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organic compounds
(3S,4Z)-3-Chloro-1-methyl-4-[(2E)-(3-methylbenzylidene)hydrazinylidene]-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxide
aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan, bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and cApplied Chemistry Research Center, PCSIR Laboratories Complex, Lahore, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
In the title compound, C17H16ClN3O2S, the dihedral angle between the benzene rings is 7.75 (13)°. The thiazine ring adopts an with the S atom as the flap at a distance of 0.813 (2) Å from the plane through the other five atoms. In the crystal, C—H⋯O hydrogen bonds link the molecules into chains propagating in [100].
Related literature
For related structures, see: Shafiq et al. (2011a,b
,c
). For further synthetic details, see: Shafiq et al. (2011d
). For puckering parameters, see: Cremer & Pople (1975
).
Experimental
Crystal data
|
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009
); 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, 1997
) and PLATON (Spek, 2009
); software used to prepare material for publication: WinGX (Farrugia, 1999
) and PLATON.
Supporting information
10.1107/S1600536811056315/hb6582sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811056315/hb6582Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811056315/hb6582Isup3.cml
Schiff base derivative of (4Z)-4-hydrazinylidene-1-methyl-3,4-dihydro -1H-2,1-benzothiazine 2,2-dioxide and 3-methylbenzaldehyde was prepared using the method reported previously (Shafiq et al. 2011d). The chlorination of the schiff base was undertaken using N-chloro succinimide and dibenzoylperoxide (Shafiq et al., 2011a). The crude product was re-crystallized from ethyl acetate to yield orange needles of (I).
The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for aryl H-atoms.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009). ![]() | Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. |
![]() | Fig. 2. The partial packing showing chains extending along the [100] direction. |
C17H16ClN3O2S | F(000) = 752 |
Mr = 361.84 | Dx = 1.372 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2106 reflections |
a = 8.7734 (2) Å | θ = 1.4–25.3° |
b = 11.1271 (2) Å | µ = 0.35 mm−1 |
c = 17.9423 (3) Å | T = 296 K |
V = 1751.57 (6) Å3 | Needle, orange |
Z = 4 | 0.26 × 0.18 × 0.12 mm |
Bruker Kappa APEXII CCD diffractometer | 4265 independent reflections |
Radiation source: fine-focus sealed tube | 3478 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 7.50 pixels mm-1 | θmax = 28.3°, θmin = 2.2° |
ω scans | h = −10→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −14→14 |
Tmin = 0.930, Tmax = 0.960 | l = −23→23 |
17152 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.041P)2 + 0.2645P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4265 reflections | Δρmax = 0.24 e Å−3 |
219 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1788 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.47 (6) |
C17H16ClN3O2S | V = 1751.57 (6) Å3 |
Mr = 361.84 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.7734 (2) Å | µ = 0.35 mm−1 |
b = 11.1271 (2) Å | T = 296 K |
c = 17.9423 (3) Å | 0.26 × 0.18 × 0.12 mm |
Bruker Kappa APEXII CCD diffractometer | 4265 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3478 reflections with I > 2σ(I) |
Tmin = 0.930, Tmax = 0.960 | Rint = 0.029 |
17152 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.088 | Δρmax = 0.24 e Å−3 |
S = 1.03 | Δρmin = −0.27 e Å−3 |
4265 reflections | Absolute structure: Flack (1983), 1788 Friedel pairs |
219 parameters | Absolute structure parameter: 0.47 (6) |
0 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | ||
Cl1 | 0.16886 (7) | 0.16151 (6) | 0.00310 (3) | 0.0619 (2) | |
S1 | 0.10071 (6) | 0.09643 (5) | 0.15565 (3) | 0.0411 (2) | |
O1 | −0.04053 (18) | 0.05118 (15) | 0.12847 (9) | 0.0559 (6) | |
O2 | 0.17040 (19) | 0.04041 (14) | 0.21814 (8) | 0.0524 (5) | |
N1 | 0.0827 (2) | 0.23974 (17) | 0.16940 (11) | 0.0453 (6) | |
N2 | 0.5175 (2) | 0.13115 (15) | 0.09335 (10) | 0.0410 (5) | |
N3 | 0.5229 (2) | 0.03374 (16) | 0.04310 (10) | 0.0467 (6) | |
C1 | 0.2182 (3) | 0.30519 (17) | 0.18673 (11) | 0.0381 (6) | |
C2 | 0.2065 (3) | 0.4082 (2) | 0.22991 (13) | 0.0523 (8) | |
C3 | 0.3334 (3) | 0.4739 (2) | 0.24869 (13) | 0.0531 (8) | |
C4 | 0.4751 (3) | 0.4373 (2) | 0.22482 (12) | 0.0499 (8) | |
C5 | 0.4885 (3) | 0.3360 (2) | 0.18144 (11) | 0.0422 (7) | |
C6 | 0.3614 (2) | 0.26764 (17) | 0.16138 (10) | 0.0338 (6) | |
C7 | −0.0609 (3) | 0.3020 (3) | 0.15644 (19) | 0.0690 (10) | |
C8 | 0.2429 (2) | 0.09333 (19) | 0.08520 (10) | 0.0380 (6) | |
C9 | 0.3815 (2) | 0.16115 (17) | 0.11258 (10) | 0.0339 (6) | |
C10 | 0.6581 (3) | 0.01494 (19) | 0.02078 (12) | 0.0455 (7) | |
C11 | 0.6974 (3) | −0.07862 (19) | −0.03287 (12) | 0.0464 (7) | |
C12 | 0.5872 (3) | −0.1500 (3) | −0.06694 (14) | 0.0668 (10) | |
C13 | 0.6332 (4) | −0.2383 (3) | −0.11655 (18) | 0.0808 (13) | |
C14 | 0.7839 (4) | −0.2554 (2) | −0.13190 (16) | 0.0751 (12) | |
C15 | 0.8968 (3) | −0.1863 (2) | −0.09916 (14) | 0.0588 (8) | |
C16 | 0.8497 (3) | −0.0975 (2) | −0.04930 (12) | 0.0513 (8) | |
C17 | 1.0632 (4) | −0.2042 (3) | −0.11637 (18) | 0.0803 (11) | |
H2 | 0.11120 | 0.43326 | 0.24642 | 0.0628* | |
H3 | 0.32356 | 0.54297 | 0.27748 | 0.0637* | |
H4 | 0.56141 | 0.48092 | 0.23799 | 0.0598* | |
H5 | 0.58447 | 0.31247 | 0.16504 | 0.0506* | |
H7A | −0.10558 | 0.32386 | 0.20337 | 0.1034* | |
H7B | −0.12931 | 0.25007 | 0.12985 | 0.1034* | |
H7C | −0.04256 | 0.37318 | 0.12755 | 0.1034* | |
H8 | 0.27104 | 0.00984 | 0.07453 | 0.0456* | |
H10 | 0.73577 | 0.06310 | 0.03951 | 0.0545* | |
H12 | 0.48435 | −0.13858 | −0.05656 | 0.0802* | |
H13 | 0.56053 | −0.28641 | −0.13963 | 0.0969* | |
H14 | 0.81172 | −0.31540 | −0.16535 | 0.0899* | |
H16 | 0.92277 | −0.04956 | −0.02640 | 0.0616* | |
H17A | 1.09454 | −0.28229 | −0.09956 | 0.1203* | |
H17B | 1.12213 | −0.14373 | −0.09134 | 0.1203* | |
H17C | 1.07907 | −0.19801 | −0.16917 | 0.1203* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0545 (4) | 0.0921 (4) | 0.0390 (3) | −0.0107 (3) | −0.0091 (3) | 0.0114 (3) |
S1 | 0.0304 (3) | 0.0494 (3) | 0.0434 (3) | −0.0036 (2) | 0.0022 (2) | 0.0065 (2) |
O1 | 0.0360 (10) | 0.0662 (10) | 0.0655 (10) | −0.0139 (8) | −0.0005 (8) | 0.0038 (8) |
O2 | 0.0459 (10) | 0.0616 (9) | 0.0497 (8) | −0.0011 (8) | 0.0023 (8) | 0.0190 (7) |
N1 | 0.0253 (10) | 0.0544 (10) | 0.0561 (11) | 0.0053 (8) | 0.0001 (8) | −0.0009 (8) |
N2 | 0.0357 (10) | 0.0437 (9) | 0.0435 (9) | 0.0038 (8) | 0.0036 (8) | −0.0065 (7) |
N3 | 0.0414 (12) | 0.0459 (10) | 0.0527 (10) | −0.0009 (9) | 0.0088 (9) | −0.0098 (8) |
C1 | 0.0322 (11) | 0.0447 (11) | 0.0374 (10) | 0.0049 (9) | −0.0006 (8) | −0.0003 (8) |
C2 | 0.0417 (13) | 0.0592 (13) | 0.0561 (13) | 0.0133 (12) | 0.0043 (11) | −0.0130 (12) |
C3 | 0.0569 (17) | 0.0487 (12) | 0.0537 (12) | 0.0045 (12) | −0.0028 (12) | −0.0115 (10) |
C4 | 0.0488 (15) | 0.0507 (12) | 0.0501 (12) | −0.0065 (11) | −0.0107 (11) | −0.0038 (10) |
C5 | 0.0331 (12) | 0.0520 (12) | 0.0414 (10) | −0.0031 (10) | 0.0002 (9) | −0.0009 (9) |
C6 | 0.0301 (11) | 0.0399 (9) | 0.0315 (9) | 0.0022 (8) | −0.0007 (8) | 0.0017 (8) |
C7 | 0.0372 (15) | 0.0779 (19) | 0.092 (2) | 0.0183 (12) | −0.0136 (14) | −0.0157 (17) |
C8 | 0.0340 (11) | 0.0412 (10) | 0.0389 (10) | −0.0015 (9) | 0.0017 (9) | 0.0008 (9) |
C9 | 0.0285 (11) | 0.0386 (9) | 0.0347 (9) | 0.0022 (9) | 0.0005 (8) | 0.0035 (8) |
C10 | 0.0416 (13) | 0.0473 (12) | 0.0475 (11) | 0.0076 (10) | 0.0017 (10) | −0.0071 (9) |
C11 | 0.0489 (14) | 0.0422 (11) | 0.0481 (11) | 0.0029 (11) | 0.0066 (10) | −0.0052 (9) |
C12 | 0.0661 (18) | 0.0677 (16) | 0.0667 (16) | −0.0120 (15) | 0.0121 (14) | −0.0195 (14) |
C13 | 0.093 (3) | 0.0663 (17) | 0.083 (2) | −0.0196 (17) | 0.0097 (18) | −0.0307 (15) |
C14 | 0.110 (3) | 0.0500 (14) | 0.0652 (16) | 0.0004 (17) | 0.0260 (17) | −0.0173 (12) |
C15 | 0.0755 (18) | 0.0493 (13) | 0.0516 (12) | 0.0193 (14) | 0.0202 (14) | 0.0017 (10) |
C16 | 0.0553 (15) | 0.0465 (12) | 0.0521 (12) | 0.0091 (12) | 0.0076 (11) | −0.0046 (10) |
C17 | 0.084 (2) | 0.080 (2) | 0.0770 (19) | 0.0358 (17) | 0.0277 (17) | 0.0024 (16) |
Cl1—C8 | 1.7797 (19) | C12—C13 | 1.386 (4) |
S1—O1 | 1.4237 (17) | C13—C14 | 1.364 (5) |
S1—O2 | 1.4211 (16) | C14—C15 | 1.385 (4) |
S1—N1 | 1.621 (2) | C15—C16 | 1.396 (3) |
S1—C8 | 1.7763 (19) | C15—C17 | 1.505 (4) |
N1—C1 | 1.428 (3) | C2—H2 | 0.9300 |
N1—C7 | 1.457 (3) | C3—H3 | 0.9300 |
N2—N3 | 1.411 (2) | C4—H4 | 0.9300 |
N2—C9 | 1.286 (2) | C5—H5 | 0.9300 |
N3—C10 | 1.269 (3) | C7—H7A | 0.9600 |
C1—C2 | 1.387 (3) | C7—H7B | 0.9600 |
C1—C6 | 1.400 (3) | C7—H7C | 0.9600 |
C2—C3 | 1.374 (4) | C8—H8 | 0.9800 |
C3—C4 | 1.377 (4) | C10—H10 | 0.9300 |
C4—C5 | 1.375 (3) | C12—H12 | 0.9300 |
C5—C6 | 1.397 (3) | C13—H13 | 0.9300 |
C6—C9 | 1.484 (3) | C14—H14 | 0.9300 |
C8—C9 | 1.513 (3) | C16—H16 | 0.9300 |
C10—C11 | 1.459 (3) | C17—H17A | 0.9600 |
C11—C12 | 1.393 (4) | C17—H17B | 0.9600 |
C11—C16 | 1.384 (4) | C17—H17C | 0.9600 |
O1—S1—O2 | 119.32 (10) | C16—C15—C17 | 120.8 (2) |
O1—S1—N1 | 108.37 (10) | C11—C16—C15 | 122.0 (2) |
O1—S1—C8 | 111.14 (9) | C1—C2—H2 | 119.00 |
O2—S1—N1 | 110.69 (10) | C3—C2—H2 | 119.00 |
O2—S1—C8 | 104.52 (9) | C2—C3—H3 | 120.00 |
N1—S1—C8 | 101.29 (10) | C4—C3—H3 | 120.00 |
S1—N1—C1 | 116.97 (14) | C3—C4—H4 | 120.00 |
S1—N1—C7 | 121.86 (17) | C5—C4—H4 | 120.00 |
C1—N1—C7 | 120.8 (2) | C4—C5—H5 | 119.00 |
N3—N2—C9 | 113.71 (16) | C6—C5—H5 | 119.00 |
N2—N3—C10 | 111.08 (17) | N1—C7—H7A | 109.00 |
N1—C1—C2 | 118.8 (2) | N1—C7—H7B | 110.00 |
N1—C1—C6 | 121.60 (17) | N1—C7—H7C | 109.00 |
C2—C1—C6 | 119.6 (2) | H7A—C7—H7B | 109.00 |
C1—C2—C3 | 121.1 (2) | H7A—C7—H7C | 109.00 |
C2—C3—C4 | 119.9 (2) | H7B—C7—H7C | 109.00 |
C3—C4—C5 | 119.7 (2) | Cl1—C8—H8 | 110.00 |
C4—C5—C6 | 121.6 (2) | S1—C8—H8 | 110.00 |
C1—C6—C5 | 118.04 (18) | C9—C8—H8 | 109.00 |
C1—C6—C9 | 122.46 (17) | N3—C10—H10 | 118.00 |
C5—C6—C9 | 119.47 (17) | C11—C10—H10 | 118.00 |
Cl1—C8—S1 | 108.93 (10) | C11—C12—H12 | 121.00 |
Cl1—C8—C9 | 110.45 (14) | C13—C12—H12 | 121.00 |
S1—C8—C9 | 108.89 (13) | C12—C13—H13 | 120.00 |
N2—C9—C6 | 118.41 (16) | C14—C13—H13 | 120.00 |
N2—C9—C8 | 121.94 (17) | C13—C14—H14 | 119.00 |
C6—C9—C8 | 119.63 (15) | C15—C14—H14 | 119.00 |
N3—C10—C11 | 123.1 (2) | C11—C16—H16 | 119.00 |
C10—C11—C12 | 122.2 (2) | C15—C16—H16 | 119.00 |
C10—C11—C16 | 118.5 (2) | C15—C17—H17A | 109.00 |
C12—C11—C16 | 119.4 (2) | C15—C17—H17B | 109.00 |
C11—C12—C13 | 119.0 (3) | C15—C17—H17C | 109.00 |
C12—C13—C14 | 120.7 (3) | H17A—C17—H17B | 109.00 |
C13—C14—C15 | 122.0 (3) | H17A—C17—H17C | 109.00 |
C14—C15—C16 | 117.0 (2) | H17B—C17—H17C | 109.00 |
C14—C15—C17 | 122.2 (2) | ||
O1—S1—N1—C1 | −171.41 (15) | C1—C2—C3—C4 | −0.3 (3) |
O1—S1—N1—C7 | 1.7 (2) | C2—C3—C4—C5 | 0.9 (3) |
O2—S1—N1—C1 | 55.99 (18) | C3—C4—C5—C6 | −0.8 (3) |
O2—S1—N1—C7 | −130.9 (2) | C4—C5—C6—C1 | 0.1 (3) |
C8—S1—N1—C1 | −54.42 (17) | C4—C5—C6—C9 | 178.17 (19) |
C8—S1—N1—C7 | 118.7 (2) | C1—C6—C9—N2 | −178.30 (18) |
O1—S1—C8—Cl1 | 49.97 (14) | C1—C6—C9—C8 | 3.4 (3) |
O1—S1—C8—C9 | 170.49 (13) | C5—C6—C9—N2 | 3.7 (3) |
O2—S1—C8—Cl1 | 179.94 (12) | C5—C6—C9—C8 | −174.64 (17) |
O2—S1—C8—C9 | −59.54 (15) | Cl1—C8—C9—N2 | −93.1 (2) |
N1—S1—C8—Cl1 | −64.97 (12) | Cl1—C8—C9—C6 | 85.20 (18) |
N1—S1—C8—C9 | 55.54 (15) | S1—C8—C9—N2 | 147.38 (16) |
S1—N1—C1—C2 | −151.50 (17) | S1—C8—C9—C6 | −34.4 (2) |
S1—N1—C1—C6 | 28.4 (3) | N3—C10—C11—C12 | 3.8 (4) |
C7—N1—C1—C2 | 35.3 (3) | N3—C10—C11—C16 | −175.3 (2) |
C7—N1—C1—C6 | −144.8 (2) | C10—C11—C12—C13 | −179.1 (2) |
C9—N2—N3—C10 | 174.07 (18) | C16—C11—C12—C13 | 0.0 (4) |
N3—N2—C9—C6 | −176.04 (16) | C10—C11—C16—C15 | 179.1 (2) |
N3—N2—C9—C8 | 2.2 (3) | C12—C11—C16—C15 | 0.0 (3) |
N2—N3—C10—C11 | −178.60 (19) | C11—C12—C13—C14 | 0.0 (4) |
N1—C1—C2—C3 | 179.5 (2) | C12—C13—C14—C15 | 0.0 (5) |
C6—C1—C2—C3 | −0.4 (3) | C13—C14—C15—C16 | 0.0 (4) |
N1—C1—C6—C5 | −179.34 (18) | C13—C14—C15—C17 | −179.5 (3) |
N1—C1—C6—C9 | 2.6 (3) | C14—C15—C16—C11 | 0.0 (3) |
C2—C1—C6—C5 | 0.5 (3) | C17—C15—C16—C11 | 179.6 (2) |
C2—C1—C6—C9 | −177.55 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.93 | 2.57 | 3.469 (3) | 163 |
C10—H10···O1ii | 0.93 | 2.53 | 3.300 (3) | 140 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C17H16ClN3O2S |
Mr | 361.84 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 8.7734 (2), 11.1271 (2), 17.9423 (3) |
V (Å3) | 1751.57 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.26 × 0.18 × 0.12 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.930, 0.960 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17152, 4265, 3478 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.088, 1.03 |
No. of reflections | 4265 |
No. of parameters | 219 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.27 |
Absolute structure | Flack (1983), 1788 Friedel pairs |
Absolute structure parameter | 0.47 (6) |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.93 | 2.57 | 3.469 (3) | 163 |
C10—H10···O1ii | 0.93 | 2.53 | 3.300 (3) | 140 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, y, z. |
Acknowledgements
MS gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Program (PIN 042–120567-PS2–276).
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The title compound (I), (Fig. 1) has been synthesized in continuation of our studies of Schiff bases (Shafiq et al., 2011a,b,c).
In (I), the benzene rings A (C1—C6) and B (C11—C16) are planar with r. m. s. deviation of 0.0033 and 0.0002 Å, respectively. The dihedral angle between A/B is 7.75 (13)°. The central group C (N2/N3/C10) is of course planar. The dihedral angle between A/C and B/C is 6.02 (19) and 5.11 (21)°, respectively. The thiazine ring D (C1/C6/C9/C8/S1/N1) is in the nvelope form, with the maximum puckering amplitude (Cremer & Pople, 1975), Q = 0.5707 (16) Å. The molecules form one-dimensional polymeric chains extending along the a-axis due to H-bonding of C—H···O type (Table 1).