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In the title compound, C14H10Cl2N2OS, the geometric parameters do not show unusual features. The thio­carbonyl and carbonyl groups are almost coplanar with the chloro­phenyl ring, as reflected by the torsion angles of 0.7 (3) and -5.8 (3)°, respectively. The structure exhibits inter- and intra­molecular hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033320/ac2037sup1.cif
Contains datablocks I, rauf-8

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033320/ac2037Isup2.hkl
Contains datablock I

CCDC reference: 620520

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.085
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O1 .. 2.83 Ang.
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C2 .. 5.19 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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); software used to prepare material for publication: SHELXL97.

1-(2-Chlorobenzoyl)-3-(3-chlorophenyl)thiourea top
Crystal data top
C14H10Cl2N2OSF(000) = 664
Mr = 325.20Dx = 1.493 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11726 reflections
a = 10.7919 (10) Åθ = 3.7–25.8°
b = 9.9331 (6) ŵ = 0.59 mm1
c = 13.7534 (12) ÅT = 173 K
β = 101.002 (7)°Block, colourless
V = 1447.2 (2) Å30.39 × 0.35 × 0.34 mm
Z = 4
Data collection top
Stoe IPDS II two-circle-
diffractometer
2704 independent reflections
Radiation source: fine-focus sealed tube2283 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ω scansθmax = 25.6°, θmin = 3.7°
Absorption correction: multi-scan
MULABS (Spek, 2003; Blessing, 1995)
h = 1313
Tmin = 0.803, Tmax = 0.825k = 1210
11996 measured reflectionsl = 1416
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0462P)2 + 0.3673P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2704 reflectionsΔρmax = 0.27 e Å3
190 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0134 (14)
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
S10.09718 (4)0.61900 (5)0.62126 (4)0.02350 (15)
Cl10.19654 (5)0.18942 (5)0.39441 (4)0.02967 (16)
Cl20.34366 (6)0.61109 (6)0.98566 (4)0.04089 (18)
C10.26911 (15)0.48371 (18)0.41021 (13)0.0160 (4)
O10.38384 (11)0.49456 (15)0.43225 (10)0.0267 (3)
N10.18950 (14)0.51784 (16)0.47287 (11)0.0181 (3)
H10.115 (2)0.502 (2)0.4535 (15)0.020 (5)*
C20.21794 (15)0.57051 (18)0.56922 (12)0.0158 (4)
N20.34125 (13)0.57936 (15)0.60952 (11)0.0163 (3)
H20.393 (2)0.559 (2)0.5700 (16)0.026 (6)*
C110.20134 (15)0.43526 (19)0.31022 (12)0.0166 (4)
C120.16164 (15)0.30190 (18)0.29595 (13)0.0179 (4)
C130.09699 (17)0.2572 (2)0.20475 (15)0.0274 (5)
H130.06970.16630.19620.033*
C140.07282 (19)0.3467 (2)0.12644 (15)0.0342 (5)
H140.02850.31710.06370.041*
C150.1128 (2)0.4790 (3)0.13873 (16)0.0373 (5)
H150.09620.53940.08420.045*
C160.17688 (18)0.5244 (2)0.23017 (15)0.0276 (5)
H160.20390.61540.23820.033*
C210.39465 (15)0.63111 (17)0.70560 (13)0.0170 (4)
C220.34532 (17)0.59870 (19)0.78886 (14)0.0214 (4)
H220.27210.54400.78360.026*
C230.40629 (18)0.64877 (19)0.88047 (14)0.0229 (4)
C240.51374 (17)0.7269 (2)0.89059 (15)0.0270 (5)
H240.55400.75930.95370.032*
C250.56174 (17)0.7570 (2)0.80604 (15)0.0278 (5)
H250.63600.81010.81170.033*
C260.50256 (16)0.71038 (19)0.71346 (14)0.0217 (4)
H260.53540.73240.65610.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0148 (2)0.0348 (3)0.0207 (3)0.00095 (18)0.00308 (18)0.0120 (2)
Cl10.0361 (3)0.0220 (3)0.0298 (3)0.0013 (2)0.0036 (2)0.0049 (2)
Cl20.0614 (4)0.0471 (4)0.0157 (3)0.0186 (3)0.0110 (2)0.0080 (2)
C10.0160 (8)0.0157 (9)0.0154 (9)0.0003 (6)0.0006 (7)0.0004 (7)
O10.0137 (6)0.0456 (9)0.0202 (7)0.0001 (6)0.0013 (5)0.0099 (6)
N10.0110 (7)0.0282 (9)0.0139 (8)0.0016 (6)0.0008 (6)0.0068 (7)
C20.0170 (8)0.0168 (9)0.0126 (9)0.0006 (7)0.0002 (7)0.0016 (7)
N20.0135 (7)0.0221 (8)0.0131 (8)0.0012 (6)0.0026 (6)0.0039 (6)
C110.0133 (7)0.0233 (9)0.0130 (9)0.0026 (7)0.0023 (6)0.0016 (7)
C120.0158 (8)0.0210 (10)0.0172 (9)0.0016 (7)0.0040 (7)0.0015 (7)
C130.0237 (9)0.0315 (11)0.0263 (11)0.0035 (8)0.0028 (8)0.0131 (9)
C140.0306 (10)0.0541 (15)0.0148 (10)0.0004 (10)0.0033 (8)0.0101 (10)
C150.0415 (12)0.0503 (15)0.0171 (11)0.0036 (10)0.0022 (9)0.0071 (10)
C160.0319 (10)0.0281 (11)0.0211 (10)0.0003 (8)0.0010 (8)0.0038 (9)
C210.0173 (8)0.0171 (9)0.0148 (9)0.0024 (7)0.0014 (7)0.0044 (7)
C220.0222 (9)0.0228 (10)0.0185 (9)0.0055 (7)0.0024 (7)0.0037 (8)
C230.0314 (10)0.0215 (10)0.0152 (9)0.0006 (8)0.0031 (8)0.0034 (8)
C240.0258 (9)0.0328 (11)0.0192 (10)0.0007 (8)0.0042 (8)0.0114 (9)
C250.0187 (9)0.0334 (11)0.0302 (11)0.0067 (8)0.0014 (8)0.0137 (9)
C260.0174 (8)0.0271 (11)0.0208 (10)0.0010 (7)0.0037 (7)0.0051 (8)
Geometric parameters (Å, º) top
S1—C21.6730 (18)C14—C151.384 (3)
Cl1—C121.7405 (18)C14—H140.9500
Cl2—C231.750 (2)C15—C161.390 (3)
C1—O11.222 (2)C15—H150.9500
C1—N11.371 (2)C16—H160.9500
C1—C111.508 (2)C21—C221.390 (3)
N1—C21.403 (2)C21—C261.393 (2)
N1—H10.82 (2)C22—C231.397 (3)
C2—N21.343 (2)C22—H220.9500
N2—C211.432 (2)C23—C241.380 (3)
N2—H20.87 (2)C24—C251.393 (3)
C11—C121.395 (3)C24—H240.9500
C11—C161.398 (3)C25—C261.390 (3)
C12—C131.387 (3)C25—H250.9500
C13—C141.383 (3)C26—H260.9500
C13—H130.9500
O1—C1—N1123.32 (16)C14—C15—C16120.6 (2)
O1—C1—C11123.12 (16)C14—C15—H15119.7
N1—C1—C11113.53 (14)C16—C15—H15119.7
C1—N1—C2129.47 (15)C15—C16—C11119.58 (19)
C1—N1—H1116.4 (15)C15—C16—H16120.2
C2—N1—H1114.0 (15)C11—C16—H16120.2
N2—C2—N1115.79 (16)C22—C21—C26120.88 (16)
N2—C2—S1126.58 (14)C22—C21—N2121.81 (16)
N1—C2—S1117.61 (12)C26—C21—N2117.23 (17)
C2—N2—C21126.63 (16)C21—C22—C23118.18 (17)
C2—N2—H2115.1 (14)C21—C22—H22120.9
C21—N2—H2117.9 (14)C23—C22—H22120.9
C12—C11—C16118.95 (16)C24—C23—C22122.22 (18)
C12—C11—C1120.93 (16)C24—C23—Cl2119.12 (14)
C16—C11—C1120.12 (17)C22—C23—Cl2118.67 (15)
C13—C12—C11121.29 (18)C23—C24—C25118.42 (17)
C13—C12—Cl1119.67 (15)C23—C24—H24120.8
C11—C12—Cl1119.03 (13)C25—C24—H24120.8
C14—C13—C12119.10 (19)C26—C25—C24120.93 (18)
C14—C13—H13120.5C26—C25—H25119.5
C12—C13—H13120.5C24—C25—H25119.5
C13—C14—C15120.51 (18)C25—C26—C21119.37 (18)
C13—C14—H14119.7C25—C26—H26120.3
C15—C14—H14119.7C21—C26—H26120.3
O1—C1—N1—C20.7 (3)C13—C14—C15—C160.5 (3)
C11—C1—N1—C2177.61 (17)C14—C15—C16—C110.1 (3)
C1—N1—C2—N25.8 (3)C12—C11—C16—C150.6 (3)
C1—N1—C2—S1172.78 (15)C1—C11—C16—C15179.09 (18)
N1—C2—N2—C21179.01 (16)C2—N2—C21—C2243.5 (3)
S1—C2—N2—C210.5 (3)C2—N2—C21—C26139.65 (19)
O1—C1—C11—C1298.6 (2)C26—C21—C22—C230.6 (3)
N1—C1—C11—C1283.1 (2)N2—C21—C22—C23177.30 (16)
O1—C1—C11—C1681.7 (2)C21—C22—C23—C240.9 (3)
N1—C1—C11—C1696.6 (2)C21—C22—C23—Cl2178.94 (14)
C16—C11—C12—C131.1 (3)C22—C23—C24—C250.5 (3)
C1—C11—C12—C13178.66 (16)Cl2—C23—C24—C25179.42 (15)
C16—C11—C12—Cl1177.91 (14)C23—C24—C25—C260.4 (3)
C1—C11—C12—Cl12.4 (2)C24—C25—C26—C210.8 (3)
C11—C12—C13—C140.7 (3)C22—C21—C26—C250.3 (3)
Cl1—C12—C13—C14178.28 (15)N2—C21—C26—C25176.61 (17)
C12—C13—C14—C150.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.87 (2)1.98 (2)2.701 (2)138.7 (18)
N1—H1···S1i0.82 (2)2.61 (2)3.4009 (16)162.9 (19)
N2—H2···O1ii0.87 (2)2.48 (2)3.2127 (19)142.6 (18)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1.
 

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