2-Methyl-6,7-di­hydro­thia­zolo­[3,2-b][1,2,4]­thia­diazine 1,1-dioxide

The title compound, C₆H₈N₂O₂S₂, represents one of the first examples of a novel sulfon­amide family. The mol­ecule, which is roughly planar, is built up from two fused rings, viz. the thia­diazine 1,1-dioxide and thia­zole rings.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.110
• Data-to-parameter ratio = 33.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: CAD-4-PC (Enraf-Nonius, 1993) and EXPOSE (Stoe & Cie, 1997); cell refinement: CELL (Stoe & Cie, 1997); data reduction: JANA2000 (Petricek & Dusek, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 1995); program(s) used to refine structure: JANA2000; molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: JANA2000.

(I)

Crystal data

C6H8N2O2S2	F(000) = 424
Mr = 204.3	Dx = 1.601 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 8000 reflections
a = 8.3906 (8) Å	θ = 12.7–27.8°
b = 8.4339 (8) Å	µ = 0.59 mm^−1
c = 12.0900 (11) Å	T = 298 K
β = 98.036 (12)°	Block, colourless
V = 847.15 (14) Å^3	0.35 × 0.28 × 0.22 mm
Z = 4

Data collection

Nonius CAD-4 and Stoe IPDS diffractometer	3729 independent reflections
Radiation source: X-ray tube	2287 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
θ/2θ and ω scans	θmax = 35.1°, θmin = 2.5°
Absorption correction: gaussian (JANA2000; Petricek & Dusek, 2000)	h = −13→13
Tmin = 0.885, Tmax = 0.909	k = −13→13
25270 measured reflections	l = −19→15

Refinement

Refinement on F^2	Weighting scheme based on measured s.u.'s w = 1/[σ^2(I) + 0.0016I^2]
R[F > 3σ(F)] = 0.045	(Δ/σ)max = 0.001
wR(F) = 0.110	Δρmax = 0.71 e Å^−3
S = 1.42	Δρmin = −0.46 e Å^−3
3729 reflections	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
110 parameters	Extinction coefficient: 0.93 (6)
H-atom parameters constrained

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

	x	y	z	Uiso*/Ueq
S1	0.18963 (4)	0.58991 (4)	0.34090 (3)	0.03952 (11)
C2	0.16226 (17)	0.65965 (17)	0.47032 (12)	0.0396 (4)
C3	0.2158 (2)	0.57792 (18)	0.56285 (12)	0.0445 (4)
N4	0.2935 (2)	0.43360 (17)	0.57205 (11)	0.0546 (5)
C4a	0.31606 (17)	0.36385 (17)	0.48137 (11)	0.0378 (4)
S5	0.41100 (6)	0.18039 (5)	0.48260 (4)	0.05554 (15)
C6	0.3601 (2)	0.1577 (2)	0.33408 (15)	0.0576 (6)
C7	0.3272 (3)	0.3168 (2)	0.28742 (15)	0.0680 (7)
N8	0.27029 (16)	0.41489 (15)	0.37505 (10)	0.0415 (4)
C9	0.0806 (3)	0.8175 (2)	0.46962 (18)	0.0631 (6)
O1	0.04106 (15)	0.56498 (18)	0.26999 (11)	0.0670 (5)
O2	0.30443 (16)	0.68336 (15)	0.29325 (11)	0.0651 (5)
H9a	−0.0269	0.8101	0.4261	0.084*
H9b	0.1441	0.8968	0.4358	0.084*
H9c	0.0709	0.8486	0.5464	0.084*
H3	0.196	0.6306	0.6319	0.058*
H6a	0.4475	0.1143	0.2974	0.077*
H6b	0.2617	0.0961	0.3119	0.077*
H7a	0.2453	0.3112	0.2216	0.09*
H7b	0.4268	0.3618	0.266	0.09*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0450 (2)	0.0451 (2)	0.02806 (17)	0.00496 (14)	0.00393 (13)	0.00669 (14)
C2	0.0451 (7)	0.0363 (7)	0.0378 (7)	−0.0020 (5)	0.0071 (6)	−0.0013 (5)
C3	0.0600 (9)	0.0430 (7)	0.0310 (7)	0.0044 (6)	0.0080 (6)	−0.0049 (6)
N4	0.0865 (10)	0.0518 (7)	0.0252 (6)	0.0205 (7)	0.0064 (6)	0.0014 (5)
C4a	0.0457 (7)	0.0391 (6)	0.0288 (6)	0.0030 (6)	0.0054 (5)	0.0013 (5)
S5	0.0758 (3)	0.0478 (2)	0.0414 (2)	0.0228 (2)	0.0022 (2)	−0.00003 (17)
C6	0.0742 (11)	0.0555 (9)	0.0441 (9)	0.0083 (8)	0.0122 (8)	−0.0097 (8)
C7	0.1083 (15)	0.0638 (11)	0.0331 (8)	0.0268 (10)	0.0144 (9)	−0.0056 (8)
N8	0.0577 (7)	0.0423 (6)	0.0250 (5)	0.0068 (5)	0.0078 (5)	0.0012 (5)
C9	0.0850 (13)	0.0439 (9)	0.0603 (11)	0.0154 (8)	0.0102 (10)	−0.0004 (8)
O1	0.0575 (7)	0.0913 (10)	0.0463 (7)	0.0157 (6)	−0.0133 (6)	−0.0114 (7)
O2	0.0800 (9)	0.0621 (8)	0.0592 (8)	0.0010 (6)	0.0307 (7)	0.0228 (6)

Geometric parameters (Å, º)

S1—C2	1.7166 (14)	S5—C6	1.797 (2)
S1—N8	1.6519 (11)	C6—C7	1.467 (2)
S1—O1	1.4260 (15)	C6—H6a	0.98
S1—O2	1.4272 (17)	C6—H6b	0.98
C2—C3	1.3380 (19)	C7—N8	1.475 (2)
C2—C9	1.497 (3)	C7—H7a	0.98
C3—N4	1.378 (2)	C7—H7b	0.98
C3—H3	0.98	C9—H9a	0.98
N4—C4a	1.280 (2)	C9—H9b	0.98
C4a—S5	1.7397 (17)	C9—H9c	0.98
C4a—N8	1.3599 (17)
C2—S1—N8	100.44 (7)	S5—C6—H6b	113.83
C2—S1—O1	112.43 (8)	C7—C6—H6a	106.24
C2—S1—O2	111.25 (8)	C7—C6—H6b	105.85
N8—S1—O1	108.15 (8)	H6a—C6—H6b	109.43
N8—S1—O2	108.57 (9)	C6—C7—N8	107.40 (13)
O1—S1—O2	114.89 (8)	C6—C7—H7a	110.00
S1—C2—C3	120.92 (13)	C6—C7—H7b	109.45
S1—C2—C9	114.79 (12)	N8—C7—H7a	110.5
C3—C2—C9	124.27 (15)	N8—C7—H7b	110.13
C2—C3—N4	128.46 (13)	H7a—C7—H7b	109.32
C2—C3—H3	113.67	S1—N8—C4a	124.78 (10)
N4—C3—H3	117.87	S1—N8—C7	118.98 (10)
C3—N4—C4a	117.53 (13)	C4a—N8—C7	115.14 (12)
N4—C4a—S5	121.58 (12)	C2—C9—H9a	109.5
N4—C4a—N8	127.44 (16)	C2—C9—H9b	109.5
S5—C4a—N8	110.96 (10)	C2—C9—H9c	109.5
C4a—S5—C6	92.40 (7)	H9a—C9—H9b	109.5
S5—C6—C7	107.03 (12)	H9a—C9—H9c	109.5
S5—C6—H6a	113.83	H9b—C9—H9c	109.5