# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm #TrackingRef '- CE-COM-09-2010-000676_revised.cif' _journal_coden_Cambridge 1350 _audit_creation_method 'SHELXL-97 plus manual editing' _publ_contact_author_name 'Andrew D. Bond' _publ_contact_author_address ; University of Southern Denmark Department of Physics and Chemistry Campusvej 55 5230 Odense Denmark ; _publ_contact_author_email adb@chem.sdu.dk _publ_contact_author_fax '+45 6615 8780' _publ_contact_author_phone '+45 6650 2545' loop_ _publ_author_name A.Bond K.Solanko 'J.van der Streek' M.Neumann data_298K _database_code_depnum_ccdc_archive 'CCDC 794782' #TrackingRef '- CE-COM-09-2010-000676_revised.cif' _chemical_name_systematic ? _chemical_name_common 2,6-bis(2,4-dichlorobenzylidene)cyclohexanone _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cl4 O' _chemical_formula_sum 'C20 H14 Cl4 O' _chemical_formula_weight 412.11 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.4171(8) _cell_length_b 8.0418(4) _cell_length_c 31.454(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3646.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1747 _cell_measurement_theta_min 3.18 _cell_measurement_theta_max 18.52 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.654 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.805 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.826085 ; _exptl_special_details ; Small crystal and relatively weak diffractor. Data are truncated to 0.95 \%A. ; _diffrn_ambient_temperature 298(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 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 23074 _diffrn_reflns_av_R_equivalents 0.0963 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 21.96 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 21.96 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 2227 _reflns_number_gt 1388 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-22 (Bruker Nonius, 2004)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10' _computing_molecular_graphics 'SHELXTL v.6.10' _computing_publication_material 'SHELXTL v.6.10' _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^)+(0.0212P)^2^+1.8224P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2227 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.185 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.046 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 0.28368(8) 0.20950(14) 0.41295(3) 0.0785(4) Uani 1 1 d . . . Cl2 Cl 0.56583(8) 0.60933(15) 0.45428(3) 0.0812(4) Uani 1 1 d . . . Cl3 Cl -0.01238(6) 0.04766(11) 0.16186(3) 0.0523(3) Uani 1 1 d . . . Cl4 Cl 0.12865(10) 0.07929(17) 0.00482(3) 0.1006(5) Uani 1 1 d . . . O1 O 0.13634(17) 0.3255(3) 0.27376(7) 0.0498(7) Uani 1 1 d . . . C1 C 0.3597(3) 0.3663(4) 0.39857(12) 0.0427(10) Uani 1 1 d . . . C2 C 0.4236(3) 0.4180(5) 0.42825(12) 0.0523(11) Uani 1 1 d . . . H2A H 0.4254 0.3697 0.4551 0.063 Uiso 1 1 calc R . . C3 C 0.4842(3) 0.5414(5) 0.41765(12) 0.0477(10) Uani 1 1 d . . . C4 C 0.4821(3) 0.6147(5) 0.37820(13) 0.0504(10) Uani 1 1 d . . . H4A H 0.5237 0.6989 0.3713 0.061 Uiso 1 1 calc R . . C5 C 0.4173(3) 0.5614(4) 0.34918(11) 0.0457(10) Uani 1 1 d . . . H5A H 0.4154 0.6117 0.3226 0.055 Uiso 1 1 calc R . . C6 C 0.3548(2) 0.4354(4) 0.35817(11) 0.0377(9) Uani 1 1 d . . . C7 C 0.2845(2) 0.3856(4) 0.32662(11) 0.0416(9) Uani 1 1 d . . . H7A H 0.2249 0.3665 0.3368 0.050 Uiso 1 1 calc R . . C8 C 0.2974(2) 0.3651(4) 0.28517(11) 0.0334(9) Uani 1 1 d . . . C9 C 0.3901(2) 0.3696(4) 0.26349(10) 0.0413(10) Uani 1 1 d . . . H9A H 0.4389 0.3555 0.2844 0.050 Uiso 1 1 calc R . . H9B H 0.3987 0.4768 0.2499 0.050 Uiso 1 1 calc R . . C10 C 0.3964(2) 0.2329(4) 0.23057(11) 0.0470(10) Uani 1 1 d . . . H10A H 0.4582 0.2318 0.2183 0.056 Uiso 1 1 calc R . . H10B H 0.3858 0.1262 0.2440 0.056 Uiso 1 1 calc R . . C11 C 0.3256(2) 0.2596(4) 0.19583(11) 0.0435(10) Uani 1 1 d . . . H11A H 0.3425 0.3578 0.1797 0.052 Uiso 1 1 calc R . . H11B H 0.3270 0.1653 0.1766 0.052 Uiso 1 1 calc R . . C12 C 0.2282(2) 0.2807(4) 0.21250(11) 0.0356(9) Uani 1 1 d . . . C13 C 0.2146(3) 0.3237(4) 0.25850(11) 0.0371(9) Uani 1 1 d . . . C14 C 0.1517(2) 0.2630(4) 0.18910(11) 0.0405(10) Uani 1 1 d . . . H14A H 0.0958 0.2780 0.2033 0.049 Uiso 1 1 calc R . . C15 C 0.1446(3) 0.2227(4) 0.14353(12) 0.0419(10) Uani 1 1 d . . . C16 C 0.2066(3) 0.2844(5) 0.11360(12) 0.0540(11) Uani 1 1 d . . . H16A H 0.2536 0.3554 0.1225 0.065 Uiso 1 1 calc R . . C17 C 0.2006(3) 0.2438(5) 0.07121(13) 0.0607(12) Uani 1 1 d . . . H17A H 0.2428 0.2877 0.0519 0.073 Uiso 1 1 calc R . . C18 C 0.1323(3) 0.1388(6) 0.05774(12) 0.0577(12) Uani 1 1 d . . . C19 C 0.0669(3) 0.0781(5) 0.08554(13) 0.0538(11) Uani 1 1 d . . . H19A H 0.0197 0.0083 0.0761 0.065 Uiso 1 1 calc R . . C20 C 0.0729(2) 0.1232(4) 0.12788(12) 0.0416(10) Uani 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 0.0952(9) 0.0898(9) 0.0506(7) 0.0130(6) -0.0018(7) -0.0475(7) Cl2 0.0750(8) 0.1084(10) 0.0601(8) -0.0148(7) -0.0130(6) -0.0282(7) Cl3 0.0388(6) 0.0637(7) 0.0544(6) 0.0000(5) 0.0009(5) -0.0027(5) Cl4 0.1084(11) 0.1530(13) 0.0403(7) -0.0120(8) -0.0014(7) -0.0073(9) O1 0.0300(16) 0.076(2) 0.0432(16) 0.0046(13) 0.0032(14) -0.0005(13) C1 0.048(3) 0.042(3) 0.038(2) 0.001(2) 0.010(2) -0.008(2) C2 0.067(3) 0.058(3) 0.032(2) -0.003(2) 0.000(2) -0.012(2) C3 0.047(3) 0.057(3) 0.040(3) -0.013(2) -0.003(2) -0.005(2) C4 0.047(3) 0.052(3) 0.052(3) -0.002(2) 0.004(2) -0.014(2) C5 0.049(3) 0.049(3) 0.038(2) 0.006(2) 0.002(2) -0.002(2) C6 0.034(2) 0.041(3) 0.038(2) -0.003(2) 0.005(2) 0.003(2) C7 0.032(2) 0.048(2) 0.044(3) 0.004(2) 0.003(2) -0.0025(19) C8 0.031(2) 0.035(2) 0.035(2) 0.0053(18) 0.0050(19) 0.0028(18) C9 0.035(2) 0.048(2) 0.041(2) 0.006(2) 0.0008(19) -0.0001(19) C10 0.033(2) 0.057(3) 0.051(3) -0.002(2) 0.004(2) 0.0054(19) C11 0.034(2) 0.054(3) 0.043(2) -0.008(2) 0.0042(19) -0.0024(18) C12 0.031(2) 0.035(2) 0.040(2) 0.0036(19) 0.004(2) 0.0006(18) C13 0.030(2) 0.039(2) 0.042(3) 0.0062(18) 0.003(2) 0.0029(19) C14 0.030(2) 0.046(3) 0.046(3) 0.003(2) 0.004(2) 0.0021(19) C15 0.036(3) 0.048(3) 0.042(2) 0.001(2) 0.000(2) 0.001(2) C16 0.045(3) 0.069(3) 0.048(3) 0.008(2) 0.003(2) -0.006(2) C17 0.054(3) 0.085(4) 0.043(3) 0.015(2) 0.006(2) 0.005(3) C18 0.060(3) 0.078(3) 0.036(3) -0.001(2) -0.006(3) 0.010(3) C19 0.046(3) 0.066(3) 0.050(3) -0.006(2) -0.009(2) 0.000(2) C20 0.035(2) 0.047(3) 0.043(3) 0.003(2) 0.003(2) 0.006(2) _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 C1 1.731(4) . ? Cl2 C3 1.735(4) . ? Cl3 C20 1.738(3) . ? Cl4 C18 1.733(4) . ? O1 C13 1.226(4) . ? C1 C2 1.376(5) . ? C1 C6 1.389(4) . ? C2 C3 1.363(5) . ? C2 H2A 0.9300 . ? C3 C4 1.374(5) . ? C4 C5 1.374(4) . ? C4 H4A 0.9300 . ? C5 C6 1.385(4) . ? C5 H5A 0.9300 . ? C6 C7 1.474(4) . ? C7 C8 1.327(4) . ? C7 H7A 0.9300 . ? C8 C13 1.497(4) . ? C8 C9 1.501(4) . ? C9 C10 1.513(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.511(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.508(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C14 1.334(4) . ? C12 C13 1.500(4) . ? C14 C15 1.473(5) . ? C14 H14A 0.9300 . ? C15 C16 1.390(4) . ? C15 C20 1.397(4) . ? C16 C17 1.375(5) . ? C16 H16A 0.9300 . ? C17 C18 1.364(5) . ? C17 H17A 0.9300 . ? C18 C19 1.376(5) . ? C19 C20 1.383(5) . ? C19 H19A 0.9300 . ? 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 C2 C1 C6 122.2(3) . . ? C2 C1 Cl1 117.8(3) . . ? C6 C1 Cl1 119.9(3) . . ? C3 C2 C1 118.9(3) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.2(4) . . ? C2 C3 Cl2 120.1(3) . . ? C4 C3 Cl2 118.7(3) . . ? C3 C4 C5 118.7(3) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C4 C5 C6 122.3(3) . . ? C4 C5 H5A 118.8 . . ? C6 C5 H5A 118.8 . . ? C5 C6 C1 116.5(3) . . ? C5 C6 C7 120.6(3) . . ? C1 C6 C7 122.8(3) . . ? C8 C7 C6 126.8(3) . . ? C8 C7 H7A 116.6 . . ? C6 C7 H7A 116.6 . . ? C7 C8 C13 117.8(3) . . ? C7 C8 C9 124.6(3) . . ? C13 C8 C9 117.5(3) . . ? C8 C9 C10 110.3(3) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 110.5(3) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 113.2(3) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.8 . . ? C14 C12 C13 116.7(3) . . ? C14 C12 C11 124.5(3) . . ? C13 C12 C11 118.9(3) . . ? O1 C13 C8 120.8(3) . . ? O1 C13 C12 120.0(3) . . ? C8 C13 C12 119.2(3) . . ? C12 C14 C15 128.2(3) . . ? C12 C14 H14A 115.9 . . ? C15 C14 H14A 115.9 . . ? C16 C15 C20 116.2(3) . . ? C16 C15 C14 122.4(3) . . ? C20 C15 C14 121.4(3) . . ? C17 C16 C15 122.1(4) . . ? C17 C16 H16A 118.9 . . ? C15 C16 H16A 118.9 . . ? C18 C17 C16 119.6(4) . . ? C18 C17 H17A 120.2 . . ? C16 C17 H17A 120.2 . . ? C17 C18 C19 121.1(4) . . ? C17 C18 Cl4 119.4(4) . . ? C19 C18 Cl4 119.5(4) . . ? C18 C19 C20 118.4(4) . . ? C18 C19 H19A 120.8 . . ? C20 C19 H19A 120.8 . . ? C19 C20 C15 122.4(3) . . ? C19 C20 Cl3 117.1(3) . . ? C15 C20 Cl3 120.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.0(6) . . . . ? Cl1 C1 C2 C3 180.0(3) . . . . ? C1 C2 C3 C4 0.4(6) . . . . ? C1 C2 C3 Cl2 -179.9(3) . . . . ? C2 C3 C4 C5 -0.1(6) . . . . ? Cl2 C3 C4 C5 -179.8(3) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C4 C5 C6 C1 1.0(5) . . . . ? C4 C5 C6 C7 178.0(3) . . . . ? C2 C1 C6 C5 -0.7(5) . . . . ? Cl1 C1 C6 C5 179.4(2) . . . . ? C2 C1 C6 C7 -177.7(3) . . . . ? Cl1 C1 C6 C7 2.4(5) . . . . ? C5 C6 C7 C8 42.8(5) . . . . ? C1 C6 C7 C8 -140.3(4) . . . . ? C6 C7 C8 C13 -176.4(3) . . . . ? C6 C7 C8 C9 7.8(6) . . . . ? C7 C8 C9 C10 138.0(3) . . . . ? C13 C8 C9 C10 -37.8(4) . . . . ? C8 C9 C10 C11 63.5(4) . . . . ? C9 C10 C11 C12 -53.3(4) . . . . ? C10 C11 C12 C14 -161.8(3) . . . . ? C10 C11 C12 C13 17.8(4) . . . . ? C7 C8 C13 O1 7.3(5) . . . . ? C9 C8 C13 O1 -176.6(3) . . . . ? C7 C8 C13 C12 -173.1(3) . . . . ? C9 C8 C13 C12 3.0(4) . . . . ? C14 C12 C13 O1 6.8(5) . . . . ? C11 C12 C13 O1 -172.9(3) . . . . ? C14 C12 C13 C8 -172.8(3) . . . . ? C11 C12 C13 C8 7.6(5) . . . . ? C13 C12 C14 C15 179.5(3) . . . . ? C11 C12 C14 C15 -0.8(6) . . . . ? C12 C14 C15 C16 -37.4(5) . . . . ? C12 C14 C15 C20 144.5(4) . . . . ? C20 C15 C16 C17 -3.0(5) . . . . ? C14 C15 C16 C17 178.8(3) . . . . ? C15 C16 C17 C18 -0.5(6) . . . . ? C16 C17 C18 C19 2.7(6) . . . . ? C16 C17 C18 Cl4 -176.6(3) . . . . ? C17 C18 C19 C20 -1.3(6) . . . . ? Cl4 C18 C19 C20 178.0(3) . . . . ? C18 C19 C20 C15 -2.4(6) . . . . ? C18 C19 C20 Cl3 178.7(3) . . . . ? C16 C15 C20 C19 4.5(5) . . . . ? C14 C15 C20 C19 -177.3(3) . . . . ? C16 C15 C20 Cl3 -176.7(3) . . . . ? C14 C15 C20 Cl3 1.6(5) . . . . ? data_250K _database_code_depnum_ccdc_archive 'CCDC 794783' #TrackingRef '- CE-COM-09-2010-000676_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 2,6-bis(2,4-dichlorobenzylidene)cyclohexanone _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cl4 O' _chemical_formula_sum 'C20 H14 Cl4 O' _chemical_formula_weight 412.11 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.4059(11) _cell_length_b 7.9797(3) _cell_length_c 31.467(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3617.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 2999 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 23.57 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.660 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.000 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 250(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 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 21985 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.81 _diffrn_reflns_theta_max 25.03 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.985 _reflns_number_total 3157 _reflns_number_gt 2068 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0253P)^2^+1.8806P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3157 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0705 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.223 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.050 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 0.28417(6) 0.20594(11) 0.41306(2) 0.0646(3) Uani 1 1 d . . . Cl2 Cl 0.56687(6) 0.60892(12) 0.45471(3) 0.0664(3) Uani 1 1 d . . . Cl3 Cl -0.01302(5) 0.04731(9) 0.16208(2) 0.0423(2) Uani 1 1 d . . . Cl4 Cl 0.12820(7) 0.07889(14) 0.00489(3) 0.0817(3) Uani 1 1 d . . . O1 O 0.13659(12) 0.3252(2) 0.27404(6) 0.0415(5) Uani 1 1 d . . . C1 C 0.35997(19) 0.3647(3) 0.39876(9) 0.0373(7) Uani 1 1 d . . . C2 C 0.4241(2) 0.4161(4) 0.42865(9) 0.0416(8) Uani 1 1 d . . . H2A H 0.4260 0.3665 0.4557 0.050 Uiso 1 1 calc R . . C3 C 0.48529(19) 0.5419(4) 0.41787(9) 0.0401(7) Uani 1 1 d . . . C4 C 0.4831(2) 0.6156(4) 0.37869(9) 0.0422(7) Uani 1 1 d . . . H4A H 0.5251 0.7015 0.3718 0.051 Uiso 1 1 calc R . . C5 C 0.41829(19) 0.5620(3) 0.34946(9) 0.0383(7) Uani 1 1 d . . . H5A H 0.4167 0.6131 0.3226 0.046 Uiso 1 1 calc R . . C6 C 0.35507(18) 0.4346(3) 0.35842(8) 0.0326(6) Uani 1 1 d . . . C7 C 0.28481(18) 0.3845(3) 0.32703(8) 0.0346(7) Uani 1 1 d . . . H7A H 0.2246 0.3646 0.3374 0.042 Uiso 1 1 calc R . . C8 C 0.29771(17) 0.3645(3) 0.28528(8) 0.0299(6) Uani 1 1 d . . . C9 C 0.39056(17) 0.3707(3) 0.26358(8) 0.0334(7) Uani 1 1 d . . . H9A H 0.4400 0.3574 0.2847 0.040 Uiso 1 1 calc R . . H9B H 0.3986 0.4798 0.2498 0.040 Uiso 1 1 calc R . . C10 C 0.39744(18) 0.2321(3) 0.23061(9) 0.0374(7) Uani 1 1 d . . . H10A H 0.4598 0.2310 0.2182 0.045 Uiso 1 1 calc R . . H10B H 0.3866 0.1233 0.2442 0.045 Uiso 1 1 calc R . . C11 C 0.32627(17) 0.2604(4) 0.19605(8) 0.0370(7) Uani 1 1 d . . . H11A H 0.3434 0.3611 0.1800 0.044 Uiso 1 1 calc R . . H11B H 0.3278 0.1652 0.1764 0.044 Uiso 1 1 calc R . . C12 C 0.22861(17) 0.2810(3) 0.21256(8) 0.0305(6) Uani 1 1 d . . . C13 C 0.21484(18) 0.3231(3) 0.25871(8) 0.0309(6) Uani 1 1 d . . . C14 C 0.15186(19) 0.2625(3) 0.18928(9) 0.0345(7) Uani 1 1 d . . . H14A H 0.0954 0.2762 0.2038 0.041 Uiso 1 1 calc R . . C15 C 0.14434(18) 0.2233(3) 0.14380(8) 0.0339(7) Uani 1 1 d . . . C16 C 0.2072(2) 0.2847(4) 0.11384(9) 0.0450(8) Uani 1 1 d . . . H16A H 0.2554 0.3557 0.1229 0.054 Uiso 1 1 calc R . . C17 C 0.2010(2) 0.2446(4) 0.07140(9) 0.0504(9) Uani 1 1 d . . . H17A H 0.2435 0.2896 0.0518 0.060 Uiso 1 1 calc R . . C18 C 0.1321(2) 0.1381(4) 0.05789(9) 0.0474(8) Uani 1 1 d . . . C19 C 0.0659(2) 0.0776(4) 0.08579(9) 0.0428(7) Uani 1 1 d . . . H19A H 0.0177 0.0076 0.0763 0.051 Uiso 1 1 calc R . . C20 C 0.07274(18) 0.1233(3) 0.12811(8) 0.0348(7) Uani 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 0.0793(6) 0.0730(6) 0.0414(5) 0.0109(4) -0.0027(4) -0.0391(5) Cl2 0.0613(6) 0.0896(7) 0.0483(5) -0.0123(5) -0.0108(4) -0.0235(5) Cl3 0.0318(4) 0.0514(4) 0.0436(4) -0.0003(4) 0.0008(3) -0.0016(3) Cl4 0.0881(7) 0.1238(9) 0.0331(5) -0.0090(5) 0.0000(5) -0.0079(7) O1 0.0258(11) 0.0624(14) 0.0363(11) 0.0045(10) 0.0053(9) -0.0004(10) C1 0.0428(18) 0.0359(17) 0.0332(17) -0.0011(14) 0.0067(14) -0.0070(14) C2 0.051(2) 0.0492(19) 0.0247(16) -0.0019(14) -0.0027(14) -0.0041(16) C3 0.0357(17) 0.0466(18) 0.0380(17) -0.0106(15) -0.0046(14) -0.0011(15) C4 0.0382(17) 0.0449(18) 0.0436(19) 0.0001(15) 0.0006(15) -0.0094(15) C5 0.0415(17) 0.0405(17) 0.0329(16) 0.0055(14) 0.0018(14) 0.0032(15) C6 0.0291(16) 0.0382(16) 0.0305(16) 0.0013(14) 0.0044(13) 0.0046(14) C7 0.0273(16) 0.0391(16) 0.0375(17) 0.0031(14) 0.0019(13) -0.0005(13) C8 0.0269(15) 0.0299(15) 0.0328(16) 0.0045(13) 0.0026(13) 0.0014(12) C9 0.0278(15) 0.0394(16) 0.0330(16) 0.0015(13) 0.0001(13) 0.0003(13) C10 0.0248(15) 0.0453(17) 0.0421(17) 0.0014(15) 0.0037(13) 0.0022(13) C11 0.0316(16) 0.0450(18) 0.0344(16) -0.0031(14) 0.0039(13) -0.0014(13) C12 0.0273(16) 0.0312(15) 0.0331(15) 0.0044(13) 0.0039(13) 0.0000(13) C13 0.0282(16) 0.0311(16) 0.0335(16) 0.0055(12) 0.0004(13) 0.0014(13) C14 0.0258(16) 0.0383(17) 0.0393(17) 0.0031(13) 0.0044(13) 0.0014(13) C15 0.0280(16) 0.0397(16) 0.0340(16) 0.0014(14) 0.0001(13) 0.0034(14) C16 0.0364(17) 0.059(2) 0.0396(18) 0.0050(16) -0.0009(15) -0.0023(16) C17 0.044(2) 0.070(2) 0.0366(18) 0.0124(17) 0.0054(15) 0.0038(18) C18 0.049(2) 0.063(2) 0.0308(17) -0.0013(16) -0.0030(16) 0.0093(18) C19 0.0418(19) 0.0497(19) 0.0371(18) -0.0022(15) -0.0071(15) 0.0013(15) C20 0.0273(16) 0.0397(17) 0.0373(18) 0.0063(14) 0.0004(13) 0.0051(14) _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 C1 1.732(3) . ? Cl2 C3 1.735(3) . ? Cl3 C20 1.742(3) . ? Cl4 C18 1.734(3) . ? O1 C13 1.226(3) . ? C1 C2 1.381(4) . ? C1 C6 1.388(4) . ? C2 C3 1.378(4) . ? C2 H2A 0.9400 . ? C3 C4 1.366(4) . ? C4 C5 1.378(4) . ? C4 H4A 0.9400 . ? C5 C6 1.394(4) . ? C5 H5A 0.9400 . ? C6 C7 1.469(4) . ? C7 C8 1.336(3) . ? C7 H7A 0.9400 . ? C8 C13 1.494(3) . ? C8 C9 1.503(3) . ? C9 C10 1.520(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C10 C11 1.511(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C11 C12 1.509(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C14 1.335(3) . ? C12 C13 1.504(3) . ? C14 C15 1.469(4) . ? C14 H14A 0.9400 . ? C15 C20 1.395(4) . ? C15 C16 1.396(4) . ? C16 C17 1.376(4) . ? C16 H16A 0.9400 . ? C17 C18 1.374(4) . ? C17 H17A 0.9400 . ? C18 C19 1.383(4) . ? C19 C20 1.384(4) . ? C19 H19A 0.9400 . ? 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 C2 C1 C6 122.5(3) . . ? C2 C1 Cl1 117.5(2) . . ? C6 C1 Cl1 120.0(2) . . ? C3 C2 C1 118.5(3) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C4 C3 C2 121.4(3) . . ? C4 C3 Cl2 119.1(2) . . ? C2 C3 Cl2 119.6(2) . . ? C3 C4 C5 119.0(3) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C4 C5 C6 122.3(3) . . ? C4 C5 H5A 118.9 . . ? C6 C5 H5A 118.9 . . ? C1 C6 C5 116.4(3) . . ? C1 C6 C7 122.7(2) . . ? C5 C6 C7 120.8(2) . . ? C8 C7 C6 126.7(2) . . ? C8 C7 H7A 116.7 . . ? C6 C7 H7A 116.7 . . ? C7 C8 C13 117.7(2) . . ? C7 C8 C9 124.5(2) . . ? C13 C8 C9 117.7(2) . . ? C8 C9 C10 110.1(2) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 109.7(2) . . ? C11 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? C11 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C10 113.6(2) . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C10 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C14 C12 C13 116.5(2) . . ? C14 C12 C11 124.9(2) . . ? C13 C12 C11 118.7(2) . . ? O1 C13 C8 120.8(2) . . ? O1 C13 C12 120.3(2) . . ? C8 C13 C12 119.0(2) . . ? C12 C14 C15 128.3(3) . . ? C12 C14 H14A 115.9 . . ? C15 C14 H14A 115.9 . . ? C20 C15 C16 116.2(3) . . ? C20 C15 C14 121.4(2) . . ? C16 C15 C14 122.4(3) . . ? C17 C16 C15 122.1(3) . . ? C17 C16 H16A 119.0 . . ? C15 C16 H16A 119.0 . . ? C18 C17 C16 119.4(3) . . ? C18 C17 H17A 120.3 . . ? C16 C17 H17A 120.3 . . ? C17 C18 C19 121.2(3) . . ? C17 C18 Cl4 119.3(2) . . ? C19 C18 Cl4 119.5(3) . . ? C18 C19 C20 118.0(3) . . ? C18 C19 H19A 121.0 . . ? C20 C19 H19A 121.0 . . ? C19 C20 C15 123.0(3) . . ? C19 C20 Cl3 116.6(2) . . ? C15 C20 Cl3 120.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.1(4) . . . . ? Cl1 C1 C2 C3 179.8(2) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C1 C2 C3 Cl2 -179.9(2) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? Cl2 C3 C4 C5 179.9(2) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C2 C1 C6 C5 -0.5(4) . . . . ? Cl1 C1 C6 C5 179.80(19) . . . . ? C2 C1 C6 C7 -177.7(2) . . . . ? Cl1 C1 C6 C7 2.6(4) . . . . ? C4 C5 C6 C1 0.6(4) . . . . ? C4 C5 C6 C7 177.9(3) . . . . ? C1 C6 C7 C8 -140.5(3) . . . . ? C5 C6 C7 C8 42.4(4) . . . . ? C6 C7 C8 C13 -176.3(2) . . . . ? C6 C7 C8 C9 7.5(4) . . . . ? C7 C8 C9 C10 137.7(3) . . . . ? C13 C8 C9 C10 -38.5(3) . . . . ? C8 C9 C10 C11 63.9(3) . . . . ? C9 C10 C11 C12 -53.7(3) . . . . ? C10 C11 C12 C14 -161.1(3) . . . . ? C10 C11 C12 C13 18.0(3) . . . . ? C7 C8 C13 O1 7.6(4) . . . . ? C9 C8 C13 O1 -175.9(2) . . . . ? C7 C8 C13 C12 -173.3(2) . . . . ? C9 C8 C13 C12 3.2(3) . . . . ? C14 C12 C13 O1 6.0(4) . . . . ? C11 C12 C13 O1 -173.1(2) . . . . ? C14 C12 C13 C8 -173.1(2) . . . . ? C11 C12 C13 C8 7.7(3) . . . . ? C13 C12 C14 C15 179.4(2) . . . . ? C11 C12 C14 C15 -1.6(4) . . . . ? C12 C14 C15 C20 144.8(3) . . . . ? C12 C14 C15 C16 -35.8(4) . . . . ? C20 C15 C16 C17 -2.1(4) . . . . ? C14 C15 C16 C17 178.5(3) . . . . ? C15 C16 C17 C18 -1.4(5) . . . . ? C16 C17 C18 C19 3.5(5) . . . . ? C16 C17 C18 Cl4 -176.6(2) . . . . ? C17 C18 C19 C20 -2.1(5) . . . . ? Cl4 C18 C19 C20 178.1(2) . . . . ? C18 C19 C20 C15 -1.6(4) . . . . ? C18 C19 C20 Cl3 179.0(2) . . . . ? C16 C15 C20 C19 3.6(4) . . . . ? C14 C15 C20 C19 -177.0(3) . . . . ? C16 C15 C20 Cl3 -177.1(2) . . . . ? C14 C15 C20 Cl3 2.3(4) . . . . ? data_200K _database_code_depnum_ccdc_archive 'CCDC 794784' #TrackingRef '- CE-COM-09-2010-000676_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 2,6-bis(2,4-dichlorobenzylidene)cyclohexanone _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cl4 O' _chemical_formula_sum 'C20 H14 Cl4 O' _chemical_formula_weight 412.11 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.3893(12) _cell_length_b 7.9176(4) _cell_length_c 31.485(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3587.0(5) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1340 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 23.57 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.665 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.000 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 200(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 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 8276 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0742 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 24.99 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.983 _reflns_number_total 3098 _reflns_number_gt 1975 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0295P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3098 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0891 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.0824 _refine_ls_wR_factor_gt 0.0699 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.295 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.061 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 0.28440(6) 0.20089(11) 0.41328(3) 0.0498(3) Uani 1 1 d . . . Cl2 Cl 0.56792(6) 0.60650(11) 0.45507(3) 0.0519(3) Uani 1 1 d . . . Cl3 Cl -0.01357(5) 0.04480(9) 0.16223(2) 0.0326(2) Uani 1 1 d . . . Cl4 Cl 0.12798(7) 0.07721(13) 0.00509(3) 0.0632(3) Uani 1 1 d . . . O1 O 0.13677(12) 0.3229(2) 0.27434(6) 0.0323(5) Uani 1 1 d . . . C1 C 0.36061(19) 0.3611(3) 0.39921(9) 0.0279(7) Uani 1 1 d . . . C2 C 0.42506(19) 0.4128(3) 0.42887(9) 0.0325(8) Uani 1 1 d . . . H2A H 0.4272 0.3620 0.4562 0.039 Uiso 1 1 calc R . . C3 C 0.48620(19) 0.5393(4) 0.41820(10) 0.0310(7) Uani 1 1 d . . . C4 C 0.4836(2) 0.6132(4) 0.37899(10) 0.0323(8) Uani 1 1 d . . . H4A H 0.5261 0.7007 0.3720 0.039 Uiso 1 1 calc R . . C5 C 0.41921(19) 0.5601(3) 0.34971(10) 0.0290(7) Uani 1 1 d . . . H5A H 0.4179 0.6118 0.3225 0.035 Uiso 1 1 calc R . . C6 C 0.35553(18) 0.4318(3) 0.35888(9) 0.0247(7) Uani 1 1 d . . . C7 C 0.28549(19) 0.3818(3) 0.32746(9) 0.0265(7) Uani 1 1 d . . . H7A H 0.2246 0.3611 0.3379 0.032 Uiso 1 1 calc R . . C8 C 0.29827(18) 0.3622(3) 0.28573(9) 0.0230(7) Uani 1 1 d . . . C9 C 0.39126(17) 0.3697(3) 0.26380(9) 0.0252(7) Uani 1 1 d . . . H9A H 0.4416 0.3558 0.2850 0.030 Uiso 1 1 calc R . . H9B H 0.3990 0.4811 0.2500 0.030 Uiso 1 1 calc R . . C10 C 0.39788(18) 0.2304(3) 0.23060(9) 0.0282(7) Uani 1 1 d . . . H10A H 0.4610 0.2295 0.2181 0.034 Uiso 1 1 calc R . . H10B H 0.3869 0.1195 0.2442 0.034 Uiso 1 1 calc R . . C11 C 0.32662(17) 0.2589(4) 0.19595(9) 0.0281(7) Uani 1 1 d . . . H11A H 0.3436 0.3616 0.1798 0.034 Uiso 1 1 calc R . . H11B H 0.3280 0.1621 0.1761 0.034 Uiso 1 1 calc R . . C12 C 0.22905(17) 0.2791(3) 0.21311(9) 0.0225(7) Uani 1 1 d . . . C13 C 0.2151(2) 0.3206(3) 0.25900(9) 0.0245(7) Uani 1 1 d . . . C14 C 0.15220(19) 0.2602(3) 0.18966(9) 0.0261(7) Uani 1 1 d . . . H14A H 0.0951 0.2738 0.2044 0.031 Uiso 1 1 calc R . . C15 C 0.14436(19) 0.2211(3) 0.14410(9) 0.0259(7) Uani 1 1 d . . . C16 C 0.2072(2) 0.2831(4) 0.11407(10) 0.0343(8) Uani 1 1 d . . . H16A H 0.2558 0.3558 0.1233 0.041 Uiso 1 1 calc R . . C17 C 0.2012(2) 0.2426(4) 0.07163(10) 0.0377(8) Uani 1 1 d . . . H17A H 0.2445 0.2879 0.0519 0.045 Uiso 1 1 calc R . . C18 C 0.1322(2) 0.1361(4) 0.05814(10) 0.0378(8) Uani 1 1 d . . . C19 C 0.0660(2) 0.0753(3) 0.08603(10) 0.0329(8) Uani 1 1 d . . . H19A H 0.0173 0.0041 0.0763 0.039 Uiso 1 1 calc R . . C20 C 0.07233(18) 0.1202(3) 0.12837(9) 0.0260(7) Uani 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 0.0593(6) 0.0584(5) 0.0318(5) 0.0093(5) -0.0028(5) -0.0295(5) Cl2 0.0462(5) 0.0723(6) 0.0370(5) -0.0106(5) -0.0079(4) -0.0187(5) Cl3 0.0237(4) 0.0413(4) 0.0326(4) 0.0002(4) 0.0007(4) -0.0017(3) Cl4 0.0675(7) 0.0967(8) 0.0253(5) -0.0069(5) 0.0005(5) -0.0061(6) O1 0.0180(11) 0.0507(13) 0.0282(13) 0.0022(11) 0.0053(10) 0.0010(10) C1 0.0309(18) 0.0298(17) 0.0230(18) 0.0016(15) 0.0034(16) -0.0016(14) C2 0.039(2) 0.0386(18) 0.0195(18) 0.0001(15) 0.0004(16) -0.0032(16) C3 0.0290(17) 0.0362(16) 0.0278(18) -0.0090(16) -0.0009(16) -0.0013(15) C4 0.0300(18) 0.0335(17) 0.033(2) -0.0018(16) 0.0030(17) -0.0092(15) C5 0.0306(17) 0.0300(16) 0.0265(18) 0.0032(15) 0.0031(16) 0.0016(15) C6 0.0187(16) 0.0280(16) 0.0272(18) -0.0004(15) 0.0018(15) 0.0034(13) C7 0.0188(16) 0.0335(16) 0.0273(18) 0.0005(15) 0.0024(15) -0.0004(13) C8 0.0179(16) 0.0236(15) 0.0276(18) 0.0034(14) 0.0041(15) 0.0028(12) C9 0.0208(16) 0.0312(16) 0.0237(18) 0.0033(14) -0.0022(14) 0.0021(13) C10 0.0185(16) 0.0311(16) 0.0349(19) 0.0009(15) 0.0039(15) 0.0016(13) C11 0.0226(17) 0.0335(17) 0.0281(18) -0.0015(15) 0.0039(15) -0.0033(13) C12 0.0142(16) 0.0244(15) 0.0289(18) 0.0041(14) 0.0013(14) -0.0014(13) C13 0.0254(17) 0.0202(15) 0.0279(19) 0.0039(14) 0.0004(16) 0.0018(14) C14 0.0205(17) 0.0296(16) 0.0284(18) 0.0020(14) 0.0026(16) 0.0006(13) C15 0.0214(16) 0.0298(16) 0.0266(18) 0.0010(15) -0.0025(15) 0.0047(14) C16 0.0282(18) 0.0441(19) 0.0307(19) 0.0065(17) -0.0010(17) -0.0025(15) C17 0.0297(19) 0.054(2) 0.0291(19) 0.0104(17) 0.0063(17) -0.0001(17) C18 0.042(2) 0.0469(19) 0.0248(19) -0.0018(17) -0.0050(18) 0.0098(17) C19 0.0283(18) 0.0388(18) 0.032(2) -0.0007(16) -0.0083(17) 0.0020(15) C20 0.0205(16) 0.0306(16) 0.0270(19) 0.0037(15) 0.0011(15) 0.0060(14) _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 C1 1.734(3) . ? Cl2 C3 1.736(3) . ? Cl3 C20 1.738(3) . ? Cl4 C18 1.735(3) . ? O1 C13 1.227(3) . ? C1 C2 1.379(4) . ? C1 C6 1.390(4) . ? C2 C3 1.375(4) . ? C2 H2A 0.9500 . ? C3 C4 1.367(4) . ? C4 C5 1.373(4) . ? C4 H4A 0.9500 . ? C5 C6 1.398(4) . ? C5 H5A 0.9500 . ? C6 C7 1.467(4) . ? C7 C8 1.336(4) . ? C7 H7A 0.9500 . ? C8 C13 1.500(4) . ? C8 C9 1.507(3) . ? C9 C10 1.522(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.514(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.513(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.338(3) . ? C12 C13 1.495(4) . ? C14 C15 1.472(4) . ? C14 H14A 0.9500 . ? C15 C16 1.398(4) . ? C15 C20 1.399(4) . ? C16 C17 1.377(4) . ? C16 H16A 0.9500 . ? C17 C18 1.371(4) . ? C17 H17A 0.9500 . ? C18 C19 1.382(4) . ? C19 C20 1.383(4) . ? C19 H19A 0.9500 . ? 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 C2 C1 C6 122.3(3) . . ? C2 C1 Cl1 118.0(2) . . ? C6 C1 Cl1 119.7(2) . . ? C3 C2 C1 118.8(3) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C4 C3 C2 121.0(3) . . ? C4 C3 Cl2 119.4(2) . . ? C2 C3 Cl2 119.6(2) . . ? C3 C4 C5 119.6(3) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C4 C5 C6 121.7(3) . . ? C4 C5 H5A 119.1 . . ? C6 C5 H5A 119.1 . . ? C1 C6 C5 116.6(3) . . ? C1 C6 C7 122.9(3) . . ? C5 C6 C7 120.5(3) . . ? C8 C7 C6 126.9(3) . . ? C8 C7 H7A 116.6 . . ? C6 C7 H7A 116.6 . . ? C7 C8 C13 117.9(2) . . ? C7 C8 C9 124.6(3) . . ? C13 C8 C9 117.4(2) . . ? C8 C9 C10 110.0(2) . . ? C8 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? C8 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C11 C10 C9 110.2(2) . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 112.8(2) . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C14 C12 C13 116.5(2) . . ? C14 C12 C11 123.9(3) . . ? C13 C12 C11 119.5(2) . . ? O1 C13 C12 120.5(3) . . ? O1 C13 C8 120.6(3) . . ? C12 C13 C8 118.9(2) . . ? C12 C14 C15 128.7(3) . . ? C12 C14 H14A 115.7 . . ? C15 C14 H14A 115.7 . . ? C16 C15 C20 116.2(3) . . ? C16 C15 C14 122.4(3) . . ? C20 C15 C14 121.4(3) . . ? C17 C16 C15 122.3(3) . . ? C17 C16 H16A 118.9 . . ? C15 C16 H16A 118.9 . . ? C18 C17 C16 119.3(3) . . ? C18 C17 H17A 120.3 . . ? C16 C17 H17A 120.3 . . ? C17 C18 C19 121.1(3) . . ? C17 C18 Cl4 119.3(3) . . ? C19 C18 Cl4 119.6(3) . . ? C18 C19 C20 118.6(3) . . ? C18 C19 H19A 120.7 . . ? C20 C19 H19A 120.7 . . ? C19 C20 C15 122.5(3) . . ? C19 C20 Cl3 117.2(2) . . ? C15 C20 Cl3 120.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.3(4) . . . . ? Cl1 C1 C2 C3 179.8(2) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C1 C2 C3 Cl2 180.0(2) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? Cl2 C3 C4 C5 179.8(2) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? Cl1 C1 C6 C5 -179.88(19) . . . . ? C2 C1 C6 C7 -178.0(3) . . . . ? Cl1 C1 C6 C7 2.4(4) . . . . ? C4 C5 C6 C1 0.1(4) . . . . ? C4 C5 C6 C7 177.9(3) . . . . ? C1 C6 C7 C8 -140.6(3) . . . . ? C5 C6 C7 C8 41.8(4) . . . . ? C6 C7 C8 C13 -176.3(2) . . . . ? C6 C7 C8 C9 7.2(4) . . . . ? C7 C8 C9 C10 137.9(3) . . . . ? C13 C8 C9 C10 -38.6(3) . . . . ? C8 C9 C10 C11 64.3(3) . . . . ? C9 C10 C11 C12 -53.6(3) . . . . ? C10 C11 C12 C14 -161.3(2) . . . . ? C10 C11 C12 C13 18.0(3) . . . . ? C14 C12 C13 O1 5.7(4) . . . . ? C11 C12 C13 O1 -173.6(2) . . . . ? C14 C12 C13 C8 -173.3(2) . . . . ? C11 C12 C13 C8 7.4(3) . . . . ? C7 C8 C13 O1 7.8(4) . . . . ? C9 C8 C13 O1 -175.4(2) . . . . ? C7 C8 C13 C12 -173.2(2) . . . . ? C9 C8 C13 C12 3.5(3) . . . . ? C13 C12 C14 C15 179.4(3) . . . . ? C11 C12 C14 C15 -1.3(4) . . . . ? C12 C14 C15 C16 -35.7(4) . . . . ? C12 C14 C15 C20 145.0(3) . . . . ? C20 C15 C16 C17 -2.4(4) . . . . ? C14 C15 C16 C17 178.2(3) . . . . ? C15 C16 C17 C18 -0.8(5) . . . . ? C16 C17 C18 C19 3.1(5) . . . . ? C16 C17 C18 Cl4 -177.0(2) . . . . ? C17 C18 C19 C20 -1.9(4) . . . . ? Cl4 C18 C19 C20 178.2(2) . . . . ? C18 C19 C20 C15 -1.7(4) . . . . ? C18 C19 C20 Cl3 178.7(2) . . . . ? C16 C15 C20 C19 3.7(4) . . . . ? C14 C15 C20 C19 -176.9(3) . . . . ? C16 C15 C20 Cl3 -176.6(2) . . . . ? C14 C15 C20 Cl3 2.8(4) . . . . ? data_150K _database_code_depnum_ccdc_archive 'CCDC 794785' #TrackingRef '- CE-COM-09-2010-000676_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 2,6-bis(2,4-dichlorobenzylidene)cyclohexanone _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cl4 O' _chemical_formula_sum 'C20 H14 Cl4 O' _chemical_formula_weight 412.11 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.3879(13) _cell_length_b 7.8591(8) _cell_length_c 31.494(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3561.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3167 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 25.02 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.670 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.000 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(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 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 15730 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 25.04 _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.918 _reflns_number_total 2893 _reflns_number_gt 2164 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0297P)^2^+1.8684P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2893 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0777 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.276 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.055 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 0.28469(5) 0.19050(10) 0.41349(2) 0.0367(2) Uani 1 1 d . . . Cl2 Cl 0.56915(5) 0.59791(11) 0.45557(2) 0.0379(2) Uani 1 1 d . . . Cl3 Cl -0.01400(4) 0.03660(9) 0.162528(18) 0.02369(17) Uani 1 1 d . . . Cl4 Cl 0.12821(5) 0.07076(12) 0.00543(2) 0.0462(3) Uani 1 1 d . . . O1 O 0.13725(11) 0.3151(2) 0.27469(5) 0.0230(4) Uani 1 1 d . . . C1 C 0.36096(17) 0.3516(3) 0.39950(7) 0.0210(6) Uani 1 1 d . . . C2 C 0.42579(17) 0.4028(4) 0.42933(7) 0.0251(6) Uani 1 1 d . . . H2A H 0.4278 0.3512 0.4566 0.030 Uiso 1 1 calc R . . C3 C 0.48724(17) 0.5298(4) 0.41871(7) 0.0244(6) Uani 1 1 d . . . C4 C 0.48476(17) 0.6068(4) 0.37934(7) 0.0246(6) Uani 1 1 d . . . H4A H 0.5272 0.6953 0.3725 0.030 Uiso 1 1 calc R . . C5 C 0.41990(16) 0.5532(4) 0.35029(7) 0.0216(6) Uani 1 1 d . . . H5A H 0.4180 0.6066 0.3232 0.026 Uiso 1 1 calc R . . C6 C 0.35673(15) 0.4234(4) 0.35900(7) 0.0188(6) Uani 1 1 d . . . C7 C 0.28561(17) 0.3733(3) 0.32787(7) 0.0203(6) Uani 1 1 d . . . H7A H 0.2248 0.3519 0.3384 0.024 Uiso 1 1 calc R . . C8 C 0.29886(16) 0.3552(3) 0.28598(7) 0.0180(6) Uani 1 1 d . . . C9 C 0.39180(15) 0.3629(4) 0.26404(7) 0.0190(6) Uani 1 1 d . . . H9A H 0.4421 0.3499 0.2852 0.023 Uiso 1 1 calc R . . H9B H 0.3993 0.4749 0.2501 0.023 Uiso 1 1 calc R . . C10 C 0.39904(16) 0.2222(4) 0.23106(7) 0.0211(6) Uani 1 1 d . . . H10A H 0.4622 0.2215 0.2185 0.025 Uiso 1 1 calc R . . H10B H 0.3881 0.1104 0.2446 0.025 Uiso 1 1 calc R . . C11 C 0.32726(16) 0.2521(4) 0.19645(7) 0.0207(6) Uani 1 1 d . . . H11A H 0.3442 0.3562 0.1805 0.025 Uiso 1 1 calc R . . H11B H 0.3290 0.1554 0.1763 0.025 Uiso 1 1 calc R . . C12 C 0.22939(15) 0.2715(3) 0.21317(7) 0.0167(6) Uani 1 1 d . . . C13 C 0.21564(16) 0.3133(3) 0.25956(7) 0.0181(6) Uani 1 1 d . . . C14 C 0.15191(16) 0.2528(3) 0.19009(7) 0.0194(6) Uani 1 1 d . . . H14A H 0.0949 0.2668 0.2049 0.023 Uiso 1 1 calc R . . C15 C 0.14450(16) 0.2132(4) 0.14453(7) 0.0205(6) Uani 1 1 d . . . C16 C 0.20780(17) 0.2772(4) 0.11470(8) 0.0258(7) Uani 1 1 d . . . H16A H 0.2561 0.3507 0.1240 0.031 Uiso 1 1 calc R . . C17 C 0.20188(17) 0.2365(4) 0.07219(8) 0.0279(7) Uani 1 1 d . . . H17A H 0.2454 0.2819 0.0525 0.033 Uiso 1 1 calc R . . C18 C 0.13247(18) 0.1297(4) 0.05857(8) 0.0270(7) Uani 1 1 d . . . C19 C 0.06604(17) 0.0678(4) 0.08623(8) 0.0255(6) Uani 1 1 d . . . H19A H 0.0175 -0.0042 0.0765 0.031 Uiso 1 1 calc R . . C20 C 0.07223(16) 0.1135(4) 0.12860(7) 0.0199(6) Uani 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 0.0446(4) 0.0416(5) 0.0237(3) 0.0067(3) -0.0029(3) -0.0223(4) Cl2 0.0347(4) 0.0523(6) 0.0266(4) -0.0089(3) -0.0054(3) -0.0139(4) Cl3 0.0181(3) 0.0288(4) 0.0242(3) -0.0004(3) 0.0008(3) -0.0012(3) Cl4 0.0511(5) 0.0689(7) 0.0187(3) -0.0059(4) 0.0008(3) -0.0062(4) O1 0.0160(9) 0.0319(13) 0.0212(9) 0.0015(8) 0.0012(7) 0.0002(8) C1 0.0243(14) 0.0196(18) 0.0193(13) -0.0009(11) 0.0038(10) -0.0023(11) C2 0.0302(15) 0.0281(19) 0.0170(13) -0.0017(12) 0.0001(11) -0.0019(13) C3 0.0238(14) 0.0286(19) 0.0208(13) -0.0094(12) -0.0013(11) -0.0003(12) C4 0.0251(14) 0.0233(18) 0.0254(13) -0.0005(12) 0.0039(11) -0.0039(12) C5 0.0233(14) 0.0223(18) 0.0193(12) 0.0025(11) 0.0017(10) -0.0002(12) C6 0.0172(13) 0.0214(19) 0.0178(12) -0.0032(11) 0.0029(10) 0.0033(11) C7 0.0183(13) 0.0182(17) 0.0244(13) 0.0012(11) 0.0017(10) 0.0026(11) C8 0.0156(13) 0.0148(17) 0.0235(13) 0.0037(11) 0.0002(10) 0.0012(10) C9 0.0164(13) 0.0196(17) 0.0210(13) 0.0029(11) -0.0015(10) 0.0006(11) C10 0.0150(13) 0.0221(18) 0.0261(13) 0.0005(12) 0.0036(10) 0.0021(11) C11 0.0185(13) 0.0241(18) 0.0196(12) -0.0023(12) 0.0034(10) -0.0017(11) C12 0.0173(13) 0.0134(16) 0.0195(12) 0.0000(11) 0.0025(10) -0.0017(11) C13 0.0186(14) 0.0151(16) 0.0206(13) 0.0058(11) 0.0007(10) 0.0019(11) C14 0.0159(13) 0.0202(18) 0.0219(13) 0.0012(11) 0.0032(10) 0.0019(11) C15 0.0195(13) 0.0220(18) 0.0199(12) 0.0020(11) -0.0007(10) 0.0049(11) C16 0.0208(14) 0.031(2) 0.0258(13) 0.0014(12) -0.0018(11) -0.0009(12) C17 0.0246(15) 0.036(2) 0.0233(13) 0.0064(13) 0.0041(11) 0.0025(13) C18 0.0289(15) 0.034(2) 0.0178(12) -0.0010(12) -0.0028(11) 0.0072(13) C19 0.0232(14) 0.0277(19) 0.0256(13) -0.0027(12) -0.0045(11) 0.0023(12) C20 0.0159(13) 0.0216(17) 0.0223(13) 0.0017(11) 0.0011(10) 0.0054(11) _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 C1 1.732(3) . ? Cl2 C3 1.738(2) . ? Cl3 C20 1.745(2) . ? Cl4 C18 1.737(3) . ? O1 C13 1.224(3) . ? C1 C2 1.384(3) . ? C1 C6 1.396(3) . ? C2 C3 1.375(4) . ? C2 H2A 0.9500 . ? C3 C4 1.380(3) . ? C4 C5 1.373(3) . ? C4 H4A 0.9500 . ? C5 C6 1.393(4) . ? C5 H5A 0.9500 . ? C6 C7 1.471(3) . ? C7 C8 1.340(3) . ? C7 H7A 0.9500 . ? C8 C13 1.495(3) . ? C8 C9 1.506(3) . ? C9 C10 1.521(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.520(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.511(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.339(3) . ? C12 C13 1.511(3) . ? C14 C15 1.472(3) . ? C14 H14A 0.9500 . ? C15 C20 1.395(4) . ? C15 C16 1.402(3) . ? C16 C17 1.379(3) . ? C16 H16A 0.9500 . ? C17 C18 1.373(4) . ? C17 H17A 0.9500 . ? C18 C19 1.382(4) . ? C19 C20 1.385(3) . ? C19 H19A 0.9500 . ? 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 C2 C1 C6 122.2(2) . . ? C2 C1 Cl1 117.82(19) . . ? C6 C1 Cl1 120.02(19) . . ? C3 C2 C1 118.6(2) . . ? C3 C2 H2A 120.7 . . ? C1 C2 H2A 120.7 . . ? C2 C3 C4 121.3(2) . . ? C2 C3 Cl2 119.80(19) . . ? C4 C3 Cl2 118.8(2) . . ? C5 C4 C3 118.8(2) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C4 C5 C6 122.5(2) . . ? C4 C5 H5A 118.8 . . ? C6 C5 H5A 118.8 . . ? C5 C6 C1 116.6(2) . . ? C5 C6 C7 121.2(2) . . ? C1 C6 C7 122.1(2) . . ? C8 C7 C6 125.8(2) . . ? C8 C7 H7A 117.1 . . ? C6 C7 H7A 117.1 . . ? C7 C8 C13 117.2(2) . . ? C7 C8 C9 125.0(2) . . ? C13 C8 C9 117.7(2) . . ? C8 C9 C10 110.2(2) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 109.3(2) . . ? C11 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? C12 C11 C10 113.50(19) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C14 C12 C13 116.1(2) . . ? C14 C12 C11 125.1(2) . . ? C13 C12 C11 118.76(19) . . ? O1 C13 C8 121.3(2) . . ? O1 C13 C12 120.0(2) . . ? C8 C13 C12 118.8(2) . . ? C12 C14 C15 127.8(2) . . ? C12 C14 H14A 116.1 . . ? C15 C14 H14A 116.1 . . ? C20 C15 C16 116.4(2) . . ? C20 C15 C14 121.5(2) . . ? C16 C15 C14 122.0(2) . . ? C17 C16 C15 121.8(3) . . ? C17 C16 H16A 119.1 . . ? C15 C16 H16A 119.1 . . ? C18 C17 C16 119.3(2) . . ? C18 C17 H17A 120.3 . . ? C16 C17 H17A 120.3 . . ? C17 C18 C19 121.4(2) . . ? C17 C18 Cl4 119.3(2) . . ? C19 C18 Cl4 119.3(2) . . ? C18 C19 C20 118.1(2) . . ? C18 C19 H19A 120.9 . . ? C20 C19 H19A 120.9 . . ? C19 C20 C15 122.7(2) . . ? C19 C20 Cl3 117.0(2) . . ? C15 C20 Cl3 120.28(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.7(4) . . . . ? Cl1 C1 C2 C3 179.7(2) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? C1 C2 C3 Cl2 179.6(2) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? Cl2 C3 C4 C5 -179.86(19) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C4 C5 C6 C1 1.4(4) . . . . ? C4 C5 C6 C7 177.5(2) . . . . ? C2 C1 C6 C5 -1.6(4) . . . . ? Cl1 C1 C6 C5 179.51(19) . . . . ? C2 C1 C6 C7 -177.7(2) . . . . ? Cl1 C1 C6 C7 3.4(3) . . . . ? C5 C6 C7 C8 42.4(4) . . . . ? C1 C6 C7 C8 -141.7(3) . . . . ? C6 C7 C8 C13 -176.4(2) . . . . ? C6 C7 C8 C9 7.6(4) . . . . ? C7 C8 C9 C10 136.9(3) . . . . ? C13 C8 C9 C10 -39.0(3) . . . . ? C8 C9 C10 C11 64.4(3) . . . . ? C9 C10 C11 C12 -54.1(3) . . . . ? C10 C11 C12 C14 -160.9(3) . . . . ? C10 C11 C12 C13 18.4(3) . . . . ? C7 C8 C13 O1 8.3(4) . . . . ? C9 C8 C13 O1 -175.5(2) . . . . ? C7 C8 C13 C12 -172.9(2) . . . . ? C9 C8 C13 C12 3.4(3) . . . . ? C14 C12 C13 O1 5.7(4) . . . . ? C11 C12 C13 O1 -173.7(2) . . . . ? C14 C12 C13 C8 -173.1(2) . . . . ? C11 C12 C13 C8 7.5(3) . . . . ? C13 C12 C14 C15 179.7(3) . . . . ? C11 C12 C14 C15 -1.0(4) . . . . ? C12 C14 C15 C20 145.7(3) . . . . ? C12 C14 C15 C16 -36.2(4) . . . . ? C20 C15 C16 C17 -3.4(4) . . . . ? C14 C15 C16 C17 178.4(3) . . . . ? C15 C16 C17 C18 -0.3(4) . . . . ? C16 C17 C18 C19 2.8(4) . . . . ? C16 C17 C18 Cl4 -177.1(2) . . . . ? C17 C18 C19 C20 -1.3(4) . . . . ? Cl4 C18 C19 C20 178.5(2) . . . . ? C18 C19 C20 C15 -2.6(4) . . . . ? C18 C19 C20 Cl3 178.8(2) . . . . ? C16 C15 C20 C19 4.9(4) . . . . ? C14 C15 C20 C19 -176.9(2) . . . . ? C16 C15 C20 Cl3 -176.6(2) . . . . ? C14 C15 C20 Cl3 1.6(4) . . . . ? data_120K _database_code_depnum_ccdc_archive 'CCDC 794786' #TrackingRef '- CE-COM-09-2010-000676_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 2,6-bis(2,4-dichlorobenzylidene)cyclohexanone _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cl4 O' _chemical_formula_sum 'C20 H14 Cl4 O' _chemical_formula_weight 412.11 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.3623(6) _cell_length_b 7.8230(4) _cell_length_c 31.5402(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3543.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3584 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 25.03 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.673 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.000 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 120(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 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 10102 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.04 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 3124 _reflns_number_gt 2568 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0365P)^2^+3.6015P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3124 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0797 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.293 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.056 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 0.28488(4) 0.18161(9) 0.413652(19) 0.02908(18) Uani 1 1 d . . . Cl2 Cl 0.57034(4) 0.58942(9) 0.455957(19) 0.02977(18) Uani 1 1 d . . . Cl3 Cl -0.01422(4) 0.02864(8) 0.162777(18) 0.01907(15) Uani 1 1 d . . . Cl4 Cl 0.12858(5) 0.06489(10) 0.005919(19) 0.0364(2) Uani 1 1 d . . . O1 O 0.13760(10) 0.3077(2) 0.27505(5) 0.0192(4) Uani 1 1 d . . . C1 C 0.36177(16) 0.3436(3) 0.39972(7) 0.0172(5) Uani 1 1 d . . . C2 C 0.42652(16) 0.3935(3) 0.42962(7) 0.0200(5) Uani 1 1 d . . . H2A H 0.4288 0.3408 0.4567 0.024 Uiso 1 1 calc R . . C3 C 0.48792(16) 0.5222(3) 0.41893(7) 0.0200(5) Uani 1 1 d . . . C4 C 0.48579(16) 0.5997(3) 0.37980(7) 0.0200(5) Uani 1 1 d . . . H4A H 0.5285 0.6882 0.3730 0.024 Uiso 1 1 calc R . . C5 C 0.42054(16) 0.5466(3) 0.35056(8) 0.0194(5) Uani 1 1 d . . . H5A H 0.4185 0.6007 0.3236 0.023 Uiso 1 1 calc R . . C6 C 0.35734(15) 0.4158(3) 0.35939(7) 0.0166(5) Uani 1 1 d . . . C7 C 0.28608(16) 0.3660(3) 0.32812(7) 0.0161(5) Uani 1 1 d . . . H7A H 0.2252 0.3446 0.3386 0.019 Uiso 1 1 calc R . . C8 C 0.29924(15) 0.3480(3) 0.28632(7) 0.0153(5) Uani 1 1 d . . . C9 C 0.39252(15) 0.3556(3) 0.26445(7) 0.0162(5) Uani 1 1 d . . . H9A H 0.4428 0.3418 0.2856 0.019 Uiso 1 1 calc R . . H9B H 0.4003 0.4684 0.2507 0.019 Uiso 1 1 calc R . . C10 C 0.39975(15) 0.2155(3) 0.23139(7) 0.0178(5) Uani 1 1 d . . . H10A H 0.4629 0.2156 0.2188 0.021 Uiso 1 1 calc R . . H10B H 0.3892 0.1029 0.2449 0.021 Uiso 1 1 calc R . . C11 C 0.32749(15) 0.2448(3) 0.19678(7) 0.0166(5) Uani 1 1 d . . . H11A H 0.3443 0.3491 0.1807 0.020 Uiso 1 1 calc R . . H11B H 0.3291 0.1472 0.1768 0.020 Uiso 1 1 calc R . . C12 C 0.22991(15) 0.2641(3) 0.21366(7) 0.0152(5) Uani 1 1 d . . . C13 C 0.21591(15) 0.3053(3) 0.26002(7) 0.0151(5) Uani 1 1 d . . . C14 C 0.15195(16) 0.2452(3) 0.19056(7) 0.0168(5) Uani 1 1 d . . . H14A H 0.0948 0.2585 0.2053 0.020 Uiso 1 1 calc R . . C15 C 0.14490(16) 0.2066(3) 0.14520(7) 0.0171(5) Uani 1 1 d . . . C16 C 0.20811(16) 0.2701(3) 0.11510(8) 0.0209(5) Uani 1 1 d . . . H16A H 0.2568 0.3433 0.1244 0.025 Uiso 1 1 calc R . . C17 C 0.20240(17) 0.2306(3) 0.07270(8) 0.0228(6) Uani 1 1 d . . . H17A H 0.2458 0.2770 0.0531 0.027 Uiso 1 1 calc R . . C18 C 0.13253(17) 0.1223(3) 0.05912(7) 0.0223(6) Uani 1 1 d . . . C19 C 0.06606(16) 0.0605(3) 0.08652(7) 0.0203(5) Uani 1 1 d . . . H19A H 0.0173 -0.0113 0.0767 0.024 Uiso 1 1 calc R . . C20 C 0.07219(15) 0.1059(3) 0.12893(7) 0.0168(5) Uani 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 0.0353(4) 0.0327(4) 0.0193(3) 0.0059(3) -0.0028(3) -0.0181(3) Cl2 0.0259(3) 0.0410(4) 0.0224(3) -0.0073(3) -0.0037(3) -0.0112(3) Cl3 0.0143(3) 0.0228(3) 0.0201(3) 0.0001(3) 0.0011(2) -0.0007(2) Cl4 0.0407(4) 0.0534(5) 0.0153(3) -0.0058(3) 0.0009(3) -0.0051(4) O1 0.0137(8) 0.0264(10) 0.0175(8) 0.0017(7) 0.0027(7) 0.0004(7) C1 0.0178(12) 0.0166(12) 0.0173(12) -0.0019(10) 0.0033(10) -0.0025(10) C2 0.0231(13) 0.0229(13) 0.0140(12) -0.0014(11) 0.0007(10) 0.0011(11) C3 0.0157(11) 0.0229(13) 0.0213(12) -0.0070(11) -0.0005(10) -0.0011(10) C4 0.0196(12) 0.0191(13) 0.0212(13) -0.0015(11) 0.0039(10) -0.0013(10) C5 0.0194(12) 0.0210(13) 0.0178(12) 0.0011(10) 0.0003(10) 0.0010(11) C6 0.0166(12) 0.0158(12) 0.0175(11) -0.0012(10) 0.0027(9) 0.0029(10) C7 0.0135(11) 0.0145(12) 0.0205(12) 0.0028(10) -0.0004(9) -0.0003(9) C8 0.0153(11) 0.0124(12) 0.0181(12) 0.0036(10) -0.0003(9) 0.0025(9) C9 0.0104(10) 0.0195(13) 0.0188(12) 0.0022(10) -0.0011(9) -0.0008(9) C10 0.0124(11) 0.0207(13) 0.0204(12) 0.0006(10) 0.0018(9) 0.0010(10) C11 0.0144(11) 0.0221(13) 0.0133(11) -0.0001(10) 0.0050(9) -0.0017(10) C12 0.0161(12) 0.0126(12) 0.0170(11) 0.0010(10) 0.0001(9) 0.0000(10) C13 0.0145(11) 0.0110(11) 0.0199(12) 0.0045(10) 0.0003(9) 0.0003(9) C14 0.0148(11) 0.0143(12) 0.0213(12) 0.0015(10) 0.0045(9) 0.0015(9) C15 0.0166(11) 0.0170(12) 0.0178(12) 0.0002(10) -0.0014(9) 0.0044(10) C16 0.0162(12) 0.0241(14) 0.0225(13) 0.0007(11) -0.0009(10) -0.0015(11) C17 0.0208(12) 0.0284(15) 0.0193(12) 0.0056(11) 0.0040(10) 0.0033(11) C18 0.0242(13) 0.0278(14) 0.0148(12) -0.0007(11) -0.0020(10) 0.0070(11) C19 0.0193(12) 0.0219(13) 0.0195(12) -0.0016(11) -0.0023(10) 0.0026(11) C20 0.0135(11) 0.0170(12) 0.0198(12) 0.0025(10) 0.0011(9) 0.0042(10) _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 C1 1.737(2) . ? Cl2 C3 1.744(2) . ? Cl3 C20 1.745(2) . ? Cl4 C18 1.738(2) . ? O1 C13 1.221(3) . ? C1 C2 1.381(3) . ? C1 C6 1.393(3) . ? C2 C3 1.380(3) . ? C2 H2A 0.9500 . ? C3 C4 1.375(3) . ? C4 C5 1.379(3) . ? C4 H4A 0.9500 . ? C5 C6 1.396(3) . ? C5 H5A 0.9500 . ? C6 C7 1.474(3) . ? C7 C8 1.339(3) . ? C7 H7A 0.9500 . ? C8 C13 1.494(3) . ? C8 C9 1.508(3) . ? C9 C10 1.516(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.523(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.507(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.344(3) . ? C12 C13 1.511(3) . ? C14 C15 1.466(3) . ? C14 H14A 0.9500 . ? C15 C16 1.405(3) . ? C15 C20 1.405(3) . ? C16 C17 1.375(3) . ? C16 H16A 0.9500 . ? C17 C18 1.381(4) . ? C17 H17A 0.9500 . ? C18 C19 1.375(3) . ? C19 C20 1.387(3) . ? C19 H19A 0.9500 . ? 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 C2 C1 C6 122.7(2) . . ? C2 C1 Cl1 117.49(18) . . ? C6 C1 Cl1 119.83(18) . . ? C3 C2 C1 118.0(2) . . ? C3 C2 H2A 121.0 . . ? C1 C2 H2A 121.0 . . ? C4 C3 C2 121.8(2) . . ? C4 C3 Cl2 118.88(19) . . ? C2 C3 Cl2 119.35(19) . . ? C3 C4 C5 118.8(2) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C4 C5 C6 122.0(2) . . ? C4 C5 H5A 119.0 . . ? C6 C5 H5A 119.0 . . ? C1 C6 C5 116.7(2) . . ? C1 C6 C7 122.4(2) . . ? C5 C6 C7 120.8(2) . . ? C8 C7 C6 126.1(2) . . ? C8 C7 H7A 117.0 . . ? C6 C7 H7A 117.0 . . ? C7 C8 C13 117.2(2) . . ? C7 C8 C9 124.9(2) . . ? C13 C8 C9 117.80(19) . . ? C8 C9 C10 110.31(19) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C9 C10 C11 109.74(19) . . ? C9 C10 H10A 109.7 . . ? C11 C10 H10A 109.7 . . ? C9 C10 H10B 109.7 . . ? C11 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C10 113.30(19) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C14 C12 C11 124.9(2) . . ? C14 C12 C13 115.9(2) . . ? C11 C12 C13 119.15(19) . . ? O1 C13 C8 121.3(2) . . ? O1 C13 C12 120.1(2) . . ? C8 C13 C12 118.59(19) . . ? C12 C14 C15 127.5(2) . . ? C12 C14 H14A 116.2 . . ? C15 C14 H14A 116.2 . . ? C16 C15 C20 115.6(2) . . ? C16 C15 C14 122.8(2) . . ? C20 C15 C14 121.6(2) . . ? C17 C16 C15 122.6(2) . . ? C17 C16 H16A 118.7 . . ? C15 C16 H16A 118.7 . . ? C16 C17 C18 118.9(2) . . ? C16 C17 H17A 120.6 . . ? C18 C17 H17A 120.6 . . ? C19 C18 C17 121.7(2) . . ? C19 C18 Cl4 119.5(2) . . ? C17 C18 Cl4 118.79(19) . . ? C18 C19 C20 118.2(2) . . ? C18 C19 H19A 120.9 . . ? C20 C19 H19A 120.9 . . ? C19 C20 C15 122.9(2) . . ? C19 C20 Cl3 117.16(18) . . ? C15 C20 Cl3 119.95(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.1(4) . . . . ? Cl1 C1 C2 C3 -179.94(18) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? C1 C2 C3 Cl2 179.67(18) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? Cl2 C3 C4 C5 -179.92(18) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C2 C1 C6 C5 -1.8(3) . . . . ? Cl1 C1 C6 C5 179.29(18) . . . . ? C2 C1 C6 C7 -177.9(2) . . . . ? Cl1 C1 C6 C7 3.2(3) . . . . ? C4 C5 C6 C1 1.5(3) . . . . ? C4 C5 C6 C7 177.7(2) . . . . ? C1 C6 C7 C8 -141.6(3) . . . . ? C5 C6 C7 C8 42.5(4) . . . . ? C6 C7 C8 C13 -176.9(2) . . . . ? C6 C7 C8 C9 7.6(4) . . . . ? C7 C8 C9 C10 137.2(2) . . . . ? C13 C8 C9 C10 -38.4(3) . . . . ? C8 C9 C10 C11 63.9(2) . . . . ? C9 C10 C11 C12 -53.6(3) . . . . ? C10 C11 C12 C14 -161.2(2) . . . . ? C10 C11 C12 C13 17.9(3) . . . . ? C7 C8 C13 O1 8.9(3) . . . . ? C9 C8 C13 O1 -175.2(2) . . . . ? C7 C8 C13 C12 -173.0(2) . . . . ? C9 C8 C13 C12 2.8(3) . . . . ? C14 C12 C13 O1 5.2(3) . . . . ? C11 C12 C13 O1 -174.0(2) . . . . ? C14 C12 C13 C8 -172.9(2) . . . . ? C11 C12 C13 C8 7.9(3) . . . . ? C11 C12 C14 C15 -1.3(4) . . . . ? C13 C12 C14 C15 179.5(2) . . . . ? C12 C14 C15 C16 -35.7(4) . . . . ? C12 C14 C15 C20 145.9(2) . . . . ? C20 C15 C16 C17 -2.9(4) . . . . ? C14 C15 C16 C17 178.6(2) . . . . ? C15 C16 C17 C18 -0.9(4) . . . . ? C16 C17 C18 C19 3.4(4) . . . . ? C16 C17 C18 Cl4 -177.14(19) . . . . ? C17 C18 C19 C20 -1.8(4) . . . . ? Cl4 C18 C19 C20 178.72(18) . . . . ? C18 C19 C20 C15 -2.3(4) . . . . ? C18 C19 C20 Cl3 178.91(18) . . . . ? C16 C15 C20 C19 4.6(3) . . . . ? C14 C15 C20 C19 -176.9(2) . . . . ? C16 C15 C20 Cl3 -176.70(17) . . . . ? C14 C15 C20 Cl3 1.8(3) . . . . ? data_110K _database_code_depnum_ccdc_archive 'CCDC 794787' #TrackingRef '- CE-COM-09-2010-000676_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 2,6-bis(2,4-dichlorobenzylidene)cyclohexanone _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cl4 O' _chemical_formula_sum 'C20 H14 Cl4 O' _chemical_formula_weight 412.11 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.3840(5) _cell_length_b 7.7638(3) _cell_length_c 31.8297(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3554.6(2) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5756 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 24.84 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.671 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.000 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 110(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 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 23015 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _reflns_number_total 3093 _reflns_number_gt 2513 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0254P)^2^+15.8809P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3093 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 1.276 _refine_ls_restrained_S_all 1.276 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.490 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.091 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 0.28702(9) 0.28724(18) 0.41538(4) 0.0290(3) Uani 1 1 d . . . Cl2 Cl 0.57381(8) 0.69260(17) 0.45817(4) 0.0242(3) Uani 1 1 d . . . Cl3 Cl -0.01260(7) 0.13322(15) 0.16510(3) 0.0169(3) Uani 1 1 d . . . Cl4 Cl 0.13614(9) 0.17099(19) 0.01078(4) 0.0308(3) Uani 1 1 d . . . O1 O 0.1402(2) 0.4126(4) 0.27832(9) 0.0180(7) Uani 1 1 d . . . C1 C 0.3643(3) 0.4496(6) 0.40163(14) 0.0165(10) Uani 1 1 d . . . C2 C 0.4292(3) 0.4998(6) 0.43193(14) 0.0189(11) Uani 1 1 d . . . H2A H 0.4303 0.4478 0.4589 0.023 Uiso 1 1 calc R . . C3 C 0.4919(3) 0.6285(6) 0.42116(14) 0.0172(10) Uani 1 1 d . . . C4 C 0.4905(3) 0.7049(6) 0.38224(14) 0.0181(10) Uani 1 1 d . . . H4A H 0.5338 0.7930 0.3755 0.022 Uiso 1 1 calc R . . C5 C 0.4254(3) 0.6526(6) 0.35287(14) 0.0171(10) Uani 1 1 d . . . H5A H 0.4246 0.7058 0.3260 0.021 Uiso 1 1 calc R . . C6 C 0.3607(3) 0.5229(6) 0.36183(14) 0.0158(10) Uani 1 1 d . . . C7 C 0.2894(3) 0.4732(6) 0.33065(14) 0.0159(10) Uani 1 1 d . . . H7A H 0.2285 0.4523 0.3410 0.019 Uiso 1 1 calc R . . C8 C 0.3022(3) 0.4547(6) 0.28919(13) 0.0136(10) Uani 1 1 d . . . C9 C 0.3946(3) 0.4635(6) 0.26707(14) 0.0156(10) Uani 1 1 d . . . H9A H 0.4455 0.4514 0.2878 0.019 Uiso 1 1 calc R . . H9B H 0.4013 0.5768 0.2531 0.019 Uiso 1 1 calc R . . C10 C 0.4018(3) 0.3206(6) 0.23445(14) 0.0177(10) Uani 1 1 d . . . H10A H 0.4649 0.3198 0.2220 0.021 Uiso 1 1 calc R . . H10B H 0.3909 0.2075 0.2480 0.021 Uiso 1 1 calc R . . C11 C 0.3294(3) 0.3508(6) 0.20017(14) 0.0172(10) Uani 1 1 d . . . H11A H 0.3462 0.4562 0.1844 0.021 Uiso 1 1 calc R . . H11B H 0.3309 0.2528 0.1803 0.021 Uiso 1 1 calc R . . C12 C 0.2319(3) 0.3702(6) 0.21716(14) 0.0148(10) Uani 1 1 d . . . C13 C 0.2187(3) 0.4106(6) 0.26311(14) 0.0148(10) Uani 1 1 d . . . C14 C 0.1536(3) 0.3511(6) 0.19426(14) 0.0164(10) Uani 1 1 d . . . H14A H 0.0965 0.3625 0.2090 0.020 Uiso 1 1 calc R . . C15 C 0.1469(3) 0.3146(6) 0.14888(14) 0.0159(10) Uani 1 1 d . . . C16 C 0.2103(3) 0.3822(6) 0.11978(14) 0.0196(11) Uani 1 1 d . . . H16A H 0.2572 0.4588 0.1293 0.024 Uiso 1 1 calc R . . C17 C 0.2065(3) 0.3406(7) 0.07758(15) 0.0218(11) Uani 1 1 d . . . H17A H 0.2506 0.3871 0.0585 0.026 Uiso 1 1 calc R . . C18 C 0.1374(3) 0.2304(6) 0.06349(14) 0.0206(11) Uani 1 1 d . . . C19 C 0.0706(3) 0.1687(6) 0.09029(14) 0.0180(10) Uani 1 1 d . . . H19A H 0.0222 0.0966 0.0801 0.022 Uiso 1 1 calc R . . C20 C 0.0746(3) 0.2129(6) 0.13231(14) 0.0150(10) Uani 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 0.0322(7) 0.0332(8) 0.0217(6) 0.0044(6) 0.0004(5) -0.0177(6) Cl2 0.0192(6) 0.0324(7) 0.0210(6) -0.0020(5) -0.0032(5) -0.0053(5) Cl3 0.0109(5) 0.0208(6) 0.0190(6) 0.0002(5) 0.0013(4) -0.0005(5) Cl4 0.0351(8) 0.0419(8) 0.0155(6) 0.0006(5) 0.0010(5) 0.0038(6) O1 0.0100(16) 0.0256(19) 0.0184(16) 0.0022(14) 0.0031(13) -0.0001(14) C1 0.011(2) 0.018(3) 0.021(2) -0.0024(19) 0.0042(19) -0.004(2) C2 0.022(3) 0.020(3) 0.015(2) 0.001(2) 0.0009(19) -0.001(2) C3 0.013(2) 0.021(3) 0.017(2) -0.006(2) -0.0029(18) 0.003(2) C4 0.013(2) 0.017(2) 0.023(2) 0.000(2) 0.0021(19) -0.001(2) C5 0.017(2) 0.015(2) 0.019(2) -0.0014(19) 0.0000(19) 0.002(2) C6 0.010(2) 0.019(3) 0.018(2) -0.0007(19) 0.0043(18) 0.0015(19) C7 0.009(2) 0.016(2) 0.023(2) 0.004(2) 0.0012(18) 0.0017(19) C8 0.011(2) 0.011(2) 0.019(2) 0.0009(18) 0.0023(19) 0.0007(18) C9 0.009(2) 0.020(3) 0.017(2) 0.0021(19) 0.0006(18) -0.0004(19) C10 0.009(2) 0.019(3) 0.025(3) 0.000(2) 0.0030(19) 0.0025(19) C11 0.010(2) 0.021(3) 0.021(2) 0.000(2) 0.0022(18) -0.001(2) C12 0.012(2) 0.012(2) 0.020(2) 0.0013(19) 0.0010(18) 0.0007(19) C13 0.010(2) 0.011(2) 0.024(2) 0.0032(19) 0.0021(19) 0.0008(18) C14 0.010(2) 0.017(2) 0.022(2) 0.007(2) 0.0019(19) -0.0005(19) C15 0.011(2) 0.015(2) 0.021(2) 0.0000(19) 0.0000(19) 0.0053(19) C16 0.012(2) 0.020(3) 0.027(3) 0.008(2) -0.0020(19) 0.000(2) C17 0.018(3) 0.025(3) 0.023(3) 0.008(2) 0.005(2) 0.005(2) C18 0.020(3) 0.025(3) 0.017(2) 0.003(2) -0.002(2) 0.009(2) C19 0.015(2) 0.018(3) 0.021(2) 0.002(2) -0.0036(19) 0.004(2) C20 0.009(2) 0.017(2) 0.019(2) 0.0014(19) 0.0020(18) 0.0046(19) _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 C1 1.737(5) . ? Cl2 C3 1.739(4) . ? Cl3 C20 1.745(4) . ? Cl4 C18 1.740(5) . ? O1 C13 1.229(5) . ? C1 C6 1.390(6) . ? C1 C2 1.397(6) . ? C2 C3 1.389(7) . ? C2 H2A 0.9500 . ? C3 C4 1.374(6) . ? C4 C5 1.384(6) . ? C4 H4A 0.9500 . ? C5 C6 1.400(6) . ? C5 H5A 0.9500 . ? C6 C7 1.479(6) . ? C7 C8 1.340(6) . ? C7 H7A 0.9500 . ? C8 C13 1.500(6) . ? C8 C9 1.506(6) . ? C9 C10 1.523(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.526(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.512(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.349(6) . ? C12 C13 1.508(6) . ? C14 C15 1.475(6) . ? C14 H14A 0.9500 . ? C15 C16 1.402(6) . ? C15 C20 1.408(6) . ? C16 C17 1.383(7) . ? C16 H16A 0.9500 . ? C17 C18 1.385(7) . ? C17 H17A 0.9500 . ? C18 C19 1.372(7) . ? C19 C20 1.382(6) . ? C19 H19A 0.9500 . ? 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 C6 C1 C2 122.7(4) . . ? C6 C1 Cl1 120.2(3) . . ? C2 C1 Cl1 117.1(3) . . ? C3 C2 C1 117.6(4) . . ? C3 C2 H2A 121.2 . . ? C1 C2 H2A 121.2 . . ? C4 C3 C2 121.6(4) . . ? C4 C3 Cl2 119.8(4) . . ? C2 C3 Cl2 118.6(3) . . ? C3 C4 C5 119.5(4) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C4 C5 C6 121.6(4) . . ? C4 C5 H5A 119.2 . . ? C6 C5 H5A 119.2 . . ? C1 C6 C5 117.0(4) . . ? C1 C6 C7 122.1(4) . . ? C5 C6 C7 120.8(4) . . ? C8 C7 C6 126.4(4) . . ? C8 C7 H7A 116.8 . . ? C6 C7 H7A 116.8 . . ? C7 C8 C13 117.3(4) . . ? C7 C8 C9 125.3(4) . . ? C13 C8 C9 117.3(4) . . ? C8 C9 C10 110.2(4) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C9 C10 C11 109.2(4) . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10A 109.8 . . ? C9 C10 H10B 109.8 . . ? C11 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? C12 C11 C10 113.1(4) . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C14 C12 C13 116.2(4) . . ? C14 C12 C11 124.8(4) . . ? C13 C12 C11 119.0(4) . . ? O1 C13 C8 121.0(4) . . ? O1 C13 C12 120.0(4) . . ? C8 C13 C12 118.9(4) . . ? C12 C14 C15 127.2(4) . . ? C12 C14 H14A 116.4 . . ? C15 C14 H14A 116.4 . . ? C16 C15 C20 116.3(4) . . ? C16 C15 C14 122.2(4) . . ? C20 C15 C14 121.6(4) . . ? C17 C16 C15 121.9(5) . . ? C17 C16 H16A 119.0 . . ? C15 C16 H16A 119.0 . . ? C16 C17 C18 119.1(4) . . ? C16 C17 H17A 120.4 . . ? C18 C17 H17A 120.4 . . ? C19 C18 C17 121.1(4) . . ? C19 C18 Cl4 120.0(4) . . ? C17 C18 Cl4 118.9(4) . . ? C18 C19 C20 119.1(4) . . ? C18 C19 H19A 120.5 . . ? C20 C19 H19A 120.5 . . ? C19 C20 C15 122.2(4) . . ? C19 C20 Cl3 117.4(4) . . ? C15 C20 Cl3 120.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.0(7) . . . . ? Cl1 C1 C2 C3 179.4(3) . . . . ? C1 C2 C3 C4 0.3(7) . . . . ? C1 C2 C3 Cl2 -179.6(4) . . . . ? C2 C3 C4 C5 -0.2(7) . . . . ? Cl2 C3 C4 C5 179.6(4) . . . . ? C3 C4 C5 C6 -0.1(7) . . . . ? C2 C1 C6 C5 -0.3(7) . . . . ? Cl1 C1 C6 C5 -179.7(3) . . . . ? C2 C1 C6 C7 -177.6(4) . . . . ? Cl1 C1 C6 C7 3.0(6) . . . . ? C4 C5 C6 C1 0.3(7) . . . . ? C4 C5 C6 C7 177.7(4) . . . . ? C1 C6 C7 C8 -141.4(5) . . . . ? C5 C6 C7 C8 41.3(7) . . . . ? C6 C7 C8 C13 -177.4(4) . . . . ? C6 C7 C8 C9 6.7(8) . . . . ? C7 C8 C9 C10 136.9(5) . . . . ? C13 C8 C9 C10 -39.1(5) . . . . ? C8 C9 C10 C11 65.0(5) . . . . ? C9 C10 C11 C12 -54.2(5) . . . . ? C10 C11 C12 C14 -161.1(5) . . . . ? C10 C11 C12 C13 17.8(6) . . . . ? C7 C8 C13 O1 8.8(7) . . . . ? C9 C8 C13 O1 -175.0(4) . . . . ? C7 C8 C13 C12 -173.6(4) . . . . ? C9 C8 C13 C12 2.7(6) . . . . ? C14 C12 C13 O1 5.1(6) . . . . ? C11 C12 C13 O1 -173.9(4) . . . . ? C14 C12 C13 C8 -172.6(4) . . . . ? C11 C12 C13 C8 8.4(6) . . . . ? C13 C12 C14 C15 178.8(4) . . . . ? C11 C12 C14 C15 -2.3(8) . . . . ? C12 C14 C15 C16 -35.5(7) . . . . ? C12 C14 C15 C20 146.1(5) . . . . ? C20 C15 C16 C17 -4.9(7) . . . . ? C14 C15 C16 C17 176.7(4) . . . . ? C15 C16 C17 C18 0.7(7) . . . . ? C16 C17 C18 C19 3.1(7) . . . . ? C16 C17 C18 Cl4 -177.2(4) . . . . ? C17 C18 C19 C20 -2.4(7) . . . . ? Cl4 C18 C19 C20 177.9(4) . . . . ? C18 C19 C20 C15 -2.2(7) . . . . ? C18 C19 C20 Cl3 179.3(4) . . . . ? C16 C15 C20 C19 5.7(7) . . . . ? C14 C15 C20 C19 -175.9(4) . . . . ? C16 C15 C20 Cl3 -175.9(3) . . . . ? C14 C15 C20 Cl3 2.5(6) . . . . ? data_100K _database_code_depnum_ccdc_archive 'CCDC 794788' #TrackingRef '- CE-COM-09-2010-000676_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 2,6-bis(2,4-dichlorobenzylidene)cyclohexanone _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cl4 O' _chemical_formula_sum 'C20 H14 Cl4 O' _chemical_formula_weight 412.11 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.3650(5) _cell_length_b 7.7434(2) _cell_length_c 31.8361(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3541.25(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9955 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 24.98 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.674 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.000 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 100(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 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 26236 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 25.02 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 3113 _reflns_number_gt 2751 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0259P)^2^+4.0321P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3113 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0744 _refine_ls_wR_factor_gt 0.0717 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.316 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.053 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 0.28706(4) 0.28918(8) 0.415554(17) 0.02619(15) Uani 1 1 d . . . Cl2 Cl 0.57403(4) 0.69492(7) 0.458454(17) 0.02188(14) Uani 1 1 d . . . Cl3 Cl -0.01253(3) 0.13557(7) 0.165183(16) 0.01548(13) Uani 1 1 d . . . Cl4 Cl 0.13708(4) 0.17440(8) 0.011161(17) 0.02725(15) Uani 1 1 d . . . O1 O 0.14038(10) 0.41464(19) 0.27861(4) 0.0165(3) Uani 1 1 d . . . C1 C 0.36449(14) 0.4520(3) 0.40185(6) 0.0153(5) Uani 1 1 d . . . C2 C 0.42905(15) 0.5020(3) 0.43201(7) 0.0168(5) Uani 1 1 d . . . H2A H 0.4298 0.4503 0.4591 0.020 Uiso 1 1 calc R . . C3 C 0.49222(15) 0.6297(3) 0.42132(6) 0.0158(5) Uani 1 1 d . . . C4 C 0.49120(15) 0.7074(3) 0.38236(7) 0.0165(5) Uani 1 1 d . . . H4A H 0.5349 0.7954 0.3757 0.020 Uiso 1 1 calc R . . C5 C 0.42570(15) 0.6555(3) 0.35306(7) 0.0158(5) Uani 1 1 d . . . H5A H 0.4247 0.7097 0.3263 0.019 Uiso 1 1 calc R . . C6 C 0.36086(14) 0.5252(3) 0.36187(6) 0.0148(4) Uani 1 1 d . . . C7 C 0.28968(15) 0.4758(3) 0.33090(7) 0.0151(4) Uani 1 1 d . . . H7A H 0.2287 0.4552 0.3413 0.018 Uiso 1 1 calc R . . C8 C 0.30238(14) 0.4569(3) 0.28939(6) 0.0132(4) Uani 1 1 d . . . C9 C 0.39513(14) 0.4659(3) 0.26718(6) 0.0145(4) Uani 1 1 d . . . H9A H 0.4461 0.4534 0.2879 0.017 Uiso 1 1 calc R . . H9B H 0.4019 0.5797 0.2533 0.017 Uiso 1 1 calc R . . C10 C 0.40209(14) 0.3235(3) 0.23460(7) 0.0153(4) Uani 1 1 d . . . H10A H 0.4651 0.3232 0.2220 0.018 Uiso 1 1 calc R . . H10B H 0.3916 0.2100 0.2481 0.018 Uiso 1 1 calc R . . C11 C 0.32967(14) 0.3528(3) 0.20049(7) 0.0152(4) Uani 1 1 d . . . H11A H 0.3462 0.4583 0.1846 0.018 Uiso 1 1 calc R . . H11B H 0.3312 0.2543 0.1807 0.018 Uiso 1 1 calc R . . C12 C 0.23207(14) 0.3719(3) 0.21744(6) 0.0135(4) Uani 1 1 d . . . C13 C 0.21888(14) 0.4136(3) 0.26339(6) 0.0136(4) Uani 1 1 d . . . C14 C 0.15394(15) 0.3541(3) 0.19455(7) 0.0144(4) Uani 1 1 d . . . H14A H 0.0968 0.3665 0.2093 0.017 Uiso 1 1 calc R . . C15 C 0.14710(14) 0.3175(3) 0.14926(6) 0.0142(4) Uani 1 1 d . . . C16 C 0.21088(15) 0.3840(3) 0.12012(7) 0.0180(5) Uani 1 1 d . . . H16A H 0.2585 0.4593 0.1298 0.022 Uiso 1 1 calc R . . C17 C 0.20714(15) 0.3441(3) 0.07799(7) 0.0191(5) Uani 1 1 d . . . H17A H 0.2511 0.3922 0.0590 0.023 Uiso 1 1 calc R . . C18 C 0.13855(16) 0.2332(3) 0.06364(7) 0.0184(5) Uani 1 1 d . . . C19 C 0.07065(15) 0.1711(3) 0.09060(7) 0.0162(5) Uani 1 1 d . . . H19A H 0.0220 0.0995 0.0804 0.019 Uiso 1 1 calc R . . C20 C 0.07512(14) 0.2156(3) 0.13264(7) 0.0143(4) Uani 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 0.0298(3) 0.0294(3) 0.0194(3) 0.0038(2) 0.0004(2) -0.0161(3) Cl2 0.0189(3) 0.0280(3) 0.0187(3) -0.0019(2) -0.0032(2) -0.0051(2) Cl3 0.0115(3) 0.0175(3) 0.0174(3) 0.0002(2) 0.0013(2) -0.0008(2) Cl4 0.0322(3) 0.0362(3) 0.0134(3) 0.0004(2) 0.0006(2) 0.0034(3) O1 0.0104(8) 0.0217(8) 0.0173(8) 0.0022(6) 0.0025(6) 0.0001(6) C1 0.0134(11) 0.0145(10) 0.0180(11) -0.0016(9) 0.0044(9) -0.0017(9) C2 0.0196(12) 0.0167(11) 0.0141(11) 0.0005(9) 0.0015(9) 0.0003(9) C3 0.0131(11) 0.0189(11) 0.0153(11) -0.0056(9) -0.0024(8) 0.0023(9) C4 0.0145(11) 0.0150(10) 0.0200(11) 0.0005(9) 0.0032(9) -0.0011(9) C5 0.0170(11) 0.0161(11) 0.0141(11) 0.0005(8) 0.0015(9) 0.0023(9) C6 0.0120(11) 0.0160(11) 0.0165(11) -0.0004(8) 0.0020(8) 0.0035(9) C7 0.0114(11) 0.0135(11) 0.0205(11) 0.0022(9) 0.0023(9) 0.0000(8) C8 0.0111(10) 0.0095(10) 0.0191(11) 0.0016(8) 0.0002(9) 0.0007(8) C9 0.0098(10) 0.0154(11) 0.0184(11) 0.0029(9) -0.0003(8) -0.0007(8) C10 0.0099(10) 0.0155(11) 0.0206(11) -0.0002(9) 0.0020(9) 0.0017(8) C11 0.0118(11) 0.0164(11) 0.0175(11) -0.0003(9) 0.0021(8) -0.0019(9) C12 0.0127(11) 0.0098(10) 0.0180(11) 0.0025(8) 0.0021(8) 0.0006(8) C13 0.0122(11) 0.0090(10) 0.0195(11) 0.0033(8) 0.0013(9) 0.0006(8) C14 0.0120(11) 0.0114(10) 0.0198(11) 0.0027(8) 0.0024(9) 0.0003(8) C15 0.0122(11) 0.0137(10) 0.0168(11) 0.0016(8) -0.0005(8) 0.0044(8) C16 0.0144(11) 0.0183(11) 0.0214(12) 0.0039(9) -0.0012(9) 0.0003(9) C17 0.0155(11) 0.0213(12) 0.0204(12) 0.0066(9) 0.0046(9) 0.0040(9) C18 0.0207(12) 0.0208(11) 0.0137(11) 0.0020(9) -0.0006(9) 0.0068(9) C19 0.0140(11) 0.0155(11) 0.0191(11) 0.0016(9) -0.0032(9) 0.0033(9) C20 0.0105(10) 0.0137(10) 0.0187(11) 0.0037(9) 0.0020(9) 0.0037(8) _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 C1 1.737(2) . ? Cl2 C3 1.742(2) . ? Cl3 C20 1.744(2) . ? Cl4 C18 1.732(2) . ? O1 C13 1.227(2) . ? C1 C2 1.390(3) . ? C1 C6 1.394(3) . ? C2 C3 1.385(3) . ? C2 H2A 0.9500 . ? C3 C4 1.378(3) . ? C4 C5 1.385(3) . ? C4 H4A 0.9500 . ? C5 C6 1.402(3) . ? C5 H5A 0.9500 . ? C6 C7 1.471(3) . ? C7 C8 1.342(3) . ? C7 H7A 0.9500 . ? C8 C13 1.495(3) . ? C8 C9 1.510(3) . ? C9 C10 1.517(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.521(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.510(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.345(3) . ? C12 C13 1.510(3) . ? C14 C15 1.473(3) . ? C14 H14A 0.9500 . ? C15 C16 1.402(3) . ? C15 C20 1.404(3) . ? C16 C17 1.377(3) . ? C16 H16A 0.9500 . ? C17 C18 1.385(3) . ? C17 H17A 0.9500 . ? C18 C19 1.385(3) . ? C19 C20 1.383(3) . ? C19 H19A 0.9500 . ? 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 C2 C1 C6 122.85(19) . . ? C2 C1 Cl1 117.11(16) . . ? C6 C1 Cl1 120.03(16) . . ? C3 C2 C1 117.79(19) . . ? C3 C2 H2A 121.1 . . ? C1 C2 H2A 121.1 . . ? C4 C3 C2 121.7(2) . . ? C4 C3 Cl2 119.41(17) . . ? C2 C3 Cl2 118.84(16) . . ? C3 C4 C5 119.1(2) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5A 119.1 . . ? C6 C5 H5A 119.1 . . ? C1 C6 C5 116.77(19) . . ? C1 C6 C7 122.14(19) . . ? C5 C6 C7 121.01(19) . . ? C8 C7 C6 126.44(19) . . ? C8 C7 H7A 116.8 . . ? C6 C7 H7A 116.8 . . ? C7 C8 C13 117.42(18) . . ? C7 C8 C9 125.17(19) . . ? C13 C8 C9 117.32(17) . . ? C8 C9 C10 110.18(17) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C9 C10 C11 109.57(17) . . ? C9 C10 H10A 109.8 . . ? C11 C10 H10A 109.8 . . ? C9 C10 H10B 109.8 . . ? C11 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C10 113.24(17) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C14 C12 C11 124.82(19) . . ? C14 C12 C13 116.23(18) . . ? C11 C12 C13 118.94(17) . . ? O1 C13 C8 121.14(18) . . ? O1 C13 C12 119.94(18) . . ? C8 C13 C12 118.91(17) . . ? C12 C14 C15 127.28(19) . . ? C12 C14 H14A 116.4 . . ? C15 C14 H14A 116.4 . . ? C16 C15 C20 116.00(19) . . ? C16 C15 C14 122.24(19) . . ? C20 C15 C14 121.75(19) . . ? C17 C16 C15 122.4(2) . . ? C17 C16 H16A 118.8 . . ? C15 C16 H16A 118.8 . . ? C16 C17 C18 119.2(2) . . ? C16 C17 H17A 120.4 . . ? C18 C17 H17A 120.4 . . ? C17 C18 C19 120.8(2) . . ? C17 C18 Cl4 119.36(17) . . ? C19 C18 Cl4 119.86(17) . . ? C20 C19 C18 118.7(2) . . ? C20 C19 H19A 120.6 . . ? C18 C19 H19A 120.6 . . ? C19 C20 C15 122.58(19) . . ? C19 C20 Cl3 116.93(16) . . ? C15 C20 Cl3 120.49(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.3(3) . . . . ? Cl1 C1 C2 C3 178.97(16) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C1 C2 C3 Cl2 -179.95(16) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? Cl2 C3 C4 C5 -179.69(16) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C2 C1 C6 C5 -0.6(3) . . . . ? Cl1 C1 C6 C5 -179.83(15) . . . . ? C2 C1 C6 C7 -177.5(2) . . . . ? Cl1 C1 C6 C7 3.3(3) . . . . ? C4 C5 C6 C1 1.0(3) . . . . ? C4 C5 C6 C7 177.89(19) . . . . ? C1 C6 C7 C8 -141.5(2) . . . . ? C5 C6 C7 C8 41.7(3) . . . . ? C6 C7 C8 C13 -177.20(19) . . . . ? C6 C7 C8 C9 6.4(3) . . . . ? C7 C8 C9 C10 137.2(2) . . . . ? C13 C8 C9 C10 -39.2(2) . . . . ? C8 C9 C10 C11 64.7(2) . . . . ? C9 C10 C11 C12 -54.0(2) . . . . ? C10 C11 C12 C14 -161.9(2) . . . . ? C10 C11 C12 C13 17.9(3) . . . . ? C7 C8 C13 O1 8.0(3) . . . . ? C9 C8 C13 O1 -175.32(18) . . . . ? C7 C8 C13 C12 -173.30(18) . . . . ? C9 C8 C13 C12 3.4(3) . . . . ? C14 C12 C13 O1 6.2(3) . . . . ? C11 C12 C13 O1 -173.55(18) . . . . ? C14 C12 C13 C8 -172.44(18) . . . . ? C11 C12 C13 C8 7.8(3) . . . . ? C11 C12 C14 C15 -1.6(3) . . . . ? C13 C12 C14 C15 178.60(19) . . . . ? C12 C14 C15 C16 -35.5(3) . . . . ? C12 C14 C15 C20 145.5(2) . . . . ? C20 C15 C16 C17 -3.8(3) . . . . ? C14 C15 C16 C17 177.1(2) . . . . ? C15 C16 C17 C18 -0.6(3) . . . . ? C16 C17 C18 C19 4.1(3) . . . . ? C16 C17 C18 Cl4 -176.84(17) . . . . ? C17 C18 C19 C20 -3.0(3) . . . . ? Cl4 C18 C19 C20 177.94(16) . . . . ? C18 C19 C20 C15 -1.7(3) . . . . ? C18 C19 C20 Cl3 179.49(16) . . . . ? C16 C15 C20 C19 4.9(3) . . . . ? C14 C15 C20 C19 -176.00(19) . . . . ? C16 C15 C20 Cl3 -176.27(15) . . . . ? C14 C15 C20 Cl3 2.8(3) . . . . ?