2-(3-Benzoyl­thio­ureido)propionic acid

The mol­ecular structure of the title compound, C₁₁H₁₂N₂O₃S, adopts a cis–trans configuration with respect to the positions of the propionic acid and benzoyl groups relative to the S atom across the thio­urea C—N bonds. In the crystal structure, mol­ecules are linked by O—H...S and C—H...O inter­actions, forming a one-dimensional chain parallel to the b axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.104
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

The title compound, (I), is isomorphous to 3-(3-benzoylthioureido)propionic acid (Yusof & Yamin, 2003) except that the 3-benzoylthioureido group is attached to the α-alanine group. The molecular structure adopts a cis--trans configuration with respect to the position of the propionic acid and benzoyl groups relative to the S atom across the C8—N2 and C8—N1 bonds, respectively.

The bond lengths and angles (Table 1) are in normal ranges (Allen et al.,1987) and comparable to its β- alanine derivative. The central carbonyl-thiourea moiety (S1/C8/N1/N2/C7), phenyl (C1–C6) and ethanoic acid [maximum deviation at C7 of 0.037 (2) Å] fragments are planar. The central carbonylthiourea moiety makes dihedral angles with phenyl and ethanoic acid fragments of 27.52 (9) and 24.20 (12)°, respectively. The phenyl ring is inclined to the ethanoic acid fragment by 4.19 (4)°.

There are three intramolecular hydrogen bonds C9—H9···S1, N2—H2A···O1 and N2—H2A···O3 (Table 2) and, as a result, two pseudo-five-membered rings (C9—H9—S1—C8—N2), (N2—H2A—O3—C11—C9) and a pseudo-six-membered ring (N2—H2A—O1—C7—N1—C8) are formed (Fig. 1). In the crystal structure, the molecules are linked by intermolecular contacts, O2—H2···S1ⁱ and C5—H5···O3ⁱⁱ (see Table 2 for symmetry codes), forming a one-dimensional network parallel to the b axis (Fig. 2).

S2. Experimental

A solution of 2-aminopropionic acid (4.45 g, 0.05 mol) in acetone (20 ml) was added dropwise to 20 ml of acetone solution containing an equimolar amount of benzoyl isothiocyanate in a two-necked round-bottomed flask. The solution was refluxed for about 5 h and then filtered off into a beaker containing ice. The yellow precipitate was washed with cold acetone–distilled water, before drying and kept in a desiccator (yield 10.72 g, 85%, m.p. 430–431 K). Recrystallization from acetonitrile yielded single crystals suitable for X-ray analysis.

S3. Refinement

H atoms were positioned geometrically [O—H = 0.82, N—H = 0.86 and C—H = 0.93 or 0.96 Å (methyl)] and constrained to ride on their parent atoms with U_iso(H) = 1.2 (1.5 methyl and hydroxyl) U_eq(C/N/O).

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON ( Spek, 2003).

Figures

	Fig. 1. The molecular structure of the title compound, (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing diagram of compound (I), viewed down the c axis. The dashed lines denote O—H···S and C—H···O hydrogen bonds.

2-(3-Benzoylthioureido)propionic acid

Crystal data

C11H12N2O3S	Z = 2
Mr = 252.29	F(000) = 264
Triclinic, P1	Dx = 1.419 Mg m^−3
Hall symbol: -P 1	Melting point = 430–431 K
a = 7.3570 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.083 (2) Å	Cell parameters from 835 reflections
c = 10.706 (3) Å	θ = 1.9–25.0°
α = 87.395 (4)°	µ = 0.27 mm^−1
β = 77.128 (4)°	T = 298 K
γ = 72.065 (5)°	Block, yellow
V = 590.3 (3) Å^3	0.49 × 0.33 × 0.31 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2076 independent reflections
Radiation source: fine-focus sealed tube	1858 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 83.66 pixels mm^-1	θmax = 25.0°, θmin = 1.9°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −9→9
Tmin = 0.878, Tmax = 0.920	l = −12→12
5591 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0479P)^2 + 0.2021P] where P = (Fo^2 + 2Fc^2)/3
2076 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.05389 (9)	0.28808 (6)	0.84620 (5)	0.0557 (2)
O1	0.2919 (3)	0.4469 (2)	0.44662 (14)	0.0715 (5)
O2	0.1648 (3)	0.88547 (17)	0.87377 (14)	0.0632 (4)
H2	0.1409	0.9875	0.8530	0.095*
O3	0.2032 (3)	0.83654 (19)	0.66515 (14)	0.0627 (4)
N1	0.1877 (3)	0.2679 (2)	0.59569 (15)	0.0493 (4)
H1	0.1603	0.1714	0.6045	0.059*
N2	0.2135 (2)	0.50137 (19)	0.69966 (14)	0.0445 (4)
H2A	0.2583	0.5351	0.6250	0.053*
C1	0.2774 (3)	0.2387 (3)	0.24629 (18)	0.0486 (5)
H1A	0.2648	0.3549	0.2285	0.058*
C2	0.2974 (3)	0.1236 (3)	0.14897 (19)	0.0558 (5)
H2B	0.2987	0.1625	0.0658	0.067*
C3	0.3153 (3)	−0.0476 (3)	0.1745 (2)	0.0596 (6)
H3	0.3275	−0.1244	0.1088	0.071*
C4	0.3152 (4)	−0.1057 (3)	0.2968 (2)	0.0631 (6)
H4	0.3280	−0.2221	0.3139	0.076*
C5	0.2962 (3)	0.0080 (3)	0.3946 (2)	0.0572 (5)
H5	0.2968	−0.0322	0.4774	0.069*
C6	0.2762 (3)	0.1812 (2)	0.37046 (17)	0.0443 (4)
C7	0.2548 (3)	0.3113 (3)	0.47101 (18)	0.0493 (5)
C8	0.1591 (3)	0.3601 (2)	0.70800 (18)	0.0430 (4)
C9	0.2007 (3)	0.6027 (2)	0.81187 (17)	0.0408 (4)
H9	0.0789	0.6063	0.8733	0.049*
C10	0.3702 (3)	0.5220 (3)	0.8767 (2)	0.0546 (5)
H10A	0.3683	0.4080	0.9049	0.082*
H10B	0.3579	0.5935	0.9492	0.082*
H10C	0.4915	0.5136	0.8170	0.082*
C11	0.1908 (3)	0.7864 (2)	0.77254 (18)	0.0453 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0881 (4)	0.0384 (3)	0.0404 (3)	−0.0303 (3)	0.0025 (3)	−0.0038 (2)
O1	0.1252 (15)	0.0572 (9)	0.0426 (8)	−0.0490 (10)	−0.0100 (8)	0.0020 (7)
O2	0.1079 (13)	0.0339 (7)	0.0526 (9)	−0.0256 (8)	−0.0215 (8)	−0.0007 (6)
O3	0.0986 (12)	0.0482 (8)	0.0453 (8)	−0.0320 (8)	−0.0121 (8)	0.0104 (6)
N1	0.0724 (11)	0.0428 (9)	0.0366 (8)	−0.0273 (8)	−0.0051 (8)	−0.0043 (7)
N2	0.0654 (10)	0.0378 (8)	0.0327 (8)	−0.0229 (7)	−0.0057 (7)	0.0004 (6)
C1	0.0562 (12)	0.0508 (11)	0.0408 (10)	−0.0211 (9)	−0.0088 (9)	0.0031 (8)
C2	0.0613 (13)	0.0722 (15)	0.0347 (10)	−0.0213 (11)	−0.0106 (9)	−0.0001 (9)
C3	0.0703 (14)	0.0617 (14)	0.0445 (12)	−0.0176 (11)	−0.0082 (10)	−0.0175 (10)
C4	0.0882 (17)	0.0453 (12)	0.0513 (12)	−0.0157 (11)	−0.0108 (11)	−0.0063 (9)
C5	0.0806 (15)	0.0494 (12)	0.0370 (10)	−0.0144 (10)	−0.0111 (10)	−0.0001 (8)
C6	0.0504 (11)	0.0460 (11)	0.0367 (10)	−0.0152 (8)	−0.0084 (8)	−0.0029 (8)
C7	0.0633 (12)	0.0478 (11)	0.0386 (10)	−0.0198 (9)	−0.0106 (9)	0.0003 (8)
C8	0.0555 (11)	0.0347 (9)	0.0383 (10)	−0.0145 (8)	−0.0079 (8)	−0.0018 (7)
C9	0.0555 (11)	0.0329 (9)	0.0353 (9)	−0.0166 (8)	−0.0081 (8)	−0.0008 (7)
C10	0.0668 (13)	0.0430 (11)	0.0588 (13)	−0.0165 (10)	−0.0236 (11)	0.0019 (9)
C11	0.0572 (12)	0.0371 (10)	0.0441 (11)	−0.0181 (8)	−0.0112 (8)	0.0013 (8)

Geometric parameters (Å, º)

S1—C8	1.6778 (19)	C2—H2B	0.9300
O1—C7	1.212 (2)	C3—C4	1.371 (3)
O2—C11	1.321 (2)	C3—H3	0.9300
O2—H2	0.8200	C4—C5	1.380 (3)
O3—C11	1.195 (2)	C4—H4	0.9300
N1—C8	1.385 (2)	C5—C6	1.380 (3)
N1—C7	1.385 (2)	C5—H5	0.9300
N1—H1	0.8600	C6—C7	1.488 (3)
N2—C8	1.315 (2)	C9—C11	1.509 (2)
N2—C9	1.454 (2)	C9—C10	1.518 (3)
N2—H2A	0.8600	C9—H9	0.9800
C1—C2	1.381 (3)	C10—H10A	0.9600
C1—C6	1.387 (3)	C10—H10B	0.9600
C1—H1A	0.9300	C10—H10C	0.9600
C2—C3	1.369 (3)
C11—O2—H2	109.5	C5—C6—C7	123.39 (17)
C8—N1—C7	128.30 (16)	C1—C6—C7	117.59 (18)
C8—N1—H1	115.8	O1—C7—N1	121.72 (18)
C7—N1—H1	115.8	O1—C7—C6	122.86 (18)
C8—N2—C9	122.46 (15)	N1—C7—C6	115.43 (17)
C8—N2—H2A	118.8	N2—C8—N1	117.74 (16)
C9—N2—H2A	118.8	N2—C8—S1	123.69 (14)
C2—C1—C6	120.12 (19)	N1—C8—S1	118.56 (14)
C2—C1—H1A	119.9	N2—C9—C11	108.88 (15)
C6—C1—H1A	119.9	N2—C9—C10	111.97 (15)
C3—C2—C1	120.27 (19)	C11—C9—C10	111.40 (16)
C3—C2—H2B	119.9	N2—C9—H9	108.2
C1—C2—H2B	119.9	C11—C9—H9	108.2
C2—C3—C4	120.02 (19)	C10—C9—H9	108.2
C2—C3—H3	120.0	C9—C10—H10A	109.5
C4—C3—H3	120.0	C9—C10—H10B	109.5
C3—C4—C5	120.2 (2)	H10A—C10—H10B	109.5
C3—C4—H4	119.9	C9—C10—H10C	109.5
C5—C4—H4	119.9	H10A—C10—H10C	109.5
C4—C5—C6	120.40 (19)	H10B—C10—H10C	109.5
C4—C5—H5	119.8	O3—C11—O2	124.35 (18)
C6—C5—H5	119.8	O3—C11—C9	125.10 (17)
C5—C6—C1	119.01 (18)	O2—C11—C9	110.54 (16)
C6—C1—C2—C3	0.3 (3)	C5—C6—C7—N1	−21.8 (3)
C1—C2—C3—C4	−0.6 (3)	C1—C6—C7—N1	158.69 (18)
C2—C3—C4—C5	0.3 (4)	C9—N2—C8—N1	−176.40 (17)
C3—C4—C5—C6	0.3 (4)	C9—N2—C8—S1	4.7 (3)
C4—C5—C6—C1	−0.6 (3)	C7—N1—C8—N2	−5.2 (3)
C4—C5—C6—C7	179.9 (2)	C7—N1—C8—S1	173.76 (17)
C2—C1—C6—C5	0.3 (3)	C8—N2—C9—C11	−156.49 (18)
C2—C1—C6—C7	179.83 (19)	C8—N2—C9—C10	79.9 (2)
C8—N1—C7—O1	−2.5 (4)	N2—C9—C11—O3	−4.1 (3)
C8—N1—C7—C6	178.01 (19)	C10—C9—C11—O3	119.9 (2)
C5—C6—C7—O1	158.7 (2)	N2—C9—C11—O2	175.48 (16)
C1—C6—C7—O1	−20.8 (3)	C10—C9—C11—O2	−60.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···S1	0.98	2.67	3.033 (2)	102
N2—H2A···O1	0.86	2.01	2.669 (2)	133
N2—H2A···O3	0.86	2.39	2.698 (2)	102
O2—H2···S1^i	0.82	2.32	3.1190 (16)	166
C5—H5···O3^ii	0.93	2.30	3.180 (3)	158

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.