2-Methyl-4,4-dioxo-N-phenyl-5,6-di-hydro-1,4-oxathiine-3-carboxamide (Oxycarboxin).

In the title compound, C(12)H(13)NO(4)S, a systemic fungicide, the heterocycle adopts a lounge chair conformation and the dihedral angle between the ring planes is 25.8 (2)°. Inter-molecular C-H⋯O hydrogen bonds are noted in the crystal structure. Also observed is a short inter-action of a methyl-ene hydrogen atom with the π-electron system of a phenyl ring in an adjacent mol-ecule.

Related literature

The title structure was determined as part of a larger project involving the structures of fungicides, see: Baughman & Paulos (2005 ▶). For the mode of biological action of the title compound, see: Ulrich & Mathre (1972 ▶).

Experimental

Crystal data

C12H13NO4S

M = 267.29

Triclinic,

a = 5.9985 (4) Å

b = 8.3178 (6) Å

c = 13.1333 (8) Å

α = 104.702 (4)°

β = 93.180 (5)°

γ = 106.876 (5)°

V = 600.59 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 295 K

0.54 × 0.44 × 0.16 mm

Data collection

Bruker P4 diffractometer

Absorption correction: integration (XSHELL; Bruker, 1999 ▶) T min = 0.888, T max = 0.959

2152 measured reflections

2152 independent reflections

1884 reflections with I > 2σ(I)

3 standard reflections every 100 reflections intensity decay: 1.2%

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.148

S = 1.17

2152 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.30 e Å−3

Data collection: XSCANS (Bruker, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC, SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037669/fb2200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037669/fb2200Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H13NO4S	Z = 2
Mr = 267.29	F(000) = 280
Triclinic, P1	Dx = 1.478 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9985 (4) Å	Cell parameters from 100 reflections
b = 8.3178 (6) Å	θ = 10.7–18.8°
c = 13.1333 (8) Å	µ = 0.28 mm−1
α = 104.702 (4)°	T = 295 K
β = 93.180 (5)°	Parrallelepiped, colorless
γ = 106.876 (5)°	0.54 × 0.44 × 0.16 mm
V = 600.59 (7) Å3

Bruker P4 diffractometer	1884 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.0000
graphite	θmax = 25.3°, θmin = 2.7°
θ/2θ scans	h = −7→7
Absorption correction: integration (XSHELL; Bruker, 1999)	k = −9→9
Tmin = 0.888, Tmax = 0.959	l = −7→15
2152 measured reflections	3 standard reflections every 100 reflections
2152 independent reflections	intensity decay: 1.2%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: difference Fourier map
wR(F2) = 0.148	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0317P)2 + 1.2476P] where P = (Fo2 + 2Fc2)/3
2152 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.30 e Å−3
51 constraints

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

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 > 2σ(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.

	x	y	z	Uiso*/Ueq
S1	0.86650 (16)	0.76152 (12)	0.09237 (7)	0.0340 (3)
O1	1.3241 (5)	0.9576 (4)	0.2477 (2)	0.0476 (7)
O2	0.7405 (5)	0.8747 (4)	0.0705 (3)	0.0533 (8)
O3	0.7619 (5)	0.5767 (4)	0.0397 (2)	0.0455 (7)
O4	0.7181 (5)	0.7679 (4)	0.3786 (2)	0.0483 (7)
N1	0.5358 (5)	0.5725 (4)	0.2219 (2)	0.0377 (7)
H1A	0.5393	0.5414	0.1546	0.045*
C1	1.2901 (7)	0.9966 (5)	0.1490 (4)	0.0467 (10)
H1B	1.4418	1.0488	0.1291	0.056*
H1C	1.2046	1.0808	0.1576	0.056*
C2	1.1548 (7)	0.8332 (5)	0.0621 (3)	0.0379 (9)
H2A	1.2291	0.7431	0.0584	0.045*
H2B	1.1517	0.8584	−0.0060	0.045*
C3	0.9171 (6)	0.7890 (5)	0.2294 (3)	0.0318 (8)
C4	1.1355 (7)	0.8708 (5)	0.2853 (3)	0.0386 (9)
C5	1.2078 (8)	0.8729 (7)	0.3958 (3)	0.0520 (11)
H5A	1.3705	0.8796	0.4045	0.078*
H5B	1.1134	0.7677	0.4095	0.078*
H5C	1.1861	0.9727	0.4449	0.078*
C6	0.7168 (6)	0.7096 (5)	0.2834 (3)	0.0344 (8)
C7	0.3405 (7)	0.4774 (5)	0.2627 (3)	0.0339 (8)
C8	0.3722 (8)	0.4250 (6)	0.3528 (3)	0.0459 (10)
H8	0.5224	0.4541	0.3891	0.055*
C9	0.1786 (9)	0.3287 (6)	0.3887 (4)	0.0555 (12)
H9	0.1990	0.2953	0.4502	0.067*
C10	−0.0441 (9)	0.2821 (6)	0.3339 (4)	0.0574 (12)
H10	−0.1735	0.2167	0.3577	0.069*
C11	−0.0730 (8)	0.3329 (6)	0.2440 (4)	0.0508 (11)
H11	−0.2229	0.3012	0.2068	0.061*
C12	0.1177 (7)	0.4309 (5)	0.2077 (3)	0.0375 (8)
H12	0.0960	0.4652	0.1467	0.045*

	U11	U22	U33	U12	U13	U23
S1	0.0286 (5)	0.0390 (5)	0.0340 (5)	0.0066 (4)	0.0065 (4)	0.0136 (4)
O1	0.0300 (14)	0.0505 (17)	0.0492 (17)	0.0020 (12)	0.0030 (12)	0.0044 (14)
O2	0.0463 (17)	0.071 (2)	0.0596 (19)	0.0272 (16)	0.0125 (14)	0.0363 (17)
O3	0.0411 (15)	0.0447 (16)	0.0344 (14)	−0.0056 (12)	0.0054 (12)	0.0049 (12)
O4	0.0473 (17)	0.0546 (18)	0.0334 (15)	0.0067 (14)	0.0095 (12)	0.0059 (13)
N1	0.0374 (17)	0.0426 (18)	0.0281 (15)	0.0051 (14)	0.0082 (13)	0.0091 (13)
C1	0.038 (2)	0.036 (2)	0.059 (3)	0.0018 (17)	0.0134 (19)	0.0106 (19)
C2	0.034 (2)	0.035 (2)	0.043 (2)	0.0063 (16)	0.0153 (16)	0.0115 (16)
C3	0.0314 (18)	0.0325 (18)	0.0314 (18)	0.0101 (15)	0.0059 (15)	0.0086 (15)
C4	0.036 (2)	0.036 (2)	0.041 (2)	0.0123 (16)	0.0089 (16)	0.0028 (16)
C5	0.043 (2)	0.068 (3)	0.038 (2)	0.019 (2)	−0.0017 (18)	0.002 (2)
C6	0.0335 (19)	0.0348 (19)	0.035 (2)	0.0106 (16)	0.0060 (15)	0.0103 (16)
C7	0.038 (2)	0.0308 (18)	0.0303 (18)	0.0076 (15)	0.0073 (15)	0.0068 (15)
C8	0.045 (2)	0.052 (2)	0.037 (2)	0.0065 (19)	0.0042 (18)	0.0171 (18)
C9	0.070 (3)	0.052 (3)	0.040 (2)	0.005 (2)	0.016 (2)	0.021 (2)
C10	0.058 (3)	0.050 (3)	0.057 (3)	0.002 (2)	0.027 (2)	0.017 (2)
C11	0.039 (2)	0.044 (2)	0.059 (3)	0.0048 (19)	0.008 (2)	0.007 (2)
C12	0.040 (2)	0.0339 (19)	0.0351 (19)	0.0086 (16)	0.0053 (16)	0.0072 (16)

S1—O2	1.438 (3)	C3—C6	1.501 (5)
S1—O3	1.445 (3)	C4—C5	1.486 (6)
S1—C3	1.754 (4)	C5—H5A	0.9600
S1—C2	1.761 (4)	C5—H5B	0.9600
O1—C4	1.346 (5)	C5—H5C	0.9600
O1—C1	1.432 (5)	C7—C12	1.382 (5)
O4—C6	1.220 (4)	C7—C8	1.383 (5)
N1—C6	1.359 (5)	C8—C9	1.388 (6)
N1—C7	1.425 (5)	C8—H8	0.9300
N1—H1A	0.8600	C9—C10	1.380 (7)
C1—C2	1.509 (5)	C9—H9	0.9300
C1—H1B	0.9700	C10—C11	1.369 (7)
C1—H1C	0.9700	C10—H10	0.9300
C2—H2A	0.9700	C11—C12	1.385 (6)
C2—H2B	0.9700	C11—H11	0.9300
C3—C4	1.357 (5)	C12—H12	0.9300
O2—S1—O3	116.48 (19)	C4—C5—H5A	109.5
O2—S1—C3	110.85 (18)	C4—C5—H5B	109.5
O3—S1—C3	108.26 (17)	H5A—C5—H5B	109.5
O2—S1—C2	108.98 (18)	C4—C5—H5C	109.5
O3—S1—C2	109.37 (18)	H5A—C5—H5C	109.5
C3—S1—C2	101.89 (18)	H5B—C5—H5C	109.5
C4—O1—C1	118.9 (3)	O4—C6—N1	122.0 (3)
C6—N1—C7	123.8 (3)	O4—C6—C3	120.6 (3)
C6—N1—H1A	118.1	N1—C6—C3	117.4 (3)
C7—N1—H1A	118.1	C12—C7—C8	120.1 (4)
O1—C1—C2	111.0 (3)	C12—C7—N1	118.7 (3)
O1—C1—H1B	109.4	C8—C7—N1	121.2 (4)
C2—C1—H1B	109.4	C7—C8—C9	119.6 (4)
O1—C1—H1C	109.4	C7—C8—H8	120.2
C2—C1—H1C	109.4	C9—C8—H8	120.2
H1B—C1—H1C	108.0	C10—C9—C8	120.4 (4)
C1—C2—S1	107.8 (3)	C10—C9—H9	119.8
C1—C2—H2A	110.2	C8—C9—H9	119.8
S1—C2—H2A	110.2	C11—C10—C9	119.4 (4)
C1—C2—H2B	110.2	C11—C10—H10	120.3
S1—C2—H2B	110.2	C9—C10—H10	120.3
H2A—C2—H2B	108.5	C10—C11—C12	121.0 (4)
C4—C3—C6	120.0 (3)	C10—C11—H11	119.5
C4—C3—S1	121.1 (3)	C12—C11—H11	119.5
C6—C3—S1	118.8 (3)	C7—C12—C11	119.5 (4)
O1—C4—C3	125.3 (4)	C7—C12—H12	120.3
O1—C4—C5	109.0 (3)	C11—C12—H12	120.3
C3—C4—C5	125.7 (4)
C4—O1—C1—C2	−53.6 (5)	C7—N1—C6—O4	−4.3 (6)
O1—C1—C2—S1	67.6 (4)	C7—N1—C6—C3	176.2 (3)
O2—S1—C2—C1	74.7 (3)	C4—C3—C6—O4	27.4 (5)
O3—S1—C2—C1	−157.0 (3)	S1—C3—C6—O4	−156.6 (3)
C3—S1—C2—C1	−42.6 (3)	C4—C3—C6—N1	−153.1 (4)
O2—S1—C3—C4	−108.1 (3)	S1—C3—C6—N1	22.9 (5)
O3—S1—C3—C4	123.0 (3)	C6—N1—C7—C12	138.0 (4)
C2—S1—C3—C4	7.8 (4)	C6—N1—C7—C8	−44.9 (6)
O2—S1—C3—C6	76.0 (3)	C12—C7—C8—C9	−1.3 (6)
O3—S1—C3—C6	−52.9 (3)	N1—C7—C8—C9	−178.4 (4)
C2—S1—C3—C6	−168.2 (3)	C7—C8—C9—C10	1.3 (7)
C1—O1—C4—C3	12.1 (6)	C8—C9—C10—C11	−0.6 (7)
C1—O1—C4—C5	−170.3 (3)	C9—C10—C11—C12	−0.3 (7)
C6—C3—C4—O1	−174.9 (3)	C8—C7—C12—C11	0.5 (6)
S1—C3—C4—O1	9.2 (5)	N1—C7—C12—C11	177.6 (4)
C6—C3—C4—C5	7.9 (6)	C10—C11—C12—C7	0.3 (6)
S1—C3—C4—C5	−168.0 (3)

Cg is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.86	2.09	2.819 (4)	142
C2—H2B···O2i	0.97	2.50	3.274 (5)	137
C5—H5A···O4ii	0.96	2.52	3.422 (6)	157
C5—H5B···O4	0.96	2.37	2.786 (6)	106
C8—H8···O4	0.93	2.58	2.926 (5)	103
C9—H9···O4iii	0.93	2.49	3.419 (5)	175
C1—H1C···Cgiv	0.97	2.82	3.645	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.86	2.09	2.819 (4)	142
C2—H2B⋯O2i	0.97	2.50	3.274 (5)	137
C5—H5A⋯O4ii	0.96	2.52	3.422 (6)	157
C9—H9⋯O4iii	0.93	2.49	3.419 (5)	175
C1—H1C⋯Cgiv	0.97	2.82	3.645	144

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .