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Acta Cryst. (2008). E64, o2102    [ doi:10.1107/S1600536808032029 ]

1-(2,6-Difluorobenzoyl)-3-(2,3,5-trichlorophenyl)urea

S.-J. Yan, C. Huang, Y.-M. Li, Y.-Y. Yan and J. Lin

Abstract top

The asymmetric unit of the title compound, C14H7Cl3F2N2O2, contains two unique molecules. The 2,3,5-trichlorophenyl ring is almost coplanar with the urea group in both molecules, whereas the 2,6-difluorophenyl ring is twisted from the urea plane by 54.83 (10)° in one molecule and 60.58 (10)° in the other. An intramolecular N-H-O hydrogen bond stabilizes the molecular conformation. The crystal packing is formed by intermolecular N-H-O hydrogen bonds and F...F interactions [2.841 (2) Å].

Comment top

Derivatives of benzoylphenylureas (BPUs) are kind of insect growth regulators (IGRs), interferes the chitin synthesis in target pests, causing death or abortive development. BPUs posses high selectivity, low acute toxicity for mammals. At the time, the different groups on the phenyl that have different bioactivity. So research the configuration of the different compound is important to find more potent insecticide. The title compound (I) (Fig. 1), C14H7Cl3F2N2O2, which possesses high bioactivity to pests (Yan et al., 2003).

The geometrical parameters for (I) (Table 1) show the conjugation present: the length of the C1═O1 and C═O2 double bond is greater than that of a normal C═O double bond. The lengths of the C1—N1, C1—N2, C8—N2 bonds are shorter than that of normal C—N single bonds. The 2,3,5-trichlorophenyl ring of the title compound is almost coplanar with the urea group, whereas the 2,6-difluorophenyl ring is twisted from the urea plane by 60.58 (10)°. An intramolecular N—H—O hydrogen bond stabilizes the molecular conformation. The crystal packing of the title compound formed by intermolecular N—H—O hydrogen bonds and F···F bond (Fig 2).

Related literature top

For general background, see: Yan et al. (2003). For synthetic details, see: Lin et al. (2003, 2005). [Please check rephrasing]

Experimental top

A solution of 2,6-difluorobenzoyl isocyanate (II) (10 mmol, 1.0 equiv.) in 1,2-dichloroethane (10 ml) was added to a stirred solution of 2,3,5-trichloroaniline (III) (10 mmol, 1.0 equiv.) in dry 1,2-dichloroethane (20 ml) and stirred at room temperature for 24 hrs, the solvent was removed in vacuo and the residue was recrystallized with ethyl acetate to give desired compounds as white needle-crystals (I) in 93% yield (Lin et al., 2003; Lin et al., 2005). The desire product recrystallized from acetone (m.p. 517 K).

Refinement top

In the absence of significant anomalous dispersion effects, Freidel pairs were merged; the absolute configuration was assigned on the basis of the known configuration of the starting material. All H atoms were placed in idealized positions and refined with riding constraints, with C—H distances in the range 0.93–0.96 Å and with Uiso(H) = 1.2 or 1.5 times Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku, 2006); cell refinement: CrystalClear (Rigaku, 2006); data reduction: CrystalClear (Rigaku, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2006).

Figures top
[Figure 1] Fig. 1. View of (I) showing 30% displacement ellipsoids (arbitrary spheres for the H atoms).
[Figure 2] Fig. 2. The crystal packing of complex 1 showing the hydrogen bonds as broken lines. Symmetry code: (i) -x, -y + 1, -z + 1; (ii) -x + 1, -y + 1, -z.
[Figure 3] Fig. 3. The formation of the title compound.
1-(2,6-Difluorobenzoyl)-3-(2,3,5-trichlorophenyl)urea top
Crystal data top
C14H7Cl3F2N2O2Dx = 1.691 Mg m−3
Mr = 379.57Melting point: 517 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
a = 7.1669 (4) ÅCell parameters from 6247 reflections
b = 22.8228 (12) Åθ = 1.8–27.9°
c = 18.2885 (10) ŵ = 0.65 mm−1
β = 94.768 (2)°T = 113 K
V = 2981.1 (3) Å3Prism, colourless
Z = 80.24 × 0.14 × 0.12 mm
F(000) = 1520
Data collection top
Rigaku Saturn
diffractometer		7091 independent reflections
Radiation source: rotating anode6011 reflections with I > 2σ(I)
confocalRint = 0.050
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.8°
ω and φ scansh = −9→9
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2006)		k = −30→30
Tmin = 0.860, Tmax = 0.927l = −24→24
27779 measured reflections
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0419P)2 + 0.1727P]
where P = (Fo2 + 2Fc2)/3
7091 reflections(Δ/σ)max = 0.001
431 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C14H7Cl3F2N2O2V = 2981.1 (3) Å3
Mr = 379.57Z = 8
Monoclinic, P21/cMo Kα radiation
a = 7.1669 (4) ŵ = 0.65 mm−1
b = 22.8228 (12) ÅT = 113 K
c = 18.2885 (10) Å0.24 × 0.14 × 0.12 mm
β = 94.768 (2)°
Data collection top
Rigaku Saturn
diffractometer		7091 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2006)		6011 reflections with I > 2σ(I)
Tmin = 0.860, Tmax = 0.927Rint = 0.050
27779 measured reflectionsθmax = 27.9°
Refinement top
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089Δρmax = 0.29 e Å−3
S = 1.07Δρmin = −0.29 e Å−3
7091 reflectionsAbsolute structure: ?
431 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Cl10.03364 (7)0.50654 (2)0.15961 (2)0.02733 (12)
Cl2−0.07937 (7)0.40202 (2)0.05408 (2)0.03038 (12)
Cl3−0.17311 (7)0.26475 (2)0.28607 (3)0.03149 (12)
Cl40.34943 (7)0.283841 (19)0.19434 (2)0.02671 (11)
Cl50.36147 (7)0.28306 (2)0.36548 (2)0.03282 (13)
Cl60.54168 (7)0.51085 (2)0.37218 (2)0.02918 (12)
F1−0.17544 (16)0.64246 (6)0.45899 (7)0.0423 (3)
F20.44718 (15)0.65048 (6)0.39926 (7)0.0414 (3)
F30.04346 (14)0.34365 (5)−0.10568 (6)0.0303 (3)
F40.67828 (15)0.39222 (5)−0.10684 (6)0.0327 (3)
O1−0.02709 (19)0.44667 (6)0.42993 (6)0.0291 (3)
O20.14058 (17)0.59069 (6)0.31730 (6)0.0248 (3)
O30.51390 (18)0.48843 (5)0.09749 (6)0.0247 (3)
O40.33939 (17)0.32720 (5)0.01436 (6)0.0240 (3)
N10.0186 (2)0.48145 (7)0.31516 (8)0.0214 (3)
N20.0531 (2)0.54179 (7)0.41771 (8)0.0225 (3)
N30.4215 (2)0.39641 (7)0.12945 (8)0.0202 (3)
N40.4259 (2)0.42336 (7)0.00736 (8)0.0201 (3)
C10.0123 (3)0.48592 (8)0.38878 (9)0.0221 (4)
C2−0.0276 (2)0.43225 (8)0.27132 (9)0.0197 (4)
C3−0.0277 (2)0.43974 (8)0.19488 (9)0.0212 (4)
C4−0.0753 (2)0.39311 (8)0.14825 (9)0.0225 (4)
C5−0.1203 (2)0.33913 (8)0.17552 (10)0.0246 (4)
H5−0.15240.30730.14340.029*
C6−0.1176 (2)0.33237 (8)0.25079 (10)0.0226 (4)
C7−0.0722 (2)0.37795 (8)0.29909 (9)0.0215 (4)
H7−0.07170.37210.35050.026*
C80.1103 (2)0.59011 (8)0.38219 (9)0.0205 (4)
C90.1360 (2)0.64407 (8)0.42805 (9)0.0207 (4)
C10−0.0058 (3)0.66965 (9)0.46427 (10)0.0270 (4)
C110.0158 (3)0.72142 (9)0.50213 (11)0.0331 (5)
H11−0.08590.73820.52500.040*
C120.1879 (3)0.74862 (9)0.50626 (10)0.0314 (5)
H120.20580.78400.53340.038*
C130.3350 (3)0.72521 (8)0.47147 (10)0.0291 (4)
H130.45370.74400.47420.035*
C140.3047 (3)0.67426 (8)0.43304 (10)0.0252 (4)
C150.4574 (2)0.43923 (8)0.08133 (9)0.0193 (4)
C160.4364 (2)0.39918 (8)0.20631 (9)0.0193 (4)
C170.4017 (2)0.34714 (8)0.24369 (9)0.0205 (4)
C180.4090 (3)0.34667 (8)0.31982 (9)0.0227 (4)
C190.4524 (2)0.39688 (8)0.36001 (9)0.0241 (4)
H190.45740.39660.41210.029*
C200.4882 (2)0.44752 (8)0.32218 (9)0.0219 (4)
C210.4809 (2)0.44985 (8)0.24629 (9)0.0208 (4)
H210.50580.48540.22200.025*
C220.3743 (2)0.37040 (7)−0.02176 (9)0.0181 (4)
C230.3613 (2)0.36860 (7)−0.10363 (9)0.0185 (4)
C240.1951 (3)0.35418 (8)−0.14347 (9)0.0219 (4)
C250.1753 (3)0.35137 (8)−0.21846 (10)0.0265 (4)
H250.05830.3416−0.24380.032*
C260.3300 (3)0.36319 (8)−0.25635 (10)0.0290 (4)
H260.31890.3617−0.30840.035*
C270.5015 (3)0.37721 (8)−0.21950 (10)0.0281 (4)
H270.60820.3848−0.24560.034*
C280.5121 (2)0.37969 (8)−0.14440 (10)0.0224 (4)
H10.050 (3)0.5150 (9)0.2941 (11)0.033 (6)*
H20.053 (3)0.5433 (10)0.4626 (12)0.039 (6)*
H30.392 (3)0.3651 (9)0.1119 (12)0.036 (7)*
H40.441 (3)0.4529 (10)−0.0251 (12)0.045 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0356 (3)0.0278 (3)0.0190 (2)−0.0018 (2)0.00479 (18)−0.00021 (17)
Cl20.0346 (3)0.0393 (3)0.0171 (2)0.0015 (2)0.00166 (18)−0.00678 (18)
Cl30.0359 (3)0.0224 (3)0.0360 (3)−0.0003 (2)0.0023 (2)−0.00089 (19)
Cl40.0352 (3)0.0200 (2)0.0249 (2)−0.00355 (19)0.00249 (19)0.00437 (17)
Cl50.0422 (3)0.0311 (3)0.0256 (2)−0.0054 (2)0.0058 (2)0.01259 (19)
Cl60.0362 (3)0.0271 (3)0.0243 (2)0.0022 (2)0.00324 (19)−0.00380 (18)
F10.0232 (6)0.0534 (9)0.0519 (8)−0.0052 (6)0.0122 (5)−0.0179 (6)
F20.0237 (6)0.0504 (8)0.0518 (8)−0.0071 (6)0.0141 (5)−0.0213 (6)
F30.0211 (6)0.0405 (7)0.0298 (6)−0.0052 (5)0.0058 (5)0.0026 (5)
F40.0204 (6)0.0436 (7)0.0345 (6)−0.0041 (5)0.0055 (5)−0.0001 (5)
O10.0437 (8)0.0258 (7)0.0185 (6)−0.0046 (6)0.0073 (6)−0.0011 (5)
O20.0277 (7)0.0292 (7)0.0178 (6)−0.0046 (6)0.0037 (5)−0.0016 (5)
O30.0349 (8)0.0192 (7)0.0204 (6)−0.0058 (6)0.0052 (5)0.0014 (5)
O40.0319 (7)0.0177 (7)0.0229 (6)−0.0010 (5)0.0050 (5)0.0041 (5)
N10.0256 (9)0.0223 (9)0.0166 (7)−0.0023 (7)0.0035 (6)−0.0022 (6)
N20.0290 (9)0.0241 (9)0.0149 (7)−0.0038 (7)0.0048 (6)−0.0033 (6)
N30.0258 (8)0.0179 (8)0.0172 (7)−0.0012 (7)0.0031 (6)0.0026 (6)
N40.0257 (8)0.0174 (8)0.0176 (7)−0.0017 (6)0.0039 (6)0.0034 (6)
C10.0236 (10)0.0244 (10)0.0184 (8)−0.0008 (8)0.0027 (7)−0.0035 (7)
C20.0163 (9)0.0248 (10)0.0182 (8)0.0019 (7)0.0023 (7)−0.0053 (7)
C30.0180 (9)0.0248 (10)0.0212 (8)0.0025 (7)0.0032 (7)−0.0002 (7)
C40.0177 (9)0.0317 (11)0.0178 (8)0.0041 (8)0.0007 (7)−0.0059 (7)
C50.0216 (10)0.0263 (10)0.0259 (9)0.0025 (8)0.0026 (7)−0.0067 (7)
C60.0179 (9)0.0216 (10)0.0286 (9)0.0031 (7)0.0031 (7)−0.0017 (7)
C70.0182 (9)0.0265 (10)0.0198 (8)0.0029 (7)0.0015 (7)−0.0006 (7)
C80.0155 (9)0.0257 (10)0.0203 (8)0.0000 (7)0.0017 (7)0.0000 (7)
C90.0220 (9)0.0226 (10)0.0173 (8)0.0009 (7)0.0005 (7)0.0004 (7)
C100.0212 (10)0.0313 (11)0.0287 (10)0.0002 (8)0.0040 (8)−0.0021 (8)
C110.0374 (12)0.0305 (12)0.0325 (11)0.0085 (9)0.0101 (9)−0.0058 (8)
C120.0482 (13)0.0213 (10)0.0249 (9)0.0001 (9)0.0043 (9)−0.0016 (8)
C130.0349 (12)0.0274 (11)0.0251 (9)−0.0068 (9)0.0028 (8)0.0001 (8)
C140.0235 (10)0.0278 (11)0.0250 (9)−0.0001 (8)0.0052 (7)−0.0012 (7)
C150.0188 (9)0.0206 (10)0.0190 (8)0.0016 (7)0.0039 (7)0.0029 (7)
C160.0171 (9)0.0221 (9)0.0190 (8)0.0025 (7)0.0027 (7)0.0039 (7)
C170.0175 (9)0.0213 (10)0.0231 (9)0.0011 (7)0.0034 (7)0.0036 (7)
C180.0219 (9)0.0244 (10)0.0221 (9)0.0023 (8)0.0047 (7)0.0090 (7)
C190.0227 (10)0.0316 (11)0.0185 (8)0.0034 (8)0.0049 (7)0.0044 (7)
C200.0184 (9)0.0243 (10)0.0232 (9)0.0040 (7)0.0027 (7)−0.0003 (7)
C210.0199 (9)0.0206 (9)0.0223 (9)0.0028 (7)0.0039 (7)0.0047 (7)
C220.0156 (9)0.0177 (9)0.0214 (8)0.0036 (7)0.0032 (7)−0.0001 (7)
C230.0217 (9)0.0147 (9)0.0197 (8)0.0030 (7)0.0049 (7)0.0013 (6)
C240.0237 (10)0.0179 (9)0.0250 (9)−0.0003 (7)0.0075 (7)0.0028 (7)
C250.0301 (11)0.0239 (10)0.0249 (9)−0.0028 (8)−0.0017 (8)0.0020 (7)
C260.0461 (13)0.0223 (10)0.0192 (9)−0.0019 (9)0.0056 (8)−0.0004 (7)
C270.0328 (11)0.0251 (11)0.0283 (10)−0.0008 (8)0.0142 (8)0.0011 (8)
C280.0209 (9)0.0203 (10)0.0265 (9)0.0010 (7)0.0040 (7)−0.0014 (7)
Geometric parameters (Å, °) top
Cl1—C31.7265 (18)C5—H50.9500
Cl2—C41.7320 (18)C6—C71.386 (2)
Cl3—C61.7317 (19)C7—H70.9500
Cl4—C171.7280 (18)C8—C91.493 (2)
Cl5—C181.7228 (18)C9—C101.387 (2)
Cl6—C201.7362 (19)C9—C141.388 (3)
F1—C101.361 (2)C10—C111.372 (3)
F2—C141.350 (2)C11—C121.377 (3)
F3—C241.357 (2)C11—H110.9500
F4—C281.355 (2)C12—C131.383 (3)
O1—C11.218 (2)C12—H120.9500
O2—C81.224 (2)C13—C141.367 (3)
O3—C151.222 (2)C13—H130.9500
O4—C221.224 (2)C16—C211.391 (2)
N1—C11.355 (2)C16—C171.403 (2)
N1—C21.403 (2)C17—C181.389 (2)
N1—H10.89 (2)C18—C191.383 (3)
N2—C81.360 (2)C19—C201.382 (2)
N2—C11.402 (2)C19—H190.9500
N2—H20.82 (2)C20—C211.386 (2)
N3—C151.354 (2)C21—H210.9500
N3—C161.402 (2)C22—C231.493 (2)
N3—H30.80 (2)C23—C241.383 (2)
N4—C221.360 (2)C23—C281.386 (2)
N4—C151.401 (2)C24—C251.369 (2)
N4—H40.91 (2)C25—C261.382 (3)
C2—C71.387 (2)C25—H250.9500
C2—C31.408 (2)C26—C271.389 (3)
C3—C41.388 (2)C26—H260.9500
C4—C51.377 (3)C27—C281.370 (2)
C5—C61.384 (2)C27—H270.9500
C1—N1—C2127.03 (16)C14—C13—C12118.06 (19)
C1—N1—H1113.2 (13)C14—C13—H13121.0
C2—N1—H1119.6 (13)C12—C13—H13121.0
C8—N2—C1128.23 (15)F2—C14—C13118.90 (17)
C8—N2—H2117.9 (15)F2—C14—C9117.26 (16)
C1—N2—H2113.4 (15)C13—C14—C9123.81 (18)
C15—N3—C16128.03 (16)O3—C15—N3125.68 (16)
C15—N3—H3116.0 (16)O3—C15—N4119.67 (15)
C16—N3—H3115.9 (16)N3—C15—N4114.65 (15)
C22—N4—C15128.67 (14)C21—C16—N3124.02 (15)
C22—N4—H4116.5 (14)C21—C16—C17119.34 (16)
C15—N4—H4114.8 (14)N3—C16—C17116.64 (15)
O1—C1—N1125.96 (17)C18—C17—C16120.11 (16)
O1—C1—N2119.17 (15)C18—C17—Cl4120.36 (14)
N1—C1—N2114.85 (15)C16—C17—Cl4119.53 (13)
C7—C2—N1123.82 (15)C19—C18—C17120.96 (16)
C7—C2—C3119.40 (16)C19—C18—Cl5119.04 (13)
N1—C2—C3116.79 (16)C17—C18—Cl5120.00 (14)
C4—C3—C2119.77 (17)C20—C19—C18118.02 (16)
C4—C3—Cl1120.30 (14)C20—C19—H19121.0
C2—C3—Cl1119.93 (14)C18—C19—H19121.0
C5—C4—C3121.06 (16)C19—C20—C21122.72 (17)
C5—C4—Cl2118.68 (14)C19—C20—Cl6118.33 (13)
C3—C4—Cl2120.25 (15)C21—C20—Cl6118.94 (14)
C4—C5—C6118.41 (17)C20—C21—C16118.84 (16)
C4—C5—H5120.8C20—C21—H21120.6
C6—C5—H5120.8C16—C21—H21120.6
C5—C6—C7122.24 (17)O4—C22—N4124.46 (16)
C5—C6—Cl3119.04 (14)O4—C22—C23121.38 (15)
C7—C6—Cl3118.72 (14)N4—C22—C23114.16 (14)
C6—C7—C2119.11 (16)C24—C23—C28115.82 (16)
C6—C7—H7120.4C24—C23—C22120.91 (15)
C2—C7—H7120.4C28—C23—C22123.25 (16)
O2—C8—N2123.81 (17)F3—C24—C25118.75 (16)
O2—C8—C9120.80 (16)F3—C24—C23117.71 (15)
N2—C8—C9115.39 (15)C25—C24—C23123.53 (17)
C10—C9—C14115.37 (17)C24—C25—C26118.19 (17)
C10—C9—C8123.65 (16)C24—C25—H25120.9
C14—C9—C8120.86 (16)C26—C25—H25120.9
F1—C10—C11119.38 (17)C25—C26—C27121.07 (17)
F1—C10—C9117.38 (17)C25—C26—H26119.5
C11—C10—C9123.19 (18)C27—C26—H26119.5
C10—C11—C12118.59 (19)C28—C27—C26117.96 (17)
C10—C11—H11120.7C28—C27—H27121.0
C12—C11—H11120.7C26—C27—H27121.0
C11—C12—C13120.94 (19)F4—C28—C27119.34 (16)
C11—C12—H12119.5F4—C28—C23117.21 (15)
C13—C12—H12119.5C27—C28—C23123.43 (17)
C2—N1—C1—O13.5 (3)C16—N3—C15—O31.6 (3)
C2—N1—C1—N2−175.52 (16)C16—N3—C15—N4−178.88 (16)
C8—N2—C1—O1175.84 (18)C22—N4—C15—O3175.83 (17)
C8—N2—C1—N1−5.1 (3)C22—N4—C15—N3−3.8 (3)
C1—N1—C2—C7−6.0 (3)C15—N3—C16—C214.5 (3)
C1—N1—C2—C3173.97 (17)C15—N3—C16—C17−176.16 (17)
C7—C2—C3—C41.1 (3)C21—C16—C17—C181.0 (3)
N1—C2—C3—C4−178.90 (16)N3—C16—C17—C18−178.33 (16)
C7—C2—C3—Cl1−178.25 (13)C21—C16—C17—Cl4−179.16 (13)
N1—C2—C3—Cl11.8 (2)N3—C16—C17—Cl41.5 (2)
C2—C3—C4—C5−0.9 (3)C16—C17—C18—C19−0.8 (3)
Cl1—C3—C4—C5178.44 (14)Cl4—C17—C18—C19179.40 (14)
C2—C3—C4—Cl2179.03 (13)C16—C17—C18—Cl5178.62 (14)
Cl1—C3—C4—Cl2−1.7 (2)Cl4—C17—C18—Cl5−1.2 (2)
C3—C4—C5—C60.2 (3)C17—C18—C19—C200.0 (3)
Cl2—C4—C5—C6−179.71 (13)Cl5—C18—C19—C20−179.39 (13)
C4—C5—C6—C70.3 (3)C18—C19—C20—C210.5 (3)
C4—C5—C6—Cl3−179.82 (13)C18—C19—C20—Cl6179.69 (14)
C5—C6—C7—C2−0.1 (3)C19—C20—C21—C16−0.3 (3)
Cl3—C6—C7—C2−179.98 (13)Cl6—C20—C21—C16−179.44 (13)
N1—C2—C7—C6179.38 (16)N3—C16—C21—C20178.79 (16)
C3—C2—C7—C6−0.6 (3)C17—C16—C21—C20−0.5 (3)
C1—N2—C8—O2−2.4 (3)C15—N4—C22—O42.9 (3)
C1—N2—C8—C9177.94 (17)C15—N4—C22—C23−177.49 (16)
O2—C8—C9—C10121.2 (2)O4—C22—C23—C2458.7 (2)
N2—C8—C9—C10−59.1 (2)N4—C22—C23—C24−120.91 (18)
O2—C8—C9—C14−54.5 (2)O4—C22—C23—C28−119.8 (2)
N2—C8—C9—C14125.14 (18)N4—C22—C23—C2860.5 (2)
C14—C9—C10—F1178.06 (16)C28—C23—C24—F3−179.26 (15)
C8—C9—C10—F12.1 (3)C22—C23—C24—F32.1 (2)
C14—C9—C10—C110.6 (3)C28—C23—C24—C25−0.8 (3)
C8—C9—C10—C11−175.38 (18)C22—C23—C24—C25−179.46 (17)
F1—C10—C11—C12−179.34 (17)F3—C24—C25—C26178.90 (16)
C9—C10—C11—C12−1.9 (3)C23—C24—C25—C260.5 (3)
C10—C11—C12—C131.7 (3)C24—C25—C26—C270.4 (3)
C11—C12—C13—C14−0.1 (3)C25—C26—C27—C28−0.8 (3)
C12—C13—C14—F2−179.42 (17)C26—C27—C28—F4178.83 (16)
C12—C13—C14—C9−1.3 (3)C26—C27—C28—C230.4 (3)
C10—C9—C14—F2179.24 (16)C24—C23—C28—F4−178.09 (15)
C8—C9—C14—F2−4.7 (3)C22—C23—C28—F40.5 (3)
C10—C9—C14—C131.1 (3)C24—C23—C28—C270.4 (3)
C8—C9—C14—C13177.14 (17)C22—C23—C28—C27178.97 (17)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.89 (2)2.46 (2)2.9126 (15)111.8 (16)
N1—H1···O20.89 (2)1.88 (2)2.641 (2)141.5 (19)
N2—H2···O1i0.82 (2)2.00 (2)2.8205 (19)173 (2)
N3—H3···Cl40.80 (2)2.43 (2)2.8944 (16)118.2 (19)
N3—H3···O40.80 (2)1.99 (2)2.658 (2)140 (2)
N4—H4···O3ii0.91 (2)1.93 (2)2.8378 (18)176 (2)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.89 (2)2.46 (2)2.9126 (15)111.8 (16)
N1—H1···O20.89 (2)1.88 (2)2.641 (2)141.5 (19)
N2—H2···O1i0.82 (2)2.00 (2)2.8205 (19)173 (2)
N3—H3···Cl40.80 (2)2.43 (2)2.8944 (16)118.2 (19)
N3—H3···O40.80 (2)1.99 (2)2.658 (2)140 (2)
N4—H4···O3ii0.91 (2)1.93 (2)2.8378 (18)176 (2)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z.
Acknowledgements top

This project was supported by the 11th Five-Year Construction Item for Yunnan University Teachers (grant No. 0030-WX069051).

references
References top

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Yan, S. J., Lin, J., Bi, F. C., Rang, L. J. & Cheng, Y. P. (2003). J. Yunnan Univ. 25, 438–441.