organic compounds
The title compound, (2S)-2-(3-benzoylthioureido)-3-(1H-imidazolium-4-yl)propionate, C14H14N4O3S, is zwitterionic with protonated positively charged imidazoyl and deprotonated negatively charged carboxylate groups. The intermolecular hydrogen bonds, C—HO and N—HO, involve all the O atoms with the H atoms from the amine and imidazoylium, forming a two-dimensional network parallel to the (100) plane.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501442X/rn6047sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680501442X/rn6047Isup2.hkl |
CCDC reference: 274615
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.039
- wR factor = 0.097
- Data-to-parameter ratio = 8.4
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 . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.08 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03
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 27.50 From the CIF: _reflns_number_total 1678 Count of symmetry unique reflns 1689 Completeness (_total/calc) 99.35% 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 4 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 2 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-(1H-imidazolium-4-yl)propionate top
Crystal data top
C14H14N4O3S | F(000) = 332 |
Mr = 318.35 | Dx = 1.488 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2717 reflections |
a = 5.6995 (13) Å | θ = 2.2–27.5° |
b = 17.916 (4) Å | µ = 0.25 mm−1 |
c = 7.0525 (17) Å | T = 298 K |
β = 99.424 (5)° | Block, colourless |
V = 710.4 (3) Å3 | 0.29 × 0.27 × 0.20 mm |
Z = 2 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1678 independent reflections |
Radiation source: fine-focus sealed tube | 1648 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.5°, θmin = 2.2° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −14→23 |
Tmin = 0.931, Tmax = 0.952 | l = −9→8 |
4765 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0477P)2 + 0.1656P] where P = (Fo2 + 2Fc2)/3 |
1678 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.32 e Å−3 |
1 restraint | Δρmin = −0.15 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.44510 (16) | 1.03238 (4) | 0.96921 (12) | 0.0483 (2) | |
O1 | 0.5463 (4) | 0.79580 (11) | 0.7691 (3) | 0.0403 (5) | |
O2 | −0.0259 (5) | 0.85282 (13) | 0.5253 (4) | 0.0583 (7) | |
O3 | −0.1620 (5) | 0.94687 (13) | 0.3377 (4) | 0.0496 (6) | |
N1 | 0.6404 (4) | 0.89898 (13) | 0.9566 (4) | 0.0348 (5) | |
H1A | 0.7334 | 0.9148 | 1.0570 | 0.042* | |
N2 | 0.3391 (4) | 0.92673 (14) | 0.7074 (3) | 0.0348 (5) | |
H2A | 0.3645 | 0.8829 | 0.6652 | 0.042* | |
C14 | 0.1589 (6) | 1.17047 (18) | 0.4594 (5) | 0.0416 (7) | |
H14A | 0.3036 | 1.1909 | 0.5159 | 0.050* | |
C13 | −0.2093 (6) | 1.16234 (18) | 0.3237 (5) | 0.0437 (8) | |
H13A | −0.3642 | 1.1748 | 0.2697 | 0.052* | |
C1 | 0.8711 (6) | 0.71091 (18) | 1.0250 (5) | 0.0369 (6) | |
H1B | 0.7312 | 0.6864 | 0.9738 | 0.044* | |
C2 | 1.0637 (6) | 0.6703 (2) | 1.1133 (5) | 0.0467 (8) | |
H2B | 1.0539 | 0.6186 | 1.1232 | 0.056* | |
C3 | 1.2701 (6) | 0.7070 (2) | 1.1867 (5) | 0.0504 (9) | |
H3A | 1.4026 | 0.6796 | 1.2418 | 0.061* | |
C4 | 1.2837 (6) | 0.7829 (2) | 1.1797 (5) | 0.0496 (9) | |
H4A | 1.4227 | 0.8070 | 1.2350 | 0.060* | |
C5 | 1.0912 (5) | 0.8245 (2) | 1.0904 (5) | 0.0405 (7) | |
H5A | 1.1013 | 0.8762 | 1.0835 | 0.049* | |
C6 | 0.8841 (5) | 0.78795 (17) | 1.0119 (4) | 0.0329 (6) | |
C7 | 0.6754 (5) | 0.82725 (16) | 0.9002 (4) | 0.0311 (6) | |
C8 | 0.4711 (5) | 0.94858 (16) | 0.8687 (4) | 0.0315 (6) | |
C9 | 0.1532 (5) | 0.97163 (15) | 0.5955 (4) | 0.0315 (6) | |
H9A | 0.0699 | 0.9987 | 0.6853 | 0.038* | |
C10 | −0.0271 (6) | 0.91853 (17) | 0.4753 (4) | 0.0361 (6) | |
C11 | 0.2616 (5) | 1.0296 (2) | 0.4732 (4) | 0.0377 (6) | |
H11A | 0.4165 | 1.0443 | 0.5413 | 0.045* | |
H11B | 0.2850 | 1.0063 | 0.3535 | 0.045* | |
C12 | 0.1135 (5) | 1.09724 (17) | 0.4289 (4) | 0.0327 (6) | |
N4 | −0.0425 (5) | 1.20926 (15) | 0.3938 (4) | 0.0415 (6) | |
H4B | −0.0577 | 1.2570 | 0.3979 | 0.050* | |
N3 | −0.1210 (5) | 1.09424 (15) | 0.3423 (4) | 0.0377 (6) | |
H3C | −0.1981 | 1.0541 | 0.3059 | 0.045* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0619 (5) | 0.0265 (4) | 0.0475 (4) | 0.0097 (4) | −0.0175 (3) | −0.0095 (3) |
O1 | 0.0449 (12) | 0.0241 (10) | 0.0461 (12) | 0.0068 (9) | −0.0096 (9) | −0.0050 (9) |
O2 | 0.0723 (17) | 0.0250 (12) | 0.0663 (16) | −0.0032 (12) | −0.0223 (13) | 0.0095 (11) |
O3 | 0.0621 (14) | 0.0265 (11) | 0.0486 (13) | 0.0002 (11) | −0.0256 (11) | −0.0010 (10) |
N1 | 0.0380 (12) | 0.0258 (12) | 0.0352 (13) | 0.0012 (10) | −0.0102 (10) | −0.0017 (10) |
N2 | 0.0450 (13) | 0.0229 (12) | 0.0314 (12) | 0.0056 (10) | −0.0090 (10) | −0.0004 (9) |
C14 | 0.0495 (18) | 0.0312 (16) | 0.0407 (16) | −0.0061 (14) | −0.0028 (13) | 0.0013 (12) |
C13 | 0.0483 (18) | 0.0336 (17) | 0.0466 (18) | 0.0081 (14) | −0.0005 (14) | 0.0035 (14) |
C1 | 0.0388 (15) | 0.0336 (15) | 0.0368 (16) | 0.0045 (13) | 0.0014 (12) | 0.0038 (12) |
C2 | 0.0513 (18) | 0.0403 (19) | 0.0478 (18) | 0.0142 (16) | 0.0061 (15) | 0.0114 (14) |
C3 | 0.0406 (17) | 0.062 (2) | 0.0469 (19) | 0.0192 (17) | 0.0015 (14) | 0.0098 (16) |
C4 | 0.0308 (15) | 0.069 (3) | 0.047 (2) | 0.0023 (15) | −0.0003 (14) | 0.0021 (17) |
C5 | 0.0350 (15) | 0.0400 (17) | 0.0451 (17) | 0.0007 (13) | 0.0022 (13) | 0.0001 (14) |
C6 | 0.0321 (14) | 0.0359 (15) | 0.0296 (15) | 0.0057 (12) | 0.0018 (11) | 0.0023 (11) |
C7 | 0.0329 (13) | 0.0269 (13) | 0.0311 (13) | 0.0023 (11) | −0.0018 (11) | 0.0030 (11) |
C8 | 0.0367 (13) | 0.0215 (12) | 0.0334 (14) | 0.0012 (11) | −0.0031 (11) | 0.0015 (11) |
C9 | 0.0373 (14) | 0.0222 (12) | 0.0312 (13) | 0.0060 (11) | −0.0057 (11) | 0.0000 (10) |
C10 | 0.0457 (16) | 0.0238 (13) | 0.0354 (15) | 0.0012 (12) | −0.0041 (13) | −0.0022 (11) |
C11 | 0.0417 (14) | 0.0300 (14) | 0.0393 (14) | 0.0038 (14) | 0.0000 (11) | 0.0068 (13) |
C12 | 0.0396 (14) | 0.0273 (14) | 0.0290 (13) | 0.0001 (12) | −0.0010 (10) | 0.0052 (11) |
N4 | 0.0646 (17) | 0.0197 (11) | 0.0380 (14) | 0.0020 (12) | 0.0013 (12) | −0.0001 (10) |
N3 | 0.0404 (13) | 0.0229 (11) | 0.0453 (14) | −0.0006 (10) | −0.0061 (11) | −0.0005 (10) |
Geometric parameters (Å, º) top
S1—C8 | 1.677 (3) | C2—C3 | 1.373 (6) |
O1—C7 | 1.221 (4) | C2—H2B | 0.9300 |
O2—C10 | 1.229 (4) | C3—C4 | 1.364 (6) |
O3—C10 | 1.244 (4) | C3—H3A | 0.9300 |
N1—C7 | 1.369 (4) | C4—C5 | 1.390 (5) |
N1—C8 | 1.382 (4) | C4—H4A | 0.9300 |
N1—H1A | 0.8600 | C5—C6 | 1.384 (4) |
N2—C8 | 1.316 (4) | C5—H5A | 0.9300 |
N2—C9 | 1.456 (3) | C6—C7 | 1.492 (4) |
N2—H2A | 0.8600 | C9—C11 | 1.542 (4) |
C14—C12 | 1.348 (4) | C9—C10 | 1.547 (4) |
C14—N4 | 1.357 (4) | C9—H9A | 0.9800 |
C14—H14A | 0.9300 | C11—C12 | 1.481 (4) |
C13—N4 | 1.304 (4) | C11—H11A | 0.9700 |
C13—N3 | 1.318 (4) | C11—H11B | 0.9700 |
C13—H13A | 0.9300 | C12—N3 | 1.377 (4) |
C1—C2 | 1.378 (4) | N4—H4B | 0.8600 |
C1—C6 | 1.386 (4) | N3—H3C | 0.8600 |
C1—H1B | 0.9300 | ||
C7—N1—C8 | 126.7 (2) | O1—C7—N1 | 123.7 (3) |
C7—N1—H1A | 116.7 | O1—C7—C6 | 120.8 (3) |
C8—N1—H1A | 116.7 | N1—C7—C6 | 115.5 (2) |
C8—N2—C9 | 124.5 (2) | N2—C8—N1 | 117.0 (3) |
C8—N2—H2A | 117.7 | N2—C8—S1 | 123.6 (2) |
C9—N2—H2A | 117.7 | N1—C8—S1 | 119.3 (2) |
C12—C14—N4 | 108.3 (3) | N2—C9—C11 | 110.6 (2) |
C12—C14—H14A | 125.8 | N2—C9—C10 | 108.4 (2) |
N4—C14—H14A | 125.8 | C11—C9—C10 | 113.5 (2) |
N4—C13—N3 | 108.4 (3) | N2—C9—H9A | 108.0 |
N4—C13—H13A | 125.8 | C11—C9—H9A | 108.0 |
N3—C13—H13A | 125.8 | C10—C9—H9A | 108.0 |
C2—C1—C6 | 120.6 (3) | O2—C10—O3 | 126.1 (3) |
C2—C1—H1B | 119.7 | O2—C10—C9 | 117.4 (3) |
C6—C1—H1B | 119.7 | O3—C10—C9 | 116.5 (3) |
C3—C2—C1 | 119.2 (3) | C12—C11—C9 | 113.8 (2) |
C3—C2—H2B | 120.4 | C12—C11—H11A | 108.8 |
C1—C2—H2B | 120.4 | C9—C11—H11A | 108.8 |
C4—C3—C2 | 120.9 (3) | C12—C11—H11B | 108.8 |
C4—C3—H3A | 119.5 | C9—C11—H11B | 108.8 |
C2—C3—H3A | 119.5 | H11A—C11—H11B | 107.7 |
C3—C4—C5 | 120.4 (4) | C14—C12—N3 | 104.8 (3) |
C3—C4—H4A | 119.8 | C14—C12—C11 | 132.5 (3) |
C5—C4—H4A | 119.8 | N3—C12—C11 | 122.7 (3) |
C6—C5—C4 | 119.1 (3) | C13—N4—C14 | 108.8 (3) |
C6—C5—H5A | 120.5 | C13—N4—H4B | 125.6 |
C4—C5—H5A | 120.5 | C14—N4—H4B | 125.6 |
C5—C6—C1 | 119.7 (3) | C13—N3—C12 | 109.6 (3) |
C5—C6—C7 | 122.8 (3) | C13—N3—H3C | 125.2 |
C1—C6—C7 | 117.3 (3) | C12—N3—H3C | 125.2 |
C6—C1—C2—C3 | −0.7 (5) | C8—N2—C9—C11 | 79.5 (4) |
C1—C2—C3—C4 | 2.5 (6) | C8—N2—C9—C10 | −155.5 (3) |
C2—C3—C4—C5 | −2.8 (6) | N2—C9—C10—O2 | 18.2 (4) |
C3—C4—C5—C6 | 1.2 (5) | C11—C9—C10—O2 | 141.6 (3) |
C4—C5—C6—C1 | 0.6 (5) | N2—C9—C10—O3 | −162.5 (3) |
C4—C5—C6—C7 | −175.1 (3) | C11—C9—C10—O3 | −39.1 (4) |
C2—C1—C6—C5 | −0.8 (5) | N2—C9—C11—C12 | −153.1 (2) |
C2—C1—C6—C7 | 175.1 (3) | C10—C9—C11—C12 | 84.7 (3) |
C8—N1—C7—O1 | −5.5 (5) | N4—C14—C12—N3 | 0.3 (4) |
C8—N1—C7—C6 | 175.2 (3) | N4—C14—C12—C11 | −178.7 (3) |
C5—C6—C7—O1 | 148.1 (3) | C9—C11—C12—C14 | 124.1 (4) |
C1—C6—C7—O1 | −27.7 (4) | C9—C11—C12—N3 | −54.8 (4) |
C5—C6—C7—N1 | −32.6 (4) | N3—C13—N4—C14 | 0.0 (4) |
C1—C6—C7—N1 | 151.6 (3) | C12—C14—N4—C13 | −0.2 (4) |
C9—N2—C8—N1 | −179.8 (3) | N4—C13—N3—C12 | 0.2 (4) |
C9—N2—C8—S1 | −0.4 (4) | C14—C12—N3—C13 | −0.3 (4) |
C7—N1—C8—N2 | −4.6 (4) | C11—C12—N3—C13 | 178.8 (3) |
C7—N1—C8—S1 | 175.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···S1 | 0.98 | 2.75 | 3.076 (3) | 100 |
N2—H2A···O1 | 0.86 | 1.95 | 2.630 (3) | 135 |
N3—H3C···O3 | 0.86 | 1.94 | 2.650 (4) | 139 |
N1—H1A···O3i | 0.86 | 2.05 | 2.870 (4) | 158 |
N4—H4B···O2ii | 0.86 | 1.84 | 2.650 (4) | 156 |
C13—H13A···O1ii | 0.93 | 2.40 | 3.070 (4) | 129 |
Symmetry codes: (i) x+1, y, z+1; (ii) −x, y+1/2, −z+1. |