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In the structure of the title compound, C16H16N2O2S, the dihedral angle between the two aromatic ring planes is 48.3 (1)°. Inter­molecular N—H...S hydrogen bonds link the mol­ecules into dimers which are stacked along [100].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037531/cs2042sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037531/cs2042Isup2.hkl
Contains datablock I

CCDC reference: 660201

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.115
  • Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2 ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. S1 .. 2.89 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 5 Informative message, check

Comment top

The background to this study has been set out in the previous paper (Saeed & Flörke, 2007). In the molecular structure of the title compound, (I), (Fig. 1) the torsion angles C8—N2—C9—O1 of -5.4 (4)° and C9—N2—C8—N1 of 4.8 (3)° reflect the almost planar conformation of I with respect to the thiocarbonyl and carbonyl parts. The two aromatic rings form a dihedral angle of 48.30 (8)°, the associated N2—C9—C10—C15 torsion angle is -17.5 (3)°. All other bond parameters (Table 1) are typical for these thiourea compounds (Saeed & Flörke, 2006). Also typical is the intramolecular N1—H···O hydrogen bond. The crystal packing is determined by intermolecular N2—H···S hydrogen bonds, forming centrosymmetric dimers which are stacked along [100].

Related literature top

For related literature, see: Saeed & Flörke (2006, 2007).

Experimental top

A solution of 4-methylbenzoyl chloride (1.75 g,10 mmol) in acetone (50 ml) was added dropwise to a suspension of potassium thiocyanate (0.97 g,10 mmol) in acetone (30 ml) and the reaction mixture was refluxed for 30 min. After cooling to room temperature, a solution of 3-methoxyaniline (10 mmol) in acetone (10 ml) was added and the resulting mixture refluxed for 2.0 h. The reaction mixture was poured into cold water when the thiourea was precipitated as a solid. Recrystallized from ethanol as colourless crystals (2.4 g, 8.0 mmol, 80%). m.p. 79°C. IR (KBr) cm-1: 3351 (free NH), 3200 (assoc. NH), 1667 (CO), 1610 (arom.), 1529 (thioureido I) 1325 II, 1160 III, 744, 762; 1H NMR (CDCl3) ?: 3.89 (3H, s, ArOCH3), 7.31–7.75 (aromatic), 9.19 (1H, s, broad, NH); 12.76 (1H, s, broad, NH); 13 C NMR (CDCl3) ? 55.6 (OCH3), 126.2 (4 CH), 129.0 (2 CH), 129.20 (2CH), 130.7 (C), 132.1 (C),134.8 (C) 142.3 (C), 168.1 (C=O), 178.4 (C=S). EIMS m/e: 300, 168.9,149, 119, 91, 64.9; Analysis calculated for C16H16N2O2S C, 63.98; H, 5.37; N, 9.33; S, 10.67 found C, 64.01; H, 5.32; N, 9.10; S, 10.65

Refinement top

Hydrogen atoms were located in difference syntheses, constrained at idealized positions riding on the C (C—H = 0.95–0.99 Å) or N (N—H = 0.88 Å) atoms with isotropic displacement parameters Uiso(H) = 1.2U(Ceq / Neq) and 1.5(methyl-C). Methyl H atoms were refined on the basis of rigid groups allowed to rotate but not tip.

Structure description top

The background to this study has been set out in the previous paper (Saeed & Flörke, 2007). In the molecular structure of the title compound, (I), (Fig. 1) the torsion angles C8—N2—C9—O1 of -5.4 (4)° and C9—N2—C8—N1 of 4.8 (3)° reflect the almost planar conformation of I with respect to the thiocarbonyl and carbonyl parts. The two aromatic rings form a dihedral angle of 48.30 (8)°, the associated N2—C9—C10—C15 torsion angle is -17.5 (3)°. All other bond parameters (Table 1) are typical for these thiourea compounds (Saeed & Flörke, 2006). Also typical is the intramolecular N1—H···O hydrogen bond. The crystal packing is determined by intermolecular N2—H···S hydrogen bonds, forming centrosymmetric dimers which are stacked along [100].

For related literature, see: Saeed & Flörke (2006, 2007).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1.  
1-(3-Methoxyphenyl)-3-(4-methylbenzoyl)thiourea top
Crystal data top
C16H16N2O2SF(000) = 632
Mr = 300.37Dx = 1.339 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1407 reflections
a = 5.3031 (6) Åθ = 2.5–21.2°
b = 21.159 (2) ŵ = 0.22 mm1
c = 13.2837 (14) ÅT = 120 K
β = 90.027 (15)°Needle, colourless
V = 1490.5 (3) Å30.52 × 0.10 × 0.09 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
3535 independent reflections
Radiation source: sealed tube2050 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.091
φ and ω scansθmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 66
Tmin = 0.893, Tmax = 0.980k = 2727
12383 measured reflectionsl = 1716
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: difference Fourier map
wR(F2) = 0.115H-atom parameters constrained
S = 0.88 w = 1/[σ2(Fo2) + (0.0434P)2]
where P = (Fo2 + 2Fc2)/3
3535 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C16H16N2O2SV = 1490.5 (3) Å3
Mr = 300.37Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.3031 (6) ŵ = 0.22 mm1
b = 21.159 (2) ÅT = 120 K
c = 13.2837 (14) Å0.52 × 0.10 × 0.09 mm
β = 90.027 (15)°
Data collection top
Bruker SMART APEX
diffractometer
3535 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
2050 reflections with I > 2σ(I)
Tmin = 0.893, Tmax = 0.980Rint = 0.091
12383 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 0.88Δρmax = 0.32 e Å3
3535 reflectionsΔρmin = 0.33 e Å3
190 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.32324 (14)1.01213 (3)0.85607 (5)0.0443 (2)
O10.6061 (3)0.81054 (7)0.82493 (11)0.0427 (5)
O20.0758 (3)0.86111 (8)0.42661 (12)0.0484 (5)
N10.3031 (3)0.90015 (8)0.76221 (13)0.0325 (5)
H10.35420.86060.76360.039*
N20.5727 (3)0.90797 (8)0.89643 (13)0.0326 (5)
H20.62530.93090.94760.039*
C10.1346 (4)0.91542 (10)0.68283 (16)0.0302 (5)
C20.0701 (5)0.95549 (10)0.69401 (18)0.0371 (6)
H2A0.10010.97670.75590.044*
C30.2299 (5)0.96387 (11)0.6126 (2)0.0447 (7)
H3A0.37060.99130.61940.054*
C40.1907 (5)0.93341 (11)0.52169 (19)0.0421 (7)
H4A0.30280.93980.46680.050*
C50.0128 (5)0.89387 (10)0.51231 (17)0.0348 (6)
C60.1752 (4)0.88476 (9)0.59290 (17)0.0321 (6)
H6A0.31540.85720.58600.039*
C70.0996 (5)0.86212 (13)0.34504 (18)0.0579 (8)
H7A0.26510.84800.36890.087*
H7B0.04070.83380.29160.087*
H7C0.11320.90520.31870.087*
C80.3948 (4)0.93659 (10)0.83449 (16)0.0304 (5)
C90.6782 (5)0.84850 (10)0.88869 (16)0.0322 (5)
C100.8808 (4)0.83358 (9)0.96113 (15)0.0278 (5)
C110.9470 (5)0.77047 (10)0.97489 (16)0.0360 (6)
H11A0.86250.73840.93780.043*
C121.1343 (5)0.75421 (10)1.04196 (16)0.0362 (6)
H12A1.17830.71101.05000.043*
C131.2603 (4)0.79982 (10)1.09818 (15)0.0317 (5)
C141.1956 (5)0.86231 (10)1.08289 (17)0.0381 (6)
H14A1.28060.89431.11980.046*
C151.0105 (4)0.87923 (10)1.01519 (16)0.0342 (6)
H15A0.97140.92261.00550.041*
C161.4626 (5)0.78203 (11)1.17233 (17)0.0431 (6)
H16A1.62140.80241.15320.065*
H16B1.48480.73601.17220.065*
H16C1.41330.79601.23980.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0624 (5)0.0291 (3)0.0416 (4)0.0117 (3)0.0172 (3)0.0020 (3)
O10.0533 (12)0.0361 (9)0.0387 (10)0.0122 (8)0.0175 (9)0.0076 (7)
O20.0523 (13)0.0539 (11)0.0390 (10)0.0027 (9)0.0230 (9)0.0015 (8)
N10.0388 (13)0.0261 (9)0.0327 (11)0.0039 (9)0.0077 (9)0.0008 (8)
N20.0410 (13)0.0304 (10)0.0264 (10)0.0067 (9)0.0094 (9)0.0023 (8)
C10.0281 (14)0.0267 (11)0.0357 (13)0.0049 (10)0.0084 (11)0.0077 (10)
C20.0311 (15)0.0371 (13)0.0429 (15)0.0004 (11)0.0023 (12)0.0045 (11)
C30.0281 (16)0.0392 (14)0.0667 (19)0.0018 (12)0.0078 (14)0.0118 (13)
C40.0345 (16)0.0438 (14)0.0479 (17)0.0037 (12)0.0199 (13)0.0147 (12)
C50.0366 (16)0.0316 (12)0.0362 (15)0.0092 (11)0.0106 (12)0.0068 (10)
C60.0306 (15)0.0281 (11)0.0376 (14)0.0010 (10)0.0091 (11)0.0036 (10)
C70.060 (2)0.076 (2)0.0387 (16)0.0074 (15)0.0272 (15)0.0082 (13)
C80.0335 (15)0.0318 (12)0.0259 (12)0.0034 (10)0.0014 (11)0.0029 (9)
C90.0377 (15)0.0315 (12)0.0274 (13)0.0043 (11)0.0006 (11)0.0007 (10)
C100.0300 (14)0.0309 (12)0.0224 (12)0.0049 (10)0.0026 (10)0.0005 (9)
C110.0426 (16)0.0319 (12)0.0337 (14)0.0029 (11)0.0105 (12)0.0056 (10)
C120.0409 (16)0.0303 (12)0.0375 (14)0.0075 (11)0.0073 (12)0.0016 (10)
C130.0291 (14)0.0442 (13)0.0217 (12)0.0018 (11)0.0011 (10)0.0008 (10)
C140.0402 (16)0.0358 (13)0.0382 (14)0.0041 (11)0.0054 (12)0.0068 (11)
C150.0390 (16)0.0270 (12)0.0366 (14)0.0007 (10)0.0030 (12)0.0003 (10)
C160.0375 (16)0.0543 (16)0.0374 (15)0.0000 (12)0.0074 (12)0.0000 (12)
Geometric parameters (Å, º) top
S1—C81.668 (2)C6—H6A0.9500
O1—C91.228 (2)C7—H7A0.9800
O2—C51.374 (3)C7—H7B0.9800
O2—C71.428 (3)C7—H7C0.9800
N1—C81.324 (3)C9—C101.477 (3)
N1—C11.419 (3)C10—C151.386 (3)
N1—H10.8800C10—C111.393 (3)
N2—C91.381 (3)C11—C121.378 (3)
N2—C81.391 (3)C11—H11A0.9500
N2—H20.8800C12—C131.391 (3)
C1—C61.376 (3)C12—H12A0.9500
C1—C21.385 (3)C13—C141.381 (3)
C2—C31.385 (3)C13—C161.504 (3)
C2—H2A0.9500C14—C151.379 (3)
C3—C41.385 (3)C14—H14A0.9500
C3—H3A0.9500C15—H15A0.9500
C4—C51.371 (3)C16—H16A0.9800
C4—H4A0.9500C16—H16B0.9800
C5—C61.387 (3)C16—H16C0.9800
C5—O2—C7117.6 (2)N1—C8—N2115.12 (18)
C8—N1—C1129.59 (18)N1—C8—S1126.83 (17)
C8—N1—H1115.2N2—C8—S1118.03 (16)
C1—N1—H1115.2O1—C9—N2121.4 (2)
C9—N2—C8128.87 (18)O1—C9—C10122.4 (2)
C9—N2—H2115.6N2—C9—C10116.18 (19)
C8—N2—H2115.6C15—C10—C11118.4 (2)
C6—C1—C2120.3 (2)C15—C10—C9123.34 (19)
C6—C1—N1116.0 (2)C11—C10—C9118.28 (19)
C2—C1—N1123.6 (2)C12—C11—C10120.4 (2)
C3—C2—C1118.3 (2)C12—C11—H11A119.8
C3—C2—H2A120.9C10—C11—H11A119.8
C1—C2—H2A120.9C11—C12—C13121.3 (2)
C2—C3—C4122.0 (2)C11—C12—H12A119.3
C2—C3—H3A119.0C13—C12—H12A119.3
C4—C3—H3A119.0C14—C13—C12117.8 (2)
C5—C4—C3118.8 (2)C14—C13—C16120.9 (2)
C5—C4—H4A120.6C12—C13—C16121.4 (2)
C3—C4—H4A120.6C15—C14—C13121.4 (2)
C4—C5—O2125.0 (2)C15—C14—H14A119.3
C4—C5—C6120.2 (2)C13—C14—H14A119.3
O2—C5—C6114.7 (2)C14—C15—C10120.7 (2)
C1—C6—C5120.5 (2)C14—C15—H15A119.7
C1—C6—H6A119.8C10—C15—H15A119.7
C5—C6—H6A119.8C13—C16—H16A109.5
O2—C7—H7A109.5C13—C16—H16B109.5
O2—C7—H7B109.5H16A—C16—H16B109.5
H7A—C7—H7B109.5C13—C16—H16C109.5
O2—C7—H7C109.5H16A—C16—H16C109.5
H7A—C7—H7C109.5H16B—C16—H16C109.5
H7B—C7—H7C109.5
C8—N1—C1—C6144.9 (2)C9—N2—C8—S1173.97 (18)
C8—N1—C1—C239.0 (3)C8—N2—C9—O15.4 (4)
C6—C1—C2—C30.3 (3)C8—N2—C9—C10174.6 (2)
N1—C1—C2—C3176.2 (2)O1—C9—C10—C15162.5 (2)
C1—C2—C3—C40.2 (3)N2—C9—C10—C1517.5 (3)
C2—C3—C4—C50.1 (4)O1—C9—C10—C1116.7 (3)
C3—C4—C5—O2179.4 (2)N2—C9—C10—C11163.3 (2)
C3—C4—C5—C60.1 (3)C15—C10—C11—C121.0 (3)
C7—O2—C5—C48.0 (3)C9—C10—C11—C12179.7 (2)
C7—O2—C5—C6172.4 (2)C10—C11—C12—C130.6 (4)
C2—C1—C6—C50.4 (3)C11—C12—C13—C141.5 (4)
N1—C1—C6—C5176.56 (19)C11—C12—C13—C16179.2 (2)
C4—C5—C6—C10.3 (3)C12—C13—C14—C150.8 (4)
O2—C5—C6—C1179.32 (18)C16—C13—C14—C15180.0 (2)
C1—N1—C8—N2175.1 (2)C13—C14—C15—C100.9 (4)
C1—N1—C8—S13.5 (4)C11—C10—C15—C141.7 (3)
C9—N2—C8—N14.8 (3)C9—C10—C15—C14179.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···S1i0.882.893.7376 (19)163
N1—H1···O10.881.892.621 (2)140
Symmetry code: (i) x+1, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC16H16N2O2S
Mr300.37
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)5.3031 (6), 21.159 (2), 13.2837 (14)
β (°) 90.027 (15)
V3)1490.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.52 × 0.10 × 0.09
Data collection
DiffractometerBruker SMART APEX
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.893, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
12383, 3535, 2050
Rint0.091
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.115, 0.88
No. of reflections3535
No. of parameters190
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.33

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXTL (Bruker, 2002), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···S1i0.882.893.7376 (19)163.3
N1—H1···O10.881.892.621 (2)139.5
Symmetry code: (i) x+1, y+2, z+2.
 

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