data_global _audit_creation_method 'APEX2 v2010.11-3' _publ_requested_journal ? _publ_contact_author_name ? _publ_contact_author_address ; ; _publ_contact_author_email ? _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ; ; _publ_section_abstract ; ; _publ_section_references ; ; _publ_section_comment ; ; data_I _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H24 Br O2 P' _chemical_formula_iupac ? _chemical_formula_weight 467.32 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_operation_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 14.349(10) _cell_length_b 9.776(7) _cell_length_c 16.959(13) _cell_angle_alpha 90 _cell_angle_beta 108.332(9) _cell_angle_gamma 90 _cell_volume 2258.(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 120 _cell_measurement_theta_min 2.5643 _cell_measurement_theta_max 22.9075 _cell_measurement_temperature 90.(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.730 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.250 _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 1.909 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.51 _exptl_absorpt_correction_T_max 0.64 _exptl_special_details ; ; _diffrn_ambient_temperature 90.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type 'Bruker SMART APEX2' _diffrn_measurement_method w _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 11422 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 20 _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. ; _reflns_number_total 4429 _reflns_number_gt 2850 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_gt 0.1030 _refine_ls_wR_factor_ref 0.1097 _refine_ls_goodness_of_fit_ref 0.907 _refine_ls_restrained_S_all 0.908 _refine_ls_number_reflns 4429 _refine_ls_number_parameters 273 _refine_ls_number_restraints 15 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.625 _refine_diff_density_min -0.427 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0015(5) 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' _computing_data_collection 'Bruker Instrument Service v2010.11.0.0' _computing_cell_refinement 'APEX2 v2010.11-3 (Bruker AXS)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br Br01 0.07137(2) 0.15772(4) 0.40211(2) 0.06878(18) Uani d . 1 . . P P1 0.54645(5) 0.32775(7) 0.33957(4) 0.03481(19) Uani d . 1 . . O O1 0.73806(14) 0.1984(2) 0.40425(13) 0.0558(6) Uani d . 1 . . H H003 0.7812 0.1376 0.411 0.084 Uiso calc RD 1 . . O O2 0.87802(17) 0.0229(3) 0.42604(15) 0.0642(7) Uani d DU 1 . . C C14 0.62459(18) 0.4738(3) 0.34773(17) 0.0384(6) Uani d . 1 . . C C8 0.42387(19) 0.3806(3) 0.33162(16) 0.0365(6) Uani d . 1 . . C C1 0.59084(19) 0.2322(3) 0.43393(17) 0.0362(6) Uani d . 1 . . C C20 0.53375(19) 0.2247(3) 0.24907(17) 0.0380(6) Uani d . 1 . . C C2 0.5349(2) 0.2144(3) 0.48688(17) 0.0389(7) Uani d . 1 . . H H009 0.471 0.2534 0.4721 0.047 Uiso calc R 1 . . C C7 0.6853(2) 0.1750(3) 0.45542(18) 0.0425(7) Uani d . 1 . . C C25 0.5681(2) 0.0921(3) 0.25404(19) 0.0475(7) Uani d . 1 . . H H00B 0.6068 0.0561 0.3061 0.057 Uiso calc R 1 . . C C3 0.5690(2) 0.1423(3) 0.55985(18) 0.0428(7) Uani d . 1 . . C C9 0.3496(2) 0.2829(3) 0.31220(19) 0.0479(8) Uani d . 1 . . H H00D 0.3628 0.1925 0.2981 0.057 Uiso calc R 1 . . C C5 0.6619(2) 0.0834(3) 0.57843(18) 0.0489(8) Uani d . 1 . . H H00E 0.6862 0.0303 0.6276 0.059 Uiso calc R 1 . . C C6 0.7189(2) 0.0998(3) 0.52820(19) 0.0496(8) Uani d . 1 . . H H00F 0.7823 0.0594 0.5432 0.059 Uiso calc R 1 . . C C13 0.4027(2) 0.5119(3) 0.35031(18) 0.0472(7) Uani d . 1 . . H H00G 0.4526 0.5799 0.3632 0.057 Uiso calc R 1 . . C C21 0.4789(2) 0.2766(3) 0.17196(19) 0.0558(8) Uani d . 1 . . H H00H 0.4547 0.3677 0.1675 0.067 Uiso calc R 1 . . C C11 0.2373(2) 0.4457(4) 0.33261(19) 0.0569(9) Uani d . 1 . . H H00I 0.1732 0.4674 0.3339 0.068 Uiso calc R 1 . . C C10 0.2579(2) 0.3166(3) 0.3133(2) 0.0559(9) Uani d . 1 . . H H00J 0.2078 0.2491 0.3005 0.067 Uiso calc R 1 . . C C4 0.5075(2) 0.1240(3) 0.6161(2) 0.0576(9) Uani d . 1 . . H H00A 0.4425 0.1643 0.5901 0.086 Uiso calc R 1 . . H H00C 0.5394 0.1696 0.6692 0.086 Uiso calc R 1 . . H H00K 0.5005 0.0263 0.6257 0.086 Uiso calc R 1 . . C C19 0.6390(2) 0.5320(3) 0.27885(19) 0.0549(8) Uani d . 1 . . H H00L 0.6083 0.494 0.2254 0.066 Uiso calc R 1 . . C C12 0.3087(2) 0.5448(3) 0.3503(2) 0.0588(9) Uani d . 1 . . H H00M 0.2937 0.6355 0.3624 0.071 Uiso calc R 1 . . C C15 0.6703(2) 0.5298(3) 0.4249(2) 0.0622(9) Uani d . 1 . . H H00N 0.6607 0.4902 0.4729 0.075 Uiso calc R 1 . . C C24 0.5466(2) 0.0119(3) 0.1838(2) 0.0622(9) Uani d . 1 . . H H00O 0.5701 -0.0795 0.1877 0.075 Uiso calc R 1 . . C C22 0.4598(3) 0.1955(4) 0.1019(2) 0.0691(10) Uani d . 1 . . H H00P 0.4246 0.2321 0.049 0.083 Uiso calc R 1 . . C C17 0.7428(2) 0.7008(4) 0.3635(2) 0.0667(10) Uani d . 1 . . H H00Q 0.7831 0.7795 0.3688 0.08 Uiso calc R 1 . . C C16 0.7296(3) 0.6428(4) 0.4326(2) 0.0729(11) Uani d . 1 . . H H00R 0.7615 0.6806 0.4859 0.087 Uiso calc R 1 . . C C18 0.6984(3) 0.6463(3) 0.2876(2) 0.0688(10) Uani d . 1 . . H H00S 0.7081 0.6869 0.2399 0.083 Uiso calc R 1 . . C C23 0.4914(3) 0.0631(4) 0.1084(2) 0.0693(10) Uani d . 1 . . H H00T 0.4751 0.0063 0.0606 0.083 Uiso calc R 1 . . H H1O 0.9273(18) 0.064(3) 0.428(2) 0.066(5) Uiso d DU 1 . . H H2O 0.885(2) -0.021(3) 0.4668(19) 0.066(5) Uiso d DU 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br01 0.0568(2) 0.0616(3) 0.0795(3) -0.00858(16) 0.00936(19) 0.01114(18) P1 0.0358(4) 0.0371(4) 0.0295(4) -0.0016(3) 0.0074(3) 0.0022(3) O1 0.0458(12) 0.0766(15) 0.0480(14) 0.0137(10) 0.0190(11) 0.0169(11) O2 0.0466(13) 0.0873(18) 0.0590(16) 0.0061(12) 0.0171(13) 0.0126(13) C14 0.0361(14) 0.0427(16) 0.0336(16) -0.0010(12) 0.0070(12) 0.0020(13) C8 0.0379(15) 0.0407(16) 0.0279(15) -0.0015(12) 0.0061(12) 0.0034(12) C1 0.0392(15) 0.0352(15) 0.0318(16) -0.0015(12) 0.0077(12) 0.0030(12) C20 0.0425(16) 0.0393(16) 0.0337(17) -0.0043(12) 0.0143(13) 0.0009(13) C2 0.0432(16) 0.0359(15) 0.0366(17) -0.0020(12) 0.0111(13) -0.0033(13) C7 0.0415(16) 0.0470(17) 0.0379(17) 0.0002(13) 0.0109(14) 0.0023(14) C25 0.0534(18) 0.0489(18) 0.0432(19) -0.0006(14) 0.0196(15) 0.0016(15) C3 0.0537(18) 0.0382(16) 0.0370(18) -0.0109(13) 0.0147(14) -0.0013(13) C9 0.0467(18) 0.0388(16) 0.056(2) -0.0066(13) 0.0127(15) -0.0048(14) C5 0.063(2) 0.0427(17) 0.0355(18) -0.0017(14) 0.0082(15) 0.0065(14) C6 0.0433(17) 0.0595(19) 0.0411(19) 0.0084(14) 0.0065(15) 0.0083(15) C13 0.0474(17) 0.0415(17) 0.051(2) -0.0024(14) 0.0122(14) -0.0038(14) C21 0.066(2) 0.057(2) 0.038(2) -0.0003(16) 0.0079(16) 0.0021(16) C11 0.0406(17) 0.084(3) 0.045(2) 0.0087(17) 0.0132(15) -0.0012(18) C10 0.0404(18) 0.066(2) 0.058(2) -0.0091(15) 0.0104(15) -0.0016(17) C4 0.074(2) 0.056(2) 0.049(2) -0.0101(17) 0.0279(18) 0.0024(16) C19 0.059(2) 0.063(2) 0.0400(19) -0.0183(16) 0.0108(15) 0.0025(16) C12 0.057(2) 0.058(2) 0.058(2) 0.0113(16) 0.0132(17) -0.0065(17) C15 0.077(2) 0.065(2) 0.039(2) -0.0265(18) 0.0098(17) -0.0017(16) C24 0.076(2) 0.053(2) 0.067(3) -0.0021(17) 0.036(2) -0.0132(19) C22 0.085(3) 0.085(3) 0.0302(19) -0.008(2) 0.0076(17) -0.0041(18) C17 0.057(2) 0.063(2) 0.082(3) -0.0246(17) 0.025(2) -0.005(2) C16 0.074(2) 0.077(3) 0.057(3) -0.033(2) 0.0052(19) -0.013(2) C18 0.076(2) 0.075(3) 0.062(3) -0.030(2) 0.031(2) 0.006(2) C23 0.089(3) 0.079(3) 0.048(2) -0.013(2) 0.033(2) -0.022(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 C1 . 1.788(3) ? P1 C14 . 1.794(3) ? P1 C20 . 1.796(3) ? P1 C8 . 1.797(3) ? O1 C7 . 1.339(3) ? O1 H003 . 0.84 ? O2 H1O . 0.80(3) ? O2 H2O . 0.79(3) ? C14 C19 . 1.372(4) ? C14 C15 . 1.379(4) ? C8 C13 . 1.379(4) ? C8 C9 . 1.391(4) ? C1 C2 . 1.391(4) ? C1 C7 . 1.404(4) ? C20 C25 . 1.380(4) ? C20 C21 . 1.392(4) ? C2 C3 . 1.374(4) ? C2 H009 . 0.95 ? C7 C6 . 1.386(4) ? C25 C24 . 1.377(4) ? C25 H00B . 0.95 ? C3 C5 . 1.393(4) ? C3 C4 . 1.500(4) ? C9 C10 . 1.362(4) ? C9 H00D . 0.95 ? C5 C6 . 1.364(4) ? C5 H00E . 0.95 ? C6 H00F . 0.95 ? C13 C12 . 1.387(4) ? C13 H00G . 0.95 ? C21 C22 . 1.383(4) ? C21 H00H . 0.95 ? C11 C10 . 1.359(4) ? C11 C12 . 1.373(4) ? C11 H00I . 0.95 ? C10 H00J . 0.95 ? C4 H00A . 0.98 ? C4 H00C . 0.98 ? C4 H00K . 0.98 ? C19 C18 . 1.385(4) ? C19 H00L . 0.95 ? C12 H00M . 0.95 ? C15 C16 . 1.376(4) ? C15 H00N . 0.95 ? C24 C23 . 1.370(5) ? C24 H00O . 0.95 ? C22 C23 . 1.364(5) ? C22 H00P . 0.95 ? C17 C18 . 1.353(5) ? C17 C16 . 1.366(5) ? C17 H00Q . 0.95 ? C16 H00R . 0.95 ? C18 H00S . 0.95 ? C23 H00T . 0.95 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 P1 C14 . . 107.97(13) ? C1 P1 C20 . . 112.57(14) ? C14 P1 C20 . . 113.90(13) ? C1 P1 C8 . . 106.38(12) ? C14 P1 C8 . . 110.51(13) ? C20 P1 C8 . . 105.26(12) ? C7 O1 H003 . . 109.5 ? H1O O2 H2O . . 111.(4) ? C19 C14 C15 . . 119.3(3) ? C19 C14 P1 . . 121.5(2) ? C15 C14 P1 . . 119.2(2) ? C13 C8 C9 . . 119.1(3) ? C13 C8 P1 . . 122.1(2) ? C9 C8 P1 . . 118.7(2) ? C2 C1 C7 . . 119.2(3) ? C2 C1 P1 . . 121.8(2) ? C7 C1 P1 . . 118.9(2) ? C25 C20 C21 . . 119.0(3) ? C25 C20 P1 . . 122.4(2) ? C21 C20 P1 . . 118.3(2) ? C3 C2 C1 . . 122.1(3) ? C3 C2 H009 . . 119.0 ? C1 C2 H009 . . 119.0 ? O1 C7 C6 . . 123.9(3) ? O1 C7 C1 . . 117.4(3) ? C6 C7 C1 . . 118.7(3) ? C24 C25 C20 . . 120.2(3) ? C24 C25 H00B . . 119.9 ? C20 C25 H00B . . 119.9 ? C2 C3 C5 . . 117.4(3) ? C2 C3 C4 . . 121.3(3) ? C5 C3 C4 . . 121.3(3) ? C10 C9 C8 . . 120.1(3) ? C10 C9 H00D . . 119.9 ? C8 C9 H00D . . 119.9 ? C6 C5 C3 . . 122.0(3) ? C6 C5 H00E . . 119.0 ? C3 C5 H00E . . 119.0 ? C5 C6 C7 . . 120.6(3) ? C5 C6 H00F . . 119.7 ? C7 C6 H00F . . 119.7 ? C8 C13 C12 . . 120.0(3) ? C8 C13 H00G . . 120.0 ? C12 C13 H00G . . 120.0 ? C22 C21 C20 . . 119.9(3) ? C22 C21 H00H . . 120.0 ? C20 C21 H00H . . 120.0 ? C10 C11 C12 . . 120.2(3) ? C10 C11 H00I . . 119.9 ? C12 C11 H00I . . 119.9 ? C11 C10 C9 . . 120.8(3) ? C11 C10 H00J . . 119.6 ? C9 C10 H00J . . 119.6 ? C3 C4 H00A . . 109.5 ? C3 C4 H00C . . 109.5 ? H00A C4 H00C . . 109.5 ? C3 C4 H00K . . 109.5 ? H00A C4 H00K . . 109.5 ? H00C C4 H00K . . 109.5 ? C14 C19 C18 . . 119.7(3) ? C14 C19 H00L . . 120.2 ? C18 C19 H00L . . 120.2 ? C11 C12 C13 . . 119.7(3) ? C11 C12 H00M . . 120.1 ? C13 C12 H00M . . 120.1 ? C16 C15 C14 . . 120.2(3) ? C16 C15 H00N . . 119.9 ? C14 C15 H00N . . 119.9 ? C23 C24 C25 . . 120.4(3) ? C23 C24 H00O . . 119.8 ? C25 C24 H00O . . 119.8 ? C23 C22 C21 . . 120.2(3) ? C23 C22 H00P . . 119.9 ? C21 C22 H00P . . 119.9 ? C18 C17 C16 . . 120.1(3) ? C18 C17 H00Q . . 120.0 ? C16 C17 H00Q . . 120.0 ? C17 C16 C15 . . 120.0(3) ? C17 C16 H00R . . 120.0 ? C15 C16 H00R . . 120.0 ? C17 C18 C19 . . 120.7(3) ? C17 C18 H00S . . 119.7 ? C19 C18 H00S . . 119.7 ? C22 C23 C24 . . 120.2(3) ? C22 C23 H00T . . 119.9 ? C24 C23 H00T . . 119.9 ?