3,3-Bis(methyl­thio)-2-oxo-N-phenylpropan­amide

Deschamps, J.R.; Suwandi, L.S.; Konaklieva, M.

doi:10.1107/S1600536803002769

3,3-Bis(methylthio)-2-oxo-N-phenylpropanamide

J. R. Deschamps, L. S. Suwandi and M. Konaklieva

The title compound, C₁₂H₁₅NO₃S₂, is the result of a rearrangement of a bis(methylthio)-β-lactam after prolonged exposure to silica gel. The compound crystallizes with a single molecule in the asymmetric unit.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803002769/om6129sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803002769/om6129Isup2.hkl Contains datablock I

CCDC reference: 206772

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Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.044
wR factor = 0.120
Data-to-parameter ratio = 13.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           67.10
         From the CIF: _reflns_number_total               2328
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         2456
         Completeness (_total/calc)             94.79%
          Alert C: < 95% complete

PLAT_369  Alert C Long   C(sp2)-C(sp2) Bond  C2     -   C3     =       1.54 Ang.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           67.10
         From the CIF: _reflns_number_total               2328
         From the CIF: _diffrn_reflns_limit_ max hkl   33.    5.   20.
         From the CIF: _diffrn_reflns_limit_ min hkl  -33.   -6.  -17.
         TEST1: Expected hkl limits for theta max
         Calculated maximum hkl   35.    6.   20.
         Calculated minimum hkl  -35.   -6.  -20.
          ALERT: Expected hkl max differ from CIF values


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000) and XPREP (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top

Crystal data top

C₁₂H₁₅NO₃S₂	F(000) = 1200
M_r = 285.37	D_x = 1.384 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 2025 reflections
a = 29.7331 (5) Å	θ = 8.4–66.9°
b = 5.3499 (1) Å	µ = 3.54 mm⁻¹
c = 17.4428 (3) Å	T = 296 K
β = 99.099 (1)°	Rod, pale yellow
V = 2739.7 (1) Å³	0.70 × 0.16 × 0.07 mm
Z = 8

Data collection top

Bruker SMART 6000 CCD diffractometer	2328 independent reflections
Radiation source: rotating anode	1977 reflections with I > 2σ(I)
Gobel optics monochromator	R_int = 0.049
ω scans	θ_max = 67.1°, θ_min = 5.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −33→33
T_min = 0.527, T_max = 0.776	k = −6→5
8381 measured reflections	l = −17→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.081P)² + 0.0191P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.003
2328 reflections	Δρ_max = 0.24 e Å⁻³
168 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (3)

Special details top

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.

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	1.00825 (2)	0.21600 (10)	0.63803 (3)	0.0575 (2)
C1A	1.02491 (8)	0.5234 (4)	0.61350 (14)	0.0710 (6)
H1AA	1.0562	0.5215	0.6061	0.106*
H1AB	1.0213	0.6367	0.6548	0.106*
H1AC	1.0061	0.5770	0.5665	0.106*
S2	0.90875 (2)	0.28954 (11)	0.55865 (3)	0.0700 (2)
C2A	0.91947 (8)	0.0014 (5)	0.51307 (12)	0.0744 (6)
H2AA	0.8994	−0.0131	0.4644	0.112*
H2AB	0.9143	−0.1355	0.5462	0.112*
H2AC	0.9505	−0.0022	0.5041	0.112*
N1	0.87084 (6)	−0.0359 (3)	0.76384 (9)	0.0494 (4)
H1	0.8806 (8)	−0.171 (4)	0.7569 (12)	0.059*
C1'	0.83335 (6)	−0.0167 (3)	0.80527 (9)	0.0456 (4)
C2'	0.80185 (7)	0.1726 (4)	0.79172 (11)	0.0545 (5)
H2'A	0.8050	0.2935	0.7547	0.065*
C3'	0.76566 (7)	0.1862 (4)	0.83212 (11)	0.0558 (5)
H3'A	0.7445	0.3148	0.8221	0.067*
C4'	0.76094 (6)	0.0066 (4)	0.88790 (10)	0.0541 (5)
O4'	0.72688 (5)	0.0047 (3)	0.93192 (8)	0.0743 (5)
C4'A	0.69421 (8)	0.2021 (5)	0.92141 (15)	0.0797 (7)
H4'A	0.6780	0.1979	0.8692	0.120*
H4'B	0.7095	0.3597	0.9307	0.120*
H4'C	0.6731	0.1814	0.9572	0.120*
C5'	0.79211 (7)	−0.1880 (4)	0.90041 (11)	0.0592 (5)
H5'A	0.7888	−0.3109	0.9368	0.071*
C6'	0.82774 (7)	−0.2000 (4)	0.85946 (10)	0.0536 (5)
H6'A	0.8483	−0.3318	0.8680	0.064*
C2	0.89239 (6)	0.1586 (4)	0.73687 (10)	0.0496 (5)
O2	0.88393 (5)	0.3790 (3)	0.74467 (9)	0.0650 (4)
C3	0.93126 (6)	0.0747 (3)	0.69416 (10)	0.0493 (4)
O3	0.94307 (5)	−0.1415 (3)	0.69422 (8)	0.0610 (4)
C4	0.95009 (7)	0.2770 (3)	0.64857 (11)	0.0527 (5)
H4A	0.9489	0.4357	0.6762	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0640 (4)	0.0403 (4)	0.0752 (3)	0.0001 (2)	0.0326 (2)	0.0014 (2)
C1A	0.0762 (14)	0.0562 (15)	0.0873 (13)	−0.0115 (11)	0.0337 (11)	0.0084 (11)
S2	0.0792 (4)	0.0551 (4)	0.0803 (4)	0.0185 (3)	0.0267 (3)	0.0137 (3)
C2A	0.0849 (16)	0.0679 (17)	0.0712 (11)	0.0025 (12)	0.0149 (11)	−0.0049 (11)
N1	0.0593 (9)	0.0341 (10)	0.0600 (7)	−0.0033 (7)	0.0257 (7)	−0.0017 (7)
C1'	0.0498 (10)	0.0387 (11)	0.0501 (7)	−0.0058 (7)	0.0137 (7)	0.0001 (7)
C2'	0.0576 (11)	0.0468 (13)	0.0615 (9)	−0.0022 (9)	0.0167 (8)	0.0108 (9)
C3'	0.0494 (10)	0.0490 (13)	0.0708 (10)	0.0023 (8)	0.0151 (8)	0.0108 (9)
C4'	0.0486 (10)	0.0556 (13)	0.0609 (9)	−0.0058 (9)	0.0173 (8)	0.0047 (9)
O4'	0.0620 (9)	0.0831 (12)	0.0864 (9)	0.0083 (8)	0.0381 (7)	0.0203 (8)
C4'A	0.0560 (13)	0.091 (2)	0.0976 (16)	0.0083 (11)	0.0293 (12)	0.0109 (14)
C5'	0.0624 (12)	0.0534 (14)	0.0658 (10)	−0.0004 (9)	0.0226 (9)	0.0176 (9)
C6'	0.0582 (11)	0.0422 (12)	0.0629 (10)	0.0014 (8)	0.0178 (8)	0.0088 (8)
C2	0.0598 (11)	0.0348 (11)	0.0585 (9)	−0.0057 (8)	0.0222 (8)	−0.0022 (8)
O2	0.0755 (9)	0.0329 (8)	0.0976 (9)	−0.0031 (7)	0.0472 (8)	−0.0080 (7)
C3	0.0618 (11)	0.0310 (11)	0.0605 (9)	−0.0017 (8)	0.0265 (8)	−0.0012 (8)
O3	0.0839 (10)	0.0293 (8)	0.0784 (8)	0.0009 (7)	0.0389 (7)	0.0002 (7)
C4	0.0686 (13)	0.0283 (11)	0.0691 (11)	−0.0003 (8)	0.0354 (10)	0.0004 (8)

Geometric parameters (Å, º) top

S1—C1A	1.789 (2)	C3'—C4'	1.390 (3)
S1—C4	1.797 (2)	C3'—H3'A	0.9300
C1A—H1AA	0.9600	C4'—O4'	1.364 (2)
C1A—H1AB	0.9600	C4'—C5'	1.388 (3)
C1A—H1AC	0.9600	O4'—C4'A	1.427 (3)
S2—C2A	1.786 (2)	C4'A—H4'A	0.9600
S2—C4	1.835 (2)	C4'A—H4'B	0.9600
C2A—H2AA	0.9600	C4'A—H4'C	0.9600
C2A—H2AB	0.9600	C5'—C6'	1.370 (3)
C2A—H2AC	0.9600	C5'—H5'A	0.9300
N1—C2	1.345 (2)	C6'—H6'A	0.9300
N1—C1'	1.425 (2)	C2—O2	1.218 (2)
N1—H1	0.80 (2)	C2—C3	1.538 (2)
C1'—C2'	1.374 (3)	C3—O3	1.209 (2)
C1'—C6'	1.391 (2)	C3—C4	1.503 (2)
C2'—C3'	1.378 (3)	C4—H4A	0.9800
C2'—H2'A	0.9300

C1A—S1—C4	99.48 (10)	O4'—C4'—C3'	124.40 (19)
S1—C1A—H1AA	109.5	C5'—C4'—C3'	119.32 (18)
S1—C1A—H1AB	109.5	C4'—O4'—C4'A	118.24 (17)
H1AA—C1A—H1AB	109.5	O4'—C4'A—H4'A	109.5
S1—C1A—H1AC	109.5	O4'—C4'A—H4'B	109.5
H1AA—C1A—H1AC	109.5	H4'A—C4'A—H4'B	109.5
H1AB—C1A—H1AC	109.5	O4'—C4'A—H4'C	109.5
C2A—S2—C4	101.91 (9)	H4'A—C4'A—H4'C	109.5
S2—C2A—H2AA	109.5	H4'B—C4'A—H4'C	109.5
S2—C2A—H2AB	109.5	C6'—C5'—C4'	120.38 (17)
H2AA—C2A—H2AB	109.5	C6'—C5'—H5'A	119.8
S2—C2A—H2AC	109.5	C4'—C5'—H5'A	119.8
H2AA—C2A—H2AC	109.5	C5'—C6'—C1'	120.47 (19)
H2AB—C2A—H2AC	109.5	C5'—C6'—H6'A	119.8
C2—N1—C1'	125.15 (17)	C1'—C6'—H6'A	119.8
C2—N1—H1	116.3 (17)	O2—C2—N1	126.26 (17)
C1'—N1—H1	118.5 (17)	O2—C2—C3	121.41 (16)
C2'—C1'—C6'	119.01 (17)	N1—C2—C3	112.32 (16)
C2'—C1'—N1	122.18 (16)	O3—C3—C4	123.86 (16)
C6'—C1'—N1	118.78 (17)	O3—C3—C2	121.29 (16)
C1'—C2'—C3'	121.15 (17)	C4—C3—C2	114.68 (15)
C1'—C2'—H2'A	119.4	C3—C4—S1	111.61 (13)
C3'—C2'—H2'A	119.4	C3—C4—S2	102.90 (13)
C2'—C3'—C4'	119.64 (19)	S1—C4—S2	116.40 (10)
C2'—C3'—H3'A	120.2	C3—C4—H4A	108.5
C4'—C3'—H3'A	120.2	S1—C4—H4A	108.5
O4'—C4'—C5'	116.27 (17)	S2—C4—H4A	108.5

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3,3-Bis(methyl­thio)-2-oxo-N-phenylpropan­amide

Supporting information

Key indicators

checkCIF results

3,3-Bis(methylthio)-2-oxo-N-phenylpropanamide