# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_nd032511_0m _database_code_depnum_ccdc_archive 'CCDC 878276' #TrackingRef 'nd032511_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 O4 P' _chemical_formula_sum 'C14 H12 O4 P' _chemical_formula_weight 275.21 _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 _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 9.6672(8) _cell_length_b 11.5278(10) _cell_length_c 12.8735(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.6630(10) _cell_angle_gamma 90.00 _cell_volume 1399.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 9318 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 27.97 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9196 _exptl_absorpt_correction_T_max 0.9806 _exptl_absorpt_process_details 'AXScale in APEX 2 (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 16803 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.97 _reflns_number_total 3362 _reflns_number_gt 3025 _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^)+(0.1000P)^2^+0.5538P] 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 3362 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1702 _refine_ls_wR_factor_gt 0.1653 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _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 0.55384(5) 0.68899(4) 0.21301(4) 0.03436(18) Uani 1 1 d . . . C1 C 0.40324(17) 0.75786(16) 0.13151(14) 0.0319(4) Uani 1 1 d . . . C2 C 0.27496(18) 0.74477(16) 0.15995(14) 0.0335(4) Uani 1 1 d . . . H2 H 0.2720 0.7073 0.2251 0.040 Uiso 1 1 calc R . . C3 C 0.14775(18) 0.78576(16) 0.09450(14) 0.0333(4) Uani 1 1 d . . . C8 C 0.15416(18) 0.84203(16) -0.00231(14) 0.0322(4) Uani 1 1 d . . . C10 C 0.40948(18) 0.81851(17) 0.03609(15) 0.0347(4) Uani 1 1 d . . . C6 C -0.1019(2) 0.86148(19) -0.04129(17) 0.0433(5) Uani 1 1 d . . . H6 H -0.1872 0.8863 -0.0876 0.052 Uiso 1 1 calc R . . C7 C 0.02482(19) 0.87901(17) -0.06970(16) 0.0383(4) Uani 1 1 d . . . H7 H 0.0264 0.9163 -0.1352 0.046 Uiso 1 1 calc R . . C5 C -0.1075(2) 0.8073(2) 0.0554(2) 0.0468(5) Uani 1 1 d . . . H5 H -0.1962 0.7965 0.0745 0.056 Uiso 1 1 calc R . . C9 C 0.28753(19) 0.86014(17) -0.02825(15) 0.0359(4) Uani 1 1 d . . . H9 H 0.2925 0.9017 -0.0911 0.043 Uiso 1 1 calc R . . C4 C 0.0145(2) 0.7702(2) 0.12218(17) 0.0428(5) Uani 1 1 d . . . H4 H 0.0102 0.7338 0.1876 0.051 Uiso 1 1 calc R . . C11 C 0.7199(3) 0.5222(3) 0.1780(3) 0.0729(8) Uani 1 1 d . . . C12 C 0.7153(11) 0.4290(9) 0.1002(11) 0.080(2) Uani 0.50 1 d P . . O1 O 0.51870(15) 0.63438(14) 0.30759(11) 0.0450(4) Uani 1 1 d . . . O2 O 0.60289(16) 0.60125(14) 0.13566(12) 0.0471(4) Uani 1 1 d . . . C13 C 0.6808(3) 0.8745(2) 0.3076(2) 0.0542(6) Uani 1 1 d . . . H13A H 0.6593 0.8498 0.3760 0.065 Uiso 1 1 calc R . . H13B H 0.6074 0.9306 0.2732 0.065 Uiso 1 1 calc R . . C14 C 0.8244(3) 0.9295(2) 0.3267(2) 0.0632(7) Uani 1 1 d . . . H14A H 0.8960 0.8738 0.3620 0.095 Uiso 1 1 calc R . . H14B H 0.8262 0.9981 0.3720 0.095 Uiso 1 1 calc R . . H14C H 0.8451 0.9528 0.2584 0.095 Uiso 1 1 calc R . . O4 O 0.53912(14) 0.83075(16) 0.01357(12) 0.0483(4) Uani 1 1 d . . . H4A H 0.5301 0.8403 -0.0523 0.072 Uiso 1 1 calc R . . C12A C 0.7675(11) 0.4620(9) 0.0949(11) 0.080(2) Uani 0.50 1 d P . . O3 O 0.68220(14) 0.77515(13) 0.23918(11) 0.0412(3) Uani 1 1 d . . . _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 0.0261(3) 0.0456(3) 0.0308(3) 0.00160(17) 0.00512(18) 0.00492(17) C1 0.0234(7) 0.0416(9) 0.0304(8) -0.0004(7) 0.0049(6) 0.0031(6) C2 0.0269(8) 0.0419(9) 0.0326(9) -0.0004(7) 0.0083(7) -0.0002(7) C3 0.0239(8) 0.0400(9) 0.0362(9) -0.0043(7) 0.0072(7) -0.0009(6) C8 0.0245(8) 0.0373(8) 0.0338(9) -0.0058(7) 0.0042(6) 0.0011(6) C10 0.0235(8) 0.0483(10) 0.0334(9) 0.0017(7) 0.0088(7) 0.0011(7) C6 0.0248(8) 0.0530(11) 0.0478(11) -0.0112(9) -0.0015(7) 0.0022(8) C7 0.0287(8) 0.0455(10) 0.0377(9) -0.0045(8) 0.0009(7) 0.0027(7) C5 0.0234(8) 0.0628(13) 0.0550(12) -0.0087(10) 0.0104(8) -0.0025(8) C9 0.0288(8) 0.0463(10) 0.0328(9) 0.0044(7) 0.0067(7) 0.0023(7) C4 0.0281(9) 0.0565(12) 0.0457(11) -0.0012(9) 0.0120(8) -0.0029(8) C11 0.0699(17) 0.0751(18) 0.0727(18) -0.0006(14) 0.0132(14) 0.0361(15) C12 0.085(6) 0.069(5) 0.095(3) -0.010(4) 0.040(5) 0.023(4) O1 0.0373(7) 0.0621(9) 0.0349(7) 0.0092(6) 0.0067(6) 0.0025(6) O2 0.0442(8) 0.0536(8) 0.0421(8) -0.0040(6) 0.0064(6) 0.0144(7) C13 0.0466(12) 0.0492(12) 0.0675(15) -0.0096(11) 0.0140(10) 0.0017(9) C14 0.0638(15) 0.0521(13) 0.0731(17) -0.0026(12) 0.0133(13) -0.0150(12) O4 0.0242(6) 0.0826(11) 0.0399(8) 0.0154(7) 0.0112(6) 0.0055(6) C12A 0.085(6) 0.069(5) 0.095(3) -0.010(4) 0.040(5) 0.023(4) O3 0.0270(6) 0.0537(8) 0.0419(8) -0.0022(6) 0.0053(5) 0.0015(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. ; _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 O1 1.4750(14) . ? P1 O2 1.5641(15) . ? P1 O3 1.5674(15) . ? P1 C1 1.7835(17) . ? C1 C2 1.376(2) . ? C1 C10 1.426(3) . ? C2 C3 1.411(2) . ? C2 H2 0.9500 . ? C3 C8 1.418(3) . ? C3 C4 1.421(2) . ? C8 C9 1.416(2) . ? C8 C7 1.422(2) . ? C10 O4 1.354(2) . ? C10 C9 1.370(3) . ? C6 C7 1.368(3) . ? C6 C5 1.405(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C5 C4 1.367(3) . ? C5 H5 0.9500 . ? C9 H9 0.9500 . ? C4 H4 0.9500 . ? C11 C12A 1.433(12) . ? C11 O2 1.462(3) . ? C11 C12 1.463(12) . ? C12 C12A 0.648(11) . ? C13 O3 1.447(3) . ? C13 C14 1.497(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O4 H4A 0.8400 . ? _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 O1 P1 O2 113.98(9) . . ? O1 P1 O3 114.07(8) . . ? O2 P1 O3 102.14(8) . . ? O1 P1 C1 111.69(8) . . ? O2 P1 C1 103.63(8) . . ? O3 P1 C1 110.49(8) . . ? C2 C1 C10 119.58(16) . . ? C2 C1 P1 117.50(14) . . ? C10 C1 P1 122.80(13) . . ? C1 C2 C3 121.51(17) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C2 C3 C8 118.53(15) . . ? C2 C3 C4 121.82(18) . . ? C8 C3 C4 119.64(17) . . ? C9 C8 C3 119.47(16) . . ? C9 C8 C7 122.41(17) . . ? C3 C8 C7 118.11(16) . . ? O4 C10 C9 123.23(17) . . ? O4 C10 C1 116.83(16) . . ? C9 C10 C1 119.94(16) . . ? C7 C6 C5 120.91(18) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 120.78(19) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C4 C5 C6 120.04(18) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C10 C9 C8 120.85(17) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C12A C11 O2 111.9(6) . . ? C12A C11 C12 25.8(4) . . ? O2 C11 C12 107.3(6) . . ? C12A C12 C11 74.4(19) . . ? C11 O2 P1 118.91(16) . . ? O3 C13 C14 107.6(2) . . ? O3 C13 H13A 110.2 . . ? C14 C13 H13A 110.2 . . ? O3 C13 H13B 110.2 . . ? C14 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 O4 H4A 109.5 . . ? C12 C12A C11 79.7(19) . . ? C13 O3 P1 121.33(13) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.976 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.063 data_pro20 _database_code_depnum_ccdc_archive 'CCDC 878277' #TrackingRef 'pro20.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H13 O P' _chemical_formula_weight 276.25 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.755(2) _cell_length_b 7.3511(13) _cell_length_c 16.433(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.790(3) _cell_angle_gamma 90.00 _cell_volume 1344.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4400 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 30.06 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9454 _exptl_absorpt_correction_T_max 0.9845 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 10573 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 30.70 _reflns_number_total 6734 _reflns_number_gt 5242 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0600P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(10) _refine_ls_number_reflns 6734 _refine_ls_number_parameters 363 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1239 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 0.21369(6) 0.52648(11) -0.25098(5) 0.02341(18) Uani 1 1 d . . . P2 P 0.05376(6) 0.36411(11) 0.25461(4) 0.01849(16) Uani 1 1 d . . . O6 O 0.43446(15) 0.3970(2) -0.19537(12) 0.0205(4) Uani 1 1 d . . . O26 O -0.16308(14) 0.5085(3) 0.20889(11) 0.0161(4) Uani 1 1 d . . . C1 C 0.4804(2) 0.4240(4) 0.1839(2) 0.0268(7) Uani 1 1 d . . . H1 H 0.5321 0.4005 0.2406 0.032 Uiso 1 1 calc R . . C2 C 0.5171(2) 0.3839(4) 0.11492(18) 0.0227(6) Uani 1 1 d . . . H2 H 0.5944 0.3322 0.1247 0.027 Uiso 1 1 calc R . . C3 C 0.4428(2) 0.4174(4) 0.02911(19) 0.0202(6) Uani 1 1 d . . . C4 C 0.4797(2) 0.3797(4) -0.04223(18) 0.0216(6) Uani 1 1 d . . . H4 H 0.5562 0.3271 -0.0350 0.026 Uiso 1 1 calc R . . C5 C 0.4032(2) 0.4205(4) -0.12245(19) 0.0205(6) Uani 1 1 d . . . C7 C 0.3427(2) 0.4501(4) -0.26717(19) 0.0219(6) Uani 1 1 d . . . C8 C 0.3694(2) 0.4299(4) -0.34737(18) 0.0213(6) Uani 1 1 d . . . C9 C 0.2892(2) 0.4939(4) -0.42539(19) 0.0257(7) Uani 1 1 d . . . H9 H 0.2196 0.5593 -0.4253 0.031 Uiso 1 1 calc R . . C10 C 0.3103(2) 0.4630(4) -0.5019(2) 0.0251(7) Uani 1 1 d . . . H10 H 0.2539 0.5057 -0.5539 0.030 Uiso 1 1 calc R . . C11 C 0.4128(2) 0.3702(4) -0.50518(18) 0.0250(6) Uani 1 1 d . . . C12 C 0.4330(3) 0.3321(5) -0.58994(19) 0.0312(7) Uani 1 1 d . . . H12A H 0.4897 0.4213 -0.5990 0.047 Uiso 1 1 calc R . . H12B H 0.3564 0.3411 -0.6367 0.047 Uiso 1 1 calc R . . H12C H 0.4660 0.2094 -0.5890 0.047 Uiso 1 1 calc R . . C13 C 0.3658(2) 0.5003(4) 0.1705(2) 0.0257(6) Uani 1 1 d . . . H13 H 0.3402 0.5270 0.2185 0.031 Uiso 1 1 calc R . . C14 C 0.3248(2) 0.4947(4) 0.01616(19) 0.0215(6) Uani 1 1 d . . . C15 C 0.2489(2) 0.5300(4) -0.06797(18) 0.0209(6) Uani 1 1 d . . . H15 H 0.1712 0.5798 -0.0768 0.025 Uiso 1 1 calc R . . C16 C 0.2863(2) 0.4928(4) -0.13828(19) 0.0214(6) Uani 1 1 d . . . C17 C 0.4743(2) 0.3418(4) -0.34988(19) 0.0245(6) Uani 1 1 d . . . H17 H 0.5319 0.3014 -0.2980 0.029 Uiso 1 1 calc R . . C18 C 0.4943(2) 0.3132(4) -0.42759(19) 0.0251(7) Uani 1 1 d . . . H18 H 0.5658 0.2531 -0.4278 0.030 Uiso 1 1 calc R . . C19 C 0.2912(2) 0.5361(4) 0.08939(19) 0.0236(6) Uani 1 1 d . . . H19 H 0.2150 0.5899 0.0819 0.028 Uiso 1 1 calc R . . C20 C -0.1609(3) 0.4269(4) 0.60223(18) 0.0302(7) Uani 1 1 d . . . H20A H -0.1537 0.3012 0.6232 0.045 Uiso 1 1 calc R . . H20B H -0.2418 0.4724 0.5954 0.045 Uiso 1 1 calc R . . H20C H -0.1014 0.5031 0.6437 0.045 Uiso 1 1 calc R . . C21 C -0.1392(3) 0.4329(4) 0.51687(17) 0.0223(6) Uani 1 1 d . . . C22 C -0.0332(2) 0.3627(4) 0.50933(18) 0.0228(6) Uani 1 1 d . . . H22 H 0.0245 0.3099 0.5581 0.027 Uiso 1 1 calc R . . C23 C -0.0107(2) 0.3687(4) 0.43165(16) 0.0202(5) Uani 1 1 d . . . H23 H 0.0622 0.3200 0.4278 0.024 Uiso 1 1 calc R . . C24 C -0.0936(2) 0.4453(4) 0.35906(18) 0.0198(6) Uani 1 1 d . . . C25 C -0.0699(2) 0.4461(4) 0.27743(17) 0.0179(5) Uani 1 1 d . . . C27 C -0.1379(2) 0.4871(4) 0.13324(17) 0.0174(6) Uani 1 1 d . . . C28 C -0.2174(2) 0.5353(4) 0.05526(16) 0.0171(5) Uani 1 1 d . . . H28 H -0.2913 0.5926 0.0516 0.020 Uiso 1 1 calc R . . C29 C -0.1875(2) 0.4984(4) -0.01954(18) 0.0186(6) Uani 1 1 d . . . C30 C -0.2647(2) 0.5423(4) -0.10240(17) 0.0200(6) Uani 1 1 d . . . H30 H -0.3390 0.6014 -0.1089 0.024 Uiso 1 1 calc R . . C31 C -0.2333(2) 0.4999(4) -0.17427(18) 0.0236(6) Uani 1 1 d . . . H31 H -0.2865 0.5296 -0.2298 0.028 Uiso 1 1 calc R . . C32 C -0.2219(2) 0.5098(4) 0.44473(17) 0.0221(6) Uani 1 1 d . . . H32 H -0.2945 0.5587 0.4490 0.027 Uiso 1 1 calc R . . C33 C -0.2004(2) 0.5167(4) 0.36585(17) 0.0201(5) Uani 1 1 d . . . H33 H -0.2581 0.5696 0.3171 0.024 Uiso 1 1 calc R . . C34 C -0.0246(2) 0.4066(4) 0.14358(17) 0.0184(6) Uani 1 1 d . . . C35 C -0.0737(2) 0.4114(4) -0.01090(17) 0.0179(6) Uani 1 1 d . . . C36 C 0.0048(2) 0.3684(4) 0.07019(16) 0.0176(5) Uani 1 1 d . . . H36 H 0.0795 0.3121 0.0753 0.021 Uiso 1 1 calc R . . C37 C -0.0462(2) 0.3708(5) -0.08719(17) 0.0216(6) Uani 1 1 d . . . H37 H 0.0277 0.3126 -0.0830 0.026 Uiso 1 1 calc R . . C38 C -0.1241(3) 0.4140(4) -0.16632(19) 0.0246(6) Uani 1 1 d . . . H38 H -0.1040 0.3854 -0.2164 0.030 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 0.0155(3) 0.0222(4) 0.0319(4) 0.0031(4) 0.0069(3) 0.0039(3) P2 0.0146(3) 0.0229(4) 0.0182(3) 0.0008(3) 0.0055(2) 0.0031(3) O6 0.0150(8) 0.0187(11) 0.0278(10) 0.0017(9) 0.0067(7) 0.0023(8) O26 0.0138(8) 0.0180(10) 0.0171(9) -0.0004(8) 0.0057(7) 0.0029(8) C1 0.0230(14) 0.0245(16) 0.0297(16) -0.0017(13) 0.0040(12) -0.0021(13) C2 0.0166(12) 0.0156(14) 0.0360(15) 0.0004(13) 0.0086(11) -0.0003(12) C3 0.0140(12) 0.0129(14) 0.0321(16) -0.0011(12) 0.0052(11) -0.0030(10) C4 0.0159(12) 0.0143(14) 0.0349(15) 0.0006(13) 0.0086(11) 0.0010(12) C5 0.0170(12) 0.0139(14) 0.0323(15) -0.0006(12) 0.0104(11) -0.0008(11) C7 0.0203(13) 0.0154(14) 0.0301(15) -0.0010(12) 0.0084(11) 0.0009(11) C8 0.0187(12) 0.0142(13) 0.0302(15) 0.0030(12) 0.0068(11) -0.0025(11) C9 0.0193(13) 0.0216(16) 0.0358(17) 0.0051(13) 0.0083(12) 0.0008(12) C10 0.0200(13) 0.0212(16) 0.0319(16) 0.0068(12) 0.0052(12) -0.0024(12) C11 0.0245(13) 0.0160(14) 0.0351(16) 0.0023(14) 0.0104(11) -0.0039(13) C12 0.0342(16) 0.0294(19) 0.0331(16) 0.0002(14) 0.0152(13) -0.0003(14) C13 0.0272(14) 0.0177(15) 0.0353(16) -0.0047(13) 0.0145(12) -0.0037(13) C14 0.0190(12) 0.0105(14) 0.0354(16) -0.0016(12) 0.0094(11) -0.0009(11) C15 0.0121(11) 0.0144(13) 0.0369(16) 0.0019(13) 0.0088(11) 0.0013(12) C16 0.0149(12) 0.0154(14) 0.0327(15) 0.0022(12) 0.0060(11) 0.0009(11) C17 0.0180(12) 0.0192(16) 0.0364(16) 0.0019(14) 0.0087(11) 0.0016(12) C18 0.0217(14) 0.0173(15) 0.0376(17) 0.0013(12) 0.0112(12) 0.0008(11) C19 0.0192(12) 0.0146(14) 0.0379(16) 0.0003(14) 0.0106(12) -0.0008(12) C20 0.0421(17) 0.0267(17) 0.0267(16) -0.0012(13) 0.0179(14) -0.0036(14) C21 0.0330(15) 0.0151(13) 0.0226(14) -0.0034(12) 0.0143(12) -0.0048(12) C22 0.0228(13) 0.0174(14) 0.0273(14) 0.0014(14) 0.0069(11) 0.0009(13) C23 0.0199(12) 0.0196(14) 0.0193(13) -0.0006(13) 0.0035(10) 0.0003(13) C24 0.0190(12) 0.0172(13) 0.0247(14) -0.0037(12) 0.0093(11) -0.0023(11) C25 0.0194(12) 0.0146(13) 0.0200(13) -0.0009(11) 0.0066(10) -0.0009(11) C27 0.0190(12) 0.0151(14) 0.0205(13) -0.0011(11) 0.0095(10) -0.0009(11) C28 0.0123(11) 0.0155(13) 0.0234(13) 0.0002(12) 0.0059(10) -0.0004(11) C29 0.0193(12) 0.0130(14) 0.0254(14) -0.0003(11) 0.0099(11) -0.0031(11) C30 0.0185(12) 0.0185(15) 0.0224(14) 0.0022(12) 0.0057(10) -0.0014(12) C31 0.0254(13) 0.0238(16) 0.0198(14) 0.0025(13) 0.0047(11) -0.0049(13) C32 0.0228(13) 0.0185(15) 0.0256(14) -0.0043(13) 0.0085(11) -0.0021(12) C33 0.0174(12) 0.0175(14) 0.0246(13) -0.0007(13) 0.0058(10) 0.0017(12) C34 0.0142(11) 0.0195(16) 0.0210(13) 0.0016(11) 0.0049(10) -0.0016(11) C35 0.0171(12) 0.0177(15) 0.0199(13) 0.0006(11) 0.0075(10) -0.0038(10) C36 0.0192(12) 0.0123(12) 0.0249(13) -0.0003(13) 0.0120(10) -0.0023(12) C37 0.0223(12) 0.0184(14) 0.0268(14) -0.0027(13) 0.0115(11) -0.0030(13) C38 0.0312(15) 0.0241(17) 0.0232(14) -0.0002(12) 0.0152(12) -0.0039(12) _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 C7 1.716(3) . ? P1 C16 1.789(3) . ? P2 C25 1.723(3) . ? P2 C34 1.787(3) . ? O6 C5 1.373(3) . ? O6 C7 1.374(3) . ? O26 C25 1.372(3) . ? O26 C27 1.376(3) . ? C1 C2 1.368(4) . ? C1 C13 1.410(4) . ? C2 C3 1.421(4) . ? C3 C4 1.403(4) . ? C3 C14 1.450(4) . ? C4 C5 1.369(4) . ? C5 C16 1.417(4) . ? C7 C8 1.458(4) . ? C8 C17 1.405(4) . ? C8 C9 1.405(4) . ? C9 C10 1.377(4) . ? C10 C11 1.401(4) . ? C11 C18 1.390(4) . ? C11 C12 1.513(4) . ? C13 C19 1.365(4) . ? C14 C15 1.407(4) . ? C14 C19 1.415(4) . ? C15 C16 1.389(4) . ? C17 C18 1.387(4) . ? C20 C21 1.505(4) . ? C21 C32 1.388(4) . ? C21 C22 1.390(4) . ? C22 C23 1.385(4) . ? C23 C24 1.393(4) . ? C24 C33 1.399(4) . ? C24 C25 1.455(4) . ? C27 C28 1.367(4) . ? C27 C34 1.417(4) . ? C28 C29 1.409(4) . ? C29 C30 1.409(4) . ? C29 C35 1.448(3) . ? C30 C31 1.382(4) . ? C31 C38 1.399(4) . ? C32 C33 1.399(4) . ? C34 C36 1.386(4) . ? C35 C36 1.391(4) . ? C35 C37 1.424(4) . ? C37 C38 1.365(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 P1 C16 87.97(13) . . ? C25 P2 C34 88.14(13) . . ? C5 O6 C7 110.9(2) . . ? C25 O26 C27 110.87(19) . . ? C2 C1 C13 119.7(3) . . ? C1 C2 C3 121.9(3) . . ? C4 C3 C2 122.6(2) . . ? C4 C3 C14 119.6(3) . . ? C2 C3 C14 117.8(3) . . ? C5 C4 C3 118.5(2) . . ? C4 C5 O6 122.4(2) . . ? C4 C5 C16 123.8(3) . . ? O6 C5 C16 113.8(2) . . ? O6 C7 C8 114.1(2) . . ? O6 C7 P1 116.6(2) . . ? C8 C7 P1 129.2(2) . . ? C17 C8 C9 117.7(3) . . ? C17 C8 C7 121.4(2) . . ? C9 C8 C7 120.9(3) . . ? C10 C9 C8 120.9(3) . . ? C9 C10 C11 121.7(3) . . ? C18 C11 C10 117.3(3) . . ? C18 C11 C12 121.5(3) . . ? C10 C11 C12 121.1(3) . . ? C19 C13 C1 120.7(3) . . ? C15 C14 C19 122.2(2) . . ? C15 C14 C3 119.4(3) . . ? C19 C14 C3 118.4(3) . . ? C16 C15 C14 120.7(2) . . ? C15 C16 C5 118.0(3) . . ? C15 C16 P1 131.3(2) . . ? C5 C16 P1 110.7(2) . . ? C18 C17 C8 120.5(3) . . ? C17 C18 C11 121.9(3) . . ? C13 C19 C14 121.5(3) . . ? C32 C21 C22 118.4(2) . . ? C32 C21 C20 121.7(3) . . ? C22 C21 C20 119.9(3) . . ? C23 C22 C21 120.8(2) . . ? C22 C23 C24 120.9(2) . . ? C23 C24 C33 118.8(2) . . ? C23 C24 C25 120.2(2) . . ? C33 C24 C25 121.0(2) . . ? O26 C25 C24 114.8(2) . . ? O26 C25 P2 116.39(18) . . ? C24 C25 P2 128.6(2) . . ? C28 C27 O26 122.4(2) . . ? C28 C27 C34 123.5(2) . . ? O26 C27 C34 114.0(2) . . ? C27 C28 C29 118.8(2) . . ? C28 C29 C30 122.3(2) . . ? C28 C29 C35 118.8(2) . . ? C30 C29 C35 118.9(2) . . ? C31 C30 C29 120.5(3) . . ? C30 C31 C38 120.8(3) . . ? C21 C32 C33 121.4(2) . . ? C24 C33 C32 119.7(2) . . ? C36 C34 C27 117.9(2) . . ? C36 C34 P2 131.5(2) . . ? C27 C34 P2 110.5(2) . . ? C36 C35 C37 121.8(2) . . ? C36 C35 C29 120.1(2) . . ? C37 C35 C29 118.1(2) . . ? C34 C36 C35 120.9(2) . . ? C38 C37 C35 121.1(3) . . ? C37 C38 C31 120.5(3) . . ? _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.692 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.070 data_pro21 _database_code_depnum_ccdc_archive 'CCDC 878278' #TrackingRef 'pro21.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 O P' _chemical_formula_weight 320.35 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.5436(4) _cell_length_b 13.3825(8) _cell_length_c 18.4075(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1611.94(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2010 _cell_measurement_theta_min 3.30 _cell_measurement_theta_max 25.37 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9564 _exptl_absorpt_correction_T_max 0.9662 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 4287 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.42 _reflns_number_total 2336 _reflns_number_gt 2168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0700P)^2^+0.2200P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.70(16) _refine_ls_number_reflns 2336 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1073 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 1.17733(11) 0.74784(5) 0.07840(3) 0.0233(2) Uani 1 1 d . . . O1 O 0.8200(3) 0.80920(13) 0.12715(9) 0.0223(4) Uani 1 1 d . . . C1 C 1.2035(5) 1.1467(2) 0.09982(15) 0.0308(7) Uani 1 1 d . . . H1A H 1.3223 1.1280 0.1303 0.037 Uiso 1 1 calc R . . H1B H 1.2083 1.2196 0.0912 0.037 Uiso 1 1 calc R . . C2 C 1.0053(4) 1.1190(2) 0.13875(13) 0.0248(6) Uani 1 1 d . . . H2 H 0.9985 1.1552 0.1862 0.030 Uiso 1 1 calc R . . C3 C 1.0009(5) 1.0064(2) 0.15258(12) 0.0232(6) Uani 1 1 d . . . H3A H 0.8746 0.9887 0.1793 0.028 Uiso 1 1 calc R . . H3B H 1.1193 0.9872 0.1830 0.028 Uiso 1 1 calc R . . C4 C 1.0082(4) 0.94863(19) 0.08002(13) 0.0182(5) Uani 1 1 d . . . C5 C 1.0011(4) 0.8386(2) 0.09439(12) 0.0204(6) Uani 1 1 d . . . C6 C 1.0038(4) 0.65926(19) 0.11928(12) 0.0203(6) Uani 1 1 d . . . C7 C 1.0185(4) 0.55740(19) 0.13203(13) 0.0212(6) Uani 1 1 d . . . H7 H 1.1388 0.5224 0.1183 0.025 Uiso 1 1 calc R . . C8 C 0.8553(5) 0.5051(2) 0.16548(12) 0.0221(6) Uani 1 1 d . . . C9 C 0.8664(5) 0.4006(2) 0.17985(13) 0.0247(6) Uani 1 1 d . . . H9 H 0.9851 0.3644 0.1659 0.030 Uiso 1 1 calc R . . C10 C 0.7094(5) 0.3514(2) 0.21328(13) 0.0283(7) Uani 1 1 d . . . H10 H 0.7202 0.2818 0.2226 0.034 Uiso 1 1 calc R . . C11 C 0.5309(5) 0.4036(2) 0.23398(13) 0.0274(6) Uani 1 1 d . . . H11 H 0.4220 0.3689 0.2570 0.033 Uiso 1 1 calc R . . C12 C 0.5144(5) 0.5037(2) 0.22098(14) 0.0250(6) Uani 1 1 d . . . H12 H 0.3937 0.5381 0.2351 0.030 Uiso 1 1 calc R . . C13 C 0.6752(4) 0.5576(2) 0.18653(12) 0.0213(6) Uani 1 1 d . . . C14 C 0.6601(5) 0.6615(2) 0.17317(13) 0.0240(6) Uani 1 1 d . . . H14 H 0.5406 0.6976 0.1861 0.029 Uiso 1 1 calc R . . C15 C 0.8222(5) 0.70840(19) 0.14116(13) 0.0211(6) Uani 1 1 d . . . C16 C 0.8228(5) 1.1494(2) 0.09173(13) 0.0250(6) Uani 1 1 d . . . H16A H 0.8259 1.2224 0.0831 0.030 Uiso 1 1 calc R . . H16B H 0.6940 1.1330 0.1173 0.030 Uiso 1 1 calc R . . C17 C 0.8309(5) 1.0939(2) 0.01907(14) 0.0248(6) Uani 1 1 d . . . H17 H 0.7115 1.1140 -0.0116 0.030 Uiso 1 1 calc R . . C18 C 0.8251(5) 0.9808(2) 0.03240(14) 0.0264(6) Uani 1 1 d . . . H18A H 0.8302 0.9451 -0.0147 0.032 Uiso 1 1 calc R . . H18B H 0.6957 0.9628 0.0570 0.032 Uiso 1 1 calc R . . C19 C 1.0299(5) 1.1214(2) -0.01994(14) 0.0299(7) Uani 1 1 d . . . H19A H 1.0364 1.0868 -0.0674 0.036 Uiso 1 1 calc R . . H19B H 1.0341 1.1943 -0.0289 0.036 Uiso 1 1 calc R . . C20 C 1.2126(4) 1.0906(2) 0.02688(15) 0.0290(7) Uani 1 1 d . . . H20 H 1.3421 1.1084 0.0011 0.035 Uiso 1 1 calc R . . C21 C 1.2073(4) 0.9767(2) 0.04043(15) 0.0284(7) Uani 1 1 d . . . H21A H 1.2150 0.9407 -0.0065 0.034 Uiso 1 1 calc R . . H21B H 1.3264 0.9567 0.0703 0.034 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 0.0264(4) 0.0177(3) 0.0258(3) 0.0017(3) 0.0036(3) 0.0029(4) O1 0.0245(11) 0.0178(10) 0.0247(9) 0.0011(7) 0.0020(9) 0.0000(9) C1 0.0292(17) 0.0181(14) 0.0452(16) 0.0049(12) -0.0082(13) -0.0047(13) C2 0.0354(16) 0.0190(13) 0.0201(12) -0.0026(10) -0.0001(12) -0.0001(14) C3 0.0296(16) 0.0208(14) 0.0191(12) -0.0021(10) 0.0002(12) 0.0000(13) C4 0.0213(14) 0.0154(13) 0.0179(11) 0.0008(9) 0.0000(11) 0.0011(12) C5 0.0265(15) 0.0206(14) 0.0140(11) 0.0005(9) -0.0005(11) -0.0038(13) C6 0.0264(15) 0.0181(13) 0.0164(12) -0.0003(9) -0.0017(11) -0.0007(13) C7 0.0272(15) 0.0199(14) 0.0165(11) -0.0013(9) -0.0005(11) 0.0039(13) C8 0.0339(16) 0.0181(14) 0.0145(11) 0.0001(9) -0.0032(11) -0.0009(13) C9 0.0387(17) 0.0192(14) 0.0163(11) -0.0025(10) -0.0005(11) 0.0032(13) C10 0.0453(19) 0.0187(14) 0.0207(12) -0.0003(10) 0.0003(13) -0.0001(14) C11 0.0375(17) 0.0240(15) 0.0208(12) 0.0014(11) 0.0031(12) -0.0076(14) C12 0.0283(15) 0.0224(14) 0.0243(12) -0.0006(10) -0.0006(12) 0.0009(13) C13 0.0268(14) 0.0195(14) 0.0178(11) -0.0016(9) -0.0042(11) -0.0012(13) C14 0.0287(15) 0.0214(14) 0.0218(12) -0.0023(10) -0.0012(12) 0.0031(14) C15 0.0273(15) 0.0180(12) 0.0180(11) 0.0013(9) -0.0037(12) 0.0000(12) C16 0.0258(14) 0.0160(13) 0.0334(14) 0.0010(11) 0.0063(12) 0.0035(13) C17 0.0281(15) 0.0196(14) 0.0267(12) 0.0020(11) -0.0081(12) 0.0025(13) C18 0.0324(15) 0.0201(14) 0.0267(13) 0.0005(10) -0.0103(13) -0.0019(14) C19 0.0452(18) 0.0213(15) 0.0231(12) 0.0056(11) 0.0059(13) 0.0023(14) C20 0.0256(16) 0.0247(15) 0.0366(14) 0.0086(12) 0.0133(13) 0.0039(13) C21 0.0300(17) 0.0228(15) 0.0325(14) 0.0050(11) 0.0099(13) 0.0045(13) _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 C5 1.700(3) . ? P1 C6 1.806(3) . ? O1 C15 1.373(3) . ? O1 C5 1.386(3) . ? C1 C2 1.527(4) . ? C1 C20 1.539(4) . ? C2 C3 1.529(4) . ? C2 C16 1.530(4) . ? C3 C4 1.544(3) . ? C4 C5 1.497(4) . ? C4 C21 1.540(4) . ? C4 C18 1.546(4) . ? C6 C7 1.387(4) . ? C6 C15 1.416(4) . ? C7 C8 1.417(4) . ? C8 C13 1.426(4) . ? C8 C9 1.426(4) . ? C9 C10 1.367(4) . ? C10 C11 1.413(4) . ? C11 C12 1.366(4) . ? C12 C13 1.425(4) . ? C13 C14 1.415(4) . ? C14 C15 1.366(4) . ? C16 C17 1.531(4) . ? C17 C19 1.532(4) . ? C17 C18 1.534(4) . ? C19 C20 1.530(4) . ? C20 C21 1.545(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 P1 C6 88.29(12) . . ? C15 O1 C5 110.6(2) . . ? C2 C1 C20 108.9(2) . . ? C1 C2 C3 109.5(2) . . ? C1 C2 C16 109.5(2) . . ? C3 C2 C16 110.0(2) . . ? C2 C3 C4 110.43(19) . . ? C5 C4 C21 110.5(2) . . ? C5 C4 C3 109.81(19) . . ? C21 C4 C3 108.3(2) . . ? C5 C4 C18 110.5(2) . . ? C21 C4 C18 108.6(2) . . ? C3 C4 C18 109.1(2) . . ? O1 C5 C4 112.5(2) . . ? O1 C5 P1 116.91(18) . . ? C4 C5 P1 130.6(2) . . ? C7 C6 C15 117.8(3) . . ? C7 C6 P1 132.2(2) . . ? C15 C6 P1 109.95(19) . . ? C6 C7 C8 120.4(3) . . ? C7 C8 C13 119.9(2) . . ? C7 C8 C9 121.8(3) . . ? C13 C8 C9 118.4(3) . . ? C10 C9 C8 121.2(3) . . ? C9 C10 C11 120.3(3) . . ? C12 C11 C10 120.2(3) . . ? C11 C12 C13 121.1(3) . . ? C14 C13 C12 121.5(3) . . ? C14 C13 C8 119.6(3) . . ? C12 C13 C8 118.8(3) . . ? C15 C14 C13 118.2(3) . . ? C14 C15 O1 121.6(3) . . ? C14 C15 C6 124.1(3) . . ? O1 C15 C6 114.3(3) . . ? C2 C16 C17 109.8(2) . . ? C16 C17 C19 108.8(2) . . ? C16 C17 C18 109.7(2) . . ? C19 C17 C18 109.4(2) . . ? C17 C18 C4 110.3(2) . . ? C20 C19 C17 109.6(2) . . ? C19 C20 C1 109.2(2) . . ? C19 C20 C21 109.8(3) . . ? C1 C20 C21 109.8(2) . . ? C4 C21 C20 109.6(2) . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.759 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.054