# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'J. Clayden' _publ_contact_author_email J.P.CLAYDEN@MAN.AC.UK _publ_section_title ; Doubly dearomatising intramolecular coupling of a nucleophilic and an electrophilic heterocycle ; loop_ _publ_author_name 'J. Clayden' 'Heloise Brice' # Attachment 'spiridon-cif-30781.txt' data_q _database_code_depnum_ccdc_archive 'CCDC 705273' #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H31 F3 N2 O5 S' _chemical_formula_weight 684.71 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' F F 0.0171 0.0103 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4401(18) _cell_length_b 11.6862(19) _cell_length_c 13.896(2) _cell_angle_alpha 71.474(4) _cell_angle_beta 67.306(4) _cell_angle_gamma 71.622(3) _cell_volume 1585.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 511 _cell_measurement_theta_min 2.1985 _cell_measurement_theta_max 18.978 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9330 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.2574 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 26.37 _reflns_number_total 6339 _reflns_number_gt 2587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6339 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1527 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1324 _refine_ls_wR_factor_gt 0.0955 _refine_ls_goodness_of_fit_ref 0.679 _refine_ls_restrained_S_all 0.679 _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 C1 C 0.1226(4) 1.1251(4) 0.7334(3) 0.0134(10) Uani 1 1 d . . . C2 C 0.0104(4) 1.2133(4) 0.7946(3) 0.0136(10) Uani 1 1 d . . . C3 C -0.0218(4) 1.2006(4) 0.9041(3) 0.0152(11) Uani 1 1 d . . . H3 H 0.0372 1.1463 0.9404 0.018 Uiso 1 1 calc R . . C4 C -0.1385(4) 1.2657(4) 0.9611(3) 0.0158(11) Uani 1 1 d . . . H4 H -0.1580 1.2564 1.0358 0.019 Uiso 1 1 calc R . . C5 C -0.2268(4) 1.3441(4) 0.9105(3) 0.0189(11) Uani 1 1 d . . . H5 H -0.3087 1.3853 0.9505 0.023 Uiso 1 1 calc R . . C6 C -0.1946(4) 1.3619(4) 0.8001(3) 0.0161(11) Uani 1 1 d . . . H6 H -0.2526 1.4187 0.7638 0.019 Uiso 1 1 calc R . . C7 C -0.0777(4) 1.2964(4) 0.7436(3) 0.0167(11) Uani 1 1 d . . . H7 H -0.0569 1.3080 0.6685 0.020 Uiso 1 1 calc R . . C8 C 0.1898(4) 1.1883(4) 0.6177(3) 0.0136(10) Uani 1 1 d . . . C9 C 0.1991(4) 1.3109(4) 0.5924(3) 0.0164(11) Uani 1 1 d . . . H9 H 0.1608 1.3577 0.6461 0.020 Uiso 1 1 calc R . . C10 C 0.2650(4) 1.3650(4) 0.4879(4) 0.0204(12) Uani 1 1 d . . . H10 H 0.2696 1.4493 0.4706 0.024 Uiso 1 1 calc R . . C11 C 0.3236(4) 1.2979(4) 0.4093(3) 0.0191(12) Uani 1 1 d . . . H11 H 0.3677 1.3358 0.3383 0.023 Uiso 1 1 calc R . . C12 C 0.3175(4) 1.1738(4) 0.4350(3) 0.0188(11) Uani 1 1 d . . . H12 H 0.3586 1.1263 0.3819 0.023 Uiso 1 1 calc R . . C13 C 0.2513(4) 1.1205(4) 0.5384(3) 0.0167(11) Uani 1 1 d . . . H13 H 0.2477 1.0359 0.5557 0.020 Uiso 1 1 calc R . . C14 C 0.2313(4) 1.0566(4) 0.7833(3) 0.0125(10) Uani 1 1 d . . . C15 C 0.2912(4) 0.9340(4) 0.7815(3) 0.0173(11) Uani 1 1 d . . . H15 H 0.2635 0.8906 0.7498 0.021 Uiso 1 1 calc R . . C16 C 0.3908(4) 0.8733(4) 0.8251(3) 0.0178(11) Uani 1 1 d . . . H16 H 0.4312 0.7893 0.8225 0.021 Uiso 1 1 calc R . . C17 C 0.4319(4) 0.9353(4) 0.8726(3) 0.0198(12) Uani 1 1 d . . . H17 H 0.4980 0.8932 0.9049 0.024 Uiso 1 1 calc R . . C18 C 0.3754(5) 1.0584(4) 0.8722(3) 0.0211(12) Uani 1 1 d . . . H18 H 0.4049 1.1021 0.9023 0.025 Uiso 1 1 calc R . . C19 C 0.2764(4) 1.1189(4) 0.8284(3) 0.0162(11) Uani 1 1 d . . . H19 H 0.2384 1.2037 0.8288 0.019 Uiso 1 1 calc R . . C20 C -0.0030(4) 0.9639(4) 0.8204(3) 0.0149(11) Uani 1 1 d . . . H20 H 0.0307 0.9565 0.8791 0.018 Uiso 1 1 calc R . . C21 C -0.1469(4) 1.0132(4) 0.8520(3) 0.0141(11) Uani 1 1 d . . . H21 H -0.1915 1.0852 0.8799 0.017 Uiso 1 1 calc R . . C22 C -0.2017(4) 0.9416(4) 0.8352(3) 0.0130(10) Uani 1 1 d . . . H22 H -0.2925 0.9540 0.8497 0.016 Uiso 1 1 calc R . . C23 C -0.1021(4) 0.8383(4) 0.7902(3) 0.0117(10) Uani 1 1 d . . . C24 C -0.0777(4) 0.8464(4) 0.6720(3) 0.0153(11) Uani 1 1 d . . . H24A H -0.1602 0.8760 0.6551 0.018 Uiso 1 1 calc R . . H24B H -0.0189 0.9028 0.6249 0.018 Uiso 1 1 calc R . . C25 C -0.0240(5) 0.6354(4) 0.7547(3) 0.0155(11) Uani 1 1 d . . . C26 C -0.1202(4) 0.7031(4) 0.8441(3) 0.0121(10) Uani 1 1 d . . . C27 C 0.0597(4) 0.6919(4) 0.5555(3) 0.0184(11) Uani 1 1 d . . . H27A H 0.0089 0.7334 0.5053 0.022 Uiso 1 1 calc R . . H27B H 0.0785 0.6017 0.5618 0.022 Uiso 1 1 calc R . . C28 C 0.1859(4) 0.7340(4) 0.5107(3) 0.0169(11) Uani 1 1 d . . . C29 C 0.2169(5) 0.8175(4) 0.4140(3) 0.0188(11) Uani 1 1 d . . . H29 H 0.1593 0.8485 0.3728 0.023 Uiso 1 1 calc R . . C30 C 0.3330(5) 0.8562(4) 0.3771(4) 0.0256(12) Uani 1 1 d . . . H30 H 0.3544 0.9133 0.3102 0.031 Uiso 1 1 calc R . . C31 C 0.4166(5) 0.8131(5) 0.4357(4) 0.0302(13) Uani 1 1 d . . . H31 H 0.4956 0.8401 0.4098 0.036 Uiso 1 1 calc R . . C32 C 0.3850(6) 0.7300(6) 0.5329(4) 0.056(2) Uani 1 1 d . . . H32 H 0.4418 0.6998 0.5748 0.067 Uiso 1 1 calc R . . C33 C 0.2693(5) 0.6908(6) 0.5691(4) 0.0444(18) Uani 1 1 d . . . H33 H 0.2481 0.6329 0.6356 0.053 Uiso 1 1 calc R . . C34 C -0.2565(4) 0.6966(4) 0.8591(3) 0.0139(10) Uani 1 1 d . . . H34 H -0.2900 0.7373 0.8011 0.017 Uiso 1 1 calc R . . C35 C -0.3312(4) 0.6384(4) 0.9473(3) 0.0146(10) Uani 1 1 d . . . H35 H -0.4145 0.6358 0.9497 0.018 Uiso 1 1 calc R . . C36 C -0.1689(4) 0.5924(4) 1.0354(3) 0.0143(10) Uani 1 1 d . . . H36 H -0.1425 0.5581 1.0975 0.017 Uiso 1 1 calc R . . C37 C -0.0928(4) 0.6507(4) 0.9478(3) 0.0148(11) Uani 1 1 d . . . H37 H -0.0149 0.6600 0.9510 0.018 Uiso 1 1 calc R . . C38 C -0.4639(5) 0.6053(5) 1.2336(4) 0.0228(12) Uani 1 1 d . . . F1 F -0.5477(3) 0.5523(3) 1.32083(19) 0.0309(8) Uani 1 1 d . . . F2 F -0.3802(3) 0.6317(3) 1.2627(2) 0.0313(8) Uani 1 1 d . . . F3 F -0.5273(3) 0.7073(2) 1.1845(2) 0.0300(7) Uani 1 1 d . . . N1 N -0.0172(4) 0.7194(3) 0.6598(3) 0.0144(9) Uani 1 1 d . . . N2 N -0.2910(4) 0.5797(3) 1.0384(3) 0.0155(9) Uani 1 1 d . . . O1 O 0.0659(3) 1.0363(3) 0.7216(2) 0.0123(7) Uani 1 1 d . . . O2 O 0.0159(3) 0.8464(3) 0.8022(2) 0.0130(7) Uani 1 1 d . . . O3 O 0.0304(3) 0.5269(3) 0.7672(2) 0.0188(8) Uani 1 1 d . . . O4 O -0.2956(3) 0.3995(3) 1.1949(2) 0.0211(8) Uani 1 1 d . . . O5 O -0.4773(3) 0.4766(3) 1.1175(2) 0.0175(8) Uani 1 1 d . . . S001 S -0.37775(12) 0.49728(11) 1.14380(9) 0.0146(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.017(3) 0.010(3) 0.018(3) -0.005(2) -0.009(2) -0.006(2) C2 0.015(3) 0.010(3) 0.018(3) -0.003(2) -0.004(2) -0.007(2) C3 0.016(3) 0.013(3) 0.017(3) -0.003(2) -0.005(2) -0.004(2) C4 0.018(3) 0.022(3) 0.013(3) -0.010(2) -0.004(2) -0.006(2) C5 0.016(3) 0.015(3) 0.024(3) -0.010(2) 0.002(2) -0.005(2) C6 0.021(3) 0.010(3) 0.016(3) -0.001(2) -0.007(2) -0.003(2) C7 0.023(3) 0.021(3) 0.008(2) 0.000(2) -0.004(2) -0.012(2) C8 0.013(3) 0.014(3) 0.013(2) -0.005(2) -0.002(2) -0.003(2) C9 0.014(3) 0.019(3) 0.015(3) -0.007(2) -0.002(2) -0.003(2) C10 0.018(3) 0.010(3) 0.027(3) -0.001(2) -0.002(2) -0.004(2) C11 0.018(3) 0.027(3) 0.010(3) 0.001(2) -0.005(2) -0.006(2) C12 0.022(3) 0.024(3) 0.012(3) -0.008(2) -0.001(2) -0.008(2) C13 0.023(3) 0.010(3) 0.021(3) -0.005(2) -0.007(2) -0.006(2) C14 0.016(3) 0.012(3) 0.007(2) -0.0010(19) 0.002(2) -0.008(2) C15 0.014(3) 0.015(3) 0.018(3) -0.001(2) 0.000(2) -0.007(2) C16 0.014(3) 0.008(3) 0.024(3) 0.000(2) 0.000(2) -0.003(2) C17 0.014(3) 0.023(3) 0.017(3) 0.002(2) -0.003(2) -0.005(2) C18 0.022(3) 0.024(3) 0.023(3) -0.001(2) -0.011(2) -0.012(3) C19 0.019(3) 0.013(3) 0.019(3) -0.005(2) -0.004(2) -0.007(2) C20 0.022(3) 0.016(3) 0.009(2) 0.001(2) -0.001(2) -0.015(2) C21 0.018(3) 0.015(3) 0.008(2) -0.004(2) -0.001(2) -0.004(2) C22 0.015(3) 0.012(3) 0.008(2) 0.0068(19) -0.002(2) -0.009(2) C23 0.014(3) 0.012(3) 0.008(2) 0.0001(19) -0.003(2) -0.006(2) C24 0.021(3) 0.012(3) 0.009(2) -0.002(2) 0.000(2) -0.004(2) C25 0.017(3) 0.020(3) 0.016(3) -0.006(2) -0.007(2) -0.009(2) C26 0.016(3) 0.008(2) 0.013(2) -0.002(2) -0.006(2) -0.002(2) C27 0.024(3) 0.020(3) 0.010(2) -0.006(2) -0.006(2) -0.002(2) C28 0.017(3) 0.023(3) 0.011(2) -0.003(2) -0.007(2) -0.002(2) C29 0.023(3) 0.019(3) 0.013(3) -0.001(2) -0.009(2) 0.000(2) C30 0.026(3) 0.018(3) 0.025(3) -0.007(2) -0.002(3) -0.001(3) C31 0.024(3) 0.039(4) 0.025(3) -0.008(3) 0.000(3) -0.010(3) C32 0.025(4) 0.110(6) 0.024(3) 0.008(4) -0.012(3) -0.022(4) C33 0.021(3) 0.083(5) 0.017(3) 0.016(3) -0.008(3) -0.021(4) C34 0.012(3) 0.012(3) 0.018(3) -0.004(2) -0.006(2) -0.002(2) C35 0.015(3) 0.013(3) 0.016(2) -0.003(2) -0.005(2) -0.003(2) C36 0.017(3) 0.009(2) 0.017(3) -0.006(2) -0.004(2) -0.003(2) C37 0.013(3) 0.015(3) 0.020(3) -0.008(2) -0.005(2) -0.003(2) C38 0.024(3) 0.025(3) 0.022(3) -0.005(2) -0.003(2) -0.015(3) F1 0.0339(19) 0.038(2) 0.0170(15) -0.0099(14) 0.0101(13) -0.0224(16) F2 0.0351(19) 0.045(2) 0.0239(16) -0.0166(15) -0.0007(14) -0.0251(17) F3 0.0323(19) 0.0188(17) 0.0305(17) -0.0056(14) -0.0030(14) -0.0030(15) N1 0.022(2) 0.016(2) 0.008(2) -0.0025(17) -0.0053(18) -0.0071(19) N2 0.018(2) 0.021(2) 0.010(2) -0.0013(17) -0.0033(18) -0.0119(19) O1 0.0143(18) 0.0118(17) 0.0113(16) -0.0041(13) 0.0010(14) -0.0085(14) O2 0.0105(18) 0.0110(17) 0.0180(17) -0.0060(14) -0.0028(14) -0.0023(14) O3 0.024(2) 0.0132(19) 0.0212(18) -0.0065(15) -0.0079(16) -0.0032(16) O4 0.025(2) 0.0175(19) 0.0173(18) 0.0031(15) -0.0083(16) -0.0055(17) O5 0.0192(19) 0.0217(19) 0.0161(18) -0.0022(15) -0.0061(15) -0.0121(16) S001 0.0174(7) 0.0132(7) 0.0123(6) -0.0019(5) -0.0016(5) -0.0070(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 C1 O1 1.462(4) . ? C1 C2 1.521(6) . ? C1 C8 1.539(5) . ? C1 C14 1.534(6) . ? C2 C7 1.400(6) . ? C2 C3 1.389(5) . ? C3 C4 1.383(6) . ? C3 H3 0.9500 . ? C4 C5 1.383(6) . ? C4 H4 0.9500 . ? C5 C6 1.393(5) . ? C5 H5 0.9500 . ? C6 C7 1.385(6) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.391(6) . ? C8 C13 1.394(6) . ? C9 C10 1.396(5) . ? C9 H9 0.9500 . ? C10 C11 1.380(6) . ? C10 H10 0.9500 . ? C11 C12 1.397(6) . ? C11 H11 0.9500 . ? C12 C13 1.384(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.383(6) . ? C14 C19 1.401(5) . ? C15 C16 1.385(6) . ? C15 H15 0.9500 . ? C16 C17 1.392(6) . ? C16 H16 0.9500 . ? C17 C18 1.379(6) . ? C17 H17 0.9500 . ? C18 C19 1.381(6) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 O2 1.409(5) . ? C20 O1 1.439(4) . ? C20 C21 1.496(6) . ? C20 H20 1.0000 . ? C21 C22 1.310(5) . ? C21 H21 0.9500 . ? C22 C23 1.486(6) . ? C22 H22 0.9500 . ? C23 O2 1.457(5) . ? C23 C24 1.532(5) . ? C23 C26 1.560(5) . ? C24 N1 1.461(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 O3 1.213(5) . ? C25 N1 1.362(5) . ? C25 C26 1.550(6) . ? C26 C37 1.488(5) . ? C26 C34 1.515(5) . ? C27 N1 1.453(5) . ? C27 C28 1.507(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C33 1.363(6) . ? C28 C29 1.379(5) . ? C29 C30 1.391(6) . ? C29 H29 0.9500 . ? C30 C31 1.367(6) . ? C30 H30 0.9500 . ? C31 C32 1.383(6) . ? C31 H31 0.9500 . ? C32 C33 1.392(6) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C35 1.313(5) . ? C34 H34 0.9500 . ? C35 N2 1.409(5) . ? C35 H35 0.9500 . ? C36 C37 1.316(5) . ? C36 N2 1.434(5) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 F3 1.317(5) . ? C38 F2 1.320(5) . ? C38 F1 1.331(5) . ? C38 S001 1.841(5) . ? N2 S001 1.626(3) . ? O4 S001 1.420(3) . ? O5 S001 1.428(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 106.5(3) . . ? O1 C1 C8 104.4(3) . . ? C2 C1 C8 113.2(4) . . ? O1 C1 C14 110.1(3) . . ? C2 C1 C14 116.1(4) . . ? C8 C1 C14 106.0(4) . . ? C7 C2 C3 117.7(4) . . ? C7 C2 C1 118.6(4) . . ? C3 C2 C1 122.6(4) . . ? C4 C3 C2 121.1(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 120.6(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 119.3(4) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C7 119.7(4) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C2 C7 C6 121.5(4) . . ? C2 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C9 C8 C13 118.9(4) . . ? C9 C8 C1 120.7(4) . . ? C13 C8 C1 120.2(4) . . ? C10 C9 C8 119.8(4) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C11 C10 C9 121.0(4) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 119.4(4) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 119.6(4) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C8 121.3(4) . . ? C12 C13 H13 119.3 . . ? C8 C13 H13 119.3 . . ? C15 C14 C19 118.0(4) . . ? C15 C14 C1 121.5(4) . . ? C19 C14 C1 120.4(4) . . ? C14 C15 C16 121.2(4) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C15 C16 C17 120.1(4) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 119.2(4) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 120.6(4) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C14 120.9(4) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? O2 C20 O1 106.8(3) . . ? O2 C20 C21 105.1(3) . . ? O1 C20 C21 112.9(4) . . ? O2 C20 H20 110.6 . . ? O1 C20 H20 110.6 . . ? C21 C20 H20 110.6 . . ? C22 C21 C20 109.4(4) . . ? C22 C21 H21 125.3 . . ? C20 C21 H21 125.3 . . ? C21 C22 C23 110.6(4) . . ? C21 C22 H22 124.7 . . ? C23 C22 H22 124.7 . . ? O2 C23 C22 103.5(3) . . ? O2 C23 C24 108.8(3) . . ? C22 C23 C24 115.5(4) . . ? O2 C23 C26 107.1(3) . . ? C22 C23 C26 118.9(4) . . ? C24 C23 C26 102.6(3) . . ? N1 C24 C23 103.8(3) . . ? N1 C24 H24A 111.0 . . ? C23 C24 H24A 111.0 . . ? N1 C24 H24B 111.0 . . ? C23 C24 H24B 111.0 . . ? H24A C24 H24B 109.0 . . ? O3 C25 N1 126.8(4) . . ? O3 C25 C26 126.2(4) . . ? N1 C25 C26 107.0(4) . . ? C37 C26 C34 109.8(3) . . ? C37 C26 C25 113.3(4) . . ? C34 C26 C25 108.3(3) . . ? C37 C26 C23 114.7(3) . . ? C34 C26 C23 109.6(4) . . ? C25 C26 C23 100.7(3) . . ? N1 C27 C28 112.1(3) . . ? N1 C27 H27A 109.2 . . ? C28 C27 H27A 109.2 . . ? N1 C27 H27B 109.2 . . ? C28 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? C33 C28 C29 119.4(4) . . ? C33 C28 C27 118.8(4) . . ? C29 C28 C27 121.7(4) . . ? C30 C29 C28 119.7(4) . . ? C30 C29 H29 120.1 . . ? C28 C29 H29 120.1 . . ? C31 C30 C29 120.9(4) . . ? C31 C30 H30 119.5 . . ? C29 C30 H30 119.5 . . ? C30 C31 C32 119.3(5) . . ? C30 C31 H31 120.3 . . ? C32 C31 H31 120.3 . . ? C33 C32 C31 119.5(5) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C28 C33 C32 121.1(5) . . ? C28 C33 H33 119.5 . . ? C32 C33 H33 119.5 . . ? C35 C34 C26 124.1(4) . . ? C35 C34 H34 118.0 . . ? C26 C34 H34 118.0 . . ? C34 C35 N2 121.6(4) . . ? C34 C35 H35 119.2 . . ? N2 C35 H35 119.2 . . ? C37 C36 N2 121.0(4) . . ? C37 C36 H36 119.5 . . ? N2 C36 H36 119.5 . . ? C36 C37 C26 124.7(4) . . ? C36 C37 H37 117.7 . . ? C26 C37 H37 117.7 . . ? F3 C38 F2 109.9(4) . . ? F3 C38 F1 109.4(4) . . ? F2 C38 F1 108.6(4) . . ? F3 C38 S001 109.8(3) . . ? F2 C38 S001 110.0(4) . . ? F1 C38 S001 109.2(3) . . ? C25 N1 C27 124.5(4) . . ? C25 N1 C24 113.4(4) . . ? C27 N1 C24 121.4(3) . . ? C35 N2 C36 118.1(3) . . ? C35 N2 S001 121.6(3) . . ? C36 N2 S001 120.2(3) . . ? C1 O1 C20 115.1(3) . . ? C20 O2 C23 108.6(3) . . ? O4 S001 O5 122.26(18) . . ? O4 S001 N2 110.01(19) . . ? O5 S001 N2 108.73(17) . . ? O4 S001 C38 106.4(2) . . ? O5 S001 C38 104.7(2) . . ? N2 S001 C38 102.8(2) . . ? 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 O1 C1 C2 C7 -69.7(5) . . . . ? C8 C1 C2 C7 44.4(5) . . . . ? C14 C1 C2 C7 167.3(4) . . . . ? O1 C1 C2 C3 98.6(4) . . . . ? C8 C1 C2 C3 -147.3(4) . . . . ? C14 C1 C2 C3 -24.4(6) . . . . ? C7 C2 C3 C4 1.5(6) . . . . ? C1 C2 C3 C4 -166.8(4) . . . . ? C2 C3 C4 C5 0.8(6) . . . . ? C3 C4 C5 C6 -3.2(6) . . . . ? C4 C5 C6 C7 3.2(6) . . . . ? C3 C2 C7 C6 -1.4(6) . . . . ? C1 C2 C7 C6 167.4(4) . . . . ? C5 C6 C7 C2 -0.9(6) . . . . ? O1 C1 C8 C9 148.6(4) . . . . ? C2 C1 C8 C9 33.1(6) . . . . ? C14 C1 C8 C9 -95.2(5) . . . . ? O1 C1 C8 C13 -36.6(5) . . . . ? C2 C1 C8 C13 -152.0(4) . . . . ? C14 C1 C8 C13 79.7(5) . . . . ? C13 C8 C9 C10 2.5(7) . . . . ? C1 C8 C9 C10 177.4(4) . . . . ? C8 C9 C10 C11 -1.3(7) . . . . ? C9 C10 C11 C12 -0.4(7) . . . . ? C10 C11 C12 C13 0.9(7) . . . . ? C11 C12 C13 C8 0.3(7) . . . . ? C9 C8 C13 C12 -2.0(7) . . . . ? C1 C8 C13 C12 -176.9(4) . . . . ? O1 C1 C14 C15 19.7(6) . . . . ? C2 C1 C14 C15 140.9(4) . . . . ? C8 C1 C14 C15 -92.6(5) . . . . ? O1 C1 C14 C19 -163.0(3) . . . . ? C2 C1 C14 C19 -41.9(5) . . . . ? C8 C1 C14 C19 84.7(5) . . . . ? C19 C14 C15 C16 1.5(6) . . . . ? C1 C14 C15 C16 178.8(4) . . . . ? C14 C15 C16 C17 0.5(7) . . . . ? C15 C16 C17 C18 -2.3(7) . . . . ? C16 C17 C18 C19 2.1(7) . . . . ? C17 C18 C19 C14 -0.1(7) . . . . ? C15 C14 C19 C18 -1.7(6) . . . . ? C1 C14 C19 C18 -179.1(4) . . . . ? O2 C20 C21 C22 -10.1(4) . . . . ? O1 C20 C21 C22 106.0(4) . . . . ? C20 C21 C22 C23 -0.4(5) . . . . ? C21 C22 C23 O2 10.4(4) . . . . ? C21 C22 C23 C24 -108.4(4) . . . . ? C21 C22 C23 C26 129.0(4) . . . . ? O2 C23 C24 N1 84.5(4) . . . . ? C22 C23 C24 N1 -159.8(4) . . . . ? C26 C23 C24 N1 -28.8(4) . . . . ? O3 C25 C26 C37 30.8(6) . . . . ? N1 C25 C26 C37 -151.9(3) . . . . ? O3 C25 C26 C34 -91.3(5) . . . . ? N1 C25 C26 C34 86.0(4) . . . . ? O3 C25 C26 C23 153.8(4) . . . . ? N1 C25 C26 C23 -28.9(4) . . . . ? O2 C23 C26 C37 41.9(5) . . . . ? C22 C23 C26 C37 -74.7(5) . . . . ? C24 C23 C26 C37 156.4(4) . . . . ? O2 C23 C26 C34 166.0(3) . . . . ? C22 C23 C26 C34 49.3(5) . . . . ? C24 C23 C26 C34 -79.5(4) . . . . ? O2 C23 C26 C25 -80.0(4) . . . . ? C22 C23 C26 C25 163.3(4) . . . . ? C24 C23 C26 C25 34.5(4) . . . . ? N1 C27 C28 C33 56.9(6) . . . . ? N1 C27 C28 C29 -121.2(5) . . . . ? C33 C28 C29 C30 0.2(8) . . . . ? C27 C28 C29 C30 178.4(4) . . . . ? C28 C29 C30 C31 -0.4(8) . . . . ? C29 C30 C31 C32 0.1(8) . . . . ? C30 C31 C32 C33 0.5(9) . . . . ? C29 C28 C33 C32 0.3(9) . . . . ? C27 C28 C33 C32 -177.9(6) . . . . ? C31 C32 C33 C28 -0.7(10) . . . . ? C37 C26 C34 C35 -8.3(6) . . . . ? C25 C26 C34 C35 115.9(5) . . . . ? C23 C26 C34 C35 -135.2(4) . . . . ? C26 C34 C35 N2 2.4(7) . . . . ? N2 C36 C37 C26 -3.0(7) . . . . ? C34 C26 C37 C36 8.6(6) . . . . ? C25 C26 C37 C36 -112.7(5) . . . . ? C23 C26 C37 C36 132.5(5) . . . . ? O3 C25 N1 C27 -0.7(7) . . . . ? C26 C25 N1 C27 -178.0(4) . . . . ? O3 C25 N1 C24 -171.1(4) . . . . ? C26 C25 N1 C24 11.6(5) . . . . ? C28 C27 N1 C25 -100.5(5) . . . . ? C28 C27 N1 C24 69.2(5) . . . . ? C23 C24 N1 C25 11.4(5) . . . . ? C23 C24 N1 C27 -159.3(4) . . . . ? C34 C35 N2 C36 4.3(7) . . . . ? C34 C35 N2 S001 -174.4(4) . . . . ? C37 C36 N2 C35 -4.1(7) . . . . ? C37 C36 N2 S001 174.7(4) . . . . ? C2 C1 O1 C20 -60.3(4) . . . . ? C8 C1 O1 C20 179.7(4) . . . . ? C14 C1 O1 C20 66.4(5) . . . . ? O2 C20 O1 C1 -146.3(3) . . . . ? C21 C20 O1 C1 98.7(4) . . . . ? O1 C20 O2 C23 -103.6(3) . . . . ? C21 C20 O2 C23 16.6(4) . . . . ? C22 C23 O2 C20 -16.7(4) . . . . ? C24 C23 O2 C20 106.6(4) . . . . ? C26 C23 O2 C20 -143.1(3) . . . . ? C35 N2 S001 O4 148.1(3) . . . . ? C36 N2 S001 O4 -30.6(4) . . . . ? C35 N2 S001 O5 11.8(4) . . . . ? C36 N2 S001 O5 -166.9(3) . . . . ? C35 N2 S001 C38 -98.8(4) . . . . ? C36 N2 S001 C38 82.4(4) . . . . ? F3 C38 S001 O4 170.7(3) . . . . ? F2 C38 S001 O4 49.6(4) . . . . ? F1 C38 S001 O4 -69.4(4) . . . . ? F3 C38 S001 O5 -58.6(3) . . . . ? F2 C38 S001 O5 -179.6(3) . . . . ? F1 C38 S001 O5 61.3(4) . . . . ? F3 C38 S001 N2 55.0(3) . . . . ? F2 C38 S001 N2 -66.0(3) . . . . ? F1 C38 S001 N2 174.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.269 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.067 # start Validation Reply Form _vrf_PLAT213_s3078n ; PROBLEM: Atom C22 has ADP max/min Ratio ............. 6.20 oblat RESPONSE: While the ratio is quite high, the numerator is quite modest; there is no evidence either of disorder or element misassignment; bond lengths are reasonable. ; _vrf_PLAT220_s3078n ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.00 Ratio RESPONSE: There are a number of rigidly bonded carbons, such as the spiro carbons as well as carbons like the phenyl carbons where more atomic movement is possible. ; # end Validation Reply Form