Crystal structure of N-(propan-2-yl-carbamo-thio-yl)benzamide.

In the crystal structure of the title compound, C11H14N2OS, the six atoms of the central C2N2OS residue are coplanar (r.m.s. deviation = 0.002 Å), which facilitates the formation of an intra-molecular N-H⋯O hydrogen bond, which closes an S(6) loop. The terminal phenyl ring is inclined with respect to the central plane [dihedral angle = 42.10 (6)°]. The most prominent feature of the crystal packing is the formation of {⋯HNCS}2 synthons resulting in centrosymmetric dimers.

Related literature

For use of thio­ureas as building blocks in the synthesis of various organic compounds, see: Burgeson et al. (2012 ▸); Vega-Pérez et al. (2012 ▸); Yao et al. (2012 ▸); Shantharam et al. (2013 ▸); Yang et al. (2013 ▸). For use of thio­urea-containing compounds in medicinal applications, see: Rodriguez-Fernandez et al. (2005 ▸); Rauf et al. (2012 ▸).

Experimental

Crystal data

C11H14N2OS

M = 222.30

Monoclinic,

a = 11.2147 (4) Å

b = 5.3988 (2) Å

c = 19.6834 (7) Å

β = 102.031 (4)°

V = 1165.57 (7) Å3

Z = 4

Cu Kα radiation

μ = 2.27 mm−1

T = 293 K

0.28 × 0.22 × 0.18 mm

Data collection

Agilent Xcalibur, Eos, Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.828, T max = 1.000

3844 measured reflections

2189 independent reflections

1944 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.146

S = 1.08

2189 reflections

146 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2014 (Gruene et al., 2014 ▸); program(s) used to refine structure: SHELXL2014 (Gruene et al., 2014 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014027133/tk5351sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027133/tk5351Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014027133/tk5351Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014027133/tk5351fig1.tif

Perspective view of the title mol­ecule with atom labeling scheme and 50% probability ellipsoids.

Click here for additional data file.

b . DOI: 10.1107/S2056989014027133/tk5351fig2.tif

Packing viewed down the b axis showing stacks of pairs of mol­ecules connected by N—H⋯S inter­actions.

CCDC reference: 1038725

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H14N2OS	F(000) = 472
Mr = 222.30	Dx = 1.267 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 1804 reflections
a = 11.2147 (4) Å	θ = 4.0–71.4°
b = 5.3988 (2) Å	µ = 2.27 mm−1
c = 19.6834 (7) Å	T = 293 K
β = 102.031 (4)°	Prism, colourless
V = 1165.57 (7) Å3	0.28 × 0.22 × 0.18 mm
Z = 4

Agilent Xcalibur, Eos, Gemini diffractometer	2189 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1944 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.0416 pixels mm-1	θmax = 71.3°, θmin = 4.0°
ω scans	h = −12→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −6→5
Tmin = 0.828, Tmax = 1.000	l = −18→24
3844 measured reflections

Refinement on F2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.146	w = 1/[σ2(Fo2) + (0.0871P)2 + 0.3862P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2189 reflections	Δρmax = 0.37 e Å−3
146 parameters	Δρmin = −0.34 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S1	0.60730 (5)	0.80543 (14)	0.08368 (3)	0.0464 (2)
O1	0.86531 (13)	1.0046 (3)	−0.05679 (8)	0.0392 (5)
N1	0.69070 (16)	1.0345 (3)	−0.01498 (9)	0.0321 (5)
N2	0.82704 (16)	0.7717 (3)	0.05595 (9)	0.0337 (5)
C1	0.63795 (19)	1.4665 (4)	−0.10695 (11)	0.0334 (6)
C2	0.5930 (2)	1.6272 (4)	−0.16095 (12)	0.0392 (6)
C3	0.6171 (2)	1.5865 (4)	−0.22650 (11)	0.0414 (7)
C4	0.6865 (2)	1.3853 (5)	−0.23779 (11)	0.0402 (7)
C5	0.73328 (19)	1.2248 (4)	−0.18386 (11)	0.0342 (6)
C6	0.70827 (17)	1.2641 (4)	−0.11803 (10)	0.0293 (5)
C7	0.76319 (18)	1.0900 (4)	−0.06135 (10)	0.0310 (6)
C8	0.71668 (19)	0.8697 (4)	0.04084 (10)	0.0322 (6)
C9	0.8684 (2)	0.5923 (4)	0.11200 (11)	0.0389 (7)
C10	0.9666 (2)	0.4305 (4)	0.09293 (13)	0.0452 (7)
C11	0.9154 (3)	0.7308 (6)	0.17988 (13)	0.0592 (9)
H1	0.62120	1.49370	−0.06320	0.0400*
H1N	0.6216 (16)	1.085 (4)	−0.0236 (11)	0.022 (5)*
H2	0.54640	1.76300	−0.15340	0.0470*
H2N	0.880 (2)	0.814 (5)	0.0317 (14)	0.048 (8)*
H3	0.58660	1.69470	−0.26270	0.0500*
H4	0.70190	1.35740	−0.28180	0.0480*
H5	0.78120	1.09110	−0.19140	0.0410*
H9	0.79950	0.48790	0.11730	0.0470*
H10A	0.93400	0.34290	0.05070	0.0680*
H10B	0.99470	0.31390	0.12960	0.0680*
H10C	1.03360	0.53220	0.08640	0.0680*
H11A	0.98180	0.83660	0.17480	0.0890*
H11B	0.94320	0.61370	0.21650	0.0890*
H11C	0.85090	0.82920	0.19110	0.0890*

	U11	U22	U33	U12	U13	U23
S1	0.0297 (3)	0.0743 (5)	0.0364 (3)	0.0061 (2)	0.0096 (2)	0.0129 (3)
O1	0.0309 (8)	0.0465 (9)	0.0415 (8)	0.0072 (6)	0.0106 (6)	0.0113 (7)
N1	0.0278 (8)	0.0390 (9)	0.0293 (8)	0.0046 (7)	0.0056 (6)	0.0054 (7)
N2	0.0306 (9)	0.0383 (10)	0.0314 (9)	0.0010 (7)	0.0046 (7)	0.0076 (7)
C1	0.0350 (10)	0.0309 (10)	0.0331 (10)	−0.0033 (8)	0.0041 (8)	−0.0023 (8)
C2	0.0400 (11)	0.0299 (10)	0.0448 (12)	−0.0012 (9)	0.0019 (9)	0.0025 (9)
C3	0.0418 (12)	0.0405 (12)	0.0377 (11)	−0.0059 (9)	−0.0014 (9)	0.0124 (9)
C4	0.0369 (11)	0.0544 (14)	0.0291 (10)	−0.0081 (10)	0.0064 (8)	0.0062 (9)
C5	0.0284 (10)	0.0408 (11)	0.0341 (10)	−0.0027 (8)	0.0080 (8)	0.0032 (8)
C6	0.0260 (9)	0.0304 (9)	0.0300 (9)	−0.0055 (7)	0.0022 (7)	0.0023 (8)
C7	0.0321 (10)	0.0314 (10)	0.0286 (9)	−0.0038 (8)	0.0043 (7)	−0.0007 (8)
C8	0.0336 (10)	0.0363 (10)	0.0255 (9)	−0.0020 (8)	0.0033 (7)	−0.0004 (8)
C9	0.0367 (11)	0.0412 (12)	0.0379 (11)	0.0022 (9)	0.0059 (9)	0.0114 (9)
C10	0.0487 (13)	0.0347 (11)	0.0506 (13)	0.0075 (10)	0.0065 (10)	0.0043 (10)
C11	0.0607 (16)	0.079 (2)	0.0334 (12)	0.0280 (14)	−0.0003 (11)	0.0010 (12)

S1—C8	1.664 (2)	C9—C11	1.526 (3)
O1—C7	1.220 (3)	C9—C10	1.513 (3)
N1—C7	1.376 (3)	C1—H1	0.9300
N1—C8	1.397 (3)	C2—H2	0.9300
N2—C8	1.322 (3)	C3—H3	0.9300
N2—C9	1.469 (3)	C4—H4	0.9300
C1—C2	1.383 (3)	C5—H5	0.9300
C1—C6	1.391 (3)	C9—H9	0.9800
N1—H1N	0.806 (19)	C10—H10A	0.9600
N2—H2N	0.87 (2)	C10—H10B	0.9600
C2—C3	1.390 (3)	C10—H10C	0.9600
C3—C4	1.381 (3)	C11—H11A	0.9600
C4—C5	1.386 (3)	C11—H11B	0.9600
C5—C6	1.398 (3)	C11—H11C	0.9600
C6—C7	1.490 (3)
C7—N1—C8	127.26 (18)	C6—C1—H1	120.00
C8—N2—C9	124.57 (18)	C1—C2—H2	120.00
C2—C1—C6	120.0 (2)	C3—C2—H2	120.00
C7—N1—H1N	117.5 (15)	C2—C3—H3	120.00
C8—N1—H1N	114.5 (15)	C4—C3—H3	120.00
C1—C2—C3	120.3 (2)	C3—C4—H4	120.00
C8—N2—H2N	119.2 (17)	C5—C4—H4	120.00
C9—N2—H2N	116.2 (17)	C4—C5—H5	120.00
C2—C3—C4	119.9 (2)	C6—C5—H5	120.00
C3—C4—C5	120.3 (2)	N2—C9—H9	109.00
C4—C5—C6	119.9 (2)	C10—C9—H9	109.00
C1—C6—C7	122.51 (18)	C11—C9—H9	109.00
C5—C6—C7	117.82 (18)	C9—C10—H10A	109.00
C1—C6—C5	119.63 (19)	C9—C10—H10B	110.00
O1—C7—N1	122.96 (19)	C9—C10—H10C	109.00
O1—C7—C6	121.90 (18)	H10A—C10—H10B	110.00
N1—C7—C6	115.14 (17)	H10A—C10—H10C	109.00
S1—C8—N1	118.47 (16)	H10B—C10—H10C	109.00
S1—C8—N2	123.87 (16)	C9—C11—H11A	110.00
N1—C8—N2	117.65 (19)	C9—C11—H11B	109.00
N2—C9—C11	109.39 (19)	C9—C11—H11C	109.00
C10—C9—C11	111.3 (2)	H11A—C11—H11B	109.00
N2—C9—C10	109.06 (18)	H11A—C11—H11C	109.00
C2—C1—H1	120.00	H11B—C11—H11C	110.00
C7—N1—C8—N2	7.1 (3)	C2—C1—C6—C7	177.6 (2)
C7—N1—C8—S1	−172.18 (17)	C1—C2—C3—C4	−0.2 (3)
C8—N1—C7—O1	−3.3 (3)	C2—C3—C4—C5	−0.6 (3)
C8—N1—C7—C6	176.95 (19)	C3—C4—C5—C6	1.2 (3)
C9—N2—C8—S1	0.4 (3)	C4—C5—C6—C7	−178.5 (2)
C9—N2—C8—N1	−178.83 (18)	C4—C5—C6—C1	−0.9 (3)
C8—N2—C9—C10	151.8 (2)	C1—C6—C7—O1	−140.9 (2)
C8—N2—C9—C11	−86.2 (3)	C5—C6—C7—O1	36.7 (3)
C6—C1—C2—C3	0.4 (3)	C5—C6—C7—N1	−143.55 (19)
C2—C1—C6—C5	0.1 (3)	C1—C6—C7—N1	38.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1i	0.81 (2)	2.66 (2)	3.4439 (19)	165 (2)
N2—H2N···O1	0.87 (2)	2.00 (3)	2.662 (2)	132 (2)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1NS1i	0.81(2)	2.66(2)	3.4439(19)	165(2)
N2H2NO1	0.87(2)	2.00(3)	2.662(2)	132(2)

Symmetry code: (i) .