# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Melchiorre, Paolo' _publ_contact_author_email pmelchiorre@iciq.es _publ_section_title ; Multiple approaches to enantiopure spirocyclic benzofuranones using organocatalytic cascade reactions ; loop_ _publ_author_name C.Cassani X.Tian E.Escudero P.Melchiorre # Attachment 'CCDC780474-CSH204.cif' data_csh204-05t _database_code_depnum_ccdc_archive 'CCDC 780474' #TrackingRef 'CCDC780474-CSH204.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H18 Cl2 O3' _chemical_formula_weight 449.30 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 Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.3195(10) _cell_length_b 9.3688(10) _cell_length_c 26.301(3) _cell_angle_alpha 82.514(4) _cell_angle_beta 88.091(4) _cell_angle_gamma 69.752(5) _cell_volume 2136.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2769 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 33.68 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.330 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ; TWINABS Version 2008/4 Bruker AXS Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 The diffraction measured fraction is low, 0.89, since the reflections of belonging to both crystal domains have been omitted. ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 29711 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 0.78 _diffrn_reflns_theta_max 34.63 _reflns_number_total 29711 _reflns_number_gt 24733 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution Sir2007 _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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. The structure refines as a twin made up of two crystal domains with a ratio 71:29. ; _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^)+(0.1691P)^2^+1.2510P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration ad _refine_ls_abs_structure_Flack 0.03(5) _refine_ls_number_reflns 29711 _refine_ls_number_parameters 1118 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0845 _refine_ls_wR_factor_ref 0.2513 _refine_ls_wR_factor_gt 0.2361 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 C1A C 0.0507(5) 0.1766(5) 0.29934(13) 0.0167(7) Uani 1 1 d . . . C2A C -0.1053(5) 0.2475(5) 0.27057(13) 0.0163(7) Uani 1 1 d . . . H2A H -0.0914 0.2064 0.2376 0.020 Uiso 1 1 calc R . . C3A C -0.2331(5) 0.1996(6) 0.29882(16) 0.0199(8) Uani 1 1 d . . . H3A1 H -0.2779 0.2686 0.3241 0.024 Uiso 1 1 calc R . . H3A2 H -0.3129 0.2107 0.2743 0.024 Uiso 1 1 calc R . . C4A C -0.1780(5) 0.0384(6) 0.32505(14) 0.0198(8) Uani 1 1 d . . . H4A H -0.2516 -0.0037 0.3370 0.024 Uiso 1 1 calc R . . C5A C -0.0314(5) -0.0498(6) 0.33266(14) 0.0190(8) Uani 1 1 d . . . C6A C 0.0996(5) -0.0019(5) 0.31052(13) 0.0168(7) Uani 1 1 d . . . H6A H 0.1828 -0.0380 0.3361 0.020 Uiso 1 1 calc R . . C7A C -0.1547(5) 0.4219(5) 0.25830(14) 0.0182(7) Uani 1 1 d . . . C8A C -0.1220(5) 0.4872(5) 0.21011(14) 0.0185(7) Uani 1 1 d . . . H8A H -0.0660 0.4233 0.1868 0.022 Uiso 1 1 calc R . . C9A C -0.1714(5) 0.6441(6) 0.19664(15) 0.0205(8) Uani 1 1 d . . . H9A H -0.1519 0.6850 0.1641 0.025 Uiso 1 1 calc R . . C10A C -0.2502(5) 0.7404(5) 0.23179(15) 0.0194(8) Uani 1 1 d . . . C11A C -0.2788(6) 0.6797(6) 0.28122(15) 0.0201(8) Uani 1 1 d . . . H11A H -0.3292 0.7443 0.3051 0.024 Uiso 1 1 calc R . . C12A C -0.2306(5) 0.5215(5) 0.29380(14) 0.0182(8) Uani 1 1 d . . . H12A H -0.2490 0.4807 0.3265 0.022 Uiso 1 1 calc R . . C13A C 0.0065(6) -0.2026(6) 0.36332(16) 0.0262(9) Uani 1 1 d . . . H13A H -0.0736 -0.2377 0.3729 0.031 Uiso 1 1 calc R . . C14A C 0.1577(5) -0.0819(5) 0.26280(14) 0.0173(7) Uani 1 1 d . . . C15A C 0.0549(5) -0.0859(6) 0.22595(14) 0.0202(8) Uani 1 1 d . . . H15A H -0.0497 -0.0404 0.2305 0.024 Uiso 1 1 calc R . . C16A C 0.1091(5) -0.1583(6) 0.18196(15) 0.0207(8) Uani 1 1 d . . . H16A H 0.0405 -0.1607 0.1575 0.025 Uiso 1 1 calc R . . C17A C 0.2621(6) -0.2247(6) 0.17548(15) 0.0214(8) Uani 1 1 d . . . C18A C 0.3693(5) -0.2242(6) 0.21193(17) 0.0231(9) Uani 1 1 d . . . H18A H 0.4737 -0.2704 0.2071 0.028 Uiso 1 1 calc R . . C19A C 0.3145(5) -0.1524(6) 0.25548(16) 0.0215(8) Uani 1 1 d . . . H19A H 0.3836 -0.1515 0.2801 0.026 Uiso 1 1 calc R . . C20A C 0.1683(5) 0.2340(5) 0.27203(13) 0.0170(7) Uani 1 1 d . . . C21A C 0.2382(6) 0.2149(6) 0.22413(14) 0.0205(8) Uani 1 1 d . . . H21A H 0.2184 0.1511 0.2032 0.025 Uiso 1 1 calc R . . C22A C 0.3380(6) 0.2935(6) 0.20858(17) 0.0227(8) Uani 1 1 d . . . H22A H 0.3874 0.2795 0.1774 0.027 Uiso 1 1 calc R . . C23A C 0.3647(6) 0.3930(6) 0.23927(18) 0.0256(9) Uani 1 1 d . . . H23A H 0.4314 0.4445 0.2279 0.031 Uiso 1 1 calc R . . C24A C 0.2937(6) 0.4172(6) 0.28666(16) 0.0245(9) Uani 1 1 d . . . H24A H 0.3099 0.4843 0.3070 0.029 Uiso 1 1 calc R . . C25A C 0.1983(5) 0.3352(6) 0.30127(14) 0.0195(8) Uani 1 1 d . . . C26A C 0.0388(5) 0.2443(5) 0.35010(13) 0.0195(8) Uani 1 1 d . . . C1B C 0.5231(5) 0.9953(5) 0.46081(12) 0.0151(7) Uani 1 1 d . . . C2B C 0.3854(5) 1.0304(5) 0.49848(13) 0.0152(7) Uani 1 1 d . . . H2B H 0.4210 1.0585 0.5291 0.018 Uiso 1 1 calc R . . C3B C 0.2489(5) 1.1711(5) 0.47687(15) 0.0189(7) Uani 1 1 d . . . H3B1 H 0.1921 1.1399 0.4529 0.023 Uiso 1 1 calc R . . H3B2 H 0.1812 1.2082 0.5048 0.023 Uiso 1 1 calc R . . C4B C 0.2946(5) 1.2990(5) 0.45037(14) 0.0182(7) Uani 1 1 d . . . H4B H 0.2190 1.3943 0.4423 0.022 Uiso 1 1 calc R . . C5B C 0.4402(5) 1.2835(5) 0.43745(13) 0.0165(7) Uani 1 1 d . . . C6B C 0.5763(5) 1.1375(5) 0.44903(13) 0.0157(7) Uani 1 1 d . . . H6B H 0.6386 1.1239 0.4181 0.019 Uiso 1 1 calc R . . C7B C 0.3404(5) 0.8917(5) 0.51660(14) 0.0166(7) Uani 1 1 d . . . C8B C 0.2751(6) 0.8235(6) 0.48386(14) 0.0210(8) Uani 1 1 d . . . H8B H 0.2567 0.8649 0.4496 0.025 Uiso 1 1 calc R . . C9B C 0.2377(5) 0.6952(6) 0.50191(15) 0.0213(8) Uani 1 1 d . . . H9B H 0.1956 0.6499 0.4798 0.026 Uiso 1 1 calc R . . C10B C 0.2635(6) 0.6350(6) 0.55317(16) 0.0218(8) Uani 1 1 d . . . C11B C 0.3230(6) 0.7024(7) 0.58673(16) 0.0256(9) Uani 1 1 d . . . H11B H 0.3368 0.6629 0.6212 0.031 Uiso 1 1 calc R . . C12B C 0.3619(6) 0.8300(6) 0.56836(15) 0.0233(9) Uani 1 1 d . . . H12B H 0.4029 0.8751 0.5908 0.028 Uiso 1 1 calc R . . C13B C 0.4674(6) 1.4189(6) 0.40950(14) 0.0213(8) Uani 1 1 d . . . H13B H 0.3853 1.5105 0.4037 0.026 Uiso 1 1 calc R . . C14B C 0.6759(5) 1.1486(5) 0.49188(13) 0.0161(7) Uani 1 1 d . . . C15B C 0.6123(5) 1.2325(6) 0.53257(15) 0.0233(9) Uani 1 1 d . . . H15B H 0.5078 1.2865 0.5328 0.028 Uiso 1 1 calc R . . C16B C 0.7053(6) 1.2353(7) 0.57269(16) 0.0276(11) Uani 1 1 d . . . H16B H 0.6628 1.2896 0.5999 0.033 Uiso 1 1 calc R . . C17B C 0.8634(6) 1.1555(6) 0.57158(15) 0.0238(9) Uani 1 1 d . . . C18B C 0.9275(5) 1.0752(6) 0.53099(16) 0.0215(8) Uani 1 1 d . . . H18B H 1.0323 1.0225 0.5303 0.026 Uiso 1 1 calc R . . C19B C 0.8325(5) 1.0745(6) 0.49117(14) 0.0194(8) Uani 1 1 d . . . H19B H 0.8756 1.0228 0.4635 0.023 Uiso 1 1 calc R . . C20B C 0.6487(5) 0.8462(5) 0.48002(14) 0.0174(7) Uani 1 1 d . . . C21B C 0.7301(5) 0.7947(6) 0.52651(15) 0.0222(9) Uani 1 1 d . . . H21B H 0.7153 0.8588 0.5519 0.027 Uiso 1 1 calc R . . C22B C 0.8341(6) 0.6447(7) 0.53390(18) 0.0282(10) Uani 1 1 d . . . H22B H 0.8905 0.6093 0.5643 0.034 Uiso 1 1 calc R . . C23B C 0.8546(6) 0.5478(7) 0.4968(2) 0.0304(11) Uani 1 1 d . . . H23B H 0.9249 0.4486 0.5027 0.036 Uiso 1 1 calc R . . C24B C 0.7713(7) 0.5960(7) 0.45030(19) 0.0280(10) Uani 1 1 d . . . H24B H 0.7834 0.5315 0.4252 0.034 Uiso 1 1 calc R . . C25B C 0.6706(5) 0.7454(6) 0.44435(15) 0.0197(8) Uani 1 1 d . . . C26B C 0.4819(5) 0.9562(6) 0.40916(13) 0.0189(8) Uani 1 1 d . . . C1C C 0.0957(5) 0.6477(5) 0.80422(13) 0.0145(7) Uani 1 1 d . . . C2C C 0.1458(5) 0.5225(5) 0.76713(13) 0.0166(7) Uani 1 1 d . . . H2C H 0.1847 0.5669 0.7363 0.020 Uiso 1 1 calc R . . C3C C 0.2772(5) 0.3806(5) 0.78949(15) 0.0190(7) Uani 1 1 d . . . H3C1 H 0.2357 0.3161 0.8128 0.023 Uiso 1 1 calc R . . H3C2 H 0.3262 0.3227 0.7618 0.023 Uiso 1 1 calc R . . C4C C 0.3945(5) 0.4159(5) 0.81734(14) 0.0183(7) Uani 1 1 d . . . H4C H 0.4860 0.3364 0.8263 0.022 Uiso 1 1 calc R . . C5C C 0.3777(5) 0.5544(5) 0.83050(13) 0.0171(7) Uani 1 1 d . . . C6C C 0.2359(5) 0.6956(5) 0.81690(13) 0.0160(7) Uani 1 1 d . . . H6C H 0.2094 0.7489 0.8474 0.019 Uiso 1 1 calc R . . C7C C 0.0104(5) 0.4834(5) 0.75015(13) 0.0182(7) Uani 1 1 d . . . C8C C -0.0603(5) 0.3996(6) 0.78317(14) 0.0194(8) Uani 1 1 d . . . H8C H -0.0227 0.3639 0.8165 0.023 Uiso 1 1 calc R . . C9C C -0.1856(5) 0.3685(6) 0.76724(14) 0.0193(8) Uani 1 1 d . . . H9C H -0.2311 0.3119 0.7896 0.023 Uiso 1 1 calc R . . C10C C -0.2426(5) 0.4224(5) 0.71763(14) 0.0179(7) Uani 1 1 d . . . C11C C -0.1738(6) 0.5043(6) 0.68371(15) 0.0218(8) Uani 1 1 d . . . H11C H -0.2114 0.5387 0.6504 0.026 Uiso 1 1 calc R . . C12C C -0.0485(6) 0.5347(6) 0.69992(13) 0.0201(8) Uani 1 1 d . . . H12C H -0.0025 0.5899 0.6772 0.024 Uiso 1 1 calc R . . C13C C 0.4998(6) 0.5742(6) 0.85820(14) 0.0218(9) Uani 1 1 d . . . H13C H 0.5887 0.4895 0.8650 0.026 Uiso 1 1 calc R . . C14C C 0.2713(5) 0.8047(5) 0.77478(13) 0.0153(7) Uani 1 1 d . . . C15C C 0.3869(5) 0.7524(5) 0.73883(14) 0.0180(7) Uani 1 1 d . . . H15C H 0.4409 0.6479 0.7402 0.022 Uiso 1 1 calc R . . C16C C 0.4217(6) 0.8536(6) 0.70148(15) 0.0209(8) Uani 1 1 d . . . H16C H 0.4994 0.8173 0.6783 0.025 Uiso 1 1 calc R . . C17C C 0.3390(6) 1.0111(6) 0.69885(15) 0.0227(8) Uani 1 1 d . . . C18C C 0.2224(6) 1.0651(6) 0.73341(16) 0.0233(9) Uani 1 1 d . . . H18C H 0.1648 1.1690 0.7307 0.028 Uiso 1 1 calc R . . C19C C 0.1924(5) 0.9636(5) 0.77176(15) 0.0199(8) Uani 1 1 d . . . H19C H 0.1187 1.0012 0.7960 0.024 Uiso 1 1 calc R . . C20C C -0.0440(5) 0.7802(5) 0.78455(14) 0.0171(7) Uani 1 1 d . . . C21C C -0.0783(6) 0.8770(5) 0.73825(15) 0.0209(8) Uani 1 1 d . . . H21C H -0.0048 0.8697 0.7130 0.025 Uiso 1 1 calc R . . C22C C -0.2256(6) 0.9853(6) 0.73063(17) 0.0251(9) Uani 1 1 d . . . H22C H -0.2500 1.0505 0.6999 0.030 Uiso 1 1 calc R . . C23C C -0.3366(6) 0.9972(7) 0.76833(18) 0.0272(10) Uani 1 1 d . . . H23C H -0.4326 1.0723 0.7626 0.033 Uiso 1 1 calc R . . C24C C -0.3072(6) 0.8994(6) 0.81444(18) 0.0243(9) Uani 1 1 d . . . H24C H -0.3812 0.9050 0.8395 0.029 Uiso 1 1 calc R . . C25C C -0.1591(5) 0.7926(6) 0.82050(14) 0.0189(8) Uani 1 1 d . . . C26C C 0.0371(5) 0.5915(5) 0.85575(13) 0.0178(7) Uani 1 1 d . . . C1D C 0.2205(5) 0.1179(5) -0.03309(13) 0.0153(7) Uani 1 1 d . . . C2D C 0.2838(5) -0.0492(5) -0.00436(13) 0.0171(7) Uani 1 1 d . . . H2D H 0.2317 -0.0471 0.0287 0.020 Uiso 1 1 calc R . . C3D C 0.2423(5) -0.1644(5) -0.03291(15) 0.0190(7) Uani 1 1 d . . . H3D1 H 0.3197 -0.2001 -0.0584 0.023 Uiso 1 1 calc R . . H3D2 H 0.2453 -0.2525 -0.0085 0.023 Uiso 1 1 calc R . . C4D C 0.0902(5) -0.1019(5) -0.05876(14) 0.0189(8) Uani 1 1 d . . . H4D H 0.0516 -0.1713 -0.0704 0.023 Uiso 1 1 calc R . . C5D C 0.0036(5) 0.0481(6) -0.06671(13) 0.0185(8) Uani 1 1 d . . . C6D C 0.0445(5) 0.1705(5) -0.04446(13) 0.0173(7) Uani 1 1 d . . . H6D H 0.0177 0.2616 -0.0702 0.021 Uiso 1 1 calc R . . C7D C 0.4525(5) -0.1002(5) 0.00773(13) 0.0169(7) Uani 1 1 d . . . C8D C 0.5003(5) -0.0861(6) 0.05640(15) 0.0196(8) Uani 1 1 d . . . H8D H 0.4275 -0.0412 0.0800 0.024 Uiso 1 1 calc R . . C9D C 0.6541(6) -0.1380(6) 0.06978(15) 0.0216(8) Uani 1 1 d . . . H9D H 0.6837 -0.1270 0.1020 0.026 Uiso 1 1 calc R . . C10D C 0.7649(5) -0.2070(6) 0.03488(15) 0.0197(8) Uani 1 1 d . . . C11D C 0.7209(5) -0.2169(6) -0.01464(16) 0.0207(8) Uani 1 1 d . . . H11D H 0.7944 -0.2588 -0.0385 0.025 Uiso 1 1 calc R . . C12D C 0.5672(5) -0.1638(6) -0.02771(14) 0.0200(8) Uani 1 1 d . . . H12D H 0.5385 -0.1700 -0.0606 0.024 Uiso 1 1 calc R . . C13D C -0.1372(6) 0.0935(6) -0.09631(15) 0.0226(9) Uani 1 1 d . . . H13D H -0.1677 0.0162 -0.1060 0.027 Uiso 1 1 calc R . . C14D C -0.0521(5) 0.2140(5) 0.00254(13) 0.0156(7) Uani 1 1 d . . . C15D C -0.0719(5) 0.1010(5) 0.03989(15) 0.0186(7) Uani 1 1 d . . . H15D H -0.0273 -0.0017 0.0351 0.022 Uiso 1 1 calc R . . C16D C -0.1562(6) 0.1380(6) 0.08384(15) 0.0220(8) Uani 1 1 d . . . H16D H -0.1670 0.0615 0.1083 0.026 Uiso 1 1 calc R . . C17D C -0.2236(5) 0.2904(6) 0.09045(15) 0.0200(8) Uani 1 1 d . . . C18D C -0.2102(6) 0.4080(6) 0.05377(17) 0.0224(8) Uani 1 1 d . . . H18D H -0.2576 0.5103 0.0586 0.027 Uiso 1 1 calc R . . C19D C -0.1243(6) 0.3684(6) 0.00984(16) 0.0213(8) Uani 1 1 d . . . H19D H -0.1150 0.4453 -0.0148 0.026 Uiso 1 1 calc R . . C20D C 0.2691(5) 0.2275(5) -0.00576(14) 0.0170(7) Uani 1 1 d . . . C21D C 0.2338(6) 0.2781(6) 0.04186(15) 0.0210(8) Uani 1 1 d . . . H21D H 0.1637 0.2491 0.0628 0.025 Uiso 1 1 calc R . . C22D C 0.3061(6) 0.3736(6) 0.05775(16) 0.0238(9) Uani 1 1 d . . . H22D H 0.2797 0.4132 0.0888 0.029 Uiso 1 1 calc R . . C23D C 0.4180(6) 0.4102(7) 0.02724(17) 0.0273(10) Uani 1 1 d . . . H23D H 0.4678 0.4709 0.0387 0.033 Uiso 1 1 calc R . . C24D C 0.4553(6) 0.3557(6) -0.02047(16) 0.0240(9) Uani 1 1 d . . . H24D H 0.5284 0.3800 -0.0413 0.029 Uiso 1 1 calc R . . C25D C 0.3807(5) 0.2665(5) -0.03498(14) 0.0187(8) Uani 1 1 d . . . C26D C 0.3060(5) 0.1244(6) -0.08441(14) 0.0202(8) Uani 1 1 d . . . Cl1A Cl -0.32631(14) 0.93818(14) 0.21348(4) 0.0251(2) Uani 1 1 d . . . Cl2A Cl 0.32799(15) -0.31882(15) 0.12167(4) 0.0269(2) Uani 1 1 d . . . Cl1B Cl 0.22075(15) 0.47074(15) 0.57629(5) 0.0287(2) Uani 1 1 d . . . Cl2B Cl 0.97963(16) 1.1611(2) 0.62086(5) 0.0377(4) Uani 1 1 d . . . Cl1C Cl -0.40166(13) 0.38589(13) 0.69768(4) 0.0219(2) Uani 1 1 d . . . Cl2C Cl 0.38595(17) 1.13773(16) 0.65278(4) 0.0318(3) Uani 1 1 d . . . Cl1D Cl 0.95562(13) -0.28790(15) 0.05336(4) 0.0257(2) Uani 1 1 d . . . Cl2D Cl -0.33404(14) 0.33851(16) 0.14469(4) 0.0275(2) Uani 1 1 d . . . O1A O 0.1327(5) -0.2835(5) 0.37657(14) 0.0327(9) Uani 1 1 d . . . O2A O 0.1197(4) 0.3437(4) 0.34740(11) 0.0214(6) Uani 1 1 d . . . O3A O -0.0295(4) 0.2223(5) 0.38809(11) 0.0257(8) Uani 1 1 d . . . O1B O 0.5930(5) 1.4157(5) 0.39369(12) 0.0276(8) Uani 1 1 d . . . O2B O 0.5760(4) 0.8106(4) 0.40100(11) 0.0225(7) Uani 1 1 d . . . O3B O 0.3897(4) 1.0336(4) 0.37756(11) 0.0230(7) Uani 1 1 d . . . O1C O 0.4949(5) 0.6930(5) 0.87322(12) 0.0273(8) Uani 1 1 d . . . O2C O -0.1120(4) 0.6852(4) 0.86393(11) 0.0205(6) Uani 1 1 d . . . O3C O 0.1015(4) 0.4868(4) 0.88734(11) 0.0230(7) Uani 1 1 d . . . O1D O -0.2190(5) 0.2268(5) -0.10949(13) 0.0315(9) Uani 1 1 d . . . O2D O 0.4062(4) 0.2026(4) -0.08126(11) 0.0228(7) Uani 1 1 d . . . O3D O 0.2978(5) 0.0703(5) -0.12219(11) 0.0262(8) 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 C1A 0.0162(18) 0.016(2) 0.0179(13) -0.0017(12) -0.0028(11) -0.0051(15) C2A 0.0143(17) 0.0140(19) 0.0205(14) -0.0005(12) -0.0022(11) -0.0054(15) C3A 0.0130(18) 0.014(2) 0.0317(17) -0.0002(14) -0.0042(12) -0.0034(15) C4A 0.019(2) 0.018(2) 0.0249(15) -0.0019(13) 0.0007(12) -0.0101(17) C5A 0.0171(18) 0.0128(19) 0.0235(15) 0.0032(12) -0.0024(12) -0.0025(15) C6A 0.0149(18) 0.0133(19) 0.0209(14) -0.0003(12) -0.0032(11) -0.0034(14) C7A 0.0156(18) 0.013(2) 0.0230(14) -0.0008(12) -0.0042(11) -0.0015(15) C8A 0.0156(18) 0.015(2) 0.0233(15) -0.0012(12) -0.0008(11) -0.0029(15) C9A 0.018(2) 0.016(2) 0.0263(16) 0.0043(13) -0.0038(12) -0.0059(16) C10A 0.0159(19) 0.012(2) 0.0301(17) -0.0002(13) -0.0056(13) -0.0055(16) C11A 0.021(2) 0.014(2) 0.0251(15) -0.0016(13) -0.0042(13) -0.0060(16) C12A 0.0141(18) 0.015(2) 0.0228(14) -0.0007(12) -0.0028(11) -0.0012(15) C13A 0.029(3) 0.023(3) 0.0268(17) 0.0061(15) -0.0035(15) -0.012(2) C14A 0.0140(18) 0.0119(19) 0.0251(15) -0.0019(12) -0.0017(11) -0.0032(15) C15A 0.0168(19) 0.017(2) 0.0232(15) -0.0024(13) -0.0041(12) -0.0014(16) C16A 0.019(2) 0.015(2) 0.0259(16) -0.0034(13) -0.0065(13) -0.0027(16) C17A 0.022(2) 0.015(2) 0.0266(16) -0.0033(14) -0.0012(13) -0.0059(17) C18A 0.0134(19) 0.022(2) 0.0371(19) -0.0101(16) 0.0010(14) -0.0079(17) C19A 0.0149(19) 0.017(2) 0.0326(18) -0.0071(15) -0.0026(13) -0.0033(16) C20A 0.0133(17) 0.016(2) 0.0212(14) 0.0017(12) -0.0032(11) -0.0051(15) C21A 0.020(2) 0.016(2) 0.0232(15) 0.0009(13) -0.0011(12) -0.0049(17) C22A 0.015(2) 0.017(2) 0.0338(18) 0.0045(14) 0.0021(13) -0.0056(17) C23A 0.018(2) 0.017(2) 0.042(2) 0.0078(16) -0.0019(15) -0.0099(18) C24A 0.028(2) 0.018(2) 0.0310(18) 0.0038(15) -0.0079(15) -0.0149(19) C25A 0.0137(18) 0.017(2) 0.0255(15) 0.0012(13) -0.0050(12) -0.0030(16) C26A 0.021(2) 0.016(2) 0.0183(14) -0.0001(12) -0.0061(12) -0.0027(16) C1B 0.0149(17) 0.0134(18) 0.0164(12) -0.0012(11) -0.0035(10) -0.0040(14) C2B 0.0115(16) 0.0122(18) 0.0208(14) -0.0009(11) -0.0031(10) -0.0026(14) C3B 0.0154(18) 0.013(2) 0.0261(15) 0.0009(13) -0.0023(12) -0.0037(15) C4B 0.0135(18) 0.014(2) 0.0235(15) -0.0023(12) -0.0030(11) 0.0003(14) C5B 0.0156(18) 0.0128(19) 0.0210(14) -0.0019(12) -0.0022(11) -0.0045(15) C6B 0.0141(17) 0.0131(19) 0.0183(13) -0.0024(11) -0.0017(10) -0.0022(14) C7B 0.0132(17) 0.0126(19) 0.0236(14) -0.0006(12) -0.0008(11) -0.0045(14) C8B 0.024(2) 0.018(2) 0.0213(14) -0.0020(13) 0.0005(13) -0.0077(17) C9B 0.019(2) 0.017(2) 0.0264(16) -0.0022(14) -0.0007(13) -0.0047(17) C10B 0.016(2) 0.013(2) 0.0322(18) 0.0035(14) 0.0015(13) -0.0029(16) C11B 0.023(2) 0.025(3) 0.0284(17) 0.0087(15) -0.0047(14) -0.0112(19) C12B 0.022(2) 0.023(2) 0.0236(16) 0.0014(14) -0.0043(13) -0.0085(19) C13B 0.025(2) 0.012(2) 0.0224(15) 0.0001(12) -0.0019(13) -0.0014(17) C14B 0.0121(16) 0.0148(19) 0.0194(13) -0.0012(11) -0.0017(10) -0.0023(14) C15B 0.017(2) 0.030(3) 0.0246(16) -0.0092(15) 0.0005(13) -0.0075(18) C16B 0.021(2) 0.037(3) 0.0256(17) -0.0136(18) -0.0011(14) -0.008(2) C17B 0.024(2) 0.025(3) 0.0239(16) -0.0054(15) -0.0034(13) -0.0085(19) C18B 0.0111(18) 0.022(2) 0.0315(17) -0.0048(15) -0.0025(12) -0.0044(16) C19B 0.0121(18) 0.021(2) 0.0247(15) -0.0050(14) 0.0000(12) -0.0043(16) C20B 0.0136(17) 0.015(2) 0.0222(14) 0.0000(12) -0.0023(11) -0.0035(15) C21B 0.018(2) 0.021(2) 0.0253(16) 0.0032(14) -0.0035(13) -0.0050(17) C22B 0.016(2) 0.025(3) 0.037(2) 0.0081(17) -0.0030(15) -0.0034(19) C23B 0.016(2) 0.016(2) 0.050(3) 0.0051(18) 0.0015(17) 0.0013(19) C24B 0.023(2) 0.015(2) 0.043(2) -0.0041(17) 0.0033(17) -0.0028(19) C25B 0.0167(19) 0.014(2) 0.0268(16) 0.0001(13) -0.0012(12) -0.0037(16) C26B 0.023(2) 0.019(2) 0.0185(14) -0.0017(12) -0.0004(12) -0.0120(17) C1C 0.0139(17) 0.0091(17) 0.0199(13) -0.0001(11) -0.0002(10) -0.0037(14) C2C 0.023(2) 0.0085(17) 0.0199(13) -0.0019(11) 0.0013(11) -0.0074(15) C3C 0.0126(18) 0.0085(18) 0.0317(17) -0.0011(13) -0.0010(12) 0.0011(14) C4C 0.0172(19) 0.0108(19) 0.0239(15) 0.0010(12) -0.0005(12) -0.0021(15) C5C 0.0117(17) 0.017(2) 0.0207(14) 0.0002(12) -0.0015(11) -0.0031(15) C6C 0.0156(18) 0.0108(18) 0.0208(13) -0.0026(11) 0.0000(11) -0.0032(14) C7C 0.022(2) 0.0127(19) 0.0192(14) -0.0020(12) -0.0003(12) -0.0050(16) C8C 0.021(2) 0.017(2) 0.0206(14) 0.0001(12) -0.0013(12) -0.0071(16) C9C 0.019(2) 0.016(2) 0.0220(15) -0.0006(12) 0.0007(12) -0.0051(16) C10C 0.0199(19) 0.0101(18) 0.0229(15) -0.0037(12) -0.0020(12) -0.0037(15) C11C 0.024(2) 0.018(2) 0.0233(15) -0.0014(13) -0.0031(13) -0.0084(17) C12C 0.024(2) 0.018(2) 0.0186(14) -0.0010(12) -0.0001(12) -0.0082(17) C13C 0.019(2) 0.020(2) 0.0208(14) 0.0011(13) -0.0033(12) -0.0004(17) C14C 0.0179(18) 0.0112(18) 0.0179(13) -0.0002(11) -0.0019(11) -0.0068(14) C15C 0.0139(18) 0.0123(19) 0.0231(15) 0.0013(12) -0.0009(11) 0.0000(15) C16C 0.020(2) 0.015(2) 0.0241(15) 0.0019(13) -0.0025(12) -0.0027(16) C17C 0.031(2) 0.016(2) 0.0239(15) 0.0036(13) -0.0067(14) -0.0136(18) C18C 0.026(2) 0.0086(19) 0.0339(18) -0.0014(14) -0.0072(15) -0.0045(17) C19C 0.020(2) 0.0090(19) 0.0289(16) -0.0029(13) -0.0031(13) -0.0020(15) C20C 0.0164(18) 0.0117(19) 0.0231(14) -0.0027(12) -0.0016(11) -0.0044(15) C21C 0.023(2) 0.011(2) 0.0270(16) -0.0014(13) -0.0036(13) -0.0045(17) C22C 0.031(3) 0.014(2) 0.0314(18) 0.0005(14) -0.0102(16) -0.0090(19) C23C 0.019(2) 0.019(2) 0.040(2) -0.0052(17) -0.0072(16) -0.0009(19) C24C 0.017(2) 0.018(2) 0.038(2) -0.0055(16) -0.0026(14) -0.0040(17) C25C 0.0149(18) 0.017(2) 0.0246(15) -0.0033(13) -0.0036(12) -0.0044(15) C26C 0.0131(17) 0.015(2) 0.0218(14) -0.0011(12) -0.0010(11) -0.0014(15) C1D 0.0141(17) 0.0109(18) 0.0219(14) 0.0004(11) -0.0008(11) -0.0062(14) C2D 0.0168(18) 0.015(2) 0.0196(14) -0.0006(12) -0.0008(11) -0.0059(15) C3D 0.0164(19) 0.0082(18) 0.0311(17) -0.0001(13) -0.0024(13) -0.0033(15) C4D 0.0164(19) 0.014(2) 0.0252(15) -0.0026(13) -0.0037(12) -0.0031(16) C5D 0.0167(19) 0.016(2) 0.0200(14) -0.0012(12) -0.0051(11) -0.0025(15) C6D 0.0183(19) 0.0118(19) 0.0198(14) 0.0024(11) -0.0018(11) -0.0043(15) C7D 0.0130(17) 0.0111(18) 0.0234(14) 0.0005(12) -0.0029(11) -0.0009(14) C8D 0.0164(19) 0.015(2) 0.0255(15) -0.0016(13) -0.0036(12) -0.0027(16) C9D 0.020(2) 0.017(2) 0.0272(16) -0.0005(14) -0.0057(13) -0.0056(17) C10D 0.0113(18) 0.016(2) 0.0307(17) 0.0018(13) -0.0025(12) -0.0051(15) C11D 0.0140(19) 0.014(2) 0.0316(17) -0.0017(14) -0.0007(13) -0.0018(16) C12D 0.0164(19) 0.020(2) 0.0213(14) -0.0001(13) -0.0012(12) -0.0036(16) C13D 0.021(2) 0.018(2) 0.0280(17) -0.0007(14) -0.0071(13) -0.0056(17) C14D 0.0117(17) 0.0105(18) 0.0237(14) 0.0007(12) -0.0008(11) -0.0038(14) C15D 0.0161(19) 0.0096(19) 0.0279(16) -0.0005(12) 0.0028(12) -0.0026(15) C16D 0.025(2) 0.016(2) 0.0236(15) 0.0007(13) -0.0002(13) -0.0074(18) C17D 0.0144(18) 0.019(2) 0.0272(16) -0.0059(14) -0.0007(12) -0.0051(16) C18D 0.016(2) 0.010(2) 0.039(2) -0.0051(15) 0.0028(14) -0.0016(16) C19D 0.020(2) 0.012(2) 0.0336(18) 0.0003(14) 0.0010(14) -0.0081(17) C20D 0.0159(18) 0.0122(19) 0.0228(14) 0.0015(12) -0.0039(11) -0.0057(15) C21D 0.020(2) 0.016(2) 0.0261(16) -0.0028(14) -0.0034(13) -0.0041(17) C22D 0.027(2) 0.016(2) 0.0277(17) -0.0048(14) -0.0066(14) -0.0054(18) C23D 0.026(2) 0.024(3) 0.0326(19) -0.0029(17) -0.0103(16) -0.008(2) C24D 0.021(2) 0.018(2) 0.0322(18) 0.0036(15) -0.0057(14) -0.0073(18) C25D 0.0161(19) 0.014(2) 0.0242(15) 0.0027(12) -0.0041(12) -0.0042(16) C26D 0.020(2) 0.014(2) 0.0231(15) 0.0022(13) -0.0021(12) -0.0036(16) Cl1A 0.0204(5) 0.0130(5) 0.0402(5) 0.0020(4) -0.0084(4) -0.0046(4) Cl2A 0.0292(6) 0.0200(6) 0.0317(4) -0.0086(4) 0.0045(4) -0.0073(5) Cl1B 0.0214(6) 0.0147(5) 0.0443(5) 0.0080(4) 0.0011(4) -0.0033(4) Cl2B 0.0269(6) 0.0495(10) 0.0379(5) -0.0155(6) -0.0109(4) -0.0101(6) Cl1C 0.0215(5) 0.0170(5) 0.0279(4) -0.0059(3) -0.0032(3) -0.0061(4) Cl2C 0.0391(7) 0.0237(7) 0.0339(5) 0.0121(4) -0.0100(4) -0.0173(6) Cl1D 0.0152(5) 0.0169(6) 0.0426(5) 0.0042(4) -0.0070(3) -0.0047(4) Cl2D 0.0215(5) 0.0321(7) 0.0313(4) -0.0113(4) 0.0040(3) -0.0101(5) O1A 0.030(2) 0.021(2) 0.0414(17) 0.0100(14) -0.0081(14) -0.0056(17) O2A 0.0229(16) 0.0191(17) 0.0238(12) -0.0020(10) -0.0052(10) -0.0090(14) O3A 0.0235(17) 0.030(2) 0.0220(12) -0.0029(12) -0.0016(10) -0.0070(15) O1B 0.029(2) 0.022(2) 0.0330(15) 0.0000(12) 0.0033(12) -0.0114(16) O2B 0.0233(17) 0.0188(18) 0.0246(12) -0.0059(11) -0.0012(10) -0.0050(14) O3B 0.0266(18) 0.0203(18) 0.0214(11) -0.0006(10) -0.0080(10) -0.0072(14) O1C 0.0254(18) 0.028(2) 0.0297(14) -0.0074(13) -0.0045(11) -0.0085(16) O2C 0.0130(14) 0.0178(17) 0.0255(12) 0.0005(10) 0.0000(9) 0.0001(12) O3C 0.0253(18) 0.0164(17) 0.0246(12) 0.0049(10) -0.0019(10) -0.0060(14) O1D 0.026(2) 0.025(2) 0.0382(16) 0.0036(14) -0.0134(13) -0.0049(17) O2D 0.0257(18) 0.0192(18) 0.0232(12) 0.0018(10) -0.0008(10) -0.0089(14) O3D 0.032(2) 0.0220(19) 0.0219(12) 0.0003(11) 0.0000(11) -0.0074(15) _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 C1A C20A 1.504(6) . ? C1A C26A 1.536(5) . ? C1A C2A 1.550(6) . ? C1A C6A 1.563(7) . ? C2A C7A 1.530(7) . ? C2A C3A 1.548(7) . ? C3A C4A 1.495(7) . ? C4A C5A 1.336(6) . ? C5A C13A 1.480(7) . ? C5A C6A 1.515(7) . ? C6A C14A 1.533(5) . ? C7A C8A 1.405(6) . ? C7A C12A 1.403(5) . ? C8A C9A 1.380(7) . ? C9A C10A 1.386(6) . ? C10A C11A 1.405(6) . ? C10A Cl1A 1.746(5) . ? C11A C12A 1.389(7) . ? C13A O1A 1.192(7) . ? C14A C19A 1.398(6) . ? C14A C15A 1.398(6) . ? C15A C16A 1.408(5) . ? C16A C17A 1.359(7) . ? C17A C18A 1.409(6) . ? C17A Cl2A 1.747(4) . ? C18A C19A 1.396(5) . ? C20A C25A 1.399(6) . ? C20A C21A 1.402(5) . ? C21A C22A 1.394(7) . ? C22A C23A 1.398(8) . ? C23A C24A 1.399(7) . ? C24A C25A 1.378(7) . ? C25A O2A 1.393(5) . ? C26A O3A 1.200(6) . ? C26A O2A 1.381(6) . ? C1B C20B 1.517(6) . ? C1B C26B 1.546(5) . ? C1B C2B 1.563(5) . ? C1B C6B 1.567(7) . ? C2B C7B 1.515(7) . ? C2B C3B 1.540(6) . ? C3B C4B 1.489(7) . ? C4B C5B 1.350(6) . ? C5B C13B 1.477(7) . ? C5B C6B 1.513(6) . ? C6B C14B 1.520(5) . ? C7B C12B 1.400(5) . ? C7B C8B 1.402(6) . ? C8B C9B 1.388(7) . ? C9B C10B 1.387(6) . ? C10B C11B 1.380(8) . ? C10B Cl1B 1.750(5) . ? C11B C12B 1.390(8) . ? C13B O1B 1.221(6) . ? C14B C19B 1.383(6) . ? C14B C15B 1.403(5) . ? C15B C16B 1.396(6) . ? C16B C17B 1.404(7) . ? C17B C18B 1.385(6) . ? C17B Cl2B 1.734(4) . ? C18B C19B 1.395(6) . ? C20B C25B 1.378(6) . ? C20B C21B 1.399(5) . ? C21B C22B 1.397(7) . ? C22B C23B 1.382(8) . ? C23B C24B 1.406(8) . ? C24B C25B 1.381(7) . ? C25B O2B 1.401(5) . ? C26B O3B 1.189(5) . ? C26B O2B 1.383(6) . ? C1C C20C 1.505(6) . ? C1C C26C 1.541(5) . ? C1C C2C 1.560(5) . ? C1C C6C 1.579(6) . ? C2C C3C 1.527(6) . ? C2C C7C 1.525(7) . ? C3C C4C 1.486(7) . ? C4C C5C 1.342(6) . ? C5C C13C 1.448(7) . ? C5C C6C 1.524(6) . ? C6C C14C 1.515(6) . ? C7C C8C 1.395(7) . ? C7C C12C 1.406(5) . ? C8C C9C 1.387(7) . ? C9C C10C 1.389(5) . ? C10C C11C 1.386(7) . ? C10C Cl1C 1.744(5) . ? C11C C12C 1.386(7) . ? C13C O1C 1.214(7) . ? C14C C19C 1.407(6) . ? C14C C15C 1.408(5) . ? C15C C16C 1.385(7) . ? C16C C17C 1.402(7) . ? C17C C18C 1.391(7) . ? C17C Cl2C 1.737(5) . ? C18C C19C 1.384(7) . ? C20C C25C 1.390(6) . ? C20C C21C 1.395(6) . ? C21C C22C 1.398(7) . ? C22C C23C 1.395(8) . ? C23C C24C 1.394(8) . ? C24C C25C 1.396(7) . ? C25C O2C 1.392(5) . ? C26C O3C 1.194(5) . ? C26C O2C 1.390(5) . ? C1D C20D 1.520(6) . ? C1D C26D 1.550(5) . ? C1D C2D 1.566(6) . ? C1D C6D 1.568(6) . ? C2D C7D 1.508(6) . ? C2D C3D 1.549(6) . ? C3D C4D 1.483(6) . ? C4D C5D 1.349(6) . ? C5D C13D 1.451(6) . ? C5D C6D 1.514(7) . ? C6D C14D 1.519(5) . ? C7D C8D 1.406(5) . ? C7D C12D 1.416(6) . ? C8D C9D 1.386(7) . ? C9D C10D 1.398(6) . ? C10D C11D 1.402(6) . ? C10D Cl1D 1.732(5) . ? C11D C12D 1.383(6) . ? C13D O1D 1.227(6) . ? C14D C19D 1.404(6) . ? C14D C15D 1.405(6) . ? C15D C16D 1.389(5) . ? C16D C17D 1.378(7) . ? C17D C18D 1.404(7) . ? C17D Cl2D 1.745(4) . ? C18D C19D 1.399(6) . ? C20D C21D 1.386(5) . ? C20D C25D 1.394(6) . ? C21D C22D 1.401(7) . ? C22D C23D 1.403(8) . ? C23D C24D 1.404(6) . ? C24D C25D 1.353(7) . ? C25D O2D 1.403(5) . ? C26D O3D 1.189(5) . ? C26D O2D 1.382(7) . ? 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 C20A C1A C26A 100.8(4) . . ? C20A C1A C2A 110.6(3) . . ? C26A C1A C2A 109.2(3) . . ? C20A C1A C6A 114.7(3) . . ? C26A C1A C6A 109.5(3) . . ? C2A C1A C6A 111.4(4) . . ? C7A C2A C3A 111.0(4) . . ? C7A C2A C1A 112.5(4) . . ? C3A C2A C1A 112.7(3) . . ? C4A C3A C2A 113.4(4) . . ? C5A C4A C3A 125.1(5) . . ? C4A C5A C13A 119.2(5) . . ? C4A C5A C6A 122.9(4) . . ? C13A C5A C6A 117.9(4) . . ? C5A C6A C14A 108.7(4) . . ? C5A C6A C1A 111.1(3) . . ? C14A C6A C1A 112.8(3) . . ? C8A C7A C12A 117.8(4) . . ? C8A C7A C2A 119.7(3) . . ? C12A C7A C2A 122.5(4) . . ? C9A C8A C7A 121.4(4) . . ? C8A C9A C10A 119.8(4) . . ? C9A C10A C11A 120.5(4) . . ? C9A C10A Cl1A 120.1(3) . . ? C11A C10A Cl1A 119.3(3) . . ? C12A C11A C10A 118.9(4) . . ? C11A C12A C7A 121.5(4) . . ? O1A C13A C5A 124.4(5) . . ? C19A C14A C15A 118.9(3) . . ? C19A C14A C6A 120.5(4) . . ? C15A C14A C6A 120.6(4) . . ? C14A C15A C16A 120.3(4) . . ? C17A C16A C15A 119.6(4) . . ? C16A C17A C18A 121.8(4) . . ? C16A C17A Cl2A 119.3(3) . . ? C18A C17A Cl2A 118.9(4) . . ? C19A C18A C17A 118.2(4) . . ? C18A C19A C14A 121.2(4) . . ? C25A C20A C21A 118.2(4) . . ? C25A C20A C1A 108.4(3) . . ? C21A C20A C1A 133.2(4) . . ? C22A C21A C20A 118.7(4) . . ? C21A C22A C23A 120.9(4) . . ? C24A C23A C22A 121.6(5) . . ? C25A C24A C23A 115.9(4) . . ? C24A C25A O2A 123.6(4) . . ? C24A C25A C20A 124.6(4) . . ? O2A C25A C20A 111.7(4) . . ? O3A C26A O2A 120.9(4) . . ? O3A C26A C1A 128.8(5) . . ? O2A C26A C1A 110.2(4) . . ? C20B C1B C26B 100.4(3) . . ? C20B C1B C2B 111.0(3) . . ? C26B C1B C2B 112.2(3) . . ? C20B C1B C6B 114.8(4) . . ? C26B C1B C6B 107.7(3) . . ? C2B C1B C6B 110.4(3) . . ? C7B C2B C3B 112.8(4) . . ? C7B C2B C1B 113.2(3) . . ? C3B C2B C1B 112.0(3) . . ? C4B C3B C2B 113.5(4) . . ? C5B C4B C3B 123.4(4) . . ? C4B C5B C13B 117.3(4) . . ? C4B C5B C6B 124.7(4) . . ? C13B C5B C6B 117.9(4) . . ? C5B C6B C14B 111.6(3) . . ? C5B C6B C1B 110.7(4) . . ? C14B C6B C1B 112.1(3) . . ? C12B C7B C8B 118.3(4) . . ? C12B C7B C2B 119.0(4) . . ? C8B C7B C2B 122.8(3) . . ? C9B C8B C7B 120.9(4) . . ? C10B C9B C8B 119.4(4) . . ? C11B C10B C9B 121.2(5) . . ? C11B C10B Cl1B 118.9(3) . . ? C9B C10B Cl1B 120.0(4) . . ? C10B C11B C12B 119.3(4) . . ? C11B C12B C7B 121.1(4) . . ? O1B C13B C5B 122.9(4) . . ? C19B C14B C15B 118.9(4) . . ? C19B C14B C6B 119.7(3) . . ? C15B C14B C6B 121.4(4) . . ? C16B C15B C14B 120.3(4) . . ? C15B C16B C17B 119.4(4) . . ? C18B C17B C16B 120.6(4) . . ? C18B C17B Cl2B 119.8(4) . . ? C16B C17B Cl2B 119.6(3) . . ? C17B C18B C19B 119.0(4) . . ? C14B C19B C18B 121.7(3) . . ? C25B C20B C21B 118.7(4) . . ? C25B C20B C1B 108.9(3) . . ? C21B C20B C1B 132.1(4) . . ? C20B C21B C22B 118.3(4) . . ? C23B C22B C21B 121.2(4) . . ? C22B C23B C24B 121.4(5) . . ? C25B C24B C23B 115.6(5) . . ? C24B C25B C20B 124.7(4) . . ? C24B C25B O2B 123.1(4) . . ? C20B C25B O2B 112.2(4) . . ? O3B C26B O2B 120.3(3) . . ? O3B C26B C1B 129.4(4) . . ? O2B C26B C1B 110.2(4) . . ? C20C C1C C26C 100.8(3) . . ? C20C C1C C2C 111.9(3) . . ? C26C C1C C2C 112.6(4) . . ? C20C C1C C6C 114.1(4) . . ? C26C C1C C6C 107.0(3) . . ? C2C C1C C6C 110.0(3) . . ? C3C C2C C7C 112.4(4) . . ? C3C C2C C1C 112.1(3) . . ? C7C C2C C1C 111.6(3) . . ? C4C C3C C2C 113.8(4) . . ? C5C C4C C3C 124.6(4) . . ? C4C C5C C13C 119.5(4) . . ? C4C C5C C6C 123.2(4) . . ? C13C C5C C6C 117.3(4) . . ? C14C C6C C5C 110.4(3) . . ? C14C C6C C1C 113.9(3) . . ? C5C C6C C1C 110.7(4) . . ? C8C C7C C12C 118.0(4) . . ? C8C C7C C2C 122.2(3) . . ? C12C C7C C2C 119.8(4) . . ? C9C C8C C7C 121.2(4) . . ? C8C C9C C10C 119.5(4) . . ? C11C C10C C9C 120.7(4) . . ? C11C C10C Cl1C 119.6(3) . . ? C9C C10C Cl1C 119.7(4) . . ? C10C C11C C12C 119.4(4) . . ? C11C C12C C7C 121.2(4) . . ? O1C C13C C5C 124.9(4) . . ? C19C C14C C15C 117.8(4) . . ? C19C C14C C6C 120.4(3) . . ? C15C C14C C6C 121.7(4) . . ? C16C C15C C14C 121.3(4) . . ? C15C C16C C17C 119.5(4) . . ? C18C C17C C16C 120.2(4) . . ? C18C C17C Cl2C 120.6(4) . . ? C16C C17C Cl2C 119.3(4) . . ? C19C C18C C17C 119.8(4) . . ? C18C C19C C14C 121.3(4) . . ? C25C C20C C21C 118.6(4) . . ? C25C C20C C1C 108.4(3) . . ? C21C C20C C1C 132.8(4) . . ? C22C C21C C20C 118.6(4) . . ? C21C C22C C23C 121.1(4) . . ? C24C C23C C22C 121.7(5) . . ? C25C C24C C23C 115.4(5) . . ? C20C C25C C24C 124.6(4) . . ? C20C C25C O2C 112.8(4) . . ? C24C C25C O2C 122.6(4) . . ? O3C C26C O2C 120.0(4) . . ? O3C C26C C1C 129.5(4) . . ? O2C C26C C1C 110.5(3) . . ? C20D C1D C26D 100.5(4) . . ? C20D C1D C2D 111.0(3) . . ? C26D C1D C2D 109.0(3) . . ? C20D C1D C6D 114.7(3) . . ? C26D C1D C6D 109.1(3) . . ? C2D C1D C6D 111.9(4) . . ? C7D C2D C3D 112.6(4) . . ? C7D C2D C1D 112.4(4) . . ? C3D C2D C1D 111.9(3) . . ? C4D C3D C2D 114.8(4) . . ? C5D C4D C3D 124.8(4) . . ? C4D C5D C13D 118.6(4) . . ? C4D C5D C6D 122.8(4) . . ? C13D C5D C6D 118.6(4) . . ? C5D C6D C14D 109.2(4) . . ? C5D C6D C1D 111.3(3) . . ? C14D C6D C1D 112.9(3) . . ? C8D C7D C12D 117.6(4) . . ? C8D C7D C2D 119.4(3) . . ? C12D C7D C2D 123.0(3) . . ? C9D C8D C7D 121.1(4) . . ? C8D C9D C10D 120.2(4) . . ? C9D C10D C11D 120.0(4) . . ? C9D C10D Cl1D 120.3(3) . . ? C11D C10D Cl1D 119.7(3) . . ? C12D C11D C10D 119.4(4) . . ? C11D C12D C7D 121.7(4) . . ? O1D C13D C5D 124.6(5) . . ? C19D C14D C15D 118.1(3) . . ? C19D C14D C6D 120.9(4) . . ? C15D C14D C6D 121.0(4) . . ? C16D C15D C14D 121.9(4) . . ? C17D C16D C15D 118.8(4) . . ? C16D C17D C18D 121.6(4) . . ? C16D C17D Cl2D 119.1(4) . . ? C18D C17D Cl2D 119.2(4) . . ? C19D C18D C17D 118.8(4) . . ? C18D C19D C14D 120.8(4) . . ? C21D C20D C25D 119.1(4) . . ? C21D C20D C1D 132.3(4) . . ? C25D C20D C1D 108.3(3) . . ? C20D C21D C22D 118.6(5) . . ? C21D C22D C23D 120.5(4) . . ? C24D C23D C22D 120.4(5) . . ? C25D C24D C23D 117.4(5) . . ? C24D C25D C20D 124.0(4) . . ? C24D C25D O2D 124.0(4) . . ? C20D C25D O2D 112.0(4) . . ? O3D C26D O2D 120.8(4) . . ? O3D C26D C1D 129.3(5) . . ? O2D C26D C1D 109.9(3) . . ? C26A O2A C25A 108.2(3) . . ? C26B O2B C25B 108.1(3) . . ? C26C O2C C25C 107.3(3) . . ? C26D O2D C25D 108.3(3) . . ? _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.887 _refine_diff_density_max 1.627 _refine_diff_density_min -0.747 _refine_diff_density_rms 0.139 # Attachment 'CCDC-781524-TX3-MOH.cif' data_tx3-moh_0m _database_code_depnum_ccdc_archive 'CCDC 781524' #TrackingRef 'CCDC-781524-TX3-MOH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H19 Cl O3' _chemical_formula_weight 402.85 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' N N 0.0061 0.0033 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.3490(9) _cell_length_b 6.8640(6) _cell_length_c 15.7148(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.578(4) _cell_angle_gamma 90.00 _cell_volume 991.31(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1603 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 23.32 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 8979 _diffrn_reflns_av_R_equivalents 0.0658 _diffrn_reflns_av_sigmaI/netI 0.0963 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 28.41 _reflns_number_total 4166 _reflns_number_gt 2922 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.1000P)^2^+0.0846P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration ad _refine_ls_abs_structure_Flack -0.06(10) _refine_ls_number_reflns 4166 _refine_ls_number_parameters 262 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1601 _refine_ls_wR_factor_gt 0.1372 _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_restrained_S_all 0.921 _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 -0.08959(10) -0.42264(15) 0.62402(6) 0.0371(3) Uani 1 1 d . . . C6 C 0.2809(4) 0.3019(6) 0.65496(19) 0.0219(8) Uani 1 1 d . . . H6 H 0.2170 0.4065 0.6717 0.026 Uiso 1 1 calc R . . C14 C 0.0710(4) 0.1055(6) 0.6861(2) 0.0272(9) Uani 1 1 d . . . H14 H 0.0497 0.2122 0.7202 0.033 Uiso 1 1 calc R . . C22 C 0.3245(4) 0.1240(7) 0.9770(2) 0.0323(11) Uani 1 1 d . . . H22 H 0.3057 0.0964 1.0331 0.039 Uiso 1 1 calc R . . C24 C 0.3862(4) 0.3422(6) 0.8738(2) 0.0255(8) Uani 1 1 d . . . C15 C -0.0150(4) -0.0571(6) 0.6800(2) 0.0296(10) Uani 1 1 d . . . H15 H -0.0942 -0.0636 0.7101 0.036 Uiso 1 1 calc R . . C2 C 0.5455(4) 0.1752(6) 0.70442(19) 0.0242(8) Uani 1 1 d . . . H2 H 0.5132 0.0378 0.6912 0.029 Uiso 1 1 calc R . . C1 C 0.4149(4) 0.2872(6) 0.73155(19) 0.0236(8) Uani 1 1 d . . . C19 C 0.3756(4) 0.1959(6) 0.8131(2) 0.0234(8) Uani 1 1 d . . . C7 C 0.6772(4) 0.1685(6) 0.7778(2) 0.0263(9) Uani 1 1 d . . . C5 C 0.3273(4) 0.3725(6) 0.5708(2) 0.0219(8) Uani 1 1 d . . . H5A H 0.2448 0.3515 0.5223 0.026 Uiso 1 1 calc R . . H5B H 0.3448 0.5147 0.5757 0.026 Uiso 1 1 calc R . . C18 C 0.2150(4) -0.0362(6) 0.5915(2) 0.0247(8) Uani 1 1 d . . . H18 H 0.2935 -0.0293 0.5608 0.030 Uiso 1 1 calc R . . C4 C 0.4593(4) 0.2786(6) 0.54757(19) 0.0226(8) Uani 1 1 d . . . C21 C 0.3143(4) -0.0259(7) 0.9161(2) 0.0290(9) Uani 1 1 d . . . H21 H 0.2893 -0.1537 0.9313 0.035 Uiso 1 1 calc R . . C20 C 0.3408(4) 0.0113(6) 0.8328(2) 0.0264(9) Uani 1 1 d . . . H20 H 0.3346 -0.0901 0.7912 0.032 Uiso 1 1 calc R . . C17 C 0.1276(4) -0.2005(6) 0.5837(2) 0.0261(8) Uani 1 1 d . . . H17 H 0.1450 -0.3047 0.5471 0.031 Uiso 1 1 calc R . . C23 C 0.3610(4) 0.3097(7) 0.9576(2) 0.0330(10) Uani 1 1 d . . . H23 H 0.3688 0.4116 0.9991 0.040 Uiso 1 1 calc R . . C16 C 0.0148(4) -0.2121(6) 0.6296(2) 0.0266(9) Uani 1 1 d . . . C25 C 0.4519(4) 0.4930(6) 0.7610(2) 0.0233(8) Uani 1 1 d . . . C13 C 0.1892(4) 0.1186(6) 0.64347(19) 0.0208(8) Uani 1 1 d . . . C3 C 0.5879(4) 0.2609(6) 0.6217(2) 0.0258(9) Uani 1 1 d . . . H3A H 0.6314 0.3914 0.6349 0.031 Uiso 1 1 calc R . . H3B H 0.6627 0.1766 0.6034 0.031 Uiso 1 1 calc R . . C8 C 0.7133(4) -0.0033(7) 0.8226(2) 0.0331(10) Uani 1 1 d . . . H8 H 0.6539 -0.1154 0.8089 0.040 Uiso 1 1 calc R . . C11 C 0.8887(5) 0.3191(8) 0.8651(3) 0.0443(13) Uani 1 1 d . . . H11 H 0.9480 0.4308 0.8801 0.053 Uiso 1 1 calc R . . C9 C 0.8362(5) -0.0132(8) 0.8880(2) 0.0412(12) Uani 1 1 d . . . H9 H 0.8595 -0.1322 0.9182 0.049 Uiso 1 1 calc R . . C12 C 0.7668(4) 0.3298(7) 0.7992(2) 0.0336(10) Uani 1 1 d . . . H12 H 0.7447 0.4484 0.7685 0.040 Uiso 1 1 calc R . . C10 C 0.9229(5) 0.1441(8) 0.9090(2) 0.0436(13) Uani 1 1 d . . . H10 H 1.0067 0.1351 0.9533 0.052 Uiso 1 1 calc R . . O2 O 0.4284(3) 0.5201(4) 0.84468(13) 0.0279(7) Uani 1 1 d . . . O1 O 0.4677(3) 0.2340(5) 0.47420(14) 0.0315(7) Uani 1 1 d . . . O3 O 0.4914(3) 0.6281(4) 0.72255(15) 0.0309(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 0.0383(6) 0.0299(7) 0.0424(5) 0.0067(4) 0.0059(4) -0.0108(5) C6 0.0287(19) 0.019(2) 0.0207(14) -0.0005(13) 0.0110(13) 0.0002(15) C14 0.034(2) 0.023(3) 0.0276(16) -0.0033(16) 0.0138(14) 0.0044(18) C22 0.030(2) 0.048(3) 0.0193(15) 0.0057(16) 0.0060(13) 0.0001(19) C24 0.0257(19) 0.029(3) 0.0239(16) -0.0002(14) 0.0087(13) 0.0033(16) C15 0.028(2) 0.037(3) 0.0266(17) 0.0039(16) 0.0124(14) 0.0069(18) C2 0.0273(19) 0.027(2) 0.0202(14) -0.0017(14) 0.0096(13) 0.0007(16) C1 0.031(2) 0.025(2) 0.0175(14) 0.0006(13) 0.0104(13) -0.0012(16) C19 0.0234(19) 0.030(3) 0.0186(15) 0.0028(14) 0.0077(13) 0.0050(15) C7 0.0296(19) 0.032(3) 0.0209(15) -0.0007(14) 0.0135(14) 0.0035(17) C5 0.026(2) 0.017(2) 0.0243(16) 0.0016(13) 0.0071(13) 0.0022(15) C18 0.028(2) 0.022(3) 0.0264(16) 0.0022(14) 0.0109(14) -0.0015(16) C4 0.036(2) 0.012(2) 0.0223(14) 0.0004(13) 0.0135(14) -0.0020(16) C21 0.029(2) 0.034(3) 0.0270(16) 0.0106(16) 0.0114(14) 0.0053(18) C20 0.029(2) 0.025(3) 0.0267(16) 0.0031(14) 0.0104(14) 0.0100(17) C17 0.032(2) 0.021(2) 0.0268(16) -0.0013(14) 0.0085(14) 0.0024(17) C23 0.033(2) 0.050(3) 0.0183(15) -0.0031(16) 0.0083(13) -0.004(2) C16 0.0212(18) 0.028(3) 0.0303(16) 0.0098(16) 0.0031(13) -0.0013(16) C25 0.030(2) 0.017(2) 0.0241(15) -0.0028(14) 0.0082(13) 0.0002(16) C13 0.0260(18) 0.017(2) 0.0211(14) 0.0042(13) 0.0090(12) 0.0062(14) C3 0.029(2) 0.028(3) 0.0238(15) 0.0001(14) 0.0138(13) 0.0003(16) C8 0.032(2) 0.043(3) 0.0271(17) 0.0033(17) 0.0127(14) 0.0000(19) C11 0.038(2) 0.062(4) 0.034(2) -0.017(2) 0.0095(17) -0.009(2) C9 0.042(3) 0.059(4) 0.0254(17) 0.0080(19) 0.0133(16) 0.010(2) C12 0.037(2) 0.035(3) 0.0314(18) -0.0036(17) 0.0145(16) -0.0032(19) C10 0.037(2) 0.069(4) 0.0253(17) -0.002(2) 0.0071(15) 0.004(2) O2 0.0363(15) 0.030(2) 0.0200(11) -0.0041(10) 0.0112(10) -0.0046(12) O1 0.0443(17) 0.032(2) 0.0209(11) -0.0050(10) 0.0134(10) 0.0008(13) O3 0.0475(16) 0.0184(19) 0.0307(12) -0.0038(11) 0.0172(11) -0.0022(12) _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 C16 1.737(4) . ? C6 C13 1.514(5) . ? C6 C5 1.544(4) . ? C6 C1 1.573(5) . ? C14 C15 1.368(6) . ? C14 C13 1.397(5) . ? C22 C23 1.368(6) . ? C22 C21 1.395(6) . ? C24 C19 1.376(5) . ? C24 O2 1.387(5) . ? C24 C23 1.397(5) . ? C15 C16 1.385(6) . ? C2 C7 1.525(5) . ? C2 C3 1.544(5) . ? C2 C1 1.566(5) . ? C1 C25 1.507(6) . ? C1 C19 1.530(5) . ? C19 C20 1.359(6) . ? C7 C8 1.383(6) . ? C7 C12 1.392(6) . ? C5 C4 1.495(5) . ? C18 C17 1.385(5) . ? C18 C13 1.388(5) . ? C4 O1 1.209(4) . ? C4 C3 1.517(5) . ? C21 C20 1.399(5) . ? C17 C16 1.385(5) . ? C25 O3 1.202(4) . ? C25 O2 1.385(4) . ? C8 C9 1.395(5) . ? C11 C10 1.393(7) . ? C11 C12 1.394(6) . ? C9 C10 1.354(7) . ? 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 C13 C6 C5 113.6(3) . . ? C13 C6 C1 113.1(3) . . ? C5 C6 C1 111.5(3) . . ? C15 C14 C13 121.7(4) . . ? C23 C22 C21 121.5(3) . . ? C19 C24 O2 113.7(3) . . ? C19 C24 C23 122.3(4) . . ? O2 C24 C23 124.0(4) . . ? C14 C15 C16 119.3(3) . . ? C7 C2 C3 110.6(3) . . ? C7 C2 C1 111.7(3) . . ? C3 C2 C1 112.1(3) . . ? C25 C1 C19 101.7(3) . . ? C25 C1 C2 113.4(3) . . ? C19 C1 C2 110.2(3) . . ? C25 C1 C6 106.3(3) . . ? C19 C1 C6 112.8(3) . . ? C2 C1 C6 112.0(3) . . ? C20 C19 C24 120.7(3) . . ? C20 C19 C1 132.7(3) . . ? C24 C19 C1 106.6(3) . . ? C8 C7 C12 118.4(4) . . ? C8 C7 C2 119.9(4) . . ? C12 C7 C2 121.7(4) . . ? C4 C5 C6 116.6(3) . . ? C17 C18 C13 120.8(3) . . ? O1 C4 C5 122.9(3) . . ? O1 C4 C3 122.0(3) . . ? C5 C4 C3 114.9(3) . . ? C22 C21 C20 120.3(4) . . ? C19 C20 C21 118.4(4) . . ? C18 C17 C16 119.6(4) . . ? C22 C23 C24 116.8(4) . . ? C17 C16 C15 120.4(4) . . ? C17 C16 Cl1 119.7(3) . . ? C15 C16 Cl1 119.9(3) . . ? O3 C25 O2 119.4(3) . . ? O3 C25 C1 130.0(3) . . ? O2 C25 C1 110.5(3) . . ? C18 C13 C14 118.1(4) . . ? C18 C13 C6 123.4(3) . . ? C14 C13 C6 118.5(3) . . ? C4 C3 C2 112.8(3) . . ? C7 C8 C9 120.5(5) . . ? C10 C11 C12 119.7(5) . . ? C10 C9 C8 121.1(5) . . ? C7 C12 C11 120.8(4) . . ? C9 C10 C11 119.6(4) . . ? C25 O2 C24 107.4(3) . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.378 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.062 # Attachment 'CCDC781708-TX2.cif' data_tx2ipap41 _database_code_depnum_ccdc_archive 'CCDC 781708' #TrackingRef 'CCDC781708-TX2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H21 Cl O3' _chemical_formula_weight 428.89 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 Tetragonal _symmetry_space_group_name_H-M P4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+1/4' 'y, -x, z+3/4' _cell_length_a 9.3547(11) _cell_length_b 9.3547(11) _cell_length_c 51.084(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4470.4(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9976 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.33 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 22500 _diffrn_reflns_av_R_equivalents 0.0714 _diffrn_reflns_av_sigmaI/netI 0.1070 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -63 _diffrn_reflns_limit_l_max 67 _diffrn_reflns_theta_min 0.80 _diffrn_reflns_theta_max 28.23 _reflns_number_total 10668 _reflns_number_gt 9044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution Sir2007 _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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. The sample was refined as a perfect merohedra ; _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^)+(0.0600P)^2^+25.0000P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration ad _refine_ls_abs_structure_Flack 0.08(17) _refine_ls_number_reflns 10668 _refine_ls_number_parameters 562 _refine_ls_number_restraints 631 _refine_ls_R_factor_all 0.1222 _refine_ls_R_factor_gt 0.1074 _refine_ls_wR_factor_ref 0.2669 _refine_ls_wR_factor_gt 0.2585 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.001 _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 C1A C 0.8108(7) 0.7505(9) 0.24326(17) 0.0168(12) Uani 1 1 d U . . C6A C 0.8113(8) 0.6069(9) 0.22785(19) 0.0193(13) Uani 1 1 d U . . H2A H 0.8771 0.6194 0.2126 0.023 Uiso 1 1 calc R . . C5A C 0.8696(8) 0.4779(10) 0.2444(2) 0.0237(16) Uani 1 1 d U . . H3A H 0.7917 0.4486 0.2566 0.028 Uiso 1 1 calc R . . C4A C 0.9972(8) 0.5172(10) 0.26081(19) 0.0233(16) Uani 1 1 d U . . H4A H 1.0529 0.4422 0.2681 0.028 Uiso 1 1 calc R . . C3A C 1.0387(9) 0.6605(10) 0.2660(2) 0.0233(15) Uani 1 1 d U . . C2A C 0.9670(9) 0.7844(10) 0.2545(2) 0.0235(14) Uani 1 1 d U . . H6A H 0.9543 0.8556 0.2690 0.028 Uiso 1 1 calc R . . C15A C 0.6688(9) 0.5679(10) 0.21718(19) 0.0218(14) Uani 1 1 d U . . C20A C 0.6374(9) 0.5838(9) 0.18998(19) 0.0241(15) Uani 1 1 d U . . H8A H 0.7098 0.6246 0.1793 0.029 Uiso 1 1 calc R . . C19A C 0.5125(9) 0.5458(9) 0.1779(2) 0.0235(15) Uani 1 1 d U . . H9A H 0.4991 0.5554 0.1596 0.028 Uiso 1 1 calc R . . C18A C 0.4045(9) 0.4912(9) 0.1946(2) 0.0237(15) Uani 1 1 d U . . C17A C 0.4178(9) 0.4801(10) 0.22152(19) 0.0248(15) Uani 1 1 d U . . H11A H 0.3412 0.4479 0.2322 0.030 Uiso 1 1 calc R . . C16A C 0.5479(9) 0.5185(10) 0.2320(2) 0.0240(16) Uani 1 1 d U . . H12A H 0.5586 0.5117 0.2504 0.029 Uiso 1 1 calc R . . C14A C 0.9048(11) 0.3527(9) 0.2283(2) 0.031(2) Uani 1 1 d U . . H13A H 0.9786 0.3786 0.2155 0.047 Uiso 1 1 calc R . . H13B H 0.8190 0.3202 0.2191 0.047 Uiso 1 1 calc R . . H13C H 0.9405 0.2758 0.2396 0.047 Uiso 1 1 calc R . . C13A C 1.1582(9) 0.6736(11) 0.2842(2) 0.0274(18) Uani 1 1 d U . . H14A H 1.2127 0.5916 0.2887 0.033 Uiso 1 1 calc R . . C7A C 1.0683(9) 0.8537(10) 0.2341(2) 0.0249(15) Uani 1 1 d U . . C8A C 1.0911(10) 1.0052(10) 0.2330(2) 0.0304(17) Uani 1 1 d U . . H16A H 1.0428 1.0625 0.2456 0.036 Uiso 1 1 calc R . . C9A C 1.1786(10) 1.0752(10) 0.2150(2) 0.0310(18) Uani 1 1 d U . . H17A H 1.1905 1.1761 0.2150 0.037 Uiso 1 1 calc R . . C10A C 1.2453(12) 0.9892(12) 0.1976(2) 0.0376(19) Uani 1 1 d U . . H18A H 1.3051 1.0316 0.1847 0.045 Uiso 1 1 calc R . . C11A C 1.2300(11) 0.8400(12) 0.1977(3) 0.0368(19) Uani 1 1 d U . . H19A H 1.2806 0.7838 0.1853 0.044 Uiso 1 1 calc R . . C12A C 1.1415(10) 0.7739(11) 0.2158(2) 0.0293(17) Uani 1 1 d U . . H20A H 1.1313 0.6729 0.2156 0.035 Uiso 1 1 calc R . . C21A C 0.7538(9) 0.8759(9) 0.22677(18) 0.0189(13) Uani 1 1 d U . . C22A C 0.7974(10) 0.9351(9) 0.2016(2) 0.0260(17) Uani 1 1 d U . . H22A H 0.8798 0.9005 0.1928 0.031 Uiso 1 1 calc R . . C23A C 0.7153(11) 1.0431(10) 0.1911(2) 0.0301(17) Uani 1 1 d U . . H23A H 0.7349 1.0779 0.1740 0.036 Uiso 1 1 calc R . . C24A C 0.6019(11) 1.1015(12) 0.2059(2) 0.0336(19) Uani 1 1 d U . . H24A H 0.5517 1.1810 0.1988 0.040 Uiso 1 1 calc R . . C25A C 0.5596(10) 1.0493(11) 0.2301(2) 0.0336(18) Uani 1 1 d U . . H25A H 0.4812 1.0878 0.2396 0.040 Uiso 1 1 calc R . . C26A C 0.6437(9) 0.9334(10) 0.2394(2) 0.0247(15) Uani 1 1 d U . . C27A C 0.7110(8) 0.7452(9) 0.26660(18) 0.0184(13) Uani 1 1 d U . . O1A O 1.1892(8) 0.7936(10) 0.29383(17) 0.0415(19) Uani 1 1 d U . . O2A O 0.6121(6) 0.8628(7) 0.26306(15) 0.0259(13) Uani 1 1 d U . . O3A O 0.7046(7) 0.6720(8) 0.28454(15) 0.0289(14) Uani 1 1 d U . . Cl1A Cl 0.2406(2) 0.4449(3) 0.18052(5) 0.0324(5) Uani 1 1 d U . . C1B C 0.2417(9) 0.3486(8) 0.07741(18) 0.0196(11) Uani 1 1 d U . . C6B C 0.0924(9) 0.3404(8) 0.09121(18) 0.0184(11) Uani 1 1 d U . . H2B H 0.1011 0.4072 0.1064 0.022 Uiso 1 1 calc R . . C5B C -0.0253(9) 0.4038(9) 0.07480(19) 0.0207(13) Uani 1 1 d U . . H3B H -0.0549 0.3268 0.0624 0.025 Uiso 1 1 calc R . . C4B C 0.0175(9) 0.5283(8) 0.05810(18) 0.0206(13) Uani 1 1 d U . . H4B H -0.0572 0.5828 0.0504 0.025 Uiso 1 1 calc R . . C3B C 0.1436(10) 0.5669(9) 0.05338(19) 0.0228(13) Uani 1 1 d U . . C2B C 0.2825(9) 0.4961(9) 0.06546(18) 0.0200(12) Uani 1 1 d U . . H6B H 0.3537 0.4805 0.0511 0.024 Uiso 1 1 calc R . . C15B C 0.0584(9) 0.1921(8) 0.10402(18) 0.0183(12) Uani 1 1 d U . . C20B C 0.0620(8) 0.1704(8) 0.12917(17) 0.0177(12) Uani 1 1 d U . . H8B H 0.0920 0.2470 0.1401 0.021 Uiso 1 1 calc R . . C19B C 0.0244(9) 0.0411(9) 0.1412(2) 0.0224(13) Uani 1 1 d U . . H9B H 0.0324 0.0275 0.1596 0.027 Uiso 1 1 calc R . . C18B C -0.0249(9) -0.0650(9) 0.1248(2) 0.0236(14) Uani 1 1 d U . . C17B C -0.0334(9) -0.0475(9) 0.0984(2) 0.0222(13) Uani 1 1 d U . . H11B H -0.0672 -0.1230 0.0876 0.027 Uiso 1 1 calc R . . C16B C 0.0092(9) 0.0860(8) 0.08694(19) 0.0204(13) Uani 1 1 d U . . H12B H 0.0041 0.1016 0.0686 0.025 Uiso 1 1 calc R . . C14B C -0.1617(10) 0.4328(11) 0.0931(2) 0.032(2) Uani 1 1 d U . . H13D H -0.1558 0.5295 0.1004 0.048 Uiso 1 1 calc R . . H13E H -0.1634 0.3629 0.1073 0.048 Uiso 1 1 calc R . . H13F H -0.2491 0.4238 0.0826 0.048 Uiso 1 1 calc R . . C13B C 0.1789(12) 0.6867(8) 0.0347(2) 0.0256(16) Uani 1 1 d U . . H14B H 0.0983 0.7407 0.0293 0.031 Uiso 1 1 calc R . . C7B C 0.3468(9) 0.5976(9) 0.08551(19) 0.0205(13) Uani 1 1 d U . . C12B C 0.2641(10) 0.6722(9) 0.1041(2) 0.0258(15) Uani 1 1 d U . . H16B H 0.1632 0.6606 0.1042 0.031 Uiso 1 1 calc R . . C11B C 0.3278(10) 0.7627(9) 0.1223(2) 0.0258(15) Uani 1 1 d U . . H17B H 0.2700 0.8169 0.1340 0.031 Uiso 1 1 calc R . . C10B C 0.4772(10) 0.7739(9) 0.1236(2) 0.0286(15) Uani 1 1 d U . . H18B H 0.5229 0.8261 0.1372 0.034 Uiso 1 1 calc R . . C9B C 0.5589(10) 0.7025(8) 0.1033(2) 0.0270(15) Uani 1 1 d U . . H19B H 0.6592 0.7177 0.1026 0.032 Uiso 1 1 calc R . . C8B C 0.4961(9) 0.6111(9) 0.0844(2) 0.0225(14) Uani 1 1 d U . . H20B H 0.5517 0.5619 0.0717 0.027 Uiso 1 1 calc R . . C21B C 0.3644(9) 0.2838(9) 0.09394(19) 0.0196(12) Uani 1 1 d U . . C22B C 0.4107(9) 0.3141(9) 0.11789(19) 0.0224(14) Uani 1 1 d U . . H22B H 0.3624 0.3829 0.1283 0.027 Uiso 1 1 calc R . . C23B C 0.5330(10) 0.2427(10) 0.1277(2) 0.0268(15) Uani 1 1 d U . . H23B H 0.5716 0.2707 0.1441 0.032 Uiso 1 1 calc R . . C24B C 0.5978(11) 0.1325(10) 0.1138(2) 0.0286(16) Uani 1 1 d U . . H24B H 0.6787 0.0842 0.1208 0.034 Uiso 1 1 calc R . . C25B C 0.5400(11) 0.0931(10) 0.0888(2) 0.0294(15) Uani 1 1 d U . . H25B H 0.5815 0.0180 0.0789 0.035 Uiso 1 1 calc R . . C26B C 0.4260(10) 0.1648(9) 0.0799(2) 0.0249(13) Uani 1 1 d U . . C27B C 0.2448(10) 0.2365(9) 0.0540(2) 0.0249(13) Uani 1 1 d U . . O1B O 0.2907(9) 0.7264(7) 0.02554(16) 0.0356(16) Uani 1 1 d U . . O2B O 0.3499(8) 0.1396(7) 0.05622(15) 0.0289(12) Uani 1 1 d U . . O3B O 0.1687(8) 0.2361(7) 0.03417(15) 0.0340(16) Uani 1 1 d U . . Cl1B Cl -0.0769(2) -0.2340(3) 0.13900(5) 0.0309(5) Uani 1 1 d U . . 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 C1A 0.005(2) 0.021(3) 0.024(3) -0.008(2) 0.000(2) 0.003(2) C6A 0.007(3) 0.023(3) 0.028(3) -0.009(3) -0.001(2) 0.009(2) C5A 0.005(3) 0.028(3) 0.038(4) -0.010(3) 0.000(3) 0.002(3) C4A 0.011(3) 0.026(3) 0.033(4) -0.007(3) -0.007(3) 0.012(3) C3A 0.011(3) 0.030(3) 0.029(4) -0.001(3) -0.007(3) 0.000(3) C2A 0.016(3) 0.025(3) 0.030(4) -0.006(3) 0.000(2) 0.008(3) C15A 0.016(3) 0.023(3) 0.027(3) -0.013(3) 0.001(2) -0.002(3) C20A 0.020(3) 0.020(3) 0.033(4) -0.008(3) -0.004(3) -0.002(3) C19A 0.022(3) 0.016(3) 0.033(4) -0.001(3) -0.004(3) -0.003(3) C18A 0.016(3) 0.017(3) 0.038(4) -0.002(3) -0.002(3) 0.006(3) C17A 0.013(3) 0.032(3) 0.030(3) -0.007(3) 0.005(2) 0.004(3) C16A 0.013(3) 0.030(3) 0.029(3) -0.005(3) 0.000(2) 0.011(2) C14A 0.030(5) 0.011(3) 0.052(6) -0.003(4) 0.014(4) 0.010(3) C13A 0.009(3) 0.037(4) 0.037(5) 0.008(3) -0.007(3) -0.004(3) C7A 0.012(3) 0.024(3) 0.039(4) -0.007(3) -0.009(3) 0.000(3) C8A 0.019(3) 0.022(3) 0.050(5) -0.008(3) -0.010(3) 0.000(3) C9A 0.018(3) 0.019(3) 0.055(5) 0.000(3) -0.015(3) -0.001(3) C10A 0.032(4) 0.043(4) 0.038(4) 0.001(4) -0.005(3) -0.006(4) C11A 0.020(4) 0.039(4) 0.052(5) -0.011(4) -0.003(3) -0.005(3) C12A 0.019(3) 0.027(4) 0.042(4) -0.010(3) -0.010(3) 0.010(3) C21A 0.014(3) 0.018(3) 0.025(3) -0.008(2) -0.003(3) 0.002(2) C22A 0.028(4) 0.021(3) 0.029(4) -0.008(3) -0.004(3) 0.017(3) C23A 0.031(4) 0.024(4) 0.036(4) -0.001(3) -0.009(3) 0.016(3) C24A 0.026(4) 0.035(4) 0.039(4) -0.011(3) -0.011(3) 0.025(3) C25A 0.025(4) 0.032(4) 0.044(4) -0.009(3) -0.007(3) 0.014(3) C26A 0.009(3) 0.030(3) 0.035(4) -0.007(3) -0.005(3) 0.003(3) C27A 0.007(3) 0.023(3) 0.025(3) -0.015(3) 0.002(3) 0.004(3) O1A 0.031(4) 0.061(5) 0.033(4) -0.014(4) -0.007(3) -0.012(4) O2A 0.014(2) 0.033(3) 0.031(3) -0.011(2) 0.007(2) 0.009(2) O3A 0.015(3) 0.047(4) 0.025(3) -0.011(3) 0.000(3) 0.008(3) Cl1A 0.0184(10) 0.0327(12) 0.0460(15) -0.0111(10) -0.0058(10) -0.0027(9) C1B 0.019(2) 0.016(2) 0.024(3) -0.0042(19) -0.006(2) 0.0023(19) C6B 0.018(2) 0.011(2) 0.026(3) -0.004(2) -0.008(2) 0.002(2) C5B 0.019(3) 0.014(3) 0.029(3) -0.003(2) -0.015(2) 0.003(2) C4B 0.024(2) 0.012(2) 0.026(3) -0.006(2) -0.014(2) -0.003(2) C3B 0.032(3) 0.010(2) 0.026(3) 0.000(2) -0.012(2) 0.003(2) C2B 0.022(2) 0.013(2) 0.025(3) 0.000(2) -0.005(2) 0.003(2) C15B 0.018(3) 0.009(2) 0.028(3) -0.007(2) -0.009(2) 0.003(2) C20B 0.015(3) 0.011(2) 0.027(3) -0.006(2) -0.008(3) 0.007(2) C19B 0.017(3) 0.022(3) 0.029(3) -0.004(2) -0.005(3) -0.002(2) C18B 0.019(3) 0.013(3) 0.039(3) -0.003(2) -0.003(3) -0.005(2) C17B 0.020(3) 0.012(2) 0.035(3) -0.008(2) -0.003(2) -0.002(2) C16B 0.023(3) 0.009(2) 0.030(3) -0.006(2) -0.008(2) -0.002(2) C14B 0.021(4) 0.030(4) 0.044(5) -0.003(4) -0.007(3) 0.016(3) C13B 0.041(4) 0.007(3) 0.029(4) 0.003(3) -0.012(3) -0.003(3) C7B 0.019(3) 0.012(2) 0.031(3) -0.002(2) -0.008(2) 0.001(2) C12B 0.018(3) 0.023(3) 0.036(4) -0.010(3) -0.010(3) 0.003(3) C11B 0.022(3) 0.017(3) 0.039(4) -0.012(3) -0.013(3) -0.002(3) C10B 0.027(3) 0.013(3) 0.045(4) -0.003(3) -0.018(3) -0.009(3) C9B 0.025(3) 0.009(3) 0.047(4) 0.004(3) -0.013(3) -0.004(2) C8B 0.016(3) 0.015(3) 0.037(4) 0.005(2) -0.011(3) 0.008(2) C21B 0.015(2) 0.014(2) 0.030(3) -0.001(2) -0.007(2) 0.005(2) C22B 0.019(3) 0.019(3) 0.029(3) 0.002(3) -0.010(3) 0.006(2) C23B 0.025(3) 0.025(3) 0.030(3) 0.005(2) -0.015(2) 0.007(2) C24B 0.028(3) 0.024(3) 0.034(3) 0.004(3) -0.005(2) 0.008(2) C25B 0.029(3) 0.023(3) 0.036(3) 0.000(3) -0.004(3) 0.013(3) C26B 0.024(3) 0.018(3) 0.033(3) 0.000(2) -0.006(2) 0.008(2) C27B 0.029(3) 0.018(3) 0.028(3) -0.002(2) -0.007(2) 0.005(3) O1B 0.051(4) 0.016(3) 0.040(4) -0.002(3) -0.007(3) -0.003(3) O2B 0.036(3) 0.020(2) 0.031(3) -0.001(2) -0.005(2) 0.008(2) O3B 0.045(4) 0.024(3) 0.034(4) -0.011(3) -0.018(3) 0.002(3) Cl1B 0.0272(11) 0.0265(11) 0.0389(14) -0.0029(10) -0.0015(10) -0.0003(9) _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 C1A C27A 1.515(11) . ? C1A C21A 1.540(12) . ? C1A C6A 1.557(11) . ? C1A C2A 1.603(11) . ? C6A C15A 1.485(11) . ? C6A C5A 1.570(13) . ? C5A C14A 1.468(12) . ? C5A C4A 1.505(12) . ? C4A C3A 1.421(13) . ? C3A C13A 1.459(12) . ? C3A C2A 1.461(12) . ? C2A C7A 1.550(14) . ? C15A C20A 1.428(14) . ? C15A C16A 1.437(12) . ? C20A C19A 1.368(12) . ? C19A C18A 1.418(13) . ? C18A C17A 1.384(14) . ? C18A Cl1A 1.748(9) . ? C17A C16A 1.377(12) . ? C13A O1A 1.260(13) . ? C7A C12A 1.380(14) . ? C7A C8A 1.435(13) . ? C8A C9A 1.395(16) . ? C9A C10A 1.352(16) . ? C10A C11A 1.403(15) . ? C11A C12A 1.388(16) . ? C21A C26A 1.330(12) . ? C21A C22A 1.456(14) . ? C22A C23A 1.379(12) . ? C23A C24A 1.413(14) . ? C24A C25A 1.386(17) . ? C25A C26A 1.423(13) . ? C26A O2A 1.406(13) . ? C27A O3A 1.146(12) . ? C27A O2A 1.448(10) . ? C1B C21B 1.548(11) . ? C1B C2B 1.556(12) . ? C1B C6B 1.567(12) . ? C1B C27B 1.593(12) . ? C6B C5B 1.506(11) . ? C6B C15B 1.566(11) . ? C5B C4B 1.498(12) . ? C5B C14B 1.603(14) . ? C4B C3B 1.258(13) . ? C3B C13B 1.507(12) . ? C3B C2B 1.584(12) . ? C2B C7B 1.520(12) . ? C15B C20B 1.301(13) . ? C15B C16B 1.400(11) . ? C20B C19B 1.401(12) . ? C19B C18B 1.378(12) . ? C18B C17B 1.362(14) . ? C18B Cl1B 1.805(9) . ? C17B C16B 1.436(12) . ? C13B O1B 1.205(14) . ? C7B C8B 1.404(12) . ? C7B C12B 1.409(13) . ? C12B C11B 1.394(12) . ? C11B C10B 1.402(12) . ? C10B C9B 1.452(15) . ? C9B C8B 1.417(13) . ? C21B C22B 1.328(13) . ? C21B C26B 1.444(12) . ? C22B C23B 1.416(11) . ? C23B C24B 1.390(14) . ? C24B C25B 1.435(15) . ? C25B C26B 1.340(12) . ? C26B O2B 1.424(13) . ? C27B O3B 1.236(12) . ? C27B O2B 1.342(11) . ? 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 C27A C1A C21A 104.0(6) . . ? C27A C1A C6A 111.8(7) . . ? C21A C1A C6A 112.5(7) . . ? C27A C1A C2A 106.6(7) . . ? C21A C1A C2A 111.2(7) . . ? C6A C1A C2A 110.5(6) . . ? C15A C6A C1A 113.3(6) . . ? C15A C6A C5A 108.7(7) . . ? C1A C6A C5A 113.1(7) . . ? C14A C5A C4A 109.2(7) . . ? C14A C5A C6A 113.0(9) . . ? C4A C5A C6A 112.9(7) . . ? C3A C4A C5A 123.4(8) . . ? C4A C3A C13A 114.0(8) . . ? C4A C3A C2A 123.3(8) . . ? C13A C3A C2A 122.7(9) . . ? C3A C2A C7A 108.7(7) . . ? C3A C2A C1A 113.9(8) . . ? C7A C2A C1A 113.5(8) . . ? C20A C15A C16A 112.5(8) . . ? C20A C15A C6A 121.1(8) . . ? C16A C15A C6A 126.3(9) . . ? C19A C20A C15A 126.0(9) . . ? C20A C19A C18A 115.5(9) . . ? C17A C18A C19A 124.1(8) . . ? C17A C18A Cl1A 118.0(7) . . ? C19A C18A Cl1A 117.8(8) . . ? C16A C17A C18A 116.5(9) . . ? C17A C16A C15A 125.1(9) . . ? O1A C13A C3A 120.1(9) . . ? C12A C7A C8A 115.7(10) . . ? C12A C7A C2A 122.2(8) . . ? C8A C7A C2A 122.1(9) . . ? C9A C8A C7A 125.3(10) . . ? C10A C9A C8A 115.2(9) . . ? C9A C10A C11A 122.9(11) . . ? C12A C11A C10A 120.4(11) . . ? C7A C12A C11A 120.6(10) . . ? C26A C21A C22A 119.5(8) . . ? C26A C21A C1A 108.0(8) . . ? C22A C21A C1A 132.4(7) . . ? C23A C22A C21A 117.9(9) . . ? C22A C23A C24A 119.5(10) . . ? C25A C24A C23A 123.7(9) . . ? C24A C25A C26A 114.3(9) . . ? C21A C26A O2A 113.0(8) . . ? C21A C26A C25A 124.9(10) . . ? O2A C26A C25A 122.1(8) . . ? O3A C27A O2A 121.4(7) . . ? O3A C27A C1A 132.9(8) . . ? O2A C27A C1A 105.7(8) . . ? C26A O2A C27A 109.2(7) . . ? C21B C1B C2B 112.3(7) . . ? C21B C1B C6B 113.3(7) . . ? C2B C1B C6B 116.0(7) . . ? C21B C1B C27B 98.0(6) . . ? C2B C1B C27B 106.5(7) . . ? C6B C1B C27B 108.8(7) . . ? C5B C6B C15B 115.7(7) . . ? C5B C6B C1B 112.5(8) . . ? C15B C6B C1B 114.4(6) . . ? C4B C5B C6B 115.3(7) . . ? C4B C5B C14B 114.4(7) . . ? C6B C5B C14B 108.9(8) . . ? C3B C4B C5B 125.7(8) . . ? C4B C3B C13B 122.7(8) . . ? C4B C3B C2B 125.1(8) . . ? C13B C3B C2B 112.2(8) . . ? C7B C2B C1B 112.7(7) . . ? C7B C2B C3B 109.0(6) . . ? C1B C2B C3B 108.8(7) . . ? C20B C15B C16B 120.9(8) . . ? C20B C15B C6B 123.1(7) . . ? C16B C15B C6B 115.7(8) . . ? C15B C20B C19B 124.1(8) . . ? C18B C19B C20B 116.1(9) . . ? C17B C18B C19B 122.3(8) . . ? C17B C18B Cl1B 119.2(7) . . ? C19B C18B Cl1B 118.6(8) . . ? C18B C17B C16B 119.6(8) . . ? C15B C16B C17B 117.0(9) . . ? O1B C13B C3B 131.7(9) . . ? C8B C7B C12B 122.0(8) . . ? C8B C7B C2B 114.9(8) . . ? C12B C7B C2B 123.1(8) . . ? C11B C12B C7B 121.1(9) . . ? C12B C11B C10B 120.1(9) . . ? C11B C10B C9B 117.3(8) . . ? C8B C9B C10B 123.1(8) . . ? C7B C8B C9B 116.0(9) . . ? C22B C21B C26B 119.4(8) . . ? C22B C21B C1B 131.3(8) . . ? C26B C21B C1B 109.1(8) . . ? C21B C22B C23B 119.3(9) . . ? C24B C23B C22B 121.5(9) . . ? C23B C24B C25B 118.7(8) . . ? C26B C25B C24B 118.3(9) . . ? C25B C26B O2B 127.1(9) . . ? C25B C26B C21B 122.3(9) . . ? O2B C26B C21B 110.5(7) . . ? O3B C27B O2B 119.3(9) . . ? O3B C27B C1B 127.4(8) . . ? O2B C27B C1B 113.1(8) . . ? C27B O2B C26B 109.1(7) . . ? 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 C27A C1A C6A C15A 60.6(10) . . . . ? C21A C1A C6A C15A -56.0(10) . . . . ? C2A C1A C6A C15A 179.1(8) . . . . ? C27A C1A C6A C5A -63.6(8) . . . . ? C21A C1A C6A C5A 179.8(6) . . . . ? C2A C1A C6A C5A 54.9(9) . . . . ? C15A C6A C5A C14A 68.1(9) . . . . ? C1A C6A C5A C14A -165.2(7) . . . . ? C15A C6A C5A C4A -167.4(7) . . . . ? C1A C6A C5A C4A -40.7(10) . . . . ? C14A C5A C4A C3A 141.3(10) . . . . ? C6A C5A C4A C3A 14.7(13) . . . . ? C5A C4A C3A C13A 175.1(9) . . . . ? C5A C4A C3A C2A -4.0(15) . . . . ? C4A C3A C2A C7A -109.2(10) . . . . ? C13A C3A C2A C7A 71.8(12) . . . . ? C4A C3A C2A C1A 18.4(13) . . . . ? C13A C3A C2A C1A -160.6(9) . . . . ? C27A C1A C2A C3A 78.6(9) . . . . ? C21A C1A C2A C3A -168.7(8) . . . . ? C6A C1A C2A C3A -43.1(11) . . . . ? C27A C1A C2A C7A -156.3(7) . . . . ? C21A C1A C2A C7A -43.6(9) . . . . ? C6A C1A C2A C7A 82.0(9) . . . . ? C1A C6A C15A C20A 104.5(10) . . . . ? C5A C6A C15A C20A -128.9(9) . . . . ? C1A C6A C15A C16A -72.3(12) . . . . ? C5A C6A C15A C16A 54.2(11) . . . . ? C16A C15A C20A C19A -5.7(13) . . . . ? C6A C15A C20A C19A 177.1(8) . . . . ? C15A C20A C19A C18A 2.7(13) . . . . ? C20A C19A C18A C17A 2.4(12) . . . . ? C20A C19A C18A Cl1A 178.4(7) . . . . ? C19A C18A C17A C16A -3.5(13) . . . . ? Cl1A C18A C17A C16A -179.5(7) . . . . ? C18A C17A C16A C15A -0.1(13) . . . . ? C20A C15A C16A C17A 4.3(13) . . . . ? C6A C15A C16A C17A -178.6(8) . . . . ? C4A C3A C13A O1A -167.8(10) . . . . ? C2A C3A C13A O1A 11.3(15) . . . . ? C3A C2A C7A C12A 46.0(12) . . . . ? C1A C2A C7A C12A -81.8(10) . . . . ? C3A C2A C7A C8A -134.4(9) . . . . ? C1A C2A C7A C8A 97.8(10) . . . . ? C12A C7A C8A C9A 0.7(14) . . . . ? C2A C7A C8A C9A -178.9(9) . . . . ? C7A C8A C9A C10A -0.1(15) . . . . ? C8A C9A C10A C11A -0.9(16) . . . . ? C9A C10A C11A C12A 1.3(18) . . . . ? C8A C7A C12A C11A -0.4(14) . . . . ? C2A C7A C12A C11A 179.3(9) . . . . ? C10A C11A C12A C7A -0.5(16) . . . . ? C27A C1A C21A C26A 1.8(8) . . . . ? C6A C1A C21A C26A 123.0(8) . . . . ? C2A C1A C21A C26A -112.5(8) . . . . ? C27A C1A C21A C22A -177.7(9) . . . . ? C6A C1A C21A C22A -56.5(12) . . . . ? C2A C1A C21A C22A 68.0(12) . . . . ? C26A C21A C22A C23A -4.6(13) . . . . ? C1A C21A C22A C23A 174.9(9) . . . . ? C21A C22A C23A C24A 6.1(14) . . . . ? C22A C23A C24A C25A -5.1(16) . . . . ? C23A C24A C25A C26A 2.0(15) . . . . ? C22A C21A C26A O2A 178.5(8) . . . . ? C1A C21A C26A O2A -1.1(10) . . . . ? C22A C21A C26A C25A 1.6(13) . . . . ? C1A C21A C26A C25A -178.0(9) . . . . ? C24A C25A C26A C21A -0.3(14) . . . . ? C24A C25A C26A O2A -176.9(9) . . . . ? C21A C1A C27A O3A 179.2(9) . . . . ? C6A C1A C27A O3A 57.6(12) . . . . ? C2A C1A C27A O3A -63.3(12) . . . . ? C21A C1A C27A O2A -1.9(8) . . . . ? C6A C1A C27A O2A -123.5(7) . . . . ? C2A C1A C27A O2A 115.7(7) . . . . ? C21A C26A O2A C27A -0.2(10) . . . . ? C25A C26A O2A C27A 176.8(8) . . . . ? O3A C27A O2A C26A -179.5(8) . . . . ? C1A C27A O2A C26A 1.4(9) . . . . ? C21B C1B C6B C5B -180.0(6) . . . . ? C2B C1B C6B C5B 48.0(10) . . . . ? C27B C1B C6B C5B -72.1(8) . . . . ? C21B C1B C6B C15B -45.4(9) . . . . ? C2B C1B C6B C15B -177.5(7) . . . . ? C27B C1B C6B C15B 62.5(9) . . . . ? C15B C6B C5B C4B -167.5(7) . . . . ? C1B C6B C5B C4B -33.5(10) . . . . ? C15B C6B C5B C14B 62.4(9) . . . . ? C1B C6B C5B C14B -163.7(7) . . . . ? C6B C5B C4B C3B 12.8(13) . . . . ? C14B C5B C4B C3B 140.3(10) . . . . ? C5B C4B C3B C13B 175.3(8) . . . . ? C5B C4B C3B C2B -3.5(15) . . . . ? C21B C1B C2B C7B -48.8(10) . . . . ? C6B C1B C2B C7B 83.8(9) . . . . ? C27B C1B C2B C7B -154.9(7) . . . . ? C21B C1B C2B C3B -169.8(7) . . . . ? C6B C1B C2B C3B -37.3(10) . . . . ? C27B C1B C2B C3B 84.0(8) . . . . ? C4B C3B C2B C7B -107.6(10) . . . . ? C13B C3B C2B C7B 73.5(10) . . . . ? C4B C3B C2B C1B 15.7(12) . . . . ? C13B C3B C2B C1B -163.2(8) . . . . ? C5B C6B C15B C20B -121.4(9) . . . . ? C1B C6B C15B C20B 105.5(9) . . . . ? C5B C6B C15B C16B 52.3(11) . . . . ? C1B C6B C15B C16B -80.8(9) . . . . ? C16B C15B C20B C19B 2.9(13) . . . . ? C6B C15B C20B C19B 176.3(7) . . . . ? C15B C20B C19B C18B -2.9(12) . . . . ? C20B C19B C18B C17B 1.6(13) . . . . ? C20B C19B C18B Cl1B -179.4(6) . . . . ? C19B C18B C17B C16B -0.4(13) . . . . ? Cl1B C18B C17B C16B -179.3(7) . . . . ? C20B C15B C16B C17B -1.4(12) . . . . ? C6B C15B C16B C17B -175.3(7) . . . . ? C18B C17B C16B C15B 0.2(12) . . . . ? C4B C3B C13B O1B -169.8(11) . . . . ? C2B C3B C13B O1B 9.1(15) . . . . ? C1B C2B C7B C8B 102.2(9) . . . . ? C3B C2B C7B C8B -136.8(8) . . . . ? C1B C2B C7B C12B -77.2(10) . . . . ? C3B C2B C7B C12B 43.7(12) . . . . ? C8B C7B C12B C11B -0.4(15) . . . . ? C2B C7B C12B C11B 179.1(9) . . . . ? C7B C12B C11B C10B -4.1(16) . . . . ? C12B C11B C10B C9B 7.5(15) . . . . ? C11B C10B C9B C8B -7.0(14) . . . . ? C12B C7B C8B C9B 1.0(13) . . . . ? C2B C7B C8B C9B -178.5(8) . . . . ? C10B C9B C8B C7B 2.8(13) . . . . ? C2B C1B C21B C22B 76.8(13) . . . . ? C6B C1B C21B C22B -57.1(13) . . . . ? C27B C1B C21B C22B -171.6(10) . . . . ? C2B C1B C21B C26B -107.8(8) . . . . ? C6B C1B C21B C26B 118.3(8) . . . . ? C27B C1B C21B C26B 3.8(9) . . . . ? C26B C21B C22B C23B 9.0(14) . . . . ? C1B C21B C22B C23B -176.0(9) . . . . ? C21B C22B C23B C24B -6.0(15) . . . . ? C22B C23B C24B C25B 1.2(15) . . . . ? C23B C24B C25B C26B 0.2(15) . . . . ? C24B C25B C26B O2B -177.7(9) . . . . ? C24B C25B C26B C21B 3.1(15) . . . . ? C22B C21B C26B C25B -7.9(15) . . . . ? C1B C21B C26B C25B 176.1(10) . . . . ? C22B C21B C26B O2B 172.7(9) . . . . ? C1B C21B C26B O2B -3.3(10) . . . . ? C21B C1B C27B O3B -178.9(10) . . . . ? C2B C1B C27B O3B -62.7(12) . . . . ? C6B C1B C27B O3B 63.1(13) . . . . ? C21B C1B C27B O2B -3.4(10) . . . . ? C2B C1B C27B O2B 112.7(9) . . . . ? C6B C1B C27B O2B -121.5(8) . . . . ? O3B C27B O2B C26B 177.6(9) . . . . ? C1B C27B O2B C26B 1.7(11) . . . . ? C25B C26B O2B C27B -178.4(10) . . . . ? C21B C26B O2B C27B 1.0(11) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.23 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.564 _refine_diff_density_min -0.795 _refine_diff_density_rms 0.123