The chlorophenyl and benzoyl groups in the title compound, C
14H
10Cl
2N
2OS, are
cis and
trans, respectively, with respect to the C=S bond. The crystal packing is characterized by N—H
O, N—H
S and N—H
Cl hydrogen bonds.
Supporting information
CCDC reference: 610764
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.040
- wR factor = 0.093
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Datablock: rauf5
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O1 .. 3.20 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. CL1 .. 2.98 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); 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-(3-Chlorobenzoyl)-3-(3-chlorophenyl)thiourea
top
Crystal data top
C14H10Cl2N2OS | Dx = 1.547 Mg m−3 |
Mr = 325.20 | Melting point: 406 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 3.9523 (4) Å | Cell parameters from 8056 reflections |
b = 23.762 (3) Å | θ = 3.7–25.8° |
c = 14.8970 (14) Å | µ = 0.61 mm−1 |
β = 93.887 (8)° | T = 173 K |
V = 1395.8 (3) Å3 | Needle, colourless |
Z = 4 | 0.34 × 0.14 × 0.13 mm |
F(000) = 664 | |
Data collection top
Stoe IPDS-II two-circle diffractometer | 2591 independent reflections |
Radiation source: fine-focus sealed tube | 2024 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.080 |
ω scans | θmax = 25.6°, θmin = 3.7° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −4→4 |
Tmin = 0.820, Tmax = 0.925 | k = −28→24 |
8762 measured reflections | l = −17→17 |
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)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0481P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.001 |
2591 reflections | Δρmax = 0.26 e Å−3 |
190 parameters | Δρmin = −0.36 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: 0.0073 (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 | x | y | z | Uiso*/Ueq | |
S1 | 0.36245 (15) | 0.53607 (3) | 0.37741 (4) | 0.01765 (17) | |
Cl1 | 0.89713 (16) | 0.70790 (3) | 0.88987 (4) | 0.02554 (19) | |
Cl2 | 0.75379 (18) | 0.56070 (3) | 0.05065 (4) | 0.0317 (2) | |
C1 | 0.8148 (6) | 0.64113 (12) | 0.55670 (17) | 0.0197 (5) | |
O1 | 0.8382 (5) | 0.68843 (9) | 0.52509 (12) | 0.0312 (5) | |
N1 | 0.6793 (5) | 0.59560 (10) | 0.50833 (13) | 0.0169 (4) | |
H1 | 0.654 (8) | 0.5624 (16) | 0.538 (2) | 0.030 (8)* | |
C2 | 0.5663 (6) | 0.59396 (11) | 0.41661 (15) | 0.0148 (5) | |
N2 | 0.6267 (5) | 0.64010 (10) | 0.36916 (14) | 0.0182 (5) | |
H2 | 0.700 (7) | 0.6713 (15) | 0.398 (2) | 0.027 (8)* | |
C11 | 0.9269 (6) | 0.62820 (11) | 0.65322 (16) | 0.0167 (5) | |
C12 | 0.8748 (6) | 0.66952 (11) | 0.71755 (16) | 0.0172 (5) | |
H12 | 0.7735 | 0.7046 | 0.7007 | 0.021* | |
C13 | 0.9756 (6) | 0.65785 (12) | 0.80722 (16) | 0.0188 (5) | |
C14 | 1.1340 (6) | 0.60757 (12) | 0.83280 (16) | 0.0205 (6) | |
H14 | 1.2005 | 0.6006 | 0.8943 | 0.025* | |
C15 | 1.1939 (6) | 0.56780 (12) | 0.76780 (17) | 0.0207 (5) | |
H15 | 1.3074 | 0.5337 | 0.7844 | 0.025* | |
C16 | 1.0876 (6) | 0.57770 (11) | 0.67772 (16) | 0.0179 (5) | |
H16 | 1.1247 | 0.5501 | 0.6333 | 0.021* | |
C21 | 0.5616 (6) | 0.64577 (12) | 0.27316 (16) | 0.0167 (5) | |
C22 | 0.6793 (6) | 0.60472 (12) | 0.21585 (16) | 0.0186 (5) | |
H22 | 0.7973 | 0.5725 | 0.2391 | 0.022* | |
C23 | 0.6189 (6) | 0.61247 (12) | 0.12386 (16) | 0.0194 (5) | |
C24 | 0.4525 (6) | 0.66035 (13) | 0.08841 (17) | 0.0229 (6) | |
H24 | 0.4160 | 0.6651 | 0.0252 | 0.027* | |
C25 | 0.3421 (6) | 0.70068 (12) | 0.14657 (17) | 0.0222 (6) | |
H25 | 0.2311 | 0.7335 | 0.1231 | 0.027* | |
C26 | 0.3924 (6) | 0.69351 (12) | 0.23986 (17) | 0.0205 (6) | |
H26 | 0.3122 | 0.7209 | 0.2798 | 0.025* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0198 (3) | 0.0169 (3) | 0.0157 (3) | −0.0033 (2) | −0.0028 (2) | 0.0012 (3) |
Cl1 | 0.0358 (4) | 0.0283 (4) | 0.0125 (3) | 0.0061 (3) | 0.0013 (2) | −0.0038 (3) |
Cl2 | 0.0403 (4) | 0.0368 (4) | 0.0184 (3) | 0.0001 (3) | 0.0054 (3) | −0.0087 (3) |
C1 | 0.0237 (13) | 0.0203 (15) | 0.0151 (12) | −0.0025 (10) | 0.0026 (9) | −0.0009 (11) |
O1 | 0.0570 (12) | 0.0210 (11) | 0.0145 (10) | −0.0099 (9) | −0.0046 (8) | 0.0011 (8) |
N1 | 0.0250 (10) | 0.0160 (12) | 0.0095 (10) | −0.0018 (9) | −0.0005 (8) | 0.0006 (9) |
C2 | 0.0145 (11) | 0.0189 (13) | 0.0114 (11) | 0.0019 (9) | 0.0027 (8) | −0.0006 (10) |
N2 | 0.0279 (11) | 0.0173 (12) | 0.0091 (10) | −0.0028 (9) | −0.0018 (8) | −0.0003 (8) |
C11 | 0.0174 (11) | 0.0186 (14) | 0.0140 (12) | −0.0049 (10) | 0.0001 (9) | 0.0000 (10) |
C12 | 0.0196 (11) | 0.0177 (14) | 0.0143 (12) | 0.0000 (10) | 0.0005 (9) | 0.0021 (10) |
C13 | 0.0207 (12) | 0.0222 (14) | 0.0137 (12) | −0.0024 (10) | 0.0022 (9) | −0.0032 (10) |
C14 | 0.0251 (13) | 0.0238 (15) | 0.0120 (12) | −0.0031 (11) | −0.0033 (9) | 0.0026 (10) |
C15 | 0.0233 (12) | 0.0157 (14) | 0.0223 (13) | 0.0010 (10) | −0.0039 (10) | 0.0036 (11) |
C16 | 0.0170 (11) | 0.0208 (14) | 0.0160 (12) | −0.0027 (10) | 0.0018 (9) | −0.0024 (10) |
C21 | 0.0168 (11) | 0.0223 (15) | 0.0106 (12) | −0.0068 (10) | −0.0028 (9) | 0.0045 (10) |
C22 | 0.0210 (12) | 0.0205 (14) | 0.0142 (12) | −0.0026 (10) | 0.0000 (9) | 0.0019 (10) |
C23 | 0.0212 (12) | 0.0218 (14) | 0.0155 (12) | −0.0067 (10) | 0.0025 (9) | −0.0043 (10) |
C24 | 0.0227 (12) | 0.0307 (16) | 0.0145 (12) | −0.0063 (11) | −0.0034 (10) | 0.0063 (11) |
C25 | 0.0230 (12) | 0.0216 (15) | 0.0210 (13) | −0.0029 (11) | −0.0063 (10) | 0.0060 (11) |
C26 | 0.0215 (12) | 0.0203 (15) | 0.0194 (13) | −0.0022 (10) | −0.0001 (9) | 0.0008 (11) |
Geometric parameters (Å, º) top
S1—C2 | 1.679 (3) | C14—C15 | 1.385 (4) |
Cl1—C13 | 1.755 (3) | C14—H14 | 0.9500 |
Cl2—C23 | 1.751 (3) | C15—C16 | 1.399 (3) |
C1—O1 | 1.224 (3) | C15—H15 | 0.9500 |
C1—N1 | 1.387 (3) | C16—H16 | 0.9500 |
C1—C11 | 1.507 (3) | C21—C26 | 1.391 (4) |
N1—C2 | 1.409 (3) | C21—C22 | 1.397 (4) |
N1—H1 | 0.92 (4) | C22—C23 | 1.387 (3) |
C2—N2 | 1.335 (3) | C22—H22 | 0.9500 |
N2—C21 | 1.442 (3) | C23—C24 | 1.399 (4) |
N2—H2 | 0.90 (4) | C24—C25 | 1.382 (4) |
C11—C16 | 1.395 (4) | C24—H24 | 0.9500 |
C11—C12 | 1.397 (4) | C25—C26 | 1.401 (4) |
C12—C13 | 1.396 (3) | C25—H25 | 0.9500 |
C12—H12 | 0.9500 | C26—H26 | 0.9500 |
C13—C14 | 1.390 (4) | | |
| | | |
O1—C1—N1 | 123.6 (2) | C14—C15—C16 | 120.1 (2) |
O1—C1—C11 | 121.9 (2) | C14—C15—H15 | 120.0 |
N1—C1—C11 | 114.5 (2) | C16—C15—H15 | 120.0 |
C1—N1—C2 | 127.7 (2) | C11—C16—C15 | 119.8 (2) |
C1—N1—H1 | 118 (2) | C11—C16—H16 | 120.1 |
C2—N1—H1 | 114 (2) | C15—C16—H16 | 120.1 |
N2—C2—N1 | 115.8 (2) | C26—C21—C22 | 121.6 (2) |
N2—C2—S1 | 125.99 (18) | C26—C21—N2 | 118.6 (2) |
N1—C2—S1 | 118.23 (19) | C22—C21—N2 | 119.8 (2) |
C2—N2—C21 | 125.1 (2) | C23—C22—C21 | 118.0 (2) |
C2—N2—H2 | 119 (2) | C23—C22—H22 | 121.0 |
C21—N2—H2 | 116 (2) | C21—C22—H22 | 121.0 |
C16—C11—C12 | 120.7 (2) | C22—C23—C24 | 121.7 (3) |
C16—C11—C1 | 121.6 (2) | C22—C23—Cl2 | 118.9 (2) |
C12—C11—C1 | 117.6 (2) | C24—C23—Cl2 | 119.42 (19) |
C13—C12—C11 | 118.1 (2) | C25—C24—C23 | 119.2 (2) |
C13—C12—H12 | 120.9 | C25—C24—H24 | 120.4 |
C11—C12—H12 | 120.9 | C23—C24—H24 | 120.4 |
C14—C13—C12 | 121.8 (2) | C24—C25—C26 | 120.5 (3) |
C14—C13—Cl1 | 119.21 (19) | C24—C25—H25 | 119.7 |
C12—C13—Cl1 | 119.0 (2) | C26—C25—H25 | 119.7 |
C15—C14—C13 | 119.3 (2) | C21—C26—C25 | 119.0 (3) |
C15—C14—H14 | 120.3 | C21—C26—H26 | 120.5 |
C13—C14—H14 | 120.3 | C25—C26—H26 | 120.5 |
| | | |
O1—C1—N1—C2 | 3.9 (4) | C13—C14—C15—C16 | −1.7 (4) |
C11—C1—N1—C2 | −177.2 (2) | C12—C11—C16—C15 | 0.9 (4) |
C1—N1—C2—N2 | 6.9 (4) | C1—C11—C16—C15 | 178.7 (2) |
C1—N1—C2—S1 | −171.6 (2) | C14—C15—C16—C11 | 1.3 (4) |
N1—C2—N2—C21 | 174.1 (2) | C2—N2—C21—C26 | 132.4 (3) |
S1—C2—N2—C21 | −7.6 (4) | C2—N2—C21—C22 | −50.0 (3) |
O1—C1—C11—C16 | −141.8 (3) | C26—C21—C22—C23 | −0.8 (4) |
N1—C1—C11—C16 | 39.3 (3) | N2—C21—C22—C23 | −178.4 (2) |
O1—C1—C11—C12 | 36.1 (4) | C21—C22—C23—C24 | 1.5 (4) |
N1—C1—C11—C12 | −142.8 (2) | C21—C22—C23—Cl2 | −178.29 (18) |
C16—C11—C12—C13 | −2.5 (4) | C22—C23—C24—C25 | −0.8 (4) |
C1—C11—C12—C13 | 179.6 (2) | Cl2—C23—C24—C25 | 179.04 (19) |
C11—C12—C13—C14 | 2.1 (4) | C23—C24—C25—C26 | −0.7 (4) |
C11—C12—C13—Cl1 | −177.43 (18) | C22—C21—C26—C25 | −0.6 (4) |
C12—C13—C14—C15 | 0.0 (4) | N2—C21—C26—C25 | 177.0 (2) |
Cl1—C13—C14—C15 | 179.5 (2) | C24—C25—C26—C21 | 1.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.90 (4) | 1.97 (3) | 2.674 (3) | 134 (3) |
N1—H1···S1i | 0.92 (4) | 2.66 (4) | 3.571 (2) | 175 (3) |
N2—H2···Cl1ii | 0.90 (4) | 2.98 (4) | 3.773 (3) | 149 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2. |