# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Petr Kilian' 'Alexandra Slawin' 'Piotr Wawrzyniak' 'J. Woollins' _publ_contact_author_name 'Petr Kilian' _publ_contact_author_email PK7@ST-ANDREWS.AC.UK _publ_section_title ; Syntheses and characterization of bis(trifluoromethyl)phosphino naphthalenes and acenaphthenes ; # Attachment '10.cif' data_piotr4 _database_code_depnum_ccdc_archive 'CCDC 743890' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 Br F6 P' _chemical_formula_sum 'C14 H8 Br F6 P' _chemical_formula_weight 401.08 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' 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' 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)/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 7.097(5) _cell_length_b 9.591(7) _cell_length_c 20.681(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.920(12) _cell_angle_gamma 90.00 _cell_volume 1402.5(16) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3881 _cell_measurement_theta_min 2.3421 _cell_measurement_theta_max 28.2238 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.0200 _exptl_crystal_size_min 0.0100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.900 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 3.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8513 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type ? _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13150 _diffrn_reflns_av_R_equivalents 0.1127 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.38 _reflns_number_total 2525 _reflns_number_gt 2380 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1147P)^2^+64.4000P] 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 0.007(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2525 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1499 _refine_ls_R_factor_gt 0.1457 _refine_ls_wR_factor_ref 0.3526 _refine_ls_wR_factor_gt 0.3501 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _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 0.1786(6) 0.8534(4) 0.6325(2) 0.0292(10) Uani 1 1 d . . . C1 C 0.235(2) 0.6744(15) 0.6118(8) 0.028(3) Uani 1 1 d . . . C2 C 0.254(2) 0.5726(16) 0.6600(8) 0.029(4) Uani 1 1 d . . . H2A H 0.2565 0.6032 0.7038 0.034 Uiso 1 1 calc R . . C3 C 0.269(2) 0.4271(17) 0.6492(8) 0.029(3) Uani 1 1 d . . . H3A H 0.2845 0.3624 0.6840 0.034 Uiso 1 1 calc R . . C4 C 0.260(2) 0.3846(14) 0.5845(8) 0.024(3) Uani 1 1 d . . . C5 C 0.250(2) 0.4813(15) 0.5355(7) 0.020(3) Uani 1 1 d . . . C6 C 0.247(2) 0.4161(15) 0.4734(7) 0.023(3) Uani 1 1 d . . . C7 C 0.242(2) 0.4987(15) 0.4193(8) 0.028(3) Uani 1 1 d . . . H7A H 0.2390 0.4579 0.3774 0.033 Uiso 1 1 calc R . . C8 C 0.240(2) 0.6408(16) 0.4262(7) 0.026(3) Uani 1 1 d . . . H8A H 0.2424 0.6965 0.3883 0.031 Uiso 1 1 calc R . . C9 C 0.236(2) 0.7059(16) 0.4840(8) 0.028(3) Uani 1 1 d . . . C10 C 0.2381(19) 0.6291(16) 0.5435(8) 0.025(3) Uani 1 1 d . . . Br9 Br 0.2412(2) 0.90475(15) 0.48337(8) 0.0291(6) Uani 1 1 d . . . C11 C 0.413(3) 0.9089(17) 0.6772(8) 0.034(4) Uani 1 1 d . . . F1 F 0.5352(15) 0.9397(12) 0.6349(6) 0.048(3) Uani 1 1 d . . . F2 F 0.3852(18) 1.0187(13) 0.7136(6) 0.055(3) Uani 1 1 d . . . F3 F 0.4954(17) 0.8131(12) 0.7170(6) 0.055(3) Uani 1 1 d . . . C12 C 0.053(2) 0.8345(19) 0.7076(9) 0.034(4) Uani 1 1 d . . . F4 F -0.0242(19) 0.9609(12) 0.7212(6) 0.059(3) Uani 1 1 d . . . F5 F 0.1376(19) 0.7873(13) 0.7623(5) 0.054(3) Uani 1 1 d . . . F6 F -0.1012(17) 0.7502(13) 0.6944(6) 0.054(3) Uani 1 1 d . . . C13 C 0.270(2) 0.2433(19) 0.5564(7) 0.028(3) Uani 1 1 d . . . H13A H 0.1607 0.1865 0.5675 0.033 Uiso 1 1 calc R . . H13B H 0.3877 0.1960 0.5736 0.033 Uiso 1 1 calc R . . C14 C 0.267(2) 0.2606(18) 0.4842(9) 0.035(4) Uani 1 1 d . . . H14A H 0.1586 0.2101 0.4618 0.042 Uiso 1 1 calc R . . H14B H 0.3855 0.2255 0.4682 0.042 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 0.036(2) 0.020(2) 0.032(2) -0.0053(17) 0.0031(17) 0.0021(17) C1 0.041(9) 0.010(7) 0.034(8) 0.002(6) 0.011(7) 0.002(6) C2 0.040(9) 0.018(8) 0.029(8) -0.012(6) 0.007(7) 0.008(7) C3 0.027(8) 0.025(8) 0.033(8) 0.012(7) 0.002(6) 0.009(6) C4 0.024(7) 0.009(6) 0.039(9) 0.011(6) 0.003(6) 0.000(5) C5 0.018(7) 0.020(7) 0.022(7) 0.004(6) -0.005(6) -0.001(6) C6 0.022(7) 0.020(8) 0.028(8) 0.005(6) 0.007(6) 0.001(6) C7 0.033(9) 0.013(7) 0.037(9) -0.004(6) 0.002(7) 0.001(6) C8 0.034(9) 0.018(7) 0.024(8) 0.002(6) -0.008(6) -0.004(6) C9 0.034(9) 0.014(7) 0.036(9) 0.000(6) 0.005(7) 0.012(6) C10 0.008(6) 0.027(8) 0.039(9) 0.001(7) 0.004(6) -0.004(6) Br9 0.0350(10) 0.0150(8) 0.0378(10) 0.0019(6) 0.0061(7) 0.0005(6) C11 0.046(10) 0.023(8) 0.031(9) -0.009(7) -0.001(7) 0.001(7) F1 0.038(6) 0.049(7) 0.059(7) -0.004(6) 0.011(5) -0.012(5) F2 0.069(8) 0.048(7) 0.047(7) -0.020(6) 0.004(6) -0.004(6) F3 0.058(7) 0.045(7) 0.059(7) 0.001(6) -0.016(6) 0.009(6) C12 0.029(9) 0.033(9) 0.042(10) -0.012(8) 0.008(7) -0.018(7) F4 0.073(9) 0.037(6) 0.070(8) -0.019(6) 0.029(7) 0.006(6) F5 0.074(8) 0.046(7) 0.042(6) -0.006(5) 0.015(6) -0.013(6) F6 0.052(7) 0.048(7) 0.065(8) -0.019(6) 0.023(6) -0.017(6) C13 0.013(7) 0.047(10) 0.023(7) -0.002(7) -0.001(6) 0.005(6) C14 0.026(9) 0.026(9) 0.049(10) 0.002(8) -0.018(8) 0.015(7) _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 C1 1.823(15) . ? P1 C12 1.865(18) . ? P1 C11 1.906(18) . ? C1 C2 1.39(2) . ? C1 C10 1.48(2) . ? C2 C3 1.42(2) . ? C2 H2A 0.9500 . ? C3 C4 1.40(2) . ? C3 H3A 0.9500 . ? C4 C5 1.37(2) . ? C4 C13 1.48(2) . ? C5 C6 1.43(2) . ? C5 C10 1.43(2) . ? C6 C7 1.37(2) . ? C6 C14 1.51(2) . ? C7 C8 1.37(2) . ? C7 H7A 0.9500 . ? C8 C9 1.35(2) . ? C8 H8A 0.9500 . ? C9 C10 1.43(2) . ? C9 Br9 1.908(15) . ? C11 F2 1.319(19) . ? C11 F1 1.32(2) . ? C11 F3 1.34(2) . ? C12 F5 1.32(2) . ? C12 F6 1.367(19) . ? C12 F4 1.37(2) . ? C13 C14 1.50(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C12 103.6(8) . . ? C1 P1 C11 100.2(8) . . ? C12 P1 C11 94.8(8) . . ? C2 C1 C10 118.0(13) . . ? C2 C1 P1 120.1(12) . . ? C10 C1 P1 121.5(11) . . ? C1 C2 C3 125.5(14) . . ? C1 C2 H2A 117.3 . . ? C3 C2 H2A 117.3 . . ? C4 C3 C2 116.1(14) . . ? C4 C3 H3A 122.0 . . ? C2 C3 H3A 122.0 . . ? C5 C4 C3 120.5(14) . . ? C5 C4 C13 109.3(14) . . ? C3 C4 C13 130.1(13) . . ? C4 C5 C6 111.4(13) . . ? C4 C5 C10 125.7(15) . . ? C6 C5 C10 122.9(13) . . ? C7 C6 C5 118.7(14) . . ? C7 C6 C14 133.4(15) . . ? C5 C6 C14 107.8(13) . . ? C6 C7 C8 119.4(15) . . ? C6 C7 H7A 120.3 . . ? C8 C7 H7A 120.3 . . ? C9 C8 C7 123.5(15) . . ? C9 C8 H8A 118.2 . . ? C7 C8 H8A 118.2 . . ? C8 C9 C10 121.6(14) . . ? C8 C9 Br9 117.0(12) . . ? C10 C9 Br9 121.4(12) . . ? C5 C10 C9 113.9(14) . . ? C5 C10 C1 114.1(13) . . ? C9 C10 C1 132.0(14) . . ? F2 C11 F1 109.8(15) . . ? F2 C11 F3 106.0(14) . . ? F1 C11 F3 106.4(15) . . ? F2 C11 P1 109.6(12) . . ? F1 C11 P1 109.7(11) . . ? F3 C11 P1 115.2(12) . . ? F5 C12 F6 105.4(15) . . ? F5 C12 F4 106.8(14) . . ? F6 C12 F4 103.9(14) . . ? F5 C12 P1 122.1(13) . . ? F6 C12 P1 108.9(11) . . ? F4 C12 P1 108.2(12) . . ? C4 C13 C14 107.0(14) . . ? C4 C13 H13A 110.3 . . ? C14 C13 H13A 110.3 . . ? C4 C13 H13B 110.3 . . ? C14 C13 H13B 110.3 . . ? H13A C13 H13B 108.6 . . ? C13 C14 C6 104.5(14) . . ? C13 C14 H14A 110.9 . . ? C6 C14 H14A 110.9 . . ? C13 C14 H14B 110.9 . . ? C6 C14 H14B 110.9 . . ? H14A C14 H14B 108.9 . . ? 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 C12 P1 C1 C2 -25.7(16) . . . . ? C11 P1 C1 C2 71.9(15) . . . . ? C12 P1 C1 C10 146.4(13) . . . . ? C11 P1 C1 C10 -116.1(13) . . . . ? C10 C1 C2 C3 -2(3) . . . . ? P1 C1 C2 C3 170.0(14) . . . . ? C1 C2 C3 C4 -2(3) . . . . ? C2 C3 C4 C5 4(2) . . . . ? C2 C3 C4 C13 -179.8(15) . . . . ? C3 C4 C5 C6 178.2(14) . . . . ? C13 C4 C5 C6 1.6(17) . . . . ? C3 C4 C5 C10 -3(2) . . . . ? C13 C4 C5 C10 179.9(14) . . . . ? C4 C5 C6 C7 -178.6(14) . . . . ? C10 C5 C6 C7 3(2) . . . . ? C4 C5 C6 C14 -2.9(17) . . . . ? C10 C5 C6 C14 178.7(13) . . . . ? C5 C6 C7 C8 0(2) . . . . ? C14 C6 C7 C8 -173.9(17) . . . . ? C6 C7 C8 C9 -3(3) . . . . ? C7 C8 C9 C10 2(3) . . . . ? C7 C8 C9 Br9 178.5(13) . . . . ? C4 C5 C10 C9 177.9(14) . . . . ? C6 C5 C10 C9 -4(2) . . . . ? C4 C5 C10 C1 -1(2) . . . . ? C6 C5 C10 C1 177.6(13) . . . . ? C8 C9 C10 C5 2(2) . . . . ? Br9 C9 C10 C5 -175.0(11) . . . . ? C8 C9 C10 C1 179.8(16) . . . . ? Br9 C9 C10 C1 3(2) . . . . ? C2 C1 C10 C5 3(2) . . . . ? P1 C1 C10 C5 -168.9(11) . . . . ? C2 C1 C10 C9 -174.8(16) . . . . ? P1 C1 C10 C9 13(2) . . . . ? C1 P1 C11 F2 -160.3(12) . . . . ? C12 P1 C11 F2 -55.6(14) . . . . ? C1 P1 C11 F1 79.0(12) . . . . ? C12 P1 C11 F1 -176.2(12) . . . . ? C1 P1 C11 F3 -41.0(14) . . . . ? C12 P1 C11 F3 63.8(14) . . . . ? C1 P1 C12 F5 65.5(15) . . . . ? C11 P1 C12 F5 -36.2(15) . . . . ? C1 P1 C12 F6 -57.6(14) . . . . ? C11 P1 C12 F6 -159.4(13) . . . . ? C1 P1 C12 F4 -170.0(11) . . . . ? C11 P1 C12 F4 88.3(12) . . . . ? C5 C4 C13 C14 0.4(17) . . . . ? C3 C4 C13 C14 -175.8(16) . . . . ? C4 C13 C14 C6 -2.0(17) . . . . ? C7 C6 C14 C13 177.8(16) . . . . ? C5 C6 C14 C13 3.0(17) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 4.951 _refine_diff_density_min -0.979 _refine_diff_density_rms 0.291 # Attachment '16.cif' data_piotr2n _database_code_depnum_ccdc_archive 'CCDC 743891' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 O4' _chemical_formula_sum 'C26 H20 O4' _chemical_formula_weight 396.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1437(15) _cell_length_b 8.3382(18) _cell_length_c 9.720(3) _cell_angle_alpha 86.224(15) _cell_angle_beta 88.075(13) _cell_angle_gamma 80.615(15) _cell_volume 490.1(2) _cell_formula_units_Z 1 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 1476 _cell_measurement_theta_min 2.1003 _cell_measurement_theta_max 28.5637 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.0500 _exptl_crystal_size_min 0.0500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7598 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3236 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0813 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.33 _reflns_number_total 1746 _reflns_number_gt 1158 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1746 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _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 O1 O 0.3117(2) 0.55204(14) 0.35987(14) 0.0250(4) Uani 1 1 d . . . C1 C 0.3682(3) 0.6258(2) 0.2328(2) 0.0219(5) Uani 1 1 d . . . C2 C 0.5577(3) 0.6935(2) 0.2101(2) 0.0246(5) Uani 1 1 d . . . H2A H 0.6598 0.6910 0.2818 0.030 Uiso 1 1 calc R . . C3 C 0.5965(4) 0.7654(2) 0.0803(2) 0.0310(6) Uani 1 1 d . . . H3A H 0.7256 0.8133 0.0631 0.037 Uiso 1 1 calc R . . C4 C 0.4480(4) 0.7676(2) -0.0235(2) 0.0336(6) Uani 1 1 d . . . H4A H 0.4744 0.8178 -0.1117 0.040 Uiso 1 1 calc R . . C5 C 0.2610(4) 0.6966(2) 0.0007(2) 0.0340(6) Uani 1 1 d . . . H5A H 0.1602 0.6972 -0.0714 0.041 Uiso 1 1 calc R . . C6 C 0.2196(3) 0.6249(2) 0.1287(2) 0.0268(5) Uani 1 1 d . . . H6A H 0.0915 0.5757 0.1453 0.032 Uiso 1 1 calc R . . C10 C 0.4397(3) 0.5640(2) 0.4709(2) 0.0213(5) Uani 1 1 d . . . O11 O 0.4320(2) 0.71659(14) 0.51750(14) 0.0240(4) Uani 1 1 d . . . C11 C 0.2407(3) 0.7864(2) 0.5875(2) 0.0200(5) Uani 1 1 d . . . C12 C 0.2384(3) 0.9437(2) 0.6251(2) 0.0241(5) Uani 1 1 d . . . H12A H 0.3603 0.9982 0.6026 0.029 Uiso 1 1 calc R . . C13 C 0.0567(3) 1.0202(2) 0.6957(2) 0.0268(5) Uani 1 1 d . . . H13A H 0.0538 1.1283 0.7220 0.032 Uiso 1 1 calc R . . C14 C -0.1214(3) 0.9421(2) 0.7289(2) 0.0261(5) Uani 1 1 d . . . H14A H -0.2455 0.9956 0.7782 0.031 Uiso 1 1 calc R . . C15 C -0.1174(3) 0.7850(2) 0.6897(2) 0.0256(5) Uani 1 1 d . . . H15A H -0.2399 0.7310 0.7116 0.031 Uiso 1 1 calc R . . C16 C 0.0641(3) 0.7058(2) 0.6186(2) 0.0230(5) Uani 1 1 d . . . H16A H 0.0669 0.5980 0.5918 0.028 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 O1 0.0258(9) 0.0294(8) 0.0214(9) 0.0009(6) -0.0031(7) -0.0098(6) C1 0.0244(12) 0.0209(11) 0.0193(12) 0.0003(8) 0.0012(9) -0.0016(8) C2 0.0234(12) 0.0276(11) 0.0225(13) -0.0009(9) -0.0020(10) -0.0031(9) C3 0.0272(13) 0.0340(12) 0.0304(14) 0.0013(10) 0.0061(11) -0.0037(9) C4 0.0363(15) 0.0399(13) 0.0215(14) 0.0048(10) 0.0022(11) -0.0003(10) C5 0.0337(14) 0.0415(13) 0.0251(14) -0.0030(10) -0.0063(11) 0.0007(10) C6 0.0261(13) 0.0282(11) 0.0263(14) -0.0016(9) -0.0013(10) -0.0049(9) C10 0.0232(12) 0.0228(11) 0.0195(12) -0.0032(8) 0.0011(9) -0.0078(8) O11 0.0231(8) 0.0223(7) 0.0276(9) -0.0056(6) 0.0033(6) -0.0063(6) C11 0.0172(11) 0.0248(11) 0.0165(11) 0.0006(8) -0.0011(9) 0.0001(8) C12 0.0243(12) 0.0250(12) 0.0235(13) 0.0005(9) 0.0005(10) -0.0066(8) C13 0.0310(13) 0.0217(11) 0.0275(13) -0.0048(9) -0.0030(10) -0.0023(9) C14 0.0242(13) 0.0279(11) 0.0255(13) -0.0032(9) 0.0015(10) -0.0014(9) C15 0.0224(12) 0.0301(12) 0.0253(13) 0.0010(9) 0.0007(10) -0.0083(9) C16 0.0246(12) 0.0225(11) 0.0223(12) -0.0020(8) -0.0024(10) -0.0044(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 O1 C10 1.375(2) . ? O1 C1 1.402(2) . ? C1 C2 1.380(3) . ? C1 C6 1.386(3) . ? C2 C3 1.391(3) . ? C2 H2A 0.9500 . ? C3 C4 1.380(3) . ? C3 H3A 0.9500 . ? C4 C5 1.383(3) . ? C4 H4A 0.9500 . ? C5 C6 1.378(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C10 C10 1.304(4) 2_666 ? C10 O11 1.372(2) . ? O11 C11 1.400(2) . ? C11 C16 1.382(3) . ? C11 C12 1.382(2) . ? C12 C13 1.378(3) . ? C12 H12A 0.9500 . ? C13 C14 1.381(3) . ? C13 H13A 0.9500 . ? C14 C15 1.384(3) . ? C14 H14A 0.9500 . ? C15 C16 1.387(3) . ? C15 H15A 0.9500 . ? C16 H16A 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 C10 O1 C1 117.80(15) . . ? C2 C1 C6 121.51(19) . . ? C2 C1 O1 123.47(18) . . ? C6 C1 O1 115.02(17) . . ? C1 C2 C3 118.7(2) . . ? C1 C2 H2A 120.6 . . ? C3 C2 H2A 120.6 . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5A 119.8 . . ? C4 C5 H5A 119.8 . . ? C5 C6 C1 118.9(2) . . ? C5 C6 H6A 120.6 . . ? C1 C6 H6A 120.6 . . ? C10 C10 O11 122.0(2) 2_666 . ? C10 C10 O1 121.3(2) 2_666 . ? O11 C10 O1 116.62(15) . . ? C10 O11 C11 118.34(14) . . ? C16 C11 C12 121.17(18) . . ? C16 C11 O11 123.26(16) . . ? C12 C11 O11 115.57(17) . . ? C13 C12 C11 119.03(19) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 120.96(18) . . ? C12 C13 H13A 119.5 . . ? C14 C13 H13A 119.5 . . ? C13 C14 C15 119.34(19) . . ? C13 C14 H14A 120.3 . . ? C15 C14 H14A 120.3 . . ? C14 C15 C16 120.58(18) . . ? C14 C15 H15A 119.7 . . ? C16 C15 H15A 119.7 . . ? C11 C16 C15 118.91(18) . . ? C11 C16 H16A 120.5 . . ? C15 C16 H16A 120.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 O1 C1 C2 7.3(2) . . . . ? C10 O1 C1 C6 -173.30(15) . . . . ? C6 C1 C2 C3 1.5(3) . . . . ? O1 C1 C2 C3 -179.21(16) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C2 C1 C6 C5 -1.4(3) . . . . ? O1 C1 C6 C5 179.23(15) . . . . ? C1 O1 C10 C10 -113.7(3) . . . 2_666 ? C1 O1 C10 O11 66.9(2) . . . . ? C10 C10 O11 C11 -107.3(3) 2_666 . . . ? O1 C10 O11 C11 72.1(2) . . . . ? C10 O11 C11 C16 3.7(3) . . . . ? C10 O11 C11 C12 -176.58(17) . . . . ? C16 C11 C12 C13 0.4(3) . . . . ? O11 C11 C12 C13 -179.30(17) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? C12 C11 C16 C15 -0.4(3) . . . . ? O11 C11 C16 C15 179.33(17) . . . . ? C14 C15 C16 C11 -0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.214 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.048 # Attachment '7.cif' data_piotr1 _database_code_depnum_ccdc_archive 'CCDC 743892' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H16 Br O2 P' _chemical_formula_sum 'C14 H16 Br O2 P' _chemical_formula_weight 327.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 12.9724(19) _cell_length_b 7.7244(9) _cell_length_c 15.217(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.655(3) _cell_angle_gamma 90.00 _cell_volume 1396.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4913 _cell_measurement_theta_min 2.9227 _cell_measurement_theta_max 28.6015 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.0300 _exptl_crystal_size_mid 0.0300 _exptl_crystal_size_min 0.0200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 3.049 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8775 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8680 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2454 _reflns_number_gt 2217 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.1805P] 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 2454 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0671 _refine_ls_wR_factor_gt 0.0649 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.79238(5) -0.04134(8) 0.49193(4) 0.01752(15) Uani 1 1 d . . . C1 C 0.76219(19) 0.0482(3) 0.59216(17) 0.0174(5) Uani 1 1 d . . . C2 C 0.65114(19) 0.0894(3) 0.57153(16) 0.0209(5) Uani 1 1 d . . . H2A H 0.5975 0.0800 0.5071 0.025 Uiso 1 1 calc R . . C3 C 0.61445(19) 0.1449(3) 0.64245(16) 0.0234(5) Uani 1 1 d . . . H3A H 0.5378 0.1750 0.6255 0.028 Uiso 1 1 calc R . . C4 C 0.68967(19) 0.1549(3) 0.73547(16) 0.0228(5) Uani 1 1 d . . . H4A H 0.6644 0.1873 0.7837 0.027 Uiso 1 1 calc R . . C5 C 0.80461(19) 0.1178(3) 0.76132(15) 0.0191(5) Uani 1 1 d . . . C6 C 0.8800(2) 0.1267(3) 0.85993(16) 0.0237(5) Uani 1 1 d . . . H6A H 0.8524 0.1594 0.9067 0.028 Uiso 1 1 calc R . . C7 C 0.9908(2) 0.0889(3) 0.88764(17) 0.0246(5) Uani 1 1 d . . . H7A H 1.0398 0.0904 0.9537 0.030 Uiso 1 1 calc R . . C8 C 1.0329(2) 0.0476(3) 0.81808(17) 0.0229(5) Uani 1 1 d . . . H8A H 1.1106 0.0222 0.8375 0.027 Uiso 1 1 calc R . . C9 C 0.9631(2) 0.0437(3) 0.72305(16) 0.0188(5) Uani 1 1 d . . . C10 C 0.84485(18) 0.0694(3) 0.68938(15) 0.0164(5) Uani 1 1 d . . . Br9 Br 1.037828(18) 0.02026(3) 0.637896(15) 0.02126(10) Uani 1 1 d . . . O11 O 0.81295(12) -0.2382(2) 0.53664(10) 0.0203(3) Uani 1 1 d . . . C11 C 0.8529(2) -0.3661(3) 0.48825(17) 0.0253(5) Uani 1 1 d . . . H11A H 0.9330 -0.3447 0.5016 0.030 Uiso 1 1 calc R . . H11B H 0.8089 -0.3592 0.4181 0.030 Uiso 1 1 calc R . . C12 C 0.8395(2) -0.5416(3) 0.52430(19) 0.0279(6) Uani 1 1 d . . . H12A H 0.8660 -0.6301 0.4922 0.042 Uiso 1 1 calc R . . H12B H 0.7600 -0.5618 0.5106 0.042 Uiso 1 1 calc R . . H12C H 0.8838 -0.5475 0.5937 0.042 Uiso 1 1 calc R . . O13 O 0.66388(13) -0.0649(2) 0.41067(11) 0.0242(4) Uani 1 1 d . . . C13 C 0.6336(2) 0.0329(3) 0.32270(18) 0.0274(6) Uani 1 1 d . . . H13A H 0.6924 0.1203 0.3304 0.033 Uiso 1 1 calc R . . H13B H 0.5618 0.0946 0.3085 0.033 Uiso 1 1 calc R . . C14 C 0.6213(2) -0.0854(4) 0.24137(17) 0.0381(7) Uani 1 1 d . . . H14A H 0.6008 -0.0178 0.1823 0.057 Uiso 1 1 calc R . . H14B H 0.5623 -0.1708 0.2333 0.057 Uiso 1 1 calc R . . H14C H 0.6928 -0.1453 0.2552 0.057 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 0.0193(3) 0.0193(3) 0.0161(3) 0.0002(2) 0.0094(3) -0.0008(2) C1 0.0204(12) 0.0135(12) 0.0205(13) 0.0010(9) 0.0104(11) -0.0012(9) C2 0.0225(12) 0.0167(13) 0.0237(13) 0.0020(9) 0.0096(10) 0.0007(9) C3 0.0219(12) 0.0194(13) 0.0332(14) 0.0017(10) 0.0157(11) 0.0031(9) C4 0.0306(13) 0.0167(13) 0.0279(14) -0.0024(10) 0.0189(12) 0.0010(10) C5 0.0288(13) 0.0097(12) 0.0237(13) -0.0002(9) 0.0158(11) -0.0018(9) C6 0.0334(14) 0.0206(13) 0.0228(13) -0.0026(10) 0.0171(11) -0.0039(10) C7 0.0310(14) 0.0257(14) 0.0163(12) -0.0007(10) 0.0087(11) -0.0077(11) C8 0.0225(12) 0.0226(13) 0.0237(15) 0.0030(10) 0.0095(11) -0.0034(10) C9 0.0228(13) 0.0154(12) 0.0203(14) -0.0001(9) 0.0109(11) -0.0020(9) C10 0.0234(12) 0.0097(11) 0.0207(13) 0.0019(9) 0.0137(10) -0.0010(9) Br9 0.01860(15) 0.02707(17) 0.02176(17) 0.00146(9) 0.01193(12) -0.00052(8) O11 0.0278(8) 0.0161(9) 0.0223(8) -0.0001(6) 0.0155(7) 0.0015(6) C11 0.0291(13) 0.0204(13) 0.0317(13) -0.0052(10) 0.0178(11) 0.0000(10) C12 0.0314(14) 0.0183(13) 0.0356(16) -0.0021(10) 0.0151(13) 0.0027(10) O13 0.0235(9) 0.0308(10) 0.0175(9) 0.0016(7) 0.0074(7) -0.0023(7) C13 0.0276(14) 0.0242(14) 0.0267(15) 0.0032(10) 0.0069(12) -0.0007(10) C14 0.0369(16) 0.054(2) 0.0235(14) -0.0059(13) 0.0125(13) -0.0074(14) _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 O13 1.6392(16) . ? P1 O11 1.6434(16) . ? P1 C1 1.854(2) . ? C1 C2 1.383(3) . ? C1 C10 1.447(3) . ? C2 C3 1.410(3) . ? C2 H2A 0.9500 . ? C3 C4 1.361(3) . ? C3 H3A 0.9500 . ? C4 C5 1.410(3) . ? C4 H4A 0.9500 . ? C5 C6 1.427(3) . ? C5 C10 1.438(3) . ? C6 C7 1.357(3) . ? C6 H6A 0.9500 . ? C7 C8 1.409(3) . ? C7 H7A 0.9500 . ? C8 C9 1.364(4) . ? C8 H8A 0.9500 . ? C9 C10 1.423(3) . ? C9 Br9 1.913(2) . ? O11 C11 1.447(3) . ? C11 C12 1.498(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? O13 C13 1.447(3) . ? C13 C14 1.495(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 O13 P1 O11 99.01(9) . . ? O13 P1 C1 100.11(9) . . ? O11 P1 C1 93.29(9) . . ? C2 C1 C10 118.9(2) . . ? C2 C1 P1 116.35(18) . . ? C10 C1 P1 124.69(17) . . ? C1 C2 C3 122.5(2) . . ? C1 C2 H2A 118.8 . . ? C3 C2 H2A 118.8 . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C4 C5 C6 119.0(2) . . ? C4 C5 C10 120.4(2) . . ? C6 C5 C10 120.5(2) . . ? C7 C6 C5 120.7(2) . . ? C7 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C6 C7 C8 119.8(2) . . ? C6 C7 H7A 120.1 . . ? C8 C7 H7A 120.1 . . ? C9 C8 C7 120.6(2) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C8 C9 C10 122.7(2) . . ? C8 C9 Br9 114.77(18) . . ? C10 C9 Br9 122.37(17) . . ? C9 C10 C5 115.5(2) . . ? C9 C10 C1 127.0(2) . . ? C5 C10 C1 117.5(2) . . ? C11 O11 P1 116.95(13) . . ? O11 C11 C12 108.29(19) . . ? O11 C11 H11A 110.0 . . ? C12 C11 H11A 110.0 . . ? O11 C11 H11B 110.0 . . ? C12 C11 H11B 110.0 . . ? H11A C11 H11B 108.4 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C13 O13 P1 117.16(15) . . ? O13 C13 C14 110.2(2) . . ? O13 C13 H13A 109.6 . . ? C14 C13 H13A 109.6 . . ? O13 C13 H13B 109.6 . . ? C14 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O13 P1 C1 C2 -7.32(19) . . . . ? O11 P1 C1 C2 -107.09(18) . . . . ? O13 P1 C1 C10 169.69(18) . . . . ? O11 P1 C1 C10 69.93(19) . . . . ? C10 C1 C2 C3 -2.6(3) . . . . ? P1 C1 C2 C3 174.59(18) . . . . ? C1 C2 C3 C4 -1.6(4) . . . . ? C2 C3 C4 C5 2.8(4) . . . . ? C3 C4 C5 C6 -178.8(2) . . . . ? C3 C4 C5 C10 0.4(3) . . . . ? C4 C5 C6 C7 178.8(2) . . . . ? C10 C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C8 2.7(4) . . . . ? C6 C7 C8 C9 -0.6(4) . . . . ? C7 C8 C9 C10 -4.1(4) . . . . ? C7 C8 C9 Br9 170.92(18) . . . . ? C8 C9 C10 C5 6.2(3) . . . . ? Br9 C9 C10 C5 -168.47(16) . . . . ? C8 C9 C10 C1 -172.2(2) . . . . ? Br9 C9 C10 C1 13.1(3) . . . . ? C4 C5 C10 C9 176.9(2) . . . . ? C6 C5 C10 C9 -4.0(3) . . . . ? C4 C5 C10 C1 -4.5(3) . . . . ? C6 C5 C10 C1 174.6(2) . . . . ? C2 C1 C10 C9 -176.1(2) . . . . ? P1 C1 C10 C9 7.0(3) . . . . ? C2 C1 C10 C5 5.5(3) . . . . ? P1 C1 C10 C5 -171.43(16) . . . . ? O13 P1 O11 C11 85.61(16) . . . . ? C1 P1 O11 C11 -173.60(16) . . . . ? P1 O11 C11 C12 -166.51(15) . . . . ? O11 P1 O13 C13 -146.54(16) . . . . ? C1 P1 O13 C13 118.46(17) . . . . ? P1 O13 C13 C14 109.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.664 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.068 # Attachment '9.cif' data_piotr9 _database_code_depnum_ccdc_archive 'CCDC 743893' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 Br O2 P' _chemical_formula_weight 449.26 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' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.2718(9) _cell_length_b 8.0587(9) _cell_length_c 33.861(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1984.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 5411 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 21.96 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.010 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 2.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8640 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16844 _diffrn_reflns_av_R_equivalents 0.1543 _diffrn_reflns_av_sigmaI/netI 0.0822 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 25.34 _reflns_number_total 3572 _reflns_number_gt 3290 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0658P)^2^+15.0510P] 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 0.023(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(3) _refine_ls_number_reflns 3572 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0927 _refine_ls_wR_factor_ref 0.2055 _refine_ls_wR_factor_gt 0.2006 _refine_ls_goodness_of_fit_ref 1.274 _refine_ls_restrained_S_all 1.274 _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 0.8356(4) 0.6041(3) 0.39132(8) 0.0213(6) Uani 1 1 d . . . C1 C 0.8330(14) 0.6212(14) 0.4454(3) 0.021(2) Uani 1 1 d . . . C2 C 0.7904(13) 0.7771(14) 0.4622(3) 0.020(2) Uani 1 1 d . . . H2A H 0.7695 0.8683 0.4450 0.024 Uiso 1 1 calc R . . C3 C 0.7773(13) 0.8039(13) 0.5035(3) 0.019(2) Uani 1 1 d . . . H3A H 0.7444 0.9099 0.5135 0.023 Uiso 1 1 calc R . . C4 C 0.8133(14) 0.6729(14) 0.5290(3) 0.023(2) Uani 1 1 d . . . C5 C 0.8640(14) 0.5170(14) 0.5128(3) 0.023(2) Uani 1 1 d . . . C6 C 0.9084(15) 0.4037(13) 0.5428(3) 0.023(2) Uani 1 1 d . . . C7 C 0.9562(13) 0.2487(14) 0.5330(3) 0.027(2) Uani 1 1 d . . . H7A H 0.9858 0.1700 0.5529 0.032 Uiso 1 1 calc R . . C8 C 0.9623(14) 0.2029(14) 0.4923(3) 0.024(2) Uani 1 1 d . . . H8A H 0.9987 0.0939 0.4850 0.029 Uiso 1 1 calc R . . Br9 Br 0.91779(15) 0.22802(11) 0.41079(3) 0.0252(3) Uani 1 1 d . . . C9 C 0.9152(16) 0.3168(12) 0.4634(3) 0.024(2) Uani 1 1 d . . . C10 C 0.8735(13) 0.4846(13) 0.4719(3) 0.019(2) Uani 1 1 d . . . O11 O 0.6154(10) 0.5504(10) 0.3886(2) 0.0273(17) Uani 1 1 d . . . C11 C 0.5308(15) 0.4961(13) 0.3539(3) 0.025(2) Uani 1 1 d . . . C12 C 0.3694(18) 0.4086(17) 0.3579(4) 0.038(3) Uani 1 1 d . . . H12A H 0.3184 0.3892 0.3833 0.046 Uiso 1 1 calc R . . C13 C 0.282(2) 0.3491(17) 0.3244(3) 0.042(3) Uani 1 1 d . . . H13A H 0.1739 0.2840 0.3268 0.051 Uiso 1 1 calc R . . C14 C 0.3522(18) 0.3842(15) 0.2877(3) 0.034(3) Uani 1 1 d . . . H14A H 0.2914 0.3442 0.2647 0.041 Uiso 1 1 calc R . . C15 C 0.5072(17) 0.4754(16) 0.2840(3) 0.031(3) Uani 1 1 d . . . H15A H 0.5520 0.5007 0.2583 0.038 Uiso 1 1 calc R . . C16 C 0.6014(18) 0.5322(16) 0.3162(3) 0.038(3) Uani 1 1 d . . . H16A H 0.7115 0.5945 0.3132 0.045 Uiso 1 1 calc R . . O17 O 0.8155(12) 0.8054(9) 0.38086(19) 0.0283(18) Uani 1 1 d . . . C17 C 0.8912(18) 0.8689(12) 0.3467(3) 0.028(3) Uani 1 1 d . . . C18 C 1.0531(17) 0.8127(15) 0.3302(3) 0.034(3) Uani 1 1 d . . . H18A H 1.1175 0.7242 0.3425 0.041 Uiso 1 1 calc R . . C19 C 1.1242(17) 0.8827(16) 0.2959(3) 0.036(3) Uani 1 1 d . . . H19A H 1.2359 0.8430 0.2848 0.043 Uiso 1 1 calc R . . C20 C 1.0268(18) 1.0141(16) 0.2780(3) 0.035(3) Uani 1 1 d . . . H20A H 1.0718 1.0639 0.2545 0.042 Uiso 1 1 calc R . . C21 C 0.8696(18) 1.0683(16) 0.2945(3) 0.036(3) Uani 1 1 d . . . H21A H 0.8062 1.1584 0.2826 0.043 Uiso 1 1 calc R . . C22 C 0.797(2) 0.9968(16) 0.3284(3) 0.037(3) Uani 1 1 d . . . H22A H 0.6841 1.0354 0.3389 0.045 Uiso 1 1 calc R . . C23 C 0.8095(15) 0.6617(13) 0.5734(3) 0.022(2) Uani 1 1 d . . . H23A H 0.6820 0.6695 0.5834 0.026 Uiso 1 1 calc R . . H23B H 0.8839 0.7514 0.5854 0.026 Uiso 1 1 calc R . . C24 C 0.8925(15) 0.4911(12) 0.5826(3) 0.022(2) Uani 1 1 d . . . H24A H 1.0150 0.5031 0.5951 0.026 Uiso 1 1 calc R . . H24B H 0.8115 0.4279 0.6007 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0241(15) 0.0224(14) 0.0173(12) -0.0012(10) 0.0002(11) 0.0007(11) C1 0.008(5) 0.040(6) 0.015(5) -0.008(4) -0.001(4) 0.007(5) C2 0.014(5) 0.024(5) 0.021(4) 0.008(4) 0.004(4) 0.003(4) C3 0.008(5) 0.028(6) 0.021(5) -0.007(4) 0.004(4) -0.001(4) C4 0.005(5) 0.036(6) 0.028(5) 0.003(4) -0.002(4) -0.005(4) C5 0.010(5) 0.033(6) 0.025(5) 0.001(4) -0.002(4) -0.007(4) C6 0.011(5) 0.036(6) 0.021(5) -0.001(4) -0.010(4) -0.008(5) C7 0.023(6) 0.037(6) 0.019(5) 0.013(5) -0.001(4) 0.002(5) C8 0.021(6) 0.027(5) 0.024(5) -0.001(4) 0.010(4) 0.008(4) Br9 0.0325(6) 0.0186(5) 0.0244(5) -0.0038(4) 0.0029(5) 0.0015(4) C9 0.015(5) 0.025(5) 0.033(5) 0.002(4) -0.002(5) -0.002(5) C10 0.005(5) 0.028(5) 0.024(5) 0.010(4) -0.001(4) -0.006(4) O11 0.023(4) 0.040(4) 0.018(3) -0.008(3) -0.006(3) -0.009(4) C11 0.028(7) 0.023(5) 0.023(5) -0.002(4) -0.010(4) 0.010(5) C12 0.037(8) 0.047(7) 0.030(6) 0.008(5) -0.001(5) -0.016(6) C13 0.051(9) 0.046(7) 0.029(6) 0.000(5) -0.014(6) -0.017(7) C14 0.043(8) 0.034(7) 0.026(6) -0.009(5) -0.009(5) 0.001(6) C15 0.038(7) 0.045(7) 0.012(5) 0.001(5) -0.002(4) -0.007(6) C16 0.027(7) 0.049(7) 0.038(6) 0.001(5) 0.001(6) -0.006(7) O17 0.047(5) 0.023(4) 0.015(3) 0.005(3) 0.004(3) 0.005(4) C17 0.048(8) 0.021(5) 0.015(4) -0.002(4) 0.002(5) 0.000(6) C18 0.034(7) 0.042(7) 0.026(5) 0.002(5) -0.002(5) -0.010(6) C19 0.023(7) 0.051(8) 0.034(6) -0.008(5) 0.006(5) -0.010(6) C20 0.047(8) 0.051(7) 0.006(4) 0.002(5) 0.001(5) -0.031(6) C21 0.041(8) 0.046(7) 0.021(5) 0.010(5) -0.012(5) -0.011(6) C22 0.049(8) 0.035(7) 0.028(6) 0.003(5) -0.009(6) 0.001(6) C23 0.022(6) 0.029(5) 0.013(4) -0.002(4) -0.001(4) -0.003(5) C24 0.027(6) 0.026(5) 0.013(4) 0.001(4) 0.002(4) 0.000(5) _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 O11 1.661(8) . ? P1 O17 1.666(8) . ? P1 C1 1.838(9) . ? C1 C2 1.414(15) . ? C1 C10 1.450(14) . ? C2 C3 1.417(13) . ? C2 H2A 0.9500 . ? C3 C4 1.390(15) . ? C3 H3A 0.9500 . ? C4 C5 1.420(15) . ? C4 C23 1.504(13) . ? C5 C6 1.403(15) . ? C5 C10 1.411(14) . ? C6 C7 1.339(16) . ? C6 C24 1.524(12) . ? C7 C8 1.427(13) . ? C7 H7A 0.9500 . ? C8 C9 1.384(14) . ? C8 H8A 0.9500 . ? Br9 C9 1.922(10) . ? C9 C10 1.415(15) . ? O11 C11 1.398(12) . ? C11 C12 1.377(16) . ? C11 C16 1.404(16) . ? C12 C13 1.385(17) . ? C12 H12A 0.9500 . ? C13 C14 1.373(17) . ? C13 H13A 0.9500 . ? C14 C15 1.351(18) . ? C14 H14A 0.9500 . ? C15 C16 1.367(16) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? O17 C17 1.380(12) . ? C17 C18 1.380(17) . ? C17 C22 1.383(16) . ? C18 C19 1.390(16) . ? C18 H18A 0.9500 . ? C19 C20 1.411(18) . ? C19 H19A 0.9500 . ? C20 C21 1.345(19) . ? C20 H20A 0.9500 . ? C21 C22 1.387(17) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23 C24 1.533(14) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 P1 O17 99.0(4) . . ? O11 P1 C1 93.7(4) . . ? O17 P1 C1 98.0(5) . . ? C2 C1 C10 118.1(8) . . ? C2 C1 P1 118.0(8) . . ? C10 C1 P1 123.9(8) . . ? C1 C2 C3 123.1(9) . . ? C1 C2 H2A 118.5 . . ? C3 C2 H2A 118.5 . . ? C4 C3 C2 119.1(10) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 118.7(9) . . ? C3 C4 C23 131.6(10) . . ? C5 C4 C23 109.7(9) . . ? C6 C5 C10 125.4(10) . . ? C6 C5 C4 110.8(9) . . ? C10 C5 C4 123.8(10) . . ? C7 C6 C5 119.1(9) . . ? C7 C6 C24 132.1(9) . . ? C5 C6 C24 108.8(9) . . ? C6 C7 C8 119.3(9) . . ? C6 C7 H7A 120.4 . . ? C8 C7 H7A 120.4 . . ? C9 C8 C7 120.2(10) . . ? C9 C8 H8A 119.9 . . ? C7 C8 H8A 119.9 . . ? C8 C9 C10 122.9(9) . . ? C8 C9 Br9 114.0(7) . . ? C10 C9 Br9 123.1(7) . . ? C5 C10 C9 112.7(9) . . ? C5 C10 C1 117.2(10) . . ? C9 C10 C1 130.1(9) . . ? C11 O11 P1 123.5(7) . . ? C12 C11 O11 116.9(10) . . ? C12 C11 C16 120.5(10) . . ? O11 C11 C16 122.5(10) . . ? C11 C12 C13 119.1(11) . . ? C11 C12 H12A 120.5 . . ? C13 C12 H12A 120.5 . . ? C14 C13 C12 120.1(12) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C15 C14 C13 120.3(11) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C14 C15 C16 121.8(11) . . ? C14 C15 H15A 119.1 . . ? C16 C15 H15A 119.1 . . ? C15 C16 C11 118.1(12) . . ? C15 C16 H16A 120.9 . . ? C11 C16 H16A 120.9 . . ? C17 O17 P1 120.3(6) . . ? O17 C17 C18 124.0(10) . . ? O17 C17 C22 117.1(11) . . ? C18 C17 C22 118.9(10) . . ? C17 C18 C19 121.5(12) . . ? C17 C18 H18A 119.3 . . ? C19 C18 H18A 119.3 . . ? C18 C19 C20 118.5(11) . . ? C18 C19 H19A 120.8 . . ? C20 C19 H19A 120.8 . . ? C21 C20 C19 119.4(10) . . ? C21 C20 H20A 120.3 . . ? C19 C20 H20A 120.3 . . ? C20 C21 C22 122.1(12) . . ? C20 C21 H21A 119.0 . . ? C22 C21 H21A 119.0 . . ? C17 C22 C21 119.6(13) . . ? C17 C22 H22A 120.2 . . ? C21 C22 H22A 120.2 . . ? C4 C23 C24 104.5(8) . . ? C4 C23 H23A 110.9 . . ? C24 C23 H23A 110.9 . . ? C4 C23 H23B 110.9 . . ? C24 C23 H23B 110.9 . . ? H23A C23 H23B 108.9 . . ? C6 C24 C23 105.3(8) . . ? C6 C24 H24A 110.7 . . ? C23 C24 H24A 110.7 . . ? C6 C24 H24B 110.7 . . ? C23 C24 H24B 110.7 . . ? H24A C24 H24B 108.8 . . ? 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 O11 P1 C1 C2 -90.8(9) . . . . ? O17 P1 C1 C2 8.9(9) . . . . ? O11 P1 C1 C10 89.7(9) . . . . ? O17 P1 C1 C10 -170.6(9) . . . . ? C10 C1 C2 C3 -3.0(15) . . . . ? P1 C1 C2 C3 177.5(8) . . . . ? C1 C2 C3 C4 2.0(14) . . . . ? C2 C3 C4 C5 0.7(14) . . . . ? C2 C3 C4 C23 -179.4(10) . . . . ? C3 C4 C5 C6 175.5(9) . . . . ? C23 C4 C5 C6 -4.4(12) . . . . ? C3 C4 C5 C10 -2.5(15) . . . . ? C23 C4 C5 C10 177.6(9) . . . . ? C10 C5 C6 C7 -3.3(16) . . . . ? C4 C5 C6 C7 178.7(10) . . . . ? C10 C5 C6 C24 176.1(9) . . . . ? C4 C5 C6 C24 -1.9(12) . . . . ? C5 C6 C7 C8 0.5(15) . . . . ? C24 C6 C7 C8 -178.7(11) . . . . ? C6 C7 C8 C9 -1.4(15) . . . . ? C7 C8 C9 C10 5.0(16) . . . . ? C7 C8 C9 Br9 -176.5(8) . . . . ? C6 C5 C10 C9 6.3(15) . . . . ? C4 C5 C10 C9 -176.0(10) . . . . ? C6 C5 C10 C1 -176.2(10) . . . . ? C4 C5 C10 C1 1.6(14) . . . . ? C8 C9 C10 C5 -7.0(15) . . . . ? Br9 C9 C10 C5 174.6(7) . . . . ? C8 C9 C10 C1 175.8(10) . . . . ? Br9 C9 C10 C1 -2.6(16) . . . . ? C2 C1 C10 C5 1.1(14) . . . . ? P1 C1 C10 C5 -179.4(8) . . . . ? C2 C1 C10 C9 178.2(10) . . . . ? P1 C1 C10 C9 -2.3(16) . . . . ? O17 P1 O11 C11 90.0(8) . . . . ? C1 P1 O11 C11 -171.3(8) . . . . ? P1 O11 C11 C12 160.4(9) . . . . ? P1 O11 C11 C16 -21.7(14) . . . . ? O11 C11 C12 C13 -178.7(11) . . . . ? C16 C11 C12 C13 3.3(19) . . . . ? C11 C12 C13 C14 -3(2) . . . . ? C12 C13 C14 C15 1(2) . . . . ? C13 C14 C15 C16 2(2) . . . . ? C14 C15 C16 C11 -1.2(19) . . . . ? C12 C11 C16 C15 -1.3(18) . . . . ? O11 C11 C16 C15 -179.1(11) . . . . ? O11 P1 O17 C17 -114.7(9) . . . . ? C1 P1 O17 C17 150.3(9) . . . . ? P1 O17 C17 C18 -34.6(14) . . . . ? P1 O17 C17 C22 145.6(9) . . . . ? O17 C17 C18 C19 -179.2(10) . . . . ? C22 C17 C18 C19 0.6(17) . . . . ? C17 C18 C19 C20 0.0(17) . . . . ? C18 C19 C20 C21 0.4(17) . . . . ? C19 C20 C21 C22 -1.3(18) . . . . ? O17 C17 C22 C21 178.3(10) . . . . ? C18 C17 C22 C21 -1.5(18) . . . . ? C20 C21 C22 C17 1.9(19) . . . . ? C3 C4 C23 C24 -171.2(10) . . . . ? C5 C4 C23 C24 8.6(11) . . . . ? C7 C6 C24 C23 -173.6(12) . . . . ? C5 C6 C24 C23 7.2(12) . . . . ? C4 C23 C24 C6 -9.3(11) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.453 _refine_diff_density_min -1.335 _refine_diff_density_rms 0.253