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

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.

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

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Computing details

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

Crystal data

C13H15N3O3S	Dx = 1.494 Mg m^−3
Mr = 293.34	Melting point = 506–508 K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 223 reflections
a = 11.142 (2) Å	θ = 12.1–79.4°
b = 14.929 (3) Å	µ = 2.33 mm^−1
c = 15.680 (3) Å	T = 293 K
V = 2608.2 (9) Å^3	Prism, colourless
Z = 8	0.25 × 0.20 × 0.20 mm
F(000) = 1232

Data collection

Bruker SMART APEX CCD diffractometer	2478 independent reflections
Radiation source: fine-focus sealed tube	2437 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ω scans	θmax = 70.1°, θmin = 5.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −13→13
Tmin = 0.588, Tmax = 0.654	k = −18→17
27602 measured reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Only H-atom coordinates refined
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0623P)^2 + 0.6394P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2478 reflections	Δρmax = 0.32 e Å^−3
227 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00073 (13)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.12118 (3)	0.05327 (2)	0.21629 (2)	0.03978 (15)
O1S	0.06360 (11)	0.07823 (8)	0.29436 (7)	0.0533 (3)
O2S	0.22613 (10)	−0.00200 (7)	0.22148 (8)	0.0557 (3)
O4	−0.14085 (10)	0.20694 (7)	0.08207 (9)	0.0585 (3)
N2	0.15304 (11)	0.13765 (8)	0.15469 (8)	0.0430 (3)
N8	0.01101 (10)	−0.08456 (7)	0.15140 (7)	0.0392 (3)
N12	0.17698 (13)	0.31775 (9)	0.18528 (9)	0.0501 (3)
H121	0.192 (2)	0.3727 (15)	0.1915 (15)	0.075*
C3	0.05537 (13)	0.19807 (9)	0.13680 (9)	0.0401 (3)
C4	−0.05521 (12)	0.16057 (9)	0.10529 (9)	0.0407 (3)
C5	−0.15850 (12)	0.01562 (9)	0.05745 (9)	0.0399 (3)
C6	−0.15806 (13)	−0.07752 (10)	0.05954 (9)	0.0422 (3)
H61	−0.2131 (18)	−0.1065 (13)	0.0279 (13)	0.063*
C7	−0.07353 (12)	−0.12614 (9)	0.10425 (9)	0.0392 (3)
C9	0.01042 (12)	0.00401 (9)	0.14913 (9)	0.0359 (3)
C10	−0.06713 (12)	0.05990 (9)	0.10338 (9)	0.0364 (3)
C11	0.07534 (14)	0.28903 (9)	0.14948 (9)	0.0430 (3)
C13	0.27362 (16)	0.25930 (12)	0.21222 (11)	0.0517 (4)
H131	0.263 (2)	0.2391 (17)	0.2726 (14)	0.078*
H132	0.347 (2)	0.2963 (16)	0.2053 (14)	0.078*
C14	0.27384 (14)	0.17758 (11)	0.15540 (11)	0.0492 (4)
H141	0.292 (2)	0.1941 (14)	0.0969 (14)	0.074*
H142	0.329 (2)	0.1333 (15)	0.1757 (14)	0.074*
C15	−0.25437 (17)	0.06139 (12)	0.00668 (13)	0.0561 (4)
H151	−0.292 (2)	0.0176 (15)	−0.0302 (15)	0.084*
H152	−0.221 (2)	0.1067 (16)	−0.0274 (16)	0.084*
H153	−0.309 (2)	0.0878 (16)	0.0437 (16)	0.084*
C16	−0.06932 (15)	−0.22622 (10)	0.10114 (12)	0.0487 (4)
H161	−0.0518 (19)	−0.2505 (14)	0.1557 (14)	0.073*
H162	−0.008 (2)	−0.2435 (14)	0.0664 (15)	0.073*
H163	−0.142 (2)	−0.2488 (15)	0.0823 (14)	0.073*
C21	−0.01002 (18)	0.36087 (10)	0.12275 (12)	0.0538 (4)
H211	−0.025 (2)	0.3590 (15)	0.0640 (16)	0.081*
H212	−0.087 (2)	0.3547 (15)	0.1510 (15)	0.081*
H213	0.021 (2)	0.4180 (17)	0.1380 (14)	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0410 (2)	0.0283 (2)	0.0500 (2)	−0.00044 (12)	−0.00860 (13)	−0.00348 (12)
O1S	0.0691 (8)	0.0432 (6)	0.0477 (6)	−0.0041 (5)	−0.0038 (5)	−0.0048 (5)
O2S	0.0479 (6)	0.0369 (5)	0.0823 (8)	0.0062 (5)	−0.0209 (5)	−0.0074 (5)
O4	0.0456 (6)	0.0398 (6)	0.0901 (9)	0.0089 (5)	−0.0090 (6)	0.0013 (6)
N2	0.0358 (6)	0.0335 (6)	0.0598 (7)	−0.0039 (5)	−0.0025 (5)	−0.0011 (5)
N8	0.0402 (6)	0.0312 (6)	0.0462 (6)	−0.0034 (4)	−0.0029 (5)	−0.0011 (5)
N12	0.0625 (8)	0.0346 (6)	0.0531 (7)	−0.0127 (6)	0.0046 (6)	−0.0040 (5)
C3	0.0420 (7)	0.0306 (6)	0.0478 (7)	−0.0004 (5)	0.0022 (6)	0.0014 (5)
C4	0.0395 (7)	0.0332 (7)	0.0493 (8)	0.0026 (5)	0.0030 (6)	0.0005 (5)
C5	0.0361 (7)	0.0420 (7)	0.0415 (7)	0.0012 (6)	0.0009 (5)	−0.0022 (6)
C6	0.0388 (7)	0.0415 (7)	0.0462 (7)	−0.0059 (6)	−0.0024 (6)	−0.0074 (6)
C7	0.0393 (7)	0.0346 (7)	0.0438 (7)	−0.0054 (5)	0.0030 (5)	−0.0034 (5)
C9	0.0345 (6)	0.0311 (6)	0.0422 (7)	−0.0027 (5)	−0.0007 (5)	−0.0029 (5)
C10	0.0342 (7)	0.0333 (7)	0.0418 (7)	0.0003 (5)	0.0034 (5)	−0.0018 (5)
C11	0.0540 (8)	0.0332 (7)	0.0417 (7)	−0.0049 (6)	0.0092 (6)	0.0006 (5)
C13	0.0497 (9)	0.0495 (9)	0.0560 (9)	−0.0168 (7)	0.0002 (7)	−0.0052 (7)
C14	0.0379 (8)	0.0481 (8)	0.0615 (9)	−0.0092 (6)	0.0012 (7)	−0.0071 (7)
C15	0.0510 (9)	0.0530 (9)	0.0642 (10)	0.0072 (7)	−0.0180 (8)	−0.0057 (8)
C16	0.0495 (9)	0.0343 (7)	0.0622 (10)	−0.0082 (6)	−0.0021 (7)	−0.0042 (7)
C21	0.0697 (11)	0.0309 (7)	0.0608 (10)	0.0025 (7)	0.0103 (8)	0.0032 (7)

Geometric parameters (Å, º)

S1—O1S	1.4314 (12)	C6—H61	0.90 (2)
S1—O2S	1.4334 (11)	C7—C16	1.4955 (19)
S1—N2	1.6266 (13)	C9—C10	1.3990 (19)
S1—C9	1.7813 (13)	C11—C21	1.494 (2)
O4—C4	1.2338 (18)	C13—C14	1.511 (2)
N2—C3	1.4411 (18)	C13—H131	1.00 (2)
N2—C14	1.4721 (18)	C13—H132	1.00 (2)
N8—C9	1.3228 (18)	C14—H141	0.97 (2)
N8—C7	1.3487 (17)	C14—H142	0.96 (2)
N12—C11	1.335 (2)	C15—H151	0.97 (2)
N12—C13	1.449 (2)	C15—H152	0.94 (3)
N12—H121	0.84 (2)	C15—H153	0.93 (3)
C3—C11	1.3902 (19)	C16—H161	0.95 (2)
C3—C4	1.441 (2)	C16—H162	0.91 (2)
C4—C10	1.5090 (19)	C16—H163	0.92 (2)
C5—C6	1.391 (2)	C21—H211	0.94 (2)
C5—C10	1.4114 (19)	C21—H212	0.97 (2)
C5—C15	1.497 (2)	C21—H213	0.95 (2)
C6—C7	1.380 (2)
O1S—S1—O2S	117.84 (7)	N12—C11—C3	120.64 (14)
O1S—S1—N2	113.83 (7)	N12—C11—C21	115.32 (13)
O2S—S1—N2	107.55 (7)	C3—C11—C21	124.01 (15)
O1S—S1—C9	107.61 (7)	N12—C13—C14	108.39 (13)
O2S—S1—C9	111.17 (7)	N12—C13—H131	111.8 (14)
N2—S1—C9	96.88 (6)	C14—C13—H131	108.4 (14)
C3—N2—C14	116.00 (12)	N12—C13—H132	104.3 (13)
C3—N2—S1	115.83 (10)	C14—C13—H132	112.5 (13)
C14—N2—S1	120.58 (11)	H131—C13—H132	111.4 (19)
C9—N8—C7	116.23 (11)	N2—C14—C13	109.27 (13)
C11—N12—C13	124.04 (12)	N2—C14—H141	106.6 (13)
C11—N12—H121	122.2 (16)	C13—C14—H141	110.7 (13)
C13—N12—H121	113.6 (16)	N2—C14—H142	108.2 (13)
C11—C3—C4	124.44 (13)	C13—C14—H142	111.2 (13)
C11—C3—N2	117.56 (13)	H141—C14—H142	110.7 (19)
C4—C3—N2	117.99 (12)	C5—C15—H151	108.7 (14)
O4—C4—C3	122.99 (13)	C5—C15—H152	110.4 (15)
O4—C4—C10	119.01 (13)	H151—C15—H152	108.6 (19)
C3—C4—C10	117.98 (12)	C5—C15—H153	109.4 (15)
C6—C5—C10	116.98 (13)	H151—C15—H153	111.6 (19)
C6—C5—C15	118.11 (13)	H152—C15—H153	108 (2)
C10—C5—C15	124.90 (13)	C7—C16—H161	111.0 (13)
C7—C6—C5	122.68 (13)	C7—C16—H162	108.9 (14)
C7—C6—H61	119.5 (12)	H161—C16—H162	106.0 (19)
C5—C6—H61	117.7 (12)	C7—C16—H163	110.4 (14)
N8—C7—C6	120.85 (13)	H161—C16—H163	109.2 (19)
N8—C7—C16	117.12 (13)	H162—C16—H163	111.3 (19)
C6—C7—C16	122.01 (13)	C11—C21—H211	111.4 (14)
N8—C9—C10	127.81 (12)	C11—C21—H212	111.6 (13)
N8—C9—S1	113.16 (10)	H211—C21—H212	107.0 (19)
C10—C9—S1	119.00 (10)	C11—C21—H213	109.8 (14)
C9—C10—C5	115.32 (12)	H211—C21—H213	109.8 (19)
C9—C10—C4	121.97 (12)	H212—C21—H213	107.2 (19)
C5—C10—C4	122.69 (12)
O1S—S1—N2—C3	−51.65 (12)	O1S—S1—C9—C10	80.31 (12)
O2S—S1—N2—C3	175.90 (10)	O2S—S1—C9—C10	−149.28 (11)
C9—S1—N2—C3	61.08 (11)	N2—S1—C9—C10	−37.41 (12)
O1S—S1—N2—C14	96.74 (12)	N8—C9—C10—C5	3.1 (2)
O2S—S1—N2—C14	−35.72 (13)	S1—C9—C10—C5	−174.87 (10)
C9—S1—N2—C14	−150.53 (12)	N8—C9—C10—C4	−178.51 (13)
C14—N2—C3—C11	−20.62 (19)	S1—C9—C10—C4	3.57 (18)
S1—N2—C3—C11	129.25 (12)	C6—C5—C10—C9	−2.83 (19)
C14—N2—C3—C4	158.05 (13)	C15—C5—C10—C9	177.61 (15)
S1—N2—C3—C4	−52.09 (16)	C6—C5—C10—C4	178.74 (13)
C11—C3—C4—O4	4.1 (2)	C15—C5—C10—C4	−0.8 (2)
N2—C3—C4—O4	−174.43 (14)	O4—C4—C10—C9	−162.30 (14)
C11—C3—C4—C10	−173.98 (13)	C3—C4—C10—C9	15.9 (2)
N2—C3—C4—C10	7.45 (19)	O4—C4—C10—C5	16.0 (2)
C10—C5—C6—C7	0.3 (2)	C3—C4—C10—C5	−165.78 (13)
C15—C5—C6—C7	179.87 (15)	C13—N12—C11—C3	1.0 (2)
C9—N8—C7—C6	−2.60 (19)	C13—N12—C11—C21	−177.23 (15)
C9—N8—C7—C16	175.94 (13)	C4—C3—C11—N12	174.63 (13)
C5—C6—C7—N8	2.6 (2)	N2—C3—C11—N12	−6.8 (2)
C5—C6—C7—C16	−175.82 (14)	C4—C3—C11—C21	−7.3 (2)
C7—N8—C9—C10	−0.3 (2)	N2—C3—C11—C21	171.22 (14)
C7—N8—C9—S1	177.74 (10)	C11—N12—C13—C14	29.7 (2)
O1S—S1—C9—N8	−97.90 (11)	C3—N2—C14—C13	50.78 (19)
O2S—S1—C9—N8	32.51 (13)	S1—N2—C14—C13	−97.56 (15)
N2—S1—C9—N8	144.37 (10)	N12—C13—C14—N2	−52.78 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N12—H121···O2S^i	0.84 (2)	2.13 (2)	2.9545 (18)	165 (2)
C13—H131···O4^ii	1.00 (2)	2.56 (2)	3.453 (2)	148.0 (17)
C13—H132···N8^i	1.00 (2)	2.53 (2)	3.479 (2)	160.8 (18)
C16—H163···O4^iii	0.92 (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) −x−1/2, y−1/2, z.