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The title compound, C14H8Cl4N2OS, shows the typical geometric parameters of substituted thio­urea derivatives. The dihedral angle formed by the two benzene ring planes is 38.39 (7)°. 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/S160053680603474X/ez2029sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603474X/ez2029Isup2.hkl
Contains datablock I

CCDC reference: 624207

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.028
  • wR factor = 0.071
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
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 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: 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); software used to prepare material for publication: SHELXL97.

1-(2,4-Dichlorobenzoyl)-3-(3,4-dichlorophenyl)thiourea top
Crystal data top
C14H8Cl4N2OSF(000) = 792
Mr = 394.08Dx = 1.628 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.7287 (11) ÅCell parameters from 10746 reflections
b = 9.2935 (6) Åθ = 3.6–25.7°
c = 14.6300 (15) ŵ = 0.87 mm1
β = 111.697 (7)°T = 173 K
V = 1608.0 (2) Å3Block, colourless
Z = 40.43 × 0.30 × 0.28 mm
Data collection top
Stoe IPDSII two-circle
diffractometer
2984 independent reflections
Radiation source: fine-focus sealed tube2703 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1515
Tmin = 0.707, Tmax = 0.794k = 1011
10362 measured reflectionsl = 1715
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)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.071 w = 1/[σ2(Fo2) + (0.0379P)2 + 0.8376P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2984 reflectionsΔρmax = 0.32 e Å3
208 parametersΔρmin = 0.37 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0082 (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
S10.67564 (3)0.41198 (4)0.57312 (3)0.01751 (12)
Cl10.48068 (4)0.81872 (5)0.29436 (4)0.03308 (14)
Cl20.05644 (4)0.67716 (6)0.06373 (4)0.04495 (17)
Cl31.12591 (4)0.40752 (5)0.72486 (3)0.03158 (14)
Cl41.22243 (3)0.19052 (6)0.60743 (4)0.03204 (14)
C10.53897 (13)0.49869 (18)0.28664 (12)0.0175 (3)
O10.60245 (10)0.47027 (16)0.24341 (9)0.0297 (3)
N10.56809 (11)0.48696 (16)0.38697 (10)0.0170 (3)
H10.5202 (18)0.502 (2)0.4088 (17)0.029 (6)*
C20.66861 (13)0.43466 (17)0.45698 (12)0.0150 (3)
N20.75004 (12)0.40355 (16)0.42214 (11)0.0201 (3)
H20.7320 (17)0.415 (2)0.3645 (18)0.020 (5)*
C110.41848 (13)0.54509 (18)0.23138 (11)0.0163 (3)
C120.38381 (13)0.68752 (18)0.23090 (12)0.0176 (3)
C130.27285 (14)0.72927 (19)0.17857 (12)0.0215 (4)
H130.25010.82670.17850.026*
C140.19605 (14)0.6247 (2)0.12645 (13)0.0237 (4)
C150.22781 (14)0.4827 (2)0.12274 (14)0.0263 (4)
H150.17430.41340.08520.032*
C160.33996 (14)0.44369 (19)0.17528 (13)0.0227 (4)
H160.36320.34710.17290.027*
C210.86052 (13)0.34701 (19)0.47421 (12)0.0180 (3)
C220.92976 (13)0.39681 (18)0.56701 (12)0.0184 (3)
H220.90210.46510.60090.022*
C231.04035 (13)0.34474 (18)0.60935 (12)0.0191 (3)
C241.08203 (13)0.24635 (19)0.55924 (13)0.0209 (4)
C251.01149 (15)0.1951 (2)0.46766 (14)0.0256 (4)
H251.03890.12560.43430.031*
C260.90106 (14)0.2453 (2)0.42487 (13)0.0236 (4)
H260.85320.21050.36220.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0138 (2)0.0245 (2)0.0141 (2)0.00157 (14)0.00506 (15)0.00315 (15)
Cl10.0211 (2)0.0235 (2)0.0466 (3)0.00615 (16)0.0031 (2)0.0049 (2)
Cl20.0196 (2)0.0376 (3)0.0549 (4)0.01039 (19)0.0128 (2)0.0086 (2)
Cl30.0182 (2)0.0416 (3)0.0260 (2)0.00446 (17)0.00220 (17)0.00923 (19)
Cl40.0156 (2)0.0468 (3)0.0337 (3)0.01381 (18)0.00907 (18)0.0069 (2)
C10.0159 (7)0.0195 (8)0.0173 (8)0.0000 (6)0.0065 (6)0.0019 (6)
O10.0197 (6)0.0531 (9)0.0187 (6)0.0108 (6)0.0098 (5)0.0036 (6)
N10.0109 (6)0.0254 (8)0.0161 (7)0.0042 (5)0.0064 (6)0.0029 (6)
C20.0129 (7)0.0151 (8)0.0166 (8)0.0006 (6)0.0050 (6)0.0004 (6)
N20.0133 (7)0.0328 (8)0.0137 (8)0.0067 (6)0.0042 (6)0.0028 (6)
C110.0143 (7)0.0227 (8)0.0123 (7)0.0013 (6)0.0054 (6)0.0034 (6)
C120.0169 (8)0.0199 (8)0.0161 (8)0.0030 (6)0.0063 (6)0.0002 (6)
C130.0217 (8)0.0187 (8)0.0219 (9)0.0049 (6)0.0053 (7)0.0034 (7)
C140.0162 (8)0.0266 (9)0.0225 (9)0.0052 (7)0.0003 (7)0.0015 (7)
C150.0195 (8)0.0230 (9)0.0290 (10)0.0009 (7)0.0003 (7)0.0035 (7)
C160.0219 (8)0.0193 (8)0.0240 (9)0.0028 (7)0.0052 (7)0.0009 (7)
C210.0112 (7)0.0248 (9)0.0178 (8)0.0023 (6)0.0052 (6)0.0036 (7)
C220.0143 (8)0.0216 (8)0.0200 (8)0.0021 (6)0.0072 (7)0.0004 (7)
C230.0138 (7)0.0236 (9)0.0183 (8)0.0009 (6)0.0042 (6)0.0016 (7)
C240.0132 (7)0.0274 (9)0.0235 (9)0.0063 (6)0.0083 (6)0.0066 (7)
C250.0243 (9)0.0327 (10)0.0225 (9)0.0083 (7)0.0119 (7)0.0013 (8)
C260.0200 (8)0.0337 (10)0.0163 (8)0.0038 (7)0.0058 (7)0.0023 (7)
Geometric parameters (Å, º) top
S1—C21.6815 (16)C13—C141.389 (3)
Cl1—C121.7385 (16)C13—H130.9500
Cl2—C141.7412 (17)C14—C151.387 (3)
Cl3—C231.7383 (17)C15—C161.396 (2)
Cl4—C241.7403 (16)C15—H150.9500
C1—O11.225 (2)C16—H160.9500
C1—N11.379 (2)C21—C221.396 (2)
C1—C111.508 (2)C21—C261.399 (2)
N1—C21.398 (2)C22—C231.398 (2)
N1—H10.80 (2)C22—H220.9500
C2—N21.345 (2)C23—C241.394 (2)
N2—C211.429 (2)C24—C251.392 (3)
N2—H20.79 (2)C25—C261.391 (2)
C11—C121.395 (2)C25—H250.9500
C11—C161.398 (2)C26—H260.9500
C12—C131.390 (2)
O1—C1—N1124.30 (15)C14—C15—C16118.62 (16)
O1—C1—C11121.27 (15)C14—C15—H15120.7
N1—C1—C11114.40 (13)C16—C15—H15120.7
C1—N1—C2128.35 (14)C15—C16—C11120.78 (16)
C1—N1—H1117.8 (16)C15—C16—H16119.6
C2—N1—H1113.4 (16)C11—C16—H16119.6
N2—C2—N1114.97 (14)C22—C21—C26120.34 (14)
N2—C2—S1126.55 (12)C22—C21—N2122.65 (15)
N1—C2—S1118.45 (11)C26—C21—N2116.84 (15)
C2—N2—C21128.43 (15)C21—C22—C23119.10 (15)
C2—N2—H2114.4 (15)C21—C22—H22120.5
C21—N2—H2117.1 (15)C23—C22—H22120.5
C12—C11—C16118.73 (14)C24—C23—C22120.72 (15)
C12—C11—C1122.09 (15)C24—C23—Cl3120.53 (12)
C16—C11—C1119.12 (15)C22—C23—Cl3118.74 (13)
C13—C12—C11121.53 (15)C25—C24—C23119.68 (15)
C13—C12—Cl1118.30 (13)C25—C24—Cl4119.21 (13)
C11—C12—Cl1120.16 (12)C23—C24—Cl4121.07 (13)
C14—C13—C12118.21 (16)C26—C25—C24120.21 (16)
C14—C13—H13120.9C26—C25—H25119.9
C12—C13—H13120.9C24—C25—H25119.9
C15—C14—C13122.06 (16)C25—C26—C21119.91 (16)
C15—C14—Cl2120.07 (14)C25—C26—H26120.0
C13—C14—Cl2117.87 (14)C21—C26—H26120.0
O1—C1—N1—C24.0 (3)Cl2—C14—C15—C16178.87 (15)
C11—C1—N1—C2173.73 (15)C14—C15—C16—C110.7 (3)
C1—N1—C2—N26.1 (2)C12—C11—C16—C152.5 (3)
C1—N1—C2—S1172.09 (14)C1—C11—C16—C15179.69 (16)
N1—C2—N2—C21179.06 (16)C2—N2—C21—C2243.7 (3)
S1—C2—N2—C211.0 (3)C2—N2—C21—C26141.01 (18)
O1—C1—C11—C12105.6 (2)C26—C21—C22—C230.7 (2)
N1—C1—C11—C1276.6 (2)N2—C21—C22—C23174.50 (15)
O1—C1—C11—C1671.6 (2)C21—C22—C23—C241.1 (2)
N1—C1—C11—C16106.29 (18)C21—C22—C23—Cl3179.95 (13)
C16—C11—C12—C132.0 (2)C22—C23—C24—C252.5 (3)
C1—C11—C12—C13179.10 (15)Cl3—C23—C24—C25178.69 (14)
C16—C11—C12—Cl1176.54 (13)C22—C23—C24—Cl4175.44 (13)
C1—C11—C12—Cl10.6 (2)Cl3—C23—C24—Cl43.4 (2)
C11—C12—C13—C140.3 (2)C23—C24—C25—C262.1 (3)
Cl1—C12—C13—C14178.84 (14)Cl4—C24—C25—C26175.87 (14)
C12—C13—C14—C152.2 (3)C24—C25—C26—C210.3 (3)
C12—C13—C14—Cl2178.37 (13)C22—C21—C26—C251.1 (3)
C13—C14—C15—C161.7 (3)N2—C21—C26—C25174.39 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1i0.80 (2)2.72 (2)3.4910 (14)162 (2)
N2—H2···O10.79 (2)1.99 (2)2.6681 (19)143 (2)
Symmetry code: (i) x+1, y+1, z+1.
 

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