# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Takeo Taguchi' _publ_contact_author_email TAGUCHI@PS.TOYAKU.AC.JP _publ_section_title ; Novel Defluorinative Alkylation of Trifluoroacetaldehyde N,O-Acetal Derivatives and Its Application to Multi-component Reaction ; loop_ _publ_author_name 'Takeo Taguchi' 'Hikaru Yanai' # Attachment '2ca.cif' #============================================================================== data_2ca _database_code_depnum_ccdc_archive 'CCDC 702162' #============================================================================== _audit_creation_date '12 September 08' _audit_creation_method 'SHELXL97 ' _chemical_name_systematic ; 3-Benzyl-2-butyl-2-(difluoromethyl)-2,3-dihydro-1,3-benzoxazole ; _chemical_name_common ;3-Benzyl-2-butyl-2-(difluoromethyl)-2,3-dihydro-1,3- benzoxazole ; _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 F2 N O' _chemical_formula_sum 'C19 H21 F2 N O' _chemical_formula_weight 317.37 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' #============================================================================== # CRYSTAL DATA #============================================================================== _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 8.979(6) _cell_length_b 9.368(6) _cell_length_c 10.983(13) _cell_angle_alpha 97.534(11) _cell_angle_beta 97.342(11) _cell_angle_gamma 113.009(8) _cell_volume 826.5(12) _cell_formula_units_Z 2 _cell_measurement_temperature 90 _cell_measurement_reflns_used 2179 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 27.33 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9734 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator 'multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3929 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.42 _reflns_number_total 3073 _reflns_number_gt 2426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.1169P)^2^+0.2045P] 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 3073 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1747 _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 N1 N 0.7603(2) 0.36960(19) 0.66935(17) 0.0182(4) Uani 1 1 d . . . O1 O 0.89987(17) 0.34985(16) 0.85360(14) 0.0210(4) Uani 1 1 d . . . C4 C 1.0182(2) 0.6850(2) 0.8333(2) 0.0215(5) Uani 1 1 d . . . H4A H 1.0984 0.6441 0.8660 0.026 Uiso 1 1 calc R . . H4B H 1.0098 0.6729 0.7415 0.026 Uiso 1 1 calc R . . C1 C 0.7842(2) 0.4121(2) 0.8056(2) 0.0184(5) Uani 1 1 d . . . C2 C 0.6237(3) 0.3130(3) 0.8448(2) 0.0242(5) Uani 1 1 d . . . H2 H 0.5908 0.1980 0.8117 0.029 Uiso 1 1 calc R . . C5 C 1.0812(3) 0.8597(2) 0.8916(2) 0.0278(6) Uani 1 1 d . . . H5A H 1.0052 0.9023 0.8538 0.033 Uiso 1 1 calc R . . H5B H 1.0804 0.8707 0.9824 0.033 Uiso 1 1 calc R . . C3 C 0.8498(2) 0.5876(2) 0.8616(2) 0.0211(5) Uani 1 1 d . . . H3A H 0.8585 0.6013 0.9535 0.025 Uiso 1 1 calc R . . H3B H 0.7700 0.6286 0.8284 0.025 Uiso 1 1 calc R . . C6 C 1.2545(3) 0.9569(3) 0.8736(3) 0.0321(6) Uani 1 1 d . . . H6A H 1.3306 0.9161 0.9116 0.048 Uiso 1 1 calc R . . H6B H 1.2893 1.0677 0.9136 0.048 Uiso 1 1 calc R . . H6C H 1.2554 0.9495 0.7839 0.048 Uiso 1 1 calc R . . C8 C 0.5883(2) 0.3433(2) 0.4663(2) 0.0174(5) Uani 1 1 d . . . C9 C 0.6090(2) 0.3822(2) 0.3514(2) 0.0210(5) Uani 1 1 d . . . H9 H 0.6972 0.4780 0.3466 0.025 Uiso 1 1 calc R . . C7 C 0.7025(2) 0.4536(2) 0.5847(2) 0.0190(5) Uani 1 1 d . . . H7A H 0.7988 0.5352 0.5622 0.023 Uiso 1 1 calc R . . H7B H 0.6438 0.5081 0.6284 0.023 Uiso 1 1 calc R . . C10 C 0.5024(3) 0.2830(3) 0.2416(2) 0.0246(5) Uani 1 1 d . . . H10 H 0.5178 0.3109 0.1626 0.030 Uiso 1 1 calc R . . C12 C 0.3520(3) 0.1039(2) 0.3642(2) 0.0295(6) Uani 1 1 d . . . H12 H 0.2634 0.0084 0.3690 0.035 Uiso 1 1 calc R . . C13 C 0.4585(3) 0.2024(2) 0.4728(2) 0.0238(5) Uani 1 1 d . . . H13 H 0.4433 0.1741 0.5517 0.029 Uiso 1 1 calc R . . C11 C 0.3736(3) 0.1433(3) 0.2492(2) 0.0274(5) Uani 1 1 d . . . H11 H 0.3005 0.0749 0.1750 0.033 Uiso 1 1 calc R . . C16 C 0.9127(2) 0.2648(2) 0.5289(2) 0.0202(5) Uani 1 1 d . . . H16 H 0.8603 0.2757 0.4521 0.024 Uiso 1 1 calc R . . C15 C 0.8755(2) 0.3107(2) 0.6423(2) 0.0171(5) Uani 1 1 d . . . C14 C 0.9559(2) 0.2974(2) 0.7526(2) 0.0179(5) Uani 1 1 d . . . C17 C 1.0308(3) 0.2016(2) 0.5329(2) 0.0231(5) Uani 1 1 d . . . H17 H 1.0576 0.1673 0.4567 0.028 Uiso 1 1 calc R . . C19 C 1.0736(2) 0.2375(2) 0.7586(2) 0.0217(5) Uani 1 1 d . . . H19 H 1.1278 0.2303 0.8362 0.026 Uiso 1 1 calc R . . C18 C 1.1093(2) 0.1877(2) 0.6441(2) 0.0224(5) Uani 1 1 d . . . H18 H 1.1885 0.1439 0.6432 0.027 Uiso 1 1 calc R . . F1 F 0.50205(15) 0.35606(16) 0.79926(14) 0.0301(4) Uani 1 1 d . . . F2 F 0.64008(16) 0.33978(17) 0.97089(13) 0.0343(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 N1 0.0191(8) 0.0195(8) 0.0160(10) 0.0060(7) 0.0004(7) 0.0083(7) O1 0.0239(8) 0.0237(7) 0.0162(9) 0.0065(6) -0.0006(6) 0.0114(6) C4 0.0224(10) 0.0206(9) 0.0182(12) 0.0054(9) 0.0009(8) 0.0061(8) C1 0.0203(10) 0.0207(9) 0.0134(12) 0.0075(9) -0.0017(8) 0.0080(8) C2 0.0233(11) 0.0285(10) 0.0193(12) 0.0091(9) 0.0025(8) 0.0082(9) C5 0.0265(11) 0.0203(10) 0.0331(15) 0.0051(10) -0.0008(10) 0.0080(9) C3 0.0225(10) 0.0217(10) 0.0180(12) 0.0049(9) 0.0006(8) 0.0088(8) C6 0.0297(12) 0.0216(10) 0.0382(16) 0.0099(10) -0.0006(10) 0.0045(9) C8 0.0178(9) 0.0172(9) 0.0166(12) 0.0050(8) -0.0004(8) 0.0073(7) C9 0.0209(10) 0.0221(9) 0.0190(12) 0.0077(9) 0.0015(8) 0.0075(8) C7 0.0224(10) 0.0165(9) 0.0168(12) 0.0083(8) -0.0001(8) 0.0064(8) C10 0.0296(11) 0.0312(11) 0.0148(12) 0.0081(9) 0.0020(9) 0.0140(9) C12 0.0243(11) 0.0199(10) 0.0329(15) 0.0039(10) -0.0015(10) 0.0000(8) C13 0.0244(11) 0.0231(10) 0.0203(13) 0.0107(9) 0.0029(9) 0.0045(8) C11 0.0258(11) 0.0247(10) 0.0260(14) -0.0011(10) -0.0044(9) 0.0094(9) C16 0.0221(10) 0.0158(8) 0.0186(12) 0.0060(8) 0.0023(8) 0.0032(7) C15 0.0171(9) 0.0129(8) 0.0170(12) 0.0055(8) 0.0002(8) 0.0020(7) C14 0.0194(9) 0.0130(8) 0.0179(12) 0.0060(8) 0.0012(8) 0.0030(7) C17 0.0244(10) 0.0141(8) 0.0277(14) 0.0046(9) 0.0082(9) 0.0038(8) C19 0.0219(10) 0.0169(9) 0.0224(13) 0.0055(9) -0.0036(8) 0.0058(8) C18 0.0208(10) 0.0165(9) 0.0290(14) 0.0068(9) 0.0028(9) 0.0068(8) F1 0.0202(6) 0.0378(7) 0.0323(9) 0.0140(6) 0.0043(5) 0.0102(5) F2 0.0321(7) 0.0459(8) 0.0223(8) 0.0136(7) 0.0079(6) 0.0106(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 N1 C15 1.395(3) . ? N1 C1 1.462(3) . ? N1 C7 1.463(3) . ? O1 C14 1.385(3) . ? O1 C1 1.453(3) . ? C4 C5 1.523(3) . ? C4 C3 1.527(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C1 C3 1.521(3) . ? C1 C2 1.530(3) . ? C2 F2 1.353(3) . ? C2 F1 1.365(3) . ? C2 H2 1.0000 . ? C5 C6 1.519(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C8 C9 1.374(3) . ? C8 C13 1.395(3) . ? C8 C7 1.512(3) . ? C9 C10 1.396(3) . ? C9 H9 0.9500 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C10 C11 1.388(3) . ? C10 H10 0.9500 . ? C12 C11 1.378(4) . ? C12 C13 1.385(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C11 H11 0.9500 . ? C16 C15 1.387(3) . ? C16 C17 1.402(3) . ? C16 H16 0.9500 . ? C15 C14 1.376(3) . ? C14 C19 1.375(3) . ? C17 C18 1.378(4) . ? C17 H17 0.9500 . ? C19 C18 1.403(3) . ? C19 H19 0.9500 . ? C18 H18 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 C15 N1 C1 107.78(16) . . ? C15 N1 C7 121.23(19) . . ? C1 N1 C7 122.71(17) . . ? C14 O1 C1 107.41(17) . . ? C5 C4 C3 111.94(18) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? O1 C1 N1 104.75(15) . . ? O1 C1 C3 109.64(16) . . ? N1 C1 C3 116.35(18) . . ? O1 C1 C2 104.14(18) . . ? N1 C1 C2 107.99(16) . . ? C3 C1 C2 112.97(18) . . ? F2 C2 F1 106.42(17) . . ? F2 C2 C1 111.16(17) . . ? F1 C2 C1 109.5(2) . . ? F2 C2 H2 109.9 . . ? F1 C2 H2 109.9 . . ? C1 C2 H2 109.9 . . ? C6 C5 C4 112.85(19) . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C1 C3 C4 113.25(17) . . ? C1 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? C1 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C9 C8 C13 119.24(19) . . ? C9 C8 C7 120.38(19) . . ? C13 C8 C7 120.4(2) . . ? C8 C9 C10 121.0(2) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? N1 C7 C8 112.12(17) . . ? N1 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C11 C10 C9 119.3(2) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C11 C12 C13 120.5(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C8 120.0(2) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? C12 C11 C10 120.0(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C15 C16 C17 117.0(2) . . ? C15 C16 H16 121.5 . . ? C17 C16 H16 121.5 . . ? C14 C15 C16 120.4(2) . . ? C14 C15 N1 108.57(19) . . ? C16 C15 N1 131.0(2) . . ? C19 C14 C15 123.4(2) . . ? C19 C14 O1 125.9(2) . . ? C15 C14 O1 110.66(19) . . ? C18 C17 C16 121.9(2) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C14 C19 C18 116.5(2) . . ? C14 C19 H19 121.8 . . ? C18 C19 H19 121.8 . . ? C17 C18 C19 120.8(2) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? _diffrn_measured_fraction_theta_max 0.813 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.813 _refine_diff_density_max 0.366 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.076 # Attachment 'anti-3h.cif' #============================================================================== data_anti-3h _database_code_depnum_ccdc_archive 'CCDC 702163' #============================================================================== _audit_creation_date '12 September 08' _audit_creation_method 'SHELXL97 ' _chemical_name_systematic ; (1S*)-2-[(2S*)-3-Allyl-2-butyl-2,3-dihydro-1,3-benzoxazol-2-yl] -1-cyclohexyl-2,2-difluoroethan-1-ol ; _chemical_name_common ; (1S*)-2-((2S*)-3-Allyl-2-butyl-2,3-dihydro-1,3-benzoxazol-2- yl) -1-cyclohexyl-2,2-difluoroethan-1-ol ; _chemical_melting_point ? _chemical_formula_moiety 'C22 H31 F2 N O2' _chemical_formula_sum 'C22 H31 F2 N O2' _chemical_formula_weight 379.48 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_absolute_configuration . 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' #============================================================================== # CRYSTAL DATA #============================================================================== _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 12.9702(11) _cell_length_b 13.2002(11) _cell_length_c 13.8440(12) _cell_angle_alpha 76.3530(10) _cell_angle_beta 68.1340(10) _cell_angle_gamma 67.3330(10) _cell_volume 2017.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 9958 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 27.62 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9758 _exptl_absorpt_correction_T_max 0.9784 _exptl_absorpt_process_details ? _exptl_special_details ; SADABS Sheldrick 1996 ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator 'multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23356 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.62 _reflns_number_total 9165 _reflns_number_gt 8197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0576P)^2^+0.7888P] 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 9165 _refine_ls_number_parameters 491 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1027 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 O3 O 0.96566(7) -0.07646(6) 0.15022(6) 0.01469(15) Uani 1 1 d . . . H3 H 0.9270 -0.0532 0.1078 0.022 Uiso 1 1 calc R . . F3 F 0.85833(6) 0.14041(5) 0.17796(5) 0.01745(14) Uani 1 1 d . . . F4 F 0.65552(6) 0.08274(5) 1.12621(5) 0.01736(14) Uani 1 1 d . . . F1 F 1.00695(5) 0.06360(5) 0.23932(5) 0.01600(13) Uani 1 1 d . . . O4 O 0.86194(7) -0.01532(6) 0.99565(6) 0.01513(15) Uani 1 1 d . . . H4 H 0.8966 0.0202 0.9434 0.023 Uiso 1 1 calc R . . O1 O 0.87239(6) 0.06845(6) 0.43952(6) 0.01471(15) Uani 1 1 d . . . O2 O 0.74530(7) 0.20628(6) 0.92510(6) 0.01489(15) Uani 1 1 d . . . F2 F 0.55283(5) 0.04578(5) 1.05296(5) 0.01780(14) Uani 1 1 d . . . N2 N 0.55692(8) 0.27972(7) 1.03187(7) 0.01550(18) Uani 1 1 d . . . N1 N 0.70246(8) 0.10300(7) 0.40143(7) 0.01482(18) Uani 1 1 d . . . C22 C 0.40268(12) 0.27382(13) 0.45265(13) 0.0386(3) Uani 1 1 d . . . H22A H 0.3744 0.2185 0.4497 0.046 Uiso 1 1 calc R . . H22B H 0.3495 0.3382 0.4856 0.046 Uiso 1 1 calc R . . C39 C 0.55322(14) 0.40820(12) 0.63157(10) 0.0349(3) Uani 1 1 d . . . H39A H 0.4750 0.4576 0.6663 0.052 Uiso 1 1 calc R . . H39B H 0.5568 0.3988 0.5621 0.052 Uiso 1 1 calc R . . H39C H 0.6128 0.4403 0.6242 0.052 Uiso 1 1 calc R . . C44 C 0.28787(12) 0.43587(12) 1.20643(11) 0.0333(3) Uani 1 1 d . . . H44A H 0.2897 0.3890 1.2699 0.040 Uiso 1 1 calc R . . H44B H 0.2364 0.5102 1.2082 0.040 Uiso 1 1 calc R . . C17 C 0.99229(12) 0.43045(11) 0.29297(10) 0.0257(3) Uani 1 1 d . . . H17A H 1.0444 0.3837 0.3341 0.038 Uiso 1 1 calc R . . H17B H 0.9711 0.5081 0.3022 0.038 Uiso 1 1 calc R . . H17C H 1.0329 0.4198 0.2188 0.038 Uiso 1 1 calc R . . C21 C 0.51567(11) 0.26129(10) 0.41105(10) 0.0247(2) Uani 1 1 d . . . H21 H 0.5415 0.3180 0.4152 0.030 Uiso 1 1 calc R . . C1 C 0.60691(11) -0.01751(10) 0.67939(9) 0.0227(2) Uani 1 1 d . . . H1 H 0.5436 -0.0357 0.7335 0.027 Uiso 1 1 calc R . . C11 C 0.71234(11) -0.04305(10) 0.69797(9) 0.0222(2) Uani 1 1 d . . . H11 H 0.7204 -0.0795 0.7640 0.027 Uiso 1 1 calc R . . C43 C 0.35660(10) 0.39792(10) 1.11608(10) 0.0222(2) Uani 1 1 d . . . H43 H 0.3527 0.4469 1.0541 0.027 Uiso 1 1 calc R . . C38 C 0.57668(10) 0.29593(10) 0.69720(9) 0.0213(2) Uani 1 1 d . . . H38A H 0.5147 0.2650 0.7064 0.026 Uiso 1 1 calc R . . H38B H 0.6532 0.2447 0.6594 0.026 Uiso 1 1 calc R . . C18 C 1.08249(11) -0.27038(10) 0.41129(9) 0.0202(2) Uani 1 1 d . . . H18A H 1.1686 -0.3007 0.3986 0.024 Uiso 1 1 calc R . . H18B H 1.0453 -0.2372 0.4783 0.024 Uiso 1 1 calc R . . C37 C 0.57881(11) 0.30406(9) 0.80464(9) 0.0200(2) Uani 1 1 d . . . H37A H 0.5046 0.3596 0.8403 0.024 Uiso 1 1 calc R . . H37B H 0.6446 0.3297 0.7954 0.024 Uiso 1 1 calc R . . C42 C 0.44082(10) 0.28204(9) 1.10487(9) 0.0199(2) Uani 1 1 d . . . H42A H 0.4485 0.2456 1.1742 0.024 Uiso 1 1 calc R . . H42B H 0.4088 0.2399 1.0796 0.024 Uiso 1 1 calc R . . C40 C 0.73947(10) -0.28814(9) 1.17207(9) 0.0191(2) Uani 1 1 d . . . H40A H 0.7354 -0.3069 1.2467 0.023 Uiso 1 1 calc R . . H40B H 0.6694 -0.2955 1.1652 0.023 Uiso 1 1 calc R . . C33 C 0.70422(10) 0.42014(9) 1.11884(9) 0.0191(2) Uani 1 1 d . . . H33 H 0.6922 0.4690 1.1655 0.023 Uiso 1 1 calc R . . C16 C 0.88103(10) 0.39909(9) 0.33005(9) 0.0190(2) Uani 1 1 d . . . H16A H 0.8260 0.4503 0.2923 0.023 Uiso 1 1 calc R . . H16B H 0.8420 0.4071 0.4057 0.023 Uiso 1 1 calc R . . C10 C 1.03686(10) -0.36381(9) 0.41965(9) 0.0190(2) Uani 1 1 d . . . H10A H 1.0799 -0.4021 0.3556 0.023 Uiso 1 1 calc R . . H10B H 1.0513 -0.4181 0.4802 0.023 Uiso 1 1 calc R . . C2 C 0.59126(10) 0.03465(9) 0.58255(9) 0.0190(2) Uani 1 1 d . . . H2 H 0.5188 0.0518 0.5701 0.023 Uiso 1 1 calc R . . C9 C 0.90522(10) -0.31862(9) 0.43341(9) 0.0191(2) Uani 1 1 d . . . H9A H 0.8616 -0.2860 0.5006 0.023 Uiso 1 1 calc R . . H9B H 0.8778 -0.3798 0.4357 0.023 Uiso 1 1 calc R . . C19 C 1.05589(10) -0.18081(9) 0.32242(9) 0.0187(2) Uani 1 1 d . . . H19A H 1.0827 -0.1197 0.3215 0.022 Uiso 1 1 calc R . . H19B H 1.0996 -0.2120 0.2545 0.022 Uiso 1 1 calc R . . C23 C 0.81532(10) 0.37955(9) 1.04817(9) 0.0189(2) Uani 1 1 d . . . H23 H 0.8773 0.4023 1.0462 0.023 Uiso 1 1 calc R . . C20 C 0.60619(10) 0.16223(9) 0.35732(9) 0.0183(2) Uani 1 1 d . . . H20A H 0.5663 0.1104 0.3606 0.022 Uiso 1 1 calc R . . H20B H 0.6398 0.1867 0.2826 0.022 Uiso 1 1 calc R . . C13 C 0.80799(10) -0.01578(9) 0.62036(9) 0.0182(2) Uani 1 1 d . . . H13 H 0.8808 -0.0328 0.6321 0.022 Uiso 1 1 calc R . . C32 C 0.85065(10) -0.36833(9) 1.10632(9) 0.0184(2) Uani 1 1 d . . . H32A H 0.9207 -0.3643 1.1162 0.022 Uiso 1 1 calc R . . H32B H 0.8489 -0.4447 1.1295 0.022 Uiso 1 1 calc R . . C31 C 0.85905(10) -0.33958(9) 0.99088(9) 0.0178(2) Uani 1 1 d . . . H31A H 0.7917 -0.3486 0.9805 0.021 Uiso 1 1 calc R . . H31B H 0.9323 -0.3910 0.9488 0.021 Uiso 1 1 calc R . . C36 C 0.59327(10) 0.19351(9) 0.87354(8) 0.0171(2) Uani 1 1 d . . . H36A H 0.5173 0.1793 0.9006 0.021 Uiso 1 1 calc R . . H36B H 0.6519 0.1339 0.8302 0.021 Uiso 1 1 calc R . . C34 C 0.60882(10) 0.39111(9) 1.12338(9) 0.0174(2) Uani 1 1 d . . . H34 H 0.5330 0.4191 1.1722 0.021 Uiso 1 1 calc R . . C41 C 0.73825(10) -0.16853(9) 1.13704(8) 0.0171(2) Uani 1 1 d . . . H41A H 0.8034 -0.1594 1.1513 0.020 Uiso 1 1 calc R . . H41B H 0.6633 -0.1182 1.1784 0.020 Uiso 1 1 calc R . . C24 C 0.83740(10) 0.30500(9) 0.97918(9) 0.0168(2) Uani 1 1 d . . . H24 H 0.9133 0.2756 0.9311 0.020 Uiso 1 1 calc R . . C15 C 0.90792(10) 0.28059(9) 0.31156(8) 0.0168(2) Uani 1 1 d . . . H15A H 0.9460 0.2729 0.2358 0.020 Uiso 1 1 calc R . . H15B H 0.9639 0.2295 0.3485 0.020 Uiso 1 1 calc R . . C8 C 0.87943(10) -0.23051(9) 0.34319(9) 0.0167(2) Uani 1 1 d . . . H8A H 0.9186 -0.2642 0.2764 0.020 Uiso 1 1 calc R . . H8B H 0.7936 -0.2010 0.3544 0.020 Uiso 1 1 calc R . . C30 C 0.85876(10) -0.22079(9) 0.95310(8) 0.0161(2) Uani 1 1 d . . . H30A H 0.8590 -0.2031 0.8794 0.019 Uiso 1 1 calc R . . H30B H 0.9315 -0.2146 0.9553 0.019 Uiso 1 1 calc R . . C14 C 0.79701(9) 0.24863(9) 0.34998(8) 0.0155(2) Uani 1 1 d . . . H14A H 0.7509 0.2877 0.3011 0.019 Uiso 1 1 calc R . . H14B H 0.7488 0.2760 0.4191 0.019 Uiso 1 1 calc R . . C3 C 0.68568(10) 0.06016(9) 0.50577(8) 0.0151(2) Uani 1 1 d . . . C25 C 0.74373(9) 0.27727(8) 0.98518(8) 0.0144(2) Uani 1 1 d . . . C35 C 0.63010(9) 0.31992(9) 1.05351(8) 0.0148(2) Uani 1 1 d . . . C12 C 0.79006(9) 0.03670(8) 0.52699(8) 0.0145(2) Uani 1 1 d . . . C26 C 0.63275(9) 0.18968(9) 0.96586(8) 0.0142(2) Uani 1 1 d . . . C29 C 0.75150(9) -0.13643(8) 1.01985(8) 0.0140(2) Uani 1 1 d . . . H29 H 0.6797 -0.1369 1.0090 0.017 Uiso 1 1 calc R . . C27 C 0.65225(9) 0.07341(9) 1.03082(8) 0.0140(2) Uani 1 1 d . . . C7 C 0.92375(9) -0.13592(8) 0.33638(8) 0.0139(2) Uani 1 1 d . . . H7 H 0.8825 -0.1040 0.4049 0.017 Uiso 1 1 calc R . . C5 C 0.89310(9) 0.06933(9) 0.25880(8) 0.0138(2) Uani 1 1 d . . . C28 C 0.76229(9) -0.02062(8) 0.97931(8) 0.01316(19) Uani 1 1 d . . . H28 H 0.7749 -0.0084 0.9022 0.016 Uiso 1 1 calc R . . C6 C 0.88987(9) -0.04366(8) 0.25128(8) 0.0133(2) Uani 1 1 d . . . H6 H 0.8078 -0.0338 0.2559 0.016 Uiso 1 1 calc R . . C4 C 0.81489(9) 0.12522(8) 0.36085(8) 0.0136(2) 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 O3 0.0160(4) 0.0183(4) 0.0099(3) -0.0020(3) -0.0038(3) -0.0057(3) F3 0.0237(3) 0.0156(3) 0.0120(3) 0.0024(2) -0.0065(3) -0.0068(3) F4 0.0218(3) 0.0189(3) 0.0111(3) -0.0025(2) -0.0043(2) -0.0067(3) F1 0.0145(3) 0.0178(3) 0.0158(3) -0.0022(2) -0.0015(2) -0.0083(2) O4 0.0147(4) 0.0190(4) 0.0134(4) 0.0017(3) -0.0051(3) -0.0088(3) O1 0.0154(4) 0.0178(4) 0.0112(3) 0.0004(3) -0.0042(3) -0.0069(3) O2 0.0144(4) 0.0163(4) 0.0145(4) -0.0034(3) -0.0022(3) -0.0068(3) F2 0.0130(3) 0.0182(3) 0.0216(3) -0.0023(2) -0.0028(2) -0.0069(2) N2 0.0137(4) 0.0154(4) 0.0168(4) -0.0046(3) -0.0025(3) -0.0047(3) N1 0.0141(4) 0.0179(4) 0.0122(4) 0.0009(3) -0.0033(3) -0.0072(3) C22 0.0207(6) 0.0359(8) 0.0461(9) -0.0018(6) -0.0037(6) -0.0035(5) C39 0.0438(8) 0.0300(7) 0.0201(6) 0.0008(5) -0.0134(6) 0.0002(6) C44 0.0225(6) 0.0369(7) 0.0321(7) -0.0127(6) -0.0028(5) -0.0014(5) C17 0.0350(7) 0.0279(6) 0.0214(6) -0.0030(5) -0.0067(5) -0.0199(5) C21 0.0199(6) 0.0236(6) 0.0272(6) 0.0000(5) -0.0084(5) -0.0043(5) C1 0.0270(6) 0.0238(6) 0.0149(5) -0.0003(4) 0.0000(5) -0.0132(5) C11 0.0328(6) 0.0208(5) 0.0118(5) 0.0012(4) -0.0059(5) -0.0106(5) C43 0.0170(5) 0.0232(6) 0.0238(6) -0.0029(4) -0.0059(4) -0.0044(4) C38 0.0209(6) 0.0234(6) 0.0166(5) -0.0028(4) -0.0062(4) -0.0036(4) C18 0.0223(6) 0.0205(5) 0.0202(5) 0.0032(4) -0.0113(4) -0.0082(4) C37 0.0245(6) 0.0177(5) 0.0182(5) -0.0015(4) -0.0093(4) -0.0048(4) C42 0.0148(5) 0.0208(5) 0.0220(6) -0.0035(4) -0.0022(4) -0.0064(4) C40 0.0216(5) 0.0195(5) 0.0167(5) 0.0010(4) -0.0037(4) -0.0110(4) C33 0.0233(6) 0.0154(5) 0.0207(5) -0.0038(4) -0.0096(4) -0.0049(4) C16 0.0247(6) 0.0172(5) 0.0171(5) -0.0011(4) -0.0066(4) -0.0093(4) C10 0.0204(5) 0.0160(5) 0.0183(5) 0.0002(4) -0.0063(4) -0.0047(4) C2 0.0186(5) 0.0202(5) 0.0168(5) -0.0018(4) -0.0018(4) -0.0085(4) C9 0.0194(5) 0.0159(5) 0.0192(5) 0.0021(4) -0.0038(4) -0.0075(4) C19 0.0191(5) 0.0206(5) 0.0195(5) 0.0044(4) -0.0092(4) -0.0104(4) C23 0.0192(5) 0.0171(5) 0.0239(6) -0.0011(4) -0.0098(4) -0.0074(4) C20 0.0167(5) 0.0223(5) 0.0175(5) 0.0010(4) -0.0071(4) -0.0083(4) C13 0.0231(6) 0.0172(5) 0.0154(5) -0.0022(4) -0.0071(4) -0.0066(4) C32 0.0215(5) 0.0156(5) 0.0197(5) 0.0009(4) -0.0081(4) -0.0077(4) C31 0.0195(5) 0.0162(5) 0.0189(5) -0.0033(4) -0.0067(4) -0.0056(4) C36 0.0198(5) 0.0168(5) 0.0166(5) -0.0022(4) -0.0076(4) -0.0059(4) C34 0.0181(5) 0.0156(5) 0.0169(5) -0.0033(4) -0.0049(4) -0.0035(4) C41 0.0197(5) 0.0166(5) 0.0135(5) -0.0010(4) -0.0025(4) -0.0074(4) C24 0.0155(5) 0.0154(5) 0.0184(5) -0.0006(4) -0.0050(4) -0.0050(4) C15 0.0190(5) 0.0172(5) 0.0149(5) -0.0018(4) -0.0036(4) -0.0084(4) C8 0.0166(5) 0.0160(5) 0.0177(5) 0.0003(4) -0.0048(4) -0.0075(4) C30 0.0166(5) 0.0162(5) 0.0138(5) -0.0022(4) -0.0036(4) -0.0044(4) C14 0.0166(5) 0.0144(5) 0.0146(5) -0.0019(4) -0.0036(4) -0.0054(4) C3 0.0192(5) 0.0131(5) 0.0124(5) -0.0017(4) -0.0032(4) -0.0062(4) C25 0.0175(5) 0.0126(5) 0.0127(5) -0.0005(4) -0.0052(4) -0.0047(4) C35 0.0156(5) 0.0138(5) 0.0147(5) 0.0002(4) -0.0055(4) -0.0049(4) C12 0.0172(5) 0.0131(5) 0.0120(5) -0.0027(4) -0.0015(4) -0.0060(4) C26 0.0134(5) 0.0144(5) 0.0141(5) -0.0021(4) -0.0033(4) -0.0045(4) C29 0.0141(5) 0.0140(5) 0.0144(5) -0.0016(4) -0.0043(4) -0.0053(4) C27 0.0141(5) 0.0175(5) 0.0121(5) -0.0021(4) -0.0035(4) -0.0071(4) C7 0.0172(5) 0.0136(5) 0.0106(4) -0.0005(4) -0.0035(4) -0.0060(4) C5 0.0149(5) 0.0158(5) 0.0108(5) 0.0015(4) -0.0044(4) -0.0067(4) C28 0.0130(5) 0.0147(5) 0.0121(5) -0.0011(4) -0.0041(4) -0.0050(4) C6 0.0144(5) 0.0151(5) 0.0104(5) -0.0016(4) -0.0027(4) -0.0060(4) C4 0.0139(5) 0.0154(5) 0.0120(5) -0.0004(4) -0.0044(4) -0.0057(4) _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 O3 C6 1.4298(12) . ? O3 H3 0.8400 . ? F3 C5 1.3750(11) . ? F4 C27 1.3724(12) . ? F1 C5 1.3733(12) . ? O4 C28 1.4219(12) . ? O4 H4 0.8400 . ? O1 C12 1.3873(12) . ? O1 C4 1.4467(12) . ? O2 C25 1.3823(13) . ? O2 C26 1.4394(12) . ? F2 C27 1.3803(12) . ? N2 C35 1.3954(14) . ? N2 C42 1.4613(14) . ? N2 C26 1.4688(13) . ? N1 C3 1.3888(13) . ? N1 C20 1.4608(14) . ? N1 C4 1.4729(13) . ? C22 C21 1.3176(19) . ? C22 H22A 0.9500 . ? C22 H22B 0.9500 . ? C39 C38 1.5289(17) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C44 C43 1.3157(18) . ? C44 H44A 0.9500 . ? C44 H44B 0.9500 . ? C17 C16 1.5250(16) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C21 C20 1.5056(17) . ? C21 H21 0.9500 . ? C1 C11 1.3840(18) . ? C1 C2 1.4043(16) . ? C1 H1 0.9500 . ? C11 C13 1.4113(16) . ? C11 H11 0.9500 . ? C43 C42 1.5017(16) . ? C43 H43 0.9500 . ? C38 C37 1.5274(15) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C18 C10 1.5260(16) . ? C18 C19 1.5316(15) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C37 C36 1.5297(15) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C40 C32 1.5261(16) . ? C40 C41 1.5341(15) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C33 C23 1.3866(17) . ? C33 C34 1.4064(16) . ? C33 H33 0.9500 . ? C16 C15 1.5284(15) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C10 C9 1.5277(16) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C2 C3 1.3865(15) . ? C2 H2 0.9500 . ? C9 C8 1.5331(15) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C19 C7 1.5330(15) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C23 C24 1.4089(15) . ? C23 H23 0.9500 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C13 C12 1.3719(15) . ? C13 H13 0.9500 . ? C32 C31 1.5250(15) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C31 C30 1.5304(15) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C36 C26 1.5282(14) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C34 C35 1.3874(15) . ? C34 H34 0.9500 . ? C41 C29 1.5380(14) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C24 C25 1.3676(15) . ? C24 H24 0.9500 . ? C15 C14 1.5239(15) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C8 C7 1.5348(14) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C30 C29 1.5373(14) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C14 C4 1.5328(14) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C3 C12 1.3947(15) . ? C25 C35 1.3990(15) . ? C26 C27 1.5643(14) . ? C29 C28 1.5405(14) . ? C29 H29 1.0000 . ? C27 C28 1.5428(14) . ? C7 C6 1.5365(14) . ? C7 H7 1.0000 . ? C5 C6 1.5368(14) . ? C5 C4 1.5546(14) . ? C28 H28 1.0000 . ? C6 H6 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 C6 O3 H3 109.5 . . ? C28 O4 H4 109.5 . . ? C12 O1 C4 107.57(8) . . ? C25 O2 C26 107.74(8) . . ? C35 N2 C42 122.28(9) . . ? C35 N2 C26 107.50(8) . . ? C42 N2 C26 122.30(9) . . ? C3 N1 C20 123.52(9) . . ? C3 N1 C4 108.00(8) . . ? C20 N1 C4 122.83(8) . . ? C21 C22 H22A 120.0 . . ? C21 C22 H22B 120.0 . . ? H22A C22 H22B 120.0 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C43 C44 H44A 120.0 . . ? C43 C44 H44B 120.0 . . ? H44A C44 H44B 120.0 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C22 C21 C20 123.70(13) . . ? C22 C21 H21 118.2 . . ? C20 C21 H21 118.2 . . ? C11 C1 C2 121.63(11) . . ? C11 C1 H1 119.2 . . ? C2 C1 H1 119.2 . . ? C1 C11 C13 121.01(10) . . ? C1 C11 H11 119.5 . . ? C13 C11 H11 119.5 . . ? C44 C43 C42 124.08(12) . . ? C44 C43 H43 118.0 . . ? C42 C43 H43 118.0 . . ? C37 C38 C39 112.10(10) . . ? C37 C38 H38A 109.2 . . ? C39 C38 H38A 109.2 . . ? C37 C38 H38B 109.2 . . ? C39 C38 H38B 109.2 . . ? H38A C38 H38B 107.9 . . ? C10 C18 C19 111.48(9) . . ? C10 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? C10 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C38 C37 C36 112.27(9) . . ? C38 C37 H37A 109.2 . . ? C36 C37 H37A 109.2 . . ? C38 C37 H37B 109.2 . . ? C36 C37 H37B 109.2 . . ? H37A C37 H37B 107.9 . . ? N2 C42 C43 111.82(9) . . ? N2 C42 H42A 109.3 . . ? C43 C42 H42A 109.3 . . ? N2 C42 H42B 109.3 . . ? C43 C42 H42B 109.3 . . ? H42A C42 H42B 107.9 . . ? C32 C40 C41 111.08(9) . . ? C32 C40 H40A 109.4 . . ? C41 C40 H40A 109.4 . . ? C32 C40 H40B 109.4 . . ? C41 C40 H40B 109.4 . . ? H40A C40 H40B 108.0 . . ? C23 C33 C34 121.92(10) . . ? C23 C33 H33 119.0 . . ? C34 C33 H33 119.0 . . ? C17 C16 C15 111.84(10) . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C9 C10 C18 110.53(9) . . ? C9 C10 H10A 109.5 . . ? C18 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C18 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C3 C2 C1 117.42(11) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? C10 C9 C8 110.80(9) . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C7 C19 C18 110.88(9) . . ? C7 C19 H19A 109.5 . . ? C18 C19 H19A 109.5 . . ? C7 C19 H19B 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? C33 C23 C24 120.78(10) . . ? C33 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? N1 C20 C21 114.76(9) . . ? N1 C20 H20A 108.6 . . ? C21 C20 H20A 108.6 . . ? N1 C20 H20B 108.6 . . ? C21 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? C12 C13 C11 116.34(10) . . ? C12 C13 H13 121.8 . . ? C11 C13 H13 121.8 . . ? C31 C32 C40 110.08(9) . . ? C31 C32 H32A 109.6 . . ? C40 C32 H32A 109.6 . . ? C31 C32 H32B 109.6 . . ? C40 C32 H32B 109.6 . . ? H32A C32 H32B 108.2 . . ? C32 C31 C30 111.06(9) . . ? C32 C31 H31A 109.4 . . ? C30 C31 H31A 109.4 . . ? C32 C31 H31B 109.4 . . ? C30 C31 H31B 109.4 . . ? H31A C31 H31B 108.0 . . ? C26 C36 C37 113.10(9) . . ? C26 C36 H36A 109.0 . . ? C37 C36 H36A 109.0 . . ? C26 C36 H36B 109.0 . . ? C37 C36 H36B 109.0 . . ? H36A C36 H36B 107.8 . . ? C35 C34 C33 117.16(10) . . ? C35 C34 H34 121.4 . . ? C33 C34 H34 121.4 . . ? C40 C41 C29 111.92(9) . . ? C40 C41 H41A 109.2 . . ? C29 C41 H41A 109.2 . . ? C40 C41 H41B 109.2 . . ? C29 C41 H41B 109.2 . . ? H41A C41 H41B 107.9 . . ? C25 C24 C23 116.42(10) . . ? C25 C24 H24 121.8 . . ? C23 C24 H24 121.8 . . ? C14 C15 C16 111.88(9) . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C7 C8 C9 110.52(9) . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C31 C30 C29 112.50(9) . . ? C31 C30 H30A 109.1 . . ? C29 C30 H30A 109.1 . . ? C31 C30 H30B 109.1 . . ? C29 C30 H30B 109.1 . . ? H30A C30 H30B 107.8 . . ? C15 C14 C4 116.58(9) . . ? C15 C14 H14A 108.1 . . ? C4 C14 H14A 108.1 . . ? C15 C14 H14B 108.1 . . ? C4 C14 H14B 108.1 . . ? H14A C14 H14B 107.3 . . ? C2 C3 N1 131.90(10) . . ? C2 C3 C12 120.10(10) . . ? N1 C3 C12 107.91(9) . . ? C24 C25 O2 126.16(10) . . ? C24 C25 C35 123.75(10) . . ? O2 C25 C35 110.08(9) . . ? C34 C35 N2 132.68(10) . . ? C34 C35 C25 119.89(10) . . ? N2 C35 C25 107.40(9) . . ? C13 C12 O1 126.05(10) . . ? C13 C12 C3 123.45(10) . . ? O1 C12 C3 110.42(9) . . ? O2 C26 N2 104.04(8) . . ? O2 C26 C36 108.28(8) . . ? N2 C26 C36 113.96(9) . . ? O2 C26 C27 106.25(8) . . ? N2 C26 C27 112.40(8) . . ? C36 C26 C27 111.26(9) . . ? C30 C29 C28 108.58(8) . . ? C30 C29 C41 111.17(9) . . ? C28 C29 C41 113.50(8) . . ? C30 C29 H29 107.8 . . ? C28 C29 H29 107.8 . . ? C41 C29 H29 107.8 . . ? F4 C27 F2 105.18(8) . . ? F4 C27 C28 109.40(8) . . ? F2 C27 C28 109.56(8) . . ? F4 C27 C26 108.55(8) . . ? F2 C27 C26 107.38(8) . . ? C28 C27 C26 116.19(8) . . ? C19 C7 C8 110.18(9) . . ? C19 C7 C6 113.88(8) . . ? C8 C7 C6 110.51(8) . . ? C19 C7 H7 107.3 . . ? C8 C7 H7 107.3 . . ? C6 C7 H7 107.3 . . ? F1 C5 F3 105.29(8) . . ? F1 C5 C6 110.09(8) . . ? F3 C5 C6 106.90(8) . . ? F1 C5 C4 108.53(8) . . ? F3 C5 C4 106.95(8) . . ? C6 C5 C4 118.27(8) . . ? O4 C28 C29 109.74(8) . . ? O4 C28 C27 109.04(8) . . ? C29 C28 C27 113.61(8) . . ? O4 C28 H28 108.1 . . ? C29 C28 H28 108.1 . . ? C27 C28 H28 108.1 . . ? O3 C6 C5 108.00(8) . . ? O3 C6 C7 109.68(8) . . ? C5 C6 C7 115.66(8) . . ? O3 C6 H6 107.7 . . ? C5 C6 H6 107.7 . . ? C7 C6 H6 107.7 . . ? O1 C4 N1 104.38(8) . . ? O1 C4 C14 108.76(8) . . ? N1 C4 C14 112.22(8) . . ? O1 C4 C5 106.93(8) . . ? N1 C4 C5 109.84(8) . . ? C14 C4 C5 114.10(8) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.430 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.044