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organic compounds
In the title compound, C10H10N2O3S·C2H6SO, the ethanoic acid fragment and benzene ring make dihedral angles of 3.61 (9) and 20.77 (9)°, respectively, with the central thiourea N2CS group. In the crystal structure, an intermolecular O—HO hydrogen bond exists between the hydroxy group of the ethanoic acid fragment and the O atom of the dimethyl sulfoxide solvent molecule.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016491/cv6512sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016491/cv6512Isup2.hkl |
CCDC reference: 274384
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.033
- wR factor = 0.077
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for S2
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.99 From the CIF: _reflns_number_total 2725 Count of symmetry unique reflns 1620 Completeness (_total/calc) 168.21% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1105 Fraction of Friedel pairs measured 0.682 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 2 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).
2-(3-Benzoylthioureido)ethanoic acid dimethyl sulfoxide solvate top
Crystal data top
C10H10N2O3S·C2H6OS | F(000) = 332 |
Mr = 316.39 | Dx = 1.412 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 734 reflections |
a = 10.074 (2) Å | θ = 1.6–26.0° |
b = 5.6289 (12) Å | µ = 0.37 mm−1 |
c = 13.969 (3) Å | T = 298 K |
β = 110.074 (4)° | Block, yellow |
V = 744.0 (3) Å3 | 0.44 × 0.34 × 0.17 mm |
Z = 2 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2725 independent reflections |
Radiation source: fine-focus sealed tube | 2537 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −6→6 |
Tmin = 0.854, Tmax = 0.940 | l = −15→17 |
4157 measured reflections |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0359P)2 + 0.1167P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2725 reflections | Δρmax = 0.19 e Å−3 |
184 parameters | Δρmin = −0.15 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1117 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (7) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | −0.14142 (6) | 0.94424 (12) | 0.92765 (5) | 0.05230 (17) | |
S2 | 0.67896 (7) | 1.04731 (12) | 0.45849 (5) | 0.05832 (19) | |
O1 | 0.13275 (16) | 1.0048 (3) | 0.73050 (12) | 0.0572 (5) | |
O2 | −0.10726 (17) | 1.5328 (4) | 0.65101 (13) | 0.0624 (5) | |
O3 | −0.3078 (2) | 1.6498 (4) | 0.67026 (15) | 0.0645 (5) | |
H3A | −0.3016 | 1.7618 | 0.6345 | 0.097* | |
O4 | 0.66629 (19) | 1.0260 (4) | 0.56209 (13) | 0.0652 (5) | |
N1 | 0.07001 (19) | 0.8614 (4) | 0.86172 (14) | 0.0460 (5) | |
H1A | 0.0931 | 0.7594 | 0.9105 | 0.055* | |
N2 | −0.07524 (19) | 1.1742 (4) | 0.78547 (14) | 0.0477 (5) | |
H2A | −0.0216 | 1.1921 | 0.7496 | 0.057* | |
C1 | 0.2733 (2) | 0.4817 (4) | 0.87876 (16) | 0.0475 (6) | |
H1 | 0.1942 | 0.4373 | 0.8943 | 0.057* | |
C2 | 0.3903 (3) | 0.3343 (5) | 0.90534 (18) | 0.0559 (6) | |
H2 | 0.3903 | 0.1920 | 0.9391 | 0.067* | |
C3 | 0.5071 (3) | 0.4003 (5) | 0.88129 (18) | 0.0565 (7) | |
H3 | 0.5862 | 0.3023 | 0.8995 | 0.068* | |
C4 | 0.5075 (3) | 0.6076 (5) | 0.8312 (2) | 0.0569 (7) | |
H4 | 0.5864 | 0.6498 | 0.8148 | 0.068* | |
C5 | 0.3913 (2) | 0.7550 (5) | 0.80467 (19) | 0.0500 (6) | |
H5 | 0.3918 | 0.8960 | 0.7701 | 0.060* | |
C6 | 0.2731 (2) | 0.6935 (4) | 0.82944 (16) | 0.0418 (5) | |
C7 | 0.1531 (2) | 0.8658 (4) | 0.80102 (17) | 0.0437 (5) | |
C8 | −0.0466 (2) | 1.0028 (4) | 0.85308 (15) | 0.0422 (5) | |
C9 | −0.1931 (2) | 1.3342 (5) | 0.76879 (18) | 0.0502 (6) | |
H9A | −0.1851 | 1.4132 | 0.8322 | 0.060* | |
H9B | −0.2806 | 1.2443 | 0.7468 | 0.060* | |
C10 | −0.1970 (2) | 1.5164 (5) | 0.68969 (16) | 0.0471 (5) | |
C11 | 0.8625 (3) | 1.0575 (8) | 0.4808 (2) | 0.0904 (10) | |
H11A | 0.9002 | 1.2056 | 0.5127 | 0.136* | |
H11B | 0.8787 | 1.0438 | 0.4172 | 0.136* | |
H11C | 0.9084 | 0.9285 | 0.5247 | 0.136* | |
C12 | 0.6429 (4) | 0.7620 (6) | 0.4031 (3) | 0.0857 (10) | |
H12A | 0.7131 | 0.6520 | 0.4428 | 0.129* | |
H12B | 0.6449 | 0.7677 | 0.3349 | 0.129* | |
H12C | 0.5512 | 0.7111 | 0.4014 | 0.129* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0525 (3) | 0.0592 (4) | 0.0565 (3) | 0.0025 (3) | 0.0333 (3) | 0.0009 (3) |
S2 | 0.0678 (4) | 0.0554 (4) | 0.0549 (3) | 0.0102 (3) | 0.0251 (3) | 0.0081 (3) |
O1 | 0.0560 (9) | 0.0661 (13) | 0.0605 (10) | 0.0169 (9) | 0.0340 (8) | 0.0176 (9) |
O2 | 0.0594 (10) | 0.0648 (12) | 0.0763 (11) | 0.0098 (9) | 0.0405 (9) | 0.0125 (10) |
O3 | 0.0651 (11) | 0.0713 (13) | 0.0686 (12) | 0.0245 (10) | 0.0376 (10) | 0.0214 (10) |
O4 | 0.0806 (12) | 0.0623 (12) | 0.0622 (10) | 0.0140 (11) | 0.0367 (9) | 0.0049 (10) |
N1 | 0.0473 (11) | 0.0540 (12) | 0.0432 (10) | 0.0108 (9) | 0.0237 (9) | 0.0063 (9) |
N2 | 0.0431 (10) | 0.0562 (12) | 0.0511 (11) | 0.0086 (9) | 0.0258 (9) | 0.0050 (10) |
C1 | 0.0548 (13) | 0.0493 (16) | 0.0468 (12) | 0.0014 (11) | 0.0283 (10) | −0.0006 (11) |
C2 | 0.0748 (18) | 0.0483 (15) | 0.0482 (13) | 0.0110 (13) | 0.0259 (13) | 0.0044 (12) |
C3 | 0.0506 (14) | 0.0632 (19) | 0.0548 (15) | 0.0172 (13) | 0.0170 (12) | −0.0045 (13) |
C4 | 0.0431 (13) | 0.0664 (19) | 0.0676 (16) | 0.0035 (12) | 0.0273 (12) | −0.0076 (13) |
C5 | 0.0543 (14) | 0.0512 (15) | 0.0542 (14) | 0.0021 (11) | 0.0314 (12) | −0.0010 (11) |
C6 | 0.0419 (11) | 0.0476 (13) | 0.0401 (11) | 0.0031 (10) | 0.0195 (9) | −0.0053 (10) |
C7 | 0.0423 (12) | 0.0493 (14) | 0.0437 (12) | 0.0013 (10) | 0.0203 (10) | 0.0000 (10) |
C8 | 0.0398 (11) | 0.0497 (16) | 0.0392 (10) | −0.0015 (10) | 0.0161 (9) | −0.0076 (10) |
C9 | 0.0464 (13) | 0.0568 (15) | 0.0536 (14) | 0.0097 (11) | 0.0253 (11) | 0.0027 (12) |
C10 | 0.0458 (12) | 0.0502 (14) | 0.0477 (12) | 0.0030 (11) | 0.0192 (10) | −0.0011 (11) |
C11 | 0.082 (2) | 0.112 (3) | 0.093 (2) | −0.014 (2) | 0.0507 (18) | −0.009 (2) |
C12 | 0.107 (3) | 0.082 (3) | 0.0675 (19) | −0.010 (2) | 0.0296 (18) | −0.0158 (17) |
Geometric parameters (Å, º) top
S1—C8 | 1.670 (2) | C2—H2 | 0.9300 |
S2—O4 | 1.5007 (19) | C3—C4 | 1.361 (4) |
S2—C12 | 1.765 (3) | C3—H3 | 0.9300 |
S2—C11 | 1.767 (3) | C4—C5 | 1.378 (3) |
O1—C7 | 1.219 (3) | C4—H4 | 0.9300 |
O2—C10 | 1.206 (3) | C5—C6 | 1.393 (3) |
O3—C10 | 1.294 (3) | C5—H5 | 0.9300 |
O3—H3A | 0.8200 | C6—C7 | 1.493 (3) |
N1—C7 | 1.381 (3) | C9—C10 | 1.498 (3) |
N1—C8 | 1.389 (3) | C9—H9A | 0.9700 |
N1—H1A | 0.8600 | C9—H9B | 0.9700 |
N2—C8 | 1.311 (3) | C11—H11A | 0.9600 |
N2—C9 | 1.444 (3) | C11—H11B | 0.9600 |
N2—H2A | 0.8600 | C11—H11C | 0.9600 |
C1—C6 | 1.377 (3) | C12—H12A | 0.9600 |
C1—C2 | 1.384 (3) | C12—H12B | 0.9600 |
C1—H1 | 0.9300 | C12—H12C | 0.9600 |
C2—C3 | 1.380 (4) | ||
O4—S2—C12 | 106.10 (15) | O1—C7—N1 | 122.6 (2) |
O4—S2—C11 | 105.22 (13) | O1—C7—C6 | 121.87 (19) |
C12—S2—C11 | 98.74 (19) | N1—C7—C6 | 115.5 (2) |
C10—O3—H3A | 109.5 | N2—C8—N1 | 117.03 (19) |
C7—N1—C8 | 127.5 (2) | N2—C8—S1 | 124.27 (17) |
C7—N1—H1A | 116.2 | N1—C8—S1 | 118.70 (17) |
C8—N1—H1A | 116.2 | N2—C9—C10 | 110.97 (18) |
C8—N2—C9 | 122.71 (19) | N2—C9—H9A | 109.4 |
C8—N2—H2A | 118.6 | C10—C9—H9A | 109.4 |
C9—N2—H2A | 118.6 | N2—C9—H9B | 109.4 |
C6—C1—C2 | 120.5 (2) | C10—C9—H9B | 109.4 |
C6—C1—H1 | 119.7 | H9A—C9—H9B | 108.0 |
C2—C1—H1 | 119.7 | O2—C10—O3 | 125.9 (2) |
C3—C2—C1 | 119.5 (3) | O2—C10—C9 | 123.3 (2) |
C3—C2—H2 | 120.3 | O3—C10—C9 | 110.75 (19) |
C1—C2—H2 | 120.3 | S2—C11—H11A | 109.5 |
C4—C3—C2 | 120.6 (2) | S2—C11—H11B | 109.5 |
C4—C3—H3 | 119.7 | H11A—C11—H11B | 109.5 |
C2—C3—H3 | 119.7 | S2—C11—H11C | 109.5 |
C3—C4—C5 | 120.2 (2) | H11A—C11—H11C | 109.5 |
C3—C4—H4 | 119.9 | H11B—C11—H11C | 109.5 |
C5—C4—H4 | 119.9 | S2—C12—H12A | 109.5 |
C4—C5—C6 | 120.2 (2) | S2—C12—H12B | 109.5 |
C4—C5—H5 | 119.9 | H12A—C12—H12B | 109.5 |
C6—C5—H5 | 119.9 | S2—C12—H12C | 109.5 |
C1—C6—C5 | 119.0 (2) | H12A—C12—H12C | 109.5 |
C1—C6—C7 | 123.9 (2) | H12B—C12—H12C | 109.5 |
C5—C6—C7 | 117.1 (2) | ||
C6—C1—C2—C3 | −0.5 (3) | C5—C6—C7—O1 | 26.0 (3) |
C1—C2—C3—C4 | −0.5 (4) | C1—C6—C7—N1 | 27.2 (3) |
C2—C3—C4—C5 | 0.5 (4) | C5—C6—C7—N1 | −152.2 (2) |
C3—C4—C5—C6 | 0.4 (4) | C9—N2—C8—N1 | −179.9 (2) |
C2—C1—C6—C5 | 1.4 (3) | C9—N2—C8—S1 | 0.6 (3) |
C2—C1—C6—C7 | −178.0 (2) | C7—N1—C8—N2 | −6.3 (3) |
C4—C5—C6—C1 | −1.3 (4) | C7—N1—C8—S1 | 173.25 (19) |
C4—C5—C6—C7 | 178.2 (2) | C8—N2—C9—C10 | 178.1 (2) |
C8—N1—C7—O1 | 1.2 (4) | N2—C9—C10—O2 | −4.4 (4) |
C8—N1—C7—C6 | 179.4 (2) | N2—C9—C10—O3 | 175.9 (2) |
C1—C6—C7—O1 | −154.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.97 | 2.645 (3) | 134 |
N2—H2A···O2 | 0.86 | 2.35 | 2.700 (3) | 105 |
N1—H1A···S1i | 0.86 | 2.78 | 3.638 (2) | 174 |
O3—H3A···O4ii | 0.82 | 1.76 | 2.562 (3) | 164 |
C1—H1···S1i | 0.93 | 2.72 | 3.404 (2) | 132 |
C4—H4···O3iii | 0.93 | 2.59 | 3.383 (4) | 144 |
Symmetry codes: (i) −x, y−1/2, −z+2; (ii) x−1, y+1, z; (iii) x+1, y−1, z. |
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