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ISSN: 2056-9890

Methyl 2-(2,3,5-tri­methyl-1,1-dioxo-2H-1λ6,2,6-thia­diazin-4-yl)benzoate

aChemistry Department, JJT University, Rajasthan, India, bSchool of Chemistry & Physics, University of KwaZulu-Natal, Durban 4000, South Africa, cDepartment of Chemistry, Government Science College, Gandhinagar, Gujarat, India, and dSchool of Pharmacology, University of KwaZulu Natal, Westville Campus, Private Bag X54001, South Africa
*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 17 September 2012; accepted 9 November 2012; online 17 November 2012)

There are two mol­ecules, A and B, in the asymmetric unit of the title compound, C14H16N2O4S, which is the first example reported in this family of compounds in which the Nsp3 atom of the thia­diazine ring is methyl­ated. The thia­diazine rings adopt shallow envelope conformations, with the S atoms displaced by 0.319 (12) and 0.182 (12) Å from the mean planes of the other ring atoms in mol­ecules A and B, respectively. The dihedral angles between the thia­diazine mean planes (excluding S) and the attached benzene rings are 86.8 (3) and 86.7 (3)° for mol­ecules A and B, respectively.

Related literature

For synthetic background, see: Wright (1964[Wright, J. B. (1964). J. Org. Chem. 29, 1905-1909.]). For a related structure, see: Bhatt et al. (2012[Bhatt, N., Bhatt, P., Vyas, K. B., Nimavat, K., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2012). Acta Cryst. E68, o2160.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16N2O4S

  • Mr = 308.35

  • Orthorhombic, P n a 21

  • a = 13.5954 (3) Å

  • b = 8.0683 (2) Å

  • c = 25.9554 (7) Å

  • V = 2847.09 (12) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 173 K

  • 0.28 × 0.22 × 0.21 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.935, Tmax = 0.950

  • 33574 measured reflections

  • 6094 independent reflections

  • 4522 reflections with I > 2σ(I)

  • Rint = 0.057

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.083

  • S = 0.99

  • 6094 reflections

  • 388 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.25 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2751 Friedel pairs

  • Flack parameter: −0.06 (5)

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (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: DENZO-SMN; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The synthesis of 1,2,6-thiadiazine-1,1-dioxides derivatives was first reported using sulfamide with alpha and beta diketones (Wright, 1964). We have reported the 3,5-dimethyl based structure with an aromatic ring at position 4 of the thiadiazine ring containing an ethyl ester functional group (Bhatt et al., 2012). The structure displayed intermolecular hydrogen bonding.

The title compound is also a 3,5 dimethyl based structure with an aromatic ring at the same position on the thiadiazine ring, but here the sp3 nitrogen atom is methylated. This prevents any equivalent hydrogen bonding features in the structure seen in previous examples. The is no π-π stacking or weak CH—π inteactions either in the crystal. The title compound has two isomeric forms in the crystal. The sulfur atoms S1A and S1B deviate from their ring planes (N1A/B, C2/AB, C3A/B, C4A/B, N2A/B) by 0.319 (12) Å and 0.182 (12) Å respectively (Fig. 1) and the benzene rings deviate from the planes by 86.8 (3) and 86.7 (3)°, respectively. The ester functional groups of the two isomers are not co-planar to the benzene ring planes but differ by 16.93 (4) and 16.48 (4)°, respectively.

Related literature top

For synthetic background, see: Wright (1964). For a related structure, see: Bhatt et al. (2012)

For related literature, see: Cremer & Pople (1975).

Experimental top

2-(3, 5-dimethyl-1, 1-dioxo-2H-1, 2, 6-thiadiazin-4-yl) benzoic acid (4.75 g,17 mmole) was dissolved in acetone (125 ml), to this K2CO3 (11.75 g, 85 mmole) was added slowly and then stirred for 10–15 min. Methyl iodide (7.23 g, 51 mmole) was added and reaction mixture was refluxed for 3 hrs. The reaction progress was monitored by TLC using ethyl acetate/hexane (8:2,Rf = 0.8). Excess solvent was completely evaporated under vacuum. The residue was treated with conc.HCl to get 2-(2,3,5-trimethyl-1,1-dioxido-2H-1,2,6-thiadiazin-4-yl)benzoic acid as a white solid (4.3 g Yield: 81.9%).

2-(2,3,5-trimethyl-1,1-dioxido-2H-1,2,6-thiadiazin-4-yl)benzoic acid (2.94 g, 10 mmole) was dissolved in methanol (25 ml), to this solution thionyl chloride (5.95 g, 50 mmole) was added slowly and the reaction mixture was refluxed for 3 hrs. The reaction progress was monitored by TLC using ethyl acetate/hexane (8:2,Rf = 0.8). Excess solvent was completely evaporated under vacuum. The residue was purified by silica gel column using methanol/ethyl acetate (1:9) as the eluent to afford the methyl ester as a colourless solid. (1.34 g,Yield: 55%).M.p.= 260 K

Recrystallization using dioxane/water at room temperature afforded yellow blocks.

Refinement top

All hydrogen atoms were placed in idealized positions and refined with geometrical constraints. Flack x parameter is -0.0586 with e.s.d. 0.0543.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with H atoms omitted for clarity. Displacement ellipsoids are drawn at 40% probability.
Methyl 2-(2,3,5-trimethyl-1,1-dioxo-2H-1λ6,2,6-thiadiazin-4-yl)benzoate top
Crystal data top
C14H16N2O4SDx = 1.439 Mg m3
Mr = 308.35Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 33574 reflections
a = 13.5954 (3) Åθ = 2.6–27.5°
b = 8.0683 (2) ŵ = 0.25 mm1
c = 25.9554 (7) ÅT = 173 K
V = 2847.09 (12) Å3Block, yellow
Z = 80.28 × 0.22 × 0.21 mm
F(000) = 1296
Data collection top
Nonius KappaCCD
diffractometer
6094 independent reflections
Radiation source: fine-focus sealed tube4522 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
1.2° ϕ scans and ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1717
Tmin = 0.935, Tmax = 0.950k = 1010
33574 measured reflectionsl = 3330
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0445P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.083(Δ/σ)max < 0.001
S = 0.99Δρmax = 0.21 e Å3
6094 reflectionsΔρmin = 0.25 e Å3
388 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0022 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2751 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.06 (5)
Crystal data top
C14H16N2O4SV = 2847.09 (12) Å3
Mr = 308.35Z = 8
Orthorhombic, Pna21Mo Kα radiation
a = 13.5954 (3) ŵ = 0.25 mm1
b = 8.0683 (2) ÅT = 173 K
c = 25.9554 (7) Å0.28 × 0.22 × 0.21 mm
Data collection top
Nonius KappaCCD
diffractometer
6094 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4522 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.950Rint = 0.057
33574 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.083Δρmax = 0.21 e Å3
S = 0.99Δρmin = 0.25 e Å3
6094 reflectionsAbsolute structure: Flack (1983), 2751 Friedel pairs
388 parametersAbsolute structure parameter: 0.06 (5)
1 restraint
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.16819 (4)0.24471 (7)0.03146 (3)0.02850 (14)
O1A0.17683 (12)0.3922 (2)0.06114 (8)0.0473 (5)
O2A0.19297 (13)0.2610 (2)0.02157 (7)0.0484 (5)
O3A0.01809 (15)0.1560 (2)0.18508 (7)0.0479 (5)
O4A0.01511 (13)0.01517 (19)0.25899 (7)0.0390 (4)
N1A0.22849 (14)0.0982 (2)0.05644 (9)0.0407 (6)
N2A0.05030 (13)0.1839 (2)0.03452 (8)0.0281 (4)
C1A0.26014 (19)0.1285 (4)0.11282 (13)0.0533 (9)
H1A10.32380.12110.09530.080*
H1A20.23550.24240.11070.080*
H1A30.26800.09710.14910.080*
C2A0.18851 (17)0.0136 (3)0.08748 (10)0.0324 (6)
C3A0.08626 (17)0.0289 (2)0.09642 (9)0.0242 (5)
C4A0.02022 (16)0.0661 (3)0.06916 (9)0.0252 (5)
C5A0.08899 (15)0.0468 (3)0.07394 (11)0.0315 (6)
H5A10.11810.15240.08470.047*
H5A20.10380.03840.09970.047*
H5A30.11650.01380.04060.047*
C6A0.01996 (19)0.2803 (3)0.00249 (11)0.0439 (7)
H6A10.05560.20490.02050.066*
H6A20.01630.36190.01810.066*
H6A30.06690.33770.02490.066*
C7A0.04993 (16)0.1651 (3)0.13101 (10)0.0254 (5)
C8A0.02189 (16)0.1410 (3)0.18317 (9)0.0248 (5)
C9A0.00644 (17)0.2776 (3)0.21258 (11)0.0334 (6)
H9A0.02600.26180.24740.040*
C10A0.00654 (18)0.4363 (3)0.19185 (10)0.0359 (6)
H10A0.02510.52840.21250.043*
C11A0.02038 (17)0.4595 (3)0.14124 (11)0.0343 (6)
H11A0.02010.56770.12680.041*
C12A0.04773 (17)0.3253 (3)0.11149 (10)0.0299 (6)
H12A0.06560.34310.07650.036*
C13A0.01886 (17)0.0251 (3)0.20735 (10)0.0303 (6)
C14A0.0134 (2)0.1689 (3)0.28670 (11)0.0429 (7)
H14A0.06720.23990.27470.064*
H14B0.02140.14710.32360.064*
H14C0.04960.22480.28080.064*
S1B0.10386 (4)0.26833 (7)0.45180 (2)0.02889 (15)
O1B0.08708 (12)0.3200 (2)0.50324 (7)0.0447 (5)
O2B0.08897 (11)0.09637 (19)0.44206 (8)0.0484 (5)
O3B0.24965 (14)0.35986 (19)0.29068 (7)0.0485 (5)
O4B0.24683 (13)0.50555 (18)0.21771 (7)0.0395 (5)
N1B0.04139 (13)0.3758 (2)0.41302 (9)0.0339 (5)
N2B0.22197 (13)0.3092 (2)0.43775 (8)0.0281 (5)
C1B0.00445 (19)0.5920 (4)0.35389 (13)0.0504 (8)
H1B10.01750.57860.31700.076*
H1B20.00860.70960.36310.076*
H1B30.06160.55040.36180.076*
C2B0.07937 (18)0.4957 (3)0.38431 (9)0.0285 (5)
C3B0.18034 (17)0.5317 (3)0.38014 (9)0.0243 (5)
C4B0.24909 (16)0.4372 (3)0.40624 (9)0.0242 (5)
C5B0.35705 (16)0.4635 (3)0.40010 (11)0.0332 (6)
H5B10.38630.48880.43370.050*
H5B20.36860.55620.37650.050*
H5B30.38720.36280.38610.050*
C6B0.29451 (18)0.2085 (3)0.46649 (11)0.0398 (7)
H6B10.34020.15650.44220.060*
H6B20.26010.12240.48610.060*
H6B30.33120.27990.49020.060*
C7B0.21176 (16)0.6741 (2)0.34682 (10)0.0250 (5)
C8B0.23889 (15)0.6576 (3)0.29426 (10)0.0259 (5)
C9B0.26085 (17)0.7992 (3)0.26573 (10)0.0318 (6)
H9B0.27880.78820.23050.038*
C10B0.25717 (18)0.9542 (3)0.28739 (11)0.0367 (6)
H10B0.27261.04900.26720.044*
C11B0.23110 (18)0.9722 (3)0.33840 (10)0.0348 (6)
H11B0.22861.07940.35350.042*
C12B0.20849 (18)0.8329 (3)0.36763 (10)0.0313 (6)
H12B0.19030.84650.40270.038*
C13B0.24545 (16)0.4921 (3)0.26875 (10)0.0283 (6)
C14B0.2508 (2)0.3515 (3)0.18876 (10)0.0433 (7)
H14D0.31510.29890.19390.065*
H14E0.24120.37480.15200.065*
H14F0.19890.27680.20080.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0315 (3)0.0281 (3)0.0259 (3)0.0024 (3)0.0061 (3)0.0015 (3)
O1A0.0388 (10)0.0397 (10)0.0635 (15)0.0022 (8)0.0006 (9)0.0202 (9)
O2A0.0550 (11)0.0627 (12)0.0276 (11)0.0042 (9)0.0155 (9)0.0088 (9)
O3A0.0854 (15)0.0268 (10)0.0315 (11)0.0043 (9)0.0104 (10)0.0007 (8)
O4A0.0536 (11)0.0373 (10)0.0261 (11)0.0004 (8)0.0042 (9)0.0035 (8)
N1A0.0275 (11)0.0427 (12)0.0520 (16)0.0031 (9)0.0068 (10)0.0163 (11)
N2A0.0270 (10)0.0294 (10)0.0280 (12)0.0015 (8)0.0031 (9)0.0067 (10)
C1A0.0287 (14)0.0637 (19)0.067 (2)0.0114 (13)0.0020 (14)0.0279 (16)
C2A0.0294 (13)0.0372 (14)0.0305 (15)0.0034 (11)0.0010 (11)0.0061 (11)
C3A0.0271 (12)0.0242 (11)0.0213 (13)0.0004 (9)0.0015 (10)0.0011 (10)
C4A0.0295 (12)0.0239 (12)0.0223 (13)0.0019 (9)0.0007 (10)0.0019 (10)
C5A0.0271 (13)0.0286 (12)0.0388 (16)0.0015 (10)0.0014 (11)0.0032 (11)
C6A0.0427 (16)0.0372 (14)0.052 (2)0.0030 (12)0.0096 (14)0.0166 (13)
C7A0.0200 (11)0.0265 (12)0.0297 (15)0.0033 (9)0.0009 (10)0.0040 (10)
C8A0.0251 (11)0.0252 (12)0.0240 (14)0.0013 (9)0.0012 (10)0.0028 (10)
C9A0.0333 (13)0.0342 (13)0.0328 (16)0.0006 (11)0.0035 (11)0.0058 (12)
C10A0.0424 (14)0.0282 (13)0.0372 (17)0.0024 (11)0.0017 (13)0.0120 (12)
C11A0.0386 (14)0.0247 (12)0.0396 (17)0.0033 (10)0.0015 (12)0.0029 (12)
C12A0.0328 (13)0.0284 (13)0.0284 (15)0.0012 (10)0.0023 (11)0.0004 (11)
C13A0.0301 (14)0.0330 (14)0.0279 (16)0.0022 (10)0.0037 (11)0.0006 (11)
C14A0.0494 (16)0.0449 (16)0.0342 (17)0.0054 (12)0.0060 (13)0.0159 (12)
S1B0.0294 (3)0.0277 (3)0.0295 (4)0.0015 (2)0.0053 (3)0.0029 (3)
O1B0.0433 (10)0.0624 (12)0.0284 (12)0.0088 (9)0.0098 (9)0.0041 (10)
O2B0.0416 (10)0.0235 (8)0.0800 (17)0.0027 (7)0.0053 (10)0.0049 (9)
O3B0.0853 (15)0.0260 (9)0.0342 (12)0.0006 (10)0.0057 (11)0.0002 (8)
O4B0.0579 (12)0.0349 (10)0.0257 (12)0.0001 (8)0.0039 (8)0.0017 (8)
N1B0.0273 (11)0.0402 (12)0.0342 (13)0.0019 (9)0.0021 (9)0.0113 (10)
N2B0.0282 (10)0.0297 (9)0.0266 (12)0.0022 (8)0.0006 (9)0.0040 (9)
C1B0.0318 (14)0.0645 (18)0.055 (2)0.0014 (13)0.0074 (14)0.0273 (15)
C2B0.0301 (12)0.0297 (12)0.0257 (14)0.0033 (10)0.0003 (10)0.0019 (10)
C3B0.0283 (12)0.0239 (11)0.0208 (13)0.0020 (9)0.0031 (10)0.0003 (10)
C4B0.0281 (11)0.0217 (11)0.0230 (13)0.0006 (9)0.0002 (10)0.0010 (10)
C5B0.0277 (12)0.0356 (13)0.0364 (16)0.0004 (10)0.0000 (11)0.0068 (11)
C6B0.0340 (13)0.0436 (13)0.0417 (19)0.0071 (11)0.0039 (12)0.0145 (13)
C7B0.0215 (11)0.0239 (12)0.0295 (15)0.0005 (9)0.0045 (10)0.0020 (10)
C8B0.0238 (12)0.0240 (12)0.0299 (15)0.0008 (9)0.0002 (10)0.0024 (10)
C9B0.0350 (13)0.0350 (13)0.0254 (15)0.0004 (10)0.0011 (11)0.0061 (11)
C10B0.0433 (15)0.0256 (13)0.0413 (18)0.0019 (11)0.0004 (13)0.0077 (12)
C11B0.0405 (14)0.0223 (12)0.0415 (18)0.0003 (10)0.0050 (12)0.0019 (11)
C12B0.0332 (13)0.0296 (13)0.0311 (16)0.0022 (11)0.0039 (11)0.0003 (11)
C13B0.0261 (12)0.0324 (14)0.0265 (15)0.0028 (10)0.0026 (11)0.0000 (11)
C14B0.0547 (17)0.0465 (16)0.0286 (17)0.0063 (12)0.0051 (13)0.0135 (12)
Geometric parameters (Å, º) top
S1A—O1A1.4223 (17)S1B—O1B1.4171 (18)
S1A—O2A1.4233 (19)S1B—O2B1.4247 (17)
S1A—N1A1.578 (2)S1B—N1B1.577 (2)
S1A—N2A1.6781 (18)S1B—N2B1.6793 (19)
O3A—C13A1.204 (3)O3B—C13B1.211 (3)
O4A—C13A1.344 (3)O4B—C13B1.329 (3)
O4A—C14A1.434 (3)O4B—C14B1.453 (3)
N1A—C2A1.326 (3)N1B—C2B1.326 (3)
N2A—C4A1.371 (3)N2B—C4B1.368 (3)
N2A—C6A1.486 (3)N2B—C6B1.480 (3)
C1A—C2A1.496 (3)C1B—C2B1.505 (3)
C1A—H1A10.9800C1B—H1B10.9800
C1A—H1A20.9800C1B—H1B20.9800
C1A—H1A30.9800C1B—H1B30.9800
C2A—C3A1.415 (3)C2B—C3B1.407 (3)
C3A—C4A1.377 (3)C3B—C4B1.383 (3)
C3A—C7A1.502 (3)C3B—C7B1.500 (3)
C4A—C5A1.498 (3)C4B—C5B1.492 (3)
C5A—H5A10.9800C5B—H5B10.9800
C5A—H5A20.9800C5B—H5B20.9800
C5A—H5A30.9800C5B—H5B30.9800
C6A—H6A10.9800C6B—H6B10.9800
C6A—H6A20.9800C6B—H6B20.9800
C6A—H6A30.9800C6B—H6B30.9800
C7A—C12A1.388 (3)C7B—C12B1.391 (3)
C7A—C8A1.420 (3)C7B—C8B1.419 (3)
C8A—C9A1.395 (3)C8B—C9B1.394 (3)
C8A—C13A1.481 (3)C8B—C13B1.493 (3)
C9A—C10A1.389 (4)C9B—C10B1.372 (3)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.376 (3)C10B—C11B1.378 (4)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.381 (3)C11B—C12B1.391 (3)
C11A—H11A0.9500C11B—H11B0.9500
C12A—H12A0.9500C12B—H12B0.9500
C14A—H14A0.9800C14B—H14D0.9800
C14A—H14B0.9800C14B—H14E0.9800
C14A—H14C0.9800C14B—H14F0.9800
O1A—S1A—O2A115.27 (12)O1B—S1B—O2B115.51 (12)
O1A—S1A—N1A111.17 (13)O1B—S1B—N1B110.67 (11)
O2A—S1A—N1A110.10 (11)O2B—S1B—N1B110.22 (11)
O1A—S1A—N2A107.33 (10)O1B—S1B—N2B107.50 (10)
O2A—S1A—N2A107.39 (11)O2B—S1B—N2B106.78 (9)
N1A—S1A—N2A104.94 (10)N1B—S1B—N2B105.57 (10)
C13A—O4A—C14A116.69 (19)C13B—O4B—C14B116.48 (18)
C2A—N1A—S1A123.12 (16)C2B—N1B—S1B123.38 (17)
C4A—N2A—C6A122.55 (19)C4B—N2B—C6B122.43 (19)
C4A—N2A—S1A121.25 (15)C4B—N2B—S1B122.41 (15)
C6A—N2A—S1A115.74 (15)C6B—N2B—S1B114.83 (16)
C2A—C1A—H1A1109.5C2B—C1B—H1B1109.5
C2A—C1A—H1A2109.5C2B—C1B—H1B2109.5
H1A1—C1A—H1A2109.5H1B1—C1B—H1B2109.5
C2A—C1A—H1A3109.5C2B—C1B—H1B3109.5
H1A1—C1A—H1A3109.5H1B1—C1B—H1B3109.5
H1A2—C1A—H1A3109.5H1B2—C1B—H1B3109.5
N1A—C2A—C3A124.2 (2)N1B—C2B—C3B125.0 (2)
N1A—C2A—C1A114.9 (2)N1B—C2B—C1B114.1 (2)
C3A—C2A—C1A120.9 (2)C3B—C2B—C1B120.9 (2)
C4A—C3A—C2A120.5 (2)C4B—C3B—C2B120.5 (2)
C4A—C3A—C7A120.01 (19)C4B—C3B—C7B120.79 (19)
C2A—C3A—C7A119.01 (19)C2B—C3B—C7B118.7 (2)
N2A—C4A—C3A121.93 (19)N2B—C4B—C3B121.77 (19)
N2A—C4A—C5A114.97 (19)N2B—C4B—C5B115.88 (19)
C3A—C4A—C5A123.1 (2)C3B—C4B—C5B122.3 (2)
C4A—C5A—H5A1109.5C4B—C5B—H5B1109.5
C4A—C5A—H5A2109.5C4B—C5B—H5B2109.5
H5A1—C5A—H5A2109.5H5B1—C5B—H5B2109.5
C4A—C5A—H5A3109.5C4B—C5B—H5B3109.5
H5A1—C5A—H5A3109.5H5B1—C5B—H5B3109.5
H5A2—C5A—H5A3109.5H5B2—C5B—H5B3109.5
N2A—C6A—H6A1109.5N2B—C6B—H6B1109.5
N2A—C6A—H6A2109.5N2B—C6B—H6B2109.5
H6A1—C6A—H6A2109.5H6B1—C6B—H6B2109.5
N2A—C6A—H6A3109.5N2B—C6B—H6B3109.5
H6A1—C6A—H6A3109.5H6B1—C6B—H6B3109.5
H6A2—C6A—H6A3109.5H6B2—C6B—H6B3109.5
C12A—C7A—C8A118.0 (2)C12B—C7B—C8B117.9 (2)
C12A—C7A—C3A118.0 (2)C12B—C7B—C3B118.2 (2)
C8A—C7A—C3A123.9 (2)C8B—C7B—C3B123.80 (19)
C9A—C8A—C7A119.2 (2)C9B—C8B—C7B119.3 (2)
C9A—C8A—C13A118.4 (2)C9B—C8B—C13B119.0 (2)
C7A—C8A—C13A122.4 (2)C7B—C8B—C13B121.7 (2)
C10A—C9A—C8A121.1 (2)C10B—C9B—C8B121.4 (2)
C10A—C9A—H9A119.4C10B—C9B—H9B119.3
C8A—C9A—H9A119.4C8B—C9B—H9B119.3
C11A—C10A—C9A119.6 (2)C9B—C10B—C11B119.9 (2)
C11A—C10A—H10A120.2C9B—C10B—H10B120.0
C9A—C10A—H10A120.2C11B—C10B—H10B120.0
C10A—C11A—C12A119.9 (2)C10B—C11B—C12B119.7 (2)
C10A—C11A—H11A120.0C10B—C11B—H11B120.2
C12A—C11A—H11A120.0C12B—C11B—H11B120.2
C11A—C12A—C7A122.1 (2)C7B—C12B—C11B121.7 (2)
C11A—C12A—H12A118.9C7B—C12B—H12B119.1
C7A—C12A—H12A118.9C11B—C12B—H12B119.1
O3A—C13A—O4A122.1 (2)O3B—C13B—O4B122.7 (2)
O3A—C13A—C8A126.2 (2)O3B—C13B—C8B125.6 (2)
O4A—C13A—C8A111.7 (2)O4B—C13B—C8B111.7 (2)
O4A—C14A—H14A109.5O4B—C14B—H14D109.5
O4A—C14A—H14B109.5O4B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
O4A—C14A—H14C109.5O4B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
O1A—S1A—N1A—C2A95.6 (2)O1B—S1B—N1B—C2B103.6 (2)
O2A—S1A—N1A—C2A135.4 (2)O2B—S1B—N1B—C2B127.4 (2)
N2A—S1A—N1A—C2A20.1 (3)N2B—S1B—N1B—C2B12.5 (2)
O1A—S1A—N2A—C4A96.67 (19)O1B—S1B—N2B—C4B106.12 (19)
O2A—S1A—N2A—C4A138.84 (18)O2B—S1B—N2B—C4B129.36 (19)
N1A—S1A—N2A—C4A21.7 (2)N1B—S1B—N2B—C4B12.1 (2)
O1A—S1A—N2A—C6A75.8 (2)O1B—S1B—N2B—C6B67.42 (19)
O2A—S1A—N2A—C6A48.72 (19)O2B—S1B—N2B—C6B57.1 (2)
N1A—S1A—N2A—C6A165.88 (19)N1B—S1B—N2B—C6B174.41 (18)
S1A—N1A—C2A—C3A8.8 (4)S1B—N1B—C2B—C3B7.2 (4)
S1A—N1A—C2A—C1A172.1 (2)S1B—N1B—C2B—C1B174.6 (2)
N1A—C2A—C3A—C4A5.5 (4)N1B—C2B—C3B—C4B1.3 (4)
C1A—C2A—C3A—C4A173.6 (2)C1B—C2B—C3B—C4B176.7 (2)
N1A—C2A—C3A—C7A177.7 (2)N1B—C2B—C3B—C7B178.7 (2)
C1A—C2A—C3A—C7A1.3 (3)C1B—C2B—C3B—C7B3.2 (3)
C6A—N2A—C4A—C3A176.2 (2)C6B—N2B—C4B—C3B179.1 (2)
S1A—N2A—C4A—C3A11.9 (3)S1B—N2B—C4B—C3B6.1 (3)
C6A—N2A—C4A—C5A2.4 (3)C6B—N2B—C4B—C5B3.4 (3)
S1A—N2A—C4A—C5A169.47 (16)S1B—N2B—C4B—C5B176.44 (17)
C2A—C3A—C4A—N2A3.3 (3)C2B—C3B—C4B—N2B1.6 (3)
C7A—C3A—C4A—N2A175.4 (2)C7B—C3B—C4B—N2B178.5 (2)
C2A—C3A—C4A—C5A175.3 (2)C2B—C3B—C4B—C5B175.7 (2)
C7A—C3A—C4A—C5A3.1 (3)C7B—C3B—C4B—C5B4.2 (3)
C4A—C3A—C7A—C12A96.2 (3)C4B—C3B—C7B—C12B97.4 (3)
C2A—C3A—C7A—C12A76.1 (3)C2B—C3B—C7B—C12B82.7 (3)
C4A—C3A—C7A—C8A86.8 (3)C4B—C3B—C7B—C8B86.7 (3)
C2A—C3A—C7A—C8A100.9 (3)C2B—C3B—C7B—C8B93.2 (3)
C12A—C7A—C8A—C9A0.1 (3)C12B—C7B—C8B—C9B0.1 (3)
C3A—C7A—C8A—C9A177.0 (2)C3B—C7B—C8B—C9B175.9 (2)
C12A—C7A—C8A—C13A178.2 (2)C12B—C7B—C8B—C13B179.3 (2)
C3A—C7A—C8A—C13A4.7 (3)C3B—C7B—C8B—C13B4.7 (3)
C7A—C8A—C9A—C10A0.7 (3)C7B—C8B—C9B—C10B0.2 (3)
C13A—C8A—C9A—C10A179.1 (2)C13B—C8B—C9B—C10B179.2 (2)
C8A—C9A—C10A—C11A0.9 (4)C8B—C9B—C10B—C11B0.1 (4)
C9A—C10A—C11A—C12A0.3 (3)C9B—C10B—C11B—C12B0.1 (4)
C10A—C11A—C12A—C7A0.5 (3)C8B—C7B—C12B—C11B0.1 (3)
C8A—C7A—C12A—C11A0.7 (3)C3B—C7B—C12B—C11B176.3 (2)
C3A—C7A—C12A—C11A176.6 (2)C10B—C11B—C12B—C7B0.2 (4)
C14A—O4A—C13A—O3A2.0 (3)C14B—O4B—C13B—O3B1.7 (3)
C14A—O4A—C13A—C8A179.1 (2)C14B—O4B—C13B—C8B178.6 (2)
C9A—C8A—C13A—O3A161.3 (2)C9B—C8B—C13B—O3B163.0 (2)
C7A—C8A—C13A—O3A16.9 (4)C7B—C8B—C13B—O3B16.5 (4)
C9A—C8A—C13A—O4A17.5 (3)C9B—C8B—C13B—O4B16.7 (3)
C7A—C8A—C13A—O4A164.2 (2)C7B—C8B—C13B—O4B163.9 (2)

Experimental details

Crystal data
Chemical formulaC14H16N2O4S
Mr308.35
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)173
a, b, c (Å)13.5954 (3), 8.0683 (2), 25.9554 (7)
V3)2847.09 (12)
Z8
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.28 × 0.22 × 0.21
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.935, 0.950
No. of measured, independent and
observed [I > 2σ(I)] reflections
33574, 6094, 4522
Rint0.057
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.083, 0.99
No. of reflections6094
No. of parameters388
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.25
Absolute structureFlack (1983), 2751 Friedel pairs
Absolute structure parameter0.06 (5)

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

 

Acknowledgements

The authors wish to thank Dr Hong Su from the University of Cape Town for assistance with the data collection and refinement.

References

First citationBhatt, N., Bhatt, P., Vyas, K. B., Nimavat, K., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2012). Acta Cryst. E68, o2160.  CSD CrossRef IUCr Journals
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationNonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
First citationOtwinowski, 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.
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWright, J. B. (1964). J. Org. Chem. 29, 1905–1909.  CrossRef CAS Web of Science

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