#------------------------------------------------------------------------------ #$Date: 2019-12-09 12:31:12 +0200 (Mon, 09 Dec 2019) $ #$Revision: 244962 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/64/1556479.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1556479 loop_ _publ_author_name 'Koch, A.' 'Krieck, S.' 'Gorls, H.' 'Westerhausen, M.' _publ_section_title ; Reduction of Bromo- and Iodo-2,6-bis(diphenylphosphanylmethyl)benzene with Magnesium and Calcium ; _journal_name_full Inorganics _journal_page_first 39 _journal_paper_doi 10.3390/inorganics4040039 _journal_volume 4 _journal_year 2016 _chemical_formula_moiety 'C32 H27 Br P2' _chemical_formula_sum 'C32 H27 Br P2' _chemical_formula_weight 553.39 _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 104.318(2) _cell_angle_beta 106.891(2) _cell_angle_gamma 95.661(2) _cell_formula_units_Z 2 _cell_length_a 9.3025(3) _cell_length_b 10.1879(4) _cell_length_c 15.2499(6) _cell_measurement_reflns_used 14817 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 27.65 _cell_measurement_theta_min 2.31 _cell_volume 1317.12(9) _computing_cell_refinement DENZO _computing_data_collection COLLECT _computing_data_reduction DENZO _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 133(2) _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _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 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 14817 _diffrn_reflns_theta_full 27.65 _diffrn_reflns_theta_max 27.65 _diffrn_reflns_theta_min 2.31 _exptl_absorpt_coefficient_mu 1.701 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker-AXS, 2002' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.048 _exptl_crystal_size_mid 0.042 _exptl_crystal_size_min 0.038 _refine_diff_density_max 0.408 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.068 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 424 _refine_ls_number_reflns 5981 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0380 _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^)+(0.0182P)^2^+1.6553P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0806 _refine_ls_wR_factor_ref 0.0863 _reflns_number_gt 5142 _reflns_number_total 5981 _reflns_threshold_expression >2sigma(I) _cod_data_source_file inorganics-2016-4-39.cif _cod_data_source_block FO5472 _cod_original_cell_volume 1317.12(8) _cod_database_code 1556479 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 Br1 Br 0.21403(3) 0.26044(3) 0.264453(18) 0.02939(8) Uani 1 1 d . . . P1 P 0.29852(8) 0.20225(7) 0.52580(5) 0.02716(15) Uani 1 1 d . . . P2 P 0.44307(7) 0.29732(6) 0.10849(4) 0.02181(13) Uani 1 1 d . . . C1 C 0.4232(3) 0.2566(2) 0.32922(17) 0.0220(5) Uani 1 1 d . . . C2 C 0.5130(3) 0.2079(2) 0.27307(17) 0.0226(5) Uani 1 1 d . . . C3 C 0.6655(3) 0.2075(3) 0.32230(19) 0.0262(5) Uani 1 1 d . . . H3 H 0.731(3) 0.179(3) 0.287(2) 0.033(8) Uiso 1 1 d . . . C4 C 0.7225(3) 0.2493(3) 0.4207(2) 0.0302(6) Uani 1 1 d . . . H4 H 0.822(3) 0.246(3) 0.451(2) 0.035(8) Uiso 1 1 d . . . C5 C 0.6291(3) 0.2940(3) 0.47382(19) 0.0283(5) Uani 1 1 d . . . H5 H 0.666(3) 0.323(3) 0.542(2) 0.036(8) Uiso 1 1 d . . . C6 C 0.4765(3) 0.2988(2) 0.42872(17) 0.0230(5) Uani 1 1 d . . . C7 C 0.4529(3) 0.1552(2) 0.16581(17) 0.0230(5) Uani 1 1 d . . . H7B H 0.516(3) 0.095(3) 0.1446(19) 0.024(7) Uiso 1 1 d . . . H7A H 0.350(3) 0.102(3) 0.143(2) 0.028(7) Uiso 1 1 d . . . C8 C 0.3785(3) 0.3470(3) 0.48912(19) 0.0261(5) Uani 1 1 d . . . H8B H 0.295(3) 0.380(3) 0.454(2) 0.034(8) Uiso 1 1 d . . . H8A H 0.436(3) 0.420(3) 0.545(2) 0.034(8) Uiso 1 1 d . . . C9 C 0.4587(3) 0.2140(2) 0.63393(18) 0.0254(5) Uani 1 1 d . . . C10 C 0.5297(3) 0.1003(3) 0.6388(2) 0.0292(6) Uani 1 1 d . . . H10 H 0.494(3) 0.021(3) 0.590(2) 0.031(7) Uiso 1 1 d . . . C11 C 0.6523(3) 0.1062(3) 0.7186(2) 0.0348(6) Uani 1 1 d . . . H11 H 0.698(4) 0.040(3) 0.718(2) 0.048(10) Uiso 1 1 d . . . C12 C 0.7054(3) 0.2240(3) 0.7954(2) 0.0326(6) Uani 1 1 d . . . H12 H 0.783(3) 0.226(3) 0.846(2) 0.029(7) Uiso 1 1 d . . . C13 C 0.6360(3) 0.3375(3) 0.7923(2) 0.0320(6) Uani 1 1 d . . . H13 H 0.668(3) 0.419(3) 0.843(2) 0.039(8) Uiso 1 1 d . . . C14 C 0.5142(3) 0.3328(3) 0.71268(19) 0.0281(5) Uani 1 1 d . . . H14 H 0.468(3) 0.410(3) 0.712(2) 0.030(7) Uiso 1 1 d . . . C15 C 0.1655(3) 0.2823(3) 0.58136(18) 0.0290(5) Uani 1 1 d . . . C16 C 0.0654(3) 0.1946(4) 0.6034(2) 0.0379(7) Uani 1 1 d . . . H16 H 0.066(3) 0.106(3) 0.584(2) 0.031(8) Uiso 1 1 d . . . C17 C -0.0355(3) 0.2458(4) 0.6484(2) 0.0488(9) Uani 1 1 d . . . H17 H -0.100(4) 0.183(4) 0.658(3) 0.066(11) Uiso 1 1 d . . . C18 C -0.0404(3) 0.3838(4) 0.6708(2) 0.0445(8) Uani 1 1 d . . . H18 H -0.104(4) 0.417(3) 0.697(3) 0.055(10) Uiso 1 1 d . . . C19 C 0.0538(3) 0.4711(4) 0.6478(2) 0.0457(8) Uani 1 1 d . . . H19 H 0.053(4) 0.563(4) 0.663(3) 0.052(10) Uiso 1 1 d . . . C20 C 0.1572(3) 0.4204(3) 0.6036(2) 0.0406(7) Uani 1 1 d . . . H20 H 0.218(4) 0.482(3) 0.592(2) 0.052(10) Uiso 1 1 d . . . C21 C 0.6330(3) 0.3298(2) 0.09668(17) 0.0227(5) Uani 1 1 d . . . C22 C 0.6883(3) 0.4637(3) 0.09992(19) 0.0299(5) Uani 1 1 d . . . H22 H 0.630(3) 0.531(3) 0.112(2) 0.034(8) Uiso 1 1 d . . . C23 C 0.8279(3) 0.4973(3) 0.0877(2) 0.0356(6) Uani 1 1 d . . . H23 H 0.861(3) 0.587(3) 0.0922(19) 0.025(7) Uiso 1 1 d . . . C24 C 0.9165(3) 0.3983(3) 0.0747(2) 0.0372(7) Uani 1 1 d . . . H24 H 1.007(3) 0.420(3) 0.066(2) 0.037(8) Uiso 1 1 d . . . C25 C 0.8634(3) 0.2652(3) 0.0722(2) 0.0359(6) Uani 1 1 d . . . H25 H 0.914(4) 0.200(3) 0.062(2) 0.046(9) Uiso 1 1 d . . . C26 C 0.7237(3) 0.2299(3) 0.0822(2) 0.0291(5) Uani 1 1 d . . . H26 H 0.687(3) 0.136(3) 0.082(2) 0.034(8) Uiso 1 1 d . . . C27 C 0.3253(3) 0.1964(2) -0.01404(17) 0.0216(5) Uani 1 1 d . . . C28 C 0.1742(3) 0.1397(3) -0.02832(19) 0.0266(5) Uani 1 1 d . . . H28 H 0.141(3) 0.148(3) 0.024(2) 0.038(8) Uiso 1 1 d . . . C29 C 0.0751(3) 0.0693(3) -0.1186(2) 0.0306(6) Uani 1 1 d . . . H29 H -0.022(3) 0.031(3) -0.126(2) 0.039(8) Uiso 1 1 d . . . C30 C 0.1236(3) 0.0547(3) -0.1975(2) 0.0320(6) Uani 1 1 d . . . H30 H 0.060(3) 0.007(3) -0.257(2) 0.038(8) Uiso 1 1 d . . . C31 C 0.2720(3) 0.1125(3) -0.18550(19) 0.0301(6) Uani 1 1 d . . . H31 H 0.305(3) 0.107(3) -0.2356(19) 0.023(7) Uiso 1 1 d . . . C32 C 0.3725(3) 0.1818(2) -0.09434(18) 0.0241(5) Uani 1 1 d . . . H32 H 0.468(3) 0.219(3) -0.086(2) 0.028(7) Uiso 1 1 d . . . 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 Br1 0.02255(13) 0.04095(16) 0.02653(14) 0.00849(11) 0.01044(10) 0.01012(10) P1 0.0304(3) 0.0271(3) 0.0231(3) 0.0025(3) 0.0134(3) -0.0005(3) P2 0.0233(3) 0.0229(3) 0.0235(3) 0.0068(2) 0.0130(2) 0.0073(2) C1 0.0209(11) 0.0224(11) 0.0242(12) 0.0072(9) 0.0096(9) 0.0034(9) C2 0.0239(12) 0.0221(11) 0.0246(12) 0.0069(9) 0.0123(10) 0.0031(9) C3 0.0253(12) 0.0285(13) 0.0288(13) 0.0068(10) 0.0157(11) 0.0059(10) C4 0.0219(13) 0.0394(15) 0.0310(14) 0.0124(12) 0.0092(11) 0.0064(11) C5 0.0281(13) 0.0351(14) 0.0210(13) 0.0068(11) 0.0084(10) 0.0036(10) C6 0.0264(12) 0.0238(11) 0.0226(12) 0.0076(9) 0.0130(10) 0.0043(9) C7 0.0248(12) 0.0240(12) 0.0229(12) 0.0057(10) 0.0126(10) 0.0050(10) C8 0.0306(13) 0.0282(13) 0.0224(13) 0.0049(10) 0.0150(11) 0.0052(10) C9 0.0292(12) 0.0255(12) 0.0269(13) 0.0076(10) 0.0184(11) 0.0020(10) C10 0.0383(14) 0.0220(12) 0.0330(14) 0.0060(11) 0.0225(12) 0.0023(11) C11 0.0376(15) 0.0312(14) 0.0492(18) 0.0196(13) 0.0256(14) 0.0122(12) C12 0.0291(14) 0.0419(16) 0.0344(15) 0.0177(13) 0.0155(12) 0.0090(12) C13 0.0343(14) 0.0345(14) 0.0282(14) 0.0055(12) 0.0147(12) 0.0067(11) C14 0.0322(13) 0.0278(13) 0.0279(13) 0.0053(10) 0.0163(11) 0.0095(11) C15 0.0211(12) 0.0440(15) 0.0217(12) 0.0099(11) 0.0078(10) 0.0024(10) C16 0.0271(14) 0.056(2) 0.0414(17) 0.0297(15) 0.0136(12) 0.0092(13) C17 0.0276(15) 0.087(3) 0.051(2) 0.044(2) 0.0208(14) 0.0130(16) C18 0.0249(14) 0.087(3) 0.0250(15) 0.0142(15) 0.0127(12) 0.0152(15) C19 0.0343(16) 0.058(2) 0.0402(18) -0.0014(15) 0.0181(14) 0.0069(14) C20 0.0351(15) 0.0424(17) 0.0434(18) -0.0002(13) 0.0246(14) 0.0000(13) C21 0.0227(11) 0.0274(12) 0.0193(12) 0.0069(9) 0.0087(9) 0.0046(9) C22 0.0314(13) 0.0281(13) 0.0300(14) 0.0094(11) 0.0095(11) 0.0038(11) C23 0.0329(14) 0.0373(15) 0.0354(16) 0.0144(12) 0.0101(12) -0.0056(12) C24 0.0226(13) 0.0575(19) 0.0353(16) 0.0212(14) 0.0106(12) 0.0003(12) C25 0.0270(13) 0.0498(17) 0.0448(17) 0.0240(14) 0.0206(13) 0.0166(13) C26 0.0272(13) 0.0334(14) 0.0348(15) 0.0150(11) 0.0166(11) 0.0092(11) C27 0.0209(11) 0.0248(11) 0.0241(12) 0.0103(9) 0.0106(9) 0.0092(9) C28 0.0235(12) 0.0328(13) 0.0287(13) 0.0111(11) 0.0129(10) 0.0093(10) C29 0.0214(12) 0.0351(14) 0.0376(15) 0.0153(12) 0.0085(11) 0.0068(10) C30 0.0311(14) 0.0342(14) 0.0271(14) 0.0118(11) 0.0022(11) 0.0040(11) C31 0.0352(14) 0.0375(14) 0.0234(13) 0.0128(11) 0.0145(11) 0.0080(11) C32 0.0240(12) 0.0280(12) 0.0255(13) 0.0108(10) 0.0128(10) 0.0061(10) 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' 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_site_symmetry_1 _geom_angle_site_symmetry_3 C15 P1 C9 99.98(11) . . C15 P1 C8 100.94(12) . . C9 P1 C8 99.43(12) . . C21 P2 C27 102.24(10) . . C21 P2 C7 103.62(11) . . C27 P2 C7 98.57(11) . . C6 C1 C2 123.6(2) . . C6 C1 Br1 118.59(17) . . C2 C1 Br1 117.82(18) . . C3 C2 C1 116.5(2) . . C3 C2 C7 120.0(2) . . C1 C2 C7 123.5(2) . . C4 C3 C2 121.5(2) . . C4 C3 H3 119.5(18) . . C2 C3 H3 119.0(18) . . C3 C4 C5 120.3(2) . . C3 C4 H4 119.9(19) . . C5 C4 H4 119.8(19) . . C4 C5 C6 120.9(2) . . C4 C5 H5 121.7(18) . . C6 C5 H5 117.4(17) . . C1 C6 C5 117.2(2) . . C1 C6 C8 123.5(2) . . C5 C6 C8 119.2(2) . . C2 C7 P2 112.30(16) . . C2 C7 H7B 108.9(16) . . P2 C7 H7B 110.3(16) . . C2 C7 H7A 111.9(16) . . P2 C7 H7A 106.1(16) . . H7B C7 H7A 107(2) . . C6 C8 P1 110.58(17) . . C6 C8 H8B 110.3(18) . . P1 C8 H8B 108.0(17) . . C6 C8 H8A 111.2(17) . . P1 C8 H8A 108.6(18) . . H8B C8 H8A 108(2) . . C10 C9 C14 117.7(2) . . C10 C9 P1 119.14(19) . . C14 C9 P1 123.12(19) . . C11 C10 C9 120.7(3) . . C11 C10 H10 119.6(18) . . C9 C10 H10 119.6(18) . . C12 C11 C10 120.8(3) . . C12 C11 H11 120(2) . . C10 C11 H11 120(2) . . C11 C12 C13 119.4(3) . . C11 C12 H12 119.8(18) . . C13 C12 H12 120.8(19) . . C12 C13 C14 120.2(3) . . C12 C13 H13 121.8(19) . . C14 C13 H13 118.0(19) . . C13 C14 C9 121.2(2) . . C13 C14 H14 119.1(17) . . C9 C14 H14 119.7(17) . . C20 C15 C16 117.7(3) . . C20 C15 P1 125.9(2) . . C16 C15 P1 116.5(2) . . C17 C16 C15 120.8(3) . . C17 C16 H16 122.4(19) . . C15 C16 H16 116.7(19) . . C18 C17 C16 120.5(3) . . C18 C17 H17 123(2) . . C16 C17 H17 116(2) . . C19 C18 C17 119.8(3) . . C19 C18 H18 119(2) . . C17 C18 H18 122(2) . . C18 C19 C20 120.0(3) . . C18 C19 H19 121(2) . . C20 C19 H19 119(2) . . C15 C20 C19 121.3(3) . . C15 C20 H20 122(2) . . C19 C20 H20 116(2) . . C22 C21 C26 118.1(2) . . C22 C21 P2 116.89(18) . . C26 C21 P2 125.01(19) . . C23 C22 C21 121.3(3) . . C23 C22 H22 120.5(18) . . C21 C22 H22 118.3(18) . . C24 C23 C22 119.9(3) . . C24 C23 H23 121.8(17) . . C22 C23 H23 118.1(17) . . C23 C24 C25 119.4(3) . . C23 C24 H24 120.0(18) . . C25 C24 H24 120.6(19) . . C26 C25 C24 121.2(3) . . C26 C25 H25 117(2) . . C24 C25 H25 122(2) . . C25 C26 C21 120.1(3) . . C25 C26 H26 121.3(17) . . C21 C26 H26 118.5(17) . . C32 C27 C28 117.9(2) . . C32 C27 P2 124.56(18) . . C28 C27 P2 117.31(18) . . C29 C28 C27 121.3(2) . . C29 C28 H28 119.4(18) . . C27 C28 H28 119.2(19) . . C28 C29 C30 120.2(2) . . C28 C29 H29 119.7(19) . . C30 C29 H29 120.1(19) . . C29 C30 C31 119.6(3) . . C29 C30 H30 120.7(19) . . C31 C30 H30 119.6(19) . . C30 C31 C32 120.1(2) . . C30 C31 H31 121.4(17) . . C32 C31 H31 118.5(17) . . C31 C32 C27 120.8(2) . . C31 C32 H32 120.8(18) . . C27 C32 H32 118.4(18) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Br1 C1 1.918(2) . P1 C15 1.839(3) . P1 C9 1.842(3) . P1 C8 1.864(3) . P2 C21 1.833(2) . P2 C27 1.840(2) . P2 C7 1.864(2) . C1 C6 1.390(3) . C1 C2 1.402(3) . C2 C3 1.400(3) . C2 C7 1.500(3) . C3 C4 1.375(4) . C3 H3 0.94(3) . C4 C5 1.386(4) . C4 H4 0.91(3) . C5 C6 1.398(3) . C5 H5 0.96(3) . C6 C8 1.508(3) . C7 H7B 0.95(3) . C7 H7A 0.97(3) . C8 H8B 0.95(3) . C8 H8A 0.95(3) . C9 C10 1.395(4) . C9 C14 1.404(3) . C10 C11 1.389(4) . C10 H10 0.91(3) . C11 C12 1.382(4) . C11 H11 0.83(3) . C12 C13 1.383(4) . C12 H12 0.88(3) . C13 C14 1.386(4) . C13 H13 0.94(3) . C14 H14 0.93(3) . C15 C20 1.378(4) . C15 C16 1.394(4) . C16 C17 1.385(4) . C16 H16 0.88(3) . C17 C18 1.371(5) . C17 H17 0.90(4) . C18 C19 1.365(5) . C18 H18 0.86(4) . C19 C20 1.396(4) . C19 H19 0.91(3) . C20 H20 0.89(3) . C21 C22 1.393(3) . C21 C26 1.402(3) . C22 C23 1.387(4) . C22 H22 0.93(3) . C23 C24 1.377(4) . C23 H23 0.92(3) . C24 C25 1.384(4) . C24 H24 0.90(3) . C25 C26 1.376(4) . C25 H25 0.86(3) . C26 H26 0.98(3) . C27 C32 1.396(3) . C27 C28 1.398(3) . C28 C29 1.379(4) . C28 H28 0.92(3) . C29 C30 1.384(4) . C29 H29 0.91(3) . C30 C31 1.387(4) . C30 H30 0.91(3) . C31 C32 1.391(4) . C31 H31 0.90(3) . C32 H32 0.89(3) .