Butyl 2-(3-benzoyl­thio­ureido)acetate

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

doi:10.1107/S1600536808033540

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2167

doi:10.1107/S1600536808033540

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Butyl 2-(3-benzoylthioureido)acetate

Ibrahim N. Hassan,^a Bohari M. Yamin ^a and Mohammad B. Kassim ^a ^*

^aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi Selangor, Malaysia
^*Correspondence e-mail: mbkassim@ukm.my

(Received 10 October 2008; accepted 15 October 2008; online 22 October 2008)

In the title compound, C₁₄H₁₈N₂O₃S, the butyl acetate fragment and the benzoyl group adopt a cis–trans configuration, respectively, with respect to the thiono S atom across the C—N bonds. In the crystal packing, the molecules are linked by intermolecular N—H⋯O and C—H⋯O hydrogen bonds to form a one-dimensional chain along the c axis. The terminal butyl C atom is disordered with occupancies 0.82 (2)and 0.18 (2).

Related literature

For information on bond lengths, see: Allen et al. (1987 ); For related structures, see: Hassan et al. (2008a ,b ); Yamin & Hassan (2004 ); Yamin & Yusof (2003 ).

Experimental

Crystal data

C₁₄H₁₈N₂O₃S
M_r = 294.36
Monoclinic, P 2₁ /c
a = 14.051 (3) Å
b = 7.9482 (18) Å
c = 14.116 (3) Å
β = 102.753 (3)°
V = 1537.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 (2) K
0.46 × 0.28 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.906, T_max = 0.947
7933 measured reflections
2853 independent reflections
2098 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.136
S = 1.03
2853 reflections
187 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.39	3.203 (2)	158
N2—H2A⋯O1	0.86	1.96	2.631 (2)	134
C2—H2⋯O1ⁱ	0.93	2.53	3.328 (3)	144
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033540/at2648sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033540/at2648Isup2.hkl

checkCIF report

Comment top

The title compound (I) is a thiourea derivative of glycine analogous to ethyl-2-(3-benzoylthioureido)acetate (II) (Hassan et al., 2008a) and propyl-2-(3-benzoylthioureido)acetate (III) (Hassan et al., 2008b), with the shorter alkyl groups replaced by a butyl group. The molecule maintains the same cis–trans configuration with respect to the positions of the butyl acetate and benzoyl groups, relative to the S atom across the C—N bonds (Fig. 1 and Fig. 2), respectively. There is a disorder in the molecules involving the terminal butyl carbon atom. 'Soft' restrains, SIMU and EADP, were applied to the disorder components, C14 and C14', to resolve the overlapping components. In the final refinement the main disorder component, C14, resides in about 80% occupancy whereas the minor component, C14', occupies 20% at a time.

The compound was synthesized by a similar procedure to that of reported in (II). The bond lengths and angles in the molecules are in normal ranges (Allen et al., 1987) and comparable to those in II and III. The phenyl ring, (C1–C6), and the central fragment, (C6/C7/C8/C9/N1/N2/S1), are essentially planar and the dihedral angle between them is 27.82 (9)°. In the butyl fragment, (C11/C12/C13/O3), the maximum deviation from the mean plane is 0.017 (3)Å for the atom C12. The dihedral angle between the phenyl ring and the butyl group is 14.5 (3)°. The intramolecular N2—H2···O1 and C9—H9B···S1 hydrogen bonds, (Table 1), force the molecule to adopt the present molecular conformation. The intermolecular N1—H1B···O2 and C2—H4A···O1 hydrogen bonds, (Table 2), link the molecules into a chain parallel to the c axis (Fig. 3).

Related literature top

For information on bond lengths, see: Allen et al. (1987); For related literature on analogous molecules, see: Hassan et al. (2008a,b). For related structures, refer to: Yamin & Hassan (2004); Yamin & Yusof (2003).

Experimental top

Preparation of the compound was carried out according to a previously reported experimental procedures (Hassan et al., 2008a). A yellowish crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from CH₂Cl₂ solution at room temperature (yield 75%).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (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

	Fig. 1. The molecular structure of (I) showing the main (80% occupancy) disorder component of the butyl terminal carbon atom, with displacement ellipsods are drawn at the 50% probability level.
	Fig. 2. The molecular structure of (I) showing the minor (20% occupancy) disorder component of the butyl terminal carbon atom, with displacement ellipsods are drawn at the 50% probability level.
	Fig. 3. Crystal packing of (I) viewed down the a axis. Hydrogen bonds are drawn as dashed lines.

Butyl 2-(3-benzoylthioureido)acetate top

Crystal data top

C₁₄H₁₈N₂O₃S	F(000) = 624
M_r = 294.36	D_x = 1.272 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2213 reflections
a = 14.051 (3) Å	θ = 3.0–25.5°
b = 7.9482 (18) Å	µ = 0.22 mm⁻¹
c = 14.116 (3) Å	T = 298 K
β = 102.753 (3)°	Block, colourless
V = 1537.5 (6) Å³	0.46 × 0.28 × 0.25 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2853 independent reflections
Radiation source: fine-focus sealed tube	2098 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 25.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −17→15
T_min = 0.906, T_max = 0.947	k = −9→9
7933 measured reflections	l = −17→16

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0696P)² + 0.3732P] where P = (F_o² + 2F_c²)/3
2853 reflections	(Δ/σ)_max < 0.001
187 parameters	Δρ_max = 0.24 e Å⁻³
6 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₄H₁₈N₂O₃S	V = 1537.5 (6) Å³
M_r = 294.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.051 (3) Å	µ = 0.22 mm⁻¹
b = 7.9482 (18) Å	T = 298 K
c = 14.116 (3) Å	0.46 × 0.28 × 0.25 mm
β = 102.753 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2853 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2098 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.947	R_int = 0.022
7933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	6 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
2853 reflections	Δρ_min = −0.27 e Å⁻³
187 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C5	0.38240 (15)	0.4009 (3)	0.51713 (17)	0.0528 (6)
H5	0.3785	0.4057	0.4506	0.063*
C4	0.31404 (17)	0.4833 (3)	0.55659 (18)	0.0588 (6)
H4	0.2645	0.5445	0.5167	0.071*
C3	0.31902 (17)	0.4750 (3)	0.65504 (18)	0.0606 (6)
H3	0.2730	0.5312	0.6816	0.073*
C2	0.39148 (17)	0.3842 (3)	0.71373 (17)	0.0626 (7)
H2	0.3936	0.3768	0.7799	0.075*
C1	0.46139 (16)	0.3037 (3)	0.67530 (16)	0.0545 (6)
H1	0.5114	0.2445	0.7158	0.065*
C6	0.45697 (14)	0.3111 (3)	0.57640 (15)	0.0460 (5)
C7	0.52769 (15)	0.2248 (3)	0.52830 (15)	0.0480 (5)
C8	0.69838 (15)	0.1216 (3)	0.55880 (15)	0.0477 (5)
C9	0.75837 (16)	−0.0258 (3)	0.43410 (16)	0.0563 (6)
H9A	0.7547	−0.1438	0.4503	0.068*
H9B	0.8220	0.0155	0.4671	0.068*
C10	0.74863 (17)	−0.0094 (3)	0.32743 (17)	0.0526 (5)
C11	0.82911 (19)	−0.0919 (4)	0.20303 (18)	0.0751 (8)
H11A	0.8197	0.0214	0.1771	0.090*
H11B	0.7797	−0.1641	0.1645	0.090*
C12	0.92815 (19)	−0.1537 (4)	0.1994 (2)	0.0751 (8)
H12A	0.9353	−0.2686	0.2231	0.090*
H12B	0.9765	−0.0855	0.2424	0.090*
C13	0.9475 (2)	−0.1483 (5)	0.0995 (2)	0.0897 (9)
H13A	0.9217	−0.2484	0.0637	0.108*
H13B	0.9161	−0.0507	0.0648	0.108*
C14'	1.050 (2)	−0.139 (7)	0.108 (2)	0.111 (3)	0.18 (2)
H14E	1.0727	−0.0282	0.1288	0.166*	0.18 (2)
H14F	1.0652	−0.1633	0.0466	0.166*	0.18 (2)
H14D	1.0819	−0.2199	0.1554	0.166*	0.18 (2)
C14	1.0392 (5)	−0.2373 (17)	0.0885 (5)	0.111 (3)	0.82 (2)
H14B	1.0456	−0.2286	0.0223	0.166*	0.82 (2)
H14A	1.0356	−0.3537	0.1055	0.166*	0.82 (2)
H14C	1.0947	−0.1862	0.1306	0.166*	0.82 (2)
S1	0.80227 (5)	0.10476 (11)	0.64102 (5)	0.0744 (3)
O1	0.50502 (11)	0.1805 (2)	0.44383 (11)	0.0647 (5)
O2	0.68594 (12)	0.0656 (2)	0.27269 (13)	0.0709 (5)
O3	0.82116 (12)	−0.0935 (2)	0.30338 (11)	0.0648 (5)
N1	0.61986 (12)	0.2016 (2)	0.58446 (12)	0.0492 (5)
H1A	0.6302	0.2413	0.6425	0.059*
N2	0.68439 (13)	0.0652 (2)	0.46870 (13)	0.0517 (5)
H2A	0.6292	0.0835	0.4295	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C5	0.0497 (12)	0.0591 (14)	0.0492 (13)	−0.0022 (11)	0.0100 (10)	0.0037 (11)
C4	0.0504 (13)	0.0584 (15)	0.0658 (15)	0.0052 (11)	0.0090 (11)	0.0063 (12)
C3	0.0552 (14)	0.0631 (16)	0.0670 (16)	0.0002 (11)	0.0209 (12)	−0.0101 (12)
C2	0.0611 (15)	0.0801 (18)	0.0481 (13)	−0.0007 (13)	0.0154 (11)	−0.0050 (12)
C1	0.0499 (12)	0.0630 (15)	0.0481 (13)	0.0003 (11)	0.0057 (10)	0.0024 (11)
C6	0.0421 (11)	0.0488 (12)	0.0463 (12)	−0.0056 (9)	0.0077 (9)	−0.0015 (10)
C7	0.0460 (12)	0.0511 (13)	0.0459 (12)	−0.0034 (10)	0.0076 (9)	0.0015 (10)
C8	0.0470 (12)	0.0481 (13)	0.0495 (13)	−0.0026 (10)	0.0137 (10)	0.0069 (10)
C9	0.0539 (13)	0.0606 (15)	0.0566 (14)	0.0078 (11)	0.0171 (11)	0.0027 (11)
C10	0.0485 (12)	0.0540 (14)	0.0575 (14)	−0.0006 (11)	0.0162 (11)	−0.0009 (11)
C11	0.0707 (17)	0.101 (2)	0.0565 (15)	0.0157 (15)	0.0201 (13)	−0.0033 (14)
C12	0.0645 (16)	0.092 (2)	0.0718 (17)	0.0078 (14)	0.0222 (13)	−0.0051 (15)
C13	0.087 (2)	0.110 (2)	0.0789 (19)	0.0225 (18)	0.0322 (16)	0.0006 (17)
C14'	0.104 (3)	0.147 (7)	0.093 (3)	0.051 (4)	0.048 (3)	0.010 (4)
C14	0.104 (3)	0.147 (7)	0.093 (3)	0.051 (4)	0.048 (3)	0.010 (4)
S1	0.0534 (4)	0.1112 (6)	0.0549 (4)	0.0174 (4)	0.0040 (3)	−0.0017 (4)
O1	0.0538 (9)	0.0881 (12)	0.0482 (10)	0.0065 (9)	0.0030 (7)	−0.0130 (9)
O2	0.0631 (11)	0.0901 (13)	0.0620 (11)	0.0204 (10)	0.0188 (9)	0.0141 (9)
O3	0.0613 (10)	0.0803 (12)	0.0557 (10)	0.0175 (9)	0.0195 (8)	−0.0007 (8)
N1	0.0449 (10)	0.0609 (12)	0.0418 (9)	0.0013 (9)	0.0096 (7)	−0.0019 (8)
N2	0.0454 (10)	0.0605 (12)	0.0494 (11)	0.0029 (9)	0.0109 (8)	−0.0034 (9)

Geometric parameters (Å, º) top

C5—C4	1.377 (3)	C10—O2	1.195 (3)
C5—C6	1.386 (3)	C10—O3	1.324 (3)
C5—H5	0.9300	C11—O3	1.445 (3)
C4—C3	1.378 (3)	C11—C12	1.487 (4)
C4—H4	0.9300	C11—H11A	0.9700
C3—C2	1.368 (3)	C11—H11B	0.9700
C3—H3	0.9300	C12—C13	1.494 (4)
C2—C1	1.380 (3)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C1—C6	1.385 (3)	C13—C14'	1.42 (3)
C1—H1	0.9300	C13—C14	1.507 (7)
C6—C7	1.489 (3)	C13—H13A	0.9700
C7—O1	1.216 (2)	C13—H13B	0.9700
C7—N1	1.373 (3)	C14'—H14E	0.9600
C8—N2	1.322 (3)	C14'—H14F	0.9600
C8—N1	1.389 (3)	C14'—H14D	0.9600
C8—S1	1.658 (2)	C14—H14B	0.9600
C9—N2	1.437 (3)	C14—H14A	0.9600
C9—C10	1.487 (3)	C14—H14C	0.9600
C9—H9A	0.9700	N1—H1A	0.8600
C9—H9B	0.9700	N2—H2A	0.8600

C4—C5—C6	120.2 (2)	O3—C11—H11B	110.1
C4—C5—H5	119.9	C12—C11—H11B	110.1
C6—C5—H5	119.9	H11A—C11—H11B	108.5
C5—C4—C3	120.0 (2)	C11—C12—C13	112.9 (2)
C5—C4—H4	120.0	C11—C12—H12A	109.0
C3—C4—H4	120.0	C13—C12—H12A	109.0
C2—C3—C4	120.1 (2)	C11—C12—H12B	109.0
C2—C3—H3	120.0	C13—C12—H12B	109.0
C4—C3—H3	120.0	H12A—C12—H12B	107.8
C3—C2—C1	120.4 (2)	C14'—C13—C12	108.2 (12)
C3—C2—H2	119.8	C14'—C13—C14	32.8 (19)
C1—C2—H2	119.8	C12—C13—C14	115.0 (3)
C2—C1—C6	119.9 (2)	C14'—C13—H13A	110.1
C2—C1—H1	120.0	C12—C13—H13A	110.1
C6—C1—H1	120.0	C14—C13—H13A	77.9
C1—C6—C5	119.4 (2)	C14'—C13—H13B	110.1
C1—C6—C7	123.66 (19)	C12—C13—H13B	110.1
C5—C6—C7	116.99 (19)	C14—C13—H13B	128.8
O1—C7—N1	122.4 (2)	H13A—C13—H13B	108.4
O1—C7—C6	121.58 (19)	C13—C14'—H14E	109.5
N1—C7—C6	115.97 (18)	C13—C14'—H14F	109.5
N2—C8—N1	116.64 (19)	C13—C14'—H14D	109.5
N2—C8—S1	124.56 (17)	C13—C14—H14B	109.5
N1—C8—S1	118.80 (16)	C13—C14—H14A	109.5
N2—C9—C10	112.83 (19)	H14B—C14—H14A	109.5
N2—C9—H9A	109.0	C13—C14—H14C	109.5
C10—C9—H9A	109.0	H14B—C14—H14C	109.5
N2—C9—H9B	109.0	H14A—C14—H14C	109.5
C10—C9—H9B	109.0	C10—O3—C11	118.49 (19)
H9A—C9—H9B	107.8	C7—N1—C8	127.81 (18)
O2—C10—O3	125.8 (2)	C7—N1—H1A	116.1
O2—C10—C9	126.0 (2)	C8—N1—H1A	116.1
O3—C10—C9	108.1 (2)	C8—N2—C9	122.18 (19)
O3—C11—C12	107.8 (2)	C8—N2—H2A	118.9
O3—C11—H11A	110.1	C9—N2—H2A	118.9
C12—C11—H11A	110.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.39	3.203 (2)	158
N2—H2A···O1	0.86	1.96	2.631 (2)	134
C2—H2···O1ⁱ	0.93	2.53	3.328 (3)	144
C9—H9B···S1	0.97	2.63	3.032 (2)	105

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈N₂O₃S
M_r	294.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.051 (3), 7.9482 (18), 14.116 (3)
β (°)	102.753 (3)
V (Å³)	1537.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.46 × 0.28 × 0.25

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.906, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	7933, 2853, 2098
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.136, 1.03
No. of reflections	2853
No. of parameters	187
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.27

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.8600	2.3900	3.203 (2)	158.00
N2—H2A···O1	0.8600	1.9600	2.631 (2)	134.00
C2—H2···O1ⁱ	0.9300	2.5300	3.328 (3)	144.00
C9—H9B···S1	0.9700	2.6300	3.032 (2)	105.00

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

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

References

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