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Volume 69 
Part 7 
Page o1042  
July 2013  

Received 30 April 2013
Accepted 28 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.041
wR = 0.112
Data-to-parameter ratio = 17.9
Details
Open access

O,O-Dimethyl O-(4-sulfamoylphenyl) phosphorothioate (cythioate)

aDepartment of Chemistry, Truman State University, Kirksville, MO 63501-4221, USA
Correspondence e-mail: baughman@truman.edu

The title molecule, C8H12NO5PS2, exhibits a crystallographic mirror plane that is perpendicular to the ring and bisects the sulfamoyl and thiophosphate ester groups. In the crystal, molecules are linked by N-H...O hydrogen-bonding interactions reminiscent of carboxylic acid hydrogen bonding pairs, forming chains parallel to the b-axis direction.

Related literature

The structure of a very similar compound {Famphur; systematic name O,O-dimethyl O-[p-[(N,N-dimethylsulfamoyl)phenyl] phosphorothioate} was published by Baughman (1997[Baughman, R. G. (1997). Acta Cryst. C53, 1928-1929.]).

[Scheme 1]

Experimental

Crystal data
  • C8H12NO5PS2

  • Mr = 297.28

  • Monoclinic, P 21 /m

  • a = 6.6634 (2) Å

  • b = 8.5514 (3) Å

  • c = 11.8716 (5) Å

  • [beta] = 105.067 (3)°

  • V = 653.21 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.54 mm-1

  • T = 295 K

  • 0.50 × 0.38 × 0.26 mm

Data collection
  • Bruker P4 diffractometer

  • Absorption correction: integration (XSHELL; Bruker, 1999[Bruker (1999). XSHELL. Bruker AXS, Inc., Madison, Wisconsin, USA.]) Tmin = 0.745, Tmax = 0.890

  • 2229 measured reflections

  • 1591 independent reflections

  • 1421 reflections with I > 2[sigma](I)

  • Rint = 0.031

  • 3 standard reflections every 100 reflections intensity decay: 1.2%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.112

  • S = 1.21

  • 1591 reflections

  • 89 parameters

  • 5 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3i 0.86 2.36 3.134 (3) 150
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: XSCANS (Bruker, 1996[Bruker (1996). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL/PC and SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5064 ).


References

Baughman, R. G. (1997). Acta Cryst. C53, 1928-1929.  [CSD] [CrossRef] [IUCr Journals]
Bruker (1996). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). XSHELL. Bruker AXS, Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1042  [ doi:10.1107/S1600536813014724 ]

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