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In the title compound, C12H14N2O4S, the dihedral angle between the 3-methoxy­benzene and the central thio­urea fragment is 7.18 (9)°. The mol­ecule exhibits a cis-trans configuration with respect to the position of the propionic acid and methoxy­benzoyl groups relative to the thiono S atom across the C-N bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017667/sa2048sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017667/sa2048Isup2.hkl
Contains datablock I

CCDC reference: 647320

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.085
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
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 26.00 From the CIF: _reflns_number_total 2297 Count of symmetry unique reflns 1339 Completeness (_total/calc) 171.55% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 958 Fraction of Friedel pairs measured 0.715 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 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-[3-(3-Methoxybenzoyl)thioureido]propionic acid top
Crystal data top
C12H14N2O4SF(000) = 592
Mr = 282.31Dx = 1.408 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 2907 reflections
a = 14.801 (6) Åθ = 2.1–26.0°
b = 4.8325 (19) ŵ = 0.26 mm1
c = 18.624 (8) ÅT = 298 K
V = 1332.1 (9) Å3Plate, colourless
Z = 40.50 × 0.40 × 0.09 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2297 independent reflections
Radiation source: fine-focus sealed tube2082 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 83.66 pixels mm-1θmax = 26.0°, θmin = 2.1°
ω scansh = 1818
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 55
Tmin = 0.883, Tmax = 0.977l = 2220
6513 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)] = 0.035H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0481P)2 + 0.0273P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2297 reflectionsΔρmax = 0.19 e Å3
174 parametersΔρmin = 0.13 e Å3
1 restraintAbsolute structure: Flack (1983), 958 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (8)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.11424 (4)0.11559 (12)0.27295 (4)0.05050 (17)
O10.05627 (15)1.3474 (4)0.06806 (12)0.0674 (5)
O20.03549 (11)0.5924 (4)0.10137 (10)0.0500 (4)
O30.25489 (12)0.4334 (4)0.33191 (9)0.0578 (5)
H30.29090.54760.31630.087*
O40.21612 (10)0.4053 (4)0.21736 (10)0.0510 (4)
N10.08777 (12)0.4735 (4)0.16645 (10)0.0379 (4)
H10.14400.50970.17330.046*
N20.03492 (12)0.2054 (4)0.19895 (10)0.0437 (5)
H20.06260.28720.16430.052*
C10.05221 (15)0.9873 (5)0.02235 (12)0.0435 (5)
H1A0.00970.96200.01670.052*
C20.09664 (17)1.1825 (5)0.01840 (12)0.0483 (6)
C30.18886 (18)1.2167 (6)0.01065 (14)0.0565 (6)
H3A0.21921.34710.03840.068*
C40.23529 (19)1.0594 (6)0.03758 (16)0.0640 (7)
H40.29731.08450.04270.077*
C50.19150 (16)0.8622 (6)0.07920 (14)0.0538 (7)
H50.22390.75480.11160.065*
C60.09973 (14)0.8274 (5)0.07202 (12)0.0408 (5)
C70.04507 (15)0.6227 (4)0.11326 (13)0.0390 (5)
C80.05016 (14)0.2713 (4)0.21010 (12)0.0376 (5)
C90.08569 (16)0.0046 (5)0.24081 (13)0.0472 (6)
H9A0.04460.13490.25910.057*
H9B0.12910.08700.20980.057*
C100.13527 (16)0.1364 (5)0.30315 (13)0.0459 (6)
H10A0.16390.00740.33150.055*
H10B0.09200.23080.33370.055*
C110.20531 (12)0.3380 (4)0.27904 (14)0.0412 (5)
C120.0389 (2)1.3385 (7)0.07289 (19)0.0727 (9)
H12A0.05761.15770.08830.109*
H12B0.05921.47400.10700.109*
H12C0.06471.37790.02670.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0500 (3)0.0452 (3)0.0562 (3)0.0002 (2)0.0026 (3)0.0140 (3)
O10.0882 (15)0.0603 (12)0.0539 (12)0.0011 (10)0.0062 (10)0.0209 (10)
O20.0443 (9)0.0523 (10)0.0535 (11)0.0019 (7)0.0038 (7)0.0103 (8)
O30.0543 (10)0.0744 (12)0.0447 (10)0.0099 (8)0.0014 (8)0.0094 (9)
O40.0434 (9)0.0620 (11)0.0476 (10)0.0015 (7)0.0024 (7)0.0009 (9)
N10.0378 (9)0.0373 (10)0.0387 (9)0.0024 (8)0.0016 (8)0.0021 (8)
N20.0412 (10)0.0414 (11)0.0485 (12)0.0028 (8)0.0030 (8)0.0056 (9)
C10.0526 (14)0.0415 (13)0.0364 (12)0.0000 (10)0.0013 (10)0.0024 (11)
C20.0719 (17)0.0420 (13)0.0310 (11)0.0003 (11)0.0008 (11)0.0006 (11)
C30.0667 (17)0.0586 (16)0.0441 (14)0.0123 (13)0.0101 (12)0.0117 (13)
C40.0536 (16)0.0747 (18)0.0636 (19)0.0082 (13)0.0058 (13)0.0172 (15)
C50.0511 (14)0.0595 (17)0.0507 (15)0.0001 (12)0.0020 (11)0.0166 (12)
C60.0509 (13)0.0360 (12)0.0355 (11)0.0002 (9)0.0041 (10)0.0023 (9)
C70.0448 (12)0.0331 (12)0.0391 (13)0.0041 (9)0.0028 (9)0.0014 (9)
C80.0447 (12)0.0298 (11)0.0383 (12)0.0029 (9)0.0065 (9)0.0014 (10)
C90.0460 (12)0.0377 (13)0.0577 (15)0.0076 (10)0.0045 (10)0.0045 (12)
C100.0442 (12)0.0474 (14)0.0460 (12)0.0073 (10)0.0008 (9)0.0041 (10)
C110.0348 (10)0.0467 (13)0.0421 (13)0.0092 (8)0.0002 (10)0.0021 (11)
C120.097 (2)0.0666 (19)0.0547 (18)0.0019 (17)0.0255 (16)0.0080 (17)
Geometric parameters (Å, º) top
S1—C81.684 (2)C3—C41.363 (4)
O1—C21.359 (3)C3—H3A0.9300
O1—C121.413 (4)C4—C51.389 (4)
O2—C71.222 (3)C4—H40.9300
O3—C111.312 (3)C5—C61.375 (3)
O3—H30.8200C5—H50.9300
O4—C111.204 (3)C6—C71.491 (3)
N1—C71.379 (3)C9—C101.514 (3)
N1—C81.388 (3)C9—H9A0.9700
N1—H10.8600C9—H9B0.9700
N2—C81.315 (3)C10—C111.492 (3)
N2—C91.454 (3)C10—H10A0.9700
N2—H20.8600C10—H10B0.9700
C1—C21.378 (3)C12—H12A0.9600
C1—C61.395 (3)C12—H12B0.9600
C1—H1A0.9300C12—H12C0.9600
C2—C31.382 (3)
C2—O1—C12117.6 (2)O2—C7—C6121.0 (2)
C11—O3—H3109.5N1—C7—C6117.94 (19)
C7—N1—C8127.26 (18)N2—C8—N1117.51 (18)
C7—N1—H1116.4N2—C8—S1122.74 (16)
C8—N1—H1116.4N1—C8—S1119.74 (16)
C8—N2—C9124.86 (19)N2—C9—C10112.4 (2)
C8—N2—H2117.6N2—C9—H9A109.1
C9—N2—H2117.6C10—C9—H9A109.1
C2—C1—C6120.2 (2)N2—C9—H9B109.1
C2—C1—H1A119.9C10—C9—H9B109.1
C6—C1—H1A119.9H9A—C9—H9B107.9
O1—C2—C1124.5 (2)C11—C10—C9112.4 (2)
O1—C2—C3115.8 (2)C11—C10—H10A109.1
C1—C2—C3119.7 (2)C9—C10—H10A109.1
C4—C3—C2120.0 (2)C11—C10—H10B109.1
C4—C3—H3A120.0C9—C10—H10B109.1
C2—C3—H3A120.0H10A—C10—H10B107.9
C3—C4—C5121.0 (3)O4—C11—O3123.1 (2)
C3—C4—H4119.5O4—C11—C10123.8 (2)
C5—C4—H4119.5O3—C11—C10113.1 (2)
C6—C5—C4119.4 (2)O1—C12—H12A109.5
C6—C5—H5120.3O1—C12—H12B109.5
C4—C5—H5120.3H12A—C12—H12B109.5
C5—C6—C1119.6 (2)O1—C12—H12C109.5
C5—C6—C7124.5 (2)H12A—C12—H12C109.5
C1—C6—C7115.8 (2)H12B—C12—H12C109.5
O2—C7—N1121.0 (2)
C12—O1—C2—C17.0 (4)C8—N1—C7—C6178.9 (2)
C12—O1—C2—C3174.0 (3)C5—C6—C7—O2176.0 (2)
C6—C1—C2—O1179.9 (2)C1—C6—C7—O22.9 (3)
C6—C1—C2—C30.9 (4)C5—C6—C7—N15.6 (3)
O1—C2—C3—C4179.6 (3)C1—C6—C7—N1175.57 (19)
C1—C2—C3—C40.6 (4)C9—N2—C8—N1178.2 (2)
C2—C3—C4—C50.4 (4)C9—N2—C8—S13.4 (3)
C3—C4—C5—C60.6 (4)C7—N1—C8—N22.3 (3)
C4—C5—C6—C11.0 (4)C7—N1—C8—S1179.25 (17)
C4—C5—C6—C7179.8 (2)C8—N2—C9—C1091.8 (3)
C2—C1—C6—C51.1 (3)N2—C9—C10—C1163.4 (3)
C2—C1—C6—C7180.0 (2)C9—C10—C11—O45.7 (3)
C8—N1—C7—O22.6 (3)C9—C10—C11—O3173.64 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O20.861.932.608 (3)135
N2—H2···O40.862.542.871 (3)104
C1—H1A···O20.932.412.737 (3)100
C9—H9A···S10.972.663.066 (3)106
O3—H3···S1i0.822.303.116 (2)177
N1—H1···O4ii0.862.263.109 (3)167
C5—H5···O4ii0.932.293.188 (3)161
Symmetry codes: (i) x1/2, y+1, z; (ii) x+1/2, y+1, z.
 

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