1-(3-Chloro­benzo­yl)-3-(2,4,6-trichloro­phen­yl)thio­urea

The title compound, C₁₄H₈Cl₄N₂OS, shows the typical geometric parameters of substituted thio­urea derivatives. Whereas one NH group is involved in an intra­molecular hydrogen bond, the other is shielded, so that no hydrogen bond is observed.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.087
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl4    ..  O1      ..       3.09 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
   2 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

---

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-(3-Chlorobenzoyl)-3-(2,4,6-trichlorophenyl)thiourea

Crystal data

C14H8Cl4N2OS	F(000) = 792
Mr = 394.08	Dx = 1.643 Mg m^−3
Monoclinic, P21/n	Melting point: 453 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.4021 (12) Å	Cell parameters from 8713 reflections
b = 9.2723 (9) Å	θ = 3.7–25.8°
c = 14.5212 (15) Å	µ = 0.87 mm^−1
β = 107.379 (8)°	T = 173 K
V = 1593.6 (3) Å^3	Block, colourless
Z = 4	0.48 × 0.46 × 0.43 mm

Data collection

Stoe IPDS-II two-circle diffractometer	2968 independent reflections
Radiation source: fine-focus sealed tube	2559 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω scans	θmax = 25.6°, θmin = 3.7°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −15→15
Tmin = 0.679, Tmax = 0.705	k = −10→11
8381 measured reflections	l = −17→17

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0446P)^2 + 0.8237P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2968 reflections	Δρmax = 0.29 e Å^−3
208 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0115 (11)

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
S1	0.48867 (5)	0.64621 (6)	0.40023 (4)	0.03379 (17)
Cl1	1.18270 (5)	0.26041 (7)	0.64907 (4)	0.03621 (17)
Cl2	0.37807 (5)	0.24399 (6)	0.34161 (4)	0.03320 (17)
Cl3	0.14322 (5)	0.44999 (8)	−0.00847 (4)	0.0461 (2)
Cl4	0.57653 (5)	0.61114 (7)	0.15187 (4)	0.03405 (17)
C1	0.77367 (16)	0.4217 (2)	0.47435 (14)	0.0226 (4)
O1	0.77429 (13)	0.33533 (19)	0.41054 (11)	0.0362 (4)
N1	0.68195 (15)	0.5075 (2)	0.46898 (13)	0.0244 (4)
H1	0.689 (2)	0.563 (3)	0.5138 (19)	0.035 (7)*
C2	0.58116 (17)	0.5201 (2)	0.39339 (14)	0.0222 (4)
N2	0.56746 (15)	0.4273 (2)	0.31999 (12)	0.0233 (4)
H2	0.619 (2)	0.373 (3)	0.3203 (19)	0.037 (7)*
C11	0.87497 (16)	0.4407 (2)	0.56192 (14)	0.0228 (4)
C12	0.96868 (17)	0.3548 (2)	0.56585 (14)	0.0236 (4)
H12	0.9664	0.2882	0.5156	0.028*
C13	1.06520 (18)	0.3680 (2)	0.64409 (15)	0.0251 (5)
C14	1.0717 (2)	0.4645 (3)	0.71836 (16)	0.0351 (5)
H14	1.1386	0.4724	0.7712	0.042*
C15	0.9785 (2)	0.5491 (3)	0.71368 (18)	0.0434 (6)
H15	0.9815	0.6155	0.7642	0.052*
C16	0.8804 (2)	0.5389 (3)	0.63639 (17)	0.0361 (6)
H16	0.8173	0.5984	0.6341	0.043*
C21	0.46731 (16)	0.4289 (2)	0.23987 (14)	0.0223 (4)
C22	0.37230 (18)	0.3495 (2)	0.24139 (15)	0.0241 (4)
C23	0.27237 (18)	0.3534 (2)	0.16524 (16)	0.0283 (5)
H23	0.2083	0.2990	0.1675	0.034*
C24	0.26891 (18)	0.4390 (2)	0.08579 (16)	0.0284 (5)
C25	0.36174 (18)	0.5174 (3)	0.08013 (15)	0.0291 (5)
H25	0.3583	0.5741	0.0248	0.035*
C26	0.46031 (17)	0.5110 (2)	0.15761 (15)	0.0240 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0379 (3)	0.0346 (3)	0.0250 (3)	0.0178 (3)	0.0035 (2)	−0.0007 (2)
Cl1	0.0231 (3)	0.0428 (4)	0.0354 (3)	0.0034 (2)	−0.0024 (2)	0.0009 (2)
Cl2	0.0365 (3)	0.0350 (3)	0.0300 (3)	−0.0010 (2)	0.0128 (2)	0.0066 (2)
Cl3	0.0272 (3)	0.0676 (5)	0.0324 (3)	0.0019 (3)	−0.0079 (2)	−0.0013 (3)
Cl4	0.0286 (3)	0.0390 (3)	0.0329 (3)	−0.0083 (2)	0.0068 (2)	0.0064 (2)
C1	0.0201 (10)	0.0261 (11)	0.0206 (10)	0.0000 (8)	0.0044 (8)	0.0012 (8)
O1	0.0263 (8)	0.0460 (10)	0.0292 (8)	0.0108 (7)	−0.0025 (6)	−0.0158 (8)
N1	0.0255 (9)	0.0267 (10)	0.0180 (9)	0.0048 (8)	0.0023 (7)	−0.0030 (7)
C2	0.0252 (11)	0.0226 (10)	0.0188 (10)	0.0009 (8)	0.0064 (8)	0.0035 (8)
N2	0.0198 (9)	0.0264 (10)	0.0219 (9)	0.0046 (8)	0.0035 (7)	−0.0030 (7)
C11	0.0216 (10)	0.0250 (11)	0.0207 (10)	−0.0025 (8)	0.0045 (8)	0.0013 (8)
C12	0.0236 (10)	0.0264 (11)	0.0190 (10)	−0.0041 (9)	0.0035 (8)	−0.0016 (8)
C13	0.0231 (10)	0.0262 (11)	0.0238 (10)	−0.0028 (9)	0.0038 (8)	0.0038 (9)
C14	0.0303 (12)	0.0428 (14)	0.0249 (11)	−0.0080 (11)	−0.0029 (9)	−0.0032 (10)
C15	0.0408 (14)	0.0513 (17)	0.0320 (13)	−0.0005 (13)	0.0016 (11)	−0.0182 (12)
C16	0.0304 (12)	0.0424 (14)	0.0318 (12)	0.0030 (11)	0.0036 (10)	−0.0130 (11)
C21	0.0208 (10)	0.0230 (10)	0.0211 (10)	0.0030 (8)	0.0034 (8)	−0.0018 (8)
C22	0.0251 (10)	0.0254 (11)	0.0223 (10)	0.0026 (9)	0.0081 (8)	−0.0017 (8)
C23	0.0222 (10)	0.0334 (12)	0.0289 (11)	−0.0041 (9)	0.0068 (9)	−0.0057 (9)
C24	0.0215 (10)	0.0347 (12)	0.0246 (11)	0.0035 (9)	0.0000 (8)	−0.0061 (9)
C25	0.0298 (11)	0.0332 (12)	0.0213 (10)	0.0035 (10)	0.0032 (9)	0.0027 (9)
C26	0.0223 (10)	0.0262 (11)	0.0227 (10)	−0.0011 (9)	0.0057 (8)	0.0003 (8)

Geometric parameters (Å, º)

S1—C2	1.662 (2)	C12—H12	0.9500
Cl1—C13	1.750 (2)	C13—C14	1.385 (3)
Cl2—C22	1.737 (2)	C14—C15	1.382 (3)
Cl3—C24	1.743 (2)	C14—H14	0.9500
Cl4—C26	1.738 (2)	C15—C16	1.390 (3)
C1—O1	1.226 (3)	C15—H15	0.9500
C1—N1	1.372 (3)	C16—H16	0.9500
C1—C11	1.507 (3)	C21—C22	1.395 (3)
N1—C2	1.400 (3)	C21—C26	1.397 (3)
N1—H1	0.82 (3)	C22—C23	1.393 (3)
C2—N2	1.340 (3)	C23—C24	1.391 (3)
N2—C21	1.426 (3)	C23—H23	0.9500
N2—H2	0.82 (3)	C24—C25	1.385 (3)
C11—C12	1.396 (3)	C25—C26	1.394 (3)
C11—C16	1.400 (3)	C25—H25	0.9500
C12—C13	1.388 (3)
O1—C1—N1	121.89 (19)	C14—C15—C16	121.2 (2)
O1—C1—C11	121.48 (18)	C14—C15—H15	119.4
N1—C1—C11	116.62 (18)	C16—C15—H15	119.4
C1—N1—C2	128.60 (18)	C15—C16—C11	119.8 (2)
C1—N1—H1	115.5 (18)	C15—C16—H16	120.1
C2—N1—H1	115.7 (18)	C11—C16—H16	120.1
N2—C2—N1	116.18 (18)	C22—C21—C26	117.63 (18)
N2—C2—S1	124.98 (16)	C22—C21—N2	121.05 (18)
N1—C2—S1	118.84 (15)	C26—C21—N2	121.31 (18)
C2—N2—C21	121.00 (17)	C23—C22—C21	121.95 (19)
C2—N2—H2	118.9 (19)	C23—C22—Cl2	118.92 (16)
C21—N2—H2	120.1 (19)	C21—C22—Cl2	119.13 (16)
C12—C11—C16	119.48 (19)	C24—C23—C22	118.2 (2)
C12—C11—C1	116.19 (18)	C24—C23—H23	120.9
C16—C11—C1	124.32 (19)	C22—C23—H23	120.9
C13—C12—C11	119.15 (19)	C25—C24—C23	121.9 (2)
C13—C12—H12	120.4	C25—C24—Cl3	119.15 (17)
C11—C12—H12	120.4	C23—C24—Cl3	118.91 (17)
C14—C13—C12	122.0 (2)	C24—C25—C26	118.3 (2)
C14—C13—Cl1	118.82 (17)	C24—C25—H25	120.9
C12—C13—Cl1	119.19 (17)	C26—C25—H25	120.9
C15—C14—C13	118.4 (2)	C25—C26—C21	121.95 (19)
C15—C14—H14	120.8	C25—C26—Cl4	118.59 (16)
C13—C14—H14	120.8	C21—C26—Cl4	119.45 (16)
O1—C1—N1—C2	−4.1 (3)	C1—C11—C16—C15	−179.3 (2)
C11—C1—N1—C2	174.76 (19)	C2—N2—C21—C22	−87.5 (2)
C1—N1—C2—N2	6.6 (3)	C2—N2—C21—C26	91.8 (2)
C1—N1—C2—S1	−173.27 (17)	C26—C21—C22—C23	−1.5 (3)
N1—C2—N2—C21	179.02 (17)	N2—C21—C22—C23	177.79 (19)
S1—C2—N2—C21	−1.1 (3)	C26—C21—C22—Cl2	179.10 (15)
O1—C1—C11—C12	0.0 (3)	N2—C21—C22—Cl2	−1.6 (3)
N1—C1—C11—C12	−178.83 (18)	C21—C22—C23—C24	0.3 (3)
O1—C1—C11—C16	178.9 (2)	Cl2—C22—C23—C24	179.63 (16)
N1—C1—C11—C16	0.0 (3)	C22—C23—C24—C25	1.1 (3)
C16—C11—C12—C13	0.4 (3)	C22—C23—C24—Cl3	−177.90 (16)
C1—C11—C12—C13	179.38 (18)	C23—C24—C25—C26	−1.1 (3)
C11—C12—C13—C14	−0.4 (3)	Cl3—C24—C25—C26	177.91 (16)
C11—C12—C13—Cl1	−179.97 (15)	C24—C25—C26—C21	−0.3 (3)
C12—C13—C14—C15	0.3 (3)	C24—C25—C26—Cl4	−179.04 (17)
Cl1—C13—C14—C15	179.92 (19)	C22—C21—C26—C25	1.5 (3)
C13—C14—C15—C16	−0.3 (4)	N2—C21—C26—C25	−177.77 (19)
C14—C15—C16—C11	0.4 (4)	C22—C21—C26—Cl4	−179.71 (15)
C12—C11—C16—C15	−0.5 (4)	N2—C21—C26—Cl4	1.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.82 (3)	2.01 (3)	2.650 (2)	135 (3)
C23—H23···S1^i	0.95	2.74	3.638 (2)	158

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.