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

Brown, J.E.; Baughman, R.G.

doi:10.1107/S1600536810037669

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2654

doi:10.1107/S1600536810037669

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

J. Emery Brown ^a and Russell G. Baughman ^a ^*

^aDepartment of Chemistry, Truman State University, Kirksville, MO 63501-4221, USA
^*Correspondence e-mail: baughman@truman.edu

(Received 3 June 2010; accepted 20 September 2010; online 30 September 2010)

In the title compound, C₁₂H₁₃NO₄S, a systemic fungicide, the heterocycle adopts a lounge chair conformation and the dihedral angle between the ring planes is 25.8 (2)°. Intermolecular C—H⋯O hydrogen bonds are noted in the crystal structure. Also observed is a short interaction of a methylene hydrogen atom with the π-electron system of a phenyl ring in an adjacent molecule.

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_r = 267.29
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.148
S = 1.17
2152 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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⋯Cg^iv	0.97	2.82	3.645	144
Symmetry codes: (i) -x+2, -y+2, -z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1; (iv) x+1, y+1, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

The crystal structure of 2,3-dihydro-5-carboxanilide-6-methyl-1,4-oxathiin-4,4-dioxide (oxycarboxin, also known as Plantvax^R) was determined as part of a larger project involving the structures of fungicides (Baughman & Paulos, 2005). It is the dioxide form of its parent compound, carboxin, and is a member of the oxathiin class of systemic (works from within the plant system) fungicides. The mode of action of this class of compounds is to inhibit succinate oxidation of succinate dehydrogenase in the fungal class Basiomycetes (Ulrich & Mathre, 1972).

The molecules of the title structure (Fig. 1) are interconnected by intermolecular hydrogen bonds, while the molecule itself contains intramolecular hydrogen bonds (Tab. 1). The N1—H1A···O3—S1 and the C8—H8···O4—C6 intramolecular hydrogen bonds restrict all of the torsion angles around the N1—C6, N1—C7, and C3—C6 bonds. H1C is observed to be interacting with the π-electron system of the adjacent phenyl ring at 1 + x, 1 + y, z (Fig. 1, Tab. 1).

The C1//C2//S1//C3//C4//O1 ring is nonplanar; C1 and C2 are located +0.435 (6) and -0.398 (6) Å, respectively, from the 4-membered planar S1//C3//C4//O4 group, which has an r.m.s. deviation from the mean plane equal to 0.030 Å.

Related literature top

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 top

A 99.9% pure sample of the title compound was purchased from Sigma-Aldrich. Crystals were grown by slow evaporation of a solution in EtOH.

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS (Bruker, 1996); data reduction: XSCANS (Bruker, 1996); 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 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The title molecule showing the labeling of the non-H atoms. The displacement ellipsoids are drawn at the 50% probability levels; the H atoms are drawn as small spheres of arbitrary radius. Intramolecular hydrogen bonds involving H1a and H8 are indicated by dashed lines.

2-methyl-4,4-dioxo-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide top

Crystal data top

C₁₂H₁₃NO₄S	Z = 2
M_r = 267.29	F(000) = 280
Triclinic, P1	D_x = 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

Data collection top

Bruker P4 diffractometer	1884 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.3°, θ_min = 2.7°
θ/2θ scans	h = −7→7
Absorption correction: integration (XSHELL; Bruker, 1999)	k = −9→9
T_min = 0.888, T_max = 0.959	l = −7→15
2152 measured reflections	3 standard reflections every 100 reflections
2152 independent reflections	intensity decay: 1.2%

Refinement top

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(F_o²) + (0.0317P)² + 1.2476P] where P = (F_o² + 2F_c²)/3
2152 reflections	(Δ/σ)_max < 0.001
165 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³
51 constraints

Crystal data top

C₁₂H₁₃NO₄S	γ = 106.876 (5)°
M_r = 267.29	V = 600.59 (7) Å³
Triclinic, P1	Z = 2
a = 5.9985 (4) Å	Mo Kα radiation
b = 8.3178 (6) Å	µ = 0.28 mm⁻¹
c = 13.1333 (8) Å	T = 295 K
α = 104.702 (4)°	0.54 × 0.44 × 0.16 mm
β = 93.180 (5)°

Data collection top

Bruker P4 diffractometer	1884 reflections with I > 2σ(I)
Absorption correction: integration (XSHELL; Bruker, 1999)	R_int = 0.000
T_min = 0.888, T_max = 0.959	3 standard reflections every 100 reflections
2152 measured reflections	intensity decay: 1.2%
2152 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.17	Δρ_max = 0.26 e Å⁻³
2152 reflections	Δρ_min = −0.30 e Å⁻³
165 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg^iv	0.97	2.82	3.645	144

Symmetry codes: (i) −x+2, −y+2, −z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃NO₄S
M_r	267.29
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	5.9985 (4), 8.3178 (6), 13.1333 (8)
α, β, γ (°)	104.702 (4), 93.180 (5), 106.876 (5)
V (Å³)	600.59 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.54 × 0.44 × 0.16

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	Integration (XSHELL; Bruker, 1999)
T_min, T_max	0.888, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	2152, 2152, 1884
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.148, 1.17
No. of reflections	2152
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.30

Computer programs: XSCANS (Bruker, 1996), XSCANS (Bruker, 1996), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected torsion angles (º) top

C7—N1—C6—O4	−4.3 (6)	C6—N1—C7—C8	−44.9 (6)
S1—C3—C6—N1	22.9 (5)

Hydrogen-bond geometry (Å, º) top

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···Cg^iv	0.97	2.82	3.645	144

Symmetry codes: (i) −x+2, −y+2, −z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) x+1, y+1, z.

Acknowledgements

This material is based upon work supported by the National Science Foundation under grant No. DUE-0431664.

References

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Volume 66| Part 10| October 2010| Page o2654

doi:10.1107/S1600536810037669

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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