#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/72/2007275.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_2007275 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 H13 Br2 P S ' _chemical_formula_sum 'C12 H13 Br2 P S' _chemical_formula_weight 380.08 _chemical_name_systematic ; 1-phenyl-2,5-dibromo-3,4-dimethyl-2,5-dihydrophosphole sulfide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90.00 _cell_angle_beta 96.95(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 7.8430(10) _cell_length_b 26.024(3) _cell_length_c 14.003(2) _cell_measurement_reflns_used 5000 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.27 _cell_measurement_theta_min 2.14 _cell_volume 2837.1(6) _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 SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device '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 0.0636 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 21397 _diffrn_reflns_theta_max 24.27 _diffrn_reflns_theta_min 2.14 _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 5.946 _exptl_absorpt_correction_T_max 0.506 _exptl_absorpt_correction_T_min 0.140 _exptl_absorpt_correction_type numerical_(Stoe,_1996c) _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.780 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description 'flat box' _exptl_crystal_F_000 1488 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.754 _refine_diff_density_min -0.590 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.193 _refine_ls_goodness_of_fit_obs 1.531 _refine_ls_hydrogen_treatment 'H atoms riding' _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 4432 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0908 _refine_ls_R_factor_obs .0509 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0424P)^2^+9.9777P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1495 _refine_ls_wR_factor_obs .1416 _reflns_number_observed 2535 _reflns_number_total 4432 _reflns_observed_criterion >2sigma(I) _cod_data_source_file sk1134.cif _cod_data_source_block 3 _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 (18 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 (18 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 (36 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0424P)^2^+9.9777P] 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^)+(0.0424P)^2^+9.9777P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 2837.1(8) _cod_original_sg_symbol_H-M 'P 21/c' _cod_original_formula_sum ' C12 H13 Br2 P S ' _cod_database_code 2007275 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' 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 .0622(7) .0630(7) .0879(8) .0047(6) .0154(6) -.0258(6) Br2 .0528(7) .1130(11) .0925(9) -.0067(8) -.0267(6) -.0155(8) P1 .0443(15) .0385(14) .0478(14) -.0007(12) -.0034(11) -.0051(11) S1 .075(2) .042(2) .078(2) -.0117(15) .006(2) -.0046(14) C1 .045(6) .045(6) .049(6) -.003(5) -.003(5) -.005(5) C2 .053(7) .049(6) .034(5) -.007(5) -.006(5) .001(4) C3 .057(7) .052(7) .044(6) .009(5) -.014(5) .001(5) C4 .051(6) .058(7) .044(6) .003(5) -.011(5) -.009(5) C21 .068(8) .077(8) .057(7) -.008(6) .004(6) .003(6) C31 .104(11) .080(9) .083(8) .037(8) .010(8) .030(7) C111 .044(6) .039(6) .041(5) -.002(5) -.002(4) -.002(4) C112 .132(11) .040(7) .041(6) -.003(7) -.013(6) .003(5) C113 .133(12) .041(7) .062(7) -.009(7) -.023(7) -.008(6) C114 .082(8) .055(7) .044(6) -.004(6) -.013(5) -.006(5) C115 .074(8) .059(7) .038(5) -.013(6) -.003(5) .006(5) C116 .064(7) .039(6) .054(6) -.006(5) -.001(5) .010(5) Br3 .0677(8) .0872(10) .1067(10) .0209(7) .0214(7) -.0241(8) Br4 .0966(10) .0679(8) .0516(6) -.0057(7) .0143(6) .0119(6) P2 .056(2) .042(2) .0430(14) -.0093(13) .0086(12) -.0087(11) S2 .120(3) .042(2) .087(2) -.014(2) .006(2) -.014(2) C11 .051(6) .054(6) .043(5) -.001(5) .017(5) .001(5) C12 .038(5) .040(6) .046(5) -.002(4) .005(4) .000(4) C13 .036(5) .042(6) .045(5) .002(4) .001(4) -.002(4) C14 .045(6) .047(6) .046(5) -.006(5) .007(4) -.011(5) C121 .054(7) .061(8) .086(8) -.011(6) .004(6) .012(6) C131 .067(7) .061(7) .058(6) .000(6) .004(5) -.023(5) C211 .041(6) .051(6) .035(5) -.008(5) .003(4) -.005(4) C212 .055(7) .062(8) .055(6) -.010(6) .006(5) -.001(5) C213 .056(7) .077(8) .072(8) -.002(6) .000(6) .016(7) C214 .041(7) .124(12) .060(7) -.006(7) -.002(5) .006(8) C215 .070(9) .119(12) .059(8) -.013(9) -.002(6) -.025(8) C216 .056(7) .073(8) .057(7) -.012(6) .003(6) -.014(6) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol Br1 .66337(15) .08569(5) .36835(9) .0705(4) Uani d . 1 . Br Br2 1.2035(2) .03907(6) .34680(10) .0890(5) Uani d . 1 . Br P1 .8625(3) .04066(10) .2029(2) .0442(6) Uani d . 1 . P S1 .9220(4) .11095(10) .1788(2) .0652(8) Uani d . 1 . S C1 .6971(12) .0279(3) .2826(6) .047(2) Uani d . 1 . C H1 .5880(12) .0202(3) .2432(6) .057 Uiso calc R 1 . H C2 .7569(13) -.0189(4) .3393(6) .046(2) Uani d . 1 . C C3 .9209(13) -.0319(4) .3381(7) .053(3) Uani d . 1 . C C4 1.0204(12) -.0008(4) .2743(7) .052(3) Uani d . 1 . C H4 1.0716(12) -.0241(4) .2306(7) .063 Uiso calc R 1 . H C21 .6305(14) -.0464(4) .3925(7) .068(3) Uani d . 1 . C H21A .5213(14) -.0294(4) .3816(7) .081 Uiso calc R 1 . H H21B .6704(14) -.0463(4) .4600(7) .081 Uiso calc R 1 . H H21C .6185(14) -.0812(4) .3699(7) .081 Uiso calc R 1 . H C31 1.0116(17) -.0768(5) .3909(9) .089(4) Uani d . 1 . C H31A 1.1291(17) -.0777(5) .3781(9) .107 Uiso calc R 1 . H H31B .9555(17) -.1082(5) .3692(9) .107 Uiso calc R 1 . H H31C 1.0077(17) -.0730(5) .4587(9) .107 Uiso calc R 1 . H C111 .7949(11) .0030(3) .0960(6) .042(2) Uani d . 1 . C C112 .7847(17) -.0495(4) .0980(7) .073(4) Uani d . 1 . C H112 .8118(17) -.0667(4) .1561(7) .087 Uiso calc R 1 . H C113 .7353(17) -.0772(4) .0160(8) .082(4) Uani d . 1 . C H113 .7311(17) -.1129(4) .0186(8) .098 Uiso calc R 1 . H C114 .6920(14) -.0522(4) -.0703(7) .062(3) Uani d . 1 . C H114 .6573(14) -.0709(4) -.1259(7) .075 Uiso calc R 1 . H C115 .7002(14) -.0004(4) -.0737(7) .058(3) Uani d . 1 . C H115 .6714(14) .0167(4) -.1317(7) .069 Uiso calc R 1 . H C116 .7523(13) .0277(4) .0104(7) .053(3) Uani d . 1 . C H116 .7578(13) .0634(4) .0078(7) .064 Uiso calc R 1 . H Br3 .2655(2) .31884(5) .28445(10) .0863(4) Uani d . 1 . Br Br4 .5906(2) .32123(5) .06374(8) .0716(4) Uani d . 1 . Br P2 .6681(3) .30510(10) .2887(2) .0465(6) Uani d . 1 . P S2 .6838(5) .37857(11) .2988(2) .0836(10) Uani d . 1 . S C11 .4664(12) .2738(4) .3088(7) .048(2) Uani d . 1 . C H11 .4755(12) .2614(4) .3753(7) .058 Uiso calc R 1 . H C12 .4487(11) .2293(3) .2422(6) .041(2) Uani d . 1 . C C13 .5440(11) .2303(3) .1715(6) .042(2) Uani d . 1 . C C14 .6656(12) .2744(4) .1702(6) .046(2) Uani d . 1 . C H14 .7806(12) .2614(4) .1631(6) .055 Uiso calc R 1 . H C121 .3206(14) .1881(4) .2592(8) .067(3) Uani d . 1 . C H12A .2678(14) .1964(4) .3156(8) .081 Uiso calc R 1 . H H12B .3784(14) .1557(4) .2680(8) .081 Uiso calc R 1 . H H12C .2341(14) .1862(4) .2046(8) .081 Uiso calc R 1 . H C131 .5411(14) .1903(4) .0916(7) .062(3) Uani d . 1 . C H13A .6226(14) .1997(4) .0487(7) .075 Uiso calc R 1 . H H13B .4282(14) .1888(4) .0565(7) .075 Uiso calc R 1 . H H13C .5709(14) .1573(4) .1192(7) .075 Uiso calc R 1 . H C211 .8279(11) .2710(4) .3687(6) .043(2) Uani d . 1 . C C212 .8665(13) .2190(4) .3577(7) .057(3) Uani d . 1 . C H212 .8107(13) .2007(4) .3061(7) .069 Uiso calc R 1 . H C213 .9861(14) .1948(5) .4224(8) .069(3) Uani d . 1 . C H213 1.0111(14) .1603(5) .4141(8) .083 Uiso calc R 1 . H C214 1.0689(14) .2214(6) .4992(8) .076(4) Uani d . 1 . C H214 1.1494(14) .2048(6) .5429(8) .091 Uiso calc R 1 . H C215 1.0320(16) .2731(6) .5115(9) .084(4) Uani d . 1 . C H215 1.0867(16) .2910(6) .5640(9) .100 Uiso calc R 1 . H C216 .9147(14) .2976(5) .4463(7) .063(3) Uani d . 1 . C H216 .8929(14) .3324(5) .4539(7) .075 Uiso calc R 1 . H 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' S S 0.1246 0.1234 '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' 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 C111 P1 C1 104.2(4) yes C111 P1 C4 104.0(4) yes C1 P1 C4 92.4(4) yes C111 P1 S1 114.9(3) yes C1 P1 S1 118.7(3) yes C4 P1 S1 119.3(3) yes C2 C1 P1 105.6(7) yes C2 C1 Br1 110.8(6) yes P1 C1 Br1 112.9(5) yes C3 C2 C21 125.8(9) yes C3 C2 C1 116.2(9) yes C21 C2 C1 118.0(9) yes C2 C3 C4 116.4(9) yes C2 C3 C31 126.0(10) yes C4 C3 C31 117.5(9) yes C3 C4 P1 106.0(7) yes C3 C4 Br2 112.4(6) yes P1 C4 Br2 112.0(5) yes C211 P2 C11 103.5(4) yes C211 P2 C14 106.1(4) yes C11 P2 C14 91.8(4) yes C211 P2 S2 114.2(3) yes C11 P2 S2 118.7(3) yes C14 P2 S2 119.4(3) yes C12 C11 P2 105.5(6) yes C12 C11 Br3 110.2(6) yes P2 C11 Br3 113.5(5) yes C13 C12 C11 116.2(8) yes C13 C12 C121 125.7(9) yes C11 C12 C121 118.0(8) yes C12 C13 C14 116.5(8) yes C12 C13 C131 125.6(9) yes C14 C13 C131 117.9(8) yes C13 C14 P2 105.1(6) yes C13 C14 Br4 110.7(6) yes P2 C14 Br4 112.7(5) 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 . 1.963(9) yes Br2 C4 . 1.953(9) yes P1 C111 . 1.814(9) yes P1 C1 . 1.841(10) yes P1 C4 . 1.843(10) yes P1 S1 . 1.928(4) yes C1 C2 . 1.498(12) yes C2 C3 . 1.332(13) yes C3 C4 . 1.494(14) yes Br3 C11 . 1.960(10) yes Br4 C14 . 1.960(9) yes P2 C211 . 1.809(9) yes P2 C11 . 1.831(9) yes P2 C14 . 1.840(9) yes P2 S2 . 1.920(4) yes C11 C12 . 1.484(12) yes C12 C13 . 1.311(12) yes C13 C14 . 1.495(12) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139056018