# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2022 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_003595 _database_code_depnum_ccdc_archive 'CCDC 1923120' loop_ _audit_author_name _audit_author_address 'Andre Alker' ;F Hoffmann La Roche AG Germany ; _audit_update_record ; 2019-06-14 deposited with the CCDC. 2022-04-22 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H30 N2 O5 S' _chemical_formula_weight 422.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.83040(10) _cell_length_b 12.83900(10) _cell_length_c 15.08690(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2291.56(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 35729 _cell_measurement_theta_min 3.7600 _cell_measurement_theta_max 68.0650 _exptl_crystal_description stubby _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_F_000 904 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.100 _exptl_absorpt_coefficient_mu 1.526 _shelx_estimated_absorpt_T_min 0.657 _shelx_estimated_absorpt_T_max 0.862 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.94529 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix3000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0.83 _diffrn_reflns_number 51264 _diffrn_reflns_av_unetI/netI 0.0123 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.522 _diffrn_reflns_theta_max 68.096 _diffrn_reflns_theta_full 67.679 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 4179 _reflns_number_gt 4032 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.757 _reflns_Friedel_fraction_max 0.998 _reflns_Friedel_fraction_full 1.000 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)' _computing_cell_refinement 'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)' _computing_structure_solution 'SHELXS-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics XSHELL _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+0.2364P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_extinction_coef 0.0020(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Flack x determined using 1701 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.014(7) _chemical_absolute_configuration ad _refine_ls_number_reflns 4179 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.006 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.41330(6) 0.20465(4) 0.88477(4) 0.06003(18) Uani 1 1 d . . . . . O2 O 0.5091(2) 0.13800(15) 0.87753(14) 0.0855(6) Uani 1 1 d . . . . . O3 O 0.3040(2) 0.16878(18) 0.86118(14) 0.0883(7) Uani 1 1 d . . . . . O4 O 0.18922(15) 0.39307(16) 0.70512(13) 0.0748(5) Uani 1 1 d . . . . . O5 O 0.47069(14) 0.17048(15) 0.56756(12) 0.0674(5) Uani 1 1 d . . . . . O6 O 0.35429(14) 0.16111(15) 0.45102(11) 0.0619(4) Uani 1 1 d . . . . . N7 N 0.33540(16) 0.29257(15) 0.65815(11) 0.0484(4) Uani 1 1 d . . . . . N8 N 0.43862(16) 0.30386(15) 0.82091(12) 0.0540(4) Uani 1 1 d . . . . . C9 C 0.4972(2) 0.2338(3) 1.05075(18) 0.0804(9) Uani 1 1 d . . . . . H9 H 0.5615 0.1995 1.0304 0.096 Uiso 1 1 calc R U . . . C10 C 0.4928(3) 0.2682(3) 1.13736(19) 0.0887(10) Uani 1 1 d . . . . . H10 H 0.5544 0.2570 1.1744 0.106 Uiso 1 1 calc R U . . . C11 C 0.4002(2) 0.31838(19) 1.16982(16) 0.0625(6) Uani 1 1 d . . . . . C12 C 0.3935(3) 0.3548(3) 1.26495(18) 0.0885(9) Uani 1 1 d . . . . . H12A H 0.4545 0.3248 1.2983 0.133 Uiso 1 1 calc R U . . . H12B H 0.3227 0.3335 1.2902 0.133 Uiso 1 1 calc R U . . . H12C H 0.3992 0.4294 1.2668 0.133 Uiso 1 1 calc R U . . . C13 C 0.3104(3) 0.3325(3) 1.11355(19) 0.0861(10) Uani 1 1 d . . . . . H13 H 0.2460 0.3665 1.1341 0.103 Uiso 1 1 calc R U . . . C14 C 0.3136(2) 0.2974(3) 1.02695(18) 0.0844(9) Uani 1 1 d . . . . . H14 H 0.2512 0.3063 0.9903 0.101 Uiso 1 1 calc R U . . . C15 C 0.4088(2) 0.24926(17) 0.99502(14) 0.0515(5) Uani 1 1 d . . . . . C16 C 0.5483(2) 0.3591(2) 0.8280(2) 0.0722(7) Uani 1 1 d . . . . . H16A H 0.6092 0.3179 0.8031 0.087 Uiso 1 1 calc R U . . . H16B H 0.5659 0.3756 0.8892 0.087 Uiso 1 1 calc R U . . . C17 C 0.5284(3) 0.4562(3) 0.7747(2) 0.0841(9) Uani 1 1 d . . . . . H17A H 0.5793 0.5115 0.7928 0.101 Uiso 1 1 calc R U . . . H17B H 0.5383 0.4430 0.7119 0.101 Uiso 1 1 calc R U . . . C18 C 0.4082(3) 0.4835(2) 0.7955(2) 0.0777(8) Uani 1 1 d . . . . . H18A H 0.3759 0.5262 0.7489 0.093 Uiso 1 1 calc R U . . . H18B H 0.4032 0.5210 0.8512 0.093 Uiso 1 1 calc R U . . . C19 C 0.3466(2) 0.37835(18) 0.80174(15) 0.0541(5) Uani 1 1 d . . . . . H19 H 0.2936 0.3798 0.8517 0.065 Uiso 1 1 calc R U . . . C20 C 0.28246(19) 0.35371(18) 0.71656(14) 0.0516(5) Uani 1 1 d . . . . . C21 C 0.29257(17) 0.26411(16) 0.57041(13) 0.0462(5) Uani 1 1 d . . . . . C22 C 0.2736(2) 0.36037(18) 0.51141(15) 0.0563(5) Uani 1 1 d . . . . . H22A H 0.2477 0.3372 0.4537 0.068 Uiso 1 1 calc R U . . . H22B H 0.2139 0.4023 0.5373 0.068 Uiso 1 1 calc R U . . . C23 C 0.3763(3) 0.4280(2) 0.49884(19) 0.0730(7) Uani 1 1 d . . . . . H23A H 0.3961 0.4599 0.5543 0.109 Uiso 1 1 calc R U . . . H23B H 0.3601 0.4811 0.4559 0.109 Uiso 1 1 calc R U . . . H23C H 0.4382 0.3861 0.4783 0.109 Uiso 1 1 calc R U . . . C24 C 0.18303(17) 0.19946(19) 0.57747(16) 0.0542(5) Uani 1 1 d . . . . . H24A H 0.1266 0.2403 0.6085 0.065 Uiso 1 1 calc R U . . . H24B H 0.1547 0.1861 0.5182 0.065 Uiso 1 1 calc R U . . . C25 C 0.1973(2) 0.0983(2) 0.62409(18) 0.0638(6) Uani 1 1 d . . . . . H25 H 0.2175 0.1004 0.6836 0.077 Uiso 1 1 calc R U . . . C26 C 0.1837(3) 0.0077(2) 0.5884(3) 0.0853(9) Uani 1 1 d . . . . . H26A H 0.1634 0.0023 0.5290 0.102 Uiso 1 1 calc R U . . . H26B H 0.1942 -0.0522 0.6221 0.102 Uiso 1 1 calc R U . . . C27 C 0.38427(17) 0.19400(17) 0.53051(14) 0.0497(5) Uani 1 1 d . . . . . C28 C 0.4268(3) 0.0835(2) 0.4094(2) 0.0775(8) Uani 1 1 d . . . . . H28A H 0.4352 0.0234 0.4478 0.093 Uiso 1 1 calc R U . . . H28B H 0.5012 0.1126 0.3982 0.093 Uiso 1 1 calc R U . . . C29 C 0.3730(4) 0.0529(3) 0.3254(3) 0.1078(13) Uani 1 1 d . . . . . H29A H 0.2986 0.0263 0.3372 0.162 Uiso 1 1 calc R U . . . H29B H 0.4175 0.0000 0.2972 0.162 Uiso 1 1 calc R U . . . H29C H 0.3676 0.1125 0.2872 0.162 Uiso 1 1 calc R U . . . H7 H 0.397(3) 0.271(2) 0.6685(18) 0.061(8) Uiso 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 S1 0.0836(4) 0.0462(3) 0.0503(3) -0.0007(2) -0.0065(3) -0.0051(3) O2 0.1316(18) 0.0572(10) 0.0677(11) -0.0050(9) 0.0033(12) 0.0295(11) O3 0.1086(16) 0.0804(12) 0.0760(12) 0.0042(10) -0.0236(11) -0.0426(12) O4 0.0614(10) 0.0905(13) 0.0723(11) -0.0219(10) -0.0081(8) 0.0234(9) O5 0.0539(9) 0.0833(12) 0.0649(10) -0.0155(9) -0.0077(8) 0.0158(8) O6 0.0638(9) 0.0701(10) 0.0519(8) -0.0170(8) -0.0015(7) 0.0050(8) N7 0.0471(9) 0.0546(10) 0.0436(9) -0.0055(8) -0.0033(7) 0.0050(8) N8 0.0613(10) 0.0550(10) 0.0458(9) 0.0016(8) -0.0063(8) -0.0041(9) C9 0.0615(14) 0.119(3) 0.0604(14) -0.0093(15) -0.0074(12) 0.0337(16) C10 0.0652(16) 0.142(3) 0.0590(15) -0.0122(17) -0.0144(12) 0.0242(18) C11 0.0750(15) 0.0627(14) 0.0497(12) 0.0047(10) 0.0037(11) 0.0023(12) C12 0.126(3) 0.0862(19) 0.0536(14) -0.0025(14) 0.0092(16) 0.007(2) C13 0.0764(17) 0.122(3) 0.0603(15) 0.0126(16) 0.0125(14) 0.0390(18) C14 0.0598(14) 0.137(3) 0.0565(14) 0.0093(16) -0.0042(11) 0.0248(17) C15 0.0565(11) 0.0497(10) 0.0483(10) 0.0074(8) -0.0035(10) -0.0005(10) C16 0.0636(14) 0.0812(18) 0.0718(16) 0.0104(14) -0.0069(12) -0.0124(13) C17 0.090(2) 0.0779(18) 0.0846(19) 0.0163(15) -0.0145(16) -0.0272(16) C18 0.099(2) 0.0534(13) 0.0808(18) -0.0028(12) -0.0200(17) -0.0065(15) C19 0.0648(13) 0.0530(12) 0.0445(11) -0.0064(9) -0.0008(10) 0.0034(10) C20 0.0543(12) 0.0537(12) 0.0466(11) -0.0040(9) 0.0009(9) 0.0009(10) C21 0.0464(10) 0.0517(11) 0.0406(9) -0.0036(8) -0.0027(8) -0.0004(8) C22 0.0630(13) 0.0557(12) 0.0502(11) 0.0013(10) -0.0032(10) 0.0056(11) C23 0.090(2) 0.0611(15) 0.0680(16) 0.0056(12) -0.0014(14) -0.0128(13) C24 0.0446(10) 0.0605(12) 0.0573(12) -0.0034(10) -0.0023(9) -0.0011(10) C25 0.0592(13) 0.0670(14) 0.0652(14) 0.0042(12) 0.0010(11) -0.0086(11) C26 0.094(2) 0.0621(16) 0.099(2) 0.0042(15) -0.0052(18) -0.0109(15) C27 0.0502(11) 0.0513(11) 0.0476(10) -0.0042(9) 0.0016(8) -0.0012(9) C28 0.0745(16) 0.0798(17) 0.0783(18) -0.0304(14) 0.0123(14) 0.0051(14) C29 0.140(3) 0.095(2) 0.088(2) -0.040(2) 0.002(2) 0.002(2) _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 S1 O3 1.418(2) . ? S1 O2 1.424(2) . ? S1 N8 1.6250(19) . ? S1 C15 1.760(2) . ? O4 C20 1.226(3) . ? O5 C27 1.204(3) . ? O6 C27 1.320(3) . ? O6 C28 1.457(3) . ? N7 C20 1.336(3) . ? N7 C21 1.464(3) . ? N7 H7 0.80(3) . ? N8 C19 1.478(3) . ? N8 C16 1.482(3) . ? C9 C15 1.357(3) . ? C9 C10 1.381(4) . ? C9 H9 0.9300 . ? C10 C11 1.361(4) . ? C10 H10 0.9300 . ? C11 C13 1.372(4) . ? C11 C12 1.512(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.383(4) . ? C13 H13 0.9300 . ? C14 C15 1.371(4) . ? C14 H14 0.9300 . ? C16 C17 1.501(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.498(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.537(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.525(3) . ? C19 H19 0.9800 . ? C21 C27 1.533(3) . ? C21 C22 1.540(3) . ? C21 C24 1.543(3) . ? C22 C23 1.505(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.486(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.293(4) . ? C25 H25 0.9300 . ? C26 H26A 0.9300 . ? C26 H26B 0.9300 . ? C28 C29 1.471(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 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 O3 S1 O2 120.74(15) . . ? O3 S1 N8 105.89(11) . . ? O2 S1 N8 106.20(12) . . ? O3 S1 C15 108.37(13) . . ? O2 S1 C15 106.99(12) . . ? N8 S1 C15 108.11(10) . . ? C27 O6 C28 116.9(2) . . ? C20 N7 C21 125.51(19) . . ? C20 N7 H7 120(2) . . ? C21 N7 H7 114(2) . . ? C19 N8 C16 110.45(19) . . ? C19 N8 S1 119.17(15) . . ? C16 N8 S1 119.58(16) . . ? C15 C9 C10 120.7(2) . . ? C15 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 121.5(3) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C10 C11 C13 117.6(2) . . ? C10 C11 C12 122.0(3) . . ? C13 C11 C12 120.4(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 C14 121.3(3) . . ? C11 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 120.1(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C9 C15 C14 118.8(2) . . ? C9 C15 S1 120.97(19) . . ? C14 C15 S1 120.22(19) . . ? N8 C16 C17 102.8(2) . . ? N8 C16 H16A 111.2 . . ? C17 C16 H16A 111.2 . . ? N8 C16 H16B 111.2 . . ? C17 C16 H16B 111.2 . . ? H16A C16 H16B 109.1 . . ? C18 C17 C16 103.4(3) . . ? C18 C17 H17A 111.1 . . ? C16 C17 H17A 111.1 . . ? C18 C17 H17B 111.1 . . ? C16 C17 H17B 111.1 . . ? H17A C17 H17B 109.1 . . ? C17 C18 C19 104.9(2) . . ? C17 C18 H18A 110.8 . . ? C19 C18 H18A 110.8 . . ? C17 C18 H18B 110.8 . . ? C19 C18 H18B 110.8 . . ? H18A C18 H18B 108.8 . . ? N8 C19 C20 113.39(18) . . ? N8 C19 C18 103.3(2) . . ? C20 C19 C18 111.5(2) . . ? N8 C19 H19 109.5 . . ? C20 C19 H19 109.5 . . ? C18 C19 H19 109.5 . . ? O4 C20 N7 124.8(2) . . ? O4 C20 C19 118.7(2) . . ? N7 C20 C19 116.39(19) . . ? N7 C21 C27 104.88(16) . . ? N7 C21 C22 111.90(18) . . ? C27 C21 C22 110.35(17) . . ? N7 C21 C24 111.26(17) . . ? C27 C21 C24 107.79(16) . . ? C22 C21 C24 110.44(17) . . ? C23 C22 C21 114.7(2) . . ? C23 C22 H22A 108.6 . . ? C21 C22 H22A 108.6 . . ? C23 C22 H22B 108.6 . . ? C21 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C21 114.05(18) . . ? C25 C24 H24A 108.7 . . ? C21 C24 H24A 108.7 . . ? C25 C24 H24B 108.7 . . ? C21 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? C26 C25 C24 125.1(3) . . ? C26 C25 H25 117.4 . . ? C24 C25 H25 117.4 . . ? C25 C26 H26A 120.0 . . ? C25 C26 H26B 120.0 . . ? H26A C26 H26B 120.0 . . ? O5 C27 O6 124.7(2) . . ? O5 C27 C21 124.5(2) . . ? O6 C27 C21 110.76(17) . . ? O6 C28 C29 107.4(3) . . ? O6 C28 H28A 110.2 . . ? C29 C28 H28A 110.2 . . ? O6 C28 H28B 110.2 . . ? C29 C28 H28B 110.2 . . ? H28A C28 H28B 108.5 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 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 O3 S1 N8 C19 39.9(2) . . . . ? O2 S1 N8 C19 169.38(17) . . . . ? C15 S1 N8 C19 -76.10(18) . . . . ? O3 S1 N8 C16 -179.1(2) . . . . ? O2 S1 N8 C16 -49.6(2) . . . . ? C15 S1 N8 C16 64.9(2) . . . . ? C15 C9 C10 C11 0.2(6) . . . . ? C9 C10 C11 C13 0.7(5) . . . . ? C9 C10 C11 C12 178.9(4) . . . . ? C10 C11 C13 C14 -0.1(5) . . . . ? C12 C11 C13 C14 -178.3(3) . . . . ? C11 C13 C14 C15 -1.5(6) . . . . ? C10 C9 C15 C14 -1.7(5) . . . . ? C10 C9 C15 S1 -179.5(3) . . . . ? C13 C14 C15 C9 2.4(5) . . . . ? C13 C14 C15 S1 -179.9(3) . . . . ? O3 S1 C15 C9 142.9(3) . . . . ? O2 S1 C15 C9 11.2(3) . . . . ? N8 S1 C15 C9 -102.8(3) . . . . ? O3 S1 C15 C14 -34.8(3) . . . . ? O2 S1 C15 C14 -166.5(3) . . . . ? N8 S1 C15 C14 79.5(3) . . . . ? C19 N8 C16 C17 -24.0(3) . . . . ? S1 N8 C16 C17 -168.1(2) . . . . ? N8 C16 C17 C18 37.3(3) . . . . ? C16 C17 C18 C19 -37.4(3) . . . . ? C16 N8 C19 C20 122.1(2) . . . . ? S1 N8 C19 C20 -93.7(2) . . . . ? C16 N8 C19 C18 1.2(3) . . . . ? S1 N8 C19 C18 145.44(18) . . . . ? C17 C18 C19 N8 22.4(3) . . . . ? C17 C18 C19 C20 -99.8(3) . . . . ? C21 N7 C20 O4 1.4(4) . . . . ? C21 N7 C20 C19 -176.25(19) . . . . ? N8 C19 C20 O4 162.3(2) . . . . ? C18 C19 C20 O4 -81.5(3) . . . . ? N8 C19 C20 N7 -19.9(3) . . . . ? C18 C19 C20 N7 96.2(3) . . . . ? C20 N7 C21 C27 179.8(2) . . . . ? C20 N7 C21 C22 60.2(3) . . . . ? C20 N7 C21 C24 -63.9(3) . . . . ? N7 C21 C22 C23 56.5(3) . . . . ? C27 C21 C22 C23 -59.9(3) . . . . ? C24 C21 C22 C23 -179.0(2) . . . . ? N7 C21 C24 C25 -62.2(2) . . . . ? C27 C21 C24 C25 52.3(2) . . . . ? C22 C21 C24 C25 172.90(19) . . . . ? C21 C24 C25 C26 -115.9(3) . . . . ? C28 O6 C27 O5 5.8(4) . . . . ? C28 O6 C27 C21 -172.7(2) . . . . ? N7 C21 C27 O5 0.2(3) . . . . ? C22 C21 C27 O5 120.9(2) . . . . ? C24 C21 C27 O5 -118.4(2) . . . . ? N7 C21 C27 O6 178.77(18) . . . . ? C22 C21 C27 O6 -60.6(2) . . . . ? C24 C21 C27 O6 60.1(2) . . . . ? C27 O6 C28 C29 175.8(3) . . . . ? _refine_diff_density_max 0.150 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.031 _shelx_res_file ; x3595_cu_rt_2.res created by SHELXL-2014/7 TITL x3595_cu_rt_2 in P2(1)2(1)2(1),U.Grether,RO7304740-000-001,AA0318VK001,Them CELL 1.54178 11.8304 12.8390 15.0869 90.000 90.000 90.000 ZERR 4.00 0.0001 0.0001 0.0001 0.000 0.000 0.000 LATT -1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O S UNIT 84 120 8 20 4 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 LIST 6 SIZE 0.3 0.25 0.1 WPDB -1 CONF WGHT 0.055400 0.236400 EXTI 0.002010 FVAR 0.15024 S1 5 0.413300 0.204646 0.884772 11.00000 0.08365 0.04619 = 0.05026 -0.00068 -0.00646 -0.00506 O2 4 0.509054 0.137997 0.877530 11.00000 0.13163 0.05722 = 0.06775 -0.00501 0.00329 0.02953 O3 4 0.303970 0.168784 0.861182 11.00000 0.10864 0.08043 = 0.07596 0.00421 -0.02361 -0.04261 O4 4 0.189225 0.393070 0.705121 11.00000 0.06143 0.09053 = 0.07230 -0.02190 -0.00815 0.02345 O5 4 0.470688 0.170483 0.567564 11.00000 0.05391 0.08327 = 0.06487 -0.01553 -0.00772 0.01583 O6 4 0.354285 0.161107 0.451015 11.00000 0.06384 0.07005 = 0.05194 -0.01698 -0.00146 0.00495 N7 3 0.335400 0.292566 0.658151 11.00000 0.04707 0.05455 = 0.04361 -0.00553 -0.00329 0.00505 N8 3 0.438622 0.303864 0.820913 11.00000 0.06126 0.05500 = 0.04578 0.00160 -0.00633 -0.00409 C9 1 0.497205 0.233754 1.050752 11.00000 0.06152 0.11914 = 0.06042 -0.00930 -0.00740 0.03373 AFIX 43 H9 2 0.561455 0.199545 1.030405 11.00000 -1.20000 AFIX 0 C10 1 0.492777 0.268238 1.137356 11.00000 0.06522 0.14201 = 0.05901 -0.01221 -0.01444 0.02417 AFIX 43 H10 2 0.554436 0.256958 1.174369 11.00000 -1.20000 AFIX 0 C11 1 0.400207 0.318381 1.169816 11.00000 0.07496 0.06275 = 0.04967 0.00473 0.00373 0.00234 C12 1 0.393538 0.354836 1.264945 11.00000 0.12565 0.08616 = 0.05355 -0.00255 0.00917 0.00741 AFIX 137 H12A 2 0.454481 0.324754 1.298261 11.00000 -1.50000 H12B 2 0.322715 0.333510 1.290151 11.00000 -1.50000 H12C 2 0.399184 0.429393 1.266837 11.00000 -1.50000 AFIX 0 C13 1 0.310367 0.332542 1.113548 11.00000 0.07636 0.12175 = 0.06032 0.01257 0.01255 0.03899 AFIX 43 H13 2 0.246025 0.366472 1.134056 11.00000 -1.20000 AFIX 0 C14 1 0.313627 0.297352 1.026951 11.00000 0.05981 0.13685 = 0.05652 0.00926 -0.00419 0.02484 AFIX 43 H14 2 0.251172 0.306318 0.990302 11.00000 -1.20000 AFIX 0 C15 1 0.408790 0.249259 0.995021 11.00000 0.05646 0.04969 = 0.04830 0.00743 -0.00351 -0.00047 C16 1 0.548263 0.359099 0.828000 11.00000 0.06362 0.08120 = 0.07178 0.01038 -0.00690 -0.01239 AFIX 23 H16A 2 0.609214 0.317908 0.803087 11.00000 -1.20000 H16B 2 0.565929 0.375604 0.889193 11.00000 -1.20000 AFIX 0 C17 1 0.528370 0.456178 0.774743 11.00000 0.08966 0.07792 = 0.08464 0.01625 -0.01454 -0.02721 AFIX 23 H17A 2 0.579305 0.511456 0.792787 11.00000 -1.20000 H17B 2 0.538271 0.443048 0.711905 11.00000 -1.20000 AFIX 0 C18 1 0.408182 0.483483 0.795511 11.00000 0.09904 0.05337 = 0.08083 -0.00277 -0.02002 -0.00646 AFIX 23 H18A 2 0.375913 0.526226 0.748924 11.00000 -1.20000 H18B 2 0.403249 0.520988 0.851189 11.00000 -1.20000 AFIX 0 C19 1 0.346566 0.378347 0.801738 11.00000 0.06484 0.05297 = 0.04452 -0.00640 -0.00076 0.00342 AFIX 13 H19 2 0.293581 0.379819 0.851654 11.00000 -1.20000 AFIX 0 C20 1 0.282464 0.353706 0.716558 11.00000 0.05431 0.05370 = 0.04664 -0.00405 0.00087 0.00090 C21 1 0.292574 0.264112 0.570409 11.00000 0.04637 0.05170 = 0.04063 -0.00360 -0.00274 -0.00040 C22 1 0.273579 0.360373 0.511411 11.00000 0.06301 0.05569 = 0.05018 0.00125 -0.00323 0.00558 AFIX 23 H22A 2 0.247679 0.337186 0.453688 11.00000 -1.20000 H22B 2 0.213877 0.402281 0.537297 11.00000 -1.20000 AFIX 0 C23 1 0.376312 0.427971 0.498835 11.00000 0.08986 0.06107 = 0.06804 0.00560 -0.00141 -0.01276 AFIX 137 H23A 2 0.396143 0.459851 0.554253 11.00000 -1.50000 H23B 2 0.360093 0.481108 0.455912 11.00000 -1.50000 H23C 2 0.438213 0.386060 0.478321 11.00000 -1.50000 AFIX 0 C24 1 0.183028 0.199455 0.577469 11.00000 0.04459 0.06054 = 0.05734 -0.00336 -0.00228 -0.00112 AFIX 23 H24A 2 0.126552 0.240271 0.608550 11.00000 -1.20000 H24B 2 0.154720 0.186130 0.518203 11.00000 -1.20000 AFIX 0 C25 1 0.197274 0.098325 0.624089 11.00000 0.05924 0.06700 = 0.06523 0.00422 0.00104 -0.00855 AFIX 43 H25 2 0.217545 0.100444 0.683621 11.00000 -1.20000 AFIX 0 C26 1 0.183705 0.007653 0.588394 11.00000 0.09449 0.06206 = 0.09930 0.00417 -0.00523 -0.01088 AFIX 93 H26A 2 0.163433 0.002293 0.529011 11.00000 -1.20000 H26B 2 0.194213 -0.052220 0.622097 11.00000 -1.20000 AFIX 0 C27 1 0.384267 0.193997 0.530509 11.00000 0.05023 0.05132 = 0.04761 -0.00415 0.00162 -0.00118 C28 1 0.426836 0.083528 0.409373 11.00000 0.07447 0.07977 = 0.07833 -0.03038 0.01226 0.00514 AFIX 23 H28A 2 0.435169 0.023432 0.447786 11.00000 -1.20000 H28B 2 0.501170 0.112585 0.398206 11.00000 -1.20000 AFIX 0 C29 1 0.372958 0.052938 0.325435 11.00000 0.13968 0.09545 = 0.08814 -0.04022 0.00194 0.00213 AFIX 137 H29A 2 0.298605 0.026344 0.337160 11.00000 -1.50000 H29B 2 0.417527 0.000010 0.297173 11.00000 -1.50000 H29C 2 0.367582 0.112498 0.287197 11.00000 -1.50000 AFIX 0 H7 2 0.397197 0.270706 0.668545 11.00000 0.06105 HKLF 4 REM x3595_cu_rt_2 in P2(1)2(1)2(1),U.Grether,RO7304740-000-001,AA0318VK001,Them REM R1 = 0.0305 for 4032 Fo > 4sig(Fo) and 0.0314 for all 4179 data REM 270 parameters refined using 0 restraints END WGHT 0.0551 0.2375 REM Highest difference peak 0.150, deepest hole -0.149, 1-sigma level 0.031 Q1 1 0.3847 0.0125 0.3997 11.00000 0.05 0.15 Q2 1 0.3667 0.3669 1.1116 11.00000 0.05 0.15 Q3 1 0.3413 0.3026 1.1445 11.00000 0.05 0.14 Q4 1 0.3989 0.2092 0.9639 11.00000 0.05 0.14 Q5 1 0.3601 0.2493 1.0134 11.00000 0.05 0.14 ; _shelx_res_checksum 37881