The title compound, C
14H
8Cl
4N
2OS, 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
CCDC reference: 624207
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.028
- wR factor = 0.071
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
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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
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
C14H8Cl4N2OS | F(000) = 792 |
Mr = 394.08 | Dx = 1.628 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.7287 (11) Å | Cell parameters from 10746 reflections |
b = 9.2935 (6) Å | θ = 3.6–25.7° |
c = 14.6300 (15) Å | µ = 0.87 mm−1 |
β = 111.697 (7)° | T = 173 K |
V = 1608.0 (2) Å3 | Block, colourless |
Z = 4 | 0.43 × 0.30 × 0.28 mm |
Data collection top
Stoe IPDSII two-circle diffractometer | 2984 independent reflections |
Radiation source: fine-focus sealed tube | 2703 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 25.6°, θmin = 3.6° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −15→15 |
Tmin = 0.707, Tmax = 0.794 | k = −10→11 |
10362 measured reflections | l = −17→15 |
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)] = 0.028 | H 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 reflections | Δρmax = 0.32 e Å−3 |
208 parameters | Δρmin = −0.37 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
S1 | 0.67564 (3) | 0.41198 (4) | 0.57312 (3) | 0.01751 (12) | |
Cl1 | 0.48068 (4) | 0.81872 (5) | 0.29436 (4) | 0.03308 (14) | |
Cl2 | 0.05644 (4) | 0.67716 (6) | 0.06373 (4) | 0.04495 (17) | |
Cl3 | 1.12591 (4) | 0.40752 (5) | 0.72486 (3) | 0.03158 (14) | |
Cl4 | 1.22243 (3) | 0.19052 (6) | 0.60743 (4) | 0.03204 (14) | |
C1 | 0.53897 (13) | 0.49869 (18) | 0.28664 (12) | 0.0175 (3) | |
O1 | 0.60245 (10) | 0.47027 (16) | 0.24341 (9) | 0.0297 (3) | |
N1 | 0.56809 (11) | 0.48696 (16) | 0.38697 (10) | 0.0170 (3) | |
H1 | 0.5202 (18) | 0.502 (2) | 0.4088 (17) | 0.029 (6)* | |
C2 | 0.66861 (13) | 0.43466 (17) | 0.45698 (12) | 0.0150 (3) | |
N2 | 0.75004 (12) | 0.40355 (16) | 0.42214 (11) | 0.0201 (3) | |
H2 | 0.7320 (17) | 0.415 (2) | 0.3645 (18) | 0.020 (5)* | |
C11 | 0.41848 (13) | 0.54509 (18) | 0.23138 (11) | 0.0163 (3) | |
C12 | 0.38381 (13) | 0.68752 (18) | 0.23090 (12) | 0.0176 (3) | |
C13 | 0.27285 (14) | 0.72927 (19) | 0.17857 (12) | 0.0215 (4) | |
H13 | 0.2501 | 0.8267 | 0.1785 | 0.026* | |
C14 | 0.19605 (14) | 0.6247 (2) | 0.12645 (13) | 0.0237 (4) | |
C15 | 0.22781 (14) | 0.4827 (2) | 0.12274 (14) | 0.0263 (4) | |
H15 | 0.1743 | 0.4134 | 0.0852 | 0.032* | |
C16 | 0.33996 (14) | 0.44369 (19) | 0.17528 (13) | 0.0227 (4) | |
H16 | 0.3632 | 0.3471 | 0.1729 | 0.027* | |
C21 | 0.86052 (13) | 0.34701 (19) | 0.47421 (12) | 0.0180 (3) | |
C22 | 0.92976 (13) | 0.39681 (18) | 0.56701 (12) | 0.0184 (3) | |
H22 | 0.9021 | 0.4651 | 0.6009 | 0.022* | |
C23 | 1.04035 (13) | 0.34474 (18) | 0.60935 (12) | 0.0191 (3) | |
C24 | 1.08203 (13) | 0.24635 (19) | 0.55924 (13) | 0.0209 (4) | |
C25 | 1.01149 (15) | 0.1951 (2) | 0.46766 (14) | 0.0256 (4) | |
H25 | 1.0389 | 0.1256 | 0.4343 | 0.031* | |
C26 | 0.90106 (14) | 0.2453 (2) | 0.42487 (13) | 0.0236 (4) | |
H26 | 0.8532 | 0.2105 | 0.3622 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0138 (2) | 0.0245 (2) | 0.0141 (2) | 0.00157 (14) | 0.00506 (15) | 0.00315 (15) |
Cl1 | 0.0211 (2) | 0.0235 (2) | 0.0466 (3) | −0.00615 (16) | 0.0031 (2) | −0.0049 (2) |
Cl2 | 0.0196 (2) | 0.0376 (3) | 0.0549 (4) | 0.01039 (19) | −0.0128 (2) | −0.0086 (2) |
Cl3 | 0.0182 (2) | 0.0416 (3) | 0.0260 (2) | 0.00446 (17) | −0.00220 (17) | −0.00923 (19) |
Cl4 | 0.0156 (2) | 0.0468 (3) | 0.0337 (3) | 0.01381 (18) | 0.00907 (18) | 0.0069 (2) |
C1 | 0.0159 (7) | 0.0195 (8) | 0.0173 (8) | 0.0000 (6) | 0.0065 (6) | 0.0019 (6) |
O1 | 0.0197 (6) | 0.0531 (9) | 0.0187 (6) | 0.0108 (6) | 0.0098 (5) | 0.0036 (6) |
N1 | 0.0109 (6) | 0.0254 (8) | 0.0161 (7) | 0.0042 (5) | 0.0064 (6) | 0.0029 (6) |
C2 | 0.0129 (7) | 0.0151 (8) | 0.0166 (8) | −0.0006 (6) | 0.0050 (6) | 0.0004 (6) |
N2 | 0.0133 (7) | 0.0328 (8) | 0.0137 (8) | 0.0067 (6) | 0.0042 (6) | 0.0028 (6) |
C11 | 0.0143 (7) | 0.0227 (8) | 0.0123 (7) | 0.0013 (6) | 0.0054 (6) | 0.0034 (6) |
C12 | 0.0169 (8) | 0.0199 (8) | 0.0161 (8) | −0.0030 (6) | 0.0063 (6) | 0.0002 (6) |
C13 | 0.0217 (8) | 0.0187 (8) | 0.0219 (9) | 0.0049 (6) | 0.0053 (7) | 0.0034 (7) |
C14 | 0.0162 (8) | 0.0266 (9) | 0.0225 (9) | 0.0052 (7) | 0.0003 (7) | 0.0015 (7) |
C15 | 0.0195 (8) | 0.0230 (9) | 0.0290 (10) | −0.0009 (7) | 0.0003 (7) | −0.0035 (7) |
C16 | 0.0219 (8) | 0.0193 (8) | 0.0240 (9) | 0.0028 (7) | 0.0052 (7) | −0.0009 (7) |
C21 | 0.0112 (7) | 0.0248 (9) | 0.0178 (8) | 0.0023 (6) | 0.0052 (6) | 0.0036 (7) |
C22 | 0.0143 (8) | 0.0216 (8) | 0.0200 (8) | 0.0021 (6) | 0.0072 (7) | −0.0004 (7) |
C23 | 0.0138 (7) | 0.0236 (9) | 0.0183 (8) | −0.0009 (6) | 0.0042 (6) | 0.0016 (7) |
C24 | 0.0132 (7) | 0.0274 (9) | 0.0235 (9) | 0.0063 (6) | 0.0083 (6) | 0.0066 (7) |
C25 | 0.0243 (9) | 0.0327 (10) | 0.0225 (9) | 0.0083 (7) | 0.0119 (7) | −0.0013 (8) |
C26 | 0.0200 (8) | 0.0337 (10) | 0.0163 (8) | 0.0038 (7) | 0.0058 (7) | −0.0023 (7) |
Geometric parameters (Å, º) top
S1—C2 | 1.6815 (16) | C13—C14 | 1.389 (3) |
Cl1—C12 | 1.7385 (16) | C13—H13 | 0.9500 |
Cl2—C14 | 1.7412 (17) | C14—C15 | 1.387 (3) |
Cl3—C23 | 1.7383 (17) | C15—C16 | 1.396 (2) |
Cl4—C24 | 1.7403 (16) | C15—H15 | 0.9500 |
C1—O1 | 1.225 (2) | C16—H16 | 0.9500 |
C1—N1 | 1.379 (2) | C21—C22 | 1.396 (2) |
C1—C11 | 1.508 (2) | C21—C26 | 1.399 (2) |
N1—C2 | 1.398 (2) | C22—C23 | 1.398 (2) |
N1—H1 | 0.80 (2) | C22—H22 | 0.9500 |
C2—N2 | 1.345 (2) | C23—C24 | 1.394 (2) |
N2—C21 | 1.429 (2) | C24—C25 | 1.392 (3) |
N2—H2 | 0.79 (2) | C25—C26 | 1.391 (2) |
C11—C12 | 1.395 (2) | C25—H25 | 0.9500 |
C11—C16 | 1.398 (2) | C26—H26 | 0.9500 |
C12—C13 | 1.390 (2) | | |
| | | |
O1—C1—N1 | 124.30 (15) | C14—C15—C16 | 118.62 (16) |
O1—C1—C11 | 121.27 (15) | C14—C15—H15 | 120.7 |
N1—C1—C11 | 114.40 (13) | C16—C15—H15 | 120.7 |
C1—N1—C2 | 128.35 (14) | C15—C16—C11 | 120.78 (16) |
C1—N1—H1 | 117.8 (16) | C15—C16—H16 | 119.6 |
C2—N1—H1 | 113.4 (16) | C11—C16—H16 | 119.6 |
N2—C2—N1 | 114.97 (14) | C22—C21—C26 | 120.34 (14) |
N2—C2—S1 | 126.55 (12) | C22—C21—N2 | 122.65 (15) |
N1—C2—S1 | 118.45 (11) | C26—C21—N2 | 116.84 (15) |
C2—N2—C21 | 128.43 (15) | C21—C22—C23 | 119.10 (15) |
C2—N2—H2 | 114.4 (15) | C21—C22—H22 | 120.5 |
C21—N2—H2 | 117.1 (15) | C23—C22—H22 | 120.5 |
C12—C11—C16 | 118.73 (14) | C24—C23—C22 | 120.72 (15) |
C12—C11—C1 | 122.09 (15) | C24—C23—Cl3 | 120.53 (12) |
C16—C11—C1 | 119.12 (15) | C22—C23—Cl3 | 118.74 (13) |
C13—C12—C11 | 121.53 (15) | C25—C24—C23 | 119.68 (15) |
C13—C12—Cl1 | 118.30 (13) | C25—C24—Cl4 | 119.21 (13) |
C11—C12—Cl1 | 120.16 (12) | C23—C24—Cl4 | 121.07 (13) |
C14—C13—C12 | 118.21 (16) | C26—C25—C24 | 120.21 (16) |
C14—C13—H13 | 120.9 | C26—C25—H25 | 119.9 |
C12—C13—H13 | 120.9 | C24—C25—H25 | 119.9 |
C15—C14—C13 | 122.06 (16) | C25—C26—C21 | 119.91 (16) |
C15—C14—Cl2 | 120.07 (14) | C25—C26—H26 | 120.0 |
C13—C14—Cl2 | 117.87 (14) | C21—C26—H26 | 120.0 |
| | | |
O1—C1—N1—C2 | −4.0 (3) | Cl2—C14—C15—C16 | −178.87 (15) |
C11—C1—N1—C2 | 173.73 (15) | C14—C15—C16—C11 | 0.7 (3) |
C1—N1—C2—N2 | 6.1 (2) | C12—C11—C16—C15 | −2.5 (3) |
C1—N1—C2—S1 | −172.09 (14) | C1—C11—C16—C15 | −179.69 (16) |
N1—C2—N2—C21 | −179.06 (16) | C2—N2—C21—C22 | −43.7 (3) |
S1—C2—N2—C21 | −1.0 (3) | C2—N2—C21—C26 | 141.01 (18) |
O1—C1—C11—C12 | −105.6 (2) | C26—C21—C22—C23 | 0.7 (2) |
N1—C1—C11—C12 | 76.6 (2) | N2—C21—C22—C23 | −174.50 (15) |
O1—C1—C11—C16 | 71.6 (2) | C21—C22—C23—C24 | 1.1 (2) |
N1—C1—C11—C16 | −106.29 (18) | C21—C22—C23—Cl3 | 179.95 (13) |
C16—C11—C12—C13 | 2.0 (2) | C22—C23—C24—C25 | −2.5 (3) |
C1—C11—C12—C13 | 179.10 (15) | Cl3—C23—C24—C25 | 178.69 (14) |
C16—C11—C12—Cl1 | −176.54 (13) | C22—C23—C24—Cl4 | 175.44 (13) |
C1—C11—C12—Cl1 | 0.6 (2) | Cl3—C23—C24—Cl4 | −3.4 (2) |
C11—C12—C13—C14 | 0.3 (2) | C23—C24—C25—C26 | 2.1 (3) |
Cl1—C12—C13—C14 | 178.84 (14) | Cl4—C24—C25—C26 | −175.87 (14) |
C12—C13—C14—C15 | −2.2 (3) | C24—C25—C26—C21 | −0.3 (3) |
C12—C13—C14—Cl2 | 178.37 (13) | C22—C21—C26—C25 | −1.1 (3) |
C13—C14—C15—C16 | 1.7 (3) | N2—C21—C26—C25 | 174.39 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.80 (2) | 2.72 (2) | 3.4910 (14) | 162 (2) |
N2—H2···O1 | 0.79 (2) | 1.99 (2) | 2.6681 (19) | 143 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |