Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_section_title ;A Molecular Mechanics Approach to Mapping the Conformational Space of Diaryl and Triarylphosphines ; _publ_contact_author_name J.Howell _publ_contact_author_email J.A.S.HOWELL@KEELE.AC.UK loop_ _publ_author_name J.Howell S.J.Coles D.Cunningham N.Few H.Gottlieb J.D.Lovatt P.McArdle P.Yates data_3a_jh62 _database_code_depnum_ccdc_archive 'CCDC 614969' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H27 P' _chemical_formula_weight 346.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n 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 10.737(2) _cell_length_b 12.291(2) _cell_length_c 15.286(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.39(2) _cell_angle_gamma 90.00 _cell_volume 2017.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 16.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.139 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3874 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -2 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3549 _reflns_number_gt 2633 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0811P)^2^+0.2248P] 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 3549 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1477 _refine_ls_wR_factor_gt 0.1393 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.000 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.02528(5) 0.78436(4) 0.52328(3) 0.0509(2) Uani 1 d . . . C1 C -0.09599(18) 0.74202(17) 0.44508(13) 0.0483(5) Uani 1 d . . . C2 C -0.1176(2) 0.80530(19) 0.37085(15) 0.0624(6) Uani 1 d . . . C3 C -0.2171(3) 0.7775(2) 0.31686(17) 0.0795(8) Uani 1 d . . . H3 H -0.2330 0.8196 0.2675 0.103 Uiso 1 calc R . . C4 C -0.2928(2) 0.6902(2) 0.33384(17) 0.0759(7) Uani 1 d . . . H4 H -0.3602 0.6750 0.2973 0.099 Uiso 1 calc R . . C5 C -0.2685(2) 0.6256(2) 0.40454(16) 0.0681(6) Uani 1 d . . . H5 H -0.3173 0.5647 0.4154 0.088 Uiso 1 calc R . . C6 C -0.1704(2) 0.65181(18) 0.45979(14) 0.0583(6) Uani 1 d . . . H6 H -0.1541 0.6078 0.5080 0.076 Uiso 1 calc R . . C7 C -0.0343(4) 0.9012(2) 0.34931(19) 0.1022(11) Uani 1 d . . . H7A H -0.0542 0.9592 0.3899 0.133 Uiso 1 calc R . . H7B H 0.0509 0.8794 0.3617 0.133 Uiso 1 calc R . . C8 C -0.0368(5) 0.9456(4) 0.2649(2) 0.171(2) Uani 1 d . . . H8A H -0.0177 0.8899 0.2231 0.239 Uiso 1 calc R . . H8B H 0.0238 1.0028 0.2610 0.239 Uiso 1 calc R . . H8C H -0.1182 0.9745 0.2528 0.239 Uiso 1 calc R . . C9 C 0.16280(19) 0.71017(17) 0.48422(13) 0.0511(5) Uani 1 d . . . C10 C 0.2809(2) 0.7386(2) 0.51731(14) 0.0596(6) Uani 1 d . . . C11 C 0.3836(2) 0.6801(3) 0.48855(17) 0.0758(7) Uani 1 d . . . H11 H 0.4620 0.6978 0.5105 0.099 Uiso 1 calc R . . C12 C 0.3731(2) 0.5969(2) 0.42876(17) 0.0751(7) Uani 1 d . . . H12 H 0.4435 0.5592 0.4108 0.098 Uiso 1 calc R . . C13 C 0.2581(2) 0.5701(2) 0.39578(15) 0.0646(6) Uani 1 d . . . H13 H 0.2500 0.5143 0.3550 0.084 Uiso 1 calc R . . C14 C 0.1547(2) 0.62624(18) 0.42339(14) 0.0555(5) Uani 1 d . . . H14 H 0.0770 0.6075 0.4007 0.072 Uiso 1 calc R . . C15 C 0.2999(2) 0.8307(2) 0.58110(16) 0.0753(7) Uani 1 d . . . H15A H 0.2264 0.8378 0.6171 0.098 Uiso 1 calc R . . H15B H 0.3698 0.8135 0.6193 0.098 Uiso 1 calc R . . C16 C 0.3244(3) 0.9372(3) 0.5360(2) 0.1039(11) Uani 1 d . . . H16A H 0.3990 0.9315 0.5020 0.145 Uiso 1 calc R . . H16B H 0.3344 0.9935 0.5790 0.145 Uiso 1 calc R . . H16C H 0.2555 0.9546 0.4982 0.145 Uiso 1 calc R . . C17 C -0.01552(19) 0.70548(17) 0.62170(13) 0.0515(5) Uani 1 d . . . C18 C -0.1118(2) 0.7439(2) 0.67621(15) 0.0619(6) Uani 1 d . . . C19 C -0.1334(3) 0.6885(3) 0.75418(16) 0.0772(8) Uani 1 d . . . H19 H -0.1956 0.7134 0.7912 0.100 Uiso 1 calc R . . C20 C -0.0661(3) 0.5986(3) 0.77803(16) 0.0832(8) Uani 1 d . . . H20 H -0.0825 0.5638 0.8307 0.108 Uiso 1 calc R . . C21 C 0.0258(3) 0.5595(2) 0.72429(15) 0.0742(7) Uani 1 d . . . H21 H 0.0703 0.4974 0.7396 0.096 Uiso 1 calc R . . C22 C 0.0512(2) 0.61371(19) 0.64708(14) 0.0590(6) Uani 1 d . . . H22 H 0.1145 0.5881 0.6113 0.077 Uiso 1 calc R . . C23 C -0.1944(2) 0.8387(2) 0.65252(19) 0.0789(8) Uani 1 d . . . H23A H -0.1964 0.8887 0.7016 0.103 Uiso 1 calc R . . H23B H -0.1580 0.8769 0.6034 0.103 Uiso 1 calc R . . C24 C -0.3259(3) 0.8074(3) 0.6289(3) 0.1144(12) Uani 1 d . . . H24A H -0.3249 0.7547 0.5826 0.160 Uiso 1 calc R . . H24B H -0.3708 0.8708 0.6099 0.160 Uiso 1 calc R . . H24C H -0.3660 0.7768 0.6792 0.160 Uiso 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 0.0491(3) 0.0503(3) 0.0531(3) 0.0006(2) -0.0042(2) -0.0073(2) C1 0.0435(11) 0.0502(11) 0.0511(11) 0.0010(9) -0.0017(9) 0.0003(9) C2 0.0729(15) 0.0594(13) 0.0548(12) 0.0067(10) -0.0070(11) -0.0050(11) C3 0.0888(19) 0.0808(18) 0.0685(16) 0.0162(13) -0.0257(14) -0.0022(15) C4 0.0631(15) 0.0902(19) 0.0739(16) -0.0022(14) -0.0262(13) -0.0037(13) C5 0.0539(13) 0.0750(16) 0.0752(15) 0.0014(13) -0.0072(12) -0.0148(11) C6 0.0560(13) 0.0595(13) 0.0594(13) 0.0079(10) -0.0111(10) -0.0097(10) C7 0.141(3) 0.085(2) 0.0803(19) 0.0312(16) -0.0260(19) -0.043(2) C8 0.220(5) 0.189(5) 0.104(3) 0.040(3) -0.006(3) -0.116(4) C9 0.0479(11) 0.0593(12) 0.0461(11) 0.0079(10) -0.0001(9) -0.0085(9) C10 0.0489(12) 0.0809(16) 0.0491(12) 0.0074(11) -0.0026(9) -0.0123(11) C11 0.0465(13) 0.107(2) 0.0738(16) 0.0063(16) -0.0027(11) -0.0070(13) C12 0.0549(14) 0.0946(19) 0.0760(16) 0.0056(15) 0.0110(12) 0.0073(14) C13 0.0661(14) 0.0652(14) 0.0627(13) 0.0039(11) 0.0123(11) -0.0005(12) C14 0.0504(12) 0.0571(12) 0.0591(12) 0.0049(10) 0.0014(10) -0.0077(10) C15 0.0579(14) 0.106(2) 0.0620(14) -0.0080(14) -0.0092(11) -0.0201(14) C16 0.120(3) 0.101(2) 0.090(2) -0.0136(18) 0.0037(18) -0.047(2) C17 0.0486(11) 0.0595(12) 0.0463(10) -0.0054(10) -0.0046(9) -0.0116(10) C18 0.0592(14) 0.0675(14) 0.0591(13) -0.0145(11) 0.0010(11) -0.0133(11) C19 0.0819(18) 0.096(2) 0.0541(14) -0.0149(14) 0.0145(13) -0.0226(16) C20 0.103(2) 0.098(2) 0.0485(13) 0.0059(14) 0.0035(14) -0.0284(18) C21 0.0852(18) 0.0802(17) 0.0571(14) 0.0123(13) -0.0110(13) -0.0125(14) C22 0.0587(13) 0.0653(14) 0.0528(12) 0.0017(11) -0.0054(10) -0.0057(11) C23 0.0724(16) 0.0744(17) 0.0901(18) -0.0208(15) 0.0113(14) 0.0001(14) C24 0.070(2) 0.102(2) 0.172(4) -0.025(2) -0.013(2) 0.0100(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.837(2) . ? P1 C9 1.839(2) . ? P1 C17 1.845(2) . ? C1 C6 1.386(3) . ? C1 C2 1.394(3) . ? C2 C3 1.388(3) . ? C2 C7 1.518(4) . ? C3 C4 1.373(4) . ? C4 C5 1.364(3) . ? C5 C6 1.383(3) . ? C7 C8 1.400(4) . ? C9 C14 1.391(3) . ? C9 C10 1.406(3) . ? C10 C11 1.390(4) . ? C10 C15 1.506(3) . ? C11 C12 1.375(4) . ? C12 C13 1.371(4) . ? C13 C14 1.376(3) . ? C15 C16 1.504(4) . ? C17 C22 1.390(3) . ? C17 C18 1.414(3) . ? C18 C19 1.394(4) . ? C18 C23 1.506(4) . ? C19 C20 1.368(4) . ? C20 C21 1.374(4) . ? C21 C22 1.384(3) . ? C23 C24 1.505(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 C1 P1 C9 102.44(9) . . ? C1 P1 C17 102.15(9) . . ? C9 P1 C17 101.53(10) . . ? C6 C1 C2 119.03(19) . . ? C6 C1 P1 121.88(16) . . ? C2 C1 P1 119.02(16) . . ? C3 C2 C1 118.1(2) . . ? C3 C2 C7 121.0(2) . . ? C1 C2 C7 121.0(2) . . ? C4 C3 C2 122.3(2) . . ? C5 C4 C3 119.6(2) . . ? C4 C5 C6 119.3(2) . . ? C5 C6 C1 121.6(2) . . ? C8 C7 C2 119.6(3) . . ? C14 C9 C10 118.5(2) . . ? C14 C9 P1 122.56(16) . . ? C10 C9 P1 118.95(17) . . ? C11 C10 C9 118.2(2) . . ? C11 C10 C15 119.2(2) . . ? C9 C10 C15 122.5(2) . . ? C12 C11 C10 122.2(2) . . ? C13 C12 C11 119.5(2) . . ? C12 C13 C14 119.5(2) . . ? C13 C14 C9 122.0(2) . . ? C16 C15 C10 112.4(2) . . ? C22 C17 C18 119.0(2) . . ? C22 C17 P1 121.94(17) . . ? C18 C17 P1 118.92(17) . . ? C19 C18 C17 117.8(2) . . ? C19 C18 C23 118.9(2) . . ? C17 C18 C23 123.3(2) . . ? C20 C19 C18 122.2(3) . . ? C19 C20 C21 120.2(2) . . ? C20 C21 C22 119.2(3) . . ? C21 C22 C17 121.6(2) . . ? C24 C23 C18 114.2(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.482 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.039 # Attachment '4a1.cif' data_4a_jh56 _database_code_depnum_ccdc_archive 'CCDC 614970' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H33 P' _chemical_formula_weight 388.50 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.005(2) _cell_length_b 12.990(3) _cell_length_c 18.795(5) _cell_angle_alpha 75.89(2) _cell_angle_beta 88.14(2) _cell_angle_gamma 69.87(2) _cell_volume 2442.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 16.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.056 _exptl_crystal_density_method ? _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6526 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 21.97 _reflns_number_total 5976 _reflns_number_observed 4452 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1000P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5976 _refine_ls_number_parameters 517 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_obs 0.0517 _refine_ls_wR_factor_all 0.1680 _refine_ls_wR_factor_obs 0.1568 _refine_ls_goodness_of_fit_all 1.218 _refine_ls_goodness_of_fit_obs 1.336 _refine_ls_restrained_S_all 1.218 _refine_ls_restrained_S_obs 1.336 _refine_ls_shift/esd_max 0.014 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.46761(6) 0.76202(6) 0.88507(4) 0.0552(3) Uani 1 d . . P2 P 0.13456(8) 0.21187(6) 0.59197(4) 0.0662(3) Uani 1 d . . C1 C 0.6100(2) 0.6962(2) 0.94983(14) 0.0538(6) Uani 1 d . . C2 C 0.7314(2) 0.6968(2) 0.92590(15) 0.0598(7) Uani 1 d . . C3 C 0.8339(3) 0.6574(3) 0.9781(2) 0.0777(9) Uani 1 d . . H3 H 0.9150(3) 0.6580(3) 0.9630(2) 0.101 Uiso 1 calc R . C4 C 0.8195(3) 0.6175(3) 1.0513(2) 0.0859(10) Uani 1 d . . H4 H 0.8894(3) 0.5938(3) 1.0851(2) 0.112 Uiso 1 calc R . C5 C 0.7024(3) 0.6126(3) 1.0744(2) 0.0807(9) Uani 1 d . . H5 H 0.6930(3) 0.5827(3) 1.1236(2) 0.105 Uiso 1 calc R . C6 C 0.5988(3) 0.6521(2) 1.0244(2) 0.0673(8) Uani 1 d . . H6 H 0.5189(3) 0.6495(2) 1.0406(2) 0.087 Uiso 1 calc R . C7 C 0.7544(3) 0.7380(3) 0.8458(2) 0.0705(8) Uani 1 d . . H7 H 0.6743(3) 0.7539(3) 0.8172(2) 0.092 Uiso 1 calc R . C8 C 0.8615(4) 0.6484(3) 0.8186(2) 0.1124(13) Uani 1 d . . H8A H 0.8739(18) 0.6778(8) 0.7680(5) 0.157 Uiso 1 calc R . H8B H 0.8377(12) 0.5827(9) 0.8234(14) 0.157 Uiso 1 calc R . H8C H 0.9406(7) 0.6282(17) 0.8474(10) 0.157 Uiso 1 calc R . C9 C 0.7824(4) 0.8477(3) 0.8320(2) 0.1167(14) Uani 1 d . . H9A H 0.7918(27) 0.8739(13) 0.7805(3) 0.163 Uiso 1 calc R . H9B H 0.8611(15) 0.8347(6) 0.8590(12) 0.163 Uiso 1 calc R . H9C H 0.7121(13) 0.9037(8) 0.8479(14) 0.163 Uiso 1 calc R . C10 C 0.3343(2) 0.7525(2) 0.94488(14) 0.0575(7) Uani 1 d . . C11 C 0.2733(3) 0.8381(3) 0.9815(2) 0.0771(9) Uani 1 d . . C12 C 0.1699(3) 0.8292(3) 1.0236(2) 0.0935(11) Uani 1 d . . H12 H 0.1296(3) 0.8849(3) 1.0482(2) 0.122 Uiso 1 calc R . C13 C 0.1247(3) 0.7412(3) 1.0302(2) 0.0883(10) Uani 1 d . . H13 H 0.0539(3) 0.7385(3) 1.0581(2) 0.115 Uiso 1 calc R . C14 C 0.1849(3) 0.6577(3) 0.9955(2) 0.0724(8) Uani 1 d . . H14 H 0.1561(3) 0.5970(3) 1.0002(2) 0.094 Uiso 1 calc R . C15 C 0.2876(3) 0.6635(2) 0.9537(2) 0.0641(7) Uani 1 d . . H15 H 0.3276(3) 0.6059(2) 0.9304(2) 0.083 Uiso 1 calc R . C16 C 0.3193(4) 0.9357(3) 0.9783(3) 0.1171(15) Uani 1 d . . H16 H 0.3865(4) 0.9325(3) 0.9425(3) 0.152 Uiso 1 calc R . C17 C 0.3815(6) 0.9238(5) 1.0552(3) 0.170(2) Uani 1 d . . H17A H 0.4072(38) 0.9879(18) 1.0534(7) 0.237 Uiso 1 calc R . H17B H 0.4562(25) 0.8558(19) 1.0674(11) 0.237 Uiso 1 calc R . H17C H 0.3193(14) 0.9203(37) 1.0919(5) 0.237 Uiso 1 calc R . C18 C 0.2146(5) 1.0468(4) 0.9546(4) 0.204(3) Uani 1 d . . H18A H 0.2469(16) 1.1057(5) 0.9573(29) 0.285 Uiso 1 calc R . H18B H 0.1440(23) 1.0491(18) 0.9863(19) 0.285 Uiso 1 calc R . H18C H 0.1848(36) 1.0576(20) 0.9050(11) 0.285 Uiso 1 calc R . C19 C 0.4824(2) 0.6518(2) 0.83609(14) 0.0545(7) Uani 1 d . . C20 C 0.4007(3) 0.6781(2) 0.77337(15) 0.0661(7) Uani 1 d . . C21 C 0.4200(3) 0.5958(3) 0.7352(2) 0.0838(9) Uani 1 d . . H21 H 0.3678(3) 0.6121(3) 0.6931(2) 0.109 Uiso 1 calc R . C22 C 0.5141(3) 0.4906(3) 0.7576(2) 0.0842(9) Uani 1 d . . H22 H 0.5256(3) 0.4373(3) 0.7304(2) 0.109 Uiso 1 calc R . C23 C 0.5901(3) 0.4646(2) 0.8194(2) 0.0751(8) Uani 1 d . . H23 H 0.6525(3) 0.3930(2) 0.8353(2) 0.098 Uiso 1 calc R . C24 C 0.5742(3) 0.5446(2) 0.85816(15) 0.0618(7) Uani 1 d . . H24 H 0.6266(3) 0.5262(2) 0.90049(15) 0.080 Uiso 1 calc R . C25 C 0.2934(4) 0.7911(3) 0.7482(2) 0.0981(12) Uani 1 d . . H25 H 0.2953(4) 0.8367(3) 0.7825(2) 0.128 Uiso 1 calc R . C26 C 0.1591(4) 0.7747(5) 0.7524(4) 0.184(3) Uani 1 d . . H26A H 0.1480(20) 0.7424(36) 0.7133(15) 0.258 Uiso 1 calc R . H26B H 0.0914(5) 0.8467(7) 0.7476(26) 0.258 Uiso 1 calc R . H26C H 0.1554(17) 0.7249(32) 0.7988(11) 0.258 Uiso 1 calc R . C27 C 0.3121(7) 0.8529(4) 0.6746(3) 0.196(3) Uani 1 d . . H27A H 0.3901(27) 0.8700(39) 0.6757(7) 0.274 Uiso 1 calc R . H27B H 0.2396(24) 0.9220(22) 0.6594(12) 0.274 Uiso 1 calc R . H27C H 0.3189(52) 0.8071(19) 0.6406(6) 0.274 Uiso 1 calc R . C101 C -0.0407(3) 0.2672(2) 0.5707(2) 0.0731(8) Uani 1 d . . C102 C -0.1225(4) 0.2468(3) 0.6267(2) 0.0848(9) Uani 1 d . . C103 C -0.2561(5) 0.2868(4) 0.6082(3) 0.1202(14) Uani 1 d . . H103 H -0.3128(5) 0.2751(4) 0.6446(3) 0.156 Uiso 1 calc R . C104 C -0.3052(5) 0.3434(4) 0.5369(4) 0.134(2) Uani 1 d . . H104 H -0.3940(5) 0.3687(4) 0.5259(4) 0.174 Uiso 1 calc R . C105 C -0.2243(5) 0.3620(4) 0.4828(3) 0.1192(14) Uani 1 d . . H105 H -0.2571(5) 0.3996(4) 0.4349(3) 0.155 Uiso 1 calc R . C106 C -0.0937(4) 0.3246(3) 0.5000(2) 0.0943(10) Uani 1 d . . H106 H -0.0387(4) 0.3380(3) 0.4631(2) 0.123 Uiso 1 calc R . C107 C -0.0730(4) 0.1865(3) 0.7055(2) 0.0990(11) Uani 1 d . . H107 H 0.0218(4) 0.1617(3) 0.7064(2) 0.129 Uiso 1 calc R . C108 C -0.1086(6) 0.0820(4) 0.7341(3) 0.149(2) Uani 1 d . . H10A H -0.1997(8) 0.1040(4) 0.7418(20) 0.209 Uiso 1 calc R . H10B H -0.0604(27) 0.0389(16) 0.7798(11) 0.209 Uiso 1 calc R . H10C H -0.0883(34) 0.0368(16) 0.6989(10) 0.209 Uiso 1 calc R . C109 C -0.1170(7) 0.2634(4) 0.7577(3) 0.178(3) Uani 1 d . . H10D H -0.0742(34) 0.2243(16) 0.8053(8) 0.249 Uiso 1 calc R . H10E H -0.2091(9) 0.2842(32) 0.7615(20) 0.249 Uiso 1 calc R . H10F H -0.0954(43) 0.3303(20) 0.7392(14) 0.249 Uiso 1 calc R . C110 C 0.1503(3) 0.3133(2) 0.64073(15) 0.0656(7) Uani 1 d . . C111 C 0.2553(3) 0.2822(3) 0.6907(2) 0.0731(8) Uani 1 d . . C112 C 0.2595(4) 0.3565(3) 0.7312(2) 0.0951(11) Uani 1 d . . H112 H 0.3291(4) 0.3360(3) 0.7647(2) 0.124 Uiso 1 calc R . C113 C 0.1627(4) 0.4603(3) 0.7230(2) 0.1018(12) Uani 1 d . . H113 H 0.1676(4) 0.5088(3) 0.7511(2) 0.132 Uiso 1 calc R . C114 C 0.0606(4) 0.4923(3) 0.6744(2) 0.0984(11) Uani 1 d . . H114 H -0.0049(4) 0.5623(3) 0.6689(2) 0.128 Uiso 1 calc R . C115 C 0.0551(4) 0.4195(3) 0.6329(2) 0.0846(10) Uani 1 d . . H115 H -0.0142(4) 0.4421(3) 0.5988(2) 0.110 Uiso 1 calc R . C116 C 0.3626(3) 0.1670(3) 0.7033(2) 0.1028(12) Uani 1 d . . H116 H 0.3385(3) 0.1257(3) 0.6722(2) 0.134 Uiso 1 calc R . C117 C 0.3774(9) 0.0987(5) 0.7778(4) 0.278(5) Uani 1 d . . H11A H 0.4306(74) 0.0221(17) 0.7791(9) 0.389 Uiso 1 calc R . H11B H 0.2938(13) 0.1006(62) 0.7950(18) 0.389 Uiso 1 calc R . H11C H 0.4177(79) 0.1280(46) 0.8087(10) 0.389 Uiso 1 calc R . C118 C 0.4864(6) 0.1782(7) 0.6784(6) 0.274(5) Uani 1 d . . H11D H 0.4703(8) 0.2422(47) 0.6369(30) 0.384 Uiso 1 calc R . H11E H 0.5389(36) 0.1109(33) 0.6645(48) 0.384 Uiso 1 calc R . H11F H 0.5311(39) 0.1889(75) 0.7175(16) 0.384 Uiso 1 calc R . C119 C 0.2015(3) 0.2525(2) 0.50291(15) 0.0681(8) Uani 1 d . . C120 C 0.2274(3) 0.1813(3) 0.4553(2) 0.0829(9) Uani 1 d . . C121 C 0.2844(4) 0.2107(3) 0.3899(2) 0.1035(12) Uani 1 d . . H121 H 0.3021(4) 0.1635(3) 0.3579(2) 0.135 Uiso 1 calc R . C122 C 0.3152(4) 0.3065(4) 0.3713(2) 0.1090(13) Uani 1 d . . H122 H 0.3521(4) 0.3246(4) 0.3269(2) 0.142 Uiso 1 calc R . C123 C 0.2915(4) 0.3759(3) 0.4182(2) 0.1034(12) Uani 1 d . . H123 H 0.3142(4) 0.4405(3) 0.4066(2) 0.134 Uiso 1 calc R . C124 C 0.2333(3) 0.3492(3) 0.4831(2) 0.0862(10) Uani 1 d . . H124 H 0.2152(3) 0.3977(3) 0.5143(2) 0.112 Uiso 1 calc R . C125 C 0.1949(5) 0.0737(3) 0.4724(2) 0.1167(15) Uani 1 d . . H125 H 0.1610(5) 0.0651(3) 0.5215(2) 0.152 Uiso 1 calc R . C126 C 0.0880(7) 0.0817(5) 0.4186(3) 0.191(3) Uani 1 d . . H12A H 0.0703(34) 0.0123(16) 0.4306(17) 0.267 Uiso 1 calc R . H12B H 0.1161(20) 0.0948(41) 0.3694(4) 0.267 Uiso 1 calc R . H12C H 0.0107(16) 0.1432(27) 0.4223(19) 0.267 Uiso 1 calc R . C127 C 0.3130(7) -0.0301(4) 0.4746(3) 0.187(3) Uani 1 d . . H12D H 0.2906(13) -0.0967(4) 0.4920(25) 0.262 Uiso 1 calc R . H12E H 0.3796(18) -0.0317(22) 0.5071(21) 0.262 Uiso 1 calc R . H12F H 0.3442(28) -0.0278(20) 0.4262(6) 0.262 Uiso 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 0.0504(4) 0.0527(4) 0.0629(5) -0.0193(3) 0.0025(3) -0.0148(3) P2 0.0860(6) 0.0616(5) 0.0563(5) -0.0192(4) 0.0052(4) -0.0291(4) C1 0.054(2) 0.0545(15) 0.057(2) -0.0220(12) 0.0054(12) -0.0190(12) C2 0.054(2) 0.063(2) 0.070(2) -0.0239(14) 0.0042(14) -0.0243(13) C3 0.059(2) 0.095(2) 0.089(2) -0.032(2) 0.001(2) -0.033(2) C4 0.074(2) 0.098(2) 0.090(3) -0.027(2) -0.023(2) -0.030(2) C5 0.091(3) 0.092(2) 0.060(2) -0.021(2) -0.012(2) -0.030(2) C6 0.066(2) 0.076(2) 0.063(2) -0.0221(15) 0.0054(15) -0.026(2) C7 0.061(2) 0.083(2) 0.075(2) -0.026(2) 0.0152(15) -0.032(2) C8 0.110(3) 0.130(3) 0.107(3) -0.059(3) 0.038(2) -0.036(3) C9 0.150(4) 0.104(3) 0.116(3) -0.029(2) 0.037(3) -0.069(3) C10 0.0465(15) 0.058(2) 0.071(2) -0.0249(13) -0.0011(13) -0.0152(13) C11 0.062(2) 0.081(2) 0.106(2) -0.051(2) 0.020(2) -0.028(2) C12 0.072(2) 0.102(3) 0.128(3) -0.066(2) 0.037(2) -0.033(2) C13 0.062(2) 0.109(3) 0.103(3) -0.039(2) 0.019(2) -0.034(2) C14 0.056(2) 0.077(2) 0.090(2) -0.024(2) 0.008(2) -0.027(2) C15 0.053(2) 0.066(2) 0.074(2) -0.0243(14) 0.0031(14) -0.0159(14) C16 0.108(3) 0.104(3) 0.183(4) -0.094(3) 0.067(3) -0.056(2) C17 0.173(5) 0.216(6) 0.208(6) -0.148(5) 0.048(4) -0.114(5) C18 0.162(5) 0.078(3) 0.375(10) -0.082(4) 0.119(6) -0.038(3) C19 0.0486(15) 0.056(2) 0.058(2) -0.0170(12) 0.0048(12) -0.0163(13) C20 0.067(2) 0.071(2) 0.061(2) -0.0222(15) -0.0028(14) -0.0207(15) C21 0.091(2) 0.099(3) 0.073(2) -0.035(2) -0.009(2) -0.036(2) C22 0.093(2) 0.082(2) 0.091(2) -0.045(2) 0.008(2) -0.031(2) C23 0.075(2) 0.059(2) 0.090(2) -0.031(2) 0.008(2) -0.0134(15) C24 0.062(2) 0.055(2) 0.066(2) -0.0196(14) -0.0016(14) -0.0138(14) C25 0.100(3) 0.085(2) 0.088(2) -0.022(2) -0.036(2) -0.002(2) C26 0.082(3) 0.167(5) 0.262(7) -0.042(5) -0.057(4) 0.008(3) C27 0.275(8) 0.104(3) 0.119(4) 0.015(3) -0.008(4) 0.017(4) C101 0.087(2) 0.063(2) 0.077(2) -0.028(2) 0.006(2) -0.029(2) C102 0.092(3) 0.074(2) 0.102(3) -0.041(2) 0.022(2) -0.034(2) C103 0.101(3) 0.112(3) 0.167(5) -0.059(3) 0.035(3) -0.048(3) C104 0.099(3) 0.119(4) 0.185(5) -0.043(4) -0.025(4) -0.032(3) C105 0.112(4) 0.120(3) 0.126(4) -0.029(3) -0.023(3) -0.039(3) C106 0.098(3) 0.095(2) 0.092(3) -0.022(2) -0.014(2) -0.035(2) C107 0.119(3) 0.102(3) 0.089(3) -0.036(2) 0.039(2) -0.047(2) C108 0.195(5) 0.108(3) 0.153(4) -0.019(3) 0.027(4) -0.074(4) C109 0.299(8) 0.136(4) 0.115(4) -0.065(3) 0.075(4) -0.077(5) C110 0.084(2) 0.060(2) 0.055(2) -0.0161(13) 0.0051(15) -0.028(2) C111 0.085(2) 0.076(2) 0.070(2) -0.024(2) 0.008(2) -0.038(2) C112 0.112(3) 0.101(3) 0.085(2) -0.036(2) -0.007(2) -0.042(2) C113 0.147(4) 0.095(3) 0.082(2) -0.042(2) -0.002(2) -0.050(3) C114 0.139(3) 0.068(2) 0.084(2) -0.032(2) -0.006(2) -0.022(2) C115 0.119(3) 0.067(2) 0.068(2) -0.021(2) -0.011(2) -0.029(2) C116 0.077(2) 0.112(3) 0.124(3) -0.047(3) -0.014(2) -0.024(2) C117 0.348(11) 0.146(5) 0.182(6) 0.042(5) 0.035(7) 0.052(6) C118 0.123(5) 0.216(7) 0.430(14) -0.056(8) 0.094(7) -0.016(5) C119 0.081(2) 0.066(2) 0.058(2) -0.0164(14) 0.0003(14) -0.024(2) C120 0.112(3) 0.085(2) 0.062(2) -0.028(2) 0.012(2) -0.040(2) C121 0.146(4) 0.106(3) 0.070(2) -0.036(2) 0.028(2) -0.049(3) C122 0.135(3) 0.115(3) 0.079(2) -0.023(2) 0.032(2) -0.048(3) C123 0.132(3) 0.100(3) 0.091(3) -0.020(2) 0.030(2) -0.060(2) C124 0.112(3) 0.081(2) 0.075(2) -0.021(2) 0.012(2) -0.044(2) C125 0.212(5) 0.101(3) 0.069(2) -0.042(2) 0.029(3) -0.081(3) C126 0.300(8) 0.211(6) 0.148(4) -0.073(4) 0.002(5) -0.176(6) C127 0.311(9) 0.094(3) 0.148(4) -0.044(3) 0.058(5) -0.054(4) _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 1.834(3) . ? P1 C10 1.839(3) . ? P1 C19 1.843(3) . ? P2 C101 1.831(3) . ? P2 C110 1.834(3) . ? P2 C119 1.838(3) . ? C1 C6 1.398(4) . ? C1 C2 1.398(4) . ? C2 C3 1.388(4) . ? C2 C7 1.514(4) . ? C3 C4 1.370(4) . ? C4 C5 1.363(4) . ? C5 C6 1.370(4) . ? C7 C9 1.520(4) . ? C7 C8 1.520(4) . ? C10 C15 1.392(4) . ? C10 C11 1.410(4) . ? C11 C12 1.387(4) . ? C11 C16 1.507(4) . ? C12 C13 1.373(4) . ? C13 C14 1.366(4) . ? C14 C15 1.368(4) . ? C16 C18 1.478(6) . ? C16 C17 1.570(7) . ? C19 C24 1.382(3) . ? C19 C20 1.406(4) . ? C20 C21 1.382(4) . ? C20 C25 1.510(4) . ? C21 C22 1.376(4) . ? C22 C23 1.356(4) . ? C23 C24 1.370(4) . ? C25 C27 1.468(6) . ? C25 C26 1.560(6) . ? C101 C106 1.388(4) . ? C101 C102 1.399(4) . ? C102 C103 1.404(6) . ? C102 C107 1.515(5) . ? C103 C104 1.388(7) . ? C104 C105 1.361(7) . ? C105 C106 1.370(5) . ? C107 C108 1.511(5) . ? C107 C109 1.519(5) . ? C110 C115 1.393(4) . ? C110 C111 1.394(4) . ? C111 C112 1.380(4) . ? C111 C116 1.523(5) . ? C112 C113 1.378(5) . ? C113 C114 1.353(5) . ? C114 C115 1.380(4) . ? C116 C117 1.443(7) . ? C116 C118 1.470(7) . ? C119 C124 1.381(4) . ? C119 C120 1.394(4) . ? C120 C121 1.392(5) . ? C120 C125 1.518(5) . ? C121 C122 1.362(5) . ? C122 C123 1.368(5) . ? C123 C124 1.383(4) . ? C125 C127 1.510(7) . ? C125 C126 1.535(7) . ? 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 C10 102.54(12) . . ? C1 P1 C19 102.55(11) . . ? C10 P1 C19 101.83(11) . . ? C101 P2 C110 100.55(13) . . ? C101 P2 C119 103.55(14) . . ? C110 P2 C119 102.91(13) . . ? C6 C1 C2 118.6(2) . . ? C6 C1 P1 121.4(2) . . ? C2 C1 P1 119.9(2) . . ? C3 C2 C1 118.0(3) . . ? C3 C2 C7 119.5(2) . . ? C1 C2 C7 122.4(2) . . ? C4 C3 C2 122.2(3) . . ? C5 C4 C3 119.9(3) . . ? C4 C5 C6 119.5(3) . . ? C5 C6 C1 121.8(3) . . ? C2 C7 C9 111.3(3) . . ? C2 C7 C8 111.9(3) . . ? C9 C7 C8 111.0(3) . . ? C15 C10 C11 118.0(3) . . ? C15 C10 P1 121.6(2) . . ? C11 C10 P1 120.4(2) . . ? C12 C11 C10 118.1(3) . . ? C12 C11 C16 119.4(3) . . ? C10 C11 C16 122.4(3) . . ? C13 C12 C11 122.5(3) . . ? C14 C13 C12 119.2(3) . . ? C13 C14 C15 119.8(3) . . ? C14 C15 C10 122.3(3) . . ? C18 C16 C11 112.7(4) . . ? C18 C16 C17 110.0(4) . . ? C11 C16 C17 109.9(4) . . ? C24 C19 C20 118.9(2) . . ? C24 C19 P1 121.8(2) . . ? C20 C19 P1 119.3(2) . . ? C21 C20 C19 117.8(3) . . ? C21 C20 C25 120.2(3) . . ? C19 C20 C25 122.0(2) . . ? C22 C21 C20 121.9(3) . . ? C23 C22 C21 120.0(3) . . ? C22 C23 C24 119.5(3) . . ? C23 C24 C19 121.8(3) . . ? C27 C25 C20 112.0(4) . . ? C27 C25 C26 111.9(4) . . ? C20 C25 C26 110.0(3) . . ? C106 C101 C102 119.4(3) . . ? C106 C101 P2 121.8(3) . . ? C102 C101 P2 118.8(3) . . ? C101 C102 C103 117.6(4) . . ? C101 C102 C107 122.8(3) . . ? C103 C102 C107 119.6(4) . . ? C104 C103 C102 121.3(4) . . ? C105 C104 C103 120.5(5) . . ? C104 C105 C106 119.0(4) . . ? C105 C106 C101 122.3(4) . . ? C108 C107 C102 113.0(4) . . ? C108 C107 C109 109.4(4) . . ? C102 C107 C109 112.8(3) . . ? C115 C110 C111 118.3(3) . . ? C115 C110 P2 121.6(2) . . ? C111 C110 P2 120.0(2) . . ? C112 C111 C110 119.0(3) . . ? C112 C111 C116 119.4(3) . . ? C110 C111 C116 121.6(3) . . ? C113 C112 C111 121.4(3) . . ? C114 C113 C112 120.4(3) . . ? C113 C114 C115 119.0(3) . . ? C114 C115 C110 121.9(3) . . ? C117 C116 C118 111.0(6) . . ? C117 C116 C111 114.2(4) . . ? C118 C116 C111 111.2(4) . . ? C124 C119 C120 118.6(3) . . ? C124 C119 P2 121.8(2) . . ? C120 C119 P2 119.6(2) . . ? C121 C120 C119 118.6(3) . . ? C121 C120 C125 119.3(3) . . ? C119 C120 C125 122.1(3) . . ? C122 C121 C120 122.0(3) . . ? C121 C122 C123 119.7(3) . . ? C122 C123 C124 119.3(3) . . ? C119 C124 C123 121.8(3) . . ? C127 C125 C120 112.2(4) . . ? C127 C125 C126 111.0(4) . . ? C120 C125 C126 111.5(4) . . ? _refine_diff_density_max 0.309 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.038 # Attachment '5a1.cif' data_5a_jh60 _database_code_depnum_ccdc_archive 'CCDC 614971' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H27 P' _chemical_formula_weight 346.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 7.4490(10) _cell_length_b 17.291(2) _cell_length_c 15.649(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.290(10) _cell_angle_gamma 90.00 _cell_volume 1989.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 16.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9263 _exptl_absorpt_correction_T_max 0.9522 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3495 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3495 _reflns_number_gt 3048 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0719P)^2^+0.3217P] 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 3495 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.23270(4) 0.49298(2) 0.24402(2) 0.03821(14) Uani 1 1 d . . . C1 C 0.31291(17) 0.41696(8) 0.17557(8) 0.0383(3) Uani 1 1 d . . . C2 C 0.27527(18) 0.33754(8) 0.18330(9) 0.0403(3) Uani 1 1 d . . . C3 C 0.3545(2) 0.28685(9) 0.13070(11) 0.0526(4) Uani 1 1 d . . . H3 H 0.3326 0.2341 0.1348 0.068 Uiso 1 1 calc R . . C4 C 0.4642(2) 0.31173(10) 0.07284(11) 0.0576(4) Uani 1 1 d . . . H4 H 0.5150 0.2759 0.0394 0.075 Uiso 1 1 calc R . . C5 C 0.4982(2) 0.38886(10) 0.06459(10) 0.0513(4) Uani 1 1 d . . . H5 H 0.5704 0.4061 0.0252 0.067 Uiso 1 1 calc R . . C6 C 0.42299(19) 0.44052(9) 0.11595(9) 0.0454(3) Uani 1 1 d . . . H6 H 0.4464 0.4930 0.1107 0.059 Uiso 1 1 calc R . . C7 C 0.15115(19) 0.30386(8) 0.24462(10) 0.0459(3) Uani 1 1 d . . . C8 C 0.2194(2) 0.32650(11) 0.33906(10) 0.0584(4) Uani 1 1 d . . . H8A H 0.1492 0.2999 0.3762 0.082 Uiso 1 1 calc R . . H8B H 0.2064 0.3813 0.3457 0.082 Uiso 1 1 calc R . . H8C H 0.3452 0.3125 0.3543 0.082 Uiso 1 1 calc R . . C9 C -0.0448(2) 0.33254(10) 0.21692(12) 0.0563(4) Uani 1 1 d . . . H9A H -0.1231 0.3079 0.2518 0.079 Uiso 1 1 calc R . . H9B H -0.0847 0.3201 0.1571 0.079 Uiso 1 1 calc R . . H9C H -0.0490 0.3876 0.2246 0.079 Uiso 1 1 calc R . . C10 C 0.1446(3) 0.21507(10) 0.24106(13) 0.0659(5) Uani 1 1 d . . . H10A H 0.2648 0.1947 0.2584 0.092 Uiso 1 1 calc R . . H10B H 0.0986 0.1987 0.1830 0.092 Uiso 1 1 calc R . . H10C H 0.0661 0.1963 0.2795 0.092 Uiso 1 1 calc R . . CLL C 0.44291(19) 0.51538(8) 0.31961(9) 0.0425(3) Uani 1 1 d . . . C12 C 0.4334(2) 0.56811(8) 0.38667(9) 0.0461(3) Uani 1 1 d . . . C13 C 0.5892(2) 0.58235(10) 0.44627(10) 0.0573(4) Uani 1 1 d . . . H13 H 0.5835 0.6174 0.4909 0.075 Uiso 1 1 calc R . . C14 C 0.7510(2) 0.54635(12) 0.44136(12) 0.0677(5) Uani 1 1 d . . . H14 H 0.8536 0.5574 0.4818 0.088 Uiso 1 1 calc R . . C15 C 0.7610(2) 0.49410(12) 0.37657(14) 0.0701(5) Uani 1 1 d . . . H15 H 0.8703 0.4692 0.3731 0.091 Uiso 1 1 calc R . . C16 C 0.6083(2) 0.47840(11) 0.31630(11) 0.0570(4) Uani 1 1 d . . . H16 H 0.6159 0.4425 0.2727 0.074 Uiso 1 1 calc R . . C17 C 0.2603(3) 0.61021(11) 0.39538(12) 0.0643(5) Uani 1 1 d . . . H17A H 0.2653 0.6272 0.4541 0.090 Uiso 1 1 calc R . . H17B H 0.1586 0.5761 0.3801 0.090 Uiso 1 1 calc R . . H17C H 0.2467 0.6542 0.3575 0.090 Uiso 1 1 calc R . . C18 C 0.20942(18) 0.57665(8) 0.17043(9) 0.0414(3) Uani 1 1 d . . . C19 C 0.0517(2) 0.58264(9) 0.10826(9) 0.0470(3) Uani 1 1 d . . . C20 C 0.0296(2) 0.64677(10) 0.05437(11) 0.0567(4) Uani 1 1 d . . . H20 H -0.0729 0.6500 0.0118 0.074 Uiso 1 1 calc R . . C21 C 0.1543(3) 0.70531(11) 0.06216(12) 0.0641(5) Uani 1 1 d . . . H21 H 0.1363 0.7479 0.0254 0.083 Uiso 1 1 calc R . . C22 C 0.3058(3) 0.70098(11) 0.12436(13) 0.0675(5) Uani 1 1 d . . . H22 H 0.3899 0.7412 0.1308 0.088 Uiso 1 1 calc R . . C23 C 0.3339(2) 0.63700(10) 0.17746(11) 0.0556(4) Uani 1 1 d . . . H23 H 0.4385 0.6342 0.2188 0.072 Uiso 1 1 calc R . . C24 C -0.0955(2) 0.52217(11) 0.10017(13) 0.0671(5) Uani 1 1 d . . . H24A H -0.1942 0.5374 0.0561 0.094 Uiso 1 1 calc R . . H24B H -0.1387 0.5170 0.1545 0.094 Uiso 1 1 calc R . . H24C H -0.0474 0.4735 0.0847 0.094 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 0.0315(2) 0.0428(2) 0.0400(2) -0.00300(13) 0.00465(15) -0.00068(13) C1 0.0296(6) 0.0454(7) 0.0390(7) -0.0030(6) 0.0025(5) 0.0006(5) C2 0.0322(6) 0.0451(7) 0.0419(7) -0.0016(6) 0.0014(5) 0.0000(5) C3 0.0515(9) 0.0446(8) 0.0629(9) -0.0047(7) 0.0129(7) 0.0019(7) C4 0.0542(9) 0.0596(10) 0.0623(10) -0.0107(8) 0.0189(8) 0.0082(7) C5 0.0428(8) 0.0640(10) 0.0498(8) -0.0014(7) 0.0157(6) 0.0017(7) C6 0.0397(7) 0.0492(8) 0.0476(8) 0.0001(6) 0.0082(6) -0.0027(6) C7 0.0402(7) 0.0471(8) 0.0502(8) 0.0040(6) 0.0063(6) -0.0029(6) C8 0.0620(10) 0.0654(10) 0.0474(9) 0.0078(7) 0.0074(7) -0.0009(8) C9 0.0380(8) 0.0660(10) 0.0655(10) 0.0072(8) 0.0103(7) -0.0063(7) C10 0.0676(11) 0.0519(10) 0.0807(12) 0.0056(8) 0.0196(9) -0.0079(8) CLL 0.0373(7) 0.0472(8) 0.0415(7) 0.0007(6) 0.0017(6) -0.0018(6) C12 0.0498(8) 0.0430(8) 0.0436(7) 0.0002(6) 0.0021(6) -0.0022(6) C13 0.0653(10) 0.0550(9) 0.0470(8) -0.0046(7) -0.0052(7) -0.0074(8) C14 0.0529(10) 0.0809(13) 0.0610(10) -0.0020(9) -0.0156(8) -0.0061(9) C15 0.0411(9) 0.0935(14) 0.0704(12) -0.0079(10) -0.0073(8) 0.0080(9) C16 0.0399(8) 0.0740(11) 0.0548(9) -0.0107(8) 0.0007(7) 0.0063(7) C17 0.0656(11) 0.0632(10) 0.0627(10) -0.0182(8) 0.0057(8) 0.0095(8) C18 0.0383(7) 0.0441(7) 0.0422(7) -0.0029(6) 0.0079(6) 0.0025(6) C19 0.0462(8) 0.0487(8) 0.0453(8) -0.0035(6) 0.0052(6) 0.0063(6) C20 0.0597(10) 0.0608(10) 0.0487(9) 0.0050(7) 0.0058(7) 0.0131(8) C21 0.0781(12) 0.0585(10) 0.0603(10) 0.0149(8) 0.0247(9) 0.0111(9) C22 0.0688(11) 0.0580(10) 0.0794(12) 0.0081(9) 0.0236(10) -0.0127(8) C23 0.0476(8) 0.0579(9) 0.0611(10) 0.0044(8) 0.0085(7) -0.0087(7) C24 0.0546(10) 0.0681(11) 0.0694(11) 0.0071(9) -0.0177(8) -0.0068(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 C18 1.8398(15) . ? P1 CLL 1.8448(14) . ? P1 C1 1.8543(14) . ? C1 C6 1.3987(19) . ? C1 C2 1.411(2) . ? C2 C3 1.397(2) . ? C2 C7 1.550(2) . ? C3 C4 1.382(2) . ? C4 C5 1.367(2) . ? C5 C6 1.379(2) . ? C7 C8 1.534(2) . ? C7 C9 1.536(2) . ? C7 C10 1.537(2) . ? CLL C16 1.396(2) . ? CLL C12 1.401(2) . ? C12 C13 1.388(2) . ? C12 C17 1.506(2) . ? C13 C14 1.370(3) . ? C14 C15 1.369(3) . ? C15 C16 1.382(2) . ? C18 C23 1.389(2) . ? C18 C19 1.403(2) . ? C19 C20 1.387(2) . ? C19 C24 1.506(2) . ? C20 C21 1.366(3) . ? C21 C22 1.368(3) . ? C22 C23 1.379(2) . ? 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 C18 P1 CLL 102.75(6) . . ? C18 P1 C1 101.68(6) . . ? CLL P1 C1 101.53(6) . . ? C6 C1 C2 119.13(13) . . ? C6 C1 P1 117.20(11) . . ? C2 C1 P1 123.61(10) . . ? C3 C2 C1 116.84(13) . . ? C3 C2 C7 118.71(13) . . ? C1 C2 C7 124.45(12) . . ? C4 C3 C2 122.78(15) . . ? C5 C4 C3 120.22(14) . . ? C4 C5 C6 118.54(14) . . ? C5 C6 C1 122.48(14) . . ? C8 C7 C9 109.96(14) . . ? C8 C7 C10 107.06(14) . . ? C9 C7 C10 106.79(13) . . ? C8 C7 C2 111.27(12) . . ? C9 C7 C2 109.80(12) . . ? C10 C7 C2 111.83(13) . . ? C16 CLL C12 118.52(14) . . ? C16 CLL P1 122.87(12) . . ? C12 CLL P1 118.47(11) . . ? C13 C12 CLL 118.75(14) . . ? C13 C12 C17 119.24(14) . . ? CLL C12 C17 122.01(14) . . ? C14 C13 C12 121.96(16) . . ? C15 C14 C13 119.67(16) . . ? C14 C15 C16 119.85(17) . . ? C15 C16 CLL 121.23(16) . . ? C23 C18 C19 118.25(14) . . ? C23 C18 P1 123.17(12) . . ? C19 C18 P1 118.41(11) . . ? C20 C19 C18 119.00(15) . . ? C20 C19 C24 119.38(15) . . ? C18 C19 C24 121.60(14) . . ? C21 C20 C19 121.72(16) . . ? C20 C21 C22 119.61(16) . . ? C21 C22 C23 120.00(17) . . ? C22 C23 C18 121.37(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.335 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.044 # Attachment '5b1.cif' data_jh66 _database_code_depnum_ccdc_archive 'CCDC 614972' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H27 O P' _chemical_formula_weight 362.43 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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z' '-x, -y, -z' '-x-1/2, y-1/2, -z' _cell_length_a 14.398(2) _cell_length_b 8.274(2) _cell_length_c 17.451(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.973(16) _cell_angle_gamma 90.00 _cell_volume 2033.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '4-circle diffractometer' _diffrn_measurement_method 'scintillation counter' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5244 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -2 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 31.99 _reflns_number_total 4853 _reflns_number_gt 2770 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius CAD4 software' _computing_cell_refinement 'Nonius CAD4 software' _computing_data_reduction 'XCAD (P.McArdle, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0795P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4853 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1342 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.000 _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 0.36195(3) 0.09234(6) 0.21861(2) 0.03867(17) Uani 1 1 d . . . O1 O 0.27370(8) -0.00421(18) 0.20976(7) 0.0539(4) Uani 1 1 d . . . H3 H 0.2365(17) 0.456(3) 0.0073(14) 0.074(7) Uiso 1 1 d . . . H4 H 0.3582(17) 0.422(3) -0.0593(15) 0.088(8) Uiso 1 1 d . . . H5 H 0.484(2) 0.247(4) -0.0070(16) 0.107(9) Uiso 1 1 d . . . H6 H 0.4887(14) 0.117(3) 0.1126(11) 0.057(6) Uiso 1 1 d . . . H7A H 0.169(3) 0.249(5) 0.144(2) 0.143(16) Uiso 1 1 d . . . H7B H 0.161(2) 0.418(4) 0.1120(19) 0.115(11) Uiso 1 1 d . . . H7C H 0.219(2) 0.341(4) 0.195(2) 0.124(11) Uiso 1 1 d . . . H10 H 0.5659(16) -0.343(3) 0.1782(13) 0.068(7) Uiso 1 1 d . . . H11 H 0.7015(16) -0.242(3) 0.2610(12) 0.068(7) Uiso 1 1 d . . . H12 H 0.6943(17) -0.002(3) 0.3315(14) 0.084(8) Uiso 1 1 d . . . H13 H 0.5527(13) 0.129(3) 0.3108(11) 0.051(6) Uiso 1 1 d . . . H14A H 0.334(2) -0.265(4) 0.1647(17) 0.112(10) Uiso 1 1 d . . . H14B H 0.415(2) -0.347(4) 0.1224(17) 0.105(10) Uiso 1 1 d . . . H14C H 0.369(2) -0.175(4) 0.0993(17) 0.113(12) Uiso 1 1 d . . . H17 H 0.3729(13) 0.342(3) 0.4785(12) 0.063(6) Uiso 1 1 d . . . H18 H 0.4334(15) 0.575(3) 0.4437(14) 0.071(7) Uiso 1 1 d . . . H19 H 0.4706(15) 0.603(3) 0.3207(12) 0.061(7) Uiso 1 1 d . . . H20 H 0.4384(15) 0.395(3) 0.2279(12) 0.066(6) Uiso 1 1 d . . . H22A H 0.1794(16) 0.169(3) 0.3863(13) 0.074(7) Uiso 1 1 d . . . H22B H 0.1740(18) -0.013(3) 0.3881(14) 0.083(8) Uiso 1 1 d . . . H22C H 0.1953(15) 0.069(3) 0.3098(15) 0.069(7) Uiso 1 1 d . . . H23A H 0.3342(14) -0.169(3) 0.4137(12) 0.057(6) Uiso 1 1 d . . . H23B H 0.4275(17) -0.081(3) 0.4093(12) 0.067(7) Uiso 1 1 d . . . H23C H 0.3543(14) -0.107(3) 0.3324(14) 0.064(6) Uiso 1 1 d . . . H24A H 0.2861(18) 0.182(4) 0.5131(15) 0.098(9) Uiso 1 1 d . . . H24B H 0.3931(18) 0.085(3) 0.5223(13) 0.075(7) Uiso 1 1 d . . . H24C H 0.3016(17) -0.020(4) 0.5114(15) 0.088(8) Uiso 1 1 d . . . C1 C 0.36188(11) 0.2072(2) 0.12968(9) 0.0424(5) Uani 1 1 d . . . C2 C 0.28572(12) 0.3093(3) 0.09788(10) 0.0491(5) Uani 1 1 d . . . C3 C 0.28776(17) 0.3888(3) 0.02798(12) 0.0653(6) Uani 1 1 d . . . C4 C 0.3587(2) 0.3672(4) -0.01122(14) 0.0793(8) Uani 1 1 d . . . C5 C 0.43258(19) 0.2677(4) 0.01908(14) 0.0835(8) Uani 1 1 d . . . C6 C 0.43497(14) 0.1882(3) 0.08948(11) 0.0600(6) Uani 1 1 d . . . C7 C 0.2033(2) 0.3365(5) 0.13612(19) 0.0821(9) Uani 1 1 d . . . C8 C 0.47090(12) -0.0266(2) 0.23372(9) 0.0430(5) Uani 1 1 d . . . C9 C 0.47610(15) -0.1724(3) 0.19359(10) 0.0523(5) Uani 1 1 d . . . C10 C 0.56318(18) -0.2504(3) 0.20502(14) 0.0658(7) Uani 1 1 d . . . C11 C 0.64268(17) -0.1917(3) 0.25383(14) 0.0673(7) Uani 1 1 d . . . C12 C 0.63815(15) -0.0499(4) 0.29454(13) 0.0648(7) Uani 1 1 d . . . C13 C 0.55244(13) 0.0306(3) 0.28427(11) 0.0516(5) Uani 1 1 d . . . C14 C 0.3921(2) -0.2448(4) 0.13922(18) 0.0774(8) Uani 1 1 d . . . C15 C 0.38166(10) 0.2400(2) 0.29885(9) 0.0378(4) Uani 1 1 d . . . C16 C 0.36184(10) 0.2209(2) 0.37513(9) 0.0379(4) Uani 1 1 d . . . C17 C 0.38457(14) 0.3524(3) 0.42580(11) 0.0509(5) Uani 1 1 d . . . C18 C 0.42416(15) 0.4935(3) 0.40618(12) 0.0564(6) Uani 1 1 d . . . C19 C 0.44379(16) 0.5097(3) 0.33323(12) 0.0576(6) Uani 1 1 d . . . C20 C 0.42298(14) 0.3843(3) 0.28089(11) 0.0498(5) Uani 1 1 d . . . C21 C 0.31472(12) 0.0731(2) 0.40493(10) 0.0446(5) Uani 1 1 d . . . C22 C 0.20868(14) 0.0734(4) 0.36784(15) 0.0591(6) Uani 1 1 d . . . C23 C 0.36029(16) -0.0851(3) 0.38837(14) 0.0553(6) Uani 1 1 d . . . C24 C 0.3237(2) 0.0793(4) 0.49470(13) 0.0683(7) 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 0.0366(2) 0.0433(4) 0.0377(2) -0.00307(19) 0.01133(15) -0.0034(2) O1 0.0482(7) 0.0603(11) 0.0554(7) -0.0080(7) 0.0160(6) -0.0158(7) C1 0.0394(8) 0.0514(14) 0.0360(8) 0.0001(8) 0.0070(6) -0.0014(8) C2 0.0469(9) 0.0519(15) 0.0446(9) -0.0079(9) 0.0003(7) 0.0038(9) C3 0.0717(14) 0.0658(18) 0.0506(11) 0.0023(11) -0.0052(10) 0.0124(13) C4 0.0987(19) 0.089(2) 0.0511(12) 0.0224(13) 0.0175(12) 0.0131(16) C5 0.0851(16) 0.110(2) 0.0659(14) 0.0294(15) 0.0401(13) 0.0144(16) C6 0.0510(10) 0.0799(18) 0.0526(11) 0.0175(11) 0.0187(8) 0.0108(11) C7 0.0585(13) 0.108(3) 0.0824(18) 0.0098(17) 0.0193(12) 0.0354(17) C8 0.0469(9) 0.0472(14) 0.0374(8) 0.0036(8) 0.0148(7) 0.0042(8) C9 0.0706(12) 0.0470(15) 0.0432(9) 0.0027(9) 0.0210(8) 0.0070(10) C10 0.0902(17) 0.0550(18) 0.0622(13) 0.0119(12) 0.0389(12) 0.0250(14) C11 0.0645(13) 0.077(2) 0.0671(13) 0.0240(13) 0.0284(11) 0.0269(14) C12 0.0486(11) 0.089(2) 0.0579(12) 0.0133(12) 0.0144(9) 0.0125(12) C13 0.0457(9) 0.0613(17) 0.0490(10) 0.0001(10) 0.0126(7) 0.0062(10) C14 0.100(2) 0.059(2) 0.0724(16) -0.0209(15) 0.0151(15) -0.0006(17) C15 0.0354(7) 0.0388(13) 0.0400(8) -0.0011(7) 0.0097(6) 0.0014(8) C16 0.0359(7) 0.0378(13) 0.0405(8) 0.0012(8) 0.0091(6) 0.0046(8) C17 0.0608(11) 0.0517(16) 0.0409(9) -0.0028(9) 0.0122(8) 0.0031(10) C18 0.0703(13) 0.0437(17) 0.0504(10) -0.0090(11) 0.0017(9) -0.0003(11) C19 0.0687(13) 0.0405(16) 0.0604(12) 0.0038(11) 0.0059(10) -0.0131(12) C20 0.0576(10) 0.0472(15) 0.0456(9) 0.0003(9) 0.0130(8) -0.0096(10) C21 0.0480(9) 0.0446(14) 0.0447(9) 0.0017(8) 0.0177(7) -0.0012(9) C22 0.0438(10) 0.0649(19) 0.0734(15) -0.0007(12) 0.0235(10) -0.0048(11) C23 0.0577(12) 0.0496(17) 0.0620(12) 0.0134(11) 0.0207(10) 0.0013(11) C24 0.0912(18) 0.071(2) 0.0478(11) 0.0062(11) 0.0253(11) -0.0108(16) _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 O1 1.4816(13) . ? P1 C1 1.8198(18) . ? P1 C8 1.8242(18) . ? P1 C15 1.8357(18) . ? C1 C6 1.389(2) . ? C1 C2 1.404(3) . ? C2 C3 1.392(3) . ? C2 C7 1.494(3) . ? C3 C4 1.354(3) . ? C4 C5 1.362(4) . ? C5 C6 1.387(3) . ? C8 C13 1.397(3) . ? C8 C9 1.405(3) . ? C9 C10 1.387(3) . ? C9 C14 1.499(3) . ? C10 C11 1.366(4) . ? C11 C12 1.380(4) . ? C12 C13 1.381(3) . ? C15 C20 1.398(3) . ? C15 C16 1.427(2) . ? C16 C17 1.397(3) . ? C16 C21 1.540(3) . ? C17 C18 1.373(3) . ? C18 C19 1.367(3) . ? C19 C20 1.374(3) . ? C21 C23 1.519(3) . ? C21 C22 1.530(3) . ? C21 C24 1.546(3) . ? 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 O1 P1 C1 110.13(8) . . ? O1 P1 C8 114.66(9) . . ? C1 P1 C8 104.69(8) . . ? O1 P1 C15 115.59(7) . . ? C1 P1 C15 105.99(9) . . ? C8 P1 C15 104.88(8) . . ? C6 C1 C2 118.67(17) . . ? C6 C1 P1 120.32(15) . . ? C2 C1 P1 120.90(13) . . ? C3 C2 C1 118.31(18) . . ? C3 C2 C7 118.9(2) . . ? C1 C2 C7 122.8(2) . . ? C4 C3 C2 122.4(2) . . ? C3 C4 C5 119.6(2) . . ? C4 C5 C6 120.3(2) . . ? C5 C6 C1 120.7(2) . . ? C13 C8 C9 118.77(18) . . ? C13 C8 P1 119.55(15) . . ? C9 C8 P1 121.64(14) . . ? C10 C9 C8 117.9(2) . . ? C10 C9 C14 119.5(2) . . ? C8 C9 C14 122.6(2) . . ? C11 C10 C9 122.7(3) . . ? C10 C11 C12 120.0(2) . . ? C11 C12 C13 118.7(2) . . ? C12 C13 C8 122.0(2) . . ? C20 C15 C16 118.71(16) . . ? C20 C15 P1 113.77(12) . . ? C16 C15 P1 127.50(14) . . ? C17 C16 C15 115.99(17) . . ? C17 C16 C21 117.79(15) . . ? C15 C16 C21 126.18(16) . . ? C18 C17 C16 123.98(18) . . ? C19 C18 C17 119.5(2) . . ? C18 C19 C20 119.1(2) . . ? C19 C20 C15 122.70(18) . . ? C23 C21 C22 110.71(19) . . ? C23 C21 C16 112.47(15) . . ? C22 C21 C16 109.06(17) . . ? C23 C21 C24 105.84(19) . . ? C22 C21 C24 107.17(17) . . ? C16 C21 C24 111.44(18) . . ? _diffrn_measured_fraction_theta_max 0.688 _diffrn_reflns_theta_full 31.99 _diffrn_measured_fraction_theta_full 0.688 _refine_diff_density_max 0.304 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.042 # Attachment '6b.cif' data_6b_jh48 _database_code_depnum_ccdc_archive 'CCDC 614973' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H17 O P' _chemical_formula_weight 244.26 _chemical_melting_point ? _chemical_compound_source ? 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 P21/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 8.2401(9) _cell_length_b 10.7830(9) _cell_length_c 15.5965(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.280(10) _cell_angle_gamma 90.00 _cell_volume 1354.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 16.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method ? _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.185 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3572 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.96 _reflns_number_total 3249 _reflns_number_observed 1977 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0811P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3249 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0875 _refine_ls_R_factor_obs 0.0468 _refine_ls_wR_factor_all 0.1431 _refine_ls_wR_factor_obs 0.1289 _refine_ls_goodness_of_fit_all 1.008 _refine_ls_goodness_of_fit_obs 1.180 _refine_ls_restrained_S_all 1.008 _refine_ls_restrained_S_obs 1.180 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.45485(6) 0.21997(5) 0.81203(3) 0.0444(2) Uani 1 d . . O1 O 0.4045(2) 0.08672(13) 0.80500(10) 0.0592(4) Uani 1 d . . C1 C 0.5660(3) 0.2634(2) 0.72961(14) 0.0571(6) Uani 1 d . . H1A H 0.5975 0.3491 0.7369 0.080 Uiso 1 calc R . H1B H 0.4963 0.2513 0.6725 0.080 Uiso 1 calc R . H1C H 0.6638 0.2130 0.7353 0.080 Uiso 1 calc R . C2 C 0.2762(2) 0.3212(2) 0.80009(14) 0.0492(5) Uani 1 d . . C3 C 0.1602(3) 0.3063(2) 0.8531(2) 0.0562(6) Uani 1 d . . C4 C 0.0159(3) 0.3793(3) 0.8336(2) 0.0759(8) Uani 1 d . . H4 H -0.0643 0.3691 0.8669 0.099 Uiso 1 calc R . C5 C -0.0105(3) 0.4645(3) 0.7676(2) 0.0815(9) Uani 1 d . . H5 H -0.1078 0.5110 0.7564 0.106 Uiso 1 calc R . C6 C 0.1041(3) 0.4817(3) 0.7185(2) 0.0795(8) Uani 1 d . . H6 H 0.0868 0.5411 0.6743 0.103 Uiso 1 calc R . C7 C 0.2478(3) 0.4107(2) 0.7341(2) 0.0636(6) Uani 1 d . . H7 H 0.3264 0.4231 0.7001 0.083 Uiso 1 calc R . C8 C 0.1861(3) 0.2179(2) 0.9289(2) 0.0749(8) Uani 1 d . . H8A H 0.0874 0.2145 0.9522 0.105 Uiso 1 calc R . H8B H 0.2775 0.2458 0.9736 0.105 Uiso 1 calc R . H8C H 0.2100 0.1368 0.9093 0.105 Uiso 1 calc R . C9 C 0.5963(2) 0.2484(2) 0.91632(13) 0.0443(5) Uani 1 d . . C10 C 0.6581(3) 0.3638(2) 0.94860(13) 0.0467(5) Uani 1 d . . C11 C 0.7751(3) 0.3670(2) 1.02856(14) 0.0594(6) Uani 1 d . . H11 H 0.8189 0.4429 1.0505 0.077 Uiso 1 calc R . C12 C 0.8261(3) 0.2609(3) 1.0749(2) 0.0704(7) Uani 1 d . . H12 H 0.9041 0.2654 1.1276 0.092 Uiso 1 calc R . C13 C 0.7628(4) 0.1485(2) 1.0441(2) 0.0811(8) Uani 1 d . . H13 H 0.7961 0.0767 1.0759 0.105 Uiso 1 calc R . C14 C 0.6499(3) 0.1424(2) 0.9657(2) 0.0650(6) Uani 1 d . . H14 H 0.6078 0.0655 0.9449 0.085 Uiso 1 calc R . C15 C 0.6063(3) 0.4847(2) 0.9030(2) 0.0598(6) Uani 1 d . . H15A H 0.6636 0.5517 0.9371 0.084 Uiso 1 calc R . H15B H 0.4886 0.4956 0.8966 0.084 Uiso 1 calc R . H15C H 0.6334 0.4841 0.8461 0.084 Uiso 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 0.0444(3) 0.0393(3) 0.0494(3) -0.0054(2) 0.0096(2) -0.0038(2) O1 0.0665(10) 0.0408(8) 0.0699(10) -0.0116(7) 0.0134(8) -0.0093(7) C1 0.0563(13) 0.0664(14) 0.0502(12) -0.0063(11) 0.0147(10) -0.0019(11) C2 0.0379(10) 0.0462(11) 0.0596(12) -0.0095(9) 0.0019(9) -0.0049(9) C3 0.0446(11) 0.0546(13) 0.0694(14) -0.0220(11) 0.0120(10) -0.0133(10) C4 0.0406(13) 0.089(2) 0.097(2) -0.038(2) 0.0114(13) -0.0080(12) C5 0.0452(14) 0.080(2) 0.105(2) -0.027(2) -0.0158(15) 0.0092(13) C6 0.0543(15) 0.076(2) 0.093(2) 0.0023(15) -0.0196(14) 0.0044(13) C7 0.0461(12) 0.0650(15) 0.0726(15) 0.0063(12) -0.0030(11) -0.0030(11) C8 0.077(2) 0.073(2) 0.083(2) -0.0122(14) 0.0364(15) -0.0154(14) C9 0.0452(10) 0.0408(11) 0.0473(10) -0.0015(8) 0.0106(9) -0.0004(8) C10 0.0497(11) 0.0455(11) 0.0450(10) -0.0037(8) 0.0105(9) -0.0003(9) C11 0.0611(14) 0.0643(15) 0.0497(12) -0.0098(11) 0.0044(10) -0.0016(11) C12 0.075(2) 0.077(2) 0.0523(13) 0.0024(12) -0.0014(12) 0.0099(13) C13 0.103(2) 0.065(2) 0.065(2) 0.0149(13) -0.0042(15) 0.017(2) C14 0.080(2) 0.0487(13) 0.0627(14) 0.0040(11) 0.0069(12) 0.0039(12) C15 0.0722(15) 0.0419(12) 0.0610(13) -0.0017(10) 0.0043(11) -0.0034(10) _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 O1 1.4930(15) . ? P1 C1 1.792(2) . ? P1 C2 1.810(2) . ? P1 C9 1.814(2) . ? C2 C7 1.394(3) . ? C2 C3 1.400(3) . ? C3 C4 1.404(3) . ? C3 C8 1.497(4) . ? C4 C5 1.362(4) . ? C5 C6 1.349(4) . ? C6 C7 1.387(3) . ? C9 C14 1.396(3) . ? C9 C10 1.397(3) . ? C10 C11 1.405(3) . ? C10 C15 1.503(3) . ? C11 C12 1.371(3) . ? C12 C13 1.366(4) . ? C13 C14 1.371(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 O1 P1 C1 112.03(10) . . ? O1 P1 C2 111.45(9) . . ? C1 P1 C2 107.30(11) . . ? O1 P1 C9 110.12(9) . . ? C1 P1 C9 105.66(10) . . ? C2 P1 C9 110.09(9) . . ? C7 C2 C3 119.2(2) . . ? C7 C2 P1 119.9(2) . . ? C3 C2 P1 120.8(2) . . ? C2 C3 C4 117.4(2) . . ? C2 C3 C8 122.6(2) . . ? C4 C3 C8 120.0(2) . . ? C5 C4 C3 122.2(3) . . ? C6 C5 C4 120.2(3) . . ? C5 C6 C7 119.9(3) . . ? C6 C7 C2 121.0(2) . . ? C14 C9 C10 118.8(2) . . ? C14 C9 P1 115.1(2) . . ? C10 C9 P1 126.1(2) . . ? C9 C10 C11 118.0(2) . . ? C9 C10 C15 123.8(2) . . ? C11 C10 C15 118.1(2) . . ? C12 C11 C10 121.6(2) . . ? C13 C12 C11 120.2(2) . . ? C12 C13 C14 119.5(2) . . ? C13 C14 C9 121.8(2) . . ? _refine_diff_density_max 0.319 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.052 # Attachment '6c2.cif' data_6c_jh52 _database_code_depnum_ccdc_archive 'CCDC 614974' _audit_creation_method SHELXL _chemical_name_systematic ; methyl-bis(2-methylphenyl)phosphinesulphide ; _chemical_formula_analytical 'C15 H17 P1 S1' _chemical_formula_sum 'C15 H17 P S' _chemical_formula_weight 260.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n 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 13.974(3) _cell_length_b 6.7730(10) _cell_length_c 15.790(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.380(10) _cell_angle_gamma 90.00 _cell_volume 1391.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 18.0 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.242 _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.323 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device CAD4 _diffrn_measurement_method Theta/2*Theta _diffrn_standards_number 3 _diffrn_standards_interval_time 30 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4018 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 29.96 _reflns_number_total 3742 _reflns_number_observed 2501 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Nonius Software' _computing_cell_refinement 'Nonius Software' _computing_data_reduction 'Nonius Software' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEX (McArdle 1994)' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1000P)^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_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3742 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_obs 0.0618 _refine_ls_wR_factor_all 0.1919 _refine_ls_wR_factor_obs 0.1811 _refine_ls_goodness_of_fit_all 1.216 _refine_ls_goodness_of_fit_obs 1.414 _refine_ls_restrained_S_all 1.216 _refine_ls_restrained_S_obs 1.414 _refine_ls_shift/esd_max -0.007 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.68664(5) 0.10681(9) 0.98199(4) 0.0384(2) Uani 1 d . . S1 S 0.60406(7) 0.34263(12) 0.97704(5) 0.0581(3) Uani 1 d . . C1 C 0.6015(2) -0.0996(4) 0.9324(2) 0.0556(7) Uani 1 d . . H1A H 0.5521 -0.0612 0.8744 0.078 Uiso 1 calc R . H1B H 0.5665 -0.1374 0.9720 0.078 Uiso 1 calc R . H1C H 0.6411 -0.2091 0.9244 0.078 Uiso 1 calc R . C2 C 0.7686(2) 0.0457(3) 1.09747(15) 0.0370(5) Uani 1 d . . C3 C 0.8496(2) 0.1696(3) 1.1486(2) 0.0393(5) Uani 1 d . . C4 C 0.9084(2) 0.1158(4) 1.2371(2) 0.0494(6) Uani 1 d . . H4 H 0.9626 0.1961 1.2715 0.064 Uiso 1 calc R . C5 C 0.8878(2) -0.0548(4) 1.2751(2) 0.0566(7) Uani 1 d . . H5 H 0.9281 -0.0881 1.3346 0.074 Uiso 1 calc R . C6 C 0.8085(3) -0.1754(4) 1.2258(2) 0.0566(7) Uani 1 d . . H6 H 0.7947 -0.2899 1.2518 0.074 Uiso 1 calc R . C7 C 0.7491(2) -0.1264(4) 1.1374(2) 0.0475(6) Uani 1 d . . H7 H 0.6954 -0.2089 1.1039 0.062 Uiso 1 calc R . C8 C 0.8747(3) 0.3609(4) 1.1123(2) 0.0527(7) Uani 1 d . . H8A H 0.8153 0.4449 1.0933 0.074 Uiso 1 calc R . H8B H 0.8947 0.3338 1.0614 0.074 Uiso 1 calc R . H8C H 0.9302 0.4255 1.1592 0.074 Uiso 1 calc R . C9 C 0.7694(2) 0.1286(3) 0.91561(15) 0.0389(5) Uani 1 d . . C10 C 0.8424(2) -0.0142(4) 0.9159(2) 0.0427(5) Uani 1 d . . C11 C 0.9019(2) 0.0221(5) 0.8641(2) 0.0576(7) Uani 1 d . . H11 H 0.9509 -0.0707 0.8641 0.075 Uiso 1 calc R . C12 C 0.8913(3) 0.1884(5) 0.8131(2) 0.0624(8) Uani 1 d . . H12 H 0.9331 0.2081 0.7795 0.081 Uiso 1 calc R . C13 C 0.8186(3) 0.3278(5) 0.8112(2) 0.0618(8) Uani 1 d . . H13 H 0.8104 0.4410 0.7759 0.080 Uiso 1 calc R . C14 C 0.7584(2) 0.2970(4) 0.8623(2) 0.0493(6) Uani 1 d . . H14 H 0.7093 0.3907 0.8612 0.064 Uiso 1 calc R . C15 C 0.8599(3) -0.2068(4) 0.9689(2) 0.0564(7) Uani 1 d . . H15A H 0.9122 -0.2820 0.9576 0.079 Uiso 1 calc R . H15B H 0.7972 -0.2813 0.9499 0.079 Uiso 1 calc R . H15C H 0.8814 -0.1786 1.0327 0.079 Uiso 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 0.0411(3) 0.0465(4) 0.0274(3) -0.0013(2) 0.0123(2) 0.0005(2) S1 0.0621(5) 0.0654(5) 0.0466(4) 0.0047(3) 0.0196(4) 0.0203(3) C1 0.052(2) 0.069(2) 0.048(2) -0.0183(13) 0.0203(13) -0.0236(13) C2 0.0428(13) 0.0425(11) 0.0280(10) 0.0013(8) 0.0156(9) 0.0035(9) C3 0.0426(13) 0.0445(12) 0.0319(11) -0.0011(9) 0.0148(10) 0.0042(9) C4 0.0467(15) 0.065(2) 0.0331(12) 0.0012(10) 0.0102(11) 0.0046(12) C5 0.057(2) 0.080(2) 0.0351(13) 0.0166(12) 0.0189(12) 0.0167(14) C6 0.067(2) 0.065(2) 0.047(2) 0.0192(13) 0.0318(14) 0.0092(14) C7 0.057(2) 0.0515(15) 0.0408(13) 0.0050(10) 0.0264(12) -0.0038(11) C8 0.060(2) 0.0458(14) 0.048(2) 0.0002(11) 0.0149(13) -0.0073(11) C9 0.0436(13) 0.0468(13) 0.0263(10) -0.0020(8) 0.0128(9) -0.0030(9) C10 0.0428(14) 0.0498(13) 0.0349(12) -0.0031(9) 0.0135(10) -0.0003(10) C11 0.054(2) 0.077(2) 0.049(2) 0.0000(13) 0.0271(14) 0.0085(14) C12 0.068(2) 0.083(2) 0.049(2) 0.0076(14) 0.036(2) -0.002(2) C13 0.075(2) 0.070(2) 0.043(2) 0.0167(13) 0.0253(15) -0.003(2) C14 0.061(2) 0.0537(15) 0.0335(12) 0.0060(10) 0.0174(11) 0.0061(12) C15 0.067(2) 0.0495(15) 0.058(2) 0.0021(12) 0.0287(15) 0.0086(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 C2 1.813(2) . ? P1 C1 1.817(3) . ? P1 C9 1.829(2) . ? P1 S1 1.9552(10) . ? C2 C7 1.399(3) . ? C2 C3 1.404(3) . ? C3 C4 1.387(3) . ? C3 C8 1.509(3) . ? C4 C5 1.379(4) . ? C5 C6 1.369(5) . ? C6 C7 1.379(4) . ? C9 C14 1.392(3) . ? C9 C10 1.404(4) . ? C10 C11 1.385(4) . ? C10 C15 1.521(4) . ? C11 C12 1.360(4) . ? C12 C13 1.379(5) . ? C13 C14 1.378(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 C2 P1 C1 109.41(13) . . ? C2 P1 C9 107.16(11) . . ? C1 P1 C9 105.43(12) . . ? C2 P1 S1 111.97(8) . . ? C1 P1 S1 109.10(12) . . ? C9 P1 S1 113.51(8) . . ? C7 C2 C3 119.2(2) . . ? C7 C2 P1 119.2(2) . . ? C3 C2 P1 121.5(2) . . ? C4 C3 C2 118.6(2) . . ? C4 C3 C8 118.3(3) . . ? C2 C3 C8 123.1(2) . . ? C5 C4 C3 121.2(3) . . ? C6 C5 C4 120.4(3) . . ? C5 C6 C7 119.7(3) . . ? C6 C7 C2 120.8(3) . . ? C14 C9 C10 119.1(2) . . ? C14 C9 P1 117.3(2) . . ? C10 C9 P1 123.6(2) . . ? C11 C10 C9 117.9(2) . . ? C11 C10 C15 117.8(2) . . ? C9 C10 C15 124.3(2) . . ? C12 C11 C10 122.5(3) . . ? C11 C12 C13 120.0(3) . . ? C14 C13 C12 119.1(3) . . ? C13 C14 C9 121.4(3) . . ? _refine_diff_density_max 0.583 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.074 _chemical_name_common methyl-bis(2-methylphenyl)phosphinesulphide # Attachment '6e1.cif' data_6e_jh55 _database_code_depnum_ccdc_archive 'CCDC 614975' _audit_creation_method SHELXL _chemical_name_systematic ; Pentacarbonyl[methylbis(2-methylphenyl)phosphine]chromium ; _chemical_formula_analytical 'C 20 H 17 O 5 P 1 Cr 1' _chemical_formula_sum 'C20 H17 Cr O5 P' _chemical_formula_weight 420.31 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' Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n 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 10.7630(10) _cell_length_b 13.300(2) _cell_length_c 14.2690(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.620(10) _cell_angle_gamma 90.00 _cell_volume 2029.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 16.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.34 _exptl_crystal_density_diffrn 1.376 _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.669 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device CAD4 _diffrn_measurement_method Theta/2*Theta _diffrn_standards_number 3 _diffrn_standards_interval_time 30 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6371 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 29.97 _reflns_number_total 5899 _reflns_number_observed 4419 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Nonius Software' _computing_cell_refinement 'Nonius Software' _computing_data_reduction 'Nonius Software' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEX (McArdle 1994)' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1000P)^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_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5899 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_obs 0.0443 _refine_ls_wR_factor_all 0.1425 _refine_ls_wR_factor_obs 0.1342 _refine_ls_goodness_of_fit_all 1.042 _refine_ls_goodness_of_fit_obs 1.140 _refine_ls_restrained_S_all 1.042 _refine_ls_restrained_S_obs 1.140 _refine_ls_shift/esd_max -0.195 _refine_ls_shift/esd_mean 0.026 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cr1 Cr 0.02379(2) 0.78591(2) 0.94480(2) 0.05178(11) Uani 1 d . . P1 P 0.19906(4) 0.72788(3) 0.86742(3) 0.04537(11) Uani 1 d . . O1 O 0.1723(2) 0.91340(14) 1.09480(13) 0.0967(5) Uani 1 d . . O3 O -0.2035(2) 0.85597(15) 1.02986(12) 0.0964(5) Uani 1 d . . O4 O 0.0584(2) 0.61165(14) 1.08299(12) 0.0953(5) Uani 1 d . . O5 O -0.0042(2) 0.95079(14) 0.79744(13) 0.1074(6) Uani 1 d . . O2 O -0.1504(2) 0.6563(2) 0.81325(15) 0.1188(7) Uani 1 d . . C1 C 0.1489(2) 0.70522(14) 0.74261(12) 0.0604(4) Uani 1 d . . H1A H 0.1308 0.7682 0.7111 0.085 Uiso 1 calc R . H1B H 0.0751 0.6641 0.7364 0.085 Uiso 1 calc R . H1C H 0.2143 0.6714 0.7147 0.085 Uiso 1 calc R . C2 C 0.33724(15) 0.80871(12) 0.86014(10) 0.0490(3) Uani 1 d . . C3 C 0.4462(2) 0.77841(13) 0.82293(12) 0.0561(4) Uani 1 d . . C4 C 0.5429(2) 0.8480(2) 0.82157(14) 0.0723(5) Uani 1 d . . H4 H 0.6157 0.8288 0.7970 0.094 Uiso 1 calc R . C5 C 0.5334(2) 0.9451(2) 0.85598(15) 0.0751(5) Uani 1 d . . H5 H 0.5998 0.9897 0.8552 0.098 Uiso 1 calc R . C6 C 0.4272(2) 0.97489(15) 0.89060(12) 0.0662(5) Uani 1 d . . H6 H 0.4202 1.0400 0.9131 0.086 Uiso 1 calc R . C7 C 0.3291(2) 0.90755(13) 0.89225(11) 0.0564(4) Uani 1 d . . H7 H 0.2560 0.9287 0.9153 0.073 Uiso 1 calc R . C8 C 0.4657(2) 0.6756(2) 0.78133(15) 0.0706(5) Uani 1 d . . H8A H 0.4221 0.6720 0.7188 0.099 Uiso 1 calc R . H8B H 0.4339 0.6249 0.8201 0.099 Uiso 1 calc R . H8C H 0.5534 0.6646 0.7787 0.099 Uiso 1 calc R . C9 C 0.25649(14) 0.60681(12) 0.91459(11) 0.0491(3) Uani 1 d . . C10 C 0.3282(2) 0.59859(13) 1.00303(12) 0.0552(4) Uani 1 d . . C11 C 0.3557(2) 0.5032(2) 1.0388(2) 0.0728(5) Uani 1 d . . H11 H 0.4044 0.4972 1.0967(2) 0.095 Uiso 1 calc R . C12 C 0.3141(2) 0.4176(2) 0.9921(2) 0.0791(6) Uani 1 d . . H12 H 0.3334 0.3549 1.0187 0.103 Uiso 1 calc R . C13 C 0.2436(2) 0.42477(14) 0.9055(2) 0.0700(5) Uani 1 d . . H13 H 0.2157 0.3670 0.8728 0.091 Uiso 1 calc R . C14 C 0.2146(2) 0.51894(13) 0.86758(13) 0.0595(4) Uani 1 d . . H14 H 0.1662 0.5237 0.8094 0.077 Uiso 1 calc R . C15 C 0.3761(2) 0.6883(2) 1.06064(14) 0.0710(5) Uani 1 d . . H15A H 0.3088 0.7348 1.0651 0.099 Uiso 1 calc R . H15B H 0.4409 0.7206 1.0308 0.099 Uiso 1 calc R . H15C H 0.4091 0.6667 1.1227 0.099 Uiso 1 calc R . C16 C 0.1190(2) 0.8661(2) 1.03588(14) 0.0661(4) Uani 1 d . . C17 C -0.0824(2) 0.7039(2) 0.8626(2) 0.0735(5) Uani 1 d . . C18 C -0.1176(2) 0.8286(2) 0.99706(14) 0.0684(5) Uani 1 d . . C19 C 0.0457(2) 0.6758(2) 1.03072(14) 0.0656(4) Uani 1 d . . C20 C 0.0062(2) 0.8903(2) 0.85456(14) 0.0703(5) Uani 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 Cr1 0.0502(2) 0.0556(2) 0.0509(2) 0.00204(10) 0.01173(11) 0.00735(10) P1 0.0482(2) 0.0481(2) 0.0401(2) -0.00082(13) 0.00664(15) 0.00281(14) O1 0.1071(13) 0.1047(13) 0.0811(10) -0.0348(9) 0.0228(9) -0.0184(10) O3 0.0774(10) 0.1180(13) 0.1001(12) 0.0053(10) 0.0368(9) 0.0325(9) O4 0.0924(11) 0.1012(12) 0.0981(11) 0.0456(10) 0.0354(9) 0.0190(9) O5 0.148(2) 0.0857(11) 0.0914(11) 0.0315(9) 0.0258(12) 0.0361(11) O2 0.0819(12) 0.162(2) 0.1111(14) -0.0372(14) 0.0067(11) -0.0381(13) C1 0.0639(10) 0.0749(11) 0.0421(8) -0.0017(7) 0.0043(7) -0.0002(8) C2 0.0517(8) 0.0551(8) 0.0402(7) 0.0040(6) 0.0052(6) -0.0005(6) C3 0.0529(8) 0.0681(10) 0.0473(8) 0.0064(7) 0.0052(7) 0.0046(7) C4 0.0525(9) 0.0974(15) 0.0671(11) 0.0122(10) 0.0079(8) -0.0024(9) C5 0.0676(12) 0.0834(13) 0.0718(12) 0.0094(10) -0.0021(9) -0.0223(10) C6 0.0786(12) 0.0631(10) 0.0542(9) 0.0066(8) -0.0042(8) -0.0123(9) C7 0.0651(10) 0.0557(8) 0.0484(8) 0.0038(7) 0.0060(7) -0.0030(7) C8 0.0654(11) 0.0763(12) 0.0730(11) 0.0001(10) 0.0204(9) 0.0170(9) C9 0.0494(7) 0.0501(7) 0.0489(7) -0.0002(6) 0.0112(6) 0.0034(6) C10 0.0525(8) 0.0570(9) 0.0562(8) 0.0056(7) 0.0063(7) 0.0070(7) C11 0.0673(11) 0.0715(12) 0.0784(12) 0.0200(10) 0.0029(9) 0.0122(9) C12 0.0747(12) 0.0570(10) 0.110(2) 0.0190(11) 0.0280(12) 0.0134(9) C13 0.0754(12) 0.0507(9) 0.0882(13) -0.0037(9) 0.0283(10) -0.0015(8) C14 0.0653(10) 0.0528(8) 0.0618(9) -0.0069(7) 0.0133(8) 0.0005(7) C15 0.0760(12) 0.0738(11) 0.0584(10) -0.0015(9) -0.0130(9) 0.0028(10) C16 0.0693(11) 0.0707(11) 0.0615(10) -0.0070(9) 0.0220(9) 0.0019(9) C17 0.0573(10) 0.0945(15) 0.0699(12) -0.0049(10) 0.0125(9) -0.0009(10) C18 0.0638(10) 0.0780(12) 0.0654(10) 0.0042(9) 0.0157(8) 0.0159(9) C19 0.0551(9) 0.0775(12) 0.0672(11) 0.0087(9) 0.0201(8) 0.0078(8) C20 0.0790(13) 0.0679(11) 0.0658(11) 0.0047(9) 0.0164(9) 0.0187(9) _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 Cr1 C18 1.859(2) . ? Cr1 C17 1.888(2) . ? Cr1 C20 1.888(2) . ? Cr1 C16 1.889(2) . ? Cr1 C19 1.907(2) . ? Cr1 P1 2.4194(5) . ? P1 C9 1.825(2) . ? P1 C1 1.826(2) . ? P1 C2 1.848(2) . ? O1 C16 1.149(2) . ? O3 C18 1.143(2) . ? O4 C19 1.131(2) . ? O5 C20 1.142(2) . ? O2 C17 1.146(3) . ? C2 C7 1.398(2) . ? C2 C3 1.401(2) . ? C3 C4 1.395(3) . ? C3 C8 1.515(3) . ? C4 C5 1.391(3) . ? C5 C6 1.355(3) . ? C6 C7 1.387(3) . ? C9 C14 1.396(2) . ? C9 C10 1.405(2) . ? C10 C11 1.387(2) . ? C10 C15 1.506(3) . ? C11 C12 1.368(3) . ? C12 C13 1.377(4) . ? C13 C14 1.385(3) . ? 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 C18 Cr1 C17 87.74(10) . . ? C18 Cr1 C20 91.52(9) . . ? C17 Cr1 C20 89.70(10) . . ? C18 Cr1 C16 87.48(9) . . ? C17 Cr1 C16 174.41(9) . . ? C20 Cr1 C16 93.34(9) . . ? C18 Cr1 C19 91.33(8) . . ? C17 Cr1 C19 88.68(10) . . ? C20 Cr1 C19 176.67(8) . . ? C16 Cr1 C19 88.52(9) . . ? C18 Cr1 P1 176.25(7) . . ? C17 Cr1 P1 88.86(7) . . ? C20 Cr1 P1 86.87(6) . . ? C16 Cr1 P1 95.98(6) . . ? C19 Cr1 P1 90.18(5) . . ? C9 P1 C1 105.28(8) . . ? C9 P1 C2 107.07(7) . . ? C1 P1 C2 101.00(8) . . ? C9 P1 Cr1 111.21(5) . . ? C1 P1 Cr1 109.83(7) . . ? C2 P1 Cr1 121.00(5) . . ? C7 C2 C3 118.8(2) . . ? C7 C2 P1 116.55(13) . . ? C3 C2 P1 124.62(13) . . ? C4 C3 C2 118.2(2) . . ? C4 C3 C8 117.1(2) . . ? C2 C3 C8 124.6(2) . . ? C5 C4 C3 121.7(2) . . ? C4 C5 C6 120.0(2) . . ? C5 C6 C7 119.6(2) . . ? C2 C7 C6 121.6(2) . . ? C14 C9 C10 118.7(2) . . ? C14 C9 P1 118.98(13) . . ? C10 C9 P1 121.81(12) . . ? C11 C10 C9 118.2(2) . . ? C11 C10 C15 118.6(2) . . ? C9 C10 C15 123.13(15) . . ? C12 C11 C10 122.6(2) . . ? C11 C12 C13 119.6(2) . . ? C12 C13 C14 119.3(2) . . ? C9 C14 C13 121.6(2) . . ? O1 C16 Cr1 176.2(2) . . ? O2 C17 Cr1 177.5(2) . . ? O3 C18 Cr1 179.0(2) . . ? O4 C19 Cr1 178.7(2) . . ? O5 C20 Cr1 177.5(2) . . ? _refine_diff_density_max 0.499 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.090 _chemical_name_common Pentacarbonyl(methylbis(2-methylphenyl)phosphine)chromium # Attachment '7b1.cif' data_7b_jh69 _database_code_depnum_ccdc_archive 'CCDC 620845' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H23 O P' _chemical_formula_weight 286.33 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 P212121 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' _cell_length_a 7.518(2) _cell_length_b 13.085(2) _cell_length_c 16.660(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1638.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 16.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.61 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.160 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3333 _diffrn_reflns_av_R_equivalents 0.0117 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 31.98 _reflns_number_total 3215 _reflns_number_gt 2386 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1011P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(13) _refine_ls_number_reflns 3215 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 -0.28716(7) -0.07823(4) -0.14655(3) 0.03825(14) Uani 1 1 d . . . O1 O -0.1138(2) -0.06482(15) -0.10578(10) 0.0525(4) Uani 1 1 d . . . C1 C -0.3653(4) -0.21088(19) -0.13183(14) 0.0519(5) Uani 1 1 d . . . C2 C -0.2110(5) -0.2774(2) -0.1638(2) 0.0777(9) Uani 1 1 d . . . H2A H -0.2365 -0.3482 -0.1537 0.109 Uiso 1 1 calc R . . H2B H -0.1027 -0.2587 -0.1370 0.109 Uiso 1 1 calc R . . H2C H -0.1980 -0.2667 -0.2205 0.109 Uiso 1 1 calc R . . C3 C -0.5356(5) -0.2406(2) -0.1769(2) 0.0699(8) Uani 1 1 d . . . H3A H -0.6344 -0.2030 -0.1555 0.098 Uiso 1 1 calc R . . H3B H -0.5568 -0.3125 -0.1706 0.098 Uiso 1 1 calc R . . H3C H -0.5221 -0.2249 -0.2329 0.098 Uiso 1 1 calc R . . C4 C -0.3842(5) -0.2289(3) -0.04071(17) 0.0702(8) Uani 1 1 d . . . H4A H -0.4066 -0.3000 -0.0308 0.098 Uiso 1 1 calc R . . H4B H -0.4815 -0.1890 -0.0204 0.098 Uiso 1 1 calc R . . H4C H -0.2764 -0.2089 -0.0142 0.098 Uiso 1 1 calc R . . C5 C -0.4483(3) 0.01569(18) -0.11211(11) 0.0407(4) Uani 1 1 d . . . C6 C -0.4002(3) 0.11918(19) -0.11304(13) 0.0484(5) Uani 1 1 d . . . C7 C -0.5269(5) 0.1910(2) -0.08817(17) 0.0675(8) Uani 1 1 d . . . H7 H -0.4963 0.2599 -0.0879 0.088 Uiso 1 1 calc R . . C8 C -0.6941(5) 0.1631(3) -0.06423(19) 0.0754(9) Uani 1 1 d . . . H8 H -0.7752 0.2128 -0.0482 0.098 Uiso 1 1 calc R . . C9 C -0.7427(4) 0.0619(3) -0.06376(16) 0.0683(8) Uani 1 1 d . . . H9 H -0.8564 0.0426 -0.0479 0.089 Uiso 1 1 calc R . . C10 C -0.6201(3) -0.0107(2) -0.08715(14) 0.0530(5) Uani 1 1 d . . . H10 H -0.6526 -0.0792 -0.0863 0.069 Uiso 1 1 calc R . . C11 C -0.2208(4) 0.1568(2) -0.1396(2) 0.0658(7) Uani 1 1 d . . . H11A H -0.2216 0.2301 -0.1420 0.092 Uiso 1 1 calc R . . H11B H -0.1941 0.1297 -0.1918 0.092 Uiso 1 1 calc R . . H11C H -0.1319 0.1346 -0.1021 0.092 Uiso 1 1 calc R . . C12 C -0.2854(3) -0.05757(15) -0.25484(10) 0.0394(4) Uani 1 1 d . . . C13 C -0.1298(3) -0.0588(2) -0.30210(13) 0.0502(5) Uani 1 1 d . . . C14 C -0.1500(4) -0.0425(3) -0.38468(14) 0.0639(7) Uani 1 1 d . . . H14 H -0.0493 -0.0428 -0.4171 0.083 Uiso 1 1 calc R . . C15 C -0.3143(4) -0.0259(2) -0.41970(13) 0.0601(7) Uani 1 1 d . . . H15 H -0.3229 -0.0159 -0.4748 0.078 Uiso 1 1 calc R . . C16 C -0.4630(4) -0.02422(19) -0.37339(12) 0.0517(5) Uani 1 1 d . . . H16 H -0.5737 -0.0130 -0.3967 0.067 Uiso 1 1 calc R . . C17 C -0.4488(3) -0.03941(19) -0.29110(11) 0.0434(4) Uani 1 1 d . . . H17 H -0.5509 -0.0374 -0.2596 0.056 Uiso 1 1 calc R . . C18 C 0.0530(3) -0.0734(3) -0.26976(18) 0.0753(9) Uani 1 1 d . . . H18A H 0.0572 -0.1352 -0.2387 0.105 Uiso 1 1 calc R . . H18B H 0.0838 -0.0164 -0.2363 0.105 Uiso 1 1 calc R . . H18C H 0.1359 -0.0781 -0.3134 0.105 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 0.0416(2) 0.0480(3) 0.02519(19) -0.00021(18) -0.00228(18) -0.0004(2) O1 0.0446(7) 0.0726(11) 0.0404(7) -0.0024(8) -0.0107(6) 0.0002(8) C1 0.0639(13) 0.0479(11) 0.0438(10) 0.0076(8) -0.0044(10) -0.0020(11) C2 0.097(2) 0.0536(14) 0.083(2) 0.0043(14) 0.005(2) 0.0150(17) C3 0.090(2) 0.0529(14) 0.0668(15) 0.0043(12) -0.0212(17) -0.0201(15) C4 0.0819(19) 0.0765(17) 0.0521(13) 0.0240(13) -0.0070(14) -0.0081(17) C5 0.0425(9) 0.0555(11) 0.0241(7) -0.0014(7) -0.0002(7) 0.0007(9) C6 0.0537(12) 0.0557(12) 0.0358(9) -0.0005(9) -0.0052(9) 0.0031(10) C7 0.085(2) 0.0613(15) 0.0562(14) -0.0082(12) -0.0084(15) 0.0177(15) C8 0.0717(19) 0.096(2) 0.0587(15) -0.0154(16) 0.0014(15) 0.0326(19) C9 0.0530(13) 0.105(2) 0.0466(12) -0.0083(14) 0.0074(10) 0.0105(14) C10 0.0458(10) 0.0757(15) 0.0375(9) -0.0039(10) 0.0038(9) -0.0051(11) C11 0.0701(16) 0.0516(12) 0.0755(17) 0.0096(12) -0.0012(17) -0.0093(13) C12 0.0444(9) 0.0465(10) 0.0275(7) -0.0021(6) 0.0008(8) 0.0001(9) C13 0.0494(11) 0.0659(15) 0.0354(9) -0.0041(9) 0.0100(9) 0.0012(11) C14 0.0702(15) 0.0864(18) 0.0350(10) -0.0005(12) 0.0176(11) -0.0078(15) C15 0.0861(19) 0.0674(14) 0.0268(8) 0.0026(9) 0.0047(11) -0.0029(14) C16 0.0722(14) 0.0543(12) 0.0287(8) 0.0019(8) -0.0084(10) 0.0037(12) C17 0.0471(10) 0.0544(11) 0.0287(8) 0.0002(8) -0.0015(8) 0.0033(10) C18 0.0461(12) 0.117(3) 0.0625(16) -0.0080(19) 0.0100(12) 0.0056(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4802(16) . ? P1 C5 1.818(2) . ? P1 C12 1.824(2) . ? P1 C1 1.849(3) . ? C1 C3 1.535(4) . ? C1 C4 1.543(4) . ? C1 C2 1.545(4) . ? C5 C10 1.400(3) . ? C5 C6 1.402(3) . ? C6 C7 1.401(4) . ? C6 C11 1.503(4) . ? C7 C8 1.369(5) . ? C8 C9 1.373(5) . ? C9 C10 1.379(4) . ? C12 C17 1.390(3) . ? C12 C13 1.410(3) . ? C13 C14 1.400(3) . ? C13 C18 1.489(4) . ? C14 C15 1.383(4) . ? C15 C16 1.359(4) . ? C16 C17 1.389(3) . ? 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 O1 P1 C5 111.20(10) . . ? O1 P1 C12 115.46(10) . . ? C5 P1 C12 102.51(9) . . ? O1 P1 C1 109.28(11) . . ? C5 P1 C1 112.40(12) . . ? C12 P1 C1 105.82(10) . . ? C3 C1 C4 111.5(3) . . ? C3 C1 C2 108.3(2) . . ? C4 C1 C2 108.8(2) . . ? C3 C1 P1 115.97(18) . . ? C4 C1 P1 107.67(19) . . ? C2 C1 P1 104.2(2) . . ? C10 C5 C6 118.6(2) . . ? C10 C5 P1 122.81(19) . . ? C6 C5 P1 118.55(17) . . ? C7 C6 C5 118.0(3) . . ? C7 C6 C11 118.5(3) . . ? C5 C6 C11 123.4(2) . . ? C8 C7 C6 122.1(3) . . ? C7 C8 C9 120.2(3) . . ? C8 C9 C10 119.0(3) . . ? C9 C10 C5 122.1(3) . . ? C17 C12 C13 119.51(17) . . ? C17 C12 P1 116.67(15) . . ? C13 C12 P1 123.82(16) . . ? C14 C13 C12 117.2(2) . . ? C14 C13 C18 118.4(2) . . ? C12 C13 C18 124.4(2) . . ? C15 C14 C13 122.3(2) . . ? C16 C15 C14 119.86(19) . . ? C15 C16 C17 119.7(2) . . ? C16 C17 C12 121.4(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 31.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.440 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.068