Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 186 _publ_contact_author_name 'Prof Hubert Schmidbaur' _publ_contact_author_address ; Anorganische und Analytische Chemie Technische Universitaet Muenchen Lichtenbergstr. 4 Garching D-85747 GERMANY ; _publ_contact_author_phone '++49 89 2891-3130' _publ_contact_author_fax '++49 89 2891-3125' _publ_contact_author_email H.Schmidbaur@lrz.tu-muenchen.de _publ_requested_journal 'Dalton Transactions' _publ_requested_coeditor_name ? _publ_contact_letter ? #============================================================================ _publ_section_title ; Trivinylphosphineborane (CH2=CH)3PBH3 and Related Compounds ; loop_ _publ_author_name _publ_author_address 'H. Schmidbaur' ; Anorganisch-chemisches Institut der Technischen Universitat Munchen Lichtenbergstrase 4 D-85747 Garching Germany ; 'U. Monkowius' ; Anorganisch-chemisches Institut der Technischen Universitat Munchen Lichtenbergstrase 4 D-85747 Garching Germany ; 'S. Nogai' ; Anorganisch-chemisches Institut der Technischen Universitat Munchen Lichtenbergstrase 4 D-85747 Garching Germany ; #===================================================================== data_uwe12 _database_code_CSD 197160 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H9 B Cl3 P' _chemical_formula_weight 229.26 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 13.6690(3) _cell_length_b 6.40700(10) _cell_length_c 12.5050(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1095.15(4) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 34487 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.922 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'NONIUS DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34487 _diffrn_reflns_av_R_equivalents 0.046 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.70 _reflns_number_total 2407 _reflns_number_gt 2346 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Structure was refined as racemic twin. ; _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^)+(0.0244P)^2^+0.2980P] 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 isotropic _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 0.49(8) _refine_ls_number_reflns 2407 _refine_ls_number_parameters 137 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0626 _refine_ls_wR_factor_gt 0.0614 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 -0.34696(4) -0.10855(7) -0.69065(4) 0.02389(11) Uani 1 1 d . . . Cl2 Cl -0.48846(4) -0.17242(9) -0.87696(4) 0.03599(14) Uani 1 1 d . . . Cl3 Cl -0.31845(5) 0.13221(9) -0.90172(4) 0.04128(15) Uani 1 1 d . . . Cl1 Cl -0.48801(3) 0.24337(8) -0.75553(5) 0.03326(13) Uani 1 1 d . . . B1 B -0.41350(17) 0.0299(4) -0.8110(2) 0.0284(4) Uani 1 1 d . . . C31 C -0.28677(17) -0.3393(3) -0.73521(19) 0.0313(5) Uani 1 1 d . . . C21 C -0.43324(18) -0.1789(4) -0.58960(18) 0.0334(5) Uani 1 1 d . . . C11 C -0.25810(18) 0.0631(4) -0.6338(2) 0.0398(5) Uani 1 1 d . . . C32 C -0.19432(19) -0.3795(5) -0.7143(3) 0.0496(7) Uani 1 1 d . . . C22 C -0.4371(2) -0.3656(4) -0.5451(2) 0.0427(6) Uani 1 1 d . . . C12 C -0.2555(3) 0.1132(5) -0.5313(3) 0.0547(8) Uani 1 1 d . . . H31A H -0.3247(19) -0.424(4) -0.773(2) 0.039(7) Uiso 1 1 d . . . H22B H -0.486(2) -0.391(5) -0.488(3) 0.044(8) Uiso 1 1 d . . . H21A H -0.475(2) -0.070(5) -0.565(2) 0.044(8) Uiso 1 1 d . . . H32B H -0.165(3) -0.516(6) -0.745(3) 0.079(11) Uiso 1 1 d . . . H22A H -0.387(2) -0.480(5) -0.566(3) 0.052(8) Uiso 1 1 d . . . H12A H -0.212(3) 0.220(6) -0.509(3) 0.075(10) Uiso 1 1 d . . . H32A H -0.155(2) -0.276(5) -0.675(3) 0.061(9) Uiso 1 1 d . . . H12B H -0.305(3) 0.055(7) -0.478(3) 0.089(13) Uiso 1 1 d . . . H11A H -0.209(2) 0.114(4) -0.688(3) 0.045(7) 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 P1 0.0264(2) 0.0217(2) 0.0236(2) -0.00032(19) -0.0018(2) -0.00048(18) Cl2 0.0446(3) 0.0294(3) 0.0340(3) -0.0039(2) -0.0131(2) -0.0020(2) Cl3 0.0499(3) 0.0381(3) 0.0358(3) 0.0077(2) 0.0136(3) -0.0030(2) Cl1 0.0330(2) 0.0244(2) 0.0425(3) -0.0027(2) -0.0006(3) 0.00325(18) B1 0.0336(11) 0.0262(11) 0.0255(10) 0.0010(9) -0.0016(10) -0.0003(9) C31 0.0325(10) 0.0258(10) 0.0356(12) 0.0012(8) 0.0063(9) 0.0015(8) C21 0.0389(12) 0.0346(11) 0.0265(11) -0.0045(9) 0.0033(9) 0.0024(10) C11 0.0412(13) 0.0331(12) 0.0450(13) 0.0040(10) -0.0138(11) -0.0068(10) C32 0.0354(13) 0.0435(14) 0.070(2) 0.0087(13) 0.0070(13) 0.0097(11) C22 0.0562(16) 0.0369(13) 0.0351(13) 0.0038(10) 0.0103(11) -0.0023(11) C12 0.0673(19) 0.0406(16) 0.0560(19) -0.0069(13) -0.0293(15) -0.0054(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 P1 C31 1.781(2) . ? P1 C11 1.786(2) . ? P1 C21 1.786(2) . ? P1 B1 1.970(2) . ? Cl2 B1 1.847(2) . ? Cl3 B1 1.845(2) . ? Cl1 B1 1.841(3) . ? C31 C32 1.316(4) . ? C31 H31A 0.89(3) . ? C21 C22 1.320(3) . ? C21 H21A 0.95(3) . ? C11 C12 1.322(4) . ? C11 H11A 1.01(3) . ? C32 H32B 1.03(4) . ? C32 H32A 0.98(4) . ? C22 H22B 0.99(3) . ? C22 H22A 1.03(3) . ? C12 H12A 0.95(4) . ? C12 H12B 1.02(4) . ? 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 C31 P1 C11 108.75(12) . . ? C31 P1 C21 108.47(11) . . ? C11 P1 C21 108.84(12) . . ? C31 P1 B1 110.36(11) . . ? C11 P1 B1 109.93(11) . . ? C21 P1 B1 110.45(11) . . ? Cl1 B1 Cl3 110.94(12) . . ? Cl1 B1 Cl2 112.51(12) . . ? Cl3 B1 Cl2 111.46(13) . . ? Cl1 B1 P1 107.56(12) . . ? Cl3 B1 P1 107.73(11) . . ? Cl2 B1 P1 106.34(11) . . ? C32 C31 P1 123.0(2) . . ? C32 C31 H31A 123.1(17) . . ? P1 C31 H31A 113.9(17) . . ? C22 C21 P1 123.6(2) . . ? C22 C21 H21A 120.1(18) . . ? P1 C21 H21A 116.2(18) . . ? C12 C11 P1 123.6(3) . . ? C12 C11 H11A 124.0(17) . . ? P1 C11 H11A 112.3(17) . . ? C31 C32 H32B 117(2) . . ? C31 C32 H32A 119.3(19) . . ? H32B C32 H32A 123(3) . . ? C21 C22 H22B 118.7(18) . . ? C21 C22 H22A 120.7(17) . . ? H22B C22 H22A 121(2) . . ? C11 C12 H12A 118(3) . . ? C11 C12 H12B 122(2) . . ? H12A C12 H12B 119(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 C31 P1 B1 Cl1 171.94(11) . . . . ? C11 P1 B1 Cl1 -68.12(15) . . . . ? C21 P1 B1 Cl1 52.00(14) . . . . ? C31 P1 B1 Cl3 -68.41(14) . . . . ? C11 P1 B1 Cl3 51.53(16) . . . . ? C21 P1 B1 Cl3 171.65(11) . . . . ? C31 P1 B1 Cl2 51.20(14) . . . . ? C11 P1 B1 Cl2 171.14(13) . . . . ? C21 P1 B1 Cl2 -68.74(14) . . . . ? C11 P1 C31 C32 8.3(3) . . . . ? C21 P1 C31 C32 -110.0(2) . . . . ? B1 P1 C31 C32 128.9(2) . . . . ? C31 P1 C21 C22 10.5(3) . . . . ? C11 P1 C21 C22 -107.6(2) . . . . ? B1 P1 C21 C22 131.6(2) . . . . ? C31 P1 C11 C12 -113.5(3) . . . . ? C21 P1 C11 C12 4.5(3) . . . . ? B1 P1 C11 C12 125.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.70 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.209 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.049 #===END data_uwe10 _database_code_CSD 197161 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H9 B Br3 P' _chemical_formula_weight 362.64 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' P P 0.1023 0.0942 '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 P2(1)/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 6.95430(10) _cell_length_b 11.3363(2) _cell_length_c 14.5709(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.1093(10) _cell_angle_gamma 90.00 _cell_volume 1147.02(3) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 45210 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.100 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 10.633 _exptl_absorpt_correction_type delabs _exptl_absorpt_correction_T_min 0.244 _exptl_absorpt_correction_T_max 0.703 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'Nonius DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45210 _diffrn_reflns_av_R_equivalents 0.050 _diffrn_reflns_av_sigmaI/netI 0.0465 _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 -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 31.90 _reflns_number_total 3930 _reflns_number_gt 3467 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0000P)^2^+0.3640P] 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 isotropic _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3930 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0680 _refine_ls_wR_factor_gt 0.0649 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.75892(7) 0.74822(4) 0.52799(4) 0.02137(10) Uani 1 1 d . . . B1 B 0.6980(3) 0.73636(19) 0.39598(16) 0.0241(4) Uani 1 1 d . . . Br1 Br 0.78086(3) 0.575373(19) 0.357258(15) 0.03210(7) Uani 1 1 d . . . Br2 Br 0.41227(3) 0.75894(2) 0.376100(16) 0.03273(7) Uani 1 1 d . . . Br3 Br 0.84628(4) 0.86312(2) 0.334877(17) 0.03800(7) Uani 1 1 d . . . C11 C 1.0121(3) 0.7311(2) 0.55300(17) 0.0319(4) Uani 1 1 d . . . H11 H 1.079(5) 0.667(3) 0.517(2) 0.053(9) Uiso 1 1 d . . . C12 C 1.1089(4) 0.7945(3) 0.6161(2) 0.0464(6) Uani 1 1 d . . . H12B H 1.046(6) 0.856(3) 0.652(3) 0.074(12) Uiso 1 1 d . . . H12A H 1.245(7) 0.793(4) 0.626(3) 0.080(13) Uiso 1 1 d . . . C21 C 0.6360(3) 0.63412(18) 0.58654(15) 0.0269(4) Uani 1 1 d . . . H21 H 0.502(6) 0.623(3) 0.563(3) 0.064(11) Uiso 1 1 d . . . C22 C 0.7179(4) 0.5725(2) 0.65482(18) 0.0359(5) Uani 1 1 d . . . H22B H 0.649(4) 0.511(3) 0.682(2) 0.033(7) Uiso 1 1 d . . . H22A H 0.850(5) 0.586(3) 0.674(2) 0.036(7) Uiso 1 1 d . . . C31 C 0.6849(3) 0.88828(19) 0.57147(17) 0.0300(4) Uani 1 1 d . . . H31 H 0.708(5) 0.951(3) 0.529(2) 0.046(8) Uiso 1 1 d . . . C32 C 0.6043(4) 0.9004(2) 0.65082(18) 0.0345(5) Uani 1 1 d . . . H32B H 0.579(4) 0.835(3) 0.689(2) 0.041(8) Uiso 1 1 d . . . H32A H 0.551(5) 0.979(3) 0.668(3) 0.064(11) 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 P1 0.0209(2) 0.0214(2) 0.0220(2) 0.00035(17) 0.00242(17) -0.00013(16) B1 0.0258(10) 0.0244(10) 0.0226(10) 0.0016(8) 0.0037(8) 0.0005(8) Br1 0.03767(13) 0.02793(11) 0.03127(12) -0.00559(8) 0.00720(9) 0.00394(8) Br2 0.02731(12) 0.03660(12) 0.03369(13) 0.00103(8) -0.00383(8) 0.00411(8) Br3 0.04585(15) 0.03475(13) 0.03425(13) 0.01030(9) 0.00993(10) -0.00590(9) C11 0.0230(10) 0.0404(11) 0.0321(11) 0.0022(9) 0.0005(8) 0.0013(8) C12 0.0283(12) 0.0635(18) 0.0468(15) -0.0041(13) -0.0038(10) -0.0080(12) C21 0.0279(10) 0.0252(9) 0.0278(10) 0.0009(7) 0.0045(7) -0.0031(7) C22 0.0414(13) 0.0334(11) 0.0332(12) 0.0085(9) 0.0043(10) -0.0030(9) C31 0.0342(11) 0.0221(8) 0.0339(11) -0.0030(8) 0.0032(8) -0.0005(8) C32 0.0349(12) 0.0335(11) 0.0352(12) -0.0097(10) 0.0030(9) 0.0037(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C11 1.789(2) . ? P1 C21 1.792(2) . ? P1 C31 1.795(2) . ? P1 B1 1.952(2) . ? B1 Br1 2.004(2) . ? B1 Br3 2.005(2) . ? B1 Br2 2.009(2) . ? C11 C12 1.322(4) . ? C11 H11 1.02(4) . ? C12 H12B 0.99(4) . ? C12 H12A 0.95(5) . ? C21 C22 1.319(3) . ? C21 H21 0.98(4) . ? C22 H22B 0.95(3) . ? C22 H22A 0.96(3) . ? C31 C32 1.319(3) . ? C31 H31 0.96(3) . ? C32 H32B 0.96(3) . ? C32 H32A 1.00(4) . ? 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 P1 C21 108.33(11) . . ? C11 P1 C31 108.76(11) . . ? C21 P1 C31 108.48(11) . . ? C11 P1 B1 110.61(11) . . ? C21 P1 B1 109.63(10) . . ? C31 P1 B1 110.96(10) . . ? P1 B1 Br1 106.84(11) . . ? P1 B1 Br3 107.39(11) . . ? Br1 B1 Br3 111.40(11) . . ? P1 B1 Br2 107.07(11) . . ? Br1 B1 Br2 111.89(11) . . ? Br3 B1 Br2 111.91(11) . . ? C12 C11 P1 122.8(2) . . ? C12 C11 H11 121(2) . . ? P1 C11 H11 116(2) . . ? C11 C12 H12B 122(2) . . ? C11 C12 H12A 124(3) . . ? H12B C12 H12A 113(4) . . ? C22 C21 P1 122.93(19) . . ? C22 C21 H21 124(2) . . ? P1 C21 H21 113(2) . . ? C21 C22 H22B 120.0(17) . . ? C21 C22 H22A 120.3(18) . . ? H22B C22 H22A 120(2) . . ? C32 C31 P1 123.03(19) . . ? C32 C31 H31 125.4(19) . . ? P1 C31 H31 111.6(19) . . ? C31 C32 H32B 122.3(19) . . ? C31 C32 H32A 119(2) . . ? H32B C32 H32A 118(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 C11 P1 B1 Br1 60.73(14) . . . . ? C21 P1 B1 Br1 -58.67(13) . . . . ? C31 P1 B1 Br1 -178.48(10) . . . . ? C11 P1 B1 Br3 -58.90(14) . . . . ? C21 P1 B1 Br3 -178.30(10) . . . . ? C31 P1 B1 Br3 61.90(13) . . . . ? C11 P1 B1 Br2 -179.25(10) . . . . ? C21 P1 B1 Br2 61.35(13) . . . . ? C31 P1 B1 Br2 -58.45(13) . . . . ? C21 P1 C11 C12 -99.3(3) . . . . ? C31 P1 C11 C12 18.4(3) . . . . ? B1 P1 C11 C12 140.5(2) . . . . ? C11 P1 C21 C22 17.1(2) . . . . ? C31 P1 C21 C22 -100.9(2) . . . . ? B1 P1 C21 C22 137.8(2) . . . . ? C11 P1 C31 C32 -98.5(2) . . . . ? C21 P1 C31 C32 19.1(3) . . . . ? B1 P1 C31 C32 139.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 31.90 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.644 _refine_diff_density_min -0.821 _refine_diff_density_rms 0.104 #===END data_uwe7 _database_code_CSD 197162 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H9 B I3 P' _chemical_formula_weight 503.61 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.25000(10) _cell_length_b 11.8070(2) _cell_length_c 15.1560(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.6730(8) _cell_angle_gamma 90.00 _cell_volume 1293.05(4) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 33405 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 7.326 _exptl_absorpt_correction_type delabs _exptl_absorpt_correction_T_min 0.444 _exptl_absorpt_correction_T_max 0.816 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'NONIUS DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33405 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.73 _reflns_number_total 3029 _reflns_number_gt 2884 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0000P)^2^+1.8809P] 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 isotropic _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3029 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0706 _refine_ls_wR_factor_gt 0.0694 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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 I1 I 0.71296(4) 0.43011(2) 0.628455(18) 0.03832(10) Uani 1 1 d . . . I2 I 1.11074(4) 0.23713(2) 0.610147(18) 0.03735(9) Uani 1 1 d . . . I3 I 0.65092(4) 0.12246(3) 0.64864(2) 0.04342(10) Uani 1 1 d . . . P1 P 0.74589(14) 0.25077(8) 0.45898(6) 0.0278(2) Uani 1 1 d . . . C21 C 0.8596(7) 0.3624(4) 0.4050(3) 0.0357(9) Uani 1 1 d . . . C11 C 0.5023(6) 0.2643(4) 0.4323(3) 0.0384(9) Uani 1 1 d . . . B1 B 0.8061(6) 0.2602(4) 0.5861(3) 0.0290(8) Uani 1 1 d . . . C31 C 0.8216(7) 0.1187(4) 0.4152(3) 0.0412(10) Uani 1 1 d . . . C22 C 0.7785(8) 0.4228(4) 0.3387(3) 0.0434(10) Uani 1 1 d . . . C32 C 0.9048(7) 0.1106(5) 0.3413(3) 0.0460(11) Uani 1 1 d . . . C12 C 0.4102(8) 0.2084(5) 0.3670(4) 0.0525(12) Uani 1 1 d . . . H111 H 0.445(7) 0.313(4) 0.475(3) 0.039(12) Uiso 1 1 d . . . H122 H 0.270(7) 0.215(4) 0.354(3) 0.033(12) Uiso 1 1 d . . . H121 H 0.466(9) 0.162(5) 0.328(4) 0.063(18) Uiso 1 1 d . . . H321 H 0.938(8) 0.184(6) 0.307(4) 0.066(17) Uiso 1 1 d . . . H221 H 0.649(8) 0.406(5) 0.318(4) 0.052(15) Uiso 1 1 d . . . H222 H 0.860(8) 0.479(5) 0.304(4) 0.052(15) Uiso 1 1 d . . . H322 H 0.963(8) 0.034(5) 0.317(4) 0.065(17) Uiso 1 1 d . . . H311 H 0.819(8) 0.066(5) 0.441(4) 0.052(17) Uiso 1 1 d . . . H211 H 0.990(9) 0.376(5) 0.425(4) 0.066(18) 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 I1 0.04639(18) 0.03317(16) 0.03615(16) -0.00520(10) 0.00791(12) 0.00603(11) I2 0.03031(15) 0.04393(17) 0.03721(16) 0.00211(11) -0.00084(11) 0.00368(11) I3 0.04253(17) 0.04106(17) 0.04755(18) 0.01845(12) 0.00902(13) -0.00074(12) P1 0.0313(5) 0.0245(4) 0.0276(5) 0.0010(3) 0.0018(4) 0.0012(4) C21 0.044(2) 0.034(2) 0.0297(19) 0.0029(16) 0.0047(17) -0.0040(18) C11 0.036(2) 0.039(2) 0.039(2) 0.0022(18) 0.0000(18) 0.0010(18) B1 0.031(2) 0.028(2) 0.028(2) 0.0013(16) 0.0020(17) 0.0010(16) C31 0.055(3) 0.029(2) 0.040(2) -0.0042(18) 0.003(2) 0.005(2) C22 0.056(3) 0.039(2) 0.036(2) 0.0107(18) 0.008(2) 0.005(2) C32 0.051(3) 0.045(3) 0.041(2) -0.011(2) 0.002(2) 0.008(2) C12 0.045(3) 0.061(3) 0.049(3) -0.002(3) -0.009(2) -0.011(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 B1 2.228(4) . ? I2 B1 2.226(5) . ? I3 B1 2.232(4) . ? P1 C11 1.787(5) . ? P1 C21 1.787(4) . ? P1 C31 1.798(5) . ? P1 B1 1.944(4) . ? C21 C22 1.330(6) . ? C21 H211 0.98(6) . ? C11 C12 1.324(7) . ? C11 H111 0.98(5) . ? C31 C32 1.318(7) . ? C31 H311 0.73(6) . ? C22 H221 0.98(6) . ? C22 H222 1.05(6) . ? C32 H321 1.05(6) . ? C32 H322 1.07(6) . ? C12 H122 1.02(5) . ? C12 H121 0.93(6) . ? 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 P1 C21 108.4(2) . . ? C11 P1 C31 108.7(2) . . ? C21 P1 C31 107.7(2) . . ? C11 P1 B1 110.9(2) . . ? C21 P1 B1 109.70(19) . . ? C31 P1 B1 111.4(2) . . ? C22 C21 P1 123.3(4) . . ? C22 C21 H211 120(4) . . ? P1 C21 H211 116(4) . . ? C12 C11 P1 123.6(4) . . ? C12 C11 H111 125(3) . . ? P1 C11 H111 112(3) . . ? P1 B1 I2 107.2(2) . . ? P1 B1 I1 106.74(19) . . ? I2 B1 I1 112.50(19) . . ? P1 B1 I3 107.4(2) . . ? I2 B1 I3 111.67(18) . . ? I1 B1 I3 111.02(19) . . ? C32 C31 P1 123.4(4) . . ? C32 C31 H311 115(5) . . ? P1 C31 H311 121(5) . . ? C21 C22 H221 118(3) . . ? C21 C22 H222 119(3) . . ? H221 C22 H222 122(4) . . ? C31 C32 H321 120(3) . . ? C31 C32 H322 125(3) . . ? H321 C32 H322 114(5) . . ? C11 C12 H122 122(3) . . ? C11 C12 H121 124(4) . . ? H122 C12 H121 114(4) . . ? 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 C11 P1 C21 C22 -16.6(5) . . . . ? C31 P1 C21 C22 100.8(4) . . . . ? B1 P1 C21 C22 -137.8(4) . . . . ? C21 P1 C11 C12 95.4(5) . . . . ? C31 P1 C11 C12 -21.4(5) . . . . ? B1 P1 C11 C12 -144.1(4) . . . . ? C11 P1 B1 I2 178.40(19) . . . . ? C21 P1 B1 I2 -61.9(2) . . . . ? C31 P1 B1 I2 57.2(3) . . . . ? C11 P1 B1 I1 -60.9(2) . . . . ? C21 P1 B1 I1 58.8(3) . . . . ? C31 P1 B1 I1 178.0(2) . . . . ? C11 P1 B1 I3 58.3(2) . . . . ? C21 P1 B1 I3 177.9(2) . . . . ? C31 P1 B1 I3 -62.9(3) . . . . ? C11 P1 C31 C32 101.0(5) . . . . ? C21 P1 C31 C32 -16.2(5) . . . . ? B1 P1 C31 C32 -136.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.73 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.006 _refine_diff_density_min -1.002 _refine_diff_density_rms 0.124 #===END data_uwe18 _database_code_CSD 197163 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H15 B F3 P' _chemical_formula_weight 185.96 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.42400(10) _cell_length_b 9.2453(2) _cell_length_c 16.2097(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 962.72(3) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 30675 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'NONIUS DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30675 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.68 _reflns_number_total 2207 _reflns_number_gt 2199 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-PLUS _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Structure was refined as racemic twin. Contribution of one specimen to the racemic twin: 0.47(8) ; _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^)+(0.0602P)^2^+0.0746P] 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 isotropic _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 0.47(8) _refine_ls_number_reflns 2207 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0797 _refine_ls_wR_factor_gt 0.0797 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 -0.31994(4) -0.01493(3) -0.341697(18) 0.02490(11) Uani 1 1 d . . . F1 F -0.71028(15) 0.06342(13) -0.40263(7) 0.0540(3) Uani 1 1 d . . . F2 F -0.69879(13) -0.16209(9) -0.34753(5) 0.0392(2) Uani 1 1 d . . . F3 F -0.70061(14) 0.03345(11) -0.26327(6) 0.0452(2) Uani 1 1 d . . . C11 C -0.2184(2) 0.16842(14) -0.34119(9) 0.0329(3) Uani 1 1 d . . . C12 C -0.2717(3) 0.2548(2) -0.41842(12) 0.0495(4) Uani 1 1 d . . . C21 C -0.2205(2) -0.10379(17) -0.43371(9) 0.0363(3) Uani 1 1 d . . . C22 C -0.2469(3) -0.26830(19) -0.43206(12) 0.0441(4) Uani 1 1 d . . . C31 C -0.2055(2) -0.10784(15) -0.25412(8) 0.0321(3) Uani 1 1 d . . . C32 C -0.2451(3) -0.0339(2) -0.17129(9) 0.0460(4) Uani 1 1 d . . . B1 B -0.6354(2) -0.01988(15) -0.33863(9) 0.0294(3) Uani 1 1 d . . . H21B H -0.298(3) -0.0594(19) -0.4778(12) 0.042(5) Uiso 1 1 d . . . H31B H -0.262(3) -0.207(2) -0.2549(11) 0.040(5) Uiso 1 1 d . . . H11B H -0.068(3) 0.158(2) -0.3351(11) 0.045(5) Uiso 1 1 d . . . H21A H -0.080(3) -0.079(2) -0.4405(12) 0.042(5) Uiso 1 1 d . . . H11A H -0.292(3) 0.215(2) -0.2895(12) 0.047(5) Uiso 1 1 d . . . H32C H -0.387(4) -0.025(2) -0.1636(14) 0.065(7) Uiso 1 1 d . . . H12C H -0.195(4) 0.210(2) -0.4674(14) 0.064(6) Uiso 1 1 d . . . H31A H -0.053(3) -0.110(2) -0.2655(12) 0.051(6) Uiso 1 1 d . . . H22C H -0.211(4) -0.306(3) -0.4844(16) 0.074(7) Uiso 1 1 d . . . H22B H -0.388(4) -0.293(2) -0.4201(12) 0.046(5) Uiso 1 1 d . . . H12B H -0.429(5) 0.263(3) -0.4287(15) 0.068(7) Uiso 1 1 d . . . H32B H -0.195(4) 0.069(3) -0.1675(14) 0.064(6) Uiso 1 1 d . . . H12A H -0.210(6) 0.357(3) -0.4120(19) 0.105(11) Uiso 1 1 d . . . H32A H -0.209(3) -0.095(2) -0.1241(13) 0.054(6) Uiso 1 1 d . . . H22A H -0.150(4) -0.308(3) -0.3862(14) 0.066(7) 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 P1 0.02034(15) 0.02868(15) 0.02566(17) -0.00105(11) -0.00030(10) -0.00039(10) F1 0.0290(4) 0.0676(6) 0.0654(6) 0.0327(5) -0.0104(4) -0.0027(4) F2 0.0317(4) 0.0356(4) 0.0504(5) -0.0055(3) 0.0046(4) -0.0079(3) F3 0.0306(4) 0.0553(5) 0.0498(5) -0.0182(4) 0.0091(3) -0.0003(4) C11 0.0289(6) 0.0323(6) 0.0376(6) 0.0007(5) -0.0017(5) -0.0033(4) C12 0.0537(10) 0.0447(8) 0.0502(9) 0.0171(7) -0.0028(7) -0.0114(7) C21 0.0309(7) 0.0460(7) 0.0320(7) -0.0074(5) 0.0026(5) -0.0010(6) C22 0.0438(9) 0.0432(8) 0.0454(8) -0.0170(6) 0.0028(6) 0.0048(6) C31 0.0293(7) 0.0343(6) 0.0327(6) 0.0022(5) -0.0025(5) 0.0032(5) C32 0.0563(10) 0.0526(9) 0.0291(7) -0.0013(6) -0.0067(6) 0.0092(7) B1 0.0211(5) 0.0325(6) 0.0347(7) 0.0020(6) 0.0001(5) -0.0003(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 C31 1.8140(13) . ? P1 C11 1.8162(13) . ? P1 C21 1.8197(14) . ? P1 B1 2.0280(14) . ? F1 B1 1.3781(17) . ? F2 B1 1.3838(15) . ? F3 B1 1.3828(16) . ? C11 C12 1.523(2) . ? C11 H11B 0.98(2) . ? C11 H11A 1.05(2) . ? C12 H12C 1.02(2) . ? C12 H12B 1.03(3) . ? C12 H12A 1.03(3) . ? C21 C22 1.531(2) . ? C21 H21B 0.961(19) . ? C21 H21A 0.94(2) . ? C22 H22C 0.95(3) . ? C22 H22B 0.95(2) . ? C22 H22A 1.04(2) . ? C31 C32 1.5281(19) . ? C31 H31B 0.99(2) . ? C31 H31A 1.00(2) . ? C32 H32C 0.92(3) . ? C32 H32B 1.01(2) . ? C32 H32A 0.98(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 C31 P1 C11 107.06(6) . . ? C31 P1 C21 106.57(6) . . ? C11 P1 C21 107.37(7) . . ? C31 P1 B1 111.96(6) . . ? C11 P1 B1 112.32(6) . . ? C21 P1 B1 111.24(6) . . ? C12 C11 P1 113.92(11) . . ? C12 C11 H11B 110.8(11) . . ? P1 C11 H11B 105.5(11) . . ? C12 C11 H11A 109.9(10) . . ? P1 C11 H11A 102.8(10) . . ? H11B C11 H11A 113.8(16) . . ? C11 C12 H12C 108.6(13) . . ? C11 C12 H12B 113.1(14) . . ? H12C C12 H12B 112.4(19) . . ? C11 C12 H12A 108.2(17) . . ? H12C C12 H12A 105(2) . . ? H12B C12 H12A 109(2) . . ? C22 C21 P1 113.28(11) . . ? C22 C21 H21B 112.3(11) . . ? P1 C21 H21B 103.6(12) . . ? C22 C21 H21A 110.6(12) . . ? P1 C21 H21A 109.0(12) . . ? H21B C21 H21A 107.7(16) . . ? C21 C22 H22C 109.1(14) . . ? C21 C22 H22B 110.3(12) . . ? H22C C22 H22B 109(2) . . ? C21 C22 H22A 107.1(14) . . ? H22C C22 H22A 111.5(19) . . ? H22B C22 H22A 109.9(19) . . ? C32 C31 P1 114.07(10) . . ? C32 C31 H31B 111.4(10) . . ? P1 C31 H31B 106.5(11) . . ? C32 C31 H31A 109.7(11) . . ? P1 C31 H31A 105.2(11) . . ? H31B C31 H31A 109.7(17) . . ? C31 C32 H32C 108.9(14) . . ? C31 C32 H32B 115.0(13) . . ? H32C C32 H32B 103.0(19) . . ? C31 C32 H32A 112.9(12) . . ? H32C C32 H32A 100.3(19) . . ? H32B C32 H32A 114.9(18) . . ? F1 B1 F3 111.10(12) . . ? F1 B1 F2 110.50(12) . . ? F3 B1 F2 109.97(11) . . ? F1 B1 P1 108.44(9) . . ? F3 B1 P1 108.53(9) . . ? F2 B1 P1 108.22(8) . . ? 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 C31 P1 C11 C12 170.80(12) . . . . ? C21 P1 C11 C12 56.68(14) . . . . ? B1 P1 C11 C12 -65.91(13) . . . . ? C31 P1 C21 C22 51.16(13) . . . . ? C11 P1 C21 C22 165.60(11) . . . . ? B1 P1 C21 C22 -71.13(13) . . . . ? C11 P1 C31 C32 56.58(13) . . . . ? C21 P1 C31 C32 171.23(12) . . . . ? B1 P1 C31 C32 -66.93(13) . . . . ? C31 P1 B1 F1 174.68(10) . . . . ? C11 P1 B1 F1 54.19(12) . . . . ? C21 P1 B1 F1 -66.20(12) . . . . ? C31 P1 B1 F3 53.89(11) . . . . ? C11 P1 B1 F3 -66.61(11) . . . . ? C21 P1 B1 F3 173.01(10) . . . . ? C31 P1 B1 F2 -65.42(11) . . . . ? C11 P1 B1 F2 174.09(8) . . . . ? C21 P1 B1 F2 53.70(11) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.68 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.141 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.047