# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_101101_cj101011_1 #TrackingRef 'web_deposit_cif_file_0_jiancao_1349072803.101101_CJ101011_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H31 P' _chemical_formula_sum 'C42 H31 P' _chemical_formula_weight 566.64 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.0368(3) _cell_length_b 30.8934(8) _cell_length_c 10.8177(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.139(4) _cell_angle_gamma 90.00 _cell_volume 3168.85(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5393 _cell_measurement_theta_min 2.6319 _cell_measurement_theta_max 29.3061 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan' _exptl_absorpt_correction_T_min 0.946 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13835 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5789 _reflns_number_gt 4487 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Oxford Diffraction, 2009)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+1.2726P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5789 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.53093(6) 0.155776(17) 0.04826(5) 0.03915(16) Uani 1 1 d . . . C1 C 0.7425(3) 0.03539(8) -0.2914(2) 0.0542(6) Uani 1 1 d . . . H1 H 0.8167 0.0165 -0.2532 0.065 Uiso 1 1 calc R . . C2 C 0.6771(3) 0.03444(9) -0.4226(2) 0.0642(7) Uani 1 1 d . . . H2 H 0.7063 0.0147 -0.4734 0.077 Uiso 1 1 calc R . . C3 C 0.5670(3) 0.06268(9) -0.4819(2) 0.0638(7) Uani 1 1 d . . . H3 H 0.5232 0.0617 -0.5721 0.077 Uiso 1 1 calc R . . C4 C 0.5228(3) 0.09160(8) -0.4094(2) 0.0558(6) Uani 1 1 d . . . H4 H 0.4494 0.1105 -0.4505 0.067 Uiso 1 1 calc R . . C5 C 0.5872(2) 0.09343(7) -0.27192(19) 0.0388(5) Uani 1 1 d . . . C6 C 0.6991(2) 0.06483(6) -0.21161(19) 0.0380(5) Uani 1 1 d . . . C7 C 0.7612(2) 0.06632(7) -0.07479(19) 0.0410(5) Uani 1 1 d . . . H7 H 0.8341 0.0472 -0.0346 0.049 Uiso 1 1 calc R . . C8 C 0.71837(19) 0.09483(6) 0.00156(18) 0.0336(4) Uani 1 1 d . . . C9 C 0.60098(19) 0.12234(6) -0.05800(18) 0.0331(4) Uani 1 1 d . . . C10 C 0.5406(2) 0.12125(7) -0.19134(19) 0.0413(5) Uani 1 1 d . . . H10 H 0.4654 0.1397 -0.2305 0.050 Uiso 1 1 calc R . . C11 C 0.7943(2) 0.09408(6) 0.14657(19) 0.0378(5) Uani 1 1 d . . . C12 C 0.7871(2) 0.05187(6) 0.21175(19) 0.0374(5) Uani 1 1 d . . . C13 C 0.6580(2) 0.03156(7) 0.1861(2) 0.0492(5) Uani 1 1 d . . . H13 H 0.5770 0.0450 0.1317 0.059 Uiso 1 1 calc R . . C14 C 0.6472(3) -0.00810(7) 0.2398(3) 0.0580(6) Uani 1 1 d . . . H14 H 0.5592 -0.0209 0.2233 0.070 Uiso 1 1 calc R . . C15 C 0.7652(3) -0.02879(7) 0.3171(2) 0.0562(6) Uani 1 1 d . . . H15 H 0.7576 -0.0556 0.3530 0.067 Uiso 1 1 calc R . . C16 C 0.8947(3) -0.01000(7) 0.3416(2) 0.0516(6) Uani 1 1 d . . . H16 H 0.9752 -0.0245 0.3926 0.062 Uiso 1 1 calc R . . C17 C 0.9064(2) 0.03033(7) 0.2911(2) 0.0434(5) Uani 1 1 d . . . H17 H 0.9946 0.0432 0.3102 0.052 Uiso 1 1 calc R . . C18 C 0.8657(2) 0.12853(7) 0.2089(2) 0.0406(5) Uani 1 1 d . . . C19 C 0.9293(2) 0.13151(6) 0.3553(2) 0.0413(5) Uani 1 1 d . . . C20 C 0.8508(3) 0.12153(8) 0.4356(2) 0.0606(7) Uani 1 1 d . . . H20 H 0.7592 0.1113 0.3984 0.073 Uiso 1 1 calc R . . C21 C 0.9055(4) 0.12644(9) 0.5687(3) 0.0772(9) Uani 1 1 d . . . H21 H 0.8511 0.1196 0.6210 0.093 Uiso 1 1 calc R . . C22 C 1.0386(4) 0.14118(9) 0.6236(3) 0.0782(9) Uani 1 1 d . . . H22 H 1.0759 0.1437 0.7141 0.094 Uiso 1 1 calc R . . C23 C 1.1202(3) 0.15253(9) 0.5481(3) 0.0742(9) Uani 1 1 d . . . H23 H 1.2108 0.1634 0.5868 0.089 Uiso 1 1 calc R . . C24 C 1.0641(2) 0.14742(7) 0.4115(2) 0.0557(6) Uani 1 1 d . . . H24 H 1.1179 0.1548 0.3590 0.067 Uiso 1 1 calc R . . C25 C 0.8811(2) 0.16880(7) 0.1368(2) 0.0422(5) Uani 1 1 d . . . C26 C 0.8467(3) 0.20849(7) 0.1780(2) 0.0544(6) Uani 1 1 d . . . H26 H 0.8120 0.2097 0.2478 0.065 Uiso 1 1 calc R . . C27 C 0.8634(3) 0.24631(8) 0.1164(3) 0.0757(9) Uani 1 1 d . . . H27 H 0.8399 0.2728 0.1448 0.091 Uiso 1 1 calc R . . C28 C 0.9144(3) 0.24489(11) 0.0134(3) 0.0842(10) Uani 1 1 d . . . H28 H 0.9263 0.2703 -0.0277 0.101 Uiso 1 1 calc R . . C29 C 0.9476(3) 0.20617(11) -0.0285(3) 0.0777(9) Uani 1 1 d . . . H29 H 0.9810 0.2053 -0.0991 0.093 Uiso 1 1 calc R . . C30 C 0.9323(2) 0.16800(9) 0.0325(2) 0.0561(6) Uani 1 1 d . . . H30 H 0.9565 0.1418 0.0035 0.067 Uiso 1 1 calc R . . C31 C 0.3874(2) 0.12128(6) 0.0616(2) 0.0402(5) Uani 1 1 d . . . C32 C 0.2958(3) 0.09791(8) -0.0398(2) 0.0570(6) Uani 1 1 d . . . H32 H 0.3050 0.0995 -0.1225 0.068 Uiso 1 1 calc R . . C33 C 0.1913(3) 0.07241(9) -0.0216(3) 0.0703(7) Uani 1 1 d . . . H33 H 0.1310 0.0570 -0.0915 0.084 Uiso 1 1 calc R . . C34 C 0.1761(3) 0.06978(9) 0.0994(3) 0.0652(7) Uani 1 1 d . . . H34 H 0.1055 0.0526 0.1119 0.078 Uiso 1 1 calc R . . C35 C 0.2651(3) 0.09244(9) 0.2015(3) 0.0678(7) Uani 1 1 d . . . H35 H 0.2550 0.0907 0.2838 0.081 Uiso 1 1 calc R . . C36 C 0.3705(3) 0.11798(8) 0.1834(2) 0.0534(6) Uani 1 1 d . . . H36 H 0.4308 0.1331 0.2539 0.064 Uiso 1 1 calc R . . C37 C 0.4376(2) 0.19828(6) -0.0653(2) 0.0403(5) Uani 1 1 d . . . C38 C 0.5124(3) 0.22310(8) -0.1266(3) 0.0649(7) Uani 1 1 d . . . H38 H 0.6062 0.2165 -0.1146 0.078 Uiso 1 1 calc R . . C39 C 0.4494(3) 0.25746(9) -0.2051(3) 0.0835(9) Uani 1 1 d . . . H39 H 0.5008 0.2738 -0.2460 0.100 Uiso 1 1 calc R . . C40 C 0.3118(3) 0.26775(9) -0.2233(3) 0.0776(8) Uani 1 1 d . . . H40 H 0.2692 0.2908 -0.2771 0.093 Uiso 1 1 calc R . . C41 C 0.2382(3) 0.24417(9) -0.1626(3) 0.0738(8) Uani 1 1 d . . . H41 H 0.1449 0.2513 -0.1742 0.089 Uiso 1 1 calc R . . C42 C 0.3002(2) 0.20955(7) -0.0833(2) 0.0549(6) Uani 1 1 d . . . H42 H 0.2483 0.1938 -0.0419 0.066 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 0.0437(3) 0.0383(3) 0.0345(3) -0.0023(2) 0.0115(2) 0.0056(2) C1 0.0676(15) 0.0504(13) 0.0502(14) -0.0036(11) 0.0269(12) 0.0093(12) C2 0.0865(19) 0.0664(16) 0.0482(15) -0.0188(13) 0.0336(14) -0.0038(15) C3 0.0699(17) 0.0861(19) 0.0345(13) -0.0119(13) 0.0160(12) -0.0052(15) C4 0.0544(14) 0.0772(17) 0.0330(12) 0.0001(11) 0.0106(10) 0.0047(12) C5 0.0394(11) 0.0460(11) 0.0319(11) -0.0009(9) 0.0128(9) -0.0039(9) C6 0.0435(11) 0.0369(11) 0.0369(11) -0.0012(9) 0.0176(9) -0.0030(9) C7 0.0409(11) 0.0426(11) 0.0385(12) 0.0048(9) 0.0119(9) 0.0087(9) C8 0.0331(10) 0.0357(10) 0.0314(10) 0.0016(8) 0.0097(8) -0.0010(8) C9 0.0331(10) 0.0338(10) 0.0314(10) 0.0000(8) 0.0092(8) -0.0012(8) C10 0.0378(11) 0.0489(12) 0.0341(11) 0.0042(9) 0.0075(9) 0.0081(9) C11 0.0354(10) 0.0405(11) 0.0364(11) 0.0019(9) 0.0103(9) 0.0040(9) C12 0.0485(12) 0.0314(10) 0.0348(11) 0.0007(8) 0.0173(9) 0.0030(9) C13 0.0468(13) 0.0471(13) 0.0525(14) 0.0062(11) 0.0145(11) 0.0021(10) C14 0.0685(16) 0.0440(13) 0.0674(16) 0.0007(12) 0.0304(13) -0.0119(12) C15 0.094(2) 0.0332(11) 0.0488(14) 0.0040(10) 0.0334(14) 0.0006(13) C16 0.0715(16) 0.0416(12) 0.0359(12) 0.0048(10) 0.0096(11) 0.0162(12) C17 0.0493(12) 0.0391(11) 0.0382(11) -0.0023(9) 0.0094(10) 0.0015(10) C18 0.0382(11) 0.0411(11) 0.0421(12) 0.0010(9) 0.0125(9) -0.0005(9) C19 0.0517(12) 0.0327(10) 0.0348(11) -0.0020(9) 0.0077(10) -0.0027(9) C20 0.0860(18) 0.0510(14) 0.0478(14) -0.0060(11) 0.0257(13) -0.0150(13) C21 0.126(3) 0.0604(17) 0.0453(16) -0.0013(13) 0.0277(17) -0.0102(17) C22 0.119(3) 0.0612(17) 0.0371(14) -0.0020(13) 0.0021(17) 0.0183(18) C23 0.0646(17) 0.0615(17) 0.0668(19) -0.0144(14) -0.0189(15) 0.0114(13) C24 0.0474(13) 0.0508(13) 0.0560(15) -0.0047(11) -0.0006(11) 0.0019(11) C25 0.0413(11) 0.0398(11) 0.0407(12) 0.0045(9) 0.0068(9) -0.0103(9) C26 0.0668(15) 0.0404(12) 0.0455(13) 0.0010(10) 0.0043(11) -0.0078(11) C27 0.094(2) 0.0403(14) 0.0686(19) 0.0049(13) -0.0064(16) -0.0190(14) C28 0.087(2) 0.069(2) 0.074(2) 0.0325(17) -0.0043(17) -0.0359(17) C29 0.0647(17) 0.103(3) 0.0617(18) 0.0273(17) 0.0157(14) -0.0275(17) C30 0.0478(13) 0.0683(16) 0.0513(14) 0.0063(12) 0.0150(11) -0.0120(12) C31 0.0492(12) 0.0359(11) 0.0377(12) 0.0043(9) 0.0175(10) 0.0111(9) C32 0.0680(16) 0.0636(15) 0.0454(14) -0.0087(12) 0.0268(12) -0.0144(13) C33 0.0771(18) 0.0731(18) 0.0653(18) -0.0109(14) 0.0299(15) -0.0239(15) C34 0.0655(16) 0.0628(16) 0.0751(19) 0.0141(14) 0.0336(15) -0.0019(13) C35 0.0773(18) 0.0824(19) 0.0560(16) 0.0176(14) 0.0386(15) 0.0060(16) C36 0.0623(15) 0.0610(15) 0.0392(13) 0.0035(11) 0.0197(11) 0.0076(12) C37 0.0419(11) 0.0351(10) 0.0427(12) -0.0017(9) 0.0125(9) 0.0009(9) C38 0.0523(14) 0.0591(15) 0.088(2) 0.0207(14) 0.0292(14) 0.0066(12) C39 0.081(2) 0.0673(18) 0.112(3) 0.0413(17) 0.0454(19) 0.0068(16) C40 0.0763(19) 0.0587(16) 0.094(2) 0.0343(16) 0.0229(17) 0.0161(15) C41 0.0525(15) 0.0635(16) 0.103(2) 0.0308(16) 0.0226(15) 0.0146(13) C42 0.0472(13) 0.0490(13) 0.0693(16) 0.0141(12) 0.0203(12) 0.0056(11) _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 C37 1.832(2) . ? P1 C31 1.835(2) . ? P1 C9 1.8473(19) . ? C1 C2 1.354(3) . ? C1 C6 1.417(3) . ? C1 H1 0.9300 . ? C2 C3 1.389(4) . ? C2 H2 0.9300 . ? C3 C4 1.355(3) . ? C3 H3 0.9300 . ? C4 C5 1.415(3) . ? C4 H4 0.9300 . ? C5 C10 1.409(3) . ? C5 C6 1.410(3) . ? C6 C7 1.406(3) . ? C7 C8 1.369(3) . ? C7 H7 0.9300 . ? C8 C9 1.424(3) . ? C8 C11 1.503(3) . ? C9 C10 1.370(3) . ? C10 H10 0.9300 . ? C11 C18 1.336(3) . ? C11 C12 1.495(3) . ? C12 C13 1.384(3) . ? C12 C17 1.393(3) . ? C13 C14 1.375(3) . ? C13 H13 0.9300 . ? C14 C15 1.364(3) . ? C14 H14 0.9300 . ? C15 C16 1.367(3) . ? C15 H15 0.9300 . ? C16 C17 1.381(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.503(3) . ? C18 C25 1.504(3) . ? C19 C24 1.380(3) . ? C19 C20 1.384(3) . ? C20 C21 1.371(4) . ? C20 H20 0.9300 . ? C21 C22 1.351(4) . ? C21 H21 0.9300 . ? C22 C23 1.379(4) . ? C22 H22 0.9300 . ? C23 C24 1.407(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C30 1.384(3) . ? C25 C26 1.387(3) . ? C26 C27 1.382(3) . ? C26 H26 0.9300 . ? C27 C28 1.371(4) . ? C27 H27 0.9300 . ? C28 C29 1.358(4) . ? C28 H28 0.9300 . ? C29 C30 1.384(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C32 1.382(3) . ? C31 C36 1.386(3) . ? C32 C33 1.377(3) . ? C32 H32 0.9300 . ? C33 C34 1.369(4) . ? C33 H33 0.9300 . ? C34 C35 1.365(4) . ? C34 H34 0.9300 . ? C35 C36 1.384(4) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C42 1.373(3) . ? C37 C38 1.384(3) . ? C38 C39 1.377(4) . ? C38 H38 0.9300 . ? C39 C40 1.367(4) . ? C39 H39 0.9300 . ? C40 C41 1.351(4) . ? C40 H40 0.9300 . ? C41 C42 1.384(3) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? 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 C37 P1 C31 103.14(9) . . ? C37 P1 C9 101.47(9) . . ? C31 P1 C9 101.13(9) . . ? C2 C1 C6 120.8(2) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C1 C2 C3 120.6(2) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.6(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.7(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C10 C5 C6 118.15(18) . . ? C10 C5 C4 123.03(19) . . ? C6 C5 C4 118.76(19) . . ? C7 C6 C5 118.53(17) . . ? C7 C6 C1 122.94(19) . . ? C5 C6 C1 118.52(19) . . ? C8 C7 C6 122.52(18) . . ? C8 C7 H7 118.7 . . ? C6 C7 H7 118.7 . . ? C7 C8 C9 119.19(17) . . ? C7 C8 C11 117.87(17) . . ? C9 C8 C11 122.88(16) . . ? C10 C9 C8 118.47(17) . . ? C10 C9 P1 122.80(15) . . ? C8 C9 P1 118.65(14) . . ? C9 C10 C5 122.99(18) . . ? C9 C10 H10 118.5 . . ? C5 C10 H10 118.5 . . ? C18 C11 C12 123.89(18) . . ? C18 C11 C8 121.30(18) . . ? C12 C11 C8 114.78(16) . . ? C13 C12 C17 117.80(18) . . ? C13 C12 C11 119.23(18) . . ? C17 C12 C11 122.83(18) . . ? C14 C13 C12 121.2(2) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C13 120.3(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.9(2) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 120.3(2) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C12 120.5(2) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? C11 C18 C19 123.58(18) . . ? C11 C18 C25 121.77(18) . . ? C19 C18 C25 114.56(17) . . ? C24 C19 C20 118.7(2) . . ? C24 C19 C18 120.1(2) . . ? C20 C19 C18 121.0(2) . . ? C21 C20 C19 121.3(3) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C22 C21 C20 119.8(3) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 121.3(3) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C22 C23 C24 118.9(3) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C19 C24 C23 120.0(3) . . ? C19 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C30 C25 C26 118.4(2) . . ? C30 C25 C18 122.5(2) . . ? C26 C25 C18 119.03(19) . . ? C27 C26 C25 120.6(3) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C28 C27 C26 120.1(3) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C29 C28 C27 119.8(3) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C30 120.9(3) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? C29 C30 C25 120.1(3) . . ? C29 C30 H30 119.9 . . ? C25 C30 H30 119.9 . . ? C32 C31 C36 117.4(2) . . ? C32 C31 P1 125.15(16) . . ? C36 C31 P1 117.48(17) . . ? C33 C32 C31 121.7(2) . . ? C33 C32 H32 119.2 . . ? C31 C32 H32 119.2 . . ? C34 C33 C32 120.0(3) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C35 C34 C33 119.7(2) . . ? C35 C34 H34 120.2 . . ? C33 C34 H34 120.2 . . ? C34 C35 C36 120.4(2) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C35 C36 C31 120.9(2) . . ? C35 C36 H36 119.5 . . ? C31 C36 H36 119.5 . . ? C42 C37 C38 117.9(2) . . ? C42 C37 P1 123.10(16) . . ? C38 C37 P1 118.68(16) . . ? C39 C38 C37 120.7(2) . . ? C39 C38 H38 119.6 . . ? C37 C38 H38 119.6 . . ? C40 C39 C38 120.4(3) . . ? C40 C39 H39 119.8 . . ? C38 C39 H39 119.8 . . ? C41 C40 C39 119.5(2) . . ? C41 C40 H40 120.3 . . ? C39 C40 H40 120.3 . . ? C40 C41 C42 120.8(2) . . ? C40 C41 H41 119.6 . . ? C42 C41 H41 119.6 . . ? C37 C42 C41 120.7(2) . . ? C37 C42 H42 119.6 . . ? C41 C42 H42 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.7(4) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C3 C4 C5 C10 -176.6(2) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C10 C5 C6 C7 -1.8(3) . . . . ? C4 C5 C6 C7 -179.03(19) . . . . ? C10 C5 C6 C1 177.23(19) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C2 C1 C6 C7 178.4(2) . . . . ? C2 C1 C6 C5 -0.6(3) . . . . ? C5 C6 C7 C8 -0.9(3) . . . . ? C1 C6 C7 C8 -179.9(2) . . . . ? C6 C7 C8 C9 3.9(3) . . . . ? C6 C7 C8 C11 -178.83(18) . . . . ? C7 C8 C9 C10 -4.2(3) . . . . ? C11 C8 C9 C10 178.74(18) . . . . ? C7 C8 C9 P1 172.63(15) . . . . ? C11 C8 C9 P1 -4.4(2) . . . . ? C37 P1 C9 C10 -24.67(18) . . . . ? C31 P1 C9 C10 81.37(18) . . . . ? C37 P1 C9 C8 158.67(15) . . . . ? C31 P1 C9 C8 -95.29(16) . . . . ? C8 C9 C10 C5 1.5(3) . . . . ? P1 C9 C10 C5 -175.13(16) . . . . ? C6 C5 C10 C9 1.4(3) . . . . ? C4 C5 C10 C9 178.6(2) . . . . ? C7 C8 C11 C18 117.8(2) . . . . ? C9 C8 C11 C18 -65.1(3) . . . . ? C7 C8 C11 C12 -60.2(2) . . . . ? C9 C8 C11 C12 116.9(2) . . . . ? C18 C11 C12 C13 133.9(2) . . . . ? C8 C11 C12 C13 -48.2(2) . . . . ? C18 C11 C12 C17 -50.6(3) . . . . ? C8 C11 C12 C17 127.4(2) . . . . ? C17 C12 C13 C14 1.6(3) . . . . ? C11 C12 C13 C14 177.3(2) . . . . ? C12 C13 C14 C15 -1.7(4) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C14 C15 C16 C17 1.5(3) . . . . ? C15 C16 C17 C12 -1.7(3) . . . . ? C13 C12 C17 C16 0.1(3) . . . . ? C11 C12 C17 C16 -175.48(19) . . . . ? C12 C11 C18 C19 -9.6(3) . . . . ? C8 C11 C18 C19 172.63(18) . . . . ? C12 C11 C18 C25 174.07(18) . . . . ? C8 C11 C18 C25 -3.8(3) . . . . ? C11 C18 C19 C24 135.6(2) . . . . ? C25 C18 C19 C24 -47.8(3) . . . . ? C11 C18 C19 C20 -49.3(3) . . . . ? C25 C18 C19 C20 127.3(2) . . . . ? C24 C19 C20 C21 -1.2(4) . . . . ? C18 C19 C20 C21 -176.4(2) . . . . ? C19 C20 C21 C22 -0.2(4) . . . . ? C20 C21 C22 C23 1.7(4) . . . . ? C21 C22 C23 C24 -1.7(4) . . . . ? C20 C19 C24 C23 1.1(3) . . . . ? C18 C19 C24 C23 176.3(2) . . . . ? C22 C23 C24 C19 0.3(4) . . . . ? C11 C18 C25 C30 -53.3(3) . . . . ? C19 C18 C25 C30 130.0(2) . . . . ? C11 C18 C25 C26 128.5(2) . . . . ? C19 C18 C25 C26 -48.2(3) . . . . ? C30 C25 C26 C27 -0.1(3) . . . . ? C18 C25 C26 C27 178.2(2) . . . . ? C25 C26 C27 C28 0.0(4) . . . . ? C26 C27 C28 C29 0.5(4) . . . . ? C27 C28 C29 C30 -0.8(4) . . . . ? C28 C29 C30 C25 0.8(4) . . . . ? C26 C25 C30 C29 -0.3(3) . . . . ? C18 C25 C30 C29 -178.5(2) . . . . ? C37 P1 C31 C32 63.9(2) . . . . ? C9 P1 C31 C32 -40.8(2) . . . . ? C37 P1 C31 C36 -116.84(17) . . . . ? C9 P1 C31 C36 138.44(17) . . . . ? C36 C31 C32 C33 0.2(4) . . . . ? P1 C31 C32 C33 179.4(2) . . . . ? C31 C32 C33 C34 0.1(4) . . . . ? C32 C33 C34 C35 -0.1(4) . . . . ? C33 C34 C35 C36 -0.1(4) . . . . ? C34 C35 C36 C31 0.4(4) . . . . ? C32 C31 C36 C35 -0.4(3) . . . . ? P1 C31 C36 C35 -179.70(19) . . . . ? C31 P1 C37 C42 24.3(2) . . . . ? C9 P1 C37 C42 128.78(19) . . . . ? C31 P1 C37 C38 -162.07(19) . . . . ? C9 P1 C37 C38 -57.6(2) . . . . ? C42 C37 C38 C39 -1.2(4) . . . . ? P1 C37 C38 C39 -175.2(2) . . . . ? C37 C38 C39 C40 0.3(5) . . . . ? C38 C39 C40 C41 0.7(5) . . . . ? C39 C40 C41 C42 -0.6(5) . . . . ? C38 C37 C42 C41 1.3(4) . . . . ? P1 C37 C42 C41 174.9(2) . . . . ? C40 C41 C42 C37 -0.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.604 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 903816' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_121224_cj121116_1 #TrackingRef 'web_deposit_cif_file_0_caojian_1356709083.121224_cj121116_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H29 P' _chemical_formula_sum 'C37 H29 P' _chemical_formula_weight 504.57 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.8232(11) _cell_length_b 30.276(2) _cell_length_c 10.9053(19) _cell_angle_alpha 90.00 _cell_angle_beta 120.527(9) _cell_angle_gamma 90.00 _cell_volume 2793.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2439 _cell_measurement_theta_min 3.3577 _cell_measurement_theta_max 29.5793 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9471 _exptl_absorpt_correction_T_max 0.9573 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11860 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5090 _reflns_number_gt 3274 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0880P)^2^+1.9506P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5090 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1220 _refine_ls_R_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.2221 _refine_ls_wR_factor_gt 0.1938 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.65669(11) 0.06913(3) 0.29928(10) 0.0569(3) Uani 1 1 d . . . C1 C 0.0929(6) 0.15983(17) -0.1948(5) 0.0904(14) Uani 1 1 d . . . H1 H 0.0926 0.1903 -0.2049 0.108 Uiso 1 1 calc R . . C2 C -0.0331(5) 0.1358(2) -0.2891(5) 0.0935(15) Uani 1 1 d . . . H2 H -0.1191 0.1499 -0.3642 0.112 Uiso 1 1 calc R . . C3 C -0.0356(5) 0.09064(19) -0.2750(4) 0.0834(13) Uani 1 1 d . . . H3 H -0.1224 0.0745 -0.3416 0.100 Uiso 1 1 calc R . . C4 C 0.0874(4) 0.06951(15) -0.1650(4) 0.0677(10) Uani 1 1 d . . . H4 H 0.0826 0.0391 -0.1553 0.081 Uiso 1 1 calc R . . C5 C 0.2225(4) 0.09304(12) -0.0651(3) 0.0524(9) Uani 1 1 d . . . C6 C 0.2255(4) 0.13879(14) -0.0805(4) 0.0640(10) Uani 1 1 d . . . C7 C 0.3646(5) 0.16221(14) 0.0158(4) 0.0779(12) Uani 1 1 d . . . H7 H 0.3679 0.1926 0.0054 0.093 Uiso 1 1 calc R . . C8 C 0.4952(4) 0.14133(12) 0.1244(4) 0.0616(10) Uani 1 1 d . . . C9 C 0.4905(4) 0.09473(11) 0.1417(3) 0.0506(8) Uani 1 1 d . . . C10 C 0.3572(4) 0.07222(11) 0.0483(3) 0.0489(8) Uani 1 1 d . . . H10 H 0.3545 0.0418 0.0593 0.059 Uiso 1 1 calc R . . C11 C 0.5848(4) 0.01316(12) 0.2923(3) 0.0542(9) Uani 1 1 d . . . C12 C 0.4689(5) 0.00694(16) 0.3274(4) 0.0785(12) Uani 1 1 d . . . H12 H 0.4277 0.0314 0.3491 0.094 Uiso 1 1 calc R . . C13 C 0.4136(6) -0.0341(2) 0.3309(6) 0.0975(16) Uani 1 1 d . . . H13 H 0.3347 -0.0373 0.3535 0.117 Uiso 1 1 calc R . . C14 C 0.4746(7) -0.07085(18) 0.3010(5) 0.0931(16) Uani 1 1 d . . . H14 H 0.4369 -0.0989 0.3029 0.112 Uiso 1 1 calc R . . C15 C 0.5903(6) -0.06576(15) 0.2687(5) 0.0856(13) Uani 1 1 d . . . H15 H 0.6329 -0.0904 0.2497 0.103 Uiso 1 1 calc R . . C16 C 0.6448(5) -0.02420(13) 0.2639(4) 0.0672(10) Uani 1 1 d . . . H16 H 0.7236 -0.0213 0.2410 0.081 Uiso 1 1 calc R . . C17 C 0.8051(4) 0.06175(11) 0.2480(4) 0.0539(9) Uani 1 1 d . . . C18 C 0.7722(5) 0.05901(14) 0.1086(4) 0.0700(11) Uani 1 1 d . . . H18 H 0.6677 0.0600 0.0345 0.084 Uiso 1 1 calc R . . C19 C 0.8918(6) 0.05482(16) 0.0778(5) 0.0839(13) Uani 1 1 d . . . H19 H 0.8677 0.0539 -0.0164 0.101 Uiso 1 1 calc R . . C20 C 1.0440(6) 0.05210(17) 0.1847(6) 0.0876(14) Uani 1 1 d . . . H20 H 1.1244 0.0491 0.1640 0.105 Uiso 1 1 calc R . . C21 C 1.0799(5) 0.05376(17) 0.3237(6) 0.0925(15) Uani 1 1 d . . . H21 H 1.1844 0.0513 0.3971 0.111 Uiso 1 1 calc R . . C22 C 0.9618(4) 0.05902(14) 0.3547(4) 0.0737(11) Uani 1 1 d . . . H22 H 0.9877 0.0608 0.4493 0.088 Uiso 1 1 calc R . . C23 C 0.6384(5) 0.16885(13) 0.2194(4) 0.0687(11) Uani 1 1 d . . . C24 C 0.7496(5) 0.17788(13) 0.1700(5) 0.0764(12) Uani 1 1 d . . . C25 C 0.7122(7) 0.16808(17) 0.0322(6) 0.0991(15) Uani 1 1 d . . . H25 H 0.6158 0.1547 -0.0291 0.119 Uiso 1 1 calc R . . C26 C 0.8130(9) 0.1776(2) -0.0164(7) 0.121(2) Uani 1 1 d . . . H26 H 0.7835 0.1704 -0.1096 0.145 Uiso 1 1 calc R . . C27 C 0.9524(8) 0.1968(2) 0.0668(9) 0.1154(19) Uani 1 1 d . . . H27 H 1.0197 0.2029 0.0324 0.138 Uiso 1 1 calc R . . C28 C 0.9951(6) 0.20767(19) 0.2044(8) 0.1105(19) Uani 1 1 d . . . H28 H 1.0916 0.2215 0.2626 0.133 Uiso 1 1 calc R . . C29 C 0.8964(5) 0.19823(17) 0.2575(6) 0.0946(15) Uani 1 1 d . . . H29 H 0.9275 0.2054 0.3511 0.114 Uiso 1 1 calc R . . C30 C 0.6580(5) 0.18717(12) 0.3371(4) 0.0689(11) Uani 1 1 d . . . H30 H 0.7491 0.2042 0.3856 0.083 Uiso 1 1 calc R . . C31 C 0.5592(5) 0.18554(13) 0.4074(4) 0.0711(11) Uani 1 1 d . . . C32 C 0.4304(6) 0.15951(15) 0.3713(5) 0.0832(13) Uani 1 1 d . . . H32 H 0.3978 0.1398 0.2960 0.100 Uiso 1 1 calc R . . C33 C 0.3468(6) 0.16102(16) 0.4410(5) 0.0925(14) Uani 1 1 d . . . H33 H 0.2587 0.1431 0.4113 0.111 Uiso 1 1 calc R . . C34 C 0.3944(7) 0.18975(17) 0.5573(5) 0.0906(15) Uani 1 1 d . . . C35 C 0.5246(7) 0.21478(16) 0.5957(5) 0.0973(16) Uani 1 1 d . . . H35 H 0.5608 0.2337 0.6733 0.117 Uiso 1 1 calc R . . C36 C 0.6041(6) 0.21280(14) 0.5226(5) 0.0884(14) Uani 1 1 d . . . H36 H 0.6923 0.2307 0.5522 0.106 Uiso 1 1 calc R . . C37 C 0.3034(8) 0.1926(2) 0.6310(6) 0.132(2) Uani 1 1 d . . . H37A H 0.2599 0.2217 0.6194 0.197 Uiso 1 1 calc R . . H37B H 0.3719 0.1866 0.7305 0.197 Uiso 1 1 calc R . . H37C H 0.2192 0.1713 0.5910 0.197 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 0.0496(6) 0.0621(6) 0.0448(5) 0.0043(4) 0.0135(4) 0.0101(4) C1 0.075(3) 0.095(3) 0.075(3) 0.024(3) 0.019(3) 0.025(3) C2 0.055(3) 0.134(5) 0.059(3) 0.023(3) 0.005(2) 0.021(3) C3 0.046(2) 0.132(4) 0.056(2) 0.008(3) 0.014(2) -0.004(2) C4 0.050(2) 0.089(3) 0.055(2) -0.004(2) 0.0210(19) -0.004(2) C5 0.0429(19) 0.072(2) 0.0394(17) 0.0003(17) 0.0187(15) 0.0081(16) C6 0.053(2) 0.075(3) 0.049(2) 0.0038(19) 0.0143(18) 0.0144(19) C7 0.078(3) 0.057(2) 0.071(3) 0.007(2) 0.018(2) 0.013(2) C8 0.059(2) 0.059(2) 0.051(2) 0.0001(18) 0.0167(18) 0.0079(17) C9 0.0453(19) 0.054(2) 0.0427(18) -0.0023(15) 0.0151(16) 0.0069(15) C10 0.0451(19) 0.0512(19) 0.0463(18) 0.0002(16) 0.0203(16) 0.0064(15) C11 0.0464(19) 0.069(2) 0.0383(17) 0.0104(16) 0.0150(15) 0.0119(17) C12 0.066(3) 0.101(3) 0.075(3) 0.017(2) 0.041(2) 0.008(2) C13 0.072(3) 0.125(5) 0.099(4) 0.022(3) 0.046(3) -0.013(3) C14 0.098(4) 0.091(4) 0.066(3) 0.016(3) 0.024(3) -0.029(3) C15 0.106(4) 0.067(3) 0.081(3) 0.004(2) 0.045(3) -0.001(3) C16 0.072(3) 0.066(3) 0.069(3) 0.009(2) 0.040(2) 0.004(2) C17 0.047(2) 0.052(2) 0.051(2) 0.0035(16) 0.0162(16) -0.0011(15) C18 0.055(2) 0.090(3) 0.051(2) 0.012(2) 0.0167(19) 0.009(2) C19 0.076(3) 0.117(4) 0.069(3) 0.017(3) 0.044(3) 0.015(3) C20 0.065(3) 0.109(4) 0.097(4) 0.012(3) 0.048(3) 0.000(2) C21 0.042(2) 0.132(4) 0.089(3) -0.004(3) 0.022(2) -0.009(2) C22 0.049(2) 0.094(3) 0.055(2) -0.003(2) 0.0091(19) -0.004(2) C23 0.068(3) 0.056(2) 0.062(2) 0.007(2) 0.019(2) 0.0008(18) C24 0.067(3) 0.057(2) 0.096(3) 0.022(2) 0.034(3) 0.006(2) C25 0.099(4) 0.100(4) 0.089(4) -0.003(3) 0.041(3) -0.018(3) C26 0.138(6) 0.126(5) 0.116(5) 0.002(4) 0.077(5) -0.007(4) C27 0.100(5) 0.095(4) 0.143(6) 0.017(4) 0.055(4) 0.003(3) C28 0.070(3) 0.101(4) 0.141(6) 0.010(4) 0.039(4) -0.006(3) C29 0.060(3) 0.106(4) 0.100(4) 0.007(3) 0.028(3) 0.000(3) C30 0.076(3) 0.051(2) 0.055(2) -0.0035(18) 0.015(2) -0.0038(19) C31 0.081(3) 0.051(2) 0.056(2) -0.0011(19) 0.016(2) 0.009(2) C32 0.090(3) 0.079(3) 0.073(3) -0.018(2) 0.036(3) 0.008(3) C33 0.084(3) 0.084(3) 0.093(3) -0.004(3) 0.033(3) 0.006(3) C34 0.117(4) 0.077(3) 0.080(3) 0.000(3) 0.053(3) 0.028(3) C35 0.135(5) 0.071(3) 0.073(3) -0.015(2) 0.043(3) 0.002(3) C36 0.117(4) 0.066(3) 0.066(3) -0.013(2) 0.035(3) -0.003(3) C37 0.177(6) 0.127(5) 0.107(4) 0.010(4) 0.084(5) 0.035(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 C17 1.821(4) . ? P1 C11 1.822(4) . ? P1 C9 1.835(3) . ? C1 C2 1.351(6) . ? C1 C6 1.417(5) . ? C1 H1 0.9300 . ? C2 C3 1.378(7) . ? C2 H2 0.9300 . ? C3 C4 1.355(6) . ? C3 H3 0.9300 . ? C4 C5 1.410(5) . ? C4 H4 0.9300 . ? C5 C6 1.398(5) . ? C5 C10 1.419(4) . ? C6 C7 1.419(5) . ? C7 C8 1.380(5) . ? C7 H7 0.9300 . ? C8 C9 1.427(5) . ? C8 C23 1.505(5) . ? C9 C10 1.364(4) . ? C10 H10 0.9300 . ? C11 C16 1.381(5) . ? C11 C12 1.387(5) . ? C12 C13 1.364(7) . ? C12 H12 0.9300 . ? C13 C14 1.380(7) . ? C13 H13 0.9300 . ? C14 C15 1.358(7) . ? C14 H14 0.9300 . ? C15 C16 1.379(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C22 1.382(5) . ? C17 C18 1.387(5) . ? C18 C19 1.382(6) . ? C18 H18 0.9300 . ? C19 C20 1.353(6) . ? C19 H19 0.9300 . ? C20 C21 1.372(6) . ? C20 H20 0.9300 . ? C21 C22 1.372(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C30 1.320(5) . ? C23 C24 1.469(6) . ? C24 C25 1.385(7) . ? C24 C29 1.404(6) . ? C25 C26 1.370(7) . ? C25 H25 0.9300 . ? C26 C27 1.333(8) . ? C26 H26 0.9300 . ? C27 C28 1.377(8) . ? C27 H27 0.9300 . ? C28 C29 1.389(7) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 C31 1.512(6) . ? C30 H30 0.9300 . ? C31 C32 1.368(6) . ? C31 C36 1.375(6) . ? C32 C33 1.373(6) . ? C32 H32 0.9300 . ? C33 C34 1.407(7) . ? C33 H33 0.9300 . ? C34 C35 1.357(7) . ? C34 C37 1.478(7) . ? C35 C36 1.372(7) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? 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 C17 P1 C11 103.08(16) . . ? C17 P1 C9 103.58(16) . . ? C11 P1 C9 102.24(15) . . ? C2 C1 C6 120.4(5) . . ? C2 C1 H1 119.8 . . ? C6 C1 H1 119.8 . . ? C1 C2 C3 120.7(4) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.6(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.8(4) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 118.5(3) . . ? C6 C5 C10 118.5(3) . . ? C4 C5 C10 123.0(3) . . ? C5 C6 C1 119.0(4) . . ? C5 C6 C7 118.5(3) . . ? C1 C6 C7 122.4(4) . . ? C8 C7 C6 122.1(4) . . ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? C7 C8 C9 119.2(3) . . ? C7 C8 C23 118.3(3) . . ? C9 C8 C23 122.5(3) . . ? C10 C9 C8 118.6(3) . . ? C10 C9 P1 123.2(3) . . ? C8 C9 P1 117.9(2) . . ? C9 C10 C5 123.0(3) . . ? C9 C10 H10 118.5 . . ? C5 C10 H10 118.5 . . ? C16 C11 C12 117.0(4) . . ? C16 C11 P1 124.8(3) . . ? C12 C11 P1 118.0(3) . . ? C13 C12 C11 121.7(5) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 120.1(5) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 119.4(5) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 120.4(5) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 121.4(4) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? C22 C17 C18 117.3(4) . . ? C22 C17 P1 118.2(3) . . ? C18 C17 P1 124.5(3) . . ? C19 C18 C17 121.2(4) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C20 C19 C18 120.0(4) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 120.1(4) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C22 120.1(4) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C17 121.3(4) . . ? C21 C22 H22 119.4 . . ? C17 C22 H22 119.4 . . ? C30 C23 C24 120.7(4) . . ? C30 C23 C8 121.7(4) . . ? C24 C23 C8 117.4(4) . . ? C25 C24 C29 116.6(5) . . ? C25 C24 C23 121.4(4) . . ? C29 C24 C23 122.0(5) . . ? C26 C25 C24 121.9(5) . . ? C26 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? C27 C26 C25 121.5(6) . . ? C27 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? C26 C27 C28 119.0(6) . . ? C26 C27 H27 120.5 . . ? C28 C27 H27 120.5 . . ? C27 C28 C29 121.0(6) . . ? C27 C28 H28 119.5 . . ? C29 C28 H28 119.5 . . ? C28 C29 C24 120.0(5) . . ? C28 C29 H29 120.0 . . ? C24 C29 H29 120.0 . . ? C23 C30 C31 131.7(4) . . ? C23 C30 H30 114.1 . . ? C31 C30 H30 114.1 . . ? C32 C31 C36 115.4(5) . . ? C32 C31 C30 127.7(4) . . ? C36 C31 C30 116.9(4) . . ? C31 C32 C33 123.2(4) . . ? C31 C32 H32 118.4 . . ? C33 C32 H32 118.4 . . ? C32 C33 C34 120.0(5) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 120.0 . . ? C35 C34 C33 117.0(5) . . ? C35 C34 C37 122.4(5) . . ? C33 C34 C37 120.7(6) . . ? C34 C35 C36 121.4(5) . . ? C34 C35 H35 119.3 . . ? C36 C35 H35 119.3 . . ? C35 C36 C31 123.0(5) . . ? C35 C36 H36 118.5 . . ? C31 C36 H36 118.5 . . ? C34 C37 H37A 109.5 . . ? C34 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C34 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.7(8) . . . . ? C1 C2 C3 C4 1.0(7) . . . . ? C2 C3 C4 C5 -2.0(6) . . . . ? C3 C4 C5 C6 1.2(5) . . . . ? C3 C4 C5 C10 -177.1(3) . . . . ? C4 C5 C6 C1 0.5(5) . . . . ? C10 C5 C6 C1 178.9(4) . . . . ? C4 C5 C6 C7 -176.9(4) . . . . ? C10 C5 C6 C7 1.5(5) . . . . ? C2 C1 C6 C5 -1.4(7) . . . . ? C2 C1 C6 C7 175.9(4) . . . . ? C5 C6 C7 C8 -0.8(6) . . . . ? C1 C6 C7 C8 -178.1(4) . . . . ? C6 C7 C8 C9 -0.5(6) . . . . ? C6 C7 C8 C23 178.8(4) . . . . ? C7 C8 C9 C10 1.1(5) . . . . ? C23 C8 C9 C10 -178.2(3) . . . . ? C7 C8 C9 P1 -173.0(3) . . . . ? C23 C8 C9 P1 7.7(5) . . . . ? C17 P1 C9 C10 103.8(3) . . . . ? C11 P1 C9 C10 -3.1(3) . . . . ? C17 P1 C9 C8 -82.4(3) . . . . ? C11 P1 C9 C8 170.7(3) . . . . ? C8 C9 C10 C5 -0.4(5) . . . . ? P1 C9 C10 C5 173.4(2) . . . . ? C6 C5 C10 C9 -0.9(5) . . . . ? C4 C5 C10 C9 177.4(3) . . . . ? C17 P1 C11 C16 4.1(3) . . . . ? C9 P1 C11 C16 111.4(3) . . . . ? C17 P1 C11 C12 179.5(3) . . . . ? C9 P1 C11 C12 -73.2(3) . . . . ? C16 C11 C12 C13 -1.4(6) . . . . ? P1 C11 C12 C13 -177.1(3) . . . . ? C11 C12 C13 C14 0.9(7) . . . . ? C12 C13 C14 C15 0.3(7) . . . . ? C13 C14 C15 C16 -0.9(7) . . . . ? C14 C15 C16 C11 0.4(7) . . . . ? C12 C11 C16 C15 0.7(6) . . . . ? P1 C11 C16 C15 176.1(3) . . . . ? C11 P1 C17 C22 -97.7(3) . . . . ? C9 P1 C17 C22 156.1(3) . . . . ? C11 P1 C17 C18 82.9(3) . . . . ? C9 P1 C17 C18 -23.4(4) . . . . ? C22 C17 C18 C19 -1.6(6) . . . . ? P1 C17 C18 C19 177.9(3) . . . . ? C17 C18 C19 C20 1.8(7) . . . . ? C18 C19 C20 C21 -0.4(8) . . . . ? C19 C20 C21 C22 -1.2(8) . . . . ? C20 C21 C22 C17 1.4(7) . . . . ? C18 C17 C22 C21 -0.1(6) . . . . ? P1 C17 C22 C21 -179.5(3) . . . . ? C7 C8 C23 C30 90.5(5) . . . . ? C9 C8 C23 C30 -90.2(5) . . . . ? C7 C8 C23 C24 -84.3(5) . . . . ? C9 C8 C23 C24 95.0(4) . . . . ? C30 C23 C24 C25 -164.2(4) . . . . ? C8 C23 C24 C25 10.7(6) . . . . ? C30 C23 C24 C29 13.5(6) . . . . ? C8 C23 C24 C29 -171.7(4) . . . . ? C29 C24 C25 C26 0.2(7) . . . . ? C23 C24 C25 C26 178.0(5) . . . . ? C24 C25 C26 C27 -0.2(9) . . . . ? C25 C26 C27 C28 -0.4(9) . . . . ? C26 C27 C28 C29 0.9(9) . . . . ? C27 C28 C29 C24 -0.8(8) . . . . ? C25 C24 C29 C28 0.3(7) . . . . ? C23 C24 C29 C28 -177.5(4) . . . . ? C24 C23 C30 C31 176.6(4) . . . . ? C8 C23 C30 C31 1.9(6) . . . . ? C23 C30 C31 C32 8.3(7) . . . . ? C23 C30 C31 C36 -172.7(4) . . . . ? C36 C31 C32 C33 2.1(7) . . . . ? C30 C31 C32 C33 -178.9(4) . . . . ? C31 C32 C33 C34 -1.3(7) . . . . ? C32 C33 C34 C35 -0.5(7) . . . . ? C32 C33 C34 C37 178.4(5) . . . . ? C33 C34 C35 C36 1.3(7) . . . . ? C37 C34 C35 C36 -177.6(5) . . . . ? C34 C35 C36 C31 -0.5(8) . . . . ? C32 C31 C36 C35 -1.2(6) . . . . ? C30 C31 C36 C35 179.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.006 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 917493' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_121123_cj121103_1 #TrackingRef 'web_deposit_cif_file_1_caojian_1356709083.121123_CJ121103_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H29 P' _chemical_formula_sum 'C37 H29 P' _chemical_formula_weight 504.57 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.8506(5) _cell_length_b 9.3011(4) _cell_length_c 29.8411(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.387(3) _cell_angle_gamma 90.00 _cell_volume 2729.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3357 _cell_measurement_theta_min 2.9943 _cell_measurement_theta_max 29.5959 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9540 _exptl_absorpt_correction_T_max 0.9634 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15308 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4992 _reflns_number_gt 3621 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0399P)^2^+0.7076P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4992 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.75250(5) 0.14320(6) 0.191840(16) 0.04238(16) Uani 1 1 d . . . C1 C 0.3767(2) -0.2086(2) 0.11933(7) 0.0466(5) Uani 1 1 d . . . H1 H 0.3456 -0.2227 0.1478 0.056 Uiso 1 1 calc R . . C2 C 0.3114(2) -0.2743(2) 0.08329(7) 0.0530(6) Uani 1 1 d . . . H2 H 0.2365 -0.3328 0.0873 0.064 Uiso 1 1 calc R . . C3 C 0.3573(2) -0.2538(2) 0.04019(7) 0.0533(6) Uani 1 1 d . . . H3 H 0.3115 -0.2972 0.0156 0.064 Uiso 1 1 calc R . . C4 C 0.4680(2) -0.1708(2) 0.03401(6) 0.0464(5) Uani 1 1 d . . . H4 H 0.4981 -0.1595 0.0053 0.056 Uiso 1 1 calc R . . C5 C 0.53825(19) -0.10136(19) 0.07058(6) 0.0369(4) Uani 1 1 d . . . C6 C 0.49066(19) -0.11970(19) 0.11412(6) 0.0376(4) Uani 1 1 d . . . C7 C 0.5608(2) -0.0490(2) 0.15047(6) 0.0399(5) Uani 1 1 d . . . H7 H 0.5309 -0.0623 0.1792 0.048 Uiso 1 1 calc R . . C8 C 0.67092(19) 0.03828(19) 0.14539(6) 0.0372(4) Uani 1 1 d . . . C9 C 0.71967(19) 0.05643(19) 0.10111(6) 0.0355(4) Uani 1 1 d . . . C10 C 0.6534(2) -0.0139(2) 0.06585(6) 0.0390(5) Uani 1 1 d . . . H10 H 0.6860 -0.0034 0.0374 0.047 Uiso 1 1 calc R . . C11 C 0.7412(3) -0.0214(2) 0.27220(7) 0.0619(6) Uani 1 1 d . . . H11 H 0.8286 -0.0529 0.2671 0.074 Uiso 1 1 calc R . . C12 C 0.6752(2) 0.0698(2) 0.24164(6) 0.0439(5) Uani 1 1 d . . . C13 C 0.5471(2) 0.1175(3) 0.25147(7) 0.0622(6) Uani 1 1 d . . . H13 H 0.5015 0.1827 0.2323 0.075 Uiso 1 1 calc R . . C14 C 0.4860(3) 0.0699(3) 0.28911(8) 0.0741(8) Uani 1 1 d . . . H14 H 0.3992 0.1017 0.2948 0.089 Uiso 1 1 calc R . . C15 C 0.5521(3) -0.0238(3) 0.31813(8) 0.0728(8) Uani 1 1 d . . . H15 H 0.5096 -0.0577 0.3431 0.087 Uiso 1 1 calc R . . C16 C 0.6800(3) -0.0670(3) 0.31037(8) 0.0749(8) Uani 1 1 d . . . H16 H 0.7269 -0.1275 0.3307 0.090 Uiso 1 1 calc R . . C17 C 0.9216(2) 0.0625(2) 0.19750(6) 0.0432(5) Uani 1 1 d . . . C18 C 0.9509(2) -0.0795(2) 0.18837(7) 0.0550(6) Uani 1 1 d . . . H18 H 0.8822 -0.1397 0.1768 0.066 Uiso 1 1 calc R . . C19 C 1.0811(3) -0.1332(3) 0.19628(8) 0.0645(6) Uani 1 1 d . . . H19 H 1.0997 -0.2286 0.1895 0.077 Uiso 1 1 calc R . . C1A C 1.1825(3) -0.0462(3) 0.21405(8) 0.0676(7) Uani 1 1 d . . . H1A H 1.2694 -0.0831 0.2202 0.081 Uiso 1 1 calc R . . C20 C 1.1560(3) 0.0943(3) 0.22276(9) 0.0739(7) Uani 1 1 d . . . H20 H 1.2252 0.1537 0.2345 0.089 Uiso 1 1 calc R . . C21 C 1.0269(2) 0.1488(3) 0.21424(7) 0.0587(6) Uani 1 1 d . . . H21 H 1.0104 0.2454 0.2199 0.070 Uiso 1 1 calc R . . C22 C 0.83902(19) 0.15024(19) 0.09248(6) 0.0371(4) Uani 1 1 d . . . C23 C 0.8171(2) 0.3079(2) 0.09916(6) 0.0389(5) Uani 1 1 d . . . C24 C 0.6957(2) 0.3713(2) 0.08384(6) 0.0436(5) Uani 1 1 d . . . H24 H 0.6287 0.3150 0.0693 0.052 Uiso 1 1 calc R . . C25 C 0.6721(2) 0.5161(2) 0.08964(8) 0.0565(6) Uani 1 1 d . . . H25 H 0.5906 0.5566 0.0785 0.068 Uiso 1 1 calc R . . C26 C 0.7686(3) 0.6004(2) 0.11176(8) 0.0653(7) Uani 1 1 d . . . H26 H 0.7525 0.6978 0.1160 0.078 Uiso 1 1 calc R . . C27 C 0.8890(3) 0.5401(2) 0.12753(8) 0.0664(7) Uani 1 1 d . . . H27 H 0.9547 0.5971 0.1424 0.080 Uiso 1 1 calc R . . C28 C 0.9138(2) 0.3952(2) 0.12148(7) 0.0521(5) Uani 1 1 d . . . H28 H 0.9959 0.3558 0.1324 0.062 Uiso 1 1 calc R . . C29 C 0.9548(2) 0.0952(2) 0.07812(6) 0.0415(5) Uani 1 1 d . . . C30 C 0.9790(2) -0.0638(2) 0.07255(8) 0.0578(6) Uani 1 1 d . . . H30A H 0.9011 -0.1163 0.0814 0.087 Uiso 1 1 calc R . . H30B H 1.0576 -0.0921 0.0910 0.087 Uiso 1 1 calc R . . H30C H 0.9939 -0.0842 0.0417 0.087 Uiso 1 1 calc R . . C31 C 1.0713(2) 0.1847(2) 0.06520(7) 0.0445(5) Uani 1 1 d . . . C32 C 1.2005(2) 0.1633(2) 0.08546(8) 0.0582(6) Uani 1 1 d . . . H32 H 1.2133 0.0939 0.1077 0.070 Uiso 1 1 calc R . . C33 C 1.3098(3) 0.2432(3) 0.07312(9) 0.0736(7) Uani 1 1 d . . . H33 H 1.3952 0.2281 0.0873 0.088 Uiso 1 1 calc R . . C34 C 1.2935(3) 0.3447(3) 0.04007(10) 0.0785(8) Uani 1 1 d . . . H34 H 1.3675 0.3990 0.0320 0.094 Uiso 1 1 calc R . . C35 C 1.1671(3) 0.3663(3) 0.01883(9) 0.0726(8) Uani 1 1 d . . . H35 H 1.1560 0.4341 -0.0040 0.087 Uiso 1 1 calc R . . C36 C 1.0566(2) 0.2872(2) 0.03140(7) 0.0561(6) Uani 1 1 d . . . H36 H 0.9715 0.3029 0.0171 0.067 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 0.0382(3) 0.0448(3) 0.0439(3) -0.0053(2) 0.0009(2) -0.0032(2) C1 0.0400(13) 0.0483(12) 0.0522(12) -0.0022(10) 0.0081(9) -0.0056(10) C2 0.0391(13) 0.0512(13) 0.0684(14) -0.0035(11) -0.0002(10) -0.0090(10) C3 0.0521(15) 0.0502(13) 0.0561(13) -0.0073(10) -0.0100(10) -0.0076(11) C4 0.0491(14) 0.0469(12) 0.0425(11) -0.0001(9) -0.0040(9) -0.0013(10) C5 0.0338(11) 0.0317(10) 0.0448(11) 0.0010(8) -0.0018(8) 0.0028(9) C6 0.0323(11) 0.0348(10) 0.0456(11) -0.0004(8) 0.0018(8) 0.0019(9) C7 0.0364(12) 0.0435(11) 0.0403(10) 0.0004(9) 0.0056(8) -0.0013(9) C8 0.0315(11) 0.0374(10) 0.0428(11) -0.0014(8) 0.0016(8) 0.0019(9) C9 0.0305(11) 0.0327(10) 0.0433(10) 0.0019(8) 0.0018(8) 0.0016(8) C10 0.0404(12) 0.0382(10) 0.0385(10) 0.0044(8) 0.0039(8) 0.0025(9) C11 0.0619(17) 0.0639(15) 0.0612(14) 0.0074(12) 0.0150(12) 0.0124(13) C12 0.0417(13) 0.0478(12) 0.0422(11) -0.0103(9) 0.0019(9) -0.0038(10) C13 0.0437(15) 0.0923(18) 0.0502(13) -0.0055(12) -0.0007(10) 0.0118(13) C14 0.0434(15) 0.122(2) 0.0572(15) -0.0203(15) 0.0104(12) -0.0009(16) C15 0.080(2) 0.0900(19) 0.0504(14) -0.0059(13) 0.0212(13) -0.0133(16) C16 0.086(2) 0.0801(18) 0.0607(15) 0.0149(13) 0.0206(14) 0.0149(16) C17 0.0393(13) 0.0506(12) 0.0397(11) -0.0029(9) 0.0031(8) -0.0064(10) C18 0.0439(14) 0.0576(14) 0.0628(14) -0.0141(11) -0.0023(10) -0.0011(11) C19 0.0539(17) 0.0662(15) 0.0729(15) -0.0129(12) 0.0013(12) 0.0136(13) C1A 0.0418(15) 0.090(2) 0.0705(16) 0.0024(14) -0.0031(11) 0.0090(14) C20 0.0467(17) 0.0774(18) 0.0950(19) -0.0030(15) -0.0179(13) -0.0090(14) C21 0.0447(15) 0.0561(14) 0.0738(15) -0.0032(12) -0.0093(11) -0.0056(12) C22 0.0351(12) 0.0352(10) 0.0408(10) 0.0016(8) 0.0017(8) -0.0021(9) C23 0.0363(12) 0.0380(10) 0.0430(10) 0.0029(8) 0.0083(8) -0.0030(9) C24 0.0374(13) 0.0434(12) 0.0505(11) 0.0038(9) 0.0074(9) -0.0014(10) C25 0.0488(15) 0.0495(13) 0.0725(15) 0.0122(11) 0.0142(11) 0.0111(12) C26 0.0659(19) 0.0382(12) 0.0937(18) 0.0001(12) 0.0223(14) 0.0042(13) C27 0.0618(18) 0.0457(13) 0.0915(18) -0.0172(12) 0.0039(13) -0.0110(13) C28 0.0403(13) 0.0469(12) 0.0686(14) -0.0045(10) -0.0005(10) -0.0020(10) C29 0.0394(13) 0.0382(10) 0.0471(11) 0.0018(9) 0.0047(9) -0.0031(9) C30 0.0508(15) 0.0440(12) 0.0800(15) -0.0023(11) 0.0162(11) 0.0023(11) C31 0.0412(13) 0.0404(11) 0.0531(12) -0.0074(9) 0.0122(9) -0.0014(10) C32 0.0413(14) 0.0598(14) 0.0742(15) 0.0004(12) 0.0092(11) -0.0018(12) C33 0.0389(15) 0.0745(18) 0.109(2) -0.0092(16) 0.0152(13) -0.0078(13) C34 0.0568(19) 0.0586(16) 0.124(2) -0.0125(16) 0.0436(17) -0.0160(14) C35 0.081(2) 0.0549(15) 0.0854(18) 0.0098(13) 0.0376(15) -0.0070(15) C36 0.0536(15) 0.0509(13) 0.0650(14) 0.0034(11) 0.0128(11) -0.0028(11) _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 C17 1.826(2) . ? P1 C12 1.840(2) . ? P1 C8 1.8406(19) . ? C1 C2 1.365(3) . ? C1 C6 1.410(3) . ? C1 H1 0.9300 . ? C2 C3 1.401(3) . ? C2 H2 0.9300 . ? C3 C4 1.358(3) . ? C3 H3 0.9300 . ? C4 C5 1.413(3) . ? C4 H4 0.9300 . ? C5 C10 1.410(3) . ? C5 C6 1.417(3) . ? C6 C7 1.414(3) . ? C7 C8 1.370(3) . ? C7 H7 0.9300 . ? C8 C9 1.442(2) . ? C9 C10 1.371(2) . ? C9 C22 1.499(3) . ? C10 H10 0.9300 . ? C11 C12 1.380(3) . ? C11 C16 1.386(3) . ? C11 H11 0.9300 . ? C12 C13 1.386(3) . ? C13 C14 1.378(3) . ? C13 H13 0.9300 . ? C14 C15 1.366(4) . ? C14 H14 0.9300 . ? C15 C16 1.356(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C21 1.381(3) . ? C17 C18 1.382(3) . ? C18 C19 1.384(3) . ? C18 H18 0.9300 . ? C19 C1A 1.367(3) . ? C19 H19 0.9300 . ? C1A C20 1.360(4) . ? C1A H1A 0.9300 . ? C20 C21 1.379(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C29 1.343(3) . ? C22 C23 1.497(3) . ? C23 C24 1.386(3) . ? C23 C28 1.391(3) . ? C24 C25 1.379(3) . ? C24 H24 0.9300 . ? C25 C26 1.372(3) . ? C25 H25 0.9300 . ? C26 C27 1.370(3) . ? C26 H26 0.9300 . ? C27 C28 1.383(3) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C31 1.487(3) . ? C29 C30 1.509(3) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 C36 1.389(3) . ? C31 C32 1.391(3) . ? C32 C33 1.376(3) . ? C32 H32 0.9300 . ? C33 C34 1.368(4) . ? C33 H33 0.9300 . ? C34 C35 1.378(4) . ? C34 H34 0.9300 . ? C35 C36 1.384(3) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? 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 C17 P1 C12 101.03(9) . . ? C17 P1 C8 101.95(9) . . ? C12 P1 C8 103.21(9) . . ? C2 C1 C6 121.13(19) . . ? C2 C1 H1 119.4 . . ? C6 C1 H1 119.4 . . ? C1 C2 C3 120.0(2) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.50(19) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 121.02(19) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C10 C5 C4 123.12(17) . . ? C10 C5 C6 118.22(16) . . ? C4 C5 C6 118.65(18) . . ? C1 C6 C7 122.99(17) . . ? C1 C6 C5 118.70(17) . . ? C7 C6 C5 118.31(17) . . ? C8 C7 C6 123.03(17) . . ? C8 C7 H7 118.5 . . ? C6 C7 H7 118.5 . . ? C7 C8 C9 118.63(17) . . ? C7 C8 P1 122.96(14) . . ? C9 C8 P1 118.27(14) . . ? C10 C9 C8 118.56(17) . . ? C10 C9 C22 119.24(16) . . ? C8 C9 C22 122.19(16) . . ? C9 C10 C5 123.22(17) . . ? C9 C10 H10 118.4 . . ? C5 C10 H10 118.4 . . ? C12 C11 C16 121.4(2) . . ? C12 C11 H11 119.3 . . ? C16 C11 H11 119.3 . . ? C11 C12 C13 117.2(2) . . ? C11 C12 P1 124.09(17) . . ? C13 C12 P1 118.53(17) . . ? C14 C13 C12 121.1(2) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 119.6(2) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C11 120.2(2) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C21 C17 C18 117.7(2) . . ? C21 C17 P1 117.14(16) . . ? C18 C17 P1 125.08(16) . . ? C17 C18 C19 120.9(2) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C1A C19 C18 120.0(2) . . ? C1A C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C20 C1A C19 119.9(2) . . ? C20 C1A H1A 120.0 . . ? C19 C1A H1A 120.0 . . ? C1A C20 C21 120.2(2) . . ? C1A C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C20 C21 C17 121.2(2) . . ? C20 C21 H21 119.4 . . ? C17 C21 H21 119.4 . . ? C29 C22 C23 123.21(17) . . ? C29 C22 C9 121.49(16) . . ? C23 C22 C9 115.24(16) . . ? C24 C23 C28 117.53(18) . . ? C24 C23 C22 120.10(18) . . ? C28 C23 C22 122.35(18) . . ? C25 C24 C23 121.5(2) . . ? C25 C24 H24 119.2 . . ? C23 C24 H24 119.2 . . ? C26 C25 C24 120.1(2) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C27 C26 C25 119.5(2) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C26 C27 C28 120.7(2) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C23 120.6(2) . . ? C27 C28 H28 119.7 . . ? C23 C28 H28 119.7 . . ? C22 C29 C31 123.53(17) . . ? C22 C29 C30 123.49(18) . . ? C31 C29 C30 112.97(17) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C36 C31 C32 117.9(2) . . ? C36 C31 C29 121.5(2) . . ? C32 C31 C29 120.53(19) . . ? C33 C32 C31 121.1(2) . . ? C33 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C34 C33 C32 120.3(3) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C33 C34 C35 119.8(2) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C34 C35 C36 120.1(2) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? C35 C36 C31 120.7(2) . . ? C35 C36 H36 119.6 . . ? C31 C36 H36 119.6 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.276 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 917494'