supplementary materials


hg2419 scheme

Acta Cryst. (2008). E64, o1500    [ doi:10.1107/S1600536808021168 ]

Bis[4-(chloroacetyl)phenyl] ether

F.-L. Meng and L.-Z. Xu

Abstract top

The title compound, C16H12Cl2O3, crystallizes with two independent molecules in the asymmetric unit. The dihedral angles between the planes of the benzene rings in the two independent molecules are 68.65 (2) and 68.47 (3)°. The short distance of 3.899 (5) Å between the centroids of the benzene rings of neighbouring molecules indicate [pi]-[pi] interactions. The crystal structure is stabilized by a network of intermolecular C-H...O hydrogen bonds.

Comment top

The title compound, was obtained unintentionally as an intermediate for the synthesis of Triazole compounds. Triazole compounds had been found to show wide spread biological activities. Many of them had been developed and used as fungicides, plant growth regulators and medicine. (Fujimoto & Quinn, 1988) we report here the crystal structure of (I).

The title compound, crystallizes in space group with two independent molecules in the asymmetric unit (Figs. 1,2). All bond lengths and angles are normal and in a good agreement with those reported previously (Grossert et al., 1984). The angles of C6—O2—C9 and C22—O15—C25 in the two independent molecules are 119.06 (2) and 120.07 (3)°. However, the two benzene rings are not coplanar planar. The dihedral angles between the planes of benzene rings in the two independent molecules are 68.65 (2) and 68.47 (3)°. π-π stacking interactions are present in the structure. The crystal structure is stabilized by a network of hydrogen bonds and van der Waals interations.

Related literature top

For biological activity, see: Fujimoto & Quinn (1988). For similar structures, see: Grossert et al. (1984). For the preparation, see: Edward & Sibelle (1963).

Experimental top

A mixture of 1-phenoxybenzene(5.0 mmol) and anhydrous aluminium chloride were added to a solution of 50 mL of dry dichloromethane in a flask equipped with stirrer and reflux condenser. Chloroacetyl chloride (10.0 mmol) was slowly added from a dropping-funnel to the boiling mixture during 30 minutes After this addition, the reaction mixture was heated with strring for two hours at boiling. The mixture was poured into ice-water and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, and dichloromethane was distilled off. The residue was purified by a column chromatography to obtain the title compound (10.1 g, yield 62%).(Edward & Sibelle, 1963). Single crystals suitable for X-ray measurement were obtained by recrystallization from petroleum ether at room temperature. mp.383-384 K.

Refinement top

All H atoms were found on difference maps, H atoms were placed in calculated positions, with C—H = 0.93 or 0.97Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2 times Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the first molecule of the title compound (I), with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the second molecule of the title compound (I), with displacement ellipsoids drawn at the 50% probability level.
[Figure 3] Fig. 3. A packing diagram of the molecule of the title compound, viewed down c axis. Hydrogen bonds are shown as dashed lines.
Bis[4-(chloroacetyl)phenyl] ether top
Crystal data top
C16H12Cl2O3F000 = 1328
Mr = 323.16Dx = 1.508 Mg m3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7912 reflections
a = 12.597 (3) Åθ = 1.7–27.9º
b = 9.2042 (18) ŵ = 0.46 mm1
c = 25.320 (5) ÅT = 113 (2) K
β = 104.18 (3)ºPlatelet, colorless
V = 2846.3 (10) Å30.24 × 0.18 × 0.04 mm
Z = 8
Data collection top
Rigaku Saturn
diffractometer
6778 independent reflections
Radiation source: Rotating Anode5751 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.039
T = 113(2) Kθmax = 27.9º
ω scansθmin = 1.7º
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
h = 16→16
Tmin = 0.897, Tmax = 0.982k = 12→12
20200 measured reflectionsl = 19→33
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.109  ' w = 1/[σ2(Fo2) + (0.0573P)2 + 0.5125P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
6778 reflectionsΔρmax = 0.64 e Å3
379 parametersΔρmin = 0.71 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C16H12Cl2O3V = 2846.3 (10) Å3
Mr = 323.16Z = 8
Monoclinic, P21/nMo Kα
a = 12.597 (3) ŵ = 0.46 mm1
b = 9.2042 (18) ÅT = 113 (2) K
c = 25.320 (5) Å0.24 × 0.18 × 0.04 mm
β = 104.18 (3)º
Data collection top
Rigaku Saturn
diffractometer
6778 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
5751 reflections with I > 2σ(I)
Tmin = 0.897, Tmax = 0.982Rint = 0.039
20200 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040379 parameters
wR(F2) = 0.109H-atom parameters constrained
S = 1.09Δρmax = 0.64 e Å3
6778 reflectionsΔρmin = 0.71 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
Cl10.28427 (4)0.08039 (4)1.058487 (17)0.02603 (11)
Cl20.47207 (5)0.29171 (9)0.48766 (2)0.0642 (2)
Cl30.35388 (5)0.50683 (6)0.343823 (18)0.04085 (14)
Cl40.12503 (4)0.05428 (4)0.234906 (17)0.02692 (11)
O10.43216 (10)0.20625 (13)0.99868 (5)0.0249 (3)
O20.48320 (10)0.08423 (12)0.77943 (5)0.0242 (3)
O30.38823 (12)0.35813 (17)0.58187 (6)0.0420 (4)
O40.33203 (11)0.32837 (12)0.24803 (5)0.0265 (3)
O50.31588 (11)0.62621 (12)0.02015 (5)0.0267 (3)
O60.26773 (10)0.30081 (13)0.20407 (5)0.0262 (3)
C10.30788 (15)0.00873 (19)0.99746 (7)0.0245 (4)
H1A0.33710.08891.00430.029*
H1B0.23870.00230.97030.029*
C20.38694 (13)0.10026 (17)0.97496 (6)0.0190 (3)
C30.40671 (13)0.05153 (16)0.92204 (6)0.0182 (3)
C40.36589 (14)0.07866 (17)0.89682 (7)0.0217 (3)
H40.32210.13740.91260.026*
C50.38986 (14)0.12143 (18)0.84859 (7)0.0225 (3)
H50.36300.20870.83210.027*
C60.45426 (13)0.03237 (17)0.82532 (7)0.0199 (3)
C70.49463 (14)0.09832 (18)0.84929 (7)0.0235 (3)
H70.53710.15770.83290.028*
C80.47138 (13)0.13953 (18)0.89752 (7)0.0219 (3)
H80.49890.22660.91390.026*
C90.47682 (13)0.00766 (17)0.73577 (7)0.0203 (3)
C100.54686 (13)0.02410 (18)0.70265 (7)0.0226 (3)
H100.59820.09830.71200.027*
C110.53955 (13)0.05576 (18)0.65557 (7)0.0225 (3)
H110.58580.03450.63310.027*
C120.46343 (13)0.16782 (18)0.64155 (7)0.0209 (3)
C130.39497 (13)0.19865 (18)0.67615 (7)0.0210 (3)
H130.34450.27400.66730.025*
C140.40084 (13)0.11975 (17)0.72302 (7)0.0209 (3)
H140.35490.14100.74570.025*
C150.44999 (14)0.2549 (2)0.59125 (7)0.0268 (4)
C160.51660 (15)0.2091 (2)0.55157 (7)0.0301 (4)
H16A0.51200.10450.54710.036*
H16B0.59280.23390.56680.036*
C170.35304 (14)0.57407 (18)0.27839 (6)0.0223 (3)
H17A0.29510.64550.26780.027*
H17B0.42210.62240.27980.027*
C180.33593 (12)0.45517 (17)0.23596 (6)0.0188 (3)
C190.32804 (12)0.50180 (16)0.17890 (6)0.0173 (3)
C200.35688 (13)0.40140 (17)0.14305 (7)0.0203 (3)
H200.37960.30870.15540.024*
C210.35203 (14)0.43836 (17)0.08969 (7)0.0221 (3)
H210.37280.37230.06630.027*
C220.31543 (14)0.57643 (17)0.07159 (6)0.0206 (3)
C230.28435 (14)0.67673 (17)0.10592 (7)0.0211 (3)
H230.25840.76780.09290.025*
C240.29241 (13)0.63979 (17)0.15968 (6)0.0188 (3)
H240.27390.70750.18320.023*
C250.29220 (14)0.53207 (17)0.02388 (6)0.0211 (3)
C260.20681 (14)0.43327 (18)0.03160 (7)0.0222 (3)
H260.16650.42310.00560.027*
C270.18197 (13)0.34955 (18)0.07870 (7)0.0206 (3)
H270.12520.28240.08400.025*
C280.24164 (13)0.36558 (17)0.11809 (6)0.0183 (3)
C290.32770 (14)0.46592 (17)0.10904 (7)0.0214 (3)
H290.36780.47740.13510.026*
C300.35398 (14)0.54819 (17)0.06193 (7)0.0221 (3)
H300.41220.61330.05590.027*
C310.21875 (13)0.27894 (17)0.16926 (6)0.0189 (3)
C320.13163 (14)0.16104 (18)0.17589 (7)0.0223 (3)
H32A0.06090.20590.17830.027*
H32B0.14790.09870.14400.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0326 (2)0.0240 (2)0.0234 (2)0.00095 (16)0.01054 (17)0.00148 (16)
Cl20.0477 (3)0.1203 (6)0.0283 (3)0.0339 (4)0.0166 (2)0.0261 (3)
Cl30.0682 (4)0.0373 (3)0.0204 (2)0.0108 (2)0.0173 (2)0.00209 (18)
Cl40.0334 (2)0.0237 (2)0.0241 (2)0.00443 (17)0.00773 (17)0.00560 (15)
O10.0278 (6)0.0218 (6)0.0239 (6)0.0053 (5)0.0036 (5)0.0020 (5)
O20.0288 (6)0.0204 (6)0.0260 (6)0.0025 (5)0.0118 (5)0.0015 (5)
O30.0343 (8)0.0576 (9)0.0377 (8)0.0234 (7)0.0157 (6)0.0208 (7)
O40.0370 (7)0.0181 (6)0.0255 (6)0.0017 (5)0.0100 (5)0.0027 (5)
O50.0445 (8)0.0182 (6)0.0190 (6)0.0065 (5)0.0109 (5)0.0015 (5)
O60.0318 (7)0.0273 (6)0.0222 (6)0.0031 (5)0.0120 (5)0.0025 (5)
C10.0286 (9)0.0235 (8)0.0221 (8)0.0047 (7)0.0077 (7)0.0036 (7)
C20.0172 (7)0.0181 (7)0.0190 (8)0.0023 (6)0.0005 (6)0.0026 (6)
C30.0175 (7)0.0171 (7)0.0184 (7)0.0019 (6)0.0016 (6)0.0023 (6)
C40.0212 (8)0.0189 (8)0.0256 (8)0.0034 (6)0.0071 (7)0.0015 (6)
C50.0223 (8)0.0166 (8)0.0284 (9)0.0013 (6)0.0061 (7)0.0017 (6)
C60.0182 (8)0.0211 (8)0.0205 (8)0.0028 (6)0.0050 (6)0.0014 (6)
C70.0237 (8)0.0237 (8)0.0233 (8)0.0055 (7)0.0058 (7)0.0026 (7)
C80.0211 (8)0.0193 (8)0.0227 (8)0.0027 (6)0.0005 (6)0.0008 (6)
C90.0195 (8)0.0204 (8)0.0209 (8)0.0024 (6)0.0049 (6)0.0016 (6)
C100.0178 (8)0.0221 (8)0.0284 (9)0.0030 (6)0.0064 (7)0.0012 (7)
C110.0169 (8)0.0281 (9)0.0242 (8)0.0006 (6)0.0081 (6)0.0033 (7)
C120.0166 (8)0.0260 (8)0.0195 (8)0.0009 (6)0.0031 (6)0.0029 (6)
C130.0172 (8)0.0206 (8)0.0242 (8)0.0022 (6)0.0033 (6)0.0031 (6)
C140.0186 (8)0.0229 (8)0.0224 (8)0.0007 (6)0.0072 (6)0.0041 (6)
C150.0177 (8)0.0386 (10)0.0235 (9)0.0038 (7)0.0040 (6)0.0021 (7)
C160.0253 (9)0.0436 (11)0.0223 (9)0.0040 (8)0.0077 (7)0.0036 (8)
C170.0280 (9)0.0234 (8)0.0157 (7)0.0015 (7)0.0052 (6)0.0001 (6)
C180.0149 (7)0.0201 (8)0.0211 (8)0.0007 (6)0.0038 (6)0.0005 (6)
C190.0169 (7)0.0173 (7)0.0179 (7)0.0035 (6)0.0050 (6)0.0017 (6)
C200.0223 (8)0.0160 (7)0.0223 (8)0.0005 (6)0.0047 (6)0.0008 (6)
C210.0255 (8)0.0194 (8)0.0222 (8)0.0011 (6)0.0076 (7)0.0040 (6)
C220.0236 (8)0.0209 (8)0.0175 (7)0.0063 (6)0.0053 (6)0.0004 (6)
C230.0253 (8)0.0155 (7)0.0222 (8)0.0025 (6)0.0056 (7)0.0003 (6)
C240.0213 (8)0.0155 (7)0.0205 (8)0.0027 (6)0.0072 (6)0.0022 (6)
C250.0292 (9)0.0168 (7)0.0166 (8)0.0010 (6)0.0043 (6)0.0006 (6)
C260.0255 (9)0.0235 (8)0.0195 (8)0.0005 (7)0.0093 (7)0.0013 (6)
C270.0201 (8)0.0210 (8)0.0204 (8)0.0006 (6)0.0046 (6)0.0014 (6)
C280.0190 (8)0.0175 (7)0.0179 (8)0.0030 (6)0.0037 (6)0.0026 (6)
C290.0259 (9)0.0197 (8)0.0202 (8)0.0000 (6)0.0089 (7)0.0020 (6)
C300.0251 (9)0.0186 (8)0.0228 (8)0.0041 (6)0.0062 (7)0.0021 (6)
C310.0195 (8)0.0182 (7)0.0189 (8)0.0045 (6)0.0044 (6)0.0020 (6)
C320.0245 (9)0.0220 (8)0.0213 (8)0.0001 (6)0.0072 (7)0.0025 (6)
Geometric parameters (Å, °) top
Cl1—C11.7711 (17)C13—C141.378 (2)
Cl2—C161.7511 (19)C13—H130.9300
Cl3—C171.7661 (17)C14—H140.9300
Cl4—C321.7732 (17)C15—C161.518 (2)
O1—C21.212 (2)C16—H16A0.9700
O2—C91.379 (2)C16—H16B0.9700
O2—C61.385 (2)C17—C181.512 (2)
O3—C151.214 (2)C17—H17A0.9700
O4—C181.2105 (19)C17—H17B0.9700
O5—C221.3821 (19)C18—C191.487 (2)
O5—C251.3854 (19)C19—C241.394 (2)
O6—C311.2104 (19)C19—C201.404 (2)
C1—C21.518 (2)C20—C211.380 (2)
C1—H1A0.9700C20—H200.9300
C1—H1B0.9700C21—C221.391 (2)
C2—C31.491 (2)C21—H210.9300
C3—C41.395 (2)C22—C231.389 (2)
C3—C81.397 (2)C23—C241.382 (2)
C4—C51.385 (2)C23—H230.9300
C4—H40.9300C24—H240.9300
C5—C61.383 (2)C25—C261.385 (2)
C5—H50.9300C25—C301.387 (2)
C6—C71.387 (2)C26—C271.390 (2)
C7—C81.377 (2)C26—H260.9300
C7—H70.9300C27—C281.396 (2)
C8—H80.9300C27—H270.9300
C9—C101.389 (2)C28—C291.400 (2)
C9—C141.390 (2)C28—C311.488 (2)
C10—C111.384 (2)C29—C301.383 (2)
C10—H100.9300C29—H290.9300
C11—C121.394 (2)C30—H300.9300
C11—H110.9300C31—C321.523 (2)
C12—C131.401 (2)C32—H32A0.9700
C12—C151.479 (2)C32—H32B0.9700
Cg2···Cg4i3.899 (5)
C9—O2—C6119.06 (12)H16A—C16—H16B107.8
C22—O5—C25120.07 (12)C18—C17—Cl3112.34 (12)
C2—C1—Cl1112.74 (12)C18—C17—H17A109.1
C2—C1—H1A109.0Cl3—C17—H17A109.1
Cl1—C1—H1A109.0C18—C17—H17B109.1
C2—C1—H1B109.0Cl3—C17—H17B109.1
Cl1—C1—H1B109.0H17A—C17—H17B107.9
H1A—C1—H1B107.8O4—C18—C19121.77 (14)
O1—C2—C3121.72 (15)O4—C18—C17121.73 (15)
O1—C2—C1122.19 (15)C19—C18—C17116.46 (13)
C3—C2—C1116.09 (14)C24—C19—C20119.07 (14)
C4—C3—C8118.95 (15)C24—C19—C18122.77 (14)
C4—C3—C2123.07 (14)C20—C19—C18118.15 (14)
C8—C3—C2117.96 (14)C21—C20—C19120.95 (15)
C5—C4—C3120.80 (15)C21—C20—H20119.5
C5—C4—H4119.6C19—C20—H20119.5
C3—C4—H4119.6C20—C21—C22118.65 (15)
C6—C5—C4118.99 (15)C20—C21—H21120.7
C6—C5—H5120.5C22—C21—H21120.7
C4—C5—H5120.5O5—C22—C23115.89 (14)
C5—C6—O2117.11 (14)O5—C22—C21122.41 (14)
C5—C6—C7121.22 (15)C23—C22—C21121.51 (15)
O2—C6—C7121.50 (14)C24—C23—C22119.28 (15)
C8—C7—C6119.49 (15)C24—C23—H23120.4
C8—C7—H7120.3C22—C23—H23120.4
C6—C7—H7120.3C23—C24—C19120.50 (14)
C7—C8—C3120.54 (16)C23—C24—H24119.8
C7—C8—H8119.7C19—C24—H24119.8
C3—C8—H8119.7O5—C25—C26122.06 (15)
O2—C9—C10115.73 (14)O5—C25—C30116.43 (15)
O2—C9—C14122.89 (14)C26—C25—C30121.37 (15)
C10—C9—C14121.25 (15)C25—C26—C27119.27 (15)
C11—C10—C9119.34 (15)C25—C26—H26120.4
C11—C10—H10120.3C27—C26—H26120.4
C9—C10—H10120.3C26—C27—C28120.47 (15)
C10—C11—C12120.59 (15)C26—C27—H27119.8
C10—C11—H11119.7C28—C27—H27119.8
C12—C11—H11119.7C27—C28—C29118.93 (15)
C11—C12—C13118.76 (15)C27—C28—C31122.82 (15)
C11—C12—C15123.15 (15)C29—C28—C31118.24 (14)
C13—C12—C15118.08 (15)C30—C29—C28120.97 (15)
C14—C13—C12121.37 (15)C30—C29—H29119.5
C14—C13—H13119.3C28—C29—H29119.5
C12—C13—H13119.3C29—C30—C25118.96 (15)
C13—C14—C9118.67 (15)C29—C30—H30120.5
C13—C14—H14120.7C25—C30—H30120.5
C9—C14—H14120.7O6—C31—C28121.36 (15)
O3—C15—C12121.69 (15)O6—C31—C32121.35 (14)
O3—C15—C16121.29 (16)C28—C31—C32117.29 (13)
C12—C15—C16117.02 (15)C31—C32—Cl4111.81 (11)
C15—C16—Cl2112.78 (13)C31—C32—H32A109.3
C15—C16—H16A109.0Cl4—C32—H32A109.3
Cl2—C16—H16A109.0C31—C32—H32B109.3
C15—C16—H16B109.0Cl4—C32—H32B109.3
Cl2—C16—H16B109.0H32A—C32—H32B107.9
Cl1—C1—C2—O13.6 (2)Cl3—C17—C18—O45.2 (2)
Cl1—C1—C2—C3176.92 (11)Cl3—C17—C18—C19176.87 (11)
O1—C2—C3—C4172.50 (15)O4—C18—C19—C24155.76 (16)
C1—C2—C3—C47.0 (2)C17—C18—C19—C2426.3 (2)
O1—C2—C3—C86.0 (2)O4—C18—C19—C2023.6 (2)
C1—C2—C3—C8174.55 (15)C17—C18—C19—C20154.32 (15)
C8—C3—C4—C50.8 (2)C24—C19—C20—C211.0 (2)
C2—C3—C4—C5177.69 (15)C18—C19—C20—C21179.55 (15)
C3—C4—C5—C60.6 (2)C19—C20—C21—C221.5 (2)
C4—C5—C6—O2175.19 (14)C25—O5—C22—C23148.34 (16)
C4—C5—C6—C70.2 (3)C25—O5—C22—C2136.6 (2)
C9—O2—C6—C5135.95 (15)C20—C21—C22—O5174.95 (15)
C9—O2—C6—C748.7 (2)C20—C21—C22—C230.2 (2)
C5—C6—C7—C80.8 (3)O5—C22—C23—C24173.52 (14)
O2—C6—C7—C8174.35 (15)C21—C22—C23—C241.6 (2)
C6—C7—C8—C30.7 (3)C22—C23—C24—C192.0 (2)
C4—C3—C8—C70.1 (2)C20—C19—C24—C230.7 (2)
C2—C3—C8—C7178.42 (15)C18—C19—C24—C23178.62 (14)
C6—O2—C9—C10153.50 (15)C22—O5—C25—C2643.4 (2)
C6—O2—C9—C1430.5 (2)C22—O5—C25—C30140.70 (16)
O2—C9—C10—C11174.92 (14)O5—C25—C26—C27175.11 (15)
C14—C9—C10—C111.1 (2)C30—C25—C26—C270.6 (3)
C9—C10—C11—C120.5 (3)C25—C26—C27—C280.6 (2)
C10—C11—C12—C130.4 (2)C26—C27—C28—C290.8 (2)
C10—C11—C12—C15178.62 (16)C26—C27—C28—C31179.98 (15)
C11—C12—C13—C140.7 (2)C27—C28—C29—C300.1 (2)
C15—C12—C13—C14178.35 (15)C31—C28—C29—C30179.09 (15)
C12—C13—C14—C90.1 (2)C28—C29—C30—C251.3 (2)
O2—C9—C14—C13174.94 (14)O5—C25—C30—C29174.43 (14)
C10—C9—C14—C130.8 (2)C26—C25—C30—C291.5 (3)
C11—C12—C15—O3174.96 (18)C27—C28—C31—O6175.80 (15)
C13—C12—C15—O36.0 (3)C29—C28—C31—O65.0 (2)
C11—C12—C15—C165.3 (3)C27—C28—C31—C324.5 (2)
C13—C12—C15—C16173.72 (16)C29—C28—C31—C32174.64 (14)
O3—C15—C16—Cl213.4 (3)O6—C31—C32—Cl46.4 (2)
C12—C15—C16—Cl2166.39 (13)C28—C31—C32—Cl4173.22 (11)
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O3ii0.972.243.103 (2)147
C10—H10···O4iii0.932.423.286 (2)155
C14—H14···O6iv0.932.383.242 (2)154
C17—H17A···O4v0.972.293.255 (2)173
C21—H21···O1vi0.932.543.469 (2)176
Symmetry codes: (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1, −y, −z+1; (iv) x, y, z+1; (v) −x+1/2, y+1/2, −z+1/2; (vi) x, y, z−1.
Table 1
Selected geometric parameters (Å)
top
Cg2···Cg4i3.899 (5)
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2.
Table 2
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O3ii0.972.243.103 (2)147
C10—H10···O4iii0.932.423.286 (2)155
C14—H14···O6iv0.932.383.242 (2)154
C17—H17A···O4v0.972.293.255 (2)173
C21—H21···O1vi0.932.543.469 (2)176
Symmetry codes: (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1, −y, −z+1; (iv) x, y, z+1; (v) −x+1/2, y+1/2, −z+1/2; (vi) x, y, z−1.
references
References top

Edward, J. W. R. & Sibelle, E. C. (1963). J. Org. Chem. 28, 674–676.

Fujimoto, T. T. & Quinn, J. A. (1988). Pestic. Biochem. Physiol. 30, 199–201.

Grossert, J. S., Dubey, P. K., Gill, G. H., Camerron, S. & Gardner, P. A. (1984). Can. J. Chem. 62, 798–807.

Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.