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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
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.035
- wR factor = 0.090
- Data-to-parameter ratio = 9.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.50 From the CIF: _reflns_number_total 1711 Count of symmetry unique reflns 1721 Completeness (_total/calc) 99.42% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion
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. |
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