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Acta Cryst. (2008). E64, o2083    [ doi:10.1107/S1600536808030596 ]

Propyl 2-(3-benzoylthioureido)acetate

I. N. Hassan, B. M. Yamin and M. B. Kassim

Abstract top

The title compound, C13H16N2O3S, is a thiourea derivative with benzoyl and propoxycarbonylmethyl groups attached to the two terminal N atoms. These groups adopt trans and cis configurations, respectively, with respect to the S atom across the thiourea C-N bonds. The compound crystallizes in the P21/c space group with Z = 8, resulting in two unique molecules in the asymmetric unit linked by C-H...S and C-H...O hydrogen bonds, forming a one-dimensional zigzag chain along the c axis.

Comment top

The title compound, (I), is an analog of the previously reported ethyl 2-(3-benzoylthioureido) acetate (II) (Hassan et al., 2008). As in most carbonylthiourea derivatives of the type R1C(O)NHC(S)NHR2, such as in N-benzoyl-N'-phenylthiourea (Yamin & Yusof, 2003) and 1-(2-morpholinoethyl)-3-(3-phenylacryloyl)thiourea (Yamin & Hassan, 2004), the molecule maintains its cis–trans configuration with respect to the positions of the propyl acetate and benzoyl groups, respectively, relative to the S atom across the C—N bonds (Fig. 1). The bond lengths and angles in the molecules are in normal ranges (Allen et al., 1987) and comparable to those in (II). However, the C═S bond length [1.658 (3) Å] is slightly shorter than that of (II) [1.666 (2) Å]. The phenyl ring [C1–C6 (A)] and the carbonyl thiourea [(S1/N1/N2/O1/C7/C8/C9) (B)] fragments are essentially planar. In the acetate fragment, [O2/O3/C9/C10 (C)], the maximum deviation from the mean plane is 0.013 (3) Å for atom C10. The dihedral angles A/B and B/C are 18.58 (15)° and 20.51 (16)°, respectively. The phenyl ring is inclined to the acetate mean plane with a dihedral angle of 37.07 (19)°. The intramolecular hydrogen bonds N2—H2B···O1 and N2—H2B···O2 (Table 2) form a pseudo-six-member ring (N2/H2B/O1/C7/N1/C8) and pseudo-five-member ring (N2/H2B/O2/C10/C9), respectively. In the crystal structure, molecules are linked by intermolecular C—H···S, C—H···O and N—H···S hydrogen bonds (Table 2), forming a one-dimensional chain parallel to the c axis as seen in (II) (Fig. 2).

Related literature top

For related literature, see: Allen et al. (1987); Hassan et al. (2008); Yamin & Hassan (2004); Yamin & Yusof (2003).

Experimental top

The title compound (I) was synthesized according to a previously reported compound (Hassan et al., 2008). A yellowish crystal, suitable for X-ray crystallography, was obtained by a recrystallization from dichloromethane (yield 75%).

Refinement top

The C-bond H atoms were positioned geometrically and allowed to ride on their parent atoms, with Uiso = 1.2Ueq (C) for aromatic 0.93 Å, Uiso = 1.2Ueq (C) for CH2 0.97 Å and Uiso = 1.5Ueq (C) for CH3 0.96 Å. The H atoms of the amine groups were located in differece Fourier map and refined isotroplically with a restrained N—H distance of 0.87 (1) Å.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsods are drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing of (I) viewed down the a axis. Hydrogen bonds are drawn as dashed lines.
Propyl 2-(3-benzoylthioureido)acetate top
Crystal data top
C13H16N2O3SF(000) = 1184
Mr = 280.34Dx = 1.317 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1848 reflections
a = 11.6722 (19) Åθ = 1.8–25.5°
b = 15.105 (3) ŵ = 0.23 mm−1
c = 16.584 (3) ÅT = 298 K
β = 104.737 (3)°Block, yellowish
V = 2827.6 (8) Å30.34 × 0.29 × 0.09 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		5262 independent reflections
Radiation source: fine-focus sealed tube2854 reflections with I > 2σ(I)
graphiteRint = 0.045
ω scansθmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −14→14
Tmin = 0.925, Tmax = 0.979k = −14→18
15002 measured reflectionsl = −19→20
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0665P)2 + 0.3497P]
where P = (Fo2 + 2Fc2)/3
5262 reflections(Δ/σ)max < 0.001
359 parametersΔρmax = 0.21 e Å−3
4 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C13H16N2O3SV = 2827.6 (8) Å3
Mr = 280.34Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.6722 (19) ŵ = 0.23 mm−1
b = 15.105 (3) ÅT = 298 K
c = 16.584 (3) Å0.34 × 0.29 × 0.09 mm
β = 104.737 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		5262 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		2854 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 0.979Rint = 0.045
15002 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.068H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.162Δρmax = 0.21 e Å−3
S = 1.05Δρmin = −0.17 e Å−3
5262 reflectionsAbsolute structure: ?
359 parametersFlack parameter: ?
4 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
C1−0.1076 (3)0.8544 (3)0.0140 (2)0.0722 (11)
H1A−0.10240.8130−0.02640.087*
C2−0.2152 (3)0.8706 (3)0.0310 (3)0.0848 (13)
H2A−0.28220.83970.00240.102*
C3−0.2240 (3)0.9320 (3)0.0899 (3)0.0768 (12)
H3A−0.29620.94180.10240.092*
C4−0.1257 (3)0.9787 (3)0.1302 (2)0.0693 (11)
H4A−0.13191.02150.16920.083*
C5−0.0180 (3)0.9630 (2)0.1138 (2)0.0574 (9)
H5A0.04810.99540.14130.069*
C6−0.0074 (3)0.8993 (2)0.05653 (19)0.0496 (8)
C70.1050 (3)0.8780 (2)0.0338 (2)0.0497 (8)
C80.3228 (3)0.9015 (2)0.0755 (2)0.0516 (8)
C90.4434 (3)0.8520 (2)−0.01556 (19)0.0613 (10)
H9A0.48690.80370.01700.074*
H9B0.49120.9052−0.00310.074*
C100.4199 (3)0.8311 (2)−0.1062 (2)0.0587 (9)
C110.5118 (3)0.7963 (3)−0.2139 (2)0.0736 (11)
H11A0.46040.8405−0.24720.088*
H11B0.47960.7382−0.23140.088*
C120.6336 (4)0.8042 (3)−0.2255 (2)0.0941 (14)
H12A0.66550.8618−0.20600.113*
H12B0.68380.7596−0.19190.113*
C130.6363 (4)0.7930 (4)−0.3139 (3)0.1222 (19)
H13A0.71640.7981−0.31840.183*
H13B0.58850.8381−0.34720.183*
H13C0.60560.7358−0.33330.183*
C140.6343 (3)0.9685 (2)0.3361 (2)0.0616 (9)
H14A0.56730.99700.30440.074*
C150.7394 (3)0.9753 (3)0.3139 (2)0.0733 (11)
H15A0.74291.00780.26700.088*
C160.8391 (3)0.9346 (3)0.3604 (3)0.0784 (12)
H16A0.90990.93800.34460.094*
C170.8334 (3)0.8889 (3)0.4306 (3)0.0912 (13)
H17A0.90130.86260.46360.109*
C180.7284 (3)0.8816 (3)0.4524 (2)0.0773 (12)
H18A0.72560.85040.50020.093*
C190.6270 (3)0.9199 (2)0.40472 (19)0.0505 (8)
C200.5155 (3)0.9068 (2)0.4304 (2)0.0577 (9)
C210.2955 (3)0.9159 (2)0.3802 (2)0.0533 (9)
C220.1736 (3)0.8807 (2)0.4749 (2)0.0619 (10)
H22A0.12180.84190.43520.074*
H22B0.13560.93810.47270.074*
C230.1951 (3)0.8429 (2)0.5608 (2)0.0577 (9)
C240.1014 (3)0.8073 (3)0.66818 (19)0.0659 (10)
H24A0.16320.83750.70910.079*
H24B0.11960.74450.67050.079*
C25−0.0153 (3)0.8223 (3)0.6859 (2)0.0830 (12)
H25A−0.07680.79510.64240.100*
H25B−0.03100.88540.68550.100*
C26−0.0200 (4)0.7843 (3)0.7694 (2)0.1020 (15)
H26A−0.09660.79530.77870.153*
H26B0.03970.81190.81280.153*
H26C−0.00600.72170.76970.153*
S10.43593 (8)0.94060 (8)0.14867 (6)0.0800 (4)
S20.18284 (8)0.94066 (8)0.30082 (6)0.0798 (4)
O10.10454 (18)0.83491 (16)−0.02851 (14)0.0655 (7)
O20.3254 (2)0.8365 (2)−0.15350 (16)0.1033 (11)
O30.51810 (19)0.80959 (16)−0.12641 (13)0.0662 (7)
O40.5165 (2)0.88349 (19)0.50080 (15)0.0841 (9)
O50.2888 (2)0.81729 (17)0.60138 (14)0.0708 (7)
O60.09492 (18)0.84165 (16)0.58525 (13)0.0653 (7)
N10.2084 (2)0.90800 (19)0.08632 (17)0.0533 (7)
N20.3327 (2)0.8649 (2)0.00618 (17)0.0571 (8)
N30.4114 (2)0.92075 (19)0.37143 (16)0.0533 (7)
N40.2860 (2)0.8897 (2)0.45399 (18)0.0600 (8)
H3B0.416 (3)0.935 (2)0.3220 (10)0.074 (12)*
H2B0.2684 (17)0.847 (2)−0.0292 (16)0.070 (12)*
H1B0.206 (3)0.9362 (19)0.1312 (13)0.069 (11)*
H4B0.346 (2)0.870 (3)0.4919 (18)0.105 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.051 (2)0.085 (3)0.079 (3)0.003 (2)0.014 (2)−0.016 (2)
C20.041 (2)0.104 (4)0.107 (3)−0.006 (2)0.015 (2)−0.014 (3)
C30.049 (2)0.100 (3)0.085 (3)0.008 (2)0.026 (2)0.005 (3)
C40.056 (2)0.096 (3)0.061 (2)0.004 (2)0.0243 (19)−0.002 (2)
C50.049 (2)0.073 (3)0.051 (2)0.0037 (18)0.0134 (16)0.0041 (18)
C60.0412 (19)0.059 (2)0.048 (2)0.0043 (17)0.0091 (16)0.0127 (17)
C70.046 (2)0.058 (2)0.044 (2)0.0019 (17)0.0083 (17)0.0041 (17)
C80.0446 (19)0.061 (2)0.051 (2)0.0042 (16)0.0159 (16)0.0015 (17)
C90.047 (2)0.085 (3)0.053 (2)0.0110 (19)0.0149 (17)−0.0033 (18)
C100.053 (2)0.073 (3)0.050 (2)0.010 (2)0.0144 (19)0.0010 (18)
C110.075 (3)0.101 (3)0.048 (2)0.008 (2)0.0221 (19)0.001 (2)
C120.081 (3)0.145 (4)0.064 (3)0.015 (3)0.033 (2)0.000 (2)
C130.102 (4)0.199 (6)0.075 (3)−0.003 (4)0.038 (3)0.000 (3)
C140.051 (2)0.081 (3)0.049 (2)−0.0051 (19)0.0066 (17)0.0075 (19)
C150.062 (2)0.103 (3)0.059 (2)−0.019 (2)0.023 (2)0.001 (2)
C160.054 (2)0.097 (3)0.091 (3)−0.007 (2)0.031 (2)−0.009 (3)
C170.051 (2)0.111 (4)0.107 (4)0.010 (2)0.010 (2)0.030 (3)
C180.048 (2)0.100 (3)0.080 (3)0.005 (2)0.009 (2)0.029 (2)
C190.0401 (18)0.062 (2)0.048 (2)−0.0049 (17)0.0094 (16)−0.0031 (17)
C200.053 (2)0.072 (3)0.048 (2)−0.0006 (18)0.0109 (18)0.0033 (18)
C210.0461 (19)0.066 (2)0.048 (2)0.0012 (17)0.0133 (16)−0.0017 (17)
C220.0465 (19)0.087 (3)0.054 (2)−0.0023 (19)0.0160 (17)0.0005 (19)
C230.050 (2)0.073 (3)0.052 (2)−0.006 (2)0.0149 (19)−0.0118 (18)
C240.064 (2)0.091 (3)0.045 (2)−0.007 (2)0.0166 (18)0.0012 (19)
C250.068 (3)0.125 (4)0.063 (3)0.006 (2)0.028 (2)0.004 (2)
C260.099 (3)0.152 (4)0.065 (3)−0.006 (3)0.040 (2)0.009 (3)
S10.0493 (5)0.1229 (10)0.0681 (7)−0.0131 (6)0.0158 (5)−0.0340 (6)
S20.0485 (5)0.1340 (10)0.0562 (6)0.0120 (6)0.0123 (5)0.0196 (6)
O10.0526 (14)0.0873 (19)0.0552 (15)0.0002 (13)0.0114 (12)−0.0157 (13)
O20.0507 (16)0.198 (3)0.0565 (17)0.0217 (19)0.0055 (14)−0.0217 (18)
O30.0530 (14)0.100 (2)0.0487 (15)0.0152 (13)0.0182 (11)−0.0011 (12)
O40.0499 (15)0.149 (3)0.0520 (16)−0.0021 (15)0.0104 (12)0.0278 (16)
O50.0522 (15)0.102 (2)0.0575 (16)0.0037 (14)0.0133 (12)0.0067 (13)
O60.0513 (14)0.100 (2)0.0476 (14)−0.0055 (13)0.0177 (11)0.0008 (12)
N10.0449 (16)0.071 (2)0.0453 (18)0.0000 (15)0.0131 (14)−0.0076 (15)
N20.0401 (17)0.085 (2)0.0465 (18)0.0048 (16)0.0106 (15)−0.0061 (15)
N30.0414 (16)0.077 (2)0.0415 (17)0.0009 (14)0.0106 (14)0.0073 (15)
N40.0470 (17)0.090 (2)0.0461 (18)−0.0001 (17)0.0174 (15)0.0069 (16)
Geometric parameters (Å, °) top
C1—C21.378 (5)C14—H14A0.9300
C1—C61.380 (4)C15—C161.367 (5)
C1—H1A0.9300C15—H15A0.9300
C2—C31.368 (5)C16—C171.370 (5)
C2—H2A0.9300C16—H16A0.9300
C3—C41.368 (5)C17—C181.368 (5)
C3—H3A0.9300C17—H17A0.9300
C4—C51.373 (4)C18—C191.373 (4)
C4—H4A0.9300C18—H18A0.9300
C5—C61.378 (4)C19—C201.482 (4)
C5—H5A0.9300C20—O41.217 (4)
C6—C71.490 (4)C20—N31.369 (4)
C7—O11.220 (3)C21—N41.317 (4)
C7—N11.373 (4)C21—N31.399 (4)
C8—N21.307 (4)C21—S21.649 (3)
C8—N11.395 (4)C22—N41.446 (4)
C8—S11.658 (3)C22—C231.496 (4)
C9—N21.440 (4)C22—H22A0.9700
C9—C101.492 (4)C22—H22B0.9700
C9—H9A0.9700C23—O51.193 (4)
C9—H9B0.9700C23—O61.332 (4)
C10—O21.182 (4)C24—O61.454 (4)
C10—O31.314 (4)C24—C251.483 (4)
C11—O31.447 (4)C24—H24A0.9700
C11—C121.487 (5)C24—H24B0.9700
C11—H11A0.9700C25—C261.512 (5)
C11—H11B0.9700C25—H25A0.9700
C12—C131.484 (5)C25—H25B0.9700
C12—H12A0.9700C26—H26A0.9600
C12—H12B0.9700C26—H26B0.9600
C13—H13A0.9600C26—H26C0.9600
C13—H13B0.9600N1—H1B0.863 (10)
C13—H13C0.9600N2—H2B0.871 (10)
C14—C151.371 (4)N3—H3B0.862 (10)
C14—C191.375 (4)N4—H4B0.867 (10)
C2—C1—C6120.4 (4)C15—C16—H16A120.4
C2—C1—H1A119.8C17—C16—H16A120.4
C6—C1—H1A119.8C18—C17—C16120.4 (4)
C3—C2—C1120.3 (4)C18—C17—H17A119.8
C3—C2—H2A119.9C16—C17—H17A119.8
C1—C2—H2A119.9C17—C18—C19120.8 (4)
C4—C3—C2119.5 (3)C17—C18—H18A119.6
C4—C3—H3A120.2C19—C18—H18A119.6
C2—C3—H3A120.2C18—C19—C14118.4 (3)
C3—C4—C5120.6 (4)C18—C19—C20118.0 (3)
C3—C4—H4A119.7C14—C19—C20123.6 (3)
C5—C4—H4A119.7O4—C20—N3121.3 (3)
C4—C5—C6120.3 (3)O4—C20—C19121.3 (3)
C4—C5—H5A119.9N3—C20—C19117.3 (3)
C6—C5—H5A119.9N4—C21—N3115.1 (3)
C5—C6—C1118.8 (3)N4—C21—S2124.8 (2)
C5—C6—C7124.3 (3)N3—C21—S2120.0 (2)
C1—C6—C7116.8 (3)N4—C22—C23108.8 (3)
O1—C7—N1121.8 (3)N4—C22—H22A109.9
O1—C7—C6121.0 (3)C23—C22—H22A109.9
N1—C7—C6117.2 (3)N4—C22—H22B109.9
N2—C8—N1116.4 (3)C23—C22—H22B109.9
N2—C8—S1124.2 (2)H22A—C22—H22B108.3
N1—C8—S1119.4 (2)O5—C23—O6125.0 (3)
N2—C9—C10109.5 (3)O5—C23—C22124.6 (3)
N2—C9—H9A109.8O6—C23—C22110.4 (3)
C10—C9—H9A109.8O6—C24—C25107.7 (3)
N2—C9—H9B109.8O6—C24—H24A110.2
C10—C9—H9B109.8C25—C24—H24A110.2
H9A—C9—H9B108.2O6—C24—H24B110.2
O2—C10—O3125.1 (3)C25—C24—H24B110.2
O2—C10—C9123.7 (3)H24A—C24—H24B108.5
O3—C10—C9111.1 (3)C24—C25—C26111.9 (3)
O3—C11—C12108.2 (3)C24—C25—H25A109.2
O3—C11—H11A110.1C26—C25—H25A109.2
C12—C11—H11A110.1C24—C25—H25B109.2
O3—C11—H11B110.1C26—C25—H25B109.2
C12—C11—H11B110.1H25A—C25—H25B107.9
H11A—C11—H11B108.4C25—C26—H26A109.5
C13—C12—C11112.4 (4)C25—C26—H26B109.5
C13—C12—H12A109.1H26A—C26—H26B109.5
C11—C12—H12A109.1C25—C26—H26C109.5
C13—C12—H12B109.1H26A—C26—H26C109.5
C11—C12—H12B109.1H26B—C26—H26C109.5
H12A—C12—H12B107.9C10—O3—C11117.6 (3)
C12—C13—H13A109.5C23—O6—C24117.0 (3)
C12—C13—H13B109.5C7—N1—C8127.7 (3)
H13A—C13—H13B109.5C7—N1—H1B120 (2)
C12—C13—H13C109.5C8—N1—H1B112 (2)
H13A—C13—H13C109.5C8—N2—C9124.3 (3)
H13B—C13—H13C109.5C8—N2—H2B118 (2)
C15—C14—C19120.7 (3)C9—N2—H2B118 (2)
C15—C14—H14A119.7C20—N3—C21128.6 (3)
C19—C14—H14A119.7C20—N3—H3B117 (2)
C16—C15—C14120.4 (4)C21—N3—H3B114 (2)
C16—C15—H15A119.8C21—N4—C22123.1 (3)
C14—C15—H15A119.8C21—N4—H4B122 (3)
C15—C16—C17119.2 (3)C22—N4—H4B114 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O10.87 (2)1.92 (2)2.617 (3)136 (2)
N2—H2B···O20.87 (2)2.33 (2)2.663 (4)103 (2)
N4—H4B···O40.87 (3)1.97 (2)2.605 (4)129 (3)
N4—H4B···O50.87 (3)2.23 (3)2.671 (4)111 (2)
C5—H5A···S20.932.843.396 (3)120
C13—H13B···O4i0.962.543.329 (6)139
C14—H14A···S10.932.783.397 (3)125
C24—H24A···O2ii0.972.573.441 (4)150
C26—H26B···O1ii0.962.573.384 (4)143
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O10.87 (2)1.92 (2)2.617 (3)136 (2)
N2—H2B···O20.87 (2)2.33 (2)2.663 (4)103 (2)
N4—H4B···O40.87 (3)1.97 (2)2.605 (4)129 (3)
N4—H4B···O50.87 (3)2.23 (3)2.671 (4)111 (2)
C5—H5A···S20.932.843.396 (3)120
C13—H13B···O4i0.962.543.329 (6)139
C14—H14A···S10.932.783.397 (3)125
C24—H24A···O2ii0.972.573.441 (4)150
C26—H26B···O1ii0.962.573.384 (4)143
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1.
Acknowledgements top

The authors thank Universiti Kebangsaan Malaysia for providing facilities, and the Ministry of Science, Technology and Innovation for research fund No. UKM-ST-01FRGS0016-2006.

references
References top

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