | −0.0015 (18) |
C10 | 0.048 (3) | 0.044 (2) | 0.046 (2) | 0.008 (2) | 0.009 (2) | 0.0055 (19) |
C11 | 0.036 (2) | 0.040 (2) | 0.045 (2) | −0.0033 (18) | 0.0075 (19) | −0.0003 (18) |
C12 | 0.041 (2) | 0.053 (3) | 0.058 (3) | 0.005 (2) | 0.005 (2) | 0.001 (2) |
C13 | 0.034 (2) | 0.051 (3) | 0.082 (3) | −0.001 (2) | 0.016 (2) | −0.008 (2) |
C14 | 0.057 (3) | 0.040 (2) | 0.061 (3) | −0.004 (2) | 0.026 (2) | −0.001 (2) |
C15 | 0.055 (3) | 0.054 (3) | 0.058 (3) | 0.004 (2) | 0.018 (2) | 0.010 (2) |
C16 | 0.037 (2) | 0.055 (3) | 0.058 (3) | 0.000 (2) | 0.012 (2) | 0.004 (2) |
S1 | 0.0448 (7) | 0.0606 (7) | 0.0593 (7) | −0.0038 (6) | 0.0111 (5) | 0.0011 (6) |
N1 | 0.053 (2) | 0.064 (2) | 0.071 (2) | 0.002 (2) | 0.032 (2) | −0.003 (2) |
N2 | 0.053 (2) | 0.058 (2) | 0.0383 (19) | 0.0034 (18) | 0.0119 (17) | 0.0118 (16) |
N3 | 0.045 (2) | 0.063 (2) | 0.045 (2) | 0.0035 (18) | 0.0116 (16) | 0.0084 (18) |
O1 | 0.0463 (19) | 0.094 (3) | 0.088 (2) | 0.0067 (18) | −0.0040 (18) | 0.017 (2) |
O2 | 0.0593 (19) | 0.0633 (19) | 0.0498 (17) | −0.0074 (16) | 0.0119 (15) | −0.0139 (15) |
Cl1 | 0.0765 (9) | 0.0449 (6) | 0.1015 (10) | −0.0031 (6) | 0.0077 (7) | 0.0103 (6) |
Cl2 | 0.1003 (11) | 0.0762 (9) | 0.1001 (10) | 0.0026 (8) | 0.0653 (9) | 0.0138 (8) |
C1—C6 | 1.396 (6) | C9—N2 | 1.281 (5) |
C1—C2 | 1.397 (5) | C10—N3 | 1.267 (5) |
C1—C9 | 1.470 (5) | C10—C11 | 1.448 (5) |
C2—C3 | 1.378 (6) | C10—H10 | 0.9300 |
C2—H2 | 0.9300 | C11—C12 | 1.381 (5) |
C3—C4 | 1.379 (7) | C11—C16 | 1.394 (5) |
C3—H3 | 0.9300 | C12—C13 | 1.387 (6) |
C4—C5 | 1.371 (7) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—C14 | 1.363 (5) |
C5—C6 | 1.394 (6) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—C15 | 1.369 (5) |
C6—N1 | 1.425 (5) | C14—Cl2 | 1.739 (4) |
C7—N1 | 1.464 (5) | C15—C16 | 1.378 (5) |
C7—H7A | 0.9600 | C15—H15 | 0.9300 |
C7—H7B | 0.9600 | C16—H16 | 0.9300 |
C7—H7C | 0.9600 | S1—O2 | 1.417 (3) |
C8—C9 | 1.498 (5) | S1—O1 | 1.428 (3) |
C8—Cl1 | 1.776 (4) | S1—N1 | 1.623 (4) |
C8—S1 | 1.776 (4) | N2—N3 | 1.406 (4) |
C8—H8 | 0.9800 | ||
C6—C1—C2 | 118.1 (4) | N3—C10—C11 | 123.0 (4) |
C6—C1—C9 | 123.0 (4) | N3—C10—H10 | 118.5 |
C2—C1—C9 | 118.9 (4) | C11—C10—H10 | 118.5 |
C3—C2—C1 | 121.9 (5) | C12—C11—C16 | 118.2 (4) |
C3—C2—H2 | 119.0 | C12—C11—C10 | 120.2 (4) |
C1—C2—H2 | 119.0 | C16—C11—C10 | 121.6 (4) |
C2—C3—C4 | 119.2 (5) | C11—C12—C13 | 121.1 (4) |
C2—C3—H3 | 120.4 | C11—C12—H12 | 119.4 |
C4—C3—H3 | 120.4 | C13—C12—H12 | 119.4 |
C5—C4—C3 | 120.1 (5) | C14—C13—C12 | 119.2 (4) |
C5—C4—H4 | 119.9 | C14—C13—H13 | 120.4 |
C3—C4—H4 | 119.9 | C12—C13—H13 | 120.4 |
C4—C5—C6 | 121.2 (5) | C13—C14—C15 | 121.1 (4) |
C4—C5—H5 | 119.4 | C13—C14—Cl2 | 119.2 (3) |
C6—C5—H5 | 119.4 | C15—C14—Cl2 | 119.6 (4) |
C5—C6—C1 | 119.5 (5) | C14—C15—C16 | 119.7 (4) |
C5—C6—N1 | 119.6 (4) | C14—C15—H15 | 120.1 |
C1—C6—N1 | 120.9 (4) | C16—C15—H15 | 120.1 |
N1—C7—H7A | 109.5 | C15—C16—C11 | 120.6 (4) |
N1—C7—H7B | 109.5 | C15—C16—H16 | 119.7 |
H7A—C7—H7B | 109.5 | C11—C16—H16 | 119.7 |
N1—C7—H7C | 109.5 | O2—S1—O1 | 119.9 (2) |
H7A—C7—H7C | 109.5 | O2—S1—N1 | 111.05 (18) |
H7B—C7—H7C | 109.5 | O1—S1—N1 | 108.9 (2) |
C9—C8—Cl1 | 111.1 (3) | O2—S1—C8 | 104.09 (18) |
C9—C8—S1 | 109.1 (3) | O1—S1—C8 | 111.11 (19) |
Cl1—C8—S1 | 110.3 (2) | N1—S1—C8 | 99.76 (19) |
C9—C8—H8 | 108.7 | C6—N1—C7 | 121.2 (4) |
Cl1—C8—H8 | 108.7 | C6—N1—S1 | 117.8 (3) |
S1—C8—H8 | 108.7 | C7—N1—S1 | 121.0 (3) |
N2—C9—C1 | 118.8 (4) | C9—N2—N3 | 113.6 (3) |
N2—C9—C8 | 122.5 (3) | C10—N3—N2 | 112.4 (3) |
C1—C9—C8 | 118.6 (4) | ||
C6—C1—C2—C3 | 0.1 (6) | C13—C14—C15—C16 | −0.6 (6) |
C9—C1—C2—C3 | −180.0 (4) | Cl2—C14—C15—C16 | 179.1 (3) |
C1—C2—C3—C4 | 0.3 (7) | C14—C15—C16—C11 | −1.0 (6) |
C2—C3—C4—C5 | −0.3 (7) | C12—C11—C16—C15 | 2.1 (6) |
C3—C4—C5—C6 | −0.3 (7) | C10—C11—C16—C15 | −178.0 (4) |
C4—C5—C6—C1 | 0.7 (6) | C9—C8—S1—O2 | −57.3 (3) |
C4—C5—C6—N1 | −178.7 (4) | Cl1—C8—S1—O2 | −179.68 (19) |
C2—C1—C6—C5 | −0.6 (6) | C9—C8—S1—O1 | 172.3 (3) |
C9—C1—C6—C5 | 179.5 (4) | Cl1—C8—S1—O1 | 49.9 (3) |
C2—C1—C6—N1 | 178.8 (3) | C9—C8—S1—N1 | 57.4 (3) |
C9—C1—C6—N1 | −1.1 (6) | Cl1—C8—S1—N1 | −64.9 (2) |
C6—C1—C9—N2 | −171.5 (4) | C5—C6—N1—C7 | 27.6 (6) |
C2—C1—C9—N2 | 8.6 (5) | C1—C6—N1—C7 | −151.8 (4) |
C6—C1—C9—C8 | 9.5 (5) | C5—C6—N1—S1 | −151.3 (3) |
C2—C1—C9—C8 | −170.4 (3) | C1—C6—N1—S1 | 29.3 (5) |
Cl1—C8—C9—N2 | −96.8 (4) | O2—S1—N1—C6 | 55.3 (3) |
S1—C8—C9—N2 | 141.3 (3) | O1—S1—N1—C6 | −170.5 (3) |
Cl1—C8—C9—C1 | 82.1 (4) | C8—S1—N1—C6 | −54.0 (3) |
S1—C8—C9—C1 | −39.7 (4) | O2—S1—N1—C7 | −123.6 (4) |
N3—C10—C11—C12 | −178.1 (4) | O1—S1—N1—C7 | 10.6 (4) |
N3—C10—C11—C16 | 1.9 (6) | C8—S1—N1—C7 | 127.1 (4) |
C16—C11—C12—C13 | −1.6 (6) | C1—C9—N2—N3 | −179.5 (3) |
C10—C11—C12—C13 | 178.5 (4) | C8—C9—N2—N3 | −0.6 (5) |
C11—C12—C13—C14 | 0.0 (6) | C11—C10—N3—N2 | 178.6 (3) |
C12—C13—C14—C15 | 1.2 (6) | C9—N2—N3—C10 | 176.2 (4) |
C12—C13—C14—Cl2 | −178.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.93 | 2.48 | 3.356 (6) | 158 |
C12—H12···O2ii | 0.93 | 2.59 | 3.419 (5) | 149 |
C13—H13···O1iii | 0.93 | 2.50 | 3.293 (5) | 143 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H13Cl2N3O2S |
Mr | 382.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 12.309 (2), 17.189 (3), 8.1837 (13) |
β (°) | 101.632 (8) |
V (Å3) | 1695.9 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.52 |
Crystal size (mm) | 0.28 × 0.16 × 0.14 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.868, 0.931 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13580, 3319, 1736 |
Rint | 0.076 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.140, 1.00 |
No. of reflections | 3319 |
No. of parameters | 218 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.33 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.93 | 2.48 | 3.356 (6) | 158 |
C12—H12···O2ii | 0.93 | 2.59 | 3.419 (5) | 149 |
C13—H13···O1iii | 0.93 | 2.50 | 3.293 (5) | 143 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z; (iii) x+1, y, z. |
Acknowledgements
MS acknowledges the HEC Pakistan for providing a PhD fellowship and the UOS, Sargodha, for X-ray diffraction facility.
References
Ahmad, M., Siddiqui, H. L., Ahmad, S., Parvez, M. & Tizzard, G. J. (2010b). J. Chem. Crystallogr. 40, 1188–1194. Web of Science CSD CrossRef CAS Google Scholar
Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M. & Parvez, M. (2010a). Eur. J. Med. Chem. 45, 698–704. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Harmata, M., Calkins, N. L., Baughman, R. G. & Barnes, C. L. (2006). J. Org. Chem. 71, 3650–3652. Web of Science CrossRef PubMed CAS Google Scholar
Misu, Y. & Togo, H. (2003). Org. Biomol. Chem. 1, 1342–1346. Web of Science CrossRef PubMed CAS Google Scholar
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011b). Asian J. Chem. 23, 2101–2106. CAS Google Scholar
Shafiq, M., Khan, I. U., Zia-ur-Rehman, M., Arshad, M. N. & Asiri, A. M. (2011c). Acta Cryst. E67, o2038. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shafiq, M., Tahir, M. N., Harrison, W. T. A., Khan, I. U. & Shafique, S. (2013). Acta Cryst. E69, o165. CSD CrossRef IUCr Journals Google Scholar
Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). J. Chil. Chem. Soc. 56, 527–531. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science 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.
Benzothiazine derivatives are versatile chiral ligands (Harmata et al., 2006) and show various biological activities (Ahmad et al., 2010a, Misu & Togo, 2003). As part of our ongoing studies in this area (Shafiq et al., 2011a,b), we now describe the synthesis and structure of the title compound, (I) (Fig. 1).
The dihedral angle between the aromatic rings C1–C6 and C11–C16 is 6.6 (2)° and the C9=N2—N3=C10 torsion angle is 176.2 (4)°. The conformation of the C1/C6/C8/C9/N1/S1 thiazine ring is an envelope, with the S atom displaced by -0.633 (6) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.037 Å). This displacement is smaller than that seen in related structures (Shafiq et al., 2013). In (I), atom C7 is displaced from the mean plane of the ring by 0.541 (7) Å and Cl1, in an axial site, is displaced by 2.015 (6) Å. Atom C8 is a stereogenic centre with an S configuration in the arbitrarily-chosen asymmetric unit. Nevertheless, crystal symmetry indicates a racemic mixture.
In the crystal, moelcules are linked by C—H···O interactions (Table 1) to generate a three-dimensional network (Fig. 2). Very weak aromatic π-π stacking interactions between the benzene rings C1—C6 and C13—C18 benzene rings [centroid-centroid separations = 3.928 (2) Å] are also observed.