3-(3-Benzoyl­thio­ureido)­propionic acid

The molecular structure of the title compound, C₁₁H₁₂N₂O₃S, adopts a cis–trans configuration with respect to the position of the benzoyl and propionic acid groups relative to the S atom across the thio­urea C—N bonds, respectively. In the crystal structure, the mol­ecules are linked by weak N—H...S, N—H...O and O—H...O interactions to form a two-dimensional network perpendicular to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.123
• Data-to-parameter ratio = 18.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

The molecular dimension of the title compound, (I), is in agreement with other benzoylthiourea derivatives, PhCONHCSNHR, where R = Ph (Yamin & Yusof, 2003a), R = p-bromophenyl (Yamin & Yusof, 2003b) and R = 3,4-dimethyphenyl (Shanmuga Sundara Raj et al., 1999). The title compound also adopt 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 central carbonyl-thiourea moiety (S1/C8/N1/N2/C7), phenyl (C1–C6) and propionic acid [maximum deviation at C9 of −0.130 (2) Å] fragments are planar. The central thiourea moeity makes angles with the phenyl and propionic acid fragments of 52.74 (9) and 75.14 (11)°, respectively. The phenyl ring is inclined to the propionic acid fragment by 22.46 (13)°. There is one intramolecular hydrogen bond, N2—H2A···O1, present (Table 2) and as a result, a pseudo-six-membered ring (N2—C8—N1—C7—O1—H2A) is formed. In the crystal structure, the molecules are linked by intermolecular contacts, N2—H2A···O1ⁱ, N1—H1A···S1ⁱⁱ and O3—H3···O2ⁱⁱⁱ (see Table 2 for symmetry codes) to form a two-dimensional network perpendicular to the a axis (Fig. 2).

S2. Experimental

A solution of 3-aminopropionic acid (2.22 g, 0.025 mol) in acetone (50 ml) was added dropwise to 50 ml of an acetone solution containing an equimolar amount of benzoylisothiocyanate in a two-necked round-bottomed flask. The solution was refluxed for about 2 h and then cooled in ice. The white precipitate was filtered off and washed with ethanol–distilled water, then dried in a vacuum (yield 85%). Recrystallization from ethanol yielded single crystals suitable for X-ray analysis.

S3. Refinement

After checking their presence in the difference fourier map, all H atoms were fixed geometrically and allowed to ride on their parent C or N atoms with C—H = 0.93–0.97 Å and N—H = 0.86 Å.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures

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

(I)

Crystal data

C11H12N2O3S	Z = 2
Mr = 252.29	F(000) = 264
Triclinic, P1	Dx = 1.334 Mg m^−3
a = 4.5868 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.582 (2) Å	Cell parameters from 2840 reflections
c = 13.080 (3) Å	θ = 1.6–27.5°
α = 94.685 (3)°	µ = 0.26 mm^−1
β = 91.341 (3)°	T = 273 K
γ = 96.759 (3)°	Slab, colourless
V = 628.0 (2) Å^3	0.58 × 0.46 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2818 independent reflections
Radiation source: fine-focus sealed tube	2363 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 83.66 pixels mm^-1	θmax = 27.5°, θmin = 1.6°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.866, Tmax = 0.955	l = −16→16
7220 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0612P)^2 + 0.1496P] where P = (Fo^2 + 2Fc^2)/3
2818 reflections	(Δ/σ)max < 0.000
155 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.36044 (11)	0.13532 (4)	0.10273 (4)	0.06111 (18)
O1	0.9292 (4)	0.39011 (12)	−0.09335 (10)	0.0719 (4)
O2	0.4306 (4)	0.50196 (17)	0.37633 (10)	0.0815 (5)
O3	0.7400 (5)	0.3907 (2)	0.44855 (12)	0.1109 (8)
H3	0.6841	0.4268	0.5011	0.166*
N1	0.7182 (3)	0.20049 (13)	−0.04471 (10)	0.0472 (3)
H1A	0.6920	0.1198	−0.0624	0.057*
N2	0.6622 (3)	0.35995 (13)	0.08252 (11)	0.0524 (4)
H2A	0.7783	0.4088	0.0480	0.063*
C1	1.1061 (4)	0.09273 (17)	−0.19906 (14)	0.0542 (4)
H1B	1.1175	0.0551	−0.1375	0.065*
C2	1.2122 (5)	0.0361 (2)	−0.28751 (17)	0.0703 (5)
H2B	1.2983	−0.0389	−0.2850	0.084*
C3	1.1911 (6)	0.0898 (2)	−0.37851 (17)	0.0779 (6)
H3A	1.2609	0.0506	−0.4378	0.094*
C4	1.0673 (6)	0.2013 (2)	−0.38280 (16)	0.0812 (7)
H4A	1.0525	0.2373	−0.4450	0.097*
C5	0.9654 (5)	0.2597 (2)	−0.29529 (15)	0.0685 (5)
H5A	0.8842	0.3359	−0.2981	0.082*
C6	0.9834 (4)	0.20516 (16)	−0.20277 (12)	0.0485 (4)
C7	0.8787 (4)	0.27413 (16)	−0.10954 (12)	0.0494 (4)
C8	0.5922 (3)	0.24015 (15)	0.04628 (12)	0.0455 (4)
C9	0.5530 (4)	0.41369 (18)	0.17796 (13)	0.0554 (4)
H9A	0.3463	0.3830	0.1824	0.067*
H9B	0.5715	0.5060	0.1782	0.067*
C10	0.7189 (5)	0.3781 (2)	0.26981 (14)	0.0679 (5)
H10B	0.7032	0.2857	0.2683	0.081*
H10C	0.9250	0.4097	0.2651	0.081*
C11	0.6123 (4)	0.4292 (2)	0.36940 (14)	0.0603 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0664 (3)	0.0559 (3)	0.0578 (3)	−0.0070 (2)	0.0181 (2)	0.0009 (2)
O1	0.1110 (12)	0.0454 (7)	0.0559 (8)	−0.0062 (7)	0.0267 (7)	−0.0013 (6)
O2	0.0981 (11)	0.1067 (12)	0.0465 (7)	0.0474 (10)	0.0087 (7)	−0.0042 (7)
O3	0.1393 (16)	0.1595 (19)	0.0484 (8)	0.0909 (15)	−0.0011 (9)	−0.0077 (10)
N1	0.0566 (8)	0.0419 (7)	0.0411 (7)	−0.0002 (6)	0.0058 (6)	−0.0010 (5)
N2	0.0636 (9)	0.0486 (8)	0.0436 (7)	0.0011 (6)	0.0135 (6)	−0.0009 (6)
C1	0.0588 (10)	0.0540 (10)	0.0491 (9)	0.0027 (8)	0.0061 (7)	0.0047 (7)
C2	0.0789 (14)	0.0658 (12)	0.0673 (13)	0.0172 (10)	0.0125 (10)	−0.0035 (10)
C3	0.0939 (16)	0.0880 (16)	0.0509 (11)	0.0158 (13)	0.0158 (10)	−0.0107 (10)
C4	0.1131 (19)	0.0905 (16)	0.0419 (10)	0.0180 (14)	0.0094 (11)	0.0070 (10)
C5	0.0985 (16)	0.0637 (12)	0.0454 (10)	0.0162 (11)	0.0065 (9)	0.0064 (8)
C6	0.0550 (9)	0.0481 (9)	0.0400 (8)	−0.0021 (7)	0.0042 (7)	0.0000 (6)
C7	0.0587 (10)	0.0469 (9)	0.0408 (8)	0.0000 (7)	0.0043 (7)	0.0017 (7)
C8	0.0460 (8)	0.0495 (9)	0.0404 (8)	0.0047 (7)	0.0005 (6)	0.0024 (6)
C9	0.0630 (11)	0.0552 (10)	0.0480 (9)	0.0098 (8)	0.0117 (8)	−0.0027 (7)
C10	0.0679 (12)	0.0863 (14)	0.0499 (10)	0.0228 (10)	0.0039 (9)	−0.0121 (9)
C11	0.0603 (11)	0.0736 (12)	0.0465 (10)	0.0126 (9)	0.0053 (8)	−0.0052 (8)

Geometric parameters (Å, º)

S1—C8	1.6728 (17)	C2—H2B	0.9300
O1—C7	1.222 (2)	C3—C4	1.373 (3)
O2—C11	1.199 (2)	C3—H3A	0.9300
O3—C11	1.296 (2)	C4—C5	1.374 (3)
O3—H3	0.8200	C4—H4A	0.9300
N1—C7	1.368 (2)	C5—C6	1.387 (3)
N1—C8	1.391 (2)	C5—H5A	0.9300
N1—H1A	0.8600	C6—C7	1.488 (2)
N2—C8	1.317 (2)	C9—C10	1.504 (3)
N2—C9	1.454 (2)	C9—H9A	0.9700
N2—H2A	0.8600	C9—H9B	0.9700
C1—C6	1.378 (3)	C10—C11	1.485 (3)
C1—C2	1.384 (3)	C10—H10B	0.9700
C1—H1B	0.9300	C10—H10C	0.9700
C2—C3	1.366 (3)
C11—O3—H3	109.5	C1—C6—C7	122.26 (15)
C7—N1—C8	127.95 (14)	C5—C6—C7	118.08 (16)
C7—N1—H1A	116.0	O1—C7—N1	122.27 (15)
C8—N1—H1A	116.0	O1—C7—C6	121.61 (15)
C8—N2—C9	123.27 (15)	N1—C7—C6	116.11 (14)
C8—N2—H2A	118.4	N2—C8—N1	117.26 (14)
C9—N2—H2A	118.4	N2—C8—S1	123.77 (13)
C6—C1—C2	119.61 (18)	N1—C8—S1	118.97 (12)
C6—C1—H1B	120.2	N2—C9—C10	111.62 (15)
C2—C1—H1B	120.2	N2—C9—H9A	109.3
C3—C2—C1	120.4 (2)	C10—C9—H9A	109.3
C3—C2—H2B	119.8	N2—C9—H9B	109.3
C1—C2—H2B	119.8	C10—C9—H9B	109.3
C2—C3—C4	120.23 (19)	H9A—C9—H9B	108.0
C2—C3—H3A	119.9	C11—C10—C9	113.63 (16)
C4—C3—H3A	119.9	C11—C10—H10B	108.8
C3—C4—C5	120.0 (2)	C9—C10—H10B	108.8
C3—C4—H4A	120.0	C11—C10—H10C	108.8
C5—C4—H4A	120.0	C9—C10—H10C	108.8
C4—C5—C6	120.1 (2)	H10B—C10—H10C	107.7
C4—C5—H5A	119.9	O2—C11—O3	122.94 (17)
C6—C5—H5A	119.9	O2—C11—C10	123.40 (18)
C1—C6—C5	119.62 (17)	O3—C11—C10	113.64 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.99	2.656 (2)	133
N2—H2A···O1^i	0.86	2.40	3.047 (2)	132
N1—H1A···S1^ii	0.86	2.69	3.5466 (16)	175
O3—H3···O2^iii	0.82	1.83	2.649 (2)	176

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y, −z; (iii) −x+1, −y+1, −z+1.