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
CCDC reference: 1508990
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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-1
H-benzo[
c][1,2]thiazine-3-carboxylate
2,2-dioxide
top
Crystal data top
C14H15NO4S | Dx = 1.366 Mg m−3 |
Mr = 293.33 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 2163 reflections |
a = 10.1970 (7) Å | θ = 3.8–25.1° |
b = 18.6174 (12) Å | µ = 0.24 mm−1 |
c = 7.5136 (5) Å | T = 293 K |
V = 1426.39 (16) Å3 | Plate, colourless |
Z = 4 | 0.20 × 0.10 × 0.02 mm |
F(000) = 616 | |
Data collection top
Agilent Xcalibur Sapphire3 diffractometer | 2425 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2111 reflections with I > 2σ(I) |
Detector resolution: 16.1827 pixels mm-1 | Rint = 0.056 |
ω–scans | θmax = 25.0°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | h = −12→10 |
Tmin = 0.706, Tmax = 1.000 | k = −22→22 |
9346 measured reflections | l = −7→8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-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 reflections | Δρmax = 0.19 e Å−3 |
181 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Absolute structure: Flack x determined using 785 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
S1 | 0.88243 (9) | 0.65549 (5) | 0.26457 (17) | 0.0457 (3) | |
O1 | 0.6502 (4) | 0.5240 (2) | 0.4865 (7) | 0.0975 (14) | |
O2 | 0.7649 (4) | 0.51032 (18) | 0.2347 (6) | 0.0801 (11) | |
O3 | 0.7789 (3) | 0.66144 (16) | 0.1376 (5) | 0.0645 (9) | |
O4 | 1.0109 (3) | 0.63899 (17) | 0.2033 (4) | 0.0590 (9) | |
N1 | 0.8881 (3) | 0.73110 (17) | 0.3775 (5) | 0.0457 (8) | |
C1 | 0.9692 (4) | 0.7307 (2) | 0.5295 (6) | 0.0443 (9) | |
C2 | 1.0333 (4) | 0.7933 (3) | 0.5818 (7) | 0.0559 (11) | |
H2 | 1.0205 | 0.8355 | 0.5180 | 0.067* | |
C3 | 1.1146 (4) | 0.7932 (3) | 0.7260 (7) | 0.0652 (14) | |
H3 | 1.1557 | 0.8355 | 0.7611 | 0.078* | |
C4 | 1.1362 (5) | 0.7308 (3) | 0.8195 (7) | 0.0722 (15) | |
H4 | 1.1956 | 0.7305 | 0.9135 | 0.087* | |
C5 | 1.0705 (5) | 0.6690 (3) | 0.7747 (8) | 0.0605 (11) | |
H5 | 1.0837 | 0.6277 | 0.8419 | 0.073* | |
C6 | 0.9842 (4) | 0.6670 (2) | 0.6302 (6) | 0.0461 (10) | |
C7 | 0.9017 (4) | 0.6034 (2) | 0.5943 (6) | 0.0490 (10) | |
C8 | 0.8424 (4) | 0.5951 (2) | 0.4353 (6) | 0.0497 (11) | |
C9 | 0.7425 (5) | 0.5388 (2) | 0.3921 (8) | 0.0623 (13) | |
C10 | 0.6651 (7) | 0.4617 (4) | 0.1624 (12) | 0.110 (3) | |
H10A | 0.6927 | 0.4446 | 0.0478 | 0.165* | |
H10B | 0.6537 | 0.4217 | 0.2415 | 0.165* | |
H10C | 0.5835 | 0.4870 | 0.1506 | 0.165* | |
C11 | 0.8826 (5) | 0.5494 (3) | 0.7415 (9) | 0.0715 (15) | |
H11A | 0.9319 | 0.5640 | 0.8442 | 0.107* | |
H11B | 0.7913 | 0.5467 | 0.7717 | 0.107* | |
H11C | 0.9126 | 0.5031 | 0.7025 | 0.107* | |
C12 | 0.7970 (4) | 0.7897 (2) | 0.3411 (7) | 0.0547 (11) | |
H12A | 0.7753 | 0.8127 | 0.4530 | 0.066* | |
H12B | 0.7168 | 0.7693 | 0.2936 | 0.066* | |
C13 | 0.8440 (5) | 0.8458 (2) | 0.2154 (8) | 0.0661 (15) | |
H13 | 0.7888 | 0.8848 | 0.1961 | 0.079* | |
C14 | 0.9528 (6) | 0.8455 (3) | 0.1316 (9) | 0.0829 (18) | |
H14A | 1.0112 | 0.8076 | 0.1466 | 0.099* | |
H14B | 0.9737 | 0.8832 | 0.0555 | 0.099* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0486 (5) | 0.0440 (5) | 0.0446 (5) | −0.0024 (4) | −0.0040 (5) | −0.0029 (5) |
O1 | 0.087 (3) | 0.089 (3) | 0.116 (4) | −0.038 (2) | 0.020 (3) | −0.007 (3) |
O2 | 0.084 (2) | 0.063 (2) | 0.094 (3) | −0.0162 (18) | −0.005 (2) | −0.028 (2) |
O3 | 0.070 (2) | 0.062 (2) | 0.062 (2) | −0.0037 (16) | −0.0255 (17) | −0.0033 (16) |
O4 | 0.0587 (18) | 0.0636 (19) | 0.0546 (19) | −0.0032 (15) | 0.0108 (14) | −0.0081 (14) |
N1 | 0.0528 (19) | 0.0364 (17) | 0.048 (2) | −0.0005 (14) | −0.0052 (15) | −0.0030 (17) |
C1 | 0.044 (2) | 0.046 (2) | 0.043 (2) | −0.0011 (18) | 0.0033 (18) | −0.0031 (18) |
C2 | 0.061 (3) | 0.053 (3) | 0.053 (3) | −0.008 (2) | 0.004 (2) | −0.005 (2) |
C3 | 0.070 (3) | 0.075 (3) | 0.051 (3) | −0.020 (3) | 0.005 (2) | −0.015 (2) |
C4 | 0.075 (3) | 0.096 (4) | 0.046 (3) | −0.009 (3) | −0.013 (2) | −0.008 (3) |
C5 | 0.070 (3) | 0.067 (3) | 0.045 (2) | 0.005 (2) | −0.009 (3) | 0.001 (3) |
C6 | 0.049 (2) | 0.047 (2) | 0.042 (2) | 0.0024 (18) | 0.0034 (18) | −0.0002 (18) |
C7 | 0.055 (2) | 0.042 (2) | 0.050 (3) | 0.0070 (18) | 0.003 (2) | 0.0025 (19) |
C8 | 0.051 (2) | 0.038 (2) | 0.060 (3) | −0.0031 (18) | 0.003 (2) | −0.0031 (19) |
C9 | 0.062 (3) | 0.046 (2) | 0.079 (4) | −0.009 (2) | 0.000 (3) | 0.000 (2) |
C10 | 0.112 (5) | 0.070 (4) | 0.149 (7) | −0.028 (4) | −0.040 (5) | −0.028 (4) |
C11 | 0.093 (4) | 0.053 (3) | 0.068 (4) | −0.001 (2) | −0.002 (3) | 0.014 (3) |
C12 | 0.054 (2) | 0.046 (2) | 0.064 (3) | 0.0025 (19) | −0.001 (2) | 0.001 (2) |
C13 | 0.067 (3) | 0.051 (3) | 0.081 (4) | 0.003 (2) | 0.000 (3) | 0.011 (2) |
C14 | 0.076 (4) | 0.090 (4) | 0.082 (4) | −0.001 (3) | −0.001 (3) | 0.026 (3) |
Geometric parameters (Å, º) top
S1—O4 | 1.422 (3) | C5—H5 | 0.9300 |
S1—O3 | 1.427 (3) | C6—C7 | 1.477 (6) |
S1—N1 | 1.645 (3) | C7—C8 | 1.348 (6) |
S1—C8 | 1.754 (4) | C7—C11 | 1.508 (7) |
O1—C9 | 1.210 (6) | C8—C9 | 1.497 (6) |
O2—C9 | 1.316 (6) | C10—H10A | 0.9600 |
O2—C10 | 1.466 (6) | C10—H10B | 0.9600 |
N1—C1 | 1.411 (5) | C10—H10C | 0.9600 |
N1—C12 | 1.458 (5) | C11—H11A | 0.9600 |
C1—C2 | 1.392 (6) | C11—H11B | 0.9600 |
C1—C6 | 1.415 (6) | C11—H11C | 0.9600 |
C2—C3 | 1.364 (7) | C12—C13 | 1.487 (7) |
C2—H2 | 0.9300 | C12—H12A | 0.9700 |
C3—C4 | 1.376 (8) | C12—H12B | 0.9700 |
C3—H3 | 0.9300 | C13—C14 | 1.276 (8) |
C4—C5 | 1.373 (7) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | C14—H14A | 0.9300 |
C5—C6 | 1.398 (6) | C14—H14B | 0.9300 |
| | | |
O4—S1—O3 | 118.8 (2) | C7—C8—C9 | 125.3 (4) |
O4—S1—N1 | 108.66 (18) | C7—C8—S1 | 118.0 (3) |
O3—S1—N1 | 107.72 (19) | C9—C8—S1 | 116.6 (4) |
O4—S1—C8 | 108.2 (2) | O1—C9—O2 | 124.8 (5) |
O3—S1—C8 | 111.5 (2) | O1—C9—C8 | 124.1 (5) |
N1—S1—C8 | 100.3 (2) | O2—C9—C8 | 111.0 (4) |
C9—O2—C10 | 117.4 (5) | O2—C10—H10A | 109.5 |
C1—N1—C12 | 122.0 (3) | O2—C10—H10B | 109.5 |
C1—N1—S1 | 115.7 (3) | H10A—C10—H10B | 109.5 |
C12—N1—S1 | 121.4 (3) | O2—C10—H10C | 109.5 |
C2—C1—N1 | 120.0 (4) | H10A—C10—H10C | 109.5 |
C2—C1—C6 | 120.0 (4) | H10B—C10—H10C | 109.5 |
N1—C1—C6 | 120.0 (3) | C7—C11—H11A | 109.5 |
C3—C2—C1 | 120.5 (5) | C7—C11—H11B | 109.5 |
C3—C2—H2 | 119.7 | H11A—C11—H11B | 109.5 |
C1—C2—H2 | 119.7 | C7—C11—H11C | 109.5 |
C2—C3—C4 | 120.3 (5) | H11A—C11—H11C | 109.5 |
C2—C3—H3 | 119.9 | H11B—C11—H11C | 109.5 |
C4—C3—H3 | 119.9 | N1—C12—C13 | 116.1 (4) |
C5—C4—C3 | 120.3 (5) | N1—C12—H12A | 108.3 |
C5—C4—H4 | 119.9 | C13—C12—H12A | 108.3 |
C3—C4—H4 | 119.9 | N1—C12—H12B | 108.3 |
C4—C5—C6 | 121.4 (5) | C13—C12—H12B | 108.3 |
C4—C5—H5 | 119.3 | H12A—C12—H12B | 107.4 |
C6—C5—H5 | 119.3 | C14—C13—C12 | 126.2 (5) |
C5—C6—C1 | 117.4 (4) | C14—C13—H13 | 116.9 |
C5—C6—C7 | 121.5 (4) | C12—C13—H13 | 116.9 |
C1—C6—C7 | 120.8 (4) | C13—C14—H14A | 120.0 |
C8—C7—C6 | 120.7 (4) | C13—C14—H14B | 120.0 |
C8—C7—C11 | 121.0 (4) | H14A—C14—H14B | 120.0 |
C6—C7—C11 | 118.3 (4) | | |
| | | |
O4—S1—N1—C1 | −60.7 (3) | C1—C6—C7—C8 | 21.7 (6) |
O3—S1—N1—C1 | 169.5 (3) | C5—C6—C7—C11 | 17.0 (6) |
C8—S1—N1—C1 | 52.7 (3) | C1—C6—C7—C11 | −156.7 (4) |
O4—S1—N1—C12 | 130.1 (3) | C6—C7—C8—C9 | −171.1 (4) |
O3—S1—N1—C12 | 0.2 (4) | C11—C7—C8—C9 | 7.3 (7) |
C8—S1—N1—C12 | −116.5 (3) | C6—C7—C8—S1 | 7.8 (6) |
C12—N1—C1—C2 | −42.8 (5) | C11—C7—C8—S1 | −173.9 (4) |
S1—N1—C1—C2 | 147.9 (3) | O4—S1—C8—C7 | 72.8 (4) |
C12—N1—C1—C6 | 136.3 (4) | O3—S1—C8—C7 | −154.8 (3) |
S1—N1—C1—C6 | −32.9 (5) | N1—S1—C8—C7 | −40.9 (4) |
N1—C1—C2—C3 | −178.4 (4) | O4—S1—C8—C9 | −108.2 (4) |
C6—C1—C2—C3 | 2.5 (6) | O3—S1—C8—C9 | 24.2 (4) |
C1—C2—C3—C4 | 1.2 (7) | N1—S1—C8—C9 | 138.1 (3) |
C2—C3—C4—C5 | −3.6 (8) | C10—O2—C9—O1 | 5.4 (8) |
C3—C4—C5—C6 | 2.4 (8) | C10—O2—C9—C8 | −171.5 (5) |
C4—C5—C6—C1 | 1.2 (7) | C7—C8—C9—O1 | 46.0 (7) |
C4—C5—C6—C7 | −172.6 (5) | S1—C8—C9—O1 | −132.9 (5) |
C2—C1—C6—C5 | −3.6 (6) | C7—C8—C9—O2 | −137.1 (5) |
N1—C1—C6—C5 | 177.2 (4) | S1—C8—C9—O2 | 44.0 (5) |
C2—C1—C6—C7 | 170.3 (4) | C1—N1—C12—C13 | 97.2 (5) |
N1—C1—C6—C7 | −8.9 (6) | S1—N1—C12—C13 | −94.2 (4) |
C5—C6—C7—C8 | −164.7 (4) | N1—C12—C13—C14 | 3.5 (8) |
Hydrogen-bond geometry (Å, º) topCg is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···Cgi | 0.97 | 2.95 | 3.576 (5) | 123 |
Symmetry code: (i) −x−1/2, y+3/2, z+1/2. |