data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Michael McGlinchey' _publ_contact_author_email MICHAEL.MCGLINCHEY@UCD.IE _publ_section_title ; Syntheses, X-ray crystal structures and reactivity of fluorenylidene- and dibenzosuberenylidene-allenes: convenient precursors to dispirotetracenes, di-indenotetracenes and 2-phenyl-11bH-dibenz[c,d,h]azulene ; loop_ _publ_author_name 'Michael McGlinchey' 'Emilie V. Banide' 'Natasha Fortune' 'Sandra Milosevic' 'Helge Muller-Bunz' ; C.O'Connor ; 'Yannick Ortin' # Attachment 'mjm59pub.cif' data_mjm59(12) _database_code_depnum_ccdc_archive 'CCDC 769734' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2 C44 H26 F6, C6 H14' _chemical_formula_sum 'C94 H66 F12' _chemical_formula_weight 1423.47 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0486(15) _cell_length_b 11.2654(19) _cell_length_c 18.715(3) _cell_angle_alpha 91.991(3) _cell_angle_beta 101.326(3) _cell_angle_gamma 109.783(3) _cell_volume 1749.6(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5592 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 28.20 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 1.20 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 738 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7106 _exptl_absorpt_correction_T_max 0.9613 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.114 before and 0.027 after correction. The Ratio of minimum to maximum transmission is 0.739251. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; Hydrogen atoms of the solvent were added at calculated positions and refined using a riding model. All other hydrogen atoms were located in the difference fourier map and allowed to refine freely. C-H bond distances range from 0.91(2) \%A to 1.00(2) \%A. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27144 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6863 _reflns_number_gt 5974 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0589P)^2^+1.1337P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6863 _refine_ls_number_parameters 583 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 C1 C 0.22375(17) 0.71602(14) 0.73674(8) 0.0163(3) Uani 1 1 d . . . C5 C 0.21173(18) 0.80137(14) 0.68876(8) 0.0170(3) Uani 1 1 d . . . C6 C 0.29348(18) 0.94105(14) 0.70530(8) 0.0178(3) Uani 1 1 d . . . C7 C 0.38466(19) 1.01737(15) 0.76992(9) 0.0201(3) Uani 1 1 d . . . H7 H 0.407(2) 0.9805(17) 0.8137(10) 0.021(4) Uiso 1 1 d . . . C8 C 0.44516(19) 1.14859(15) 0.76924(9) 0.0220(3) Uani 1 1 d . . . H8 H 0.506(2) 1.2020(18) 0.8138(11) 0.023(5) Uiso 1 1 d . . . C9 C 0.41529(19) 1.20424(15) 0.70554(9) 0.0214(3) Uani 1 1 d . . . H9 H 0.459(2) 1.2960(18) 0.7063(10) 0.021(4) Uiso 1 1 d . . . C10 C 0.32471(19) 1.12905(15) 0.64050(9) 0.0211(3) Uani 1 1 d . . . H10 H 0.302(2) 1.1673(17) 0.5962(10) 0.023(5) Uiso 1 1 d . . . C11 C 0.26443(18) 0.99830(15) 0.64097(8) 0.0186(3) Uani 1 1 d . . . C12 C 0.16566(18) 0.89809(15) 0.58156(8) 0.0195(3) Uani 1 1 d . . . C13 C 0.1120(2) 0.90710(16) 0.50787(9) 0.0234(3) Uani 1 1 d . . . H13 H 0.138(2) 0.9901(18) 0.4888(10) 0.025(5) Uiso 1 1 d . . . C14 C 0.0194(2) 0.79660(17) 0.46176(9) 0.0256(4) Uani 1 1 d . . . H14 H -0.022(2) 0.8026(19) 0.4110(12) 0.031(5) Uiso 1 1 d . . . C15 C -0.0167(2) 0.67955(17) 0.48908(9) 0.0263(4) Uani 1 1 d . . . H15 H -0.081(2) 0.6017(19) 0.4562(11) 0.030(5) Uiso 1 1 d . . . C16 C 0.0391(2) 0.66996(16) 0.56266(9) 0.0230(3) Uani 1 1 d . . . H16 H 0.014(2) 0.5892(19) 0.5803(10) 0.023(5) Uiso 1 1 d . . . C17 C 0.13040(18) 0.78004(15) 0.60984(8) 0.0182(3) Uani 1 1 d . . . C2 C 0.16696(18) 0.57754(14) 0.73669(8) 0.0160(3) Uani 1 1 d . . . C18 C 0.03097(18) 0.48304(14) 0.70245(8) 0.0169(3) Uani 1 1 d . . . H18 H -0.048(2) 0.5078(16) 0.6701(9) 0.014(4) Uiso 1 1 d . . . C19 C -0.01848(18) 0.34713(14) 0.70978(8) 0.0171(3) Uani 1 1 d . . . C20 C 0.08928(18) 0.28645(15) 0.73746(8) 0.0181(3) Uani 1 1 d . . . H20 H 0.203(2) 0.3367(17) 0.7505(10) 0.021(4) Uiso 1 1 d . . . C21 C 0.03530(19) 0.15709(15) 0.74121(8) 0.0194(3) Uani 1 1 d . . . H21 H 0.111(2) 0.1175(17) 0.7606(10) 0.020(4) Uiso 1 1 d . . . C22 C -0.12751(19) 0.08537(14) 0.71665(8) 0.0195(3) Uani 1 1 d . . . C43 C -0.1839(2) -0.05529(16) 0.71921(10) 0.0256(4) Uani 1 1 d . . . F1 F -0.11412(16) -0.08776(10) 0.78092(7) 0.0485(3) Uani 1 1 d . . . F2 F -0.15223(18) -0.11560(11) 0.66508(7) 0.0533(4) Uani 1 1 d . . . F3 F -0.34186(13) -0.10599(10) 0.71400(9) 0.0517(4) Uani 1 1 d . . . C23 C -0.23646(19) 0.14293(15) 0.68829(9) 0.0208(3) Uani 1 1 d . . . H23 H -0.346(2) 0.0949(18) 0.6709(10) 0.024(5) Uiso 1 1 d . . . C24 C -0.18189(18) 0.27263(15) 0.68497(8) 0.0200(3) Uani 1 1 d . . . H24 H -0.260(2) 0.3142(16) 0.6647(9) 0.017(4) Uiso 1 1 d . . . C3 C 0.30244(17) 0.58536(14) 0.80285(8) 0.0161(3) Uani 1 1 d . . . C25 C 0.26792(18) 0.50961(14) 0.86655(8) 0.0172(3) Uani 1 1 d . . . C26 C 0.14241(19) 0.48890(15) 0.90244(9) 0.0205(3) Uani 1 1 d . . . H26 H 0.061(2) 0.5244(17) 0.8874(10) 0.019(4) Uiso 1 1 d . . . C27 C 0.1368(2) 0.41398(16) 0.95999(9) 0.0245(4) Uani 1 1 d . . . H27 H 0.049(2) 0.3994(19) 0.9837(11) 0.031(5) Uiso 1 1 d . . . C28 C 0.2539(2) 0.36047(16) 0.98124(9) 0.0255(4) Uani 1 1 d . . . H28 H 0.249(2) 0.3106(19) 1.0184(11) 0.028(5) Uiso 1 1 d . . . C29 C 0.3798(2) 0.38094(15) 0.94579(9) 0.0231(3) Uani 1 1 d . . . H29 H 0.463(2) 0.3449(19) 0.9601(11) 0.028(5) Uiso 1 1 d . . . C30 C 0.38662(18) 0.45646(14) 0.88867(8) 0.0183(3) Uani 1 1 d . . . C31 C 0.50230(18) 0.49185(14) 0.84116(8) 0.0183(3) Uani 1 1 d . . . C32 C 0.64432(19) 0.46871(15) 0.84262(9) 0.0216(3) Uani 1 1 d . . . H32 H 0.682(2) 0.4205(17) 0.8795(10) 0.017(4) Uiso 1 1 d . . . C33 C 0.72971(19) 0.51301(16) 0.78900(9) 0.0247(4) Uani 1 1 d . . . H33 H 0.826(2) 0.4972(18) 0.7879(11) 0.029(5) Uiso 1 1 d . . . C34 C 0.6742(2) 0.57859(15) 0.73473(9) 0.0239(3) Uani 1 1 d . . . H34 H 0.734(2) 0.6103(18) 0.6975(10) 0.024(5) Uiso 1 1 d . . . C35 C 0.53331(19) 0.60364(15) 0.73367(9) 0.0203(3) Uani 1 1 d . . . H35 H 0.497(2) 0.6507(18) 0.6969(10) 0.022(4) Uiso 1 1 d . . . C36 C 0.44913(17) 0.56124(13) 0.78765(8) 0.0170(3) Uani 1 1 d . . . C4 C 0.33544(18) 0.73546(14) 0.81217(8) 0.0162(3) Uani 1 1 d . . . H4 H 0.447(2) 0.7844(16) 0.8127(9) 0.014(4) Uiso 1 1 d . . . C37 C 0.28647(18) 0.78136(13) 0.87716(8) 0.0174(3) Uani 1 1 d . . . C38 C 0.13909(19) 0.79706(15) 0.87178(9) 0.0209(3) Uani 1 1 d . . . H38 H 0.067(2) 0.7833(17) 0.8254(11) 0.023(5) Uiso 1 1 d . . . C39 C 0.0989(2) 0.84022(16) 0.93315(9) 0.0238(3) Uani 1 1 d . . . H39 H -0.001(2) 0.8518(18) 0.9271(10) 0.025(5) Uiso 1 1 d . . . C40 C 0.2063(2) 0.86690(15) 1.00071(9) 0.0237(3) Uani 1 1 d . . . C44 C 0.1695(2) 0.91828(19) 1.06734(10) 0.0334(4) Uani 1 1 d . . . F4 F 0.01647(12) 0.90715(10) 1.05941(6) 0.0345(3) Uani 1 1 d . . . F5 F 0.25387(17) 1.04310(14) 1.08490(9) 0.0753(6) Uani 1 1 d . . . F6 F 0.20382(19) 0.86036(18) 1.12556(6) 0.0696(5) Uani 1 1 d . . . C41 C 0.3542(2) 0.85090(16) 1.00696(9) 0.0237(3) Uani 1 1 d . . . H41 H 0.429(2) 0.8695(17) 1.0542(11) 0.024(5) Uiso 1 1 d . . . C42 C 0.39332(19) 0.80831(15) 0.94568(9) 0.0201(3) Uani 1 1 d . . . H42 H 0.494(2) 0.7998(16) 0.9489(9) 0.018(4) Uiso 1 1 d . . . C45 C 0.5410(3) 0.2294(3) 0.48492(14) 0.0551(6) Uani 1 1 d . . . H45A H 0.4248 0.1820 0.4731 0.083 Uiso 1 1 calc R . . H45B H 0.5956 0.1842 0.5180 0.083 Uiso 1 1 calc R . . H45C H 0.5813 0.2373 0.4398 0.083 Uiso 1 1 calc R . . C46 C 0.5737(3) 0.3598(3) 0.52172(17) 0.0686(8) Uani 1 1 d . . . H46A H 0.5472 0.3502 0.5706 0.082 Uiso 1 1 calc R . . H46B H 0.6906 0.4083 0.5297 0.082 Uiso 1 1 calc R . . C47 C 0.4863(3) 0.4358(3) 0.48261(14) 0.0565(6) Uani 1 1 d . . . H47A H 0.3697 0.3862 0.4739 0.068 Uiso 1 1 calc R . . H47B H 0.5139 0.4456 0.4340 0.068 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 C1 0.0170(7) 0.0166(7) 0.0154(7) -0.0021(5) 0.0039(6) 0.0064(6) C5 0.0182(7) 0.0166(7) 0.0164(7) -0.0015(6) 0.0037(6) 0.0070(6) C6 0.0178(7) 0.0175(7) 0.0200(7) 0.0019(6) 0.0057(6) 0.0079(6) C7 0.0221(8) 0.0196(8) 0.0184(8) 0.0020(6) 0.0026(6) 0.0082(6) C8 0.0208(8) 0.0190(8) 0.0235(8) -0.0024(6) 0.0023(6) 0.0054(6) C9 0.0194(8) 0.0163(8) 0.0293(9) 0.0033(6) 0.0081(6) 0.0055(6) C10 0.0220(8) 0.0213(8) 0.0235(8) 0.0063(6) 0.0082(6) 0.0099(6) C11 0.0192(7) 0.0203(8) 0.0189(7) 0.0017(6) 0.0060(6) 0.0095(6) C12 0.0211(8) 0.0213(8) 0.0192(8) 0.0007(6) 0.0057(6) 0.0107(6) C13 0.0310(9) 0.0252(9) 0.0189(8) 0.0044(6) 0.0068(7) 0.0152(7) C14 0.0339(9) 0.0327(9) 0.0145(8) 0.0010(7) 0.0024(7) 0.0189(8) C15 0.0328(9) 0.0266(9) 0.0184(8) -0.0049(7) 0.0002(7) 0.0128(7) C16 0.0291(9) 0.0202(8) 0.0194(8) 0.0003(6) 0.0030(7) 0.0098(7) C17 0.0202(7) 0.0209(8) 0.0156(7) 0.0005(6) 0.0038(6) 0.0102(6) C2 0.0191(7) 0.0181(7) 0.0135(7) 0.0007(5) 0.0047(6) 0.0093(6) C18 0.0172(7) 0.0200(8) 0.0145(7) 0.0005(6) 0.0029(6) 0.0082(6) C19 0.0185(7) 0.0181(7) 0.0134(7) -0.0029(5) 0.0036(6) 0.0052(6) C20 0.0167(7) 0.0193(8) 0.0153(7) -0.0030(6) 0.0016(6) 0.0040(6) C21 0.0217(8) 0.0201(8) 0.0166(7) -0.0003(6) 0.0028(6) 0.0088(6) C22 0.0222(8) 0.0175(8) 0.0179(7) -0.0007(6) 0.0055(6) 0.0054(6) C43 0.0242(8) 0.0209(8) 0.0311(9) 0.0016(7) 0.0061(7) 0.0073(7) F1 0.0603(8) 0.0253(6) 0.0504(7) 0.0127(5) -0.0054(6) 0.0118(5) F2 0.0805(9) 0.0220(6) 0.0610(8) -0.0052(5) 0.0354(7) 0.0126(6) F3 0.0273(6) 0.0222(6) 0.1019(11) 0.0159(6) 0.0154(6) 0.0024(5) C23 0.0160(8) 0.0202(8) 0.0227(8) -0.0012(6) 0.0027(6) 0.0030(6) C24 0.0182(7) 0.0212(8) 0.0200(8) -0.0006(6) 0.0021(6) 0.0077(6) C3 0.0177(7) 0.0137(7) 0.0153(7) -0.0007(5) 0.0026(6) 0.0044(6) C25 0.0202(7) 0.0124(7) 0.0147(7) -0.0022(5) -0.0005(6) 0.0030(6) C26 0.0211(8) 0.0183(8) 0.0200(8) -0.0013(6) 0.0037(6) 0.0049(6) C27 0.0260(8) 0.0223(8) 0.0203(8) -0.0005(6) 0.0075(7) 0.0014(7) C28 0.0336(9) 0.0193(8) 0.0169(8) 0.0046(6) 0.0010(7) 0.0032(7) C29 0.0259(8) 0.0181(8) 0.0206(8) 0.0004(6) -0.0023(6) 0.0063(7) C30 0.0193(7) 0.0145(7) 0.0166(7) -0.0036(6) -0.0016(6) 0.0037(6) C31 0.0198(7) 0.0132(7) 0.0172(7) -0.0049(6) -0.0011(6) 0.0033(6) C32 0.0211(8) 0.0186(8) 0.0217(8) -0.0054(6) -0.0031(6) 0.0079(6) C33 0.0173(8) 0.0235(8) 0.0308(9) -0.0085(7) 0.0014(7) 0.0072(6) C34 0.0219(8) 0.0208(8) 0.0265(8) -0.0047(6) 0.0080(7) 0.0034(6) C35 0.0214(8) 0.0166(7) 0.0208(8) -0.0012(6) 0.0038(6) 0.0047(6) C36 0.0168(7) 0.0128(7) 0.0179(7) -0.0039(5) 0.0001(6) 0.0036(6) C4 0.0174(7) 0.0134(7) 0.0165(7) 0.0006(5) 0.0025(6) 0.0045(6) C37 0.0220(7) 0.0110(7) 0.0177(7) 0.0008(5) 0.0043(6) 0.0041(6) C38 0.0217(8) 0.0204(8) 0.0191(8) -0.0014(6) 0.0015(6) 0.0074(6) C39 0.0215(8) 0.0246(8) 0.0259(8) -0.0009(6) 0.0064(7) 0.0085(7) C40 0.0282(8) 0.0208(8) 0.0203(8) -0.0016(6) 0.0080(7) 0.0053(7) C44 0.0289(9) 0.0396(11) 0.0266(9) -0.0084(8) 0.0080(7) 0.0058(8) F4 0.0337(6) 0.0356(6) 0.0342(6) -0.0066(5) 0.0156(5) 0.0090(5) F5 0.0553(8) 0.0582(9) 0.0870(11) -0.0527(8) 0.0443(8) -0.0222(7) F6 0.0781(10) 0.1380(15) 0.0198(6) 0.0089(7) 0.0156(6) 0.0699(10) C41 0.0264(8) 0.0230(8) 0.0173(8) -0.0003(6) 0.0013(7) 0.0054(7) C42 0.0216(8) 0.0184(8) 0.0194(8) 0.0011(6) 0.0029(6) 0.0069(6) C45 0.0504(14) 0.0746(18) 0.0479(13) 0.0082(12) 0.0135(11) 0.0298(13) C46 0.0496(15) 0.080(2) 0.0713(18) 0.0069(15) -0.0019(13) 0.0256(14) C47 0.0476(13) 0.0756(18) 0.0476(14) 0.0076(12) 0.0057(11) 0.0261(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C5 1.355(2) . ? C1 C2 1.468(2) . ? C1 C4 1.527(2) . ? C5 C6 1.486(2) . ? C5 C17 1.486(2) . ? C6 C7 1.392(2) . ? C6 C11 1.407(2) . ? C7 C8 1.393(2) . ? C7 H7 0.949(19) . ? C8 C9 1.388(2) . ? C8 H8 0.96(2) . ? C9 C10 1.392(2) . ? C9 H9 0.972(19) . ? C10 C11 1.388(2) . ? C10 H10 0.967(19) . ? C11 C12 1.466(2) . ? C12 C13 1.388(2) . ? C12 C17 1.407(2) . ? C13 C14 1.390(2) . ? C13 H13 0.982(19) . ? C14 C15 1.388(2) . ? C14 H14 0.96(2) . ? C15 C16 1.392(2) . ? C15 H15 0.98(2) . ? C16 C17 1.394(2) . ? C16 H16 0.948(19) . ? C2 C18 1.347(2) . ? C2 C3 1.538(2) . ? C18 C19 1.462(2) . ? C18 H18 0.964(17) . ? C19 C20 1.401(2) . ? C19 C24 1.403(2) . ? C20 C21 1.381(2) . ? C20 H20 0.970(19) . ? C21 C22 1.392(2) . ? C21 H21 0.962(19) . ? C22 C23 1.387(2) . ? C22 C43 1.497(2) . ? C43 F1 1.329(2) . ? C43 F3 1.329(2) . ? C43 F2 1.330(2) . ? C23 C24 1.383(2) . ? C23 H23 0.941(19) . ? C24 H24 0.995(18) . ? C3 C25 1.511(2) . ? C3 C36 1.518(2) . ? C3 C4 1.611(2) . ? C25 C26 1.388(2) . ? C25 C30 1.400(2) . ? C26 C27 1.389(2) . ? C26 H26 0.956(18) . ? C27 C28 1.389(3) . ? C27 H27 0.95(2) . ? C28 C29 1.386(3) . ? C28 H28 0.91(2) . ? C29 C30 1.387(2) . ? C29 H29 0.97(2) . ? C30 C31 1.467(2) . ? C31 C32 1.391(2) . ? C31 C36 1.402(2) . ? C32 C33 1.390(2) . ? C32 H32 0.972(18) . ? C33 C34 1.390(3) . ? C33 H33 0.95(2) . ? C34 C35 1.393(2) . ? C34 H34 0.97(2) . ? C35 C36 1.385(2) . ? C35 H35 0.960(19) . ? C4 C37 1.505(2) . ? C4 H4 0.974(18) . ? C37 C38 1.388(2) . ? C37 C42 1.399(2) . ? C38 C39 1.390(2) . ? C38 H38 0.950(19) . ? C39 C40 1.388(2) . ? C39 H39 0.94(2) . ? C40 C41 1.393(2) . ? C40 C44 1.498(2) . ? C44 F4 1.325(2) . ? C44 F6 1.328(2) . ? C44 F5 1.346(2) . ? C41 C42 1.381(2) . ? C41 H41 0.970(19) . ? C42 H42 0.943(18) . ? C45 C46 1.508(4) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 C47 1.473(4) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 C47 1.484(5) 2_666 ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? 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 C5 C1 C2 137.79(14) . . ? C5 C1 C4 129.65(14) . . ? C2 C1 C4 91.83(11) . . ? C1 C5 C6 124.76(14) . . ? C1 C5 C17 129.71(14) . . ? C6 C5 C17 105.36(12) . . ? C7 C6 C11 119.21(14) . . ? C7 C6 C5 131.91(14) . . ? C11 C6 C5 108.87(13) . . ? C6 C7 C8 119.16(15) . . ? C6 C7 H7 120.5(11) . . ? C8 C7 H7 120.4(11) . . ? C9 C8 C7 121.20(15) . . ? C9 C8 H8 119.1(11) . . ? C7 C8 H8 119.7(11) . . ? C8 C9 C10 120.23(15) . . ? C8 C9 H9 119.9(11) . . ? C10 C9 H9 119.9(11) . . ? C11 C10 C9 118.71(15) . . ? C11 C10 H10 120.7(11) . . ? C9 C10 H10 120.6(11) . . ? C10 C11 C6 121.47(14) . . ? C10 C11 C12 130.17(15) . . ? C6 C11 C12 108.36(13) . . ? C13 C12 C17 121.45(15) . . ? C13 C12 C11 129.69(15) . . ? C17 C12 C11 108.85(13) . . ? C12 C13 C14 118.78(15) . . ? C12 C13 H13 120.6(11) . . ? C14 C13 H13 120.7(11) . . ? C15 C14 C13 120.30(15) . . ? C15 C14 H14 120.6(12) . . ? C13 C14 H14 119.1(12) . . ? C14 C15 C16 121.09(16) . . ? C14 C15 H15 120.0(12) . . ? C16 C15 H15 118.9(12) . . ? C15 C16 C17 119.33(16) . . ? C15 C16 H16 119.9(11) . . ? C17 C16 H16 120.8(11) . . ? C16 C17 C12 119.04(14) . . ? C16 C17 C5 132.34(14) . . ? C12 C17 C5 108.53(13) . . ? C18 C2 C1 133.42(14) . . ? C18 C2 C3 133.11(14) . . ? C1 C2 C3 92.19(11) . . ? C2 C18 C19 129.07(14) . . ? C2 C18 H18 116.3(10) . . ? C19 C18 H18 114.5(10) . . ? C20 C19 C24 118.23(14) . . ? C20 C19 C18 123.58(14) . . ? C24 C19 C18 118.14(14) . . ? C21 C20 C19 120.72(14) . . ? C21 C20 H20 121.0(11) . . ? C19 C20 H20 118.2(11) . . ? C20 C21 C22 119.95(15) . . ? C20 C21 H21 119.3(11) . . ? C22 C21 H21 120.7(11) . . ? C23 C22 C21 120.47(15) . . ? C23 C22 C43 120.07(14) . . ? C21 C22 C43 119.45(14) . . ? F1 C43 F3 106.56(15) . . ? F1 C43 F2 105.92(15) . . ? F3 C43 F2 106.35(15) . . ? F1 C43 C22 112.53(14) . . ? F3 C43 C22 112.57(14) . . ? F2 C43 C22 112.42(14) . . ? C24 C23 C22 119.35(14) . . ? C24 C23 H23 119.7(11) . . ? C22 C23 H23 121.0(11) . . ? C23 C24 C19 121.26(15) . . ? C23 C24 H24 119.5(10) . . ? C19 C24 H24 119.2(10) . . ? C25 C3 C36 102.40(12) . . ? C25 C3 C2 121.18(12) . . ? C36 C3 C2 117.61(12) . . ? C25 C3 C4 119.19(12) . . ? C36 C3 C4 110.47(12) . . ? C2 C3 C4 86.13(11) . . ? C26 C25 C30 120.26(14) . . ? C26 C25 C3 129.66(14) . . ? C30 C25 C3 110.09(13) . . ? C25 C26 C27 118.65(15) . . ? C25 C26 H26 120.7(11) . . ? C27 C26 H26 120.6(11) . . ? C28 C27 C26 120.87(16) . . ? C28 C27 H27 121.2(12) . . ? C26 C27 H27 117.9(12) . . ? C29 C28 C27 120.82(15) . . ? C29 C28 H28 118.4(13) . . ? C27 C28 H28 120.8(13) . . ? C28 C29 C30 118.52(15) . . ? C28 C29 H29 122.0(12) . . ? C30 C29 H29 119.5(12) . . ? C29 C30 C25 120.87(15) . . ? C29 C30 C31 130.29(15) . . ? C25 C30 C31 108.82(13) . . ? C32 C31 C36 120.40(15) . . ? C32 C31 C30 131.28(15) . . ? C36 C31 C30 108.32(13) . . ? C33 C32 C31 118.63(15) . . ? C33 C32 H32 120.6(10) . . ? C31 C32 H32 120.7(10) . . ? C32 C33 C34 120.83(15) . . ? C32 C33 H33 120.6(12) . . ? C34 C33 H33 118.5(12) . . ? C33 C34 C35 120.74(16) . . ? C33 C34 H34 120.9(11) . . ? C35 C34 H34 118.4(11) . . ? C36 C35 C34 118.58(15) . . ? C36 C35 H35 120.8(11) . . ? C34 C35 H35 120.6(11) . . ? C35 C36 C31 120.77(14) . . ? C35 C36 C3 129.08(14) . . ? C31 C36 C3 110.04(13) . . ? C37 C4 C1 118.18(13) . . ? C37 C4 C3 114.99(12) . . ? C1 C4 C3 87.29(11) . . ? C37 C4 H4 110.4(10) . . ? C1 C4 H4 113.1(10) . . ? C3 C4 H4 111.0(10) . . ? C38 C37 C42 118.85(14) . . ? C38 C37 C4 122.53(14) . . ? C42 C37 C4 118.63(14) . . ? C37 C38 C39 120.67(15) . . ? C37 C38 H38 120.1(11) . . ? C39 C38 H38 119.1(11) . . ? C40 C39 C38 119.83(15) . . ? C40 C39 H39 121.9(12) . . ? C38 C39 H39 118.2(12) . . ? C39 C40 C41 120.09(15) . . ? C39 C40 C44 121.17(16) . . ? C41 C40 C44 118.69(15) . . ? F4 C44 F6 106.38(15) . . ? F4 C44 F5 105.32(16) . . ? F6 C44 F5 107.26(17) . . ? F4 C44 C40 113.74(15) . . ? F6 C44 C40 111.97(16) . . ? F5 C44 C40 111.68(15) . . ? C42 C41 C40 119.71(15) . . ? C42 C41 H41 120.3(11) . . ? C40 C41 H41 120.0(11) . . ? C41 C42 C37 120.85(15) . . ? C41 C42 H42 120.4(11) . . ? C37 C42 H42 118.7(11) . . ? C46 C45 H45A 109.5 . . ? C46 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C46 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C47 C46 C45 116.6(2) . . ? C47 C46 H46A 108.2 . . ? C45 C46 H46A 108.2 . . ? C47 C46 H46B 108.2 . . ? C45 C46 H46B 108.2 . . ? H46A C46 H46B 107.3 . . ? C46 C47 C47 118.3(3) . 2_666 ? C46 C47 H47A 107.7 . . ? C47 C47 H47A 107.7 2_666 . ? C46 C47 H47B 107.7 . . ? C47 C47 H47B 107.7 2_666 . ? H47A C47 H47B 107.1 . . ? 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 C2 C1 C5 C6 -176.60(16) . . . . ? C4 C1 C5 C6 -9.4(3) . . . . ? C2 C1 C5 C17 -2.1(3) . . . . ? C4 C1 C5 C17 165.17(15) . . . . ? C1 C5 C6 C7 -6.1(3) . . . . ? C17 C5 C6 C7 178.27(16) . . . . ? C1 C5 C6 C11 175.07(14) . . . . ? C17 C5 C6 C11 -0.57(16) . . . . ? C11 C6 C7 C8 -0.1(2) . . . . ? C5 C6 C7 C8 -178.87(15) . . . . ? C6 C7 C8 C9 0.4(2) . . . . ? C7 C8 C9 C10 -0.6(2) . . . . ? C8 C9 C10 C11 0.5(2) . . . . ? C9 C10 C11 C6 -0.2(2) . . . . ? C9 C10 C11 C12 179.37(15) . . . . ? C7 C6 C11 C10 0.1(2) . . . . ? C5 C6 C11 C10 179.06(14) . . . . ? C7 C6 C11 C12 -179.63(14) . . . . ? C5 C6 C11 C12 -0.62(17) . . . . ? C10 C11 C12 C13 3.3(3) . . . . ? C6 C11 C12 C13 -177.09(16) . . . . ? C10 C11 C12 C17 -177.99(15) . . . . ? C6 C11 C12 C17 1.66(17) . . . . ? C17 C12 C13 C14 1.0(2) . . . . ? C11 C12 C13 C14 179.60(15) . . . . ? C12 C13 C14 C15 -0.8(3) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 1.1(3) . . . . ? C15 C16 C17 C12 -0.8(2) . . . . ? C15 C16 C17 C5 -177.05(16) . . . . ? C13 C12 C17 C16 -0.2(2) . . . . ? C11 C12 C17 C16 -179.07(14) . . . . ? C13 C12 C17 C5 176.86(14) . . . . ? C11 C12 C17 C5 -2.01(17) . . . . ? C1 C5 C17 C16 2.8(3) . . . . ? C6 C5 C17 C16 178.12(16) . . . . ? C1 C5 C17 C12 -173.75(15) . . . . ? C6 C5 C17 C12 1.60(16) . . . . ? C5 C1 C2 C18 -34.5(3) . . . . ? C4 C1 C2 C18 155.26(17) . . . . ? C5 C1 C2 C3 157.54(19) . . . . ? C4 C1 C2 C3 -12.66(11) . . . . ? C1 C2 C18 C19 -175.71(15) . . . . ? C3 C2 C18 C19 -12.4(3) . . . . ? C2 C18 C19 C20 -20.5(2) . . . . ? C2 C18 C19 C24 162.20(15) . . . . ? C24 C19 C20 C21 -1.0(2) . . . . ? C18 C19 C20 C21 -178.31(14) . . . . ? C19 C20 C21 C22 0.7(2) . . . . ? C20 C21 C22 C23 0.0(2) . . . . ? C20 C21 C22 C43 178.43(14) . . . . ? C23 C22 C43 F1 -139.63(16) . . . . ? C21 C22 C43 F1 42.0(2) . . . . ? C23 C22 C43 F3 -19.2(2) . . . . ? C21 C22 C43 F3 162.39(15) . . . . ? C23 C22 C43 F2 100.88(18) . . . . ? C21 C22 C43 F2 -77.53(19) . . . . ? C21 C22 C23 C24 -0.3(2) . . . . ? C43 C22 C23 C24 -178.72(14) . . . . ? C22 C23 C24 C19 -0.1(2) . . . . ? C20 C19 C24 C23 0.7(2) . . . . ? C18 C19 C24 C23 178.16(14) . . . . ? C18 C2 C3 C25 -33.9(2) . . . . ? C1 C2 C3 C25 134.04(13) . . . . ? C18 C2 C3 C36 92.9(2) . . . . ? C1 C2 C3 C36 -99.11(14) . . . . ? C18 C2 C3 C4 -155.98(17) . . . . ? C1 C2 C3 C4 12.00(11) . . . . ? C36 C3 C25 C26 -176.17(15) . . . . ? C2 C3 C25 C26 -42.7(2) . . . . ? C4 C3 C25 C26 61.6(2) . . . . ? C36 C3 C25 C30 3.90(15) . . . . ? C2 C3 C25 C30 137.35(14) . . . . ? C4 C3 C25 C30 -118.31(14) . . . . ? C30 C25 C26 C27 -0.5(2) . . . . ? C3 C25 C26 C27 179.59(14) . . . . ? C25 C26 C27 C28 -0.2(2) . . . . ? C26 C27 C28 C29 0.3(2) . . . . ? C27 C28 C29 C30 0.2(2) . . . . ? C28 C29 C30 C25 -0.8(2) . . . . ? C28 C29 C30 C31 -178.69(15) . . . . ? C26 C25 C30 C29 1.0(2) . . . . ? C3 C25 C30 C29 -179.07(13) . . . . ? C26 C25 C30 C31 179.26(13) . . . . ? C3 C25 C30 C31 -0.80(16) . . . . ? C29 C30 C31 C32 -5.5(3) . . . . ? C25 C30 C31 C32 176.40(15) . . . . ? C29 C30 C31 C36 175.05(15) . . . . ? C25 C30 C31 C36 -3.00(16) . . . . ? C36 C31 C32 C33 -1.6(2) . . . . ? C30 C31 C32 C33 179.08(15) . . . . ? C31 C32 C33 C34 -0.3(2) . . . . ? C32 C33 C34 C35 1.3(2) . . . . ? C33 C34 C35 C36 -0.3(2) . . . . ? C34 C35 C36 C31 -1.6(2) . . . . ? C34 C35 C36 C3 174.13(14) . . . . ? C32 C31 C36 C35 2.6(2) . . . . ? C30 C31 C36 C35 -177.97(13) . . . . ? C32 C31 C36 C3 -173.89(13) . . . . ? C30 C31 C36 C3 5.59(16) . . . . ? C25 C3 C36 C35 178.15(15) . . . . ? C2 C3 C36 C35 42.7(2) . . . . ? C4 C3 C36 C35 -53.9(2) . . . . ? C25 C3 C36 C31 -5.79(15) . . . . ? C2 C3 C36 C31 -141.29(13) . . . . ? C4 C3 C36 C31 122.17(13) . . . . ? C5 C1 C4 C37 83.6(2) . . . . ? C2 C1 C4 C37 -104.95(14) . . . . ? C5 C1 C4 C3 -159.37(16) . . . . ? C2 C1 C4 C3 12.08(11) . . . . ? C25 C3 C4 C37 -15.39(19) . . . . ? C36 C3 C4 C37 -133.50(13) . . . . ? C2 C3 C4 C37 108.43(13) . . . . ? C25 C3 C4 C1 -135.36(13) . . . . ? C36 C3 C4 C1 106.53(12) . . . . ? C2 C3 C4 C1 -11.54(10) . . . . ? C1 C4 C37 C38 5.1(2) . . . . ? C3 C4 C37 C38 -95.93(17) . . . . ? C1 C4 C37 C42 -175.42(13) . . . . ? C3 C4 C37 C42 83.59(17) . . . . ? C42 C37 C38 C39 0.8(2) . . . . ? C4 C37 C38 C39 -179.72(15) . . . . ? C37 C38 C39 C40 -0.6(2) . . . . ? C38 C39 C40 C41 0.2(3) . . . . ? C38 C39 C40 C44 177.64(16) . . . . ? C39 C40 C44 F4 14.8(3) . . . . ? C41 C40 C44 F4 -167.76(16) . . . . ? C39 C40 C44 F6 135.43(18) . . . . ? C41 C40 C44 F6 -47.1(2) . . . . ? C39 C40 C44 F5 -104.3(2) . . . . ? C41 C40 C44 F5 73.2(2) . . . . ? C39 C40 C41 C42 0.0(2) . . . . ? C44 C40 C41 C42 -177.52(16) . . . . ? C40 C41 C42 C37 0.2(2) . . . . ? C38 C37 C42 C41 -0.6(2) . . . . ? C4 C37 C42 C41 179.88(14) . . . . ? C45 C46 C47 C47 179.3(3) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.708 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.048 #===END data_mjm61(14) _database_code_depnum_ccdc_archive 'CCDC 769735' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H26 F6, C6 H14' _chemical_formula_sum 'C50 H40 F6' _chemical_formula_weight 754.82 _chemical_absolute_configuration unk 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 0.0000 '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' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'I b a 2' _symmetry_space_group_name_Hall 'I 2 -2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 10.154(3) _cell_length_b 16.592(4) _cell_length_c 23.131(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3897.0(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1968 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 22.27 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7172 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.064 before and 0.038 after correction. The Ratio of minimum to maximum transmission is 0.720484. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; The PLATON "squeeze" procedure was used to treat regions of diffuse solvent(s) which could not be modelled in terms of atomic sites. The number of electrons thus located, 199 per unit cell, is included in the formula, formula weight, calculated density, \m and F(000). This residual electron density was assigned to 4 molecules of hexane per unit cell. 4 molecules of hexane would give 200 e^-^. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9426 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1976 _reflns_number_gt 1672 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0916P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1976 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1361 _refine_ls_wR_factor_gt 0.1311 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 C1 C 0.4336(3) 0.01668(17) 0.06649(14) 0.0163(7) Uani 1 1 d . . . C3 C 0.3605(3) 0.06478(18) 0.10083(14) 0.0178(7) Uani 1 1 d . . . C4 C 0.3968(3) 0.10288(19) 0.15604(15) 0.0183(7) Uani 1 1 d . . . C5 C 0.5089(4) 0.09466(18) 0.19081(15) 0.0193(7) Uani 1 1 d . . . H5 H 0.5778 0.0590 0.1800 0.023 Uiso 1 1 calc R . . C6 C 0.5178(4) 0.13959(19) 0.24148(16) 0.0232(8) Uani 1 1 d . . . H6 H 0.5931 0.1339 0.2655 0.028 Uiso 1 1 calc R . . C7 C 0.4182(4) 0.1928(2) 0.25750(16) 0.0285(9) Uani 1 1 d . . . H7 H 0.4255 0.2224 0.2925 0.034 Uiso 1 1 calc R . . C8 C 0.3080(4) 0.2029(2) 0.22238(16) 0.0272(9) Uani 1 1 d . . . H8 H 0.2408 0.2400 0.2328 0.033 Uiso 1 1 calc R . . C9 C 0.2977(4) 0.1577(2) 0.17175(16) 0.0222(8) Uani 1 1 d . . . C10 C 0.1936(4) 0.1560(2) 0.12823(15) 0.0202(8) Uani 1 1 d . . . C11 C 0.0741(4) 0.1963(2) 0.12527(16) 0.0252(9) Uani 1 1 d . . . H11 H 0.0503 0.2346 0.1540 0.030 Uiso 1 1 calc R . . C12 C -0.0094(4) 0.1797(2) 0.07974(19) 0.0302(9) Uani 1 1 d . . . H12 H -0.0909 0.2075 0.0768 0.036 Uiso 1 1 calc R . . C13 C 0.0243(4) 0.1223(2) 0.03781(18) 0.0276(8) Uani 1 1 d . . . H13 H -0.0348 0.1113 0.0070 0.033 Uiso 1 1 calc R . . C14 C 0.1441(4) 0.0813(2) 0.04103(16) 0.0215(8) Uani 1 1 d . . . H14 H 0.1663 0.0420 0.0128 0.026 Uiso 1 1 calc R . . C15 C 0.2299(3) 0.09844(18) 0.08549(15) 0.0183(7) Uani 1 1 d . . . C2 C 0.4226(3) 0.00565(18) 0.00108(14) 0.0182(7) Uani 1 1 d . . . H2 H 0.3949 0.0563 -0.0189 0.022 Uiso 1 1 calc R . . C16 C 0.3523(3) -0.06749(19) -0.02228(15) 0.0187(7) Uani 1 1 d . . . C17 C 0.3405(3) -0.13822(19) 0.00904(14) 0.0178(7) Uani 1 1 d . . . H17 H 0.3693 -0.1396 0.0481 0.021 Uiso 1 1 calc R . . C18 C 0.2875(4) -0.2067(2) -0.01548(16) 0.0208(8) Uani 1 1 d . . . H18 H 0.2798 -0.2549 0.0064 0.025 Uiso 1 1 calc R . . C19 C 0.2459(4) -0.2045(2) -0.07219(16) 0.0211(8) Uani 1 1 d . . . C22 C 0.1897(4) -0.2792(2) -0.09921(18) 0.0302(9) Uani 1 1 d . . . F1 F 0.1771(5) -0.27517(19) -0.15415(12) 0.0877(15) Uani 1 1 d . . . F2 F 0.0818(4) -0.3029(2) -0.07508(19) 0.0988(16) Uani 1 1 d . . . F3 F 0.2671(4) -0.34351(18) -0.0905(2) 0.0962(16) Uani 1 1 d . . . C20 C 0.2520(4) -0.1333(2) -0.10351(17) 0.0299(9) Uani 1 1 d . . . H20 H 0.2184 -0.1312 -0.1418 0.036 Uiso 1 1 calc R . . C21 C 0.3069(4) -0.0662(2) -0.07885(15) 0.0265(9) Uani 1 1 d . . . H21 H 0.3139 -0.0180 -0.1008 0.032 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 C1 0.0192(18) 0.0100(14) 0.0199(16) 0.0045(12) -0.0053(14) -0.0048(12) C3 0.0194(19) 0.0130(14) 0.0209(18) 0.0015(12) 0.0035(15) -0.0023(13) C4 0.0214(18) 0.0146(15) 0.0188(17) 0.0006(13) 0.0021(15) -0.0037(14) C5 0.0222(19) 0.0134(14) 0.0222(18) 0.0013(13) -0.0006(15) -0.0045(13) C6 0.027(2) 0.0217(16) 0.0208(18) -0.0029(14) -0.0024(17) -0.0067(15) C7 0.037(2) 0.0273(18) 0.0212(18) -0.0070(15) 0.0043(18) -0.0051(17) C8 0.028(2) 0.0267(18) 0.027(2) -0.0080(15) 0.0036(17) -0.0012(16) C9 0.0184(18) 0.0175(16) 0.031(2) 0.0009(14) 0.0046(16) -0.0008(14) C10 0.0214(19) 0.0160(15) 0.0231(19) -0.0048(13) -0.0040(15) 0.0005(13) C11 0.020(2) 0.0257(18) 0.030(2) -0.0060(15) 0.0046(17) 0.0025(15) C12 0.025(2) 0.0279(18) 0.038(2) -0.0030(17) 0.0026(18) 0.0107(16) C13 0.025(2) 0.0261(17) 0.032(2) -0.0030(16) -0.0063(18) 0.0037(16) C14 0.0217(19) 0.0170(15) 0.0259(19) 0.0007(14) 0.0000(16) 0.0009(14) C15 0.0207(19) 0.0153(14) 0.0191(16) 0.0013(13) 0.0026(15) -0.0007(13) C2 0.0225(19) 0.0136(13) 0.0186(17) 0.0031(13) 0.0031(15) 0.0002(14) C16 0.0158(18) 0.0198(16) 0.0205(17) -0.0011(13) 0.0052(14) 0.0034(14) C17 0.0163(18) 0.0215(16) 0.0157(17) 0.0018(13) -0.0015(15) 0.0009(13) C18 0.0182(18) 0.0207(16) 0.0235(18) -0.0007(14) 0.0054(16) 0.0002(14) C19 0.0176(18) 0.0245(17) 0.0213(18) -0.0049(14) 0.0082(16) -0.0046(14) C22 0.032(2) 0.029(2) 0.030(2) -0.0036(16) 0.0024(19) -0.0157(17) F1 0.174(4) 0.0569(18) 0.0322(16) 0.0009(13) -0.021(2) -0.070(2) F2 0.080(3) 0.083(2) 0.134(4) -0.059(2) 0.055(3) -0.062(2) F3 0.108(3) 0.0352(16) 0.145(4) -0.045(2) -0.065(3) 0.0160(18) C20 0.039(2) 0.029(2) 0.0221(19) -0.0020(16) -0.0072(18) -0.0041(17) C21 0.040(2) 0.0204(18) 0.0193(19) 0.0017(14) 0.0037(17) -0.0008(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 C1 C3 1.349(5) . ? C1 C1 1.458(7) 2_655 ? C1 C2 1.528(4) . ? C3 C4 1.472(5) . ? C3 C15 1.482(5) . ? C4 C5 1.400(5) . ? C4 C9 1.405(5) . ? C5 C6 1.392(5) . ? C5 H5 0.9500 . ? C6 C7 1.393(5) . ? C6 H6 0.9500 . ? C7 C8 1.393(6) . ? C7 H7 0.9500 . ? C8 C9 1.394(5) . ? C8 H8 0.9500 . ? C9 C10 1.460(5) . ? C10 C11 1.387(5) . ? C10 C15 1.423(5) . ? C11 C12 1.380(6) . ? C11 H11 0.9500 . ? C12 C13 1.402(5) . ? C12 H12 0.9500 . ? C13 C14 1.396(5) . ? C13 H13 0.9500 . ? C14 C15 1.377(5) . ? C14 H14 0.9500 . ? C2 C16 1.508(5) . ? C2 C2 1.584(7) 2_655 ? C2 H2 1.0000 . ? C16 C17 1.384(5) . ? C16 C21 1.388(5) . ? C17 C18 1.379(5) . ? C17 H17 0.9500 . ? C18 C19 1.379(5) . ? C18 H18 0.9500 . ? C19 C20 1.386(5) . ? C19 C22 1.501(5) . ? C22 F1 1.279(5) . ? C22 F2 1.291(5) . ? C22 F3 1.340(5) . ? C20 C21 1.370(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C1 C1 137.2(3) . 2_655 ? C3 C1 C2 127.9(3) . . ? C1 C1 C2 91.27(18) 2_655 . ? C1 C3 C4 128.8(3) . . ? C1 C3 C15 125.1(3) . . ? C4 C3 C15 105.7(3) . . ? C5 C4 C9 119.8(3) . . ? C5 C4 C3 131.3(3) . . ? C9 C4 C3 108.8(3) . . ? C6 C5 C4 119.0(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 121.1(4) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C8 120.3(3) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C9 119.1(4) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C8 C9 C4 120.8(4) . . ? C8 C9 C10 130.1(3) . . ? C4 C9 C10 109.1(3) . . ? C11 C10 C15 121.1(3) . . ? C11 C10 C9 131.1(3) . . ? C15 C10 C9 107.7(3) . . ? C12 C11 C10 118.6(3) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C13 120.9(4) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 120.5(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.4(3) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C10 119.6(3) . . ? C14 C15 C3 131.8(3) . . ? C10 C15 C3 108.6(3) . . ? C16 C2 C1 119.1(3) . . ? C16 C2 C2 112.0(3) . 2_655 ? C1 C2 C2 86.65(18) . 2_655 ? C16 C2 H2 112.2 . . ? C1 C2 H2 112.2 . . ? C2 C2 H2 112.2 2_655 . ? C17 C16 C21 118.5(3) . . ? C17 C16 C2 122.4(3) . . ? C21 C16 C2 118.9(3) . . ? C18 C17 C16 121.1(3) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C17 119.2(3) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 120.4(3) . . ? C18 C19 C22 119.4(3) . . ? C20 C19 C22 120.2(3) . . ? F1 C22 F2 111.1(4) . . ? F1 C22 F3 104.4(4) . . ? F2 C22 F3 100.9(4) . . ? F1 C22 C19 114.1(3) . . ? F2 C22 C19 113.2(3) . . ? F3 C22 C19 111.9(4) . . ? C21 C20 C19 119.5(3) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C16 121.0(3) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? 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 C1 C1 C3 C4 -0.4(6) 2_655 . . . ? C2 C1 C3 C4 -152.2(3) . . . . ? C1 C1 C3 C15 171.1(4) 2_655 . . . ? C2 C1 C3 C15 19.3(5) . . . . ? C1 C3 C4 C5 -6.9(6) . . . . ? C15 C3 C4 C5 -179.6(3) . . . . ? C1 C3 C4 C9 170.7(3) . . . . ? C15 C3 C4 C9 -2.0(4) . . . . ? C9 C4 C5 C6 1.9(5) . . . . ? C3 C4 C5 C6 179.3(3) . . . . ? C4 C5 C6 C7 -0.8(5) . . . . ? C5 C6 C7 C8 -0.9(5) . . . . ? C6 C7 C8 C9 1.3(6) . . . . ? C7 C8 C9 C4 -0.1(5) . . . . ? C7 C8 C9 C10 179.3(4) . . . . ? C5 C4 C9 C8 -1.5(5) . . . . ? C3 C4 C9 C8 -179.5(3) . . . . ? C5 C4 C9 C10 178.9(3) . . . . ? C3 C4 C9 C10 1.0(4) . . . . ? C8 C9 C10 C11 -2.2(7) . . . . ? C4 C9 C10 C11 177.3(4) . . . . ? C8 C9 C10 C15 -179.0(4) . . . . ? C4 C9 C10 C15 0.5(4) . . . . ? C15 C10 C11 C12 -0.2(5) . . . . ? C9 C10 C11 C12 -176.6(4) . . . . ? C10 C11 C12 C13 1.1(6) . . . . ? C11 C12 C13 C14 -0.6(6) . . . . ? C12 C13 C14 C15 -0.7(5) . . . . ? C13 C14 C15 C10 1.6(5) . . . . ? C13 C14 C15 C3 178.8(3) . . . . ? C11 C10 C15 C14 -1.2(5) . . . . ? C9 C10 C15 C14 176.0(3) . . . . ? C11 C10 C15 C3 -179.0(3) . . . . ? C9 C10 C15 C3 -1.8(4) . . . . ? C1 C3 C15 C14 11.8(6) . . . . ? C4 C3 C15 C14 -175.1(3) . . . . ? C1 C3 C15 C10 -170.8(3) . . . . ? C4 C3 C15 C10 2.3(3) . . . . ? C3 C1 C2 C16 -100.7(4) . . . . ? C1 C1 C2 C16 98.0(3) 2_655 . . . ? C3 C1 C2 C2 145.9(3) . . . 2_655 ? C1 C1 C2 C2 -15.4(3) 2_655 . . 2_655 ? C1 C2 C16 C17 -24.7(5) . . . . ? C2 C2 C16 C17 74.1(3) 2_655 . . . ? C1 C2 C16 C21 160.5(3) . . . . ? C2 C2 C16 C21 -100.7(3) 2_655 . . . ? C21 C16 C17 C18 1.4(5) . . . . ? C2 C16 C17 C18 -173.4(3) . . . . ? C16 C17 C18 C19 0.0(5) . . . . ? C17 C18 C19 C20 -2.7(5) . . . . ? C17 C18 C19 C22 179.3(3) . . . . ? C18 C19 C22 F1 -167.7(4) . . . . ? C20 C19 C22 F1 14.3(6) . . . . ? C18 C19 C22 F2 63.9(5) . . . . ? C20 C19 C22 F2 -114.2(5) . . . . ? C18 C19 C22 F3 -49.4(5) . . . . ? C20 C19 C22 F3 132.6(4) . . . . ? C18 C19 C20 C21 3.8(6) . . . . ? C22 C19 C20 C21 -178.2(4) . . . . ? C19 C20 C21 C16 -2.3(6) . . . . ? C17 C16 C21 C20 -0.3(6) . . . . ? C2 C16 C21 C20 174.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.377 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.052 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.267 226 50 'C6 H14' 2 0.000 0.000 0.767 226 50 'C6 H14' 3 0.500 0.500 0.766 222 49 'C6 H14' 4 0.500 0.500 0.266 222 50 'C6 H14' _platon_squeeze_details ; ; #===END data_mjm95(13) _database_code_depnum_ccdc_archive 'CCDC 769736' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4 (C44 H26 F6), C H2 Cl2' _chemical_formula_sum 'C177 H106 F24 Cl2' _chemical_formula_weight 2759.52 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' F F 0.0171 0.0103 '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 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.118(3) _cell_length_b 16.177(4) _cell_length_c 22.818(6) _cell_angle_alpha 110.541(4) _cell_angle_beta 97.597(5) _cell_angle_gamma 94.218(5) _cell_volume 3437.7(16) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5203 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 22.25 _exptl_crystal_description chunk _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1418 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8416 _exptl_absorpt_correction_T_max 0.9732 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.128 before and 0.021 after correction. The Ratio of minimum to maximum transmission is 0.864794. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45731 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 24.00 _reflns_number_total 10807 _reflns_number_gt 8184 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0524P)^2^+0.9344P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10807 _refine_ls_number_parameters 1031 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.051 _refine_ls_shift/su_mean 0.003 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 C1 C 0.0226(2) 0.02871(13) 0.29055(10) 0.0556(5) Uani 1 1 d . . . C5 C 0.0021(2) -0.00873(12) 0.22633(9) 0.0553(5) Uani 1 1 d . . . C6 C -0.1312(2) -0.04230(12) 0.18500(10) 0.0585(5) Uani 1 1 d . . . C7 C -0.2569(2) -0.06073(14) 0.19925(12) 0.0696(6) Uani 1 1 d . . . H7 H -0.2669 -0.0532 0.2407 0.084 Uiso 1 1 calc R . . C8 C -0.3668(2) -0.09040(15) 0.15098(14) 0.0808(7) Uani 1 1 d . . . H8 H -0.4511 -0.1032 0.1600 0.097 Uiso 1 1 calc R . . C9 C -0.3530(3) -0.10121(15) 0.08979(14) 0.0854(8) Uani 1 1 d . . . H9 H -0.4289 -0.1187 0.0584 0.103 Uiso 1 1 calc R . . C10 C -0.2288(3) -0.08673(14) 0.07402(11) 0.0760(7) Uani 1 1 d . . . H10 H -0.2203 -0.0955 0.0322 0.091 Uiso 1 1 calc R . . C11 C -0.1157(2) -0.05865(12) 0.12199(10) 0.0619(5) Uani 1 1 d . . . C12 C 0.0268(2) -0.04072(12) 0.12008(10) 0.0598(5) Uani 1 1 d . . . C13 C 0.0933(3) -0.04714(15) 0.06989(11) 0.0748(6) Uani 1 1 d . . . H13 H 0.0459 -0.0673 0.0286 0.090 Uiso 1 1 calc R . . C14 C 0.2301(3) -0.02348(15) 0.08157(13) 0.0811(7) Uani 1 1 d . . . H14 H 0.2754 -0.0283 0.0478 0.097 Uiso 1 1 calc R . . C15 C 0.3018(3) 0.00754(14) 0.14308(12) 0.0737(6) Uani 1 1 d . . . H15 H 0.3942 0.0241 0.1501 0.088 Uiso 1 1 calc R . . C16 C 0.2365(2) 0.01406(13) 0.19413(10) 0.0620(5) Uani 1 1 d . . . H16 H 0.2845 0.0354 0.2353 0.074 Uiso 1 1 calc R . . C17 C 0.0985(2) -0.01181(12) 0.18273(9) 0.0556(5) Uani 1 1 d . . . C2 C 0.1367(2) 0.06783(13) 0.34198(9) 0.0571(5) Uani 1 1 d . . . C18 C 0.2580(2) 0.04570(13) 0.36044(9) 0.0577(5) Uani 1 1 d . . . C19 C 0.3208(2) -0.03536(13) 0.33129(9) 0.0577(5) Uani 1 1 d . . . C20 C 0.2774(2) -0.11081(14) 0.27767(11) 0.0708(6) Uani 1 1 d . . . H20 H 0.1965 -0.1154 0.2514 0.085 Uiso 1 1 calc R . . C21 C 0.3560(3) -0.17962(16) 0.26360(12) 0.0853(7) Uani 1 1 d . . . H21 H 0.3272 -0.2306 0.2277 0.102 Uiso 1 1 calc R . . C22 C 0.4760(3) -0.17357(18) 0.30201(13) 0.0883(8) Uani 1 1 d . . . H22 H 0.5285 -0.2198 0.2912 0.106 Uiso 1 1 calc R . . C23 C 0.5190(2) -0.09975(17) 0.35630(12) 0.0773(7) Uani 1 1 d . . . H23 H 0.5994 -0.0963 0.3826 0.093 Uiso 1 1 calc R . . C24 C 0.4415(2) -0.03099(14) 0.37124(10) 0.0605(5) Uani 1 1 d . . . C25 C 0.4592(2) 0.05209(15) 0.42650(10) 0.0621(5) Uani 1 1 d . . . C26 C 0.5620(2) 0.08704(18) 0.47815(11) 0.0763(7) Uani 1 1 d . . . H26 H 0.6346 0.0561 0.4821 0.092 Uiso 1 1 calc R . . C27 C 0.5546(3) 0.1683(2) 0.52332(12) 0.0913(8) Uani 1 1 d . . . H27 H 0.6227 0.1925 0.5585 0.110 Uiso 1 1 calc R . . C28 C 0.4475(3) 0.2147(2) 0.51741(12) 0.0973(8) Uani 1 1 d . . . H28 H 0.4446 0.2698 0.5485 0.117 Uiso 1 1 calc R . . C29 C 0.3450(3) 0.18038(17) 0.46600(11) 0.0821(7) Uani 1 1 d . . . H29 H 0.2737 0.2122 0.4620 0.098 Uiso 1 1 calc R . . C30 C 0.3495(2) 0.09800(14) 0.42040(10) 0.0618(5) Uani 1 1 d . . . C3 C 0.0516(2) 0.13040(14) 0.38347(10) 0.0625(5) Uani 1 1 d . . . H3 H 0.0580 0.1266 0.4257 0.075 Uiso 1 1 calc R . . C31 C 0.0574(2) 0.22493(14) 0.38641(9) 0.0601(5) Uani 1 1 d . . . C32 C 0.1187(2) 0.25355(15) 0.34486(11) 0.0691(6) Uani 1 1 d . . . H32 H 0.1707 0.2167 0.3188 0.083 Uiso 1 1 calc R . . C33 C 0.1036(2) 0.33582(16) 0.34166(12) 0.0762(6) Uani 1 1 d . . . H33 H 0.1452 0.3541 0.3135 0.091 Uiso 1 1 calc R . . C34 C 0.0274(2) 0.39099(15) 0.37998(11) 0.0735(6) Uani 1 1 d . A . C43 C 0.0031(4) 0.4778(2) 0.3738(2) 0.0997(9) Uani 1 1 d . . . F1A F 0.0069(8) 0.4788(4) 0.3168(3) 0.112(2) Uani 0.641(14) 1 d P A 1 F2A F -0.1115(10) 0.5036(8) 0.3870(8) 0.170(4) Uani 0.641(14) 1 d P A 1 F3A F 0.0996(10) 0.5446(4) 0.4080(3) 0.145(4) Uani 0.641(14) 1 d P A 1 F1B F -0.041(3) 0.5285(9) 0.4221(7) 0.168(8) Uani 0.359(14) 1 d P A 2 F2B F 0.106(2) 0.5202(16) 0.375(3) 0.323(19) Uani 0.359(14) 1 d P A 2 F3B F -0.082(5) 0.4633(11) 0.3251(14) 0.301(15) Uani 0.359(14) 1 d P A 2 C35 C -0.0294(3) 0.36474(17) 0.42330(12) 0.0827(7) Uani 1 1 d . . . H35 H -0.0788 0.4026 0.4503 0.099 Uiso 1 1 calc R A . C36 C -0.0133(3) 0.28309(16) 0.42692(10) 0.0756(6) Uani 1 1 d . A . H36 H -0.0505 0.2666 0.4570 0.091 Uiso 1 1 calc R . . C4 C -0.0762(2) 0.06836(14) 0.33539(10) 0.0599(5) Uani 1 1 d . . . H4 H -0.1106 0.0243 0.3520 0.072 Uiso 1 1 calc R . . C37 C -0.1885(2) 0.11524(13) 0.31792(10) 0.0578(5) Uani 1 1 d . . . C38 C -0.1826(2) 0.15862(13) 0.27549(9) 0.0597(5) Uani 1 1 d . . . H38 H -0.1116 0.1531 0.2529 0.072 Uiso 1 1 calc R . . C39 C -0.2800(2) 0.20947(14) 0.26637(10) 0.0648(5) Uani 1 1 d . . . H39 H -0.2741 0.2387 0.2380 0.078 Uiso 1 1 calc R . . C40 C -0.3865(2) 0.21756(15) 0.29893(12) 0.0702(6) Uani 1 1 d . B . C44 C -0.4930(3) 0.2718(3) 0.2880(2) 0.1004(9) Uani 1 1 d . . . F4A F -0.5981(12) 0.2206(6) 0.2478(9) 0.184(6) Uani 0.545(16) 1 d P B 1 F5A F -0.5467(15) 0.3091(11) 0.3396(5) 0.170(5) Uani 0.545(16) 1 d P B 1 F6A F -0.4617(8) 0.3305(7) 0.2683(10) 0.163(6) Uani 0.545(16) 1 d P B 1 F4B F -0.4559(19) 0.3568(7) 0.3331(7) 0.174(6) Uani 0.455(16) 1 d P B 2 F5B F -0.4927(18) 0.2894(17) 0.2373(8) 0.209(10) Uani 0.455(16) 1 d P B 2 F6B F -0.6039(10) 0.2495(13) 0.2958(13) 0.184(8) Uani 0.455(16) 1 d P B 2 C41 C -0.3951(2) 0.17367(18) 0.34033(14) 0.0868(8) Uani 1 1 d . . . H41 H -0.4674 0.1781 0.3621 0.104 Uiso 1 1 calc R B . C42 C -0.2964(2) 0.12319(16) 0.34950(12) 0.0778(7) Uani 1 1 d . B . H42 H -0.3028 0.0938 0.3777 0.093 Uiso 1 1 calc R . . C45 C 0.94789(18) 0.52850(11) 0.12330(8) 0.0476(4) Uani 1 1 d . . . C49 C 1.05573(18) 0.52838(11) 0.09343(8) 0.0461(4) Uani 1 1 d . . . C50 C 1.13566(18) 0.60870(11) 0.09277(8) 0.0461(4) Uani 1 1 d . . . C51 C 1.1197(2) 0.69808(12) 0.11641(9) 0.0551(5) Uani 1 1 d . . . H51 H 1.0526 0.7173 0.1403 0.066 Uiso 1 1 calc R . . C52 C 1.2049(2) 0.75824(13) 0.10397(10) 0.0625(5) Uani 1 1 d . . . H52 H 1.1935 0.8182 0.1191 0.075 Uiso 1 1 calc R . . C53 C 1.3064(2) 0.73147(14) 0.06967(10) 0.0667(6) Uani 1 1 d . . . H53 H 1.3613 0.7731 0.0611 0.080 Uiso 1 1 calc R . . C54 C 1.3269(2) 0.64314(13) 0.04789(10) 0.0604(5) Uani 1 1 d . . . H54 H 1.3970 0.6250 0.0257 0.073 Uiso 1 1 calc R . . C55 C 1.24197(18) 0.58223(12) 0.05949(8) 0.0485(4) Uani 1 1 d . . . C56 C 1.23432(19) 0.48499(12) 0.03862(8) 0.0496(4) Uani 1 1 d . . . C57 C 1.3160(2) 0.42726(13) 0.00562(9) 0.0600(5) Uani 1 1 d . . . H57 H 1.3965 0.4491 -0.0025 0.072 Uiso 1 1 calc R . . C58 C 1.2768(2) 0.33660(14) -0.01524(10) 0.0659(6) Uani 1 1 d . . . H58 H 1.3320 0.2970 -0.0365 0.079 Uiso 1 1 calc R . . C59 C 1.1562(2) 0.30527(13) -0.00456(9) 0.0644(6) Uani 1 1 d . . . H59 H 1.1280 0.2443 -0.0213 0.077 Uiso 1 1 calc R . . C60 C 1.0755(2) 0.36183(12) 0.03043(9) 0.0551(5) Uani 1 1 d . . . H60 H 0.9942 0.3393 0.0374 0.066 Uiso 1 1 calc R . . C61 C 1.11764(18) 0.45264(11) 0.05487(8) 0.0468(4) Uani 1 1 d . . . C46 C 0.84686(18) 0.46182(12) 0.12657(8) 0.0488(4) Uani 1 1 d . . . C62 C 0.84186(19) 0.37895(12) 0.12868(9) 0.0520(5) Uani 1 1 d . . . C63 C 0.9550(2) 0.33252(12) 0.14160(9) 0.0545(5) Uani 1 1 d . . . C64 C 1.0899(2) 0.36310(14) 0.16319(9) 0.0630(5) Uani 1 1 d . . . H64 H 1.1222 0.4221 0.1716 0.076 Uiso 1 1 calc R . . C65 C 1.1766(3) 0.30428(17) 0.17219(11) 0.0793(7) Uani 1 1 d . . . H65 H 1.2679 0.3237 0.1865 0.095 Uiso 1 1 calc R . . C66 C 1.1268(4) 0.21660(18) 0.15979(13) 0.0943(9) Uani 1 1 d . . . H66 H 1.1859 0.1773 0.1650 0.113 Uiso 1 1 calc R . . C67 C 0.9925(3) 0.18670(16) 0.14005(12) 0.0881(8) Uani 1 1 d . . . H67 H 0.9605 0.1279 0.1325 0.106 Uiso 1 1 calc R . . C68 C 0.9052(3) 0.24456(13) 0.13154(10) 0.0653(6) Uani 1 1 d . . . C69 C 0.7595(3) 0.23269(13) 0.11378(10) 0.0653(6) Uani 1 1 d . . . C70 C 0.6647(3) 0.15856(16) 0.09785(11) 0.0877(8) Uani 1 1 d . . . H70 H 0.6911 0.1043 0.0969 0.105 Uiso 1 1 calc R . . C71 C 0.5309(4) 0.16650(19) 0.08340(13) 0.0974(9) Uani 1 1 d . . . H71 H 0.4666 0.1172 0.0730 0.117 Uiso 1 1 calc R . . C72 C 0.4910(3) 0.24589(18) 0.08414(11) 0.0834(7) Uani 1 1 d . . . H72 H 0.4000 0.2499 0.0745 0.100 Uiso 1 1 calc R . . C73 C 0.5843(2) 0.32019(15) 0.09911(10) 0.0681(6) Uani 1 1 d . . . H73 H 0.5566 0.3735 0.0985 0.082 Uiso 1 1 calc R . . C74 C 0.7192(2) 0.31455(13) 0.11495(9) 0.0573(5) Uani 1 1 d . . . C47 C 0.74140(19) 0.52611(12) 0.13406(9) 0.0514(5) Uani 1 1 d . . . H47 H 0.6877 0.5147 0.0923 0.062 Uiso 1 1 calc R . . C75 C 0.64921(18) 0.53609(12) 0.18170(9) 0.0520(5) Uani 1 1 d . . . C76 C 0.5248(2) 0.56316(14) 0.17064(10) 0.0636(5) Uani 1 1 d . . . H76 H 0.5007 0.5755 0.1341 0.076 Uiso 1 1 calc R . . C77 C 0.4360(2) 0.57213(15) 0.21255(11) 0.0704(6) Uani 1 1 d . . . H77 H 0.3521 0.5892 0.2038 0.084 Uiso 1 1 calc R . . C78 C 0.4711(2) 0.55583(13) 0.26725(10) 0.0618(5) Uani 1 1 d . C . C87 C 0.3733(3) 0.5623(2) 0.31158(14) 0.0812(7) Uani 1 1 d . . . F7A F 0.3103(13) 0.4851(4) 0.3022(6) 0.134(5) Uani 0.522(15) 1 d P C 1 F8A F 0.4295(9) 0.5857(12) 0.3697(3) 0.160(6) Uani 0.522(15) 1 d P C 1 F9A F 0.2906(16) 0.6157(13) 0.3111(10) 0.199(8) Uani 0.522(15) 1 d P C 1 F7B F 0.3684(15) 0.6438(6) 0.3465(6) 0.158(6) Uani 0.478(15) 1 d P C 2 F8B F 0.2474(5) 0.5390(12) 0.2831(2) 0.128(5) Uani 0.478(15) 1 d P C 2 F9B F 0.3947(16) 0.5226(16) 0.3495(10) 0.198(9) Uani 0.478(15) 1 d P C 2 C79 C 0.5954(2) 0.53070(14) 0.27963(10) 0.0661(6) Uani 1 1 d . . . H79 H 0.6203 0.5204 0.3169 0.079 Uiso 1 1 calc R C . C80 C 0.6831(2) 0.52074(14) 0.23730(10) 0.0624(5) Uani 1 1 d . C . H80 H 0.7666 0.5034 0.2462 0.075 Uiso 1 1 calc R . . C48 C 0.86165(19) 0.60271(12) 0.14750(9) 0.0505(4) Uani 1 1 d . . . H48 H 0.8468 0.6347 0.1183 0.061 Uiso 1 1 calc R . . C81 C 0.89829(18) 0.66606(12) 0.21534(9) 0.0503(4) Uani 1 1 d . . . C82 C 0.8361(2) 0.74149(14) 0.23569(11) 0.0714(6) Uani 1 1 d . . . H82 H 0.7739 0.7535 0.2069 0.086 Uiso 1 1 calc R . . C83 C 0.8644(3) 0.79953(15) 0.29795(11) 0.0803(7) Uani 1 1 d . . . H83 H 0.8202 0.8497 0.3108 0.096 Uiso 1 1 calc R . . C84 C 0.9569(2) 0.78395(14) 0.34108(10) 0.0675(6) Uani 1 1 d . D . C88 C 0.9884(4) 0.8475(2) 0.40828(13) 0.0935(8) Uani 1 1 d . . . F10A F 0.8883(10) 0.8892(11) 0.4286(5) 0.163(7) Uani 0.508(18) 1 d P D 1 F11A F 1.0270(18) 0.8137(5) 0.4472(3) 0.137(5) Uani 0.508(18) 1 d P D 1 F12A F 1.0867(17) 0.9122(8) 0.4169(3) 0.160(6) Uani 0.508(18) 1 d P D 1 F10B F 1.1032(14) 0.8488(13) 0.4373(7) 0.214(10) Uani 0.492(18) 1 d P D 2 F11B F 0.966(3) 0.9249(6) 0.4167(4) 0.184(9) Uani 0.492(18) 1 d P D 2 F12B F 0.911(2) 0.8191(12) 0.4421(5) 0.213(8) Uani 0.492(18) 1 d P D 2 C85 C 1.0196(3) 0.70925(16) 0.32128(11) 0.0806(7) Uani 1 1 d . . . H85 H 1.0822 0.6975 0.3501 0.097 Uiso 1 1 calc R D . C86 C 0.9908(2) 0.65126(15) 0.25894(11) 0.0736(6) Uani 1 1 d . D . H86 H 1.0351 0.6011 0.2462 0.088 Uiso 1 1 calc R . . C89 C 0.4743(16) 0.5798(10) 0.5193(7) 0.51(3) Uani 0.50 1 d PD . . H89A H 0.4930 0.6205 0.5632 0.616 Uiso 0.50 1 calc PR . . H89B H 0.4333 0.6091 0.4924 0.616 Uiso 0.50 1 calc PR . . Cl Cl 0.6272(5) 0.5281(4) 0.4914(2) 0.555(4) Uani 1 1 d 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 C1 0.0556(12) 0.0508(11) 0.0639(13) 0.0248(10) 0.0092(10) 0.0107(9) C5 0.0596(12) 0.0438(11) 0.0626(13) 0.0197(9) 0.0071(10) 0.0120(9) C6 0.0618(13) 0.0406(10) 0.0682(13) 0.0162(9) 0.0017(10) 0.0114(9) C7 0.0615(14) 0.0574(13) 0.0845(15) 0.0228(11) 0.0032(12) 0.0064(11) C8 0.0655(15) 0.0589(14) 0.104(2) 0.0200(13) -0.0041(14) 0.0036(11) C9 0.0761(18) 0.0579(14) 0.101(2) 0.0157(13) -0.0187(15) 0.0067(12) C10 0.097(2) 0.0470(12) 0.0681(14) 0.0094(10) -0.0094(14) 0.0148(12) C11 0.0756(15) 0.0367(10) 0.0675(14) 0.0145(9) 0.0006(11) 0.0151(10) C12 0.0824(16) 0.0385(10) 0.0599(13) 0.0172(9) 0.0130(11) 0.0189(10) C13 0.104(2) 0.0564(13) 0.0682(15) 0.0240(11) 0.0172(14) 0.0214(13) C14 0.117(2) 0.0633(14) 0.0792(17) 0.0338(13) 0.0415(16) 0.0275(15) C15 0.0793(16) 0.0603(14) 0.0973(19) 0.0393(13) 0.0336(14) 0.0203(12) C16 0.0720(15) 0.0485(11) 0.0725(14) 0.0275(10) 0.0162(11) 0.0170(10) C17 0.0645(14) 0.0402(10) 0.0652(13) 0.0204(9) 0.0124(10) 0.0170(9) C2 0.0594(13) 0.0577(12) 0.0574(12) 0.0248(10) 0.0095(10) 0.0092(10) C18 0.0575(13) 0.0607(12) 0.0591(12) 0.0284(10) 0.0064(10) 0.0059(10) C19 0.0608(13) 0.0572(12) 0.0614(12) 0.0300(10) 0.0070(10) 0.0098(10) C20 0.0739(15) 0.0611(14) 0.0758(15) 0.0279(12) -0.0039(12) 0.0133(11) C21 0.0957(19) 0.0661(15) 0.0875(17) 0.0237(13) -0.0035(15) 0.0256(14) C22 0.0910(19) 0.0794(17) 0.0973(19) 0.0343(15) 0.0063(15) 0.0356(14) C23 0.0682(15) 0.0868(17) 0.0850(17) 0.0427(15) 0.0033(13) 0.0210(13) C24 0.0569(13) 0.0696(14) 0.0659(13) 0.0383(11) 0.0086(10) 0.0095(11) C25 0.0602(13) 0.0752(14) 0.0588(12) 0.0370(11) 0.0054(10) 0.0022(11) C26 0.0684(15) 0.0981(19) 0.0684(15) 0.0423(14) 0.0017(12) 0.0045(13) C27 0.0865(19) 0.111(2) 0.0643(15) 0.0275(16) -0.0098(13) -0.0020(17) C28 0.103(2) 0.097(2) 0.0701(16) 0.0106(14) -0.0042(15) 0.0085(17) C29 0.0861(17) 0.0833(17) 0.0652(14) 0.0172(13) -0.0009(13) 0.0140(14) C30 0.0633(13) 0.0689(14) 0.0564(12) 0.0288(11) 0.0065(10) 0.0050(11) C3 0.0708(14) 0.0693(14) 0.0532(11) 0.0274(10) 0.0124(10) 0.0153(11) C31 0.0588(13) 0.0646(13) 0.0552(12) 0.0200(10) 0.0077(10) 0.0111(10) C32 0.0675(14) 0.0641(14) 0.0782(15) 0.0233(12) 0.0257(12) 0.0127(11) C33 0.0767(16) 0.0726(16) 0.0883(16) 0.0349(13) 0.0293(13) 0.0095(13) C34 0.0768(16) 0.0667(14) 0.0798(15) 0.0275(12) 0.0177(13) 0.0151(12) C43 0.107(3) 0.088(2) 0.126(3) 0.053(2) 0.041(2) 0.034(2) F1A 0.139(4) 0.102(3) 0.126(4) 0.072(3) 0.036(3) 0.031(3) F2A 0.145(5) 0.177(7) 0.291(12) 0.164(8) 0.125(6) 0.106(5) F3A 0.198(9) 0.066(2) 0.149(4) 0.029(2) -0.010(5) 0.004(3) F1B 0.29(2) 0.091(5) 0.155(9) 0.048(6) 0.102(10) 0.109(10) F2B 0.23(2) 0.145(13) 0.74(5) 0.25(2) 0.29(3) 0.093(14) F3B 0.41(3) 0.172(10) 0.27(2) 0.097(13) -0.18(2) 0.074(16) C35 0.1024(19) 0.0763(16) 0.0750(15) 0.0242(13) 0.0316(14) 0.0346(14) C36 0.0962(18) 0.0783(16) 0.0617(13) 0.0287(12) 0.0283(12) 0.0269(14) C4 0.0604(13) 0.0618(12) 0.0667(13) 0.0326(10) 0.0155(10) 0.0099(10) C37 0.0542(12) 0.0600(12) 0.0641(12) 0.0268(10) 0.0156(10) 0.0064(10) C38 0.0582(13) 0.0655(13) 0.0592(12) 0.0252(10) 0.0150(10) 0.0103(10) C39 0.0652(14) 0.0676(14) 0.0654(13) 0.0296(11) 0.0085(11) 0.0103(11) C40 0.0553(13) 0.0685(14) 0.0897(16) 0.0316(12) 0.0129(12) 0.0110(11) C44 0.080(2) 0.098(3) 0.132(3) 0.045(2) 0.028(2) 0.034(2) F4A 0.115(6) 0.130(4) 0.270(11) 0.074(6) -0.093(7) 0.004(4) F5A 0.140(9) 0.197(11) 0.185(7) 0.057(6) 0.050(6) 0.109(8) F6A 0.120(4) 0.106(5) 0.329(17) 0.137(7) 0.078(7) 0.049(4) F4B 0.198(11) 0.126(6) 0.196(9) 0.043(6) 0.025(8) 0.091(7) F5B 0.214(14) 0.36(2) 0.162(8) 0.182(11) 0.089(7) 0.215(16) F6B 0.051(5) 0.241(18) 0.33(2) 0.177(16) 0.068(9) 0.053(7) C41 0.0610(15) 0.0987(19) 0.122(2) 0.0550(17) 0.0426(15) 0.0197(14) C42 0.0695(15) 0.0881(17) 0.1016(18) 0.0571(15) 0.0361(14) 0.0176(13) C45 0.0518(11) 0.0401(10) 0.0521(10) 0.0192(8) 0.0051(9) 0.0078(8) C49 0.0511(11) 0.0398(10) 0.0467(10) 0.0169(8) 0.0021(8) 0.0068(8) C50 0.0500(11) 0.0408(10) 0.0471(10) 0.0176(8) 0.0025(8) 0.0052(8) C51 0.0594(12) 0.0422(11) 0.0626(12) 0.0178(9) 0.0103(10) 0.0059(9) C52 0.0716(14) 0.0389(11) 0.0736(14) 0.0187(10) 0.0080(11) 0.0025(10) C53 0.0696(14) 0.0529(13) 0.0786(14) 0.0285(11) 0.0106(12) -0.0056(11) C54 0.0564(12) 0.0576(13) 0.0710(13) 0.0267(10) 0.0153(10) 0.0052(10) C55 0.0495(11) 0.0465(10) 0.0497(10) 0.0201(8) 0.0022(9) 0.0052(9) C56 0.0561(12) 0.0473(10) 0.0482(10) 0.0208(8) 0.0063(9) 0.0119(9) C57 0.0650(13) 0.0599(13) 0.0626(12) 0.0276(10) 0.0167(10) 0.0169(10) C58 0.0845(16) 0.0574(13) 0.0635(13) 0.0238(10) 0.0226(12) 0.0296(12) C59 0.0917(17) 0.0436(11) 0.0578(12) 0.0168(9) 0.0140(11) 0.0147(11) C60 0.0712(13) 0.0429(11) 0.0510(11) 0.0178(9) 0.0078(10) 0.0066(9) C61 0.0538(11) 0.0411(10) 0.0458(10) 0.0175(8) 0.0042(8) 0.0080(8) C46 0.0517(11) 0.0435(10) 0.0532(11) 0.0206(8) 0.0068(9) 0.0067(8) C62 0.0601(12) 0.0436(10) 0.0558(11) 0.0215(9) 0.0120(9) 0.0073(9) C63 0.0695(14) 0.0478(11) 0.0527(11) 0.0231(9) 0.0146(10) 0.0160(10) C64 0.0762(15) 0.0602(12) 0.0610(12) 0.0287(10) 0.0137(11) 0.0232(11) C65 0.0889(17) 0.0870(18) 0.0735(15) 0.0374(13) 0.0140(13) 0.0420(14) C66 0.129(3) 0.0750(18) 0.0946(19) 0.0415(15) 0.0199(18) 0.0561(18) C67 0.131(3) 0.0549(14) 0.0881(18) 0.0348(13) 0.0159(17) 0.0311(15) C68 0.1015(18) 0.0443(11) 0.0586(12) 0.0251(10) 0.0203(12) 0.0177(11) C69 0.0945(18) 0.0457(12) 0.0577(12) 0.0229(10) 0.0140(11) -0.0005(11) C70 0.134(3) 0.0523(14) 0.0743(16) 0.0266(12) 0.0102(16) -0.0107(15) C71 0.119(3) 0.0788(19) 0.0840(18) 0.0323(15) 0.0025(17) -0.0378(18) C72 0.0838(17) 0.0842(18) 0.0752(16) 0.0286(13) 0.0080(13) -0.0209(14) C73 0.0693(15) 0.0646(14) 0.0678(13) 0.0241(11) 0.0104(11) -0.0052(11) C74 0.0731(14) 0.0487(11) 0.0520(11) 0.0208(9) 0.0141(10) 0.0005(10) C47 0.0497(11) 0.0493(11) 0.0586(11) 0.0252(9) 0.0039(9) 0.0086(9) C75 0.0472(11) 0.0465(10) 0.0633(12) 0.0233(9) 0.0034(9) 0.0076(9) C76 0.0569(13) 0.0685(14) 0.0682(13) 0.0293(11) 0.0030(11) 0.0169(11) C77 0.0505(13) 0.0758(15) 0.0826(16) 0.0248(12) 0.0077(12) 0.0210(11) C78 0.0517(12) 0.0570(12) 0.0710(14) 0.0156(10) 0.0133(11) 0.0069(10) C87 0.0676(18) 0.083(2) 0.0824(19) 0.0163(16) 0.0166(15) 0.0097(16) F7A 0.126(7) 0.097(4) 0.163(7) 0.015(4) 0.080(6) -0.029(4) F8A 0.122(5) 0.232(12) 0.075(3) -0.002(5) 0.034(3) -0.035(7) F9A 0.177(12) 0.257(16) 0.294(17) 0.187(13) 0.168(11) 0.164(12) F7B 0.175(10) 0.113(5) 0.138(8) -0.033(5) 0.085(7) 0.000(6) F8B 0.053(3) 0.200(11) 0.098(3) 0.019(5) 0.014(2) -0.009(4) F9B 0.165(11) 0.33(2) 0.266(16) 0.248(16) 0.148(11) 0.158(12) C79 0.0645(14) 0.0727(14) 0.0677(13) 0.0328(11) 0.0114(11) 0.0125(11) C80 0.0500(12) 0.0759(14) 0.0716(13) 0.0380(11) 0.0090(10) 0.0179(10) C48 0.0557(11) 0.0430(10) 0.0589(11) 0.0255(9) 0.0082(9) 0.0119(9) C81 0.0508(11) 0.0430(10) 0.0620(12) 0.0239(9) 0.0111(9) 0.0101(8) C82 0.0838(16) 0.0570(13) 0.0711(14) 0.0208(11) 0.0014(12) 0.0275(12) C83 0.0980(18) 0.0580(13) 0.0782(16) 0.0135(12) 0.0107(14) 0.0337(13) C84 0.0770(15) 0.0626(13) 0.0618(13) 0.0199(11) 0.0132(11) 0.0131(11) C88 0.119(3) 0.090(2) 0.0685(18) 0.0216(16) 0.0188(19) 0.026(2) F10A 0.148(6) 0.201(14) 0.097(6) -0.016(7) 0.036(3) 0.079(8) F11A 0.236(14) 0.106(4) 0.058(3) 0.029(3) -0.005(5) 0.009(6) F12A 0.217(11) 0.108(7) 0.102(4) -0.012(4) 0.037(6) -0.075(7) F10B 0.140(8) 0.197(16) 0.168(10) -0.070(9) -0.073(7) 0.050(8) F11B 0.36(3) 0.085(5) 0.080(4) 0.004(3) 0.009(11) 0.078(10) F12B 0.260(15) 0.256(14) 0.087(4) 0.019(6) 0.069(7) -0.040(12) C85 0.0893(17) 0.0839(17) 0.0651(14) 0.0231(13) 0.0002(12) 0.0334(14) C86 0.0796(16) 0.0687(14) 0.0694(14) 0.0191(12) 0.0044(12) 0.0357(12) C89 1.13(8) 0.198(14) 0.130(9) 0.014(10) 0.14(2) -0.23(3) Cl 0.458(5) 0.620(9) 0.460(7) 0.102(6) -0.137(5) 0.149(6) _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 C1 C5 1.355(3) . ? C1 C2 1.457(3) . ? C1 C4 1.537(3) . ? C5 C17 1.474(3) . ? C5 C6 1.483(3) . ? C6 C7 1.391(3) . ? C6 C11 1.400(3) . ? C7 C8 1.380(3) . ? C7 H7 0.9300 . ? C8 C9 1.372(4) . ? C8 H8 0.9300 . ? C9 C10 1.378(4) . ? C9 H9 0.9300 . ? C10 C11 1.399(3) . ? C10 H10 0.9300 . ? C11 C12 1.459(3) . ? C12 C13 1.380(3) . ? C12 C17 1.413(3) . ? C13 C14 1.374(4) . ? C13 H13 0.9300 . ? C14 C15 1.390(3) . ? C14 H14 0.9300 . ? C15 C16 1.389(3) . ? C15 H15 0.9300 . ? C16 C17 1.391(3) . ? C16 H16 0.9300 . ? C2 C18 1.359(3) . ? C2 C3 1.527(3) . ? C18 C30 1.477(3) . ? C18 C19 1.479(3) . ? C19 C20 1.383(3) . ? C19 C24 1.405(3) . ? C20 C21 1.387(3) . ? C20 H20 0.9300 . ? C21 C22 1.376(3) . ? C21 H21 0.9300 . ? C22 C23 1.376(3) . ? C22 H22 0.9300 . ? C23 C24 1.379(3) . ? C23 H23 0.9300 . ? C24 C25 1.464(3) . ? C25 C26 1.383(3) . ? C25 C30 1.398(3) . ? C26 C27 1.371(4) . ? C26 H26 0.9300 . ? C27 C28 1.382(4) . ? C27 H27 0.9300 . ? C28 C29 1.377(3) . ? C28 H28 0.9300 . ? C29 C30 1.382(3) . ? C29 H29 0.9300 . ? C3 C31 1.503(3) . ? C3 C4 1.595(3) . ? C3 H3 0.9800 . ? C31 C36 1.384(3) . ? C31 C32 1.385(3) . ? C32 C33 1.377(3) . ? C32 H32 0.9300 . ? C33 C34 1.374(3) . ? C33 H33 0.9300 . ? C34 C35 1.377(3) . ? C34 C43 1.495(4) . ? C43 F2B 1.195(17) . ? C43 F3B 1.248(13) . ? C43 F1B 1.279(11) . ? C43 F2A 1.298(6) . ? C43 F1A 1.311(6) . ? C43 F3A 1.335(8) . ? C35 C36 1.372(3) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C4 C37 1.498(3) . ? C4 H4 0.9800 . ? C37 C42 1.375(3) . ? C37 C38 1.385(3) . ? C38 C39 1.370(3) . ? C38 H38 0.9300 . ? C39 C40 1.377(3) . ? C39 H39 0.9300 . ? C40 C41 1.374(3) . ? C40 C44 1.488(4) . ? C44 F6B 1.209(8) . ? C44 F6A 1.223(8) . ? C44 F5B 1.286(9) . ? C44 F4A 1.318(8) . ? C44 F5A 1.330(8) . ? C44 F4B 1.386(11) . ? C41 C42 1.376(3) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? C45 C49 1.361(3) . ? C45 C46 1.459(3) . ? C45 C48 1.525(2) . ? C49 C61 1.473(2) . ? C49 C50 1.485(2) . ? C50 C51 1.385(2) . ? C50 C55 1.405(3) . ? C51 C52 1.381(3) . ? C51 H51 0.9300 . ? C52 C53 1.376(3) . ? C52 H52 0.9300 . ? C53 C54 1.380(3) . ? C53 H53 0.9300 . ? C54 C55 1.378(3) . ? C54 H54 0.9300 . ? C55 C56 1.468(3) . ? C56 C57 1.381(3) . ? C56 C61 1.402(3) . ? C57 C58 1.382(3) . ? C57 H57 0.9300 . ? C58 C59 1.370(3) . ? C58 H58 0.9300 . ? C59 C60 1.383(3) . ? C59 H59 0.9300 . ? C60 C61 1.386(3) . ? C60 H60 0.9300 . ? C46 C62 1.356(2) . ? C46 C47 1.528(3) . ? C62 C63 1.468(3) . ? C62 C74 1.484(3) . ? C63 C64 1.379(3) . ? C63 C68 1.402(3) . ? C64 C65 1.389(3) . ? C64 H64 0.9300 . ? C65 C66 1.386(4) . ? C65 H65 0.9300 . ? C66 C67 1.368(4) . ? C66 H66 0.9300 . ? C67 C68 1.378(3) . ? C67 H67 0.9300 . ? C68 C69 1.456(3) . ? C69 C70 1.387(3) . ? C69 C74 1.407(3) . ? C70 C71 1.377(4) . ? C70 H70 0.9300 . ? C71 C72 1.369(4) . ? C71 H71 0.9300 . ? C72 C73 1.383(3) . ? C72 H72 0.9300 . ? C73 C74 1.383(3) . ? C73 H73 0.9300 . ? C47 C75 1.498(3) . ? C47 C48 1.588(3) . ? C47 H47 0.9800 . ? C75 C80 1.381(3) . ? C75 C76 1.384(3) . ? C76 C77 1.375(3) . ? C76 H76 0.9300 . ? C77 C78 1.372(3) . ? C77 H77 0.9300 . ? C78 C79 1.374(3) . ? C78 C87 1.490(3) . ? C87 F9A 1.248(6) . ? C87 F9B 1.252(6) . ? C87 F8A 1.281(8) . ? C87 F7B 1.288(8) . ? C87 F7A 1.293(6) . ? C87 F8B 1.313(5) . ? C79 C80 1.373(3) . ? C79 H79 0.9300 . ? C80 H80 0.9300 . ? C48 C81 1.504(3) . ? C48 H48 0.9800 . ? C81 C86 1.370(3) . ? C81 C82 1.376(3) . ? C82 C83 1.378(3) . ? C82 H82 0.9300 . ? C83 C84 1.369(3) . ? C83 H83 0.9300 . ? C84 C85 1.368(3) . ? C84 C88 1.492(3) . ? C88 F11A 1.234(7) . ? C88 F11B 1.242(7) . ? C88 F10B 1.254(8) . ? C88 F10A 1.304(8) . ? C88 F12A 1.331(7) . ? C88 F12B 1.331(10) . ? C85 C86 1.379(3) . ? C85 H85 0.9300 . ? C86 H86 0.9300 . ? C89 Cl 1.879(11) 2_666 ? C89 Cl 1.892(14) . ? C89 H89A 0.9700 . ? C89 H89B 0.9700 . ? 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 C5 C1 C2 137.28(19) . . ? C5 C1 C4 129.84(18) . . ? C2 C1 C4 91.21(16) . . ? C1 C5 C17 128.86(19) . . ? C1 C5 C6 125.10(19) . . ? C17 C5 C6 105.34(17) . . ? C7 C6 C11 120.2(2) . . ? C7 C6 C5 131.0(2) . . ? C11 C6 C5 108.81(19) . . ? C8 C7 C6 119.0(2) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C9 C8 C7 120.8(3) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 121.3(2) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C9 C10 C11 118.8(2) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C10 C11 C6 119.7(2) . . ? C10 C11 C12 131.6(2) . . ? C6 C11 C12 108.68(18) . . ? C13 C12 C17 120.6(2) . . ? C13 C12 C11 131.1(2) . . ? C17 C12 C11 108.32(18) . . ? C14 C13 C12 119.3(2) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 120.9(2) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C16 C15 C14 120.6(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 119.0(2) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C16 C17 C12 119.55(19) . . ? C16 C17 C5 131.50(19) . . ? C12 C17 C5 108.74(18) . . ? C18 C2 C1 137.39(19) . . ? C18 C2 C3 127.75(18) . . ? C1 C2 C3 91.91(16) . . ? C2 C18 C30 124.31(19) . . ? C2 C18 C19 129.84(19) . . ? C30 C18 C19 105.59(17) . . ? C20 C19 C24 119.47(19) . . ? C20 C19 C18 131.89(19) . . ? C24 C19 C18 108.47(18) . . ? C19 C20 C21 119.1(2) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C22 C21 C20 121.0(2) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C23 120.6(2) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C24 119.2(2) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C23 C24 C19 120.7(2) . . ? C23 C24 C25 130.7(2) . . ? C19 C24 C25 108.59(18) . . ? C26 C25 C30 121.0(2) . . ? C26 C25 C24 130.5(2) . . ? C30 C25 C24 108.47(18) . . ? C27 C26 C25 118.5(2) . . ? C27 C26 H26 120.8 . . ? C25 C26 H26 120.8 . . ? C26 C27 C28 121.0(2) . . ? C26 C27 H27 119.5 . . ? C28 C27 H27 119.5 . . ? C29 C28 C27 120.8(3) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C30 119.2(2) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C29 C30 C25 119.5(2) . . ? C29 C30 C18 131.5(2) . . ? C25 C30 C18 108.89(18) . . ? C31 C3 C2 119.23(18) . . ? C31 C3 C4 112.11(16) . . ? C2 C3 C4 86.50(15) . . ? C31 C3 H3 112.2 . . ? C2 C3 H3 112.2 . . ? C4 C3 H3 112.2 . . ? C36 C31 C32 118.2(2) . . ? C36 C31 C3 119.2(2) . . ? C32 C31 C3 122.18(19) . . ? C33 C32 C31 120.8(2) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C34 C33 C32 120.2(2) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C33 C34 C35 119.4(2) . . ? C33 C34 C43 120.5(2) . . ? C35 C34 C43 120.1(2) . . ? F2B C43 F3B 113.5(16) . . ? F2B C43 F1B 102.8(15) . . ? F3B C43 F1B 109.1(14) . . ? F2A C43 F1A 105.2(6) . . ? F2A C43 F3A 107.9(6) . . ? F1A C43 F3A 100.4(5) . . ? F2B C43 C34 111.3(9) . . ? F3B C43 C34 109.0(8) . . ? F1B C43 C34 111.1(6) . . ? F2A C43 C34 114.8(4) . . ? F1A C43 C34 113.8(3) . . ? F3A C43 C34 113.5(4) . . ? C36 C35 C34 120.3(2) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C31 120.9(2) . . ? C35 C36 H36 119.6 . . ? C31 C36 H36 119.6 . . ? C37 C4 C1 122.65(17) . . ? C37 C4 C3 116.13(17) . . ? C1 C4 C3 86.48(15) . . ? C37 C4 H4 109.8 . . ? C1 C4 H4 109.8 . . ? C3 C4 H4 109.8 . . ? C42 C37 C38 118.0(2) . . ? C42 C37 C4 119.01(19) . . ? C38 C37 C4 122.64(18) . . ? C39 C38 C37 120.88(19) . . ? C39 C38 H38 119.6 . . ? C37 C38 H38 119.6 . . ? C38 C39 C40 120.3(2) . . ? C38 C39 H39 119.8 . . ? C40 C39 H39 119.8 . . ? C41 C40 C39 119.5(2) . . ? C41 C40 C44 120.5(3) . . ? C39 C40 C44 120.0(3) . . ? F6B C44 F5B 113.7(8) . . ? F6A C44 F4A 106.9(7) . . ? F6A C44 F5A 107.3(7) . . ? F4A C44 F5A 101.6(7) . . ? F6B C44 F4B 104.6(8) . . ? F5B C44 F4B 99.5(9) . . ? F6B C44 C40 116.2(6) . . ? F6A C44 C40 117.0(4) . . ? F5B C44 C40 113.9(5) . . ? F4A C44 C40 110.8(5) . . ? F5A C44 C40 112.0(5) . . ? F4B C44 C40 106.7(5) . . ? C40 C41 C42 119.7(2) . . ? C40 C41 H41 120.1 . . ? C42 C41 H41 120.1 . . ? C37 C42 C41 121.5(2) . . ? C37 C42 H42 119.3 . . ? C41 C42 H42 119.3 . . ? C49 C45 C46 136.45(17) . . ? C49 C45 C48 128.74(16) . . ? C46 C45 C48 92.06(14) . . ? C45 C49 C61 129.45(16) . . ? C45 C49 C50 125.46(16) . . ? C61 C49 C50 105.08(15) . . ? C51 C50 C55 119.19(17) . . ? C51 C50 C49 131.89(17) . . ? C55 C50 C49 108.89(15) . . ? C52 C51 C50 119.00(19) . . ? C52 C51 H51 120.5 . . ? C50 C51 H51 120.5 . . ? C53 C52 C51 121.46(19) . . ? C53 C52 H52 119.3 . . ? C51 C52 H52 119.3 . . ? C52 C53 C54 120.24(19) . . ? C52 C53 H53 119.9 . . ? C54 C53 H53 119.9 . . ? C55 C54 C53 118.93(19) . . ? C55 C54 H54 120.5 . . ? C53 C54 H54 120.5 . . ? C54 C55 C50 121.10(17) . . ? C54 C55 C56 130.58(18) . . ? C50 C55 C56 108.18(16) . . ? C57 C56 C61 120.76(17) . . ? C57 C56 C55 130.89(18) . . ? C61 C56 C55 108.27(16) . . ? C56 C57 C58 119.2(2) . . ? C56 C57 H57 120.4 . . ? C58 C57 H57 120.4 . . ? C59 C58 C57 119.84(19) . . ? C59 C58 H58 120.1 . . ? C57 C58 H58 120.1 . . ? C58 C59 C60 121.78(19) . . ? C58 C59 H59 119.1 . . ? C60 C59 H59 119.1 . . ? C59 C60 C61 118.8(2) . . ? C59 C60 H60 120.6 . . ? C61 C60 H60 120.6 . . ? C60 C61 C56 119.07(17) . . ? C60 C61 C49 131.61(18) . . ? C56 C61 C49 109.13(15) . . ? C62 C46 C45 137.44(18) . . ? C62 C46 C47 131.11(17) . . ? C45 C46 C47 91.20(14) . . ? C46 C62 C63 127.79(18) . . ? C46 C62 C74 126.41(18) . . ? C63 C62 C74 105.73(16) . . ? C64 C63 C68 120.57(19) . . ? C64 C63 C62 130.72(18) . . ? C68 C63 C62 108.63(19) . . ? C63 C64 C65 118.9(2) . . ? C63 C64 H64 120.6 . . ? C65 C64 H64 120.6 . . ? C66 C65 C64 119.9(3) . . ? C66 C65 H65 120.0 . . ? C64 C65 H65 120.0 . . ? C67 C66 C65 121.3(2) . . ? C67 C66 H66 119.4 . . ? C65 C66 H66 119.4 . . ? C66 C67 C68 119.4(2) . . ? C66 C67 H67 120.3 . . ? C68 C67 H67 120.3 . . ? C67 C68 C63 119.9(2) . . ? C67 C68 C69 131.3(2) . . ? C63 C68 C69 108.80(18) . . ? C70 C69 C74 120.3(2) . . ? C70 C69 C68 131.2(2) . . ? C74 C69 C68 108.44(18) . . ? C71 C70 C69 119.0(2) . . ? C71 C70 H70 120.5 . . ? C69 C70 H70 120.5 . . ? C72 C71 C70 121.0(2) . . ? C72 C71 H71 119.5 . . ? C70 C71 H71 119.5 . . ? C71 C72 C73 120.8(3) . . ? C71 C72 H72 119.6 . . ? C73 C72 H72 119.6 . . ? C72 C73 C74 119.5(2) . . ? C72 C73 H73 120.3 . . ? C74 C73 H73 120.3 . . ? C73 C74 C69 119.43(19) . . ? C73 C74 C62 132.19(19) . . ? C69 C74 C62 108.12(19) . . ? C75 C47 C46 121.63(15) . . ? C75 C47 C48 119.10(16) . . ? C46 C47 C48 87.09(13) . . ? C75 C47 H47 109.0 . . ? C46 C47 H47 109.0 . . ? C48 C47 H47 109.0 . . ? C80 C75 C76 117.70(19) . . ? C80 C75 C47 123.05(17) . . ? C76 C75 C47 119.24(17) . . ? C77 C76 C75 121.4(2) . . ? C77 C76 H76 119.3 . . ? C75 C76 H76 119.3 . . ? C78 C77 C76 119.97(19) . . ? C78 C77 H77 120.0 . . ? C76 C77 H77 120.0 . . ? C77 C78 C79 119.4(2) . . ? C77 C78 C87 120.1(2) . . ? C79 C78 C87 120.5(2) . . ? F9A C87 F8A 105.6(7) . . ? F9B C87 F7B 105.4(8) . . ? F9A C87 F7A 109.7(6) . . ? F8A C87 F7A 100.8(6) . . ? F9B C87 F8B 108.3(7) . . ? F7B C87 F8B 100.0(6) . . ? F9A C87 C78 114.9(4) . . ? F9B C87 C78 116.2(4) . . ? F8A C87 C78 113.3(4) . . ? F7B C87 C78 111.5(5) . . ? F7A C87 C78 111.5(3) . . ? F8B C87 C78 113.8(3) . . ? C80 C79 C78 120.4(2) . . ? C80 C79 H79 119.8 . . ? C78 C79 H79 119.8 . . ? C79 C80 C75 121.09(19) . . ? C79 C80 H80 119.5 . . ? C75 C80 H80 119.5 . . ? C81 C48 C45 118.54(15) . . ? C81 C48 C47 115.36(15) . . ? C45 C48 C47 86.57(13) . . ? C81 C48 H48 111.4 . . ? C45 C48 H48 111.4 . . ? C47 C48 H48 111.4 . . ? C86 C81 C82 117.68(19) . . ? C86 C81 C48 122.57(17) . . ? C82 C81 C48 119.74(17) . . ? C81 C82 C83 121.2(2) . . ? C81 C82 H82 119.4 . . ? C83 C82 H82 119.4 . . ? C84 C83 C82 120.5(2) . . ? C84 C83 H83 119.7 . . ? C82 C83 H83 119.7 . . ? C85 C84 C83 118.7(2) . . ? C85 C84 C88 120.9(2) . . ? C83 C84 C88 120.4(2) . . ? F11B C88 F10B 109.6(8) . . ? F11A C88 F10A 105.8(7) . . ? F11A C88 F12A 104.6(6) . . ? F10A C88 F12A 104.5(6) . . ? F11B C88 F12B 105.7(8) . . ? F10B C88 F12B 100.8(8) . . ? F11A C88 C84 114.5(4) . . ? F11B C88 C84 115.3(4) . . ? F10B C88 C84 115.5(5) . . ? F10A C88 C84 114.2(5) . . ? F12A C88 C84 112.2(4) . . ? F12B C88 C84 108.4(6) . . ? C84 C85 C86 120.6(2) . . ? C84 C85 H85 119.7 . . ? C86 C85 H85 119.7 . . ? C81 C86 C85 121.3(2) . . ? C81 C86 H86 119.4 . . ? C85 C86 H86 119.4 . . ? Cl C89 Cl 95.4(8) 2_666 . ? Cl C89 H89A 112.7 2_666 . ? Cl C89 H89A 112.7 . . ? Cl C89 H89B 112.7 2_666 . ? Cl C89 H89B 112.7 . . ? H89A C89 H89B 110.1 . . ? 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 C2 C1 C5 C17 -9.7(4) . . . . ? C4 C1 C5 C17 151.1(2) . . . . ? C2 C1 C5 C6 -178.7(2) . . . . ? C4 C1 C5 C6 -17.8(3) . . . . ? C1 C5 C6 C7 -14.6(3) . . . . ? C17 C5 C6 C7 174.3(2) . . . . ? C1 C5 C6 C11 167.65(18) . . . . ? C17 C5 C6 C11 -3.5(2) . . . . ? C11 C6 C7 C8 -3.7(3) . . . . ? C5 C6 C7 C8 178.86(19) . . . . ? C6 C7 C8 C9 -0.4(3) . . . . ? C7 C8 C9 C10 2.9(4) . . . . ? C8 C9 C10 C11 -1.4(3) . . . . ? C9 C10 C11 C6 -2.7(3) . . . . ? C9 C10 C11 C12 177.9(2) . . . . ? C7 C6 C11 C10 5.2(3) . . . . ? C5 C6 C11 C10 -176.82(17) . . . . ? C7 C6 C11 C12 -175.25(17) . . . . ? C5 C6 C11 C12 2.7(2) . . . . ? C10 C11 C12 C13 -0.9(4) . . . . ? C6 C11 C12 C13 179.6(2) . . . . ? C10 C11 C12 C17 178.6(2) . . . . ? C6 C11 C12 C17 -0.9(2) . . . . ? C17 C12 C13 C14 -1.2(3) . . . . ? C11 C12 C13 C14 178.2(2) . . . . ? C12 C13 C14 C15 -0.7(3) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C14 C15 C16 C17 0.7(3) . . . . ? C15 C16 C17 C12 -2.5(3) . . . . ? C15 C16 C17 C5 -176.68(19) . . . . ? C13 C12 C17 C16 2.8(3) . . . . ? C11 C12 C17 C16 -176.71(16) . . . . ? C13 C12 C17 C5 178.22(17) . . . . ? C11 C12 C17 C5 -1.3(2) . . . . ? C1 C5 C17 C16 6.9(3) . . . . ? C6 C5 C17 C16 177.54(19) . . . . ? C1 C5 C17 C12 -167.77(19) . . . . ? C6 C5 C17 C12 2.9(2) . . . . ? C5 C1 C2 C18 -49.9(4) . . . . ? C4 C1 C2 C18 144.7(3) . . . . ? C5 C1 C2 C3 149.9(2) . . . . ? C4 C1 C2 C3 -15.50(15) . . . . ? C1 C2 C18 C30 -174.0(2) . . . . ? C3 C2 C18 C30 -19.3(3) . . . . ? C1 C2 C18 C19 -0.8(4) . . . . ? C3 C2 C18 C19 153.9(2) . . . . ? C2 C18 C19 C20 0.7(4) . . . . ? C30 C18 C19 C20 174.9(2) . . . . ? C2 C18 C19 C24 -174.4(2) . . . . ? C30 C18 C19 C24 -0.2(2) . . . . ? C24 C19 C20 C21 -1.8(3) . . . . ? C18 C19 C20 C21 -176.4(2) . . . . ? C19 C20 C21 C22 -0.2(4) . . . . ? C20 C21 C22 C23 1.7(4) . . . . ? C21 C22 C23 C24 -1.1(4) . . . . ? C22 C23 C24 C19 -0.8(3) . . . . ? C22 C23 C24 C25 176.8(2) . . . . ? C20 C19 C24 C23 2.3(3) . . . . ? C18 C19 C24 C23 178.06(19) . . . . ? C20 C19 C24 C25 -175.79(19) . . . . ? C18 C19 C24 C25 0.0(2) . . . . ? C23 C24 C25 C26 3.2(4) . . . . ? C19 C24 C25 C26 -178.9(2) . . . . ? C23 C24 C25 C30 -177.6(2) . . . . ? C19 C24 C25 C30 0.2(2) . . . . ? C30 C25 C26 C27 -0.4(3) . . . . ? C24 C25 C26 C27 178.7(2) . . . . ? C25 C26 C27 C28 -0.4(4) . . . . ? C26 C27 C28 C29 0.2(4) . . . . ? C27 C28 C29 C30 0.7(4) . . . . ? C28 C29 C30 C25 -1.5(4) . . . . ? C28 C29 C30 C18 -178.4(2) . . . . ? C26 C25 C30 C29 1.3(3) . . . . ? C24 C25 C30 C29 -178.0(2) . . . . ? C26 C25 C30 C18 178.90(19) . . . . ? C24 C25 C30 C18 -0.4(2) . . . . ? C2 C18 C30 C29 -7.8(4) . . . . ? C19 C18 C30 C29 177.6(2) . . . . ? C2 C18 C30 C25 174.96(19) . . . . ? C19 C18 C30 C25 0.4(2) . . . . ? C18 C2 C3 C31 98.3(3) . . . . ? C1 C2 C3 C31 -98.5(2) . . . . ? C18 C2 C3 C4 -148.2(2) . . . . ? C1 C2 C3 C4 14.95(15) . . . . ? C2 C3 C31 C36 -176.13(19) . . . . ? C4 C3 C31 C36 85.1(2) . . . . ? C2 C3 C31 C32 11.3(3) . . . . ? C4 C3 C31 C32 -87.4(2) . . . . ? C36 C31 C32 C33 -3.4(3) . . . . ? C3 C31 C32 C33 169.2(2) . . . . ? C31 C32 C33 C34 0.1(4) . . . . ? C32 C33 C34 C35 2.5(4) . . . . ? C32 C33 C34 C43 -175.9(3) . . . . ? C33 C34 C43 F2B -51(3) . . . . ? C35 C34 C43 F2B 131(3) . . . . ? C33 C34 C43 F3B 75(3) . . . . ? C35 C34 C43 F3B -103(3) . . . . ? C33 C34 C43 F1B -164.4(16) . . . . ? C35 C34 C43 F1B 17.1(16) . . . . ? C33 C34 C43 F2A 148.8(9) . . . . ? C35 C34 C43 F2A -29.7(10) . . . . ? C33 C34 C43 F1A 27.5(6) . . . . ? C35 C34 C43 F1A -151.0(5) . . . . ? C33 C34 C43 F3A -86.5(7) . . . . ? C35 C34 C43 F3A 95.1(7) . . . . ? C33 C34 C35 C36 -1.9(4) . . . . ? C43 C34 C35 C36 176.5(3) . . . . ? C34 C35 C36 C31 -1.4(4) . . . . ? C32 C31 C36 C35 4.0(3) . . . . ? C3 C31 C36 C35 -168.9(2) . . . . ? C5 C1 C4 C37 -33.3(3) . . . . ? C2 C1 C4 C37 133.84(19) . . . . ? C5 C1 C4 C3 -152.3(2) . . . . ? C2 C1 C4 C3 14.85(14) . . . . ? C31 C3 C4 C37 -18.8(2) . . . . ? C2 C3 C4 C37 -139.06(17) . . . . ? C31 C3 C4 C1 106.04(17) . . . . ? C2 C3 C4 C1 -14.18(14) . . . . ? C1 C4 C37 C42 159.1(2) . . . . ? C3 C4 C37 C42 -97.5(2) . . . . ? C1 C4 C37 C38 -27.3(3) . . . . ? C3 C4 C37 C38 76.1(2) . . . . ? C42 C37 C38 C39 1.4(3) . . . . ? C4 C37 C38 C39 -172.25(19) . . . . ? C37 C38 C39 C40 -0.7(3) . . . . ? C38 C39 C40 C41 -0.5(3) . . . . ? C38 C39 C40 C44 -179.0(3) . . . . ? C41 C40 C44 F6B -27.4(16) . . . . ? C39 C40 C44 F6B 151.1(16) . . . . ? C41 C40 C44 F6A 156.9(11) . . . . ? C39 C40 C44 F6A -24.6(11) . . . . ? C41 C40 C44 F5B -162.5(14) . . . . ? C39 C40 C44 F5B 16.0(15) . . . . ? C41 C40 C44 F4A -80.2(11) . . . . ? C39 C40 C44 F4A 98.3(11) . . . . ? C41 C40 C44 F5A 32.5(11) . . . . ? C39 C40 C44 F5A -149.1(11) . . . . ? C41 C40 C44 F4B 88.8(12) . . . . ? C39 C40 C44 F4B -92.7(11) . . . . ? C39 C40 C41 C42 0.9(4) . . . . ? C44 C40 C41 C42 179.4(3) . . . . ? C38 C37 C42 C41 -1.0(4) . . . . ? C4 C37 C42 C41 172.9(2) . . . . ? C40 C41 C42 C37 -0.2(4) . . . . ? C46 C45 C49 C61 -6.0(3) . . . . ? C48 C45 C49 C61 -161.64(18) . . . . ? C46 C45 C49 C50 172.88(19) . . . . ? C48 C45 C49 C50 17.3(3) . . . . ? C45 C49 C50 C51 -4.7(3) . . . . ? C61 C49 C50 C51 174.45(19) . . . . ? C45 C49 C50 C55 177.49(17) . . . . ? C61 C49 C50 C55 -3.38(19) . . . . ? C55 C50 C51 C52 3.1(3) . . . . ? C49 C50 C51 C52 -174.56(18) . . . . ? C50 C51 C52 C53 -1.2(3) . . . . ? C51 C52 C53 C54 -1.4(3) . . . . ? C52 C53 C54 C55 1.9(3) . . . . ? C53 C54 C55 C50 0.1(3) . . . . ? C53 C54 C55 C56 175.33(19) . . . . ? C51 C50 C55 C54 -2.6(3) . . . . ? C49 C50 C55 C54 175.54(16) . . . . ? C51 C50 C55 C56 -178.78(16) . . . . ? C49 C50 C55 C56 -0.63(19) . . . . ? C54 C55 C56 C57 5.7(3) . . . . ? C50 C55 C56 C57 -178.63(19) . . . . ? C54 C55 C56 C61 -171.01(19) . . . . ? C50 C55 C56 C61 4.7(2) . . . . ? C61 C56 C57 C58 4.5(3) . . . . ? C55 C56 C57 C58 -171.86(19) . . . . ? C56 C57 C58 C59 1.8(3) . . . . ? C57 C58 C59 C60 -4.3(3) . . . . ? C58 C59 C60 C61 0.5(3) . . . . ? C59 C60 C61 C56 5.8(3) . . . . ? C59 C60 C61 C49 -179.75(18) . . . . ? C57 C56 C61 C60 -8.3(3) . . . . ? C55 C56 C61 C60 168.79(16) . . . . ? C57 C56 C61 C49 176.05(16) . . . . ? C55 C56 C61 C49 -6.86(19) . . . . ? C45 C49 C61 C60 10.5(3) . . . . ? C50 C49 C61 C60 -168.58(18) . . . . ? C45 C49 C61 C56 -174.59(18) . . . . ? C50 C49 C61 C56 6.32(19) . . . . ? C49 C45 C46 C62 38.3(4) . . . . ? C48 C45 C46 C62 -160.5(2) . . . . ? C49 C45 C46 C47 -147.4(2) . . . . ? C48 C45 C46 C47 13.80(14) . . . . ? C45 C46 C62 C63 14.0(4) . . . . ? C47 C46 C62 C63 -158.40(19) . . . . ? C45 C46 C62 C74 -162.6(2) . . . . ? C47 C46 C62 C74 25.0(3) . . . . ? C46 C62 C63 C64 10.3(3) . . . . ? C74 C62 C63 C64 -172.5(2) . . . . ? C46 C62 C63 C68 -172.91(19) . . . . ? C74 C62 C63 C68 4.3(2) . . . . ? C68 C63 C64 C65 2.8(3) . . . . ? C62 C63 C64 C65 179.20(19) . . . . ? C63 C64 C65 C66 -0.3(3) . . . . ? C64 C65 C66 C67 -1.5(4) . . . . ? C65 C66 C67 C68 0.9(4) . . . . ? C66 C67 C68 C63 1.6(4) . . . . ? C66 C67 C68 C69 -177.1(2) . . . . ? C64 C63 C68 C67 -3.4(3) . . . . ? C62 C63 C68 C67 179.42(19) . . . . ? C64 C63 C68 C69 175.56(18) . . . . ? C62 C63 C68 C69 -1.6(2) . . . . ? C67 C68 C69 C70 -2.6(4) . . . . ? C63 C68 C69 C70 178.6(2) . . . . ? C67 C68 C69 C74 176.9(2) . . . . ? C63 C68 C69 C74 -1.9(2) . . . . ? C74 C69 C70 C71 -0.1(3) . . . . ? C68 C69 C70 C71 179.4(2) . . . . ? C69 C70 C71 C72 0.5(4) . . . . ? C70 C71 C72 C73 0.4(4) . . . . ? C71 C72 C73 C74 -1.5(3) . . . . ? C72 C73 C74 C69 1.8(3) . . . . ? C72 C73 C74 C62 175.2(2) . . . . ? C70 C69 C74 C73 -1.0(3) . . . . ? C68 C69 C74 C73 179.39(18) . . . . ? C70 C69 C74 C62 -175.84(19) . . . . ? C68 C69 C74 C62 4.6(2) . . . . ? C46 C62 C74 C73 -2.1(3) . . . . ? C63 C62 C74 C73 -179.3(2) . . . . ? C46 C62 C74 C69 171.81(18) . . . . ? C63 C62 C74 C69 -5.4(2) . . . . ? C62 C46 C47 C75 38.9(3) . . . . ? C45 C46 C47 C75 -135.97(17) . . . . ? C62 C46 C47 C48 161.6(2) . . . . ? C45 C46 C47 C48 -13.24(14) . . . . ? C46 C47 C75 C80 27.7(3) . . . . ? C48 C47 C75 C80 -78.2(2) . . . . ? C46 C47 C75 C76 -153.24(18) . . . . ? C48 C47 C75 C76 100.8(2) . . . . ? C80 C75 C76 C77 -1.8(3) . . . . ? C47 C75 C76 C77 179.12(19) . . . . ? C75 C76 C77 C78 1.3(3) . . . . ? C76 C77 C78 C79 0.1(3) . . . . ? C76 C77 C78 C87 -177.8(2) . . . . ? C77 C78 C87 F9A -28.7(14) . . . . ? C79 C78 C87 F9A 153.5(14) . . . . ? C77 C78 C87 F9B 159.8(15) . . . . ? C79 C78 C87 F9B -18.1(15) . . . . ? C77 C78 C87 F8A -150.1(10) . . . . ? C79 C78 C87 F8A 32.1(10) . . . . ? C77 C78 C87 F7B -79.3(10) . . . . ? C79 C78 C87 F7B 102.8(10) . . . . ? C77 C78 C87 F7A 96.9(9) . . . . ? C79 C78 C87 F7A -80.9(9) . . . . ? C77 C78 C87 F8B 32.9(10) . . . . ? C79 C78 C87 F8B -145.0(9) . . . . ? C77 C78 C79 C80 -0.9(3) . . . . ? C87 C78 C79 C80 177.0(2) . . . . ? C78 C79 C80 C75 0.4(3) . . . . ? C76 C75 C80 C79 1.0(3) . . . . ? C47 C75 C80 C79 -179.99(19) . . . . ? C49 C45 C48 C81 -92.7(2) . . . . ? C46 C45 C48 C81 103.82(17) . . . . ? C49 C45 C48 C47 150.17(19) . . . . ? C46 C45 C48 C47 -13.29(14) . . . . ? C75 C47 C48 C81 17.5(2) . . . . ? C46 C47 C48 C81 -107.39(16) . . . . ? C75 C47 C48 C45 137.62(16) . . . . ? C46 C47 C48 C45 12.68(13) . . . . ? C45 C48 C81 C86 -11.3(3) . . . . ? C47 C48 C81 C86 89.2(2) . . . . ? C45 C48 C81 C82 169.80(18) . . . . ? C47 C48 C81 C82 -89.7(2) . . . . ? C86 C81 C82 C83 -0.9(3) . . . . ? C48 C81 C82 C83 178.0(2) . . . . ? C81 C82 C83 C84 0.9(4) . . . . ? C82 C83 C84 C85 -0.7(4) . . . . ? C82 C83 C84 C88 179.3(3) . . . . ? C85 C84 C88 F11A -27.7(10) . . . . ? C83 C84 C88 F11A 152.4(10) . . . . ? C85 C84 C88 F11B 155.7(15) . . . . ? C83 C84 C88 F11B -24.3(16) . . . . ? C85 C84 C88 F10B 26.1(16) . . . . ? C83 C84 C88 F10B -153.8(16) . . . . ? C85 C84 C88 F10A -149.9(11) . . . . ? C83 C84 C88 F10A 30.1(12) . . . . ? C85 C84 C88 F12A 91.4(11) . . . . ? C83 C84 C88 F12A -88.5(11) . . . . ? C85 C84 C88 F12B -86.0(14) . . . . ? C83 C84 C88 F12B 94.0(14) . . . . ? C83 C84 C85 C86 0.6(4) . . . . ? C88 C84 C85 C86 -179.4(3) . . . . ? C82 C81 C86 C85 0.8(3) . . . . ? C48 C81 C86 C85 -178.1(2) . . . . ? C84 C85 C86 C81 -0.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.471 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.026 #===END data_mjm114(24a) _database_code_depnum_ccdc_archive 'CCDC 769737' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H16' _chemical_formula_sum 'C23 H16' _chemical_formula_weight 292.36 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.6169(7) _cell_length_b 19.620(3) _cell_length_c 17.062(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.789(3) _cell_angle_gamma 90.00 _cell_volume 1543.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3973 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 30.39 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7220 _exptl_absorpt_correction_T_max 0.9894 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.062 before and 0.023 after correction. The Ratio of minimum to maximum transmission is 0.729736. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; All ordered hydrogen atoms were located in the difference fourier map and allowed to refine freely. Refined C-H bond lengths range from 0.97(2) \%A to 1.00(2) \%A. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12287 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3032 _reflns_number_gt 2558 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0386P)^2^+0.4460P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3032 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0915 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 C1 C -0.0563(3) 0.18540(7) 1.21121(8) 0.0288(3) Uani 1 1 d . . . H1 H -0.142(3) 0.1515(7) 1.2458(8) 0.029(4) Uiso 1 1 d . . . C2 C 0.1462(3) 0.23128(7) 1.24140(8) 0.0308(3) Uani 1 1 d . . . H2 H 0.209(3) 0.2293(7) 1.2971(9) 0.035(4) Uiso 1 1 d . . . C3 C 0.2621(3) 0.27940(7) 1.19255(8) 0.0313(3) Uani 1 1 d . . . H3 H 0.406(3) 0.3119(8) 1.2142(9) 0.036(4) Uiso 1 1 d . . . C4 C 0.1705(3) 0.28195(6) 1.11403(8) 0.0271(3) Uani 1 1 d . . . H4 H 0.246(3) 0.3172(7) 1.0791(8) 0.027(4) Uiso 1 1 d . . . C4A C -0.0337(3) 0.23602(6) 1.08318(7) 0.0231(3) Uani 1 1 d . . . C5 C -0.1503(3) 0.23938(6) 0.99824(7) 0.0240(3) Uani 1 1 d . . . H5 H -0.365(3) 0.2350(7) 0.9998(8) 0.027(3) Uiso 1 1 d . . . C5A C -0.0430(3) 0.17888(6) 0.95223(7) 0.0223(3) Uani 1 1 d . . . C6 C 0.1548(3) 0.18593(6) 0.89372(7) 0.0234(3) Uani 1 1 d . . . H6 H 0.228(3) 0.2310(7) 0.8823(8) 0.022(3) Uiso 1 1 d . . . C7 C 0.2395(3) 0.13035(7) 0.85087(7) 0.0262(3) Uani 1 1 d . . . H7 H 0.383(3) 0.1369(7) 0.8100(8) 0.031(4) Uiso 1 1 d . . . C8 C 0.1209(3) 0.06678(7) 0.86467(8) 0.0287(3) Uani 1 1 d . . . H8 H 0.177(3) 0.0271(7) 0.8342(8) 0.031(4) Uiso 1 1 d . . . C9 C -0.0749(3) 0.05922(7) 0.92241(8) 0.0279(3) Uani 1 1 d . . . H9 H -0.157(3) 0.0144(7) 0.9333(8) 0.029(4) Uiso 1 1 d . . . C9A C -0.1554(3) 0.11430(6) 0.96867(7) 0.0243(3) Uani 1 1 d . . . C10 C -0.3529(3) 0.10282(7) 1.03195(8) 0.0278(3) Uani 1 1 d . . . H10 H -0.489(3) 0.0652(7) 1.0225(8) 0.030(4) Uiso 1 1 d . . . C11 C -0.3489(3) 0.13344(7) 1.10185(8) 0.0278(3) Uani 1 1 d . . . H11 H -0.482(3) 0.1164(7) 1.1400(8) 0.032(4) Uiso 1 1 d . . . C11A C -0.1442(3) 0.18562(6) 1.13160(7) 0.0247(3) Uani 1 1 d . . . C12 C -0.0910(3) 0.30490(6) 0.96060(8) 0.0276(3) Uani 1 1 d . . . C13 C -0.0390(3) 0.35788(7) 0.92978(8) 0.0299(3) Uani 1 1 d . A . C14 C 0.0249(3) 0.42338(6) 0.89711(7) 0.0236(3) Uani 1 1 d . . . C15A C 0.2838(5) 0.45019(13) 0.91405(14) 0.0238(7) Uani 0.504(3) 1 d P A 1 H15A H 0.4258 0.4239 0.9427 0.029 Uiso 0.504(3) 1 calc PR A 1 C16A C 0.3515(6) 0.51547(13) 0.89100(15) 0.0256(7) Uani 0.504(3) 1 d P A 1 H16A H 0.5321 0.5356 0.9067 0.031 Uiso 0.504(3) 1 calc PR A 1 C15B C 0.1529(5) 0.47842(12) 0.94841(14) 0.0216(7) Uani 0.496(3) 1 d P A 2 H15B H 0.2035 0.4702 1.0022 0.026 Uiso 0.496(3) 1 calc PR A 2 C16B C 0.1956(6) 0.54171(13) 0.91528(15) 0.0239(7) Uani 0.496(3) 1 d P A 2 H16B H 0.2710 0.5777 0.9474 0.029 Uiso 0.496(3) 1 calc PR A 2 C17 C 0.1352(3) 0.55315(7) 0.84115(8) 0.0288(3) Uani 1 1 d . . . H17 H 0.174(3) 0.5995(8) 0.8222(9) 0.037(4) Uiso 1 1 d . . . C18A C -0.1083(7) 0.52352(15) 0.82035(18) 0.0265(7) Uani 0.504(3) 1 d P A 1 H18A H -0.2442 0.5477 0.7873 0.032 Uiso 0.504(3) 1 calc PR A 1 C19A C -0.1790(7) 0.45842(14) 0.84403(16) 0.0246(6) Uani 0.504(3) 1 d P A 1 H19A H -0.3554 0.4374 0.8261 0.029 Uiso 0.504(3) 1 calc PR A 1 C18B C -0.0019(6) 0.50107(16) 0.79138(17) 0.0250(6) Uani 0.496(3) 1 d P A 2 H18B H -0.0604 0.5104 0.7383 0.030 Uiso 0.496(3) 1 calc PR A 2 C19B C -0.0443(7) 0.43759(14) 0.82369(16) 0.0218(6) Uani 0.496(3) 1 d P A 2 H19B H -0.1274 0.4027 0.7912 0.026 Uiso 0.496(3) 1 calc PR A 2 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 C1 0.0267(7) 0.0288(7) 0.0311(7) 0.0051(6) 0.0033(5) 0.0076(5) C2 0.0297(7) 0.0337(7) 0.0288(7) -0.0037(6) -0.0014(6) 0.0113(6) C3 0.0286(7) 0.0271(7) 0.0382(8) -0.0087(6) 0.0007(6) 0.0035(6) C4 0.0264(7) 0.0205(6) 0.0348(7) -0.0023(5) 0.0062(6) 0.0029(5) C4A 0.0194(6) 0.0211(6) 0.0291(7) 0.0014(5) 0.0039(5) 0.0070(5) C5 0.0189(6) 0.0224(6) 0.0307(7) 0.0073(5) 0.0022(5) 0.0022(5) C5A 0.0181(6) 0.0238(6) 0.0242(6) 0.0054(5) -0.0061(5) 0.0007(5) C6 0.0214(6) 0.0231(6) 0.0251(6) 0.0059(5) -0.0043(5) -0.0013(5) C7 0.0248(7) 0.0298(7) 0.0235(6) 0.0028(5) -0.0036(5) 0.0006(5) C8 0.0326(7) 0.0259(7) 0.0267(7) -0.0009(5) -0.0082(5) 0.0017(5) C9 0.0301(7) 0.0230(7) 0.0296(7) 0.0056(5) -0.0097(5) -0.0051(5) C9A 0.0208(6) 0.0252(6) 0.0260(6) 0.0073(5) -0.0070(5) -0.0018(5) C10 0.0229(6) 0.0252(7) 0.0347(7) 0.0094(5) -0.0036(5) -0.0059(5) C11 0.0226(7) 0.0280(7) 0.0329(7) 0.0117(6) 0.0025(5) -0.0002(5) C11A 0.0196(6) 0.0244(6) 0.0304(7) 0.0043(5) 0.0027(5) 0.0065(5) C12 0.0251(7) 0.0248(7) 0.0335(7) 0.0052(5) 0.0057(5) 0.0050(5) C13 0.0283(7) 0.0256(7) 0.0365(7) 0.0050(6) 0.0094(6) 0.0071(5) C14 0.0231(6) 0.0212(6) 0.0271(6) 0.0038(5) 0.0074(5) 0.0040(5) C15A 0.0230(13) 0.0280(13) 0.0205(13) 0.0018(11) 0.0006(10) 0.0053(11) C16A 0.0208(14) 0.0290(14) 0.0272(13) -0.0014(11) 0.0026(11) -0.0030(11) C15B 0.0240(13) 0.0240(13) 0.0170(12) -0.0001(10) 0.0016(10) 0.0027(11) C16B 0.0244(15) 0.0183(12) 0.0294(14) -0.0037(10) 0.0053(11) 0.0008(11) C17 0.0351(8) 0.0212(6) 0.0311(7) 0.0045(5) 0.0128(6) -0.0005(5) C18A 0.0280(15) 0.0276(15) 0.0236(14) 0.0086(12) -0.0024(12) 0.0040(12) C19A 0.0241(15) 0.0261(14) 0.0232(13) -0.0017(11) -0.0021(12) -0.0015(12) C18B 0.0237(14) 0.0324(15) 0.0190(13) 0.0056(12) 0.0022(11) 0.0055(12) C19B 0.0193(14) 0.0248(14) 0.0215(13) -0.0029(11) 0.0021(11) 0.0002(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.379(2) . ? C1 C11A 1.3986(18) . ? C1 H1 0.985(14) . ? C2 C3 1.384(2) . ? C2 H2 0.980(15) . ? C3 C4 1.386(2) . ? C3 H3 0.981(16) . ? C4 C4A 1.3891(18) . ? C4 H4 0.988(14) . ? C4A C11A 1.4007(17) . ? C4A C5 1.5226(18) . ? C5 C12 1.4687(17) . ? C5 C5A 1.5192(17) . ? C5 H5 0.999(14) . ? C5A C6 1.3922(17) . ? C5A C9A 1.4027(17) . ? C6 C7 1.3801(18) . ? C6 H6 0.970(14) . ? C7 C8 1.3869(18) . ? C7 H7 0.991(14) . ? C8 C9 1.377(2) . ? C8 H8 0.979(15) . ? C9 C9A 1.3992(18) . ? C9 H9 0.979(14) . ? C9A C10 1.4642(18) . ? C10 C11 1.3347(19) . ? C10 H10 0.979(15) . ? C11 C11A 1.4670(18) . ? C11 H11 0.975(15) . ? C12 C13 1.1946(18) . ? C13 C14 1.4370(18) . ? C14 C19B 1.308(3) . ? C14 C15A 1.325(3) . ? C14 C19A 1.448(3) . ? C14 C15B 1.494(3) . ? C15A C16A 1.380(4) . ? C15A H15A 0.9500 . ? C16A C17 1.478(3) . ? C16A H16A 0.9500 . ? C15B C16B 1.382(3) . ? C15B H15B 0.9500 . ? C16B C17 1.301(3) . ? C16B H16B 0.9500 . ? C17 C18A 1.299(3) . ? C17 C18B 1.454(3) . ? C17 H17 0.985(15) . ? C18A C19A 1.383(4) . ? C18A H18A 0.9500 . ? C19A H19A 0.9500 . ? C18B C19B 1.380(4) . ? C18B H18B 0.9500 . ? C19B H19B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11A 121.34(13) . . ? C2 C1 H1 120.1(8) . . ? C11A C1 H1 118.6(8) . . ? C1 C2 C3 119.67(13) . . ? C1 C2 H2 119.8(9) . . ? C3 C2 H2 120.5(9) . . ? C2 C3 C4 119.88(13) . . ? C2 C3 H3 119.4(9) . . ? C4 C3 H3 120.7(9) . . ? C3 C4 C4A 120.82(13) . . ? C3 C4 H4 120.5(8) . . ? C4A C4 H4 118.6(8) . . ? C4 C4A C11A 119.64(12) . . ? C4 C4A C5 122.31(11) . . ? C11A C4A C5 118.02(11) . . ? C12 C5 C5A 112.68(10) . . ? C12 C5 C4A 112.91(11) . . ? C5A C5 C4A 110.43(10) . . ? C12 C5 H5 107.1(8) . . ? C5A C5 H5 107.2(8) . . ? C4A C5 H5 106.1(8) . . ? C6 C5A C9A 119.67(11) . . ? C6 C5A C5 122.31(11) . . ? C9A C5A C5 117.99(11) . . ? C7 C6 C5A 120.94(12) . . ? C7 C6 H6 120.2(8) . . ? C5A C6 H6 118.9(8) . . ? C6 C7 C8 119.75(12) . . ? C6 C7 H7 119.1(8) . . ? C8 C7 H7 121.2(8) . . ? C9 C8 C7 119.78(12) . . ? C9 C8 H8 119.6(8) . . ? C7 C8 H8 120.6(8) . . ? C8 C9 C9A 121.46(12) . . ? C8 C9 H9 120.4(8) . . ? C9A C9 H9 118.1(8) . . ? C9 C9A C5A 118.29(12) . . ? C9 C9A C10 119.29(11) . . ? C5A C9A C10 122.42(12) . . ? C11 C10 C9A 127.41(12) . . ? C11 C10 H10 117.9(8) . . ? C9A C10 H10 114.4(8) . . ? C10 C11 C11A 127.16(12) . . ? C10 C11 H11 117.4(9) . . ? C11A C11 H11 115.1(9) . . ? C1 C11A C4A 118.56(12) . . ? C1 C11A C11 119.05(12) . . ? C4A C11A C11 122.39(11) . . ? C13 C12 C5 179.09(14) . . ? C12 C13 C14 176.71(15) . . ? C19B C14 C13 121.14(16) . . ? C15A C14 C13 118.05(15) . . ? C15A C14 C19A 120.01(17) . . ? C13 C14 C19A 121.87(15) . . ? C19B C14 C15B 118.58(17) . . ? C13 C14 C15B 120.13(14) . . ? C14 C15A C16A 121.4(2) . . ? C14 C15A H15A 119.3 . . ? C16A C15A H15A 119.3 . . ? C15A C16A C17 118.2(2) . . ? C15A C16A H16A 120.9 . . ? C17 C16A H16A 120.9 . . ? C16B C15B C14 118.0(2) . . ? C16B C15B H15B 121.0 . . ? C14 C15B H15B 121.0 . . ? C17 C16B C15B 121.6(2) . . ? C17 C16B H16B 119.2 . . ? C15B C16B H16B 119.2 . . ? C16B C17 C18B 120.88(18) . . ? C18A C17 C16A 119.00(18) . . ? C18A C17 H17 119.5(9) . . ? C16B C17 H17 116.4(9) . . ? C18B C17 H17 122.6(9) . . ? C16A C17 H17 121.5(9) . . ? C17 C18A C19A 123.1(2) . . ? C17 C18A H18A 118.4 . . ? C19A C18A H18A 118.4 . . ? C18A C19A C14 117.8(2) . . ? C18A C19A H19A 121.1 . . ? C14 C19A H19A 121.1 . . ? C19B C18B C17 117.9(2) . . ? C19B C18B H18B 121.1 . . ? C17 C18B H18B 121.1 . . ? C14 C19B C18B 122.8(2) . . ? C14 C19B H19B 118.6 . . ? C18B C19B H19B 118.6 . . ? 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 C11A C1 C2 C3 1.1(2) . . . . ? C1 C2 C3 C4 1.10(19) . . . . ? C2 C3 C4 C4A -0.99(19) . . . . ? C3 C4 C4A C11A -1.29(18) . . . . ? C3 C4 C4A C5 176.98(11) . . . . ? C4 C4A C5 C12 -16.15(16) . . . . ? C11A C4A C5 C12 162.15(11) . . . . ? C4 C4A C5 C5A 111.01(13) . . . . ? C11A C4A C5 C5A -70.69(14) . . . . ? C12 C5 C5A C6 16.10(16) . . . . ? C4A C5 C5A C6 -111.19(12) . . . . ? C12 C5 C5A C9A -162.22(11) . . . . ? C4A C5 C5A C9A 70.50(14) . . . . ? C9A C5A C6 C7 0.83(17) . . . . ? C5 C5A C6 C7 -177.46(11) . . . . ? C5A C6 C7 C8 1.67(18) . . . . ? C6 C7 C8 C9 -1.66(18) . . . . ? C7 C8 C9 C9A -0.86(19) . . . . ? C8 C9 C9A C5A 3.31(18) . . . . ? C8 C9 C9A C10 -176.86(11) . . . . ? C6 C5A C9A C9 -3.25(17) . . . . ? C5 C5A C9A C9 175.11(11) . . . . ? C6 C5A C9A C10 176.92(11) . . . . ? C5 C5A C9A C10 -4.71(17) . . . . ? C9 C9A C10 C11 144.23(14) . . . . ? C5A C9A C10 C11 -35.9(2) . . . . ? C9A C10 C11 C11A -0.3(2) . . . . ? C2 C1 C11A C4A -3.34(18) . . . . ? C2 C1 C11A C11 176.86(12) . . . . ? C4 C4A C11A C1 3.39(17) . . . . ? C5 C4A C11A C1 -174.95(11) . . . . ? C4 C4A C11A C11 -176.82(11) . . . . ? C5 C4A C11A C11 4.84(17) . . . . ? C10 C11 C11A C1 -144.02(14) . . . . ? C10 C11 C11A C4A 36.2(2) . . . . ? C19B C14 C15A C16A 44.7(3) . . . . ? C13 C14 C15A C16A -173.9(2) . . . . ? C19A C14 C15A C16A 9.1(3) . . . . ? C15B C14 C15A C16A -68.9(3) . . . . ? C14 C15A C16A C17 -4.8(4) . . . . ? C19B C14 C15B C16B -0.8(3) . . . . ? C15A C14 C15B C16B 83.8(3) . . . . ? C13 C14 C15B C16B -176.48(19) . . . . ? C19A C14 C15B C16B -35.2(3) . . . . ? C14 C15B C16B C17 -2.0(4) . . . . ? C15B C16B C17 C18A 41.5(3) . . . . ? C15B C16B C17 C18B 5.0(4) . . . . ? C15B C16B C17 C16A -70.8(3) . . . . ? C15A C16A C17 C18A -0.6(3) . . . . ? C15A C16A C17 C16B 86.0(3) . . . . ? C15A C16A C17 C18B -34.9(3) . . . . ? C16B C17 C18A C19A -42.7(4) . . . . ? C18B C17 C18A C19A 74.0(4) . . . . ? C16A C17 C18A C19A 1.4(4) . . . . ? C17 C18A C19A C14 2.6(5) . . . . ? C19B C14 C19A C18A -85.0(4) . . . . ? C15A C14 C19A C18A -8.0(4) . . . . ? C13 C14 C19A C18A 175.1(2) . . . . ? C15B C14 C19A C18A 34.6(3) . . . . ? C18A C17 C18B C19B -84.4(4) . . . . ? C16B C17 C18B C19B -5.1(4) . . . . ? C16A C17 C18B C19B 36.1(3) . . . . ? C15A C14 C19B C18B -43.8(4) . . . . ? C13 C14 C19B C18B 176.1(2) . . . . ? C19A C14 C19B C18B 74.0(4) . . . . ? C15B C14 C19B C18B 0.6(4) . . . . ? C17 C18B C19B C14 2.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.218 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.034 #===END data_mjm118(20a) _database_code_depnum_ccdc_archive 'CCDC 769738' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 Br' _chemical_formula_sum 'C23 H15 Br' _chemical_formula_weight 371.26 _chemical_absolute_configuration ad 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1828(8) _cell_length_b 9.6681(12) _cell_length_c 27.580(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1648.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7228 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 30.36 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 2.493 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5937 _exptl_absorpt_correction_T_max 0.9518 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.128 before and 0.046 after correction. The Ratio of minimum to maximum transmission is 0.623764. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34485 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4803 _reflns_number_gt 4572 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0636P)^2^+0.1289P] 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 -0.005(7) _refine_ls_number_reflns 4803 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.003 _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 C1 C 1.0187(4) 0.9341(2) 0.88111(8) 0.0206(4) Uani 1 1 d . . . H1 H 1.1428 0.9901 0.8862 0.025 Uiso 1 1 calc R . . C2 C 0.8523(5) 0.9849(3) 0.85289(9) 0.0242(5) Uani 1 1 d . . . H2 H 0.8626 1.0746 0.8390 0.029 Uiso 1 1 calc R . . C3 C 0.6711(4) 0.9050(3) 0.84495(8) 0.0231(4) Uani 1 1 d . . . H3 H 0.5545 0.9399 0.8262 0.028 Uiso 1 1 calc R . . C4 C 0.6606(4) 0.7730(2) 0.86468(8) 0.0185(4) Uani 1 1 d . . . H4 H 0.5366 0.7176 0.8586 0.022 Uiso 1 1 calc R . . C4A C 0.8280(3) 0.7194(2) 0.89329(7) 0.0147(4) Uani 1 1 d . . . C5 C 0.8057(3) 0.5726(2) 0.90911(8) 0.0154(4) Uani 1 1 d . . . C5A C 0.8731(4) 0.5199(2) 0.95751(7) 0.0153(4) Uani 1 1 d . . . C6 C 0.7360(4) 0.4232(2) 0.97928(8) 0.0183(4) Uani 1 1 d . . . H6 H 0.6036 0.4003 0.9637 0.022 Uiso 1 1 calc R . . C7 C 0.7868(5) 0.3599(2) 1.02275(8) 0.0210(4) Uani 1 1 d . . . H7 H 0.6908 0.2945 1.0368 0.025 Uiso 1 1 calc R . . C8 C 0.9808(4) 0.3933(2) 1.04575(8) 0.0213(4) Uani 1 1 d . . . H8 H 1.0193 0.3496 1.0754 0.026 Uiso 1 1 calc R . . C9 C 1.1165(4) 0.4902(2) 1.02518(8) 0.0200(4) Uani 1 1 d . . . H9 H 1.2483 0.5122 1.0411 0.024 Uiso 1 1 calc R . . C9A C 1.0661(4) 0.5574(2) 0.98145(8) 0.0158(4) Uani 1 1 d . . . C10 C 1.2186(4) 0.6617(2) 0.96510(8) 0.0195(4) Uani 1 1 d . . . H10 H 1.3574 0.6569 0.9798 0.023 Uiso 1 1 calc R . . C11 C 1.1948(4) 0.7635(2) 0.93269(8) 0.0191(4) Uani 1 1 d . . . H11 H 1.3189 0.8203 0.9286 0.023 Uiso 1 1 calc R . . C11A C 1.0107(4) 0.8021(2) 0.90260(8) 0.0163(4) Uani 1 1 d . . . C12 C 0.7012(4) 0.4873(2) 0.87984(7) 0.0175(4) Uani 1 1 d . . . C13 C 0.5800(4) 0.4086(2) 0.85313(7) 0.0159(4) Uani 1 1 d . . . Br Br 0.27865(4) 0.40130(2) 0.871959(8) 0.02068(7) Uani 1 1 d . . . C14 C 0.6399(4) 0.3292(2) 0.80952(7) 0.0155(4) Uani 1 1 d . . . C15 C 0.5090(4) 0.2266(2) 0.78929(9) 0.0215(5) Uani 1 1 d . . . H15 H 0.3738 0.2051 0.8038 0.026 Uiso 1 1 calc R . . C16 C 0.5756(5) 0.1561(3) 0.74808(9) 0.0276(5) Uani 1 1 d . . . H16 H 0.4859 0.0861 0.7347 0.033 Uiso 1 1 calc R . . C17 C 0.7712(5) 0.1867(3) 0.72643(9) 0.0308(6) Uani 1 1 d . . . H17 H 0.8154 0.1383 0.6981 0.037 Uiso 1 1 calc R . . C18 C 0.9036(5) 0.2886(3) 0.74619(9) 0.0284(5) Uani 1 1 d . . . H18 H 1.0385 0.3098 0.7315 0.034 Uiso 1 1 calc R . . C19 C 0.8382(4) 0.3591(2) 0.78728(8) 0.0207(4) Uani 1 1 d . . . H19 H 0.9290 0.4287 0.8006 0.025 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 C1 0.0264(11) 0.0201(10) 0.0152(10) -0.0019(7) 0.0041(8) -0.0052(8) C2 0.0327(12) 0.0242(11) 0.0158(10) 0.0018(8) 0.0050(9) -0.0011(10) C3 0.0284(11) 0.0265(10) 0.0142(9) 0.0027(9) 0.0010(8) 0.0029(10) C4 0.0210(10) 0.0245(10) 0.0100(9) -0.0013(7) 0.0008(7) -0.0014(8) C4A 0.0174(10) 0.0193(9) 0.0074(8) -0.0009(7) 0.0013(7) -0.0011(7) C5 0.0157(9) 0.0173(9) 0.0132(9) -0.0011(7) -0.0014(7) -0.0007(7) C5A 0.0199(10) 0.0159(9) 0.0101(9) -0.0041(7) -0.0008(7) 0.0014(8) C6 0.0224(10) 0.0185(9) 0.0141(9) -0.0024(7) -0.0014(8) -0.0023(8) C7 0.0286(11) 0.0183(9) 0.0160(10) -0.0012(7) -0.0015(9) -0.0007(9) C8 0.0318(12) 0.0195(10) 0.0127(9) -0.0023(8) -0.0045(8) 0.0036(10) C9 0.0237(11) 0.0215(10) 0.0147(10) -0.0052(8) -0.0047(8) 0.0037(9) C9A 0.0185(10) 0.0169(9) 0.0121(9) -0.0055(7) -0.0006(7) 0.0017(7) C10 0.0160(9) 0.0220(10) 0.0204(10) -0.0060(8) -0.0023(9) 0.0000(9) C11 0.0171(10) 0.0227(10) 0.0175(10) -0.0062(7) 0.0015(8) -0.0031(8) C11A 0.0176(10) 0.0204(9) 0.0109(9) -0.0035(8) 0.0027(7) -0.0007(8) C12 0.0208(10) 0.0208(9) 0.0109(9) -0.0006(7) 0.0002(8) -0.0003(8) C13 0.0190(9) 0.0178(9) 0.0109(8) -0.0004(8) -0.0028(7) 0.0007(9) Br 0.01820(10) 0.02756(11) 0.01629(11) -0.00013(8) 0.00014(7) -0.00011(8) C14 0.0218(10) 0.0158(9) 0.0089(9) 0.0003(7) -0.0045(7) 0.0009(7) C15 0.0284(12) 0.0197(10) 0.0164(11) -0.0020(8) -0.0046(9) -0.0024(9) C16 0.0433(15) 0.0238(11) 0.0158(11) -0.0071(9) -0.0090(11) 0.0005(11) C17 0.0464(17) 0.0335(12) 0.0125(10) -0.0060(9) -0.0040(10) 0.0141(13) C18 0.0307(13) 0.0380(13) 0.0166(11) 0.0034(10) 0.0030(9) 0.0058(11) C19 0.0230(11) 0.0245(10) 0.0144(10) 0.0004(8) -0.0016(8) -0.0005(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.380(4) . ? C1 C11A 1.408(3) . ? C1 H1 0.9500 . ? C2 C3 1.378(4) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C4A 1.401(3) . ? C4 H4 0.9500 . ? C4A C11A 1.408(3) . ? C4A C5 1.491(3) . ? C5 C12 1.322(3) . ? C5 C5A 1.488(3) . ? C5A C6 1.397(3) . ? C5A C9A 1.411(3) . ? C6 C7 1.382(3) . ? C6 H6 0.9500 . ? C7 C8 1.395(3) . ? C7 H7 0.9500 . ? C8 C9 1.380(4) . ? C8 H8 0.9500 . ? C9 C9A 1.405(3) . ? C9 H9 0.9500 . ? C9A C10 1.452(3) . ? C10 C11 1.338(3) . ? C10 H10 0.9500 . ? C11 C11A 1.457(3) . ? C11 H11 0.9500 . ? C12 C13 1.298(3) . ? C13 C14 1.474(3) . ? C13 Br 1.935(2) . ? C14 C15 1.396(3) . ? C14 C19 1.401(3) . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 C17 1.381(5) . ? C16 H16 0.9500 . ? C17 C18 1.392(4) . ? C17 H17 0.9500 . ? C18 C19 1.383(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11A 122.3(2) . . ? C2 C1 H1 118.9 . . ? C11A C1 H1 118.9 . . ? C3 C2 C1 119.7(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 119.4(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C4A 121.7(2) . . ? C3 C4 H4 119.1 . . ? C4A C4 H4 119.1 . . ? C4 C4A C11A 119.1(2) . . ? C4 C4A C5 116.64(19) . . ? C11A C4A C5 124.2(2) . . ? C12 C5 C5A 118.10(19) . . ? C12 C5 C4A 117.38(19) . . ? C5A C5 C4A 124.22(18) . . ? C6 C5A C9A 119.0(2) . . ? C6 C5A C5 116.39(19) . . ? C9A C5A C5 124.6(2) . . ? C7 C6 C5A 122.1(2) . . ? C7 C6 H6 119.0 . . ? C5A C6 H6 119.0 . . ? C6 C7 C8 119.2(2) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C9 C8 C7 119.5(2) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C9A 122.2(2) . . ? C8 C9 H9 118.9 . . ? C9A C9 H9 118.9 . . ? C9 C9A C5A 118.0(2) . . ? C9 C9A C10 116.4(2) . . ? C5A C9A C10 125.6(2) . . ? C11 C10 C9A 130.3(2) . . ? C11 C10 H10 114.8 . . ? C9A C10 H10 114.8 . . ? C10 C11 C11A 130.9(2) . . ? C10 C11 H11 114.5 . . ? C11A C11 H11 114.5 . . ? C4A C11A C1 117.8(2) . . ? C4A C11A C11 125.8(2) . . ? C1 C11A C11 116.4(2) . . ? C13 C12 C5 173.9(2) . . ? C12 C13 C14 128.6(2) . . ? C12 C13 Br 115.15(17) . . ? C14 C13 Br 116.24(16) . . ? C15 C14 C19 118.6(2) . . ? C15 C14 C13 123.4(2) . . ? C19 C14 C13 118.0(2) . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 120.6(2) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 119.8(2) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 119.8(3) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C14 120.9(2) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? 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 C11A C1 C2 C3 -0.2(4) . . . . ? C1 C2 C3 C4 -1.4(3) . . . . ? C2 C3 C4 C4A 1.2(3) . . . . ? C3 C4 C4A C11A 0.5(3) . . . . ? C3 C4 C4A C5 -175.3(2) . . . . ? C4 C4A C5 C12 31.0(3) . . . . ? C11A C4A C5 C12 -144.6(2) . . . . ? C4 C4A C5 C5A -142.5(2) . . . . ? C11A C4A C5 C5A 41.9(3) . . . . ? C12 C5 C5A C6 -33.4(3) . . . . ? C4A C5 C5A C6 140.1(2) . . . . ? C12 C5 C5A C9A 144.6(2) . . . . ? C4A C5 C5A C9A -42.0(3) . . . . ? C9A C5A C6 C7 -2.2(3) . . . . ? C5 C5A C6 C7 175.9(2) . . . . ? C5A C6 C7 C8 0.1(3) . . . . ? C6 C7 C8 C9 1.0(3) . . . . ? C7 C8 C9 C9A 0.1(3) . . . . ? C8 C9 C9A C5A -2.1(3) . . . . ? C8 C9 C9A C10 177.2(2) . . . . ? C6 C5A C9A C9 3.1(3) . . . . ? C5 C5A C9A C9 -174.8(2) . . . . ? C6 C5A C9A C10 -176.2(2) . . . . ? C5 C5A C9A C10 6.0(3) . . . . ? C9 C9A C10 C11 -162.4(2) . . . . ? C5A C9A C10 C11 16.9(4) . . . . ? C9A C10 C11 C11A -1.2(4) . . . . ? C4 C4A C11A C1 -2.0(3) . . . . ? C5 C4A C11A C1 173.5(2) . . . . ? C4 C4A C11A C11 178.0(2) . . . . ? C5 C4A C11A C11 -6.5(3) . . . . ? C2 C1 C11A C4A 1.9(3) . . . . ? C2 C1 C11A C11 -178.2(2) . . . . ? C10 C11 C11A C4A -15.3(4) . . . . ? C10 C11 C11A C1 164.8(2) . . . . ? C12 C13 C14 C15 166.7(2) . . . . ? Br C13 C14 C15 -16.1(3) . . . . ? C12 C13 C14 C19 -13.6(3) . . . . ? Br C13 C14 C19 163.62(17) . . . . ? C19 C14 C15 C16 0.2(3) . . . . ? C13 C14 C15 C16 179.9(2) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? C15 C16 C17 C18 0.3(4) . . . . ? C16 C17 C18 C19 -0.2(4) . . . . ? C17 C18 C19 C14 0.1(4) . . . . ? C15 C14 C19 C18 -0.1(3) . . . . ? C13 C14 C19 C18 -179.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.905 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.136 #===END data_mjm121(21a) _database_code_depnum_ccdc_archive 'CCDC 769739' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H16' _chemical_formula_sum 'C23 H16' _chemical_formula_weight 292.36 _chemical_absolute_configuration unk 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 0.0000 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.8227(7) _cell_length_b 9.1562(10) _cell_length_c 25.406(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1587.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5008 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 28.23 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8709 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.047 before and 0.029 after correction. The Ratio of minimum to maximum transmission is 0.873993. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14065 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1644 _reflns_number_gt 1546 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0303P)^2^+0.3567P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1644 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0674 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 C1 C 1.4087(3) 0.0797(2) 0.01428(7) 0.0270(5) Uani 1 1 d . . . H1 H 1.5325 0.1035 -0.0005 0.032 Uiso 1 1 calc R . . C2 C 1.3126(3) -0.0430(2) -0.00289(7) 0.0292(5) Uani 1 1 d . . . H2 H 1.3693 -0.1024 -0.0295 0.035 Uiso 1 1 calc R . . C3 C 1.1330(3) -0.0799(2) 0.01856(7) 0.0290(5) Uani 1 1 d . . . H3 H 1.0648 -0.1640 0.0065 0.035 Uiso 1 1 calc R . . C4 C 1.0537(3) 0.00669(19) 0.05762(7) 0.0241(4) Uani 1 1 d . . . H4 H 0.9306 -0.0192 0.0724 0.029 Uiso 1 1 calc R . . C4A C 1.1491(3) 0.13057(19) 0.07595(6) 0.0201(4) Uani 1 1 d . . . C5 C 1.0641(3) 0.20892(19) 0.12218(6) 0.0193(4) Uani 1 1 d . . . C5A C 1.0368(3) 0.37066(19) 0.12350(6) 0.0198(4) Uani 1 1 d . . . C6 C 0.8627(3) 0.4253(2) 0.14407(6) 0.0224(4) Uani 1 1 d . . . H6 H 0.7604 0.3594 0.1529 0.027 Uiso 1 1 calc R . . C7 C 0.8350(3) 0.5732(2) 0.15203(7) 0.0276(4) Uani 1 1 d . . . H7 H 0.7158 0.6083 0.1667 0.033 Uiso 1 1 calc R . . C8 C 0.9827(3) 0.6696(2) 0.13848(7) 0.0293(5) Uani 1 1 d . . . H8 H 0.9656 0.7716 0.1437 0.035 Uiso 1 1 calc R . . C9 C 1.1542(3) 0.6171(2) 0.11741(7) 0.0263(4) Uani 1 1 d . . . H9 H 1.2541 0.6844 0.1079 0.032 Uiso 1 1 calc R . . C9A C 1.1868(3) 0.4676(2) 0.10947(6) 0.0213(4) Uani 1 1 d . . . C10 C 1.3791(3) 0.4248(2) 0.08998(7) 0.0249(4) Uani 1 1 d . . . H10 H 1.4782 0.4967 0.0942 0.030 Uiso 1 1 calc R . . C11 C 1.4396(3) 0.3014(2) 0.06714(6) 0.0255(4) Uani 1 1 d . . . H11 H 1.5753 0.2981 0.0588 0.031 Uiso 1 1 calc R . . C11A C 1.3289(3) 0.17095(19) 0.05313(6) 0.0217(4) Uani 1 1 d . . . C12 C 1.0028(3) 0.13102(18) 0.16212(6) 0.0201(4) Uani 1 1 d . . . C13 C 0.9479(3) 0.05082(18) 0.20220(6) 0.0201(4) Uani 1 1 d . . . H13 H 1.0392 0.0389 0.2301 0.024 Uiso 1 1 calc R . . C14 C 0.7571(3) -0.02234(18) 0.20776(6) 0.0191(4) Uani 1 1 d . . . C15 C 0.7233(3) -0.1097(2) 0.25141(7) 0.0240(4) Uani 1 1 d . . . H15 H 0.8217 -0.1186 0.2777 0.029 Uiso 1 1 calc R . . C16 C 0.5485(3) -0.1841(2) 0.25725(7) 0.0286(5) Uani 1 1 d . . . H16 H 0.5275 -0.2436 0.2874 0.034 Uiso 1 1 calc R . . C17 C 0.4044(3) -0.1721(2) 0.21951(7) 0.0288(5) Uani 1 1 d . . . H17 H 0.2843 -0.2235 0.2234 0.035 Uiso 1 1 calc R . . C18 C 0.4361(3) -0.0844(2) 0.17586(7) 0.0253(4) Uani 1 1 d . . . H18 H 0.3368 -0.0752 0.1498 0.030 Uiso 1 1 calc R . . C19 C 0.6105(3) -0.01056(19) 0.16996(7) 0.0215(4) Uani 1 1 d . . . H19 H 0.6309 0.0489 0.1398 0.026 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 C1 0.0279(12) 0.0317(10) 0.0215(8) 0.0048(8) 0.0048(8) 0.0072(9) C2 0.0419(13) 0.0254(10) 0.0203(9) 0.0014(8) 0.0043(9) 0.0097(10) C3 0.0435(13) 0.0209(9) 0.0226(9) 0.0009(8) -0.0012(9) 0.0003(10) C4 0.0292(11) 0.0204(9) 0.0227(8) 0.0036(7) 0.0009(8) -0.0006(9) C4A 0.0239(10) 0.0185(8) 0.0180(8) 0.0054(7) -0.0005(8) 0.0035(8) C5 0.0160(10) 0.0227(9) 0.0192(8) 0.0015(7) -0.0003(7) -0.0020(8) C5A 0.0233(10) 0.0230(9) 0.0130(7) -0.0001(7) -0.0047(7) -0.0009(9) C6 0.0214(10) 0.0270(9) 0.0187(8) -0.0010(7) -0.0013(8) -0.0009(8) C7 0.0282(11) 0.0305(10) 0.0242(9) -0.0050(8) -0.0027(8) 0.0074(10) C8 0.0418(13) 0.0202(9) 0.0258(9) -0.0040(8) -0.0048(9) 0.0033(10) C9 0.0340(12) 0.0226(9) 0.0222(9) -0.0015(8) -0.0037(9) -0.0079(9) C9A 0.0232(11) 0.0259(9) 0.0149(8) 0.0003(7) -0.0030(7) -0.0025(8) C10 0.0219(10) 0.0290(10) 0.0238(9) 0.0021(8) -0.0017(8) -0.0084(9) C11 0.0177(10) 0.0334(10) 0.0254(9) 0.0026(8) 0.0032(8) -0.0018(9) C11A 0.0231(11) 0.0245(9) 0.0175(8) 0.0057(7) -0.0008(8) 0.0048(8) C12 0.0176(10) 0.0199(8) 0.0228(8) -0.0054(7) -0.0016(7) 0.0009(8) C13 0.0214(10) 0.0218(9) 0.0171(8) -0.0014(7) -0.0009(7) 0.0019(8) C14 0.0215(10) 0.0176(9) 0.0182(8) -0.0025(7) 0.0042(7) 0.0033(8) C15 0.0254(11) 0.0272(10) 0.0194(8) 0.0016(8) 0.0005(8) 0.0007(9) C16 0.0321(12) 0.0273(10) 0.0266(9) 0.0062(8) 0.0079(9) -0.0031(10) C17 0.0221(11) 0.0261(10) 0.0383(10) -0.0035(8) 0.0063(9) -0.0045(9) C18 0.0231(11) 0.0238(9) 0.0291(9) -0.0032(8) -0.0022(8) 0.0035(9) C19 0.0256(11) 0.0188(9) 0.0200(8) 0.0020(7) 0.0025(8) 0.0040(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.372(3) . ? C1 C11A 1.403(2) . ? C1 H1 0.9500 . ? C2 C3 1.383(3) . ? C2 H2 0.9500 . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C4A 1.388(3) . ? C4 H4 0.9500 . ? C4A C11A 1.406(3) . ? C4A C5 1.494(2) . ? C5 C12 1.309(2) . ? C5 C5A 1.493(2) . ? C5A C6 1.391(3) . ? C5A C9A 1.401(3) . ? C6 C7 1.382(3) . ? C6 H6 0.9500 . ? C7 C8 1.383(3) . ? C7 H7 0.9500 . ? C8 C9 1.374(3) . ? C8 H8 0.9500 . ? C9 C9A 1.402(3) . ? C9 H9 0.9500 . ? C9A C10 1.457(3) . ? C10 C11 1.336(3) . ? C10 H10 0.9500 . ? C11 C11A 1.457(3) . ? C11 H11 0.9500 . ? C12 C13 1.310(2) . ? C13 C14 1.471(3) . ? C13 H13 0.9500 . ? C14 C15 1.387(2) . ? C14 C19 1.391(2) . ? C15 C16 1.381(3) . ? C15 H15 0.9500 . ? C16 C17 1.377(3) . ? C16 H16 0.9500 . ? C17 C18 1.386(3) . ? C17 H17 0.9500 . ? C18 C19 1.377(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11A 121.73(19) . . ? C2 C1 H1 119.1 . . ? C11A C1 H1 119.1 . . ? C1 C2 C3 119.89(18) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 119.34(19) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C4A 121.79(19) . . ? C3 C4 H4 119.1 . . ? C4A C4 H4 119.1 . . ? C4 C4A C11A 119.04(17) . . ? C4 C4A C5 118.31(16) . . ? C11A C4A C5 122.46(16) . . ? C12 C5 C5A 118.90(16) . . ? C12 C5 C4A 118.16(16) . . ? C5A C5 C4A 122.86(15) . . ? C6 C5A C9A 119.43(17) . . ? C6 C5A C5 118.16(17) . . ? C9A C5A C5 122.13(18) . . ? C7 C6 C5A 121.64(19) . . ? C7 C6 H6 119.2 . . ? C5A C6 H6 119.2 . . ? C6 C7 C8 119.28(19) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C9 C8 C7 119.62(17) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C9A 122.19(19) . . ? C8 C9 H9 118.9 . . ? C9A C9 H9 118.9 . . ? C5A C9A C9 117.83(18) . . ? C5A C9A C10 125.04(17) . . ? C9 C9A C10 117.03(17) . . ? C11 C10 C9A 130.83(18) . . ? C11 C10 H10 114.6 . . ? C9A C10 H10 114.6 . . ? C10 C11 C11A 129.74(19) . . ? C10 C11 H11 115.1 . . ? C11A C11 H11 115.1 . . ? C1 C11A C4A 118.15(17) . . ? C1 C11A C11 117.31(17) . . ? C4A C11A C11 124.54(16) . . ? C5 C12 C13 177.9(2) . . ? C12 C13 C14 125.67(17) . . ? C12 C13 H13 117.2 . . ? C14 C13 H13 117.2 . . ? C15 C14 C19 118.52(17) . . ? C15 C14 C13 119.13(16) . . ? C19 C14 C13 122.33(15) . . ? C16 C15 C14 120.91(17) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C17 C16 C15 120.14(17) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.46(18) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 120.42(17) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C14 120.54(16) . . ? C18 C19 H19 119.7 . . ? C14 C19 H19 119.7 . . ? 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 C11A C1 C2 C3 -0.6(3) . . . . ? C1 C2 C3 C4 -0.8(3) . . . . ? C2 C3 C4 C4A 0.2(3) . . . . ? C3 C4 C4A C11A 1.7(3) . . . . ? C3 C4 C4A C5 -173.46(17) . . . . ? C4 C4A C5 C12 43.9(2) . . . . ? C11A C4A C5 C12 -131.03(18) . . . . ? C4 C4A C5 C5A -132.79(19) . . . . ? C11A C4A C5 C5A 52.2(3) . . . . ? C12 C5 C5A C6 -39.4(2) . . . . ? C4A C5 C5A C6 137.26(17) . . . . ? C12 C5 C5A C9A 134.43(18) . . . . ? C4A C5 C5A C9A -48.9(3) . . . . ? C9A C5A C6 C7 -1.3(3) . . . . ? C5 C5A C6 C7 172.77(17) . . . . ? C5A C6 C7 C8 1.0(3) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? C7 C8 C9 C9A -0.6(3) . . . . ? C6 C5A C9A C9 0.6(2) . . . . ? C5 C5A C9A C9 -173.23(16) . . . . ? C6 C5A C9A C10 176.86(15) . . . . ? C5 C5A C9A C10 3.1(3) . . . . ? C8 C9 C9A C5A 0.4(3) . . . . ? C8 C9 C9A C10 -176.21(16) . . . . ? C5A C9A C10 C11 21.8(3) . . . . ? C9 C9A C10 C11 -161.93(19) . . . . ? C9A C10 C11 C11A 2.0(3) . . . . ? C2 C1 C11A C4A 2.4(3) . . . . ? C2 C1 C11A C11 -177.80(16) . . . . ? C4 C4A C11A C1 -2.9(2) . . . . ? C5 C4A C11A C1 171.99(16) . . . . ? C4 C4A C11A C11 177.32(16) . . . . ? C5 C4A C11A C11 -7.7(3) . . . . ? C10 C11 C11A C1 158.57(19) . . . . ? C10 C11 C11A C4A -21.7(3) . . . . ? C12 C13 C14 C15 176.89(17) . . . . ? C12 C13 C14 C19 -1.2(3) . . . . ? C19 C14 C15 C16 0.3(3) . . . . ? C13 C14 C15 C16 -177.90(16) . . . . ? C14 C15 C16 C17 -0.1(3) . . . . ? C15 C16 C17 C18 -0.3(3) . . . . ? C16 C17 C18 C19 0.5(3) . . . . ? C17 C18 C19 C14 -0.2(3) . . . . ? C15 C14 C19 C18 -0.1(3) . . . . ? C13 C14 C19 C18 177.98(15) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.154 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.029 #===END data_mjm125(34) _database_code_depnum_ccdc_archive 'CCDC 769740' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H17 Br' _chemical_formula_sum 'C23 H17 Br' _chemical_formula_weight 373.28 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 10.3403(12) _cell_length_b 15.2026(18) _cell_length_c 11.2081(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.127(2) _cell_angle_gamma 90.00 _cell_volume 1692.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5243 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 29.89 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.428 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2579 _exptl_absorpt_correction_T_max 0.6423 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.153 before and 0.038 after correction. The Ratio of minimum to maximum transmission is 0.401593. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; All hydrogen atoms were located in the difference fourier map and allowed to refine freely. C-H bond lengths vary from 0.89(3) \%A to 1.02(3) \%A. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14572 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3684 _reflns_number_gt 3115 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0458P)^2^+0.5007P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3684 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0801 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.002 _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 C1 C 0.2652(2) 0.17570(14) 0.4635(2) 0.0211(4) Uani 1 1 d . . . H1 H 0.353(3) 0.1956(17) 0.447(2) 0.031(7) Uiso 1 1 d . . . C2 C 0.1400(2) 0.17020(15) 0.3783(2) 0.0238(5) Uani 1 1 d . . . H2 H 0.133(2) 0.1856(16) 0.295(2) 0.028(6) Uiso 1 1 d . . . C3 C 0.0315(2) 0.13992(16) 0.4151(2) 0.0245(5) Uani 1 1 d . . . H3 H -0.051(3) 0.1350(17) 0.359(2) 0.029(7) Uiso 1 1 d . . . C4 C 0.0482(2) 0.11515(14) 0.5375(2) 0.0194(4) Uani 1 1 d . . . H4 H -0.023(2) 0.0976(14) 0.561(2) 0.015(6) Uiso 1 1 d . . . C4A C 0.1733(2) 0.12107(13) 0.62569(18) 0.0145(4) Uani 1 1 d . . . C5 C 0.1842(2) 0.09840(13) 0.75981(18) 0.0153(4) Uani 1 1 d . . . H5 H 0.098(2) 0.0800(15) 0.761(2) 0.013(5) Uiso 1 1 d . . . C5A C 0.2803(2) 0.02241(13) 0.80619(17) 0.0166(4) Uani 1 1 d . . . C6 C 0.2325(2) -0.05398(14) 0.84750(19) 0.0225(5) Uani 1 1 d . . . H6 H 0.141(2) -0.0563(15) 0.848(2) 0.014(6) Uiso 1 1 d . . . C7 C 0.3188(3) -0.12398(16) 0.8947(2) 0.0326(6) Uani 1 1 d . . . H7 H 0.286(3) -0.175(2) 0.920(3) 0.049(9) Uiso 1 1 d . . . C8 C 0.4528(3) -0.11822(16) 0.9015(2) 0.0330(6) Uani 1 1 d . . . H8 H 0.519(3) -0.166(2) 0.934(3) 0.043(8) Uiso 1 1 d . . . C9 C 0.5018(2) -0.04273(16) 0.8617(2) 0.0269(5) Uani 1 1 d . . . H9 H 0.595(3) -0.0364(16) 0.869(2) 0.022(6) Uiso 1 1 d . . . C9A C 0.4171(2) 0.02818(14) 0.81195(18) 0.0190(4) Uani 1 1 d . . . C10 C 0.4768(2) 0.10404(14) 0.7685(2) 0.0209(5) Uani 1 1 d . . . H10 H 0.565(3) 0.1135(15) 0.807(2) 0.023(6) Uiso 1 1 d . . . C11 C 0.4208(2) 0.15636(14) 0.67177(19) 0.0197(4) Uani 1 1 d . . . H11 H 0.478(2) 0.1995(16) 0.647(2) 0.023(6) Uiso 1 1 d . . . C11A C 0.2845(2) 0.15069(13) 0.58812(18) 0.0159(4) Uani 1 1 d . . . C12 C 0.21655(19) 0.17934(13) 0.84175(18) 0.0148(4) Uani 1 1 d . . . H12 H 0.261(2) 0.2254(18) 0.814(2) 0.029(7) Uiso 1 1 d . . . C13 C 0.18651(19) 0.19401(13) 0.94748(18) 0.0153(4) Uani 1 1 d . . . Br Br 0.09804(2) 0.104371(14) 1.017078(18) 0.02166(9) Uani 1 1 d . . . C14 C 0.21109(19) 0.27631(14) 1.02035(18) 0.0155(4) Uani 1 1 d . . . C15 C 0.1680(2) 0.35629(15) 0.9613(2) 0.0200(4) Uani 1 1 d . . . H15 H 0.124(3) 0.3563(17) 0.880(2) 0.028(7) Uiso 1 1 d . . . C16 C 0.1889(2) 0.43416(15) 1.0282(2) 0.0253(5) Uani 1 1 d . . . H16 H 0.155(2) 0.4869(18) 0.986(2) 0.027(6) Uiso 1 1 d . . . C17 C 0.2538(2) 0.43358(16) 1.1540(2) 0.0261(5) Uani 1 1 d . . . H17 H 0.268(2) 0.4891(18) 1.196(2) 0.032(7) Uiso 1 1 d . . . C18 C 0.2981(2) 0.35454(16) 1.2134(2) 0.0233(5) Uani 1 1 d . . . H18 H 0.348(3) 0.3555(17) 1.297(3) 0.030(7) Uiso 1 1 d . . . C19 C 0.2765(2) 0.27660(15) 1.14729(19) 0.0185(4) Uani 1 1 d . . . H19 H 0.305(2) 0.2241(15) 1.185(2) 0.012(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0336(12) 0.0170(10) 0.0174(10) -0.0003(8) 0.0147(9) 0.0032(9) C2 0.0365(13) 0.0235(11) 0.0120(10) 0.0017(8) 0.0080(9) 0.0090(9) C3 0.0248(12) 0.0303(12) 0.0150(10) -0.0019(9) 0.0001(9) 0.0103(10) C4 0.0178(11) 0.0246(11) 0.0166(10) -0.0019(8) 0.0064(8) 0.0027(8) C4A 0.0185(10) 0.0139(9) 0.0126(9) -0.0001(7) 0.0066(8) 0.0035(7) C5 0.0150(10) 0.0198(10) 0.0125(10) 0.0000(8) 0.0060(8) -0.0026(8) C5A 0.0244(11) 0.0157(10) 0.0086(9) -0.0027(7) 0.0028(8) -0.0023(8) C6 0.0348(13) 0.0202(11) 0.0118(10) -0.0034(8) 0.0051(9) -0.0066(9) C7 0.0649(19) 0.0169(11) 0.0125(11) -0.0005(9) 0.0050(11) -0.0030(11) C8 0.0513(17) 0.0247(12) 0.0150(11) -0.0019(9) -0.0042(11) 0.0131(11) C9 0.0302(13) 0.0313(13) 0.0135(10) -0.0060(9) -0.0031(9) 0.0098(10) C9A 0.0236(11) 0.0218(11) 0.0094(9) -0.0036(8) 0.0010(8) 0.0026(8) C10 0.0133(10) 0.0317(12) 0.0180(10) -0.0081(9) 0.0048(8) -0.0033(9) C11 0.0223(11) 0.0230(11) 0.0170(10) -0.0053(8) 0.0107(8) -0.0067(9) C11A 0.0219(10) 0.0128(9) 0.0150(10) -0.0013(8) 0.0087(8) 0.0006(8) C12 0.0147(9) 0.0168(10) 0.0132(9) 0.0011(8) 0.0046(7) -0.0002(8) C13 0.0146(10) 0.0179(10) 0.0133(9) 0.0027(8) 0.0037(7) -0.0014(8) Br 0.02930(14) 0.02468(13) 0.01404(12) -0.00060(8) 0.01109(9) -0.00894(9) C14 0.0145(9) 0.0212(10) 0.0137(9) -0.0005(8) 0.0084(7) -0.0017(8) C15 0.0227(11) 0.0237(11) 0.0162(10) 0.0018(9) 0.0095(9) 0.0011(9) C16 0.0330(13) 0.0191(11) 0.0301(12) 0.0042(10) 0.0193(10) 0.0004(10) C17 0.0320(12) 0.0222(12) 0.0319(13) -0.0100(10) 0.0219(10) -0.0094(10) C18 0.0230(11) 0.0321(13) 0.0177(11) -0.0057(9) 0.0107(9) -0.0066(9) C19 0.0197(10) 0.0228(11) 0.0151(10) 0.0003(8) 0.0083(8) -0.0004(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.381(3) . ? C1 C11A 1.407(3) . ? C1 H1 1.02(3) . ? C2 C3 1.377(3) . ? C2 H2 0.95(3) . ? C3 C4 1.387(3) . ? C3 H3 0.91(3) . ? C4 C4A 1.396(3) . ? C4 H4 0.89(2) . ? C4A C11A 1.404(3) . ? C4A C5 1.516(3) . ? C5 C12 1.516(3) . ? C5 C5A 1.518(3) . ? C5 H5 0.94(2) . ? C5A C6 1.391(3) . ? C5A C9A 1.401(3) . ? C6 C7 1.395(4) . ? C6 H6 0.95(2) . ? C7 C8 1.369(4) . ? C7 H7 0.92(3) . ? C8 C9 1.378(4) . ? C8 H8 0.99(3) . ? C9 C9A 1.404(3) . ? C9 H9 0.95(2) . ? C9A C10 1.454(3) . ? C10 C11 1.340(3) . ? C10 H10 0.90(3) . ? C11 C11A 1.462(3) . ? C11 H11 0.97(2) . ? C12 C13 1.325(3) . ? C12 H12 0.94(3) . ? C13 C14 1.477(3) . ? C13 Br 1.9232(19) . ? C14 C19 1.395(3) . ? C14 C15 1.397(3) . ? C15 C16 1.386(3) . ? C15 H15 0.90(3) . ? C16 C17 1.383(3) . ? C16 H16 0.95(3) . ? C17 C18 1.389(4) . ? C17 H17 0.96(3) . ? C18 C19 1.383(3) . ? C18 H18 0.94(3) . ? C19 H19 0.92(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11A 121.1(2) . . ? C2 C1 H1 126.8(15) . . ? C11A C1 H1 112.0(15) . . ? C3 C2 C1 119.9(2) . . ? C3 C2 H2 122.5(15) . . ? C1 C2 H2 117.6(15) . . ? C2 C3 C4 119.9(2) . . ? C2 C3 H3 120.7(17) . . ? C4 C3 H3 119.4(17) . . ? C3 C4 C4A 121.3(2) . . ? C3 C4 H4 119.0(15) . . ? C4A C4 H4 119.6(15) . . ? C4 C4A C11A 118.91(19) . . ? C4 C4A C5 119.10(18) . . ? C11A C4A C5 121.95(18) . . ? C4A C5 C12 111.05(16) . . ? C4A C5 C5A 111.94(16) . . ? C12 C5 C5A 113.38(16) . . ? C4A C5 H5 105.8(14) . . ? C12 C5 H5 106.6(14) . . ? C5A C5 H5 107.6(14) . . ? C6 C5A C9A 119.0(2) . . ? C6 C5A C5 119.33(19) . . ? C9A C5A C5 121.64(18) . . ? C5A C6 C7 120.9(2) . . ? C5A C6 H6 118.7(14) . . ? C7 C6 H6 120.3(14) . . ? C8 C7 C6 120.2(2) . . ? C8 C7 H7 119.3(19) . . ? C6 C7 H7 120.5(19) . . ? C7 C8 C9 119.5(2) . . ? C7 C8 H8 123.8(17) . . ? C9 C8 H8 116.7(17) . . ? C8 C9 C9A 121.5(2) . . ? C8 C9 H9 120.9(15) . . ? C9A C9 H9 117.5(15) . . ? C5A C9A C9 118.8(2) . . ? C5A C9A C10 123.46(19) . . ? C9 C9A C10 117.8(2) . . ? C11 C10 C9A 127.9(2) . . ? C11 C10 H10 116.1(16) . . ? C9A C10 H10 115.7(15) . . ? C10 C11 C11A 127.4(2) . . ? C10 C11 H11 118.1(14) . . ? C11A C11 H11 114.2(14) . . ? C4A C11A C1 118.81(19) . . ? C4A C11A C11 123.37(18) . . ? C1 C11A C11 117.82(19) . . ? C13 C12 C5 127.68(19) . . ? C13 C12 H12 115.6(16) . . ? C5 C12 H12 116.7(16) . . ? C12 C13 C14 126.16(18) . . ? C12 C13 Br 119.98(16) . . ? C14 C13 Br 113.84(13) . . ? C19 C14 C15 118.7(2) . . ? C19 C14 C13 121.77(19) . . ? C15 C14 C13 119.50(18) . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H15 120.5(17) . . ? C14 C15 H15 119.0(17) . . ? C17 C16 C15 120.3(2) . . ? C17 C16 H16 121.5(15) . . ? C15 C16 H16 118.2(15) . . ? C16 C17 C18 119.8(2) . . ? C16 C17 H17 117.5(15) . . ? C18 C17 H17 122.7(15) . . ? C19 C18 C17 120.1(2) . . ? C19 C18 H18 120.9(16) . . ? C17 C18 H18 118.9(16) . . ? C18 C19 C14 120.7(2) . . ? C18 C19 H19 120.9(14) . . ? C14 C19 H19 118.4(14) . . ? 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 C11A C1 C2 C3 0.1(3) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C4A 0.7(3) . . . . ? C3 C4 C4A C11A -1.6(3) . . . . ? C3 C4 C4A C5 176.30(19) . . . . ? C4 C4A C5 C12 -112.5(2) . . . . ? C11A C4A C5 C12 65.4(2) . . . . ? C4 C4A C5 C5A 119.7(2) . . . . ? C11A C4A C5 C5A -62.5(2) . . . . ? C4A C5 C5A C6 -119.8(2) . . . . ? C12 C5 C5A C6 113.6(2) . . . . ? C4A C5 C5A C9A 62.1(2) . . . . ? C12 C5 C5A C9A -64.4(2) . . . . ? C9A C5A C6 C7 0.3(3) . . . . ? C5 C5A C6 C7 -177.81(19) . . . . ? C5A C6 C7 C8 0.3(3) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C7 C8 C9 C9A -1.2(3) . . . . ? C6 C5A C9A C9 -1.3(3) . . . . ? C5 C5A C9A C9 176.75(18) . . . . ? C6 C5A C9A C10 178.45(19) . . . . ? C5 C5A C9A C10 -3.5(3) . . . . ? C8 C9 C9A C5A 1.8(3) . . . . ? C8 C9 C9A C10 -178.0(2) . . . . ? C5A C9A C10 C11 -34.6(3) . . . . ? C9 C9A C10 C11 145.2(2) . . . . ? C9A C10 C11 C11A 1.5(4) . . . . ? C4 C4A C11A C1 1.7(3) . . . . ? C5 C4A C11A C1 -176.10(18) . . . . ? C4 C4A C11A C11 -177.74(19) . . . . ? C5 C4A C11A C11 4.4(3) . . . . ? C2 C1 C11A C4A -1.0(3) . . . . ? C2 C1 C11A C11 178.5(2) . . . . ? C10 C11 C11A C4A 32.3(3) . . . . ? C10 C11 C11A C1 -147.2(2) . . . . ? C4A C5 C12 C13 153.0(2) . . . . ? C5A C5 C12 C13 -79.9(3) . . . . ? C5 C12 C13 C14 -175.31(19) . . . . ? C5 C12 C13 Br 2.9(3) . . . . ? C12 C13 C14 C19 -129.2(2) . . . . ? Br C13 C14 C19 52.5(2) . . . . ? C12 C13 C14 C15 50.8(3) . . . . ? Br C13 C14 C15 -127.53(17) . . . . ? C19 C14 C15 C16 -0.6(3) . . . . ? C13 C14 C15 C16 179.37(19) . . . . ? C14 C15 C16 C17 0.6(3) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C16 C17 C18 C19 -0.6(3) . . . . ? C17 C18 C19 C14 0.5(3) . . . . ? C15 C14 C19 C18 0.1(3) . . . . ? C13 C14 C19 C18 -179.91(19) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.519 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.078 #===END data_mjm133(38) _database_code_depnum_ccdc_archive 'CCDC 769741' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H20' _chemical_formula_sum 'C29 H20' _chemical_formula_weight 368.45 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.337(3) _cell_length_b 5.7025(7) _cell_length_c 28.668(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.404(2) _cell_angle_gamma 90.00 _cell_volume 3925.2(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4571 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 30.34 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7528 _exptl_absorpt_correction_T_max 0.9792 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.200 before and 0.028 after correction. The Ratio of minimum to maximum transmission is 0.768817. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15216 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3836 _reflns_number_gt 3199 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0363P)^2^+2.0171P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3836 _refine_ls_number_parameters 343 _refine_ls_number_restraints 53 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0865 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.040 _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 C10 C 0.40310(5) 1.3931(2) 0.25214(4) 0.0283(3) Uani 1 1 d . . . C11 C 0.36966(5) 1.3315(2) 0.28518(4) 0.0321(3) Uani 1 1 d . A . H11 H 0.3501 1.1866 0.2823 0.039 Uiso 1 1 calc R . . C12 C 0.36483(6) 1.4807(3) 0.32218(5) 0.0377(3) Uani 1 1 d . . . H12 H 0.3414 1.4395 0.3444 0.045 Uiso 1 1 calc R A . C13 C 0.39387(6) 1.6895(3) 0.32704(5) 0.0404(4) Uani 1 1 d . A . H13 H 0.3913 1.7893 0.3531 0.049 Uiso 1 1 calc R . . C14 C 0.42645(6) 1.7533(3) 0.29424(5) 0.0404(3) Uani 1 1 d . . . H14 H 0.4460 1.8983 0.2975 0.049 Uiso 1 1 calc R A . C15 C 0.43085(5) 1.6075(3) 0.25671(5) 0.0347(3) Uani 1 1 d . A . H15 H 0.4529 1.6534 0.2338 0.042 Uiso 1 1 calc R . . C24 C 0.34196(6) 0.4974(2) -0.04049(4) 0.0349(3) Uani 1 1 d . . . H24 H 0.3425 0.3699 -0.0617 0.042 Uiso 0.858(2) 1 calc PR A 1 H24B H 0.3525 0.3924 -0.0632 0.042 Uiso 0.142(2) 1 calc PR A 2 C25 C 0.30772(5) 0.6866(2) -0.05358(4) 0.0335(3) Uani 1 1 d . A . H25 H 0.2858 0.6922 -0.0842 0.040 Uiso 1 1 calc R . . C26 C 0.30542(5) 0.8685(2) -0.02200(4) 0.0307(3) Uani 1 1 d . . . H26 H 0.2811 0.9972 -0.0305 0.037 Uiso 0.858(2) 1 calc PR A 1 H26B H 0.2884 1.0128 -0.0328 0.037 Uiso 0.142(2) 1 calc PR A 2 C1 C 0.41323(5) 0.6774(2) 0.08305(5) 0.0238(3) Uani 0.858(2) 1 d PD A 1 H1 H 0.4260 0.5136 0.0913 0.029 Uiso 0.858(2) 1 calc PR A 1 C2 C 0.38854(9) 0.7816(3) 0.12400(6) 0.0222(4) Uani 0.858(2) 1 d PD A 1 C3 C 0.41971(5) 0.9684(2) 0.14225(4) 0.0220(3) Uani 0.858(2) 1 d PD A 1 C3A C 0.46574(7) 1.0055(4) 0.11578(5) 0.0222(3) Uani 0.858(2) 1 d PD A 1 C4 C 0.50701(8) 1.1770(3) 0.12071(6) 0.0247(4) Uani 0.858(2) 1 d PD A 1 H4 H 0.5085 1.2961 0.1441 0.030 Uiso 0.858(2) 1 calc PR A 1 C5 C 0.54601(7) 1.1681(4) 0.09035(7) 0.0268(4) Uani 0.858(2) 1 d PD A 1 H5 H 0.5743 1.2844 0.0927 0.032 Uiso 0.858(2) 1 calc PR A 1 C6 C 0.54438(7) 0.9920(4) 0.05660(6) 0.0308(4) Uani 0.858(2) 1 d PD A 1 H6 H 0.5718 0.9884 0.0366 0.037 Uiso 0.858(2) 1 calc PR A 1 C7 C 0.50291(8) 0.8205(3) 0.05184(5) 0.0293(4) Uani 0.858(2) 1 d PD A 1 H7 H 0.5018 0.6997 0.0289 0.035 Uiso 0.858(2) 1 calc PR A 1 C7A C 0.46335(8) 0.8311(3) 0.08149(6) 0.0233(3) Uani 0.858(2) 1 d PD A 1 C8 C 0.41367(6) 1.1148(3) 0.18112(5) 0.0239(3) Uani 0.858(2) 1 d PD A 1 C9 C 0.41039(7) 1.2465(3) 0.21326(5) 0.0254(4) Uani 0.858(2) 1 d PD A 1 C16 C 0.33941(7) 0.6762(3) 0.13977(7) 0.0241(4) Uani 0.858(2) 1 d PD A 1 C17 C 0.31704(8) 0.4659(4) 0.11976(6) 0.0287(4) Uani 0.858(2) 1 d PD A 1 H17 H 0.3327 0.3954 0.0949 0.034 Uiso 0.858(2) 1 calc PR A 1 C18 C 0.27221(10) 0.3589(3) 0.13581(7) 0.0358(5) Uani 0.858(2) 1 d PD A 1 H18 H 0.2576 0.2161 0.1218 0.043 Uiso 0.858(2) 1 calc PR A 1 C19 C 0.24876(11) 0.4581(6) 0.17177(10) 0.0374(7) Uani 0.858(2) 1 d PD A 1 H19 H 0.2185 0.3835 0.1830 0.045 Uiso 0.858(2) 1 calc PR A 1 C20 C 0.26987(9) 0.6679(3) 0.19135(6) 0.0365(5) Uani 0.858(2) 1 d PD A 1 H20 H 0.2537 0.7379 0.2160 0.044 Uiso 0.858(2) 1 calc PR A 1 C21 C 0.31411(7) 0.7770(3) 0.17558(6) 0.0293(4) Uani 0.858(2) 1 d PD A 1 H21 H 0.3276 0.9222 0.1892 0.035 Uiso 0.858(2) 1 calc PR A 1 C22 C 0.37445(8) 0.6757(3) 0.03561(5) 0.0238(4) Uani 0.858(2) 1 d PD A 1 C23 C 0.37625(10) 0.4916(3) 0.00423(7) 0.0283(4) Uani 0.858(2) 1 d PD A 1 H23 H 0.4004 0.3624 0.0128 0.034 Uiso 0.858(2) 1 calc PR A 1 C27 C 0.33887(14) 0.8624(4) 0.02224(10) 0.0269(6) Uani 0.858(2) 1 d PD A 1 H27 H 0.3373 0.9884 0.0437 0.032 Uiso 0.858(2) 1 calc PR A 1 C1B C 0.3757(3) 0.5878(14) 0.0908(3) 0.025(2) Uiso 0.142(2) 1 d PD A 2 H1B H 0.4014 0.4498 0.0940 0.030 Uiso 0.142(2) 1 calc PR A 2 C2B C 0.4043(5) 0.791(2) 0.1165(4) 0.033(4) Uiso 0.142(2) 1 d PD A 2 C3B C 0.3772(3) 0.8578(15) 0.1530(3) 0.029(2) Uiso 0.142(2) 1 d PD A 2 C3AB C 0.3305(4) 0.700(2) 0.1548(4) 0.017(3) Uiso 0.142(2) 1 d PD A 2 C4B C 0.2938(5) 0.687(2) 0.1862(4) 0.027(3) Uiso 0.142(2) 1 d PD A 2 H4B H 0.2953 0.7963 0.2115 0.033 Uiso 0.142(2) 1 calc PR A 2 C5B C 0.2548(7) 0.511(4) 0.1798(7) 0.030(5) Uiso 0.142(2) 1 d PD A 2 H5B H 0.2283 0.5006 0.2007 0.036 Uiso 0.142(2) 1 calc PR A 2 C6B C 0.2530(6) 0.347(3) 0.1434(6) 0.045(4) Uiso 0.142(2) 1 d PD A 2 H6B H 0.2260 0.2252 0.1405 0.054 Uiso 0.142(2) 1 calc PR A 2 C7B C 0.2900(4) 0.3590(18) 0.1115(4) 0.026(2) Uiso 0.142(2) 1 d PD A 2 H7B H 0.2891 0.2496 0.0864 0.032 Uiso 0.142(2) 1 calc PR A 2 C7AB C 0.3289(5) 0.543(2) 0.1185(4) 0.026(3) Uiso 0.142(2) 1 d PD A 2 C8B C 0.3891(4) 1.0390(17) 0.1881(3) 0.031(2) Uiso 0.142(2) 1 d PD A 2 C9B C 0.3938(5) 1.182(2) 0.2169(4) 0.035(3) Uiso 0.142(2) 1 d PD A 2 C16B C 0.4560(4) 0.905(2) 0.1030(4) 0.021(2) Uiso 0.142(2) 1 d PD A 2 C17B C 0.4834(5) 0.7828(18) 0.0733(4) 0.022(2) Uiso 0.142(2) 1 d PD A 2 H17B H 0.4703 0.6328 0.0622 0.026 Uiso 0.142(2) 1 calc PR A 2 C18B C 0.5306(6) 0.877(3) 0.0593(4) 0.039(3) Uiso 0.142(2) 1 d PD A 2 H18B H 0.5503 0.7911 0.0390 0.047 Uiso 0.142(2) 1 calc PR A 2 C19B C 0.5486(5) 1.095(2) 0.0750(5) 0.029(3) Uiso 0.142(2) 1 d PD A 2 H19B H 0.5797 1.1645 0.0641 0.035 Uiso 0.142(2) 1 calc PR A 2 C20B C 0.5220(6) 1.213(2) 0.1063(5) 0.031(3) Uiso 0.142(2) 1 d PD A 2 H20B H 0.5363 1.3582 0.1190 0.037 Uiso 0.142(2) 1 calc PR A 2 C21B C 0.4746(6) 1.121(2) 0.1194(4) 0.029(3) Uiso 0.142(2) 1 d PD A 2 H21B H 0.4548 1.2065 0.1397 0.035 Uiso 0.142(2) 1 calc PR A 2 C22B C 0.3549(5) 0.6366(19) 0.0383(3) 0.025(3) Uiso 0.142(2) 1 d PD A 2 C23B C 0.3588(5) 0.471(2) 0.0036(5) 0.029(4) Uiso 0.142(2) 1 d PD A 2 H23B H 0.3754 0.3244 0.0136 0.034 Uiso 0.142(2) 1 calc PR A 2 C27B C 0.3267(8) 0.843(3) 0.0231(8) 0.035(6) Uiso 0.142(2) 1 d PD A 2 H27B H 0.3228 0.9636 0.0451 0.043 Uiso 0.142(2) 1 calc PR A 2 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 C10 0.0230(6) 0.0349(7) 0.0245(6) -0.0033(5) -0.0038(5) 0.0092(5) C11 0.0266(6) 0.0311(7) 0.0373(7) 0.0001(6) 0.0012(5) 0.0038(5) C12 0.0351(7) 0.0475(9) 0.0312(7) 0.0016(6) 0.0073(6) 0.0148(7) C13 0.0477(8) 0.0399(8) 0.0294(7) -0.0119(6) -0.0064(6) 0.0157(7) C14 0.0401(8) 0.0328(8) 0.0421(8) -0.0039(6) -0.0120(6) -0.0006(6) C15 0.0262(6) 0.0433(8) 0.0325(7) 0.0032(6) -0.0010(5) 0.0010(6) C24 0.0425(8) 0.0355(8) 0.0275(7) -0.0067(6) 0.0077(6) -0.0087(6) C25 0.0302(7) 0.0455(8) 0.0239(6) 0.0020(6) 0.0015(5) -0.0093(6) C26 0.0269(6) 0.0345(7) 0.0301(7) 0.0060(6) 0.0023(5) -0.0008(5) C1 0.0237(7) 0.0210(7) 0.0261(7) 0.0001(6) 0.0026(5) 0.0003(6) C2 0.0242(9) 0.0205(8) 0.0205(8) 0.0030(6) -0.0008(8) 0.0038(7) C3 0.0223(7) 0.0224(7) 0.0206(7) 0.0030(5) 0.0007(5) 0.0019(6) C3A 0.0232(8) 0.0202(10) 0.0217(7) 0.0017(7) -0.0010(6) 0.0040(7) C4 0.0225(10) 0.0265(8) 0.0240(8) 0.0021(7) 0.0005(7) 0.0009(7) C5 0.0229(9) 0.0306(10) 0.0257(9) 0.0023(8) 0.0007(7) -0.0049(7) C6 0.0240(8) 0.0415(12) 0.0274(9) 0.0004(9) 0.0056(6) 0.0017(8) C7 0.0267(9) 0.0351(9) 0.0254(8) -0.0041(7) 0.0026(7) 0.0024(7) C7A 0.0214(8) 0.0229(8) 0.0248(9) -0.0011(7) 0.0010(7) 0.0040(7) C8 0.0198(7) 0.0257(8) 0.0255(7) 0.0029(6) 0.0017(5) -0.0008(6) C9 0.0211(8) 0.0263(9) 0.0273(8) 0.0013(7) -0.0003(6) 0.0004(7) C16 0.0224(8) 0.0262(10) 0.0222(9) 0.0046(8) -0.0007(7) 0.0005(6) C17 0.0290(9) 0.0247(10) 0.0302(9) 0.0046(8) -0.0014(7) -0.0018(9) C18 0.0342(11) 0.0302(10) 0.0390(12) 0.0088(8) -0.0062(10) -0.0071(9) C19 0.0245(10) 0.0476(19) 0.0387(14) 0.0135(13) 0.0012(9) -0.0117(10) C20 0.0246(9) 0.0524(13) 0.0322(9) 0.0048(8) 0.0038(7) -0.0064(9) C21 0.0233(8) 0.0361(9) 0.0278(8) 0.0023(8) 0.0025(6) -0.0027(7) C22 0.0224(8) 0.0242(8) 0.0248(8) 0.0003(6) 0.0041(6) -0.0041(7) C23 0.0285(12) 0.0271(10) 0.0291(9) -0.0025(6) 0.0039(8) -0.0017(8) C27 0.0275(13) 0.0258(10) 0.0269(11) -0.0028(6) 0.0030(9) -0.0022(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C10 C11 1.3910(18) . ? C10 C15 1.3923(19) . ? C10 C9 1.4275(19) . ? C10 C9B 1.564(11) . ? C11 C12 1.3795(18) . ? C11 H11 0.9500 . ? C12 C13 1.380(2) . ? C12 H12 0.9500 . ? C13 C14 1.374(2) . ? C13 H13 0.9500 . ? C14 C15 1.3781(19) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C24 C23B 1.272(14) . ? C24 C25 1.3771(19) . ? C24 C23 1.411(2) . ? C24 H24 0.9500 . ? C24 H24B 0.9500 . ? C25 C26 1.3839(18) . ? C25 H25 0.9500 . ? C26 C27B 1.32(2) . ? C26 C27 1.391(3) . ? C26 H26 0.9500 . ? C26 H26B 0.9500 . ? C1 C7A 1.509(2) . ? C1 C22 1.5235(19) . ? C1 C2 1.524(2) . ? C1 H1 1.0000 . ? C2 C3 1.361(2) . ? C2 C16 1.474(3) . ? C3 C8 1.4192(19) . ? C3 C3A 1.467(2) . ? C3A C4 1.393(3) . ? C3A C7A 1.393(2) . ? C4 C5 1.390(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(3) . ? C5 H5 0.9500 . ? C6 C7 1.396(3) . ? C6 H6 0.9500 . ? C7 C7A 1.386(2) . ? C7 H7 0.9500 . ? C8 C9 1.201(2) . ? C16 C17 1.400(3) . ? C16 C21 1.404(2) . ? C17 C18 1.393(3) . ? C17 H17 0.9500 . ? C18 C19 1.379(4) . ? C18 H18 0.9500 . ? C19 C20 1.385(4) . ? C19 H19 0.9500 . ? C20 C21 1.382(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C27 1.386(2) . ? C22 C23 1.388(2) . ? C23 H23 0.9500 . ? C27 H27 0.9500 . ? C1B C2B 1.483(12) . ? C1B C7AB 1.513(11) . ? C1B C22B 1.533(11) . ? C1B H1B 1.0000 . ? C2B C3B 1.378(11) . ? C2B C16B 1.522(12) . ? C3B C8B 1.439(11) . ? C3B C3AB 1.458(11) . ? C3AB C4B 1.368(13) . ? C3AB C7AB 1.370(13) . ? C4B C5B 1.375(15) . ? C4B H4B 0.9500 . ? C5B C6B 1.397(15) . ? C5B H5B 0.9500 . ? C6B C7B 1.386(13) . ? C6B H6B 0.9500 . ? C7B C7AB 1.405(12) . ? C7B H7B 0.9500 . ? C8B C9B 1.153(12) . ? C16B C17B 1.357(12) . ? C16B C21B 1.365(12) . ? C17B C18B 1.384(13) . ? C17B H17B 0.9500 . ? C18B C19B 1.370(14) . ? C18B H18B 0.9500 . ? C19B C20B 1.365(13) . ? C19B H19B 0.9500 . ? C20B C21B 1.374(13) . ? C20B H20B 0.9500 . ? C21B H21B 0.9500 . ? C22B C23B 1.388(13) . ? C22B C27B 1.394(15) . ? C23B H23B 0.9500 . ? C27B H27B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 C10 C15 119.12(12) . . ? C11 C10 C9 123.02(14) . . ? C15 C10 C9 117.86(13) . . ? C11 C10 C9B 101.9(5) . . ? C15 C10 C9B 138.9(5) . . ? C12 C11 C10 120.04(13) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.20(13) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 120.19(13) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.09(14) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 120.32(13) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? C23B C24 C25 116.6(6) . . ? C25 C24 C23 120.50(13) . . ? C23B C24 H24 120.5 . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C23B C24 H24B 121.7 . . ? C25 C24 H24B 121.7 . . ? C23 C24 H24B 115.0 . . ? C24 C25 C26 119.75(12) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C27B C26 C25 120.4(8) . . ? C25 C26 C27 119.84(15) . . ? C27B C26 H26 117.8 . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C27B C26 H26B 119.8 . . ? C25 C26 H26B 119.8 . . ? C27 C26 H26B 118.6 . . ? C7A C1 C22 111.28(12) . . ? C7A C1 C2 102.62(14) . . ? C22 C1 C2 115.17(12) . . ? C7A C1 H1 109.2 . . ? C22 C1 H1 109.2 . . ? C2 C1 H1 109.2 . . ? C3 C2 C16 129.07(17) . . ? C3 C2 C1 109.64(17) . . ? C16 C2 C1 121.25(15) . . ? C2 C3 C8 129.74(15) . . ? C2 C3 C3A 109.78(16) . . ? C8 C3 C3A 120.46(15) . . ? C4 C3A C7A 121.29(15) . . ? C4 C3A C3 130.4(2) . . ? C7A C3A C3 108.4(2) . . ? C5 C4 C3A 117.78(15) . . ? C5 C4 H4 121.1 . . ? C3A C4 H4 121.1 . . ? C4 C5 C6 121.15(15) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C7 120.80(14) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C7A C7 C6 118.22(14) . . ? C7A C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? C7 C7A C3A 120.74(15) . . ? C7 C7A C1 129.70(18) . . ? C3A C7A C1 109.55(19) . . ? C9 C8 C3 176.71(18) . . ? C8 C9 C10 175.8(2) . . ? C17 C16 C21 117.57(17) . . ? C17 C16 C2 120.3(2) . . ? C21 C16 C2 122.14(16) . . ? C18 C17 C16 120.88(19) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C19 C18 C17 120.6(2) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 119.1(2) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? C21 C20 C19 120.91(18) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C16 120.87(16) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? C27 C22 C23 119.10(18) . . ? C27 C22 C1 120.65(17) . . ? C23 C22 C1 120.18(15) . . ? C22 C23 C24 119.63(17) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C22 C27 C26 121.1(2) . . ? C22 C27 H27 119.4 . . ? C26 C27 H27 119.4 . . ? C2B C1B C7AB 101.8(8) . . ? C2B C1B C22B 113.5(8) . . ? C7AB C1B C22B 113.0(8) . . ? C2B C1B H1B 109.4 . . ? C7AB C1B H1B 109.4 . . ? C22B C1B H1B 109.4 . . ? C3B C2B C1B 110.4(8) . . ? C3B C2B C16B 126.3(10) . . ? C1B C2B C16B 123.3(9) . . ? C2B C3B C8B 131.6(8) . . ? C2B C3B C3AB 109.3(8) . . ? C8B C3B C3AB 119.1(9) . . ? C4B C3AB C7AB 121.7(9) . . ? C4B C3AB C3B 130.8(12) . . ? C7AB C3AB C3B 107.5(10) . . ? C3AB C4B C5B 117.4(10) . . ? C3AB C4B H4B 121.3 . . ? C5B C4B H4B 121.3 . . ? C4B C5B C6B 121.8(14) . . ? C4B C5B H5B 119.1 . . ? C6B C5B H5B 119.1 . . ? C7B C6B C5B 121.0(13) . . ? C7B C6B H6B 119.5 . . ? C5B C6B H6B 119.5 . . ? C6B C7B C7AB 116.0(10) . . ? C6B C7B H7B 122.0 . . ? C7AB C7B H7B 122.0 . . ? C3AB C7AB C7B 122.1(9) . . ? C3AB C7AB C1B 111.0(9) . . ? C7B C7AB C1B 126.8(11) . . ? C9B C8B C3B 173.9(12) . . ? C8B C9B C10 173.7(12) . . ? C17B C16B C21B 120.6(10) . . ? C17B C16B C2B 116.7(11) . . ? C21B C16B C2B 122.7(12) . . ? C16B C17B C18B 119.8(10) . . ? C16B C17B H17B 120.1 . . ? C18B C17B H17B 120.1 . . ? C19B C18B C17B 119.7(11) . . ? C19B C18B H18B 120.2 . . ? C17B C18B H18B 120.2 . . ? C20B C19B C18B 119.9(11) . . ? C20B C19B H19B 120.1 . . ? C18B C19B H19B 120.1 . . ? C19B C20B C21B 120.1(11) . . ? C19B C20B H20B 119.9 . . ? C21B C20B H20B 119.9 . . ? C16B C21B C20B 119.7(11) . . ? C16B C21B H21B 120.1 . . ? C20B C21B H21B 120.1 . . ? C23B C22B C27B 116.0(13) . . ? C23B C22B C1B 122.0(10) . . ? C27B C22B C1B 121.8(12) . . ? C24 C23B C22B 125.5(12) . . ? C24 C23B H23B 117.2 . . ? C22B C23B H23B 117.2 . . ? C26 C27B C22B 119.7(17) . . ? C26 C27B H27B 120.2 . . ? C22B C27B H27B 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 C10 C11 C12 -0.75(18) . . . . ? C9 C10 C11 C12 179.42(12) . . . . ? C9B C10 C11 C12 -177.7(5) . . . . ? C10 C11 C12 C13 -1.14(19) . . . . ? C11 C12 C13 C14 2.0(2) . . . . ? C12 C13 C14 C15 -0.9(2) . . . . ? C13 C14 C15 C10 -1.0(2) . . . . ? C11 C10 C15 C14 1.83(18) . . . . ? C9 C10 C15 C14 -178.33(12) . . . . ? C9B C10 C15 C14 177.3(7) . . . . ? C23B C24 C25 C26 17.5(7) . . . . ? C23 C24 C25 C26 -2.3(2) . . . . ? C24 C25 C26 C27B -13.5(10) . . . . ? C24 C25 C26 C27 1.9(2) . . . . ? C7A C1 C2 C3 0.79(16) . . . . ? C22 C1 C2 C3 -120.29(15) . . . . ? C7A C1 C2 C16 -177.03(14) . . . . ? C22 C1 C2 C16 61.89(19) . . . . ? C16 C2 C3 C8 -0.5(3) . . . . ? C1 C2 C3 C8 -178.10(13) . . . . ? C16 C2 C3 C3A 178.24(15) . . . . ? C1 C2 C3 C3A 0.65(16) . . . . ? C2 C3 C3A C4 178.09(15) . . . . ? C8 C3 C3A C4 -3.0(2) . . . . ? C2 C3 C3A C7A -1.97(16) . . . . ? C8 C3 C3A C7A 176.91(12) . . . . ? C7A C3A C4 C5 -0.2(2) . . . . ? C3 C3A C4 C5 179.69(14) . . . . ? C3A C4 C5 C6 -0.9(2) . . . . ? C4 C5 C6 C7 0.9(2) . . . . ? C5 C6 C7 C7A 0.2(2) . . . . ? C6 C7 C7A C3A -1.4(2) . . . . ? C6 C7 C7A C1 177.39(15) . . . . ? C4 C3A C7A C7 1.4(2) . . . . ? C3 C3A C7A C7 -178.54(13) . . . . ? C4 C3A C7A C1 -177.59(13) . . . . ? C3 C3A C7A C1 2.47(16) . . . . ? C22 C1 C7A C7 -57.2(2) . . . . ? C2 C1 C7A C7 179.12(16) . . . . ? C22 C1 C7A C3A 121.70(13) . . . . ? C2 C1 C7A C3A -2.01(15) . . . . ? C3 C2 C16 C17 -172.20(16) . . . . ? C1 C2 C16 C17 5.1(2) . . . . ? C3 C2 C16 C21 6.4(3) . . . . ? C1 C2 C16 C21 -176.27(14) . . . . ? C21 C16 C17 C18 -1.6(2) . . . . ? C2 C16 C17 C18 177.08(15) . . . . ? C16 C17 C18 C19 0.1(3) . . . . ? C17 C18 C19 C20 0.9(3) . . . . ? C18 C19 C20 C21 -0.5(3) . . . . ? C19 C20 C21 C16 -1.0(3) . . . . ? C17 C16 C21 C20 2.0(2) . . . . ? C2 C16 C21 C20 -176.63(15) . . . . ? C7A C1 C22 C27 -77.9(3) . . . . ? C2 C1 C22 C27 38.4(3) . . . . ? C7A C1 C22 C23 99.0(2) . . . . ? C2 C1 C22 C23 -144.71(18) . . . . ? C27 C22 C23 C24 -0.1(3) . . . . ? C1 C22 C23 C24 -177.07(16) . . . . ? C23B C24 C23 C22 -81(2) . . . . ? C25 C24 C23 C22 1.5(3) . . . . ? C23 C22 C27 C26 -0.4(4) . . . . ? C1 C22 C27 C26 176.6(2) . . . . ? C27B C26 C27 C22 96(4) . . . . ? C25 C26 C27 C22 -0.5(4) . . . . ? C7AB C1B C2B C3B -1.4(13) . . . . ? C22B C1B C2B C3B 120.3(10) . . . . ? C7AB C1B C2B C16B 179.1(12) . . . . ? C22B C1B C2B C16B -59.2(15) . . . . ? C1B C2B C3B C8B 178.6(9) . . . . ? C16B C2B C3B C8B -2(2) . . . . ? C1B C2B C3B C3AB 2.0(14) . . . . ? C16B C2B C3B C3AB -178.6(12) . . . . ? C2B C3B C3AB C4B 175.6(13) . . . . ? C8B C3B C3AB C4B -1.5(17) . . . . ? C2B C3B C3AB C7AB -1.7(13) . . . . ? C8B C3B C3AB C7AB -178.8(9) . . . . ? C7AB C3AB C4B C5B 0(2) . . . . ? C3B C3AB C4B C5B -177.5(14) . . . . ? C3AB C4B C5B C6B 1(3) . . . . ? C4B C5B C6B C7B -2(3) . . . . ? C5B C6B C7B C7AB 1(2) . . . . ? C4B C3AB C7AB C7B -0.5(19) . . . . ? C3B C3AB C7AB C7B 177.2(10) . . . . ? C4B C3AB C7AB C1B -176.9(10) . . . . ? C3B C3AB C7AB C1B 0.8(13) . . . . ? C6B C7B C7AB C3AB 0.4(18) . . . . ? C6B C7B C7AB C1B 176.2(11) . . . . ? C2B C1B C7AB C3AB 0.3(13) . . . . ? C22B C1B C7AB C3AB -121.7(10) . . . . ? C2B C1B C7AB C7B -175.9(12) . . . . ? C22B C1B C7AB C7B 62.1(14) . . . . ? C3B C2B C16B C17B 165.6(12) . . . . ? C1B C2B C16B C17B -15.0(17) . . . . ? C3B C2B C16B C21B -15(2) . . . . ? C1B C2B C16B C21B 164.7(11) . . . . ? C21B C16B C17B C18B -0.2(16) . . . . ? C2B C16B C17B C18B 179.5(11) . . . . ? C16B C17B C18B C19B -1.1(18) . . . . ? C17B C18B C19B C20B 4(2) . . . . ? C18B C19B C20B C21B -4.9(19) . . . . ? C17B C16B C21B C20B -1.1(17) . . . . ? C2B C16B C21B C20B 179.2(11) . . . . ? C19B C20B C21B C16B 3.7(18) . . . . ? C2B C1B C22B C23B 140.0(11) . . . . ? C7AB C1B C22B C23B -104.8(12) . . . . ? C2B C1B C22B C27B -45.7(15) . . . . ? C7AB C1B C22B C27B 69.5(15) . . . . ? C25 C24 C23B C22B -13.4(14) . . . . ? C23 C24 C23B C22B 94(2) . . . . ? C27B C22B C23B C24 4.6(19) . . . . ? C1B C22B C23B C24 179.2(9) . . . . ? C25 C26 C27B C22B 4(2) . . . . ? C27 C26 C27B C22B -87(4) . . . . ? C23B C22B C27B C26 0(2) . . . . ? C1B C22B C27B C26 -174.3(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.219 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.030 #===END data_mjm165(23c) _database_code_depnum_ccdc_archive 'CCDC 769742' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H15 O F3' _chemical_formula_sum 'C24 H15 O F3' _chemical_formula_weight 376.36 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.334(7) _cell_length_b 8.900(5) _cell_length_c 20.175(13) _cell_angle_alpha 90.00 _cell_angle_beta 100.490(13) _cell_angle_gamma 90.00 _cell_volume 1825(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4417 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 24.29 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7410 _exptl_absorpt_correction_T_max 0.9846 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.075 before and 0.018 after correction. The Ratio of minimum to maximum transmission is 0.752541. The \l/2 correction factor is 0.0015. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12850 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.00 _reflns_number_total 2856 _reflns_number_gt 2370 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0516P)^2^+0.4104P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2856 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 C1 C 0.1736(2) 1.0117(2) 0.93414(9) 0.0672(5) Uani 1 1 d . . . H1 H 0.1223 1.0958 0.9383 0.081 Uiso 1 1 calc R . . C2 C 0.3048(2) 1.0292(2) 0.93696(10) 0.0764(6) Uani 1 1 d . . . H2 H 0.3427 1.1241 0.9436 0.092 Uiso 1 1 calc R . . C3 C 0.38142(19) 0.9069(2) 0.92997(9) 0.0688(5) Uani 1 1 d . . . H3 H 0.4710 0.9188 0.9304 0.083 Uiso 1 1 calc R . . C4 C 0.32536(16) 0.76585(19) 0.92221(8) 0.0573(4) Uani 1 1 d . . . H4 H 0.3781 0.6832 0.9176 0.069 Uiso 1 1 calc R . . C4A C 0.19270(15) 0.74502(17) 0.92109(7) 0.0470(4) Uani 1 1 d . . . C5 C 0.13838(15) 0.59067(17) 0.91795(8) 0.0493(4) Uani 1 1 d . . . C5A C 0.03164(16) 0.55449(18) 0.86088(8) 0.0537(4) Uani 1 1 d . . . C6 C 0.0476(2) 0.4368(2) 0.81804(9) 0.0707(5) Uani 1 1 d . . . H6 H 0.1266 0.3840 0.8248 0.085 Uiso 1 1 calc R . . C7 C -0.0507(3) 0.3968(3) 0.76593(10) 0.0888(7) Uani 1 1 d . . . H7 H -0.0379 0.3187 0.7372 0.107 Uiso 1 1 calc R . . C8 C -0.1674(2) 0.4722(3) 0.75652(11) 0.0895(7) Uani 1 1 d . . . H8 H -0.2346 0.4453 0.7213 0.107 Uiso 1 1 calc R . . C9 C -0.1859(2) 0.5869(2) 0.79853(10) 0.0762(6) Uani 1 1 d . . . H9 H -0.2669 0.6355 0.7922 0.091 Uiso 1 1 calc R . . C9A C -0.08637(16) 0.63298(19) 0.85072(8) 0.0578(4) Uani 1 1 d . . . C10 C -0.11163(18) 0.7601(2) 0.89165(9) 0.0646(5) Uani 1 1 d . . . H10 H -0.1986 0.7726 0.8967 0.078 Uiso 1 1 calc R . . C11 C -0.02673(18) 0.8613(2) 0.92295(9) 0.0624(5) Uani 1 1 d . . . H11 H -0.0626 0.9357 0.9465 0.075 Uiso 1 1 calc R . . C11A C 0.11323(16) 0.87067(18) 0.92516(8) 0.0529(4) Uani 1 1 d . . . C12 C 0.18838(16) 0.48232(18) 0.96069(8) 0.0565(4) Uani 1 1 d . . . H12 H 0.1468 0.3895 0.9537 0.068 Uiso 1 1 calc R . . C13 C 0.30010(16) 0.48916(18) 1.01725(8) 0.0554(4) Uani 1 1 d . . . O O 0.37624(13) 0.38426(14) 1.02534(7) 0.0780(4) Uani 1 1 d . . . C14 C 0.31831(15) 0.61620(17) 1.06631(8) 0.0506(4) Uani 1 1 d . . . C15 C 0.21453(17) 0.6972(2) 1.08128(8) 0.0584(4) Uani 1 1 d . . . H15 H 0.1301 0.6799 1.0574 0.070 Uiso 1 1 calc R . . C16 C 0.23447(18) 0.8041(2) 1.13157(9) 0.0654(5) Uani 1 1 d . . . H16 H 0.1633 0.8572 1.1421 0.079 Uiso 1 1 calc R . . C17 C 0.35878(18) 0.8322(2) 1.16603(8) 0.0616(5) Uani 1 1 d . A . C20 C 0.3823(3) 0.9451(3) 1.22156(12) 0.0858(6) Uani 1 1 d . . . F1A F 0.2807(5) 0.9899(12) 1.2429(4) 0.139(4) Uani 0.571(14) 1 d P A 1 F2A F 0.4651(8) 0.9015(8) 1.2727(3) 0.126(3) Uani 0.571(14) 1 d P A 1 F3A F 0.4271(13) 1.0716(6) 1.2003(3) 0.135(3) Uani 0.571(14) 1 d P A 1 F1B F 0.5036(8) 1.002(2) 1.2305(8) 0.166(6) Uani 0.429(14) 1 d P A 2 F2B F 0.3046(16) 1.0512(12) 1.2153(5) 0.169(6) Uani 0.429(14) 1 d P A 2 F3B F 0.373(2) 0.8834(9) 1.2791(3) 0.188(7) Uani 0.429(14) 1 d P A 2 C18 C 0.46320(18) 0.7539(2) 1.15029(9) 0.0657(5) Uani 1 1 d . . . H18 H 0.5481 0.7744 1.1729 0.079 Uiso 1 1 calc R A . C19 C 0.44279(17) 0.6458(2) 1.10135(9) 0.0602(4) Uani 1 1 d . A . H19 H 0.5140 0.5916 1.0916 0.072 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 C1 0.0907(14) 0.0426(10) 0.0672(11) -0.0021(8) 0.0115(10) 0.0021(9) C2 0.0966(16) 0.0557(12) 0.0735(12) -0.0019(9) 0.0064(10) -0.0216(11) C3 0.0667(11) 0.0685(13) 0.0681(11) 0.0041(9) 0.0040(9) -0.0181(10) C4 0.0576(10) 0.0559(10) 0.0566(9) 0.0045(8) 0.0056(7) -0.0002(8) C4A 0.0551(9) 0.0433(9) 0.0404(8) 0.0015(6) 0.0029(6) 0.0003(7) C5 0.0523(9) 0.0436(9) 0.0521(9) -0.0022(7) 0.0097(7) 0.0026(7) C5A 0.0593(10) 0.0490(9) 0.0522(9) 0.0007(7) 0.0082(7) -0.0065(8) C6 0.0791(12) 0.0678(12) 0.0657(11) -0.0159(9) 0.0146(9) -0.0073(10) C7 0.1076(18) 0.0920(16) 0.0653(12) -0.0255(11) 0.0120(12) -0.0200(14) C8 0.0972(17) 0.0971(17) 0.0644(12) -0.0038(12) -0.0118(11) -0.0280(14) C9 0.0689(12) 0.0802(14) 0.0714(12) 0.0115(11) -0.0090(10) -0.0112(10) C9A 0.0582(10) 0.0570(10) 0.0555(9) 0.0066(8) 0.0035(8) -0.0066(8) C10 0.0548(10) 0.0706(12) 0.0686(11) 0.0086(9) 0.0116(8) 0.0113(9) C11 0.0696(11) 0.0551(11) 0.0625(10) -0.0006(8) 0.0121(9) 0.0146(9) C11A 0.0664(10) 0.0445(9) 0.0466(8) 0.0005(7) 0.0072(7) 0.0040(8) C12 0.0598(10) 0.0396(9) 0.0685(10) -0.0014(8) 0.0073(8) -0.0018(7) C13 0.0578(9) 0.0437(9) 0.0637(10) 0.0075(8) 0.0089(8) 0.0063(8) O 0.0784(9) 0.0551(8) 0.0936(10) -0.0031(7) -0.0028(7) 0.0221(7) C14 0.0553(9) 0.0448(9) 0.0510(9) 0.0106(7) 0.0079(7) 0.0068(7) C15 0.0561(10) 0.0593(10) 0.0585(10) 0.0076(8) 0.0069(8) 0.0083(8) C16 0.0679(11) 0.0666(12) 0.0631(11) 0.0047(9) 0.0153(9) 0.0222(9) C17 0.0712(11) 0.0587(11) 0.0537(9) 0.0031(8) 0.0083(8) 0.0095(9) C20 0.0954(18) 0.0848(17) 0.0739(15) -0.0128(12) 0.0062(13) 0.0151(15) F1A 0.113(3) 0.198(8) 0.111(5) -0.068(5) 0.035(3) 0.033(3) F2A 0.143(5) 0.131(5) 0.082(3) -0.037(3) -0.034(3) 0.044(4) F3A 0.189(8) 0.081(3) 0.148(4) -0.043(2) 0.068(5) -0.029(3) F1B 0.097(4) 0.187(11) 0.216(11) -0.133(10) 0.031(5) -0.030(5) F2B 0.268(14) 0.118(6) 0.093(5) -0.045(4) -0.038(6) 0.116(7) F3B 0.38(2) 0.131(5) 0.053(3) -0.003(3) 0.045(7) -0.009(10) C18 0.0598(11) 0.0712(12) 0.0628(10) -0.0044(9) 0.0026(8) 0.0030(9) C19 0.0550(10) 0.0617(11) 0.0628(10) 0.0003(8) 0.0078(8) 0.0099(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.356(3) . ? C1 C11A 1.399(3) . ? C1 H1 0.9300 . ? C2 C3 1.368(3) . ? C2 H2 0.9300 . ? C3 C4 1.379(3) . ? C3 H3 0.9300 . ? C4 C4A 1.380(2) . ? C4 H4 0.9300 . ? C4A C11A 1.399(2) . ? C4A C5 1.481(2) . ? C5 C12 1.333(2) . ? C5 C5A 1.478(2) . ? C5A C6 1.387(2) . ? C5A C9A 1.388(2) . ? C6 C7 1.369(3) . ? C6 H6 0.9300 . ? C7 C8 1.363(3) . ? C7 H7 0.9300 . ? C8 C9 1.362(3) . ? C8 H8 0.9300 . ? C9 C9A 1.393(3) . ? C9 H9 0.9300 . ? C9A C10 1.452(3) . ? C10 C11 1.333(3) . ? C10 H10 0.9300 . ? C11 C11A 1.441(3) . ? C11 H11 0.9300 . ? C12 C13 1.469(2) . ? C12 H12 0.9300 . ? C13 O 1.213(2) . ? C13 C14 1.492(2) . ? C14 C15 1.371(2) . ? C14 C19 1.376(2) . ? C15 C16 1.379(3) . ? C15 H15 0.9300 . ? C16 C17 1.368(3) . ? C16 H16 0.9300 . ? C17 C18 1.369(3) . ? C17 C20 1.492(3) . ? C20 F2B 1.231(7) . ? C20 F1A 1.269(5) . ? C20 F2A 1.275(6) . ? C20 F3B 1.302(7) . ? C20 F3A 1.319(5) . ? C20 F1B 1.335(7) . ? C18 C19 1.368(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11A 121.87(18) . . ? C2 C1 H1 119.1 . . ? C11A C1 H1 119.1 . . ? C1 C2 C3 119.79(18) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 119.80(19) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C4A 121.31(17) . . ? C3 C4 H4 119.3 . . ? C4A C4 H4 119.3 . . ? C4 C4A C11A 118.94(15) . . ? C4 C4A C5 119.55(14) . . ? C11A C4A C5 121.47(15) . . ? C12 C5 C5A 119.51(15) . . ? C12 C5 C4A 122.95(15) . . ? C5A C5 C4A 117.31(13) . . ? C6 C5A C9A 119.29(16) . . ? C6 C5A C5 119.57(16) . . ? C9A C5A C5 121.10(15) . . ? C7 C6 C5A 121.2(2) . . ? C7 C6 H6 119.4 . . ? C5A C6 H6 119.4 . . ? C8 C7 C6 119.5(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C9 C8 C7 120.21(19) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C9A 121.5(2) . . ? C8 C9 H9 119.2 . . ? C9A C9 H9 119.2 . . ? C5A C9A C9 118.12(18) . . ? C5A C9A C10 123.53(15) . . ? C9 C9A C10 118.35(18) . . ? C11 C10 C9A 128.66(17) . . ? C11 C10 H10 115.7 . . ? C9A C10 H10 115.7 . . ? C10 C11 C11A 128.59(17) . . ? C10 C11 H11 115.7 . . ? C11A C11 H11 115.7 . . ? C1 C11A C4A 118.18(16) . . ? C1 C11A C11 118.51(15) . . ? C4A C11A C11 123.27(15) . . ? C5 C12 C13 129.00(16) . . ? C5 C12 H12 115.5 . . ? C13 C12 H12 115.5 . . ? O C13 C12 118.13(16) . . ? O C13 C14 119.59(15) . . ? C12 C13 C14 122.21(14) . . ? C15 C14 C19 118.82(16) . . ? C15 C14 C13 122.38(15) . . ? C19 C14 C13 118.63(15) . . ? C14 C15 C16 120.46(17) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 120.04(16) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 119.76(17) . . ? C16 C17 C20 120.94(18) . . ? C18 C17 C20 119.29(18) . . ? F1A C20 F2A 107.2(4) . . ? F2B C20 F3B 105.4(6) . . ? F1A C20 F3A 101.7(4) . . ? F2A C20 F3A 107.4(4) . . ? F2B C20 F1B 107.4(7) . . ? F3B C20 F1B 104.9(6) . . ? F2B C20 C17 115.2(4) . . ? F1A C20 C17 115.8(3) . . ? F2A C20 C17 113.4(3) . . ? F3B C20 C17 110.9(4) . . ? F3A C20 C17 110.4(3) . . ? F1B C20 C17 112.3(3) . . ? C19 C18 C17 120.06(17) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C14 120.83(16) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? 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 C11A C1 C2 C3 0.9(3) . . . . ? C1 C2 C3 C4 -2.0(3) . . . . ? C2 C3 C4 C4A 0.2(3) . . . . ? C3 C4 C4A C11A 2.6(2) . . . . ? C3 C4 C4A C5 -175.30(15) . . . . ? C4 C4A C5 C12 52.1(2) . . . . ? C11A C4A C5 C12 -125.82(18) . . . . ? C4 C4A C5 C5A -122.42(16) . . . . ? C11A C4A C5 C5A 59.7(2) . . . . ? C12 C5 C5A C6 -52.3(2) . . . . ? C4A C5 C5A C6 122.36(18) . . . . ? C12 C5 C5A C9A 125.40(18) . . . . ? C4A C5 C5A C9A -59.9(2) . . . . ? C9A C5A C6 C7 0.1(3) . . . . ? C5 C5A C6 C7 177.87(18) . . . . ? C5A C6 C7 C8 -1.1(3) . . . . ? C6 C7 C8 C9 0.2(4) . . . . ? C7 C8 C9 C9A 1.7(3) . . . . ? C6 C5A C9A C9 1.8(2) . . . . ? C5 C5A C9A C9 -175.99(16) . . . . ? C6 C5A C9A C10 -178.40(16) . . . . ? C5 C5A C9A C10 3.9(3) . . . . ? C8 C9 C9A C5A -2.7(3) . . . . ? C8 C9 C9A C10 177.46(18) . . . . ? C5A C9A C10 C11 30.7(3) . . . . ? C9 C9A C10 C11 -149.45(19) . . . . ? C9A C10 C11 C11A -0.8(3) . . . . ? C2 C1 C11A C4A 1.9(3) . . . . ? C2 C1 C11A C11 179.77(17) . . . . ? C4 C4A C11A C1 -3.7(2) . . . . ? C5 C4A C11A C1 174.26(15) . . . . ? C4 C4A C11A C11 178.63(14) . . . . ? C5 C4A C11A C11 -3.5(2) . . . . ? C10 C11 C11A C1 152.52(19) . . . . ? C10 C11 C11A C4A -29.8(3) . . . . ? C5A C5 C12 C13 174.90(16) . . . . ? C4A C5 C12 C13 0.5(3) . . . . ? C5 C12 C13 O -138.43(19) . . . . ? C5 C12 C13 C14 44.7(3) . . . . ? O C13 C14 C15 -148.36(17) . . . . ? C12 C13 C14 C15 28.5(2) . . . . ? O C13 C14 C19 26.8(2) . . . . ? C12 C13 C14 C19 -156.40(16) . . . . ? C19 C14 C15 C16 -1.4(2) . . . . ? C13 C14 C15 C16 173.77(15) . . . . ? C14 C15 C16 C17 1.3(3) . . . . ? C15 C16 C17 C18 0.1(3) . . . . ? C15 C16 C17 C20 -178.72(19) . . . . ? C16 C17 C20 F2B -31.0(12) . . . . ? C18 C17 C20 F2B 150.1(11) . . . . ? C16 C17 C20 F1A 13.1(7) . . . . ? C18 C17 C20 F1A -165.7(7) . . . . ? C16 C17 C20 F2A 137.6(6) . . . . ? C18 C17 C20 F2A -41.2(7) . . . . ? C16 C17 C20 F3B 88.5(12) . . . . ? C18 C17 C20 F3B -90.3(12) . . . . ? C16 C17 C20 F3A -101.7(7) . . . . ? C18 C17 C20 F3A 79.4(7) . . . . ? C16 C17 C20 F1B -154.4(11) . . . . ? C18 C17 C20 F1B 26.8(12) . . . . ? C16 C17 C18 C19 -1.5(3) . . . . ? C20 C17 C18 C19 177.39(19) . . . . ? C17 C18 C19 C14 1.4(3) . . . . ? C15 C14 C19 C18 0.0(3) . . . . ? C13 C14 C19 C18 -175.31(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.128 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.027 #===END data_mjm173(30) _database_code_depnum_ccdc_archive 'CCDC 769743' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H16' _chemical_formula_sum 'C23 H16' _chemical_formula_weight 292.36 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 19.553(3) _cell_length_b 28.605(5) _cell_length_c 5.3564(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2995.9(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6106 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 23.26 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8277 _exptl_absorpt_correction_T_max 0.9993 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.153 before and 0.038 after correction. The Ratio of minimum to maximum transmission is 0.828312. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16917 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 23.29 _reflns_number_total 2135 _reflns_number_gt 1846 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0384P)^2^+1.7376P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2135 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _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 C1 C 0.50577(9) 0.41079(6) 0.1705(4) 0.0209(4) Uani 1 1 d . . . H1 H 0.5427 0.4313 0.2061 0.025 Uiso 1 1 calc R . . C2 C 0.49816(9) 0.36842(6) 0.2752(3) 0.0207(4) Uani 1 1 d . . . C12 C 0.54685(10) 0.34495(6) 0.4446(4) 0.0209(5) Uani 1 1 d . . . C13 C 0.61714(10) 0.34877(7) 0.4040(4) 0.0240(5) Uani 1 1 d . . . H13 H 0.6334 0.3665 0.2663 0.029 Uiso 1 1 calc R . . C14 C 0.66346(10) 0.32710(7) 0.5612(4) 0.0288(5) Uani 1 1 d . . . H14 H 0.7111 0.3302 0.5314 0.035 Uiso 1 1 calc R . . C15 C 0.64046(11) 0.30093(7) 0.7617(4) 0.0295(5) Uani 1 1 d . . . H15 H 0.6722 0.2858 0.8691 0.035 Uiso 1 1 calc R . . C16 C 0.57123(11) 0.29697(6) 0.8044(4) 0.0272(5) Uani 1 1 d . . . H16 H 0.5553 0.2792 0.9427 0.033 Uiso 1 1 calc R . . C17 C 0.52461(10) 0.31856(6) 0.6481(3) 0.0223(5) Uani 1 1 d . . . H17 H 0.4770 0.3154 0.6795 0.027 Uiso 1 1 calc R . . C2A C 0.43434(9) 0.34752(6) 0.1782(3) 0.0195(4) Uani 1 1 d . . . C3 C 0.40537(9) 0.30344(6) 0.2087(4) 0.0217(4) Uani 1 1 d . . . H3 H 0.4242 0.2816 0.3232 0.026 Uiso 1 1 calc R . . C4 C 0.34816(9) 0.29231(6) 0.0669(4) 0.0233(5) Uani 1 1 d . . . H4 H 0.3272 0.2626 0.0884 0.028 Uiso 1 1 calc R . . C5 C 0.32095(9) 0.32324(6) -0.1044(4) 0.0226(5) Uani 1 1 d . . . H5 H 0.2826 0.3142 -0.2018 0.027 Uiso 1 1 calc R . . C5A C 0.34930(9) 0.36797(6) -0.1364(3) 0.0206(4) Uani 1 1 d . . . C6 C 0.32218(9) 0.40066(7) -0.3216(4) 0.0236(5) Uani 1 1 d . . . H6 H 0.2990 0.3873 -0.4600 0.028 Uiso 1 1 calc R . . C7 C 0.32650(9) 0.44742(7) -0.3175(4) 0.0248(5) Uani 1 1 d . . . H7 H 0.3091 0.4629 -0.4610 0.030 Uiso 1 1 calc R . . C7A C 0.35428(9) 0.47806(6) -0.1228(4) 0.0215(5) Uani 1 1 d . . . C8 C 0.32242(10) 0.52148(7) -0.0895(4) 0.0250(5) Uani 1 1 d . . . H8 H 0.2874 0.5307 -0.2021 0.030 Uiso 1 1 calc R . . C9 C 0.34043(10) 0.55127(7) 0.1021(4) 0.0264(5) Uani 1 1 d . . . H9 H 0.3175 0.5803 0.1221 0.032 Uiso 1 1 calc R . . C10 C 0.39176(10) 0.53858(7) 0.2640(4) 0.0257(5) Uani 1 1 d . . . H10 H 0.4037 0.5585 0.3988 0.031 Uiso 1 1 calc R . . C11 C 0.42600(10) 0.49663(6) 0.2302(4) 0.0240(5) Uani 1 1 d . . . H11 H 0.4618 0.4884 0.3415 0.029 Uiso 1 1 calc R . . C11A C 0.40900(9) 0.46643(6) 0.0368(3) 0.0201(4) Uani 1 1 d . . . C11B C 0.44922(9) 0.42187(6) -0.0090(3) 0.0202(4) Uani 1 1 d . . . H11B H 0.4691 0.4234 -0.1808 0.024 Uiso 1 1 calc R . . C11C C 0.40558(9) 0.37882(6) 0.0084(3) 0.0194(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0218(10) 0.0216(10) 0.0193(10) -0.0004(8) 0.0002(8) -0.0019(8) C2 0.0252(10) 0.0215(10) 0.0153(10) -0.0012(8) 0.0025(8) 0.0006(8) C12 0.0293(11) 0.0154(10) 0.0181(10) -0.0037(8) -0.0022(9) 0.0010(8) C13 0.0290(11) 0.0219(11) 0.0211(11) 0.0000(9) -0.0008(9) 0.0011(8) C14 0.0264(11) 0.0284(11) 0.0316(12) -0.0045(10) -0.0037(10) 0.0026(9) C15 0.0376(12) 0.0243(11) 0.0267(12) -0.0023(10) -0.0107(10) 0.0071(9) C16 0.0441(13) 0.0191(10) 0.0185(11) 0.0006(8) -0.0033(10) 0.0004(9) C17 0.0298(11) 0.0186(10) 0.0185(11) -0.0035(8) -0.0002(9) 0.0002(8) C2A 0.0223(10) 0.0200(10) 0.0163(10) -0.0028(8) 0.0052(8) 0.0026(8) C3 0.0258(10) 0.0192(10) 0.0200(10) 0.0005(8) 0.0044(9) 0.0041(8) C4 0.0257(11) 0.0179(10) 0.0262(11) -0.0015(8) 0.0054(9) -0.0021(8) C5 0.0217(10) 0.0214(10) 0.0246(11) -0.0040(9) -0.0005(9) -0.0018(8) C5A 0.0207(10) 0.0227(11) 0.0185(11) -0.0034(8) 0.0030(8) 0.0024(8) C6 0.0233(10) 0.0261(11) 0.0214(11) -0.0014(9) -0.0026(9) -0.0017(8) C7 0.0255(10) 0.0279(11) 0.0208(11) 0.0041(9) -0.0025(9) -0.0006(8) C7A 0.0214(10) 0.0218(10) 0.0213(11) 0.0037(8) 0.0032(9) -0.0043(8) C8 0.0227(10) 0.0236(11) 0.0286(12) 0.0066(9) 0.0005(9) -0.0016(8) C9 0.0261(11) 0.0205(10) 0.0325(12) 0.0023(9) 0.0063(9) -0.0012(8) C10 0.0325(11) 0.0213(11) 0.0235(11) -0.0016(9) 0.0056(9) -0.0062(9) C11 0.0280(11) 0.0237(11) 0.0201(11) 0.0048(9) 0.0002(9) -0.0050(8) C11A 0.0216(10) 0.0188(10) 0.0199(11) 0.0045(8) 0.0023(9) -0.0056(8) C11B 0.0221(10) 0.0221(10) 0.0165(10) 0.0015(8) 0.0015(8) -0.0026(8) C11C 0.0227(10) 0.0189(10) 0.0165(10) -0.0017(8) 0.0042(8) 0.0033(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.344(3) . ? C1 C11B 1.499(3) . ? C1 H1 0.9500 . ? C2 C12 1.477(3) . ? C2 C2A 1.478(3) . ? C12 C17 1.395(3) . ? C12 C13 1.396(3) . ? C13 C14 1.383(3) . ? C13 H13 0.9500 . ? C14 C15 1.385(3) . ? C14 H14 0.9500 . ? C15 C16 1.377(3) . ? C15 H15 0.9500 . ? C16 C17 1.384(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C2A C3 1.392(3) . ? C2A C11C 1.395(3) . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 C5A 1.405(3) . ? C5 H5 0.9500 . ? C5A C11C 1.382(3) . ? C5A C6 1.463(3) . ? C6 C7 1.340(3) . ? C6 H6 0.9500 . ? C7 C7A 1.467(3) . ? C7 H7 0.9500 . ? C7A C8 1.401(3) . ? C7A C11A 1.409(3) . ? C8 C9 1.380(3) . ? C8 H8 0.9500 . ? C9 C10 1.375(3) . ? C9 H9 0.9500 . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C11A 1.389(3) . ? C11 H11 0.9500 . ? C11A C11B 1.518(3) . ? C11B C11C 1.501(3) . ? C11B H11B 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11B 112.14(16) . . ? C2 C1 H1 123.9 . . ? C11B C1 H1 123.9 . . ? C1 C2 C12 126.53(17) . . ? C1 C2 C2A 108.16(16) . . ? C12 C2 C2A 125.20(16) . . ? C17 C12 C13 118.10(17) . . ? C17 C12 C2 121.67(17) . . ? C13 C12 C2 120.23(17) . . ? C14 C13 C12 120.98(19) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 120.13(19) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 119.50(19) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.68(19) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C12 120.60(18) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C3 C2A C11C 119.62(17) . . ? C3 C2A C2 131.97(17) . . ? C11C C2A C2 108.05(16) . . ? C4 C3 C2A 118.11(17) . . ? C4 C3 H3 120.9 . . ? C2A C3 H3 120.9 . . ? C5 C4 C3 121.77(17) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C5A 120.84(18) . . ? C4 C5 H5 119.6 . . ? C5A C5 H5 119.6 . . ? C11C C5A C5 116.77(17) . . ? C11C C5A C6 121.73(17) . . ? C5 C5A C6 121.46(17) . . ? C7 C6 C5A 127.16(18) . . ? C7 C6 H6 116.4 . . ? C5A C6 H6 116.4 . . ? C6 C7 C7A 129.14(18) . . ? C6 C7 H7 115.4 . . ? C7A C7 H7 115.4 . . ? C8 C7A C11A 117.99(17) . . ? C8 C7A C7 117.12(17) . . ? C11A C7A C7 124.86(17) . . ? C9 C8 C7A 121.94(19) . . ? C9 C8 H8 119.0 . . ? C7A C8 H8 119.0 . . ? C10 C9 C8 119.48(18) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 119.93(19) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C11A 121.34(18) . . ? C10 C11 H11 119.3 . . ? C11A C11 H11 119.3 . . ? C11 C11A C7A 119.16(17) . . ? C11 C11A C11B 121.24(17) . . ? C7A C11A C11B 119.58(16) . . ? C1 C11B C11C 101.89(15) . . ? C1 C11B C11A 117.15(16) . . ? C11C C11B C11A 112.61(15) . . ? C1 C11B H11B 108.3 . . ? C11C C11B H11B 108.3 . . ? C11A C11B H11B 108.3 . . ? C5A C11C C2A 122.88(17) . . ? C5A C11C C11B 127.04(17) . . ? C2A C11C C11B 109.76(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11B C1 C2 C12 174.99(17) . . . . ? C11B C1 C2 C2A -1.2(2) . . . . ? C1 C2 C12 C17 141.6(2) . . . . ? C2A C2 C12 C17 -42.8(3) . . . . ? C1 C2 C12 C13 -38.4(3) . . . . ? C2A C2 C12 C13 137.20(19) . . . . ? C17 C12 C13 C14 -0.1(3) . . . . ? C2 C12 C13 C14 179.84(17) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 -0.5(3) . . . . ? C14 C15 C16 C17 0.5(3) . . . . ? C15 C16 C17 C12 -0.3(3) . . . . ? C13 C12 C17 C16 0.1(3) . . . . ? C2 C12 C17 C16 -179.88(17) . . . . ? C1 C2 C2A C3 174.11(19) . . . . ? C12 C2 C2A C3 -2.1(3) . . . . ? C1 C2 C2A C11C 1.3(2) . . . . ? C12 C2 C2A C11C -174.97(17) . . . . ? C11C C2A C3 C4 -0.1(3) . . . . ? C2 C2A C3 C4 -172.21(19) . . . . ? C2A C3 C4 C5 1.4(3) . . . . ? C3 C4 C5 C5A -1.8(3) . . . . ? C4 C5 C5A C11C 0.8(3) . . . . ? C4 C5 C5A C6 178.38(17) . . . . ? C11C C5A C6 C7 -27.5(3) . . . . ? C5 C5A C6 C7 155.1(2) . . . . ? C5A C6 C7 C7A -5.0(3) . . . . ? C6 C7 C7A C8 -145.8(2) . . . . ? C6 C7 C7A C11A 32.2(3) . . . . ? C11A C7A C8 C9 -3.9(3) . . . . ? C7 C7A C8 C9 174.22(18) . . . . ? C7A C8 C9 C10 1.0(3) . . . . ? C8 C9 C10 C11 1.5(3) . . . . ? C9 C10 C11 C11A -0.9(3) . . . . ? C10 C11 C11A C7A -2.1(3) . . . . ? C10 C11 C11A C11B 176.41(17) . . . . ? C8 C7A C11A C11 4.4(3) . . . . ? C7 C7A C11A C11 -173.56(17) . . . . ? C8 C7A C11A C11B -174.15(16) . . . . ? C7 C7A C11A C11B 7.9(3) . . . . ? C2 C1 C11B C11C 0.7(2) . . . . ? C2 C1 C11B C11A 123.99(18) . . . . ? C11 C11A C11B C1 2.8(3) . . . . ? C7A C11A C11B C1 -178.60(16) . . . . ? C11 C11A C11B C11C 120.51(19) . . . . ? C7A C11A C11B C11C -60.9(2) . . . . ? C5 C5A C11C C2A 0.5(3) . . . . ? C6 C5A C11C C2A -177.01(17) . . . . ? C5 C5A C11C C11B 173.22(17) . . . . ? C6 C5A C11C C11B -4.3(3) . . . . ? C3 C2A C11C C5A -0.9(3) . . . . ? C2 C2A C11C C5A 172.96(17) . . . . ? C3 C2A C11C C11B -174.73(16) . . . . ? C2 C2A C11C C11B -0.9(2) . . . . ? C1 C11B C11C C5A -173.32(17) . . . . ? C11A C11B C11C C5A 60.3(2) . . . . ? C1 C11B C11C C2A 0.17(19) . . . . ? C11A C11B C11C C2A -126.19(17) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.200 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.037 #===END data_mjm192(17) _database_code_depnum_ccdc_archive 'CCDC 769744' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C49 H27 N O2 F6' _chemical_formula_sum 'C49 H27 N O2 F6' _chemical_formula_weight 775.72 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4052(11) _cell_length_b 14.5518(17) _cell_length_c 14.8501(17) _cell_angle_alpha 110.752(2) _cell_angle_beta 107.181(2) _cell_angle_gamma 99.085(2) _cell_volume 1735.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3884 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 24.15 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6942 _exptl_absorpt_correction_T_max 0.9944 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.043 before and 0.022 after correction. The Ratio of minimum to maximum transmission is 0.698118. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12790 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 24.19 _reflns_number_total 5529 _reflns_number_gt 4441 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0718P)^2^+1.1192P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5529 _refine_ls_number_parameters 524 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1363 _refine_ls_wR_factor_gt 0.1290 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 C1 C 1.2401(3) 0.69404(17) 0.30531(19) 0.0243(6) Uani 1 1 d . . . H1 H 1.2125 0.6817 0.2342 0.029 Uiso 1 1 calc R . . C2 C 1.3948(3) 0.72102(18) 0.3702(2) 0.0272(6) Uani 1 1 d . . . H2 H 1.4720 0.7267 0.3416 0.033 Uiso 1 1 calc R . . C3 C 1.4431(3) 0.74016(18) 0.4747(2) 0.0256(6) Uani 1 1 d . . . H3 H 1.5505 0.7604 0.5172 0.031 Uiso 1 1 calc R . . C3A C 1.3283(3) 0.72868(17) 0.51509(19) 0.0231(5) Uani 1 1 d . . . C3B C 1.3244(3) 0.73383(17) 0.61476(18) 0.0240(5) Uani 1 1 d . . . C4 C 1.4461(3) 0.75669(19) 0.70737(19) 0.0281(6) Uani 1 1 d . . . H4 H 1.5513 0.7781 0.7149 0.034 Uiso 1 1 calc R . . C5 C 1.4099(3) 0.74740(19) 0.7887(2) 0.0285(6) Uani 1 1 d . . . H5 H 1.4913 0.7631 0.8527 0.034 Uiso 1 1 calc R . . C6 C 1.2577(3) 0.71574(18) 0.77730(19) 0.0263(6) Uani 1 1 d . . . H6 H 1.2356 0.7084 0.8332 0.032 Uiso 1 1 calc R . . C7 C 1.1347(3) 0.69404(17) 0.68538(18) 0.0228(5) Uani 1 1 d . . . H7 H 1.0299 0.6713 0.6781 0.027 Uiso 1 1 calc R . . C7A C 1.1687(3) 0.70631(17) 0.60493(18) 0.0208(5) Uani 1 1 d . . . C7B C 1.0593(3) 0.68845(17) 0.49618(18) 0.0212(5) Uani 1 1 d . . . C7C C 0.9638(3) 0.76147(17) 0.47770(18) 0.0199(5) Uani 1 1 d . . . C8 C 0.9448(3) 0.84126(17) 0.55354(18) 0.0208(5) Uani 1 1 d . . . C17 C 1.0188(3) 0.87317(17) 0.66779(18) 0.0218(5) Uani 1 1 d . . . C18 C 1.1721(3) 0.93373(18) 0.72291(19) 0.0259(6) Uani 1 1 d . . . H18 H 1.2327 0.9507 0.6868 0.031 Uiso 1 1 calc R . . C19 C 1.2380(3) 0.96978(19) 0.83000(19) 0.0291(6) Uani 1 1 d . . . H19 H 1.3430 1.0118 0.8673 0.035 Uiso 1 1 calc R . . C20 C 1.1504(3) 0.94448(18) 0.88254(19) 0.0260(6) Uani 1 1 d . . . C23 C 1.2236(3) 0.9865(2) 0.9983(2) 0.0325(6) Uani 1 1 d . . . F1 F 1.2384(2) 1.08746(12) 1.04392(12) 0.0427(4) Uani 1 1 d . . . F2 F 1.1417(2) 0.94089(13) 1.03811(12) 0.0475(5) Uani 1 1 d . . . F3 F 1.3666(2) 0.97843(15) 1.03137(13) 0.0553(5) Uani 1 1 d . . . C21 C 0.9975(3) 0.88447(19) 0.82856(19) 0.0279(6) Uani 1 1 d . . . H21 H 0.9373 0.8674 0.8648 0.033 Uiso 1 1 calc R . . C22 C 0.9315(3) 0.84902(19) 0.72125(19) 0.0257(6) Uani 1 1 d . . . H22 H 0.8259 0.8080 0.6842 0.031 Uiso 1 1 calc R . . C8A C 0.8488(3) 0.89951(18) 0.52227(18) 0.0223(5) Uani 1 1 d . . . C8B C 0.7669(3) 0.86557(17) 0.41616(18) 0.0212(5) Uani 1 1 d . . . C9 C 0.8249(3) 0.98760(18) 0.5896(2) 0.0269(6) Uani 1 1 d . . . H9 H 0.8783 1.0139 0.6628 0.032 Uiso 1 1 calc R . . C10 C 0.7247(3) 1.03498(18) 0.54932(19) 0.0275(6) Uani 1 1 d . . . H10 H 0.7136 1.0954 0.5958 0.033 Uiso 1 1 calc R . . C11 C 0.6388(3) 0.99794(19) 0.4431(2) 0.0280(6) Uani 1 1 d . . . H11 H 0.5683 1.0314 0.4177 0.034 Uiso 1 1 calc R . . C11A C 0.6581(3) 0.91197(18) 0.37561(19) 0.0241(5) Uani 1 1 d . . . C11B C 0.5875(3) 0.84955(18) 0.26350(19) 0.0250(6) Uani 1 1 d . . . C12 C 0.4632(3) 0.8554(2) 0.1889(2) 0.0301(6) Uani 1 1 d . . . H12 H 0.4181 0.9098 0.2071 0.036 Uiso 1 1 calc R . . C13 C 0.4065(3) 0.7805(2) 0.0877(2) 0.0334(6) Uani 1 1 d . . . H13 H 0.3230 0.7842 0.0355 0.040 Uiso 1 1 calc R . . C14 C 0.4704(3) 0.7008(2) 0.0622(2) 0.0307(6) Uani 1 1 d . . . H14 H 0.4297 0.6499 -0.0077 0.037 Uiso 1 1 calc R . . C15 C 0.5928(3) 0.69267(19) 0.13605(19) 0.0259(6) Uani 1 1 d . . . H15 H 0.6327 0.6356 0.1175 0.031 Uiso 1 1 calc R . . C15A C 0.6561(3) 0.76905(18) 0.23732(18) 0.0227(5) Uani 1 1 d . . . C15B C 0.7789(3) 0.78175(17) 0.33622(18) 0.0216(5) Uani 1 1 d . . . C15C C 0.8918(3) 0.73639(17) 0.36724(18) 0.0207(5) Uani 1 1 d . . . C16 C 0.9471(3) 0.65575(17) 0.29597(18) 0.0222(5) Uani 1 1 d . . . C16A C 1.1255(3) 0.68533(17) 0.34674(19) 0.0226(5) Uani 1 1 d . . . C16B C 1.1756(3) 0.70173(17) 0.44873(18) 0.0219(5) Uani 1 1 d . . . C24 C 0.9088(3) 0.64622(18) 0.18640(18) 0.0229(5) Uani 1 1 d . . . C25 C 0.8584(3) 0.55346(18) 0.10005(19) 0.0245(6) Uani 1 1 d . . . H25 H 0.8342 0.4913 0.1074 0.029 Uiso 1 1 calc R . . C26 C 0.8423(3) 0.54930(19) 0.00223(19) 0.0259(6) Uani 1 1 d . . . H26 H 0.8053 0.4849 -0.0568 0.031 Uiso 1 1 calc R . . C27 C 0.8810(3) 0.64004(19) -0.00821(19) 0.0264(6) Uani 1 1 d . . . C30 C 0.8738(3) 0.63928(19) -0.1097(2) 0.0298(6) Uani 1 1 d . . . F4 F 0.78003(19) 0.69150(12) -0.14083(12) 0.0401(4) Uani 1 1 d . . . F5 F 0.8255(2) 0.54556(12) -0.18627(11) 0.0427(4) Uani 1 1 d . . . F6 F 1.01378(19) 0.68382(15) -0.10526(13) 0.0504(5) Uani 1 1 d . . . C28 C 0.9327(3) 0.73367(19) 0.07779(19) 0.0268(6) Uani 1 1 d . . . H28 H 0.9583 0.7958 0.0706 0.032 Uiso 1 1 calc R . . C29 C 0.9470(3) 0.73657(18) 0.17391(19) 0.0249(6) Uani 1 1 d . . . H29 H 0.9834 0.8011 0.2327 0.030 Uiso 1 1 calc R . . C31 C 0.9485(3) 0.57637(17) 0.42542(18) 0.0212(5) Uani 1 1 d . . . H31 H 1.0068 0.5264 0.4348 0.025 Uiso 1 1 calc R . . C32 C 0.8038(3) 0.55475(17) 0.44819(19) 0.0226(5) Uani 1 1 d . . . O1 O 0.7964(2) 0.56260(13) 0.53077(13) 0.0297(4) Uani 1 1 d . . . N N 0.6751(2) 0.52350(15) 0.35836(15) 0.0232(5) Uani 1 1 d . . . C33 C 0.5165(3) 0.4935(2) 0.3525(2) 0.0316(6) Uani 1 1 d . . . H33A H 0.4592 0.5373 0.3299 0.047 Uiso 1 1 calc R . . H33B H 0.5183 0.5016 0.4212 0.047 Uiso 1 1 calc R . . H33C H 0.4650 0.4215 0.3023 0.047 Uiso 1 1 calc R . . C34 C 0.7113(3) 0.52069(17) 0.27404(19) 0.0238(6) Uani 1 1 d . . . O2 O 0.6151(2) 0.49351(13) 0.18777(13) 0.0305(4) Uani 1 1 d . . . C35 C 0.8868(3) 0.55558(18) 0.30884(18) 0.0223(5) Uani 1 1 d . . . H35 H 0.9223 0.4990 0.2689 0.027 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 C1 0.0345(15) 0.0152(12) 0.0285(13) 0.0101(11) 0.0170(12) 0.0094(11) C2 0.0307(15) 0.0199(13) 0.0396(15) 0.0140(11) 0.0217(12) 0.0102(11) C3 0.0238(13) 0.0187(12) 0.0364(15) 0.0113(11) 0.0139(11) 0.0075(10) C3A 0.0259(14) 0.0150(12) 0.0296(13) 0.0094(10) 0.0112(11) 0.0084(10) C3B 0.0274(14) 0.0160(12) 0.0272(13) 0.0077(11) 0.0094(11) 0.0083(10) C4 0.0248(14) 0.0226(13) 0.0324(15) 0.0091(11) 0.0071(11) 0.0086(11) C5 0.0326(15) 0.0227(13) 0.0251(13) 0.0085(11) 0.0051(11) 0.0105(11) C6 0.0365(16) 0.0184(13) 0.0233(13) 0.0082(11) 0.0102(11) 0.0098(11) C7 0.0260(14) 0.0162(12) 0.0272(13) 0.0095(10) 0.0101(11) 0.0082(10) C7A 0.0252(13) 0.0135(11) 0.0230(13) 0.0067(10) 0.0082(10) 0.0078(10) C7B 0.0249(13) 0.0185(12) 0.0229(13) 0.0104(10) 0.0099(10) 0.0082(10) C7C 0.0215(13) 0.0158(12) 0.0244(13) 0.0104(10) 0.0095(10) 0.0043(10) C8 0.0230(13) 0.0171(12) 0.0225(13) 0.0087(10) 0.0097(10) 0.0034(10) C17 0.0283(14) 0.0148(12) 0.0253(13) 0.0087(10) 0.0119(11) 0.0107(10) C18 0.0329(15) 0.0209(13) 0.0258(13) 0.0111(11) 0.0128(11) 0.0072(11) C19 0.0325(15) 0.0220(13) 0.0262(14) 0.0087(11) 0.0065(11) 0.0035(11) C20 0.0366(16) 0.0207(13) 0.0242(13) 0.0106(11) 0.0126(12) 0.0134(11) C23 0.0387(17) 0.0292(15) 0.0319(15) 0.0122(12) 0.0164(13) 0.0122(12) F1 0.0549(11) 0.0329(9) 0.0312(9) 0.0068(7) 0.0150(8) 0.0080(8) F2 0.0686(12) 0.0448(10) 0.0306(9) 0.0195(8) 0.0202(8) 0.0095(9) F3 0.0538(12) 0.0818(14) 0.0363(10) 0.0290(10) 0.0122(8) 0.0357(10) C21 0.0376(16) 0.0276(14) 0.0287(14) 0.0153(12) 0.0193(12) 0.0155(12) C22 0.0254(14) 0.0239(13) 0.0303(14) 0.0115(11) 0.0126(11) 0.0096(11) C8A 0.0241(13) 0.0187(12) 0.0261(13) 0.0111(11) 0.0113(11) 0.0043(10) C8B 0.0251(13) 0.0156(12) 0.0266(13) 0.0116(10) 0.0114(11) 0.0060(10) C9 0.0320(15) 0.0199(13) 0.0284(14) 0.0079(11) 0.0140(12) 0.0072(11) C10 0.0394(15) 0.0150(12) 0.0308(14) 0.0085(11) 0.0168(12) 0.0113(11) C11 0.0343(15) 0.0235(13) 0.0378(15) 0.0183(12) 0.0191(12) 0.0154(11) C11A 0.0274(14) 0.0210(13) 0.0310(14) 0.0163(11) 0.0137(11) 0.0085(11) C11B 0.0293(14) 0.0233(13) 0.0298(14) 0.0171(11) 0.0130(11) 0.0095(11) C12 0.0326(15) 0.0301(14) 0.0362(15) 0.0206(12) 0.0137(12) 0.0151(12) C13 0.0327(15) 0.0406(16) 0.0286(14) 0.0197(13) 0.0054(12) 0.0151(13) C14 0.0321(15) 0.0304(14) 0.0251(14) 0.0132(12) 0.0052(11) 0.0054(12) C15 0.0282(14) 0.0233(13) 0.0293(14) 0.0130(11) 0.0124(11) 0.0087(11) C15A 0.0246(13) 0.0219(13) 0.0261(13) 0.0150(11) 0.0101(11) 0.0063(10) C15B 0.0249(13) 0.0186(12) 0.0255(13) 0.0132(11) 0.0109(11) 0.0056(10) C15C 0.0244(13) 0.0145(12) 0.0233(13) 0.0079(10) 0.0107(10) 0.0031(10) C16 0.0276(14) 0.0161(12) 0.0249(13) 0.0090(10) 0.0119(11) 0.0075(10) C16A 0.0286(14) 0.0119(12) 0.0292(14) 0.0087(10) 0.0128(11) 0.0079(10) C16B 0.0278(14) 0.0149(12) 0.0275(13) 0.0101(10) 0.0139(11) 0.0091(10) C24 0.0238(13) 0.0234(13) 0.0254(13) 0.0116(11) 0.0115(11) 0.0095(10) C25 0.0293(14) 0.0209(13) 0.0287(14) 0.0124(11) 0.0144(11) 0.0102(11) C26 0.0284(14) 0.0234(13) 0.0286(14) 0.0104(11) 0.0135(11) 0.0109(11) C27 0.0275(14) 0.0289(14) 0.0280(14) 0.0144(12) 0.0123(11) 0.0134(11) C30 0.0281(15) 0.0272(14) 0.0321(15) 0.0120(12) 0.0088(12) 0.0095(12) F4 0.0525(10) 0.0394(9) 0.0360(9) 0.0224(8) 0.0149(8) 0.0215(8) F5 0.0625(11) 0.0385(10) 0.0271(8) 0.0123(7) 0.0160(8) 0.0207(8) F6 0.0396(10) 0.0775(13) 0.0396(10) 0.0314(9) 0.0190(8) 0.0082(9) C28 0.0325(15) 0.0232(13) 0.0309(14) 0.0149(11) 0.0156(12) 0.0089(11) C29 0.0288(14) 0.0186(12) 0.0262(13) 0.0073(11) 0.0118(11) 0.0072(10) C31 0.0242(13) 0.0178(12) 0.0228(13) 0.0094(10) 0.0084(10) 0.0086(10) C32 0.0270(14) 0.0167(12) 0.0258(14) 0.0100(10) 0.0101(11) 0.0081(10) O1 0.0290(10) 0.0345(10) 0.0280(10) 0.0157(8) 0.0119(8) 0.0079(8) N 0.0232(11) 0.0208(11) 0.0258(11) 0.0098(9) 0.0093(9) 0.0069(9) C33 0.0239(14) 0.0303(15) 0.0363(15) 0.0133(12) 0.0083(12) 0.0056(11) C34 0.0322(15) 0.0134(12) 0.0264(14) 0.0099(10) 0.0099(12) 0.0072(10) O2 0.0308(10) 0.0274(10) 0.0267(10) 0.0125(8) 0.0043(8) 0.0020(8) C35 0.0289(14) 0.0161(12) 0.0248(13) 0.0095(10) 0.0126(11) 0.0080(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.386(4) . ? C1 C16A 1.400(3) . ? C1 H1 0.9500 . ? C2 C3 1.389(4) . ? C2 H2 0.9500 . ? C3 C3A 1.396(3) . ? C3 H3 0.9500 . ? C3A C16B 1.378(3) . ? C3A C3B 1.467(3) . ? C3B C4 1.392(3) . ? C3B C7A 1.405(3) . ? C4 C5 1.391(4) . ? C4 H4 0.9500 . ? C5 C6 1.372(4) . ? C5 H5 0.9500 . ? C6 C7 1.395(3) . ? C6 H6 0.9500 . ? C7 C7A 1.386(3) . ? C7 H7 0.9500 . ? C7A C7B 1.540(3) . ? C7B C16B 1.489(3) . ? C7B C7C 1.540(3) . ? C7B C31 1.566(3) . ? C7C C8 1.381(3) . ? C7C C15C 1.457(3) . ? C8 C8A 1.422(3) . ? C8 C17 1.490(3) . ? C17 C18 1.384(4) . ? C17 C22 1.385(3) . ? C18 C19 1.383(3) . ? C18 H18 0.9500 . ? C19 C20 1.382(4) . ? C19 H19 0.9500 . ? C20 C21 1.379(4) . ? C20 C23 1.491(4) . ? C23 F3 1.328(3) . ? C23 F2 1.331(3) . ? C23 F1 1.346(3) . ? C21 C22 1.387(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C8A C8B 1.390(3) . ? C8A C9 1.418(3) . ? C8B C15B 1.417(3) . ? C8B C11A 1.417(3) . ? C9 C10 1.373(4) . ? C9 H9 0.9500 . ? C10 C11 1.393(4) . ? C10 H10 0.9500 . ? C11 C11A 1.376(3) . ? C11 H11 0.9500 . ? C11A C11B 1.457(3) . ? C11B C12 1.391(3) . ? C11B C15A 1.416(3) . ? C12 C13 1.383(4) . ? C12 H12 0.9500 . ? C13 C14 1.377(4) . ? C13 H13 0.9500 . ? C14 C15 1.389(4) . ? C14 H14 0.9500 . ? C15 C15A 1.389(3) . ? C15 H15 0.9500 . ? C15A C15B 1.505(3) . ? C15B C15C 1.387(3) . ? C15C C16 1.551(3) . ? C16 C24 1.508(3) . ? C16 C16A 1.537(3) . ? C16 C35 1.576(3) . ? C16A C16B 1.364(3) . ? C24 C25 1.380(3) . ? C24 C29 1.398(3) . ? C25 C26 1.393(3) . ? C25 H25 0.9500 . ? C26 C27 1.388(3) . ? C26 H26 0.9500 . ? C27 C28 1.384(4) . ? C27 C30 1.484(4) . ? C30 F5 1.327(3) . ? C30 F4 1.337(3) . ? C30 F6 1.344(3) . ? C28 C29 1.378(3) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C31 C32 1.510(3) . ? C31 C35 1.551(3) . ? C31 H31 1.0000 . ? C32 O1 1.215(3) . ? C32 N 1.376(3) . ? N C34 1.381(3) . ? N C33 1.454(3) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 O2 1.208(3) . ? C34 C35 1.514(4) . ? C35 H35 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C16A 118.6(2) . . ? C2 C1 H1 120.7 . . ? C16A C1 H1 120.7 . . ? C1 C2 C3 123.6(2) . . ? C1 C2 H2 118.2 . . ? C3 C2 H2 118.2 . . ? C2 C3 C3A 117.7(2) . . ? C2 C3 H3 121.2 . . ? C3A C3 H3 121.2 . . ? C16B C3A C3 117.4(2) . . ? C16B C3A C3B 106.4(2) . . ? C3 C3A C3B 136.2(2) . . ? C4 C3B C7A 120.9(2) . . ? C4 C3B C3A 129.9(2) . . ? C7A C3B C3A 109.1(2) . . ? C5 C4 C3B 118.4(2) . . ? C5 C4 H4 120.8 . . ? C3B C4 H4 120.8 . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 121.5(2) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C7A C7 C6 118.7(2) . . ? C7A C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C7 C7A C3B 119.8(2) . . ? C7 C7A C7B 130.2(2) . . ? C3B C7A C7B 109.9(2) . . ? C16B C7B C7A 99.84(19) . . ? C16B C7B C7C 103.97(18) . . ? C7A C7B C7C 123.17(19) . . ? C16B C7B C31 105.25(18) . . ? C7A C7B C31 115.53(18) . . ? C7C C7B C31 106.68(18) . . ? C8 C7C C15C 122.3(2) . . ? C8 C7C C7B 126.1(2) . . ? C15C C7C C7B 111.56(19) . . ? C7C C8 C8A 118.6(2) . . ? C7C C8 C17 125.2(2) . . ? C8A C8 C17 116.2(2) . . ? C18 C17 C22 119.2(2) . . ? C18 C17 C8 120.4(2) . . ? C22 C17 C8 120.3(2) . . ? C19 C18 C17 120.7(2) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 119.8(2) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C21 C20 C19 120.2(2) . . ? C21 C20 C23 121.3(2) . . ? C19 C20 C23 118.5(2) . . ? F3 C23 F2 107.3(2) . . ? F3 C23 F1 105.5(2) . . ? F2 C23 F1 106.4(2) . . ? F3 C23 C20 112.7(2) . . ? F2 C23 C20 113.0(2) . . ? F1 C23 C20 111.5(2) . . ? C20 C21 C22 119.9(2) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C17 C22 C21 120.3(2) . . ? C17 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C8B C8A C9 116.6(2) . . ? C8B C8A C8 117.3(2) . . ? C9 C8A C8 126.0(2) . . ? C8A C8B C15B 125.4(2) . . ? C8A C8B C11A 122.7(2) . . ? C15B C8B C11A 111.9(2) . . ? C10 C9 C8A 120.2(2) . . ? C10 C9 H9 119.9 . . ? C8A C9 H9 119.9 . . ? C9 C10 C11 122.6(2) . . ? C9 C10 H10 118.7 . . ? C11 C10 H10 118.7 . . ? C11A C11 C10 118.7(2) . . ? C11A C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C11A C8B 119.0(2) . . ? C11 C11A C11B 134.7(2) . . ? C8B C11A C11B 106.2(2) . . ? C12 C11B C15A 121.2(2) . . ? C12 C11B C11A 129.4(2) . . ? C15A C11B C11A 109.2(2) . . ? C13 C12 C11B 118.8(2) . . ? C13 C12 H12 120.6 . . ? C11B C12 H12 120.6 . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 121.7(2) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C15A C15 C14 119.1(2) . . ? C15A C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C15A C11B 118.8(2) . . ? C15 C15A C15B 133.3(2) . . ? C11B C15A C15B 107.5(2) . . ? C15C C15B C8B 116.4(2) . . ? C15C C15B C15A 138.6(2) . . ? C8B C15B C15A 105.0(2) . . ? C15B C15C C7C 118.4(2) . . ? C15B C15C C16 127.0(2) . . ? C7C C15C C16 114.50(19) . . ? C24 C16 C16A 106.48(19) . . ? C24 C16 C15C 116.70(19) . . ? C16A C16 C15C 107.80(19) . . ? C24 C16 C35 117.12(19) . . ? C16A C16 C35 104.80(18) . . ? C15C C16 C35 103.08(18) . . ? C16B C16A C1 116.6(2) . . ? C16B C16A C16 112.1(2) . . ? C1 C16A C16 131.2(2) . . ? C16A C16B C3A 126.1(2) . . ? C16A C16B C7B 119.4(2) . . ? C3A C16B C7B 114.5(2) . . ? C25 C24 C29 118.3(2) . . ? C25 C24 C16 123.6(2) . . ? C29 C24 C16 117.5(2) . . ? C24 C25 C26 121.2(2) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C27 C26 C25 119.4(2) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C28 C27 C26 120.0(2) . . ? C28 C27 C30 118.6(2) . . ? C26 C27 C30 121.4(2) . . ? F5 C30 F4 107.1(2) . . ? F5 C30 F6 105.7(2) . . ? F4 C30 F6 105.5(2) . . ? F5 C30 C27 113.5(2) . . ? F4 C30 C27 112.4(2) . . ? F6 C30 C27 112.0(2) . . ? C29 C28 C27 119.9(2) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C24 121.2(2) . . ? C28 C29 H29 119.4 . . ? C24 C29 H29 119.4 . . ? C32 C31 C35 104.55(19) . . ? C32 C31 C7B 113.25(19) . . ? C35 C31 C7B 111.56(18) . . ? C32 C31 H31 109.1 . . ? C35 C31 H31 109.1 . . ? C7B C31 H31 109.1 . . ? O1 C32 N 123.6(2) . . ? O1 C32 C31 127.6(2) . . ? N C32 C31 108.9(2) . . ? C32 N C34 113.5(2) . . ? C32 N C33 123.0(2) . . ? C34 N C33 123.4(2) . . ? N C33 H33A 109.5 . . ? N C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O2 C34 N 123.8(2) . . ? O2 C34 C35 127.5(2) . . ? N C34 C35 108.7(2) . . ? C34 C35 C31 104.35(19) . . ? C34 C35 C16 112.85(19) . . ? C31 C35 C16 110.40(18) . . ? C34 C35 H35 109.7 . . ? C31 C35 H35 109.7 . . ? C16 C35 H35 109.7 . . ? 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 C16A C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C3A 1.8(3) . . . . ? C2 C3 C3A C16B -1.6(3) . . . . ? C2 C3 C3A C3B 175.2(2) . . . . ? C16B C3A C3B C4 179.3(2) . . . . ? C3 C3A C3B C4 2.3(4) . . . . ? C16B C3A C3B C7A 2.0(3) . . . . ? C3 C3A C3B C7A -175.1(3) . . . . ? C7A C3B C4 C5 2.7(3) . . . . ? C3A C3B C4 C5 -174.3(2) . . . . ? C3B C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C7 -1.4(4) . . . . ? C5 C6 C7 C7A -0.8(3) . . . . ? C6 C7 C7A C3B 3.9(3) . . . . ? C6 C7 C7A C7B 179.9(2) . . . . ? C4 C3B C7A C7 -5.0(3) . . . . ? C3A C3B C7A C7 172.6(2) . . . . ? C4 C3B C7A C7B 178.3(2) . . . . ? C3A C3B C7A C7B -4.1(3) . . . . ? C7 C7A C7B C16B -172.0(2) . . . . ? C3B C7A C7B C16B 4.3(2) . . . . ? C7 C7A C7B C7C 74.0(3) . . . . ? C3B C7A C7B C7C -109.7(2) . . . . ? C7 C7A C7B C31 -59.7(3) . . . . ? C3B C7A C7B C31 116.5(2) . . . . ? C16B C7B C7C C8 -122.1(2) . . . . ? C7A C7B C7C C8 -10.2(4) . . . . ? C31 C7B C7C C8 127.0(2) . . . . ? C16B C7B C7C C15C 58.3(2) . . . . ? C7A C7B C7C C15C 170.2(2) . . . . ? C31 C7B C7C C15C -52.7(2) . . . . ? C15C C7C C8 C8A 1.3(3) . . . . ? C7B C7C C8 C8A -178.3(2) . . . . ? C15C C7C C8 C17 -178.0(2) . . . . ? C7B C7C C8 C17 2.4(4) . . . . ? C7C C8 C17 C18 80.0(3) . . . . ? C8A C8 C17 C18 -99.4(3) . . . . ? C7C C8 C17 C22 -104.9(3) . . . . ? C8A C8 C17 C22 75.8(3) . . . . ? C22 C17 C18 C19 0.1(3) . . . . ? C8 C17 C18 C19 175.3(2) . . . . ? C17 C18 C19 C20 0.5(4) . . . . ? C18 C19 C20 C21 -0.7(4) . . . . ? C18 C19 C20 C23 -178.6(2) . . . . ? C21 C20 C23 F3 136.9(2) . . . . ? C19 C20 C23 F3 -45.2(3) . . . . ? C21 C20 C23 F2 15.2(3) . . . . ? C19 C20 C23 F2 -166.9(2) . . . . ? C21 C20 C23 F1 -104.6(3) . . . . ? C19 C20 C23 F1 73.3(3) . . . . ? C19 C20 C21 C22 0.3(4) . . . . ? C23 C20 C21 C22 178.2(2) . . . . ? C18 C17 C22 C21 -0.5(3) . . . . ? C8 C17 C22 C21 -175.7(2) . . . . ? C20 C21 C22 C17 0.3(4) . . . . ? C7C C8 C8A C8B 6.5(3) . . . . ? C17 C8 C8A C8B -174.1(2) . . . . ? C7C C8 C8A C9 -175.6(2) . . . . ? C17 C8 C8A C9 3.8(3) . . . . ? C9 C8A C8B C15B 177.5(2) . . . . ? C8 C8A C8B C15B -4.4(3) . . . . ? C9 C8A C8B C11A -3.2(3) . . . . ? C8 C8A C8B C11A 174.9(2) . . . . ? C8B C8A C9 C10 0.1(3) . . . . ? C8 C8A C9 C10 -177.8(2) . . . . ? C8A C9 C10 C11 2.4(4) . . . . ? C9 C10 C11 C11A -1.7(4) . . . . ? C10 C11 C11A C8B -1.4(4) . . . . ? C10 C11 C11A C11B 177.1(3) . . . . ? C8A C8B C11A C11 4.0(4) . . . . ? C15B C8B C11A C11 -176.7(2) . . . . ? C8A C8B C11A C11B -174.9(2) . . . . ? C15B C8B C11A C11B 4.4(3) . . . . ? C11 C11A C11B C12 -5.9(5) . . . . ? C8B C11A C11B C12 172.7(2) . . . . ? C11 C11A C11B C15A 179.7(3) . . . . ? C8B C11A C11B C15A -1.6(3) . . . . ? C15A C11B C12 C13 0.2(4) . . . . ? C11A C11B C12 C13 -173.5(3) . . . . ? C11B C12 C13 C14 1.2(4) . . . . ? C12 C13 C14 C15 -0.2(4) . . . . ? C13 C14 C15 C15A -2.4(4) . . . . ? C14 C15 C15A C11B 3.8(3) . . . . ? C14 C15 C15A C15B 175.5(2) . . . . ? C12 C11B C15A C15 -2.8(4) . . . . ? C11A C11B C15A C15 172.1(2) . . . . ? C12 C11B C15A C15B -176.4(2) . . . . ? C11A C11B C15A C15B -1.5(3) . . . . ? C8A C8B C15B C15C -5.8(3) . . . . ? C11A C8B C15B C15C 174.8(2) . . . . ? C8A C8B C15B C15A 174.1(2) . . . . ? C11A C8B C15B C15A -5.3(3) . . . . ? C15 C15A C15B C15C 11.6(5) . . . . ? C11B C15A C15B C15C -176.1(3) . . . . ? C15 C15A C15B C8B -168.3(3) . . . . ? C11B C15A C15B C8B 4.1(2) . . . . ? C8B C15B C15C C7C 13.4(3) . . . . ? C15A C15B C15C C7C -166.5(3) . . . . ? C8B C15B C15C C16 -169.8(2) . . . . ? C15A C15B C15C C16 10.3(4) . . . . ? C8 C7C C15C C15B -11.8(3) . . . . ? C7B C7C C15C C15B 167.9(2) . . . . ? C8 C7C C15C C16 171.0(2) . . . . ? C7B C7C C15C C16 -9.3(3) . . . . ? C15B C15C C16 C24 17.9(3) . . . . ? C7C C15C C16 C24 -165.2(2) . . . . ? C15B C15C C16 C16A 137.6(2) . . . . ? C7C C15C C16 C16A -45.5(2) . . . . ? C15B C15C C16 C35 -111.9(2) . . . . ? C7C C15C C16 C35 65.0(2) . . . . ? C2 C1 C16A C16B -1.7(3) . . . . ? C2 C1 C16A C16 -179.0(2) . . . . ? C24 C16 C16A C16B 176.72(19) . . . . ? C15C C16 C16A C16B 50.8(2) . . . . ? C35 C16 C16A C16B -58.5(2) . . . . ? C24 C16 C16A C1 -5.9(3) . . . . ? C15C C16 C16A C1 -131.9(2) . . . . ? C35 C16 C16A C1 118.8(3) . . . . ? C1 C16A C16B C3A 1.9(3) . . . . ? C16 C16A C16B C3A 179.7(2) . . . . ? C1 C16A C16B C7B -176.9(2) . . . . ? C16 C16A C16B C7B 0.9(3) . . . . ? C3 C3A C16B C16A -0.2(4) . . . . ? C3B C3A C16B C16A -177.9(2) . . . . ? C3 C3A C16B C7B 178.7(2) . . . . ? C3B C3A C16B C7B 0.9(3) . . . . ? C7A C7B C16B C16A 175.8(2) . . . . ? C7C C7B C16B C16A -56.2(3) . . . . ? C31 C7B C16B C16A 55.7(3) . . . . ? C7A C7B C16B C3A -3.1(2) . . . . ? C7C C7B C16B C3A 124.8(2) . . . . ? C31 C7B C16B C3A -123.2(2) . . . . ? C16A C16 C24 C25 101.0(3) . . . . ? C15C C16 C24 C25 -138.6(2) . . . . ? C35 C16 C24 C25 -15.8(3) . . . . ? C16A C16 C24 C29 -70.0(3) . . . . ? C15C C16 C24 C29 50.4(3) . . . . ? C35 C16 C24 C29 173.2(2) . . . . ? C29 C24 C25 C26 -1.4(4) . . . . ? C16 C24 C25 C26 -172.3(2) . . . . ? C24 C25 C26 C27 1.4(4) . . . . ? C25 C26 C27 C28 -1.0(4) . . . . ? C25 C26 C27 C30 176.7(2) . . . . ? C28 C27 C30 F5 178.8(2) . . . . ? C26 C27 C30 F5 1.1(3) . . . . ? C28 C27 C30 F4 -59.5(3) . . . . ? C26 C27 C30 F4 122.8(2) . . . . ? C28 C27 C30 F6 59.1(3) . . . . ? C26 C27 C30 F6 -118.6(3) . . . . ? C26 C27 C28 C29 0.5(4) . . . . ? C30 C27 C28 C29 -177.2(2) . . . . ? C27 C28 C29 C24 -0.5(4) . . . . ? C25 C24 C29 C28 0.9(4) . . . . ? C16 C24 C29 C28 172.4(2) . . . . ? C16B C7B C31 C32 -168.74(19) . . . . ? C7A C7B C31 C32 82.2(2) . . . . ? C7C C7B C31 C32 -58.7(2) . . . . ? C16B C7B C31 C35 -51.1(2) . . . . ? C7A C7B C31 C35 -160.17(19) . . . . ? C7C C7B C31 C35 58.9(2) . . . . ? C35 C31 C32 O1 -178.8(2) . . . . ? C7B C31 C32 O1 -57.1(3) . . . . ? C35 C31 C32 N 1.2(2) . . . . ? C7B C31 C32 N 122.9(2) . . . . ? O1 C32 N C34 179.7(2) . . . . ? C31 C32 N C34 -0.2(3) . . . . ? O1 C32 N C33 -2.0(4) . . . . ? C31 C32 N C33 178.1(2) . . . . ? C32 N C34 O2 178.6(2) . . . . ? C33 N C34 O2 0.3(4) . . . . ? C32 N C34 C35 -0.9(3) . . . . ? C33 N C34 C35 -179.2(2) . . . . ? O2 C34 C35 C31 -177.9(2) . . . . ? N C34 C35 C31 1.6(2) . . . . ? O2 C34 C35 C16 62.3(3) . . . . ? N C34 C35 C16 -118.3(2) . . . . ? C32 C31 C35 C34 -1.6(2) . . . . ? C7B C31 C35 C34 -124.4(2) . . . . ? C32 C31 C35 C16 119.9(2) . . . . ? C7B C31 C35 C16 -2.9(3) . . . . ? C24 C16 C35 C34 -68.8(3) . . . . ? C16A C16 C35 C34 173.52(19) . . . . ? C15C C16 C35 C34 60.8(2) . . . . ? C24 C16 C35 C31 174.89(19) . . . . ? C16A C16 C35 C31 57.2(2) . . . . ? C15C C16 C35 C31 -55.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.19 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.440 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.057 #===END data_mjm353(20b) _database_code_depnum_ccdc_archive 'CCDC 769745' #TrackingRef 'mjm59pub.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H19 Br Si' _chemical_formula_sum 'C20 H19 Br Si' _chemical_formula_weight 367.35 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 16.2272(1) _cell_length_b 9.46594(8) _cell_length_c 11.59176(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1780.56(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 26831 _cell_measurement_theta_min 3.8102 _cell_measurement_theta_max 76.2704 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4061 _exptl_crystal_size_mid 0.2983 _exptl_crystal_size_min 0.2050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 3.725 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.079 _exptl_absorpt_correction_T_max 0.312 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _exptl_special_details ; The crystal was refined as an inversion twin. 1672 Friedel pairs were measured. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27644 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 5.41 _diffrn_reflns_theta_max 76.47 _reflns_number_total 3619 _reflns_number_gt 3616 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0441P)^2^+1.7313P] 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 0.08(2) _refine_ls_number_reflns 3619 _refine_ls_number_parameters 203 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 C1 C 0.2804(2) 0.7183(3) 0.6430(3) 0.0279(7) Uani 1 1 d . . . H1 H 0.2781 0.7684 0.5720 0.034 Uiso 1 1 calc R . . C2 C 0.35640(19) 0.7004(3) 0.6976(3) 0.0287(6) Uani 1 1 d . . . H2 H 0.4048 0.7409 0.6655 0.034 Uiso 1 1 calc R . . C3 C 0.36072(19) 0.6233(4) 0.7985(3) 0.0288(6) Uani 1 1 d . . . H3 H 0.4123 0.6098 0.8357 0.035 Uiso 1 1 calc R . . C4 C 0.29015(17) 0.5657(3) 0.8453(3) 0.0243(6) Uani 1 1 d . . . H4 H 0.2938 0.5126 0.9147 0.029 Uiso 1 1 calc R . . C4A C 0.21287(17) 0.5841(3) 0.7925(3) 0.0224(6) Uani 1 1 d . A . C5 C 0.14114(17) 0.5139(3) 0.8475(2) 0.0227(5) Uani 1 1 d . . . C12 C 0.15239(17) 0.3879(3) 0.8933(3) 0.0246(6) Uani 1 1 d . A 1 C13 C 0.16521(19) 0.2665(3) 0.9431(3) 0.0248(6) Uani 1 1 d . A 1 Br Br 0.212171(16) 0.28168(3) 1.09977(4) 0.02830(10) Uani 1 1 d . A 1 Si Si 0.14582(5) 0.08206(8) 0.89180(7) 0.02398(16) Uani 1 1 d . A 1 C14 C 0.2473(2) -0.0088(3) 0.8789(3) 0.0306(6) Uani 1 1 d . A 1 H14A H 0.2766 -0.0032 0.9527 0.046 Uiso 1 1 calc R A 1 H14B H 0.2802 0.0372 0.8188 0.046 Uiso 1 1 calc R A 1 H14C H 0.2386 -0.1081 0.8585 0.046 Uiso 1 1 calc R A 1 C15 C 0.08999(18) 0.0967(3) 0.7412(3) 0.0241(6) Uani 1 1 d . A 1 H15A H 0.0729 0.0024 0.7157 0.036 Uiso 1 1 calc R A 1 H15B H 0.1279 0.1374 0.6845 0.036 Uiso 1 1 calc R A 1 H15C H 0.0414 0.1575 0.7486 0.036 Uiso 1 1 calc R A 1 C16 C 0.0795(2) -0.0062(3) 1.0010(3) 0.0304(6) Uani 1 1 d . A 1 H16A H 0.1047 0.0031 1.0774 0.046 Uiso 1 1 calc R A 1 H16B H 0.0739 -0.1066 0.9816 0.046 Uiso 1 1 calc R A 1 H16C H 0.0249 0.0382 1.0014 0.046 Uiso 1 1 calc R A 1 C5A C 0.06295(16) 0.5908(3) 0.8702(2) 0.0215(5) Uani 1 1 d . A . C6 C 0.02566(17) 0.5709(3) 0.9780(3) 0.0242(6) Uani 1 1 d . . . H6 H 0.0515 0.5108 1.0327 0.029 Uiso 1 1 calc R A . C7 C -0.04825(17) 0.6369(3) 1.0072(3) 0.0272(6) Uani 1 1 d . A . H7 H -0.0729 0.6211 1.0804 0.033 Uiso 1 1 calc R . . C8 C -0.08540(19) 0.7264(3) 0.9273(3) 0.0290(7) Uani 1 1 d . . . H8 H -0.1352 0.7738 0.9464 0.035 Uiso 1 1 calc R A . C9 C -0.05000(19) 0.7463(3) 0.8206(3) 0.0280(6) Uani 1 1 d . A . H9 H -0.0762 0.8070 0.7667 0.034 Uiso 1 1 calc R . . C9A C 0.02412(17) 0.6789(3) 0.7893(3) 0.0237(6) Uani 1 1 d . . . C10 C 0.05399(19) 0.7032(3) 0.6713(3) 0.0266(6) Uani 1 1 d . A . H10 H 0.0128 0.7277 0.6166 0.032 Uiso 1 1 calc R . . C11 C 0.13064(19) 0.6959(3) 0.6295(2) 0.0251(6) Uani 1 1 d . . . H11 H 0.1360 0.7136 0.5492 0.030 Uiso 1 1 calc R A . C11A C 0.20731(17) 0.6643(3) 0.6903(3) 0.0242(6) Uani 1 1 d . A . 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 C1 0.0341(16) 0.0253(18) 0.0243(13) 0.0040(11) 0.0037(11) 0.0014(11) C2 0.0261(14) 0.0266(15) 0.0334(16) 0.0025(13) 0.0089(12) 0.0006(11) C3 0.0254(13) 0.0264(16) 0.0346(16) 0.0008(13) 0.0035(12) 0.0034(11) C4 0.0250(14) 0.0200(15) 0.0279(14) 0.0017(12) 0.0006(11) 0.0031(10) C4A 0.0272(14) 0.0160(14) 0.0239(14) -0.0008(11) 0.0024(11) 0.0018(10) C5 0.0236(12) 0.0191(13) 0.0253(12) -0.0006(11) -0.0020(10) 0.0016(10) C12 0.0232(12) 0.0204(14) 0.0303(14) -0.0036(12) 0.0033(11) -0.0002(10) C13 0.0251(13) 0.0226(15) 0.0266(14) -0.0017(11) 0.0020(11) -0.0008(11) Br 0.02974(14) 0.02822(16) 0.02696(14) 0.00140(15) -0.00036(15) -0.00170(10) Si 0.0269(3) 0.0180(3) 0.0270(4) 0.0011(3) 0.0005(3) -0.0007(3) C14 0.0303(13) 0.0203(13) 0.0411(18) -0.0011(12) 0.0057(16) 0.0002(11) C15 0.0243(12) 0.0103(12) 0.0377(15) -0.0013(10) 0.0047(11) -0.0059(9) C16 0.0342(15) 0.0224(15) 0.0346(15) 0.0061(12) 0.0037(12) -0.0045(12) C5A 0.0192(12) 0.0182(12) 0.0270(14) -0.0011(10) -0.0023(10) -0.0014(9) C6 0.0223(12) 0.0180(13) 0.0321(14) -0.0021(11) -0.0015(11) -0.0012(10) C7 0.0221(13) 0.0221(14) 0.0374(16) -0.0022(12) 0.0037(12) -0.0031(10) C8 0.0194(13) 0.0234(16) 0.0443(19) -0.0015(12) 0.0009(12) -0.0004(11) C9 0.0246(14) 0.0203(14) 0.0391(17) -0.0005(13) -0.0088(12) -0.0009(11) C9A 0.0227(13) 0.0185(14) 0.0300(15) -0.0025(11) -0.0043(11) -0.0028(11) C10 0.0319(15) 0.0222(14) 0.0258(14) -0.0005(11) -0.0121(12) -0.0002(11) C11 0.0344(15) 0.0210(14) 0.0200(14) -0.0012(9) -0.0029(10) -0.0005(11) C11A 0.0306(14) 0.0188(15) 0.0232(13) -0.0024(11) -0.0008(11) -0.0001(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.397(5) . ? C1 C11A 1.403(4) . ? C1 H1 0.9500 . ? C2 C3 1.380(5) . ? C2 H2 0.9500 . ? C3 C4 1.379(4) . ? C3 H3 0.9500 . ? C4 C4A 1.406(4) . ? C4 H4 0.9500 . ? C4A C11A 1.410(4) . ? C4A C5 1.484(4) . ? C5 C12 1.318(4) . ? C5 C5A 1.486(4) . ? C12 C13 1.303(4) . ? C13 Si 1.871(3) . ? C13 Br 1.975(3) . ? Si C16 1.860(3) . ? Si C14 1.864(3) . ? Si C15 1.971(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C5A C6 1.401(4) . ? C5A C9A 1.404(4) . ? C6 C7 1.394(4) . ? C6 H6 0.9500 . ? C7 C8 1.393(5) . ? C7 H7 0.9500 . ? C8 C9 1.376(5) . ? C8 H8 0.9500 . ? C9 C9A 1.409(4) . ? C9 H9 0.9500 . ? C9A C10 1.470(4) . ? C10 C11 1.337(4) . ? C10 H10 0.9500 . ? C11 C11A 1.461(4) . ? C11 H11 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11A 121.6(3) . . ? C2 C1 H1 119.2 . . ? C11A C1 H1 119.2 . . ? C3 C2 C1 119.5(3) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C4A 121.3(3) . . ? C3 C4 H4 119.3 . . ? C4A C4 H4 119.3 . . ? C4 C4A C11A 119.3(3) . . ? C4 C4A C5 117.2(3) . . ? C11A C4A C5 123.5(3) . . ? C12 C5 C4A 118.0(3) . . ? C12 C5 C5A 119.3(3) . . ? C4A C5 C5A 121.8(3) . . ? C13 C12 C5 177.1(3) . . ? C12 C13 Si 130.9(3) . . ? C12 C13 Br 113.9(2) . . ? Si C13 Br 115.15(16) . . ? C16 Si C14 111.01(14) . . ? C16 Si C13 107.49(14) . . ? C14 Si C13 107.89(14) . . ? C16 Si C15 111.59(13) . . ? C14 Si C15 111.57(14) . . ? C13 Si C15 107.05(13) . . ? C6 C5A C9A 118.8(3) . . ? C6 C5A C5 117.4(3) . . ? C9A C5A C5 123.8(3) . . ? C7 C6 C5A 121.9(3) . . ? C7 C6 H6 119.1 . . ? C5A C6 H6 119.1 . . ? C8 C7 C6 118.9(3) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C9 C8 C7 120.0(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C9A 121.8(3) . . ? C8 C9 H9 119.1 . . ? C9A C9 H9 119.1 . . ? C5A C9A C9 118.7(3) . . ? C5A C9A C10 124.5(3) . . ? C9 C9A C10 116.8(3) . . ? C11 C10 C9A 129.5(3) . . ? C11 C10 H10 115.2 . . ? C9A C10 H10 115.2 . . ? C10 C11 C11A 128.9(3) . . ? C10 C11 H11 115.5 . . ? C11A C11 H11 115.5 . . ? C1 C11A C4A 118.1(3) . . ? C1 C11A C11 117.1(3) . . ? C4A C11A C11 124.8(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11A C1 C2 C3 2.4(5) . . . . ? C1 C2 C3 C4 -0.6(5) . . . . ? C2 C3 C4 C4A -0.2(5) . . . . ? C3 C4 C4A C11A -0.7(5) . . . . ? C3 C4 C4A C5 178.0(3) . . . . ? C4 C4A C5 C12 -37.2(4) . . . . ? C11A C4A C5 C12 141.4(3) . . . . ? C4 C4A C5 C5A 131.8(3) . . . . ? C11A C4A C5 C5A -49.6(4) . . . . ? C12 C13 Si C16 -124.6(3) . . . . ? Br C13 Si C16 54.8(2) . . . . ? C12 C13 Si C14 115.6(3) . . . . ? Br C13 Si C14 -64.97(19) . . . . ? C12 C13 Si C15 -4.6(4) . . . . ? Br C13 Si C15 174.82(14) . . . . ? C12 C5 C5A C6 33.3(4) . . . . ? C4A C5 C5A C6 -135.6(3) . . . . ? C12 C5 C5A C9A -145.3(3) . . . . ? C4A C5 C5A C9A 45.8(4) . . . . ? C9A C5A C6 C7 -0.5(4) . . . . ? C5 C5A C6 C7 -179.2(3) . . . . ? C5A C6 C7 C8 -0.8(5) . . . . ? C6 C7 C8 C9 1.3(5) . . . . ? C7 C8 C9 C9A -0.5(5) . . . . ? C6 C5A C9A C9 1.3(4) . . . . ? C5 C5A C9A C9 179.9(3) . . . . ? C6 C5A C9A C10 -176.7(3) . . . . ? C5 C5A C9A C10 1.9(4) . . . . ? C8 C9 C9A C5A -0.8(4) . . . . ? C8 C9 C9A C10 177.3(3) . . . . ? C5A C9A C10 C11 -26.9(5) . . . . ? C9 C9A C10 C11 155.0(3) . . . . ? C9A C10 C11 C11A -1.4(6) . . . . ? C2 C1 C11A C4A -3.3(5) . . . . ? C2 C1 C11A C11 176.7(3) . . . . ? C4 C4A C11A C1 2.4(4) . . . . ? C5 C4A C11A C1 -176.2(3) . . . . ? C4 C4A C11A C11 -177.5(3) . . . . ? C5 C4A C11A C11 3.9(5) . . . . ? C10 C11 C11A C1 -154.1(3) . . . . ? C10 C11 C11A C4A 25.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 76.47 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.877 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.070