Ethyl 4-[3-(2-methyl-benzo-yl)thio-ureido]benzoate.

The mol-ecular conformation of the title compound, C(18)H(18)N(2)O(3)S, is stabilized by an intra-molecular N-H⋯O hydrogen bond. The crystal packing shows centrosymmetric dimers connected by N-H⋯S hydrogen bonds. The terminal eth-oxy substituents are statistically disordered [occupancy ratio 0.527 (5):0.473 (5)].

Related literature

For the use of thio­urea derivatives in organic synthesis and analysis, see: Eynde & Watte (2003 ▶); Fu et al. (1999 ▶); Rashdan et al. (2006 ▶); Maryanoff et al. (1986 ▶); Wang et al.(2005 ▶); Saeed et al. (2008 ▶); Koch, (2001 ▶). For their bioactivity and pharmaceutical applications, see: Upadhyaya & Srivastava (1982 ▶); Ramadas et al. (1998 ▶); Blum & Hayes (1979 ▶); DeBeer et al. (1936 ▶). For related structures, see: Saeed & Flörke (2007a ▶,b ▶); Saeed et al. (2009 ▶).

Experimental

Crystal data

C18H18N2O3S

M = 342.40

Triclinic,

a = 7.4555 (3) Å

b = 7.6311 (4) Å

c = 15.2468 (8) Å

α = 96.456 (4)°

β = 103.860 (5)°

γ = 92.908 (4)°

V = 834.13 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 173 K

0.33 × 0.32 × 0.28 mm

Data collection

Stoe IPDS II two-circle-diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.933, T max = 0.943

22798 measured reflections

4659 independent reflections

4311 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.04

4659 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.37 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904183X/im2145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904183X/im2145Isup2.hkl

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

C18H18N2O3S	Z = 2
Mr = 342.40	F(000) = 360
Triclinic, P1	Dx = 1.363 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4555 (3) Å	Cell parameters from 42517 reflections
b = 7.6311 (4) Å	θ = 3.4–29.9°
c = 15.2468 (8) Å	µ = 0.21 mm−1
α = 96.456 (4)°	T = 173 K
β = 103.860 (5)°	Block, colourless
γ = 92.908 (4)°	0.33 × 0.32 × 0.28 mm
V = 834.13 (7) Å3

Stoe IPDS II two-circle-diffractometer	4659 independent reflections
Radiation source: fine-focus sealed tube	4311 reflections with I > 2σ(I)
graphite	Rint = 0.057
ω scans	θmax = 29.6°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −10→10
Tmin = 0.933, Tmax = 0.943	k = −10→10
22798 measured reflections	l = −21→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.2098P] where P = (Fo2 + 2Fc2)/3
4659 reflections	(Δ/σ)max = 0.002
246 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
S1	1.09603 (4)	0.22920 (4)	0.599200 (16)	0.02926 (8)
O1	0.54635 (11)	0.37544 (11)	0.42973 (5)	0.03282 (18)
O2	1.1748 (4)	1.1151 (2)	0.86115 (13)	0.0302 (5)	0.527 (5)
O2A	1.0912 (4)	1.1206 (2)	0.88161 (14)	0.0309 (6)	0.473 (5)
O3	1.23261 (17)	0.91072 (12)	0.96012 (6)	0.0521 (3)
N1	0.82261 (12)	0.44800 (11)	0.57980 (5)	0.02358 (17)
H1	0.7282	0.4728	0.5478	0.028*
N2	0.77873 (12)	0.19546 (11)	0.47488 (6)	0.02420 (17)
H2	0.8242	0.0956	0.4570	0.029*
C1	0.89035 (13)	0.29850 (13)	0.55169 (6)	0.02227 (18)
C2	0.61524 (13)	0.23496 (13)	0.41838 (6)	0.02368 (18)
C11	0.90732 (12)	0.57062 (12)	0.65792 (6)	0.02124 (17)
C12	0.98398 (14)	0.51635 (13)	0.74226 (7)	0.02457 (19)
H12	0.9840	0.3941	0.7490	0.029*
C13	1.06022 (14)	0.64342 (13)	0.81625 (7)	0.02587 (19)
H13	1.1131	0.6075	0.8739	0.031*
C14	1.06025 (15)	0.82288 (13)	0.80705 (7)	0.0273 (2)
C15	0.97895 (15)	0.87601 (13)	0.72331 (7)	0.0286 (2)
H15	0.9755	0.9983	0.7170	0.034*
C16	0.90262 (14)	0.74958 (13)	0.64881 (6)	0.02458 (19)
H16	0.8471	0.7856	0.5915	0.029*
C17	1.1522 (2)	0.95152 (16)	0.88788 (9)	0.0456 (3)
C18	1.2785 (4)	1.2514 (3)	0.93166 (16)	0.0336 (6)	0.527 (5)
H18A	1.3222	1.3504	0.9033	0.040*	0.527 (5)
H18B	1.3886	1.2024	0.9681	0.040*	0.527 (5)
C19	1.1602 (4)	1.3183 (4)	0.9924 (2)	0.0404 (6)	0.527 (5)
H19A	1.2319	1.4107	1.0394	0.061*	0.527 (5)
H19B	1.1193	1.2206	1.0215	0.061*	0.527 (5)
H19C	1.0518	1.3673	0.9564	0.061*	0.527 (5)
C18A	1.1603 (4)	1.2562 (4)	0.9587 (2)	0.0324 (6)	0.473 (5)
H18C	1.1639	1.2048	1.0158	0.039*	0.473 (5)
H18D	1.0751	1.3519	0.9553	0.039*	0.473 (5)
C19A	1.3507 (5)	1.3318 (4)	0.9602 (2)	0.0419 (8)	0.473 (5)
H19D	1.3942	1.4226	1.0131	0.063*	0.473 (5)
H19E	1.3469	1.3849	0.9043	0.063*	0.473 (5)
H19F	1.4356	1.2375	0.9644	0.063*	0.473 (5)
C21	0.53091 (13)	0.08983 (13)	0.34332 (7)	0.02406 (19)
C22	0.50526 (15)	−0.08026 (14)	0.36571 (8)	0.0294 (2)
H22	0.5425	−0.1013	0.4275	0.035*
C23	0.42550 (17)	−0.21929 (16)	0.29831 (9)	0.0373 (3)
H23	0.4064	−0.3349	0.3136	0.045*
C24	0.37444 (18)	−0.18683 (18)	0.20872 (9)	0.0419 (3)
H24	0.3212	−0.2812	0.1621	0.050*
C25	0.40002 (17)	−0.01808 (17)	0.18616 (8)	0.0369 (3)
H25	0.3647	0.0011	0.1241	0.044*
C26	0.47678 (14)	0.12474 (15)	0.25293 (7)	0.0277 (2)
C27	0.49622 (18)	0.30658 (17)	0.22573 (8)	0.0363 (2)
H27A	0.3852	0.3678	0.2291	0.054*
H27B	0.5109	0.2969	0.1632	0.054*
H27C	0.6053	0.3737	0.2671	0.054*

	U11	U22	U33	U12	U13	U23
S1	0.02783 (13)	0.03461 (14)	0.02109 (12)	0.01339 (10)	−0.00154 (9)	−0.00282 (9)
O1	0.0292 (4)	0.0317 (4)	0.0296 (4)	0.0119 (3)	−0.0037 (3)	−0.0098 (3)
O2	0.0369 (11)	0.0226 (7)	0.0255 (8)	−0.0031 (6)	0.0009 (7)	−0.0036 (6)
O2A	0.0409 (14)	0.0227 (8)	0.0229 (8)	0.0024 (7)	−0.0005 (8)	−0.0048 (6)
O3	0.0761 (7)	0.0317 (4)	0.0293 (4)	−0.0019 (4)	−0.0204 (4)	−0.0010 (3)
N1	0.0232 (4)	0.0242 (4)	0.0187 (3)	0.0062 (3)	−0.0018 (3)	−0.0032 (3)
N2	0.0249 (4)	0.0245 (4)	0.0195 (4)	0.0070 (3)	0.0007 (3)	−0.0045 (3)
C1	0.0242 (4)	0.0250 (4)	0.0161 (4)	0.0044 (3)	0.0029 (3)	−0.0004 (3)
C2	0.0224 (4)	0.0264 (4)	0.0199 (4)	0.0046 (3)	0.0031 (3)	−0.0032 (3)
C11	0.0198 (4)	0.0235 (4)	0.0180 (4)	0.0019 (3)	0.0021 (3)	−0.0020 (3)
C12	0.0290 (4)	0.0217 (4)	0.0205 (4)	0.0023 (3)	0.0022 (3)	0.0007 (3)
C13	0.0305 (5)	0.0248 (4)	0.0188 (4)	0.0020 (4)	−0.0003 (3)	0.0017 (3)
C14	0.0304 (5)	0.0234 (4)	0.0219 (4)	−0.0016 (4)	−0.0035 (4)	−0.0004 (3)
C15	0.0337 (5)	0.0215 (4)	0.0252 (5)	−0.0009 (4)	−0.0020 (4)	0.0024 (3)
C16	0.0262 (4)	0.0253 (4)	0.0193 (4)	0.0023 (3)	0.0002 (3)	0.0025 (3)
C17	0.0634 (8)	0.0239 (5)	0.0322 (6)	−0.0038 (5)	−0.0185 (6)	−0.0001 (4)
C18	0.0361 (12)	0.0261 (11)	0.0317 (11)	−0.0045 (10)	0.0014 (9)	−0.0073 (9)
C19	0.0509 (14)	0.0331 (13)	0.0341 (14)	0.0081 (11)	0.0081 (11)	−0.0053 (11)
C18A	0.0436 (14)	0.0228 (12)	0.0262 (13)	0.0009 (10)	0.0060 (10)	−0.0101 (10)
C19A	0.0430 (15)	0.0352 (15)	0.0415 (15)	−0.0034 (13)	0.0032 (12)	−0.0028 (12)
C21	0.0200 (4)	0.0269 (4)	0.0222 (4)	0.0034 (3)	0.0035 (3)	−0.0065 (3)
C22	0.0272 (5)	0.0292 (5)	0.0310 (5)	0.0026 (4)	0.0085 (4)	−0.0031 (4)
C23	0.0334 (5)	0.0283 (5)	0.0479 (7)	−0.0032 (4)	0.0129 (5)	−0.0090 (5)
C24	0.0357 (6)	0.0405 (6)	0.0406 (6)	−0.0035 (5)	0.0054 (5)	−0.0208 (5)
C25	0.0342 (5)	0.0455 (6)	0.0244 (5)	0.0044 (5)	0.0018 (4)	−0.0121 (4)
C26	0.0243 (4)	0.0336 (5)	0.0222 (4)	0.0049 (4)	0.0036 (3)	−0.0053 (4)
C27	0.0398 (6)	0.0395 (6)	0.0283 (5)	0.0073 (5)	0.0056 (4)	0.0034 (4)

S1—C1	1.6709 (10)	C18—H18A	0.9900
O1—C2	1.2247 (12)	C18—H18B	0.9900
O2—C17	1.370 (2)	C19—H19A	0.9800
O2—C18	1.451 (3)	C19—H19B	0.9800
O2A—C17	1.395 (2)	C19—H19C	0.9800
O2A—C18A	1.449 (4)	C18A—C19A	1.499 (4)
O3—C17	1.2038 (15)	C18A—H18C	0.9900
N1—C1	1.3388 (12)	C18A—H18D	0.9900
N1—C11	1.4220 (11)	C19A—H19D	0.9800
N1—H1	0.7998	C19A—H19E	0.9800
N2—C2	1.3824 (12)	C19A—H19F	0.9800
N2—C1	1.3936 (12)	C21—C22	1.3941 (15)
N2—H2	0.8911	C21—C26	1.4001 (14)
C2—C21	1.4937 (13)	C22—C23	1.3904 (15)
C11—C16	1.3895 (13)	C22—H22	0.9500
C11—C12	1.3941 (13)	C23—C24	1.382 (2)
C12—C13	1.3881 (13)	C23—H23	0.9500
C12—H12	0.9500	C24—C25	1.385 (2)
C13—C14	1.3923 (14)	C24—H24	0.9500
C13—H13	0.9500	C25—C26	1.4000 (14)
C14—C15	1.3900 (14)	C25—H25	0.9500
C14—C17	1.4858 (14)	C26—C27	1.5021 (17)
C15—C16	1.3904 (13)	C27—H27A	0.9800
C15—H15	0.9500	C27—H27B	0.9800
C16—H16	0.9500	C27—H27C	0.9800
C18—C19	1.493 (4)
C17—O2—C18	115.67 (16)	C18—C19—H19A	109.5
C17—O2A—C18A	118.32 (17)	C18—C19—H19B	109.5
C1—N1—C11	126.33 (8)	H19A—C19—H19B	109.5
C1—N1—H1	116.3	C18—C19—H19C	109.5
C11—N1—H1	117.2	H19A—C19—H19C	109.5
C2—N2—C1	128.53 (8)	H19B—C19—H19C	109.5
C2—N2—H2	115.7	O2A—C18A—C19A	111.2 (4)
C1—N2—H2	115.5	O2A—C18A—H18C	109.4
N1—C1—N2	116.03 (8)	C19A—C18A—H18C	109.4
N1—C1—S1	125.74 (7)	O2A—C18A—H18D	109.4
N2—C1—S1	118.21 (7)	C19A—C18A—H18D	109.4
O1—C2—N2	122.79 (9)	H18C—C18A—H18D	108.0
O1—C2—C21	123.60 (9)	C18A—C19A—H19D	109.5
N2—C2—C21	113.61 (8)	C18A—C19A—H19E	109.5
C16—C11—C12	120.35 (8)	H19D—C19A—H19E	109.5
C16—C11—N1	117.45 (8)	C18A—C19A—H19F	109.5
C12—C11—N1	122.11 (9)	H19D—C19A—H19F	109.5
C13—C12—C11	119.08 (9)	H19E—C19A—H19F	109.5
C13—C12—H12	120.5	C22—C21—C26	120.98 (9)
C11—C12—H12	120.5	C22—C21—C2	118.37 (9)
C12—C13—C14	120.85 (9)	C26—C21—C2	120.65 (9)
C12—C13—H13	119.6	C23—C22—C21	120.47 (11)
C14—C13—H13	119.6	C23—C22—H22	119.8
C15—C14—C13	119.70 (9)	C21—C22—H22	119.8
C15—C14—C17	122.23 (10)	C24—C23—C22	119.01 (12)
C13—C14—C17	118.05 (9)	C24—C23—H23	120.5
C14—C15—C16	119.80 (9)	C22—C23—H23	120.5
C14—C15—H15	120.1	C23—C24—C25	120.70 (10)
C16—C15—H15	120.1	C23—C24—H24	119.7
C11—C16—C15	120.18 (9)	C25—C24—H24	119.7
C11—C16—H16	119.9	C24—C25—C26	121.39 (11)
C15—C16—H16	119.9	C24—C25—H25	119.3
O3—C17—O2	124.17 (12)	C26—C25—H25	119.3
O3—C17—O2A	120.61 (13)	C25—C26—C21	117.44 (11)
O3—C17—C14	124.28 (11)	C25—C26—C27	119.59 (10)
O2—C17—C14	109.38 (11)	C21—C26—C27	122.97 (9)
O2A—C17—C14	112.60 (11)	C26—C27—H27A	109.5
O2—C18—C19	110.5 (3)	C26—C27—H27B	109.5
O2—C18—H18A	109.6	H27A—C27—H27B	109.5
C19—C18—H18A	109.6	C26—C27—H27C	109.5
O2—C18—H18B	109.6	H27A—C27—H27C	109.5
C19—C18—H18B	109.6	H27B—C27—H27C	109.5
H18A—C18—H18B	108.1
C11—N1—C1—N2	177.55 (9)	C15—C14—C17—O3	−175.89 (16)
C11—N1—C1—S1	−3.80 (15)	C13—C14—C17—O3	2.8 (2)
C2—N2—C1—N1	6.94 (15)	C15—C14—C17—O2	−12.1 (2)
C2—N2—C1—S1	−171.82 (9)	C13—C14—C17—O2	166.59 (17)
C1—N2—C2—O1	0.83 (17)	C15—C14—C17—O2A	22.0 (2)
C1—N2—C2—C21	−178.64 (9)	C13—C14—C17—O2A	−159.3 (2)
C1—N1—C11—C16	137.72 (11)	C17—O2—C18—C19	−77.4 (3)
C1—N1—C11—C12	−45.70 (15)	C17—O2A—C18A—C19A	79.8 (3)
C16—C11—C12—C13	−1.85 (15)	O1—C2—C21—C22	−128.25 (12)
N1—C11—C12—C13	−178.34 (9)	N2—C2—C21—C22	51.21 (12)
C11—C12—C13—C14	0.19 (16)	O1—C2—C21—C26	50.88 (15)
C12—C13—C14—C15	1.59 (17)	N2—C2—C21—C26	−129.66 (10)
C12—C13—C14—C17	−177.10 (12)	C26—C21—C22—C23	0.19 (16)
C13—C14—C15—C16	−1.71 (17)	C2—C21—C22—C23	179.32 (9)
C17—C14—C15—C16	176.93 (12)	C21—C22—C23—C24	0.89 (17)
C12—C11—C16—C15	1.74 (15)	C22—C23—C24—C25	−0.76 (19)
N1—C11—C16—C15	178.39 (9)	C23—C24—C25—C26	−0.44 (19)
C14—C15—C16—C11	0.06 (17)	C24—C25—C26—C21	1.48 (17)
C18—O2—C17—O3	−10.6 (4)	C24—C25—C26—C27	−177.99 (11)
C18—O2—C17—O2A	83.6 (3)	C22—C21—C26—C25	−1.35 (15)
C18—O2—C17—C14	−174.5 (2)	C2—C21—C26—C25	179.54 (9)
C18A—O2A—C17—O3	13.0 (4)	C22—C21—C26—C27	178.11 (10)
C18A—O2A—C17—O2	−93.5 (4)	C2—C21—C26—C27	−1.00 (15)
C18A—O2A—C17—C14	175.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.80	2.01	2.669 (1)	139
N2—H2···S1i	0.89	2.67	3.5551 (9)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.80	2.01	2.669 (1)	139
N2—H2⋯S1i	0.89	2.67	3.5551 (9)	170

Symmetry code: (i) .