The title compound, C
14H
8Cl
4N
2OS, shows the typical geometric parameters of substituted thiourea derivatives. The crystal packing is characterized by N—H
O and N—H
S hydrogen bonds.
Supporting information
CCDC reference: 640502
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C)= 0.003 Å
- R factor = 0.036
- wR factor = 0.100
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
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No errors found in this datablock
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: PLATON (Spek 2003) and XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
1-(2,6-Dichlorobenzoyl)-3-(3,4-dichlorophenyl)thiourea
top
Crystal data top
C14H8Cl4N2OS | Z = 2 |
Mr = 394.08 | F(000) = 396 |
Triclinic, P1 | Dx = 1.660 Mg m−3 |
Hall symbol: -P 1 | Melting point: 401 K |
a = 6.9755 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.0363 (14) Å | Cell parameters from 6274 reflections |
c = 11.0603 (15) Å | θ = 3.6–25.8° |
α = 101.72 (1)° | µ = 0.88 mm−1 |
β = 94.826 (11)° | T = 173 K |
γ = 106.931 (10)° | Block, colourless |
V = 788.19 (18) Å3 | 0.36 × 0.33 × 0.32 mm |
Data collection top
Stoe IPDS-II two-circle diffractometer | 2941 independent reflections |
Radiation source: fine-focus sealed tube | 2721 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ω scans | θmax = 25.6°, θmin = 3.6° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −8→8 |
Tmin = 0.741, Tmax = 0.760 | k = −13→12 |
6274 measured reflections | l = −13→13 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0649P)2 + 0.2763P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2941 reflections | Δρmax = 0.45 e Å−3 |
200 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.035 (4) |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.70543 (7) | 0.37573 (5) | 0.40267 (4) | 0.01979 (16) | |
Cl1 | 0.78855 (8) | 0.79392 (5) | 0.85575 (5) | 0.02886 (17) | |
Cl2 | 1.13628 (8) | 0.41293 (5) | 0.83649 (5) | 0.02774 (17) | |
Cl3 | 0.25687 (8) | −0.12720 (5) | 0.29435 (5) | 0.02916 (17) | |
Cl4 | −0.18163 (7) | −0.09846 (5) | 0.23686 (5) | 0.02887 (17) | |
C1 | 0.7915 (3) | 0.51584 (19) | 0.77223 (18) | 0.0194 (4) | |
O1 | 0.6427 (2) | 0.46950 (16) | 0.81852 (14) | 0.0306 (4) | |
N1 | 0.8024 (2) | 0.48559 (15) | 0.64598 (14) | 0.0174 (3) | |
H1 | 0.9154 | 0.5284 | 0.6230 | 0.021* | |
C2 | 0.6555 (3) | 0.39515 (17) | 0.55011 (17) | 0.0159 (4) | |
N2 | 0.4821 (2) | 0.33134 (15) | 0.58500 (15) | 0.0182 (3) | |
H2 | 0.4655 | 0.3544 | 0.6634 | 0.022* | |
C11 | 0.9849 (3) | 0.61450 (18) | 0.84872 (16) | 0.0185 (4) | |
C12 | 0.9994 (3) | 0.7453 (2) | 0.89054 (18) | 0.0201 (4) | |
C13 | 1.1768 (3) | 0.8375 (2) | 0.9590 (2) | 0.0260 (5) | |
H13 | 1.1850 | 0.9265 | 0.9854 | 0.031* | |
C14 | 1.3430 (3) | 0.7964 (2) | 0.9881 (2) | 0.0275 (5) | |
H14 | 1.4652 | 0.8587 | 1.0341 | 0.033* | |
C15 | 1.3331 (3) | 0.6669 (2) | 0.95130 (19) | 0.0240 (4) | |
H15 | 1.4462 | 0.6398 | 0.9728 | 0.029* | |
C16 | 1.1530 (3) | 0.57662 (19) | 0.88169 (18) | 0.0197 (4) | |
C21 | 0.3220 (3) | 0.22758 (19) | 0.50170 (17) | 0.0174 (4) | |
C22 | 0.3600 (3) | 0.11453 (19) | 0.44397 (18) | 0.0183 (4) | |
H22 | 0.4916 | 0.1068 | 0.4589 | 0.022* | |
C23 | 0.2052 (3) | 0.01270 (18) | 0.36432 (18) | 0.0185 (4) | |
C24 | 0.0106 (3) | 0.02433 (19) | 0.34264 (18) | 0.0193 (4) | |
C25 | −0.0272 (3) | 0.1359 (2) | 0.40262 (18) | 0.0208 (4) | |
H25 | −0.1594 | 0.1431 | 0.3888 | 0.025* | |
C26 | 0.1275 (3) | 0.23850 (19) | 0.48349 (19) | 0.0198 (4) | |
H26 | 0.1007 | 0.3145 | 0.5254 | 0.024* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0181 (3) | 0.0212 (3) | 0.0150 (3) | 0.00013 (19) | 0.00198 (18) | 0.00219 (19) |
Cl1 | 0.0252 (3) | 0.0298 (3) | 0.0355 (3) | 0.0116 (2) | 0.0061 (2) | 0.0116 (2) |
Cl2 | 0.0286 (3) | 0.0206 (3) | 0.0333 (3) | 0.0075 (2) | 0.0054 (2) | 0.0050 (2) |
Cl3 | 0.0278 (3) | 0.0220 (3) | 0.0326 (3) | 0.0090 (2) | −0.0005 (2) | −0.0041 (2) |
Cl4 | 0.0215 (3) | 0.0252 (3) | 0.0298 (3) | −0.0014 (2) | −0.0090 (2) | 0.0023 (2) |
C1 | 0.0164 (9) | 0.0205 (10) | 0.0187 (9) | 0.0026 (7) | 0.0017 (7) | 0.0039 (7) |
O1 | 0.0220 (8) | 0.0383 (9) | 0.0199 (7) | −0.0060 (6) | 0.0059 (6) | 0.0026 (6) |
N1 | 0.0135 (7) | 0.0179 (8) | 0.0153 (8) | −0.0018 (6) | 0.0009 (6) | 0.0024 (6) |
C2 | 0.0154 (9) | 0.0128 (9) | 0.0179 (9) | 0.0033 (7) | −0.0003 (7) | 0.0028 (7) |
N2 | 0.0154 (8) | 0.0178 (8) | 0.0166 (8) | 0.0000 (6) | 0.0024 (6) | 0.0009 (6) |
C11 | 0.0169 (9) | 0.0210 (10) | 0.0127 (9) | −0.0010 (8) | 0.0027 (7) | 0.0029 (7) |
C12 | 0.0204 (10) | 0.0233 (10) | 0.0167 (9) | 0.0064 (8) | 0.0040 (7) | 0.0053 (7) |
C13 | 0.0258 (11) | 0.0199 (10) | 0.0249 (10) | 0.0001 (8) | 0.0023 (8) | 0.0002 (8) |
C14 | 0.0202 (10) | 0.0296 (12) | 0.0232 (10) | −0.0015 (9) | −0.0018 (8) | 0.0010 (9) |
C15 | 0.0183 (10) | 0.0307 (11) | 0.0209 (10) | 0.0041 (8) | 0.0017 (8) | 0.0074 (8) |
C16 | 0.0220 (9) | 0.0184 (10) | 0.0171 (9) | 0.0041 (8) | 0.0052 (7) | 0.0032 (7) |
C21 | 0.0150 (9) | 0.0176 (9) | 0.0162 (9) | −0.0006 (7) | 0.0007 (7) | 0.0051 (7) |
C22 | 0.0128 (8) | 0.0201 (10) | 0.0208 (9) | 0.0030 (7) | 0.0009 (7) | 0.0064 (8) |
C23 | 0.0197 (9) | 0.0158 (9) | 0.0189 (9) | 0.0032 (7) | 0.0028 (7) | 0.0051 (7) |
C24 | 0.0161 (9) | 0.0192 (10) | 0.0186 (9) | −0.0010 (7) | −0.0008 (7) | 0.0062 (7) |
C25 | 0.0136 (9) | 0.0243 (10) | 0.0246 (10) | 0.0042 (8) | 0.0021 (8) | 0.0088 (8) |
C26 | 0.0174 (9) | 0.0174 (10) | 0.0245 (10) | 0.0044 (7) | 0.0050 (8) | 0.0056 (8) |
Geometric parameters (Å, º) top
S1—C2 | 1.6804 (19) | C13—C14 | 1.398 (3) |
Cl1—C12 | 1.746 (2) | C13—H13 | 0.9500 |
Cl2—C16 | 1.740 (2) | C14—C15 | 1.383 (3) |
Cl3—C23 | 1.7316 (19) | C14—H14 | 0.9500 |
Cl4—C24 | 1.743 (2) | C15—C16 | 1.400 (3) |
C1—O1 | 1.219 (2) | C15—H15 | 0.9500 |
C1—N1 | 1.382 (3) | C21—C22 | 1.390 (3) |
C1—C11 | 1.517 (3) | C21—C26 | 1.398 (3) |
N1—C2 | 1.401 (2) | C22—C23 | 1.392 (3) |
N1—H1 | 0.8800 | C22—H22 | 0.9500 |
C2—N2 | 1.342 (2) | C23—C24 | 1.406 (3) |
N2—C21 | 1.435 (2) | C24—C25 | 1.383 (3) |
N2—H2 | 0.8800 | C25—C26 | 1.400 (3) |
C11—C12 | 1.395 (3) | C25—H25 | 0.9500 |
C11—C16 | 1.399 (3) | C26—H26 | 0.9500 |
C12—C13 | 1.391 (3) | | |
| | | |
O1—C1—N1 | 124.23 (18) | C14—C15—C16 | 118.62 (19) |
O1—C1—C11 | 122.86 (17) | C14—C15—H15 | 120.7 |
N1—C1—C11 | 112.90 (16) | C16—C15—H15 | 120.7 |
C1—N1—C2 | 127.91 (16) | C15—C16—C11 | 121.60 (18) |
C1—N1—H1 | 116.0 | C15—C16—Cl2 | 119.31 (16) |
C2—N1—H1 | 116.0 | C11—C16—Cl2 | 119.08 (15) |
N2—C2—N1 | 115.98 (16) | C22—C21—C26 | 120.53 (17) |
N2—C2—S1 | 125.13 (14) | C22—C21—N2 | 119.49 (16) |
N1—C2—S1 | 118.88 (13) | C26—C21—N2 | 119.92 (17) |
C2—N2—C21 | 123.73 (16) | C21—C22—C23 | 119.94 (17) |
C2—N2—H2 | 118.1 | C21—C22—H22 | 120.0 |
C21—N2—H2 | 118.1 | C23—C22—H22 | 120.0 |
C12—C11—C16 | 117.91 (18) | C22—C23—C24 | 119.90 (18) |
C12—C11—C1 | 121.05 (17) | C22—C23—Cl3 | 118.87 (15) |
C16—C11—C1 | 121.03 (17) | C24—C23—Cl3 | 121.23 (15) |
C13—C12—C11 | 121.76 (18) | C25—C24—C23 | 119.82 (18) |
C13—C12—Cl1 | 119.44 (16) | C25—C24—Cl4 | 119.60 (15) |
C11—C12—Cl1 | 118.80 (15) | C23—C24—Cl4 | 120.54 (15) |
C12—C13—C14 | 118.7 (2) | C24—C25—C26 | 120.59 (18) |
C12—C13—H13 | 120.7 | C24—C25—H25 | 119.7 |
C14—C13—H13 | 120.7 | C26—C25—H25 | 119.7 |
C15—C14—C13 | 121.41 (19) | C21—C26—C25 | 119.17 (18) |
C15—C14—H14 | 119.3 | C21—C26—H26 | 120.4 |
C13—C14—H14 | 119.3 | C25—C26—H26 | 120.4 |
| | | |
O1—C1—N1—C2 | −3.2 (3) | C12—C11—C16—C15 | −1.9 (3) |
C11—C1—N1—C2 | 177.25 (17) | C1—C11—C16—C15 | 179.41 (17) |
C1—N1—C2—N2 | 0.9 (3) | C12—C11—C16—Cl2 | 177.39 (13) |
C1—N1—C2—S1 | −179.89 (15) | C1—C11—C16—Cl2 | −1.4 (2) |
N1—C2—N2—C21 | −174.46 (16) | C2—N2—C21—C22 | 61.2 (2) |
S1—C2—N2—C21 | 6.4 (3) | C2—N2—C21—C26 | −121.6 (2) |
O1—C1—C11—C12 | −78.0 (3) | C26—C21—C22—C23 | 2.0 (3) |
N1—C1—C11—C12 | 101.6 (2) | N2—C21—C22—C23 | 179.17 (16) |
O1—C1—C11—C16 | 100.7 (2) | C21—C22—C23—C24 | −0.1 (3) |
N1—C1—C11—C16 | −79.7 (2) | C21—C22—C23—Cl3 | −179.70 (14) |
C16—C11—C12—C13 | 2.4 (3) | C22—C23—C24—C25 | −1.3 (3) |
C1—C11—C12—C13 | −178.89 (18) | Cl3—C23—C24—C25 | 178.24 (15) |
C16—C11—C12—Cl1 | −177.58 (14) | C22—C23—C24—Cl4 | 176.56 (14) |
C1—C11—C12—Cl1 | 1.2 (2) | Cl3—C23—C24—Cl4 | −3.9 (2) |
C11—C12—C13—C14 | −1.2 (3) | C23—C24—C25—C26 | 0.9 (3) |
Cl1—C12—C13—C14 | 178.76 (16) | Cl4—C24—C25—C26 | −176.96 (15) |
C12—C13—C14—C15 | −0.6 (3) | C22—C21—C26—C25 | −2.3 (3) |
C13—C14—C15—C16 | 1.1 (3) | N2—C21—C26—C25 | −179.52 (16) |
C14—C15—C16—C11 | 0.2 (3) | C24—C25—C26—C21 | 0.9 (3) |
C14—C15—C16—Cl2 | −179.07 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.88 | 2.61 | 3.4647 (17) | 164 |
N2—H2···O1 | 0.88 | 1.98 | 2.678 (2) | 135 |
Symmetry code: (i) −x+2, −y+1, −z+1. |