organic compounds
The 3-methylbutyric acid and benzoyl fragments in the title compound, C13H16N2O3S, are cis and trans, respectively, with respect to the thiono group across the thiourea C—N bonds. In the crystal structure the molecules are stabilized by intermolecular N—HO, O—HS and C—HO hydrogen bonds to form zigzag chains parallel to the b axis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014662/is6074sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014662/is6074Isup2.hkl |
CCDC reference: 274445
Computing details top
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; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
(9S)-2-(3-Benzoylthioureido)-3-methylbutyric acid top
Crystal data top
C13H16N2O3S | F(000) = 592 |
Mr = 280.34 | Dx = 1.331 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 947 reflections |
a = 5.2223 (13) Å | θ = 1.7–26.5° |
b = 11.781 (3) Å | µ = 0.24 mm−1 |
c = 22.738 (5) Å | T = 298 K |
V = 1399.0 (6) Å3 | Block, colourless |
Z = 4 | 0.48 × 0.44 × 0.26 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1711 independent reflections |
Radiation source: fine-focus sealed tube | 1624 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.5°, θmin = 1.7° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −14→14 |
Tmin = 0.894, Tmax = 0.941 | l = −28→21 |
7838 measured reflections |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0544P)2 + 0.2185P] where P = (Fo2 + 2Fc2)/3 |
1711 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.12 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.70636 (13) | 0.09519 (5) | 0.76476 (2) | 0.04777 (18) | |
O1 | 0.1909 (5) | 0.13572 (17) | 0.92241 (8) | 0.0670 (6) | |
O2 | 0.3691 (4) | −0.17534 (19) | 0.81277 (9) | 0.0629 (5) | |
H2 | 0.3356 | −0.2289 | 0.7911 | 0.075* | |
O3 | 0.7717 (4) | −0.21307 (14) | 0.78644 (8) | 0.0550 (4) | |
N1 | 0.3330 (4) | 0.18026 (15) | 0.83078 (8) | 0.0409 (4) | |
H1A | 0.3147 | 0.2269 | 0.8020 | 0.049* | |
N2 | 0.5274 (4) | 0.01827 (15) | 0.86560 (8) | 0.0428 (4) | |
H2A | 0.4291 | 0.0262 | 0.8957 | 0.051* | |
C1 | −0.1791 (6) | 0.3007 (2) | 0.92366 (11) | 0.0587 (7) | |
H1B | −0.1726 | 0.2478 | 0.9540 | 0.070* | |
C2 | −0.3606 (7) | 0.3852 (3) | 0.92467 (14) | 0.0685 (8) | |
H2B | −0.4766 | 0.3892 | 0.9556 | 0.082* | |
C3 | −0.3711 (6) | 0.4637 (2) | 0.88008 (14) | 0.0650 (8) | |
H3A | −0.4953 | 0.5203 | 0.8807 | 0.078* | |
C4 | −0.1994 (7) | 0.4587 (3) | 0.83489 (14) | 0.0688 (8) | |
H4A | −0.2057 | 0.5125 | 0.8050 | 0.083* | |
C5 | −0.0164 (6) | 0.3742 (2) | 0.83333 (12) | 0.0585 (7) | |
H5A | 0.0999 | 0.3713 | 0.8024 | 0.070* | |
C6 | −0.0053 (5) | 0.29382 (18) | 0.87756 (10) | 0.0435 (5) | |
C7 | 0.1777 (5) | 0.19717 (19) | 0.87916 (10) | 0.0454 (5) | |
C8 | 0.5148 (5) | 0.09605 (17) | 0.82384 (9) | 0.0386 (4) | |
C9 | 0.6960 (5) | −0.07956 (17) | 0.86419 (9) | 0.0398 (5) | |
H9A | 0.8711 | −0.0534 | 0.8566 | 0.048* | |
C10 | 0.6892 (6) | −0.13945 (19) | 0.92466 (9) | 0.0464 (5) | |
H10A | 0.5128 | −0.1642 | 0.9319 | 0.056* | |
C11 | 0.7644 (8) | −0.0594 (2) | 0.97371 (11) | 0.0743 (10) | |
H11A | 0.7589 | −0.0990 | 1.0106 | 0.111* | |
H11B | 0.6472 | 0.0034 | 0.9748 | 0.111* | |
H11C | 0.9347 | −0.0317 | 0.9669 | 0.111* | |
C12 | 0.8588 (8) | −0.2442 (3) | 0.92482 (13) | 0.0751 (9) | |
H12A | 0.8504 | −0.2801 | 0.9627 | 0.113* | |
H12B | 1.0323 | −0.2225 | 0.9167 | 0.113* | |
H12C | 0.8007 | −0.2963 | 0.8952 | 0.113* | |
C13 | 0.6196 (5) | −0.1626 (2) | 0.81610 (10) | 0.0434 (5) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0558 (3) | 0.0455 (3) | 0.0420 (3) | 0.0078 (3) | 0.0104 (3) | 0.0061 (2) |
O1 | 0.0832 (14) | 0.0667 (11) | 0.0509 (10) | 0.0215 (11) | 0.0243 (10) | 0.0177 (8) |
O2 | 0.0511 (11) | 0.0708 (12) | 0.0667 (12) | −0.0067 (10) | −0.0047 (9) | −0.0251 (10) |
O3 | 0.0582 (11) | 0.0539 (9) | 0.0528 (9) | 0.0019 (9) | 0.0034 (9) | −0.0123 (8) |
N1 | 0.0497 (11) | 0.0369 (8) | 0.0362 (8) | 0.0028 (9) | 0.0055 (8) | 0.0027 (7) |
N2 | 0.0541 (12) | 0.0375 (8) | 0.0369 (9) | 0.0014 (9) | 0.0061 (9) | 0.0023 (7) |
C1 | 0.0718 (18) | 0.0533 (14) | 0.0509 (13) | 0.0048 (14) | 0.0176 (14) | −0.0027 (11) |
C2 | 0.071 (2) | 0.0691 (17) | 0.0654 (17) | 0.0084 (16) | 0.0262 (16) | −0.0111 (14) |
C3 | 0.0578 (17) | 0.0547 (15) | 0.083 (2) | 0.0127 (13) | 0.0083 (16) | −0.0142 (15) |
C4 | 0.075 (2) | 0.0629 (16) | 0.0682 (16) | 0.0204 (17) | 0.0097 (17) | 0.0106 (14) |
C5 | 0.0615 (16) | 0.0596 (14) | 0.0545 (13) | 0.0141 (13) | 0.0151 (14) | 0.0053 (12) |
C6 | 0.0463 (12) | 0.0419 (11) | 0.0425 (11) | −0.0012 (10) | 0.0037 (11) | −0.0058 (9) |
C7 | 0.0507 (13) | 0.0435 (11) | 0.0420 (11) | −0.0024 (11) | 0.0062 (10) | 0.0009 (9) |
C8 | 0.0459 (11) | 0.0348 (9) | 0.0352 (9) | −0.0051 (10) | −0.0029 (9) | −0.0033 (8) |
C9 | 0.0456 (11) | 0.0364 (10) | 0.0373 (10) | −0.0031 (10) | −0.0034 (9) | 0.0009 (8) |
C10 | 0.0547 (14) | 0.0440 (11) | 0.0405 (11) | −0.0096 (11) | −0.0064 (11) | 0.0062 (9) |
C11 | 0.115 (3) | 0.0666 (17) | 0.0415 (12) | −0.024 (2) | −0.0114 (17) | 0.0030 (12) |
C12 | 0.096 (3) | 0.0655 (17) | 0.0642 (17) | 0.0146 (18) | −0.0091 (18) | 0.0198 (14) |
C13 | 0.0502 (13) | 0.0404 (11) | 0.0396 (11) | −0.0021 (10) | −0.0046 (10) | 0.0006 (9) |
Geometric parameters (Å, º) top
S1—C8 | 1.675 (2) | C4—C5 | 1.381 (4) |
O1—C7 | 1.223 (3) | C4—H4A | 0.9300 |
O2—C13 | 1.319 (3) | C5—C6 | 1.382 (3) |
O2—H2 | 0.8200 | C5—H5A | 0.9300 |
O3—C13 | 1.199 (3) | C6—C7 | 1.487 (3) |
N1—C7 | 1.381 (3) | C9—C13 | 1.521 (3) |
N1—C8 | 1.382 (3) | C9—C10 | 1.546 (3) |
N1—H1A | 0.8600 | C9—H9A | 0.9800 |
N2—C8 | 1.321 (3) | C10—C11 | 1.513 (3) |
N2—C9 | 1.451 (3) | C10—C12 | 1.519 (4) |
N2—H2A | 0.8600 | C10—H10A | 0.9800 |
C1—C2 | 1.375 (4) | C11—H11A | 0.9600 |
C1—C6 | 1.389 (3) | C11—H11B | 0.9600 |
C1—H1B | 0.9300 | C11—H11C | 0.9600 |
C2—C3 | 1.374 (4) | C12—H12A | 0.9600 |
C2—H2B | 0.9300 | C12—H12B | 0.9600 |
C3—C4 | 1.365 (4) | C12—H12C | 0.9600 |
C3—H3A | 0.9300 | ||
C13—O2—H2 | 109.5 | N2—C8—S1 | 122.84 (18) |
C7—N1—C8 | 126.71 (18) | N1—C8—S1 | 120.41 (15) |
C7—N1—H1A | 116.6 | N2—C9—C13 | 111.61 (19) |
C8—N1—H1A | 116.6 | N2—C9—C10 | 109.21 (18) |
C8—N2—C9 | 124.44 (19) | C13—C9—C10 | 109.86 (17) |
C8—N2—H2A | 117.8 | N2—C9—H9A | 108.7 |
C9—N2—H2A | 117.8 | C13—C9—H9A | 108.7 |
C2—C1—C6 | 120.4 (2) | C10—C9—H9A | 108.7 |
C2—C1—H1B | 119.8 | C11—C10—C12 | 110.7 (3) |
C6—C1—H1B | 119.8 | C11—C10—C9 | 111.42 (18) |
C3—C2—C1 | 120.2 (3) | C12—C10—C9 | 111.1 (2) |
C3—C2—H2B | 119.9 | C11—C10—H10A | 107.8 |
C1—C2—H2B | 119.9 | C12—C10—H10A | 107.8 |
C4—C3—C2 | 120.0 (3) | C9—C10—H10A | 107.8 |
C4—C3—H3A | 120.0 | C10—C11—H11A | 109.5 |
C2—C3—H3A | 120.0 | C10—C11—H11B | 109.5 |
C3—C4—C5 | 120.4 (3) | H11A—C11—H11B | 109.5 |
C3—C4—H4A | 119.8 | C10—C11—H11C | 109.5 |
C5—C4—H4A | 119.8 | H11A—C11—H11C | 109.5 |
C4—C5—C6 | 120.3 (3) | H11B—C11—H11C | 109.5 |
C4—C5—H5A | 119.9 | C10—C12—H12A | 109.5 |
C6—C5—H5A | 119.9 | C10—C12—H12B | 109.5 |
C5—C6—C1 | 118.8 (2) | H12A—C12—H12B | 109.5 |
C5—C6—C7 | 124.7 (2) | C10—C12—H12C | 109.5 |
C1—C6—C7 | 116.5 (2) | H12A—C12—H12C | 109.5 |
O1—C7—N1 | 121.5 (2) | H12B—C12—H12C | 109.5 |
O1—C7—C6 | 120.6 (2) | O3—C13—O2 | 124.6 (2) |
N1—C7—C6 | 117.92 (19) | O3—C13—C9 | 123.3 (2) |
N2—C8—N1 | 116.75 (19) | O2—C13—C9 | 112.0 (2) |
C6—C1—C2—C3 | −0.1 (5) | C9—N2—C8—N1 | 176.5 (2) |
C1—C2—C3—C4 | −0.7 (5) | C9—N2—C8—S1 | −3.5 (3) |
C2—C3—C4—C5 | 0.8 (5) | C7—N1—C8—N2 | 5.9 (3) |
C3—C4—C5—C6 | −0.1 (5) | C7—N1—C8—S1 | −174.17 (19) |
C4—C5—C6—C1 | −0.7 (4) | C8—N2—C9—C13 | −67.6 (3) |
C4—C5—C6—C7 | 177.8 (3) | C8—N2—C9—C10 | 170.7 (2) |
C2—C1—C6—C5 | 0.8 (4) | N2—C9—C10—C11 | −57.3 (3) |
C2—C1—C6—C7 | −177.9 (3) | C13—C9—C10—C11 | 180.0 (3) |
C8—N1—C7—O1 | 0.5 (4) | N2—C9—C10—C12 | 178.7 (2) |
C8—N1—C7—C6 | 179.8 (2) | C13—C9—C10—C12 | 56.0 (3) |
C5—C6—C7—O1 | 173.3 (3) | N2—C9—C13—O3 | 141.2 (2) |
C1—C6—C7—O1 | −8.1 (4) | C10—C9—C13—O3 | −97.5 (3) |
C5—C6—C7—N1 | −5.9 (4) | N2—C9—C13—O2 | −41.2 (3) |
C1—C6—C7—N1 | 172.7 (2) | C10—C9—C13—O2 | 80.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.89 | 2.583 (3) | 136 |
C1—H1B···O1 | 0.93 | 2.42 | 2.741 (4) | 100 |
C11—H11B···N2 | 0.96 | 2.57 | 2.900 (4) | 101 |
N1—H1A···O3i | 0.86 | 2.18 | 2.997 (3) | 159 |
O2—H2···S1ii | 0.82 | 2.44 | 3.251 (2) | 170 |
C5—H5A···O3i | 0.93 | 2.35 | 3.179 (3) | 148 |
C11—H11C···O1iii | 0.96 | 2.59 | 3.407 (4) | 143 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x+1, y, z. |