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Volume 69 
Part 11 
Page o1698  
November 2013  

Received 12 September 2013
Accepted 17 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.011 Å
R = 0.069
wR = 0.218
Data-to-parameter ratio = 12.7
Details
Open access

Methyl 1-allyl-4-hy­droxy-2,2-dioxo-1H-2[lambda]6,1-benzo­thia­zine-3-carboxyl­ate

aSTC "Institute for Single Crystals", National Academy of Sciences of Ukraine, 60 Lenina ave., Kharkiv 61001, Ukraine, and bNational University of Pharmacy, 4 Blyukhera St, Kharkiv 61168, Ukraine
Correspondence e-mail: sveta@xray.isc.kharkov.com

There are two independent mol­ecules in the asymmetric unit of the title compound, C13H13NO5S, in both of which the ester substituent is nearly coplanar [C-C-C-O torsion angles = 2.7 (7) and -0.8 (7)°] with the planar fragment of the bicycle due to the formation of a strong O-H...O intra­molecular hydrogen bond. The vinyl group at the ring N atom is approximately orthogonal to the heterocyclic mean plane [C-N-C-C torsion angles = 103.1 (6) and 98.2 (5)°]. The refinement was performed on a two-component, non-merohedrally twinned crystal [population ratio = 0.483 (3):0.517 (3).

Related literature

For general properties of oxicams, see: Kleemann et al. (2008[Kleemann, A., Engel, J., Kutscher, B. & Reihert, D. (2008). Pharmaceutical Substances: Syntheses, Patents, Applications of the most relevant APIs, 5th ed. Stuttgart: Thieme.]). For H...O contacts, see: Zefirov (1997[Zefirov, Y. V. (1997). Kristallografiya, 42, 936-958.]) and for C-N bond lengths, see: Bürgi & Dunitz (1994[Bürgi, H.-B. & Dunitz, J. D. (1994). Structure Correlation, Vol. 2, pp. 767-784. Weinheim: VCH.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13NO5S

  • Mr = 295.30

  • Monoclinic, P 21 /c

  • a = 17.8654 (12) Å

  • b = 6.9444 (5) Å

  • c = 21.1462 (16) Å

  • [beta] = 90.122 (7)°

  • V = 2623.5 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 293 K

  • 0.30 × 0.10 × 0.10 mm

Data collection
  • Agilent Xcalibur3 diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011[Agilent (2011). CrysAlis CCD and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.925, Tmax = 0.974

  • 4647 measured reflections

  • 4647 independent reflections

  • 3728 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.218

  • S = 1.15

  • 4647 reflections

  • 366 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1A-H1OA...O2A 0.82 1.84 2.553 (8) 144
O1B-H1OB...O2B 0.82 1.87 2.588 (8) 146

Data collection: CrysAlis CCD (Agilent, 2011[Agilent (2011). CrysAlis CCD and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Agilent, 2011[Agilent (2011). CrysAlis CCD and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2518 ).


References

Agilent (2011). CrysAlis CCD and CrysAlis RED. Agilent Technologies, Yarnton, England.
Bürgi, H.-B. & Dunitz, J. D. (1994). Structure Correlation, Vol. 2, pp. 767-784. Weinheim: VCH.
Kleemann, A., Engel, J., Kutscher, B. & Reihert, D. (2008). Pharmaceutical Substances: Syntheses, Patents, Applications of the most relevant APIs, 5th ed. Stuttgart: Thieme.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Zefirov, Y. V. (1997). Kristallografiya, 42, 936-958.  [ChemPort]


Acta Cryst (2013). E69, o1698  [ doi:10.1107/S1600536813028572 ]

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