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The title compound, C14H10Cl2N2OS, crystallizes with two mol­ecules in the asymmetric unit. The two mol­ecules, differing only in the conformation of the dichloro­phenyl ring, show the typical geometric parameters of substituted thio­urea derivatives. The crystal packing is characterized by N—H...O and N—H...S hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004527/fl2099sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004527/fl2099Isup2.hkl
Contains datablock I

CCDC reference: 640327

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.105
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.61 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.44 PLAT432_ALERT_2_C Short Inter X...Y Contact S1A .. C16 .. 3.20 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 4 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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 and PLATON (Spek, 2003).

1-(2,4-Dichlorobenzoyl)-3-phenylthiourea top
Crystal data top
C14H10Cl2N2OSZ = 4
Mr = 325.20F(000) = 664
Triclinic, P1Dx = 1.482 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0222 (10) ÅCell parameters from 11336 reflections
b = 13.8576 (15) Åθ = 3.6–25.7°
c = 14.1496 (17) ŵ = 0.58 mm1
α = 108.539 (9)°T = 173 K
β = 91.077 (10)°Block, colourless
γ = 101.126 (9)°0.42 × 0.37 × 0.33 mm
V = 1457.9 (3) Å3
Data collection top
Stoe IPDS-II two-circle
diffractometer
5382 independent reflections
Radiation source: fine-focus sealed tube4738 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω scansθmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 99
Tmin = 0.792, Tmax = 0.831k = 1615
15382 measured reflectionsl = 017
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0618P)2 + 0.6908P]
where P = (Fo2 + 2Fc2)/3
5382 reflections(Δ/σ)max = 0.001
361 parametersΔρmax = 0.86 e Å3
0 restraintsΔρmin = 0.54 e Å3
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
xyzUiso*/Ueq
S10.47333 (6)0.37717 (4)0.11111 (3)0.02697 (13)
Cl10.39272 (8)0.82463 (4)0.14586 (4)0.04424 (16)
Cl20.26913 (10)0.96585 (5)0.53363 (5)0.0615 (2)
C10.2281 (2)0.60914 (14)0.15009 (13)0.0253 (4)
O10.13688 (19)0.59834 (11)0.07572 (10)0.0361 (4)
N10.32596 (18)0.53984 (11)0.15756 (10)0.0217 (3)
H10.38810.55680.21460.026*
C20.3384 (2)0.44564 (13)0.08516 (12)0.0187 (3)
N20.24144 (19)0.42011 (12)0.00079 (10)0.0224 (3)
H20.18540.46640.00790.027*
C110.2375 (2)0.69858 (14)0.24587 (13)0.0241 (4)
C120.3089 (2)0.80025 (15)0.25016 (14)0.0286 (4)
C130.3195 (3)0.88272 (16)0.33842 (15)0.0352 (5)
H130.36940.95180.34150.042*
C140.2557 (3)0.86237 (17)0.42208 (15)0.0359 (5)
C150.1832 (3)0.76277 (17)0.42136 (15)0.0328 (4)
H150.14080.75070.47970.039*
C160.1746 (2)0.68092 (16)0.33187 (14)0.0291 (4)
H160.12520.61200.32930.035*
C210.2206 (2)0.32422 (14)0.08225 (12)0.0198 (3)
C220.2418 (2)0.32961 (17)0.17812 (14)0.0303 (4)
H220.27870.39490.18780.036*
C230.2082 (3)0.2382 (2)0.25907 (15)0.0434 (6)
H230.22390.24090.32460.052*
C240.1515 (3)0.14264 (19)0.24512 (17)0.0470 (6)
H240.12620.08040.30100.056*
C250.1324 (3)0.13880 (17)0.14970 (18)0.0410 (5)
H250.09520.07350.14010.049*
C260.1668 (2)0.22948 (15)0.06718 (14)0.0282 (4)
H260.15350.22640.00160.034*
S1A0.49571 (6)0.38633 (4)0.59972 (3)0.02846 (13)
Cl1A0.07452 (7)0.58273 (4)0.82675 (4)0.04341 (15)
Cl2A0.27936 (12)0.99550 (5)0.99523 (5)0.0693 (2)
C1A0.2300 (2)0.60794 (14)0.63869 (13)0.0223 (4)
O1A0.13419 (18)0.59328 (11)0.56419 (10)0.0336 (3)
N1A0.33102 (18)0.54130 (11)0.64675 (11)0.0218 (3)
H1A0.39700.56130.70280.026*
C2A0.3428 (2)0.44561 (13)0.57742 (12)0.0196 (3)
N2A0.23072 (19)0.40979 (11)0.49704 (11)0.0223 (3)
H2A0.15880.44880.49200.027*
C11A0.2463 (2)0.70382 (14)0.72900 (13)0.0233 (4)
C12A0.1803 (2)0.70024 (15)0.81869 (14)0.0277 (4)
C13A0.1918 (3)0.78885 (18)0.90184 (15)0.0358 (5)
H13A0.14880.78460.96280.043*
C14A0.2680 (3)0.88303 (17)0.89246 (16)0.0395 (5)
C15A0.3333 (3)0.89103 (17)0.80503 (18)0.0463 (6)
H15A0.38500.95720.80110.056*
C16A0.3230 (3)0.80114 (16)0.72229 (15)0.0356 (5)
H16A0.36760.80600.66190.043*
C21A0.2183 (2)0.31197 (13)0.41772 (12)0.0200 (3)
C22A0.2328 (2)0.31295 (16)0.31997 (14)0.0291 (4)
H22A0.25420.37700.30650.035*
C23A0.2154 (3)0.21918 (18)0.24266 (15)0.0400 (5)
H23A0.22480.21920.17580.048*
C24A0.1844 (3)0.12516 (17)0.26184 (16)0.0393 (5)
H24A0.17460.06140.20860.047*
C25A0.1680 (3)0.12514 (16)0.35896 (17)0.0366 (5)
H25A0.14440.06100.37220.044*
C26A0.1857 (2)0.21838 (14)0.43727 (14)0.0272 (4)
H26A0.17560.21810.50400.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0285 (2)0.0245 (2)0.0231 (2)0.01438 (19)0.00891 (18)0.00342 (18)
Cl10.0539 (3)0.0434 (3)0.0306 (3)0.0027 (2)0.0058 (2)0.0096 (2)
Cl20.0833 (5)0.0459 (4)0.0335 (3)0.0161 (3)0.0094 (3)0.0186 (3)
C10.0236 (9)0.0255 (9)0.0222 (9)0.0092 (7)0.0042 (7)0.0004 (7)
O10.0427 (8)0.0324 (8)0.0274 (7)0.0209 (6)0.0160 (6)0.0047 (6)
N10.0236 (7)0.0220 (7)0.0143 (7)0.0103 (6)0.0064 (5)0.0039 (6)
C20.0186 (8)0.0186 (8)0.0153 (8)0.0054 (6)0.0013 (6)0.0000 (6)
N20.0279 (8)0.0222 (8)0.0129 (7)0.0121 (6)0.0050 (6)0.0036 (6)
C110.0226 (9)0.0263 (9)0.0202 (9)0.0140 (7)0.0056 (7)0.0015 (7)
C120.0293 (9)0.0268 (10)0.0251 (9)0.0110 (8)0.0017 (7)0.0007 (8)
C130.0389 (11)0.0271 (10)0.0334 (11)0.0116 (9)0.0027 (9)0.0012 (8)
C140.0391 (11)0.0336 (11)0.0260 (10)0.0153 (9)0.0011 (8)0.0071 (8)
C150.0321 (10)0.0403 (12)0.0234 (9)0.0146 (9)0.0039 (8)0.0028 (8)
C160.0267 (9)0.0298 (10)0.0278 (10)0.0124 (8)0.0053 (7)0.0018 (8)
C210.0159 (8)0.0231 (9)0.0137 (8)0.0057 (6)0.0024 (6)0.0038 (7)
C220.0315 (10)0.0366 (11)0.0198 (9)0.0070 (8)0.0002 (7)0.0052 (8)
C230.0468 (13)0.0613 (16)0.0119 (9)0.0138 (11)0.0025 (8)0.0036 (9)
C240.0454 (13)0.0423 (14)0.0317 (12)0.0127 (10)0.0053 (10)0.0192 (10)
C250.0362 (11)0.0256 (11)0.0466 (13)0.0011 (9)0.0052 (9)0.0033 (9)
C260.0276 (9)0.0282 (10)0.0233 (9)0.0016 (8)0.0014 (7)0.0034 (8)
S1A0.0291 (2)0.0262 (2)0.0253 (2)0.01592 (19)0.01042 (18)0.00339 (18)
Cl1A0.0412 (3)0.0403 (3)0.0455 (3)0.0040 (2)0.0076 (2)0.0167 (2)
Cl2A0.1125 (6)0.0396 (4)0.0405 (3)0.0358 (4)0.0132 (4)0.0184 (3)
C1A0.0200 (8)0.0216 (9)0.0220 (9)0.0050 (7)0.0030 (7)0.0025 (7)
O1A0.0349 (7)0.0276 (7)0.0305 (7)0.0151 (6)0.0153 (6)0.0051 (6)
N1A0.0237 (7)0.0196 (7)0.0161 (7)0.0076 (6)0.0079 (6)0.0034 (6)
C2A0.0197 (8)0.0197 (8)0.0171 (8)0.0059 (6)0.0015 (6)0.0021 (7)
N2A0.0243 (7)0.0201 (8)0.0184 (7)0.0104 (6)0.0047 (6)0.0025 (6)
C11A0.0213 (8)0.0211 (9)0.0230 (9)0.0097 (7)0.0056 (7)0.0015 (7)
C12A0.0187 (8)0.0293 (10)0.0301 (10)0.0056 (7)0.0036 (7)0.0028 (8)
C13A0.0288 (10)0.0463 (13)0.0250 (10)0.0163 (9)0.0029 (8)0.0031 (9)
C14A0.0509 (13)0.0302 (11)0.0293 (11)0.0184 (10)0.0085 (9)0.0066 (9)
C15A0.0671 (16)0.0192 (10)0.0431 (13)0.0051 (10)0.0071 (11)0.0002 (9)
C16A0.0516 (13)0.0254 (10)0.0254 (10)0.0041 (9)0.0040 (9)0.0049 (8)
C21A0.0177 (8)0.0205 (8)0.0168 (8)0.0062 (6)0.0036 (6)0.0017 (7)
C22A0.0323 (10)0.0306 (10)0.0200 (9)0.0038 (8)0.0043 (7)0.0041 (8)
C23A0.0453 (12)0.0446 (13)0.0161 (9)0.0001 (10)0.0019 (8)0.0038 (9)
C24A0.0379 (11)0.0311 (11)0.0286 (11)0.0020 (9)0.0034 (8)0.0151 (8)
C25A0.0370 (11)0.0207 (10)0.0421 (12)0.0031 (8)0.0012 (9)0.0016 (9)
C26A0.0330 (10)0.0241 (10)0.0194 (9)0.0060 (8)0.0009 (7)0.0001 (7)
Geometric parameters (Å, º) top
S1—C21.6761 (17)S1A—C2A1.6785 (17)
Cl1—C121.735 (2)Cl1A—C12A1.724 (2)
Cl2—C141.747 (2)Cl2A—C14A1.747 (2)
C1—O11.222 (2)C1A—O1A1.231 (2)
C1—N11.379 (2)C1A—N1A1.369 (2)
C1—C111.507 (2)C1A—C11A1.504 (2)
N1—C21.403 (2)N1A—C2A1.398 (2)
N1—H10.8800N1A—H1A0.8800
C2—N21.339 (2)C2A—N2A1.334 (2)
N2—C211.434 (2)N2A—C21A1.443 (2)
N2—H20.8800N2A—H2A0.8800
C11—C121.396 (3)C11A—C12A1.396 (3)
C11—C161.400 (3)C11A—C16A1.403 (3)
C12—C131.387 (3)C12A—C13A1.391 (3)
C13—C141.386 (3)C13A—C14A1.378 (3)
C13—H130.9500C13A—H13A0.9500
C14—C151.387 (3)C14A—C15A1.381 (4)
C15—C161.396 (3)C15A—C16A1.399 (3)
C15—H150.9500C15A—H15A0.9500
C16—H160.9500C16A—H16A0.9500
C21—C261.385 (3)C21A—C26A1.388 (3)
C21—C221.394 (3)C21A—C22A1.394 (3)
C22—C231.387 (3)C22A—C23A1.387 (3)
C22—H220.9500C22A—H22A0.9500
C23—C241.392 (4)C23A—C24A1.391 (3)
C23—H230.9500C23A—H23A0.9500
C24—C251.378 (4)C24A—C25A1.383 (3)
C24—H240.9500C24A—H24A0.9500
C25—C261.393 (3)C25A—C26A1.389 (3)
C25—H250.9500C25A—H25A0.9500
C26—H260.9500C26A—H26A0.9500
O1—C1—N1124.47 (17)O1A—C1A—N1A124.09 (16)
O1—C1—C11122.54 (16)O1A—C1A—C11A121.46 (16)
N1—C1—C11112.92 (15)N1A—C1A—C11A114.44 (14)
C1—N1—C2127.81 (14)C1A—N1A—C2A128.38 (14)
C1—N1—H1116.1C1A—N1A—H1A115.8
C2—N1—H1116.1C2A—N1A—H1A115.8
N2—C2—N1115.48 (14)N2A—C2A—N1A116.04 (14)
N2—C2—S1125.91 (13)N2A—C2A—S1A125.34 (13)
N1—C2—S1118.59 (12)N1A—C2A—S1A118.62 (12)
C2—N2—C21125.93 (14)C2A—N2A—C21A125.05 (14)
C2—N2—H2117.0C2A—N2A—H2A117.5
C21—N2—H2117.0C21A—N2A—H2A117.5
C12—C11—C16119.03 (17)C12A—C11A—C16A118.36 (17)
C12—C11—C1120.53 (17)C12A—C11A—C1A122.14 (17)
C16—C11—C1120.44 (17)C16A—C11A—C1A119.43 (17)
C13—C12—C11120.74 (19)C13A—C12A—C11A122.46 (19)
C13—C12—Cl1118.96 (16)C13A—C12A—Cl1A118.14 (16)
C11—C12—Cl1120.26 (14)C11A—C12A—Cl1A119.38 (14)
C14—C13—C12118.7 (2)C14A—C13A—C12A117.5 (2)
C14—C13—H13120.7C14A—C13A—H13A121.2
C12—C13—H13120.7C12A—C13A—H13A121.2
C13—C14—C15122.67 (18)C13A—C14A—C15A122.33 (19)
C13—C14—Cl2118.89 (17)C13A—C14A—Cl2A118.16 (18)
C15—C14—Cl2118.43 (17)C15A—C14A—Cl2A119.52 (18)
C14—C15—C16117.69 (19)C14A—C15A—C16A119.6 (2)
C14—C15—H15121.2C14A—C15A—H15A120.2
C16—C15—H15121.2C16A—C15A—H15A120.2
C15—C16—C11121.20 (19)C15A—C16A—C11A119.7 (2)
C15—C16—H16119.4C15A—C16A—H16A120.2
C11—C16—H16119.4C11A—C16A—H16A120.2
C26—C21—C22121.01 (16)C26A—C21A—C22A120.42 (16)
C26—C21—N2120.85 (16)C26A—C21A—N2A120.99 (15)
C22—C21—N2117.91 (17)C22A—C21A—N2A118.54 (16)
C23—C22—C21119.0 (2)C23A—C22A—C21A119.10 (19)
C23—C22—H22120.5C23A—C22A—H22A120.5
C21—C22—H22120.5C21A—C22A—H22A120.5
C22—C23—C24120.6 (2)C22A—C23A—C24A120.79 (19)
C22—C23—H23119.7C22A—C23A—H23A119.6
C24—C23—H23119.7C24A—C23A—H23A119.6
C25—C24—C23119.57 (19)C25A—C24A—C23A119.56 (18)
C25—C24—H24120.2C25A—C24A—H24A120.2
C23—C24—H24120.2C23A—C24A—H24A120.2
C24—C25—C26120.8 (2)C24A—C25A—C26A120.4 (2)
C24—C25—H25119.6C24A—C25A—H25A119.8
C26—C25—H25119.6C26A—C25A—H25A119.8
C21—C26—C25118.98 (18)C21A—C26A—C25A119.77 (18)
C21—C26—H26120.5C21A—C26A—H26A120.1
C25—C26—H26120.5C25A—C26A—H26A120.1
O1—C1—N1—C21.2 (3)O1A—C1A—N1A—C2A2.2 (3)
C11—C1—N1—C2175.89 (16)C11A—C1A—N1A—C2A178.66 (16)
C1—N1—C2—N20.9 (3)C1A—N1A—C2A—N2A6.8 (3)
C1—N1—C2—S1177.64 (15)C1A—N1A—C2A—S1A172.22 (15)
N1—C2—N2—C21174.22 (16)N1A—C2A—N2A—C21A178.59 (16)
S1—C2—N2—C217.4 (3)S1A—C2A—N2A—C21A2.5 (3)
O1—C1—C11—C1267.5 (3)O1A—C1A—C11A—C12A108.7 (2)
N1—C1—C11—C12115.34 (19)N1A—C1A—C11A—C12A72.2 (2)
O1—C1—C11—C16112.4 (2)O1A—C1A—C11A—C16A68.2 (2)
N1—C1—C11—C1664.7 (2)N1A—C1A—C11A—C16A111.0 (2)
C16—C11—C12—C130.7 (3)C16A—C11A—C12A—C13A1.8 (3)
C1—C11—C12—C13179.35 (17)C1A—C11A—C12A—C13A178.64 (16)
C16—C11—C12—Cl1178.47 (14)C16A—C11A—C12A—Cl1A176.27 (15)
C1—C11—C12—Cl11.6 (2)C1A—C11A—C12A—Cl1A0.6 (2)
C11—C12—C13—C140.8 (3)C11A—C12A—C13A—C14A1.7 (3)
Cl1—C12—C13—C14178.59 (16)Cl1A—C12A—C13A—C14A176.34 (16)
C12—C13—C14—C150.6 (3)C12A—C13A—C14A—C15A0.8 (3)
C12—C13—C14—Cl2179.80 (15)C12A—C13A—C14A—Cl2A178.59 (15)
C13—C14—C15—C160.3 (3)C13A—C14A—C15A—C16A0.0 (4)
Cl2—C14—C15—C16179.52 (15)Cl2A—C14A—C15A—C16A179.41 (18)
C14—C15—C16—C110.2 (3)C14A—C15A—C16A—C11A0.0 (4)
C12—C11—C16—C150.4 (3)C12A—C11A—C16A—C15A0.9 (3)
C1—C11—C16—C15179.63 (16)C1A—C11A—C16A—C15A177.83 (19)
C2—N2—C21—C2655.3 (2)C2A—N2A—C21A—C26A59.5 (2)
C2—N2—C21—C22130.16 (19)C2A—N2A—C21A—C22A123.13 (19)
C26—C21—C22—C230.0 (3)C26A—C21A—C22A—C23A0.5 (3)
N2—C21—C22—C23174.56 (17)N2A—C21A—C22A—C23A177.88 (17)
C21—C22—C23—C241.0 (3)C21A—C22A—C23A—C24A0.1 (3)
C22—C23—C24—C251.4 (3)C22A—C23A—C24A—C25A1.0 (3)
C23—C24—C25—C260.9 (3)C23A—C24A—C25A—C26A1.3 (3)
C22—C21—C26—C250.5 (3)C22A—C21A—C26A—C25A0.2 (3)
N2—C21—C26—C25173.86 (17)N2A—C21A—C26A—C25A177.54 (16)
C24—C25—C26—C210.1 (3)C24A—C25A—C26A—C21A0.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1Ai0.882.593.4502 (15)167
N2—H2···O10.881.952.666 (2)137
N1A—H1A···S1i0.882.623.4829 (15)167
N2A—H2A···O1A0.881.992.687 (2)136
N2A—H2A···O1Aii0.882.373.026 (2)132
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1.
 

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