O-(3,5-Di­methoxy­phenyl) N,N-di­methyl­thio­carbamate

Vande Velde, C.M.L.; Geise, H.J.; Blockhuys, F.

doi:10.1107/S1600536804000467

O-(3,5-Dimethoxyphenyl) N,N-dimethylthiocarbamate

C. M. L. Vande Velde, H. J. Geise and F. Blockhuys

Molecules of the title compound, C₁₁H₁₅NO₃S, display a conformation where the aromatic group is almost orthogonal to the thiocarbamate moiety. The packing arrangement is such that two parallel thiocarbamate moieties are sandwiched between two phenyl rings, with molecules separated by normal van der Waals contacts.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000467/tk6147sup1.cif Contains datablocks thiocbm, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000467/tk6147Isup2.hkl Contains datablock I

CCDC reference: 234865

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.034
wR factor = 0.097
Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....        H8A
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....        H8B
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....        H8C
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....        H9A
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....        H9B
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....        H9C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C8       =       5.37 su
PLAT350_ALERT_3_C Short   C-H Bond (0.96A)   C4     -   H4       =       0.83 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 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
   1 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

O-(3,5-dimethoxyphenyl)-N,N-dimethylthiocarbamate top

Crystal data top

C₁₁H₁₅NO₃S	D_x = 1.323 Mg m⁻³
M_r = 241.30	Melting point = 349–351 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ac 2ab	Cell parameters from 25 reflections
a = 13.113 (3) Å	θ = 6–18°
b = 9.999 (3) Å	µ = 0.26 mm⁻¹
c = 18.474 (3) Å	T = 293 K
V = 2422.2 (10) Å³	Prism, colourless
Z = 8	0.4 × 0.2 × 0.2 mm
F(000) = 1024

Data collection top

Enraf-Nonius MACH3 diffractometer	R_int = 0.059
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 2.2°
Graphite monochromator	h = −15→15
ω/2θ scans	k = 0→12
4457 measured reflections	l = 0→22
2241 independent reflections	3 standard reflections every 60 min
1159 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0445P)²] where P = (F_o² + 2F_c²)/3
2241 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻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	0.03899 (6)	0.03280 (7)	0.63759 (4)	0.0547 (2)
O5	0.23043 (14)	0.42672 (18)	0.77810 (9)	0.0578 (5)
O3	−0.02344 (14)	0.57373 (17)	0.61201 (9)	0.0573 (5)
C5	0.18068 (19)	0.4051 (2)	0.71422 (13)	0.0440 (6)
C1	0.14130 (19)	0.2892 (2)	0.60666 (12)	0.0430 (6)
O1	0.16281 (13)	0.18447 (17)	0.55796 (9)	0.0498 (5)
N1	0.14936 (16)	−0.0247 (2)	0.52075 (10)	0.0460 (5)
C4	0.10547 (19)	0.4986 (3)	0.69767 (15)	0.0451 (6)
C6	0.1985 (2)	0.2984 (3)	0.66914 (13)	0.0458 (6)
C7	0.11917 (19)	0.0619 (2)	0.57030 (12)	0.0408 (6)
C8	0.2209 (2)	0.0079 (3)	0.46337 (15)	0.0650 (9)
H8A	0.1873 (6)	0.014 (2)	0.4209 (8)	0.098*
H8B	0.2687 (12)	−0.0565 (15)	0.4604 (7)	0.098*
H8C	0.2510 (13)	0.0869 (17)	0.4732 (6)	0.098*
C11	0.3139 (2)	0.3408 (4)	0.79478 (18)	0.0622 (8)
C3	0.05107 (18)	0.4872 (2)	0.63404 (13)	0.0442 (6)
C2	0.0696 (2)	0.3813 (3)	0.58678 (14)	0.0463 (6)
C9	0.1089 (2)	−0.1610 (2)	0.52162 (16)	0.0620 (8)
H9A	0.1424 (11)	−0.2112 (10)	0.5582 (9)	0.093*
H9B	0.1203 (12)	−0.2018 (9)	0.4759 (8)	0.093*
H9C	0.0378 (12)	−0.1585 (3)	0.5313 (10)	0.093*
C10	−0.0568 (3)	0.6730 (3)	0.6621 (2)	0.0671 (8)
H6	0.2472 (18)	0.238 (3)	0.6808 (11)	0.046 (7)*
H3A	−0.083 (2)	0.629 (3)	0.7078 (17)	0.081 (10)*
H3B	−0.002 (2)	0.730 (3)	0.6761 (15)	0.074 (10)*
H3C	−0.110 (2)	0.722 (3)	0.6358 (15)	0.083 (10)*
H4	0.0943 (17)	0.561 (2)	0.7263 (12)	0.044 (7)*
H5A	0.3665 (19)	0.348 (2)	0.7531 (14)	0.059 (8)*
H5B	0.289 (2)	0.242 (3)	0.8017 (16)	0.088 (10)*
H5C	0.345 (2)	0.375 (3)	0.8371 (15)	0.071 (9)*
H2	0.0308 (17)	0.377 (2)	0.5428 (11)	0.042 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0651 (4)	0.0491 (4)	0.0499 (4)	−0.0062 (3)	0.0105 (4)	−0.0024 (3)
O5	0.0589 (12)	0.0665 (13)	0.0479 (10)	0.0047 (10)	−0.0069 (9)	−0.0152 (9)
O3	0.0652 (12)	0.0483 (11)	0.0583 (11)	0.0088 (9)	−0.0042 (10)	−0.0007 (8)
C5	0.0434 (14)	0.0468 (15)	0.0418 (14)	−0.0070 (12)	0.0082 (11)	−0.0054 (12)
C1	0.0498 (14)	0.0399 (14)	0.0394 (13)	−0.0100 (12)	0.0110 (12)	−0.0085 (11)
O1	0.0606 (11)	0.0414 (10)	0.0475 (10)	−0.0092 (9)	0.0130 (9)	−0.0115 (8)
N1	0.0537 (12)	0.0435 (11)	0.0409 (11)	0.0007 (10)	0.0001 (10)	−0.0105 (10)
C4	0.0548 (16)	0.0371 (15)	0.0434 (15)	−0.0056 (13)	0.0080 (12)	−0.0106 (12)
C6	0.0464 (15)	0.0425 (15)	0.0486 (15)	0.0005 (13)	0.0041 (14)	−0.0052 (13)
C7	0.0428 (14)	0.0399 (14)	0.0395 (13)	0.0001 (12)	−0.0065 (11)	−0.0032 (11)
C8	0.0685 (19)	0.071 (2)	0.0553 (16)	0.0046 (16)	0.0084 (14)	−0.0205 (15)
C11	0.0500 (18)	0.085 (3)	0.0517 (17)	0.0001 (18)	−0.0053 (16)	−0.0091 (17)
C3	0.0450 (14)	0.0384 (13)	0.0492 (14)	−0.0038 (12)	0.0084 (13)	0.0018 (12)
C2	0.0502 (16)	0.0466 (15)	0.0419 (14)	−0.0093 (13)	0.0017 (13)	−0.0014 (12)
C9	0.076 (2)	0.0430 (16)	0.0675 (18)	0.0041 (15)	−0.0147 (15)	−0.0140 (14)
C10	0.073 (2)	0.0533 (19)	0.075 (2)	0.0122 (18)	0.004 (2)	−0.0028 (18)

Geometric parameters (Å, º) top

S1—C7	1.654 (3)	C6—H6	0.90 (2)
O5—C5	1.365 (3)	C8—H8A	0.9010
O5—C11	1.425 (3)	C8—H8B	0.9010
O3—C3	1.367 (3)	C8—H8C	0.9010
O3—C10	1.426 (4)	C11—H5A	1.04 (3)
C5—C6	1.374 (3)	C11—H5B	1.05 (3)
C5—C4	1.392 (3)	C11—H5C	0.95 (3)
C1—C2	1.366 (4)	C3—C2	1.394 (3)
C1—C6	1.380 (3)	C2—H2	0.96 (2)
C1—O1	1.409 (3)	C9—H9A	0.9498
O1—C7	1.372 (3)	C9—H9B	0.9498
N1—C7	1.320 (3)	C9—H9C	0.9498
N1—C8	1.452 (3)	C10—H3A	1.01 (3)
N1—C9	1.462 (3)	C10—H3B	0.95 (3)
C4—C3	1.380 (4)	C10—H3C	0.98 (3)
C4—H4	0.83 (2)

C5—O5—C11	117.3 (2)	H8B—C8—H8C	109.5
C3—O3—C10	117.8 (2)	O5—C11—H5A	108.0 (14)
O5—C5—C6	124.4 (2)	O5—C11—H5B	110.9 (17)
O5—C5—C4	115.0 (2)	H5A—C11—H5B	111 (2)
C6—C5—C4	120.6 (2)	O5—C11—H5C	107.0 (18)
C2—C1—C6	123.7 (2)	H5A—C11—H5C	108 (2)
C2—C1—O1	117.8 (2)	H5B—C11—H5C	112 (2)
C6—C1—O1	118.3 (2)	O3—C3—C4	124.8 (2)
C7—O1—C1	118.32 (18)	O3—C3—C2	114.8 (2)
C7—N1—C8	123.5 (2)	C4—C3—C2	120.4 (2)
C7—N1—C9	119.6 (2)	C1—C2—C3	117.6 (2)
C8—N1—C9	116.8 (2)	C1—C2—H2	124.3 (14)
C3—C4—C5	119.9 (2)	C3—C2—H2	118.1 (14)
C3—C4—H4	120.9 (16)	N1—C9—H9A	109.5
C5—C4—H4	119.2 (16)	N1—C9—H9B	109.5
C5—C6—C1	117.8 (3)	H9A—C9—H9B	109.5
C5—C6—H6	119.6 (15)	N1—C9—H9C	109.5
C1—C6—H6	122.6 (14)	H9A—C9—H9C	109.5
N1—C7—O1	110.2 (2)	H9B—C9—H9C	109.5
N1—C7—S1	126.6 (2)	O3—C10—H3A	110.0 (17)
O1—C7—S1	123.16 (17)	O3—C10—H3B	111.4 (18)
N1—C8—H8A	109.5	H3A—C10—H3B	107 (2)
N1—C8—H8B	109.5	O3—C10—H3C	104.3 (18)
H8A—C8—H8B	109.5	H3A—C10—H3C	113 (2)
N1—C8—H8C	109.5	H3B—C10—H3C	111 (3)
H8A—C8—H8C	109.5

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O-(3,5-Di­methoxy­phenyl) N,N-di­methyl­thio­carbamate

Supporting information

Key indicators

checkCIF/PLATON results

O-(3,5-Dimethoxyphenyl) N,N-dimethylthiocarbamate