organic compounds
6-Bromo-1-methyl-4-[2-(4-nitrobenzylidene)hydrazin-1-ylidene]-2,2-dioxo-3,4-dihydro-1H-2λ6,1-benzothiazine
aDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan, bDepartment of Chemistry, University of Aberdeen, Mston Walk, Aberdeen AB24 3UE, Scotland, and cMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan
*Correspondence e-mail: hafizshafique@hotmail.com
In the title compound, C16H13BrN4O4S, the dihedral angle between the aromatic rings is 4.1 (2)° and the C=N—N=C torsion angle is 175.5 (3)°. The nitro group is almost coplanar with the benzene ring to which it is attached [dihedral angle = 2.9 (7)°]. The thiazine ring has an S-envelope conformation with the S atom displaced by 0.819 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.017 Å). In the crystal, C—H⋯O interactions link the molecules and weak aromatic π–π stacking [centroid–centroid separation = 3.874 (2) Å] is also observed.
Related literature
For the synthesis and biological activity of the title compound and related materials, see: Shafiq, Zia-ur-Rehman et al. (2011). For related structures, see: Shafiq, Khan et al. (2011); Shafiq, Harrison et al. (2012).
Experimental
Crystal data
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Refinement
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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 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812035374/pv2578sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035374/pv2578Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035374/pv2578Isup3.cml
The compound was synthesized following the literature procedure (Shafiq, Zia-ur-Rehman et al., 2011) and recrystalized from an ethylacetate solution under slow evaporation.
The 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. The (0 0 1) and (0 1 0) reflections were obstructed by the beamstop and were omitted from the refinement.
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 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius. Fig. 2. A view of the C—-H···O hydrogen bonds (orange double-dashed lines) in the of the title compound. |
C16H13BrN4O4S | Z = 2 |
Mr = 437.27 | F(000) = 440 |
Triclinic, P1 | Dx = 1.672 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2772 (4) Å | Cell parameters from 4062 reflections |
b = 9.0572 (4) Å | θ = 2.3–22.1° |
c = 12.6868 (6) Å | µ = 2.52 mm−1 |
α = 87.132 (4)° | T = 296 K |
β = 70.976 (3)° | Needle, yellow |
γ = 75.098 (2)° | 0.36 × 0.09 × 0.07 mm |
V = 868.32 (7) Å3 |
Bruker APEXII CCD diffractometer | 4251 independent reflections |
Radiation source: fine-focus sealed tube | 2484 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 28.4°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −11→11 |
Tmin = 0.464, Tmax = 0.843 | k = −12→12 |
17474 measured reflections | l = −16→16 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0415P)2 + 0.5116P] where P = (Fo2 + 2Fc2)/3 |
4251 reflections | (Δ/σ)max = 0.001 |
236 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C16H13BrN4O4S | γ = 75.098 (2)° |
Mr = 437.27 | V = 868.32 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.2772 (4) Å | Mo Kα radiation |
b = 9.0572 (4) Å | µ = 2.52 mm−1 |
c = 12.6868 (6) Å | T = 296 K |
α = 87.132 (4)° | 0.36 × 0.09 × 0.07 mm |
β = 70.976 (3)° |
Bruker APEXII CCD diffractometer | 4251 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 2484 reflections with I > 2σ(I) |
Tmin = 0.464, Tmax = 0.843 | Rint = 0.043 |
17474 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.58 e Å−3 |
4251 reflections | Δρmin = −0.40 e Å−3 |
236 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 | 0.8000 (4) | 0.2966 (4) | 0.3910 (3) | 0.0429 (8) | |
C2 | 0.8376 (5) | 0.4239 (4) | 0.4267 (3) | 0.0591 (10) | |
H2 | 0.8240 | 0.4365 | 0.5017 | 0.071* | |
C3 | 0.8940 (5) | 0.5298 (4) | 0.3531 (3) | 0.0516 (9) | |
H3 | 0.9165 | 0.6146 | 0.3784 | 0.062* | |
C4 | 0.9175 (4) | 0.5116 (3) | 0.2422 (3) | 0.0443 (8) | |
C5 | 0.8801 (4) | 0.3880 (3) | 0.2041 (3) | 0.0385 (7) | |
H5 | 0.8956 | 0.3769 | 0.1287 | 0.046* | |
C6 | 0.8192 (4) | 0.2795 (3) | 0.2783 (2) | 0.0371 (7) | |
C7 | 0.7760 (4) | 0.1511 (3) | 0.2351 (2) | 0.0336 (7) | |
C8 | 0.7034 (4) | 0.0381 (4) | 0.3145 (2) | 0.0438 (8) | |
H8A | 0.7315 | −0.0590 | 0.2750 | 0.053* | |
H8B | 0.5757 | 0.0744 | 0.3446 | 0.053* | |
C9 | 0.6400 (6) | 0.2323 (5) | 0.5848 (3) | 0.0799 (13) | |
H9A | 0.7166 | 0.2499 | 0.6229 | 0.120* | |
H9B | 0.5874 | 0.1518 | 0.6195 | 0.120* | |
H9C | 0.5488 | 0.3242 | 0.5886 | 0.120* | |
C10 | 0.7637 (4) | 0.0248 (3) | −0.0055 (3) | 0.0390 (7) | |
H10 | 0.8022 | 0.1039 | −0.0472 | 0.047* | |
C11 | 0.7208 (4) | −0.0903 (3) | −0.0607 (2) | 0.0362 (7) | |
C12 | 0.6593 (4) | −0.2102 (4) | −0.0032 (2) | 0.0413 (7) | |
H12 | 0.6451 | −0.2187 | 0.0724 | 0.050* | |
C13 | 0.6194 (4) | −0.3163 (4) | −0.0580 (3) | 0.0454 (8) | |
H13 | 0.5775 | −0.3964 | −0.0199 | 0.054* | |
C14 | 0.6428 (4) | −0.3016 (4) | −0.1703 (3) | 0.0404 (7) | |
C15 | 0.7034 (4) | −0.1855 (4) | −0.2294 (3) | 0.0431 (8) | |
H15 | 0.7184 | −0.1782 | −0.3052 | 0.052* | |
C16 | 0.7415 (4) | −0.0794 (4) | −0.1731 (2) | 0.0414 (8) | |
H16 | 0.7820 | 0.0010 | −0.2116 | 0.050* | |
S1 | 0.79259 (11) | 0.01247 (9) | 0.42342 (6) | 0.0432 (2) | |
O1 | 0.9788 (3) | −0.0430 (3) | 0.37576 (19) | 0.0558 (6) | |
O2 | 0.7010 (3) | −0.0721 (3) | 0.50933 (18) | 0.0569 (6) | |
O3 | 0.6135 (4) | −0.3959 (3) | −0.3268 (2) | 0.0759 (8) | |
O4 | 0.5483 (5) | −0.5195 (3) | −0.1767 (3) | 0.0898 (10) | |
N1 | 0.7408 (4) | 0.1889 (3) | 0.4696 (2) | 0.0498 (7) | |
N2 | 0.7990 (3) | 0.1447 (3) | 0.1299 (2) | 0.0404 (6) | |
N3 | 0.7509 (3) | 0.0216 (3) | 0.0964 (2) | 0.0396 (6) | |
N4 | 0.5998 (4) | −0.4145 (4) | −0.2289 (3) | 0.0559 (8) | |
Br1 | 1.00058 (6) | 0.65482 (4) | 0.13996 (3) | 0.06700 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.048 (2) | 0.0466 (19) | 0.0369 (18) | −0.0160 (15) | −0.0144 (15) | −0.0020 (15) |
C2 | 0.076 (3) | 0.063 (2) | 0.046 (2) | −0.022 (2) | −0.0239 (19) | −0.0153 (18) |
C3 | 0.069 (2) | 0.0375 (18) | 0.058 (2) | −0.0180 (17) | −0.0296 (18) | −0.0092 (16) |
C4 | 0.051 (2) | 0.0363 (17) | 0.052 (2) | −0.0126 (15) | −0.0240 (16) | 0.0005 (15) |
C5 | 0.0415 (19) | 0.0375 (16) | 0.0399 (18) | −0.0096 (14) | −0.0175 (14) | −0.0018 (14) |
C6 | 0.0370 (18) | 0.0389 (17) | 0.0387 (17) | −0.0117 (14) | −0.0143 (13) | −0.0046 (13) |
C7 | 0.0338 (17) | 0.0365 (16) | 0.0320 (17) | −0.0101 (13) | −0.0115 (13) | −0.0018 (13) |
C8 | 0.050 (2) | 0.0496 (19) | 0.0379 (18) | −0.0230 (16) | −0.0139 (15) | 0.0011 (15) |
C9 | 0.094 (3) | 0.081 (3) | 0.046 (2) | −0.023 (2) | 0.006 (2) | −0.013 (2) |
C10 | 0.0408 (19) | 0.0436 (17) | 0.0361 (18) | −0.0185 (14) | −0.0109 (14) | 0.0002 (14) |
C11 | 0.0338 (17) | 0.0423 (17) | 0.0352 (17) | −0.0125 (13) | −0.0121 (13) | −0.0018 (13) |
C12 | 0.049 (2) | 0.0495 (19) | 0.0304 (17) | −0.0177 (15) | −0.0161 (14) | 0.0016 (14) |
C13 | 0.056 (2) | 0.0424 (18) | 0.046 (2) | −0.0217 (16) | −0.0201 (16) | 0.0032 (15) |
C14 | 0.0412 (19) | 0.0451 (18) | 0.0381 (18) | −0.0107 (15) | −0.0158 (14) | −0.0079 (14) |
C15 | 0.0395 (19) | 0.060 (2) | 0.0315 (17) | −0.0118 (16) | −0.0128 (14) | −0.0055 (15) |
C16 | 0.0431 (19) | 0.0498 (19) | 0.0353 (18) | −0.0197 (15) | −0.0123 (14) | 0.0032 (14) |
S1 | 0.0471 (5) | 0.0504 (5) | 0.0333 (4) | −0.0180 (4) | −0.0110 (3) | 0.0065 (4) |
O1 | 0.0443 (15) | 0.0642 (15) | 0.0522 (14) | −0.0085 (11) | −0.0126 (11) | 0.0132 (12) |
O2 | 0.0661 (17) | 0.0680 (16) | 0.0400 (13) | −0.0306 (13) | −0.0132 (11) | 0.0155 (11) |
O3 | 0.100 (2) | 0.091 (2) | 0.0488 (17) | −0.0368 (17) | −0.0284 (15) | −0.0191 (15) |
O4 | 0.143 (3) | 0.076 (2) | 0.085 (2) | −0.063 (2) | −0.055 (2) | 0.0059 (17) |
N1 | 0.064 (2) | 0.0584 (18) | 0.0280 (14) | −0.0241 (15) | −0.0083 (12) | −0.0028 (12) |
N2 | 0.0479 (17) | 0.0391 (14) | 0.0405 (16) | −0.0188 (12) | −0.0163 (12) | −0.0023 (12) |
N3 | 0.0482 (16) | 0.0375 (14) | 0.0382 (16) | −0.0167 (12) | −0.0157 (12) | −0.0036 (11) |
N4 | 0.058 (2) | 0.060 (2) | 0.057 (2) | −0.0167 (16) | −0.0241 (15) | −0.0144 (16) |
Br1 | 0.0932 (4) | 0.0392 (2) | 0.0830 (3) | −0.0297 (2) | −0.0394 (2) | 0.01409 (18) |
C1—C6 | 1.398 (4) | C10—N3 | 1.262 (4) |
C1—C2 | 1.400 (4) | C10—C11 | 1.459 (4) |
C1—N1 | 1.420 (4) | C10—H10 | 0.9300 |
C2—C3 | 1.367 (5) | C11—C16 | 1.380 (4) |
C2—H2 | 0.9300 | C11—C12 | 1.391 (4) |
C3—C4 | 1.368 (4) | C12—C13 | 1.376 (4) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.382 (4) | C13—C14 | 1.379 (4) |
C4—Br1 | 1.884 (3) | C13—H13 | 0.9300 |
C5—C6 | 1.400 (4) | C14—C15 | 1.366 (4) |
C5—H5 | 0.9300 | C14—N4 | 1.470 (4) |
C6—C7 | 1.478 (4) | C15—C16 | 1.381 (4) |
C7—N2 | 1.288 (4) | C15—H15 | 0.9300 |
C7—C8 | 1.497 (4) | C16—H16 | 0.9300 |
C8—S1 | 1.748 (3) | S1—O1 | 1.420 (2) |
C8—H8A | 0.9700 | S1—O2 | 1.423 (2) |
C8—H8B | 0.9700 | S1—N1 | 1.631 (3) |
C9—N1 | 1.443 (4) | O3—N4 | 1.217 (4) |
C9—H9A | 0.9600 | O4—N4 | 1.219 (4) |
C9—H9B | 0.9600 | N2—N3 | 1.402 (3) |
C9—H9C | 0.9600 | ||
C6—C1—C2 | 119.1 (3) | N3—C10—H10 | 118.6 |
C6—C1—N1 | 121.3 (3) | C11—C10—H10 | 118.6 |
C2—C1—N1 | 119.7 (3) | C16—C11—C12 | 119.2 (3) |
C3—C2—C1 | 121.0 (3) | C16—C11—C10 | 119.0 (3) |
C3—C2—H2 | 119.5 | C12—C11—C10 | 121.8 (3) |
C1—C2—H2 | 119.5 | C13—C12—C11 | 120.2 (3) |
C2—C3—C4 | 120.2 (3) | C13—C12—H12 | 119.9 |
C2—C3—H3 | 119.9 | C11—C12—H12 | 119.9 |
C4—C3—H3 | 119.9 | C12—C13—C14 | 118.7 (3) |
C3—C4—C5 | 120.3 (3) | C12—C13—H13 | 120.6 |
C3—C4—Br1 | 120.3 (2) | C14—C13—H13 | 120.6 |
C5—C4—Br1 | 119.3 (2) | C15—C14—C13 | 122.6 (3) |
C4—C5—C6 | 120.4 (3) | C15—C14—N4 | 118.6 (3) |
C4—C5—H5 | 119.8 | C13—C14—N4 | 118.8 (3) |
C6—C5—H5 | 119.8 | C14—C15—C16 | 117.9 (3) |
C1—C6—C5 | 118.9 (3) | C14—C15—H15 | 121.0 |
C1—C6—C7 | 122.2 (3) | C16—C15—H15 | 121.0 |
C5—C6—C7 | 118.9 (3) | C11—C16—C15 | 121.3 (3) |
N2—C7—C6 | 117.6 (3) | C11—C16—H16 | 119.3 |
N2—C7—C8 | 123.0 (2) | C15—C16—H16 | 119.3 |
C6—C7—C8 | 119.4 (2) | O1—S1—O2 | 118.22 (15) |
C7—C8—S1 | 110.5 (2) | O1—S1—N1 | 110.53 (15) |
C7—C8—H8A | 109.6 | O2—S1—N1 | 108.09 (14) |
S1—C8—H8A | 109.6 | O1—S1—C8 | 107.65 (15) |
C7—C8—H8B | 109.6 | O2—S1—C8 | 110.70 (14) |
S1—C8—H8B | 109.6 | N1—S1—C8 | 100.17 (15) |
H8A—C8—H8B | 108.1 | C1—N1—C9 | 122.1 (3) |
N1—C9—H9A | 109.5 | C1—N1—S1 | 116.7 (2) |
N1—C9—H9B | 109.5 | C9—N1—S1 | 121.3 (2) |
H9A—C9—H9B | 109.5 | C7—N2—N3 | 113.8 (2) |
N1—C9—H9C | 109.5 | C10—N3—N2 | 112.1 (2) |
H9A—C9—H9C | 109.5 | O3—N4—O4 | 123.4 (3) |
H9B—C9—H9C | 109.5 | O3—N4—C14 | 117.9 (3) |
N3—C10—C11 | 122.9 (3) | O4—N4—C14 | 118.7 (3) |
C6—C1—C2—C3 | −0.6 (5) | C13—C14—C15—C16 | −0.2 (5) |
N1—C1—C2—C3 | −179.7 (3) | N4—C14—C15—C16 | 179.3 (3) |
C1—C2—C3—C4 | −1.1 (6) | C12—C11—C16—C15 | −0.3 (5) |
C2—C3—C4—C5 | 1.7 (5) | C10—C11—C16—C15 | 179.8 (3) |
C2—C3—C4—Br1 | −178.5 (3) | C14—C15—C16—C11 | 0.5 (5) |
C3—C4—C5—C6 | −0.5 (5) | C7—C8—S1—O1 | −60.1 (3) |
Br1—C4—C5—C6 | 179.6 (2) | C7—C8—S1—O2 | 169.3 (2) |
C2—C1—C6—C5 | 1.7 (5) | C7—C8—S1—N1 | 55.4 (2) |
N1—C1—C6—C5 | −179.2 (3) | C6—C1—N1—C9 | −149.0 (4) |
C2—C1—C6—C7 | −177.8 (3) | C2—C1—N1—C9 | 30.0 (5) |
N1—C1—C6—C7 | 1.2 (5) | C6—C1—N1—S1 | 31.0 (4) |
C4—C5—C6—C1 | −1.2 (5) | C2—C1—N1—S1 | −149.9 (3) |
C4—C5—C6—C7 | 178.4 (3) | O1—S1—N1—C1 | 57.5 (3) |
C1—C6—C7—N2 | −179.6 (3) | O2—S1—N1—C1 | −171.7 (2) |
C5—C6—C7—N2 | 0.8 (4) | C8—S1—N1—C1 | −55.9 (3) |
C1—C6—C7—C8 | 2.2 (4) | O1—S1—N1—C9 | −122.5 (3) |
C5—C6—C7—C8 | −177.4 (3) | O2—S1—N1—C9 | 8.3 (4) |
N2—C7—C8—S1 | 148.6 (3) | C8—S1—N1—C9 | 124.2 (3) |
C6—C7—C8—S1 | −33.3 (4) | C6—C7—N2—N3 | −178.5 (3) |
N3—C10—C11—C16 | −178.9 (3) | C8—C7—N2—N3 | −0.4 (4) |
N3—C10—C11—C12 | 1.2 (5) | C11—C10—N3—N2 | −179.8 (3) |
C16—C11—C12—C13 | −0.1 (5) | C7—N2—N3—C10 | 175.5 (3) |
C10—C11—C12—C13 | 179.7 (3) | C15—C14—N4—O3 | −2.8 (5) |
C11—C12—C13—C14 | 0.4 (5) | C13—C14—N4—O3 | 176.7 (3) |
C12—C13—C14—C15 | −0.3 (5) | C15—C14—N4—O4 | 178.9 (3) |
C12—C13—C14—N4 | −179.8 (3) | C13—C14—N4—O4 | −1.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O3i | 0.93 | 2.56 | 3.325 (4) | 139 |
C8—H8B···O2ii | 0.97 | 2.44 | 3.310 (4) | 150 |
C13—H13···O4iii | 0.93 | 2.53 | 3.306 (5) | 141 |
C15—H15···O2iv | 0.93 | 2.53 | 3.426 (4) | 162 |
C16—H16···O1v | 0.93 | 2.45 | 3.218 (4) | 139 |
Symmetry codes: (i) x, y+1, z+1; (ii) −x+1, −y, −z+1; (iii) −x+1, −y−1, −z; (iv) x, y, z−1; (v) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C16H13BrN4O4S |
Mr | 437.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 8.2772 (4), 9.0572 (4), 12.6868 (6) |
α, β, γ (°) | 87.132 (4), 70.976 (3), 75.098 (2) |
V (Å3) | 868.32 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.52 |
Crystal size (mm) | 0.36 × 0.09 × 0.07 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.464, 0.843 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17474, 4251, 2484 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.106, 1.00 |
No. of reflections | 4251 |
No. of parameters | 236 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.58, −0.40 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O3i | 0.93 | 2.56 | 3.325 (4) | 139 |
C8—H8B···O2ii | 0.97 | 2.44 | 3.310 (4) | 150 |
C13—H13···O4iii | 0.93 | 2.53 | 3.306 (5) | 141 |
C15—H15···O2iv | 0.93 | 2.53 | 3.426 (4) | 162 |
C16—H16···O1v | 0.93 | 2.45 | 3.218 (4) | 139 |
Symmetry codes: (i) x, y+1, z+1; (ii) −x+1, −y, −z+1; (iii) −x+1, −y−1, −z; (iv) x, y, z−1; (v) −x+2, −y, −z. |
Acknowledgements
MS acknowledges the Higher Education Commission of Pakistan for financial support and GC University Lahore, Pakistan for provision of facilities during his PhD studies.
References
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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.
A number of benzothiazine derivatives have been found to be effective as drugs (Shafiq, Zia-ur-Rehman et al., 2011). As a part of our ongoing studies in this area, we now describe the crystal structure of the title compound in this areticle.
The bond distances and angles in the title compound (Fig. 1) agree very well with the corresponding bond distances and angles reported in closely related compounds (Shafiq, Khan et al., 2011; Shafiq, Harrison et al., 2012). In the title molecule, the dihedral angle between the aromatic rings (C1–C6 and C11–C16) is 4.1 (2)° and the C7═N2—N3═C10 torsion angle is 175.5 (3)°. The nitro group is almost coplanar with benzene ring ((C11–C16) to which it is attached [dihedral angle = 2.9 (7)°]. The thiazine ring adopts an S-envelope conformation with S1 atom displaced by 0.819 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.017 Å).
The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1) linking the molecules to generate a three-dimensional network with all four O atoms acting as acceptors. Weak aromatic π-π stacking [centroid-centroid separation = 3.874 (2) Å] is also observed.