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The title compound, C13H17NO3S2, is shown to have a trans arrangement of the S=O group and the methyl groups in the thia­zine ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001320/cf6141sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001320/cf6141Isup2.hkl
Contains datablock I

CCDC reference: 180808

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.117
  • Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2275 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2503 Completeness (_total/calc) 90.89% Alert C: < 95% complete General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2275 From the CIF: _diffrn_reflns_limit_ max hkl 9. 14. 13. From the CIF: _diffrn_reflns_limit_ min hkl 0. 0. -14. TEST1: Expected hkl limits for theta max Calculated maximum hkl 11. 14. 14. Calculated minimum hkl -11. -14. -14. ALERT: Expected hkl max differ from CIF values
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: CAD-4-PC Software (Enraf-Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1993).

(I) top
Crystal data top
C13H17NO3S2F(000) = 632
Mr = 299.40Dx = 1.399 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
a = 9.8136 (16) ÅCell parameters from 25 reflections
b = 12.485 (2) Åθ = 12–18°
c = 11.9359 (19) ŵ = 0.38 mm1
β = 103.610 (14)°T = 298 K
V = 1421.3 (4) Å3Block, colourless
Z = 40.5 × 0.4 × 0.3 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
1998 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.011
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
ω–2θ scansh = 09
Absorption correction: ψ scan
[McArdle & Daly (1999) (ABSCALC in OSCAIL) and North et al. (1986)]
k = 014
Tmin = 0.828, Tmax = 0.893l = 1413
2478 measured reflections3 standard reflections every 120 min
2275 independent reflections intensity decay: 2%
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0842P)2 + 0.3859P]
where P = (Fo2 + 2Fc2)/3
2275 reflections(Δ/σ)max = 0.018
175 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.39 e Å3
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.0335 (0.0079) x + 8.7543 (0.0089) y + 2.4610 (0.0108) z = 4.0109 (0.0041)

* -0.0164 (0.0015) C6 * 0.0057 (0.0016) C7 * 0.0110 (0.0016) C8 * -0.0170 (0.0016) C9 * 0.0065 (0.0017) C10 * 0.0101 (0.0016) C11 - 0.0936 (0.0042) C12 - 0.2290 (0.0030) S2

Rms deviation of fitted atoms = 0.0119

6.4395 (0.0106) x + 7.1688 (0.0114) y - 7.5227 (0.0176) z = 3.8344 (0.0106)

Angle to previous plane (with approximate e.s.d.) = 51.00 (0.09)

* -0.0066 (0.0006) C1 * 0.0154 (0.0015) C2 * -0.0157 (0.0016) C3 * 0.0068 (0.0007) C4 - 1.0746 (0.0040) S1 - 0.3030 (0.0042) N1 - 2.4111 (0.0033) O1 1.3667 (0.0038) C5 - 0.5879 (0.0065) S2 1.3564 (0.0042) C13

Rms deviation of fitted atoms = 0.0120

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
S10.14314 (6)0.42195 (4)0.15777 (4)0.0482 (2)
S20.23368 (6)0.26504 (4)0.02104 (4)0.0486 (2)
O20.3303 (2)0.17909 (12)0.05321 (14)0.0654 (5)
O30.08842 (19)0.24716 (14)0.01194 (15)0.0655 (5)
N10.28094 (18)0.36306 (13)0.11703 (13)0.0425 (4)
O10.1136 (2)0.36751 (15)0.25826 (15)0.0690 (5)
C10.2354 (3)0.54430 (18)0.2114 (2)0.0534 (6)
H10.17570.58370.25240.069*
C20.3679 (3)0.51861 (19)0.29735 (18)0.0561 (6)
H20.39630.56420.36010.073*
C30.4463 (3)0.43584 (19)0.28974 (19)0.0560 (6)
H30.52350.42500.35090.073*
C40.4258 (2)0.35676 (17)0.19383 (18)0.0489 (5)
H40.43970.28470.22710.064*
C50.5347 (3)0.3759 (2)0.1246 (2)0.0675 (7)
H5A0.51930.44470.08790.095*
H5B0.52720.32120.06690.095*
H5C0.62670.37390.17500.095*
C60.2498 (2)0.31580 (15)0.11257 (16)0.0432 (5)
C70.3428 (2)0.27011 (17)0.16917 (18)0.0502 (5)
H70.40570.21790.13320.065*
C80.3410 (3)0.30314 (19)0.28020 (18)0.0541 (6)
H80.40400.27310.31850.070*
C90.2478 (3)0.37961 (18)0.33502 (17)0.0523 (6)
C100.1591 (3)0.42668 (19)0.2754 (2)0.0584 (6)
H100.09800.48030.31060.076*
C110.1595 (3)0.39564 (18)0.16447 (19)0.0534 (6)
H110.09950.42820.12500.069*
C120.2417 (4)0.4098 (2)0.4587 (2)0.0771 (8)
H12A0.32080.37940.48180.108*
H12B0.24400.48640.46540.108*
H12C0.15660.38280.50750.108*
C130.2526 (3)0.6146 (2)0.1119 (3)0.0724 (8)
H13A0.29370.68170.14130.101*
H13B0.16260.62720.06110.101*
H13C0.31250.57940.07040.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0510 (4)0.0497 (3)0.0443 (3)0.0041 (2)0.0118 (2)0.0042 (2)
S20.0693 (5)0.0376 (3)0.0385 (3)0.0082 (2)0.0119 (3)0.00235 (19)
O20.1072 (15)0.0376 (8)0.0503 (9)0.0070 (8)0.0160 (9)0.0036 (6)
O30.0748 (13)0.0687 (11)0.0547 (10)0.0310 (9)0.0188 (8)0.0120 (8)
N10.0504 (11)0.0407 (9)0.0349 (8)0.0016 (7)0.0071 (7)0.0037 (6)
O10.0841 (13)0.0745 (11)0.0575 (10)0.0212 (10)0.0350 (9)0.0053 (8)
C10.0637 (15)0.0438 (11)0.0543 (12)0.0003 (10)0.0171 (11)0.0085 (9)
C20.0658 (16)0.0582 (14)0.0427 (11)0.0110 (12)0.0095 (10)0.0120 (10)
C30.0617 (16)0.0600 (14)0.0394 (11)0.0060 (11)0.0020 (10)0.0014 (9)
C40.0558 (14)0.0441 (11)0.0420 (11)0.0048 (9)0.0019 (9)0.0056 (9)
C50.0563 (16)0.0795 (17)0.0650 (15)0.0069 (13)0.0108 (12)0.0042 (13)
C60.0532 (14)0.0389 (10)0.0355 (10)0.0031 (9)0.0064 (9)0.0035 (8)
C70.0596 (15)0.0458 (11)0.0431 (11)0.0055 (10)0.0082 (10)0.0030 (9)
C80.0654 (16)0.0560 (13)0.0436 (11)0.0020 (11)0.0179 (10)0.0082 (10)
C90.0671 (15)0.0499 (12)0.0368 (10)0.0128 (11)0.0062 (10)0.0032 (9)
C100.0647 (17)0.0548 (13)0.0499 (13)0.0065 (11)0.0023 (11)0.0064 (10)
C110.0588 (15)0.0545 (12)0.0462 (12)0.0100 (11)0.0111 (10)0.0009 (9)
C120.115 (2)0.0752 (17)0.0377 (12)0.0114 (16)0.0119 (13)0.0050 (12)
C130.083 (2)0.0478 (13)0.0824 (18)0.0017 (12)0.0122 (15)0.0132 (12)
Geometric parameters (Å, º) top
S1—O11.4658 (17)C5—H5C0.960
S1—N11.7075 (18)C6—C111.380 (3)
S1—C11.814 (2)C6—C71.381 (3)
S2—O31.4216 (19)C7—C81.384 (3)
S2—O21.4233 (17)C7—H70.930
S2—N11.6659 (16)C8—C91.376 (3)
S2—C61.757 (2)C8—H80.930
N1—C41.501 (3)C9—C101.379 (3)
C1—C21.489 (3)C9—C121.511 (3)
C1—C131.517 (3)C10—C111.379 (3)
C1—H10.980C10—H100.930
C2—C31.304 (3)C11—H110.930
C2—H20.930C12—H12A0.960
C3—C41.489 (3)C12—H12B0.960
C3—H30.930C12—H12C0.960
C4—C51.517 (3)C13—H13A0.960
C4—H40.980C13—H13B0.960
C5—H5A0.960C13—H13C0.960
C5—H5B0.960
O1—S1—N1110.84 (10)C4—C5—H5C109.5
O1—S1—C1106.28 (10)H5A—C5—H5C109.5
N1—S1—C195.74 (10)H5B—C5—H5C109.5
O3—S2—O2119.63 (11)C11—C6—C7120.50 (19)
O3—S2—N1106.25 (10)C11—C6—S2118.86 (17)
O2—S2—N1107.96 (9)C7—C6—S2120.40 (16)
O3—S2—C6106.85 (10)C6—C7—C8119.0 (2)
O2—S2—C6108.68 (10)C6—C7—H7120.5
N1—S2—C6106.81 (9)C8—C7—H7120.5
C4—N1—S2116.87 (13)C9—C8—C7121.3 (2)
C4—N1—S1123.24 (13)C9—C8—H8119.4
S2—N1—S1113.65 (10)C7—C8—H8119.4
C2—C1—C13115.1 (2)C8—C9—C10118.7 (2)
C2—C1—S1110.13 (16)C8—C9—C12120.4 (2)
C13—C1—S1110.45 (17)C10—C9—C12120.9 (2)
C2—C1—H1106.9C11—C10—C9121.1 (2)
C13—C1—H1106.9C11—C10—H10119.5
S1—C1—H1106.9C9—C10—H10119.5
C3—C2—C1123.8 (2)C10—C11—C6119.4 (2)
C3—C2—H2118.1C10—C11—H11120.3
C1—C2—H2118.1C6—C11—H11120.3
C2—C3—C4127.1 (2)C9—C12—H12A109.5
C2—C3—H3116.4C9—C12—H12B109.5
C4—C3—H3116.4H12A—C12—H12B109.5
C3—C4—N1111.84 (18)C9—C12—H12C109.5
C3—C4—C5109.2 (2)H12A—C12—H12C109.5
N1—C4—C5110.28 (18)H12B—C12—H12C109.5
C3—C4—H4108.5C1—C13—H13A109.5
N1—C4—H4108.5C1—C13—H13B109.5
C5—C4—H4108.5H13A—C13—H13B109.5
C4—C5—H5A109.5C1—C13—H13C109.5
C4—C5—H5B109.5H13A—C13—H13C109.5
H5A—C5—H5B109.5H13B—C13—H13C109.5
O3—S2—N1—C4144.86 (16)S1—N1—C4—C318.6 (2)
O2—S2—N1—C415.38 (18)S2—N1—C4—C569.1 (2)
C6—S2—N1—C4101.34 (16)S1—N1—C4—C5140.43 (17)
O3—S2—N1—S18.36 (13)O3—S2—C6—C1145.53 (19)
O2—S2—N1—S1137.84 (11)O2—S2—C6—C11175.90 (17)
C6—S2—N1—S1105.43 (12)N1—S2—C6—C1167.85 (19)
O1—S1—N1—C461.10 (18)O3—S2—C6—C7128.86 (18)
C1—S1—N1—C448.76 (17)O2—S2—C6—C71.5 (2)
O1—S1—N1—S290.18 (12)N1—S2—C6—C7117.76 (18)
C1—S1—N1—S2159.96 (11)C11—C6—C7—C82.1 (3)
O1—S1—C1—C259.93 (19)S2—C6—C7—C8172.22 (17)
N1—S1—C1—C253.76 (17)C6—C7—C8—C90.6 (3)
O1—S1—C1—C13171.87 (19)C7—C8—C9—C102.7 (3)
N1—S1—C1—C1374.44 (19)C7—C8—C9—C12176.4 (2)
C13—C1—C2—C389.4 (3)C8—C9—C10—C112.3 (4)
S1—C1—C2—C336.2 (3)C12—C9—C10—C11176.8 (2)
C1—C2—C3—C44.1 (4)C9—C10—C11—C60.3 (4)
C2—C3—C4—N115.6 (3)C7—C6—C11—C102.5 (3)
C2—C3—C4—C5106.8 (3)S2—C6—C11—C10171.88 (18)
S2—N1—C4—C3169.08 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O2i0.982.623.463 (6)144
C12—H12B···O2ii0.962.663.564 (6)158
C2—H2···O3i0.932.733.612 (6)158
C13—H13A···O1i0.962.673.625 (3)173
C8—H8···O1iii0.932.703.365 (6)130
C12—H12C···O1iv0.962.743.358 (6)123
C7—H7···O20.932.552.916 (6)104
C5—H5B···O20.962.603.160 (6)117
C4—H4···O20.982.482.806 (6)99
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z1/2; (iii) x+1/2, y+1/2, z1/2; (iv) x, y, z1.
 

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