(E)-O-Ethyl N-(4-methyl­phen­yl)thio­carbamate

The title compound, C₁₀H₁₃NOS, displays an E conformation about the central C—N bond and exists in the thione form. N—H...S hydrogen-bonding inter­actions link centrosymmetrically related mol­ecules into dimers.

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.056
• wR factor = 0.158
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.790     1.000
            Tmin(prime) and Tmax expected:      0.916     0.992
            RR(prime) =      0.856
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         300 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.13
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(E)—O-Ethyl N-(4-methylphenyl)thiocarbamate

Crystal data

C10H13NOS	Z = 2
Mr = 195.27	F(000) = 208
Triclinic, P1	Dx = 1.247 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 5.9054 (8) Å	Cell parameters from 1346 reflections
b = 7.4497 (10) Å	θ = 2.8–30.0°
c = 11.9638 (16) Å	µ = 0.27 mm^−1
α = 89.321 (3)°	T = 223 K
β = 82.207 (3)°	Plate, colourless
γ = 85.931 (3)°	0.32 × 0.13 × 0.03 mm
V = 520.15 (12) Å^3

Data collection

Bruker SMART CCD diffractometer	1824 independent reflections
Radiation source: fine-focus sealed tube	1482 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω and φ scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −5→7
Tmin = 0.790, Tmax = 1	k = −8→8
3011 measured reflections	l = −14→14

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0932P)^2 + 0.0601P] where P = (Fo^2 + 2Fc^2)/3
1824 reflections	(Δ/σ)max = 0.001
119 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.26 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
S1	1.22909 (14)	0.21652 (11)	−0.01959 (6)	0.0469 (3)
O1	1.0880 (3)	0.4060 (2)	0.16626 (15)	0.0357 (5)
N1	0.8889 (4)	0.1711 (3)	0.14337 (19)	0.0361 (6)
H1	0.8692	0.0800	0.1018	0.043*
C1	1.0641 (5)	0.2676 (4)	0.1017 (2)	0.0320 (6)
C2	0.7298 (4)	0.1909 (3)	0.2431 (2)	0.0295 (6)
C3	0.5264 (5)	0.1079 (4)	0.2452 (2)	0.0337 (6)
H3	0.4978	0.0465	0.1809	0.040*
C4	0.3660 (5)	0.1143 (4)	0.3401 (2)	0.0359 (7)
H4	0.2299	0.0562	0.3396	0.043*
C5	0.4008 (4)	0.2049 (4)	0.4369 (2)	0.0329 (6)
C5'	0.2239 (5)	0.2134 (4)	0.5399 (3)	0.0427 (7)
H5'a	0.2996	0.2131	0.6070	0.064*
H5'b	0.1328	0.1098	0.5414	0.064*
H5'c	0.1251	0.3228	0.5379	0.064*
C6	0.6050 (5)	0.2857 (4)	0.4336 (2)	0.0349 (6)
H6	0.6334	0.3465	0.4981	0.042*
C7	0.7698 (5)	0.2810 (4)	0.3393 (2)	0.0350 (7)
H7	0.9067	0.3378	0.3401	0.042*
C8	1.2741 (5)	0.5231 (4)	0.1335 (3)	0.0407 (7)
H8A	1.2507	0.5888	0.0641	0.049*
H8B	1.4217	0.4525	0.1209	0.049*
C9	1.2681 (7)	0.6499 (5)	0.2291 (3)	0.0745 (13)
H9A	1.3888	0.7318	0.2120	0.112*
H9B	1.2910	0.5826	0.2970	0.112*
H9C	1.1207	0.7181	0.2406	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0504 (5)	0.0507 (5)	0.0365 (5)	−0.0208 (4)	0.0158 (3)	−0.0150 (4)
O1	0.0410 (11)	0.0300 (10)	0.0342 (11)	−0.0133 (8)	0.0079 (9)	−0.0063 (8)
N1	0.0401 (13)	0.0357 (13)	0.0313 (13)	−0.0129 (10)	0.0059 (10)	−0.0120 (10)
C1	0.0348 (15)	0.0316 (14)	0.0294 (15)	−0.0074 (11)	−0.0004 (11)	−0.0011 (11)
C2	0.0307 (14)	0.0272 (13)	0.0294 (14)	−0.0045 (10)	0.0018 (11)	−0.0003 (11)
C3	0.0352 (15)	0.0332 (15)	0.0325 (15)	−0.0067 (11)	−0.0009 (12)	−0.0062 (12)
C4	0.0279 (14)	0.0348 (15)	0.0436 (17)	−0.0071 (11)	0.0033 (12)	−0.0028 (12)
C5	0.0311 (15)	0.0292 (14)	0.0352 (15)	0.0010 (11)	0.0045 (12)	0.0005 (11)
C5'	0.0407 (17)	0.0432 (17)	0.0402 (18)	−0.0020 (13)	0.0091 (13)	−0.0011 (13)
C6	0.0383 (16)	0.0358 (15)	0.0295 (15)	−0.0039 (12)	0.0011 (12)	−0.0073 (12)
C7	0.0337 (15)	0.0389 (15)	0.0318 (15)	−0.0101 (12)	0.0023 (12)	−0.0045 (12)
C8	0.0424 (17)	0.0377 (16)	0.0402 (17)	−0.0192 (13)	0.0095 (13)	−0.0039 (13)
C9	0.092 (3)	0.068 (2)	0.060 (2)	−0.052 (2)	0.028 (2)	−0.0239 (19)

Geometric parameters (Å, º)

S1—C1	1.666 (3)	C5—C5'	1.503 (4)
O1—C1	1.322 (3)	C5'—H5'a	0.9700
O1—C8	1.461 (3)	C5'—H5'b	0.9700
N1—C1	1.339 (3)	C5'—H5'c	0.9700
N1—C2	1.417 (3)	C6—C7	1.385 (4)
N1—H1	0.8700	C6—H6	0.9400
C2—C3	1.386 (4)	C7—H7	0.9400
C2—C7	1.394 (4)	C8—C9	1.487 (5)
C3—C4	1.375 (4)	C8—H8A	0.9800
C3—H3	0.9400	C8—H8B	0.9800
C4—C5	1.394 (4)	C9—H9A	0.9700
C4—H4	0.9400	C9—H9B	0.9700
C5—C6	1.381 (4)	C9—H9C	0.9700
C1—O1—C8	119.5 (2)	C5—C5'—H5'c	109.5
C1—N1—C2	131.5 (2)	H5'a—C5'—H5'c	109.5
C1—N1—H1	114.2	H5'b—C5'—H5'c	109.5
C2—N1—H1	114.2	C5—C6—C7	122.9 (3)
S1—C1—O1	124.73 (19)	C5—C6—H6	118.6
S1—C1—N1	122.5 (2)	C7—C6—H6	118.6
O1—C1—N1	112.7 (2)	C6—C7—C2	119.1 (2)
C3—C2—C7	118.8 (2)	C6—C7—H7	120.5
C3—C2—N1	116.9 (2)	C2—C7—H7	120.5
C7—C2—N1	124.2 (2)	O1—C8—C9	105.7 (2)
C4—C3—C2	120.9 (3)	O1—C8—H8A	110.6
C4—C3—H3	119.6	C9—C8—H8A	110.6
C2—C3—H3	119.6	O1—C8—H8B	110.6
C3—C4—C5	121.4 (3)	C9—C8—H8B	110.6
C3—C4—H4	119.3	H8A—C8—H8B	108.7
C5—C4—H4	119.3	C8—C9—H9A	109.5
C6—C5—C4	116.9 (2)	C8—C9—H9B	109.5
C6—C5—C5'	121.8 (3)	H9A—C9—H9B	109.5
C4—C5—C5'	121.3 (3)	C8—C9—H9C	109.5
C5—C5'—H5'a	109.5	H9A—C9—H9C	109.5
C5—C5'—H5'b	109.5	H9B—C9—H9C	109.5
H5'a—C5'—H5'b	109.5
C8—O1—C1—N1	179.0 (2)	C3—C4—C5—C6	−0.9 (4)
C8—O1—C1—S1	−1.5 (4)	C3—C4—C5—C5'	179.4 (3)
C2—N1—C1—O1	−0.4 (4)	C4—C5—C6—C7	0.9 (4)
C2—N1—C1—S1	−180.0 (2)	C5'—C5—C6—C7	−179.4 (3)
C1—N1—C2—C7	−23.3 (5)	C3—C2—C7—C6	−0.1 (4)
C1—N1—C2—C3	159.4 (3)	N1—C2—C7—C6	−177.4 (2)
C7—C2—C3—C4	0.1 (4)	C5—C6—C7—C2	−0.4 (4)
N1—C2—C3—C4	177.6 (2)	C1—O1—C8—C9	−174.1 (3)
C2—C3—C4—C5	0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1^i	0.87	2.56	3.418 (2)	168

Symmetry code: (i) −x+2, −y, −z.