# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Shigang Wen.' 'Pengfei Li.' 'Haibo Wu.' 'Feng Yu.' 'Xinmiao Liang .' 'Jinxing Ye.' _publ_contact_author_name 'Xinmiao Liang' _publ_contact_author_email liangxm@ecust.edu.cn _publ_section_title ; Enantioselective Organocatalytic Phospha-Michael Reaction of \^I+-, \^I^2^-Unsaturated Ketones ; # Attachment '15ba.cif.txt' data_15ba _database_code_depnum_ccdc_archive 'CCDC 767563' #TrackingRef '15ba.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C19 H21 O2 P' _chemical_formula_sum 'C19 H21 O2 P' _chemical_formula_weight 312.33 _chemical_absolute_configuration R 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 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 6.3328(2) _cell_length_b 9.3463(3) _cell_length_c 28.2033(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1669.30(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9992 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.40 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9111 _exptl_absorpt_correction_T_max 0.9292 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 '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_% none _diffrn_reflns_number 19388 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2953 _reflns_number_gt 2896 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0411P)^2^+0.3067P] 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 0.03(8) _refine_ls_number_reflns 2953 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0781 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 0.97048(6) 0.88037(4) 0.127553(14) 0.03358(12) Uani 1 1 d . . . O1 O 1.20548(17) 0.87240(13) 0.12732(5) 0.0475(3) Uani 1 1 d . . . O2 O 0.9346(3) 1.29037(15) 0.01172(6) 0.0661(4) Uani 1 1 d . . . C1 C 0.8599(3) 0.70211(17) 0.13428(5) 0.0355(3) Uani 1 1 d . . . C2 C 0.6507(3) 0.6664(2) 0.14238(7) 0.0455(4) Uani 1 1 d . . . H2A H 0.5479 0.7375 0.1430 0.055 Uiso 1 1 calc R . . C3 C 0.5948(4) 0.5249(2) 0.14955(7) 0.0532(5) Uani 1 1 d . . . H3A H 0.4546 0.5016 0.1556 0.064 Uiso 1 1 calc R . . C4 C 0.7443(4) 0.4186(2) 0.14779(8) 0.0594(5) Uani 1 1 d . . . H4A H 0.7056 0.3238 0.1528 0.071 Uiso 1 1 calc R . . C5 C 0.9492(4) 0.4525(2) 0.13867(10) 0.0689(6) Uani 1 1 d . . . H5A H 1.0503 0.3804 0.1372 0.083 Uiso 1 1 calc R . . C6 C 1.0082(3) 0.59315(19) 0.13163(7) 0.0532(5) Uani 1 1 d . . . H6A H 1.1485 0.6150 0.1251 0.064 Uiso 1 1 calc R . . C7 C 0.8824(3) 0.99106(19) 0.17687(6) 0.0405(4) Uani 1 1 d . . . C8 C 1.0356(3) 1.0764(2) 0.19760(7) 0.0551(5) Uani 1 1 d . . . H8A H 1.1732 1.0742 0.1861 0.066 Uiso 1 1 calc R . . C9 C 0.9853(4) 1.1650(3) 0.23543(8) 0.0722(7) Uani 1 1 d . . . H9A H 1.0893 1.2220 0.2490 0.087 Uiso 1 1 calc R . . C10 C 0.7844(4) 1.1690(3) 0.25283(8) 0.0709(7) Uani 1 1 d . . . H10A H 0.7517 1.2284 0.2783 0.085 Uiso 1 1 calc R . . C11 C 0.6313(4) 1.0855(3) 0.23274(7) 0.0656(6) Uani 1 1 d . . . H11A H 0.4945 1.0878 0.2447 0.079 Uiso 1 1 calc R . . C12 C 0.6785(3) 0.9977(3) 0.19475(7) 0.0542(5) Uani 1 1 d . . . H12A H 0.5726 0.9425 0.1811 0.065 Uiso 1 1 calc R . . C13 C 0.8694(3) 0.96019(17) 0.07234(5) 0.0335(4) Uani 1 1 d . . . C14 C 0.9163(3) 0.85691(18) 0.03138(6) 0.0465(4) Uani 1 1 d . . . H14A H 1.0650 0.8318 0.0319 0.056 Uiso 1 1 calc R . . H14B H 0.8355 0.7698 0.0358 0.056 Uiso 1 1 calc R . . C15 C 0.8619(4) 0.9216(2) -0.01669(7) 0.0570(5) Uani 1 1 d . . . H15A H 0.7106 0.9370 -0.0185 0.068 Uiso 1 1 calc R . . H15B H 0.9009 0.8549 -0.0415 0.068 Uiso 1 1 calc R . . C16 C 0.9759(4) 1.0636(2) -0.02474(7) 0.0639(6) Uani 1 1 d . . . H16A H 1.1233 1.0442 -0.0316 0.077 Uiso 1 1 calc R . . H16B H 0.9155 1.1102 -0.0523 0.077 Uiso 1 1 calc R . . C17 C 0.9634(3) 1.1628(2) 0.01627(7) 0.0473(4) Uani 1 1 d . . . C18 C 0.9987(3) 1.09862(18) 0.06448(6) 0.0443(4) Uani 1 1 d . . . H18A H 0.9600 1.1681 0.0885 0.053 Uiso 1 1 calc R . . H18B H 1.1476 1.0773 0.0683 0.053 Uiso 1 1 calc R . . C19 C 0.6336(3) 0.9952(2) 0.07531(7) 0.0506(5) Uani 1 1 d . . . H19A H 0.5878 1.0366 0.0459 0.076 Uiso 1 1 calc R . . H19B H 0.6097 1.0620 0.1006 0.076 Uiso 1 1 calc R . . H19C H 0.5554 0.9091 0.0813 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 P1 0.02837(19) 0.0353(2) 0.0370(2) 0.00467(17) -0.00006(15) 0.00131(15) O1 0.0321(6) 0.0526(7) 0.0577(7) 0.0091(7) -0.0012(5) 0.0020(5) O2 0.0681(10) 0.0503(9) 0.0798(10) 0.0260(7) 0.0113(8) 0.0011(7) C1 0.0387(8) 0.0348(8) 0.0329(8) 0.0042(7) -0.0007(7) 0.0027(6) C2 0.0428(10) 0.0382(9) 0.0556(10) 0.0052(8) 0.0022(8) 0.0023(7) C3 0.0533(11) 0.0494(11) 0.0570(11) 0.0068(9) 0.0015(9) -0.0100(9) C4 0.0777(15) 0.0332(10) 0.0675(13) 0.0038(9) -0.0066(11) -0.0049(10) C5 0.0643(13) 0.0371(10) 0.1053(18) -0.0038(11) -0.0056(13) 0.0117(10) C6 0.0463(10) 0.0449(10) 0.0684(12) -0.0018(9) 0.0007(9) 0.0070(8) C7 0.0462(10) 0.0394(9) 0.0359(8) 0.0048(7) -0.0051(7) 0.0010(8) C8 0.0493(11) 0.0596(12) 0.0563(11) -0.0076(9) -0.0097(9) -0.0009(10) C9 0.0744(16) 0.0756(14) 0.0666(13) -0.0246(12) -0.0196(13) -0.0048(13) C10 0.0856(18) 0.0794(15) 0.0476(11) -0.0191(11) -0.0053(11) 0.0167(13) C11 0.0632(13) 0.0878(17) 0.0457(11) -0.0145(11) 0.0072(10) 0.0056(13) C12 0.0516(11) 0.0652(13) 0.0457(10) -0.0087(9) 0.0056(9) -0.0069(10) C13 0.0318(8) 0.0336(8) 0.0350(8) 0.0068(6) 0.0030(6) 0.0008(7) C14 0.0592(11) 0.0384(10) 0.0420(9) -0.0025(7) 0.0009(8) -0.0024(9) C15 0.0735(14) 0.0587(12) 0.0387(10) -0.0007(9) 0.0011(9) -0.0087(11) C16 0.0784(15) 0.0722(13) 0.0410(9) 0.0116(9) 0.0079(10) -0.0147(12) C17 0.0397(9) 0.0481(10) 0.0541(10) 0.0149(8) 0.0066(8) -0.0088(8) C18 0.0518(11) 0.0367(9) 0.0442(9) 0.0027(7) 0.0015(8) -0.0073(8) C19 0.0361(10) 0.0674(13) 0.0483(10) 0.0209(9) 0.0027(8) 0.0074(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4901(11) . ? P1 C1 1.8173(16) . ? P1 C7 1.8210(18) . ? P1 C13 1.8416(16) . ? O2 C17 1.212(2) . ? C1 C2 1.385(2) . ? C1 C6 1.388(2) . ? C2 C3 1.384(3) . ? C2 H2A 0.9300 . ? C3 C4 1.374(3) . ? C3 H3A 0.9300 . ? C4 C5 1.361(4) . ? C4 H4A 0.9300 . ? C5 C6 1.381(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.385(3) . ? C7 C12 1.387(3) . ? C8 C9 1.388(3) . ? C8 H8A 0.9300 . ? C9 C10 1.364(4) . ? C9 H9A 0.9300 . ? C10 C11 1.368(3) . ? C10 H10A 0.9300 . ? C11 C12 1.383(3) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C19 1.531(2) . ? C13 C14 1.534(2) . ? C13 C18 1.547(2) . ? C14 C15 1.524(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.528(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.485(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.503(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 O1 P1 C1 109.86(7) . . ? O1 P1 C7 109.73(8) . . ? C1 P1 C7 108.85(8) . . ? O1 P1 C13 111.33(7) . . ? C1 P1 C13 109.01(7) . . ? C7 P1 C13 108.01(8) . . ? C2 C1 C6 118.68(16) . . ? C2 C1 P1 127.35(13) . . ? C6 C1 P1 113.96(13) . . ? C3 C2 C1 119.93(17) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C4 C3 C2 120.6(2) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C5 C4 C3 119.72(19) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C5 C6 C1 120.50(19) . . ? C5 C6 H6A 119.7 . . ? C1 C6 H6A 119.7 . . ? C8 C7 C12 118.21(18) . . ? C8 C7 P1 115.78(15) . . ? C12 C7 P1 126.01(15) . . ? C7 C8 C9 120.5(2) . . ? C7 C8 H8A 119.8 . . ? C9 C8 H8A 119.8 . . ? C10 C9 C8 120.5(2) . . ? C10 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? C9 C10 C11 119.7(2) . . ? C9 C10 H10A 120.1 . . ? C11 C10 H10A 120.1 . . ? C10 C11 C12 120.4(2) . . ? C10 C11 H11A 119.8 . . ? C12 C11 H11A 119.8 . . ? C11 C12 C7 120.6(2) . . ? C11 C12 H12A 119.7 . . ? C7 C12 H12A 119.7 . . ? C19 C13 C14 111.40(16) . . ? C19 C13 C18 110.18(15) . . ? C14 C13 C18 108.40(13) . . ? C19 C13 P1 112.29(11) . . ? C14 C13 P1 108.32(11) . . ? C18 C13 P1 106.02(11) . . ? C15 C14 C13 112.10(15) . . ? C15 C14 H14A 109.2 . . ? C13 C14 H14A 109.2 . . ? C15 C14 H14B 109.2 . . ? C13 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C14 C15 C16 111.70(17) . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 113.69(16) . . ? C17 C16 H16A 108.8 . . ? C15 C16 H16A 108.8 . . ? C17 C16 H16B 108.8 . . ? C15 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? O2 C17 C16 122.69(18) . . ? O2 C17 C18 120.70(18) . . ? C16 C17 C18 116.55(16) . . ? C17 C18 C13 112.64(14) . . ? C17 C18 H18A 109.1 . . ? C13 C18 H18A 109.1 . . ? C17 C18 H18B 109.1 . . ? C13 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? C13 C19 H19A 109.5 . . ? C13 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C13 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 O1 P1 C1 C2 170.71(15) . . . . ? C7 P1 C1 C2 50.54(17) . . . . ? C13 P1 C1 C2 -67.05(17) . . . . ? O1 P1 C1 C6 -7.98(15) . . . . ? C7 P1 C1 C6 -128.15(14) . . . . ? C13 P1 C1 C6 114.25(14) . . . . ? C6 C1 C2 C3 2.6(3) . . . . ? P1 C1 C2 C3 -176.03(15) . . . . ? C1 C2 C3 C4 -1.3(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C4 C5 C6 C1 0.7(4) . . . . ? C2 C1 C6 C5 -2.3(3) . . . . ? P1 C1 C6 C5 176.49(18) . . . . ? O1 P1 C7 C8 15.76(16) . . . . ? C1 P1 C7 C8 136.00(14) . . . . ? C13 P1 C7 C8 -105.77(14) . . . . ? O1 P1 C7 C12 -164.78(17) . . . . ? C1 P1 C7 C12 -44.53(19) . . . . ? C13 P1 C7 C12 73.69(19) . . . . ? C12 C7 C8 C9 0.4(3) . . . . ? P1 C7 C8 C9 179.94(17) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C9 C10 C11 C12 -0.4(4) . . . . ? C10 C11 C12 C7 1.0(4) . . . . ? C8 C7 C12 C11 -1.0(3) . . . . ? P1 C7 C12 C11 179.52(17) . . . . ? O1 P1 C13 C19 -169.34(13) . . . . ? C1 P1 C13 C19 69.31(15) . . . . ? C7 P1 C13 C19 -48.81(15) . . . . ? O1 P1 C13 C14 67.21(13) . . . . ? C1 P1 C13 C14 -54.13(13) . . . . ? C7 P1 C13 C14 -172.26(12) . . . . ? O1 P1 C13 C18 -48.96(13) . . . . ? C1 P1 C13 C18 -170.31(11) . . . . ? C7 P1 C13 C18 71.57(13) . . . . ? C19 C13 C14 C15 62.8(2) . . . . ? C18 C13 C14 C15 -58.6(2) . . . . ? P1 C13 C14 C15 -173.20(13) . . . . ? C13 C14 C15 C16 56.0(2) . . . . ? C14 C15 C16 C17 -46.9(3) . . . . ? C15 C16 C17 O2 -139.0(2) . . . . ? C15 C16 C17 C18 43.9(3) . . . . ? O2 C17 C18 C13 134.99(18) . . . . ? C16 C17 C18 C13 -47.8(2) . . . . ? C19 C13 C18 C17 -68.8(2) . . . . ? C14 C13 C18 C17 53.37(19) . . . . ? P1 C13 C18 C17 169.49(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.243 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.033 # Attachment '20ca.cif.txt' data_pbrbf _database_code_depnum_ccdc_archive 'CCDC 767564' #TrackingRef '20ca.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_absolute_configuration R _chemical_formula_moiety 'C22 H20 Br O2 P' _chemical_formula_sum 'C22 H20 Br O2 P' _chemical_formula_weight 427.26 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' Br Br -0.2901 2.4595 '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 C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 19.698(4) _cell_length_b 5.7772(13) _cell_length_c 17.469(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.705(4) _cell_angle_gamma 90.00 _cell_volume 1983.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 889 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 18.87 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 2.166 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8126 _exptl_absorpt_correction_T_max 0.8994 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 '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_% none _diffrn_reflns_number 3306 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0763 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 20.80 _reflns_number_total 1965 _reflns_number_gt 1596 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0000P)^2^+4.3491P] 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 0.05(2) _refine_ls_number_reflns 1965 _refine_ls_number_parameters 235 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 Br Br 0.47871(5) 0.1435(4) 0.10635(6) 0.1251(6) Uani 1 1 d . . . P P 0.16893(9) 0.3508(4) 0.27021(11) 0.0384(5) Uani 1 1 d . . . O1 O 0.1847(2) 0.6050(9) 0.2794(3) 0.0534(14) Uani 1 1 d . . . O2 O 0.3072(3) -0.1321(14) 0.4223(3) 0.0640(16) Uani 1 1 d . . . C1 C 0.4046(4) 0.150(2) 0.1710(4) 0.064(2) Uani 1 1 d . . . C2 C 0.3956(4) 0.345(2) 0.2165(5) 0.066(3) Uani 1 1 d . . . H2 H 0.4258 0.4687 0.2157 0.080 Uiso 1 1 calc R . . C3 C 0.3411(4) 0.3516(18) 0.2631(5) 0.054(2) Uani 1 1 d . . . H3 H 0.3341 0.4813 0.2932 0.065 Uiso 1 1 calc R . . C4 C 0.2967(3) 0.1635(15) 0.2648(4) 0.0353(17) Uani 1 1 d . . . C5 C 0.3086(4) -0.0234(16) 0.2194(4) 0.049(2) Uani 1 1 d . . . H5 H 0.2794 -0.1496 0.2201 0.059 Uiso 1 1 calc R . . C6 C 0.3622(5) -0.0315(18) 0.1725(5) 0.062(2) Uani 1 1 d . . . H6 H 0.3689 -0.1611 0.1424 0.075 Uiso 1 1 calc R . . C7 C 0.2359(3) 0.1620(14) 0.3140(3) 0.0327(16) Uani 1 1 d . . . H7 H 0.2180 0.0038 0.3144 0.039 Uiso 1 1 calc R . . C8 C 0.2542(4) 0.2339(12) 0.3974(4) 0.045(2) Uani 1 1 d . . . H8A H 0.2728 0.3894 0.3980 0.054 Uiso 1 1 calc R . . H8B H 0.2131 0.2369 0.4251 0.054 Uiso 1 1 calc R . . C9 C 0.3047(4) 0.0742(19) 0.4378(4) 0.051(2) Uani 1 1 d . . . C10 C 0.3510(4) 0.1757(19) 0.5000(4) 0.072(3) Uani 1 1 d . . . H10A H 0.3805 0.0573 0.5217 0.107 Uiso 1 1 calc R . . H10B H 0.3244 0.2387 0.5392 0.107 Uiso 1 1 calc R . . H10C H 0.3777 0.2964 0.4791 0.107 Uiso 1 1 calc R . . C11 C 0.0910(4) 0.2760(13) 0.3149(4) 0.038(2) Uani 1 1 d . . . C12 C 0.0801(4) 0.0655(14) 0.3515(5) 0.051(2) Uani 1 1 d . . . H12 H 0.1129 -0.0503 0.3516 0.061 Uiso 1 1 calc R . . C13 C 0.0205(4) 0.0290(15) 0.3877(5) 0.059(3) Uani 1 1 d . . . H13 H 0.0144 -0.1096 0.4135 0.071 Uiso 1 1 calc R . . C14 C -0.0289(4) 0.1907(17) 0.3863(4) 0.057(2) Uani 1 1 d . . . H14 H -0.0687 0.1624 0.4106 0.068 Uiso 1 1 calc R . . C15 C -0.0207(4) 0.3998(15) 0.3485(5) 0.058(3) Uani 1 1 d . . . H15 H -0.0548 0.5112 0.3470 0.070 Uiso 1 1 calc R . . C16 C 0.0388(4) 0.4391(14) 0.3132(5) 0.056(2) Uani 1 1 d . . . H16 H 0.0443 0.5783 0.2877 0.067 Uiso 1 1 calc R . . C17 C 0.1597(4) 0.2644(13) 0.1715(4) 0.040(2) Uani 1 1 d . . . C18 C 0.1848(5) 0.4028(16) 0.1168(5) 0.074(3) Uani 1 1 d . . . H18 H 0.2045 0.5438 0.1312 0.089 Uiso 1 1 calc R . . C19 C 0.1815(6) 0.339(2) 0.0410(5) 0.106(4) Uani 1 1 d . . . H19 H 0.1992 0.4359 0.0048 0.127 Uiso 1 1 calc R . . C20 C 0.1530(5) 0.136(2) 0.0188(4) 0.085(3) Uani 1 1 d . . . H20 H 0.1496 0.0945 -0.0328 0.102 Uiso 1 1 calc R . . C21 C 0.1290(5) -0.0095(19) 0.0728(5) 0.085(3) Uani 1 1 d . . . H21 H 0.1110 -0.1526 0.0579 0.101 Uiso 1 1 calc R . . C22 C 0.1310(5) 0.0536(15) 0.1494(5) 0.067(3) Uani 1 1 d . . . H22 H 0.1134 -0.0441 0.1856 0.080 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 Br 0.0680(7) 0.2289(16) 0.0830(8) 0.0114(11) 0.0394(6) -0.0072(10) P 0.0391(11) 0.0330(12) 0.0430(11) 0.0025(11) 0.0026(9) -0.0006(11) O1 0.055(3) 0.036(4) 0.070(3) 0.000(3) 0.004(3) -0.008(3) O2 0.072(4) 0.056(4) 0.064(4) -0.002(4) -0.004(3) 0.014(4) C1 0.041(5) 0.093(7) 0.059(6) 0.004(7) 0.015(4) 0.010(7) C2 0.049(6) 0.071(6) 0.079(6) 0.025(7) 0.003(5) -0.016(6) C3 0.040(5) 0.050(5) 0.072(6) -0.008(6) 0.007(5) -0.004(5) C4 0.032(4) 0.034(4) 0.039(4) 0.004(5) -0.003(3) 0.001(5) C5 0.050(6) 0.037(4) 0.061(5) -0.003(5) 0.013(5) -0.001(4) C6 0.066(6) 0.068(6) 0.055(6) -0.019(5) 0.020(5) -0.001(6) C7 0.030(4) 0.031(4) 0.038(4) -0.007(4) 0.003(3) 0.003(4) C8 0.052(5) 0.041(5) 0.043(5) 0.004(4) -0.003(4) 0.005(4) C9 0.039(5) 0.080(8) 0.035(5) 0.006(5) 0.007(4) 0.003(5) C10 0.077(6) 0.070(6) 0.065(5) 0.009(6) -0.012(5) -0.008(6) C11 0.035(5) 0.037(6) 0.043(5) -0.004(4) 0.000(4) 0.003(4) C12 0.041(5) 0.040(6) 0.072(6) -0.001(5) 0.011(5) 0.008(4) C13 0.044(6) 0.061(7) 0.076(6) 0.016(5) 0.020(5) 0.007(5) C14 0.039(5) 0.071(7) 0.063(6) 0.004(6) 0.014(4) -0.007(6) C15 0.040(5) 0.056(9) 0.080(6) 0.010(5) 0.015(5) 0.018(5) C16 0.058(6) 0.045(6) 0.065(6) 0.003(4) 0.000(5) 0.009(5) C17 0.037(5) 0.045(6) 0.039(5) 0.004(4) 0.000(4) 0.001(4) C18 0.122(8) 0.055(8) 0.045(6) 0.008(5) 0.000(6) -0.035(6) C19 0.176(12) 0.094(8) 0.051(7) 0.002(7) 0.028(7) -0.071(10) C20 0.137(9) 0.083(8) 0.035(5) 0.002(7) 0.007(5) -0.026(8) C21 0.111(8) 0.075(7) 0.066(7) -0.010(7) -0.002(6) -0.036(7) C22 0.106(8) 0.059(7) 0.037(5) -0.005(5) 0.010(5) -0.028(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 Br C1 1.903(7) . ? P O1 1.508(5) . ? P C17 1.793(8) . ? P C11 1.819(8) . ? P C7 1.840(7) . ? O2 C9 1.224(10) . ? C1 C6 1.342(13) . ? C1 C2 1.397(14) . ? C2 C3 1.391(10) . ? C2 H2 0.9300 . ? C3 C4 1.396(12) . ? C3 H3 0.9300 . ? C4 C5 1.369(10) . ? C4 C7 1.518(8) . ? C5 C6 1.378(11) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.535(8) . ? C7 H7 0.9800 . ? C8 C9 1.500(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.492(11) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.393(10) . ? C11 C12 1.397(10) . ? C12 C13 1.385(10) . ? C12 H12 0.9300 . ? C13 C14 1.348(11) . ? C13 H13 0.9300 . ? C14 C15 1.391(12) . ? C14 H14 0.9300 . ? C15 C16 1.377(10) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.363(10) . ? C17 C22 1.387(10) . ? C18 C19 1.373(11) . ? C18 H18 0.9300 . ? C19 C20 1.346(15) . ? C19 H19 0.9300 . ? C20 C21 1.371(13) . ? C20 H20 0.9300 . ? C21 C22 1.385(11) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? 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 O1 P C17 112.4(3) . . ? O1 P C11 111.1(3) . . ? C17 P C11 108.1(3) . . ? O1 P C7 113.3(3) . . ? C17 P C7 105.1(3) . . ? C11 P C7 106.5(3) . . ? C6 C1 C2 121.1(7) . . ? C6 C1 Br 119.9(9) . . ? C2 C1 Br 118.9(8) . . ? C3 C2 C1 119.1(9) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120.0(9) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 118.1(7) . . ? C5 C4 C7 119.6(7) . . ? C3 C4 C7 122.3(7) . . ? C4 C5 C6 122.5(8) . . ? C4 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C1 C6 C5 119.2(9) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C4 C7 C8 113.0(5) . . ? C4 C7 P 109.4(4) . . ? C8 C7 P 110.6(5) . . ? C4 C7 H7 107.9 . . ? C8 C7 H7 107.9 . . ? P C7 H7 107.9 . . ? C9 C8 C7 112.8(6) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? O2 C9 C10 120.8(8) . . ? O2 C9 C8 122.0(7) . . ? C10 C9 C8 117.2(9) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 117.6(7) . . ? C16 C11 P 118.2(6) . . ? C12 C11 P 124.2(6) . . ? C13 C12 C11 120.1(7) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 121.2(8) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 120.3(7) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 118.9(7) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C11 121.8(8) . . ? C15 C16 H16 119.1 . . ? C11 C16 H16 119.1 . . ? C18 C17 C22 118.7(7) . . ? C18 C17 P 119.4(6) . . ? C22 C17 P 121.8(6) . . ? C17 C18 C19 121.4(8) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C20 C19 C18 120.4(9) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 119.4(8) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C20 C21 C22 121.0(9) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C21 C22 C17 119.1(9) . . ? C21 C22 H22 120.5 . . ? C17 C22 H22 120.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 20.80 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.239 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.054