Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Trans 2' loop_ _publ_author_name Kianmehr, Ebrahim 41042 Liao, Fen-Ling 41039 Rashidi-Ranjbar, Parviz 41041 Wang, Sue-Lein _publ_contact_author_name 'Dr Parviz Rashidi-Ranjbar' _publ_contact_author_address ; Dr Parviz Rashidi-Ranjbar Department of Chemistry, Faculty of Science Tehran University Tehran IRAN ; _publ_contact_author_email 'RANJBAR@KHAYAM.UT.AC.IR' _publ_section_title ; The Stereochemistry of the stable conformational diastereomers in subsituted dibenzo [ef, kl] cycloeptene, a doubly bridged biphenyl. Synthesis, structural elucidation and barrier to conformational diastereomerism. ; data_jl11sad _database_code_CSD 173087 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Cl2 O2' _chemical_formula_weight 359.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5229(2) _cell_length_b 17.2091(3) _cell_length_c 10.37020(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.0960(10) _cell_angle_gamma 90.00 _cell_volume 1692.76(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5438 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Equant _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.392 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3301 _exptl_absorpt_correction_T_max 0.9623 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9258 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.74 _reflns_number_total 3575 _reflns_number_gt 2615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0733P)^2^+0.0164P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3575 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.11314(6) 0.08783(3) 0.57957(5) 0.05708(18) Uani 1 1 d . . . Cl2 Cl -0.70464(6) 0.26908(4) 0.88353(7) 0.0743(2) Uani 1 1 d . . . O1 O 0.03287(15) 0.01602(8) 0.82116(15) 0.0555(4) Uani 1 1 d . . . O2 O -0.38811(16) 0.15135(8) 1.02112(14) 0.0562(4) Uani 1 1 d . . . C1 C -0.0404(2) 0.08645(10) 0.7963(2) 0.0459(5) Uani 1 1 d . . . C2 C 0.0099(2) 0.13427(11) 0.6862(2) 0.0466(5) Uani 1 1 d . . . C3 C -0.0360(2) 0.20689(12) 0.6639(2) 0.0482(5) Uani 1 1 d . . . C4 C -0.1283(2) 0.24717(11) 0.74872(19) 0.0451(4) Uani 1 1 d . . . C5 C -0.1020(2) 0.32686(11) 0.7680(2) 0.0537(5) Uani 1 1 d . . . C6 C -0.1762(2) 0.37014(11) 0.8503(2) 0.0572(6) Uani 1 1 d . . . C7 C -0.2790(2) 0.33488(12) 0.9159(2) 0.0538(5) Uani 1 1 d . . . C8 C -0.3130(2) 0.25699(11) 0.89498(18) 0.0455(4) Uani 1 1 d . . . C9 C -0.4325(2) 0.22295(12) 0.9627(2) 0.0504(5) Uani 1 1 d . . . C10 C -0.5558(2) 0.21371(11) 0.8607(2) 0.0494(5) Uani 1 1 d . . . C11 C -0.5540(2) 0.16706(11) 0.7578(2) 0.0472(5) Uani 1 1 d . . . C12 C -0.4361(2) 0.11512(11) 0.73496(17) 0.0422(4) Uani 1 1 d . . . C13 C -0.4749(2) 0.04382(12) 0.67606(19) 0.0492(5) Uani 1 1 d . . . C14 C -0.3760(2) -0.01349(11) 0.6603(2) 0.0525(5) Uani 1 1 d . . . C15 C -0.2364(2) -0.00078(11) 0.7031(2) 0.0481(5) Uani 1 1 d . . . C16 C -0.1943(2) 0.07079(11) 0.75655(18) 0.0421(4) Uani 1 1 d . . . C17 C -0.29115(19) 0.13143(10) 0.76914(17) 0.0390(4) Uani 1 1 d . . . C18 C -0.24143(19) 0.21135(10) 0.80796(18) 0.0416(4) Uani 1 1 d . . . C19 C 0.1616(3) 0.02552(15) 0.9012(3) 0.0693(6) Uani 1 1 d . . . C20 C -0.4909(3) 0.11698(16) 1.0931(3) 0.0723(7) Uani 1 1 d . . . H1A H -0.0343 0.1188 0.8792 0.080 Uiso 1 1 d . . . H3A H -0.0065 0.2364 0.5919 0.080 Uiso 1 1 d . . . H5A H -0.0279 0.3540 0.7233 0.080 Uiso 1 1 d . . . H6A H -0.1546 0.4205 0.8671 0.080 Uiso 1 1 d . . . H7A H -0.3286 0.3627 0.9886 0.080 Uiso 1 1 d . . . H9A H -0.4586 0.2589 1.0363 0.080 Uiso 1 1 d . . . H11A H -0.6407 0.1654 0.6938 0.080 Uiso 1 1 d . . . H13A H -0.5833 0.0359 0.6494 0.080 Uiso 1 1 d . . . H14A H -0.4055 -0.0649 0.6222 0.080 Uiso 1 1 d . . . H15A H -0.1692 -0.0403 0.7010 0.080 Uiso 1 1 d . . . H19A H 0.1939 -0.0236 0.9110 0.080 Uiso 1 1 d . . . H19B H 0.1424 0.0523 0.9707 0.080 Uiso 1 1 d . . . H19C H 0.2262 0.0622 0.8545 0.080 Uiso 1 1 d . . . H20A H -0.5256 0.1545 1.1585 0.080 Uiso 1 1 d . . . H20B H -0.4451 0.0809 1.1459 0.080 Uiso 1 1 d . . . H20C H -0.5837 0.1187 1.0517 0.080 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0482(3) 0.0610(3) 0.0640(3) -0.0028(2) 0.0159(2) 0.0027(2) Cl2 0.0527(4) 0.0700(4) 0.1014(5) -0.0100(3) 0.0130(3) 0.0154(3) O1 0.0477(8) 0.0505(8) 0.0678(10) 0.0043(7) 0.0022(7) 0.0080(6) O2 0.0582(9) 0.0593(9) 0.0521(8) 0.0090(7) 0.0106(7) 0.0045(7) C1 0.0436(11) 0.0418(10) 0.0520(11) 0.0041(8) 0.0035(8) 0.0041(8) C2 0.0355(10) 0.0504(11) 0.0543(12) -0.0053(9) 0.0070(8) -0.0036(8) C3 0.0423(11) 0.0465(11) 0.0562(12) 0.0023(9) 0.0064(9) -0.0083(8) C4 0.0429(11) 0.0404(10) 0.0516(11) 0.0015(8) 0.0014(8) -0.0026(8) C5 0.0514(12) 0.0426(11) 0.0665(13) -0.0006(10) 0.0017(10) -0.0084(9) C6 0.0610(14) 0.0399(11) 0.0692(15) -0.0053(10) -0.0036(11) -0.0066(9) C7 0.0562(13) 0.0483(11) 0.0557(12) -0.0088(9) -0.0012(10) 0.0043(9) C8 0.0439(11) 0.0446(10) 0.0472(11) -0.0040(9) 0.0005(8) 0.0011(8) C9 0.0507(12) 0.0515(12) 0.0499(11) -0.0046(9) 0.0096(9) 0.0012(9) C10 0.0421(11) 0.0462(10) 0.0610(13) 0.0045(9) 0.0113(9) 0.0025(8) C11 0.0390(10) 0.0476(11) 0.0551(12) 0.0054(9) 0.0042(8) -0.0026(8) C12 0.0439(11) 0.0409(10) 0.0425(10) 0.0026(8) 0.0070(8) -0.0046(8) C13 0.0480(11) 0.0490(11) 0.0512(11) -0.0026(9) 0.0072(8) -0.0094(9) C14 0.0591(13) 0.0430(10) 0.0566(12) -0.0075(9) 0.0113(10) -0.0096(9) C15 0.0536(12) 0.0404(10) 0.0514(11) -0.0003(8) 0.0106(9) 0.0019(9) C16 0.0431(10) 0.0407(10) 0.0433(10) 0.0024(8) 0.0087(8) -0.0012(8) C17 0.0397(10) 0.0376(9) 0.0403(9) -0.0002(7) 0.0063(7) -0.0020(7) C18 0.0390(10) 0.0393(9) 0.0461(10) 0.0011(8) 0.0011(8) -0.0005(7) C19 0.0558(14) 0.0744(15) 0.0764(16) 0.0098(13) -0.0016(12) 0.0107(12) C20 0.0687(16) 0.0809(17) 0.0695(16) 0.0173(13) 0.0185(12) -0.0016(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.738(2) . ? Cl2 C10 1.742(2) . ? O1 C1 1.411(2) . ? O1 C19 1.427(3) . ? O2 C20 1.412(3) . ? O2 C9 1.421(2) . ? C1 C16 1.510(3) . ? C1 C2 1.519(3) . ? C2 C3 1.337(3) . ? C3 C4 1.472(3) . ? C4 C5 1.405(3) . ? C4 C18 1.426(3) . ? C5 C6 1.375(3) . ? C6 C7 1.381(3) . ? C7 C8 1.391(3) . ? C8 C18 1.416(3) . ? C8 C9 1.508(3) . ? C9 C10 1.517(3) . ? C10 C11 1.337(3) . ? C11 C12 1.471(3) . ? C12 C13 1.405(3) . ? C12 C17 1.422(3) . ? C13 C14 1.383(3) . ? C14 C15 1.381(3) . ? C15 C16 1.395(3) . ? C16 C17 1.407(3) . ? C17 C18 1.498(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C19 113.17(16) . . ? C20 O2 C9 113.25(17) . . ? O1 C1 C16 110.42(15) . . ? O1 C1 C2 114.77(16) . . ? C16 C1 C2 104.78(15) . . ? C3 C2 C1 121.11(17) . . ? C3 C2 Cl1 120.93(16) . . ? C1 C2 Cl1 117.58(14) . . ? C2 C3 C4 122.67(18) . . ? C5 C4 C18 119.53(18) . . ? C5 C4 C3 115.83(18) . . ? C18 C4 C3 124.62(17) . . ? C6 C5 C4 121.4(2) . . ? C5 C6 C7 119.59(18) . . ? C6 C7 C8 120.77(19) . . ? C7 C8 C18 121.02(19) . . ? C7 C8 C9 118.45(18) . . ? C18 C8 C9 120.47(16) . . ? O2 C9 C8 109.09(16) . . ? O2 C9 C10 112.89(16) . . ? C8 C9 C10 106.59(17) . . ? C11 C10 C9 123.78(18) . . ? C11 C10 Cl2 120.32(17) . . ? C9 C10 Cl2 115.90(15) . . ? C10 C11 C12 123.87(18) . . ? C13 C12 C17 119.50(17) . . ? C13 C12 C11 115.18(17) . . ? C17 C12 C11 125.30(16) . . ? C14 C13 C12 121.24(18) . . ? C15 C14 C13 119.66(18) . . ? C14 C15 C16 120.14(18) . . ? C15 C16 C17 121.63(17) . . ? C15 C16 C1 120.22(17) . . ? C17 C16 C1 118.07(16) . . ? C16 C17 C12 117.41(16) . . ? C16 C17 C18 120.79(16) . . ? C12 C17 C18 121.66(16) . . ? C8 C18 C4 117.33(17) . . ? C8 C18 C17 121.47(16) . . ? C4 C18 C17 120.92(17) . . ? _diffrn_measured_fraction_theta_max 0.895 _diffrn_reflns_theta_full 27.74 _diffrn_measured_fraction_theta_full 0.895 _refine_diff_density_max 0.199 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.047 data_jl10m _database_code_CSD 173088 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Cl2 O2' _chemical_formula_weight 359.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 9.8062(7) _cell_length_b 22.3707(15) _cell_length_c 8.4900(6) _cell_angle_alpha 90.00 _cell_angle_beta 115.9140(10) _cell_angle_gamma 90.00 _cell_volume 1675.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4048 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.397 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7973 _exptl_absorpt_correction_T_max 0.9297 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4696 _diffrn_reflns_av_R_equivalents 0.0542 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.93 _reflns_number_total 2330 _reflns_number_gt 2250 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0688P)^2^+0.8893P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0059(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(7) _refine_ls_number_reflns 2330 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.2314 0.87427(4) 0.7019 0.0603(3) Uani 1 1 d . . . Cl2 Cl -0.28445(18) 0.77477(4) 1.3245(2) 0.0635(3) Uani 1 1 d . . . O1 O 0.3137(3) 0.94994(11) 1.0143(4) 0.0579(7) Uani 1 1 d . . . O2 O -0.2651(4) 0.90096(11) 1.2968(4) 0.0549(6) Uani 1 1 d . . . C1 C 0.1779(4) 0.91931(15) 0.9764(5) 0.0445(7) Uani 1 1 d . . . C2 C 0.1137(4) 0.88548(15) 0.8033(5) 0.0443(7) Uani 1 1 d . . . C3 C -0.0246(5) 0.86265(15) 0.7366(5) 0.0459(7) Uani 1 1 d . . . C4 C -0.1288(4) 0.86994(13) 0.8162(5) 0.0415(7) Uani 1 1 d . . . C5 C -0.2824(5) 0.87740(15) 0.6971(5) 0.0483(8) Uani 1 1 d . . . C6 C -0.3915(4) 0.88649(18) 0.7576(5) 0.0518(8) Uani 1 1 d . . . C7 C -0.3502(5) 0.88841(16) 0.9366(5) 0.0479(8) Uani 1 1 d . . . C8 C -0.1992(4) 0.87903(13) 1.0549(5) 0.0404(7) Uani 1 1 d . . . C9 C -0.1580(4) 0.87514(13) 1.2489(5) 0.0427(7) Uani 1 1 d . . . C10 C -0.1415(4) 0.80883(14) 1.2902(5) 0.0438(7) Uani 1 1 d . . . C11 C -0.0282(5) 0.77790(14) 1.2879(5) 0.0450(7) Uani 1 1 d . . . C12 C 0.0931(4) 0.80426(13) 1.2531(4) 0.0408(7) Uani 1 1 d . . . C13 C 0.2391(5) 0.78232(16) 1.3521(5) 0.0502(8) Uani 1 1 d . . . C14 C 0.3635(5) 0.80517(19) 1.3389(5) 0.0565(9) Uani 1 1 d . . . C15 C 0.3451(5) 0.85132(17) 1.2207(5) 0.0518(8) Uani 1 1 d . . . C16 C 0.2012(4) 0.87305(13) 1.1167(5) 0.0426(7) Uani 1 1 d . . . C17 C 0.0705(4) 0.84988(13) 1.1269(4) 0.0392(6) Uani 1 1 d . . . C18 C -0.0851(4) 0.86889(12) 0.9992(5) 0.0396(6) Uani 1 1 d . . . C19 C 0.2937(7) 1.00272(19) 0.9158(7) 0.0716(12) Uani 1 1 d . . . C20 C -0.2563(8) 0.96420(19) 1.3073(9) 0.0848(17) Uani 1 1 d . . . H1A H 0.0989 0.9583 0.9823 0.080 Uiso 1 1 d . . . H3A H -0.0563 0.8423 0.6367 0.080 Uiso 1 1 d . . . H5A H -0.3206 0.8692 0.5591 0.080 Uiso 1 1 d . . . H6A H -0.4976 0.8880 0.6772 0.080 Uiso 1 1 d . . . H7A H -0.4308 0.8947 0.9940 0.080 Uiso 1 1 d . . . H9A H -0.0538 0.8930 1.3148 0.080 Uiso 1 1 d . . . H11A H -0.0218 0.7367 1.3175 0.080 Uiso 1 1 d . . . H13A H 0.2412 0.7484 1.4191 0.080 Uiso 1 1 d . . . H14A H 0.4768 0.7923 1.4021 0.080 Uiso 1 1 d . . . H15A H 0.4313 0.8710 1.2162 0.080 Uiso 1 1 d . . . H19A H 0.2393 1.0094 0.8009 0.080 Uiso 1 1 d . . . H19B H 0.2368 1.0298 0.9415 0.080 Uiso 1 1 d . . . H19C H 0.3843 1.0156 0.9332 0.080 Uiso 1 1 d . . . H20A H -0.1696 0.9689 1.3912 0.080 Uiso 1 1 d . . . H20B H -0.3248 0.9807 1.3381 0.080 Uiso 1 1 d . . . H20C H -0.2305 0.9808 1.2102 0.080 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0595(5) 0.0724(5) 0.0652(6) -0.0054(4) 0.0423(5) -0.0060(4) Cl2 0.0654(6) 0.0553(5) 0.0877(8) -0.0023(4) 0.0500(6) -0.0082(4) O1 0.0531(15) 0.0635(14) 0.0574(17) -0.0004(12) 0.0243(13) -0.0184(13) O2 0.0681(17) 0.0506(12) 0.0603(16) -0.0015(11) 0.0414(14) 0.0079(12) C1 0.0419(17) 0.0492(16) 0.0437(17) -0.0026(13) 0.0198(14) -0.0079(14) C2 0.0444(17) 0.0505(15) 0.0435(19) 0.0035(13) 0.0243(15) 0.0011(14) C3 0.0468(17) 0.0565(17) 0.0330(16) -0.0049(13) 0.0162(14) -0.0022(15) C4 0.0394(17) 0.0453(14) 0.0384(17) 0.0014(12) 0.0157(14) -0.0017(12) C5 0.0449(19) 0.0568(17) 0.0415(17) 0.0011(14) 0.0173(15) -0.0037(15) C6 0.0404(18) 0.0646(19) 0.046(2) 0.0060(15) 0.0149(16) 0.0003(16) C7 0.0444(18) 0.0536(17) 0.047(2) 0.0054(14) 0.0211(16) 0.0035(15) C8 0.0432(17) 0.0379(13) 0.0408(17) 0.0040(11) 0.0191(14) 0.0030(12) C9 0.0456(17) 0.0450(15) 0.0402(18) -0.0029(12) 0.0213(15) 0.0010(13) C10 0.0474(18) 0.0459(14) 0.0405(17) 0.0003(13) 0.0214(14) -0.0032(14) C11 0.0490(19) 0.0444(15) 0.0434(18) 0.0037(13) 0.0218(16) 0.0003(14) C12 0.0413(17) 0.0445(15) 0.0374(17) -0.0008(12) 0.0180(14) 0.0022(13) C13 0.047(2) 0.0555(17) 0.0454(19) 0.0076(14) 0.0172(16) 0.0086(16) C14 0.044(2) 0.075(2) 0.048(2) 0.0084(17) 0.0179(17) 0.0134(18) C15 0.0421(18) 0.065(2) 0.0475(19) -0.0006(16) 0.0189(15) 0.0014(16) C16 0.0407(17) 0.0485(16) 0.0395(17) -0.0040(12) 0.0183(15) -0.0054(13) C17 0.0403(16) 0.0407(13) 0.0353(15) -0.0005(11) 0.0153(12) -0.0002(13) C18 0.0405(16) 0.0376(13) 0.0406(17) -0.0006(11) 0.0175(14) -0.0020(11) C19 0.086(3) 0.055(2) 0.080(3) 0.0027(19) 0.042(3) -0.013(2) C20 0.120(5) 0.051(2) 0.110(4) -0.006(2) 0.074(4) 0.011(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.733(3) . ? Cl2 C10 1.728(3) . ? O1 C1 1.404(4) . ? O1 C19 1.410(5) . ? O2 C9 1.406(4) . ? O2 C20 1.418(5) . ? C1 C16 1.518(4) . ? C1 C2 1.523(5) . ? C2 C3 1.322(5) . ? C3 C4 1.460(5) . ? C4 C5 1.410(6) . ? C4 C18 1.420(5) . ? C5 C6 1.390(6) . ? C6 C7 1.392(5) . ? C7 C8 1.395(5) . ? C8 C18 1.410(4) . ? C8 C9 1.517(5) . ? C9 C10 1.517(4) . ? C10 C11 1.316(5) . ? C11 C12 1.469(5) . ? C12 C13 1.394(5) . ? C12 C17 1.425(4) . ? C13 C14 1.371(6) . ? C14 C15 1.396(5) . ? C15 C16 1.385(5) . ? C16 C17 1.420(4) . ? C17 C18 1.496(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C19 113.6(3) . . ? C9 O2 C20 113.3(3) . . ? O1 C1 C16 110.5(3) . . ? O1 C1 C2 114.5(3) . . ? C16 C1 C2 106.0(3) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 Cl1 120.8(3) . . ? C1 C2 Cl1 117.8(3) . . ? C2 C3 C4 123.5(3) . . ? C5 C4 C18 120.3(3) . . ? C5 C4 C3 115.2(3) . . ? C18 C4 C3 124.6(3) . . ? C6 C5 C4 120.4(4) . . ? C5 C6 C7 120.3(3) . . ? C6 C7 C8 119.5(3) . . ? C7 C8 C18 122.1(3) . . ? C7 C8 C9 119.0(3) . . ? C18 C8 C9 118.7(3) . . ? O2 C9 C10 110.6(3) . . ? O2 C9 C8 114.4(3) . . ? C10 C9 C8 105.0(2) . . ? C11 C10 C9 121.0(3) . . ? C11 C10 Cl2 121.5(2) . . ? C9 C10 Cl2 117.3(2) . . ? C10 C11 C12 123.7(3) . . ? C13 C12 C17 119.1(3) . . ? C13 C12 C11 116.5(3) . . ? C17 C12 C11 124.4(3) . . ? C14 C13 C12 122.3(3) . . ? C13 C14 C15 119.6(3) . . ? C16 C15 C14 119.6(3) . . ? C15 C16 C17 121.9(3) . . ? C15 C16 C1 120.1(3) . . ? C17 C16 C1 117.8(3) . . ? C16 C17 C12 117.3(3) . . ? C16 C17 C18 120.9(3) . . ? C12 C17 C18 121.5(3) . . ? C8 C18 C4 117.4(3) . . ? C8 C18 C17 120.7(3) . . ? C4 C18 C17 121.5(3) . . ? _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.891 _refine_diff_density_max 0.184 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.049 data_my06m _database_code_CSD 173089 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Cl2 O2' _chemical_formula_weight 359.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.3267(3) _cell_length_b 12.84100(10) _cell_length_c 11.7222(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.53 _cell_angle_gamma 90.00 _cell_volume 1726.06(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5496 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.385 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6156 _exptl_absorpt_correction_T_max 0.9202 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10033 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.01 _reflns_number_total 3791 _reflns_number_gt 2943 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.8123P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3791 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1325 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.55503(6) 0.16008(5) 0.65438(7) 0.0689(2) Uani 1 1 d . . . Cl2 Cl -0.08696(7) 0.04862(9) 0.84995(8) 0.1093(4) Uani 1 1 d . . . O1 O 0.55224(13) 0.02445(12) 0.86006(16) 0.0608(4) Uani 1 1 d . . . O2 O 0.01142(13) 0.20016(13) 0.63035(14) 0.0600(4) Uani 1 1 d . . . C1 C 0.25247(16) 0.21026(16) 0.81303(18) 0.0447(5) Uani 1 1 d . . . C2 C 0.24305(17) 0.10290(15) 0.76076(18) 0.0424(4) Uani 1 1 d . . . C3 C 0.34424(17) 0.04689(15) 0.76864(19) 0.0442(5) Uani 1 1 d . . . C4 C 0.46146(17) 0.09895(16) 0.8288(2) 0.0485(5) Uani 1 1 d . . . C5 C 0.46748(17) 0.18238(16) 0.7388(2) 0.0486(5) Uani 1 1 d . . . C6 C 0.40108(18) 0.26640(16) 0.7203(2) 0.0496(5) Uani 1 1 d . . . C7 C 0.32621(18) 0.28625(16) 0.7918(2) 0.0487(5) Uani 1 1 d . . . C8 C 0.3319(2) 0.38653(18) 0.8400(3) 0.0650(7) Uani 1 1 d . . . C9 C 0.2745(3) 0.4111(2) 0.9171(3) 0.0756(8) Uani 1 1 d . . . C10 C 0.2046(2) 0.3380(2) 0.9414(2) 0.0686(7) Uani 1 1 d . . . C11 C 0.18746(18) 0.23905(19) 0.88648(19) 0.0534(5) Uani 1 1 d . . . C12 C 0.0990(2) 0.1737(2) 0.9075(2) 0.0645(7) Uani 1 1 d . . . C13 C 0.0233(2) 0.1164(2) 0.8223(2) 0.0648(7) Uani 1 1 d . . . C14 C 0.02184(18) 0.1041(2) 0.6928(2) 0.0542(5) Uani 1 1 d . . . C15 C 0.13459(18) 0.05267(17) 0.70196(19) 0.0475(5) Uani 1 1 d . . . C16 C 0.1301(2) -0.04802(18) 0.6554(2) 0.0573(6) Uani 1 1 d . . . C17 C 0.2304(2) -0.10086(18) 0.6664(2) 0.0635(6) Uani 1 1 d . . . C18 C 0.3374(2) -0.05372(17) 0.7219(2) 0.0553(6) Uani 1 1 d . . . C19 C 0.6601(2) 0.0636(2) 0.9453(3) 0.0726(7) Uani 1 1 d . . . C20 C -0.0887(3) 0.2583(3) 0.6234(3) 0.0873(9) Uani 1 1 d . . . H4A H 0.4674 0.1320 0.9071 0.080 Uiso 1 1 d . . . H6A H 0.4028 0.3171 0.6651 0.080 Uiso 1 1 d . . . H8A H 0.3778 0.4321 0.8243 0.080 Uiso 1 1 d . . . H9A H 0.2810 0.4776 0.9531 0.080 Uiso 1 1 d . . . H10A H 0.1580 0.3500 0.9986 0.080 Uiso 1 1 d . . . H12A H 0.0911 0.1810 0.9891 0.080 Uiso 1 1 d . . . H14A H -0.0471 0.0611 0.6425 0.080 Uiso 1 1 d . . . H16A H 0.0537 -0.0790 0.6128 0.080 Uiso 1 1 d . . . H17A H 0.2238 -0.1705 0.6377 0.080 Uiso 1 1 d . . . H18A H 0.4094 -0.0877 0.7320 0.080 Uiso 1 1 d . . . H19A H 0.6863 0.1251 0.9086 0.080 Uiso 1 1 d . . . H19B H 0.7222 0.0085 0.9643 0.080 Uiso 1 1 d . . . H19C H 0.6485 0.0865 1.0201 0.080 Uiso 1 1 d . . . H20A H -0.1708 0.2119 0.5936 0.080 Uiso 1 1 d . . . H20B H -0.0946 0.2747 0.6908 0.080 Uiso 1 1 d . . . H20C H -0.1042 0.3136 0.5543 0.080 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0658(4) 0.0707(4) 0.0876(5) 0.0014(3) 0.0488(3) -0.0005(3) Cl2 0.0740(5) 0.1859(10) 0.0852(5) -0.0008(6) 0.0493(4) -0.0380(6) O1 0.0439(8) 0.0570(9) 0.0809(11) 0.0054(8) 0.0223(8) 0.0097(7) O2 0.0489(8) 0.0743(10) 0.0564(9) 0.0057(8) 0.0189(7) 0.0115(8) C1 0.0390(10) 0.0516(11) 0.0414(10) -0.0001(9) 0.0123(8) 0.0068(9) C2 0.0416(10) 0.0456(11) 0.0430(10) 0.0032(9) 0.0191(8) -0.0012(8) C3 0.0439(10) 0.0423(10) 0.0511(11) 0.0030(9) 0.0231(9) -0.0015(8) C4 0.0389(10) 0.0448(11) 0.0645(13) 0.0029(10) 0.0219(10) 0.0051(8) C5 0.0421(10) 0.0475(11) 0.0605(13) -0.0031(10) 0.0240(10) -0.0067(9) C6 0.0468(11) 0.0437(11) 0.0578(13) 0.0011(9) 0.0188(10) -0.0075(9) C7 0.0431(10) 0.0442(11) 0.0550(12) -0.0016(9) 0.0138(9) 0.0040(9) C8 0.0610(14) 0.0463(12) 0.0808(17) -0.0081(12) 0.0179(13) 0.0050(11) C9 0.0757(18) 0.0616(16) 0.0798(18) -0.0234(14) 0.0170(15) 0.0155(14) C10 0.0598(14) 0.0859(19) 0.0560(14) -0.0141(13) 0.0165(12) 0.0222(13) C11 0.0429(11) 0.0721(14) 0.0422(11) -0.0016(10) 0.0123(9) 0.0126(10) C12 0.0500(12) 0.103(2) 0.0473(12) 0.0032(13) 0.0257(10) 0.0108(13) C13 0.0430(11) 0.105(2) 0.0524(13) 0.0066(14) 0.0244(10) -0.0005(12) C14 0.0399(10) 0.0751(15) 0.0498(12) 0.0021(11) 0.0190(9) -0.0030(10) C15 0.0437(10) 0.0575(12) 0.0450(11) 0.0043(9) 0.0205(9) -0.0049(9) C16 0.0542(13) 0.0579(13) 0.0606(14) -0.0020(11) 0.0221(11) -0.0173(11) C17 0.0715(16) 0.0461(12) 0.0776(17) -0.0057(12) 0.0328(13) -0.0099(11) C18 0.0586(13) 0.0448(12) 0.0696(15) -0.0001(10) 0.0318(11) 0.0012(10) C19 0.0433(12) 0.095(2) 0.0734(17) 0.0100(15) 0.0139(11) 0.0072(13) C20 0.0705(17) 0.114(2) 0.0781(19) 0.0036(18) 0.0283(15) 0.0359(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C5 1.735(2) . ? Cl2 C13 1.742(2) . ? O1 C4 1.414(2) . ? O1 C19 1.429(3) . ? O2 C14 1.416(3) . ? O2 C20 1.419(3) . ? C1 C7 1.417(3) . ? C1 C11 1.424(3) . ? C1 C2 1.496(3) . ? C2 C3 1.413(3) . ? C2 C15 1.415(3) . ? C3 C18 1.394(3) . ? C3 C4 1.511(3) . ? C4 C5 1.524(3) . ? C5 C6 1.323(3) . ? C6 C7 1.478(3) . ? C7 C8 1.398(3) . ? C8 C9 1.373(4) . ? C9 C10 1.374(4) . ? C10 C11 1.405(4) . ? C11 C12 1.467(3) . ? C12 C13 1.313(4) . ? C13 C14 1.519(3) . ? C14 C15 1.507(3) . ? C15 C16 1.397(3) . ? C16 C17 1.374(4) . ? C17 C18 1.378(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C19 112.80(18) . . ? C14 O2 C20 113.6(2) . . ? C7 C1 C11 117.9(2) . . ? C7 C1 C2 121.41(17) . . ? C11 C1 C2 120.72(19) . . ? C3 C2 C15 116.97(18) . . ? C3 C2 C1 120.55(17) . . ? C15 C2 C1 122.49(18) . . ? C18 C3 C2 121.44(19) . . ? C18 C3 C4 120.18(18) . . ? C2 C3 C4 118.38(18) . . ? O1 C4 C3 110.60(17) . . ? O1 C4 C5 114.84(17) . . ? C3 C4 C5 105.62(17) . . ? C6 C5 C4 120.15(19) . . ? C6 C5 Cl1 121.21(18) . . ? C4 C5 Cl1 118.50(15) . . ? C5 C6 C7 121.7(2) . . ? C8 C7 C1 120.2(2) . . ? C8 C7 C6 116.0(2) . . ? C1 C7 C6 123.73(18) . . ? C9 C8 C7 121.1(3) . . ? C8 C9 C10 119.6(2) . . ? C9 C10 C11 121.5(2) . . ? C10 C11 C1 119.3(2) . . ? C10 C11 C12 115.9(2) . . ? C1 C11 C12 124.8(2) . . ? C13 C12 C11 123.9(2) . . ? C12 C13 C14 124.2(2) . . ? C12 C13 Cl2 121.58(19) . . ? C14 C13 Cl2 114.20(18) . . ? O2 C14 C15 108.96(17) . . ? O2 C14 C13 113.0(2) . . ? C15 C14 C13 107.60(18) . . ? C16 C15 C2 120.5(2) . . ? C16 C15 C14 118.36(19) . . ? C2 C15 C14 121.1(2) . . ? C17 C16 C15 121.0(2) . . ? C16 C17 C18 120.0(2) . . ? C17 C18 C3 120.1(2) . . ? _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.908 _refine_diff_density_max 0.207 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.042