# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Naya, Shin-ichi' 'Nitta, Makoto' _publ_contact_author_name 'Dr Makoto Nitta' _publ_contact_author_address ; Department of Chemistry School of Science and Engineering Materials Research Laboratory for b Waseda University Shinjuku-ku Tokyo 169-8555 JAPAN ; _publ_contact_author_email 'NITTA@MN.WASEDA.AC.JP' _publ_section_title ; Studies on the structure of 2,2,2-triphenyl-2H-cyclohepta[d]-1,2lambda5-oxaphosphole [2-(1-triphenylphosphoranylidene)methyltropone] derivatives: reactivity of 3-methyl-2,2,2-triphenyl-2H-cyclohepta[d]-1,2lambda5-oxaphosphole with heterocumulenes ; _publ_section_abstract ; We present the crystal and molecular structure of ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using maXus (Nonius, Delft & MacScience, Japan). ; data__NMeP_____________________ _database_code_CSD 172471 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C27 H23 O P ' _chemical_formula_moiety 'C27 H23 O P ' _chemical_formula_weight 394.45 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'Pbca' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' '-x+1/2,y+1/2,z' 'x+1/2,-y+1/2,-z' 'x,-y+1/2,z+1/2' '-x,y+1/2,-z+1/2' '-x+1/2,-y,z+1/2' 'x+1/2,y,-z+1/2' #------------------------------------------------------------------------------ _cell_length_a 17.5193(4) _cell_length_b 13.2112(8) _cell_length_c 17.8502(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4131.4(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 21472 _cell_measurement_theta_min 1.1 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 123.1 #------------------------------------------------------------------------------ _exptl_crystal_description 'prism' _exptl_crystal_colour 'Reddish' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.916 _exptl_absorpt_correction_T_max 0.971 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 39328 _diffrn_reflns_av_R_equivalents 0.119 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.9918 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.9918 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 9841 _reflns_number_gt 3539 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.1410 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3539 _refine_ls_number_parameters 354 _refine_ls_goodness_of_fit_ref 1.347 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.010Fo^2^ + 1.000\s^2^(Fo)]' _refine_ls_shift/su_max 0.0030 _refine_diff_density_max 0.77 _refine_diff_density_min -0.67 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'H' 'H' 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; 'O' 'O' 0.017 0.010 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'P' 'P' 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 P1 P 0.38776(5) 0.20126(7) 0.57990(5) 0.0133(3) Uani 1.00 1 d . . . O1 O 0.2979(1) 0.1475(2) 0.6363(1) 0.0154(7) Uani 1.00 1 d . . . C1 C 0.2577(2) 0.2177(3) 0.6678(2) 0.0135(8) Uani 1.00 1 d . . . C2 C 0.2012(2) 0.1913(3) 0.7190(2) 0.0152(9) Uani 1.00 1 d . . . C3 C 0.1489(2) 0.2525(3) 0.7577(2) 0.0173(9) Uani 1.00 1 d . . . C4 C 0.1390(2) 0.3554(3) 0.7545(2) 0.0181(9) Uani 1.00 1 d . . . C5 C 0.1809(2) 0.4250(3) 0.7116(2) 0.0178(9) Uani 1.00 1 d . . . C6 C 0.2405(2) 0.4102(3) 0.6639(2) 0.0158(9) Uani 1.00 1 d . . . C7 C 0.2794(2) 0.3200(3) 0.6423(2) 0.0137(9) Uani 1.00 1 d . . . C8 C 0.3406(2) 0.3198(3) 0.5928(2) 0.0141(9) Uani 1.00 1 d . . . C9 C 0.3636(2) 0.4140(3) 0.5508(2) 0.019(1) Uani 1.00 1 d . . . C10 C 0.4397(2) 0.1402(3) 0.6559(2) 0.0169(9) Uani 1.00 1 d . . . C11 C 0.4276(3) 0.1717(4) 0.7308(2) 0.023(1) Uani 1.00 1 d . . . C12 C 0.4673(3) 0.1245(4) 0.7887(3) 0.033(1) Uani 1.00 1 d . . . C13 C 0.5170(3) 0.0452(4) 0.7731(3) 0.036(1) Uani 1.00 1 d . . . C14 C 0.5289(3) 0.0150(4) 0.7007(3) 0.034(1) Uani 1.00 1 d . . . C15 C 0.4917(2) 0.0623(3) 0.6420(3) 0.024(1) Uani 1.00 1 d . . . C16 C 0.3524(2) 0.1186(3) 0.5057(2) 0.0170(9) Uani 1.00 1 d . . . C17 C 0.3189(3) 0.1656(4) 0.4439(3) 0.024(1) Uani 1.00 1 d . . . C18 C 0.2888(3) 0.1073(4) 0.3864(3) 0.032(1) Uani 1.00 1 d . . . C19 C 0.2917(3) 0.0026(4) 0.3901(3) 0.031(1) Uani 1.00 1 d . . . C20 C 0.3247(3) -0.0438(4) 0.4509(3) 0.029(1) Uani 1.00 1 d . . . C21 C 0.3550(2) 0.0132(3) 0.5095(3) 0.022(1) Uani 1.00 1 d . . . C22 C 0.4774(2) 0.2456(3) 0.5332(2) 0.0164(9) Uani 1.00 1 d . . . C23 C 0.5231(2) 0.3134(3) 0.5733(2) 0.020(1) Uani 1.00 1 d . . . C24 C 0.5921(2) 0.3468(4) 0.5451(2) 0.023(1) Uani 1.00 1 d . . . C25 C 0.6176(3) 0.3120(3) 0.4754(3) 0.023(1) Uani 1.00 1 d . . . C26 C 0.5733(2) 0.2439(4) 0.4359(2) 0.023(1) Uani 1.00 1 d . . . C27 C 0.5038(2) 0.2114(3) 0.4642(2) 0.0177(9) Uani 1.00 1 d . . . H1 H 0.504(3) 0.340(3) 0.617(3) 0.02(1) Uiso 1.00 1 c . . . H2 H 0.622(3) 0.391(4) 0.574(3) 0.02(1) Uiso 1.00 1 c . . . H3 H 0.668(3) 0.331(4) 0.455(3) 0.02(1) Uiso 1.00 1 c . . . H4 H 0.474(3) 0.170(4) 0.431(3) 0.02(1) Uiso 1.00 1 c . . . H5 H 0.590(3) 0.227(4) 0.387(3) 0.03(1) Uiso 1.00 1 c . . . H6 H 0.383(3) -0.013(4) 0.556(3) 0.02(1) Uiso 1.00 1 c . . . H7 H 0.319(3) 0.238(4) 0.438(3) 0.03(1) Uiso 1.00 1 c . . . H8 H 0.271(3) 0.142(5) 0.339(3) 0.04(2) Uiso 1.00 1 c . . . H9 H 0.268(3) -0.042(4) 0.347(3) 0.02(1) Uiso 1.00 1 c . . . H10 H 0.394(3) 0.234(5) 0.743(3) 0.04(2) Uiso 1.00 1 c . . . H11 H 0.461(3) 0.144(4) 0.842(3) 0.02(1) Uiso 1.00 1 c . . . H12 H 0.547(4) 0.027(5) 0.815(4) 0.05(2) Uiso 1.00 1 c . . . H13 H 0.561(3) -0.041(4) 0.694(3) 0.02(1) Uiso 1.00 1 c . . . H14 H 0.401(3) 0.450(4) 0.586(3) 0.02(1) Uiso 1.00 1 c . . . H15 H 0.394(3) 0.396(5) 0.506(3) 0.04(2) Uiso 1.00 1 c . . . H16 H 0.201(3) 0.117(4) 0.727(3) 0.03(1) Uiso 1.00 1 c . . . H17 H 0.115(2) 0.215(3) 0.789(2) 0.001(9) Uiso 1.00 1 c . . . H18 H 0.099(3) 0.382(4) 0.786(3) 0.01(1) Uiso 1.00 1 c . . . H19 H 0.162(3) 0.493(4) 0.717(3) 0.02(1) Uiso 1.00 1 c . . . H20 H 0.260(3) 0.475(4) 0.638(3) 0.02(1) Uiso 1.00 1 c . . . H21 H 0.328(4) 0.443(4) 0.533(3) 0.04(2) Uiso 1.00 1 c . . . H22 H 0.328(3) -0.112(5) 0.455(3) 0.04(2) Uiso 1.00 1 c . . . H23 H 0.503(3) 0.047(4) 0.596(3) 0.03(1) Uiso 1.00 1 c . . . 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 0.0121(5) 0.0143(5) 0.0136(5) 0.0009(4) -0.0009(4) -0.0003(4) O1 0.015(1) 0.013(1) 0.019(1) -0.000(1) 0.001(1) 0.000(1) C1 0.015(2) 0.012(2) 0.013(2) -0.001(1) -0.003(1) -0.000(1) C2 0.014(2) 0.015(2) 0.016(2) -0.001(1) -0.004(1) 0.004(1) C3 0.016(2) 0.023(2) 0.014(2) -0.004(2) 0.002(1) 0.003(2) C4 0.015(2) 0.024(2) 0.015(2) 0.003(2) -0.001(1) -0.004(2) C5 0.022(2) 0.015(2) 0.017(2) 0.004(2) -0.003(2) -0.002(2) C6 0.018(2) 0.016(2) 0.014(2) 0.003(2) -0.002(1) -0.002(1) C7 0.016(2) 0.013(2) 0.012(2) -0.002(1) -0.005(1) 0.001(1) C8 0.013(2) 0.014(2) 0.015(2) 0.002(1) -0.003(1) 0.002(1) C9 0.016(2) 0.019(2) 0.021(2) -0.002(2) -0.001(2) 0.003(2) C10 0.014(2) 0.017(2) 0.020(2) 0.001(1) -0.001(1) 0.009(2) C11 0.022(2) 0.027(2) 0.020(2) -0.009(2) -0.002(2) -0.001(2) C12 0.035(3) 0.043(3) 0.020(2) -0.017(2) -0.011(2) 0.003(2) C13 0.025(2) 0.043(3) 0.039(3) -0.011(2) -0.014(2) 0.029(2) C14 0.021(2) 0.035(3) 0.046(3) 0.001(2) -0.005(2) 0.021(2) C15 0.016(2) 0.025(2) 0.031(2) 0.001(2) 0.000(2) 0.008(2) C16 0.012(2) 0.023(2) 0.017(2) -0.000(2) 0.000(1) -0.006(2) C17 0.019(2) 0.029(2) 0.023(2) 0.004(2) -0.003(2) -0.007(2) C18 0.022(2) 0.048(3) 0.025(2) 0.005(2) -0.004(2) -0.009(2) C19 0.024(2) 0.042(3) 0.027(2) -0.011(2) 0.000(2) -0.018(2) C20 0.031(2) 0.024(2) 0.033(3) -0.008(2) 0.007(2) -0.013(2) C21 0.019(2) 0.024(2) 0.022(2) -0.002(2) 0.003(2) -0.005(2) C22 0.015(2) 0.018(2) 0.017(2) 0.001(2) -0.003(1) 0.002(1) C23 0.017(2) 0.026(2) 0.017(2) -0.002(2) 0.004(1) -0.001(2) C24 0.018(2) 0.027(2) 0.022(2) -0.002(2) -0.002(2) 0.000(2) C25 0.019(2) 0.025(2) 0.024(2) -0.003(2) 0.004(2) 0.006(2) C26 0.020(2) 0.027(2) 0.020(2) 0.002(2) 0.009(2) -0.003(2) C27 0.016(2) 0.020(2) 0.017(2) 0.001(2) -0.003(1) -0.001(2) #============================================================================== _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'CrystalStructure' _computing_structure_solution 'SIR92' _computing_structure_refinement 'CRYSTALS' _computing_publication_material 'CrystalStructure Ver. 2.00' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 . O1 . 1.999(3) yes P1 . C8 . 1.785(4) yes P1 . C10 . 1.822(4) yes P1 . C16 . 1.825(4) yes P1 . C22 . 1.871(4) yes O1 . C1 . 1.293(5) yes C1 . C2 . 1.392(5) yes C1 . C7 . 1.476(5) yes C2 . C3 . 1.403(6) yes C2 . H16 . 0.99(6) no C3 . C4 . 1.372(6) yes C3 . H17 . 0.96(4) no C4 . C5 . 1.404(6) yes C4 . H18 . 0.97(5) no C5 . C6 . 1.362(6) yes C5 . H19 . 0.96(5) no C6 . C7 . 1.426(5) yes C6 . H20 . 1.03(5) no C7 . C8 . 1.390(5) yes C8 . C9 . 1.509(5) yes C9 . H14 . 1.02(5) no C9 . H15 . 0.98(6) no C9 . H21 . 0.80(6) no C10 . C11 . 1.416(6) yes C10 . C15 . 1.397(6) yes C11 . C12 . 1.393(7) yes C11 . H10 . 1.03(6) no C12 . C13 . 1.390(8) yes C12 . H11 . 0.99(5) no C13 . C14 . 1.370(8) yes C13 . H12 . 0.95(6) no C14 . C15 . 1.382(6) yes C14 . H13 . 0.94(5) no C15 . H23 . 0.88(6) no C16 . C17 . 1.395(6) yes C16 . C21 . 1.394(6) yes C17 . C18 . 1.388(6) yes C17 . H7 . 0.97(6) no C18 . C19 . 1.385(8) yes C18 . H8 . 1.02(6) no C19 . C20 . 1.374(8) yes C19 . H9 . 1.05(5) no C20 . C21 . 1.395(6) yes C20 . H22 . 0.90(6) no C21 . H6 . 1.02(5) no C22 . C23 . 1.399(6) yes C22 . C27 . 1.391(5) yes C23 . C24 . 1.381(6) yes C23 . H1 . 0.92(5) no C24 . C25 . 1.400(6) yes C24 . H2 . 0.94(5) no C25 . C26 . 1.383(6) yes C25 . H3 . 0.99(5) no C26 . C27 . 1.387(6) yes C26 . H5 . 0.94(6) no C27 . H4 . 0.96(5) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . P1 . C8 . 83.24(15) yes O1 . P1 . C10 . 82.01(15) yes C8 . P1 . C10 . 121.52(19) yes O1 . P1 . C16 . 83.42(15) yes C8 . P1 . C16 . 117.52(18) yes C10 . P1 . C16 . 116.41(19) yes O1 . P1 . C22 . 174.92(15) yes C8 . P1 . C22 . 99.86(18) yes C10 . P1 . C22 . 92.93(17) yes C16 . P1 . C22 . 98.56(18) yes P1 . O1 . C1 . 113.1(2) yes O1 . C1 . C2 . 119.6(3) yes O1 . C1 . C7 . 112.5(3) yes C2 . C1 . C7 . 127.9(4) yes C1 . C2 . C3 . 130.0(4) yes C1 . C2 . H16 . 109.6(31) no C3 . C2 . H16 . 120.4(31) no C2 . C3 . C4 . 129.2(4) yes C2 . C3 . H17 . 113.0(24) no C4 . C3 . H17 . 117.7(24) no C3 . C4 . C5 . 127.3(4) yes C3 . C4 . H18 . 115.5(28) no C5 . C4 . H18 . 117.1(28) no C4 . C5 . C6 . 130.4(4) yes C4 . C5 . H19 . 112.3(28) no C6 . C5 . H19 . 117.3(28) no C5 . C6 . C7 . 131.0(4) yes C5 . C6 . H20 . 114.3(27) no C7 . C6 . H20 . 114.7(27) no C1 . C7 . C6 . 124.0(3) yes C1 . C7 . C8 . 113.1(3) yes C6 . C7 . C8 . 122.9(3) yes P1 . C8 . C7 . 116.2(3) yes P1 . C8 . C9 . 122.4(3) yes C7 . C8 . C9 . 121.3(3) yes C8 . C9 . H14 . 104.3(28) no C8 . C9 . H15 . 110.3(35) no H14 . C9 . H15 . 105.2(42) no C8 . C9 . H21 . 112.4(41) no H14 . C9 . H21 . 121.4(50) no H15 . C9 . H21 . 102.8(50) no P1 . C10 . C11 . 119.9(3) yes P1 . C10 . C15 . 121.3(3) yes C11 . C10 . C15 . 118.8(4) yes C10 . C11 . C12 . 119.6(4) yes C10 . C11 . H10 . 120.8(34) no C12 . C11 . H10 . 119.2(34) no C11 . C12 . C13 . 120.1(5) yes C11 . C12 . H11 . 122.7(29) no C13 . C12 . H11 . 117.2(29) no C12 . C13 . C14 . 120.3(4) yes C12 . C13 . H12 . 112.6(39) no C14 . C13 . H12 . 126.0(39) no C13 . C14 . C15 . 120.8(5) yes C13 . C14 . H13 . 116.0(32) no C15 . C14 . H13 . 123.1(32) no C10 . C15 . C14 . 120.4(5) yes C10 . C15 . H23 . 119.3(37) no C14 . C15 . H23 . 120.2(37) no P1 . C16 . C17 . 116.7(3) yes P1 . C16 . C21 . 123.4(3) yes C17 . C16 . C21 . 119.8(4) yes C16 . C17 . C18 . 119.9(5) yes C16 . C17 . H7 . 121.7(31) no C18 . C17 . H7 . 118.3(31) no C17 . C18 . C19 . 120.3(5) yes C17 . C18 . H8 . 118.9(35) no C19 . C18 . H8 . 120.3(34) no C18 . C19 . C20 . 119.9(4) yes C18 . C19 . H9 . 120.8(26) no C20 . C19 . H9 . 119.3(26) no C19 . C20 . C21 . 120.8(5) yes C19 . C20 . H22 . 122.1(37) no C21 . C20 . H22 . 117.1(38) no C16 . C21 . C20 . 119.3(4) yes C16 . C21 . H6 . 113.1(30) no C20 . C21 . H6 . 127.4(30) no P1 . C22 . C23 . 116.9(3) yes P1 . C22 . C27 . 124.9(3) yes C23 . C22 . C27 . 118.1(4) yes C22 . C23 . C24 . 121.2(4) yes C22 . C23 . H1 . 118.1(28) no C24 . C23 . H1 . 120.4(29) no C23 . C24 . C25 . 119.9(4) yes C23 . C24 . H2 . 119.5(29) no C25 . C24 . H2 . 120.5(29) no C24 . C25 . C26 . 119.2(4) yes C24 . C25 . H3 . 122.3(29) no C26 . C25 . H3 . 118.4(29) no C25 . C26 . C27 . 120.5(4) yes C25 . C26 . H5 . 116.4(32) no C27 . C26 . H5 . 122.7(32) no C22 . C27 . C26 . 121.0(4) yes C22 . C27 . H4 . 123.1(30) no C26 . C27 . H4 . 115.6(30) no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_site_symmetry_1 _geom_torsion_atom_site_label_2 _geom_torsion_site_symmetry_2 _geom_torsion_atom_site_label_3 _geom_torsion_site_symmetry_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C8 . P1 . O1 . C1 . -12.7(5) yes C10 . P1 . O1 . C1 . 110.6(5) yes C16 . P1 . O1 . C1 . -131.5(5) yes C22 . P1 . O1 . C1 . 115.2(5) yes O1 . P1 . C8 . C7 . 10.8(5) yes O1 . P1 . C8 . C9 . -167.1(5) yes C10 . P1 . C8 . C7 . -65.5(7) yes C10 . P1 . C8 . C9 . 116.6(6) yes C16 . P1 . C8 . C7 . 89.7(7) yes C16 . P1 . C8 . C9 . -88.1(7) yes C22 . P1 . C8 . C7 . -165.2(5) yes C22 . P1 . C8 . C9 . 17.0(7) yes O1 . P1 . C10 . C11 . -60.7(6) yes O1 . P1 . C10 . C15 . 119.2(6) yes C8 . P1 . C10 . C11 . 16.2(9) yes C8 . P1 . C10 . C15 . -163.8(6) yes C16 . P1 . C10 . C11 . -139.3(6) yes C16 . P1 . C10 . C15 . 40.7(8) yes C22 . P1 . C10 . C11 . 119.7(6) yes C22 . P1 . C10 . C15 . -60.4(7) yes O1 . P1 . C16 . C17 . 108.2(6) yes O1 . P1 . C16 . C21 . -69.5(6) yes C8 . P1 . C16 . C17 . 29.4(8) yes C8 . P1 . C16 . C21 . -148.3(6) yes C10 . P1 . C16 . C17 . -174.1(5) yes C10 . P1 . C16 . C21 . 8.2(9) yes C22 . P1 . C16 . C17 . -76.5(6) yes C22 . P1 . C16 . C21 . 105.8(6) yes O1 . P1 . C22 . C23 . -67.4(4) yes O1 . P1 . C22 . C27 . 108.4(4) yes C8 . P1 . C22 . C23 . 59.9(7) yes C8 . P1 . C22 . C27 . -124.3(6) yes C10 . P1 . C22 . C23 . -62.8(6) yes C10 . P1 . C22 . C27 . 113.0(7) yes C16 . P1 . C22 . C23 . 179.9(5) yes C16 . P1 . C22 . C27 . -4.3(8) yes P1 . O1 . C1 . C2 . -169.4(3) yes P1 . O1 . C1 . C7 . 11.1(4) yes O1 . C1 . C2 . C3 . -177.2(5) yes C7 . C1 . C2 . C3 . 2.2(9) yes O1 . C1 . C7 . C6 . 175.1(4) yes O1 . C1 . C7 . C8 . -3.0(6) yes C2 . C1 . C7 . C6 . -4.3(9) yes C2 . C1 . C7 . C8 . 177.6(5) yes C1 . C2 . C3 . C4 . 1.1(1) yes C2 . C3 . C4 . C5 . -1.3(1) yes C3 . C4 . C5 . C6 . -0.4(1) yes C4 . C5 . C6 . C7 . -0.1(1) yes C5 . C6 . C7 . C1 . 3.0(9) yes C5 . C6 . C7 . C8 . -179.1(5) yes C1 . C7 . C8 . P1 . -7.8(6) yes C1 . C7 . C8 . C9 . 170.1(5) yes C6 . C7 . C8 . P1 . 174.1(4) yes C6 . C7 . C8 . C9 . -8.1(8) yes P1 . C10 . C11 . C12 . 179.7(4) yes C15 . C10 . C11 . C12 . -0.2(9) yes P1 . C10 . C15 . C14 . -178.2(4) yes C11 . C10 . C15 . C14 . 1.8(9) yes C10 . C11 . C12 . C13 . -1.6(9) yes C11 . C12 . C13 . C14 . 1.8(1) yes C12 . C13 . C14 . C15 . -0.2(1) yes C13 . C14 . C15 . C10 . -1.6(1) yes P1 . C16 . C17 . C18 . -178.1(4) yes C21 . C16 . C17 . C18 . -0.4(9) yes P1 . C16 . C21 . C20 . 178.3(4) yes C17 . C16 . C21 . C20 . 0.7(9) yes C16 . C17 . C18 . C19 . 0.1(9) yes C17 . C18 . C19 . C20 . -0.1(1) yes C18 . C19 . C20 . C21 . 0.4(1) yes C19 . C20 . C21 . C16 . -0.6(9) yes P1 . C22 . C23 . C24 . 177.0(4) yes C27 . C22 . C23 . C24 . 0.9(8) yes P1 . C22 . C27 . C26 . -176.0(4) yes C23 . C22 . C27 . C26 . -0.3(8) yes C22 . C23 . C24 . C25 . -0.6(8) yes C23 . C24 . C25 . C26 . -0.3(9) yes C24 . C25 . C26 . C27 . 0.9(9) yes C25 . C26 . C27 . C22 . -0.6(9) yes loop_ _geom_contact_atom_site_label_1 _geom_contact_site_symmetry_1 _geom_contact_atom_site_label_2 _geom_contact_site_symmetry_2 _geom_contact_distance _geom_contact_publ_flag P1 . O1 . 1.999(3) yes P1 . C1 . 2.775(4) yes P1 . C7 . 2.703(4) yes P1 . C8 . 1.785(4) yes P1 . C9 . 2.890(5) yes P1 . C10 . 1.822(4) yes P1 . C11 . 2.810(4) yes P1 . C15 . 2.813(4) yes P1 . C16 . 1.825(4) yes P1 . C17 . 2.751(5) yes P1 . C21 . 2.842(4) yes P1 . C22 . 1.871(4) yes P1 . C23 . 2.798(4) yes P1 . C27 . 2.900(4) yes P1 . H1 . 2.82(5) no P1 . H4 . 3.08(5) no P1 . H6 . 2.86(5) no P1 . H7 . 2.84(5) no P1 . H10 . 2.94(6) no P1 . H14 . 3.29(5) no P1 . H15 . 2.89(6) no P1 . H21 . 3.47(6) no P1 . H23 . 2.89(5) no O1 . C1 . 1.293(5) yes O1 . C2 . 2.321(5) yes O1 . C5 3_545 3.252(5) yes O1 . C6 3_545 3.243(5) yes O1 . C7 . 2.305(5) yes O1 . C8 . 2.519(5) yes O1 . C10 . 2.511(5) yes O1 . C11 . 2.848(5) yes O1 . C15 . 3.578(5) yes O1 . C16 . 2.548(5) yes O1 . C17 . 3.462(5) yes O1 . C21 . 3.044(5) yes O1 . H3 4_456 2.81(5) no O1 . H6 . 2.97(5) no O1 . H10 . 2.79(6) no O1 . H16 . 2.37(5) no O1 . H19 3_545 2.59(5) no O1 . H20 3_545 2.49(5) no C1 . C2 . 1.392(5) yes C1 . C3 . 2.534(5) yes C1 . C4 . 3.167(6) yes C1 . C5 . 3.151(5) yes C1 . C6 . 2.563(6) yes C1 . C7 . 1.476(5) yes C1 . C8 . 2.392(5) yes C1 . C10 . 3.355(5) yes C1 . C11 . 3.239(6) yes C1 . C16 . 3.583(5) yes C1 . C25 4_456 3.566(6) yes C1 . H3 4_456 2.77(5) no C1 . H5 4_456 3.18(5) no C1 . H8 5_555 3.58(6) no C1 . H10 . 2.75(6) no C1 . H16 . 1.96(5) no C1 . H17 . 3.31(4) no C1 . H19 3_545 3.40(5) no C1 . H20 . 3.44(5) no C1 . H20 3_545 3.27(5) no C2 . C3 . 1.403(6) yes C2 . C4 . 2.508(6) yes C2 . C5 . 3.111(6) yes C2 . C6 . 3.132(6) yes C2 . C7 . 2.577(5) yes C2 . H3 4_456 3.17(5) no C2 . H5 4_456 2.92(5) no C2 . H8 5_555 3.30(6) no C2 . H9 7_555 3.07(5) no C2 . H10 . 3.46(6) no C2 . H12 8_456 3.52(6) no C2 . H16 . 0.99(6) no C2 . H17 . 1.98(4) no C2 . H18 . 3.32(5) no C2 . H19 3_545 3.55(5) no C2 . H20 3_545 3.28(5) no C3 . C4 . 1.372(6) yes C3 . C5 . 2.488(6) yes C3 . C6 . 3.118(6) yes C3 . C7 . 3.204(5) yes C3 . H1 8_456 3.57(5) no C3 . H2 8_456 3.55(5) no C3 . H5 4_456 2.80(6) no C3 . H8 5_555 2.93(6) no C3 . H9 7_555 3.52(5) no C3 . H16 . 2.09(6) no C3 . H17 . 0.96(4) no C3 . H18 . 1.99(5) no C3 . H19 . 3.27(5) no C4 . C5 . 1.404(6) yes C4 . C6 . 2.510(6) yes C4 . C7 . 3.206(6) yes C4 . C18 5_555 3.560(6) yes C4 . H1 8_456 3.30(5) no C4 . H2 8_456 3.11(5) no C4 . H5 4_456 2.89(6) no C4 . H8 5_555 2.75(6) no C4 . H16 . 3.37(6) no C4 . H17 . 2.01(4) no C4 . H18 . 0.97(5) no C4 . H19 . 1.98(5) no C4 . H20 . 3.36(5) no C5 . C6 . 1.362(6) yes C5 . C7 . 2.536(6) yes C5 . H5 4_456 3.11(6) no C5 . H6 3_555 3.11(5) no C5 . H8 5_555 2.90(6) no C5 . H9 5_555 3.26(5) no C5 . H16 3_555 3.28(6) no C5 . H17 . 3.31(4) no C5 . H18 . 2.04(5) no C5 . H19 . 0.96(5) no C5 . H20 . 2.01(5) no C6 . C7 . 1.426(5) yes C6 . C8 . 2.473(5) yes C6 . C9 . 2.955(6) yes C6 . C21 3_555 3.498(6) yes C6 . H5 4_456 3.33(5) no C6 . H6 3_555 3.08(5) no C6 . H8 5_555 3.24(6) no C6 . H14 . 3.18(5) no C6 . H16 3_555 3.12(6) no C6 . H18 . 3.32(5) no C6 . H19 . 1.99(5) no C6 . H20 . 1.03(5) no C6 . H21 . 2.82(6) no C7 . C8 . 1.390(5) yes C7 . C9 . 2.527(6) yes C7 . H3 4_456 3.28(5) no C7 . H5 4_456 3.41(5) no C7 . H8 5_555 3.55(6) no C7 . H10 . 2.92(6) no C7 . H14 . 2.92(5) no C7 . H15 . 3.30(6) no C7 . H16 . 3.37(6) no C7 . H19 . 3.35(5) no C7 . H20 . 2.08(5) no C7 . H21 . 2.68(6) no C8 . C9 . 1.509(5) yes C8 . C10 . 3.147(5) yes C8 . C11 . 3.494(6) yes C8 . C16 . 3.087(5) yes C8 . C17 . 3.371(6) yes C8 . C22 . 2.799(5) yes C8 . C23 . 3.217(6) yes C8 . H1 . 2.91(4) no C8 . H7 . 2.99(5) no C8 . H10 . 3.05(6) no C8 . H14 . 2.02(5) no C8 . H15 . 2.07(6) no C8 . H20 . 2.62(5) no C8 . H21 . 1.96(6) no C9 . C22 . 3.004(6) yes C9 . C23 . 3.121(6) yes C9 . H1 . 2.90(5) no C9 . H2 2_666 3.41(5) no C9 . H3 2_666 3.41(5) no C9 . H7 . 3.17(6) no C9 . H12 6_656 3.22(7) no C9 . H14 . 1.02(5) no C9 . H15 . 0.98(6) no C9 . H20 . 2.53(5) no C9 . H21 . 0.80(6) no C10 . C11 . 1.416(6) yes C10 . C12 . 2.429(6) yes C10 . C13 . 2.791(6) yes C10 . C14 . 2.411(6) yes C10 . C15 . 1.397(6) yes C10 . C16 . 3.100(6) yes C10 . C21 . 3.441(6) yes C10 . C22 . 2.678(5) yes C10 . C23 . 3.089(6) yes C10 . H1 . 2.95(5) no C10 . H6 . 2.88(5) no C10 . H10 . 2.14(6) no C10 . H11 . 3.34(5) no C10 . H13 . 3.28(5) no C10 . H17 8_556 3.37(4) no C10 . H19 3_545 2.85(5) no C10 . H23 . 1.98(6) no C11 . C12 . 1.393(7) yes C11 . C13 . 2.411(7) yes C11 . C14 . 2.779(7) yes C11 . C15 . 2.421(7) yes C11 . H1 . 3.29(5) no C11 . H10 . 1.03(6) no C11 . H11 . 2.10(5) no C11 . H12 . 3.22(7) no C11 . H17 8_556 3.35(4) no C11 . H19 3_545 2.85(5) no C11 . H23 . 3.21(6) no C12 . C13 . 1.390(8) yes C12 . C14 . 2.394(8) yes C12 . C15 . 2.779(7) yes C12 . H5 5_555 3.40(5) no C12 . H10 . 2.10(6) no C12 . H11 . 0.99(5) no C12 . H12 . 1.96(7) no C12 . H13 . 3.22(5) no C12 . H17 8_556 3.17(4) no C12 . H18 3_545 3.40(5) no C12 . H19 3_545 3.13(5) no C13 . C14 . 1.370(8) yes C13 . C15 . 2.393(7) yes C13 . H1 6_646 3.37(5) no C13 . H10 . 3.34(6) no C13 . H11 . 2.04(5) no C13 . H12 . 0.95(6) no C13 . H13 . 1.97(5) no C13 . H14 6_646 3.16(5) no C13 . H16 8_556 3.37(5) no C13 . H17 8_556 3.03(4) no C13 . H18 3_545 2.97(5) no C13 . H19 3_545 3.36(5) no C13 . H23 . 3.18(6) no C14 . C15 . 1.382(6) yes C14 . C19 2_656 3.544(7) yes C14 . H4 2_656 3.39(5) no C14 . H11 . 3.27(5) no C14 . H12 . 2.08(6) no C14 . H13 . 0.94(5) no C14 . H16 8_556 3.56(5) no C14 . H17 8_556 3.04(4) no C14 . H18 3_545 3.22(5) no C14 . H19 3_545 3.37(5) no C14 . H23 . 1.97(6) no C15 . C16 . 3.525(6) yes C15 . C21 . 3.426(6) yes C15 . C22 . 3.115(6) yes C15 . C23 . 3.580(6) yes C15 . H4 2_656 3.39(5) no C15 . H6 . 2.64(5) no C15 . H10 . 3.36(6) no C15 . H12 . 3.28(7) no C15 . H13 . 2.05(5) no C15 . H17 8_556 3.20(4) no C15 . H19 3_545 3.14(5) no C15 . H23 . 0.88(6) no C16 . C17 . 1.395(6) yes C16 . C18 . 2.409(6) yes C16 . C19 . 2.782(6) yes C16 . C20 . 2.407(6) yes C16 . C21 . 1.394(6) yes C16 . C22 . 2.802(5) yes C16 . C27 . 3.014(6) yes C16 . H3 4_456 3.37(5) no C16 . H4 . 2.60(5) no C16 . H6 . 2.02(5) no C16 . H7 . 2.07(6) no C16 . H8 . 3.32(6) no C16 . H22 . 3.20(6) no C16 . H23 . 3.23(5) no C17 . C18 . 1.388(6) yes C17 . C19 . 2.405(7) yes C17 . C20 . 2.771(7) yes C17 . C21 . 2.413(7) yes C17 . C22 . 3.371(6) yes C17 . C27 . 3.315(6) yes C17 . H2 4_456 3.54(5) no C17 . H3 4_456 3.20(5) no C17 . H4 . 2.72(5) no C17 . H6 . 3.29(5) no C17 . H7 . 0.97(6) no C17 . H8 . 2.08(6) no C17 . H9 . 3.36(5) no C17 . H15 . 3.50(6) no C18 . C19 . 1.385(8) yes C18 . C20 . 2.389(8) yes C18 . C21 . 2.779(7) yes C18 . H2 4_456 3.00(5) no C18 . H4 . 3.44(5) no C18 . H7 . 2.03(6) no C18 . H8 . 1.02(6) no C18 . H9 . 2.12(5) no C18 . H13 2_656 3.12(5) no C18 . H22 . 3.21(6) no C19 . C20 . 1.374(8) yes C19 . C21 . 2.408(6) yes C19 . H2 4_456 3.34(5) no C19 . H6 . 3.37(5) no C19 . H7 . 3.27(6) no C19 . H8 . 2.09(6) no C19 . H9 . 1.05(5) no C19 . H13 2_656 3.03(5) no C19 . H16 7_554 3.32(5) no C19 . H21 3_545 3.39(6) no C19 . H22 . 2.00(6) no C20 . C21 . 1.395(6) yes C20 . H6 . 2.17(5) no C20 . H8 . 3.31(6) no C20 . H9 . 2.10(5) no C20 . H13 2_656 3.46(5) no C20 . H21 3_545 3.05(6) no C20 . H22 . 0.90(6) no C20 . H23 2_656 3.13(5) no C21 . H4 . 3.25(5) no C21 . H6 . 1.02(5) no C21 . H7 . 3.30(6) no C21 . H9 . 3.35(5) no C21 . H20 3_545 3.09(5) no C21 . H21 3_545 3.36(6) no C21 . H22 . 1.97(6) no C21 . H23 . 3.05(5) no C21 . H23 2_656 3.22(6) no C22 . C23 . 1.399(6) yes C22 . C24 . 2.423(6) yes C22 . C25 . 2.806(6) yes C22 . C26 . 2.417(5) yes C22 . C27 . 1.391(5) yes C22 . H1 . 2.00(5) no C22 . H2 . 3.27(5) no C22 . H4 . 2.08(5) no C22 . H5 . 3.28(6) no C22 . H7 . 3.25(5) no C22 . H14 . 3.15(5) no C22 . H15 . 2.52(6) no C22 . H23 . 2.89(6) no C23 . C24 . 1.381(6) yes C23 . C25 . 2.407(6) yes C23 . C26 . 2.764(6) yes C23 . C27 . 2.392(6) yes C23 . H1 . 0.92(5) no C23 . H2 . 2.02(5) no C23 . H3 . 3.32(5) no C23 . H4 . 3.28(5) no C23 . H14 . 2.81(5) no C23 . H15 . 2.79(6) no C23 . H17 8_556 3.21(4) no C23 . H18 8_556 2.98(5) no C23 . H23 . 3.56(6) no C24 . C25 . 1.400(6) yes C24 . C26 . 2.400(6) yes C24 . C27 . 2.771(6) yes C24 . H1 . 2.01(5) no C24 . H2 . 0.94(5) no C24 . H3 . 2.11(5) no C24 . H5 . 3.23(6) no C24 . H14 2_666 3.56(5) no C24 . H15 2_666 3.53(6) no C24 . H17 8_556 3.46(4) no C24 . H18 8_556 3.06(4) no C24 . H21 2_666 3.41(6) no C24 . H22 2_656 3.41(6) no C25 . C26 . 1.383(6) yes C25 . C27 . 2.405(6) yes C25 . H1 . 3.24(5) no C25 . H2 . 2.05(5) no C25 . H3 . 0.99(5) no C25 . H4 . 3.24(5) no C25 . H5 . 1.99(6) no C25 . H14 2_666 3.35(5) no C25 . H21 2_666 3.38(6) no C25 . H22 2_656 3.08(6) no C26 . C27 . 1.387(6) yes C26 . H2 . 3.26(5) no C26 . H3 . 2.05(5) no C26 . H4 . 2.00(5) no C26 . H5 . 0.94(6) no C26 . H6 2_656 3.15(5) no C26 . H11 5_554 2.98(5) no C26 . H22 2_656 3.14(6) no C27 . H1 . 3.21(5) no C27 . H3 . 3.29(5) no C27 . H4 . 0.96(5) no C27 . H5 . 2.06(5) no C27 . H6 2_656 3.30(5) no C27 . H7 . 3.29(5) no C27 . H11 5_554 3.00(5) no C27 . H15 . 3.20(6) no C27 . H22 2_656 3.54(6) no C27 . H23 . 3.20(6) no C27 . H23 2_656 3.58(6) no H1 . H2 . 2.31(6) no H1 . H10 . 3.27(8) no H1 . H12 6_656 2.89(8) no H1 . H14 . 2.38(7) no H1 . H15 . 2.86(7) no H1 . H17 8_556 3.05(6) no H1 . H18 8_556 2.46(7) no H2 . H3 . 2.41(7) no H2 . H8 4_556 3.06(8) no H2 . H9 4_556 3.53(7) no H2 . H14 2_666 3.56(7) no H2 . H15 2_666 3.17(7) no H2 . H17 8_556 3.38(6) no H2 . H18 8_556 2.54(6) no H2 . H21 2_666 3.03(8) no H3 . H5 . 2.28(7) no H3 . H7 4_556 3.39(7) no H3 . H14 2_666 3.22(7) no H3 . H16 4_556 3.36(7) no H3 . H20 2_666 3.30(7) no H3 . H21 2_666 2.99(8) no H3 . H22 2_656 3.32(8) no H4 . H5 . 2.31(7) no H4 . H6 2_656 3.26(7) no H4 . H7 . 2.86(7) no H4 . H11 5_554 2.94(7) no H4 . H13 2_656 2.87(7) no H4 . H15 . 3.56(8) no H4 . H23 . 3.39(8) no H4 . H23 2_656 2.93(8) no H5 . H6 2_656 3.05(8) no H5 . H11 5_554 2.95(7) no H5 . H12 5_554 3.58(8) no H5 . H16 4_556 3.49(7) no H5 . H17 4_556 3.27(7) no H5 . H18 4_556 3.42(7) no H5 . H22 2_656 3.51(8) no H6 . H19 3_545 2.98(6) no H6 . H20 3_545 2.91(7) no H6 . H22 . 2.43(8) no H6 . H23 . 2.35(7) no H6 . H23 2_656 3.38(7) no H7 . H8 . 2.34(8) no H7 . H11 5_554 3.40(7) no H7 . H15 . 2.74(8) no H7 . H21 . 3.20(8) no H7 . H22 3_555 3.26(8) no H8 . H9 . 2.44(8) no H8 . H10 5_554 3.21(9) no H8 . H13 2_656 3.29(8) no H8 . H17 5_554 3.43(7) no H8 . H18 5_554 3.17(8) no H8 . H19 5_554 3.40(8) no H9 . H13 2_656 3.27(7) no H9 . H16 7_554 2.43(7) no H9 . H17 7_554 3.24(6) no H9 . H19 5_554 3.05(6) no H9 . H22 . 2.37(8) no H10 . H11 . 2.43(8) no H10 . H13 6_656 3.27(8) no H10 . H19 3_545 3.37(8) no H11 . H12 . 2.22(8) no H11 . H15 5_555 3.20(8) no H12 . H13 . 2.36(8) no H12 . H14 6_646 2.23(8) no H12 . H16 8_556 3.05(8) no H12 . H17 8_556 3.33(8) no H12 . H18 3_545 3.23(8) no H12 . H20 6_646 3.55(8) no H13 . H16 8_556 3.52(7) no H13 . H17 8_556 3.52(7) no H13 . H18 3_545 3.40(7) no H13 . H23 . 2.34(8) no H14 . H15 . 1.59(7) no H14 . H20 . 2.67(7) no H14 . H21 . 1.60(7) no H15 . H20 . 3.48(8) no H15 . H21 . 1.40(8) no H16 . H17 . 2.28(7) no H16 . H19 3_545 2.91(7) no H16 . H20 3_545 2.55(7) no H17 . H18 . 2.23(6) no H17 . H22 7_555 3.41(7) no H18 . H19 . 2.21(7) no H19 . H20 . 2.23(7) no H20 . H21 . 2.26(7) no H21 . H22 3_555 3.14(8) no H22 . H23 2_656 3.21(8) no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data_b _database_code_CSD 172472 _audit_creation_method 'maXus' _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Prisms' _exptl_crystal_colour 'Orange' _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment 'refxyz' _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 loop_ _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 -0.02598 _diffrn_orient_matrix_UB_12 0.04824 _diffrn_orient_matrix_UB_13 -0.02088 _diffrn_orient_matrix_UB_21 -0.02638 _diffrn_orient_matrix_UB_22 0.00237 _diffrn_orient_matrix_UB_23 0.06635 _diffrn_orient_matrix_UB_31 0.04336 _diffrn_orient_matrix_UB_32 0.03055 _diffrn_orient_matrix_UB_33 0.02786 _cell_formula_units_Z 8 _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 380.427 _diffrn_radiation_type ' CuK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,-Y,-Z' '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,+Y,-Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X+ 1/2,+Y+ 1/2,+Z' '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P b c a ' _symmetry_cell_setting 'Orthorhombic' _chemical_formula_moiety 'C26 H21 O P ' _chemical_formula_sum 'C26 H21 O P ' _chemical_name_systematic ; ? ; _cell_length_a 17.54 _cell_length_b 17.50 _cell_length_c 13.35 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4095.59 _diffrn_reflns_number 4529 _diffrn_reflns_theta_max 69.99 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_full 69.99 _diffrn_reflns_av_R_equivalents 0.021 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _exptl_absorpt_coefficient_mu 1.277 _reflns_number_total 3689 _reflns_number_gt 3524 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1033P)^2^+3.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3689 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.1765 _refine_ls_wR_factor_gt 0.1751 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 P1 P 0.91377(3) 0.10145(3) 0.71488(5) 0.0422(2) Uani 1 1 d . . . O1 O 0.84899(10) 0.19956(10) 0.65396(12) 0.0458(4) Uani 1 1 d . . . C1 C 0.82037(13) 0.23959(12) 0.72499(16) 0.0381(5) Uani 1 1 d . . . C8 C 0.88998(14) 0.15000(14) 0.82470(18) 0.0441(5) Uani 1 1 d . . . C7 C 0.84451(13) 0.21476(13) 0.82505(17) 0.0388(5) Uani 1 1 d . . . C2 C 0.77034(14) 0.29909(14) 0.70198(18) 0.0441(5) Uani 1 1 d . . . C5 C 0.78148(15) 0.31671(15) 0.93239(19) 0.0486(6) Uani 1 1 d . . . C10 C 0.84038(14) 0.04978(13) 0.64646(19) 0.0452(5) Uani 1 1 d . . . C16 C 0.98596(14) 0.14279(14) 0.6345(2) 0.0473(6) Uani 1 1 d . . . C3 C 0.73473(15) 0.35268(14) 0.7638(2) 0.0486(6) Uani 1 1 d . . . C22 C 0.96520(15) 0.01775(14) 0.7650(2) 0.0483(6) Uani 1 1 d . . . C15 C 0.85875(18) -0.00047(15) 0.5700(2) 0.0561(7) Uani 1 1 d . . . C21 C 0.97793(16) 0.15014(17) 0.5320(2) 0.0560(7) Uani 1 1 d . . . C27 C 1.02596(16) -0.01597(17) 0.7140(2) 0.0564(7) Uani 1 1 d . . . C17 C 1.05107(18) 0.17178(18) 0.6808(3) 0.0624(8) Uani 1 1 d . . . C4 C 0.74023(16) 0.36166(15) 0.8656(2) 0.0515(6) Uani 1 1 d . . . C11 C 0.76386(16) 0.05934(16) 0.6730(2) 0.0579(7) Uani 1 1 d . . . C6 C 0.82566(15) 0.25315(14) 0.91565(18) 0.0463(6) Uani 1 1 d . . . C23 C 0.9390(2) -0.01906(17) 0.8506(3) 0.0690(9) Uani 1 1 d . . . C12 C 0.70792(19) 0.0189(2) 0.6220(3) 0.0751(10) Uani 1 1 d . . . C26 C 1.05862(18) -0.08315(18) 0.7482(3) 0.0673(8) Uani 1 1 d . . . C25 C 1.03188(19) -0.11865(18) 0.8334(3) 0.0713(9) Uani 1 1 d . . . C20 C 1.0342(2) 0.18652(19) 0.4750(3) 0.0697(8) Uani 1 1 d . . . C14 C 0.8012(2) -0.03897(18) 0.5188(3) 0.0756(10) Uani 1 1 d . . . C18 C 1.1066(2) 0.2084(2) 0.6236(3) 0.0758(10) Uani 1 1 d . . . C19 C 1.0981(2) 0.2154(2) 0.5228(3) 0.0763(10) Uani 1 1 d . . . C13 C 0.7268(2) -0.0294(2) 0.5457(3) 0.0802(11) Uani 1 1 d . . . C24 C 0.9724(2) -0.08613(19) 0.8850(3) 0.0817(11) Uani 1 1 d . . . H4 H 0.9061 0.1314 0.8912 0.053 Uiso 1 1 d R . . H6 H 0.7581 0.3021 0.6321 0.053 Uiso 1 1 d R . . H7 H 0.7798 0.3359 1.0161 0.058 Uiso 1 1 d R . . H10 H 0.6914 0.3884 0.7217 0.058 Uiso 1 1 d R . . H12 H 0.9199 -0.0122 0.5531 0.067 Uiso 1 1 d R . . H13 H 0.9262 0.1307 0.4983 0.067 Uiso 1 1 d R . . H14 H 1.0522 0.0139 0.6494 0.068 Uiso 1 1 d R . . H15 H 1.0602 0.1666 0.7618 0.075 Uiso 1 1 d R . . H16 H 0.7091 0.4048 0.9046 0.062 Uiso 1 1 d R . . H17 H 0.7572 0.0970 0.7452 0.070 Uiso 1 1 d R . . H18 H 0.8542 0.2194 0.9849 0.056 Uiso 1 1 d R . . H19 H 0.9057 0.0090 0.9013 0.083 Uiso 1 1 d R . . H20 H 0.6502 0.0249 0.6439 0.090 Uiso 1 1 d R . . H21 H 1.1039 -0.1078 0.7087 0.081 Uiso 1 1 d R . . H22 H 1.0549 -0.1723 0.8713 0.086 Uiso 1 1 d R . . H23 H 1.0191 0.2001 0.3948 0.084 Uiso 1 1 d R . . H24 H 0.8172 -0.0819 0.4682 0.091 Uiso 1 1 d R . . H25 H 1.1551 0.2235 0.6657 0.091 Uiso 1 1 d R . . H26 H 1.1427 0.2429 0.4814 0.092 Uiso 1 1 d R . . H27 H 0.6794 -0.0618 0.5209 0.096 Uiso 1 1 d R . . H28 H 0.9462 -0.1135 0.9536 0.098 Uiso 1 1 d 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 P1 0.0427(4) 0.0375(3) 0.0464(4) -0.0037(2) 0.0025(2) 0.0008(2) O1 0.0567(10) 0.0429(9) 0.0378(8) -0.0039(7) 0.0026(7) 0.0034(8) C1 0.0436(12) 0.0318(10) 0.0388(11) -0.0007(8) 0.0000(9) -0.0026(9) C8 0.0518(13) 0.0395(12) 0.0411(12) 0.0015(9) -0.0022(10) 0.0074(10) C7 0.0428(12) 0.0351(11) 0.0385(11) -0.0010(9) 0.0011(9) -0.0007(9) C2 0.0501(13) 0.0395(12) 0.0425(12) 0.0036(10) -0.0014(10) 0.0017(10) C5 0.0514(14) 0.0467(13) 0.0479(13) -0.0117(11) 0.0030(11) -0.0003(11) C10 0.0499(13) 0.0362(12) 0.0495(13) 0.0041(10) 0.0002(11) -0.0013(10) C16 0.0460(13) 0.0382(12) 0.0576(15) -0.0049(10) 0.0038(11) -0.0009(10) C3 0.0500(14) 0.0382(12) 0.0576(15) 0.0027(11) 0.0022(11) 0.0036(10) C22 0.0443(13) 0.0397(12) 0.0608(15) -0.0028(11) -0.0010(11) 0.0012(10) C15 0.0674(18) 0.0433(13) 0.0577(16) -0.0042(12) -0.0084(13) 0.0006(12) C21 0.0505(14) 0.0571(16) 0.0605(16) 0.0016(13) 0.0061(12) -0.0014(12) C27 0.0493(14) 0.0555(15) 0.0643(17) -0.0052(13) 0.0001(12) 0.0120(12) C17 0.0590(17) 0.0571(16) 0.0711(18) -0.0092(14) -0.0001(14) -0.0153(14) C4 0.0549(14) 0.0423(12) 0.0575(15) -0.0103(11) 0.0043(12) 0.0049(11) C11 0.0484(14) 0.0477(14) 0.0776(19) 0.0088(13) 0.0007(13) -0.0064(12) C6 0.0515(13) 0.0456(13) 0.0419(12) -0.0033(10) 0.0001(11) -0.0006(11) C23 0.0705(19) 0.0463(15) 0.090(2) 0.0152(15) 0.0184(17) 0.0109(14) C12 0.0534(17) 0.0643(19) 0.108(3) 0.028(2) -0.0133(17) -0.0155(15) C26 0.0578(17) 0.0583(16) 0.086(2) -0.0076(17) -0.0055(16) 0.0190(14) C25 0.0657(19) 0.0478(15) 0.100(3) 0.0048(16) -0.0100(18) 0.0119(14) C20 0.0713(19) 0.0687(19) 0.0692(19) 0.0083(15) 0.0170(16) -0.0019(16) C14 0.107(3) 0.0493(16) 0.070(2) -0.0036(14) -0.0298(19) -0.0053(17) C18 0.0611(18) 0.0662(19) 0.100(3) -0.0101(19) 0.0078(18) -0.0215(16) C19 0.0645(19) 0.0649(19) 0.099(3) 0.0003(18) 0.0244(18) -0.0141(16) C13 0.088(3) 0.0542(17) 0.098(3) 0.0223(18) -0.046(2) -0.0193(17) C24 0.089(2) 0.0511(16) 0.105(3) 0.0239(18) 0.018(2) 0.0116(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C8 1.745(2) . ? P1 C16 1.810(3) . ? P1 C10 1.819(3) . ? P1 C22 1.845(3) . ? P1 O1 2.2132(18) . ? O1 C1 1.281(3) . ? C1 C2 1.396(3) . ? C1 C7 1.467(3) . ? C8 C7 1.386(3) . ? C7 C6 1.422(3) . ? C2 C3 1.397(4) . ? C5 C6 1.374(4) . ? C5 C4 1.392(4) . ? C10 C15 1.385(4) . ? C10 C11 1.398(4) . ? C16 C21 1.382(4) . ? C16 C17 1.394(4) . ? C3 C4 1.371(4) . ? C22 C23 1.389(4) . ? C22 C27 1.396(4) . ? C15 C14 1.392(4) . ? C21 C20 1.399(4) . ? C27 C26 1.385(4) . ? C17 C18 1.394(5) . ? C11 C12 1.388(5) . ? C23 C24 1.390(4) . ? C12 C13 1.364(6) . ? C26 C25 1.378(5) . ? C25 C24 1.373(5) . ? C20 C19 1.386(5) . ? C14 C13 1.365(6) . ? C18 C19 1.359(6) . ? C8 H4 0.9871 . ? C2 H6 0.9590 . ? C5 H7 1.1670 . ? C3 H10 1.1331 . ? C15 H12 1.1151 . ? C21 H13 1.0680 . ? C27 H14 1.1091 . ? C17 H15 1.0960 . ? C4 H16 1.0681 . ? C11 H17 1.1730 . ? C6 H18 1.2060 . ? C23 H19 1.0191 . ? C12 H20 1.0589 . ? C26 H21 1.0461 . ? C25 H22 1.1410 . ? C20 H23 1.1270 . ? C14 H24 1.0489 . ? C18 H25 1.0521 . ? C19 H26 1.0719 . ? C13 H27 1.0591 . ? C24 H28 1.1301 . ? 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 _geom_angle_publ_flag C8 P1 C16 118.07(12) . . ? C8 P1 C10 119.64(12) . . ? C16 P1 C10 113.34(12) . . ? C8 P1 C22 101.45(12) . . ? C16 P1 C22 100.96(12) . . ? C10 P1 C22 97.68(11) . . ? C8 P1 O1 78.94(9) . . ? C16 P1 O1 80.30(10) . . ? C10 P1 O1 80.66(9) . . ? C22 P1 O1 178.24(10) . . ? C1 O1 P1 110.70(14) . . ? O1 C1 C2 119.4(2) . . ? O1 C1 C7 113.5(2) . . ? C2 C1 C7 127.1(2) . . ? C7 C8 P1 122.59(19) . . ? C8 C7 C6 121.5(2) . . ? C8 C7 C1 113.9(2) . . ? C6 C7 C1 124.5(2) . . ? C1 C2 C3 130.7(2) . . ? C6 C5 C4 130.3(2) . . ? C15 C10 C11 119.1(3) . . ? C15 C10 P1 121.4(2) . . ? C11 C10 P1 119.5(2) . . ? C21 C16 C17 119.3(3) . . ? C21 C16 P1 123.6(2) . . ? C17 C16 P1 117.1(2) . . ? C4 C3 C2 129.1(2) . . ? C23 C22 C27 117.2(3) . . ? C23 C22 P1 120.3(2) . . ? C27 C22 P1 122.1(2) . . ? C10 C15 C14 120.0(3) . . ? C16 C21 C20 120.6(3) . . ? C26 C27 C22 120.9(3) . . ? C18 C17 C16 119.8(3) . . ? C3 C4 C5 127.3(2) . . ? C12 C11 C10 119.6(3) . . ? C5 C6 C7 130.7(2) . . ? C22 C23 C24 121.6(3) . . ? C13 C12 C11 120.7(3) . . ? C25 C26 C27 120.9(3) . . ? C24 C25 C26 119.1(3) . . ? C19 C20 C21 119.1(3) . . ? C13 C14 C15 120.3(3) . . ? C19 C18 C17 120.5(3) . . ? C18 C19 C20 120.8(3) . . ? C12 C13 C14 120.3(3) . . ? C25 C24 C23 120.3(3) . . ? C7 C8 H4 115.5 . . ? P1 C8 H4 121.8 . . ? C1 C2 H6 113.4 . . ? C3 C2 H6 115.9 . . ? C6 C5 H7 113.8 . . ? C4 C5 H7 115.9 . . ? C4 C3 H10 118.4 . . ? C2 C3 H10 112.1 . . ? C10 C15 H12 119.3 . . ? C14 C15 H12 120.5 . . ? C16 C21 H13 118.3 . . ? C20 C21 H13 121.0 . . ? C26 C27 H14 119.0 . . ? C22 C27 H14 119.8 . . ? C18 C17 H15 118.5 . . ? C16 C17 H15 121.8 . . ? C3 C4 H16 121.9 . . ? C5 C4 H16 110.7 . . ? C12 C11 H17 128.2 . . ? C10 C11 H17 111.8 . . ? C5 C6 H18 120.4 . . ? C7 C6 H18 108.9 . . ? C22 C23 H19 120.8 . . ? C24 C23 H19 115.4 . . ? C13 C12 H20 120.0 . . ? C11 C12 H20 119.3 . . ? C25 C26 H21 119.3 . . ? C27 C26 H21 119.8 . . ? C24 C25 H22 112.8 . . ? C26 C25 H22 128.1 . . ? C19 C20 H23 123.4 . . ? C21 C20 H23 116.5 . . ? C13 C14 H24 120.9 . . ? C15 C14 H24 118.0 . . ? C19 C18 H25 126.4 . . ? C17 C18 H25 112.8 . . ? C18 C19 H26 118.1 . . ? C20 C19 H26 121.1 . . ? C12 C13 H27 112.0 . . ? C14 C13 H27 127.1 . . ? C25 C24 H28 122.7 . . ? C23 C24 H28 117.0 . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.225 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.064