# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Zeng, Zhiping' 'Luo, Ping' 'Jiang, Yao' 'Liu, Yan' 'Tang, Guo' 'Xu, Pengxiang' 'Zhao, Yu-Fen' 'Blackburn, G' _publ_contact_author_name 'Dr Zhiping Zeng' _publ_contact_author_email yfzhao@xmu.edu.cn _publ_section_title ; Chiral Phosphoproline-Catalyzed Asymmetric Michael Addition of Ketones to Nitroolefins: an Experimental and Theoretical Study. ; # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 826958' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R)-(diphenylphosphoryl)((S)-1-(quinolin-8-ylsulfonyl)pyrrolidin-2-yl)methanol ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration . _chemical_formula_moiety 'C30 H33 N2 O6 P S' _chemical_formula_sum 'C30 H33 N2 O6 P S' _chemical_formula_weight 580.62 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' N N 0.0061 0.0033 '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' 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 p_21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.494(2) _cell_length_b 11.250(3) _cell_length_c 14.974(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.010(4) _cell_angle_gamma 90.00 _cell_volume 1429.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 446(2) _cell_measurement_reflns_used 6006 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 28.18 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8295 _exptl_absorpt_correction_T_max 0.9808 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 446(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11914 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6076 _reflns_number_gt 5630 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _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^)+(0.0764P)^2^+0.1466P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(8) _refine_ls_number_reflns 6076 _refine_ls_number_parameters 361 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.39600(7) 0.18807(5) 0.54260(4) 0.02087(14) Uani 1 1 d . . . S2 S 0.62962(8) 0.05883(6) 0.26403(4) 0.02933(16) Uani 1 1 d . . . C1 C 0.1892(3) 0.1953(3) 0.55669(16) 0.0251(5) Uani 1 1 d . . . O2 O 0.3424(2) -0.01848(15) 0.46294(12) 0.0253(4) Uani 1 1 d . . . H2A H 0.4002 -0.0767 0.4684 0.038 Uiso 1 1 calc R . . N3 N 0.4504(2) 0.0605(2) 0.29107(13) 0.0282(5) Uani 1 1 d . . . O4 O 0.7243(2) 0.0392(2) 0.34359(13) 0.0408(5) Uani 1 1 d . . . O5 O 0.6393(3) -0.02207(19) 0.19186(14) 0.0410(5) Uani 1 1 d . . . O6 O 0.4599(2) 0.30653(17) 0.52192(13) 0.0295(4) Uani 1 1 d . . . C7 C 0.6872(3) 0.2019(3) 0.22817(18) 0.0337(6) Uani 1 1 d . . . C8 C 0.4021(3) 0.1412(2) 0.36223(17) 0.0251(5) Uani 1 1 d . . . H8A H 0.4594 0.2166 0.3594 0.030 Uiso 1 1 calc R . . C9 C 0.4851(3) 0.1270(2) 0.64388(17) 0.0248(5) Uani 1 1 d . . . C10 C 0.2264(3) 0.1610(3) 0.33856(18) 0.0347(7) Uani 1 1 d . . . H10A H 0.1626 0.1101 0.3745 0.042 Uiso 1 1 calc R . . H10B H 0.1977 0.2431 0.3489 0.042 Uiso 1 1 calc R . . C11 C 0.1182(3) 0.3056(3) 0.5462(2) 0.0326(6) Uani 1 1 d . . . H11A H 0.1784 0.3723 0.5347 0.039 Uiso 1 1 calc R . . C12 C 0.4337(3) 0.0835(2) 0.45318(16) 0.0209(5) Uani 1 1 d . . . H12A H 0.5451 0.0605 0.4588 0.025 Uiso 1 1 calc R . . C13 C 0.1014(3) 0.0969(3) 0.57612(19) 0.0329(6) Uani 1 1 d . . . H13A H 0.1496 0.0234 0.5853 0.039 Uiso 1 1 calc R . . C14 C 0.6822(5) 0.3639(3) 0.1217(3) 0.0585(11) Uani 1 1 d . . . C15 C 0.6192(4) 0.2546(3) 0.1502(2) 0.0392(7) Uani 1 1 d . . . N16 N 0.4961(4) 0.2008(3) 0.10564(17) 0.0488(7) Uani 1 1 d . . . C17 C 0.5334(3) 0.0111(3) 0.65372(19) 0.0336(6) Uani 1 1 d . . . H17A H 0.5160 -0.0429 0.6073 0.040 Uiso 1 1 calc R . . C18 C 0.6080(4) -0.0242(3) 0.7331(2) 0.0439(7) Uani 1 1 d . . . H18A H 0.6412 -0.1026 0.7398 0.053 Uiso 1 1 calc R . . C19 C 0.8076(4) 0.2554(3) 0.2762(2) 0.0457(8) Uani 1 1 d . . . H19A H 0.8498 0.2204 0.3284 0.055 Uiso 1 1 calc R . . C20 C 0.5112(4) 0.2070(3) 0.7143(2) 0.0407(7) Uani 1 1 d . . . H20A H 0.4777 0.2854 0.7082 0.049 Uiso 1 1 calc R . . C21 C 0.8681(5) 0.3641(4) 0.2464(3) 0.0643(11) Uani 1 1 d . . . H21A H 0.9508 0.4003 0.2793 0.077 Uiso 1 1 calc R . . C22 C 0.6341(4) 0.0538(4) 0.8020(2) 0.0504(8) Uani 1 1 d . . . H22A H 0.6842 0.0288 0.8554 0.060 Uiso 1 1 calc R . . C24 C -0.1299(3) 0.2170(3) 0.5700(2) 0.0493(9) Uani 1 1 d . . . H24A H -0.2385 0.2241 0.5736 0.059 Uiso 1 1 calc R . . C25 C 0.8099(6) 0.4157(4) 0.1727(3) 0.0683(13) Uani 1 1 d . . . H25A H 0.8531 0.4869 0.1540 0.082 Uiso 1 1 calc R . . C26 C 0.3163(4) 0.0283(3) 0.2294(2) 0.0402(7) Uani 1 1 d . . . H26A H 0.2702 -0.0469 0.2461 0.048 Uiso 1 1 calc R . . H26B H 0.3481 0.0232 0.1682 0.048 Uiso 1 1 calc R . . C27 C 0.4368(6) 0.2564(5) 0.0336(2) 0.0650(12) Uani 1 1 d . . . H27A H 0.3508 0.2214 0.0029 0.078 Uiso 1 1 calc R . . C28 C -0.0423(4) 0.3157(3) 0.5530(2) 0.0454(8) Uani 1 1 d . . . H28A H -0.0910 0.3894 0.5460 0.054 Uiso 1 1 calc R . . C29 C 0.2027(4) 0.1301(3) 0.2408(2) 0.0438(8) Uani 1 1 d . . . H29A H 0.2281 0.1971 0.2034 0.053 Uiso 1 1 calc R . . H29B H 0.0949 0.1057 0.2263 0.053 Uiso 1 1 calc R . . C30 C 0.6159(7) 0.4148(4) 0.0448(3) 0.0796(17) Uani 1 1 d . . . H30A H 0.6564 0.4855 0.0235 0.096 Uiso 1 1 calc R . . C31 C -0.0608(4) 0.1088(3) 0.5818(2) 0.0434(8) Uani 1 1 d . . . H31A H -0.1220 0.0427 0.5937 0.052 Uiso 1 1 calc R . . C33 C 0.5854(4) 0.1699(4) 0.7915(2) 0.0521(9) Uani 1 1 d . . . H33A H 0.6038 0.2236 0.8381 0.062 Uiso 1 1 calc R . . C34 C 0.4918(7) 0.3619(5) 0.0003(3) 0.0758(15) Uani 1 1 d . . . H34A H 0.4452 0.3957 -0.0513 0.091 Uiso 1 1 calc R . . O1 O 0.9560(4) 0.6768(3) 0.07182(19) 0.0789(9) Uani 1 1 d . . . C39 C 1.0068(5) 0.7684(4) 0.1190(3) 0.0620(10) Uani 1 1 d . . . O3 O 1.1007(5) 0.8375(5) 0.0924(3) 0.1106(14) Uani 1 1 d . . . C37 C 0.9325(6) 0.7765(5) 0.2046(3) 0.0766(14) Uani 1 1 d . . . H37A H 0.9744 0.8436 0.2375 0.115 Uiso 1 1 calc R . . H37B H 0.9536 0.7052 0.2384 0.115 Uiso 1 1 calc R . . H37C H 0.8207 0.7859 0.1942 0.115 Uiso 1 1 calc R . . C36 C 1.1090(9) 0.5696(7) -0.0239(3) 0.121(3) Uani 1 1 d . . . H36A H 1.1435 0.5685 -0.0839 0.182 Uiso 1 1 calc R . . H36B H 1.0505 0.4985 -0.0130 0.182 Uiso 1 1 calc R . . H36C H 1.1990 0.5738 0.0176 0.182 Uiso 1 1 calc R . . C35 C 1.0215(13) 0.6598(7) -0.0136(4) 0.152(4) Uani 1 1 d . . . H35B H 0.9348 0.6556 -0.0582 0.182 Uiso 1 1 calc R . . H35C H 1.0823 0.7301 -0.0265 0.182 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 0.0151(3) 0.0194(3) 0.0284(3) -0.0002(3) 0.0030(2) -0.0002(2) S2 0.0290(3) 0.0318(3) 0.0278(3) 0.0025(3) 0.0071(2) 0.0037(3) C1 0.0170(10) 0.0283(13) 0.0303(12) -0.0011(11) 0.0044(9) 0.0014(11) O2 0.0193(8) 0.0187(9) 0.0385(10) -0.0002(7) 0.0054(7) 0.0005(7) N3 0.0262(11) 0.0316(11) 0.0271(10) -0.0017(10) 0.0038(8) -0.0029(10) O4 0.0286(10) 0.0595(15) 0.0349(10) 0.0090(10) 0.0075(8) 0.0067(10) O5 0.0468(13) 0.0371(12) 0.0402(11) -0.0030(9) 0.0134(9) 0.0034(10) O6 0.0225(9) 0.0238(9) 0.0423(11) -0.0013(8) 0.0027(8) -0.0020(7) C7 0.0358(14) 0.0320(15) 0.0349(14) -0.0030(12) 0.0155(11) -0.0019(12) C8 0.0237(12) 0.0233(12) 0.0285(13) -0.0004(10) 0.0035(9) -0.0014(10) C9 0.0179(11) 0.0333(14) 0.0234(12) 0.0003(10) 0.0028(9) -0.0019(10) C10 0.0265(13) 0.0433(18) 0.0340(14) 0.0040(12) -0.0019(10) 0.0080(11) C11 0.0231(13) 0.0326(15) 0.0425(15) 0.0020(12) 0.0040(11) 0.0077(11) C12 0.0141(10) 0.0226(13) 0.0261(12) -0.0014(9) 0.0030(8) 0.0020(8) C13 0.0256(13) 0.0325(14) 0.0415(16) -0.0010(12) 0.0114(11) 0.0010(11) C14 0.077(3) 0.0414(19) 0.061(2) 0.0129(17) 0.046(2) 0.0154(19) C15 0.0483(19) 0.0355(16) 0.0356(15) 0.0018(13) 0.0181(13) 0.0076(14) N16 0.0579(17) 0.0541(18) 0.0348(13) 0.0109(13) 0.0069(12) 0.0145(16) C17 0.0375(15) 0.0304(14) 0.0326(14) 0.0034(11) 0.0007(12) -0.0024(12) C18 0.0477(18) 0.0424(18) 0.0408(17) 0.0069(14) -0.0038(14) 0.0048(15) C19 0.0403(18) 0.0489(19) 0.0495(18) -0.0118(15) 0.0160(14) -0.0076(15) C20 0.0475(17) 0.0387(18) 0.0359(15) -0.0092(13) 0.0032(12) 0.0039(14) C21 0.059(2) 0.050(2) 0.086(3) -0.020(2) 0.028(2) -0.0221(19) C22 0.054(2) 0.066(2) 0.0299(14) 0.0099(16) -0.0079(13) -0.0020(19) C24 0.0173(13) 0.067(3) 0.064(2) -0.0028(17) 0.0069(13) 0.0093(14) C25 0.078(3) 0.0325(19) 0.099(4) -0.005(2) 0.048(3) -0.0139(19) C26 0.0386(16) 0.0449(18) 0.0366(15) -0.0072(13) -0.0017(12) -0.0073(13) C27 0.076(3) 0.081(3) 0.0387(19) 0.0155(19) 0.0085(17) 0.030(2) C28 0.0277(15) 0.050(2) 0.059(2) 0.0052(16) 0.0036(13) 0.0180(14) C29 0.0333(16) 0.061(2) 0.0365(16) 0.0016(14) -0.0076(12) 0.0051(15) C30 0.108(4) 0.061(3) 0.076(3) 0.035(2) 0.057(3) 0.032(3) C31 0.0260(15) 0.0528(19) 0.0525(19) -0.0032(15) 0.0142(13) -0.0113(14) C33 0.059(2) 0.063(3) 0.0334(15) -0.0116(16) -0.0021(14) -0.0026(18) C34 0.099(4) 0.083(3) 0.049(2) 0.034(2) 0.028(2) 0.049(3) O1 0.123(3) 0.066(2) 0.0507(15) 0.0032(15) 0.0363(16) -0.003(2) C39 0.050(2) 0.078(3) 0.058(2) 0.014(2) -0.0061(18) 0.003(2) O3 0.081(3) 0.140(4) 0.111(3) 0.016(3) 0.012(2) -0.044(3) C37 0.098(4) 0.080(3) 0.052(2) -0.001(2) 0.010(2) 0.024(3) C36 0.164(6) 0.145(6) 0.060(3) 0.027(4) 0.056(3) 0.063(5) C35 0.290(11) 0.106(6) 0.070(4) 0.025(3) 0.101(5) 0.048(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O6 1.478(2) . ? P1 C1 1.782(2) . ? P1 C9 1.796(3) . ? P1 C12 1.824(2) . ? S2 O5 1.419(2) . ? S2 O4 1.419(2) . ? S2 N3 1.596(2) . ? S2 C7 1.774(3) . ? C1 C13 1.375(4) . ? C1 C11 1.385(4) . ? O2 C12 1.397(3) . ? O2 H2A 0.8200 . ? N3 C26 1.473(4) . ? N3 C8 1.475(3) . ? C7 C19 1.360(4) . ? C7 C15 1.406(4) . ? C8 C12 1.520(3) . ? C8 C10 1.532(4) . ? C8 H8A 0.9800 . ? C9 C17 1.372(4) . ? C9 C20 1.395(4) . ? C10 C29 1.508(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C28 1.377(4) . ? C11 H11A 0.9300 . ? C12 H12A 0.9800 . ? C13 C31 1.391(4) . ? C13 H13A 0.9300 . ? C14 C30 1.379(6) . ? C14 C15 1.416(5) . ? C14 C25 1.419(7) . ? C15 N16 1.353(5) . ? N16 C27 1.324(4) . ? C17 C18 1.376(4) . ? C17 H17A 0.9300 . ? C18 C22 1.364(5) . ? C18 H18A 0.9300 . ? C19 C21 1.408(6) . ? C19 H19A 0.9300 . ? C20 C33 1.353(5) . ? C20 H20A 0.9300 . ? C21 C25 1.320(7) . ? C21 H21A 0.9300 . ? C22 C33 1.377(6) . ? C22 H22A 0.9300 . ? C24 C31 1.358(5) . ? C24 C28 1.368(5) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C26 C29 1.514(5) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C34 1.378(7) . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C34 1.355(8) . ? C30 H30A 0.9300 . ? C31 H31A 0.9300 . ? C33 H33A 0.9300 . ? C34 H34A 0.9300 . ? O1 C39 1.309(6) . ? O1 C35 1.434(5) . ? C39 O3 1.197(6) . ? C39 C37 1.461(6) . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C36 C35 1.272(9) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C35 H35B 0.9700 . ? C35 H35C 0.9700 . ? 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 O6 P1 C1 111.02(12) . . ? O6 P1 C9 112.28(12) . . ? C1 P1 C9 106.97(11) . . ? O6 P1 C12 110.33(11) . . ? C1 P1 C12 109.20(12) . . ? C9 P1 C12 106.89(12) . . ? O5 S2 O4 119.11(14) . . ? O5 S2 N3 107.17(13) . . ? O4 S2 N3 107.13(11) . . ? O5 S2 C7 108.88(13) . . ? O4 S2 C7 104.04(14) . . ? N3 S2 C7 110.37(13) . . ? C13 C1 C11 120.5(2) . . ? C13 C1 P1 122.5(2) . . ? C11 C1 P1 117.0(2) . . ? C12 O2 H2A 109.5 . . ? C26 N3 C8 111.6(2) . . ? C26 N3 S2 123.68(18) . . ? C8 N3 S2 119.74(18) . . ? C19 C7 C15 121.2(3) . . ? C19 C7 S2 116.9(3) . . ? C15 C7 S2 121.8(2) . . ? N3 C8 C12 110.0(2) . . ? N3 C8 C10 103.1(2) . . ? C12 C8 C10 113.2(2) . . ? N3 C8 H8A 110.1 . . ? C12 C8 H8A 110.1 . . ? C10 C8 H8A 110.1 . . ? C17 C9 C20 119.8(3) . . ? C17 C9 P1 124.4(2) . . ? C20 C9 P1 115.7(2) . . ? C29 C10 C8 105.7(2) . . ? C29 C10 H10A 110.6 . . ? C8 C10 H10A 110.6 . . ? C29 C10 H10B 110.6 . . ? C8 C10 H10B 110.6 . . ? H10A C10 H10B 108.7 . . ? C28 C11 C1 119.5(3) . . ? C28 C11 H11A 120.2 . . ? C1 C11 H11A 120.2 . . ? O2 C12 C8 111.8(2) . . ? O2 C12 P1 109.45(15) . . ? C8 C12 P1 110.65(17) . . ? O2 C12 H12A 108.3 . . ? C8 C12 H12A 108.3 . . ? P1 C12 H12A 108.3 . . ? C1 C13 C31 119.0(3) . . ? C1 C13 H13A 120.5 . . ? C31 C13 H13A 120.5 . . ? C30 C14 C15 117.9(5) . . ? C30 C14 C25 123.1(4) . . ? C15 C14 C25 119.0(4) . . ? N16 C15 C7 119.6(3) . . ? N16 C15 C14 122.2(3) . . ? C7 C15 C14 118.1(3) . . ? C27 N16 C15 116.2(4) . . ? C9 C17 C18 119.3(3) . . ? C9 C17 H17A 120.4 . . ? C18 C17 H17A 120.4 . . ? C22 C18 C17 121.1(3) . . ? C22 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? C7 C19 C21 119.6(4) . . ? C7 C19 H19A 120.2 . . ? C21 C19 H19A 120.2 . . ? C33 C20 C9 119.7(3) . . ? C33 C20 H20A 120.2 . . ? C9 C20 H20A 120.2 . . ? C25 C21 C19 121.3(4) . . ? C25 C21 H21A 119.3 . . ? C19 C21 H21A 119.3 . . ? C18 C22 C33 119.2(3) . . ? C18 C22 H22A 120.4 . . ? C33 C22 H22A 120.4 . . ? C31 C24 C28 121.0(3) . . ? C31 C24 H24A 119.5 . . ? C28 C24 H24A 119.5 . . ? C21 C25 C14 120.8(4) . . ? C21 C25 H25A 119.6 . . ? C14 C25 H25A 119.6 . . ? N3 C26 C29 102.7(2) . . ? N3 C26 H26A 111.2 . . ? C29 C26 H26A 111.2 . . ? N3 C26 H26B 111.2 . . ? C29 C26 H26B 111.2 . . ? H26A C26 H26B 109.1 . . ? N16 C27 C34 125.5(5) . . ? N16 C27 H27A 117.3 . . ? C34 C27 H27A 117.3 . . ? C24 C28 C11 119.8(3) . . ? C24 C28 H28A 120.1 . . ? C11 C28 H28A 120.1 . . ? C10 C29 C26 103.3(2) . . ? C10 C29 H29A 111.1 . . ? C26 C29 H29A 111.1 . . ? C10 C29 H29B 111.1 . . ? C26 C29 H29B 111.1 . . ? H29A C29 H29B 109.1 . . ? C34 C30 C14 120.1(4) . . ? C34 C30 H30A 119.9 . . ? C14 C30 H30A 119.9 . . ? C24 C31 C13 120.1(3) . . ? C24 C31 H31A 120.0 . . ? C13 C31 H31A 120.0 . . ? C20 C33 C22 120.9(3) . . ? C20 C33 H33A 119.5 . . ? C22 C33 H33A 119.5 . . ? C30 C34 C27 118.0(4) . . ? C30 C34 H34A 121.0 . . ? C27 C34 H34A 121.0 . . ? C39 O1 C35 117.0(5) . . ? O3 C39 O1 122.6(5) . . ? O3 C39 C37 125.3(5) . . ? O1 C39 C37 112.1(4) . . ? C39 C37 H37A 109.5 . . ? C39 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C39 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C36 C35 O1 118.1(5) . . ? C36 C35 H35B 107.8 . . ? O1 C35 H35B 107.8 . . ? C36 C35 H35C 107.8 . . ? O1 C35 H35C 107.8 . . ? H35B C35 H35C 107.1 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.406 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.061