# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 897834' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 O4 P' _chemical_formula_weight 356.34 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.524(2) _cell_length_b 12.391(2) _cell_length_c 11.553(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.019(3) _cell_angle_gamma 90.00 _cell_volume 1714.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4478 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 28.16 _exptl_crystal_description blocky _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.957 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker Smart Aepex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8504 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3177 _reflns_number_gt 2799 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0723P)^2^+0.9721P] 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 3177 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1457 _refine_ls_wR_factor_gt 0.1430 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.53918(4) 0.20613(5) 0.28425(5) 0.0352(2) Uani 1 1 d . . . O1 O 0.65899(12) 0.17671(14) 0.27616(14) 0.0411(4) Uani 1 1 d . . . O2 O 0.55395(14) 0.23580(15) 0.41900(16) 0.0488(5) Uani 1 1 d . . . O3 O 0.48868(15) 0.29326(14) 0.20181(18) 0.0540(5) Uani 1 1 d . . . O4 O 0.49891(15) 0.01033(14) 0.34501(17) 0.0531(5) Uani 1 1 d . . . H4A H 0.5000 -0.0519 0.3212 0.080 Uiso 1 1 calc R . . C1 C 0.46198(18) 0.07945(19) 0.2455(2) 0.0410(5) Uani 1 1 d . . . H1A H 0.4864 0.0470 0.1801 0.049 Uiso 1 1 calc R . . C2 C 0.33617(18) 0.09352(17) 0.1959(2) 0.0381(5) Uani 1 1 d . . . C3 C 0.26828(19) 0.10677(17) 0.2739(2) 0.0386(5) Uani 1 1 d . . . C4 C 0.3110(2) 0.1205(2) 0.4012(2) 0.0459(6) Uani 1 1 d . . . H4B H 0.3878 0.1183 0.4374 0.055 Uiso 1 1 calc R . . C5 C 0.2431(2) 0.1367(2) 0.4703(3) 0.0531(7) Uani 1 1 d . . . H5A H 0.2738 0.1475 0.5531 0.064 Uiso 1 1 calc R . . C6 C 0.1255(2) 0.1378(2) 0.4196(3) 0.0562(7) Uani 1 1 d . . . H6A H 0.0796 0.1477 0.4691 0.067 Uiso 1 1 calc R . . C7 C 0.0802(2) 0.1243(2) 0.2994(3) 0.0510(7) Uani 1 1 d . . . H7A H 0.0030 0.1240 0.2666 0.061 Uiso 1 1 calc R . . C8 C 0.14903(19) 0.11055(18) 0.2218(2) 0.0406(5) Uani 1 1 d . . . C9 C 0.10397(19) 0.10210(19) 0.0977(2) 0.0443(6) Uani 1 1 d . . . H9A H 0.0267 0.1013 0.0651 0.053 Uiso 1 1 calc R . . C10 C 0.1694(2) 0.09485(18) 0.0204(2) 0.0414(6) Uani 1 1 d . . . C11 C 0.1204(2) 0.0909(2) -0.1084(2) 0.0524(7) Uani 1 1 d . . . H11A H 0.0430 0.0905 -0.1400 0.063 Uiso 1 1 calc R . . C12 C 0.1833(3) 0.0878(2) -0.1843(3) 0.0609(8) Uani 1 1 d . . . H12A H 0.1496 0.0854 -0.2675 0.073 Uiso 1 1 calc R . . C13 C 0.2995(3) 0.0884(2) -0.1384(3) 0.0596(7) Uani 1 1 d . . . H13A H 0.3426 0.0875 -0.1917 0.071 Uiso 1 1 calc R . . C14 C 0.3508(2) 0.0903(2) -0.0177(3) 0.0511(6) Uani 1 1 d . . . H14A H 0.4284 0.0905 0.0098 0.061 Uiso 1 1 calc R . . C15 C 0.28857(19) 0.09199(18) 0.0695(2) 0.0396(5) Uani 1 1 d . . . C16 C 0.74764(19) 0.1387(2) 0.3788(2) 0.0437(6) Uani 1 1 d . . . H16A H 0.8180 0.1420 0.3598 0.052 Uiso 1 1 calc R . . H16B H 0.7338 0.0639 0.3949 0.052 Uiso 1 1 calc R . . C18 C 0.6458(2) 0.1953(3) 0.5182(2) 0.0543(7) Uani 1 1 d . . . H18A H 0.6325 0.1202 0.5328 0.065 Uiso 1 1 calc R . . H18B H 0.6493 0.2356 0.5912 0.065 Uiso 1 1 calc R . . C17 C 0.7559(2) 0.20541(19) 0.4904(2) 0.0425(6) Uani 1 1 d . . . C19 C 0.7819(3) 0.3217(2) 0.4691(3) 0.0677(9) Uani 1 1 d . . . H19A H 0.7240 0.3501 0.4021 0.102 Uiso 1 1 calc R . . H19B H 0.8521 0.3253 0.4513 0.102 Uiso 1 1 calc R . . H19C H 0.7861 0.3634 0.5403 0.102 Uiso 1 1 calc R . . C20 C 0.8471(3) 0.1586(3) 0.5979(3) 0.0666(9) Uani 1 1 d . . . H20A H 0.8295 0.0850 0.6106 0.100 Uiso 1 1 calc R . . H20B H 0.8513 0.2000 0.6692 0.100 Uiso 1 1 calc R . . H20C H 0.9177 0.1614 0.5809 0.100 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 0.0278(3) 0.0327(3) 0.0445(4) 0.0012(2) 0.0095(2) -0.0025(2) O1 0.0322(8) 0.0551(10) 0.0373(9) 0.0007(7) 0.0122(7) -0.0022(7) O2 0.0357(9) 0.0608(11) 0.0522(11) -0.0148(9) 0.0162(7) 0.0002(8) O3 0.0440(10) 0.0380(10) 0.0721(13) 0.0121(8) 0.0045(9) -0.0036(7) O4 0.0545(11) 0.0388(10) 0.0566(11) 0.0036(8) 0.0016(9) 0.0030(8) C1 0.0345(12) 0.0326(12) 0.0521(14) 0.0027(10) 0.0066(10) -0.0008(9) C2 0.0305(11) 0.0273(11) 0.0536(14) 0.0019(10) 0.0075(10) -0.0046(9) C3 0.0336(11) 0.0295(11) 0.0487(13) 0.0037(10) 0.0059(10) -0.0036(9) C4 0.0454(13) 0.0395(13) 0.0499(14) 0.0038(11) 0.0095(11) -0.0077(11) C5 0.0646(17) 0.0429(15) 0.0491(15) 0.0005(12) 0.0123(13) -0.0065(13) C6 0.0630(17) 0.0495(16) 0.0649(18) -0.0016(13) 0.0325(15) 0.0009(13) C7 0.0402(13) 0.0462(14) 0.0690(18) 0.0020(13) 0.0196(12) 0.0037(11) C8 0.0332(11) 0.0328(12) 0.0532(14) 0.0018(10) 0.0084(10) -0.0010(9) C9 0.0296(11) 0.0400(13) 0.0575(15) 0.0029(11) 0.0038(11) -0.0001(10) C10 0.0387(12) 0.0313(12) 0.0499(14) 0.0025(10) 0.0060(10) -0.0014(10) C11 0.0525(15) 0.0444(14) 0.0520(16) 0.0014(12) 0.0025(12) -0.0020(12) C12 0.073(2) 0.0566(17) 0.0473(16) -0.0014(13) 0.0088(14) 0.0007(15) C13 0.0733(19) 0.0580(17) 0.0506(16) -0.0008(13) 0.0231(14) 0.0010(15) C14 0.0437(14) 0.0474(15) 0.0636(17) -0.0002(13) 0.0178(12) -0.0018(11) C15 0.0380(12) 0.0283(11) 0.0506(14) 0.0004(10) 0.0102(10) -0.0036(9) C16 0.0349(12) 0.0476(14) 0.0481(14) 0.0022(11) 0.0113(10) 0.0082(10) C18 0.0530(16) 0.0726(19) 0.0373(13) -0.0107(12) 0.0134(11) -0.0064(14) C17 0.0363(12) 0.0384(13) 0.0470(14) -0.0001(10) 0.0030(10) -0.0041(10) C19 0.0570(17) 0.0455(16) 0.084(2) 0.0021(15) -0.0061(15) -0.0151(13) C20 0.0623(18) 0.0626(19) 0.0584(18) 0.0028(15) -0.0083(14) -0.0012(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O3 1.4560(18) . ? P1 O2 1.5570(18) . ? P1 O1 1.5733(16) . ? P1 C1 1.829(2) . ? O1 C16 1.446(3) . ? O2 C18 1.455(3) . ? O4 C1 1.400(3) . ? O4 H4A 0.8200 . ? C1 C2 1.521(3) . ? C1 H1A 0.9800 . ? C2 C15 1.406(3) . ? C2 C3 1.418(3) . ? C3 C4 1.421(4) . ? C3 C8 1.438(3) . ? C4 C5 1.341(4) . ? C4 H4B 0.9300 . ? C5 C6 1.417(4) . ? C5 H5A 0.9300 . ? C6 C7 1.348(4) . ? C6 H6A 0.9300 . ? C7 C8 1.423(4) . ? C7 H7A 0.9300 . ? C8 C9 1.382(4) . ? C9 C10 1.381(4) . ? C9 H9A 0.9300 . ? C10 C15 1.434(3) . ? C10 C11 1.434(4) . ? C11 C12 1.340(4) . ? C11 H11A 0.9300 . ? C12 C13 1.396(4) . ? C12 H12A 0.9300 . ? C13 C14 1.354(4) . ? C13 H13A 0.9300 . ? C14 C15 1.443(4) . ? C14 H14A 0.9300 . ? C16 C17 1.509(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C18 C17 1.510(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C17 C19 1.513(4) . ? C17 C20 1.534(4) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 O3 P1 O2 112.37(11) . . ? O3 P1 O1 111.86(11) . . ? O2 P1 O1 106.13(9) . . ? O3 P1 C1 112.26(10) . . ? O2 P1 C1 110.32(11) . . ? O1 P1 C1 103.38(10) . . ? C16 O1 P1 122.93(14) . . ? C18 O2 P1 122.77(16) . . ? C1 O4 H4A 109.5 . . ? O4 C1 C2 115.9(2) . . ? O4 C1 P1 107.45(16) . . ? C2 C1 P1 114.14(16) . . ? O4 C1 H1A 106.2 . . ? C2 C1 H1A 106.2 . . ? P1 C1 H1A 106.2 . . ? C15 C2 C3 120.7(2) . . ? C15 C2 C1 117.9(2) . . ? C3 C2 C1 121.5(2) . . ? C2 C3 C4 123.9(2) . . ? C2 C3 C8 118.7(2) . . ? C4 C3 C8 117.3(2) . . ? C5 C4 C3 121.5(2) . . ? C5 C4 H4B 119.3 . . ? C3 C4 H4B 119.3 . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C7 C6 C5 119.8(3) . . ? C7 C6 H6A 120.1 . . ? C5 C6 H6A 120.1 . . ? C6 C7 C8 120.9(2) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? C9 C8 C7 121.5(2) . . ? C9 C8 C3 119.3(2) . . ? C7 C8 C3 119.1(2) . . ? C10 C9 C8 122.4(2) . . ? C10 C9 H9A 118.8 . . ? C8 C9 H9A 118.8 . . ? C9 C10 C15 119.4(2) . . ? C9 C10 C11 121.2(2) . . ? C15 C10 C11 119.3(2) . . ? C12 C11 C10 121.6(3) . . ? C12 C11 H11A 119.2 . . ? C10 C11 H11A 119.2 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C14 C13 C12 121.3(3) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C13 C14 C15 122.0(3) . . ? C13 C14 H14A 119.0 . . ? C15 C14 H14A 119.0 . . ? C2 C15 C10 119.1(2) . . ? C2 C15 C14 125.0(2) . . ? C10 C15 C14 115.9(2) . . ? O1 C16 C17 111.50(19) . . ? O1 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? O1 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? O2 C18 C17 111.4(2) . . ? O2 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? O2 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C16 C17 C18 107.3(2) . . ? C16 C17 C19 110.3(2) . . ? C18 C17 C19 111.5(2) . . ? C16 C17 C20 109.4(2) . . ? C18 C17 C20 107.9(2) . . ? C19 C17 C20 110.3(2) . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.898 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.056 data_2 _database_code_depnum_ccdc_archive 'CCDC 897835' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Br O3 P' _chemical_formula_weight 419.24 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)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 21.510(3) _cell_length_b 5.6451(8) _cell_length_c 14.508(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.285(3) _cell_angle_gamma 90.00 _cell_volume 1733.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2883 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 27.62 _exptl_crystal_description blocky _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 2.481 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.64 _exptl_absorpt_correction_T_max 0.78 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker Smart Aepex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8068 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3045 _reflns_number_gt 2213 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0729P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3045 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Br1 Br 0.019015(18) 0.40059(9) 0.63010(3) 0.0712(2) Uani 1 1 d . . . P1 P 0.35719(4) 0.38529(15) 0.65393(7) 0.0400(3) Uani 1 1 d . . . O2 O 0.33763(11) 0.3166(4) 0.74937(17) 0.0520(7) Uani 1 1 d . . . O1 O 0.41910(10) 0.5382(4) 0.68164(15) 0.0407(6) Uani 1 1 d . . . O3 O 0.36836(12) 0.1745(4) 0.6014(2) 0.0655(8) Uani 1 1 d . . . C2 C 0.22995(14) 0.5383(5) 0.6005(2) 0.0317(7) Uani 1 1 d . . . C15 C 0.19606(14) 0.3537(5) 0.5508(2) 0.0332(7) Uani 1 1 d . . . C14 C 0.22345(15) 0.1970(6) 0.4915(2) 0.0398(8) Uani 1 1 d . . . H14A H 0.2655 0.2183 0.4860 0.048 Uiso 1 1 calc R . . C13 C 0.19056(17) 0.0206(7) 0.4436(2) 0.0471(9) Uani 1 1 d . . . H13A H 0.2098 -0.0769 0.4053 0.057 Uiso 1 1 calc R . . C12 C 0.12730(18) -0.0173(7) 0.4510(3) 0.0535(10) Uani 1 1 d . . . H12A H 0.1050 -0.1407 0.4178 0.064 Uiso 1 1 calc R . . C11 C 0.09859(17) 0.1222(6) 0.5051(3) 0.0503(10) Uani 1 1 d . . . H11A H 0.0565 0.0944 0.5086 0.060 Uiso 1 1 calc R . . C10 C 0.13125(14) 0.3127(6) 0.5577(2) 0.0353(7) Uani 1 1 d . . . C9 C 0.10401(14) 0.4587(6) 0.6166(2) 0.0393(8) Uani 1 1 d . . . C8 C 0.13579(15) 0.6434(6) 0.6665(2) 0.0356(8) Uani 1 1 d . . . C7 C 0.10782(16) 0.7975(7) 0.7250(2) 0.0463(9) Uani 1 1 d . . . H7A H 0.0661 0.7719 0.7315 0.056 Uiso 1 1 calc R . . C6 C 0.13992(18) 0.9800(7) 0.7714(3) 0.0503(9) Uani 1 1 d . . . H6A H 0.1204 1.0763 0.8098 0.060 Uiso 1 1 calc R . . C5 C 0.20218(18) 1.0239(6) 0.7618(3) 0.0462(9) Uani 1 1 d . . . H5A H 0.2239 1.1510 0.7933 0.055 Uiso 1 1 calc R . . C4 C 0.23113(16) 0.8844(5) 0.7076(2) 0.0396(8) Uani 1 1 d . . . H4A H 0.2726 0.9187 0.7020 0.048 Uiso 1 1 calc R . . C3 C 0.20064(14) 0.6856(6) 0.6581(2) 0.0326(7) Uani 1 1 d . . . C1 C 0.29811(14) 0.5813(5) 0.5908(2) 0.0347(7) Uani 1 1 d . . . H1A H 0.3007 0.5733 0.5255 0.042 Uiso 1 1 d R . . H1B H 0.3089 0.7400 0.6114 0.042 Uiso 1 1 d R . . C18 C 0.34519(16) 0.4808(7) 0.8266(3) 0.0505(9) Uani 1 1 d . . . H18A H 0.3373 0.3986 0.8821 0.061 Uiso 1 1 calc R . . H18B H 0.3140 0.6056 0.8124 0.061 Uiso 1 1 calc R . . C17 C 0.40996(16) 0.5900(5) 0.8470(2) 0.0405(8) Uani 1 1 d . . . C16 C 0.42275(16) 0.7062(6) 0.7577(2) 0.0438(8) Uani 1 1 d . . . H16A H 0.3922 0.8316 0.7396 0.053 Uiso 1 1 calc R . . H16B H 0.4645 0.7773 0.7696 0.053 Uiso 1 1 calc R . . C19 C 0.45945(18) 0.4041(6) 0.8815(3) 0.0505(9) Uani 1 1 d . . . H19A H 0.4503 0.3325 0.9376 0.076 Uiso 1 1 calc R . . H19B H 0.5004 0.4772 0.8946 0.076 Uiso 1 1 calc R . . H19C H 0.4591 0.2849 0.8342 0.076 Uiso 1 1 calc R . . C20 C 0.4107(2) 0.7812(7) 0.9210(3) 0.0643(11) Uani 1 1 d . . . H20A H 0.4027 0.7108 0.9779 0.096 Uiso 1 1 calc R . . H20B H 0.3786 0.8965 0.8993 0.096 Uiso 1 1 calc R . . H20C H 0.4513 0.8569 0.9324 0.096 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 Br1 0.0355(3) 0.0984(4) 0.0840(4) -0.0061(2) 0.0228(2) -0.0113(2) P1 0.0290(5) 0.0363(5) 0.0540(6) -0.0026(4) 0.0059(4) -0.0008(4) O2 0.0402(13) 0.0523(15) 0.0622(17) 0.0129(13) 0.0053(12) -0.0147(12) O1 0.0290(12) 0.0512(14) 0.0443(13) -0.0036(11) 0.0129(10) -0.0059(11) O3 0.0536(16) 0.0489(16) 0.087(2) -0.0217(15) -0.0060(14) 0.0128(13) C2 0.0256(15) 0.0361(18) 0.0339(17) 0.0054(14) 0.0066(13) -0.0012(14) C15 0.0319(17) 0.0374(19) 0.0305(17) 0.0062(13) 0.0063(13) -0.0001(14) C14 0.0362(18) 0.049(2) 0.0356(19) 0.0002(16) 0.0091(15) -0.0023(16) C13 0.052(2) 0.051(2) 0.040(2) -0.0052(17) 0.0107(17) -0.0040(19) C12 0.055(2) 0.056(2) 0.048(2) -0.0086(19) 0.0060(18) -0.019(2) C11 0.038(2) 0.064(3) 0.048(2) -0.0015(18) 0.0059(17) -0.0169(18) C10 0.0306(16) 0.0413(19) 0.0345(18) 0.0056(15) 0.0067(14) -0.0021(15) C9 0.0242(16) 0.055(2) 0.0393(19) 0.0115(16) 0.0073(14) -0.0019(16) C8 0.0299(16) 0.043(2) 0.0353(18) 0.0088(14) 0.0093(14) 0.0033(14) C7 0.0373(19) 0.058(2) 0.048(2) 0.0069(18) 0.0199(16) 0.0059(18) C6 0.060(2) 0.045(2) 0.052(2) 0.0011(18) 0.0257(19) 0.011(2) C5 0.054(2) 0.039(2) 0.049(2) -0.0043(17) 0.0152(17) -0.0013(18) C4 0.0381(19) 0.0364(19) 0.045(2) 0.0036(15) 0.0098(15) 0.0006(15) C3 0.0300(16) 0.0348(17) 0.0343(17) 0.0080(14) 0.0093(13) 0.0036(14) C1 0.0313(17) 0.0342(18) 0.0407(18) -0.0015(14) 0.0119(14) -0.0044(14) C18 0.041(2) 0.059(2) 0.055(2) 0.0156(19) 0.0201(17) 0.0032(18) C17 0.0401(19) 0.0378(19) 0.045(2) 0.0015(15) 0.0127(15) 0.0043(15) C16 0.0396(18) 0.0421(19) 0.051(2) -0.0012(17) 0.0121(16) -0.0122(16) C19 0.044(2) 0.051(2) 0.055(2) -0.0020(18) 0.0037(17) 0.0066(17) C20 0.081(3) 0.059(3) 0.054(2) -0.006(2) 0.016(2) 0.021(2) _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 Br1 C9 1.902(3) . ? P1 O3 1.456(3) . ? P1 O2 1.566(3) . ? P1 O1 1.578(2) . ? P1 C1 1.806(3) . ? O2 C18 1.440(5) . ? O1 C16 1.447(4) . ? C2 C15 1.396(4) . ? C2 C3 1.406(4) . ? C2 C1 1.517(4) . ? C15 C14 1.433(4) . ? C15 C10 1.434(4) . ? C14 C13 1.342(5) . ? C14 H14A 0.9300 . ? C13 C12 1.400(5) . ? C13 H13A 0.9300 . ? C12 C11 1.339(5) . ? C12 H12A 0.9300 . ? C11 C10 1.429(5) . ? C11 H11A 0.9300 . ? C10 C9 1.390(5) . ? C9 C8 1.379(5) . ? C8 C7 1.421(5) . ? C8 C3 1.441(4) . ? C7 C6 1.351(5) . ? C7 H7A 0.9300 . ? C6 C5 1.393(5) . ? C6 H6A 0.9300 . ? C5 C4 1.343(5) . ? C5 H5A 0.9300 . ? C4 C3 1.427(4) . ? C4 H4A 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C18 C17 1.504(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C17 C19 1.515(5) . ? C17 C16 1.520(4) . ? C17 C20 1.520(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 O3 P1 O2 110.88(17) . . ? O3 P1 O1 111.70(14) . . ? O2 P1 O1 104.95(13) . . ? O3 P1 C1 113.70(16) . . ? O2 P1 C1 108.91(14) . . ? O1 P1 C1 106.23(13) . . ? C18 O2 P1 121.2(2) . . ? C16 O1 P1 118.77(19) . . ? C15 C2 C3 120.0(3) . . ? C15 C2 C1 119.7(3) . . ? C3 C2 C1 120.3(3) . . ? C2 C15 C14 122.6(3) . . ? C2 C15 C10 120.6(3) . . ? C14 C15 C10 116.8(3) . . ? C13 C14 C15 122.3(3) . . ? C13 C14 H14A 118.8 . . ? C15 C14 H14A 118.8 . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C11 C12 C13 120.8(3) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C12 C11 C10 121.5(3) . . ? C12 C11 H11A 119.3 . . ? C10 C11 H11A 119.3 . . ? C9 C10 C11 123.6(3) . . ? C9 C10 C15 118.0(3) . . ? C11 C10 C15 118.4(3) . . ? C8 C9 C10 123.2(3) . . ? C8 C9 Br1 118.2(2) . . ? C10 C9 Br1 118.6(2) . . ? C9 C8 C7 123.6(3) . . ? C9 C8 C3 118.5(3) . . ? C7 C8 C3 117.9(3) . . ? C6 C7 C8 122.1(3) . . ? C6 C7 H7A 119.0 . . ? C8 C7 H7A 119.0 . . ? C7 C6 C5 120.0(3) . . ? C7 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C5 C4 C3 122.4(3) . . ? C5 C4 H4A 118.8 . . ? C3 C4 H4A 118.8 . . ? C2 C3 C4 123.3(3) . . ? C2 C3 C8 119.7(3) . . ? C4 C3 C8 116.9(3) . . ? C2 C1 P1 117.3(2) . . ? C2 C1 H1A 108.1 . . ? P1 C1 H1A 108.2 . . ? C2 C1 H1B 107.7 . . ? P1 C1 H1B 107.7 . . ? H1A C1 H1B 107.3 . . ? O2 C18 C17 112.9(3) . . ? O2 C18 H18A 109.0 . . ? C17 C18 H18A 109.0 . . ? O2 C18 H18B 109.0 . . ? C17 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C18 C17 C19 110.6(3) . . ? C18 C17 C16 108.2(3) . . ? C19 C17 C16 110.9(3) . . ? C18 C17 C20 108.9(3) . . ? C19 C17 C20 109.9(3) . . ? C16 C17 C20 108.3(3) . . ? O1 C16 C17 111.9(3) . . ? O1 C16 H16A 109.2 . . ? C17 C16 H16A 109.2 . . ? O1 C16 H16B 109.2 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.431 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.076 data_3 _database_code_depnum_ccdc_archive 'CCDC 897836' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 Br2 O3 P' _chemical_formula_weight 500.16 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) ' _symmetry_space_group_name_Hall 'P 2ac 2ab c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.3845(17) _cell_length_b 13.615(4) _cell_length_c 22.618(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1966.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 315 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 14.79 _exptl_crystal_description blocky _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 4.222 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.60 _exptl_absorpt_correction_T_max 0.65 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker Smart Aepex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9612 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0767 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3852 _reflns_number_gt 2932 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0501P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.058(15) _chemical_absolute_configuration unk _refine_ls_number_reflns 3852 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 Br1 Br 0.65071(12) 0.30652(6) 0.35691(3) 0.0587(2) Uani 1 1 d . . . Br2 Br 1.29762(11) 0.55060(5) -0.03871(3) 0.04659(18) Uani 1 1 d . . . P1 P 0.7907(3) 0.30876(11) 0.04723(6) 0.0355(3) Uani 1 1 d . . . O1 O 0.5594(7) 0.3310(3) 0.06517(17) 0.0381(10) Uani 1 1 d . . . H1A H 0.4694 0.3153 0.0325 0.057 Uiso 1 1 d R . . O2 O 0.9187(7) 0.4030(3) 0.05956(17) 0.0411(10) Uani 1 1 d . . . O3 O 0.8153(7) 0.2647(3) -0.01325(17) 0.0430(10) Uani 1 1 d . . . C2 C 0.8406(9) 0.2430(3) 0.1622(2) 0.0300(11) Uani 1 1 d . . . C15 C 0.6594(5) 0.1975(3) 0.18540(14) 0.0330(12) Uani 1 1 d G . . C14 C 0.5295(6) 0.1393(3) 0.15064(11) 0.0366(13) Uani 1 1 d G . . H14 H 0.5619 0.1288 0.1110 0.044 Uiso 1 1 calc R . . C13 C 0.3513(6) 0.0970(3) 0.17504(15) 0.0463(15) Uani 1 1 d G . . H13 H 0.2644 0.0581 0.1518 0.056 Uiso 1 1 calc R . . C12 C 0.3030(5) 0.1128(3) 0.23420(16) 0.0414(14) Uani 1 1 d G . . H12 H 0.1837 0.0844 0.2505 0.050 Uiso 1 1 calc R . . C11 C 0.4329(6) 0.1709(3) 0.26897(11) 0.0463(16) Uani 1 1 d G . . H11 H 0.4005 0.1814 0.3086 0.056 Uiso 1 1 calc R . . C10 C 0.6111(5) 0.2132(3) 0.24456(14) 0.0379(14) Uani 1 1 d G . . C9 C 0.7287(10) 0.2739(4) 0.2779(2) 0.0400(15) Uani 1 1 d . . . C8 C 0.9112(10) 0.3232(4) 0.2555(3) 0.0394(14) Uani 1 1 d . . . C7 C 1.0481(11) 0.3852(5) 0.2905(3) 0.0483(18) Uani 1 1 d . . . H7 H 1.0153 0.3976 0.3299 0.058 Uiso 1 1 calc R . . C6 C 1.2194(11) 0.4247(4) 0.2671(3) 0.0459(15) Uani 1 1 d . . . H6 H 1.3002 0.4679 0.2894 0.055 Uiso 1 1 calc R . . C5 C 1.2770(11) 0.4026(5) 0.2113(3) 0.0479(16) Uani 1 1 d . . . H5 H 1.4011 0.4274 0.1958 0.057 Uiso 1 1 calc R . . C4 C 1.1532(10) 0.3442(4) 0.1781(3) 0.0366(13) Uani 1 1 d . . . H4 H 1.1961 0.3299 0.1398 0.044 Uiso 1 1 calc R . . C3 C 0.9595(9) 0.3030(5) 0.1983(2) 0.0356(13) Uani 1 1 d . . . C1 C 0.9020(9) 0.2227(4) 0.0967(2) 0.0339(12) Uani 1 1 d . . . H1C H 0.8560 0.1572 0.0859 0.041 Uiso 1 1 calc R . . H1B H 1.0534 0.2247 0.0931 0.041 Uiso 1 1 calc R . . C18 C 0.8501(11) 0.4925(4) 0.0292(3) 0.0465(16) Uani 1 1 d . . . H18A H 0.7029 0.5047 0.0368 0.056 Uiso 1 1 calc R . . H18B H 0.8703 0.4861 -0.0132 0.056 Uiso 1 1 calc R . . C17 C 0.9807(10) 0.5743(5) 0.0530(3) 0.0452(17) Uani 1 1 d . . . C16 C 1.2178(11) 0.5581(5) 0.0435(3) 0.0459(14) Uani 1 1 d . . . H16A H 1.2590 0.4978 0.0631 0.055 Uiso 1 1 calc R . . H16B H 1.2938 0.6116 0.0620 0.055 Uiso 1 1 calc R . . C19 C 0.9112(11) 0.6703(5) 0.0233(3) 0.0486(17) Uani 1 1 d . . . H19A H 0.9730 0.6747 -0.0153 0.073 Uiso 1 1 calc R . . H19B H 0.9558 0.7251 0.0468 0.073 Uiso 1 1 calc R . . H19C H 0.7613 0.6710 0.0198 0.073 Uiso 1 1 calc R . . C20 C 0.9451(12) 0.5786(5) 0.1200(3) 0.0508(18) Uani 1 1 d . . . H20A H 0.8403 0.5314 0.1309 0.076 Uiso 1 1 calc R . . H20B H 0.8989 0.6432 0.1309 0.076 Uiso 1 1 calc R . . H20C H 1.0737 0.5638 0.1401 0.076 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 Br1 0.0682(5) 0.0599(4) 0.0480(4) -0.0069(3) 0.0032(3) 0.0262(4) Br2 0.0436(3) 0.0493(3) 0.0469(3) -0.0099(3) 0.0133(3) -0.0069(3) P1 0.0392(8) 0.0399(7) 0.0275(6) 0.0017(6) -0.0006(6) -0.0010(7) O1 0.040(2) 0.041(2) 0.034(2) -0.0179(17) 0.0080(17) 0.0046(18) O2 0.037(2) 0.044(2) 0.043(2) 0.0162(19) -0.0040(18) -0.0075(19) O3 0.040(2) 0.053(3) 0.037(2) 0.0003(18) -0.0023(19) 0.010(2) C2 0.043(3) 0.017(2) 0.030(2) 0.0027(18) -0.004(2) 0.010(2) C15 0.032(3) 0.040(3) 0.026(2) 0.008(2) -0.003(2) 0.002(3) C14 0.038(3) 0.035(3) 0.037(3) 0.003(3) 0.001(2) -0.001(3) C13 0.045(4) 0.051(4) 0.043(3) 0.006(3) -0.001(3) -0.003(3) C12 0.034(3) 0.043(3) 0.047(3) 0.009(3) 0.013(3) 0.023(3) C11 0.040(4) 0.051(4) 0.048(4) 0.023(3) -0.002(3) 0.018(3) C10 0.031(3) 0.049(4) 0.034(3) 0.007(2) -0.001(2) 0.014(3) C9 0.044(4) 0.039(3) 0.037(3) -0.001(2) 0.005(3) 0.011(3) C8 0.037(3) 0.036(3) 0.045(3) 0.000(3) -0.009(3) 0.020(3) C7 0.047(4) 0.049(4) 0.048(4) -0.033(3) -0.017(3) 0.018(4) C6 0.046(4) 0.037(3) 0.055(4) -0.008(3) -0.021(3) 0.000(3) C5 0.044(4) 0.042(3) 0.058(4) 0.007(3) -0.010(3) -0.004(3) C4 0.035(3) 0.030(3) 0.044(3) 0.000(2) -0.007(2) 0.016(2) C3 0.035(3) 0.045(3) 0.027(3) -0.009(3) -0.007(2) 0.009(3) C1 0.031(3) 0.031(3) 0.040(3) 0.000(2) 0.001(2) 0.000(2) C18 0.045(4) 0.043(3) 0.052(4) 0.013(3) -0.009(3) -0.007(3) C17 0.036(4) 0.046(4) 0.054(4) 0.012(3) -0.007(3) 0.014(3) C16 0.051(4) 0.039(3) 0.047(3) -0.007(3) 0.001(3) -0.012(3) C19 0.048(4) 0.051(4) 0.047(4) 0.022(3) 0.001(3) 0.009(3) C20 0.067(5) 0.036(4) 0.050(4) -0.002(3) 0.024(3) 0.017(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 Br1 C9 1.908(6) . ? Br2 C16 1.930(6) . ? P1 O3 1.502(4) . ? P1 O2 1.546(4) . ? P1 O1 1.561(4) . ? P1 C1 1.770(6) . ? O1 H1A 0.9600 . ? O2 C18 1.466(7) . ? C2 C3 1.383(8) . ? C2 C15 1.413(6) . ? C2 C1 1.557(7) . ? C15 C14 1.3900 . ? C15 C10 1.3900 . ? C14 C13 1.3900 . ? C14 H14 0.9300 . ? C13 C12 1.3900 . ? C13 H13 0.9300 . ? C12 C11 1.3900 . ? C12 H12 0.9300 . ? C11 C10 1.3900 . ? C11 H11 0.9300 . ? C10 C9 1.347(7) . ? C9 C8 1.437(9) . ? C8 C3 1.356(8) . ? C8 C7 1.451(9) . ? C7 C6 1.329(10) . ? C7 H7 0.9300 . ? C6 C5 1.350(9) . ? C6 H6 0.9300 . ? C5 C4 1.348(9) . ? C5 H5 0.9300 . ? C4 C3 1.433(9) . ? C4 H4 0.9300 . ? C1 H1C 0.9700 . ? C1 H1B 0.9700 . ? C18 C17 1.493(9) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C17 C20 1.532(9) . ? C17 C19 1.535(8) . ? C17 C16 1.545(10) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 O3 P1 O2 116.1(3) . . ? O3 P1 O1 114.4(2) . . ? O2 P1 O1 107.0(2) . . ? O3 P1 C1 105.7(3) . . ? O2 P1 C1 102.9(3) . . ? O1 P1 C1 110.1(3) . . ? P1 O1 H1A 108.9 . . ? C18 O2 P1 116.6(4) . . ? C3 C2 C15 119.3(5) . . ? C3 C2 C1 121.9(5) . . ? C15 C2 C1 118.8(4) . . ? C14 C15 C10 120.0 . . ? C14 C15 C2 121.9(3) . . ? C10 C15 C2 118.1(3) . . ? C13 C14 C15 120.0 . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C13 C12 120.0 . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C11 C12 C13 120.0 . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C11 C10 120.0 . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C9 C10 C11 119.3(4) . . ? C9 C10 C15 120.6(4) . . ? C11 C10 C15 120.0 . . ? C10 C9 C8 122.8(5) . . ? C10 C9 Br1 121.4(4) . . ? C8 C9 Br1 115.7(4) . . ? C3 C8 C9 115.2(6) . . ? C3 C8 C7 120.1(6) . . ? C9 C8 C7 124.6(6) . . ? C6 C7 C8 121.0(6) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C7 C6 C5 120.4(6) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C4 C5 C6 119.5(7) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C4 C3 124.0(6) . . ? C5 C4 H4 118.0 . . ? C3 C4 H4 118.0 . . ? C8 C3 C2 123.9(6) . . ? C8 C3 C4 114.9(5) . . ? C2 C3 C4 121.1(5) . . ? C2 C1 P1 112.5(4) . . ? C2 C1 H1C 109.1 . . ? P1 C1 H1C 109.1 . . ? C2 C1 H1B 109.1 . . ? P1 C1 H1B 109.1 . . ? H1C C1 H1B 107.8 . . ? O2 C18 C17 106.5(5) . . ? O2 C18 H18A 110.4 . . ? C17 C18 H18A 110.4 . . ? O2 C18 H18B 110.4 . . ? C17 C18 H18B 110.4 . . ? H18A C18 H18B 108.6 . . ? C18 C17 C20 107.6(6) . . ? C18 C17 C19 108.4(5) . . ? C20 C17 C19 111.0(5) . . ? C18 C17 C16 113.0(6) . . ? C20 C17 C16 106.8(5) . . ? C19 C17 C16 110.1(6) . . ? C17 C16 Br2 113.6(4) . . ? C17 C16 H16A 108.8 . . ? Br2 C16 H16A 108.8 . . ? C17 C16 H16B 108.8 . . ? Br2 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.377 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.087