#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/72/2007276.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_2007276 loop_ _publ_author_name 'Tissot, Olivier' 'Gouygou, Maryse' 'Daran, Jean-Claude' 'Balavoine, Gilbert' _publ_section_title ; Key Intermediates in the Synthesis of 2,2'-Biphosphole ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 676 _journal_page_last 679 _journal_paper_doi 10.1107/S0108270197018179 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety ' C12 H12 Br P S ' _chemical_formula_sum 'C12 H12 Br P S' _chemical_formula_weight 299.16 _chemical_name_systematic ; 1-phenyl-2-bromo-3,4-dimethylphosphole sulfide ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 92.61(2) _cell_angle_beta 96.96(2) _cell_angle_gamma 109.53(2) _cell_formula_units_Z 2 _cell_length_a 7.3535(15) _cell_length_b 7.9457(17) _cell_length_c 11.731(2) _cell_measurement_reflns_used 3713 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 24.27 _cell_measurement_theta_min 2.73 _cell_volume 638.5(2) _computing_cell_refinement 'IPDS software' _computing_data_collection 'IPDS software (Stoe, 1996a)' _computing_data_reduction 'X-RED (Stoe, 1996b)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 180(2) _diffrn_measured_fraction_theta_full 0.899 _diffrn_measured_fraction_theta_max 0.899 _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method '\f rotation' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3713 _diffrn_reflns_theta_full 24.27 _diffrn_reflns_theta_max 24.27 _diffrn_reflns_theta_min 2.73 _diffrn_standards_decay_% negligible _diffrn_standards_interval_count 'Area detector used' _diffrn_standards_interval_time 'Area detector used' _diffrn_standards_number '200 for each image' _exptl_absorpt_coefficient_mu 3.473 _exptl_absorpt_correction_T_max 0.311 _exptl_absorpt_correction_T_min 0.157 _exptl_absorpt_correction_type 'numerical (Stoe, 1996c)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 300 _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.64 _exptl_crystal_size_min 0.42 _refine_diff_density_max 0.552 _refine_diff_density_min -0.395 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment 'H atoms riding' _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 1866 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0364 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0411P)^2^+1.8879P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs .0950 _refine_ls_wR_factor_ref 0.0997 _reflns_number_gt 1611 _reflns_number_total 1866 _reflns_threshold_expression >2sigma(I) _cod_data_source_file sk1134.cif _cod_data_source_block 4 _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'YES' changed to 'yes' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_geom_bond_publ_flag' value 'YES' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8 times). '_geom_angle_publ_flag' value 'YES' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (16 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0411P)^2^+1.8879P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0411P)^2^+1.8879P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_formula_sum ' C12 H12 Br P S ' _cod_database_code 2007276 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 Br1 -.01409(8) .98512(7) .15524(4) .0458(2) Uani d . 1 . . Br P1 -.05589(17) .64799(15) .30108(10) .0299(3) Uani d . 1 . . P S1 .21529(19) .66202(18) .31461(11) .0429(3) Uani d . 1 . . S C1 -.1007(7) .8548(6) .2789(4) .0312(10) Uani d . 1 . . C C2 -.1977(7) .8952(6) .3585(4) .0363(11) Uani d . 1 . . C C3 -.2356(7) .7615(7) .4467(4) .0361(11) Uani d . 1 . . C C4 -.1705(7) .6260(6) .4280(4) .0368(11) Uani d . 1 . . C H4 -.1833 .5326 .4749 .044 Uiso calc R 1 . . H C21 -.2643(9) 1.0544(7) .3638(5) .0523(14) Uani d . 1 . . C H21A -.3288 1.0540 .4302 .063 Uiso calc R 1 . . H H21B -.3531 1.0483 .2953 .063 Uiso calc R 1 . . H H21C -.1535 1.1627 .3691 .063 Uiso calc R 1 . . H C31 -.3373(8) .7842(8) .5455(4) .0489(13) Uani d . 1 . . C H31A -.3496 .6863 .5925 .059 Uiso calc R 1 . . H H31B -.4646 .7859 .5169 .059 Uiso calc R 1 . . H H31C -.2633 .8951 .5908 .059 Uiso calc R 1 . . H C111 -.2183(7) .4854(6) .1883(4) .0312(10) Uani d . 1 . . C C112 -.1442(8) .4016(6) .1094(4) .0412(12) Uani d . 1 . . C H112 -.0106 .4248 .1159 .049 Uiso calc R 1 . . H C113 -.2691(9) .2828(7) .0202(5) .0511(14) Uani d . 1 . . C H113 -.2187 .2287 -.0339 .061 Uiso calc R 1 . . H C114 -.4665(9) .2448(7) .0118(5) .0545(15) Uani d . 1 . . C H114 -.5500 .1634 -.0472 .065 Uiso calc R 1 . . H C115 -.5417(8) .3275(7) .0911(5) .0547(15) Uani d . 1 . . C H115 -.6758 .3015 .0850 .066 Uiso calc R 1 . . H C116 -.4195(7) .4479(7) .1788(5) .0443(12) Uani d . 1 . . C H116 -.4706 .5040 .2315 .053 Uiso calc R 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 Br1 .0536(4) .0378(3) .0474(3) .0138(2) .0124(2) .0176(2) P1 .0306(7) .0324(6) .0312(6) .0147(5) .0081(5) .0094(5) S1 .0318(7) .0564(8) .0450(7) .0208(6) .0052(5) .0083(6) C1 .027(2) .030(2) .037(2) .0097(19) .0037(19) .0056(18) C2 .027(3) .037(3) .043(3) .010(2) .000(2) -.002(2) C3 .025(3) .046(3) .034(2) .009(2) .0047(19) .001(2) C4 .038(3) .043(3) .029(2) .012(2) .006(2) .010(2) C21 .054(4) .046(3) .063(4) .027(3) .008(3) -.007(3) C31 .035(3) .066(4) .042(3) .013(3) .009(2) -.003(2) C111 .037(3) .026(2) .033(2) .0111(19) .0109(19) .0144(18) C112 .044(3) .038(3) .045(3) .020(2) .004(2) .002(2) C113 .067(4) .037(3) .053(3) .024(3) .008(3) -.003(2) C114 .054(4) .035(3) .065(4) .008(3) -.005(3) -.004(3) C115 .035(3) .045(3) .071(4) -.002(3) .005(3) .007(3) C116 .031(3) .043(3) .057(3) .008(2) .013(2) .006(2) 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' 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' S S 0.1246 0.1234 '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 _geom_angle_publ_flag C4 P1 C1 90.6(2) yes C4 P1 C111 108.3(2) yes C1 P1 C111 105.6(2) yes C4 P1 S1 118.66(17) yes C1 P1 S1 116.01(16) yes C111 P1 S1 114.69(16) yes C2 C1 P1 111.9(3) yes C2 C1 Br1 127.6(4) yes P1 C1 Br1 120.5(3) yes C1 C2 C3 112.1(4) yes C1 C2 C21 125.9(5) yes C3 C2 C21 122.0(4) yes C4 C3 C31 124.7(5) yes C4 C3 C2 114.4(4) yes C31 C3 C2 120.9(5) yes C3 C4 P1 111.0(3) yes 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 Br1 C1 . 1.871(4) yes P1 C4 . 1.785(5) yes P1 C1 . 1.805(5) yes P1 C111 . 1.810(5) yes P1 S1 . 1.9460(18) yes C1 C2 . 1.331(7) yes C2 C3 . 1.499(7) yes C3 C4 . 1.336(7) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 10448687 2 PubChem 139056019