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In the title benzo­thia­zine compound, the di­hydro­thia­zine ring adopts a sofa-like conformation with the S atom displaced from the mean plane through the N and C ring atoms by 0.767 (1) Å. In the crystal, mol­ecules are linked by C—H...π inter­actions, forming chains propagating along the a-axis direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016015978/su5329sup1.cif
Contains datablocks I, Global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989016015978/su5329Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989016015978/su5329Isup3.cml
Supplementary material

CCDC reference: 1508990

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.044
  • wR factor = 0.120
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00692 Ang. PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density 0 Note
Alert level G PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C11 Check PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still 67 % PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 3 Note PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Agilent, 2012); cell refinement: CrysAlis CCD (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Methyl 1-allyl-4-methyl-1H-benzo[c][1,2]thiazine-3-carboxylate 2,2-dioxide top
Crystal data top
C14H15NO4SDx = 1.366 Mg m3
Mr = 293.33Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 2163 reflections
a = 10.1970 (7) Åθ = 3.8–25.1°
b = 18.6174 (12) ŵ = 0.24 mm1
c = 7.5136 (5) ÅT = 293 K
V = 1426.39 (16) Å3Plate, colourless
Z = 40.20 × 0.10 × 0.02 mm
F(000) = 616
Data collection top
Agilent Xcalibur Sapphire3
diffractometer
2425 independent reflections
Radiation source: Enhance (Mo) X-ray Source2111 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm-1Rint = 0.056
ω–scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan
(CrysAlis RED; Agilent, 2012)
h = 1210
Tmin = 0.706, Tmax = 1.000k = 2222
9346 measured reflectionsl = 78
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0618P)2 + 0.1291P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2425 reflectionsΔρmax = 0.19 e Å3
181 parametersΔρmin = 0.20 e Å3
1 restraintAbsolute structure: Flack x determined using 785 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.09 (8)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.88243 (9)0.65549 (5)0.26457 (17)0.0457 (3)
O10.6502 (4)0.5240 (2)0.4865 (7)0.0975 (14)
O20.7649 (4)0.51032 (18)0.2347 (6)0.0801 (11)
O30.7789 (3)0.66144 (16)0.1376 (5)0.0645 (9)
O41.0109 (3)0.63899 (17)0.2033 (4)0.0590 (9)
N10.8881 (3)0.73110 (17)0.3775 (5)0.0457 (8)
C10.9692 (4)0.7307 (2)0.5295 (6)0.0443 (9)
C21.0333 (4)0.7933 (3)0.5818 (7)0.0559 (11)
H21.02050.83550.51800.067*
C31.1146 (4)0.7932 (3)0.7260 (7)0.0652 (14)
H31.15570.83550.76110.078*
C41.1362 (5)0.7308 (3)0.8195 (7)0.0722 (15)
H41.19560.73050.91350.087*
C51.0705 (5)0.6690 (3)0.7747 (8)0.0605 (11)
H51.08370.62770.84190.073*
C60.9842 (4)0.6670 (2)0.6302 (6)0.0461 (10)
C70.9017 (4)0.6034 (2)0.5943 (6)0.0490 (10)
C80.8424 (4)0.5951 (2)0.4353 (6)0.0497 (11)
C90.7425 (5)0.5388 (2)0.3921 (8)0.0623 (13)
C100.6651 (7)0.4617 (4)0.1624 (12)0.110 (3)
H10A0.69270.44460.04780.165*
H10B0.65370.42170.24150.165*
H10C0.58350.48700.15060.165*
C110.8826 (5)0.5494 (3)0.7415 (9)0.0715 (15)
H11A0.93190.56400.84420.107*
H11B0.79130.54670.77170.107*
H11C0.91260.50310.70250.107*
C120.7970 (4)0.7897 (2)0.3411 (7)0.0547 (11)
H12A0.77530.81270.45300.066*
H12B0.71680.76930.29360.066*
C130.8440 (5)0.8458 (2)0.2154 (8)0.0661 (15)
H130.78880.88480.19610.079*
C140.9528 (6)0.8455 (3)0.1316 (9)0.0829 (18)
H14A1.01120.80760.14660.099*
H14B0.97370.88320.05550.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0486 (5)0.0440 (5)0.0446 (5)0.0024 (4)0.0040 (5)0.0029 (5)
O10.087 (3)0.089 (3)0.116 (4)0.038 (2)0.020 (3)0.007 (3)
O20.084 (2)0.063 (2)0.094 (3)0.0162 (18)0.005 (2)0.028 (2)
O30.070 (2)0.062 (2)0.062 (2)0.0037 (16)0.0255 (17)0.0033 (16)
O40.0587 (18)0.0636 (19)0.0546 (19)0.0032 (15)0.0108 (14)0.0081 (14)
N10.0528 (19)0.0364 (17)0.048 (2)0.0005 (14)0.0052 (15)0.0030 (17)
C10.044 (2)0.046 (2)0.043 (2)0.0011 (18)0.0033 (18)0.0031 (18)
C20.061 (3)0.053 (3)0.053 (3)0.008 (2)0.004 (2)0.005 (2)
C30.070 (3)0.075 (3)0.051 (3)0.020 (3)0.005 (2)0.015 (2)
C40.075 (3)0.096 (4)0.046 (3)0.009 (3)0.013 (2)0.008 (3)
C50.070 (3)0.067 (3)0.045 (2)0.005 (2)0.009 (3)0.001 (3)
C60.049 (2)0.047 (2)0.042 (2)0.0024 (18)0.0034 (18)0.0002 (18)
C70.055 (2)0.042 (2)0.050 (3)0.0070 (18)0.003 (2)0.0025 (19)
C80.051 (2)0.038 (2)0.060 (3)0.0031 (18)0.003 (2)0.0031 (19)
C90.062 (3)0.046 (2)0.079 (4)0.009 (2)0.000 (3)0.000 (2)
C100.112 (5)0.070 (4)0.149 (7)0.028 (4)0.040 (5)0.028 (4)
C110.093 (4)0.053 (3)0.068 (4)0.001 (2)0.002 (3)0.014 (3)
C120.054 (2)0.046 (2)0.064 (3)0.0025 (19)0.001 (2)0.001 (2)
C130.067 (3)0.051 (3)0.081 (4)0.003 (2)0.000 (3)0.011 (2)
C140.076 (4)0.090 (4)0.082 (4)0.001 (3)0.001 (3)0.026 (3)
Geometric parameters (Å, º) top
S1—O41.422 (3)C5—H50.9300
S1—O31.427 (3)C6—C71.477 (6)
S1—N11.645 (3)C7—C81.348 (6)
S1—C81.754 (4)C7—C111.508 (7)
O1—C91.210 (6)C8—C91.497 (6)
O2—C91.316 (6)C10—H10A0.9600
O2—C101.466 (6)C10—H10B0.9600
N1—C11.411 (5)C10—H10C0.9600
N1—C121.458 (5)C11—H11A0.9600
C1—C21.392 (6)C11—H11B0.9600
C1—C61.415 (6)C11—H11C0.9600
C2—C31.364 (7)C12—C131.487 (7)
C2—H20.9300C12—H12A0.9700
C3—C41.376 (8)C12—H12B0.9700
C3—H30.9300C13—C141.276 (8)
C4—C51.373 (7)C13—H130.9300
C4—H40.9300C14—H14A0.9300
C5—C61.398 (6)C14—H14B0.9300
O4—S1—O3118.8 (2)C7—C8—C9125.3 (4)
O4—S1—N1108.66 (18)C7—C8—S1118.0 (3)
O3—S1—N1107.72 (19)C9—C8—S1116.6 (4)
O4—S1—C8108.2 (2)O1—C9—O2124.8 (5)
O3—S1—C8111.5 (2)O1—C9—C8124.1 (5)
N1—S1—C8100.3 (2)O2—C9—C8111.0 (4)
C9—O2—C10117.4 (5)O2—C10—H10A109.5
C1—N1—C12122.0 (3)O2—C10—H10B109.5
C1—N1—S1115.7 (3)H10A—C10—H10B109.5
C12—N1—S1121.4 (3)O2—C10—H10C109.5
C2—C1—N1120.0 (4)H10A—C10—H10C109.5
C2—C1—C6120.0 (4)H10B—C10—H10C109.5
N1—C1—C6120.0 (3)C7—C11—H11A109.5
C3—C2—C1120.5 (5)C7—C11—H11B109.5
C3—C2—H2119.7H11A—C11—H11B109.5
C1—C2—H2119.7C7—C11—H11C109.5
C2—C3—C4120.3 (5)H11A—C11—H11C109.5
C2—C3—H3119.9H11B—C11—H11C109.5
C4—C3—H3119.9N1—C12—C13116.1 (4)
C5—C4—C3120.3 (5)N1—C12—H12A108.3
C5—C4—H4119.9C13—C12—H12A108.3
C3—C4—H4119.9N1—C12—H12B108.3
C4—C5—C6121.4 (5)C13—C12—H12B108.3
C4—C5—H5119.3H12A—C12—H12B107.4
C6—C5—H5119.3C14—C13—C12126.2 (5)
C5—C6—C1117.4 (4)C14—C13—H13116.9
C5—C6—C7121.5 (4)C12—C13—H13116.9
C1—C6—C7120.8 (4)C13—C14—H14A120.0
C8—C7—C6120.7 (4)C13—C14—H14B120.0
C8—C7—C11121.0 (4)H14A—C14—H14B120.0
C6—C7—C11118.3 (4)
O4—S1—N1—C160.7 (3)C1—C6—C7—C821.7 (6)
O3—S1—N1—C1169.5 (3)C5—C6—C7—C1117.0 (6)
C8—S1—N1—C152.7 (3)C1—C6—C7—C11156.7 (4)
O4—S1—N1—C12130.1 (3)C6—C7—C8—C9171.1 (4)
O3—S1—N1—C120.2 (4)C11—C7—C8—C97.3 (7)
C8—S1—N1—C12116.5 (3)C6—C7—C8—S17.8 (6)
C12—N1—C1—C242.8 (5)C11—C7—C8—S1173.9 (4)
S1—N1—C1—C2147.9 (3)O4—S1—C8—C772.8 (4)
C12—N1—C1—C6136.3 (4)O3—S1—C8—C7154.8 (3)
S1—N1—C1—C632.9 (5)N1—S1—C8—C740.9 (4)
N1—C1—C2—C3178.4 (4)O4—S1—C8—C9108.2 (4)
C6—C1—C2—C32.5 (6)O3—S1—C8—C924.2 (4)
C1—C2—C3—C41.2 (7)N1—S1—C8—C9138.1 (3)
C2—C3—C4—C53.6 (8)C10—O2—C9—O15.4 (8)
C3—C4—C5—C62.4 (8)C10—O2—C9—C8171.5 (5)
C4—C5—C6—C11.2 (7)C7—C8—C9—O146.0 (7)
C4—C5—C6—C7172.6 (5)S1—C8—C9—O1132.9 (5)
C2—C1—C6—C53.6 (6)C7—C8—C9—O2137.1 (5)
N1—C1—C6—C5177.2 (4)S1—C8—C9—O244.0 (5)
C2—C1—C6—C7170.3 (4)C1—N1—C12—C1397.2 (5)
N1—C1—C6—C78.9 (6)S1—N1—C12—C1394.2 (4)
C5—C6—C7—C8164.7 (4)N1—C12—C13—C143.5 (8)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C12—H12A···Cgi0.972.953.576 (5)123
Symmetry code: (i) x1/2, y+3/2, z+1/2.
 

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