#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/26/2012644.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_2012644 loop_ _publ_author_name 'Rabis, Annegrit' 'Ziemer, Burkhard' 'Wulff-Molder, Dirk' 'Meisel, Manfred' 'Beck, Sebastian' _publ_section_title ; Triorganophosphine--dithiomonometaphosphoryl halides ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o247 _journal_page_last o250 _journal_paper_doi 10.1107/S0108270102004080 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C14 H15 Cl P2 S2' _chemical_formula_sum 'C14 H15 Cl P2 S2' _chemical_formula_weight 344.77 _chemical_name_systematic ; Diphenylmonoethylphosphine-dithiomonometaphosphoryl chloride ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 117.110(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.2040(10) _cell_length_b 9.6940(10) _cell_length_c 13.6550(10) _cell_measurement_reflns_used 5000 _cell_measurement_temperature 190(2) _cell_measurement_theta_max 28.3 _cell_measurement_theta_min 6.9 _cell_volume 1555.8(3) _computing_cell_refinement IPDS _computing_data_collection 'IPDS (Stoe & Cie, 1996)' _computing_data_reduction IPDS _computing_molecular_graphics 'DIAMOND (Brandenburg, 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 190(2) _diffrn_detector_area_resol_mean 6.667 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device 'Stoe IPDS' _diffrn_measurement_method \f _diffrn_radiation_monochromator 'planar graphite' _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.022 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 18747 _diffrn_reflns_theta_full 28.09 _diffrn_reflns_theta_max 28.09 _diffrn_reflns_theta_min 2.69 _diffrn_standards_decay_% 0.0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.702 _exptl_absorpt_correction_T_max 0.875 _exptl_absorpt_correction_T_min 0.659 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details '(ABSCOR; Stoe & Cie, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.41 _refine_diff_density_min -0.37 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 3738 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.030 _refine_ls_R_factor_gt 0.028 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.4476P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.080 _refine_ls_wR_factor_ref 0.081 _reflns_number_gt 3485 _reflns_number_total 3738 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ln1136.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. 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 ; _cod_database_code 2012644 _cod_database_fobs_code 2012644 loop_ _symmetry_equiv_pos_as_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' 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 0.01792(15) 0.0192(2) 0.0192(2) 0.00010(10) 0.00992(12) -0.00047(11) C11 0.0277(6) 0.0260(6) 0.0250(6) -0.0018(5) 0.0144(5) -0.0059(5) C21 0.0299(6) 0.0394(8) 0.0309(7) 0.0020(6) 0.0198(6) -0.0027(6) C12 0.0182(5) 0.0210(5) 0.0212(5) -0.0002(4) 0.0097(4) 0.0006(4) C22 0.0225(6) 0.0283(6) 0.0206(6) -0.0005(5) 0.0092(5) 0.0012(5) C32 0.0280(6) 0.0325(7) 0.0256(6) 0.0015(5) 0.0112(5) 0.0079(5) C42 0.0274(6) 0.0233(6) 0.0366(7) 0.0026(5) 0.0141(5) 0.0063(5) C52 0.0348(7) 0.0238(6) 0.0312(7) 0.0024(5) 0.0165(6) -0.0018(5) C62 0.0307(6) 0.0247(6) 0.0233(6) 0.0029(5) 0.0140(5) 0.0010(5) C13 0.0206(5) 0.0231(6) 0.0225(6) -0.0022(4) 0.0115(4) -0.0007(5) C23 0.0262(6) 0.0234(6) 0.0361(7) -0.0004(5) 0.0154(5) 0.0009(5) C33 0.0317(7) 0.0273(7) 0.0352(7) -0.0058(5) 0.0150(6) 0.0043(6) C43 0.0271(6) 0.0395(8) 0.0282(7) -0.0086(6) 0.0161(5) -0.0011(6) C53 0.0246(6) 0.0355(7) 0.0336(7) -0.0008(5) 0.0175(5) -0.0028(6) C63 0.0230(6) 0.0251(6) 0.0301(6) 0.0004(5) 0.0145(5) -0.0006(5) P2 0.0219(2) 0.0232(2) 0.0205(2) 0.00246(11) 0.00795(12) 0.00144(11) Cl2 0.0459(2) 0.0393(2) 0.0236(2) 0.00746(15) 0.01980(15) 0.00098(13) S12 0.0257(2) 0.0314(2) 0.0414(2) -0.00534(13) 0.00848(15) 0.00362(15) S22 0.0319(2) 0.0238(2) 0.0395(2) 0.00751(12) 0.01640(15) 0.00435(14) 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 P1 0.57851(2) 0.33775(3) 0.80861(2) 0.01820(9) Uani d . 1 . P C11 0.59187(11) 0.24627(14) 0.69960(11) 0.0253(3) Uani d . 1 . C H11A 0.59616 0.14616 0.71535 0.030 Uiso calc R 1 . H H11B 0.52231 0.26257 0.62973 0.030 Uiso calc R 1 . H C21 0.69530(12) 0.2873(2) 0.68391(12) 0.0311(3) Uani d . 1 . C H21A 0.69630 0.2333 0.62367 0.037 Uiso calc R 1 . H H21B 0.76496 0.2691 0.75189 0.037 Uiso calc R 1 . H H21C 0.69098 0.3858 0.66612 0.037 Uiso calc R 1 . H C12 0.55253(10) 0.51783(13) 0.77587(10) 0.0198(2) Uani d . 1 . C C22 0.52019(10) 0.56438(14) 0.66855(10) 0.0241(2) Uani d . 1 . C H22 0.51341 0.50105 0.61279 0.029 Uiso calc R 1 . H C32 0.49810(12) 0.7036(2) 0.64411(12) 0.0291(3) Uani d . 1 . C H32 0.47656 0.7356 0.57152 0.035 Uiso calc R 1 . H C42 0.50735(12) 0.79576(14) 0.72500(13) 0.0293(3) Uani d . 1 . C H42 0.49124 0.89068 0.70756 0.035 Uiso calc R 1 . H C52 0.54016(12) 0.75017(15) 0.83193(12) 0.0294(3) Uani d . 1 . C H52 0.54697 0.81406 0.88735 0.035 Uiso calc R 1 . H C62 0.56288(11) 0.61172(14) 0.85752(11) 0.0256(3) Uani d . 1 . C H62 0.58547 0.58063 0.93053 0.031 Uiso calc R 1 . H C13 0.46268(10) 0.26518(13) 0.82703(10) 0.0215(2) Uani d . 1 . C C23 0.46365(12) 0.12464(14) 0.85078(12) 0.0281(3) Uani d . 1 . C H23 0.52279 0.06686 0.85303 0.034 Uiso calc R 1 . H C33 0.37785(12) 0.0700(2) 0.87103(12) 0.0315(3) Uani d . 1 . C H33 0.37799 -0.0255 0.88671 0.038 Uiso calc R 1 . H C43 0.29182(12) 0.1546(2) 0.86842(12) 0.0303(3) Uani d . 1 . C H43 0.23350 0.1169 0.88278 0.036 Uiso calc R 1 . H C53 0.29073(11) 0.2935(2) 0.84498(12) 0.0296(3) Uani d . 1 . C H53 0.23177 0.3510 0.84350 0.036 Uiso calc R 1 . H C63 0.37566(11) 0.34947(14) 0.82356(11) 0.0251(3) Uani d . 1 . C H63 0.37431 0.44472 0.80664 0.030 Uiso calc R 1 . H P2 0.74202(3) 0.30647(4) 0.96374(3) 0.02250(9) Uani d . 1 . P Cl2 0.67714(3) 0.34038(4) 1.07421(3) 0.03474(10) Uani d . 1 . Cl S12 0.84799(3) 0.45134(4) 0.97461(3) 0.03541(11) Uani d . 1 . S S22 0.77716(3) 0.11146(4) 0.96454(3) 0.03167(10) Uani d . 1 . S 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' Cl Cl 0.1484 0.1585 '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 C12 P1 C13 109.64(6) y C12 P1 C11 110.54(6) y C13 P1 C11 109.31(6) y C12 P1 P2 110.95(4) y C13 P1 P2 109.08(4) y C11 P1 P2 107.27(5) y C21 C11 P1 114.59(10) ? C62 C12 C22 119.82(12) ? C62 C12 P1 119.77(10) ? C22 C12 P1 120.40(10) ? C32 C22 C12 119.66(12) ? C42 C32 C22 120.25(13) ? C32 C42 C52 120.31(13) ? C62 C52 C42 120.03(13) ? C52 C62 C12 119.92(12) ? C63 C13 C23 119.97(12) ? C63 C13 P1 120.37(10) ? C23 C13 P1 119.58(10) ? C33 C23 C13 119.71(13) ? C23 C33 C43 120.16(14) ? C53 C43 C33 120.20(12) ? C43 C53 C63 120.27(13) ? C53 C63 C13 119.69(13) ? S12 P2 S22 122.76(2) y S12 P2 Cl2 110.64(2) y S22 P2 Cl2 109.07(2) y S12 P2 P1 108.87(2) y S22 P2 P1 105.08(2) y Cl2 P2 P1 97.25(2) y C21 C11 H11A 108.5 ? P1 C11 H11A 108.6 ? C21 C11 H11B 108.8 ? P1 C11 H11B 108.6 ? H11A C11 H11B 107.6 ? C11 C21 H21A 109.5 ? C11 C21 H21B 109.7 ? H21A C21 H21B 109.4 ? C11 C21 H21C 109.4 ? H21A C21 H21C 109.4 ? H21B C21 H21C 109.4 ? C32 C22 H22 120.5 ? C12 C22 H22 119.9 ? C33 C23 H23 120.0 ? C13 C23 H23 120.2 ? C42 C32 H32 119.9 ? C22 C32 H32 119.5 ? C23 C33 H33 120.1 ? C43 C33 H33 119.6 ? C32 C42 H42 119.8 ? C52 C42 H42 119.8 ? C53 C43 H43 119.9 ? C33 C43 H43 120.3 ? C62 C52 H52 120.1 ? C42 C52 H52 120.0 ? C43 C53 H53 119.9 ? C63 C53 H53 120.5 ? C52 C62 H62 119.9 ? C12 C62 H62 120.3 ? C53 C63 H63 119.6 ? C13 C63 H63 120.1 ? 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 C12 . 1.7958(13) y P1 C13 . 1.8023(12) y P1 C11 . 1.8090(13) y P1 P2 . 2.2522(5) y C11 C21 . 1.528(2) ? C12 C62 . 1.397(2) ? C12 C22 . 1.401(2) ? C22 C32 . 1.389(2) ? C32 C42 . 1.382(2) ? C42 C52 . 1.392(2) ? C52 C62 . 1.385(2) ? C13 C63 . 1.393(2) ? C13 C23 . 1.399(2) ? C23 C33 . 1.388(2) ? C33 C43 . 1.388(2) ? C43 C53 . 1.383(2) ? C53 C63 . 1.392(2) ? P2 S12 . 1.9399(5) y P2 S22 . 1.9454(5) y P2 Cl2 . 2.0724(5) y C11 H11A . 0.990 ? C11 H11B . 0.990 ? C21 H21A . 0.980 ? C21 H21B . 0.980 ? C21 H21C . 0.980 ? C22 H22 . 0.950 ? C23 H23 . 0.950 ? C32 H32 . 0.950 ? C33 H33 . 0.950 ? C42 H42 . 0.950 ? C43 H43 . 0.950 ? C52 H52 . 0.950 ? C53 H53 . 0.950 ? C62 H62 . 0.950 ? C63 H63 . 0.950 ?