# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Xinmiao Liang' _publ_contact_author_email LIANGXM@ECUST.EDU.CN _publ_section_title ; Asymmetric Organocatalytic Michael Addition of Anthrones to ?, ?-Unsaturated Ketones ; loop_ _publ_author_name 'Xinmiao Liang.' 'Wenjun Li.' 'Chunlin Wu.' 'Juanjuan Yang.' 'Jinxing Ye.' # Attachment 'W134D.cif' data_w134d _database_code_depnum_ccdc_archive 'CCDC 764606' #TrackingRef 'W134D.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C24 H19 Cl O2' _chemical_formula_sum 'C24 H19 Cl O2' _chemical_formula_weight 374.84 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 P2(1)2(1)2(1) 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' _cell_length_a 12.5855(10) _cell_length_b 14.0795(11) _cell_length_c 21.9701(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3893.0(5) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3801 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 20.91 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9589 _exptl_absorpt_correction_T_max 0.9791 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 16570 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 23.23 _reflns_number_total 5543 _reflns_number_gt 4172 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0842P)^2^+1.0534P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(14) _refine_ls_number_reflns 5543 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1440 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.05312(11) -0.10650(15) -0.14764(13) 0.1715(10) Uani 1 1 d . . . Cl2 Cl 0.07046(12) 0.08126(18) 0.11196(16) 0.2303(17) Uani 1 1 d . . . O1 O 0.1009(2) 0.2498(2) -0.13361(14) 0.0824(9) Uani 1 1 d . . . O2 O -0.1003(2) -0.2424(2) 0.13343(14) 0.0769(9) Uani 1 1 d . . . O3 O 0.6084(2) 0.0366(3) -0.07597(16) 0.0913(10) Uani 1 1 d . . . O4 O -0.6332(3) -0.0404(3) 0.06155(19) 0.1136(13) Uani 1 1 d . . . C1 C 0.2406(4) 0.1921(3) -0.3014(2) 0.0754(14) Uani 1 1 d . . . H1 H 0.2038 0.1994 -0.3379 0.091 Uiso 1 1 calc R . . C2 C 0.3438(4) 0.1586(3) -0.3016(2) 0.0771(14) Uani 1 1 d . . . H2 H 0.3773 0.1452 -0.3383 0.092 Uiso 1 1 calc R . . C3 C 0.3976(3) 0.1449(3) -0.24739(16) 0.0622(11) Uani 1 1 d . . . H3 H 0.4670 0.1222 -0.2483 0.075 Uiso 1 1 calc R . . C4 C 0.3502(3) 0.1643(3) -0.19177(16) 0.0477(9) Uani 1 1 d . . . C5 C 0.2465(3) 0.2002(3) -0.19226(17) 0.0491(10) Uani 1 1 d . . . C6 C 0.1925(4) 0.2146(4) -0.24688(18) 0.0668(12) Uani 1 1 d . . . H6 H 0.1241 0.2394 -0.2465 0.080 Uiso 1 1 calc R . . C7 C 0.4045(3) 0.1427(2) -0.13313(16) 0.0510(9) Uani 1 1 d . . . H7 H 0.4802 0.1565 -0.1385 0.061 Uiso 1 1 calc R . . C8 C 0.1945(3) 0.2291(3) -0.13422(19) 0.0601(11) Uani 1 1 d . . . C9 C 0.3654(3) 0.2019(3) -0.08093(17) 0.0553(10) Uani 1 1 d . . . C10 C 0.4302(4) 0.2155(3) -0.02993(19) 0.0736(13) Uani 1 1 d . . . H10 H 0.4992 0.1919 -0.0300 0.088 Uiso 1 1 calc R . . C11 C 0.3930(5) 0.2634(4) 0.0203(2) 0.0960(18) Uani 1 1 d . . . H11 H 0.4372 0.2729 0.0536 0.115 Uiso 1 1 calc R . . C12 C 0.2907(5) 0.2972(4) 0.0213(2) 0.0946(18) Uani 1 1 d . . . H12 H 0.2656 0.3296 0.0552 0.113 Uiso 1 1 calc R . . C13 C 0.2251(4) 0.2829(4) -0.02825(19) 0.0761(14) Uani 1 1 d . . . H13 H 0.1552 0.3043 -0.0270 0.091 Uiso 1 1 calc R . . C14 C 0.2627(3) 0.2368(3) -0.07993(18) 0.0538(10) Uani 1 1 d . . . C15 C -0.3018(5) -0.2909(4) -0.0169(2) 0.0903(16) Uani 1 1 d . . . H15 H -0.2791 -0.3230 -0.0515 0.108 Uiso 1 1 calc R . . C16 C -0.4028(5) -0.2544(4) -0.0138(2) 0.0894(16) Uani 1 1 d . . . H16 H -0.4490 -0.2629 -0.0463 0.107 Uiso 1 1 calc R . . C17 C -0.4367(4) -0.2055(3) 0.03682(19) 0.0714(13) Uani 1 1 d . . . H17 H -0.5054 -0.1811 0.0379 0.086 Uiso 1 1 calc R . . C18 C -0.3700(3) -0.1919(3) 0.08624(16) 0.0515(9) Uani 1 1 d . . . C19 C -0.2672(3) -0.2301(3) 0.08401(18) 0.0538(10) Uani 1 1 d . . . C20 C -0.2346(4) -0.2792(3) 0.0320(2) 0.0753(14) Uani 1 1 d . . . H20 H -0.1663 -0.3043 0.0303 0.090 Uiso 1 1 calc R . . C21 C -0.1957(3) -0.2241(3) 0.13693(17) 0.0537(10) Uani 1 1 d . . . C22 C -0.2462(3) -0.2007(3) 0.19633(18) 0.0509(10) Uani 1 1 d . . . C23 C -0.3487(3) -0.1621(3) 0.19852(16) 0.0463(9) Uani 1 1 d . . . C24 C -0.4054(3) -0.1353(2) 0.14040(15) 0.0479(9) Uani 1 1 d . . . H24 H -0.4812 -0.1478 0.1464 0.057 Uiso 1 1 calc R . . C25 C -0.3937(3) -0.1456(3) 0.25517(16) 0.0650(12) Uani 1 1 d . . . H25 H -0.4619 -0.1203 0.2576 0.078 Uiso 1 1 calc R . . C26 C -0.3392(4) -0.1660(4) 0.30770(19) 0.0801(14) Uani 1 1 d . . . H26 H -0.3707 -0.1543 0.3452 0.096 Uiso 1 1 calc R . . C27 C -0.2384(4) -0.2037(4) 0.3053(2) 0.0788(14) Uani 1 1 d . . . H27 H -0.2019 -0.2176 0.3410 0.095 Uiso 1 1 calc R . . C28 C -0.1929(4) -0.2205(3) 0.25049(17) 0.0618(11) Uani 1 1 d . . . H28 H -0.1246 -0.2457 0.2489 0.074 Uiso 1 1 calc R . . C29 C -0.3915(3) -0.0241(3) 0.13176(16) 0.0526(9) Uani 1 1 d . . . H29 H -0.4161 0.0048 0.1698 0.063 Uiso 1 1 calc R . . C30 C -0.2766(3) 0.0034(3) 0.12571(19) 0.0558(10) Uani 1 1 d . . . C31 C -0.2201(3) -0.0086(4) 0.0710(2) 0.0784(13) Uani 1 1 d . . . H31 H -0.2537 -0.0337 0.0369 0.094 Uiso 1 1 calc R . . C32 C -0.2223(4) 0.0404(3) 0.1744(3) 0.0794(14) Uani 1 1 d . . . H32 H -0.2576 0.0493 0.2111 0.095 Uiso 1 1 calc R . . C33 C 0.3942(3) 0.0337(3) -0.11417(17) 0.0533(9) Uani 1 1 d . . . H33 H 0.4079 0.0314 -0.0703 0.064 Uiso 1 1 calc R . . C34 C 0.2822(3) -0.0021(3) -0.12258(19) 0.0550(10) Uani 1 1 d . . . C35 C 0.2100(3) 0.0052(4) -0.0757(2) 0.0758(13) Uani 1 1 d . . . H35 H 0.2307 0.0299 -0.0382 0.091 Uiso 1 1 calc R . . C36 C 0.2484(3) -0.0414(3) -0.1776(2) 0.0662(12) Uani 1 1 d . . . H36 H 0.2960 -0.0453 -0.2099 0.079 Uiso 1 1 calc R . . C37 C 0.1462(4) -0.0747(3) -0.1854(2) 0.0828(14) Uani 1 1 d . . . H37 H 0.1252 -0.1039 -0.2214 0.099 Uiso 1 1 calc R . . C38 C 0.0768(4) -0.0629(4) -0.1379(3) 0.0930(16) Uani 1 1 d . . . C39 C 0.1051(4) -0.0250(4) -0.0848(3) 0.0960(16) Uani 1 1 d . . . H39 H 0.0553 -0.0185 -0.0538 0.115 Uiso 1 1 calc R . . C40 C -0.0626(4) 0.0498(6) 0.1161(5) 0.135(3) Uani 1 1 d . . . C41 C -0.1139(4) 0.0173(4) 0.0682(3) 0.113(2) Uani 1 1 d . . . H41 H -0.0778 0.0115 0.0314 0.136 Uiso 1 1 calc R . . C43 C 0.4783(3) -0.0270(3) -0.14308(18) 0.0582(10) Uani 1 1 d . . . H43A H 0.4808 -0.0122 -0.1862 0.070 Uiso 1 1 calc R . . H43B H 0.4572 -0.0929 -0.1392 0.070 Uiso 1 1 calc R . . C44 C 0.5889(3) -0.0164(3) -0.1174(2) 0.0650(11) Uani 1 1 d . . . C45 C 0.6722(4) -0.0738(4) -0.1463(3) 0.116(2) Uani 1 1 d . . . H45A H 0.7380 -0.0649 -0.1250 0.173 Uiso 1 1 calc R . . H45B H 0.6805 -0.0543 -0.1879 0.173 Uiso 1 1 calc R . . H45C H 0.6525 -0.1396 -0.1450 0.173 Uiso 1 1 calc R . . C46 C -0.4617(3) 0.0172(3) 0.08196(17) 0.0582(9) Uani 1 1 d . . . H46A H -0.4450 0.0841 0.0774 0.070 Uiso 1 1 calc R . . H46B H -0.4447 -0.0140 0.0438 0.070 Uiso 1 1 calc R . . C47 C -0.5784(3) 0.0072(3) 0.0935(2) 0.0604(10) Uani 1 1 d . . . C48 C -0.6270(4) 0.0608(4) 0.1443(2) 0.1063(18) Uani 1 1 d . . . H48A H -0.7005 0.0435 0.1479 0.159 Uiso 1 1 calc R . . H48B H -0.6214 0.1276 0.1363 0.159 Uiso 1 1 calc R . . H48C H -0.5905 0.0460 0.1814 0.159 Uiso 1 1 calc R . . C49 C -0.1153(5) 0.0649(4) 0.1700(4) 0.112(2) Uani 1 1 d . . . H49 H -0.0800 0.0910 0.2032 0.135 Uiso 1 1 calc R . . 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 0.0515(8) 0.1559(16) 0.307(3) 0.0174(18) -0.0388(12) -0.0255(9) Cl2 0.0481(9) 0.218(2) 0.425(5) 0.136(3) -0.0289(15) -0.0366(11) O1 0.050(2) 0.110(3) 0.086(2) 0.0078(18) 0.0021(17) 0.0225(17) O2 0.052(2) 0.094(2) 0.084(2) 0.0023(17) -0.0005(16) 0.0130(16) O3 0.0591(19) 0.106(3) 0.109(2) -0.016(2) -0.0107(18) 0.0057(18) O4 0.069(2) 0.121(3) 0.151(3) -0.038(3) -0.014(2) -0.009(2) C1 0.093(4) 0.078(3) 0.055(3) 0.008(2) -0.010(3) -0.003(3) C2 0.100(4) 0.078(3) 0.054(3) -0.004(2) 0.014(3) 0.001(3) C3 0.067(3) 0.063(3) 0.056(3) 0.009(2) 0.009(2) 0.003(2) C4 0.048(2) 0.047(2) 0.048(2) -0.0015(18) 0.0019(18) -0.0051(18) C5 0.049(2) 0.049(2) 0.049(2) 0.0038(18) -0.0027(18) -0.0035(19) C6 0.061(3) 0.072(3) 0.068(3) 0.013(2) -0.010(2) -0.009(2) C7 0.0374(19) 0.055(2) 0.061(2) 0.0039(19) 0.0012(18) 0.0007(17) C8 0.047(3) 0.063(3) 0.071(3) 0.013(2) 0.004(2) 0.014(2) C9 0.060(2) 0.052(2) 0.054(2) 0.0006(19) -0.002(2) 0.011(2) C10 0.069(3) 0.081(3) 0.071(3) -0.010(2) -0.026(2) 0.022(2) C11 0.123(5) 0.110(4) 0.055(3) -0.017(3) -0.023(3) 0.044(4) C12 0.123(4) 0.106(4) 0.054(3) 0.000(3) 0.012(3) 0.049(4) C13 0.083(3) 0.094(4) 0.052(3) 0.004(2) 0.012(2) 0.036(3) C14 0.056(2) 0.055(2) 0.050(2) 0.0094(19) 0.0020(19) 0.016(2) C15 0.121(4) 0.100(4) 0.050(3) -0.014(3) -0.011(3) 0.028(4) C16 0.107(4) 0.099(4) 0.062(3) -0.013(3) -0.026(3) 0.019(3) C17 0.078(3) 0.077(3) 0.060(3) -0.005(2) -0.008(2) 0.013(2) C18 0.054(2) 0.051(2) 0.049(2) 0.0044(18) -0.0040(19) 0.0015(19) C19 0.055(2) 0.059(2) 0.047(2) 0.0036(19) 0.0028(19) 0.005(2) C20 0.084(3) 0.076(3) 0.065(3) 0.001(2) 0.002(3) 0.023(3) C21 0.047(2) 0.055(2) 0.059(2) 0.000(2) 0.002(2) 0.0022(19) C22 0.049(2) 0.048(2) 0.056(2) 0.0051(19) -0.0055(18) -0.0052(19) C23 0.046(2) 0.045(2) 0.048(2) 0.0066(18) 0.0030(17) -0.0030(18) C24 0.0401(19) 0.053(2) 0.050(2) 0.0047(17) 0.0029(18) 0.0019(17) C25 0.061(3) 0.077(3) 0.057(3) -0.001(2) 0.009(2) -0.006(2) C26 0.092(4) 0.104(4) 0.045(3) 0.002(3) 0.003(2) -0.008(3) C27 0.089(4) 0.097(4) 0.050(3) 0.011(3) -0.018(3) -0.001(3) C28 0.065(3) 0.061(3) 0.060(3) 0.004(2) -0.014(2) 0.001(2) C29 0.050(2) 0.054(2) 0.054(2) 0.0015(18) -0.0049(17) 0.0049(18) C30 0.045(2) 0.046(2) 0.077(3) 0.015(2) -0.005(2) -0.0002(18) C31 0.050(3) 0.081(3) 0.104(4) 0.013(3) 0.013(3) -0.004(2) C32 0.066(3) 0.072(3) 0.100(3) 0.012(3) -0.023(3) -0.016(2) C33 0.037(2) 0.053(2) 0.069(2) 0.0029(19) 0.0017(18) 0.0044(17) C34 0.043(2) 0.051(2) 0.070(3) 0.005(2) 0.002(2) 0.0023(19) C35 0.054(3) 0.083(3) 0.090(3) 0.006(3) 0.013(2) -0.001(2) C36 0.061(3) 0.058(3) 0.079(3) 0.009(2) -0.010(2) -0.006(2) C37 0.078(3) 0.073(3) 0.097(3) 0.007(3) -0.026(3) -0.006(3) C38 0.057(3) 0.076(3) 0.147(5) 0.014(4) -0.023(4) -0.005(3) C39 0.056(3) 0.103(4) 0.130(4) 0.015(4) 0.031(3) 0.001(3) C40 0.042(3) 0.136(6) 0.228(9) 0.084(6) -0.019(5) -0.007(3) C41 0.055(3) 0.119(5) 0.166(6) 0.051(5) 0.039(4) 0.011(3) C43 0.048(2) 0.053(2) 0.074(2) -0.002(2) 0.0021(19) 0.0043(17) C44 0.049(2) 0.060(3) 0.086(3) -0.002(2) 0.004(2) 0.010(2) C45 0.067(3) 0.118(5) 0.162(5) -0.024(4) 0.022(3) 0.028(3) C46 0.053(2) 0.056(2) 0.066(2) 0.0099(19) -0.0041(19) 0.0066(19) C47 0.045(2) 0.057(2) 0.080(3) 0.007(2) -0.008(2) 0.002(2) C48 0.077(3) 0.122(5) 0.120(4) -0.040(4) 0.024(3) 0.005(3) C49 0.089(4) 0.081(4) 0.168(6) 0.026(4) -0.063(4) -0.026(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C38 1.760(5) . ? Cl2 C40 1.735(6) . ? O1 C8 1.214(5) . ? O2 C21 1.231(4) . ? O3 C44 1.201(5) . ? O4 C47 1.191(5) . ? C1 C6 1.379(6) . ? C1 C2 1.382(6) . ? C1 H1 0.9300 . ? C2 C3 1.383(6) . ? C2 H2 0.9300 . ? C3 C4 1.387(5) . ? C3 H3 0.9300 . ? C4 C5 1.399(5) . ? C4 C7 1.489(5) . ? C5 C6 1.394(5) . ? C5 C8 1.490(6) . ? C6 H6 0.9300 . ? C7 C9 1.500(5) . ? C7 C33 1.596(5) . ? C7 H7 0.9800 . ? C8 C14 1.473(6) . ? C9 C14 1.383(5) . ? C9 C10 1.399(5) . ? C10 C11 1.375(6) . ? C10 H10 0.9300 . ? C11 C12 1.373(7) . ? C11 H11 0.9300 . ? C12 C13 1.381(7) . ? C12 H12 0.9300 . ? C13 C14 1.391(6) . ? C13 H13 0.9300 . ? C15 C16 1.373(7) . ? C15 C20 1.376(7) . ? C15 H15 0.9300 . ? C16 C17 1.375(6) . ? C16 H16 0.9300 . ? C17 C18 1.386(5) . ? C17 H17 0.9300 . ? C18 C19 1.402(5) . ? C18 C24 1.500(5) . ? C19 C20 1.397(6) . ? C19 C21 1.473(6) . ? C20 H20 0.9300 . ? C21 C22 1.488(5) . ? C22 C28 1.394(5) . ? C22 C23 1.400(5) . ? C23 C25 1.387(5) . ? C23 C24 1.511(5) . ? C24 C29 1.587(5) . ? C24 H24 0.9800 . ? C25 C26 1.373(6) . ? C25 H25 0.9300 . ? C26 C27 1.376(7) . ? C26 H26 0.9300 . ? C27 C28 1.354(6) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C30 1.503(5) . ? C29 C46 1.521(5) . ? C29 H29 0.9800 . ? C30 C32 1.372(6) . ? C30 C31 1.407(6) . ? C31 C41 1.387(7) . ? C31 H31 0.9300 . ? C32 C49 1.393(7) . ? C32 H32 0.9300 . ? C33 C43 1.502(5) . ? C33 C34 1.508(5) . ? C33 H33 0.9800 . ? C34 C35 1.378(6) . ? C34 C36 1.397(6) . ? C35 C39 1.401(7) . ? C35 H35 0.9300 . ? C36 C37 1.378(6) . ? C36 H36 0.9300 . ? C37 C38 1.371(7) . ? C37 H37 0.9300 . ? C38 C39 1.331(8) . ? C39 H39 0.9300 . ? C40 C41 1.317(10) . ? C40 C49 1.374(10) . ? C41 H41 0.9300 . ? C43 C44 1.510(6) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.468(6) . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 C47 1.498(5) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 C48 1.478(6) . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? C49 H49 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 C6 C1 C2 119.5(4) . . ? C6 C1 H1 120.3 . . ? C2 C1 H1 120.3 . . ? C1 C2 C3 120.4(4) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C2 C3 C4 121.3(4) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 117.7(4) . . ? C3 C4 C7 121.6(3) . . ? C5 C4 C7 120.5(3) . . ? C6 C5 C4 120.9(4) . . ? C6 C5 C8 118.9(4) . . ? C4 C5 C8 120.1(3) . . ? C1 C6 C5 120.1(4) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C4 C7 C9 113.4(3) . . ? C4 C7 C33 112.6(3) . . ? C9 C7 C33 107.9(3) . . ? C4 C7 H7 107.5 . . ? C9 C7 H7 107.5 . . ? C33 C7 H7 107.5 . . ? O1 C8 C14 122.6(4) . . ? O1 C8 C5 120.1(4) . . ? C14 C8 C5 117.2(3) . . ? C14 C9 C10 118.9(4) . . ? C14 C9 C7 121.0(4) . . ? C10 C9 C7 119.9(3) . . ? C11 C10 C9 120.8(4) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C10 120.1(5) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 119.9(5) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 120.5(4) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C9 C14 C13 119.8(4) . . ? C9 C14 C8 120.4(4) . . ? C13 C14 C8 119.8(4) . . ? C16 C15 C20 119.0(5) . . ? C16 C15 H15 120.5 . . ? C20 C15 H15 120.5 . . ? C15 C16 C17 121.0(4) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C16 C17 C18 120.9(4) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C17 C18 C19 118.6(4) . . ? C17 C18 C24 121.0(4) . . ? C19 C18 C24 120.4(3) . . ? C20 C19 C18 119.3(4) . . ? C20 C19 C21 119.7(4) . . ? C18 C19 C21 120.9(4) . . ? C15 C20 C19 121.1(5) . . ? C15 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? O2 C21 C19 122.3(4) . . ? O2 C21 C22 121.2(4) . . ? C19 C21 C22 116.3(3) . . ? C28 C22 C23 119.4(4) . . ? C28 C22 C21 119.9(4) . . ? C23 C22 C21 120.6(3) . . ? C25 C23 C22 118.2(4) . . ? C25 C23 C24 121.5(3) . . ? C22 C23 C24 120.2(3) . . ? C18 C24 C23 113.4(3) . . ? C18 C24 C29 113.4(3) . . ? C23 C24 C29 107.2(3) . . ? C18 C24 H24 107.5 . . ? C23 C24 H24 107.5 . . ? C29 C24 H24 107.5 . . ? C26 C25 C23 121.0(4) . . ? C26 C25 H25 119.5 . . ? C23 C25 H25 119.5 . . ? C25 C26 C27 120.6(4) . . ? C25 C26 H26 119.7 . . ? C27 C26 H26 119.7 . . ? C28 C27 C26 119.5(4) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C27 C28 C22 121.3(4) . . ? C27 C28 H28 119.3 . . ? C22 C28 H28 119.3 . . ? C30 C29 C46 113.3(3) . . ? C30 C29 C24 111.7(3) . . ? C46 C29 C24 113.5(3) . . ? C30 C29 H29 105.8 . . ? C46 C29 H29 105.8 . . ? C24 C29 H29 105.8 . . ? C32 C30 C31 117.3(4) . . ? C32 C30 C29 120.6(4) . . ? C31 C30 C29 122.1(4) . . ? C41 C31 C30 119.6(5) . . ? C41 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? C30 C32 C49 121.5(6) . . ? C30 C32 H32 119.3 . . ? C49 C32 H32 119.3 . . ? C43 C33 C34 114.6(3) . . ? C43 C33 C7 112.3(3) . . ? C34 C33 C7 111.4(3) . . ? C43 C33 H33 105.9 . . ? C34 C33 H33 105.9 . . ? C7 C33 H33 105.9 . . ? C35 C34 C36 118.5(4) . . ? C35 C34 C33 120.0(4) . . ? C36 C34 C33 121.6(4) . . ? C34 C35 C39 119.4(5) . . ? C34 C35 H35 120.3 . . ? C39 C35 H35 120.3 . . ? C37 C36 C34 121.7(4) . . ? C37 C36 H36 119.2 . . ? C34 C36 H36 119.2 . . ? C38 C37 C36 117.4(5) . . ? C38 C37 H37 121.3 . . ? C36 C37 H37 121.3 . . ? C39 C38 C37 123.0(5) . . ? C39 C38 Cl1 119.7(5) . . ? C37 C38 Cl1 117.2(5) . . ? C38 C39 C35 120.0(5) . . ? C38 C39 H39 120.0 . . ? C35 C39 H39 120.0 . . ? C41 C40 C49 120.4(5) . . ? C41 C40 Cl2 121.3(7) . . ? C49 C40 Cl2 118.2(7) . . ? C40 C41 C31 121.8(6) . . ? C40 C41 H41 119.1 . . ? C31 C41 H41 119.1 . . ? C33 C43 C44 115.8(3) . . ? C33 C43 H43A 108.3 . . ? C44 C43 H43A 108.3 . . ? C33 C43 H43B 108.3 . . ? C44 C43 H43B 108.3 . . ? H43A C43 H43B 107.4 . . ? O3 C44 C45 121.6(4) . . ? O3 C44 C43 122.2(4) . . ? C45 C44 C43 116.2(4) . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C47 C46 C29 114.3(3) . . ? C47 C46 H46A 108.7 . . ? C29 C46 H46A 108.7 . . ? C47 C46 H46B 108.7 . . ? C29 C46 H46B 108.7 . . ? H46A C46 H46B 107.6 . . ? O4 C47 C48 119.5(4) . . ? O4 C47 C46 121.4(4) . . ? C48 C47 C46 119.1(4) . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C40 C49 C32 119.2(6) . . ? C40 C49 H49 120.4 . . ? C32 C49 H49 120.4 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.23 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.464 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.036