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The structure of the title compound, C13H15N3O3S, is the first report of a structure comprising a novel pyrido[3,2-e]pyrazino[1,2-b][1,2]thiazine ring system. The partially saturated thia­zine and pyrazine rings adopt screw-boat and sofa conformations, respectively. The crystal structure contains inter­molecular N—H...O hydrogen bonds, short C—H...X (X = N, O) contacts and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048355/kp2062sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048355/kp2062Isup2.hkl
Contains datablock I

CCDC reference: 630042

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.097
  • Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).

2,4,6-Trimethyl-8,9-dihydro-5H,7H-pyrido[3,2-e]pyrazino[1,2-b][1,2]thiazin-5-one 11,11-dioxide top
Crystal data top
C13H15N3O3SDx = 1.494 Mg m3
Mr = 293.34Melting point = 506–508 K
Orthorhombic, PbcaCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2abCell parameters from 223 reflections
a = 11.142 (2) Åθ = 12.1–79.4°
b = 14.929 (3) ŵ = 2.33 mm1
c = 15.680 (3) ÅT = 293 K
V = 2608.2 (9) Å3Prism, colourless
Z = 80.25 × 0.20 × 0.20 mm
F(000) = 1232
Data collection top
Bruker SMART APEX CCD
diffractometer
2478 independent reflections
Radiation source: fine-focus sealed tube2437 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 70.1°, θmin = 5.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 1313
Tmin = 0.588, Tmax = 0.654k = 1817
27602 measured reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Only H-atom coordinates refined
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0623P)2 + 0.6394P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2478 reflectionsΔρmax = 0.32 e Å3
227 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00073 (13)
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)

- 6.7527 (0.0052) x + 0.2850 (0.0080) y + 12.4686 (0.0059) z = 1.7797 (0.0007)

* 0.0114 (0.0010) C5 * 0.0079 (0.0010) C6 * -0.0192 (0.0009) C7 * 0.0097 (0.0009) N8 * 0.0106 (0.0009) C9 * -0.0203 (0.0009) C10 0.0388 (0.0028) C15 - 0.1150 (0.0025) C16

Rms deviation of fitted atoms = 0.0140

- 4.1551 (0.0204) x - 0.3216 (0.0183) y + 14.5449 (0.0115) z = 1.7341 (0.0022)

Angle to previous plane (with approximate e.s.d.) = 15.59 (0.16)

* 0.0292 (0.0006) C10 * -0.0250 (0.0005) C4 * -0.0382 (0.0008) C3 * 0.0340 (0.0007) C11 - 0.0217 (0.0042) O4 - 0.1643 (0.0044) N2 - 0.0232 (0.0041) C21

Rms deviation of fitted atoms = 0.0320

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
S10.12118 (3)0.05327 (2)0.21629 (2)0.03978 (15)
O1S0.06360 (11)0.07823 (8)0.29436 (7)0.0533 (3)
O2S0.22613 (10)0.00200 (7)0.22148 (8)0.0557 (3)
O40.14085 (10)0.20694 (7)0.08207 (9)0.0585 (3)
N20.15304 (11)0.13765 (8)0.15469 (8)0.0430 (3)
N80.01101 (10)0.08456 (7)0.15140 (7)0.0392 (3)
N120.17698 (13)0.31775 (9)0.18528 (9)0.0501 (3)
H1210.192 (2)0.3727 (15)0.1915 (15)0.075*
C30.05537 (13)0.19807 (9)0.13680 (9)0.0401 (3)
C40.05521 (12)0.16057 (9)0.10529 (9)0.0407 (3)
C50.15850 (12)0.01562 (9)0.05745 (9)0.0399 (3)
C60.15806 (13)0.07752 (10)0.05954 (9)0.0422 (3)
H610.2131 (18)0.1065 (13)0.0279 (13)0.063*
C70.07353 (12)0.12614 (9)0.10425 (9)0.0392 (3)
C90.01042 (12)0.00401 (9)0.14913 (9)0.0359 (3)
C100.06713 (12)0.05990 (9)0.10338 (9)0.0364 (3)
C110.07534 (14)0.28903 (9)0.14948 (9)0.0430 (3)
C130.27362 (16)0.25930 (12)0.21222 (11)0.0517 (4)
H1310.263 (2)0.2391 (17)0.2726 (14)0.078*
H1320.347 (2)0.2963 (16)0.2053 (14)0.078*
C140.27384 (14)0.17758 (11)0.15540 (11)0.0492 (4)
H1410.292 (2)0.1941 (14)0.0969 (14)0.074*
H1420.329 (2)0.1333 (15)0.1757 (14)0.074*
C150.25437 (17)0.06139 (12)0.00668 (13)0.0561 (4)
H1510.292 (2)0.0176 (15)0.0302 (15)0.084*
H1520.221 (2)0.1067 (16)0.0274 (16)0.084*
H1530.309 (2)0.0878 (16)0.0437 (16)0.084*
C160.06932 (15)0.22622 (10)0.10114 (12)0.0487 (4)
H1610.0518 (19)0.2505 (14)0.1557 (14)0.073*
H1620.008 (2)0.2435 (14)0.0664 (15)0.073*
H1630.142 (2)0.2488 (15)0.0823 (14)0.073*
C210.01002 (18)0.36087 (10)0.12275 (12)0.0538 (4)
H2110.025 (2)0.3590 (15)0.0640 (16)0.081*
H2120.087 (2)0.3547 (15)0.1510 (15)0.081*
H2130.021 (2)0.4180 (17)0.1380 (14)0.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0410 (2)0.0283 (2)0.0500 (2)0.00044 (12)0.00860 (13)0.00348 (12)
O1S0.0691 (8)0.0432 (6)0.0477 (6)0.0041 (5)0.0038 (5)0.0048 (5)
O2S0.0479 (6)0.0369 (5)0.0823 (8)0.0062 (5)0.0209 (5)0.0074 (5)
O40.0456 (6)0.0398 (6)0.0901 (9)0.0089 (5)0.0090 (6)0.0013 (6)
N20.0358 (6)0.0335 (6)0.0598 (7)0.0039 (5)0.0025 (5)0.0011 (5)
N80.0402 (6)0.0312 (6)0.0462 (6)0.0034 (4)0.0029 (5)0.0011 (5)
N120.0625 (8)0.0346 (6)0.0531 (7)0.0127 (6)0.0046 (6)0.0040 (5)
C30.0420 (7)0.0306 (6)0.0478 (7)0.0004 (5)0.0022 (6)0.0014 (5)
C40.0395 (7)0.0332 (7)0.0493 (8)0.0026 (5)0.0030 (6)0.0005 (5)
C50.0361 (7)0.0420 (7)0.0415 (7)0.0012 (6)0.0009 (5)0.0022 (6)
C60.0388 (7)0.0415 (7)0.0462 (7)0.0059 (6)0.0024 (6)0.0074 (6)
C70.0393 (7)0.0346 (7)0.0438 (7)0.0054 (5)0.0030 (5)0.0034 (5)
C90.0345 (6)0.0311 (6)0.0422 (7)0.0027 (5)0.0007 (5)0.0029 (5)
C100.0342 (7)0.0333 (7)0.0418 (7)0.0003 (5)0.0034 (5)0.0018 (5)
C110.0540 (8)0.0332 (7)0.0417 (7)0.0049 (6)0.0092 (6)0.0006 (5)
C130.0497 (9)0.0495 (9)0.0560 (9)0.0168 (7)0.0002 (7)0.0052 (7)
C140.0379 (8)0.0481 (8)0.0615 (9)0.0092 (6)0.0012 (7)0.0071 (7)
C150.0510 (9)0.0530 (9)0.0642 (10)0.0072 (7)0.0180 (8)0.0057 (8)
C160.0495 (9)0.0343 (7)0.0622 (10)0.0082 (6)0.0021 (7)0.0042 (7)
C210.0697 (11)0.0309 (7)0.0608 (10)0.0025 (7)0.0103 (8)0.0032 (7)
Geometric parameters (Å, º) top
S1—O1S1.4314 (12)C6—H610.90 (2)
S1—O2S1.4334 (11)C7—C161.4955 (19)
S1—N21.6266 (13)C9—C101.3990 (19)
S1—C91.7813 (13)C11—C211.494 (2)
O4—C41.2338 (18)C13—C141.511 (2)
N2—C31.4411 (18)C13—H1311.00 (2)
N2—C141.4721 (18)C13—H1321.00 (2)
N8—C91.3228 (18)C14—H1410.97 (2)
N8—C71.3487 (17)C14—H1420.96 (2)
N12—C111.335 (2)C15—H1510.97 (2)
N12—C131.449 (2)C15—H1520.94 (3)
N12—H1210.84 (2)C15—H1530.93 (3)
C3—C111.3902 (19)C16—H1610.95 (2)
C3—C41.441 (2)C16—H1620.91 (2)
C4—C101.5090 (19)C16—H1630.92 (2)
C5—C61.391 (2)C21—H2110.94 (2)
C5—C101.4114 (19)C21—H2120.97 (2)
C5—C151.497 (2)C21—H2130.95 (2)
C6—C71.380 (2)
O1S—S1—O2S117.84 (7)N12—C11—C3120.64 (14)
O1S—S1—N2113.83 (7)N12—C11—C21115.32 (13)
O2S—S1—N2107.55 (7)C3—C11—C21124.01 (15)
O1S—S1—C9107.61 (7)N12—C13—C14108.39 (13)
O2S—S1—C9111.17 (7)N12—C13—H131111.8 (14)
N2—S1—C996.88 (6)C14—C13—H131108.4 (14)
C3—N2—C14116.00 (12)N12—C13—H132104.3 (13)
C3—N2—S1115.83 (10)C14—C13—H132112.5 (13)
C14—N2—S1120.58 (11)H131—C13—H132111.4 (19)
C9—N8—C7116.23 (11)N2—C14—C13109.27 (13)
C11—N12—C13124.04 (12)N2—C14—H141106.6 (13)
C11—N12—H121122.2 (16)C13—C14—H141110.7 (13)
C13—N12—H121113.6 (16)N2—C14—H142108.2 (13)
C11—C3—C4124.44 (13)C13—C14—H142111.2 (13)
C11—C3—N2117.56 (13)H141—C14—H142110.7 (19)
C4—C3—N2117.99 (12)C5—C15—H151108.7 (14)
O4—C4—C3122.99 (13)C5—C15—H152110.4 (15)
O4—C4—C10119.01 (13)H151—C15—H152108.6 (19)
C3—C4—C10117.98 (12)C5—C15—H153109.4 (15)
C6—C5—C10116.98 (13)H151—C15—H153111.6 (19)
C6—C5—C15118.11 (13)H152—C15—H153108 (2)
C10—C5—C15124.90 (13)C7—C16—H161111.0 (13)
C7—C6—C5122.68 (13)C7—C16—H162108.9 (14)
C7—C6—H61119.5 (12)H161—C16—H162106.0 (19)
C5—C6—H61117.7 (12)C7—C16—H163110.4 (14)
N8—C7—C6120.85 (13)H161—C16—H163109.2 (19)
N8—C7—C16117.12 (13)H162—C16—H163111.3 (19)
C6—C7—C16122.01 (13)C11—C21—H211111.4 (14)
N8—C9—C10127.81 (12)C11—C21—H212111.6 (13)
N8—C9—S1113.16 (10)H211—C21—H212107.0 (19)
C10—C9—S1119.00 (10)C11—C21—H213109.8 (14)
C9—C10—C5115.32 (12)H211—C21—H213109.8 (19)
C9—C10—C4121.97 (12)H212—C21—H213107.2 (19)
C5—C10—C4122.69 (12)
O1S—S1—N2—C351.65 (12)O1S—S1—C9—C1080.31 (12)
O2S—S1—N2—C3175.90 (10)O2S—S1—C9—C10149.28 (11)
C9—S1—N2—C361.08 (11)N2—S1—C9—C1037.41 (12)
O1S—S1—N2—C1496.74 (12)N8—C9—C10—C53.1 (2)
O2S—S1—N2—C1435.72 (13)S1—C9—C10—C5174.87 (10)
C9—S1—N2—C14150.53 (12)N8—C9—C10—C4178.51 (13)
C14—N2—C3—C1120.62 (19)S1—C9—C10—C43.57 (18)
S1—N2—C3—C11129.25 (12)C6—C5—C10—C92.83 (19)
C14—N2—C3—C4158.05 (13)C15—C5—C10—C9177.61 (15)
S1—N2—C3—C452.09 (16)C6—C5—C10—C4178.74 (13)
C11—C3—C4—O44.1 (2)C15—C5—C10—C40.8 (2)
N2—C3—C4—O4174.43 (14)O4—C4—C10—C9162.30 (14)
C11—C3—C4—C10173.98 (13)C3—C4—C10—C915.9 (2)
N2—C3—C4—C107.45 (19)O4—C4—C10—C516.0 (2)
C10—C5—C6—C70.3 (2)C3—C4—C10—C5165.78 (13)
C15—C5—C6—C7179.87 (15)C13—N12—C11—C31.0 (2)
C9—N8—C7—C62.60 (19)C13—N12—C11—C21177.23 (15)
C9—N8—C7—C16175.94 (13)C4—C3—C11—N12174.63 (13)
C5—C6—C7—N82.6 (2)N2—C3—C11—N126.8 (2)
C5—C6—C7—C16175.82 (14)C4—C3—C11—C217.3 (2)
C7—N8—C9—C100.3 (2)N2—C3—C11—C21171.22 (14)
C7—N8—C9—S1177.74 (10)C11—N12—C13—C1429.7 (2)
O1S—S1—C9—N897.90 (11)C3—N2—C14—C1350.78 (19)
O2S—S1—C9—N832.51 (13)S1—N2—C14—C1397.56 (15)
N2—S1—C9—N8144.37 (10)N12—C13—C14—N252.78 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12—H121···O2Si0.84 (2)2.13 (2)2.9545 (18)165 (2)
C13—H131···O4ii1.00 (2)2.56 (2)3.453 (2)148.0 (17)
C13—H132···N8i1.00 (2)2.53 (2)3.479 (2)160.8 (18)
C16—H163···O4iii0.92 (2)2.51 (2)3.393 (2)160.1 (18)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y, z+1/2; (iii) x1/2, y1/2, z.
 

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