Methyl 2-methyl-7-oxo-1,2,4-triazolo­[3,2-b]-1,3-thia­zine-5-carboxyl­ate

In the title mol­ecule, C₈H₇N₃O₃S, the triazole and thia­zine rings are nearly coplanar, with a dihedral angle of 2.27 (9)°. The methyl carboxyl­ate moiety is also planar and makes a dihedral angle of 7.31 (13)° with the thia­zine-triazole mean plane.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.125
• Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTY_02  Alert C An _exptl_absorpt_correction_type has been given without
          a literature citation. This should be contained in the
          _exptl_absorpt_process_details field.
          Absorption correction given as \y scan


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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, 1999); software used to prepare material for publication: PARST (Nardelli, 1995).

(I)

Crystal data

C8H7N3O3S	Z = 2
Mr = 225.23	F(000) = 232
Triclinic, P1	Dx = 1.587 Mg m^−3
a = 4.0299 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2866 (7) Å	Cell parameters from 25 reflections
c = 11.9615 (9) Å	θ = 9.4–18.4°
α = 104.870 (6)°	µ = 0.33 mm^−1
β = 96.745 (6)°	T = 295 K
γ = 95.831 (6)°	Prism, colorless
V = 471.42 (6) Å^3	0.4 × 0.32 × 0.12 mm

Data collection

Enraf-Nonius TurboCAD-4 diffractometer	Rint = 0.011
non–profiled θ/2θ scans	θmax = 26.3°, θmin = 3.1°
Absorption correction: ψ scan	h = −5→0
Tmin = 0.880, Tmax = 0.961	k = −12→12
2173 measured reflections	l = −14→14
1893 independent reflections	3 standard reflections every 120 min
1504 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 0.1626P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.125	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.34 e Å^−3
1891 reflections	Δρmin = −0.31 e Å^−3
140 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C8	0.2340 (10)	0.9164 (3)	0.5996 (3)	0.0781 (10)
H8A	0.112	0.9243	0.5283	0.117*
H8B	0.4689	0.9167	0.5924	0.117*
H8C	0.2075	0.9915	0.6632	0.117*
H3	−0.206 (7)	0.562 (3)	0.584 (2)	0.045 (7)*
C1	0.1252 (6)	0.4384 (2)	0.83787 (19)	0.0366 (5)
C2	0.1100 (6)	0.6283 (2)	0.72732 (19)	0.0390 (5)
C3	−0.1236 (6)	0.5413 (3)	0.6464 (2)	0.0427 (6)
C4	−0.2641 (6)	0.4073 (2)	0.6507 (2)	0.0436 (6)
C5	0.0011 (6)	0.2438 (2)	0.8576 (2)	0.0432 (6)
C6	0.0099 (8)	0.1272 (3)	0.9099 (3)	0.0591 (7)
H6A	0.1668	0.1536	0.9812	0.089*
H6B	0.0794	0.0522	0.8559	0.089*
H6C	−0.2108	0.1008	0.9261	0.089*
C7	0.2438 (7)	0.7655 (3)	0.7171 (2)	0.0448 (6)
N1	−0.1906 (6)	0.2374 (2)	0.75994 (19)	0.0468 (5)
N2	−0.1111 (5)	0.36492 (19)	0.74501 (17)	0.0395 (5)
N3	0.2004 (5)	0.36592 (19)	0.90980 (17)	0.0427 (5)
O1	−0.4942 (5)	0.3354 (2)	0.58140 (17)	0.0627 (6)
O2	0.4580 (6)	0.8389 (2)	0.7893 (2)	0.0752 (7)
O3	0.1037 (5)	0.7906 (2)	0.62205 (18)	0.0625 (6)
S1	0.30459 (16)	0.60316 (6)	0.85551 (5)	0.0407 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C8	0.104 (3)	0.066 (2)	0.082 (2)	0.0145 (19)	0.013 (2)	0.0509 (19)
C1	0.0394 (12)	0.0322 (11)	0.0351 (11)	0.0000 (9)	0.0012 (9)	0.0075 (9)
C2	0.0414 (13)	0.0413 (12)	0.0347 (11)	0.0057 (10)	0.0024 (9)	0.0124 (9)
C3	0.0438 (13)	0.0502 (14)	0.0337 (11)	0.0063 (11)	−0.0011 (10)	0.0137 (10)
C4	0.0439 (14)	0.0459 (13)	0.0359 (12)	0.0024 (11)	−0.0001 (10)	0.0061 (10)
C5	0.0469 (14)	0.0321 (11)	0.0491 (14)	0.0020 (10)	0.0057 (11)	0.0106 (10)
C6	0.0713 (19)	0.0362 (13)	0.0714 (19)	0.0035 (12)	0.0032 (15)	0.0224 (13)
C7	0.0504 (15)	0.0423 (13)	0.0449 (13)	0.0082 (11)	0.0031 (11)	0.0185 (11)
N1	0.0504 (12)	0.0327 (10)	0.0523 (12)	−0.0026 (9)	0.0037 (10)	0.0079 (9)
N2	0.0414 (11)	0.0333 (10)	0.0386 (10)	−0.0023 (8)	−0.0008 (8)	0.0063 (8)
N3	0.0515 (12)	0.0343 (10)	0.0408 (11)	0.0016 (9)	−0.0008 (9)	0.0125 (8)
O1	0.0598 (12)	0.0580 (12)	0.0553 (11)	−0.0104 (10)	−0.0196 (9)	0.0081 (9)
O2	0.0961 (17)	0.0452 (11)	0.0741 (14)	−0.0178 (11)	−0.0261 (12)	0.0263 (10)
O3	0.0712 (13)	0.0638 (13)	0.0574 (12)	−0.0020 (10)	−0.0058 (10)	0.0366 (10)
S1	0.0492 (4)	0.0338 (3)	0.0351 (3)	−0.0032 (2)	−0.0060 (2)	0.0112 (2)

Geometric parameters (Å, º)

C8—O3	1.447 (3)	C4—O1	1.208 (3)
C8—H8A	0.96	C4—N2	1.409 (3)
C8—H8B	0.96	C5—N1	1.305 (3)
C8—H8C	0.96	C5—N3	1.374 (3)
C1—N3	1.305 (3)	C5—C6	1.489 (3)
C1—N2	1.373 (3)	C6—H6A	0.96
C1—S1	1.723 (2)	C6—H6B	0.96
C2—C3	1.339 (4)	C6—H6C	0.96
C2—C7	1.498 (3)	C7—O2	1.191 (3)
C2—S1	1.731 (2)	C7—O3	1.307 (3)
C3—C4	1.452 (3)	N1—N2	1.380 (3)
C3—H3	0.87 (3)
O3—C8—H8A	109.5	N1—C5—C6	123.0 (2)
O3—C8—H8B	109.5	N3—C5—C6	121.4 (2)
H8A—C8—H8B	109.5	C5—C6—H6A	109.5
O3—C8—H8C	109.5	C5—C6—H6B	109.5
H8A—C8—H8C	109.5	H6A—C6—H6B	109.5
H8B—C8—H8C	109.5	C5—C6—H6C	109.5
N3—C1—N2	110.9 (2)	H6A—C6—H6C	109.5
N3—C1—S1	124.53 (18)	H6B—C6—H6C	109.5
N2—C1—S1	124.57 (17)	O2—C7—O3	126.1 (2)
C3—C2—C7	123.2 (2)	O2—C7—C2	121.4 (2)
C3—C2—S1	127.09 (19)	O3—C7—C2	112.5 (2)
C7—C2—S1	109.74 (17)	C5—N1—N2	102.76 (19)
C2—C3—C4	126.0 (2)	C1—N2—N1	108.02 (19)
C2—C3—H3	120.6 (18)	C1—N2—C4	128.5 (2)
C4—C3—H3	113.4 (18)	N1—N2—C4	123.5 (2)
O1—C4—N2	120.9 (2)	C1—N3—C5	102.8 (2)
O1—C4—C3	124.6 (2)	C7—O3—C8	116.8 (2)
N2—C4—C3	114.5 (2)	C1—S1—C2	98.98 (11)
N1—C5—N3	115.6 (2)
C7—C2—C3—C4	−180.0 (2)	C5—N1—N2—C4	−178.5 (2)
S1—C2—C3—C4	0.6 (4)	O1—C4—N2—C1	−172.3 (2)
C2—C3—C4—O1	173.6 (3)	C3—C4—N2—C1	7.2 (4)
C2—C3—C4—N2	−5.9 (4)	O1—C4—N2—N1	5.4 (4)
C3—C2—C7—O2	−178.0 (3)	C3—C4—N2—N1	−175.1 (2)
S1—C2—C7—O2	1.5 (3)	N2—C1—N3—C5	0.1 (3)
C3—C2—C7—O3	1.0 (4)	S1—C1—N3—C5	−178.67 (18)
S1—C2—C7—O3	−179.53 (18)	N1—C5—N3—C1	−0.4 (3)
N3—C5—N1—N2	0.5 (3)	C6—C5—N3—C1	178.9 (2)
C6—C5—N1—N2	−178.8 (2)	O2—C7—O3—C8	3.5 (5)
N3—C1—N2—N1	0.2 (3)	C2—C7—O3—C8	−175.5 (2)
S1—C1—N2—N1	178.98 (16)	N3—C1—S1—C2	176.5 (2)
N3—C1—N2—C4	178.2 (2)	N2—C1—S1—C2	−2.1 (2)
S1—C1—N2—C4	−3.1 (4)	C3—C2—S1—C1	3.2 (3)
C5—N1—N2—C1	−0.4 (3)	C7—C2—S1—C1	−176.26 (17)