# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_nd062711_0m #TrackingRef 'web_deposit_cif_file_0_JohnProtasiewicz_1354307221.nd062711_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H27 O P' _chemical_formula_sum 'C22 H27 O P' _chemical_formula_weight 338.41 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)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.7787(8) _cell_length_b 26.404(3) _cell_length_c 9.4840(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.7840(10) _cell_angle_gamma 90.00 _cell_volume 1943.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 8845 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.39 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9528 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details 'AXScale in APEX 2 (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 AXS APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 24183 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.41 _reflns_number_total 4812 _reflns_number_gt 4118 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0578P)^2^+0.5563P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4812 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.007 _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 0.07374(4) 0.923141(12) 0.30881(3) 0.02777(10) Uani 1 1 d . . . O1 O 0.33723(11) 0.86628(3) 0.25540(9) 0.02570(19) Uani 1 1 d . . . C3 C 0.14071(15) 0.87379(4) 0.43053(12) 0.0228(2) Uani 1 1 d . . . C2 C 0.28125(14) 0.84835(4) 0.38065(12) 0.0229(2) Uani 1 1 d . . . C1 C 0.23765(16) 0.90616(4) 0.20726(12) 0.0252(2) Uani 1 1 d . . . C6 C 0.15995(15) 0.81558(5) 0.62456(12) 0.0251(2) Uani 1 1 d . . . H6 H 0.1188 0.8038 0.7108 0.030 Uiso 1 1 calc R . . C4 C 0.36357(15) 0.80718(4) 0.44639(12) 0.0244(2) Uani 1 1 d . . . H4 H 0.4586 0.7912 0.4067 0.029 Uiso 1 1 calc R . . C7 C 0.07629(15) 0.85649(4) 0.55913(12) 0.0236(2) Uani 1 1 d . . . C12 C 0.37989(16) 0.74442(5) 0.65212(13) 0.0272(3) Uani 1 1 d . . . C5 C 0.30233(15) 0.79019(4) 0.57174(12) 0.0235(2) Uani 1 1 d . . . C10 C -0.23992(16) 0.87076(5) 0.51598(15) 0.0351(3) Uani 1 1 d . . . H10A H -0.2227 0.8873 0.4255 0.053 Uiso 1 1 calc R . . H10B H -0.3434 0.8845 0.5556 0.053 Uiso 1 1 calc R . . H10C H -0.2540 0.8342 0.5011 0.053 Uiso 1 1 calc R . . C8 C -0.08295(16) 0.88053(5) 0.61887(13) 0.0272(3) Uani 1 1 d . . . C9 C -0.1201(2) 0.85827(6) 0.76310(16) 0.0434(4) Uani 1 1 d . . . H9A H -0.1439 0.8220 0.7530 0.065 Uiso 1 1 calc R . . H9B H -0.2204 0.8753 0.7988 0.065 Uiso 1 1 calc R . . H9C H -0.0198 0.8633 0.8297 0.065 Uiso 1 1 calc R . . C11 C -0.05888(19) 0.93787(5) 0.63926(16) 0.0370(3) Uani 1 1 d . . . H11A H 0.0379 0.9442 0.7085 0.056 Uiso 1 1 calc R . . H11B H -0.1642 0.9525 0.6734 0.056 Uiso 1 1 calc R . . H11C H -0.0350 0.9535 0.5489 0.056 Uiso 1 1 calc R . . C16 C 0.28477(16) 0.92727(5) 0.07227(13) 0.0269(2) Uani 1 1 d . . . C19 C 0.36762(17) 0.96834(6) -0.18855(14) 0.0357(3) Uani 1 1 d . . . C17 C 0.23975(18) 0.97696(5) 0.03543(13) 0.0320(3) Uani 1 1 d . . . H17 H 0.1793 0.9971 0.0988 0.038 Uiso 1 1 calc R . . C21 C 0.37141(18) 0.89825(5) -0.02385(14) 0.0352(3) Uani 1 1 d . . . H21 H 0.4040 0.8644 -0.0008 0.042 Uiso 1 1 calc R . . C20 C 0.40997(19) 0.91868(6) -0.15297(15) 0.0393(3) Uani 1 1 d . . . H20 H 0.4664 0.8983 -0.2182 0.047 Uiso 1 1 calc R . . C18 C 0.28223(18) 0.99715(5) -0.09223(14) 0.0353(3) Uani 1 1 d . . . H18 H 0.2526 1.0313 -0.1145 0.042 Uiso 1 1 calc R . . C13 C 0.54333(18) 0.72513(5) 0.58866(14) 0.0352(3) Uani 1 1 d . . . H13A H 0.6302 0.7520 0.5924 0.053 Uiso 1 1 calc R . . H13B H 0.5164 0.7152 0.4901 0.053 Uiso 1 1 calc R . . H13C H 0.5881 0.6958 0.6427 0.053 Uiso 1 1 calc R . . C14 C 0.4267(2) 0.75880(6) 0.80691(14) 0.0395(3) Uani 1 1 d . . . H14A H 0.4784 0.7295 0.8571 0.059 Uiso 1 1 calc R . . H14B H 0.3223 0.7691 0.8518 0.059 Uiso 1 1 calc R . . H14C H 0.5091 0.7869 0.8105 0.059 Uiso 1 1 calc R . . C15 C 0.2464(2) 0.70134(5) 0.64469(17) 0.0412(3) Uani 1 1 d . . . H15A H 0.2191 0.6920 0.5458 0.062 Uiso 1 1 calc R . . H15B H 0.1413 0.7127 0.6868 0.062 Uiso 1 1 calc R . . H15C H 0.2937 0.6719 0.6968 0.062 Uiso 1 1 calc R . . C22 C 0.4110(2) 0.99040(7) -0.32874(16) 0.0502(4) Uani 1 1 d . . . H22A H 0.5233 1.0073 -0.3180 0.075 Uiso 1 1 calc R . . H22B H 0.3225 1.0150 -0.3605 0.075 Uiso 1 1 calc R . . H22C H 0.4154 0.9632 -0.3987 0.075 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 0.03050(18) 0.02422(17) 0.02893(18) 0.00492(12) 0.00457(12) 0.00535(12) O1 0.0260(4) 0.0265(4) 0.0251(4) 0.0058(3) 0.0047(3) 0.0020(3) C3 0.0228(5) 0.0210(5) 0.0245(5) 0.0008(4) 0.0004(4) -0.0005(4) C2 0.0224(5) 0.0242(5) 0.0221(5) 0.0021(4) 0.0024(4) -0.0023(4) C1 0.0279(6) 0.0224(5) 0.0252(6) 0.0027(4) 0.0008(4) -0.0011(4) C6 0.0259(6) 0.0271(6) 0.0225(5) 0.0015(4) 0.0034(4) 0.0000(4) C4 0.0220(5) 0.0255(6) 0.0258(6) 0.0013(4) 0.0027(4) 0.0016(4) C7 0.0218(5) 0.0248(5) 0.0244(6) -0.0016(4) 0.0022(4) -0.0002(4) C12 0.0300(6) 0.0267(6) 0.0249(6) 0.0040(4) 0.0017(5) 0.0047(5) C5 0.0241(5) 0.0229(5) 0.0232(5) 0.0018(4) -0.0004(4) -0.0002(4) C10 0.0238(6) 0.0395(7) 0.0422(7) -0.0056(6) 0.0028(5) 0.0001(5) C8 0.0245(6) 0.0299(6) 0.0277(6) -0.0011(5) 0.0050(4) 0.0033(5) C9 0.0398(8) 0.0557(9) 0.0366(7) 0.0084(6) 0.0169(6) 0.0148(7) C11 0.0362(7) 0.0338(7) 0.0415(7) -0.0120(6) 0.0059(6) 0.0030(6) C16 0.0262(6) 0.0287(6) 0.0255(6) 0.0043(5) 0.0009(4) -0.0023(5) C19 0.0260(6) 0.0516(8) 0.0293(6) 0.0125(6) 0.0004(5) -0.0029(6) C17 0.0385(7) 0.0297(6) 0.0278(6) 0.0034(5) 0.0019(5) 0.0021(5) C21 0.0371(7) 0.0345(7) 0.0349(7) 0.0066(5) 0.0088(5) 0.0061(5) C20 0.0358(7) 0.0505(9) 0.0327(7) 0.0063(6) 0.0105(6) 0.0070(6) C18 0.0379(7) 0.0335(7) 0.0338(7) 0.0111(5) -0.0026(5) -0.0002(5) C13 0.0384(7) 0.0333(7) 0.0341(7) 0.0056(5) 0.0048(5) 0.0130(6) C14 0.0469(8) 0.0454(8) 0.0257(6) 0.0024(6) -0.0021(6) 0.0138(6) C15 0.0452(8) 0.0308(7) 0.0476(8) 0.0114(6) 0.0035(6) -0.0022(6) C22 0.0439(9) 0.0708(11) 0.0363(8) 0.0217(8) 0.0069(6) -0.0006(8) _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 C1 1.7077(13) . ? P1 C3 1.7952(12) . ? O1 C1 1.3677(14) . ? O1 C2 1.3760(13) . ? C3 C2 1.3922(16) . ? C3 C7 1.4241(16) . ? C2 C4 1.3883(16) . ? C1 C16 1.4649(16) . ? C6 C7 1.3863(16) . ? C6 C5 1.4142(16) . ? C4 C5 1.3843(16) . ? C7 C8 1.5333(16) . ? C12 C13 1.5294(18) . ? C12 C5 1.5314(16) . ? C12 C14 1.5366(18) . ? C12 C15 1.5386(19) . ? C10 C8 1.5337(18) . ? C8 C9 1.5338(18) . ? C8 C11 1.5361(18) . ? C16 C17 1.3965(18) . ? C16 C21 1.3976(18) . ? C19 C20 1.388(2) . ? C19 C18 1.391(2) . ? C19 C22 1.5101(18) . ? C17 C18 1.3827(18) . ? C21 C20 1.3889(19) . ? 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 C1 P1 C3 88.64(6) . . ? C1 O1 C2 110.40(9) . . ? C2 C3 C7 117.69(10) . . ? C2 C3 P1 109.44(8) . . ? C7 C3 P1 132.85(9) . . ? O1 C2 C4 119.62(10) . . ? O1 C2 C3 115.32(10) . . ? C4 C2 C3 125.06(10) . . ? O1 C1 C16 114.57(10) . . ? O1 C1 P1 116.19(8) . . ? C16 C1 P1 129.21(9) . . ? C7 C6 C5 124.48(11) . . ? C5 C4 C2 117.69(11) . . ? C6 C7 C3 116.87(10) . . ? C6 C7 C8 121.60(10) . . ? C3 C7 C8 121.47(10) . . ? C13 C12 C5 112.18(10) . . ? C13 C12 C14 107.91(11) . . ? C5 C12 C14 109.96(10) . . ? C13 C12 C15 108.16(11) . . ? C5 C12 C15 108.55(10) . . ? C14 C12 C15 110.06(11) . . ? C4 C5 C6 118.20(10) . . ? C4 C5 C12 122.45(10) . . ? C6 C5 C12 119.33(10) . . ? C9 C8 C10 108.29(11) . . ? C9 C8 C7 112.05(10) . . ? C10 C8 C7 108.90(10) . . ? C9 C8 C11 107.10(11) . . ? C10 C8 C11 109.34(11) . . ? C7 C8 C11 111.09(10) . . ? C17 C16 C21 118.40(11) . . ? C17 C16 C1 120.20(11) . . ? C21 C16 C1 121.38(11) . . ? C20 C19 C18 118.22(12) . . ? C20 C19 C22 121.00(14) . . ? C18 C19 C22 120.77(14) . . ? C18 C17 C16 120.71(13) . . ? C20 C21 C16 120.24(13) . . ? C19 C20 C21 121.30(13) . . ? C17 C18 C19 121.09(13) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.278 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 913439' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_nd111411_0m #TrackingRef 'web_deposit_cif_file_1_JohnProtasiewicz_1354307221.nd111411_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 O P' _chemical_formula_sum 'C21 H25 O P' _chemical_formula_weight 324.38 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.5448(9) _cell_length_b 10.0465(8) _cell_length_c 35.559(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3767.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5476 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 21.47 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9575 _exptl_absorpt_correction_T_max 0.9945 _exptl_absorpt_process_details 'AXScale in APEX 2 (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'AXScale in APX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 40817 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4307 _reflns_number_gt 3114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0507P)^2^+1.1230P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4307 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1139 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.002 _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 0.64239(4) 1.04567(4) 0.634453(12) 0.03073(13) Uani 1 1 d . . . C3 C 0.58206(16) 1.04716(16) 0.59004(5) 0.0300(4) Uani 1 1 d . . . C1 C 0.51060(15) 0.84547(15) 0.60846(4) 0.0274(3) Uani 1 1 d . . . C11 C 0.43969(14) 0.64054(15) 0.63407(5) 0.0281(3) Uani 1 1 d . . . C2 C 0.57262(14) 0.88396(15) 0.64110(4) 0.0256(3) Uani 1 1 d . . . C13 C 0.56630(14) 0.79691(15) 0.67259(4) 0.0256(3) Uani 1 1 d . . . C12 C 0.49981(14) 0.67903(16) 0.66787(5) 0.0286(4) Uani 1 1 d . . . H12 H 0.4943 0.6203 0.6887 0.034 Uiso 1 1 calc R . . C14 C 0.62820(15) 0.83432(15) 0.71015(4) 0.0285(4) Uani 1 1 d . . . C18 C 0.36810(16) 0.50767(17) 0.63231(5) 0.0334(4) Uani 1 1 d . . . C10 C 0.44576(15) 0.72624(16) 0.60379(5) 0.0303(4) Uani 1 1 d . . . H10 H 0.4069 0.7044 0.5805 0.036 Uiso 1 1 calc R . . C4 C 0.58820(17) 1.15091(16) 0.56131(5) 0.0322(4) Uani 1 1 d . . . C16 C 0.56785(18) 0.96272(16) 0.72513(5) 0.0366(4) Uani 1 1 d . . . H16A H 0.5839 1.0356 0.7074 0.055 Uiso 1 1 calc R . . H16B H 0.6049 0.9848 0.7496 0.055 Uiso 1 1 calc R . . H16C H 0.4762 0.9499 0.7279 0.055 Uiso 1 1 calc R . . C15 C 0.61047(19) 0.72655(17) 0.74025(5) 0.0411(5) Uani 1 1 d . . . H15A H 0.5197 0.7125 0.7447 0.062 Uiso 1 1 calc R . . H15B H 0.6512 0.7551 0.7637 0.062 Uiso 1 1 calc R . . H15C H 0.6491 0.6433 0.7316 0.062 Uiso 1 1 calc R . . C17 C 0.77123(16) 0.85522(18) 0.70457(5) 0.0377(4) Uani 1 1 d . . . H17A H 0.8091 0.7737 0.6944 0.057 Uiso 1 1 calc R . . H17B H 0.8107 0.8764 0.7288 0.057 Uiso 1 1 calc R . . H17C H 0.7852 0.9288 0.6870 0.057 Uiso 1 1 calc R . . C5 C 0.50441(19) 1.15271(19) 0.53094(5) 0.0432(5) Uani 1 1 d . . . H5 H 0.4431 1.0841 0.5283 0.052 Uiso 1 1 calc R . . C9 C 0.67687(18) 1.25340(19) 0.56442(5) 0.0417(4) Uani 1 1 d . . . H9 H 0.7345 1.2539 0.5850 0.050 Uiso 1 1 calc R . . C7 C 0.5989(2) 1.3544(2) 0.50804(5) 0.0488(5) Uani 1 1 d . . . H7 H 0.6027 1.4235 0.4898 0.059 Uiso 1 1 calc R . . C8 C 0.6818(2) 1.3542(2) 0.53798(6) 0.0488(5) Uani 1 1 d . . . H8 H 0.7426 1.4234 0.5405 0.059 Uiso 1 1 calc R . . C21 C 0.25284(19) 0.5141(2) 0.65846(6) 0.0471(5) Uani 1 1 d . . . H21A H 0.1944 0.5831 0.6496 0.071 Uiso 1 1 calc R . . H21B H 0.2809 0.5355 0.6840 0.071 Uiso 1 1 calc R . . H21C H 0.2096 0.4278 0.6585 0.071 Uiso 1 1 calc R . . C19 C 0.45453(19) 0.39389(18) 0.64558(6) 0.0487(5) Uani 1 1 d . . . H19A H 0.4105 0.3087 0.6424 0.073 Uiso 1 1 calc R . . H19B H 0.4757 0.4067 0.6722 0.073 Uiso 1 1 calc R . . H19C H 0.5326 0.3936 0.6306 0.073 Uiso 1 1 calc R . . C20 C 0.3239(2) 0.4750(2) 0.59249(6) 0.0550(6) Uani 1 1 d . . . H20A H 0.2799 0.3890 0.5925 0.082 Uiso 1 1 calc R . . H20B H 0.3974 0.4703 0.5757 0.082 Uiso 1 1 calc R . . H20C H 0.2659 0.5446 0.5837 0.082 Uiso 1 1 calc R . . C6 C 0.5103(2) 1.2543(2) 0.50454(6) 0.0508(5) Uani 1 1 d . . . H6 H 0.4529 1.2549 0.4839 0.061 Uiso 1 1 calc R . . O1 O 0.51499(11) 0.93609(11) 0.57944(3) 0.0315(3) Uani 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 P1 0.0341(2) 0.0259(2) 0.0322(2) -0.00164(18) -0.00073(18) -0.00677(18) C3 0.0299(9) 0.0265(8) 0.0337(9) -0.0029(7) 0.0026(7) -0.0050(7) C1 0.0264(8) 0.0260(8) 0.0299(8) 0.0001(6) 0.0016(7) -0.0010(6) C11 0.0209(8) 0.0253(8) 0.0381(9) -0.0025(7) 0.0003(7) -0.0019(6) C2 0.0211(8) 0.0238(8) 0.0318(9) -0.0043(6) 0.0025(6) -0.0001(6) C13 0.0208(8) 0.0236(7) 0.0324(8) -0.0045(6) 0.0024(6) 0.0017(6) C12 0.0245(8) 0.0263(8) 0.0351(9) -0.0006(7) 0.0002(7) -0.0001(6) C14 0.0323(9) 0.0246(8) 0.0285(8) -0.0020(6) -0.0009(7) -0.0008(7) C18 0.0300(9) 0.0273(8) 0.0428(10) -0.0012(7) -0.0041(8) -0.0071(7) C10 0.0268(8) 0.0307(9) 0.0335(9) -0.0049(7) -0.0022(7) -0.0036(7) C4 0.0367(9) 0.0297(9) 0.0302(9) -0.0020(7) 0.0039(7) -0.0026(7) C16 0.0466(11) 0.0304(9) 0.0328(9) -0.0048(7) 0.0075(8) 0.0014(8) C15 0.0554(12) 0.0318(9) 0.0361(10) 0.0011(8) -0.0066(9) -0.0039(8) C17 0.0330(9) 0.0374(10) 0.0428(10) -0.0057(8) -0.0087(8) -0.0006(8) C5 0.0550(12) 0.0374(10) 0.0371(10) 0.0013(8) -0.0054(9) -0.0131(9) C9 0.0433(11) 0.0404(10) 0.0414(10) 0.0039(8) -0.0045(8) -0.0115(9) C7 0.0684(13) 0.0392(10) 0.0387(11) 0.0102(9) 0.0008(10) -0.0074(10) C8 0.0563(13) 0.0403(11) 0.0497(12) 0.0072(9) -0.0026(10) -0.0170(9) C21 0.0322(10) 0.0453(11) 0.0638(13) 0.0013(10) 0.0037(9) -0.0118(9) C19 0.0435(11) 0.0294(9) 0.0733(14) -0.0042(9) -0.0076(10) -0.0021(9) C20 0.0698(14) 0.0450(12) 0.0501(12) -0.0007(9) -0.0119(11) -0.0291(11) C6 0.0675(14) 0.0478(11) 0.0370(11) 0.0061(9) -0.0116(9) -0.0103(10) O1 0.0361(6) 0.0275(6) 0.0308(6) -0.0006(5) -0.0012(5) -0.0067(5) _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 C3 1.7028(17) . ? P1 C2 1.7991(16) . ? C3 O1 1.3737(18) . ? C3 C4 1.461(2) . ? C1 O1 1.3770(18) . ? C1 C2 1.387(2) . ? C1 C10 1.389(2) . ? C11 C10 1.380(2) . ? C11 C12 1.413(2) . ? C11 C18 1.535(2) . ? C2 C13 1.422(2) . ? C13 C12 1.386(2) . ? C13 C14 1.533(2) . ? C12 H12 0.9500 . ? C14 C16 1.534(2) . ? C14 C15 1.534(2) . ? C14 C17 1.536(2) . ? C18 C20 1.526(3) . ? C18 C21 1.532(3) . ? C18 C19 1.536(3) . ? C10 H10 0.9500 . ? C4 C5 1.395(2) . ? C4 C9 1.395(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C5 C6 1.388(3) . ? C5 H5 0.9500 . ? C9 C8 1.383(3) . ? C9 H9 0.9500 . ? C7 C8 1.378(3) . ? C7 C6 1.378(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C6 H6 0.9500 . ? 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 C3 P1 C2 88.68(7) . . ? O1 C3 C4 114.24(14) . . ? O1 C3 P1 116.08(11) . . ? C4 C3 P1 129.66(12) . . ? O1 C1 C2 115.27(13) . . ? O1 C1 C10 119.80(14) . . ? C2 C1 C10 124.93(15) . . ? C10 C11 C12 118.18(14) . . ? C10 C11 C18 122.24(14) . . ? C12 C11 C18 119.56(14) . . ? C1 C2 C13 117.72(14) . . ? C1 C2 P1 109.55(12) . . ? C13 C2 P1 132.68(12) . . ? C12 C13 C2 116.98(14) . . ? C12 C13 C14 122.01(14) . . ? C2 C13 C14 121.00(13) . . ? C13 C12 C11 124.31(15) . . ? C13 C12 H12 117.8 . . ? C11 C12 H12 117.8 . . ? C13 C14 C16 109.39(13) . . ? C13 C14 C15 112.51(13) . . ? C16 C14 C15 107.50(13) . . ? C13 C14 C17 109.82(13) . . ? C16 C14 C17 109.72(14) . . ? C15 C14 C17 107.84(14) . . ? C20 C18 C21 109.25(16) . . ? C20 C18 C11 112.05(15) . . ? C21 C18 C11 109.21(14) . . ? C20 C18 C19 107.83(16) . . ? C21 C18 C19 108.39(16) . . ? C11 C18 C19 110.05(13) . . ? C11 C10 C1 117.86(15) . . ? C11 C10 H10 121.1 . . ? C1 C10 H10 121.1 . . ? C5 C4 C9 118.45(16) . . ? C5 C4 C3 121.49(16) . . ? C9 C4 C3 120.04(16) . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C6 C5 C4 120.31(17) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C8 C9 C4 120.77(18) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? C8 C7 C6 119.94(18) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.17(18) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C7 C6 C5 120.36(18) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C3 O1 C1 110.41(12) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.228 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 913440'