(E)-O-Ethyl N-(3-methoxy­phen­yl)thio­carbamate

The mol­ecule of the title compound, C₁₀H₁₃NO₂S, is not planar and displays an E conformation about the (S)C—N bond. It is in the thione form. Intra­molecular C—H...O and inter­molecular N—H...S hydrogen bonds are present.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.057
• wR factor = 0.152
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

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Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
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S1. Comment

The title compound, (I), was investigated as a part of a study of related O-alkyl thiocarbamate molecules (Ho et al., 2005) and their phosphine gold(I) complexes (Ho et al., 2006).

In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The dihedral angles between the planar A (O2/C6/C10) and B (S1/O1/N1/C1—C4) moieties and benzene ring C (C1—C6) are A/B = 8.72 (3)°, A/C = 3.12 (3)° and B/C = 11.47 (2)°. The C3—S1 [1.663 (2) Å] bond distance indicates that the molecule is in the thione form; the conformation about the central C—N bond is E.

The intramolecular C—H···O and intermolecular N—H···S hydrogen bonds (Table 1) may be effective in the stabilization of the crystal structure.

Related literature

For general backgroud, see: Allen et al. (1987). For related literature, see: Ho et al. (2005, 2006).

S2. Experimental

Compound (I) was prepared by refluxing 3-methoxyphenyl isothiocyanate (1.65 g, 10 mmol) with absolute ethanol (50 ml) using a literature procedure (Ho et al., 2005). The white precipitate, which was obtained upon concentration of the reaction solution, was dissolved in hot dichloromethane and layered with ethanol, which resulted in the formation of colorless crystals (yield: 1.32 g, 80%, m.p. 425–427 K).

S3. Refinement

H atom of NH group was located in difference syntheses and refined isotropically [N—H = 0.87 (3) Å and U_iso(H) = 0.059 (8) Ų]. The remaining H atoms were positioned geometrically, with C—H = 0.93, 0.96 and 0.96 Å for aromatic, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with U_iso(H) = xU_eq(C), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick,1997); program(s) used to refine structure: SHELXL97 (Sheldrick,1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)..

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The synthetic route for the formation of the title compound.

(E)—O-Ethyl N-(3-methoxyphenyl)thiocarbamate

Crystal data

C10H13NO2S	F(000) = 448
Mr = 211.27	Dx = 1.305 Mg m^−3
Monoclinic, P21/n	Melting point: 425(2) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.931 (3) Å	Cell parameters from 1520 reflections
b = 4.866 (1) Å	θ = 2.7–24.9°
c = 15.538 (3) Å	µ = 0.28 mm^−1
β = 107.75 (3)°	T = 294 K
V = 1075.2 (4) Å^3	Block, colorless
Z = 4	0.46 × 0.26 × 0.20 mm

Data collection

Bruker APEX II diffractometer	2089 independent reflections
Radiation source: fine-focus sealed tube	1596 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 0→18
Tmin = 0.879, Tmax = 0.946	k = 0→5
2170 measured reflections	l = −19→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0832P)^2 + 0.1652P] where P = (Fo^2 + 2Fc^2)/3
2089 reflections	(Δ/σ)max = 0.001
133 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.46 e Å^−3

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6768 (2)	1.1857 (7)	0.39864 (18)	0.0726 (8)
H1A	0.6188	1.2469	0.4067	0.109*
H1B	0.7273	1.3002	0.4333	0.109*
H1C	0.6885	0.9988	0.4187	0.109*
C2	0.67037 (17)	1.2031 (6)	0.30106 (17)	0.0558 (6)
H2A	0.6543	1.3885	0.2787	0.067*
H2B	0.7299	1.1531	0.2923	0.067*
C3	0.56958 (16)	1.0016 (5)	0.16453 (15)	0.0472 (6)
C4	0.44867 (16)	0.6494 (5)	0.17244 (16)	0.0473 (6)
C5	0.46054 (18)	0.6384 (5)	0.26386 (17)	0.0557 (6)
H5	0.5033	0.7549	0.3032	0.067*
C6	0.40873 (18)	0.4539 (5)	0.29714 (18)	0.0548 (6)
C7	0.34422 (18)	0.2818 (6)	0.2405 (2)	0.0613 (7)
H7	0.3093	0.1585	0.2630	0.074*
C8	0.3328 (2)	0.2977 (6)	0.1490 (2)	0.0705 (8)
H8	0.2888	0.1843	0.1096	0.085*
C9	0.38430 (19)	0.4755 (6)	0.11432 (18)	0.0624 (7)
H9	0.3762	0.4795	0.0526	0.075*
C10	0.3885 (3)	0.2534 (7)	0.4304 (2)	0.0796 (9)
H10A	0.3212	0.2683	0.4096	0.119*
H10B	0.4106	0.2764	0.4948	0.119*
H10C	0.4068	0.0757	0.4149	0.119*
N1	0.49870 (15)	0.8261 (4)	0.13049 (15)	0.0520 (5)
O1	0.59723 (11)	1.0119 (4)	0.25404 (10)	0.0557 (5)
O2	0.42811 (17)	0.4596 (5)	0.38897 (14)	0.0848 (7)
S1	0.61763 (5)	1.18383 (16)	0.09943 (4)	0.0622 (3)
H1	0.4762 (19)	0.813 (6)	0.072 (2)	0.059 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0718 (17)	0.095 (2)	0.0482 (14)	−0.0156 (17)	0.0135 (13)	−0.0013 (15)
C2	0.0533 (13)	0.0623 (16)	0.0503 (13)	−0.0124 (12)	0.0134 (11)	0.0039 (12)
C3	0.0488 (12)	0.0462 (13)	0.0456 (12)	0.0041 (11)	0.0126 (9)	0.0063 (10)
C4	0.0500 (12)	0.0399 (13)	0.0509 (12)	0.0040 (10)	0.0136 (10)	0.0069 (10)
C5	0.0599 (14)	0.0531 (15)	0.0545 (14)	−0.0074 (12)	0.0181 (11)	0.0019 (12)
C6	0.0584 (14)	0.0501 (14)	0.0593 (14)	0.0019 (12)	0.0230 (12)	0.0057 (12)
C7	0.0529 (14)	0.0526 (16)	0.0768 (18)	−0.0034 (12)	0.0175 (12)	0.0162 (14)
C8	0.0651 (17)	0.0644 (19)	0.0716 (18)	−0.0197 (14)	0.0052 (14)	0.0072 (15)
C9	0.0656 (15)	0.0607 (17)	0.0528 (14)	−0.0098 (13)	0.0059 (12)	0.0093 (13)
C10	0.100 (2)	0.078 (2)	0.0716 (19)	−0.0127 (18)	0.0423 (17)	0.0170 (16)
N1	0.0602 (12)	0.0513 (13)	0.0428 (11)	−0.0061 (10)	0.0134 (9)	0.0024 (9)
O1	0.0588 (10)	0.0622 (11)	0.0434 (9)	−0.0128 (8)	0.0116 (7)	0.0052 (8)
O2	0.1115 (16)	0.0883 (16)	0.0626 (12)	−0.0362 (14)	0.0383 (12)	0.0054 (11)
S1	0.0624 (4)	0.0757 (5)	0.0499 (4)	−0.0128 (3)	0.0190 (3)	0.0094 (3)

Geometric parameters (Å, º)

N1—H1	0.87 (3)	C5—C6	1.384 (3)
C1—C2	1.492 (4)	C5—H5	0.9300
C1—H1A	0.9600	C6—O2	1.367 (3)
C1—H1B	0.9600	C6—C7	1.374 (4)
C1—H1C	0.9600	C7—C8	1.381 (4)
C2—O1	1.451 (3)	C7—H7	0.9300
C2—H2A	0.9600	C8—C9	1.372 (4)
C2—H2B	0.9600	C8—H8	0.9300
C3—O1	1.326 (3)	C9—H9	0.9300
C3—N1	1.337 (3)	C10—O2	1.415 (3)
C3—S1	1.663 (2)	C10—H10A	0.9600
C4—C5	1.378 (3)	C10—H10B	0.9600
C4—C9	1.388 (4)	C10—H10C	0.9600
C4—N1	1.421 (3)
O1—C2—C1	106.3 (2)	O2—C6—C5	114.3 (2)
O1—C3—N1	113.3 (2)	C7—C6—C5	121.2 (2)
O1—C3—S1	124.31 (18)	C6—C7—C8	117.9 (2)
N1—C3—S1	122.42 (18)	C9—C8—C7	122.1 (3)
C5—C4—C9	119.5 (2)	C8—C9—C4	119.3 (3)
C5—C4—N1	125.2 (2)	C3—N1—C4	131.9 (2)
C9—C4—N1	115.3 (2)	C6—N1—H1B	82.0
C4—C5—C6	120.0 (2)	C3—O1—C2	119.90 (18)
O2—C6—C7	124.4 (2)	C6—O2—C10	118.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1^i	0.87 (3)	2.60 (3)	3.464 (2)	170.0 (3)
C5—H5···O1	0.93	2.18	2.772 (3)	120

Symmetry code: (i) −x+1, −y+2, −z.