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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o2009.
Published online 2009 July 29. doi:  10.1107/S1600536809027287
PMCID: PMC2977354

2,7-Dichloro-4-(chloro­acet­yl)fluorene

Abstract

There are two mol­ecules in the asymmetric unit of the title compound, C15H9Cl3O. The fluorene rings of the two mol­ecules are both coplanar within 066 (3) Å. In the crystal, C—H(...)O and C—H(...)Cl hydrogen bonds link the mol­ecules into sheets running parallel to (100).

Related literature

The title compound is an important inter­mediate in the synthesis of benflumetol, see: Deng et al. (2000 [triangle]). Benflumetol conforms structurally and in mode of action to the structure and mode of action of the aryl amino alcohol group of anti­malarial drugs, including quinine, mefloquine, and halofantrine, see: Pradines et al. (1999 [triangle]). For our ongoing work on structure–activity relationships, see: Rao & Hu (2005 [triangle], 2006 [triangle]); Hu et al. (2004 [triangle]).

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Object name is e-65-o2009-scheme1.jpg

Experimental

Crystal data

  • C15H9Cl3O
  • M r = 311.57
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2009-efi1.jpg
  • a = 7.607 (6) Å
  • b = 13.227 (10) Å
  • c = 14.957 (11) Å
  • α = 64.942 (9)°
  • β = 81.653 (10)°
  • γ = 76.433 (10)°
  • V = 1323.5 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.68 mm−1
  • T = 298 K
  • 0.25 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART CCD area detector diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.849, T max = 0.935
  • 6098 measured reflections
  • 5096 independent reflections
  • 3419 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.174
  • S = 0.96
  • 5096 reflections
  • 343 parameters
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 [triangle]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027287/kp2225sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027287/kp2225Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work is supported by the Open Foundation of Zhejiang Provincial Top Key Pharmaceutical Discipline (No. 20060611) and the Department of Education of Zhejiang Province of China (No. 20060806).

supplementary crystallographic information

Comment

Benflumetol is a racemic fluorene derivative. It conforms to the structure and reactivity of the aryl amino alcohol group of antimalarial drugs, including quinine, mefloquine, and halofantrine (Pradines et al., 1999). 2,7-Dichloro-4-chloroacetyl fluorene, (I), is an important intermediate in the synthesis of benflumetol (Deng et al., 2000). In a continuation of our work on the structure-activity relationships (Rao et al., 2004, 2005, 2006) we have obtained a colourless crystalline compound as the product of the reaction of 2-chloroacetyl chloride and 2,7-dichloro-9H-fluorene. The structural characterization of our product, (I), was performed by single-crystal X-ray diffraction.

The two essentially identical molecules form the asymmetric unit of (I) (Fig. 1). The two independent molecules are roughly parallel to each other, with a head-to-head orientation. The molecular structure is built up from three fused ring, two of which are six-membered and one five-membered. In both molecules, the three rings in the fluorene are coplanar with the largest deviation from the planes being 0.0664 (27) Å for atom C9 and 0.0656 (28)Å for atom C29, respectively. In both molecules, the dihedral angle between the two planes of the fluorene ring is 35.59 (6)°. The torsion angles for substituted COCH2Cl (O1/C14/C15/Cl3 and O2/C34/C35/Cl6) are -8.4 (5) and 31.8 (5)o, respectively.

The crystal packing of (I) is defined by C—H···O and C—H···Cl hydrogen bonds that link the molecules into sheets running parallel to the (100) plane (Table 1, Fig. 2).

Experimental

The title compound was prepared from 2-chloroacetyl chloride and 2,7-dichloro-9H-fluorene according to the procedure of Deng et al. (2000). A solution of the compound in ethanol was concentrated gradually at room temperature to afford colourless prisms (m.p. 398–399 K).

Refinement

H atoms were included in calculated positions and refined using a riding model. H atoms were given isotropic displacement parameters equal to 1.2 times the equivalent isotropic displacement parameters of their parent atoms and C—H distances were restrained to 0.97 Å for methylene H atoms, 0.93 Å for aromatic H atoms.

Figures

Fig. 1.
The structure of (I) showing the atom-labelling scheme. Ellipsoids are drawn at the 30% probability level.
Fig. 2.
The crystal packing of (I) showing the C—H···O and C—H···Cl hydrogen bonds.

Crystal data

C15H9Cl3OZ = 4
Mr = 311.57F(000) = 632
Triclinic, P1Dx = 1.564 Mg m3
Hall symbol: -P 1Melting point = 398–399 K
a = 7.607 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.227 (10) ÅCell parameters from 868 reflections
c = 14.957 (11) Åθ = 2.7–23.5°
α = 64.942 (9)°µ = 0.68 mm1
β = 81.653 (10)°T = 298 K
γ = 76.433 (10)°Prismatic, colorless
V = 1323.5 (17) Å30.25 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area detector diffractometer5096 independent reflections
Radiation source: fine-focus sealed tube3419 reflections with I > 2σ(I)
graphiteRint = 0.035
[var phi] and ω scansθmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −9→9
Tmin = 0.849, Tmax = 0.935k = −16→14
6098 measured reflectionsl = −17→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.1131P)2] where P = (Fo2 + 2Fc2)/3
5096 reflections(Δ/σ)max < 0.001
343 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = −0.44 e Å3

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 (Å2)

xyzUiso*/Ueq
Cl10.38813 (15)1.35826 (8)0.52879 (8)0.0682 (3)
Cl21.12004 (16)0.64244 (10)0.44936 (9)0.0768 (4)
Cl30.74877 (16)0.60526 (8)0.91826 (7)0.0685 (3)
O10.8430 (4)0.81774 (19)0.77151 (16)0.0514 (6)
C10.5934 (5)1.0272 (3)0.6453 (2)0.0436 (8)
H10.59190.96730.70720.052*
C20.5018 (5)1.1346 (3)0.6318 (2)0.0462 (8)
H20.43821.14740.68530.055*
C30.5023 (5)1.2242 (3)0.5401 (2)0.0469 (8)
C40.5926 (5)1.2073 (3)0.4590 (2)0.0468 (8)
H40.59191.26750.39710.056*
C50.7849 (5)1.0590 (3)0.3956 (2)0.0462 (8)
H5A0.70581.07060.34530.055*
H5B0.88511.09780.36410.055*
C60.9522 (5)0.8548 (3)0.4220 (3)0.0503 (9)
H60.98990.87490.35570.060*
C70.9956 (5)0.7454 (3)0.4890 (3)0.0530 (9)
C80.9454 (5)0.7127 (3)0.5885 (3)0.0489 (8)
H80.97590.63700.63220.059*
C90.8482 (4)0.7941 (3)0.6235 (2)0.0408 (7)
C100.6833 (4)1.0998 (3)0.4718 (2)0.0403 (7)
C110.6891 (4)1.0092 (3)0.5647 (2)0.0381 (7)
C120.8510 (4)0.9354 (3)0.4544 (2)0.0436 (8)
C130.7963 (4)0.9061 (3)0.5552 (2)0.0384 (7)
C140.8187 (4)0.7600 (3)0.7319 (2)0.0419 (7)
C150.7535 (6)0.6491 (3)0.7895 (3)0.0588 (10)
H15A0.83230.59030.77190.071*
H15B0.63270.65740.77040.071*
Cl40.11626 (18)1.38515 (8)0.82118 (10)0.0877 (4)
Cl50.41632 (16)0.54224 (8)1.28292 (6)0.0645 (3)
Cl60.26609 (15)0.64588 (9)0.81998 (8)0.0681 (3)
O20.3758 (4)0.8383 (2)0.84044 (17)0.0593 (7)
C210.1871 (5)1.0602 (3)0.8631 (3)0.0507 (8)
H210.18061.01960.82630.061*
C220.1468 (5)1.1780 (3)0.8212 (3)0.0566 (9)
H220.11131.21700.75640.068*
C230.1596 (5)1.2369 (3)0.8761 (3)0.0534 (9)
C240.2074 (5)1.1838 (3)0.9724 (3)0.0553 (9)
H240.21571.22551.00790.066*
C250.2907 (5)0.9899 (3)1.1187 (3)0.0512 (9)
H25A0.19471.00191.16560.061*
H25B0.40231.00131.13390.061*
C260.3527 (5)0.7703 (3)1.1986 (2)0.0467 (8)
H260.36860.76661.26050.056*
C270.3686 (5)0.6728 (3)1.1837 (2)0.0466 (8)
C280.3466 (5)0.6773 (3)1.0921 (2)0.0448 (8)
H280.35860.61011.08380.054*
C290.3065 (4)0.7813 (3)1.0120 (2)0.0404 (7)
C300.2427 (5)1.0668 (3)1.0149 (3)0.0461 (8)
C310.2373 (4)1.0032 (3)0.9603 (2)0.0417 (7)
C320.3128 (4)0.8733 (3)1.1198 (2)0.0431 (8)
C330.2860 (4)0.8817 (3)1.0262 (2)0.0400 (7)
C340.3009 (5)0.7782 (3)0.9140 (2)0.0432 (8)
C350.1889 (5)0.6998 (3)0.9112 (2)0.0503 (9)
H35A0.06480.74050.89940.060*
H35B0.18900.63640.97540.060*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0712 (7)0.0497 (5)0.0737 (7)0.0006 (5)−0.0030 (5)−0.0222 (5)
Cl20.0728 (8)0.0785 (7)0.0839 (8)−0.0045 (6)0.0218 (6)−0.0507 (6)
Cl30.0938 (9)0.0535 (5)0.0483 (5)−0.0204 (5)0.0077 (5)−0.0116 (4)
O10.0671 (18)0.0449 (13)0.0426 (13)−0.0150 (12)−0.0028 (11)−0.0162 (11)
C10.045 (2)0.0457 (18)0.0358 (17)−0.0127 (15)0.0024 (14)−0.0115 (14)
C20.043 (2)0.051 (2)0.0451 (19)−0.0108 (15)0.0053 (15)−0.0218 (16)
C30.044 (2)0.0435 (18)0.054 (2)−0.0081 (15)−0.0047 (16)−0.0193 (16)
C40.050 (2)0.0472 (19)0.0362 (17)−0.0163 (16)−0.0021 (15)−0.0066 (14)
C50.043 (2)0.060 (2)0.0384 (17)−0.0213 (16)0.0038 (14)−0.0190 (15)
C60.047 (2)0.068 (2)0.0434 (19)−0.0190 (17)0.0103 (15)−0.0300 (18)
C70.039 (2)0.069 (2)0.062 (2)−0.0100 (17)0.0099 (16)−0.041 (2)
C80.044 (2)0.0499 (19)0.055 (2)−0.0104 (16)0.0046 (16)−0.0243 (16)
C90.0338 (18)0.0481 (18)0.0427 (17)−0.0126 (14)0.0025 (13)−0.0194 (14)
C100.0360 (18)0.0502 (18)0.0377 (17)−0.0173 (15)0.0014 (13)−0.0171 (14)
C110.0341 (18)0.0473 (17)0.0363 (16)−0.0149 (14)0.0004 (13)−0.0171 (14)
C120.0333 (19)0.060 (2)0.0445 (18)−0.0183 (15)0.0038 (14)−0.0246 (16)
C130.0339 (18)0.0483 (18)0.0381 (16)−0.0161 (14)0.0034 (13)−0.0198 (14)
C140.0335 (18)0.0433 (17)0.0435 (18)−0.0041 (14)−0.0001 (14)−0.0148 (15)
C150.074 (3)0.058 (2)0.048 (2)−0.026 (2)0.0118 (18)−0.0220 (17)
Cl40.0814 (9)0.0455 (6)0.1137 (10)−0.0057 (5)0.0130 (7)−0.0201 (6)
Cl50.0920 (8)0.0550 (5)0.0389 (5)−0.0111 (5)−0.0018 (5)−0.0140 (4)
Cl60.0670 (7)0.0870 (7)0.0757 (7)−0.0203 (5)0.0155 (5)−0.0601 (6)
O20.081 (2)0.0623 (15)0.0380 (13)−0.0298 (14)0.0168 (12)−0.0212 (12)
C210.045 (2)0.055 (2)0.049 (2)−0.0091 (16)0.0083 (15)−0.0218 (17)
C220.046 (2)0.054 (2)0.058 (2)−0.0065 (17)0.0090 (17)−0.0156 (18)
C230.035 (2)0.0398 (18)0.075 (3)−0.0065 (14)0.0175 (17)−0.0202 (18)
C240.045 (2)0.054 (2)0.070 (3)−0.0129 (17)0.0195 (18)−0.0344 (19)
C250.051 (2)0.060 (2)0.053 (2)−0.0159 (17)0.0136 (16)−0.0355 (17)
C260.046 (2)0.063 (2)0.0339 (17)−0.0135 (17)0.0067 (14)−0.0238 (16)
C270.049 (2)0.0513 (19)0.0378 (18)−0.0147 (16)0.0075 (14)−0.0167 (15)
C280.049 (2)0.0480 (18)0.0399 (18)−0.0103 (15)0.0048 (14)−0.0222 (15)
C290.0381 (19)0.0473 (17)0.0365 (16)−0.0106 (14)0.0091 (13)−0.0198 (14)
C300.0359 (19)0.0514 (19)0.055 (2)−0.0129 (15)0.0160 (15)−0.0285 (16)
C310.0313 (18)0.0479 (18)0.0475 (19)−0.0103 (14)0.0116 (14)−0.0239 (15)
C320.0358 (19)0.0544 (19)0.0451 (18)−0.0145 (15)0.0143 (14)−0.0279 (16)
C330.0318 (18)0.0523 (18)0.0374 (17)−0.0116 (14)0.0113 (13)−0.0220 (14)
C340.044 (2)0.0453 (17)0.0377 (17)−0.0058 (15)0.0055 (14)−0.0181 (14)
C350.057 (2)0.061 (2)0.0386 (18)−0.0169 (18)0.0086 (15)−0.0269 (16)

Geometric parameters (Å, °)

Cl1—C31.730 (4)Cl4—C231.744 (4)
Cl2—C71.737 (4)Cl5—C271.735 (3)
Cl3—C151.758 (4)Cl6—C351.764 (3)
O1—C141.203 (4)O2—C341.207 (4)
C1—C21.371 (5)C21—C221.385 (5)
C1—C111.395 (5)C21—C311.388 (5)
C1—H10.9300C21—H210.9300
C2—C31.382 (4)C22—C231.375 (5)
C2—H20.9300C22—H220.9300
C3—C41.383 (5)C23—C241.369 (5)
C4—C101.372 (5)C24—C301.375 (5)
C4—H40.9300C24—H240.9300
C5—C121.491 (5)C25—C301.494 (5)
C5—C101.503 (5)C25—C321.504 (5)
C5—H5A0.9700C25—H25A0.9700
C5—H5B0.9700C25—H25B0.9700
C6—C71.361 (5)C26—C271.374 (5)
C6—C121.382 (5)C26—C321.375 (5)
C6—H60.9300C26—H260.9300
C7—C81.384 (5)C27—C281.379 (5)
C8—C91.403 (5)C28—C291.391 (4)
C8—H80.9300C28—H280.9300
C9—C131.397 (4)C29—C331.401 (4)
C9—C141.486 (5)C29—C341.491 (4)
C10—C111.396 (4)C30—C311.409 (4)
C11—C131.468 (5)C31—C331.475 (5)
C12—C131.412 (4)C32—C331.398 (5)
C14—C151.512 (5)C34—C351.505 (5)
C15—H15A0.9700C35—H35A0.9700
C15—H15B0.9700C35—H35B0.9700
C2—C1—C11118.9 (3)C22—C21—C31119.6 (3)
C2—C1—H1120.5C22—C21—H21120.2
C11—C1—H1120.5C31—C21—H21120.2
C1—C2—C3121.0 (3)C23—C22—C21119.5 (4)
C1—C2—H2119.5C23—C22—H22120.3
C3—C2—H2119.5C21—C22—H22120.3
C2—C3—C4120.8 (3)C24—C23—C22122.7 (3)
C2—C3—Cl1118.7 (3)C24—C23—Cl4118.3 (3)
C4—C3—Cl1120.5 (3)C22—C23—Cl4119.1 (3)
C10—C4—C3118.4 (3)C23—C24—C30117.9 (3)
C10—C4—H4120.8C23—C24—H24121.0
C3—C4—H4120.8C30—C24—H24121.0
C12—C5—C10103.2 (3)C30—C25—C32102.9 (3)
C12—C5—H5A111.1C30—C25—H25A111.2
C10—C5—H5A111.1C32—C25—H25A111.2
C12—C5—H5B111.1C30—C25—H25B111.2
C10—C5—H5B111.1C32—C25—H25B111.2
H5A—C5—H5B109.1H25A—C25—H25B109.1
C7—C6—C12118.6 (3)C27—C26—C32118.3 (3)
C7—C6—H6120.7C27—C26—H26120.9
C12—C6—H6120.7C32—C26—H26120.9
C6—C7—C8122.3 (3)C26—C27—C28121.3 (3)
C6—C7—Cl2119.3 (3)C26—C27—Cl5118.8 (3)
C8—C7—Cl2118.4 (3)C28—C27—Cl5119.9 (3)
C7—C8—C9119.9 (3)C27—C28—C29120.6 (3)
C7—C8—H8120.0C27—C28—H28119.7
C9—C8—H8120.0C29—C28—H28119.7
C13—C9—C8118.6 (3)C28—C29—C33118.9 (3)
C13—C9—C14122.6 (3)C28—C29—C34117.0 (3)
C8—C9—C14118.6 (3)C33—C29—C34124.0 (3)
C4—C10—C11121.4 (3)C24—C30—C31121.3 (3)
C4—C10—C5128.6 (3)C24—C30—C25128.1 (3)
C11—C10—C5110.0 (3)C31—C30—C25110.6 (3)
C1—C11—C10119.3 (3)C21—C31—C30118.9 (3)
C1—C11—C13131.7 (3)C21—C31—C33133.4 (3)
C10—C11—C13108.9 (3)C30—C31—C33107.7 (3)
C6—C12—C13121.1 (3)C26—C32—C33122.2 (3)
C6—C12—C5128.5 (3)C26—C32—C25127.4 (3)
C13—C12—C5110.4 (3)C33—C32—C25110.4 (3)
C9—C13—C12119.4 (3)C32—C33—C29118.6 (3)
C9—C13—C11133.0 (3)C32—C33—C31108.4 (3)
C12—C13—C11107.5 (3)C29—C33—C31133.0 (3)
O1—C14—C9122.1 (3)O2—C34—C29122.0 (3)
O1—C14—C15122.0 (3)O2—C34—C35121.9 (3)
C9—C14—C15115.9 (3)C29—C34—C35116.1 (3)
C14—C15—Cl3113.4 (2)C34—C35—Cl6113.8 (2)
C14—C15—H15A108.9C34—C35—H35A108.8
Cl3—C15—H15A108.9Cl6—C35—H35A108.8
C14—C15—H15B108.9C34—C35—H35B108.8
Cl3—C15—H15B108.9Cl6—C35—H35B108.8
H15A—C15—H15B107.7H35A—C35—H35B107.7
C11—C1—C2—C30.3 (5)C31—C21—C22—C230.9 (5)
C1—C2—C3—C41.3 (5)C21—C22—C23—C24−1.5 (6)
C1—C2—C3—Cl1−178.6 (3)C21—C22—C23—Cl4177.8 (3)
C2—C3—C4—C10−0.7 (5)C22—C23—C24—C30−0.3 (5)
Cl1—C3—C4—C10179.1 (2)Cl4—C23—C24—C30−179.5 (3)
C12—C6—C7—C8−1.4 (5)C32—C26—C27—C280.5 (5)
C12—C6—C7—Cl2179.1 (3)C32—C26—C27—Cl5−179.3 (3)
C6—C7—C8—C9−0.9 (5)C26—C27—C28—C29−0.3 (5)
Cl2—C7—C8—C9178.6 (3)Cl5—C27—C28—C29179.4 (3)
C7—C8—C9—C133.3 (5)C27—C28—C29—C33−1.0 (5)
C7—C8—C9—C14−171.5 (3)C27—C28—C29—C34174.8 (3)
C3—C4—C10—C11−1.5 (5)C23—C24—C30—C312.5 (5)
C3—C4—C10—C5177.6 (3)C23—C24—C30—C25−177.7 (3)
C12—C5—C10—C4−179.6 (3)C32—C25—C30—C24−179.9 (3)
C12—C5—C10—C11−0.4 (3)C32—C25—C30—C31−0.1 (4)
C2—C1—C11—C10−2.5 (5)C22—C21—C31—C301.2 (5)
C2—C1—C11—C13−179.1 (3)C22—C21—C31—C33179.2 (3)
C4—C10—C11—C13.1 (5)C24—C30—C31—C21−3.0 (5)
C5—C10—C11—C1−176.1 (3)C25—C30—C31—C21177.2 (3)
C4—C10—C11—C13−179.6 (3)C24—C30—C31—C33178.5 (3)
C5—C10—C11—C131.2 (3)C25—C30—C31—C33−1.3 (4)
C7—C6—C12—C131.2 (5)C27—C26—C32—C330.8 (5)
C7—C6—C12—C5−179.0 (3)C27—C26—C32—C25−179.5 (3)
C10—C5—C12—C6179.6 (3)C30—C25—C32—C26−178.2 (3)
C10—C5—C12—C13−0.6 (3)C30—C25—C32—C331.6 (4)
C8—C9—C13—C12−3.4 (4)C26—C32—C33—C29−2.2 (5)
C14—C9—C13—C12171.2 (3)C25—C32—C33—C29178.1 (3)
C8—C9—C13—C11176.7 (3)C26—C32—C33—C31177.3 (3)
C14—C9—C13—C11−8.8 (5)C25—C32—C33—C31−2.4 (4)
C6—C12—C13—C91.2 (5)C28—C29—C33—C322.2 (5)
C5—C12—C13—C9−178.6 (3)C34—C29—C33—C32−173.4 (3)
C6—C12—C13—C11−178.9 (3)C28—C29—C33—C31−177.1 (3)
C5—C12—C13—C111.3 (3)C34—C29—C33—C317.3 (6)
C1—C11—C13—C9−4.8 (6)C21—C31—C33—C32−175.9 (4)
C10—C11—C13—C9178.4 (3)C30—C31—C33—C322.3 (4)
C1—C11—C13—C12175.3 (3)C21—C31—C33—C293.5 (6)
C10—C11—C13—C12−1.6 (3)C30—C31—C33—C29−178.3 (3)
C13—C9—C14—O1−40.8 (5)C28—C29—C34—O2−133.1 (4)
C8—C9—C14—O1133.8 (4)C33—C29—C34—O242.6 (5)
C13—C9—C14—C15138.3 (3)C28—C29—C34—C3549.7 (4)
C8—C9—C14—C15−47.1 (4)C33—C29—C34—C35−134.6 (3)
O1—C14—C15—Cl3−8.4 (5)O2—C34—C35—Cl631.8 (5)
C9—C14—C15—Cl3172.5 (3)C29—C34—C35—Cl6−151.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.932.372.998 (4)124
C15—H15B···Cl6i0.972.803.678 (5)151
C21—H21···O2i0.932.453.086 (5)126
C35—H35A···O1i0.972.453.261 (5)140

Symmetry codes: i; (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2225).

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