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In the title mol­ecule, C15H9Cl5N2O2S, all bond lengths and angles are normal. Weak inter­molecular C—H...S hydrogen bonds link the mol­ecules into spiral chains running along the c axis. The crystal packing exhibits a short Cl...Cl distance of 3.364 (3) Å, which suggests the existence of inter­molecular Cl...Cl inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054201/cv2164sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054201/cv2164Isup2.hkl
Contains datablock I

CCDC reference: 636225

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.057
  • wR factor = 0.145
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 25.98 From the CIF: _reflns_number_total 3624 From the CIF: _diffrn_reflns_limit_ max hkl 6. 9. 36. From the CIF: _diffrn_reflns_limit_ min hkl -6. 0. -36. TEST1: Expected hkl limits for theta max Calculated maximum hkl 9. 9. 36. Calculated minimum hkl -9. -9. -36. REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.98 From the CIF: _reflns_number_total 3624 Count of symmetry unique reflns 1848 Completeness (_total/calc) 196.10% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1776 Fraction of Friedel pairs measured 0.961 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 4 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

N-(2,4-Dichlorophenoxyacetyl)-N'-(2,4,6-trichlorophenyl)thiourea top
Crystal data top
C15H9Cl5N2O2SDx = 1.644 Mg m3
Mr = 458.55Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43Cell parameters from 25 reflections
Hall symbol: P 4cwθ = 10–13°
a = 7.9580 (11) ŵ = 0.91 mm1
c = 29.249 (6) ÅT = 293 K
V = 1852.3 (5) Å3Prism, colourless
Z = 40.40 × 0.20 × 0.20 mm
F(000) = 920
Data collection top
Enraf–Nonius CAD-4
diffractometer
2336 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 26.0°, θmin = 2.6°
ω/2θ scansh = 66
Absorption correction: ψ scan
(North et al., 1968)
k = 09
Tmin = 0.713, Tmax = 0.839l = 3636
3624 measured reflections3 standard reflections every 200 reflections
3624 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.07P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.006
3624 reflectionsΔρmax = 0.24 e Å3
226 parametersΔρmin = 0.34 e Å3
1 restraintAbsolute structure: Flack (1983), 1776 Friedel pairs???
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (12)
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
S10.6686 (3)0.3937 (2)0.39062 (8)0.0810 (6)
Cl11.2450 (3)0.8182 (3)0.66398 (7)0.0858 (6)
Cl21.0157 (3)0.4708 (2)0.51962 (8)0.0819 (6)
Cl30.7136 (2)0.5389 (4)0.26936 (8)0.1014 (8)
Cl40.2147 (2)0.6939 (2)0.38658 (6)0.0677 (5)
Cl50.0780 (2)0.3914 (2)0.22704 (6)0.0638 (4)
O10.9299 (7)0.7892 (6)0.48303 (17)0.0772 (15)
O20.6981 (6)0.9649 (6)0.39357 (17)0.0731 (14)
N10.7582 (6)0.6956 (6)0.41544 (18)0.0539 (13)
H1A0.82130.64090.43410.065*
N20.5692 (6)0.6866 (7)0.35613 (19)0.0600 (14)
H2A0.57970.79420.35560.072*
C11.1079 (9)0.9624 (10)0.5899 (3)0.0663 (18)
H1B1.12881.06400.60460.080*
C21.0313 (9)0.9593 (9)0.5469 (2)0.0625 (18)
H2B1.00041.05880.53250.075*
C31.0028 (8)0.8075 (8)0.5264 (2)0.0554 (16)
C41.0491 (8)0.6605 (8)0.5473 (2)0.0533 (15)
C51.1220 (8)0.6615 (9)0.5895 (2)0.0570 (16)
H5A1.15120.56210.60420.068*
C61.1506 (8)0.8169 (9)0.6096 (2)0.0581 (17)
C70.8657 (9)0.9301 (9)0.4602 (2)0.0610 (18)
H7A0.95671.00220.45010.073*
H7B0.79350.99420.48040.073*
C80.7649 (7)0.8658 (8)0.4188 (2)0.0529 (16)
C90.6611 (7)0.5973 (8)0.3853 (2)0.0555 (16)
C100.4545 (8)0.6081 (8)0.3258 (2)0.0546 (16)
C110.2845 (7)0.6078 (7)0.3353 (2)0.0470 (15)
C120.1656 (8)0.5411 (8)0.3066 (2)0.0537 (15)
H12A0.05190.54180.31400.064*
C130.2244 (7)0.4718 (7)0.2656 (2)0.0509 (15)
C140.3894 (7)0.4720 (9)0.2537 (2)0.0570 (16)
H14A0.42430.42750.22590.068*
C150.5041 (8)0.5400 (9)0.2839 (2)0.0589 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0936 (14)0.0606 (11)0.0888 (15)0.0047 (10)0.0382 (12)0.0091 (10)
Cl10.0808 (13)0.1205 (17)0.0562 (11)0.0190 (12)0.0094 (10)0.0146 (12)
Cl20.0963 (14)0.0579 (10)0.0916 (14)0.0038 (10)0.0091 (12)0.0167 (10)
Cl30.0469 (10)0.180 (2)0.0775 (14)0.0014 (12)0.0057 (10)0.0122 (15)
Cl40.0723 (11)0.0752 (11)0.0556 (10)0.0063 (9)0.0029 (9)0.0125 (9)
Cl50.0597 (10)0.0808 (12)0.0509 (9)0.0009 (9)0.0092 (8)0.0051 (8)
O10.104 (4)0.061 (3)0.067 (3)0.001 (3)0.031 (3)0.013 (3)
O20.078 (3)0.064 (3)0.077 (4)0.008 (2)0.017 (3)0.019 (3)
N10.050 (3)0.055 (3)0.056 (3)0.002 (2)0.009 (3)0.002 (3)
N20.053 (3)0.061 (3)0.066 (4)0.009 (3)0.020 (3)0.004 (3)
C10.072 (5)0.063 (4)0.064 (5)0.002 (4)0.004 (4)0.012 (4)
C20.071 (5)0.056 (4)0.061 (4)0.005 (3)0.004 (4)0.006 (3)
C30.053 (4)0.054 (4)0.059 (4)0.001 (3)0.007 (3)0.008 (3)
C40.051 (4)0.051 (4)0.058 (4)0.004 (3)0.002 (3)0.009 (3)
C50.052 (4)0.062 (4)0.057 (4)0.003 (3)0.000 (3)0.002 (3)
C60.043 (4)0.076 (5)0.055 (4)0.005 (3)0.002 (3)0.009 (4)
C70.075 (5)0.054 (4)0.054 (4)0.018 (4)0.004 (3)0.000 (3)
C80.040 (3)0.056 (4)0.062 (4)0.009 (3)0.004 (3)0.006 (3)
C90.043 (3)0.068 (4)0.055 (4)0.000 (3)0.009 (3)0.003 (3)
C100.050 (4)0.062 (4)0.052 (4)0.001 (3)0.009 (3)0.006 (3)
C110.050 (4)0.043 (3)0.047 (4)0.009 (3)0.000 (3)0.005 (3)
C120.049 (4)0.059 (4)0.053 (4)0.005 (3)0.001 (3)0.000 (3)
C130.047 (3)0.052 (4)0.054 (4)0.002 (3)0.007 (3)0.008 (3)
C140.047 (4)0.073 (4)0.051 (4)0.002 (3)0.001 (3)0.001 (3)
C150.041 (3)0.079 (5)0.057 (4)0.004 (3)0.005 (3)0.009 (3)
Geometric parameters (Å, º) top
S1—C91.629 (7)C2—C31.368 (9)
Cl1—C61.759 (7)C2—H2B0.9300
Cl2—C41.733 (6)C3—C41.370 (8)
Cl3—C151.721 (6)C4—C51.364 (9)
Cl4—C111.739 (6)C5—C61.388 (9)
Cl5—C131.744 (6)C5—H5A0.9300
O1—C71.402 (8)C7—C81.541 (9)
O1—C31.403 (8)C7—H7A0.9700
O2—C81.203 (7)C7—H7B0.9700
N1—C81.359 (8)C10—C111.381 (9)
N1—C91.409 (8)C10—C151.398 (9)
N1—H1A0.8600C11—C121.372 (9)
N2—C91.330 (8)C12—C131.400 (9)
N2—C101.417 (8)C12—H12A0.9300
N2—H2A0.8600C13—C141.358 (8)
C1—C61.337 (10)C14—C151.381 (8)
C1—C21.398 (9)C14—H14A0.9300
C1—H1B0.9300
C7—O1—C3119.9 (5)O1—C7—H7B110.2
C8—N1—C9128.3 (6)C8—C7—H7B110.2
C8—N1—H1A115.9H7A—C7—H7B108.5
C9—N1—H1A115.9O2—C8—N1126.3 (6)
C9—N2—C10121.3 (6)O2—C8—C7119.6 (6)
C9—N2—H2A119.3N1—C8—C7114.1 (6)
C10—N2—H2A119.3N2—C9—N1114.0 (6)
C6—C1—C2118.9 (7)N2—C9—S1127.8 (5)
C6—C1—H1B120.6N1—C9—S1118.2 (5)
C2—C1—H1B120.6C11—C10—C15116.9 (6)
C3—C2—C1118.8 (7)C11—C10—N2120.4 (6)
C3—C2—H2B120.6C15—C10—N2122.5 (6)
C1—C2—H2B120.6C12—C11—C10123.6 (6)
C2—C3—C4121.0 (6)C12—C11—Cl4117.4 (5)
C2—C3—O1123.8 (6)C10—C11—Cl4119.1 (5)
C4—C3—O1115.2 (6)C11—C12—C13116.5 (6)
C5—C4—C3120.8 (6)C11—C12—H12A121.8
C5—C4—Cl2119.5 (5)C13—C12—H12A121.8
C3—C4—Cl2119.6 (5)C14—C13—C12122.9 (6)
C4—C5—C6117.3 (6)C14—C13—Cl5118.7 (5)
C4—C5—H5A121.4C12—C13—Cl5118.4 (5)
C6—C5—H5A121.4C13—C14—C15118.3 (6)
C1—C6—C5123.2 (7)C13—C14—H14A120.8
C1—C6—Cl1119.5 (6)C15—C14—H14A120.8
C5—C6—Cl1117.3 (6)C14—C15—C10121.8 (6)
O1—C7—C8107.4 (5)C14—C15—Cl3118.7 (5)
O1—C7—H7A110.2C10—C15—Cl3119.5 (5)
C8—C7—H7A110.2
C6—C1—C2—C30.0 (10)C10—N2—C9—S13.1 (10)
C1—C2—C3—C40.5 (10)C8—N1—C9—N21.9 (9)
C1—C2—C3—O1178.7 (6)C8—N1—C9—S1176.4 (5)
C7—O1—C3—C26.8 (10)C9—N2—C10—C11101.4 (8)
C7—O1—C3—C4174.9 (6)C9—N2—C10—C1583.7 (8)
C2—C3—C4—C51.4 (10)C15—C10—C11—C121.8 (9)
O1—C3—C4—C5179.7 (6)N2—C10—C11—C12176.9 (5)
C2—C3—C4—Cl2178.4 (5)C15—C10—C11—Cl4179.0 (5)
O1—C3—C4—Cl20.0 (8)N2—C10—C11—Cl43.8 (8)
C3—C4—C5—C61.6 (10)C10—C11—C12—C130.5 (9)
Cl2—C4—C5—C6178.1 (5)Cl4—C11—C12—C13179.8 (4)
C2—C1—C6—C50.3 (11)C11—C12—C13—C141.2 (9)
C2—C1—C6—Cl1179.4 (5)C11—C12—C13—Cl5178.0 (4)
C4—C5—C6—C11.1 (10)C12—C13—C14—C151.6 (10)
C4—C5—C6—Cl1179.8 (5)Cl5—C13—C14—C15178.3 (5)
C3—O1—C7—C8169.0 (5)C13—C14—C15—C100.2 (10)
C9—N1—C8—O26.7 (11)C13—C14—C15—Cl3179.4 (5)
C9—N1—C8—C7171.6 (6)C11—C10—C15—C141.4 (9)
O1—C7—C8—O2179.5 (6)N2—C10—C15—C14176.4 (6)
O1—C7—C8—N12.0 (7)C11—C10—C15—Cl3179.0 (5)
C10—N2—C9—N1175.1 (6)N2—C10—C15—Cl34.0 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.862.052.516 (7)113
N2—H2A···O20.861.992.675 (7)136
C1—H1B···O2i0.932.573.326 (9)139
C5—H5A···S1ii0.932.873.716 (7)152
Symmetry codes: (i) y, x+2, z+1/4; (ii) y+1, x+1, z+1/4.
 

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