# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'John Protasiewicz' 'Xufang Chen' 'Rhett C. Smith' _publ_contact_author_name 'Prof John Protasiewicz' _publ_contact_author_address ; Department of Chemistry Case Western Reserve University 10900 Euclid Ave Cleveland Ohio 44106-7078 UNITED STATES OF AMERICA ; _publ_contact_author_email JDP5@PO.CWRU.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Cycloaddition of phosphanylidene-?4-phosphoranes ArP=PMe3 and quinones to yield 1,3,2-dioxophospholanes ; data_dmpqc1 _database_code_CSD 216923 _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetrachlorobenzo-2,6-dimesitylphenyl-1,3,2-dioxophospholane ; _chemical_name_common tetrachlorobenzo-2,6-dimesitylphenyl-1,3,2-dioxophospholane _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H25 Cl4 O2 P' _chemical_formula_weight 590.27 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 8.451(3) _cell_length_b 24.614(8) _cell_length_c 14.068(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.55(2) _cell_angle_gamma 90.00 _cell_volume 2819.1(14) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 39 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 12.47 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.503 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1924 _exptl_absorpt_correction_T_max 0.4126 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5714 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.1548 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 24.00 _reflns_number_total 4432 _reflns_number_gt 1851 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1382P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4432 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2103 _refine_ls_R_factor_gt 0.0800 _refine_ls_wR_factor_ref 0.2652 _refine_ls_wR_factor_gt 0.1900 _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_restrained_S_all 0.910 _refine_ls_shift/su_max 0.482 _refine_ls_shift/su_mean 0.016 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 0.2569(3) 0.39735(8) 0.81380(16) 0.0514(7) Uani 1 1 d . . . Cl2 Cl 0.5412(4) 0.15336(10) 0.8752(2) 0.0898(10) Uani 1 1 d . . . Cl3 Cl 0.1644(4) 0.13744(9) 0.7859(2) 0.0914(10) Uani 1 1 d . . . Cl4 Cl -0.0639(3) 0.23925(12) 0.7287(3) 0.1091(12) Uani 1 1 d . . . Cl1 Cl 0.6865(3) 0.27149(12) 0.9075(2) 0.0938(10) Uani 1 1 d . . . O2 O 0.1278(7) 0.3457(2) 0.7730(4) 0.0573(16) Uani 1 1 d . . . O1 O 0.4235(7) 0.3574(2) 0.8395(4) 0.0508(15) Uani 1 1 d . . . C11 C 0.1978(13) 0.2653(4) 0.5497(6) 0.058(2) Uani 1 1 d . . . H11 H 0.1060 0.2437 0.5236 0.069 Uiso 1 1 calc R . . C30 C 0.2110(10) 0.2971(3) 0.7919(6) 0.044(2) Uani 1 1 d . . . C25 C 0.3777(10) 0.3042(3) 0.8298(5) 0.043(2) Uani 1 1 d . . . C28 C 0.2462(13) 0.2018(3) 0.8041(6) 0.054(2) Uani 1 1 d . . . C29 C 0.1445(11) 0.2466(3) 0.7783(6) 0.052(2) Uani 1 1 d . . . C16 C 0.2051(11) 0.5159(3) 0.7960(6) 0.043(2) Uani 1 1 d . . . C6 C 0.2415(10) 0.4905(3) 0.7081(6) 0.048(2) Uani 1 1 d . . . C10 C 0.3496(14) 0.2407(4) 0.5774(6) 0.059(3) Uani 1 1 d . . . C2 C 0.2944(10) 0.4113(3) 0.6150(6) 0.045(2) Uani 1 1 d . . . C1 C 0.2656(10) 0.4340(3) 0.7026(5) 0.043(2) Uani 1 1 d . . . C12 C 0.1752(11) 0.3207(3) 0.5589(6) 0.052(2) Uani 1 1 d . . . C19 C 0.1350(14) 0.5678(3) 0.9575(6) 0.058(2) Uani 1 1 d . . . C9 C 0.4827(13) 0.2733(4) 0.6126(6) 0.060(3) Uani 1 1 d . . . H9 H 0.5866 0.2575 0.6288 0.072 Uiso 1 1 calc R . . C26 C 0.4796(11) 0.2599(4) 0.8576(6) 0.059(2) Uani 1 1 d . . . C18 C 0.2921(12) 0.5662(3) 0.9480(6) 0.058(2) Uani 1 1 d . . . H18 H 0.3754 0.5828 0.9960 0.069 Uiso 1 1 calc R . . C20 C 0.0129(11) 0.5433(3) 0.8857(7) 0.058(2) Uani 1 1 d . . . H20 H -0.0940 0.5440 0.8918 0.070 Uiso 1 1 calc R . . C7 C 0.3137(12) 0.3526(3) 0.6002(6) 0.048(2) Uani 1 1 d . . . C4 C 0.2874(13) 0.5025(4) 0.5487(7) 0.074(3) Uani 1 1 d . . . H4 H 0.2969 0.5254 0.4980 0.089 Uiso 1 1 calc R . . C5 C 0.2538(12) 0.5234(4) 0.6309(7) 0.065(3) Uani 1 1 d . . . H5 H 0.2387 0.5606 0.6350 0.079 Uiso 1 1 calc R . . C8 C 0.4703(11) 0.3297(4) 0.6256(6) 0.052(2) Uani 1 1 d . . . C13 C 0.6244(11) 0.3635(4) 0.6641(7) 0.075(3) Uani 1 1 d . . . H13A H 0.6537 0.3804 0.6097 0.113 Uiso 1 1 calc R . . H13B H 0.7126 0.3405 0.6991 0.113 Uiso 1 1 calc R . . H13C H 0.6043 0.3910 0.7079 0.113 Uiso 1 1 calc R . . C17 C 0.3315(11) 0.5407(3) 0.8693(6) 0.047(2) Uani 1 1 d . . . C27 C 0.4133(13) 0.2082(3) 0.8437(6) 0.052(2) Uani 1 1 d . . . C21 C 0.0423(11) 0.5176(3) 0.8047(6) 0.051(2) Uani 1 1 d . . . C22 C 0.5068(11) 0.5377(4) 0.8634(7) 0.070(3) Uani 1 1 d . . . H22A H 0.5219 0.5625 0.8138 0.106 Uiso 1 1 calc R . . H22B H 0.5305 0.5014 0.8464 0.106 Uiso 1 1 calc R . . H22C H 0.5795 0.5473 0.9261 0.106 Uiso 1 1 calc R . . C3 C 0.3073(12) 0.4476(4) 0.5410(6) 0.066(3) Uani 1 1 d . . . H3 H 0.3301 0.4339 0.4844 0.079 Uiso 1 1 calc R . . C23 C 0.0931(14) 0.5963(4) 1.0424(8) 0.092(3) Uani 1 1 d . . . H23A H 0.1900 0.5993 1.0965 0.138 Uiso 1 1 calc R . . H23B H 0.0113 0.5758 1.0628 0.138 Uiso 1 1 calc R . . H23C H 0.0514 0.6319 1.0219 0.138 Uiso 1 1 calc R . . C15 C 0.0068(12) 0.3454(4) 0.5263(7) 0.079(3) Uani 1 1 d . . . H15A H -0.0330 0.3523 0.5830 0.119 Uiso 1 1 calc R . . H15B H -0.0662 0.3207 0.4829 0.119 Uiso 1 1 calc R . . H15C H 0.0118 0.3789 0.4923 0.119 Uiso 1 1 calc R . . C14 C 0.3727(16) 0.1804(4) 0.5722(7) 0.092(4) Uani 1 1 d . . . H14A H 0.4553 0.1729 0.5385 0.138 Uiso 1 1 calc R . . H14B H 0.2710 0.1638 0.5370 0.138 Uiso 1 1 calc R . . H14C H 0.4068 0.1657 0.6378 0.138 Uiso 1 1 calc R . . C24 C -0.0955(12) 0.4925(4) 0.7274(7) 0.083(3) Uani 1 1 d . . . H24A H -0.1985 0.5032 0.7384 0.125 Uiso 1 1 calc R . . H24B H -0.0856 0.4537 0.7309 0.125 Uiso 1 1 calc R . . H24C H -0.0908 0.5047 0.6634 0.125 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 P1 0.0717(17) 0.0385(12) 0.0495(14) 0.0088(11) 0.0260(12) 0.0059(13) Cl2 0.112(2) 0.0621(16) 0.099(2) 0.0217(15) 0.0347(18) 0.0439(16) Cl3 0.129(3) 0.0447(14) 0.100(2) 0.0003(14) 0.0291(19) -0.0159(16) Cl4 0.0593(18) 0.088(2) 0.168(3) 0.029(2) 0.0091(18) -0.0189(16) Cl1 0.0551(17) 0.092(2) 0.120(2) 0.0317(17) -0.0001(16) 0.0092(15) O2 0.053(4) 0.034(3) 0.091(4) 0.015(3) 0.031(3) 0.014(3) O1 0.055(4) 0.041(3) 0.050(3) 0.001(3) 0.005(3) -0.007(3) C11 0.075(7) 0.050(6) 0.047(5) -0.001(4) 0.015(5) -0.010(5) C30 0.034(5) 0.050(5) 0.049(5) 0.008(4) 0.014(4) 0.003(4) C25 0.049(6) 0.044(5) 0.036(5) -0.006(4) 0.012(4) -0.005(5) C28 0.083(8) 0.031(5) 0.051(5) -0.002(4) 0.023(5) 0.004(5) C29 0.051(6) 0.041(5) 0.060(6) 0.004(4) 0.011(4) -0.008(5) C16 0.052(6) 0.027(4) 0.047(5) 0.003(4) 0.005(4) 0.006(4) C6 0.058(6) 0.038(5) 0.049(5) 0.001(4) 0.019(5) -0.006(4) C10 0.084(8) 0.043(5) 0.051(6) -0.006(5) 0.018(5) 0.001(6) C2 0.054(5) 0.030(4) 0.050(5) -0.001(4) 0.011(4) -0.002(4) C1 0.047(5) 0.040(5) 0.040(5) 0.002(4) 0.007(4) -0.002(4) C12 0.050(6) 0.041(5) 0.060(6) -0.010(4) 0.008(5) 0.000(5) C19 0.078(8) 0.041(5) 0.057(6) -0.011(5) 0.023(6) -0.003(5) C9 0.073(7) 0.067(7) 0.046(5) 0.001(5) 0.023(5) 0.027(6) C26 0.052(6) 0.065(6) 0.056(6) 0.007(5) 0.009(5) 0.013(5) C18 0.061(7) 0.042(5) 0.064(6) -0.014(5) 0.007(5) -0.010(5) C20 0.049(6) 0.052(5) 0.077(7) 0.001(5) 0.022(5) 0.010(5) C7 0.061(6) 0.043(5) 0.042(5) 0.001(4) 0.020(5) 0.009(5) C4 0.121(9) 0.052(6) 0.048(6) 0.003(5) 0.020(6) -0.006(6) C5 0.093(8) 0.037(5) 0.066(6) 0.004(5) 0.021(6) -0.008(5) C8 0.059(7) 0.065(6) 0.036(5) -0.006(4) 0.019(5) 0.003(5) C13 0.061(7) 0.075(7) 0.084(7) -0.007(6) 0.009(6) -0.003(6) C17 0.050(6) 0.034(5) 0.053(5) 0.000(4) 0.007(5) 0.008(4) C27 0.073(7) 0.045(6) 0.043(5) 0.001(4) 0.022(5) 0.013(5) C21 0.049(6) 0.047(5) 0.056(6) 0.001(5) 0.011(5) 0.003(5) C22 0.057(7) 0.076(7) 0.072(7) -0.006(5) 0.007(5) -0.005(5) C3 0.093(8) 0.055(6) 0.052(6) -0.009(5) 0.025(5) -0.005(5) C23 0.106(9) 0.074(7) 0.109(9) -0.016(7) 0.052(7) -0.008(7) C15 0.063(7) 0.082(7) 0.085(7) -0.009(6) 0.006(6) -0.006(6) C14 0.153(11) 0.056(6) 0.073(7) -0.012(5) 0.040(7) -0.005(7) C24 0.063(7) 0.092(8) 0.088(8) -0.012(6) 0.008(6) -0.011(6) _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 O2 1.674(6) . ? P1 O1 1.675(6) . ? P1 C1 1.824(8) . ? Cl2 C27 1.712(9) . ? Cl3 C28 1.721(9) . ? Cl4 C29 1.722(9) . ? Cl1 C26 1.724(10) . ? O2 C30 1.376(9) . ? O1 C25 1.362(9) . ? C11 C10 1.377(12) . ? C11 C12 1.389(11) . ? C30 C29 1.356(11) . ? C30 C25 1.378(11) . ? C25 C26 1.379(11) . ? C28 C27 1.381(12) . ? C28 C29 1.385(11) . ? C16 C21 1.413(11) . ? C16 C17 1.410(11) . ? C16 C6 1.489(10) . ? C6 C5 1.380(11) . ? C6 C1 1.412(11) . ? C10 C9 1.362(12) . ? C10 C14 1.503(12) . ? C2 C3 1.398(11) . ? C2 C1 1.431(10) . ? C2 C7 1.476(11) . ? C12 C7 1.399(11) . ? C12 C15 1.501(12) . ? C19 C18 1.371(12) . ? C19 C20 1.375(12) . ? C19 C23 1.506(12) . ? C9 C8 1.408(12) . ? C26 C27 1.383(12) . ? C18 C17 1.389(11) . ? C20 C21 1.383(11) . ? C7 C8 1.394(11) . ? C4 C3 1.370(12) . ? C4 C5 1.364(12) . ? C8 C13 1.518(12) . ? C17 C22 1.507(12) . ? C21 C24 1.497(12) . ? 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 O2 P1 O1 93.5(3) . . ? O2 P1 C1 104.7(3) . . ? O1 P1 C1 104.5(3) . . ? C30 O2 P1 110.0(5) . . ? C25 O1 P1 110.1(5) . . ? C10 C11 C12 123.1(9) . . ? C29 C30 O2 126.7(7) . . ? C29 C30 C25 120.9(8) . . ? O2 C30 C25 112.4(7) . . ? O1 C25 C30 113.2(7) . . ? O1 C25 C26 126.4(8) . . ? C30 C25 C26 120.4(8) . . ? C27 C28 C29 120.7(8) . . ? C27 C28 Cl3 119.4(7) . . ? C29 C28 Cl3 119.8(8) . . ? C30 C29 C28 119.2(8) . . ? C30 C29 Cl4 119.6(7) . . ? C28 C29 Cl4 121.2(7) . . ? C21 C16 C17 119.2(8) . . ? C21 C16 C6 120.5(7) . . ? C17 C16 C6 120.3(8) . . ? C5 C6 C1 119.4(8) . . ? C5 C6 C16 119.0(7) . . ? C1 C6 C16 121.6(7) . . ? C9 C10 C11 117.5(8) . . ? C9 C10 C14 119.6(10) . . ? C11 C10 C14 122.9(10) . . ? C3 C2 C1 117.3(7) . . ? C3 C2 C7 119.1(7) . . ? C1 C2 C7 123.6(7) . . ? C6 C1 C2 119.5(7) . . ? C6 C1 P1 113.6(6) . . ? C2 C1 P1 127.0(6) . . ? C7 C12 C11 118.0(8) . . ? C7 C12 C15 121.3(8) . . ? C11 C12 C15 120.7(8) . . ? C18 C19 C20 118.1(8) . . ? C18 C19 C23 122.0(9) . . ? C20 C19 C23 119.8(10) . . ? C10 C9 C8 123.0(9) . . ? C25 C26 C27 119.3(8) . . ? C25 C26 Cl1 118.2(7) . . ? C27 C26 Cl1 122.5(7) . . ? C19 C18 C17 122.5(8) . . ? C19 C20 C21 122.7(9) . . ? C12 C7 C8 120.7(8) . . ? C12 C7 C2 119.7(8) . . ? C8 C7 C2 119.5(8) . . ? C3 C4 C5 119.8(9) . . ? C6 C5 C4 121.6(8) . . ? C7 C8 C9 117.6(9) . . ? C7 C8 C13 122.3(8) . . ? C9 C8 C13 120.0(9) . . ? C18 C17 C16 118.8(8) . . ? C18 C17 C22 121.0(8) . . ? C16 C17 C22 120.1(8) . . ? C28 C27 C26 119.5(8) . . ? C28 C27 Cl2 121.4(7) . . ? C26 C27 Cl2 119.0(8) . . ? C20 C21 C16 118.6(8) . . ? C20 C21 C24 120.7(8) . . ? C16 C21 C24 120.7(8) . . ? C4 C3 C2 122.3(8) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.253 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.063 data_xcdmpq2 _database_code_CSD 216924 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-di-t-butylbenzo-2,6-dimesitylphenyl-1,3,2-dioxophospholane ; _chemical_name_common 3,5-di-t-butylbenzo-2,6-dimesitylphenyl-1,3,2-dioxophospholane _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H45 O2 P' _chemical_formula_weight 564.71 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 13.623(2) _cell_length_b 11.2320(17) _cell_length_c 22.372(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.531(12) _cell_angle_gamma 90.00 _cell_volume 3385.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 12.42 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3807 _exptl_absorpt_correction_T_max 0.4004 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6758 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 24.00 _reflns_number_total 5315 _reflns_number_gt 2896 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1993P)^2^+1.1298P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5315 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1598 _refine_ls_R_factor_gt 0.0930 _refine_ls_wR_factor_ref 0.3236 _refine_ls_wR_factor_gt 0.2680 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.488 _refine_ls_shift/su_mean 0.039 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 0.11432(10) 1.00281(14) 0.17267(6) 0.0555(5) Uani 1 1 d . . . O2 O 0.1152(3) 0.9424(3) 0.10526(16) 0.0587(10) Uani 1 1 d . . . O1 O 0.2098(2) 0.9204(3) 0.20521(15) 0.0563(10) Uani 1 1 d . . . C30 C 0.1978(4) 0.8711(4) 0.1050(2) 0.0487(13) Uani 1 1 d . . . C25 C 0.2520(4) 0.8588(5) 0.1612(2) 0.0474(12) Uani 1 1 d . . . C26 C 0.3364(4) 0.7877(5) 0.1703(3) 0.0575(14) Uani 1 1 d . . . C28 C 0.3048(5) 0.7429(5) 0.0614(3) 0.0623(15) Uani 1 1 d . . . C1 C 0.1764(4) 1.1482(5) 0.1672(2) 0.0531(14) Uani 1 1 d . . . C29 C 0.2213(4) 0.8156(5) 0.0542(3) 0.0590(15) Uani 1 1 d . . . C7 C 0.2295(4) 1.1359(5) 0.0610(2) 0.0567(14) Uani 1 1 d . . . C2 C 0.2237(4) 1.1923(5) 0.1201(2) 0.0592(15) Uani 1 1 d . . . C27 C 0.3603(4) 0.7300(5) 0.1185(3) 0.0669(16) Uani 1 1 d . . . C16 C 0.1107(4) 1.1823(5) 0.2670(3) 0.0649(16) Uani 1 1 d . . . C6 C 0.1676(4) 1.2225(5) 0.2173(2) 0.0627(15) Uani 1 1 d . . . C12 C 0.3198(5) 1.0910(5) 0.0478(3) 0.0673(17) Uani 1 1 d . . . C3 C 0.2668(5) 1.3066(6) 0.1262(3) 0.0790(19) Uani 1 1 d . . . C21 C 0.1594(5) 1.1333(6) 0.3205(3) 0.0717(17) Uani 1 1 d . . . C8 C 0.1470(6) 1.1424(6) 0.0152(3) 0.083(2) Uani 1 1 d . . . C4 C 0.2616(6) 1.3776(6) 0.1769(3) 0.087(2) Uani 1 1 d . . . C35 C 0.3343(6) 0.6744(6) 0.0076(3) 0.092(2) Uani 1 1 d . . . C31 C 0.4013(4) 0.7748(6) 0.2328(3) 0.0739(18) Uani 1 1 d . . . C5 C 0.2096(6) 1.3357(6) 0.2215(3) 0.086(2) Uani 1 1 d . . . C17 C 0.0080(5) 1.1996(6) 0.2595(3) 0.0774(19) Uani 1 1 d . . . C20 C 0.1048(5) 1.0967(6) 0.3648(3) 0.0806(19) Uani 1 1 d . . . C11 C 0.3284(7) 1.0547(6) -0.0116(3) 0.090(2) Uani 1 1 d . . . C18 C -0.0456(5) 1.1614(6) 0.3045(3) 0.0798(19) Uani 1 1 d . . . C9 C 0.1591(8) 1.1041(7) -0.0438(3) 0.100(3) Uani 1 1 d . . . C15 C 0.4103(4) 1.0798(7) 0.0961(3) 0.084(2) Uani 1 1 d . . . C36 C 0.330(3) 0.535(3) 0.0139(14) 0.116(13) Uani 0.50 1 d P . . C10 C 0.2489(9) 1.0611(7) -0.0564(3) 0.106(3) Uani 1 1 d . . . C19 C 0.0029(6) 1.1088(6) 0.3579(3) 0.0796(19) Uani 1 1 d . . . C22 C -0.0470(6) 1.2591(9) 0.2025(3) 0.110(3) Uani 1 1 d . . . C24 C 0.2733(5) 1.1187(8) 0.3323(3) 0.101(3) Uani 1 1 d . . . C33 C 0.3437(15) 0.725(2) 0.2760(11) 0.080(6) Uani 0.50 1 d P . . C13 C 0.0457(6) 1.1887(8) 0.0284(4) 0.113(3) Uani 1 1 d . . . C32 C 0.4442(12) 0.8877(15) 0.2475(8) 0.064(4) Uani 0.50 1 d P . . C23 C -0.0560(6) 1.0640(8) 0.4063(4) 0.108(3) Uani 1 1 d . . . C38A C 0.251(3) 0.6919(19) -0.0496(11) 0.093(9) Uani 0.50 1 d P . . C37 C 0.450(5) 0.716(5) 0.0107(13) 0.125(15) Uani 0.50 1 d P . . C34 C 0.484(3) 0.679(3) 0.2231(17) 0.123(13) Uani 0.50 1 d P . . C14 C 0.2561(10) 1.0242(9) -0.1214(3) 0.154(5) Uani 1 1 d . . . C36A C 0.343(3) 0.547(3) 0.0259(16) 0.150(18) Uani 0.50 1 d P . . C32A C 0.428(3) 0.909(3) 0.2675(15) 0.19(2) Uani 0.50 1 d P . . C37A C 0.437(5) 0.715(5) -0.0140(13) 0.125(11) Uani 0.50 1 d P . . C33A C 0.328(4) 0.688(4) 0.275(2) 0.23(2) Uani 0.50 1 d P . . C38 C 0.283(4) 0.715(4) -0.0574(18) 0.18(2) Uani 0.50 1 d P . . C34A C 0.504(2) 0.717(4) 0.2349(18) 0.148(18) Uani 0.50 1 d P . . 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 0.0452(8) 0.0570(9) 0.0644(9) -0.0057(7) 0.0088(6) 0.0024(7) O2 0.050(2) 0.056(2) 0.067(2) -0.0080(18) -0.0020(17) 0.0042(18) O1 0.056(2) 0.057(2) 0.056(2) -0.0007(17) 0.0070(17) 0.0030(18) C30 0.042(3) 0.042(3) 0.062(3) 0.003(3) 0.006(2) 0.000(2) C25 0.046(3) 0.047(3) 0.051(3) 0.003(2) 0.013(2) 0.000(2) C26 0.052(3) 0.046(3) 0.074(4) 0.018(3) 0.007(3) 0.004(3) C28 0.074(4) 0.051(3) 0.068(4) 0.002(3) 0.029(3) -0.001(3) C1 0.051(3) 0.051(3) 0.054(3) -0.004(3) -0.001(3) 0.009(3) C29 0.072(4) 0.044(3) 0.064(3) -0.003(3) 0.020(3) -0.004(3) C7 0.065(4) 0.055(3) 0.049(3) 0.002(3) 0.003(3) -0.003(3) C2 0.057(3) 0.058(4) 0.060(3) 0.003(3) 0.001(3) 0.001(3) C27 0.065(4) 0.054(4) 0.087(5) 0.001(3) 0.027(3) -0.002(3) C16 0.071(4) 0.060(4) 0.064(4) -0.011(3) 0.012(3) 0.009(3) C6 0.068(4) 0.061(4) 0.058(3) -0.002(3) 0.004(3) 0.006(3) C12 0.090(5) 0.057(4) 0.059(4) 0.011(3) 0.025(3) -0.010(3) C3 0.097(5) 0.058(4) 0.079(4) -0.005(3) 0.003(4) -0.012(4) C21 0.075(4) 0.077(4) 0.062(4) -0.006(3) 0.007(3) 0.012(3) C8 0.108(5) 0.067(4) 0.063(4) 0.013(3) -0.017(4) -0.001(4) C4 0.109(6) 0.074(5) 0.078(4) -0.009(4) 0.012(4) -0.012(4) C35 0.134(7) 0.056(4) 0.103(6) 0.001(4) 0.071(5) 0.005(4) C31 0.054(3) 0.071(4) 0.093(4) 0.014(4) -0.002(3) 0.010(3) C5 0.106(5) 0.063(4) 0.083(5) -0.017(4) 0.002(4) -0.016(4) C17 0.076(4) 0.082(5) 0.076(4) -0.016(4) 0.015(3) 0.025(4) C20 0.089(5) 0.080(5) 0.076(4) -0.006(4) 0.024(4) 0.004(4) C11 0.149(7) 0.070(5) 0.058(4) 0.007(3) 0.036(5) -0.018(5) C18 0.081(4) 0.082(5) 0.080(4) -0.013(4) 0.025(4) 0.014(4) C9 0.171(9) 0.063(4) 0.054(4) 0.006(3) -0.019(5) -0.010(5) C15 0.051(3) 0.106(5) 0.092(5) 0.016(4) 0.004(3) 0.002(4) C36 0.18(3) 0.059(18) 0.103(16) 0.026(12) -0.017(16) -0.015(15) C10 0.187(9) 0.074(5) 0.064(5) 0.002(4) 0.037(6) -0.007(6) C19 0.095(5) 0.068(4) 0.083(5) -0.018(4) 0.040(4) 0.002(4) C22 0.094(5) 0.148(8) 0.085(5) 0.009(5) 0.006(4) 0.053(5) C24 0.066(4) 0.146(8) 0.089(5) 0.015(5) 0.007(4) 0.011(5) C33 0.071(9) 0.111(14) 0.052(9) 0.045(9) -0.015(7) -0.048(10) C13 0.092(5) 0.114(6) 0.119(6) -0.008(5) -0.031(5) 0.043(5) C32 0.058(8) 0.047(9) 0.076(11) -0.023(8) -0.025(7) 0.004(7) C23 0.120(6) 0.106(6) 0.110(6) -0.005(5) 0.056(5) -0.005(5) C38A 0.20(3) 0.056(9) 0.034(9) -0.013(7) 0.037(12) 0.033(12) C37 0.18(3) 0.129(18) 0.09(2) -0.03(3) 0.12(3) -0.01(2) C34 0.12(2) 0.122(19) 0.098(15) -0.012(14) -0.062(14) 0.070(18) C14 0.289(14) 0.129(8) 0.048(4) -0.004(4) 0.035(6) -0.023(9) C36A 0.29(4) 0.053(14) 0.14(2) -0.028(14) 0.16(3) 0.022(19) C32A 0.24(4) 0.15(2) 0.16(3) -0.11(2) -0.07(2) 0.04(2) C37A 0.19(2) 0.133(19) 0.08(2) -0.02(2) 0.10(3) -0.032(16) C33A 0.31(5) 0.25(4) 0.10(2) 0.09(2) -0.01(2) -0.15(3) C38 0.20(4) 0.27(4) 0.089(19) 0.03(2) 0.06(2) 0.07(3) C34A 0.060(12) 0.24(5) 0.14(3) -0.04(2) -0.001(17) 0.039(18) _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 O2 1.656(4) . ? P1 O1 1.673(4) . ? P1 C1 1.851(6) . ? O2 C30 1.382(6) . ? O1 C25 1.395(6) . ? C30 C25 1.368(7) . ? C30 C29 1.375(7) . ? C25 C26 1.390(7) . ? C26 C27 1.408(8) . ? C26 C31 1.546(8) . ? C28 C29 1.390(8) . ? C28 C27 1.391(8) . ? C28 C35 1.532(8) . ? C1 C2 1.404(8) . ? C1 C6 1.418(7) . ? C7 C12 1.401(8) . ? C7 C8 1.405(8) . ? C7 C2 1.480(8) . ? C2 C3 1.410(8) . ? C16 C21 1.392(8) . ? C16 C17 1.399(9) . ? C16 C6 1.515(8) . ? C6 C5 1.392(9) . ? C12 C11 1.411(9) . ? C12 C15 1.519(9) . ? C3 C4 1.397(9) . ? C21 C20 1.386(9) . ? C21 C24 1.544(9) . ? C8 C9 1.422(10) . ? C8 C13 1.544(11) . ? C4 C5 1.388(10) . ? C35 C36A 1.49(4) . ? C35 C37A 1.61(6) . ? C35 C38 1.58(5) . ? C35 C38A 1.59(3) . ? C35 C37 1.63(6) . ? C31 C32 1.414(18) . ? C31 C33 1.45(2) . ? C31 C34A 1.54(3) . ? C31 C34 1.59(3) . ? C31 C32A 1.71(3) . ? C31 C33A 1.77(4) . ? C17 C18 1.396(9) . ? C17 C22 1.532(10) . ? C20 C19 1.380(10) . ? C11 C10 1.364(12) . ? C18 C19 1.408(9) . ? C9 C10 1.383(12) . ? C10 C14 1.529(10) . ? C19 C23 1.527(10) . ? C33 C33A 0.47(5) . ? C32 C32A 0.58(4) . ? C38A C38 0.56(7) . ? C37 C37A 0.55(6) . ? C34 C34A 0.55(8) . ? 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 O2 P1 O1 93.40(18) . . ? O2 P1 C1 103.7(2) . . ? O1 P1 C1 100.6(2) . . ? C30 O2 P1 110.9(3) . . ? C25 O1 P1 110.0(3) . . ? C25 C30 C29 123.6(5) . . ? C25 C30 O2 112.6(4) . . ? C29 C30 O2 123.8(5) . . ? C30 C25 C26 121.0(5) . . ? C30 C25 O1 112.1(4) . . ? C26 C25 O1 126.9(5) . . ? C25 C26 C27 115.6(5) . . ? C25 C26 C31 122.3(5) . . ? C27 C26 C31 122.1(5) . . ? C29 C28 C27 119.4(5) . . ? C29 C28 C35 120.7(6) . . ? C27 C28 C35 119.9(6) . . ? C2 C1 C6 119.2(5) . . ? C2 C1 P1 128.8(4) . . ? C6 C1 P1 111.9(4) . . ? C30 C29 C28 117.3(5) . . ? C12 C7 C8 119.9(5) . . ? C12 C7 C2 120.5(5) . . ? C8 C7 C2 119.1(6) . . ? C1 C2 C3 118.7(5) . . ? C1 C2 C7 127.6(5) . . ? C3 C2 C7 113.6(5) . . ? C28 C27 C26 123.2(5) . . ? C21 C16 C17 120.0(6) . . ? C21 C16 C6 121.2(5) . . ? C17 C16 C6 118.8(6) . . ? C5 C6 C1 120.6(6) . . ? C5 C6 C16 118.3(5) . . ? C1 C6 C16 121.2(5) . . ? C7 C12 C11 120.0(6) . . ? C7 C12 C15 121.7(5) . . ? C11 C12 C15 118.3(6) . . ? C4 C3 C2 121.8(6) . . ? C20 C21 C16 119.6(6) . . ? C20 C21 C24 118.6(6) . . ? C16 C21 C24 121.9(6) . . ? C7 C8 C9 118.1(7) . . ? C7 C8 C13 121.3(6) . . ? C9 C8 C13 120.6(7) . . ? C5 C4 C3 118.9(6) . . ? C36A C35 C28 106.6(11) . . ? C36A C35 C37A 109(3) . . ? C28 C35 C37A 115.7(16) . . ? C36A C35 C38 123(2) . . ? C28 C35 C38 116.3(16) . . ? C37A C35 C38 86(2) . . ? C36A C35 C38A 111(2) . . ? C28 C35 C38A 109.3(10) . . ? C37A C35 C38A 106(2) . . ? C38 C35 C38A 20(3) . . ? C36A C35 C37 103(3) . . ? C28 C35 C37 100.7(13) . . ? C37A C35 C37 20(2) . . ? C38 C35 C37 104(2) . . ? C38A C35 C37 124.6(19) . . ? C32 C31 C33 116.0(15) . . ? C32 C31 C34A 92(2) . . ? C33 C31 C34A 113(2) . . ? C32 C31 C26 106.7(9) . . ? C33 C31 C26 110.3(9) . . ? C34A C31 C26 117.5(16) . . ? C32 C31 C34 111.1(18) . . ? C33 C31 C34 107.1(19) . . ? C34A C31 C34 20(3) . . ? C26 C31 C34 105.1(13) . . ? C32 C31 C32A 18.5(19) . . ? C33 C31 C32A 97.8(19) . . ? C34A C31 C32A 103(2) . . ? C26 C31 C32A 112.5(14) . . ? C34 C31 C32A 123(2) . . ? C32 C31 C33A 128(2) . . ? C33 C31 C33A 12(3) . . ? C34A C31 C33A 109(3) . . ? C26 C31 C33A 103.9(15) . . ? C34 C31 C33A 100(3) . . ? C32A C31 C33A 110(2) . . ? C6 C5 C4 120.7(6) . . ? C18 C17 C16 119.4(6) . . ? C18 C17 C22 119.3(6) . . ? C16 C17 C22 121.2(6) . . ? C19 C20 C21 121.9(7) . . ? C10 C11 C12 120.7(8) . . ? C17 C18 C19 120.7(6) . . ? C10 C9 C8 121.5(7) . . ? C11 C10 C9 119.9(7) . . ? C11 C10 C14 122.0(10) . . ? C9 C10 C14 118.2(10) . . ? C20 C19 C18 118.3(6) . . ? C20 C19 C23 121.0(7) . . ? C18 C19 C23 120.7(7) . . ? C33A C33 C31 127(10) . . ? C32A C32 C31 111(6) . . ? C38 C38A C35 79(8) . . ? C37A C37 C35 78(10) . . ? C34A C34 C31 74(6) . . ? C32 C32A C31 51(4) . . ? C37 C37A C35 82(10) . . ? C33 C33A C31 41(8) . . ? C38A C38 C35 80(7) . . ? C34 C34A C31 86(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.449 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.074