N-(2,6-Diisopropyl-phen-yl)thio-amide.

In the crystal structure of the title compound, C(13)H(19)NS {systematic name: N-[2,6-bis-(propan-2-yl)phen-yl]carbothio-amide}, mol-ecules assemble via N-H⋯S=C hydrogen bonds into helical chains along the b axis. The thio-amide moiety, with a syn disposition of the N- and C-bound H atoms, is twisted out of the plane of the benzene ring to which it is connected, forming a dihedral angle angle of 77.60 (14)°.

Related literature

For the synthesis of related aryl­thio­amides, see: Fernandes & Reid (2003 ▶). For related thio­n class="Chemical">amide structures, see: Chitanda et al. (2008 ▶); Michta et al. (2008 ▶); Omondi et al. (2009a ▶); Jarchow & Schmalle (1977 ▶). For related N-2,6-disubstituted-aryl­formamides, see: Omondi et al. (2008 ▶, 2009b ▶,c ▶). For phase transformations in N-2,6-phenyl­formamides and N-2,6-dichloro­phenyl­formamide, see: Omondi et al. (2005 ▶); Gowda et al. (2000 ▶).

Experimental

Crystal data

C13H19NS

M = 221.35

Monoclinic,

a = 9.0230 (12) Å

b = 9.3670 (12) Å

c = 16.269 (2) Å

β = 101.453 (3)°

V = 1347.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.36 × 0.14 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

6974 measured reflections

2508 independent reflections

1456 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.160

S = 0.97

2508 reflections

143 parameters

42 restraints

H atoms treated by a mixture of independent and con class="Chemical">nstrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033685/tk5134sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033685/tk5134Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033685/tk5134Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H19NS	F(000) = 480
Mr = 221.35	Dx = 1.091 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 883 reflections
a = 9.0230 (12) Å	θ = 2.2–23.3°
b = 9.3670 (12) Å	µ = 0.21 mm−1
c = 16.269 (2) Å	T = 293 K
β = 101.453 (3)°	Block, colourless
V = 1347.7 (3) Å3	0.36 × 0.14 × 0.12 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	Rint = 0.098
Graphite monochromator	θmax = 25.5°, θmin = 2.3°
ω scans	h = −9→10
6974 measured reflections	k = −11→11
2508 independent reflections	l = −19→16
1456 reflections with I > 2σ(I)

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.085P)2] where P = (Fo2 + 2Fc2)/3
2508 reflections	(Δ/σ)max = 0.002
143 parameters	Δρmax = 0.23 e Å−3
42 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.4519 (3)	0.8487 (2)	0.32841 (15)	0.0460 (6)
C2	0.2981 (3)	0.8173 (2)	0.31060 (17)	0.0570 (7)
C3	0.2441 (3)	0.7287 (3)	0.3670 (2)	0.0702 (9)
H3	0.1419	0.7056	0.3572	0.084*
C4	0.3383 (4)	0.6750 (3)	0.4364 (2)	0.0733 (9)
H4	0.2995	0.6166	0.4732	0.088*
C5	0.4902 (4)	0.7070 (3)	0.45191 (17)	0.0639 (7)
H5	0.5535	0.6683	0.4987	0.077*
C6	0.5497 (3)	0.7954 (2)	0.39911 (15)	0.0500 (6)
C7	0.5833 (3)	0.9161 (3)	0.21651 (16)	0.0571 (7)
H7	0.6092	0.9935	0.1864	0.068*
C8	0.1944 (3)	0.8753 (3)	0.2333 (2)	0.0851 (10)
H8	0.245	0.9589	0.2153	0.102*
C9	0.7154 (3)	0.8385 (3)	0.42054 (16)	0.0612 (7)
H9	0.7428	0.877	0.3696	0.073*
C10	0.1760 (6)	0.7693 (4)	0.1626 (3)	0.1243 (15)
H10A	0.2739	0.7378	0.1553	0.186*
H10B	0.1238	0.8135	0.1118	0.186*
H10C	0.1188	0.6889	0.1755	0.186*
C11	0.0449 (5)	0.9259 (5)	0.2488 (4)	0.168 (2)
H11A	−0.0073	0.8477	0.2685	0.252*
H11B	−0.0146	0.9622	0.1975	0.252*
H11C	0.0609	1.0001	0.2903	0.252*
C12	0.7377 (4)	0.9566 (3)	0.4862 (2)	0.0986 (11)
H12A	0.6709	1.0345	0.4666	0.148*
H12B	0.8405	0.9894	0.4956	0.148*
H12C	0.7159	0.9204	0.5377	0.148*
C13	0.8196 (4)	0.7135 (4)	0.4498 (3)	0.1098 (13)
H13A	0.8007	0.6786	0.5023	0.165*
H13B	0.9229	0.7441	0.457	0.165*
H13C	0.8011	0.6387	0.4087	0.165*
S1	0.63900 (10)	0.75914 (7)	0.18895 (5)	0.0724 (3)
N1	0.5084 (2)	0.9469 (2)	0.27423 (14)	0.0530 (6)
H1	0.485 (3)	1.032 (3)	0.2817 (16)	0.064*

	U11	U22	U33	U12	U13	U23
C1	0.0531 (16)	0.0339 (10)	0.0526 (15)	−0.0004 (10)	0.0145 (12)	−0.0042 (10)
C2	0.0520 (17)	0.0388 (12)	0.0803 (19)	0.0005 (11)	0.0134 (14)	−0.0093 (12)
C3	0.0604 (19)	0.0535 (15)	0.104 (3)	−0.0078 (13)	0.0352 (19)	−0.0198 (16)
C4	0.104 (3)	0.0558 (15)	0.073 (2)	−0.0112 (16)	0.049 (2)	−0.0065 (15)
C5	0.088 (2)	0.0606 (14)	0.0467 (15)	0.0014 (15)	0.0216 (15)	−0.0021 (12)
C6	0.0627 (17)	0.0431 (11)	0.0450 (14)	0.0023 (11)	0.0125 (13)	−0.0047 (11)
C7	0.0667 (18)	0.0506 (13)	0.0508 (15)	−0.0163 (12)	0.0040 (14)	0.0105 (12)
C8	0.0568 (19)	0.0644 (16)	0.122 (3)	−0.0023 (14)	−0.0107 (19)	0.0111 (18)
C9	0.0608 (18)	0.0717 (16)	0.0479 (15)	−0.0006 (13)	0.0030 (13)	−0.0004 (13)
C10	0.122 (4)	0.141 (3)	0.090 (3)	0.020 (3)	−0.028 (2)	−0.002 (2)
C11	0.088 (3)	0.166 (4)	0.232 (6)	0.066 (3)	−0.010 (3)	−0.018 (4)
C12	0.094 (3)	0.092 (2)	0.106 (3)	−0.0292 (19)	0.013 (2)	−0.032 (2)
C13	0.072 (2)	0.109 (2)	0.135 (3)	0.0240 (19)	−0.011 (2)	−0.007 (2)
S1	0.0962 (7)	0.0621 (4)	0.0675 (5)	−0.0117 (4)	0.0370 (4)	−0.0061 (3)
N1	0.0592 (14)	0.0341 (9)	0.0634 (14)	−0.0014 (9)	0.0067 (12)	0.0048 (10)

C1—C2	1.392 (3)	C8—H8	0.98
C1—C6	1.395 (3)	C9—C13	1.518 (4)
C1—N1	1.436 (3)	C9—C12	1.523 (4)
C2—C3	1.395 (4)	C9—H9	0.98
C2—C8	1.512 (4)	C10—H10A	0.96
C3—C4	1.367 (4)	C10—H10B	0.96
C3—H3	0.93	C10—H10C	0.96
C4—C5	1.377 (4)	C11—H11A	0.96
C4—H4	0.93	C11—H11B	0.96
C5—C6	1.377 (4)	C11—H11C	0.96
C5—H5	0.93	C12—H12A	0.96
C6—C9	1.521 (4)	C12—H12B	0.96
C7—N1	1.294 (3)	C12—H12C	0.96
C7—S1	1.645 (3)	C13—H13A	0.96
C7—H7	0.93	C13—H13B	0.96
C8—C11	1.497 (5)	C13—H13C	0.96
C8—C10	1.503 (5)	N1—H1	0.84 (3)
C2—C1—C6	122.5 (2)	C13—C9—H9	107.8
C2—C1—N1	117.9 (2)	C6—C9—H9	107.8
C6—C1—N1	119.5 (2)	C12—C9—H9	107.8
C1—C2—C3	116.9 (2)	C8—C10—H10A	109.5
C1—C2—C8	121.6 (3)	C8—C10—H10B	109.5
C3—C2—C8	121.5 (3)	H10A—C10—H10B	109.5
C4—C3—C2	121.4 (3)	C8—C10—H10C	109.5
C4—C3—H3	119.3	H10A—C10—H10C	109.5
C2—C3—H3	119.3	H10B—C10—H10C	109.5
C3—C4—C5	120.3 (3)	C8—C11—H11A	109.5
C3—C4—H4	119.8	C8—C11—H11B	109.5
C5—C4—H4	119.8	H11A—C11—H11B	109.5
C6—C5—C4	120.9 (3)	C8—C11—H11C	109.5
C6—C5—H5	119.5	H11A—C11—H11C	109.5
C4—C5—H5	119.5	H11B—C11—H11C	109.5
C5—C6—C1	117.9 (2)	C9—C12—H12A	109.5
C5—C6—C9	120.3 (2)	C9—C12—H12B	109.5
C1—C6—C9	121.7 (2)	H12A—C12—H12B	109.5
N1—C7—S1	128.99 (19)	C9—C12—H12C	109.5
N1—C7—H7	115.5	H12A—C12—H12C	109.5
S1—C7—H7	115.5	H12B—C12—H12C	109.5
C11—C8—C10	111.8 (3)	C9—C13—H13A	109.5
C11—C8—C2	113.8 (4)	C9—C13—H13B	109.5
C10—C8—C2	110.8 (2)	H13A—C13—H13B	109.5
C11—C8—H8	106.7	C9—C13—H13C	109.5
C10—C8—H8	106.7	H13A—C13—H13C	109.5
C2—C8—H8	106.7	H13B—C13—H13C	109.5
C13—C9—C6	112.7 (2)	C7—N1—C1	127.1 (2)
C13—C9—C12	110.7 (3)	C7—N1—H1	119.7 (19)
C6—C9—C12	109.9 (2)	C1—N1—H1	113.2 (19)
C6—C1—C2—C3	−0.2 (3)	N1—C1—C6—C9	−0.1 (3)
N1—C1—C2—C3	−176.1 (2)	C1—C2—C8—C11	−138.2 (3)
C6—C1—C2—C8	−179.6 (2)	C3—C2—C8—C11	42.4 (4)
N1—C1—C2—C8	4.5 (3)	C1—C2—C8—C10	94.8 (4)
C1—C2—C3—C4	−0.1 (4)	C3—C2—C8—C10	−84.6 (4)
C8—C2—C3—C4	179.3 (2)	C5—C6—C9—C13	45.2 (4)
C2—C3—C4—C5	−0.4 (4)	C1—C6—C9—C13	−137.9 (3)
C3—C4—C5—C6	1.2 (4)	C5—C6—C9—C12	−78.7 (3)
C4—C5—C6—C1	−1.5 (4)	C1—C6—C9—C12	98.1 (3)
C4—C5—C6—C9	175.5 (2)	S1—C7—N1—C1	−1.3 (4)
C2—C1—C6—C5	1.0 (3)	C2—C1—N1—C7	−103.4 (3)
N1—C1—C6—C5	176.8 (2)	C6—C1—N1—C7	80.6 (3)
C2—C1—C6—C9	−176.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.84 (3)	2.49 (3)	3.316 (2)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.84 (3)	2.49 (3)	3.316 (2)	166 (2)

Symmetry code: (i) .