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organic compounds
1-Propyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide
aMaterials Chemistry laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan
*Correspondence e-mail: iukhan.gcu@gmail.com
In the title compound, C11H13NO3S, a benzothiazine derivative, the heterocycle adopts a sofa conformation. In the crystal, weak C—H⋯O hydrogen bonds connect the molecules into a three-dimensional network.
Related literature
For the synthesis of the title compound, see: Volovenko et al. (2007). For a related structure, see: Shafiq et al. (2009
).
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, 1997
) and PLATON (Spek, 2009
); software used to prepare material for publication: WinGX (Farrugia, 1999
) and PLATON.
Supporting information
https://doi.org/10.1107/S160053681004078X/bt5369sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004078X/bt5369Isup2.hkl
The title compound was prepared following the available literature procedure (Volovenko et al., 2007).
All the C—H H-atoms were positioned with idealized geometry with C—H = 0.93 Å for aromatic C—H = 0.97 Å for methylene C—H = 0.96 Å for methyl and were refined using a riding model with Uiso(H) = 1.2 Ueq(C) for aromatic, with Uiso(H) = 1.2 Ueq(C) for methylene, with Uiso(H) = 1.5 Ueq(C) for methyl.
Here we report the
of title compound in countinuation to the previously published 3,3-dichloro-1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide derivative (Shafiq et al., 2009). The difference between the two compounds is a propyl which differ just only in substitution at N and at the methylene C atom in the benzothiazine ring. The heterocycle adopts a sofa conformation. Weak C—H···O type hydrogen bonds connect the molecules to a three dimensional network.For the synthesis of the title compound, see: Volovenko et al. (2007). For a related structure, see: Shafiq et al. (2009).
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, 1997) and PLATON (Spek, 2009); 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 level. |
![]() | Fig. 2. Unit cell packing diagram showing the hydrogen bonding with dashed lines. |
C11H13NO3S | Z = 2 |
Mr = 239.28 | F(000) = 252 |
Triclinic, P1 | Dx = 1.435 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9448 (2) Å | Cell parameters from 5097 reflections |
b = 8.0701 (3) Å | θ = 2.2–21.8° |
c = 9.6267 (2) Å | µ = 0.28 mm−1 |
α = 87.468 (2)° | T = 296 K |
β = 84.097 (2)° | Needle, light brown |
γ = 64.453 (1)° | 0.28 × 0.21 × 0.12 mm |
V = 553.92 (2) Å3 |
Bruker Kappa APEXII CCD diffractometer | 2765 independent reflections |
Radiation source: fine-focus sealed tube | 2229 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 28.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −10→10 |
Tmin = 0.925, Tmax = 0.967 | k = −10→10 |
12058 measured reflections | l = −12→12 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0604P)2 + 0.0882P] where P = (Fo2 + 2Fc2)/3 |
2765 reflections | (Δ/σ)max < 0.001 |
146 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C11H13NO3S | γ = 64.453 (1)° |
Mr = 239.28 | V = 553.92 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9448 (2) Å | Mo Kα radiation |
b = 8.0701 (3) Å | µ = 0.28 mm−1 |
c = 9.6267 (2) Å | T = 296 K |
α = 87.468 (2)° | 0.28 × 0.21 × 0.12 mm |
β = 84.097 (2)° |
Bruker Kappa APEXII CCD diffractometer | 2765 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 2229 reflections with I > 2σ(I) |
Tmin = 0.925, Tmax = 0.967 | Rint = 0.027 |
12058 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.30 e Å−3 |
2765 reflections | Δρmin = −0.38 e Å−3 |
146 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | 0.44648 (6) | 0.31465 (5) | 0.66978 (4) | 0.04181 (14) | |
O1 | 0.2757 (2) | 0.71661 (17) | 0.91660 (14) | 0.0633 (4) | |
O2 | 0.62535 (17) | 0.25460 (17) | 0.71992 (15) | 0.0584 (3) | |
O3 | 0.4391 (2) | 0.2879 (2) | 0.52525 (12) | 0.0680 (4) | |
N1 | 0.31827 (18) | 0.22605 (17) | 0.76115 (12) | 0.0380 (3) | |
C1 | 0.28023 (19) | 0.26527 (18) | 0.90617 (14) | 0.0313 (3) | |
C2 | 0.2496 (2) | 0.1412 (2) | 0.99954 (16) | 0.0408 (3) | |
H2 | 0.2519 | 0.0338 | 0.9661 | 0.049* | |
C3 | 0.2161 (2) | 0.1770 (2) | 1.14058 (16) | 0.0473 (4) | |
H3 | 0.1951 | 0.0935 | 1.2012 | 0.057* | |
C4 | 0.2129 (2) | 0.3344 (2) | 1.19393 (17) | 0.0494 (4) | |
H4 | 0.1947 | 0.3549 | 1.2898 | 0.059* | |
C5 | 0.2372 (2) | 0.4602 (2) | 1.10331 (16) | 0.0421 (3) | |
H5 | 0.2322 | 0.5679 | 1.1384 | 0.051* | |
C6 | 0.26911 (19) | 0.42939 (18) | 0.95988 (14) | 0.0323 (3) | |
C7 | 0.2874 (2) | 0.57493 (19) | 0.87064 (16) | 0.0376 (3) | |
C8 | 0.3163 (3) | 0.5469 (2) | 0.71447 (16) | 0.0447 (4) | |
H8A | 0.3812 | 0.6171 | 0.6723 | 0.054* | |
H8B | 0.1953 | 0.5924 | 0.6773 | 0.054* | |
C9 | 0.3171 (2) | 0.0585 (2) | 0.70536 (16) | 0.0398 (3) | |
H9A | 0.3717 | −0.0425 | 0.7696 | 0.048* | |
H9B | 0.3936 | 0.0264 | 0.6168 | 0.048* | |
C10 | 0.1214 (2) | 0.0854 (2) | 0.68464 (17) | 0.0461 (4) | |
H10A | 0.0411 | 0.1345 | 0.7699 | 0.055* | |
H10B | 0.1236 | −0.0331 | 0.6673 | 0.055* | |
C11 | 0.0384 (3) | 0.2133 (3) | 0.5651 (2) | 0.0662 (5) | |
H11A | 0.0339 | 0.3315 | 0.5821 | 0.099* | |
H11B | −0.0860 | 0.2258 | 0.5575 | 0.099* | |
H11C | 0.1149 | 0.1637 | 0.4797 | 0.099* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0535 (3) | 0.0410 (2) | 0.0377 (2) | −0.02944 (19) | 0.01063 (16) | −0.00505 (15) |
O1 | 0.0991 (11) | 0.0410 (7) | 0.0630 (8) | −0.0439 (7) | 0.0020 (7) | −0.0069 (6) |
O2 | 0.0442 (7) | 0.0516 (7) | 0.0801 (9) | −0.0240 (6) | 0.0097 (6) | −0.0051 (6) |
O3 | 0.1086 (11) | 0.0773 (9) | 0.0367 (7) | −0.0615 (9) | 0.0177 (7) | −0.0119 (6) |
N1 | 0.0526 (7) | 0.0369 (6) | 0.0339 (6) | −0.0295 (6) | 0.0055 (5) | −0.0063 (5) |
C1 | 0.0338 (7) | 0.0295 (7) | 0.0321 (7) | −0.0157 (5) | −0.0007 (5) | −0.0004 (5) |
C2 | 0.0499 (9) | 0.0319 (7) | 0.0438 (8) | −0.0219 (7) | 0.0001 (6) | 0.0035 (6) |
C3 | 0.0532 (10) | 0.0467 (9) | 0.0407 (9) | −0.0222 (8) | −0.0008 (7) | 0.0127 (7) |
C4 | 0.0580 (10) | 0.0567 (10) | 0.0307 (7) | −0.0227 (8) | −0.0012 (7) | 0.0008 (7) |
C5 | 0.0479 (9) | 0.0413 (8) | 0.0382 (8) | −0.0201 (7) | −0.0012 (6) | −0.0070 (6) |
C6 | 0.0338 (7) | 0.0294 (7) | 0.0353 (7) | −0.0151 (5) | −0.0021 (5) | −0.0008 (5) |
C7 | 0.0419 (8) | 0.0297 (7) | 0.0438 (8) | −0.0184 (6) | −0.0010 (6) | −0.0004 (6) |
C8 | 0.0595 (10) | 0.0351 (8) | 0.0426 (8) | −0.0249 (7) | 0.0003 (7) | 0.0064 (6) |
C9 | 0.0488 (9) | 0.0321 (7) | 0.0419 (8) | −0.0211 (6) | 0.0016 (6) | −0.0089 (6) |
C10 | 0.0573 (10) | 0.0497 (9) | 0.0436 (8) | −0.0347 (8) | −0.0039 (7) | −0.0002 (7) |
C11 | 0.0646 (12) | 0.0862 (15) | 0.0562 (11) | −0.0401 (11) | −0.0128 (9) | 0.0161 (10) |
S1—O2 | 1.4191 (14) | C5—C6 | 1.3915 (19) |
S1—O3 | 1.4282 (13) | C5—H5 | 0.9300 |
S1—N1 | 1.6464 (12) | C6—C7 | 1.473 (2) |
S1—C8 | 1.7535 (16) | C7—C8 | 1.509 (2) |
O1—C7 | 1.2069 (18) | C8—H8A | 0.9700 |
N1—C1 | 1.4178 (17) | C8—H8B | 0.9700 |
N1—C9 | 1.4808 (17) | C9—C10 | 1.508 (2) |
C1—C2 | 1.3982 (19) | C9—H9A | 0.9700 |
C1—C6 | 1.4070 (18) | C9—H9B | 0.9700 |
C2—C3 | 1.375 (2) | C10—C11 | 1.513 (3) |
C2—H2 | 0.9300 | C10—H10A | 0.9700 |
C3—C4 | 1.380 (2) | C10—H10B | 0.9700 |
C3—H3 | 0.9300 | C11—H11A | 0.9600 |
C4—C5 | 1.373 (2) | C11—H11B | 0.9600 |
C4—H4 | 0.9300 | C11—H11C | 0.9600 |
O2—S1—O3 | 117.98 (9) | O1—C7—C6 | 122.99 (14) |
O2—S1—N1 | 111.54 (7) | O1—C7—C8 | 118.84 (13) |
O3—S1—N1 | 107.86 (7) | C6—C7—C8 | 118.14 (12) |
O2—S1—C8 | 107.87 (8) | C7—C8—S1 | 111.75 (10) |
O3—S1—C8 | 110.27 (9) | C7—C8—H8A | 109.3 |
N1—S1—C8 | 99.80 (7) | S1—C8—H8A | 109.3 |
C1—N1—C9 | 120.81 (11) | C7—C8—H8B | 109.3 |
C1—N1—S1 | 116.96 (9) | S1—C8—H8B | 109.3 |
C9—N1—S1 | 117.37 (10) | H8A—C8—H8B | 107.9 |
C2—C1—C6 | 118.28 (13) | N1—C9—C10 | 111.75 (13) |
C2—C1—N1 | 120.18 (12) | N1—C9—H9A | 109.3 |
C6—C1—N1 | 121.53 (12) | C10—C9—H9A | 109.3 |
C3—C2—C1 | 120.42 (14) | N1—C9—H9B | 109.3 |
C3—C2—H2 | 119.8 | C10—C9—H9B | 109.3 |
C1—C2—H2 | 119.8 | H9A—C9—H9B | 107.9 |
C2—C3—C4 | 121.32 (14) | C9—C10—C11 | 113.28 (15) |
C2—C3—H3 | 119.3 | C9—C10—H10A | 108.9 |
C4—C3—H3 | 119.3 | C11—C10—H10A | 108.9 |
C5—C4—C3 | 118.96 (14) | C9—C10—H10B | 108.9 |
C5—C4—H4 | 120.5 | C11—C10—H10B | 108.9 |
C3—C4—H4 | 120.5 | H10A—C10—H10B | 107.7 |
C4—C5—C6 | 121.20 (14) | C10—C11—H11A | 109.5 |
C4—C5—H5 | 119.4 | C10—C11—H11B | 109.5 |
C6—C5—H5 | 119.4 | H11A—C11—H11B | 109.5 |
C5—C6—C1 | 119.74 (13) | C10—C11—H11C | 109.5 |
C5—C6—C7 | 117.26 (12) | H11A—C11—H11C | 109.5 |
C1—C6—C7 | 122.99 (12) | H11B—C11—H11C | 109.5 |
O2—S1—N1—C1 | 59.41 (12) | C2—C1—C6—C5 | 3.0 (2) |
O3—S1—N1—C1 | −169.51 (11) | N1—C1—C6—C5 | −178.04 (13) |
C8—S1—N1—C1 | −54.35 (12) | C2—C1—C6—C7 | −176.18 (14) |
O2—S1—N1—C9 | −96.15 (12) | N1—C1—C6—C7 | 2.8 (2) |
O3—S1—N1—C9 | 34.93 (14) | C5—C6—C7—O1 | −0.1 (2) |
C8—S1—N1—C9 | 150.09 (12) | C1—C6—C7—O1 | 179.13 (15) |
C9—N1—C1—C2 | 3.0 (2) | C5—C6—C7—C8 | −178.19 (13) |
S1—N1—C1—C2 | −151.64 (12) | C1—C6—C7—C8 | 1.0 (2) |
C9—N1—C1—C6 | −175.92 (13) | O1—C7—C8—S1 | 148.80 (14) |
S1—N1—C1—C6 | 29.41 (17) | C6—C7—C8—S1 | −32.99 (17) |
C6—C1—C2—C3 | −2.2 (2) | O2—S1—C8—C7 | −61.58 (13) |
N1—C1—C2—C3 | 178.80 (14) | O3—S1—C8—C7 | 168.29 (11) |
C1—C2—C3—C4 | −0.5 (2) | N1—S1—C8—C7 | 54.98 (12) |
C2—C3—C4—C5 | 2.4 (3) | C1—N1—C9—C10 | 82.62 (17) |
C3—C4—C5—C6 | −1.6 (3) | S1—N1—C9—C10 | −122.81 (12) |
C4—C5—C6—C1 | −1.1 (2) | N1—C9—C10—C11 | 70.53 (19) |
C4—C5—C6—C7 | 178.08 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11B···O2i | 0.96 | 2.57 | 3.346 (2) | 138 |
C8—H8A···O3ii | 0.97 | 2.55 | 3.453 (2) | 155 |
C2—H2···O1iii | 0.93 | 2.55 | 3.4665 (19) | 170 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C11H13NO3S |
Mr | 239.28 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 7.9448 (2), 8.0701 (3), 9.6267 (2) |
α, β, γ (°) | 87.468 (2), 84.097 (2), 64.453 (1) |
V (Å3) | 553.92 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.28 × 0.21 × 0.12 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.925, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12058, 2765, 2229 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.111, 1.07 |
No. of reflections | 2765 |
No. of parameters | 146 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.38 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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 |
C11—H11B···O2i | 0.96 | 2.57 | 3.346 (2) | 138.4 |
C8—H8A···O3ii | 0.97 | 2.55 | 3.453 (2) | 155.0 |
C2—H2···O1iii | 0.93 | 2.55 | 3.4665 (19) | 169.9 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z. |
Acknowledgements
The authors acknowledge the Higher Education Commission of Pakistan for providing a grant for the project to strengthen the Materials Chemistry Laboratory at GC University Lahore.
References
Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Here we report the crystal structure of title compound in countinuation to the previously published 3,3-dichloro-1-ethyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide derivative (Shafiq et al., 2009). The difference between the two compounds is a propyl which differ just only in substitution at N and at the methylene C atom in the benzothiazine ring. The heterocycle adopts a sofa conformation. Weak C—H···O type hydrogen bonds connect the molecules to a three dimensional network.