1-(2-Chloro­phen­yl)-3-(2,6-dichloro­benzo­yl)thio­urea toluene hemisolvate

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)°.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0517P)^2 + 1.0113P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (3)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C2T^i	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—C2T^i	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—C2T^i	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)	C2T^i—C5T—C4T	128.7 (12)
C21—C22—Cl3	119.8 (2)	C2T^i—C5T—H4TA	161.3
C23—C22—Cl3	119.7 (2)	C4T—C5T—H4TA	42.3
C24—C23—C22	118.7 (3)	C2T^i—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)	C2T^i—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—C2T^i	17.6 (12)
C12—C11—C16—Cl2	−178.33 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1^ii	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.