organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 64| Part 7| July 2008| Pages o1213-o1214

N-Butyl-4-hydr­­oxy-2-methyl-2H-1,2-benzo­thia­zine-3-carboxamide 1,1-dioxide

aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, bDepartment of Chemistry, University of Science and Technology, Bannu, Pakistan, and cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
*Correspondence e-mail: drhamidlatif@yahoo.com

(Received 10 May 2008; accepted 1 June 2008; online 7 June 2008)

The title compound, C14H18N2O4S, contains hydrogen-bonded dimeric pairs of mol­ecules arranged around inversion centers, forming 14-membered rings with an R22(14) motif. The structure is stabilized by extensive intra­molecular inter­actions. The thia­zine ring adopts a half-chair conformation, with the S and N atoms displaced by −0.485 (3) and 0.296 (3) Å, respectively, from the plane formed by the remaining atoms of the ring.

Related literature

For related literature, see: Ahmad, Siddiqui, Ahmad et al. (2008[Ahmad, M., Siddiqui, H. L., Ahmad, S., Irfan Ashiq, M. & Tizzard, G. J. (2008). Acta Cryst. E64, o594.]); Ahmad, Siddiqui, Zia-ur-Rehman et al. (2008[Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M., Ashiq, M. I. & Tizzard, G. J. (2008). Acta Cryst. E64, o788.]); Bernstein et al. (1994[Bernstein, J., Etter, M. C. & Leiserowitz, L. (1994). Structure Correlation, edited by H.-B. Bürgi & J. D. Dunitz, Vol. 2, pp. 431-507. New York: VCH.]); Gupta et al. (1993[Gupta, R. R., Dev, P. K., Sharma, M. L., Rajoria, C. M., Gupta, A. & Nyati, M. (1993). Anticancer Drugs, 4, 589-592.], 2002[Gupta, S. K., Bansal, P., Bhardwaj, R. K., Jaiswal, J. & Velpandian, T. (2002). Skin Pharmacol. Appl. Skin Physiol. 15, 105-111.]); Kojić-Prodić & Rużić-Toroš (1982[Kojić-Prodić, B. & Rużić-Toroš, Ž. (1982). Acta Cryst. B38, 2948-2951.]); Lombardino (1971[Lombardino, J. G. (1971). US Patent No. 3 591 584.]); Lombardino & Wiseman (1972[Lombardino, J. G. & Wiseman, E. H. (1972). J. Med. Chem. 15, 848-849.]); Rehman et al. (2005[Rehman, M. Z., Choudary, J. A. & Ahmad, S. (2005). Bull. Korean Chem. Soc. 54, 1171-1175.], 2006[Rehman, M. Z., Choudary, J. A., Ahmad, S. & Siddiqui, H. L. (2006). Chem. Pharm. Bull. 54, 1175-1178.]); Sianesi et al. (1973[Sianesi, E., Redaelli, R., Magistretti, M. J. & Massarani, E. (1973). J. Med. Chem. 16, 1133-1137.]); Siddiqui et al. (2008[Siddiqui, W. A., Ahmad, S., Tariq, M. I., Siddiqui, H. L. & Parvez, M. (2008). Acta Cryst. C64, o4-o6.]); Zinnes et al. (1982[Zinnes, H., Sircar, J. C., Lindo, N., Schwartz, M. L., Fabian, A. C., Shavel, J. Jr, Kasulanis, C. F., Genzer, J. D., Lutomski, C. & DiPasquale, G. (1982). J. Med. Chem. 25, 12-18.]); Drebushchak et al. (2006[Drebushchak, T. N., Pankrushina, N. N., Shakhtshneider, T. P. & Apenina, S. A. (2006). Acta Cryst. C62, o429-o431.]).

[Scheme 1]

Experimental

Crystal data
  • C14H18N2O4S

  • Mr = 310.36

  • Monoclinic, P 21 /c

  • a = 10.233 (2) Å

  • b = 14.780 (4) Å

  • c = 10.365 (5) Å

  • β = 108.79 (2)°

  • V = 1484.1 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.23 mm−1

  • T = 173 (2) K

  • 0.14 × 0.12 × 0.06 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1997[Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.]) Tmin = 0.968, Tmax = 0.986

  • 12380 measured reflections

  • 3405 independent reflections

  • 2646 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.100

  • S = 1.03

  • 3405 reflections

  • 198 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3O⋯O4 0.88 (2) 1.76 (2) 2.572 (2) 153 (2)
N2—H2N⋯O2i 0.87 (2) 2.21 (2) 3.052 (2) 161 (2)
N2—H2N⋯N1 0.87 (2) 2.34 (2) 2.753 (2) 109 (2)
C9—H9B⋯O2 0.98 2.49 2.864 (2) 102
Symmetry code: (i) -x+1, -y, -z+2.

Data collection: COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: HKL DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); program(s) used to solve structure: SHELXS97 (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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Several benzothiazine derivatives like piroxicam, sudoxicam (Lombardino & Wiseman, 1972; Rehman et al., 2005) and isoxicam (Zinnes et al., 1982) have been reported in the literature to be potential anti-inflammatory agents. Some of the derivatives of benzothiazines are found to be analgesic (Gupta et al., 2002), anti-cancer (Gupta et al., 1993) and exhibitors of central nervous system activity (Sianesi et al., 1973). We have reported anti-bacterial activities (Rehman et al., 2006) of a series of 1,2-benzothiazines. In continuation of our work on 1,2-benzothiazines 1,1-dioxides (Ahmad, Siddiqui, Ahmad, Irfan Ashiq & Tizzard, 2008; Ahmad, Siddiqui, Zia-ur-Rehman, Ashiq & Tizzard, 2008), we report in this paper the crystal structure of the title compound, (I), which was patented for Pfizer Inc. (Lombardino, 1971).

The structure of (I), (Fig. 1), contains dimeric pairs of molecules lying about inversion centers resulting from N2—H2N···O2 hydrogen bonds (Fig. 2). The 14-membered rings thus formed represent R22(14) motif in the graph set notation (Bernstein et al., 1994). Similar hydrogen-bonded dimers have been reported in structures related to the title compound (Siddiqui et al., 2008; Drebushchak et al., 2006; Kojić-Prodić & Rużić-Toroš, 1982). The structure is stabilized by extensive intramolecular interactions (Fig. 1 and Table 1). The thiazine ring in (I) adopts a half-chair conformation with atoms S1 and N1 displaced by -0.485 (3) and 0.296 (3) Å, respectively, from the plane formed by the remaining atoms of the ring.

Related literature top

For related literature, see: Ahmad, Siddiqui, Ahmad et al. (2008); Ahmad, Siddiqui, Zia-ur-Rehman et al. (2008); Bernstein et al. (1994); Gupta et al. (1993, 2002); Kojić-Prodić & Rużić-Toroš (1982); Lombardino (1971); Lombardino & Wiseman (1972); Rehman et al. (2005, 2006); Sianesi et al. (1973); Siddiqui et al. (2008); Zinnes et al. (1982); Drebushchak et al. (2006).

Experimental top

Methyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide (1.0 g, 3.72 mmoles) was dissolved in n-butyl amine (5 ml) in a test tube. The mixture was placed at room temperature for 7 days. Crystals of (I) suitable for crystallographic analysis were found, which were washed with MeOH.

Refinement top

Though all the H atoms could be found in a difference map, the H atoms bonded to C atoms were included at geometrically idealized positions and refined in riding-model approximation with the following constraints: C—H distances were set to 0.95, 0.98 and 0.99 Å for aryl, methyl and methylene H atoms, respectively, and Uiso(H) = 1.2Ueq(C). H atoms bonded to N2 and O3 were taken from a difference map and were allowed to refine with Uiso = 1.2 times Ueq of the parent atom. The final difference map was free of any chemically significant features.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of (I) with displacement ellipsoids plotted at 50% probability level; intramolecular interactions have been indicated by dashed lines.
[Figure 2] Fig. 2. Unit cell packing of (I) showing hydrogen bonds with dashed lines; H atoms not involved in hydrogen bonds have been omitted.
N-Butyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide top
Crystal data top
C14H18N2O4SF(000) = 656
Mr = 310.36Dx = 1.389 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12380 reflections
a = 10.233 (2) Åθ = 3.4–27.6°
b = 14.780 (4) ŵ = 0.24 mm1
c = 10.365 (5) ÅT = 173 K
β = 108.79 (2)°Prism, colorless
V = 1484.1 (9) Å30.14 × 0.12 × 0.06 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
3405 independent reflections
Radiation source: fine-focus sealed tube2646 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω and ϕ scansθmax = 27.6°, θmin = 3.4°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1313
Tmin = 0.968, Tmax = 0.986k = 1919
12380 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.045P)2 + 0.606P]
where P = (Fo2 + 2Fc2)/3
3405 reflections(Δ/σ)max = 0.001
198 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C14H18N2O4SV = 1484.1 (9) Å3
Mr = 310.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.233 (2) ŵ = 0.24 mm1
b = 14.780 (4) ÅT = 173 K
c = 10.365 (5) Å0.14 × 0.12 × 0.06 mm
β = 108.79 (2)°
Data collection top
Nonius KappaCCD
diffractometer
3405 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
2646 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.986Rint = 0.041
12380 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.30 e Å3
3405 reflectionsΔρmin = 0.43 e Å3
198 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.53051 (4)0.13868 (3)0.96872 (5)0.03033 (13)
O10.45310 (12)0.12905 (9)0.82760 (14)0.0384 (3)
O20.46724 (13)0.11547 (9)1.06916 (15)0.0400 (3)
O30.86081 (13)0.22923 (9)0.83438 (13)0.0336 (3)
H3O0.899 (2)0.1799 (16)0.816 (2)0.050*
O40.92527 (12)0.06200 (9)0.82242 (13)0.0356 (3)
N10.67274 (13)0.07980 (9)0.99855 (14)0.0265 (3)
N20.78434 (15)0.04424 (10)0.86553 (16)0.0327 (3)
H2N0.714 (2)0.0525 (14)0.894 (2)0.039*
C10.59359 (17)0.24980 (11)0.99677 (17)0.0283 (4)
C20.53309 (18)0.31325 (12)1.05849 (19)0.0342 (4)
H20.45870.29671.08970.041*
C30.58309 (19)0.40116 (12)1.07376 (19)0.0359 (4)
H30.54300.44551.11590.043*
C40.69144 (19)0.42436 (12)1.02763 (18)0.0349 (4)
H40.72350.48511.03630.042*
C50.75381 (17)0.36033 (12)0.96906 (18)0.0309 (4)
H50.82890.37720.93920.037*
C60.70664 (17)0.27103 (11)0.95385 (17)0.0276 (4)
C70.77716 (16)0.19970 (12)0.90287 (17)0.0272 (4)
C80.76003 (16)0.11021 (12)0.92283 (17)0.0269 (4)
C90.74832 (19)0.05636 (13)1.14249 (18)0.0355 (4)
H9A0.82060.01211.14570.043*
H9B0.68390.03051.18480.043*
H9C0.79050.11101.19210.043*
C100.82934 (17)0.04054 (12)0.86719 (17)0.0288 (4)
C110.8470 (2)0.12047 (12)0.8176 (2)0.0385 (4)
H11A0.94780.11070.84300.046*
H11B0.80910.12380.71700.046*
C120.82004 (18)0.20820 (12)0.8775 (2)0.0335 (4)
H12A0.71920.21890.84860.040*
H12B0.85370.20340.97810.040*
C130.88952 (19)0.28900 (12)0.83487 (19)0.0339 (4)
H13A0.84960.29750.73510.041*
H13B0.98920.27610.85620.041*
C140.8724 (2)0.37560 (13)0.9058 (2)0.0405 (5)
H14A0.92370.42450.87990.049*
H14B0.77430.39160.87870.049*
H14C0.90790.36681.00480.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0252 (2)0.0286 (2)0.0417 (3)0.00243 (16)0.01704 (18)0.00165 (18)
O10.0263 (6)0.0414 (8)0.0450 (8)0.0039 (5)0.0078 (5)0.0038 (6)
O20.0400 (7)0.0340 (7)0.0597 (9)0.0031 (5)0.0352 (7)0.0005 (6)
O30.0347 (7)0.0328 (7)0.0411 (7)0.0041 (5)0.0232 (6)0.0015 (6)
O40.0316 (6)0.0379 (7)0.0455 (8)0.0004 (5)0.0239 (6)0.0008 (6)
N10.0267 (7)0.0273 (7)0.0306 (8)0.0003 (5)0.0160 (6)0.0018 (6)
N20.0306 (8)0.0311 (8)0.0433 (9)0.0001 (6)0.0215 (7)0.0031 (7)
C10.0269 (8)0.0267 (8)0.0330 (9)0.0003 (6)0.0121 (7)0.0023 (7)
C20.0317 (9)0.0342 (10)0.0404 (10)0.0042 (7)0.0167 (8)0.0028 (8)
C30.0400 (10)0.0296 (9)0.0393 (10)0.0073 (8)0.0142 (8)0.0019 (8)
C40.0407 (10)0.0269 (9)0.0353 (10)0.0007 (7)0.0097 (8)0.0024 (7)
C50.0306 (9)0.0309 (9)0.0315 (9)0.0027 (7)0.0104 (7)0.0040 (7)
C60.0255 (8)0.0307 (9)0.0267 (8)0.0011 (7)0.0087 (7)0.0019 (7)
C70.0229 (8)0.0338 (9)0.0264 (8)0.0028 (6)0.0098 (7)0.0014 (7)
C80.0234 (8)0.0318 (9)0.0282 (9)0.0018 (6)0.0122 (7)0.0008 (7)
C90.0385 (10)0.0390 (10)0.0331 (10)0.0019 (8)0.0171 (8)0.0021 (8)
C100.0245 (8)0.0345 (9)0.0290 (9)0.0006 (7)0.0107 (7)0.0003 (7)
C110.0432 (10)0.0326 (10)0.0502 (12)0.0037 (8)0.0294 (9)0.0028 (8)
C120.0324 (9)0.0340 (10)0.0398 (10)0.0013 (7)0.0194 (8)0.0026 (8)
C130.0329 (9)0.0348 (10)0.0367 (10)0.0015 (7)0.0152 (8)0.0036 (8)
C140.0365 (10)0.0356 (10)0.0486 (12)0.0003 (8)0.0128 (9)0.0003 (9)
Geometric parameters (Å, º) top
S1—O11.4286 (15)C5—C61.397 (2)
S1—O21.4335 (14)C5—H50.9500
S1—N11.6375 (14)C6—C71.469 (2)
S1—C11.7543 (18)C7—C81.359 (2)
O3—C71.349 (2)C8—C101.470 (2)
O3—H3O0.88 (2)C9—H9A0.9800
O4—C101.254 (2)C9—H9B0.9800
N1—C81.438 (2)C9—H9C0.9800
N1—C91.484 (2)C11—C121.501 (3)
N2—C101.333 (2)C11—H11A0.9900
N2—C111.460 (2)C11—H11B0.9900
N2—H2N0.87 (2)C12—C131.526 (2)
C1—C21.388 (2)C12—H12A0.9900
C1—C61.402 (2)C12—H12B0.9900
C2—C31.387 (3)C13—C141.514 (3)
C2—H20.9500C13—H13A0.9900
C3—C41.385 (3)C13—H13B0.9900
C3—H30.9500C14—H14A0.9800
C4—C51.386 (3)C14—H14B0.9800
C4—H40.9500C14—H14C0.9800
O1—S1—O2119.25 (9)C7—C8—C10121.34 (15)
O1—S1—N1107.84 (8)N1—C8—C10117.28 (14)
O2—S1—N1108.51 (8)N1—C9—H9A109.5
O1—S1—C1108.42 (8)N1—C9—H9B109.5
O2—S1—C1109.38 (8)H9A—C9—H9B109.5
N1—S1—C1102.07 (8)N1—C9—H9C109.5
C7—O3—H3O104.4 (15)H9A—C9—H9C109.5
C8—N1—C9114.06 (13)H9B—C9—H9C109.5
C8—N1—S1113.67 (11)O4—C10—N2122.76 (16)
C9—N1—S1117.24 (11)O4—C10—C8120.15 (15)
C10—N2—C11122.83 (15)N2—C10—C8117.08 (15)
C10—N2—H2N116.6 (14)N2—C11—C12111.55 (15)
C11—N2—H2N120.6 (14)N2—C11—H11A109.3
C2—C1—C6122.08 (16)C12—C11—H11A109.3
C2—C1—S1120.92 (13)N2—C11—H11B109.3
C6—C1—S1117.00 (13)C12—C11—H11B109.3
C3—C2—C1118.85 (16)H11A—C11—H11B108.0
C3—C2—H2120.6C11—C12—C13113.08 (14)
C1—C2—H2120.6C11—C12—H12A109.0
C4—C3—C2119.98 (17)C13—C12—H12A109.0
C4—C3—H3120.0C11—C12—H12B109.0
C2—C3—H3120.0C13—C12—H12B109.0
C3—C4—C5121.00 (17)H12A—C12—H12B107.8
C3—C4—H4119.5C14—C13—C12112.53 (15)
C5—C4—H4119.5C14—C13—H13A109.1
C4—C5—C6120.23 (16)C12—C13—H13A109.1
C4—C5—H5119.9C14—C13—H13B109.1
C6—C5—H5119.9C12—C13—H13B109.1
C5—C6—C1117.78 (16)H13A—C13—H13B107.8
C5—C6—C7121.80 (15)C13—C14—H14A109.5
C1—C6—C7120.31 (15)C13—C14—H14B109.5
O3—C7—C8122.01 (15)H14A—C14—H14B109.5
O3—C7—C6115.20 (15)C13—C14—H14C109.5
C8—C7—C6122.79 (15)H14A—C14—H14C109.5
C7—C8—N1121.38 (14)H14B—C14—H14C109.5
O1—S1—N1—C861.67 (13)S1—C1—C6—C76.9 (2)
O2—S1—N1—C8167.86 (11)C5—C6—C7—O319.3 (2)
C1—S1—N1—C852.42 (13)C1—C6—C7—O3164.56 (15)
O1—S1—N1—C9161.75 (12)C5—C6—C7—C8160.65 (16)
O2—S1—N1—C931.28 (14)C1—C6—C7—C815.5 (2)
C1—S1—N1—C984.16 (13)O3—C7—C8—N1178.67 (14)
O1—S1—C1—C2103.81 (15)C6—C7—C8—N11.3 (2)
O2—S1—C1—C227.73 (17)O3—C7—C8—C101.7 (3)
N1—S1—C1—C2142.53 (15)C6—C7—C8—C10178.33 (15)
O1—S1—C1—C676.03 (15)C9—N1—C8—C798.65 (19)
O2—S1—C1—C6152.43 (13)S1—N1—C8—C739.3 (2)
N1—S1—C1—C637.63 (15)C9—N1—C8—C1081.71 (18)
C6—C1—C2—C32.3 (3)S1—N1—C8—C10140.30 (13)
S1—C1—C2—C3177.53 (14)C11—N2—C10—O43.1 (3)
C1—C2—C3—C40.1 (3)C11—N2—C10—C8177.77 (16)
C2—C3—C4—C51.7 (3)C7—C8—C10—O413.4 (3)
C3—C4—C5—C60.9 (3)N1—C8—C10—O4166.94 (15)
C4—C5—C6—C11.4 (2)C7—C8—C10—N2165.76 (16)
C4—C5—C6—C7174.82 (16)N1—C8—C10—N213.9 (2)
C2—C1—C6—C53.0 (3)C10—N2—C11—C12156.43 (17)
S1—C1—C6—C5176.82 (13)N2—C11—C12—C13177.35 (16)
C2—C1—C6—C7173.25 (16)C11—C12—C13—C14174.83 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O40.88 (2)1.76 (2)2.572 (2)153 (2)
N2—H2N···O2i0.87 (2)2.21 (2)3.052 (2)161 (2)
N2—H2N···N10.87 (2)2.34 (2)2.753 (2)109 (2)
C9—H9B···O20.982.492.864 (2)102
Symmetry code: (i) x+1, y, z+2.

Experimental details

Crystal data
Chemical formulaC14H18N2O4S
Mr310.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)10.233 (2), 14.780 (4), 10.365 (5)
β (°) 108.79 (2)
V3)1484.1 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.14 × 0.12 × 0.06
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1997)
Tmin, Tmax0.968, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
12380, 3405, 2646
Rint0.041
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.100, 1.03
No. of reflections3405
No. of parameters198
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.30, 0.43

Computer programs: COLLECT (Hooft, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O40.88 (2)1.76 (2)2.572 (2)153 (2)
N2—H2N···O2i0.87 (2)2.21 (2)3.052 (2)161 (2)
N2—H2N···N10.87 (2)2.34 (2)2.753 (2)109 (2)
C9—H9B···O20.982.492.864 (2)102
Symmetry code: (i) x+1, y, z+2.
 

References

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Volume 64| Part 7| July 2008| Pages o1213-o1214
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