In the title compound, C14H9Cl3N2OS·0.5C7H8, the toluene molecule is disordered over a centre of inversion. The dihedral angle formed by the two benzene ring planes is 2.26(8)°.
Supporting information
CCDC reference: 618226
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.048
- wR factor = 0.123
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT073_ALERT_1_A H-atoms ref, but _hydrogen_treatment reported as constr
PLAT770_ALERT_2_A Suspect C-H Bond in CIF: C5T -H4TA .. 1.32 Ang.
Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact H4TC .. H14 .. 2.06 Ang.
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.00 Ratio
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C2T
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C4T
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C3T
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.16
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 30.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 42.30 Deg.
C4T -C5T -H4TA 1.555 1.555 1.555
2 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
5 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, 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-(2-Chlorophenyl)-3-(2,6-dichlorobenzoyl)thiourea toluene hemisolvate
top
Crystal data top
C14H9Cl3N2OS·0.5C7H8 | Z = 2 |
Mr = 405.71 | F(000) = 414 |
Triclinic, P1 | Dx = 1.432 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9672 (16) Å | Cell parameters from 6951 reflections |
b = 10.6954 (16) Å | θ = 3.7–25.8° |
c = 10.7104 (16) Å | µ = 0.61 mm−1 |
α = 64.032 (11)° | T = 173 K |
β = 67.438 (11)° | Block, colourless |
γ = 86.053 (12)° | 0.47 × 0.45 × 0.39 mm |
V = 941.1 (2) Å3 | |
Data collection top
Stoe IPDS-II two-circle diffractometer | 3438 independent reflections |
Radiation source: fine-focus sealed tube | 2938 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω scans | θmax = 25.5°, θmin = 3.7° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −12→12 |
Tmin = 0.764, Tmax = 0.798 | k = −12→12 |
6951 measured reflections | l = −12→12 |
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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0517P)2 + 1.0113P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3438 reflections | Δρmax = 0.64 e Å−3 |
236 parameters | Δρmin = −0.61 e Å−3 |
8 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.022 (3) |
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 | Occ. (<1) |
O1 | 0.6179 (2) | 0.42867 (19) | 0.9216 (2) | 0.0413 (5) | |
C1 | 0.7152 (3) | 0.3916 (2) | 0.9684 (3) | 0.0293 (5) | |
N1 | 0.8143 (2) | 0.4812 (2) | 0.9609 (2) | 0.0285 (4) | |
H1 | 0.8781 | 0.4418 | 1.0003 | 0.034* | |
C2 | 0.8250 (2) | 0.6274 (2) | 0.8979 (3) | 0.0270 (5) | |
S1 | 0.96035 (7) | 0.71715 (6) | 0.89215 (8) | 0.0388 (2) | |
N2 | 0.7218 (2) | 0.6855 (2) | 0.8475 (2) | 0.0334 (5) | |
H2 | 0.6510 | 0.6299 | 0.8614 | 0.040* | |
Cl1 | 0.56842 (8) | 0.24123 (8) | 1.30759 (8) | 0.0518 (2) | |
Cl2 | 0.90340 (10) | 0.27588 (13) | 0.75906 (13) | 0.0789 (4) | |
Cl3 | 0.87288 (10) | 0.81562 (10) | 0.51186 (10) | 0.0612 (3) | |
C11 | 0.7350 (3) | 0.2394 (3) | 1.0413 (3) | 0.0341 (6) | |
C12 | 0.6670 (3) | 0.1580 (3) | 1.1975 (3) | 0.0418 (7) | |
C13 | 0.6756 (4) | 0.0159 (3) | 1.2649 (5) | 0.0638 (11) | |
H13 | 0.6288 | −0.0376 | 1.3714 | 0.077* | |
C14 | 0.7523 (5) | −0.0464 (4) | 1.1760 (7) | 0.0815 (15) | |
H14 | 0.7577 | −0.1443 | 1.2222 | 0.098* | |
C15 | 0.8226 (4) | 0.0284 (4) | 1.0207 (7) | 0.0745 (13) | |
H15 | 0.8752 | −0.0171 | 0.9608 | 0.089* | |
C16 | 0.8144 (3) | 0.1735 (3) | 0.9534 (4) | 0.0507 (8) | |
C21 | 0.7203 (3) | 0.8336 (3) | 0.7719 (3) | 0.0318 (5) | |
C22 | 0.7857 (3) | 0.9051 (3) | 0.6157 (3) | 0.0382 (6) | |
C23 | 0.7800 (4) | 1.0492 (3) | 0.5411 (4) | 0.0502 (8) | |
H23 | 0.8264 | 1.0988 | 0.4342 | 0.060* | |
C24 | 0.7057 (4) | 1.1176 (3) | 0.6260 (4) | 0.0540 (8) | |
H24 | 0.7001 | 1.2151 | 0.5763 | 0.065* | |
C25 | 0.6400 (4) | 1.0483 (3) | 0.7798 (4) | 0.0536 (8) | |
H25 | 0.5901 | 1.0980 | 0.8357 | 0.064* | |
C26 | 0.6457 (3) | 0.9051 (3) | 0.8555 (4) | 0.0427 (6) | |
H26 | 0.5995 | 0.8568 | 0.9625 | 0.051* | |
C1T | 0.4033 (11) | 0.4951 (7) | 0.5539 (11) | 0.073 (2) | 0.50 |
C2T | 0.4550 (9) | 0.5283 (5) | 0.4018 (6) | 0.0899 (16) | |
H2T | 0.3830 | 0.5295 | 0.3636 | 0.108* | 0.50 |
H2T' | 0.4688 | 0.5757 | 0.2985 | 0.108* | 0.50 |
C3T | 0.5775 (12) | 0.5573 (9) | 0.3138 (13) | 0.074 (2) | 0.50 |
H3T | 0.5910 | 0.5936 | 0.2109 | 0.089* | 0.50 |
C4T | 0.7179 (11) | 0.5443 (6) | 0.3429 (9) | 0.164 (4) | |
H4TA | 0.7947 | 0.5246 | 0.3826 | 0.247* | 0.50 |
H4TB | 0.7298 | 0.4949 | 0.2815 | 0.247* | 0.50 |
H4TC | 0.7256 | 0.6454 | 0.2808 | 0.247* | 0.50 |
H4T | 0.8153 (11) | 0.5532 (6) | 0.2733 (9) | 0.197* | 0.50 |
C5T | 0.6719 (16) | 0.5156 (10) | 0.4942 (19) | 0.100 (4) | 0.50 |
H5T | 0.7457 | 0.5311 | 0.5232 | 0.121* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0362 (10) | 0.0352 (10) | 0.0634 (13) | 0.0045 (8) | −0.0326 (9) | −0.0203 (9) |
C1 | 0.0252 (12) | 0.0305 (12) | 0.0349 (13) | 0.0011 (9) | −0.0135 (10) | −0.0152 (10) |
N1 | 0.0256 (10) | 0.0248 (10) | 0.0371 (11) | 0.0007 (8) | −0.0187 (9) | −0.0098 (8) |
C2 | 0.0257 (11) | 0.0252 (11) | 0.0275 (11) | 0.0010 (9) | −0.0114 (9) | −0.0084 (9) |
S1 | 0.0369 (4) | 0.0246 (3) | 0.0581 (4) | −0.0008 (2) | −0.0318 (3) | −0.0093 (3) |
N2 | 0.0280 (10) | 0.0261 (10) | 0.0467 (13) | 0.0014 (8) | −0.0225 (10) | −0.0099 (9) |
Cl1 | 0.0479 (4) | 0.0582 (5) | 0.0414 (4) | −0.0059 (3) | −0.0170 (3) | −0.0143 (3) |
Cl2 | 0.0559 (5) | 0.1170 (9) | 0.0878 (7) | 0.0077 (5) | −0.0129 (5) | −0.0788 (7) |
Cl3 | 0.0609 (5) | 0.0737 (6) | 0.0526 (5) | 0.0145 (4) | −0.0162 (4) | −0.0376 (4) |
C11 | 0.0284 (12) | 0.0303 (13) | 0.0565 (17) | 0.0050 (10) | −0.0259 (12) | −0.0227 (12) |
C12 | 0.0409 (15) | 0.0317 (13) | 0.0573 (17) | −0.0016 (11) | −0.0323 (14) | −0.0117 (12) |
C13 | 0.072 (2) | 0.0289 (15) | 0.097 (3) | −0.0014 (15) | −0.061 (2) | −0.0095 (17) |
C14 | 0.093 (3) | 0.0332 (17) | 0.159 (5) | 0.0188 (19) | −0.098 (3) | −0.039 (2) |
C15 | 0.063 (2) | 0.066 (2) | 0.160 (5) | 0.036 (2) | −0.074 (3) | −0.084 (3) |
C16 | 0.0392 (15) | 0.0552 (18) | 0.088 (2) | 0.0133 (13) | −0.0357 (16) | −0.0494 (18) |
C21 | 0.0285 (12) | 0.0289 (12) | 0.0405 (14) | 0.0029 (9) | −0.0210 (11) | −0.0113 (11) |
C22 | 0.0360 (14) | 0.0412 (15) | 0.0395 (14) | 0.0006 (11) | −0.0175 (12) | −0.0170 (12) |
C23 | 0.0562 (19) | 0.0406 (16) | 0.0458 (17) | −0.0064 (14) | −0.0290 (15) | −0.0032 (13) |
C24 | 0.064 (2) | 0.0332 (15) | 0.082 (2) | 0.0116 (14) | −0.0497 (19) | −0.0235 (16) |
C25 | 0.0593 (19) | 0.0499 (18) | 0.076 (2) | 0.0225 (15) | −0.0414 (18) | −0.0381 (17) |
C26 | 0.0418 (15) | 0.0423 (15) | 0.0549 (17) | 0.0126 (12) | −0.0267 (14) | −0.0255 (13) |
C1T | 0.096 (6) | 0.028 (3) | 0.073 (5) | −0.007 (4) | −0.007 (5) | −0.024 (4) |
C2T | 0.159 (6) | 0.054 (3) | 0.074 (3) | 0.004 (3) | −0.062 (4) | −0.028 (2) |
C3T | 0.088 (6) | 0.053 (5) | 0.094 (7) | 0.023 (5) | −0.040 (6) | −0.041 (5) |
C4T | 0.232 (10) | 0.073 (4) | 0.131 (6) | −0.054 (5) | −0.007 (7) | −0.043 (4) |
C5T | 0.130 (10) | 0.044 (5) | 0.169 (14) | 0.020 (6) | −0.093 (11) | −0.055 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.223 (3) | C23—C24 | 1.379 (5) |
C1—N1 | 1.379 (3) | C23—H23 | 0.9500 |
C1—C11 | 1.503 (3) | C24—C25 | 1.364 (5) |
N1—C2 | 1.399 (3) | C24—H24 | 0.9500 |
N1—H1 | 0.8800 | C25—C26 | 1.394 (4) |
C2—N2 | 1.334 (3) | C25—H25 | 0.9500 |
C2—S1 | 1.676 (2) | C26—H26 | 0.9500 |
N2—C21 | 1.430 (3) | C1T—C2T | 1.385 (11) |
N2—H2 | 0.8800 | C1T—C2Ti | 1.626 (13) |
Cl1—C12 | 1.749 (3) | C2T—C3T | 1.178 (11) |
Cl2—C16 | 1.744 (4) | C2T—H2T | 0.9500 |
Cl3—C22 | 1.727 (3) | C2T—H2T' | 0.9500 |
C11—C16 | 1.393 (4) | C3T—C4T | 1.531 (13) |
C11—C12 | 1.397 (4) | C3T—H2T' | 1.1479 |
C12—C13 | 1.381 (4) | C3T—H3T | 0.9500 |
C13—C14 | 1.365 (7) | C4T—C5T | 1.394 (16) |
C13—H13 | 0.9500 | C4T—H4TA | 0.9801 |
C14—C15 | 1.384 (7) | C4T—H4TB | 0.9801 |
C14—H14 | 0.9500 | C4T—H4TC | 0.9800 |
C15—C16 | 1.408 (5) | C4T—H4T | 0.9501 |
C15—H15 | 0.9500 | C5T—C2Ti | 1.266 (15) |
C21—C22 | 1.386 (4) | C5T—H4TA | 1.3152 |
C21—C26 | 1.396 (4) | C5T—H5T | 0.9500 |
C22—C23 | 1.400 (4) | | |
| | | |
O1—C1—N1 | 124.6 (2) | C25—C24—H24 | 119.3 |
O1—C1—C11 | 121.1 (2) | C23—C24—H24 | 119.3 |
N1—C1—C11 | 114.2 (2) | C24—C25—C26 | 120.5 (3) |
C1—N1—C2 | 127.5 (2) | C24—C25—H25 | 119.8 |
C1—N1—H1 | 116.2 | C26—C25—H25 | 119.8 |
C2—N1—H1 | 116.2 | C25—C26—C21 | 119.1 (3) |
N2—C2—N1 | 115.8 (2) | C25—C26—H26 | 120.4 |
N2—C2—S1 | 124.52 (18) | C21—C26—H26 | 120.4 |
N1—C2—S1 | 119.68 (17) | C2T—C1T—C2Ti | 106.6 (7) |
C2—N2—C21 | 123.5 (2) | C3T—C2T—C1T | 127.8 (9) |
C2—N2—H2 | 118.3 | C3T—C2T—H2T | 116.1 |
C21—N2—H2 | 118.3 | C1T—C2T—H2T | 116.1 |
C16—C11—C12 | 118.1 (3) | C3T—C2T—H2T' | 64.2 |
C16—C11—C1 | 120.6 (3) | C1T—C2T—H2T' | 160.0 |
C12—C11—C1 | 121.2 (2) | H2T—C2T—H2T' | 54.6 |
C13—C12—C11 | 121.8 (3) | C2T—C3T—C4T | 128.7 (10) |
C13—C12—Cl1 | 120.2 (3) | C2T—C3T—H2T' | 48.2 |
C11—C12—Cl1 | 118.0 (2) | C4T—C3T—H2T' | 173.3 |
C14—C13—C12 | 118.9 (4) | C2T—C3T—H3T | 115.6 |
C14—C13—H13 | 120.5 | C4T—C3T—H3T | 115.6 |
C12—C13—H13 | 120.5 | H2T'—C3T—H3T | 67.8 |
C13—C14—C15 | 122.1 (3) | C5T—C4T—C3T | 105.1 (9) |
C13—C14—H14 | 119.0 | C5T—C4T—H4TA | 64.5 |
C15—C14—H14 | 119.0 | C3T—C4T—H4TA | 168.6 |
C14—C15—C16 | 118.5 (4) | C5T—C4T—H4TB | 139.6 |
C14—C15—H15 | 120.8 | C3T—C4T—H4TB | 75.0 |
C16—C15—H15 | 120.8 | H4TA—C4T—H4TB | 109.3 |
C11—C16—C15 | 120.6 (4) | C5T—C4T—H4TC | 109.7 |
C11—C16—Cl2 | 118.1 (2) | C3T—C4T—H4TC | 78.2 |
C15—C16—Cl2 | 121.3 (3) | H4TA—C4T—H4TC | 109.2 |
C22—C21—C26 | 119.8 (2) | H4TB—C4T—H4TC | 109.8 |
C22—C21—N2 | 120.4 (2) | C5T—C4T—H4T | 127.3 |
C26—C21—N2 | 119.8 (2) | C3T—C4T—H4T | 127.6 |
C21—C22—C23 | 120.5 (3) | C2Ti—C5T—C4T | 128.7 (12) |
C21—C22—Cl3 | 119.8 (2) | C2Ti—C5T—H4TA | 161.3 |
C23—C22—Cl3 | 119.7 (2) | C4T—C5T—H4TA | 42.3 |
C24—C23—C22 | 118.7 (3) | C2Ti—C5T—H5T | 115.6 |
C24—C23—H23 | 120.6 | C4T—C5T—H5T | 115.6 |
C22—C23—H23 | 120.6 | H4TA—C5T—H5T | 76.1 |
C25—C24—C23 | 121.4 (3) | | |
| | | |
O1—C1—N1—C2 | −1.4 (4) | C1—C11—C16—Cl2 | 5.8 (3) |
C11—C1—N1—C2 | 178.9 (2) | C14—C15—C16—C11 | −1.1 (4) |
C1—N1—C2—N2 | 4.3 (4) | C14—C15—C16—Cl2 | 178.5 (3) |
C1—N1—C2—S1 | −176.6 (2) | C2—N2—C21—C22 | 92.4 (3) |
N1—C2—N2—C21 | −176.2 (2) | C2—N2—C21—C26 | −91.0 (3) |
S1—C2—N2—C21 | 4.6 (4) | C26—C21—C22—C23 | 1.2 (4) |
O1—C1—C11—C16 | 84.0 (3) | N2—C21—C22—C23 | 177.8 (2) |
N1—C1—C11—C16 | −96.3 (3) | C26—C21—C22—Cl3 | −177.9 (2) |
O1—C1—C11—C12 | −91.8 (3) | N2—C21—C22—Cl3 | −1.4 (3) |
N1—C1—C11—C12 | 87.9 (3) | C21—C22—C23—C24 | −1.3 (4) |
C16—C11—C12—C13 | −0.6 (4) | Cl3—C22—C23—C24 | 177.9 (2) |
C1—C11—C12—C13 | 175.3 (2) | C22—C23—C24—C25 | 0.9 (5) |
C16—C11—C12—Cl1 | 179.60 (19) | C23—C24—C25—C26 | −0.4 (5) |
C1—C11—C12—Cl1 | −4.5 (3) | C24—C25—C26—C21 | 0.4 (4) |
C11—C12—C13—C14 | −0.2 (4) | C22—C21—C26—C25 | −0.8 (4) |
Cl1—C12—C13—C14 | 179.5 (2) | N2—C21—C26—C25 | −177.4 (2) |
C12—C13—C14—C15 | 0.5 (5) | C2Ti—C1T—C2T—C3T | −11.5 (7) |
C13—C14—C15—C16 | 0.2 (5) | C1T—C2T—C3T—C4T | 11.1 (11) |
C12—C11—C16—C15 | 1.3 (4) | C2T—C3T—C4T—C5T | −11.0 (11) |
C1—C11—C16—C15 | −174.6 (2) | C3T—C4T—C5T—C2Ti | 17.6 (12) |
C12—C11—C16—Cl2 | −178.33 (19) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1ii | 0.88 | 2.48 | 3.340 (2) | 167 |
N2—H2···O1 | 0.88 | 1.97 | 2.665 (3) | 135 |
Symmetry code: (ii) −x+2, −y+1, −z+2. |