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The benzoyl and dimethylphenyl groups in the title compound, C17H18N2OS, are cis and trans, respectively, with respect to the C=S bond. The crystal packing is characterized by N—H...O and N—H...S hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005582/hg2182sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005582/hg2182Isup2.hkl
Contains datablock I

CCDC reference: 640360

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.093
  • Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 800 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C1 .. 6.56 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

1-(2,3-Dimethylphenyl)-3-(2-methylbenzoyl)thiourea top
Crystal data top
C17H18N2OSZ = 2
Mr = 298.39F(000) = 316
Triclinic, P1Dx = 1.230 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3810 (8) ÅCell parameters from 8978 reflections
b = 9.2105 (9) Åθ = 3.8–28.3°
c = 12.9581 (13) ŵ = 0.20 mm1
α = 103.459 (8)°T = 173 K
β = 102.892 (8)°Block, colourless
γ = 101.407 (8)°0.41 × 0.38 × 0.33 mm
V = 805.65 (14) Å3
Data collection top
Stoe IPDS II two-circle
diffractometer
3696 independent reflections
Radiation source: fine-focus sealed tube3429 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 99
Tmin = 0.912, Tmax = 0.927k = 1111
9126 measured reflectionsl = 016
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0494P)2 + 0.2161P]
where P = (Fo2 + 2Fc2)/3
3696 reflections(Δ/σ)max = 0.001
201 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.24 e Å3
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
S10.63850 (4)0.63978 (3)0.91349 (2)0.03164 (10)
O10.09850 (14)0.28590 (12)0.67028 (7)0.0417 (2)
C10.45015 (15)0.51590 (12)0.81235 (9)0.0237 (2)
N10.43022 (14)0.49334 (12)0.70459 (8)0.0274 (2)
H10.329 (2)0.4249 (18)0.6611 (13)0.035 (4)*
N20.30125 (14)0.42812 (11)0.84074 (8)0.0258 (2)
H20.329 (2)0.438 (2)0.9106 (15)0.046 (4)*
C20.13867 (16)0.31811 (13)0.77132 (9)0.0250 (2)
C110.57757 (15)0.56453 (13)0.66082 (8)0.0237 (2)
C120.56837 (15)0.69863 (13)0.62969 (9)0.0244 (2)
C130.70997 (16)0.75878 (13)0.58186 (9)0.0261 (2)
C140.85482 (16)0.68441 (14)0.56971 (9)0.0276 (2)
H140.95080.72560.53850.033*
C150.86185 (17)0.55188 (15)0.60220 (10)0.0297 (2)
H150.96220.50360.59370.036*
C160.72118 (17)0.49016 (14)0.64732 (9)0.0279 (2)
H160.72310.39840.66860.033*
C170.41307 (18)0.77912 (16)0.64642 (12)0.0364 (3)
H17A0.32870.72290.68090.055*
H17B0.33710.78150.57470.055*
H17C0.47260.88520.69450.055*
C180.7068 (2)0.90127 (16)0.54378 (13)0.0401 (3)
H18A0.81440.92460.51240.060*
H18B0.71890.98900.60690.060*
H18C0.58500.88280.48740.060*
C210.01133 (15)0.23868 (12)0.82882 (8)0.0236 (2)
C220.01114 (16)0.08730 (13)0.83071 (10)0.0286 (2)
C230.12184 (19)0.01164 (15)0.87545 (11)0.0371 (3)
H230.12580.09150.87710.044*
C240.24812 (19)0.08496 (18)0.91751 (12)0.0415 (3)
H240.33890.03090.94630.050*
C250.24302 (19)0.23643 (17)0.91786 (11)0.0392 (3)
H250.32800.28670.94820.047*
C260.11197 (18)0.31470 (14)0.87329 (10)0.0308 (2)
H260.10690.41860.87330.037*
C270.1542 (2)0.00961 (16)0.78930 (13)0.0429 (3)
H27A0.12860.09660.79440.064*
H27B0.28520.06720.83460.064*
H27C0.14140.00790.71210.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.03292 (16)0.03391 (17)0.02026 (15)0.00966 (11)0.00946 (11)0.00685 (11)
O10.0380 (5)0.0545 (6)0.0205 (4)0.0123 (4)0.0067 (3)0.0103 (4)
C10.0254 (5)0.0257 (5)0.0215 (5)0.0024 (4)0.0116 (4)0.0083 (4)
N10.0249 (5)0.0357 (5)0.0192 (4)0.0022 (4)0.0098 (4)0.0087 (4)
N20.0272 (5)0.0296 (5)0.0180 (4)0.0028 (4)0.0104 (3)0.0070 (3)
C20.0248 (5)0.0276 (5)0.0224 (5)0.0016 (4)0.0094 (4)0.0087 (4)
C110.0225 (5)0.0323 (5)0.0165 (5)0.0017 (4)0.0092 (4)0.0085 (4)
C120.0213 (5)0.0305 (5)0.0213 (5)0.0049 (4)0.0084 (4)0.0070 (4)
C130.0244 (5)0.0320 (6)0.0226 (5)0.0033 (4)0.0080 (4)0.0116 (4)
C140.0229 (5)0.0403 (6)0.0220 (5)0.0044 (4)0.0113 (4)0.0120 (4)
C150.0259 (5)0.0417 (6)0.0264 (5)0.0125 (5)0.0127 (4)0.0111 (5)
C160.0312 (6)0.0324 (6)0.0245 (5)0.0092 (4)0.0106 (4)0.0135 (4)
C170.0290 (6)0.0405 (7)0.0440 (7)0.0128 (5)0.0166 (5)0.0111 (5)
C180.0394 (7)0.0408 (7)0.0476 (8)0.0085 (5)0.0154 (6)0.0255 (6)
C210.0217 (5)0.0274 (5)0.0194 (5)0.0010 (4)0.0066 (4)0.0078 (4)
C220.0271 (5)0.0284 (5)0.0281 (5)0.0017 (4)0.0069 (4)0.0095 (4)
C230.0365 (6)0.0324 (6)0.0390 (7)0.0036 (5)0.0077 (5)0.0177 (5)
C240.0319 (6)0.0532 (8)0.0390 (7)0.0054 (5)0.0146 (5)0.0219 (6)
C250.0312 (6)0.0532 (8)0.0364 (7)0.0073 (5)0.0187 (5)0.0132 (6)
C260.0319 (6)0.0330 (6)0.0299 (6)0.0064 (5)0.0133 (5)0.0107 (5)
C270.0421 (7)0.0365 (7)0.0519 (8)0.0142 (6)0.0153 (6)0.0114 (6)
Geometric parameters (Å, º) top
S1—C11.6781 (12)C17—H17A0.9800
O1—C21.2253 (14)C17—H17B0.9800
C1—N11.3325 (14)C17—H17C0.9800
C1—N21.4016 (13)C18—H18A0.9800
N1—C111.4495 (13)C18—H18B0.9800
N1—H10.856 (17)C18—H18C0.9800
N2—C21.3744 (15)C21—C261.3959 (16)
N2—H20.861 (18)C21—C221.3999 (16)
C2—C211.5059 (14)C22—C231.3988 (17)
C11—C161.3920 (16)C22—C271.5124 (18)
C11—C121.3949 (16)C23—C241.388 (2)
C12—C131.4153 (15)C23—H230.9500
C12—C171.5108 (15)C24—C251.387 (2)
C13—C141.3971 (16)C24—H240.9500
C13—C181.5083 (16)C25—C261.3986 (17)
C14—C151.3872 (17)C25—H250.9500
C14—H140.9500C26—H260.9500
C15—C161.3911 (16)C27—H27A0.9800
C15—H150.9500C27—H27B0.9800
C16—H160.9500C27—H27C0.9800
N1—C1—N2116.32 (10)C12—C17—H17C109.5
N1—C1—S1124.64 (8)H17A—C17—H17C109.5
N2—C1—S1119.04 (8)H17B—C17—H17C109.5
C1—N1—C11123.48 (10)C13—C18—H18A109.5
C1—N1—H1115.8 (11)C13—C18—H18B109.5
C11—N1—H1120.4 (11)H18A—C18—H18B109.5
C2—N2—C1128.17 (9)C13—C18—H18C109.5
C2—N2—H2118.9 (12)H18A—C18—H18C109.5
C1—N2—H2112.2 (12)H18B—C18—H18C109.5
O1—C2—N2123.25 (10)C26—C21—C22121.58 (10)
O1—C2—C21121.88 (10)C26—C21—C2119.02 (10)
N2—C2—C21114.87 (9)C22—C21—C2119.29 (10)
C16—C11—C12122.28 (10)C23—C22—C21117.82 (11)
C16—C11—N1117.31 (10)C23—C22—C27120.91 (11)
C12—C11—N1120.36 (10)C21—C22—C27121.24 (11)
C11—C12—C13118.11 (10)C24—C23—C22121.00 (12)
C11—C12—C17121.57 (10)C24—C23—H23119.5
C13—C12—C17120.32 (10)C22—C23—H23119.5
C14—C13—C12119.25 (10)C25—C24—C23120.62 (11)
C14—C13—C18119.59 (10)C25—C24—H24119.7
C12—C13—C18121.16 (10)C23—C24—H24119.7
C15—C14—C13121.55 (10)C24—C25—C26119.59 (12)
C15—C14—H14119.2C24—C25—H25120.2
C13—C14—H14119.2C26—C25—H25120.2
C14—C15—C16119.63 (10)C21—C26—C25119.34 (11)
C14—C15—H15120.2C21—C26—H26120.3
C16—C15—H15120.2C25—C26—H26120.3
C15—C16—C11119.16 (10)C22—C27—H27A109.5
C15—C16—H16120.4C22—C27—H27B109.5
C11—C16—H16120.4H27A—C27—H27B109.5
C12—C17—H17A109.5C22—C27—H27C109.5
C12—C17—H17B109.5H27A—C27—H27C109.5
H17A—C17—H17B109.5H27B—C27—H27C109.5
N2—C1—N1—C11174.63 (10)C14—C15—C16—C111.14 (17)
S1—C1—N1—C115.22 (17)C12—C11—C16—C150.60 (17)
N1—C1—N2—C21.87 (17)N1—C11—C16—C15177.94 (10)
S1—C1—N2—C2177.99 (9)O1—C2—C21—C26100.95 (14)
C1—N2—C2—O13.0 (2)N2—C2—C21—C2679.05 (13)
C1—N2—C2—C21176.98 (10)O1—C2—C21—C2275.34 (15)
C1—N1—C11—C1684.92 (14)N2—C2—C21—C22104.66 (12)
C1—N1—C11—C1297.69 (14)C26—C21—C22—C232.15 (17)
C16—C11—C12—C130.62 (16)C2—C21—C22—C23174.04 (10)
N1—C11—C12—C13176.63 (10)C26—C21—C22—C27175.87 (11)
C16—C11—C12—C17179.13 (11)C2—C21—C22—C277.95 (17)
N1—C11—C12—C173.61 (16)C21—C22—C23—C240.60 (18)
C11—C12—C13—C141.30 (16)C27—C22—C23—C24177.42 (13)
C17—C12—C13—C14178.46 (11)C22—C23—C24—C251.1 (2)
C11—C12—C13—C18178.61 (11)C23—C24—C25—C261.3 (2)
C17—C12—C13—C181.64 (17)C22—C21—C26—C251.96 (18)
C12—C13—C14—C150.78 (17)C2—C21—C26—C25174.23 (11)
C18—C13—C14—C15179.12 (12)C24—C25—C26—C210.20 (19)
C13—C14—C15—C160.46 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.856 (17)1.963 (16)2.6667 (13)138.8 (14)
N2—H2···S1i0.861 (18)2.520 (18)3.3371 (10)158.8 (15)
Symmetry code: (i) x+1, y+1, z+2.
 

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