# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Janine Cossy' 'Jean-Roger Desmurs' 'Olivier Mirguet' 'Domingo Gomez Pardo' _publ_contact_author_name 'Dr Janine Cossy' _publ_contact_author_address ; Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris Laboratoire de Chimie Organique - Bat. F. 10 rue Vauquelin Paris 75231 Cedex 05 FRANCE ; _publ_requested_journal 'New Journal of Chemistry' _publ_contact_author_phone ' 33 01 44 27 34 83 ' _publ_contact_author_fax ' 33 01 44 27 55 13' _publ_contact_author_email ' jmvalery@ccr.jussieu.fr ' _publ_requested_coeditor_name ' ? ' _publ_contact_letter ; ; #============================================================================= # TITLE AND AUTHOR LIST _publ_section_title ; Diastereoselective conjugate addition of organocuprates to chiral racemic olefinic amido esters. Synthesis of paroxetine ; data_CRYSTALS_cif _database_code_CSD 162939 _audit_creation_date 01-03-08 _audit_creation_method CRYSTALS #**************************************************************************** #============================================================================== _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994) ; _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; # _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' #========================================================================== _chemical_melting_point ? _diffrn_radiation_monochromator ' graphite' _diffrn_measurement_device ' Enraf-nonius CAD4 ' _refine_ls_matrix_type ' full' _refine_ls_weighting_scheme ; Chebychev polynomial (Carruthers & Watkin, 1979) ; _atom_sites_solution_primary 'Direct_Methods' _atom_sites_solution_hydrogens ' Geometric' _refine_ls_hydrogen_treatment ; H atoms placed geometrically after each cycle, one overall isotropic thermal parameter refined ; #**************************************************************************** _chemical_name_systematic ; # IUPAC name, in full ? ; _cell_length_a 11.849(7) _cell_angle_alpha 66.36(3) _cell_length_b 12.894(3) _cell_angle_beta 73.83(4) _cell_length_c 14.747(6) _cell_angle_gamma 72.44(3) _cell_volume 1936(2) _symmetry_cell_setting 'Triclinic ' _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'F ' 0.0140 0.0100 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' 'S ' 0.1100 0.1240 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C41 H49 S1 F1 N2 O7' _chemical_formula_moiety ' C41 H49 S1 F1 N2 O7 ' _chemical_compound_source ; ? ; _chemical_formula_weight 732.91 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 10.2 _cell_measurement_temperature 295K _cell_formula_units_Z 2 _exptl_crystal_description 'plate ' _exptl_crystal_colour ' none ' _exptl_crystal_size_min 0.1 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_max 0.6 _exptl_crystal_density_diffrn 1.26 _exptl_crystal_density_meas ? _exptl_crystal_F_000 780.44 _exptl_absorpt_coefficient_mu 0.13 _exptl_absorpt_correction_type 'none' _diffrn_standards_interval_time 3600 _diffrn_standards_interval_count ? _diffrn_standards_number 2 _diffrn_standards_decay_% 7.65 _diffrn_ambient_temperature 295K _diffrn_reflns_number 7147 _reflns_number_total 6786 _diffrn_reflns_av_R_equivalents 0.02 _reflns_number_observed 3163 _diffrn_reflns_theta_min 1 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _reflns_observed_criterion >3.00\s(I) _refine_diff_density_min -0.91 _refine_diff_density_max 1.00 _refine_ls_number_reflns 3163 _refine_ls_number_parameters 471 _refine_ls_R_factor_obs 0.0549 _refine_ls_wR_factor_obs 0.0670 _refine_ls_goodness_of_fit_obs 1.1397 _refine_ls_shift/esd_max 12.134171 _refine_ls_structure_factor_coef 'F' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_method 2\q/\w loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type S1 0.26777(9) 0.53158(9) 0.44953(8) 0.0465 1.0000 Uani F1 0.6495(5) 0.0825(4) 0.4427(4) 0.1442 1.0000 Uani O1 0.1905(3) 0.4945(3) 0.4158(2) 0.0576 1.0000 Uani O2 0.3934(2) 0.4865(2) 0.4321(2) 0.0565 1.0000 Uani O3 0.3603(2) 0.6493(2) 0.2283(2) 0.0421 1.0000 Uani O4 0.5212(3) 0.5655(3) 0.1420(3) 0.0643 1.0000 Uani O5 0.2619(3) 0.7111(3) 0.0506(3) 0.0674 1.0000 Uani O6 0.0904(4) 0.6262(4) -0.0754(3) 0.0832 1.0000 Uani O7 0.0378(3) 0.7180(3) 0.0343(2) 0.0597 1.0000 Uani N1 0.2475(3) 0.6720(3) 0.4004(2) 0.0436 1.0000 Uani N2 0.1906(3) 0.5657(3) 0.0536(3) 0.0561 1.0000 Uani C1 0.3547(3) 0.7234(3) 0.3574(3) 0.0424 1.0000 Uani C2 0.4281(3) 0.7006(3) 0.2601(3) 0.0417 1.0000 Uani C3 0.4478(3) 0.8198(4) 0.1849(3) 0.0486 1.0000 Uani C4 0.3274(4) 0.8880(4) 0.1512(3) 0.0556 1.0000 Uani C5 0.2473(4) 0.9100(4) 0.2450(3) 0.0586 1.0000 Uani C6 0.3307(4) 0.8546(4) 0.3237(3) 0.0538 1.0000 Uani C7 0.4519(4) 0.8769(4) 0.2572(3) 0.0585 1.0000 Uani C8 0.5601(5) 0.8199(5) 0.3119(4) 0.0761 1.0000 Uani C9 0.4533(6) 1.0059(5) 0.2081(4) 0.0805 1.0000 Uani C10 0.5532(5) 0.8161(5) 0.1001(4) 0.0696 1.0000 Uani C11 0.4178(4) 0.5806(4) 0.1757(3) 0.0472 1.0000 Uani C12 0.3314(4) 0.5236(4) 0.1643(3) 0.0472 1.0000 Uani C13 0.2596(4) 0.6106(4) 0.0841(3) 0.0494 1.0000 Uani C14 0.2332(5) 0.4501(5) 0.0455(4) 0.0720 1.0000 Uani C15 0.2939(5) 0.3653(4) 0.1317(4) 0.0668 1.0000 Uani C16 0.3915(4) 0.4101(4) 0.1445(3) 0.0573 1.0000 Uani C17 0.1028(4) 0.6401(4) -0.0044(4) 0.0583 1.0000 Uani C18 0.4595(4) 0.3222(4) 0.2257(3) 0.0580 1.0000 Uani C19 0.5754(6) 0.2716(6) 0.2022(5) 0.0979 1.0000 Uani C20 0.6406(6) 0.1905(7) 0.2749(7) 0.1152 1.0000 Uani C21 0.5867(8) 0.1619(7) 0.3696(7) 0.1053 1.0000 Uani C22 0.4705(8) 0.2035(7) 0.3970(5) 0.1053 1.0000 Uani C23 0.4064(5) 0.2856(6) 0.3243(4) 0.0860 1.0000 Uani C24 -0.0438(4) 0.8202(4) -0.0219(4) 0.0633 1.0000 Uani C25 -0.1382(5) 0.7851(5) -0.0471(4) 0.0733 1.0000 Uani C26 0.0293(5) 0.8907(5) -0.1150(5) 0.0836 1.0000 Uani C27 -0.0989(6) 0.8814(5) 0.0521(5) 0.0898 1.0000 Uani C28 0.1319(3) 0.7342(3) 0.4362(3) 0.0448 1.0000 Uani C29 0.0344(4) 0.7472(4) 0.3959(4) 0.0586 1.0000 Uani C30 -0.0772(4) 0.8018(5) 0.4321(5) 0.0703 1.0000 Uani C31 -0.0897(5) 0.8410(5) 0.5082(5) 0.0765 1.0000 Uani C32 0.0060(5) 0.8287(4) 0.5498(4) 0.0686 1.0000 Uani C33 0.1178(4) 0.7748(4) 0.5123(3) 0.0533 1.0000 Uani C34 -0.1835(5) 0.8173(7) 0.3870(7) 0.1034 1.0000 Uani C35 -0.0104(7) 0.8687(6) 0.6361(5) 0.1012 1.0000 Uani C36 0.2166(4) 0.5036(3) 0.5792(3) 0.0479 1.0000 Uani C37 0.1031(4) 0.4838(4) 0.6211(3) 0.0606 1.0000 Uani C38 0.0611(5) 0.4724(5) 0.7201(4) 0.0749 1.0000 Uani C39 0.1287(6) 0.4832(5) 0.7747(4) 0.0730 1.0000 Uani C40 0.2412(5) 0.5032(5) 0.7325(4) 0.0676 1.0000 Uani C41 0.2868(4) 0.5139(4) 0.6337(3) 0.0557 1.0000 Uani H11 0.3948 0.6846 0.4177 0.069(2) 1.0000 Uiso H21 0.5061 0.6423 0.2667 0.068(2) 1.0000 Uiso H41 0.3366 0.9628 0.0949 0.074(2) 1.0000 Uiso H42 0.2937 0.8414 0.1289 0.074(2) 1.0000 Uiso H51 0.2169 0.9950 0.2324 0.081(2) 1.0000 Uiso H52 0.1768 0.8720 0.2678 0.081(2) 1.0000 Uiso H61 0.2984 0.8823 0.3822 0.081(2) 1.0000 Uiso H81 0.5562 0.8620 0.3572 0.115(2) 1.0000 Uiso H82 0.6363 0.8245 0.2610 0.115(2) 1.0000 Uiso H83 0.5579 0.7371 0.3524 0.115(2) 1.0000 Uiso H91 0.4561 1.0363 0.2600 0.112(2) 1.0000 Uiso H92 0.5258 1.0169 0.1538 0.112(2) 1.0000 Uiso H93 0.3790 1.0489 0.1786 0.112(2) 1.0000 Uiso H101 0.5599 0.8966 0.0547 0.093(2) 1.0000 Uiso H102 0.6290 0.7749 0.1284 0.093(2) 1.0000 Uiso H103 0.5415 0.7732 0.0611 0.093(2) 1.0000 Uiso H121 0.2769 0.4992 0.2310 0.074(2) 1.0000 Uiso H141 0.2922 0.4554 -0.0193 0.098(2) 1.0000 Uiso H142 0.1634 0.4226 0.0448 0.098(2) 1.0000 Uiso H151 0.2324 0.3519 0.1948 0.082(2) 1.0000 Uiso H152 0.3313 0.2907 0.1189 0.082(2) 1.0000 Uiso H161 0.4540 0.4246 0.0817 0.082(2) 1.0000 Uiso H191 0.6152 0.2928 0.1299 0.133(2) 1.0000 Uiso H201 0.7275 0.1550 0.2551 0.115(2) 1.0000 Uiso H221 0.4297 0.1763 0.4692 0.109(2) 1.0000 Uiso H231 0.3194 0.3184 0.3444 0.130(2) 1.0000 Uiso H251 -0.1927 0.8560 -0.0851 0.103(2) 1.0000 Uiso H252 -0.1866 0.7408 0.0165 0.103(2) 1.0000 Uiso H253 -0.0985 0.7351 -0.0892 0.103(2) 1.0000 Uiso H261 -0.0254 0.9605 -0.1535 0.113(2) 1.0000 Uiso H262 0.0880 0.9157 -0.0949 0.113(2) 1.0000 Uiso H263 0.0741 0.8423 -0.1578 0.113(2) 1.0000 Uiso H271 -0.1568 0.9543 0.0217 0.124(2) 1.0000 Uiso H272 -0.0336 0.9017 0.0690 0.124(2) 1.0000 Uiso H273 -0.1414 0.8303 0.1143 0.124(2) 1.0000 Uiso H291 0.0457 0.7169 0.3403 0.069(2) 1.0000 Uiso H311 -0.1718 0.8803 0.5348 0.093(2) 1.0000 Uiso H331 0.1895 0.7649 0.5410 0.093(2) 1.0000 Uiso H341 -0.2572 0.8583 0.4218 0.136(2) 1.0000 Uiso H342 -0.1683 0.8645 0.3138 0.136(2) 1.0000 Uiso H343 -0.1937 0.7398 0.3956 0.136(2) 1.0000 Uiso H351 0.0694 0.8524 0.6551 0.135(2) 1.0000 Uiso H352 -0.0452 0.9541 0.6150 0.135(2) 1.0000 Uiso H353 -0.0660 0.8269 0.6944 0.135(2) 1.0000 Uiso H371 0.0524 0.4777 0.5802 0.104(2) 1.0000 Uiso H381 -0.0207 0.4555 0.7526 0.086(2) 1.0000 Uiso H391 0.0947 0.4776 0.8465 0.097(2) 1.0000 Uiso H401 0.2912 0.5092 0.7740 0.081(2) 1.0000 Uiso H411 0.3692 0.5291 0.6019 0.097(2) 1.0000 Uiso 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 S1 0.0455(6) 0.0479(6) 0.0447(6) -0.0158(5) -0.0032(5) -0.0119(5) F1 0.171(4) 0.152(4) 0.145(4) -0.026(3) -0.091(3) 0.046(3) O1 0.072(2) 0.065(2) 0.056(2) -0.026(2) -0.009(1) -0.028(2) O2 0.047(2) 0.051(2) 0.064(2) -0.016(1) 0.000(1) -0.004(1) O3 0.038(1) 0.050(2) 0.043(1) -0.018(1) -0.008(1) -0.011(1) O4 0.044(2) 0.097(3) 0.088(2) -0.058(2) 0.010(2) -0.021(2) O5 0.102(3) 0.060(2) 0.073(2) -0.006(2) -0.041(2) -0.035(2) O6 0.114(3) 0.121(3) 0.104(3) -0.079(3) -0.059(3) 0.020(3) O7 0.066(2) 0.066(2) 0.061(2) -0.031(2) -0.019(2) -0.008(2) N1 0.040(2) 0.048(2) 0.042(2) -0.016(2) -0.001(1) -0.012(1) N2 0.058(2) 0.067(3) 0.059(2) -0.031(2) -0.014(2) -0.015(2) C1 0.045(2) 0.048(2) 0.039(2) -0.015(2) -0.010(2) -0.014(2) C2 0.035(2) 0.051(2) 0.044(2) -0.018(2) -0.009(2) -0.010(2) C3 0.044(2) 0.057(3) 0.046(2) -0.011(2) -0.005(2) -0.020(2) C4 0.066(3) 0.047(3) 0.051(2) -0.007(2) -0.016(2) -0.012(2) C5 0.051(3) 0.051(3) 0.063(3) -0.007(2) -0.008(2) -0.006(2) C6 0.065(3) 0.051(3) 0.055(3) -0.024(2) -0.006(2) -0.017(2) C7 0.063(3) 0.058(3) 0.062(3) -0.016(2) -0.012(2) -0.025(2) C8 0.075(3) 0.104(4) 0.093(4) -0.026(3) -0.029(3) -0.043(3) C9 0.106(4) 0.071(4) 0.090(4) -0.026(3) -0.009(3) -0.044(3) C10 0.072(3) 0.073(3) 0.061(3) -0.013(3) 0.010(2) -0.028(3) C11 0.048(3) 0.051(3) 0.042(2) -0.017(2) -0.003(2) -0.012(2) C12 0.049(2) 0.056(3) 0.042(2) -0.018(2) -0.003(2) -0.018(2) C13 0.062(3) 0.059(3) 0.043(2) -0.022(2) -0.008(2) -0.022(2) C14 0.083(4) 0.071(4) 0.090(4) -0.045(3) -0.026(3) -0.009(3) C15 0.076(3) 0.061(3) 0.083(3) -0.037(3) -0.019(3) -0.012(3) C16 0.061(3) 0.059(3) 0.054(3) -0.025(2) -0.003(2) -0.012(2) C17 0.059(3) 0.074(3) 0.062(3) -0.037(3) -0.015(2) -0.011(2) C18 0.058(3) 0.055(3) 0.063(3) -0.027(2) -0.006(2) -0.007(2) C19 0.070(4) 0.118(5) 0.089(4) -0.013(4) 0.003(3) 0.001(4) C20 0.071(4) 0.129(7) 0.137(7) -0.008(6) -0.015(4) 0.016(4) C21 0.108(6) 0.106(6) 0.112(6) -0.031(5) -0.052(5) 0.018(5) C22 0.150(7) 0.123(6) 0.060(4) -0.022(4) -0.026(4) 0.040(5) C23 0.094(4) 0.103(5) 0.062(3) -0.030(3) -0.007(3) 0.019(4) C24 0.068(3) 0.055(3) 0.074(3) -0.021(2) -0.023(3) -0.012(2) C25 0.065(3) 0.072(4) 0.098(4) -0.024(3) -0.030(3) -0.018(3) C26 0.096(4) 0.082(4) 0.090(4) -0.013(3) -0.025(3) -0.043(3) C27 0.100(4) 0.084(4) 0.118(5) -0.059(4) -0.028(4) -0.001(3) C28 0.039(2) 0.048(2) 0.045(2) -0.016(2) -0.005(2) -0.008(2) C29 0.054(3) 0.059(3) 0.067(3) -0.017(2) -0.016(2) -0.016(2) C30 0.042(3) 0.073(3) 0.112(4) -0.032(3) -0.017(3) -0.005(2) C31 0.053(3) 0.074(4) 0.117(5) -0.044(4) 0.010(3) -0.005(3) C32 0.076(3) 0.058(3) 0.071(3) -0.029(3) 0.003(3) -0.007(3) C33 0.058(3) 0.051(3) 0.049(2) -0.020(2) -0.005(2) -0.007(2) C34 0.054(3) 0.123(6) 0.216(9) -0.068(6) -0.052(4) 0.002(3) C35 0.133(6) 0.108(5) 0.097(5) -0.066(4) 0.015(4) -0.008(4) C36 0.056(2) 0.042(2) 0.044(2) -0.013(2) -0.006(2) -0.012(2) C37 0.066(3) 0.075(3) 0.049(3) -0.020(2) 0.001(2) -0.029(2) C38 0.077(3) 0.108(5) 0.058(3) -0.027(3) 0.015(3) -0.043(3) C39 0.098(4) 0.084(4) 0.045(3) -0.020(3) -0.006(3) -0.022(3) C40 0.085(4) 0.080(4) 0.055(3) -0.018(3) -0.031(3) -0.015(3) C41 0.057(3) 0.060(3) 0.052(3) -0.014(2) -0.022(2) -0.006(2) _refine_ls_extinction_coef 549 _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . O1 . 1.422(3) yes S1 . O2 . 1.416(3) yes S1 . N1 . 1.626(3) yes S1 . C36 . 1.757(4) yes F1 . C21 . 1.367(7) yes O3 . C2 . 1.442(4) yes O3 . C11 . 1.320(5) yes O4 . C11 . 1.176(5) yes O5 . C13 . 1.193(5) yes O6 . C17 . 1.184(5) yes O7 . C17 . 1.295(5) yes O7 . C24 . 1.469(5) yes N1 . C1 . 1.475(5) yes N1 . C28 . 1.439(5) yes N2 . C13 . 1.380(5) yes N2 . C14 . 1.465(6) yes N2 . C17 . 1.403(6) yes C1 . C2 . 1.547(5) yes C1 . C6 . 1.517(6) yes C1 . H11 . 1.000(4) no C2 . C3 . 1.534(6) yes C2 . H21 . 1.001(4) no C3 . C4 . 1.531(6) yes C3 . C7 . 1.537(6) yes C3 . C10 . 1.505(6) yes C4 . C5 . 1.521(6) yes C4 . H41 . 1.001(4) no C4 . H42 . 1.002(5) no C5 . C6 . 1.543(6) yes C5 . H51 . 1.001(5) no C5 . H52 . 1.005(5) no C6 . C7 . 1.531(6) yes C6 . H61 . 1.001(4) no C7 . C8 . 1.538(7) yes C7 . C9 . 1.529(7) yes C8 . H81 . 0.999(6) no C8 . H82 . 1.000(6) no C8 . H83 . 0.997(6) no C9 . H91 . 1.001(6) no C9 . H92 . 1.000(6) no C9 . H93 . 0.999(6) no C10 . H101 . 0.997(5) no C10 . H102 . 1.003(5) no C10 . H103 . 1.003(6) no C11 . C12 . 1.505(6) yes C12 . C13 . 1.518(6) yes C12 . C16 . 1.527(6) yes C12 . H121 . 1.002(4) no C14 . C15 . 1.500(7) yes C14 . H141 . 1.005(6) no C14 . H142 . 0.997(5) no C15 . C16 . 1.522(7) yes C15 . H151 . 0.999(5) no C15 . H152 . 0.999(5) no C16 . C18 . 1.506(6) yes C16 . H161 . 1.002(4) no C18 . C19 . 1.344(7) yes C18 . C23 . 1.361(7) yes C19 . C20 . 1.38(1) yes C19 . H191 . 1.000(6) no C20 . C21 . 1.31(1) yes C20 . H201 . 1.005(7) no C21 . C22 . 1.33(1) yes C22 . C23 . 1.380(8) yes C22 . H221 . 1.003(7) no C23 . H231 . 0.999(6) no C24 . C25 . 1.506(6) yes C24 . C26 . 1.508(7) yes C24 . C27 . 1.491(7) yes C25 . H251 . 1.000(5) no C25 . H252 . 1.002(6) no C25 . H253 . 0.999(6) no C26 . H261 . 0.998(6) no C26 . H262 . 1.002(5) no C26 . H263 . 0.999(6) no C27 . H271 . 0.999(6) no C27 . H272 . 1.005(6) no C27 . H273 . 0.994(7) no C28 . C29 . 1.378(6) yes C28 . C33 . 1.371(6) yes C29 . C30 . 1.370(7) yes C29 . H291 . 1.004(5) no C30 . C31 . 1.362(8) yes C30 . C34 . 1.510(8) yes C31 . C32 . 1.374(8) yes C31 . H311 . 1.003(5) no C32 . C33 . 1.374(6) yes C32 . C35 . 1.501(8) yes C33 . H331 . 1.004(4) no C34 . H341 . 0.998(7) no C34 . H342 . 1.00(1) no C34 . H343 . 0.996(8) no C35 . H351 . 0.999(8) no C35 . H352 . 1.002(7) no C35 . H353 . 0.996(7) no C36 . C37 . 1.369(6) yes C36 . C41 . 1.371(6) yes C37 . C38 . 1.366(7) yes C37 . H371 . 1.000(5) no C38 . C39 . 1.351(7) yes C38 . H381 . 1.000(5) no C39 . C40 . 1.359(7) yes C39 . H391 . 1.003(5) no C40 . C41 . 1.372(7) yes C40 . H401 . 0.999(5) no C41 . H411 . 0.999(5) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . S1 . O2 . 119.4(2) no O1 . S1 . N1 . 109.1(2) no O2 . S1 . N1 . 106.9(2) no O1 . S1 . C36 . 107.1(2) no O2 . S1 . C36 . 109.1(2) no N1 . S1 . C36 . 104.4(2) no C2 . O3 . C11 . 119.5(3) no C17 . O7 . C24 . 121.3(3) no S1 . N1 . C1 . 118.2(2) no S1 . N1 . C28 . 114.8(2) no C1 . N1 . C28 . 122.6(3) no C13 . N2 . C14 . 121.1(4) no C13 . N2 . C17 . 120.3(4) no C14 . N2 . C17 . 114.7(4) no N1 . C1 . C2 . 113.6(3) no N1 . C1 . C6 . 115.9(3) no C2 . C1 . C6 . 101.9(3) no N1 . C1 . H11 . 98.0(3) no C2 . C1 . H11 . 116.1(3) no C6 . C1 . H11 . 112.2(3) no O3 . C2 . C1 . 108.6(3) no O3 . C2 . C3 . 113.4(3) no C1 . C2 . C3 . 104.9(3) no O3 . C2 . H21 . 102.9(3) no C1 . C2 . H21 . 116.1(3) no C3 . C2 . H21 . 111.2(3) no C2 . C3 . C4 . 106.8(3) no C2 . C3 . C7 . 100.2(3) no C4 . C3 . C7 . 101.2(3) no C2 . C3 . C10 . 114.7(4) no C4 . C3 . C10 . 114.6(4) no C7 . C3 . C10 . 117.5(4) no C3 . C4 . C5 . 103.8(3) no C3 . C4 . H41 . 111.0(4) no C5 . C4 . H41 . 110.9(4) no C3 . C4 . H42 . 110.9(4) no C5 . C4 . H42 . 111.0(4) no H41 . C4 . H42 . 109.2(4) no C4 . C5 . C6 . 103.9(3) no C4 . C5 . H51 . 111.1(4) no C6 . C5 . H51 . 111.1(4) no C4 . C5 . H52 . 110.9(4) no C6 . C5 . H52 . 110.9(4) no H51 . C5 . H52 . 109.0(4) no C1 . C6 . C5 . 110.0(3) no C1 . C6 . C7 . 100.7(3) no C5 . C6 . C7 . 101.3(3) no C1 . C6 . H61 . 111.5(4) no C5 . C6 . H61 . 112.5(4) no C7 . C6 . H61 . 119.8(4) no C3 . C7 . C6 . 94.7(3) no C3 . C7 . C8 . 114.3(4) no C6 . C7 . C8 . 114.8(4) no C3 . C7 . C9 . 114.4(4) no C6 . C7 . C9 . 112.7(4) no C8 . C7 . C9 . 106.0(4) no C7 . C8 . H81 . 109.3(5) no C7 . C8 . H82 . 109.2(5) no H81 . C8 . H82 . 109.5(5) no C7 . C8 . H83 . 109.4(4) no H81 . C8 . H83 . 109.7(5) no H82 . C8 . H83 . 109.7(6) no C7 . C9 . H91 . 109.4(5) no C7 . C9 . H92 . 109.5(5) no H91 . C9 . H92 . 109.4(5) no C7 . C9 . H93 . 109.5(4) no H91 . C9 . H93 . 109.5(6) no H92 . C9 . H93 . 109.6(6) no C3 . C10 . H101 . 109.8(4) no C3 . C10 . H102 . 109.5(4) no H101 . C10 . H102 . 109.5(5) no C3 . C10 . H103 . 109.5(4) no H101 . C10 . H103 . 109.5(5) no H102 . C10 . H103 . 109.1(5) no O3 . C11 . O4 . 125.6(4) no O3 . C11 . C12 . 110.2(3) no O4 . C11 . C12 . 124.2(4) no C11 . C12 . C13 . 108.8(3) no C11 . C12 . C16 . 113.8(3) no C13 . C12 . C16 . 112.5(3) no C11 . C12 . H121 . 107.3(3) no C13 . C12 . H121 . 110.5(4) no C16 . C12 . H121 . 103.7(4) no O5 . C13 . N2 . 122.5(4) no O5 . C13 . C12 . 122.0(4) no N2 . C13 . C12 . 115.4(4) no N2 . C14 . C15 . 111.3(4) no N2 . C14 . H141 . 108.6(5) no C15 . C14 . H141 . 109.0(5) no N2 . C14 . H142 . 109.2(4) no C15 . C14 . H142 . 109.4(5) no H141 . C14 . H142 . 109.4(4) no C14 . C15 . C16 . 111.7(4) no C14 . C15 . H151 . 108.8(4) no C16 . C15 . H151 . 108.8(4) no C14 . C15 . H152 . 109.0(4) no C16 . C15 . H152 . 108.8(4) no H151 . C15 . H152 . 109.7(5) no C12 . C16 . C15 . 107.5(4) no C12 . C16 . C18 . 112.6(4) no C15 . C16 . C18 . 112.3(4) no C12 . C16 . H161 . 109.7(4) no C15 . C16 . H161 . 110.1(4) no C18 . C16 . H161 . 104.6(4) no O6 . C17 . O7 . 127.3(5) no O6 . C17 . N2 . 122.3(4) no O7 . C17 . N2 . 110.3(4) no C16 . C18 . C19 . 120.5(5) no C16 . C18 . C23 . 122.4(4) no C19 . C18 . C23 . 117.0(5) no C18 . C19 . C20 . 122.0(6) no C18 . C19 . H191 . 118.8(6) no C20 . C19 . H191 . 119.2(6) no C19 . C20 . C21 . 118.6(6) no C19 . C20 . H201 . 120.3(9) no C21 . C20 . H201 . 121.2(8) no F1 . C21 . C20 . 119.6(7) no F1 . C21 . C22 . 118.1(8) no C20 . C21 . C22 . 122.2(7) no C21 . C22 . C23 . 118.8(6) no C21 . C22 . H221 . 120.9(7) no C23 . C22 . H221 . 120.3(7) no C18 . C23 . C22 . 121.2(6) no C18 . C23 . H231 . 119.5(5) no C22 . C23 . H231 . 119.4(6) no O7 . C24 . C25 . 111.0(4) no O7 . C24 . C26 . 109.0(4) no C25 . C24 . C26 . 111.7(4) no O7 . C24 . C27 . 101.8(4) no C25 . C24 . C27 . 110.8(5) no C26 . C24 . C27 . 112.0(5) no C24 . C25 . H251 . 109.5(5) no C24 . C25 . H252 . 109.5(5) no H251 . C25 . H252 . 109.3(5) no C24 . C25 . H253 . 109.6(4) no H251 . C25 . H253 . 109.6(5) no H252 . C25 . H253 . 109.4(5) no C24 . C26 . H261 . 109.5(5) no C24 . C26 . H262 . 109.3(5) no H261 . C26 . H262 . 109.5(5) no C24 . C26 . H263 . 109.4(5) no H261 . C26 . H263 . 109.7(6) no H262 . C26 . H263 . 109.4(6) no C24 . C27 . H271 . 109.3(5) no C24 . C27 . H272 . 109.0(5) no H271 . C27 . H272 . 109.1(6) no C24 . C27 . H273 . 109.8(5) no H271 . C27 . H273 . 110.0(6) no H272 . C27 . H273 . 109.6(6) no N1 . C28 . C29 . 118.8(4) no N1 . C28 . C33 . 120.6(4) no C29 . C28 . C33 . 120.5(4) no C28 . C29 . C30 . 119.6(5) no C28 . C29 . H291 . 119.9(4) no C30 . C29 . H291 . 120.5(4) no C29 . C30 . C31 . 119.1(5) no C29 . C30 . C34 . 119.5(6) no C31 . C30 . C34 . 121.4(5) no C30 . C31 . C32 . 122.4(5) no C30 . C31 . H311 . 118.8(6) no C32 . C31 . H311 . 118.9(6) no C31 . C32 . C33 . 118.1(5) no C31 . C32 . C35 . 121.6(5) no C33 . C32 . C35 . 120.3(5) no C28 . C33 . C32 . 120.3(4) no C28 . C33 . H331 . 119.8(4) no C32 . C33 . H331 . 119.9(4) no C30 . C34 . H341 . 109.1(7) no C30 . C34 . H342 . 108.9(6) no H341 . C34 . H342 . 109.7(7) no C30 . C34 . H343 . 109.3(6) no H341 . C34 . H343 . 110.0(7) no H342 . C34 . H343 . 109.8(8) no C32 . C35 . H351 . 109.3(5) no C32 . C35 . H352 . 109.1(6) no H351 . C35 . H352 . 109.4(7) no C32 . C35 . H353 . 109.4(6) no H351 . C35 . H353 . 109.9(7) no H352 . C35 . H353 . 109.7(6) no S1 . C36 . C37 . 119.3(3) no S1 . C36 . C41 . 118.8(3) no C37 . C36 . C41 . 121.6(4) no C36 . C37 . C38 . 118.4(4) no C36 . C37 . H371 . 120.6(4) no C38 . C37 . H371 . 121.0(5) no C37 . C38 . C39 . 120.9(5) no C37 . C38 . H381 . 119.5(6) no C39 . C38 . H381 . 119.6(5) no C38 . C39 . C40 . 120.4(5) no C38 . C39 . H391 . 119.5(6) no C40 . C39 . H391 . 120.1(6) no C39 . C40 . C41 . 120.3(5) no C39 . C40 . H401 . 119.8(5) no C41 . C40 . H401 . 119.9(5) no C36 . C41 . C40 . 118.5(4) no C36 . C41 . H411 . 120.7(4) no C40 . C41 . H411 . 120.9(4) no