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organic compounds
Methyl 2-(but-3-enyl)-4-hydroxy-1,1-dioxo-2H-1λ6,2-benzothiazine-3-carboxylate
aDepartment of Chemistry, University of Gujrat, Gujrat 50781, Pakistan, bMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, cApplied Chemistry Research Centre PCSIR Laboratories Complex, Lahore 54600, Pakistan, and dDepartment of Chemistry, Georgetown University, 37th and `O' Streets NW Washington, DC 20057-1227, USA
*Correspondence e-mail: mnachemist@hotmail.com
In the title compound, C14H15NO5S, the thiazine ring adopts a sofa conformation and an intramolecular O—H⋯O hydrogen bond forms an S(6) ring. In the crystal, molecules are linked viaC—H⋯O interactions.
Related literature
For the synthesis, see: Arshad et al. (2011b); Zia-ur-Rehman, et al. (2006
). For related structures, see: Arshad et al. (2011a
, 2012
). For graph-set notation, see: Bernstein et al. (1995
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: PLATON (Spek, 2009
) and X-SEED (Barbour 2001
); software used to prepare material for publication: WinGX (Farrugia, 1999
) and PLATON.
Supporting information
10.1107/S1600536812022908/bt5926sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812022908/bt5926Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812022908/bt5926Isup3.cml
The synthesis of the titled compound has been published (Arshad et al., 2011a). The title compound was recrystallized from ethylacetate under slow evaporation of the solvent.
The H-atoms bonded to C were positioned with idealized geometry with C—H ranging from 0.95 Å to = 0.99Å and refined using a riding model with Uiso(H) = 1.5 Ueq(C) for methyl and Uiso(H) = 1.2 Ueq(C) for the remaining H atoms. The coordinates of the H atom bonded to O were refined with Uiso(H) 1.5Ueq(O).
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and X-SEED (Barbour 2001); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009). ![]() | Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability. |
C14H15NO5S | F(000) = 1296 |
Mr = 309.33 | Dx = 1.447 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 4741 reflections |
a = 25.265 (8) Å | θ = 2.4–27.3° |
b = 8.929 (3) Å | µ = 0.25 mm−1 |
c = 12.584 (4) Å | T = 100 K |
V = 2839.0 (15) Å3 | Block, colorless |
Z = 8 | 0.41 × 0.36 × 0.19 mm |
Bruker SMART 1K diffractometer | 3445 independent reflections |
Radiation source: fine-focus sealed tube | 2643 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
ϕ and ω scans | θmax = 28.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −33→32 |
Tmin = 0.905, Tmax = 0.954 | k = −11→11 |
22868 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0432P)2 + 1.393P] where P = (Fo2 + 2Fc2)/3 |
3445 reflections | (Δ/σ)max = 0.001 |
194 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
C14H15NO5S | V = 2839.0 (15) Å3 |
Mr = 309.33 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 25.265 (8) Å | µ = 0.25 mm−1 |
b = 8.929 (3) Å | T = 100 K |
c = 12.584 (4) Å | 0.41 × 0.36 × 0.19 mm |
Bruker SMART 1K diffractometer | 3445 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2643 reflections with I > 2σ(I) |
Tmin = 0.905, Tmax = 0.954 | Rint = 0.081 |
22868 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.33 e Å−3 |
3445 reflections | Δρmin = −0.52 e Å−3 |
194 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 | ||
S1 | 0.383769 (17) | 0.36570 (5) | 0.46460 (3) | 0.01998 (13) | |
O1 | 0.28657 (5) | 0.22258 (15) | 0.20949 (10) | 0.0233 (3) | |
O2 | 0.38708 (5) | 0.20923 (14) | 0.48963 (10) | 0.0237 (3) | |
O3 | 0.41184 (5) | 0.47125 (15) | 0.52964 (10) | 0.0252 (3) | |
O4 | 0.37180 (5) | 0.18207 (15) | 0.10068 (10) | 0.0242 (3) | |
O5 | 0.44900 (5) | 0.25535 (14) | 0.17283 (10) | 0.0218 (3) | |
N1 | 0.40302 (6) | 0.38813 (17) | 0.34120 (11) | 0.0193 (3) | |
C1 | 0.31660 (7) | 0.4152 (2) | 0.45726 (14) | 0.0206 (4) | |
C2 | 0.29195 (7) | 0.4945 (2) | 0.53786 (14) | 0.0234 (4) | |
H2 | 0.3113 | 0.5258 | 0.5987 | 0.028* | |
C3 | 0.23838 (7) | 0.5274 (2) | 0.52817 (15) | 0.0260 (4) | |
H3 | 0.2210 | 0.5839 | 0.5819 | 0.031* | |
C4 | 0.21024 (7) | 0.4782 (2) | 0.44037 (15) | 0.0256 (4) | |
H4 | 0.1734 | 0.4989 | 0.4354 | 0.031* | |
C5 | 0.23497 (7) | 0.3991 (2) | 0.35976 (15) | 0.0233 (4) | |
H5 | 0.2151 | 0.3656 | 0.3003 | 0.028* | |
C6 | 0.28911 (7) | 0.36857 (19) | 0.36578 (14) | 0.0194 (4) | |
C7 | 0.31751 (7) | 0.29795 (19) | 0.27785 (14) | 0.0198 (4) | |
C8 | 0.37096 (7) | 0.3116 (2) | 0.26458 (14) | 0.0190 (4) | |
C9 | 0.39673 (7) | 0.2439 (2) | 0.17199 (14) | 0.0202 (4) | |
C10 | 0.47565 (8) | 0.1946 (2) | 0.08044 (15) | 0.0271 (4) | |
H10A | 0.4664 | 0.0886 | 0.0725 | 0.041* | |
H10B | 0.5140 | 0.2044 | 0.0894 | 0.041* | |
H10C | 0.4645 | 0.2496 | 0.0169 | 0.041* | |
C11 | 0.42697 (7) | 0.5340 (2) | 0.30952 (15) | 0.0228 (4) | |
H11A | 0.4436 | 0.5221 | 0.2387 | 0.027* | |
H11B | 0.4554 | 0.5591 | 0.3606 | 0.027* | |
C12 | 0.38804 (8) | 0.6648 (2) | 0.30478 (16) | 0.0272 (4) | |
H12A | 0.3576 | 0.6377 | 0.2591 | 0.033* | |
H12B | 0.3745 | 0.6864 | 0.3770 | 0.033* | |
C13 | 0.41478 (8) | 0.8014 (2) | 0.26092 (17) | 0.0316 (5) | |
H13 | 0.4245 | 0.8001 | 0.1880 | 0.038* | |
C14 | 0.42573 (8) | 0.9223 (2) | 0.31568 (17) | 0.0306 (5) | |
H14A | 0.4166 | 0.9276 | 0.3888 | 0.037* | |
H14B | 0.4428 | 1.0045 | 0.2823 | 0.037* | |
H1O | 0.3066 (11) | 0.199 (3) | 0.159 (2) | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0183 (2) | 0.0232 (2) | 0.0185 (2) | −0.00070 (17) | −0.00184 (16) | −0.00094 (17) |
O1 | 0.0193 (6) | 0.0285 (7) | 0.0221 (7) | −0.0037 (5) | −0.0026 (5) | −0.0032 (5) |
O2 | 0.0240 (7) | 0.0246 (7) | 0.0227 (7) | 0.0010 (5) | −0.0039 (5) | 0.0011 (5) |
O3 | 0.0231 (7) | 0.0310 (7) | 0.0217 (7) | −0.0030 (5) | −0.0018 (5) | −0.0041 (6) |
O4 | 0.0211 (6) | 0.0284 (7) | 0.0230 (7) | −0.0001 (5) | −0.0031 (5) | −0.0043 (6) |
O5 | 0.0174 (6) | 0.0261 (7) | 0.0219 (6) | 0.0018 (5) | −0.0002 (5) | −0.0021 (5) |
N1 | 0.0171 (7) | 0.0230 (8) | 0.0178 (7) | −0.0020 (6) | −0.0010 (6) | −0.0018 (6) |
C1 | 0.0194 (8) | 0.0202 (9) | 0.0221 (9) | −0.0026 (7) | 0.0016 (7) | 0.0027 (7) |
C2 | 0.0250 (9) | 0.0250 (10) | 0.0201 (9) | −0.0023 (8) | 0.0012 (7) | −0.0004 (7) |
C3 | 0.0264 (9) | 0.0256 (10) | 0.0260 (10) | 0.0012 (8) | 0.0076 (7) | 0.0014 (8) |
C4 | 0.0193 (9) | 0.0278 (10) | 0.0297 (10) | 0.0015 (7) | 0.0036 (7) | 0.0062 (8) |
C5 | 0.0192 (9) | 0.0267 (10) | 0.0241 (9) | −0.0029 (7) | −0.0001 (7) | 0.0043 (8) |
C6 | 0.0189 (8) | 0.0187 (9) | 0.0205 (9) | −0.0026 (7) | 0.0001 (7) | 0.0028 (7) |
C7 | 0.0200 (8) | 0.0194 (9) | 0.0198 (9) | −0.0010 (7) | −0.0022 (7) | 0.0018 (7) |
C8 | 0.0186 (8) | 0.0194 (8) | 0.0189 (9) | −0.0013 (7) | −0.0025 (7) | −0.0004 (7) |
C9 | 0.0196 (9) | 0.0196 (9) | 0.0213 (9) | 0.0006 (7) | −0.0008 (7) | 0.0027 (7) |
C10 | 0.0241 (9) | 0.0319 (11) | 0.0253 (10) | 0.0034 (8) | 0.0040 (8) | −0.0036 (8) |
C11 | 0.0210 (9) | 0.0243 (10) | 0.0230 (9) | −0.0048 (7) | 0.0010 (7) | −0.0020 (8) |
C12 | 0.0281 (10) | 0.0249 (10) | 0.0286 (10) | −0.0031 (8) | −0.0032 (8) | −0.0006 (8) |
C13 | 0.0398 (12) | 0.0307 (11) | 0.0242 (10) | −0.0041 (9) | −0.0020 (9) | 0.0037 (9) |
C14 | 0.0343 (11) | 0.0261 (10) | 0.0313 (11) | −0.0013 (8) | −0.0053 (8) | 0.0042 (9) |
S1—O2 | 1.4346 (14) | C5—C6 | 1.397 (2) |
S1—O3 | 1.4356 (13) | C5—H5 | 0.9500 |
S1—N1 | 1.6396 (16) | C6—C7 | 1.462 (2) |
S1—C1 | 1.7561 (19) | C7—C8 | 1.366 (2) |
O1—C7 | 1.343 (2) | C8—C9 | 1.465 (3) |
O1—H1O | 0.84 (3) | C10—H10A | 0.9800 |
O4—C9 | 1.227 (2) | C10—H10B | 0.9800 |
O5—C9 | 1.325 (2) | C10—H10C | 0.9800 |
O5—C10 | 1.449 (2) | C11—C12 | 1.528 (3) |
N1—C8 | 1.433 (2) | C11—H11A | 0.9900 |
N1—C11 | 1.490 (2) | C11—H11B | 0.9900 |
C1—C2 | 1.385 (3) | C12—C13 | 1.499 (3) |
C1—C6 | 1.407 (2) | C12—H12A | 0.9900 |
C2—C3 | 1.391 (3) | C12—H12B | 0.9900 |
C2—H2 | 0.9500 | C13—C14 | 1.310 (3) |
C3—C4 | 1.386 (3) | C13—H13 | 0.9500 |
C3—H3 | 0.9500 | C14—H14A | 0.9500 |
C4—C5 | 1.385 (3) | C14—H14B | 0.9500 |
C4—H4 | 0.9500 | ||
O2—S1—O3 | 119.04 (8) | C8—C7—C6 | 122.63 (16) |
O2—S1—N1 | 108.04 (8) | C7—C8—N1 | 121.29 (16) |
O3—S1—N1 | 108.25 (8) | C7—C8—C9 | 119.96 (16) |
O2—S1—C1 | 108.24 (8) | N1—C8—C9 | 118.73 (15) |
O3—S1—C1 | 110.00 (8) | O4—C9—O5 | 123.51 (17) |
N1—S1—C1 | 101.90 (8) | O4—C9—C8 | 122.61 (16) |
C7—O1—H1O | 104.9 (18) | O5—C9—C8 | 113.87 (15) |
C9—O5—C10 | 115.33 (14) | O5—C10—H10A | 109.5 |
C8—N1—C11 | 117.79 (14) | O5—C10—H10B | 109.5 |
C8—N1—S1 | 114.29 (12) | H10A—C10—H10B | 109.5 |
C11—N1—S1 | 118.72 (12) | O5—C10—H10C | 109.5 |
C2—C1—C6 | 121.90 (17) | H10A—C10—H10C | 109.5 |
C2—C1—S1 | 121.65 (14) | H10B—C10—H10C | 109.5 |
C6—C1—S1 | 116.46 (13) | N1—C11—C12 | 114.66 (15) |
C1—C2—C3 | 118.80 (17) | N1—C11—H11A | 108.6 |
C1—C2—H2 | 120.6 | C12—C11—H11A | 108.6 |
C3—C2—H2 | 120.6 | N1—C11—H11B | 108.6 |
C4—C3—C2 | 120.14 (17) | C12—C11—H11B | 108.6 |
C4—C3—H3 | 119.9 | H11A—C11—H11B | 107.6 |
C2—C3—H3 | 119.9 | C13—C12—C11 | 110.25 (17) |
C5—C4—C3 | 120.96 (17) | C13—C12—H12A | 109.6 |
C5—C4—H4 | 119.5 | C11—C12—H12A | 109.6 |
C3—C4—H4 | 119.5 | C13—C12—H12B | 109.6 |
C4—C5—C6 | 120.12 (18) | C11—C12—H12B | 109.6 |
C4—C5—H5 | 119.9 | H12A—C12—H12B | 108.1 |
C6—C5—H5 | 119.9 | C14—C13—C12 | 124.9 (2) |
C5—C6—C1 | 118.02 (17) | C14—C13—H13 | 117.6 |
C5—C6—C7 | 121.60 (16) | C12—C13—H13 | 117.6 |
C1—C6—C7 | 120.29 (16) | C13—C14—H14A | 120.0 |
O1—C7—C8 | 122.81 (16) | C13—C14—H14B | 120.0 |
O1—C7—C6 | 114.53 (15) | H14A—C14—H14B | 120.0 |
O2—S1—N1—C8 | 61.69 (14) | C5—C6—C7—O1 | −20.8 (2) |
O3—S1—N1—C8 | −168.15 (12) | C1—C6—C7—O1 | 162.66 (16) |
C1—S1—N1—C8 | −52.19 (14) | C5—C6—C7—C8 | 157.21 (18) |
O2—S1—N1—C11 | −152.15 (12) | C1—C6—C7—C8 | −19.3 (3) |
O3—S1—N1—C11 | −21.99 (15) | O1—C7—C8—N1 | −177.64 (15) |
C1—S1—N1—C11 | 93.96 (14) | C6—C7—C8—N1 | 4.5 (3) |
O2—S1—C1—C2 | 104.25 (16) | O1—C7—C8—C9 | 0.7 (3) |
O3—S1—C1—C2 | −27.34 (18) | C6—C7—C8—C9 | −177.14 (16) |
N1—S1—C1—C2 | −142.01 (15) | C11—N1—C8—C7 | −110.93 (19) |
O2—S1—C1—C6 | −75.07 (15) | S1—N1—C8—C7 | 35.6 (2) |
O3—S1—C1—C6 | 153.34 (13) | C11—N1—C8—C9 | 70.7 (2) |
N1—S1—C1—C6 | 38.67 (15) | S1—N1—C8—C9 | −142.81 (14) |
C6—C1—C2—C3 | 0.6 (3) | C10—O5—C9—O4 | 2.4 (3) |
S1—C1—C2—C3 | −178.67 (14) | C10—O5—C9—C8 | −177.74 (15) |
C1—C2—C3—C4 | 1.6 (3) | C7—C8—C9—O4 | 4.8 (3) |
C2—C3—C4—C5 | −1.7 (3) | N1—C8—C9—O4 | −176.84 (16) |
C3—C4—C5—C6 | −0.3 (3) | C7—C8—C9—O5 | −175.05 (16) |
C4—C5—C6—C1 | 2.4 (3) | N1—C8—C9—O5 | 3.3 (2) |
C4—C5—C6—C7 | −174.17 (17) | C8—N1—C11—C12 | 74.1 (2) |
C2—C1—C6—C5 | −2.6 (3) | S1—N1—C11—C12 | −70.88 (19) |
S1—C1—C6—C5 | 176.72 (14) | N1—C11—C12—C13 | −173.83 (15) |
C2—C1—C6—C7 | 174.05 (17) | C11—C12—C13—C14 | −111.0 (2) |
S1—C1—C6—C7 | −6.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.95 | 2.52 | 3.269 (2) | 136 |
O1—H1O···O4 | 0.84 (3) | 1.81 (3) | 2.577 (2) | 151 (3) |
Symmetry code: (i) −x+1/2, y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C14H15NO5S |
Mr | 309.33 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 100 |
a, b, c (Å) | 25.265 (8), 8.929 (3), 12.584 (4) |
V (Å3) | 2839.0 (15) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.41 × 0.36 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART 1K diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.905, 0.954 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22868, 3445, 2643 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.109, 1.05 |
No. of reflections | 3445 |
No. of parameters | 194 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.52 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and X-SEED (Barbour 2001), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.95 | 2.52 | 3.269 (2) | 136.2 |
O1—H1O···O4 | 0.84 (3) | 1.81 (3) | 2.577 (2) | 151 (3) |
Symmetry code: (i) −x+1/2, y+1/2, z. |
Acknowledgements
The authors acknowledge the Higher Education Commission of Pakistan for providing fellowships to MNA (PIN
042–120607-Ps2–183 and PIN IRSIP-10-PS-2).References
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Herein we report the crystal structure of the title compound in continuation of our research on the synthesis (Arshad et al., 2011b), biological activities (Zia-ur-Rehman et al., 2006) and crystal structures (Arshad et al., 2011a, 2012) of thiazine related heterocyles.
The title compound is the N-3-butenyl derivative of methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide. The planar methyl ester moiety (r.m.s deviation 0.008Å) is oriented at dihedral angles of 11.39 (10)° and 16.97 (11)° with respect to the thiazine (C1/C6/C7/C8/N1/S1) and benzene (C1/C2/C3/C4/C5/C6) rings. The thiazine ring adopts a sofa conformation and is inclined at 17.27 (12)° with respect to the benzene ring. A six membered (C7/O1/H1O/O4/C9/C8) ring with graph set notation S11(6) (Bernstein et al., 1995) is formed through an O—H···O intramolecular hydrogen bond. The crystal structure is stabilized by weak C—H···O interactions (Tab. 1).