Ethyl 4-(3-benzoyl-thio-ureido)benzoate.

The title compound, C(17)H(16)N(2)O(3)S, crystallizes in the thio-amide form with an intra-molecular N-H⋯O hydrogen bond across the thio-urea system. Mol-ecules are connected in chains parallel to [10] by hydrogen bonds from the second thio-urea N-H group to the benzoate C=O function.

Related literature

For related literature, see: Huebner et al. (1953 ▶); Xu et al. (2004 ▶); Xue et al. (2003 ▶); Zeng et al. (2003 ▶); Zheng et al. (2004 ▶); Douglas & Dains (1934 ▶); Glasser & Doughty (1964 ▶); Morales et al. (2000 ▶); D’hooghe et al. (2005 ▶); Dušek (1985 ▶).

Experimental

Crystal data

C17H16N2O3S

M = 328.38

Monoclinic,

a = 9.6018 (3) Å

b = 8.3882 (3) Å

c = 19.3199 (6) Å

β = 91.393 (4)°

V = 1555.60 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 100 (2) K

0.38 × 0.24 × 0.13 mm

Data collection

Oxford Diffraction Xcalibur S diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.943, T max = 1.000 (expected range = 0.916–0.971)

31428 measured reflections

5103 independent reflections

3676 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.092

S = 0.94

5103 reflections

217 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis RED (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017856/im2071sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017856/im2071Isup2.hkl

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

C17H16N2O3S	F000 = 688
Mr = 328.38	Dx = 1.402 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11202 reflections
a = 9.6018 (3) Å	θ = 2.6–32.1º
b = 8.3882 (3) Å	µ = 0.23 mm−1
c = 19.3199 (6) Å	T = 100 (2) K
β = 91.393 (4)º	Tablet, colourless
V = 1555.60 (9) Å3	0.38 × 0.24 × 0.13 mm
Z = 4

Oxford Diffraction Xcalibur S diffractometer	5103 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3676 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.048
Detector resolution: 16.1057 pixels mm-1	θmax = 32.2º
T = 100(2) K	θmin = 2.7º
ω scans	h = −14→13
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2008)	k = −12→12
Tmin = 0.943, Tmax = 1.000	l = −27→28
31428 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0546P)2
S = 0.94	(Δ/σ)max < 0.001
5103 reflections	Δρmax = 0.43 e Å−3
217 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18)

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
S	0.10457 (3)	0.58015 (4)	0.231857 (14)	0.01866 (8)
O1	0.51573 (9)	0.70720 (10)	0.34044 (4)	0.01821 (18)
O2	0.50845 (9)	0.81469 (9)	−0.09004 (4)	0.01765 (18)
O3	0.35152 (9)	0.61785 (9)	−0.10425 (4)	0.01525 (17)
N1	0.28549 (11)	0.63504 (11)	0.33385 (5)	0.01329 (19)
H01	0.2098 (15)	0.6256 (15)	0.3555 (7)	0.020 (4)*
N2	0.37602 (11)	0.65342 (11)	0.22473 (5)	0.0146 (2)
H02	0.4445 (16)	0.6886 (17)	0.2488 (7)	0.028 (4)*
C1	0.39896 (12)	0.67621 (12)	0.44636 (5)	0.0126 (2)
C2	0.48431 (13)	0.78318 (13)	0.48262 (6)	0.0171 (2)
H2	0.5431	0.8536	0.4582	0.021*
C3	0.48347 (13)	0.78691 (14)	0.55439 (6)	0.0196 (2)
H3	0.5392	0.8624	0.5791	0.023*
C4	0.40113 (13)	0.68031 (14)	0.59006 (6)	0.0190 (2)
H4	0.4013	0.6822	0.6392	0.023*
C5	0.31886 (13)	0.57135 (14)	0.55422 (6)	0.0188 (2)
H5	0.2644	0.4969	0.5789	0.023*
C6	0.31562 (12)	0.57034 (13)	0.48250 (6)	0.0158 (2)
H6	0.2567	0.4977	0.4580	0.019*
C7	0.40746 (12)	0.67435 (12)	0.36961 (5)	0.0131 (2)
C8	0.26324 (12)	0.62392 (12)	0.26210 (5)	0.0128 (2)
C9	0.38365 (12)	0.66358 (13)	0.15181 (5)	0.0125 (2)
C10	0.32131 (12)	0.55175 (13)	0.10741 (5)	0.0142 (2)
H10	0.2696	0.4656	0.1257	0.017*
C11	0.33527 (12)	0.56701 (13)	0.03650 (5)	0.0130 (2)
H11	0.2917	0.4920	0.0061	0.016*
C12	0.41293 (11)	0.69188 (12)	0.00951 (5)	0.0117 (2)
C13	0.47771 (12)	0.80015 (13)	0.05441 (5)	0.0139 (2)
H13	0.5328	0.8837	0.0363	0.017*
C14	0.46254 (12)	0.78708 (13)	0.12517 (5)	0.0146 (2)
H14	0.5059	0.8623	0.1555	0.018*
C15	0.43123 (12)	0.71552 (12)	−0.06585 (5)	0.0123 (2)
C16	0.36048 (13)	0.63785 (14)	−0.17859 (5)	0.0173 (2)
H16A	0.4578	0.6239	−0.1932	0.021*
H16B	0.3287	0.7458	−0.1924	0.021*
C17	0.26837 (14)	0.51324 (15)	−0.21156 (6)	0.0235 (3)
H17A	0.3001	0.4072	−0.1968	0.035*
H17B	0.2728	0.5216	−0.2621	0.035*
H17C	0.1722	0.5295	−0.1973	0.035*

	U11	U22	U33	U12	U13	U23
S	0.01261 (15)	0.03287 (18)	0.01044 (13)	−0.00304 (12)	−0.00088 (10)	0.00021 (11)
O1	0.0142 (4)	0.0261 (5)	0.0143 (4)	−0.0035 (3)	0.0007 (3)	0.0017 (3)
O2	0.0229 (5)	0.0169 (4)	0.0133 (4)	−0.0043 (3)	0.0029 (3)	0.0005 (3)
O3	0.0168 (4)	0.0195 (4)	0.0094 (3)	−0.0034 (3)	−0.0011 (3)	−0.0005 (3)
N1	0.0111 (5)	0.0198 (5)	0.0090 (4)	−0.0013 (4)	0.0007 (3)	0.0001 (3)
N2	0.0140 (5)	0.0205 (5)	0.0092 (4)	−0.0031 (4)	−0.0002 (4)	−0.0004 (3)
C1	0.0131 (6)	0.0139 (5)	0.0106 (5)	0.0026 (4)	−0.0014 (4)	0.0000 (4)
C2	0.0190 (6)	0.0169 (6)	0.0155 (5)	−0.0030 (5)	−0.0005 (4)	−0.0001 (4)
C3	0.0226 (7)	0.0208 (6)	0.0151 (5)	−0.0013 (5)	−0.0037 (5)	−0.0043 (4)
C4	0.0197 (6)	0.0264 (6)	0.0110 (5)	0.0032 (5)	−0.0003 (4)	−0.0005 (4)
C5	0.0168 (6)	0.0254 (6)	0.0141 (5)	−0.0013 (5)	0.0009 (4)	0.0046 (4)
C6	0.0143 (6)	0.0193 (6)	0.0136 (5)	−0.0018 (4)	−0.0023 (4)	0.0003 (4)
C7	0.0142 (6)	0.0128 (5)	0.0121 (5)	0.0007 (4)	−0.0016 (4)	0.0000 (4)
C8	0.0151 (6)	0.0135 (5)	0.0099 (5)	0.0012 (4)	0.0000 (4)	0.0005 (4)
C9	0.0118 (5)	0.0158 (5)	0.0098 (5)	0.0019 (4)	0.0010 (4)	0.0002 (4)
C10	0.0144 (6)	0.0146 (5)	0.0137 (5)	−0.0013 (4)	0.0027 (4)	0.0001 (4)
C11	0.0126 (5)	0.0139 (5)	0.0125 (5)	−0.0002 (4)	0.0008 (4)	−0.0026 (4)
C12	0.0113 (5)	0.0136 (5)	0.0103 (5)	0.0029 (4)	0.0012 (4)	−0.0002 (4)
C13	0.0148 (6)	0.0136 (5)	0.0135 (5)	−0.0011 (4)	0.0017 (4)	0.0004 (4)
C14	0.0147 (6)	0.0171 (5)	0.0121 (5)	−0.0017 (4)	0.0003 (4)	−0.0025 (4)
C15	0.0129 (5)	0.0132 (5)	0.0107 (5)	0.0030 (4)	0.0001 (4)	−0.0007 (4)
C16	0.0224 (6)	0.0216 (6)	0.0078 (5)	−0.0010 (5)	−0.0014 (4)	0.0005 (4)
C17	0.0232 (7)	0.0311 (7)	0.0161 (6)	−0.0049 (5)	−0.0019 (5)	−0.0042 (5)

S—C8	1.6594 (12)	C12—C13	1.3921 (15)
O1—C7	1.2259 (14)	C12—C15	1.4839 (14)
O2—C15	1.2153 (13)	C13—C14	1.3827 (14)
O3—C15	1.3342 (13)	C16—C17	1.5010 (16)
O3—C16	1.4505 (12)	N1—H01	0.852 (15)
N1—C7	1.3850 (14)	N2—H02	0.849 (15)
N1—C8	1.4005 (13)	C2—H2	0.9500
N2—C8	1.3391 (15)	C3—H3	0.9500
N2—C9	1.4151 (13)	C4—H4	0.9500
C1—C2	1.3926 (15)	C5—H5	0.9500
C1—C6	1.3941 (15)	C6—H6	0.9500
C1—C7	1.4871 (14)	C10—H10	0.9500
C2—C3	1.3872 (15)	C11—H11	0.9500
C3—C4	1.3879 (17)	C13—H13	0.9500
C4—C5	1.3829 (17)	C14—H14	0.9500
C5—C6	1.3852 (15)	C16—H16A	0.9900
C9—C14	1.3895 (15)	C16—H16B	0.9900
C9—C10	1.3961 (15)	C17—H17A	0.9800
C10—C11	1.3857 (14)	C17—H17B	0.9800
C11—C12	1.3943 (15)	C17—H17C	0.9800
C15—O3—C16	115.63 (9)	C8—N1—H01	111.7 (9)
C7—N1—C8	128.05 (10)	C8—N2—H02	113.3 (10)
C8—N2—C9	127.59 (10)	C9—N2—H02	117.8 (10)
C2—C1—C6	119.77 (10)	C3—C2—H2	120.0
C2—C1—C7	117.54 (10)	C1—C2—H2	120.0
C6—C1—C7	122.59 (10)	C2—C3—H3	120.0
C3—C2—C1	119.97 (11)	C4—C3—H3	120.0
C2—C3—C4	119.94 (11)	C5—C4—H4	119.9
C5—C4—C3	120.17 (10)	C3—C4—H4	119.9
C4—C5—C6	120.24 (11)	C4—C5—H5	119.9
C5—C6—C1	119.85 (10)	C6—C5—H5	119.9
O1—C7—N1	122.71 (10)	C5—C6—H6	120.1
O1—C7—C1	121.58 (10)	C1—C6—H6	120.1
N1—C7—C1	115.70 (10)	C11—C10—H10	120.2
N2—C8—N1	114.55 (10)	C9—C10—H10	120.2
N2—C8—S	126.77 (8)	C10—C11—H11	119.8
N1—C8—S	118.68 (8)	C12—C11—H11	119.8
C14—C9—C10	120.19 (10)	C14—C13—H13	119.7
C14—C9—N2	117.10 (9)	C12—C13—H13	119.7
C10—C9—N2	122.64 (10)	C13—C14—H14	120.1
C11—C10—C9	119.67 (10)	C9—C14—H14	120.1
C10—C11—C12	120.31 (10)	O3—C16—H16A	110.3
C13—C12—C11	119.47 (10)	C17—C16—H16A	110.3
C13—C12—C15	117.54 (10)	O3—C16—H16B	110.3
C11—C12—C15	122.99 (9)	C17—C16—H16B	110.3
C14—C13—C12	120.54 (10)	H16A—C16—H16B	108.6
C13—C14—C9	119.78 (10)	C16—C17—H17A	109.5
O2—C15—O3	123.60 (9)	C16—C17—H17B	109.5
O2—C15—C12	123.83 (10)	H17A—C17—H17B	109.5
O3—C15—C12	112.56 (9)	C16—C17—H17C	109.5
O3—C16—C17	106.93 (9)	H17A—C17—H17C	109.5
C7—N1—H01	119.9 (9)	H17B—C17—H17C	109.5
C6—C1—C2—C3	−1.67 (17)	C8—N2—C9—C10	−46.16 (17)
C7—C1—C2—C3	−178.22 (10)	C14—C9—C10—C11	−1.79 (17)
C1—C2—C3—C4	2.21 (18)	N2—C9—C10—C11	−178.66 (10)
C2—C3—C4—C5	−0.63 (18)	C9—C10—C11—C12	1.00 (17)
C3—C4—C5—C6	−1.51 (18)	C10—C11—C12—C13	0.73 (16)
C4—C5—C6—C1	2.04 (18)	C10—C11—C12—C15	−179.62 (10)
C2—C1—C6—C5	−0.45 (17)	C11—C12—C13—C14	−1.70 (17)
C7—C1—C6—C5	175.92 (10)	C15—C12—C13—C14	178.63 (10)
C8—N1—C7—O1	0.74 (17)	C12—C13—C14—C9	0.92 (17)
C8—N1—C7—C1	−179.93 (10)	C10—C9—C14—C13	0.83 (17)
C2—C1—C7—O1	30.47 (15)	N2—C9—C14—C13	177.88 (10)
C6—C1—C7—O1	−145.97 (11)	C16—O3—C15—O2	−0.79 (16)
C2—C1—C7—N1	−148.86 (10)	C16—O3—C15—C12	178.03 (9)
C6—C1—C7—N1	34.69 (15)	C13—C12—C15—O2	6.55 (16)
C9—N2—C8—N1	−174.63 (10)	C11—C12—C15—O2	−173.11 (11)
C9—N2—C8—S	4.22 (17)	C13—C12—C15—O3	−172.27 (10)
C7—N1—C8—N2	0.99 (16)	C11—C12—C15—O3	8.07 (15)
C7—N1—C8—S	−177.97 (9)	C15—O3—C16—C17	177.67 (10)
C8—N2—C9—C14	136.88 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H02···O1	0.85 (2)	1.89 (2)	2.618 (1)	143 (1)
N1—H01···O2i	0.85 (2)	2.28 (2)	3.099 (1)	162 (1)
C3—H3···Sii	0.95	3.04	3.763 (1)	134
C17—H17C···Siii	0.98	2.88	3.677 (1)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H02⋯O1	0.85 (2)	1.89 (2)	2.618 (1)	143 (1)
N1—H01⋯O2i	0.85 (2)	2.28 (2)	3.099 (1)	162 (1)
C3—H3⋯Sii	0.95	3.04	3.763 (1)	134
C17—H17C⋯Siii	0.98	2.88	3.677 (1)	140

Symmetry codes: (i) ; (ii) ; (iii) .