# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full MedChemComm _journal_coden_cambridge 1476 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name F.Gabbai _publ_contact_author_email gabbai@chem.tamu.edu loop_ _publ_author_name 'Zibo Li' 'Kantapat Chansaenpak' 'Shuanglong Liu' 'Casey Wade' 'Peter Conti' F.Gabbai # Attachment '- cif.cif' data_ia _database_code_depnum_ccdc_archive 'CCDC 879075' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common none _chemical_melting_point ? _chemical_formula_moiety 'C13 H21 B F3 P' _chemical_formula_sum 'C13 H21 B F3 P' _chemical_formula_weight 276.08 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' B B 0.0013 0.0007 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 11.372(4) _cell_length_b 11.428(5) _cell_length_c 11.129(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1446.3(10) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4914 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 27.33 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9510 _exptl_absorpt_correction_T_max 0.9605 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14159 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2844 _reflns_number_gt 2710 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0382P)^2^+0.2933P] 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 constra _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2844 _refine_ls_number_parameters 163 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0715 _refine_ls_wR_factor_gt 0.0706 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 P1 P 0.14066(3) 1.00073(4) 0.57208(5) 0.01506(10) Uani 1 1 d . . . F1 F 0.12989(8) 0.91989(9) 0.31464(10) 0.0232(2) Uani 1 1 d . . . F2 F 0.28696(9) 0.84661(9) 0.21249(9) 0.0232(2) Uani 1 1 d . . . F3 F 0.20156(10) 0.73913(9) 0.35965(10) 0.0245(2) Uani 1 1 d . . . C4 C 0.14036(16) 1.05894(17) 0.72153(17) 0.0202(4) Uani 1 1 d . . . H4A H 0.1775 1.0029 0.7763 0.030 Uiso 1 1 calc R . . H4B H 0.0592 1.0731 0.7472 0.030 Uiso 1 1 calc R . . H4C H 0.1842 1.1327 0.7229 0.030 Uiso 1 1 calc R . . C5 C 0.32266(15) 0.91140(14) 0.42382(16) 0.0160(3) Uani 1 1 d . . . C6 C 0.06095(15) 0.86252(14) 0.57664(19) 0.0197(3) Uani 1 1 d . . . H6A H 0.0782 0.8200 0.5001 0.024 Uiso 1 1 calc R . . C7 C 0.07101(15) 1.11152(15) 0.47696(17) 0.0191(4) Uani 1 1 d . . . H7A H 0.0354 1.0707 0.4063 0.023 Uiso 1 1 calc R . . C8 C 0.52858(16) 0.94487(16) 0.47706(18) 0.0228(4) Uani 1 1 d . . . H8A H 0.6094 0.9342 0.4586 0.027 Uiso 1 1 calc R . . C9 C 0.44313(15) 0.89790(16) 0.40292(16) 0.0197(4) Uani 1 1 d . . . H9A H 0.4675 0.8544 0.3345 0.024 Uiso 1 1 calc R . . C10 C 0.37766(16) 1.02169(16) 0.60346(16) 0.0204(4) Uani 1 1 d . . . H10A H 0.3547 1.0644 0.6728 0.025 Uiso 1 1 calc R . . C11 C 0.29183(15) 0.97393(15) 0.52794(17) 0.0160(3) Uani 1 1 d . . . C12 C -0.02758(18) 1.17653(18) 0.54305(19) 0.0290(5) Uani 1 1 d . . . H12A H -0.0630 1.2344 0.4890 0.044 Uiso 1 1 calc R . . H12B H 0.0050 1.2164 0.6136 0.044 Uiso 1 1 calc R . . H12C H -0.0877 1.1204 0.5688 0.044 Uiso 1 1 calc R . . B13 B 0.23393(17) 0.85313(18) 0.32608(18) 0.0171(4) Uani 1 1 d . . . C14 C 0.16276(17) 1.19777(17) 0.4298(2) 0.0269(4) Uani 1 1 d . . . H14A H 0.1242 1.2563 0.3790 0.040 Uiso 1 1 calc R . . H14B H 0.2218 1.1555 0.3826 0.040 Uiso 1 1 calc R . . H14C H 0.2012 1.2368 0.4977 0.040 Uiso 1 1 calc R . . C15 C 0.49604(15) 1.00715(16) 0.5777(2) 0.0239(4) Uani 1 1 d . . . H15A H 0.5542 1.0398 0.6290 0.029 Uiso 1 1 calc R . . C16 C 0.1094(2) 0.78829(18) 0.6802(2) 0.0304(5) Uani 1 1 d . . . H16A H 0.0670 0.7137 0.6835 0.046 Uiso 1 1 calc R . . H16B H 0.0989 0.8303 0.7562 0.046 Uiso 1 1 calc R . . H16C H 0.1933 0.7734 0.6670 0.046 Uiso 1 1 calc R . . C17 C -0.07226(16) 0.87734(18) 0.5849(2) 0.0289(4) Uani 1 1 d . . . H17A H -0.1098 0.8002 0.5867 0.043 Uiso 1 1 calc R . . H17B H -0.1005 0.9211 0.5149 0.043 Uiso 1 1 calc R . . H17C H -0.0920 0.9202 0.6584 0.043 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 P1 0.01373(19) 0.01604(19) 0.0154(2) -0.00281(16) 0.0011(2) -0.00071(16) F1 0.0187(5) 0.0296(6) 0.0211(5) -0.0056(5) -0.0038(4) 0.0039(4) F2 0.0226(5) 0.0305(6) 0.0167(5) -0.0037(5) 0.0043(4) -0.0041(5) F3 0.0275(6) 0.0214(5) 0.0247(6) -0.0049(5) 0.0069(4) -0.0057(4) C4 0.0188(9) 0.0247(9) 0.0173(9) -0.0059(8) 0.0024(7) -0.0001(7) C5 0.0172(8) 0.0147(8) 0.0161(9) 0.0036(7) 0.0013(7) 0.0001(7) C6 0.0220(8) 0.0176(8) 0.0196(8) -0.0045(8) 0.0043(8) -0.0055(7) C7 0.0181(9) 0.0204(9) 0.0187(9) 0.0002(7) -0.0011(7) 0.0027(7) C8 0.0167(8) 0.0226(9) 0.0292(10) 0.0015(8) 0.0016(8) 0.0021(7) C9 0.0199(9) 0.0197(9) 0.0196(9) -0.0008(7) 0.0014(7) 0.0030(7) C10 0.0208(9) 0.0189(9) 0.0216(11) -0.0040(7) -0.0013(7) 0.0002(7) C11 0.0138(8) 0.0155(8) 0.0188(8) 0.0011(7) -0.0003(7) 0.0002(7) C12 0.0277(10) 0.0302(10) 0.0293(11) 0.0002(8) 0.0024(8) 0.0115(9) B13 0.0169(9) 0.0189(10) 0.0154(9) -0.0028(8) 0.0024(8) -0.0009(8) C14 0.0265(10) 0.0226(9) 0.0316(11) 0.0073(9) 0.0009(9) 0.0002(8) C15 0.0172(8) 0.0242(8) 0.0301(10) -0.0028(9) -0.0061(10) -0.0014(7) C16 0.0403(12) 0.0225(10) 0.0284(11) 0.0027(9) 0.0070(9) -0.0028(9) C17 0.0234(9) 0.0320(10) 0.0314(11) -0.0080(10) 0.0078(9) -0.0104(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 P1 C4 1.791(2) . ? P1 C11 1.8139(19) . ? P1 C6 1.8219(17) . ? P1 C7 1.8305(19) . ? F1 B13 1.414(2) . ? F2 B13 1.403(2) . ? F3 B13 1.404(2) . ? C5 C9 1.398(3) . ? C5 C11 1.406(3) . ? C5 B13 1.626(3) . ? C6 C17 1.527(2) . ? C6 C16 1.533(3) . ? C7 C14 1.528(3) . ? C7 C12 1.533(3) . ? C8 C15 1.378(3) . ? C8 C9 1.383(3) . ? C10 C15 1.386(3) . ? C10 C11 1.399(3) . ? 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 C4 P1 C11 108.42(9) . . ? C4 P1 C6 107.17(9) . . ? C11 P1 C6 109.43(8) . . ? C4 P1 C7 106.22(9) . . ? C11 P1 C7 111.73(8) . . ? C6 P1 C7 113.60(9) . . ? C9 C5 C11 115.95(16) . . ? C9 C5 B13 116.84(16) . . ? C11 C5 B13 127.21(16) . . ? C17 C6 C16 111.88(17) . . ? C17 C6 P1 113.52(13) . . ? C16 C6 P1 108.76(13) . . ? C14 C7 C12 110.57(16) . . ? C14 C7 P1 110.43(12) . . ? C12 C7 P1 111.97(14) . . ? C15 C8 C9 119.79(17) . . ? C8 C9 C5 123.11(17) . . ? C15 C10 C11 120.45(18) . . ? C10 C11 C5 121.30(16) . . ? C10 C11 P1 115.64(14) . . ? C5 C11 P1 123.05(13) . . ? F2 B13 F3 107.65(15) . . ? F2 B13 F1 107.90(15) . . ? F3 B13 F1 107.77(14) . . ? F2 B13 C5 110.97(15) . . ? F3 B13 C5 111.38(15) . . ? F1 B13 C5 111.01(15) . . ? C8 C15 C10 119.38(18) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.254 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.036 data_i _database_code_depnum_ccdc_archive 'CCDC 897246' #TrackingRef '- COOHPh2P_BF3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 B F3 O2 P' _chemical_formula_weight 382.99 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' B B 0.0013 0.0007 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P21/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 9.163(10) _cell_length_b 12.426(14) _cell_length_c 17.335(19) _cell_angle_alpha 90.00 _cell_angle_beta 100.483(18) _cell_angle_gamma 90.00 _cell_volume 1941(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9510 _exptl_absorpt_correction_T_max 0.9605 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11053 _diffrn_reflns_av_R_equivalents 0.0675 _diffrn_reflns_av_sigmaI/netI 0.0753 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 24.52 _reflns_number_total 3212 _reflns_number_gt 1862 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.1533P)^2^+2.9538P] 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 SHELXL _refine_ls_extinction_coef 0.013(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3212 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1446 _refine_ls_R_factor_gt 0.0895 _refine_ls_wR_factor_ref 0.2884 _refine_ls_wR_factor_gt 0.2502 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 P1 P 0.67350(18) 0.03428(12) 0.16857(8) 0.0442(6) Uani 1 1 d . . . F2 F 0.6668(6) 0.2699(4) 0.2199(3) 0.1045(18) Uani 1 1 d . . . F1 F 0.8955(7) 0.3325(6) 0.2168(4) 0.158(3) Uani 1 1 d . . . F3 F 0.6953(8) 0.3988(4) 0.1371(3) 0.132(2) Uani 1 1 d . . . O2 O 0.9694(5) 0.0435(4) 0.4100(2) 0.0586(13) Uani 1 1 d . . . O1 O 0.8135(6) -0.0539(4) 0.4627(2) 0.0690(15) Uani 1 1 d . . . H1A H 0.8821 -0.0499 0.5020 0.103 Uiso 1 1 calc R . . C21 C 0.8528(8) -0.0031(5) 0.4038(3) 0.0480(16) Uani 1 1 d . . . C8 C 0.5432(7) -0.1559(5) 0.1074(4) 0.0555(17) Uani 1 1 d . . . H8A H 0.4537 -0.1159 0.0944 0.067 Uiso 1 1 calc R . . C3 C 0.8539(7) 0.0994(6) -0.0216(4) 0.0552(17) Uani 1 1 d . . . H3A H 0.8759 0.0595 -0.0648 0.066 Uiso 1 1 calc R . . C1 C 0.7562(6) 0.1081(5) 0.0978(3) 0.0411(14) Uani 1 1 d . . . C6 C 0.7862(7) 0.2195(5) 0.1052(4) 0.0504(16) Uani 1 1 d . . . C2 C 0.7912(7) 0.0491(5) 0.0351(3) 0.0458(15) Uani 1 1 d . . . H2A H 0.7717 -0.0260 0.0316 0.055 Uiso 1 1 calc R . . C16 C 0.1929(8) 0.1388(6) 0.1570(4) 0.0628(19) Uani 1 1 d . . . H16A H 0.0929 0.1607 0.1546 0.075 Uiso 1 1 calc R . . C17 C 0.2785(8) 0.1870(5) 0.1097(4) 0.0620(19) Uani 1 1 d . . . H17A H 0.2368 0.2421 0.0745 0.074 Uiso 1 1 calc R . . C12 C 0.8025(8) -0.1682(6) 0.1631(4) 0.0569(18) Uani 1 1 d . . . H12A H 0.8930 -0.1370 0.1889 0.068 Uiso 1 1 calc R . . C7 C 0.6735(7) -0.1057(5) 0.1457(3) 0.0443(15) Uani 1 1 d . . . C14 C 0.3959(8) 0.0261(5) 0.2108(4) 0.0548(17) Uani 1 1 d . . . H14A H 0.4348 -0.0308 0.2451 0.066 Uiso 1 1 calc R . . C9 C 0.5456(10) -0.2648(5) 0.0884(4) 0.070(2) Uani 1 1 d . . . H9A H 0.4572 -0.2989 0.0627 0.083 Uiso 1 1 calc R . . C15 C 0.2517(8) 0.0594(6) 0.2075(4) 0.0592(18) Uani 1 1 d . . . H15A H 0.1925 0.0268 0.2406 0.071 Uiso 1 1 calc R . . C18 C 0.4244(8) 0.1566(5) 0.1123(4) 0.0524(17) Uani 1 1 d . . . H18A H 0.4825 0.1907 0.0792 0.063 Uiso 1 1 calc R . . C4 C 0.8845(8) 0.2078(6) -0.0155(4) 0.0605(18) Uani 1 1 d . . . H4A H 0.9300 0.2427 -0.0538 0.073 Uiso 1 1 calc R . . C19 C 0.7873(8) 0.0521(5) 0.2648(3) 0.0550(18) Uani 1 1 d . . . H19A H 0.8902 0.0305 0.2618 0.066 Uiso 1 1 calc R . . H19B H 0.7893 0.1297 0.2778 0.066 Uiso 1 1 calc R . . C10 C 0.6700(11) -0.3215(5) 0.1058(4) 0.071(2) Uani 1 1 d . . . H10A H 0.6700 -0.3957 0.0925 0.085 Uiso 1 1 calc R . . C13 C 0.4856(7) 0.0758(5) 0.1638(3) 0.0459(15) Uani 1 1 d . . . C20 C 0.7405(8) -0.0087(5) 0.3311(3) 0.0561(18) Uani 1 1 d . . . H20A H 0.6458 0.0213 0.3413 0.067 Uiso 1 1 calc R . . H20B H 0.7232 -0.0850 0.3157 0.067 Uiso 1 1 calc R . . C5 C 0.8496(8) 0.2650(6) 0.0456(5) 0.0626(19) Uani 1 1 d . . . H5A H 0.8695 0.3401 0.0478 0.075 Uiso 1 1 calc R . . C11 C 0.7970(9) -0.2743(6) 0.1425(4) 0.069(2) Uani 1 1 d . . . H11A H 0.8849 -0.3163 0.1543 0.082 Uiso 1 1 calc R . . B1 B 0.7612(10) 0.3078(7) 0.1715(5) 0.067(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 P1 0.0509(10) 0.0468(10) 0.0325(8) 0.0011(6) 0.0008(7) 0.0043(7) F2 0.154(5) 0.081(3) 0.090(4) -0.024(3) 0.053(4) -0.021(3) F1 0.107(5) 0.191(7) 0.161(6) -0.110(5) -0.016(4) -0.015(4) F3 0.212(7) 0.078(4) 0.108(4) 0.007(3) 0.035(4) 0.055(4) O2 0.068(3) 0.064(3) 0.039(2) 0.007(2) -0.004(2) -0.013(2) O1 0.083(4) 0.081(3) 0.038(2) 0.009(2) -0.002(2) -0.027(3) C21 0.066(5) 0.043(3) 0.033(3) -0.001(3) 0.003(3) -0.002(3) C8 0.053(4) 0.052(4) 0.058(4) -0.002(3) 0.000(3) 0.009(3) C3 0.057(4) 0.066(5) 0.043(4) 0.000(3) 0.010(3) 0.003(3) C1 0.038(3) 0.047(3) 0.035(3) 0.005(3) -0.001(2) 0.001(3) C6 0.049(4) 0.053(4) 0.047(4) -0.001(3) 0.002(3) 0.001(3) C2 0.049(4) 0.046(4) 0.041(3) 0.002(3) 0.004(3) 0.007(3) C16 0.059(5) 0.063(4) 0.068(5) -0.005(4) 0.018(4) 0.014(4) C17 0.058(5) 0.052(4) 0.071(5) 0.005(3) 0.001(4) 0.018(3) C12 0.056(4) 0.062(4) 0.052(4) 0.013(3) 0.006(3) 0.010(3) C7 0.052(4) 0.044(3) 0.036(3) 0.002(3) 0.006(3) 0.008(3) C14 0.069(5) 0.055(4) 0.040(3) 0.006(3) 0.010(3) 0.003(3) C9 0.093(6) 0.043(4) 0.074(5) -0.010(3) 0.020(4) -0.013(4) C15 0.055(4) 0.073(5) 0.054(4) -0.006(3) 0.020(3) -0.002(4) C18 0.065(5) 0.044(3) 0.047(4) 0.007(3) 0.009(3) 0.002(3) C4 0.058(4) 0.061(4) 0.065(5) 0.011(4) 0.019(4) -0.001(3) C19 0.070(5) 0.051(4) 0.037(3) 0.000(3) -0.007(3) -0.001(3) C10 0.118(7) 0.035(4) 0.068(5) 0.009(3) 0.041(5) 0.019(4) C13 0.054(4) 0.046(3) 0.036(3) 0.001(3) 0.004(3) 0.006(3) C20 0.072(5) 0.054(4) 0.037(3) 0.007(3) -0.002(3) -0.004(3) C5 0.058(5) 0.049(4) 0.079(5) 0.008(4) 0.009(4) -0.007(3) C11 0.077(6) 0.066(5) 0.066(5) 0.018(4) 0.022(4) 0.033(4) B1 0.068(6) 0.062(5) 0.065(5) 0.010(4) 0.000(5) 0.002(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 P1 C7 1.784(6) . ? P1 C13 1.785(7) . ? P1 C1 1.805(6) . ? P1 C19 1.813(6) . ? F2 B1 1.391(11) . ? F1 B1 1.368(10) . ? F3 B1 1.367(10) . ? O2 C21 1.202(8) . ? O1 C21 1.305(8) . ? O1 H1A 0.8400 . ? C21 C20 1.476(8) . ? C8 C9 1.394(9) . ? C8 C7 1.403(9) . ? C8 H8A 0.9500 . ? C3 C2 1.376(9) . ? C3 C4 1.377(10) . ? C3 H3A 0.9500 . ? C1 C2 1.395(8) . ? C1 C6 1.413(9) . ? C6 C5 1.394(10) . ? C6 B1 1.635(11) . ? C2 H2A 0.9500 . ? C16 C15 1.362(10) . ? C16 C17 1.372(10) . ? C16 H16A 0.9500 . ? C17 C18 1.381(9) . ? C17 H17A 0.9500 . ? C12 C11 1.365(10) . ? C12 C7 1.401(9) . ? C12 H12A 0.9500 . ? C14 C15 1.376(9) . ? C14 C13 1.402(9) . ? C14 H14A 0.9500 . ? C9 C10 1.328(11) . ? C9 H9A 0.9500 . ? C15 H15A 0.9500 . ? C18 C13 1.392(8) . ? C18 H18A 0.9500 . ? C4 C5 1.361(10) . ? C4 H4A 0.9500 . ? C19 C20 1.502(9) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C10 C11 1.353(11) . ? C10 H10A 0.9500 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C5 H5A 0.9500 . ? C11 H11A 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 C7 P1 C13 108.1(3) . . ? C7 P1 C1 109.1(3) . . ? C13 P1 C1 110.0(3) . . ? C7 P1 C19 107.5(3) . . ? C13 P1 C19 113.3(3) . . ? C1 P1 C19 108.7(3) . . ? C21 O1 H1A 109.5 . . ? O2 C21 O1 122.0(6) . . ? O2 C21 C20 124.7(6) . . ? O1 C21 C20 113.3(6) . . ? C9 C8 C7 119.7(6) . . ? C9 C8 H8A 120.2 . . ? C7 C8 H8A 120.2 . . ? C2 C3 C4 119.7(6) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C2 C1 C6 121.1(6) . . ? C2 C1 P1 116.5(4) . . ? C6 C1 P1 122.3(5) . . ? C5 C6 C1 115.5(6) . . ? C5 C6 B1 112.3(6) . . ? C1 C6 B1 132.2(6) . . ? C3 C2 C1 120.2(6) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? C15 C16 C17 119.8(7) . . ? C15 C16 H16A 120.1 . . ? C17 C16 H16A 120.1 . . ? C16 C17 C18 121.1(6) . . ? C16 C17 H17A 119.5 . . ? C18 C17 H17A 119.5 . . ? C11 C12 C7 119.3(7) . . ? C11 C12 H12A 120.3 . . ? C7 C12 H12A 120.3 . . ? C12 C7 C8 117.9(6) . . ? C12 C7 P1 121.8(5) . . ? C8 C7 P1 120.3(4) . . ? C15 C14 C13 120.2(6) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C10 C9 C8 120.7(7) . . ? C10 C9 H9A 119.6 . . ? C8 C9 H9A 119.6 . . ? C16 C15 C14 120.6(7) . . ? C16 C15 H15A 119.7 . . ? C14 C15 H15A 119.7 . . ? C17 C18 C13 119.5(6) . . ? C17 C18 H18A 120.2 . . ? C13 C18 H18A 120.2 . . ? C5 C4 C3 119.8(7) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? C20 C19 P1 116.5(5) . . ? C20 C19 H19A 108.2 . . ? P1 C19 H19A 108.2 . . ? C20 C19 H19B 108.2 . . ? P1 C19 H19B 108.2 . . ? H19A C19 H19B 107.3 . . ? C9 C10 C11 120.4(7) . . ? C9 C10 H10A 119.8 . . ? C11 C10 H10A 119.8 . . ? C18 C13 C14 118.7(6) . . ? C18 C13 P1 120.7(5) . . ? C14 C13 P1 120.6(5) . . ? C21 C20 C19 112.2(6) . . ? C21 C20 H20A 109.2 . . ? C19 C20 H20A 109.2 . . ? C21 C20 H20B 109.2 . . ? C19 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C4 C5 C6 123.6(6) . . ? C4 C5 H5A 118.2 . . ? C6 C5 H5A 118.2 . . ? C10 C11 C12 121.9(7) . . ? C10 C11 H11A 119.0 . . ? C12 C11 H11A 119.0 . . ? F3 B1 F1 110.1(8) . . ? F3 B1 F2 105.6(8) . . ? F1 B1 F2 108.9(7) . . ? F3 B1 C6 110.8(7) . . ? F1 B1 C6 109.1(7) . . ? F2 B1 C6 112.3(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 C7 P1 C1 C2 6.1(5) . . . . ? C13 P1 C1 C2 -112.3(5) . . . . ? C19 P1 C1 C2 123.0(5) . . . . ? C7 P1 C1 C6 -173.1(5) . . . . ? C13 P1 C1 C6 68.4(5) . . . . ? C19 P1 C1 C6 -56.2(6) . . . . ? C2 C1 C6 C5 1.1(8) . . . . ? P1 C1 C6 C5 -179.7(5) . . . . ? C2 C1 C6 B1 -178.7(6) . . . . ? P1 C1 C6 B1 0.5(9) . . . . ? C4 C3 C2 C1 1.2(9) . . . . ? C6 C1 C2 C3 -1.1(8) . . . . ? P1 C1 C2 C3 179.7(5) . . . . ? C15 C16 C17 C18 -0.2(11) . . . . ? C11 C12 C7 C8 0.0(9) . . . . ? C11 C12 C7 P1 -178.4(5) . . . . ? C9 C8 C7 C12 0.3(10) . . . . ? C9 C8 C7 P1 178.7(5) . . . . ? C13 P1 C7 C12 -163.8(5) . . . . ? C1 P1 C7 C12 76.6(6) . . . . ? C19 P1 C7 C12 -41.1(6) . . . . ? C13 P1 C7 C8 17.9(6) . . . . ? C1 P1 C7 C8 -101.7(5) . . . . ? C19 P1 C7 C8 140.5(5) . . . . ? C7 C8 C9 C10 -0.3(11) . . . . ? C17 C16 C15 C14 -0.8(11) . . . . ? C13 C14 C15 C16 1.9(10) . . . . ? C16 C17 C18 C13 0.0(10) . . . . ? C2 C3 C4 C5 -1.5(10) . . . . ? C7 P1 C19 C20 -58.8(6) . . . . ? C13 P1 C19 C20 60.6(6) . . . . ? C1 P1 C19 C20 -176.7(5) . . . . ? C8 C9 C10 C11 0.1(12) . . . . ? C17 C18 C13 C14 1.1(9) . . . . ? C17 C18 C13 P1 179.8(5) . . . . ? C15 C14 C13 C18 -2.1(9) . . . . ? C15 C14 C13 P1 179.3(5) . . . . ? C7 P1 C13 C18 -120.7(5) . . . . ? C1 P1 C13 C18 -1.7(6) . . . . ? C19 P1 C13 C18 120.2(5) . . . . ? C7 P1 C13 C14 57.9(5) . . . . ? C1 P1 C13 C14 176.9(5) . . . . ? C19 P1 C13 C14 -61.1(6) . . . . ? O2 C21 C20 C19 -0.7(10) . . . . ? O1 C21 C20 C19 178.9(6) . . . . ? P1 C19 C20 C21 170.6(5) . . . . ? C3 C4 C5 C6 1.7(11) . . . . ? C1 C6 C5 C4 -1.4(10) . . . . ? B1 C6 C5 C4 178.5(7) . . . . ? C9 C10 C11 C12 0.2(12) . . . . ? C7 C12 C11 C10 -0.2(11) . . . . ? C5 C6 B1 F3 47.5(9) . . . . ? C1 C6 B1 F3 -132.6(8) . . . . ? C5 C6 B1 F1 -73.9(8) . . . . ? C1 C6 B1 F1 106.0(9) . . . . ? C5 C6 B1 F2 165.4(6) . . . . ? C1 C6 B1 F2 -14.8(10) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.52 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.907 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.087