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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—H...O hydrogen bond exists between the hydr­oxy group of the ethanoic acid fragment and the O atom of the dimeth­yl sulfoxide solvent mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016491/cv6512sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016491/cv6512Isup2.hkl
Contains datablock I

CCDC reference: 274384

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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·C2H6OSF(000) = 332
Mr = 316.39Dx = 1.412 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 734 reflections
a = 10.074 (2) Åθ = 1.6–26.0°
b = 5.6289 (12) ŵ = 0.37 mm1
c = 13.969 (3) ÅT = 298 K
β = 110.074 (4)°Block, yellow
V = 744.0 (3) Å30.44 × 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 tube2537 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
Detector resolution: 83.66 pixels mm-1θmax = 26.0°, θmin = 1.6°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 66
Tmin = 0.854, Tmax = 0.940l = 1517
4157 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-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 reflectionsΔρmax = 0.19 e Å3
184 parametersΔρmin = 0.15 e Å3
1 restraintAbsolute structure: Flack (1983), 1117 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (7)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.14142 (6)0.94424 (12)0.92765 (5)0.05230 (17)
S20.67896 (7)1.04731 (12)0.45849 (5)0.05832 (19)
O10.13275 (16)1.0048 (3)0.73050 (12)0.0572 (5)
O20.10726 (17)1.5328 (4)0.65101 (13)0.0624 (5)
O30.3078 (2)1.6498 (4)0.67026 (15)0.0645 (5)
H3A0.30161.76180.63450.097*
O40.66629 (19)1.0260 (4)0.56209 (13)0.0652 (5)
N10.07001 (19)0.8614 (4)0.86172 (14)0.0460 (5)
H1A0.09310.75940.91050.055*
N20.07524 (19)1.1742 (4)0.78547 (14)0.0477 (5)
H2A0.02161.19210.74960.057*
C10.2733 (2)0.4817 (4)0.87876 (16)0.0475 (6)
H10.19420.43730.89430.057*
C20.3903 (3)0.3343 (5)0.90534 (18)0.0559 (6)
H20.39030.19200.93910.067*
C30.5071 (3)0.4003 (5)0.88129 (18)0.0565 (7)
H30.58620.30230.89950.068*
C40.5075 (3)0.6076 (5)0.8312 (2)0.0569 (7)
H40.58640.64980.81480.068*
C50.3913 (2)0.7550 (5)0.80467 (19)0.0500 (6)
H50.39180.89600.77010.060*
C60.2731 (2)0.6935 (4)0.82944 (16)0.0418 (5)
C70.1531 (2)0.8658 (4)0.80102 (17)0.0437 (5)
C80.0466 (2)1.0028 (4)0.85308 (15)0.0422 (5)
C90.1931 (2)1.3342 (5)0.76879 (18)0.0502 (6)
H9A0.18511.41320.83220.060*
H9B0.28061.24430.74680.060*
C100.1970 (2)1.5164 (5)0.68969 (16)0.0471 (5)
C110.8625 (3)1.0575 (8)0.4808 (2)0.0904 (10)
H11A0.90021.20560.51270.136*
H11B0.87871.04380.41720.136*
H11C0.90840.92850.52470.136*
C120.6429 (4)0.7620 (6)0.4031 (3)0.0857 (10)
H12A0.71310.65200.44280.129*
H12B0.64490.76770.33490.129*
H12C0.55120.71110.40140.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0525 (3)0.0592 (4)0.0565 (3)0.0025 (3)0.0333 (3)0.0009 (3)
S20.0678 (4)0.0554 (4)0.0549 (3)0.0102 (3)0.0251 (3)0.0081 (3)
O10.0560 (9)0.0661 (13)0.0605 (10)0.0169 (9)0.0340 (8)0.0176 (9)
O20.0594 (10)0.0648 (12)0.0763 (11)0.0098 (9)0.0405 (9)0.0125 (10)
O30.0651 (11)0.0713 (13)0.0686 (12)0.0245 (10)0.0376 (10)0.0214 (10)
O40.0806 (12)0.0623 (12)0.0622 (10)0.0140 (11)0.0367 (9)0.0049 (10)
N10.0473 (11)0.0540 (12)0.0432 (10)0.0108 (9)0.0237 (9)0.0063 (9)
N20.0431 (10)0.0562 (12)0.0511 (11)0.0086 (9)0.0258 (9)0.0050 (10)
C10.0548 (13)0.0493 (16)0.0468 (12)0.0014 (11)0.0283 (10)0.0006 (11)
C20.0748 (18)0.0483 (15)0.0482 (13)0.0110 (13)0.0259 (13)0.0044 (12)
C30.0506 (14)0.0632 (19)0.0548 (15)0.0172 (13)0.0170 (12)0.0045 (13)
C40.0431 (13)0.0664 (19)0.0676 (16)0.0035 (12)0.0273 (12)0.0076 (13)
C50.0543 (14)0.0512 (15)0.0542 (14)0.0021 (11)0.0314 (12)0.0010 (11)
C60.0419 (11)0.0476 (13)0.0401 (11)0.0031 (10)0.0195 (9)0.0053 (10)
C70.0423 (12)0.0493 (14)0.0437 (12)0.0013 (10)0.0203 (10)0.0000 (10)
C80.0398 (11)0.0497 (16)0.0392 (10)0.0015 (10)0.0161 (9)0.0076 (10)
C90.0464 (13)0.0568 (15)0.0536 (14)0.0097 (11)0.0253 (11)0.0027 (12)
C100.0458 (12)0.0502 (14)0.0477 (12)0.0030 (11)0.0192 (10)0.0011 (11)
C110.082 (2)0.112 (3)0.093 (2)0.014 (2)0.0507 (18)0.009 (2)
C120.107 (3)0.082 (3)0.0675 (19)0.010 (2)0.0296 (18)0.0158 (17)
Geometric parameters (Å, º) top
S1—C81.670 (2)C2—H20.9300
S2—O41.5007 (19)C3—C41.361 (4)
S2—C121.765 (3)C3—H30.9300
S2—C111.767 (3)C4—C51.378 (3)
O1—C71.219 (3)C4—H40.9300
O2—C101.206 (3)C5—C61.393 (3)
O3—C101.294 (3)C5—H50.9300
O3—H3A0.8200C6—C71.493 (3)
N1—C71.381 (3)C9—C101.498 (3)
N1—C81.389 (3)C9—H9A0.9700
N1—H1A0.8600C9—H9B0.9700
N2—C81.311 (3)C11—H11A0.9600
N2—C91.444 (3)C11—H11B0.9600
N2—H2A0.8600C11—H11C0.9600
C1—C61.377 (3)C12—H12A0.9600
C1—C21.384 (3)C12—H12B0.9600
C1—H10.9300C12—H12C0.9600
C2—C31.380 (4)
O4—S2—C12106.10 (15)O1—C7—N1122.6 (2)
O4—S2—C11105.22 (13)O1—C7—C6121.87 (19)
C12—S2—C1198.74 (19)N1—C7—C6115.5 (2)
C10—O3—H3A109.5N2—C8—N1117.03 (19)
C7—N1—C8127.5 (2)N2—C8—S1124.27 (17)
C7—N1—H1A116.2N1—C8—S1118.70 (17)
C8—N1—H1A116.2N2—C9—C10110.97 (18)
C8—N2—C9122.71 (19)N2—C9—H9A109.4
C8—N2—H2A118.6C10—C9—H9A109.4
C9—N2—H2A118.6N2—C9—H9B109.4
C6—C1—C2120.5 (2)C10—C9—H9B109.4
C6—C1—H1119.7H9A—C9—H9B108.0
C2—C1—H1119.7O2—C10—O3125.9 (2)
C3—C2—C1119.5 (3)O2—C10—C9123.3 (2)
C3—C2—H2120.3O3—C10—C9110.75 (19)
C1—C2—H2120.3S2—C11—H11A109.5
C4—C3—C2120.6 (2)S2—C11—H11B109.5
C4—C3—H3119.7H11A—C11—H11B109.5
C2—C3—H3119.7S2—C11—H11C109.5
C3—C4—C5120.2 (2)H11A—C11—H11C109.5
C3—C4—H4119.9H11B—C11—H11C109.5
C5—C4—H4119.9S2—C12—H12A109.5
C4—C5—C6120.2 (2)S2—C12—H12B109.5
C4—C5—H5119.9H12A—C12—H12B109.5
C6—C5—H5119.9S2—C12—H12C109.5
C1—C6—C5119.0 (2)H12A—C12—H12C109.5
C1—C6—C7123.9 (2)H12B—C12—H12C109.5
C5—C6—C7117.1 (2)
C6—C1—C2—C30.5 (3)C5—C6—C7—O126.0 (3)
C1—C2—C3—C40.5 (4)C1—C6—C7—N127.2 (3)
C2—C3—C4—C50.5 (4)C5—C6—C7—N1152.2 (2)
C3—C4—C5—C60.4 (4)C9—N2—C8—N1179.9 (2)
C2—C1—C6—C51.4 (3)C9—N2—C8—S10.6 (3)
C2—C1—C6—C7178.0 (2)C7—N1—C8—N26.3 (3)
C4—C5—C6—C11.3 (4)C7—N1—C8—S1173.25 (19)
C4—C5—C6—C7178.2 (2)C8—N2—C9—C10178.1 (2)
C8—N1—C7—O11.2 (4)N2—C9—C10—O24.4 (4)
C8—N1—C7—C6179.4 (2)N2—C9—C10—O3175.9 (2)
C1—C6—C7—O1154.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.861.972.645 (3)134
N2—H2A···O20.862.352.700 (3)105
N1—H1A···S1i0.862.783.638 (2)174
O3—H3A···O4ii0.821.762.562 (3)164
C1—H1···S1i0.932.723.404 (2)132
C4—H4···O3iii0.932.593.383 (4)144
Symmetry codes: (i) x, y1/2, z+2; (ii) x1, y+1, z; (iii) x+1, y1, z.
 

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