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The crystal structure of the title compound, C12H13NO3S, is stabilized by inter­molecular N—H...O hydrogen bonds, which are formed between the NH groups and the sulfoxide O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023548/su6218sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023548/su6218Isup2.hkl
Contains datablock I

CCDC reference: 282647

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.033
  • wR factor = 0.082
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.79 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.14 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C6 .. 5.15 su
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.15 From the CIF: _reflns_number_total 2369 Count of symmetry unique reflns 1392 Completeness (_total/calc) 170.19% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 977 Fraction of Friedel pairs measured 0.702 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Ethyl 3-methyl-1-oxo-4H-1,4-benzothiazine-2-carboxylate top
Crystal data top
C12H13NO3SF(000) = 2112
Mr = 251.30Dx = 1.394 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 9568 reflections
a = 12.9935 (13) Åθ = 2.5–27.3°
b = 33.042 (4) ŵ = 0.27 mm1
c = 11.1555 (13) ÅT = 296 K
V = 4789.4 (9) Å3Prism, pale yellow
Z = 160.58 × 0.32 × 0.10 mm
Data collection top
Stoe IPDS-II
diffractometer
2369 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2037 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.034
Detector resolution: 6.67 pixels mm-1θmax = 27.2°, θmin = 2.5°
ω scansh = 1616
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 4140
Tmin = 0.861, Tmax = 0.974l = 1214
6798 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.0541P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.082(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.33 e Å3
2369 reflectionsΔρmin = 0.18 e Å3
157 parametersExtinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
1 restraintExtinction coefficient: 0.0009 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 977 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.001 (3)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S10.11438 (4)0.22389 (1)0.41762 (4)0.0380 (1)
O10.00760 (14)0.20995 (5)0.38434 (15)0.0510 (6)
O20.12503 (17)0.33960 (5)0.36163 (19)0.0633 (7)
O30.12934 (14)0.28300 (5)0.25140 (15)0.0500 (6)
N10.07603 (14)0.26397 (5)0.66416 (17)0.0408 (5)
C10.11329 (14)0.22473 (6)0.66626 (19)0.0375 (6)
C20.12719 (19)0.20536 (9)0.7769 (2)0.0504 (8)
C30.1628 (2)0.16653 (9)0.7801 (2)0.0573 (9)
C40.1871 (2)0.14584 (8)0.6762 (3)0.0564 (8)
C50.17560 (19)0.16488 (7)0.5674 (2)0.0463 (7)
C60.13752 (15)0.20439 (7)0.56190 (19)0.0369 (6)
C70.10662 (16)0.27514 (7)0.45611 (19)0.0378 (6)
C80.07635 (17)0.28856 (6)0.5677 (2)0.0381 (6)
C90.0408 (2)0.33058 (7)0.5941 (2)0.0523 (8)
C100.12073 (17)0.30315 (7)0.3555 (2)0.0431 (7)
C110.1445 (2)0.30665 (9)0.1440 (2)0.0652 (10)
C120.2532 (3)0.31506 (14)0.1235 (4)0.1030 (19)
H10.050600.273400.729600.0490*
H20.112200.218900.847900.0600*
H30.170900.153700.853800.0690*
H40.211000.119300.679800.0680*
H50.193300.151400.497200.0560*
H9A0.006800.331100.670500.0780*
H9B0.006300.339200.532900.0780*
H9C0.099000.348500.595800.0780*
H11A0.107300.332000.151200.0780*
H11B0.116800.292100.075800.0780*
H12A0.282400.327200.193800.1540*
H12B0.260300.333200.056800.1540*
H12C0.288700.290200.106200.1540*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0528 (3)0.0331 (2)0.0282 (2)0.0001 (2)0.0013 (2)0.0010 (2)
O10.0700 (11)0.0429 (9)0.0402 (9)0.0140 (7)0.0187 (7)0.0066 (7)
O20.0918 (15)0.0366 (10)0.0615 (12)0.0072 (9)0.0094 (9)0.0094 (9)
O30.0675 (10)0.0462 (10)0.0362 (9)0.0024 (7)0.0038 (7)0.0097 (7)
N10.0538 (9)0.0370 (9)0.0315 (8)0.0030 (7)0.0081 (8)0.0039 (8)
C10.0421 (10)0.0365 (11)0.0339 (11)0.0001 (7)0.0008 (10)0.0009 (10)
C20.0648 (14)0.0550 (15)0.0314 (12)0.0034 (11)0.0016 (10)0.0009 (11)
C30.0738 (17)0.0574 (17)0.0407 (13)0.0055 (12)0.0080 (12)0.0126 (12)
C40.0675 (14)0.0436 (13)0.0580 (15)0.0126 (11)0.0034 (13)0.0076 (12)
C50.0553 (13)0.0397 (12)0.0438 (12)0.0084 (10)0.0000 (10)0.0056 (10)
C60.0415 (11)0.0333 (11)0.0359 (11)0.0010 (8)0.0002 (8)0.0006 (9)
C70.0451 (11)0.0310 (10)0.0373 (11)0.0021 (8)0.0005 (8)0.0019 (8)
C80.0430 (10)0.0320 (11)0.0392 (11)0.0030 (8)0.0027 (8)0.0018 (9)
C90.0634 (14)0.0372 (13)0.0564 (15)0.0049 (11)0.0100 (11)0.0022 (11)
C100.0470 (12)0.0392 (13)0.0431 (12)0.0015 (9)0.0012 (9)0.0046 (10)
C110.0831 (19)0.0703 (18)0.0422 (17)0.0003 (15)0.0064 (12)0.0226 (13)
C120.104 (3)0.124 (4)0.081 (3)0.021 (2)0.016 (2)0.037 (3)
Geometric parameters (Å, º) top
S1—O11.5083 (19)C7—C101.466 (3)
S1—C61.760 (2)C8—C91.493 (3)
S1—C71.750 (2)C11—C121.458 (5)
O2—C101.208 (3)C2—H20.9300
O3—C101.343 (3)C3—H30.9300
O3—C111.444 (3)C4—H40.9300
N1—C11.384 (3)C5—H50.9300
N1—C81.348 (3)C9—H9A0.9600
N1—H10.8600C9—H9B0.9600
C1—C61.381 (3)C9—H9C0.9600
C1—C21.402 (3)C11—H11A0.9700
C2—C31.364 (4)C11—H11B0.9700
C3—C41.382 (4)C12—H12A0.9600
C4—C51.375 (4)C12—H12B0.9600
C5—C61.398 (3)C12—H12C0.9600
C7—C81.379 (3)
S1···O32.7002 (18)C11···C1ii3.515 (3)
S1···N13.0930 (19)C12···O23.239 (5)
S1···C7i3.651 (2)C4···H9Ci2.9300
S1···C10i3.623 (2)C5···H9Ci2.9800
S1···H1ii3.0000C7···H2ii3.1000
O1···N1ii2.821 (3)C9···H5vii2.9000
O2···C123.239 (5)C10···H9C3.0800
O2···C9iii3.411 (3)C10···H12A2.8800
O2···C92.831 (3)C10···H9B2.8400
O3···C1ii3.303 (3)H1···H22.3700
O3···C2ii3.367 (3)H1···H9A2.1000
O3···N1ii3.237 (3)H1···S1iv3.0000
O3···S12.7002 (18)H1···O1iv1.9600
O1···H9Aii2.7500H2···H12.3700
O1···H11Biv2.6800H2···O1iv2.8500
O1···H1ii1.9600H2···C7iv3.1000
O1···H2ii2.8500H3···H11Aviii2.4500
O1···H4v2.7400H3···H12Bix2.4700
O2···H5i2.8200H4···O1x2.7400
O2···H12A2.8000H5···C9xi2.9000
O2···H9B2.5600H5···H9Axi2.5600
O2···H9C2.6500H5···H9Cxi2.4900
O2···H11A2.3700H5···O2i2.8200
N1···S13.0930 (19)H9A···H12.1000
N1···O1iv2.821 (3)H9A···H5vii2.5600
N1···O3iv3.237 (3)H9A···O1iv2.7500
C1···O3iv3.303 (3)H9B···O22.5600
C1···C11iv3.515 (3)H9B···C102.8400
C2···O3iv3.367 (3)H9C···O22.6500
C2···C10iv3.350 (3)H9C···C103.0800
C5···C8i3.571 (3)H9C···H5vii2.4900
C6···C7i3.592 (3)H9C···C4i2.9300
C7···S1i3.651 (2)H9C···C5i2.9800
C7···C6i3.592 (3)H11A···O22.3700
C8···C5i3.571 (3)H11A···H3xii2.4500
C9···O2vi3.411 (3)H11B···O1ii2.6800
C9···O22.831 (3)H12A···O22.8000
C10···S1i3.623 (2)H12A···C102.8800
C10···C2ii3.350 (3)H12B···H3xiii2.4700
O1—S1—C6105.70 (10)O3—C11—C12111.4 (3)
O1—S1—C7107.63 (10)C1—C2—H2120.00
C6—S1—C798.03 (10)C3—C2—H2120.00
C10—O3—C11117.42 (19)C2—C3—H3119.00
C1—N1—C8125.23 (19)C4—C3—H3119.00
C8—N1—H1117.00C3—C4—H4120.00
C1—N1—H1117.00C5—C4—H4120.00
N1—C1—C6121.43 (19)C4—C5—H5120.00
N1—C1—C2119.2 (2)C6—C5—H5120.00
C2—C1—C6119.4 (2)C8—C9—H9A110.00
C1—C2—C3119.7 (2)C8—C9—H9B109.00
C2—C3—C4121.4 (2)C8—C9—H9C109.00
C3—C4—C5119.3 (2)H9A—C9—H9B109.00
C4—C5—C6120.3 (2)H9A—C9—H9C109.00
S1—C6—C5116.28 (16)H9B—C9—H9C109.00
C1—C6—C5119.9 (2)O3—C11—H11A109.00
S1—C6—C1123.65 (17)O3—C11—H11B109.00
C8—C7—C10121.6 (2)C12—C11—H11A109.00
S1—C7—C8123.31 (17)C12—C11—H11B109.00
S1—C7—C10114.57 (16)H11A—C11—H11B108.00
C7—C8—C9124.4 (2)C11—C12—H12A110.00
N1—C8—C7121.85 (19)C11—C12—H12B109.00
N1—C8—C9113.71 (19)C11—C12—H12C109.00
O2—C10—O3122.6 (2)H12A—C12—H12B110.00
O2—C10—C7126.3 (2)H12A—C12—H12C109.00
O3—C10—C7111.06 (19)H12B—C12—H12C109.00
O1—S1—C6—C585.45 (18)N1—C1—C2—C3179.3 (2)
C7—S1—C6—C5163.61 (18)C2—C1—C6—S1174.97 (17)
O1—S1—C7—C882.2 (2)N1—C1—C6—S15.4 (3)
C6—S1—C7—C827.2 (2)C6—C1—C2—C31.1 (3)
O1—S1—C7—C1089.56 (17)C1—C2—C3—C40.9 (4)
C6—S1—C7—C10161.07 (16)C2—C3—C4—C50.3 (4)
O1—S1—C6—C189.75 (19)C3—C4—C5—C61.5 (4)
C7—S1—C6—C121.19 (19)C4—C5—C6—S1174.06 (19)
C11—O3—C10—O20.1 (3)C4—C5—C6—C11.3 (3)
C11—O3—C10—C7179.51 (19)S1—C7—C10—O2175.0 (2)
C10—O3—C11—C1286.8 (3)C10—C7—C8—N1171.3 (2)
C1—N1—C8—C9174.35 (19)C10—C7—C8—C99.1 (3)
C8—N1—C1—C2167.4 (2)S1—C7—C8—N117.5 (3)
C1—N1—C8—C76.0 (3)S1—C7—C8—C9162.10 (18)
C8—N1—C1—C612.3 (3)C8—C7—C10—O213.1 (4)
C2—C1—C6—C50.1 (3)C8—C7—C10—O3167.3 (2)
N1—C1—C6—C5179.59 (19)S1—C7—C10—O34.6 (2)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y+1/2, z1/2; (iii) x+1/4, y+3/4, z1/4; (iv) x, y+1/2, z+1/2; (v) x1/4, y+1/4, z1/4; (vi) x1/4, y+3/4, z+1/4; (vii) x+1/4, y+1/4, z+1/4; (viii) x+1/4, y1/4, z+3/4; (ix) x+1/2, y+1/2, z+1; (x) x+1/4, y+1/4, z+1/4; (xi) x+1/4, y1/4, z1/4; (xii) x+1/4, y+1/4, z3/4; (xiii) x+1/2, y+1/2, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1iv0.861.962.821 (3)175
Symmetry code: (iv) x, y+1/2, z+1/2.
 

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