#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202185.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2202185 loop_ _publ_author_name 'Michael L. Williams' 'Peter C. Healy' 'Nicholas K. Loh' 'Samuel P. C. Dunstan' 'Graham Smith' _publ_section_title ; 1-(Diphenylphosphino)-4-(diphenylphosphinoyl)butane ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o596 _journal_page_last o598 _journal_paper_doi 10.1107/S1600536803006561 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C28 H28 O P2' _chemical_formula_moiety 'C28 H28 O P2' _chemical_formula_sum 'C28 H28 O P2' _chemical_formula_weight 442.44 _chemical_melting_point 463.5(5) _chemical_name_common ; 1,4-bis(diphenylphosphino)butane half oxide ; _chemical_name_systematic ; 1-(Diphenylphosphino)-4-(diphenylphosphinoyl)butane ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 102.98(2) _cell_angle_beta 102.23(3) _cell_angle_gamma 100.71(2) _cell_formula_units_Z 1 _cell_length_a 8.927(2) _cell_length_b 12.514(3) _cell_length_c 5.802(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 17.2 _cell_measurement_theta_min 12.6 _cell_volume 598.4(3) _computing_cell_refinement ; MSC/AFC Diffractometer Control Software ; _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999) ; _computing_data_reduction ; TEXSAN for Windows (Molecular Structure Corporation, 1999). ; _computing_molecular_graphics 'PLATON for Windows (Spek, 1999)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku AFC-7R' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator ' graphite' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'MoK\a ' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.038 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_number 3238 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.6 _diffrn_standards_decay_% 0.54 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.20 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 234 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.28 _refine_diff_density_min -0.28 _refine_ls_goodness_of_fit_ref 0.86 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 2752 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.86 _refine_ls_R_factor_all 0.069 _refine_ls_R_factor_gt 0.048 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1P)^2^+0.507P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.137 _refine_ls_wR_factor_ref 0.154 _reflns_number_gt 2133 _reflns_number_total 2752 _reflns_threshold_expression I>2\s(I) _cod_data_source_file tk6098.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '463 -- 464' was changed to '463.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '463 -- 464' was changed to '463.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 598.5(3) _cod_database_code 2202185 _cod_database_fobs_code 2202185 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _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 _atom_site_type_symbol P1 0.65422(6) 0.83393(5) 0.03061(11) 0.0430(2) Uani d . 1 . . P O1 0.6811(5) 0.8512(3) 0.2806(6) 0.0645(9) Uani d P 0.50 . . O C1A 0.6990(2) 0.70021(18) -0.1015(4) 0.0462(5) Uani d . 1 . . C C1B 0.4514(2) 0.81581(17) -0.1441(4) 0.0416(5) Uani d . 1 . . C C2A 0.6673(4) 0.6513(2) -0.3496(6) 0.0734(8) Uani d . 1 . . C C2B 0.3325(3) 0.7541(2) -0.0705(5) 0.0579(6) Uani d . 1 . . C C3A 0.7037(5) 0.5488(3) -0.4348(7) 0.0904(11) Uani d . 1 . . C C3B 0.1752(3) 0.7383(2) -0.1886(7) 0.0725(9) Uani d . 1 . . C C4A 0.7705(5) 0.4955(3) -0.2796(9) 0.0884(11) Uani d . 1 . . C C4B 0.1349(3) 0.7840(3) -0.3795(6) 0.0742(9) Uani d . 1 . . C C5A 0.8059(5) 0.5434(3) -0.0369(9) 0.0923(12) Uani d . 1 . . C C5B 0.2503(3) 0.8458(3) -0.4539(5) 0.0712(8) Uani d . 1 . . C C6A 0.7702(4) 0.6462(3) 0.0565(6) 0.0698(8) Uani d . 1 . . C C6B 0.4085(3) 0.8611(2) -0.3378(5) 0.0570(6) Uani d . 1 . . C C11 0.7732(2) 0.93418(16) -0.0831(4) 0.0400(4) Uani d . 1 . . C C21 0.9487(2) 0.95868(17) 0.0481(4) 0.0417(5) Uani d . 1 . . C H2A 0.6210 0.6881 -0.4617 0.088 Uiso d . 1 . . H H2B 0.3597 0.7231 0.0631 0.068 Uiso d . 1 . . H H3A 0.6798 0.5155 -0.6059 0.108 Uiso d . 1 . . H H3B 0.0951 0.6949 -0.1406 0.087 Uiso d . 1 . . H H4A 0.7934 0.4253 -0.3382 0.106 Uiso d . 1 . . H H4B 0.0266 0.7743 -0.4597 0.087 Uiso d . 1 . . H H5A 0.8556 0.5077 0.0770 0.111 Uiso d . 1 . . H H5B 0.2216 0.8770 -0.5865 0.084 Uiso d . 1 . . H H6A 0.7950 0.6790 0.2286 0.083 Uiso d . 1 . . H H6B 0.4874 0.9032 -0.3912 0.067 Uiso d . 1 . . H H11A 0.7400 0.9921 -0.0584 0.044 Uiso d . 1 . . H H11B 0.7570 0.8937 -0.2792 0.044 Uiso d . 1 . . H H21A 0.9755 0.8818 0.0023 0.044 Uiso d . 1 . . H H21B 0.9634 1.0103 0.2240 0.044 Uiso d . 1 . . H 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 P1 0.0383(3) 0.0411(3) 0.0502(3) 0.0063(2) 0.0115(2) 0.0167(2) O1 0.077(2) 0.065(2) 0.0479(19) 0.0127(18) 0.0167(17) 0.0124(17) C1A 0.0387(10) 0.0375(10) 0.0627(14) 0.0059(8) 0.0129(9) 0.0178(10) C1B 0.0364(10) 0.0387(10) 0.0489(11) 0.0091(8) 0.0155(8) 0.0065(9) C2A 0.098(2) 0.0522(15) 0.0722(18) 0.0282(15) 0.0218(16) 0.0150(13) C2B 0.0476(13) 0.0491(13) 0.0816(18) 0.0100(10) 0.0287(12) 0.0177(12) C3A 0.125(3) 0.0554(17) 0.097(3) 0.0284(18) 0.049(2) 0.0091(17) C3B 0.0426(13) 0.0546(15) 0.114(3) 0.0030(11) 0.0322(15) 0.0065(16) C4A 0.102(3) 0.0486(16) 0.138(3) 0.0318(16) 0.064(2) 0.0294(19) C4B 0.0378(12) 0.0668(17) 0.093(2) 0.0117(12) 0.0041(13) -0.0143(16) C5A 0.097(3) 0.075(2) 0.137(3) 0.050(2) 0.042(2) 0.057(2) C5B 0.0582(16) 0.087(2) 0.0616(16) 0.0295(15) 0.0012(13) 0.0102(15) C6A 0.0722(18) 0.0657(17) 0.0789(19) 0.0264(14) 0.0154(15) 0.0313(15) C6B 0.0448(12) 0.0708(16) 0.0574(14) 0.0155(11) 0.0128(10) 0.0213(12) C11 0.0353(10) 0.0344(10) 0.0513(12) 0.0081(8) 0.0125(8) 0.0132(8) C21 0.0346(10) 0.0363(10) 0.0537(12) 0.0076(8) 0.0115(9) 0.0127(9) 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' P P 0.1023 0.0942 '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' 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 O1 P1 C1A . . 108.97(19) no O1 P1 C1B . . 117.0(2) no O1 P1 C11 . . 118.56(19) no C1A P1 C1B . . 102.84(10) no C1A P1 C11 . . 102.76(10) no C1B P1 C11 . . 104.76(10) no P1 C1A C2A . . 123.81(19) no P1 C1A C6A . . 118.1(2) no C2A C1A C6A . . 118.1(2) no P1 C1B C2B . . 116.70(18) no P1 C1B C6B . . 124.72(18) no C2B C1B C6B . . 118.6(2) no C1A C2A C3A . . 120.1(3) no C1B C2B C3B . . 120.7(2) no C2A C3A C4A . . 121.4(4) no C2B C3B C4B . . 119.9(3) no C3A C4A C5A . . 119.3(4) no C3B C4B C5B . . 120.3(3) no C4A C5A C6A . . 121.1(4) no C4B C5B C6B . . 120.1(3) no C1A C6A C5A . . 119.9(3) no C1B C6B C5B . . 120.4(3) no P1 C11 C21 . . 111.04(15) no C11 C21 C21 . 2_775 111.89(18) no C1A C2A H2A . . 119.55 no C3A C2A H2A . . 120.30 no C1B C2B H2B . . 119.71 no C3B C2B H2B . . 119.58 no C2A C3A H3A . . 119.29 no C4A C3A H3A . . 119.30 no C2B C3B H3B . . 120.41 no C4B C3B H3B . . 119.64 no C3A C4A H4A . . 121.13 no C5A C4A H4A . . 119.61 no C3B C4B H4B . . 120.19 no C5B C4B H4B . . 119.52 no C4A C5A H5A . . 120.68 no C6A C5A H5A . . 118.20 no C4B C5B H5B . . 119.84 no C6B C5B H5B . . 120.03 no C1A C6A H6A . . 119.70 no C5A C6A H6A . . 120.39 no C1B C6B H6B . . 119.99 no C5B C6B H6B . . 119.62 no P1 C11 H11A . . 106.17 no P1 C11 H11B . . 106.70 no C21 C11 H11A . . 111.35 no C21 C11 H11B . . 108.18 no H11A C11 H11B . . 113.32 no C11 C21 H21A . . 103.89 no C11 C21 H21B . . 106.15 no H21A C21 H21B . . 127.48 no C21 C21 H21A 2_775 . 108.14 no C21 C21 H21B 2_775 . 99.18 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 O1 . . 1.379(3) no P1 C1A . . 1.830(2) no P1 C1B . . 1.823(2) no P1 C11 . . 1.820(2) no C1A C2A . . 1.376(4) no C1A C6A . . 1.376(4) no C1B C2B . . 1.393(3) no C1B C6B . . 1.384(3) no C2A C3A . . 1.390(5) no C2B C3B . . 1.382(4) no C3A C4A . . 1.342(6) no C3B C4B . . 1.369(5) no C4A C5A . . 1.343(7) no C4B C5B . . 1.374(5) no C5A C6A . . 1.401(6) no C5B C6B . . 1.387(4) no C11 C21 . . 1.529(3) no C21 C21 . 2_775 1.531(3) no C2A H2A . . 0.9473 no C2B H2B . . 0.9490 no C3A H3A . . 0.9466 no C3B H3B . . 0.9444 no C4A H4A . . 0.9440 no C4B H4B . . 0.9520 no C5A H5A . . 0.9567 no C5B H5B . . 0.9479 no C6A H6A . . 0.9503 no C6B H6B . . 0.9474 no C11 H11A . . 0.8276 no C11 H11B . . 1.1028 no C21 H21A . . 1.0252 no C21 H21B . . 1.0448 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C6A H6A O1 . 0.95 2.53 2.933(6) 105 no C11 H11B O1 1_554 1.10 2.41 3.473(4) 163 no 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_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 P1 C1A C2A . . 172.1(3) no O1 P1 C1A C6A . . -8.7(3) no C1B P1 C1A C2A . . 47.3(2) no C1B P1 C1A C6A . . -133.5(2) no C11 P1 C1A C2A . . -61.3(2) no C11 P1 C1A C6A . . 117.9(2) no O1 P1 C1B C2B . . -38.2(3) no O1 P1 C1B C6B . . 140.1(3) no C1A P1 C1B C2B . . 81.2(2) no C1A P1 C1B C6B . . -100.6(2) no C11 P1 C1B C2B . . -171.73(18) no C11 P1 C1B C6B . . 6.5(2) no O1 P1 C11 C21 . . 47.2(3) no C1A P1 C11 C21 . . -73.00(16) no C1B P1 C11 C21 . . 179.82(17) no P1 C1A C6A C5A . . 179.7(3) no P1 C1A C2A C3A . . -179.3(3) no C6A C1A C2A C3A . . 1.5(5) no C2A C1A C6A C5A . . -1.0(5) no P1 C1B C2B C3B . . 178.5(2) no C6B C1B C2B C3B . . 0.1(4) no C2B C1B C6B C5B . . 0.5(4) no P1 C1B C6B C5B . . -177.7(2) no C1A C2A C3A C4A . . -0.3(6) no C1B C2B C3B C4B . . -0.3(5) no C2A C3A C4A C5A . . -1.4(7) no C2B C3B C4B C5B . . -0.2(5) no C3A C4A C5A C6A . . 1.8(7) no C3B C4B C5B C6B . . 0.8(5) no C4A C5A C6A C1A . . -0.6(6) no C4B C5B C6B C1B . . -1.0(5) no P1 C11 C21 C21 . 2_775 178.99(15) no C11 C21 C21 C11 2_775 2_775 180.0(4) no