#------------------------------------------------------------------------------ #$Date: 2008-06-25 12:31:45 +0300 (Wed, 25 Jun 2008) $ #$Revision: 403 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/7101823.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_7101823 loop_ _publ_author_name 'Hua, Guoxiong' 'Li, Yang' 'Slawin, Alexandra M Z' 'Woollins, J Derek' _publ_section_title ; Unexpected four- and eight-membered organo P-Se heterocycles. ; _journal_issue 14 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 1465 _journal_page_last 1467 _journal_year 2007 _chemical_formula_moiety 'C18 H23 P Se2' _chemical_formula_sum 'C18 H23 P Se2' _chemical_formula_weight 428.25 _chemical_name_systematic ; ? ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 92.984(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.1765(10) _cell_length_b 25.499(3) _cell_length_c 9.2946(11) _cell_measurement_reflns_used 7696 _cell_measurement_temperature 93(2) _cell_measurement_theta_max 28.16 _cell_measurement_theta_min 2.28 _cell_volume 1935.2(4) _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_molecular_graphics PLATON _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 93(2) _diffrn_detector_area_resol_mean 0.83 _diffrn_measured_fraction_theta_full 0.948 _diffrn_measured_fraction_theta_max 0.797 _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_radiation_monochromator confocal _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 10297 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_min 2.34 _exptl_absorpt_coefficient_mu 3.897 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.5096 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour Orange _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 856 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.723 _refine_diff_density_min -0.716 _refine_diff_density_rms 0.200 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 196 _refine_ls_number_reflns 3523 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.169 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0375 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+1.1519P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0995 _refine_ls_wR_factor_ref 0.1048 _reflns_number_gt 2993 _reflns_number_total 3523 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file b617418c.txt _[local]_cod_data_source_block p21c _[local]_cod_cif_authors_sg_H-M P21/c 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_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 Se1 Se 1.25588(5) 0.026753(17) 0.41290(4) 0.01954(14) Uani 1 1 d . Se2 Se 0.90358(4) 0.095651(15) 0.58065(4) 0.01450(13) Uani 1 1 d . P1 P 1.16459(11) 0.06358(4) 0.59345(10) 0.0123(2) Uani 1 1 d . C1 C 1.2027(4) 0.02858(15) 0.7621(4) 0.0138(8) Uani 1 1 d . C2 C 1.1471(5) 0.05019(18) 0.8884(5) 0.0225(9) Uani 1 1 d . H2 H 1.0829 0.0812 0.8845 0.027 Uiso 1 1 calc R C3 C 1.1858(5) 0.02628(18) 1.0194(5) 0.0261(10) Uani 1 1 d . H3 H 1.1483 0.0409 1.1057 0.031 Uiso 1 1 calc R C4 C 1.2794(5) -0.01910(17) 1.0244(5) 0.0221(9) Uani 1 1 d . H4 H 1.3054 -0.0355 1.1144 0.026 Uiso 1 1 calc R C5 C 1.3352(5) -0.04071(17) 0.8997(5) 0.0206(9) Uani 1 1 d . H5 H 1.4000 -0.0716 0.9042 0.025 Uiso 1 1 calc R C6 C 1.2962(5) -0.01695(16) 0.7673(4) 0.0166(8) Uani 1 1 d . H6 H 1.3332 -0.0318 0.6810 0.020 Uiso 1 1 calc R C7 C 1.0587(4) 0.15384(15) 0.6120(4) 0.0126(8) Uani 1 1 d . C8 C 1.2113(4) 0.13251(15) 0.6241(4) 0.0139(8) Uani 1 1 d . C9 C 1.3774(5) 0.15797(17) 0.6516(4) 0.0195(9) Uani 1 1 d . C10 C 1.4401(7) 0.1766(3) 0.5082(6) 0.0576(19) Uani 1 1 d . H10A H 1.4450 0.1469 0.4420 0.086 Uiso 1 1 calc R H10B H 1.5498 0.1917 0.5245 0.086 Uiso 1 1 calc R H10C H 1.3657 0.2033 0.4664 0.086 Uiso 1 1 calc R C11 C 1.3679(6) 0.2035(2) 0.7581(7) 0.0396(13) Uani 1 1 d . H11A H 1.3041 0.2322 0.7131 0.059 Uiso 1 1 calc R H11B H 1.4787 0.2158 0.7852 0.059 Uiso 1 1 calc R H11C H 1.3148 0.1915 0.8444 0.059 Uiso 1 1 calc R C12 C 1.4983(5) 0.11785(19) 0.7197(6) 0.0312(11) Uani 1 1 d . H12A H 1.4589 0.1059 0.8119 0.047 Uiso 1 1 calc R H12B H 1.6061 0.1343 0.7357 0.047 Uiso 1 1 calc R H12C H 1.5071 0.0878 0.6548 0.047 Uiso 1 1 calc R C13 C 1.0049(4) 0.20676(16) 0.6178(4) 0.0156(8) Uani 1 1 d . C14 C 0.9549(5) 0.25099(16) 0.6238(4) 0.0151(8) Uani 1 1 d . C15 C 0.9045(4) 0.30643(16) 0.6335(4) 0.0157(8) Uani 1 1 d . C16 C 0.8513(6) 0.32597(17) 0.4813(5) 0.0270(10) Uani 1 1 d . H16A H 0.9417 0.3214 0.4173 0.040 Uiso 1 1 calc R H16B H 0.8219 0.3632 0.4856 0.040 Uiso 1 1 calc R H16C H 0.7563 0.3057 0.4442 0.040 Uiso 1 1 calc R C17 C 0.7620(5) 0.31068(18) 0.7339(5) 0.0253(10) Uani 1 1 d . H17A H 0.6681 0.2908 0.6932 0.038 Uiso 1 1 calc R H17B H 0.7311 0.3476 0.7439 0.038 Uiso 1 1 calc R H17C H 0.7958 0.2964 0.8287 0.038 Uiso 1 1 calc R C18 C 1.0493(5) 0.33926(19) 0.6938(5) 0.0289(10) Uani 1 1 d . H18A H 1.0832 0.3267 0.7905 0.043 Uiso 1 1 calc R H18B H 1.0165 0.3761 0.6989 0.043 Uiso 1 1 calc R H18C H 1.1410 0.3359 0.6306 0.043 Uiso 1 1 calc R 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 Se1 0.0278(2) 0.0178(3) 0.0134(2) -0.00242(17) 0.00422(16) 0.00506(16) Se2 0.0133(2) 0.0133(2) 0.0167(2) -0.00037(16) -0.00133(14) 0.00081(14) P1 0.0155(5) 0.0101(5) 0.0113(5) 0.0003(4) 0.0000(4) 0.0026(4) C1 0.0149(18) 0.014(2) 0.013(2) 0.0019(16) -0.0025(15) -0.0026(14) C2 0.029(2) 0.020(2) 0.018(2) 0.0042(18) 0.0041(17) 0.0083(17) C3 0.033(2) 0.031(3) 0.014(2) 0.0017(19) 0.0046(18) 0.0080(19) C4 0.027(2) 0.022(2) 0.017(2) 0.0062(18) -0.0065(17) -0.0040(17) C5 0.023(2) 0.013(2) 0.025(2) 0.0031(18) -0.0051(17) 0.0019(16) C6 0.021(2) 0.015(2) 0.015(2) -0.0027(17) -0.0006(15) 0.0005(15) C7 0.0186(18) 0.0077(19) 0.0116(19) 0.0029(16) 0.0010(15) 0.0011(14) C8 0.0181(19) 0.013(2) 0.0104(19) 0.0042(16) 0.0001(15) 0.0027(15) C9 0.0173(19) 0.021(2) 0.020(2) -0.0002(19) 0.0029(16) -0.0039(16) C10 0.046(3) 0.090(5) 0.036(3) 0.023(3) -0.001(3) -0.041(3) C11 0.020(2) 0.027(3) 0.070(4) -0.019(3) -0.015(2) 0.0020(19) C12 0.016(2) 0.025(3) 0.052(3) -0.008(2) -0.005(2) 0.0006(18) C13 0.0146(18) 0.019(2) 0.013(2) 0.0006(17) -0.0012(15) 0.0002(16) C14 0.0170(19) 0.014(2) 0.014(2) 0.0004(17) -0.0011(15) 0.0026(15) C15 0.0203(19) 0.013(2) 0.014(2) 0.0022(17) 0.0019(15) 0.0025(15) C16 0.046(3) 0.015(2) 0.020(2) 0.0016(19) -0.0005(19) 0.0120(19) C17 0.030(2) 0.016(2) 0.031(3) -0.002(2) 0.0114(19) 0.0061(17) C18 0.032(2) 0.025(3) 0.030(3) -0.005(2) 0.003(2) -0.0035(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Se1 P1 2.0941(11) Se2 C7 1.964(4) Se2 P1 2.2828(10) P1 C1 1.816(4) P1 C8 1.818(4) C1 C6 1.389(6) C1 C2 1.394(6) C2 C3 1.384(6) C2 H2 0.9500 C3 C4 1.387(6) C3 H3 0.9500 C4 C5 1.382(6) C4 H4 0.9500 C5 C6 1.394(6) C5 H5 0.9500 C6 H6 0.9500 C7 C8 1.361(5) C7 C13 1.421(5) C8 C9 1.515(5) C9 C10 1.528(7) C9 C11 1.530(6) C9 C12 1.536(6) C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 C11 H11A 0.9800 C11 H11B 0.9800 C11 H11C 0.9800 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 C14 1.202(6) C14 C15 1.477(6) C15 C18 1.532(6) C15 C17 1.534(6) C15 C16 1.541(6) C16 H16A 0.9800 C16 H16B 0.9800 C16 H16C 0.9800 C17 H17A 0.9800 C17 H17B 0.9800 C17 H17C 0.9800 C18 H18A 0.9800 C18 H18B 0.9800 C18 H18C 0.9800 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C7 Se2 P1 70.62(11) C1 P1 C8 108.33(17) C1 P1 Se1 114.77(14) C8 P1 Se1 118.58(13) C1 P1 Se2 109.80(13) C8 P1 Se2 81.37(12) Se1 P1 Se2 119.35(5) C6 C1 C2 120.3(4) C6 C1 P1 120.6(3) C2 C1 P1 118.9(3) C3 C2 C1 119.8(4) C3 C2 H2 120.1 C1 C2 H2 120.1 C2 C3 C4 119.8(4) C2 C3 H3 120.1 C4 C3 H3 120.1 C5 C4 C3 120.7(4) C5 C4 H4 119.7 C3 C4 H4 119.7 C4 C5 C6 119.8(4) C4 C5 H5 120.1 C6 C5 H5 120.1 C1 C6 C5 119.6(4) C1 C6 H6 120.2 C5 C6 H6 120.2 C8 C7 C13 131.4(4) C8 C7 Se2 107.0(3) C13 C7 Se2 121.6(3) C7 C8 C9 130.8(4) C7 C8 P1 100.9(3) C9 C8 P1 128.3(3) C8 C9 C10 109.0(3) C8 C9 C11 111.0(3) C10 C9 C11 111.0(5) C8 C9 C12 109.7(3) C10 C9 C12 109.2(4) C11 C9 C12 106.9(4) C9 C10 H10A 109.5 C9 C10 H10B 109.5 H10A C10 H10B 109.5 C9 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 C9 C11 H11A 109.5 C9 C11 H11B 109.5 H11A C11 H11B 109.5 C9 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 C9 C12 H12A 109.5 C9 C12 H12B 109.5 H12A C12 H12B 109.5 C9 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C14 C13 C7 178.1(4) C13 C14 C15 176.3(4) C14 C15 C18 109.4(3) C14 C15 C17 109.2(3) C18 C15 C17 109.6(4) C14 C15 C16 108.6(3) C18 C15 C16 109.6(4) C17 C15 C16 110.4(3) C15 C16 H16A 109.5 C15 C16 H16B 109.5 H16A C16 H16B 109.5 C15 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C15 C17 H17A 109.5 C15 C17 H17B 109.5 H17A C17 H17B 109.5 C15 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 C15 C18 H18A 109.5 C15 C18 H18B 109.5 H18A C18 H18B 109.5 C15 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 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 C7 Se2 P1 C1 108.06(18) C7 Se2 P1 C8 1.59(17) C7 Se2 P1 Se1 -116.44(13) P1 Se2 C7 C8 -2.2(2) P1 Se2 C7 C13 177.5(3) C8 P1 C1 C6 -130.6(3) Se1 P1 C1 C6 4.5(3) Se2 P1 C1 C6 142.2(3) C8 P1 C1 C2 44.6(4) Se1 P1 C1 C2 179.7(3) Se2 P1 C1 C2 -42.6(3) C6 C1 C2 C3 0.2(6) P1 C1 C2 C3 -175.0(3) C13 C7 C8 C9 1.6(7) Se2 C7 C8 C9 -178.8(3) C13 C7 C8 P1 -177.0(4) Se2 C7 C8 P1 2.6(3) C1 P1 C8 C7 -110.3(3) Se1 P1 C8 C7 116.6(2) Se2 P1 C8 C7 -2.2(2) C1 P1 C8 C9 71.1(4) Se1 P1 C8 C9 -62.0(4) Se2 P1 C8 C9 179.2(4) C7 C8 C9 C10 -85.1(6) P1 C8 C9 C10 93.1(5) C7 C8 C9 C11 37.5(6) P1 C8 C9 C11 -144.3(4) C7 C8 C9 C12 155.4(4) P1 C8 C9 C12 -26.3(5) C6 C5 C4 C3 -0.5(6) C2 C1 C6 C5 -0.5(6) P1 C1 C6 C5 174.7(3) C4 C5 C6 C1 0.6(6) C1 C2 C3 C4 -0.1(7) C5 C4 C3 C2 0.3(7)