# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2020 ####################################################################### # # 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_mesaconitine _database_code_depnum_ccdc_archive 'CCDC 1990874' loop_ _audit_author_name _audit_author_address 'Gabriele Kociok-Kohn' ;University of Bath United Kingdom ; _audit_update_record ; 2020-03-17 deposited with the CCDC. 2020-05-04 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common mesaconitine _chemical_melting_point ? _chemical_formula_moiety 'C33 H45 N O11' _chemical_formula_sum 'C33 H45 N O11' _chemical_formula_weight 631.70 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' _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 12.70194(13) _cell_length_b 15.37677(17) _cell_length_c 15.55588(17) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3038.29(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 35001 _cell_measurement_theta_min 4.0280 _cell_measurement_theta_max 73.0660 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_F_000 1352 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.282 _exptl_crystal_size_mid 0.136 _exptl_crystal_size_min 0.116 _exptl_absorpt_coefficient_mu 0.857 _shelx_estimated_absorpt_T_min 0.794 _shelx_estimated_absorpt_T_max 0.907 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 9 4 0.1134 8 -1 2 0.0274 -8 0 -2 0.0777 -3 -8 -4 0.1545 8 -3 1 0.0477 6 0 -7 0.0375 1 9 5 0.0999 -6 -2 7 0.0725 -6 0 7 0.0782 1 -1 -10 0.0569 2 7 -7 0.0800 -1 0 10 0.0744 -1 -8 6 0.1030 7 0 6 0.0316 -7 1 5 0.0777 -4 6 -6 0.1104 4 -7 5 0.0827 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.4325 9.3188 3.5629 0.3117 -0.0735 0.9473 8.0870 -0.7324 1.8489 -0.9373 0.2247 0.2665 -8.0392 -0.3058 -2.2459 0.9026 -0.2165 -0.3720 -3.4976 -8.0742 -4.1107 0.1689 -0.0416 -0.9848 7.7250 -3.4252 0.6906 -0.9721 0.2327 -0.0279 5.5481 -0.1693 -7.4650 -0.7532 -0.6443 -0.1324 1.2731 8.5101 5.0347 0.1136 0.0986 0.9886 -6.0055 -1.5041 6.7485 0.7588 0.6488 -0.0578 -5.6304 -0.0841 7.3737 0.7558 0.6465 0.1038 0.5330 -0.5292 -10.0620 -0.2102 -0.8797 -0.4265 2.3352 6.6367 -6.9787 -0.2154 -0.8980 0.3836 -0.6932 -0.0419 10.0616 0.2158 0.9032 0.3711 -1.0691 -8.0043 5.8871 0.0214 0.8619 -0.5067 6.7373 0.1177 5.8306 -0.7063 0.5420 0.4554 -7.2233 0.6085 4.8283 0.9236 0.3832 0.0136 -4.3604 5.8938 -6.1580 0.5615 -0.8161 0.1369 3.7120 -7.3876 5.0422 -0.5349 0.7765 -0.3332 _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _oxdiff_exptl_absorpt_empirical_full_min 0.773 _oxdiff_exptl_absorpt_empirical_full_max 1.235 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _diffrn_ambient_temperature 150.00(10) _diffrn_ambient_environment N~2~ _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_monochromator mirror _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, EosS2' _diffrn_measurement_method '\w scans' _diffrn_detector 'CCD plate' _diffrn_detector_type EosS2 _diffrn_detector_area_resol_mean 8.1150 _diffrn_reflns_number 55167 _diffrn_reflns_av_unetI/netI 0.0159 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.042 _diffrn_reflns_theta_max 73.372 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 6062 _reflns_number_gt 5983 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.781 _reflns_Friedel_fraction_max 0.991 _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 1.171.40.67a (Rigaku OD, 2019)' _computing_cell_refinement 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_refinement ; SHELXL-2018/3 (Sheldrick, 2018) Sheldrick GM (2008) Acta Crystallogr A64:112--122 and C. B. H\"ubschle, G. M. Sheldrick and B. Dittrich ShelXle: a Qt graphical user interface for SHELXL J. Appl. Cryst., 44, (2011) 1281-1284. ; _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _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^)+(0.0385P)^2^+0.5749P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary dual _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 2587 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.03(4) _chemical_absolute_configuration ad _refine_ls_number_reflns 6062 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0683 _refine_ls_wR_factor_gt 0.0680 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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_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 N N 0.52643(11) 0.86069(9) 0.26770(9) 0.0205(3) Uani 1 1 d . . . . . O1 O 0.17480(10) 0.47413(8) 0.27757(10) 0.0294(3) Uani 1 1 d . . . . . O2 O 0.10769(9) 0.60888(7) 0.26538(8) 0.0214(2) Uani 1 1 d . . . . . O3 O 0.06300(10) 0.73249(9) 0.12162(8) 0.0256(3) Uani 1 1 d . . . . . H3A H 0.013(2) 0.7440(15) 0.1558(15) 0.029(6) Uiso 1 1 d . . . . . O4 O 0.03201(10) 0.78324(8) 0.27628(8) 0.0253(3) Uani 1 1 d . . . . . O5 O 0.23949(11) 0.83730(8) 0.37530(9) 0.0244(3) Uani 1 1 d . . . . . H5A H 0.259(2) 0.8200(18) 0.4243(18) 0.042(7) Uiso 1 1 d . . . . . O6 O 0.29463(9) 0.62429(7) 0.38065(7) 0.0201(2) Uani 1 1 d . . . . . O7 O 0.29445(12) 0.71217(9) 0.49738(8) 0.0301(3) Uani 1 1 d . . . . . O8 O 0.56733(10) 0.65364(8) 0.37040(8) 0.0268(3) Uani 1 1 d . . . . . O9 O 0.73247(10) 0.60391(8) 0.19504(9) 0.0293(3) Uani 1 1 d . . . . . O10 O 0.77732(10) 0.81028(9) 0.12353(9) 0.0267(3) Uani 1 1 d . . . . . H10A H 0.777(2) 0.859(2) 0.154(2) 0.056(9) Uiso 1 1 d . . . . . O11 O 0.41097(10) 0.86564(8) 0.07391(8) 0.0230(3) Uani 1 1 d . . . . . C1 C 0.11294(13) 0.52916(11) 0.30009(12) 0.0211(3) Uani 1 1 d . . . . . C2 C 0.03122(13) 0.51982(11) 0.36762(12) 0.0217(3) Uani 1 1 d . . . . . C3 C -0.03016(15) 0.59084(12) 0.39236(12) 0.0262(4) Uani 1 1 d . . . . . H3 H -0.018625 0.646269 0.367087 0.031 Uiso 1 1 calc R U . . . C4 C -0.10780(16) 0.58024(14) 0.45376(13) 0.0315(4) Uani 1 1 d . . . . . H4 H -0.149847 0.628516 0.470295 0.038 Uiso 1 1 calc R U . . . C5 C -0.12474(16) 0.50003(14) 0.49127(13) 0.0312(4) Uani 1 1 d . . . . . H5 H -0.177592 0.493384 0.533977 0.037 Uiso 1 1 calc R U . . . C6 C -0.06465(16) 0.42958(14) 0.46652(14) 0.0342(4) Uani 1 1 d . . . . . H6 H -0.076965 0.374239 0.491749 0.041 Uiso 1 1 calc R U . . . C7 C 0.01353(15) 0.43905(13) 0.40512(14) 0.0307(4) Uani 1 1 d . . . . . H7 H 0.054997 0.390404 0.388652 0.037 Uiso 1 1 calc R U . . . C8 C 0.18192(13) 0.63552(11) 0.20093(10) 0.0197(3) Uani 1 1 d . . . . . H8 H 0.178608 0.595559 0.150284 0.024 Uiso 1 1 calc R U . . . C9 C 0.15419(13) 0.72785(11) 0.17405(11) 0.0208(3) Uani 1 1 d . . . . . C10 C 0.14139(13) 0.78637(11) 0.25411(11) 0.0209(3) Uani 1 1 d . . . . . H10 H 0.159914 0.847438 0.237998 0.025 Uiso 1 1 calc R U . . . C11 C -0.00206(17) 0.84882(14) 0.33401(14) 0.0355(5) Uani 1 1 d . . . . . H11A H 0.019887 0.905894 0.312453 0.053 Uiso 1 1 calc R U . . . H11B H 0.029358 0.838768 0.390690 0.053 Uiso 1 1 calc R U . . . H11C H -0.078960 0.847122 0.338798 0.053 Uiso 1 1 calc R U . . . C12 C 0.20850(13) 0.75941(11) 0.33284(11) 0.0198(3) Uani 1 1 d . . . . . H12 H 0.159729 0.728545 0.373034 0.024 Uiso 1 1 calc R U . . . C13 C 0.30308(13) 0.69624(10) 0.31680(10) 0.0179(3) Uani 1 1 d . . . . . C14 C 0.29259(14) 0.64082(12) 0.46560(11) 0.0235(4) Uani 1 1 d . . . . . C15 C 0.2861(2) 0.55752(14) 0.51538(13) 0.0376(5) Uani 1 1 d . . . . . H15A H 0.227525 0.522423 0.493590 0.056 Uiso 1 1 calc R U . . . H15B H 0.274573 0.570540 0.576327 0.056 Uiso 1 1 calc R U . . . H15C H 0.352091 0.525130 0.508783 0.056 Uiso 1 1 calc R U . . . C16 C 0.29528(13) 0.64586(10) 0.23116(10) 0.0183(3) Uani 1 1 d . . . . . H16 H 0.329692 0.587641 0.236715 0.022 Uiso 1 1 calc R U . . . C17 C 0.34550(13) 0.69800(11) 0.15546(10) 0.0188(3) Uani 1 1 d . . . . . H17 H 0.361991 0.655016 0.109139 0.023 Uiso 1 1 calc R U . . . C18 C 0.25148(13) 0.75453(11) 0.12233(11) 0.0225(3) Uani 1 1 d . . . . . H18A H 0.266657 0.817082 0.130896 0.027 Uiso 1 1 calc R U . . . H18B H 0.239678 0.744101 0.060272 0.027 Uiso 1 1 calc R U . . . C19 C 0.44961(12) 0.74866(10) 0.17466(10) 0.0177(3) Uani 1 1 d . . . . . C20 C 0.43344(13) 0.80626(11) 0.25394(11) 0.0185(3) Uani 1 1 d . . . . . H20 H 0.369370 0.843324 0.246656 0.022 Uiso 1 1 calc R U . . . C21 C 0.41377(13) 0.73540(10) 0.32336(10) 0.0185(3) Uani 1 1 d . . . . . H21 H 0.426733 0.759087 0.382286 0.022 Uiso 1 1 calc R U . . . C22 C 0.49433(13) 0.66250(11) 0.30144(11) 0.0202(3) Uani 1 1 d . . . . . H22 H 0.455000 0.606484 0.295524 0.024 Uiso 1 1 calc R U . . . C23 C 0.58941(18) 0.56567(15) 0.39046(18) 0.0450(6) Uani 1 1 d . . . . . H23A H 0.523436 0.534921 0.402426 0.068 Uiso 1 1 calc R U . . . H23B H 0.635052 0.563082 0.441189 0.068 Uiso 1 1 calc R U . . . H23C H 0.625016 0.538132 0.341650 0.068 Uiso 1 1 calc R U . . . C24 C 0.53863(13) 0.68815(11) 0.21055(11) 0.0186(3) Uani 1 1 d . . . . . H24 H 0.547046 0.635452 0.173517 0.022 Uiso 1 1 calc R U . . . C25 C 0.64380(13) 0.73915(11) 0.21671(11) 0.0199(3) Uani 1 1 d . . . . . C26 C 0.73411(14) 0.68052(11) 0.24709(12) 0.0239(4) Uani 1 1 d . . . . . H26A H 0.802337 0.710973 0.240726 0.029 Uiso 1 1 calc R U . . . H26B H 0.724527 0.665065 0.308373 0.029 Uiso 1 1 calc R U . . . C27 C 0.81477(16) 0.54594(13) 0.21533(14) 0.0339(4) Uani 1 1 d . . . . . H27A H 0.809832 0.494380 0.178528 0.051 Uiso 1 1 calc R U . . . H27B H 0.809051 0.528455 0.275733 0.051 Uiso 1 1 calc R U . . . H27C H 0.882637 0.574698 0.205848 0.051 Uiso 1 1 calc R U . . . C28 C 0.62753(13) 0.81502(11) 0.28023(11) 0.0214(3) Uani 1 1 d . . . . . H28A H 0.630504 0.792189 0.339683 0.026 Uiso 1 1 calc R U . . . H28B H 0.685850 0.857158 0.273306 0.026 Uiso 1 1 calc R U . . . C29 C 0.51128(15) 0.92555(12) 0.33453(12) 0.0270(4) Uani 1 1 d . . . . . H29A H 0.568909 0.967875 0.332471 0.041 Uiso 1 1 calc R U . . . H29B H 0.510595 0.897007 0.390858 0.041 Uiso 1 1 calc R U . . . H29C H 0.444116 0.955506 0.325336 0.041 Uiso 1 1 calc R U . . . C30 C 0.67437(13) 0.77162(11) 0.12594(11) 0.0210(3) Uani 1 1 d . . . . . H30 H 0.676224 0.719561 0.087435 0.025 Uiso 1 1 calc R U . . . C31 C 0.59400(13) 0.83338(11) 0.08932(11) 0.0216(3) Uani 1 1 d . . . . . H31A H 0.613325 0.847469 0.029263 0.026 Uiso 1 1 calc R U . . . H31B H 0.595220 0.888133 0.122784 0.026 Uiso 1 1 calc R U . . . C32 C 0.48272(13) 0.79598(10) 0.09085(11) 0.0192(3) Uani 1 1 d . . . . . H32 H 0.476840 0.753374 0.042518 0.023 Uiso 1 1 calc R U . . . C33 C 0.39538(16) 0.88158(13) -0.01490(12) 0.0290(4) Uani 1 1 d . . . . . H33A H 0.461393 0.901873 -0.040612 0.043 Uiso 1 1 calc R U . . . H33B H 0.340957 0.926145 -0.022254 0.043 Uiso 1 1 calc R U . . . H33C H 0.372997 0.827762 -0.043266 0.043 Uiso 1 1 calc R U . . . 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 N 0.0210(7) 0.0172(7) 0.0233(7) -0.0029(5) 0.0023(5) -0.0035(5) O1 0.0246(6) 0.0200(6) 0.0435(8) -0.0014(5) 0.0087(6) 0.0014(5) O2 0.0189(6) 0.0180(6) 0.0272(6) 0.0000(5) 0.0029(5) -0.0026(5) O3 0.0188(6) 0.0334(7) 0.0246(6) -0.0014(5) -0.0047(5) -0.0003(5) O4 0.0199(6) 0.0256(6) 0.0303(6) -0.0043(5) 0.0004(5) 0.0022(5) O5 0.0288(6) 0.0194(6) 0.0249(6) -0.0065(5) -0.0028(5) 0.0002(5) O6 0.0220(5) 0.0179(5) 0.0205(5) 0.0025(5) 0.0014(4) -0.0024(5) O7 0.0399(8) 0.0281(7) 0.0224(6) -0.0012(5) -0.0016(6) -0.0027(6) O8 0.0261(6) 0.0267(6) 0.0276(6) 0.0069(5) -0.0059(5) -0.0007(5) O9 0.0273(7) 0.0230(6) 0.0375(7) -0.0058(5) -0.0081(6) 0.0080(5) O10 0.0205(6) 0.0264(6) 0.0331(7) -0.0040(6) 0.0054(5) -0.0055(5) O11 0.0256(6) 0.0192(6) 0.0241(6) 0.0032(5) 0.0038(5) 0.0039(5) C1 0.0183(7) 0.0165(8) 0.0286(9) -0.0024(6) -0.0014(7) -0.0028(6) C2 0.0176(7) 0.0225(8) 0.0251(8) -0.0016(7) -0.0013(7) -0.0023(6) C3 0.0293(9) 0.0229(9) 0.0263(9) -0.0028(7) 0.0019(7) -0.0010(7) C4 0.0334(10) 0.0310(10) 0.0301(10) -0.0075(8) 0.0078(8) 0.0002(8) C5 0.0273(9) 0.0409(11) 0.0255(9) -0.0040(8) 0.0045(8) -0.0090(8) C6 0.0284(9) 0.0322(10) 0.0419(11) 0.0108(9) 0.0025(8) -0.0057(8) C7 0.0226(8) 0.0237(9) 0.0457(11) 0.0049(8) 0.0046(8) 0.0001(7) C8 0.0190(8) 0.0201(8) 0.0201(8) -0.0026(6) 0.0020(6) -0.0027(6) C9 0.0188(8) 0.0218(8) 0.0216(8) -0.0005(7) -0.0030(6) -0.0017(7) C10 0.0204(8) 0.0187(8) 0.0235(8) -0.0009(6) -0.0003(6) 0.0001(6) C11 0.0291(10) 0.0358(11) 0.0417(11) -0.0104(9) 0.0014(8) 0.0083(8) C12 0.0208(8) 0.0174(8) 0.0213(8) -0.0027(6) 0.0003(6) -0.0011(6) C13 0.0197(8) 0.0164(7) 0.0176(7) 0.0013(6) 0.0003(6) -0.0010(6) C14 0.0235(8) 0.0261(9) 0.0210(8) 0.0022(7) 0.0001(7) -0.0025(7) C15 0.0565(14) 0.0298(10) 0.0265(9) 0.0069(8) 0.0008(9) -0.0059(10) C16 0.0186(7) 0.0159(7) 0.0205(8) -0.0019(6) 0.0014(6) -0.0027(6) C17 0.0197(8) 0.0186(8) 0.0182(7) -0.0015(6) 0.0014(6) -0.0026(6) C18 0.0209(8) 0.0259(8) 0.0207(8) 0.0029(7) -0.0018(6) -0.0019(7) C19 0.0176(7) 0.0160(7) 0.0194(8) 0.0003(6) 0.0013(6) -0.0021(6) C20 0.0191(7) 0.0166(7) 0.0197(7) -0.0008(6) 0.0013(6) -0.0017(6) C21 0.0202(7) 0.0168(7) 0.0184(7) -0.0004(6) -0.0006(6) -0.0025(6) C22 0.0188(7) 0.0186(8) 0.0231(8) 0.0014(6) -0.0008(6) -0.0019(6) C23 0.0334(11) 0.0392(12) 0.0625(15) 0.0256(11) -0.0097(10) -0.0010(9) C24 0.0180(7) 0.0160(7) 0.0218(8) -0.0003(6) 0.0000(6) -0.0009(6) C25 0.0180(7) 0.0191(8) 0.0227(8) -0.0022(7) 0.0001(6) -0.0021(6) C26 0.0208(8) 0.0224(8) 0.0284(9) -0.0014(7) -0.0016(7) -0.0015(7) C27 0.0327(10) 0.0311(10) 0.0379(10) -0.0007(8) -0.0059(8) 0.0107(8) C28 0.0195(8) 0.0214(8) 0.0232(8) -0.0022(7) 0.0002(6) -0.0043(6) C29 0.0289(9) 0.0213(9) 0.0309(9) -0.0077(7) 0.0026(7) -0.0033(7) C30 0.0180(7) 0.0207(8) 0.0243(8) -0.0037(7) 0.0034(6) -0.0038(6) C31 0.0226(8) 0.0199(8) 0.0224(8) 0.0010(6) 0.0041(6) -0.0031(7) C32 0.0211(8) 0.0163(8) 0.0200(7) 0.0002(6) 0.0015(6) 0.0014(6) C33 0.0304(9) 0.0307(10) 0.0259(9) 0.0045(7) -0.0023(7) 0.0060(8) _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 N C29 1.453(2) . ? N C20 1.463(2) . ? N C28 1.477(2) . ? O1 C1 1.207(2) . ? O2 C1 1.341(2) . ? O2 C8 1.436(2) . ? O3 C9 1.418(2) . ? O3 H3A 0.85(3) . ? O4 C11 1.418(2) . ? O4 C10 1.432(2) . ? O5 C12 1.423(2) . ? O5 H5A 0.84(3) . ? O6 C14 1.346(2) . ? O6 C13 1.4907(19) . ? O7 C14 1.204(2) . ? O8 C23 1.416(2) . ? O8 C22 1.424(2) . ? O9 C27 1.410(2) . ? O9 C26 1.430(2) . ? O10 C30 1.4369(19) . ? O10 H10A 0.88(3) . ? O11 C33 1.417(2) . ? O11 C32 1.431(2) . ? C1 C2 1.484(2) . ? C2 C7 1.390(3) . ? C2 C3 1.396(3) . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 C6 1.380(3) . ? C5 H5 0.9500 . ? C6 C7 1.386(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.521(2) . ? C8 C16 1.523(2) . ? C8 H8 1.0000 . ? C9 C18 1.531(2) . ? C9 C10 1.545(2) . ? C10 C12 1.549(2) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.565(2) . ? C12 H12 1.0000 . ? C13 C21 1.533(2) . ? C13 C16 1.544(2) . ? C14 C15 1.499(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.561(2) . ? C16 H16 1.0000 . ? C17 C19 1.564(2) . ? C17 C18 1.564(2) . ? C17 H17 1.0000 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.532(2) . ? C19 C32 1.551(2) . ? C19 C24 1.567(2) . ? C20 C21 1.554(2) . ? C20 H20 1.0000 . ? C21 C22 1.556(2) . ? C21 H21 1.0000 . ? C22 C24 1.572(2) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.552(2) . ? C24 H24 1.0000 . ? C25 C26 1.534(2) . ? C25 C28 1.543(2) . ? C25 C30 1.547(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C31 1.506(2) . ? C30 H30 1.0000 . ? C31 C32 1.526(2) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32 1.0000 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? 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 C29 N C20 112.97(14) . . ? C29 N C28 110.31(14) . . ? C20 N C28 116.69(13) . . ? C1 O2 C8 120.61(13) . . ? C9 O3 H3A 105.1(16) . . ? C11 O4 C10 115.13(14) . . ? C12 O5 H5A 103.6(18) . . ? C14 O6 C13 121.02(13) . . ? C23 O8 C22 112.72(15) . . ? C27 O9 C26 112.54(15) . . ? C30 O10 H10A 109(2) . . ? C33 O11 C32 113.46(13) . . ? O1 C1 O2 123.81(16) . . ? O1 C1 C2 126.38(16) . . ? O2 C1 C2 109.80(14) . . ? C7 C2 C3 119.53(17) . . ? C7 C2 C1 119.77(16) . . ? C3 C2 C1 120.67(16) . . ? C4 C3 C2 119.77(17) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.55(19) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C6 C5 C4 119.80(18) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 120.41(18) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C2 119.93(18) . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? O2 C8 C9 107.82(13) . . ? O2 C8 C16 115.79(13) . . ? C9 C8 C16 101.91(13) . . ? O2 C8 H8 110.3 . . ? C9 C8 H8 110.3 . . ? C16 C8 H8 110.3 . . ? O3 C9 C8 113.20(14) . . ? O3 C9 C18 110.10(13) . . ? C8 C9 C18 101.98(13) . . ? O3 C9 C10 110.39(14) . . ? C8 C9 C10 110.26(13) . . ? C18 C9 C10 110.64(14) . . ? O4 C10 C9 106.05(13) . . ? O4 C10 C12 109.54(14) . . ? C9 C10 C12 115.07(14) . . ? O4 C10 H10 108.7 . . ? C9 C10 H10 108.7 . . ? C12 C10 H10 108.7 . . ? O4 C11 H11A 109.5 . . ? O4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O5 C12 C10 107.10(13) . . ? O5 C12 C13 112.58(13) . . ? C10 C12 C13 117.55(13) . . ? O5 C12 H12 106.3 . . ? C10 C12 H12 106.3 . . ? C13 C12 H12 106.3 . . ? O6 C13 C21 108.26(12) . . ? O6 C13 C16 101.41(12) . . ? C21 C13 C16 108.26(13) . . ? O6 C13 C12 107.41(12) . . ? C21 C13 C12 116.73(13) . . ? C16 C13 C12 113.56(13) . . ? O7 C14 O6 125.10(16) . . ? O7 C14 C15 124.60(17) . . ? O6 C14 C15 110.29(16) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C8 C16 C13 112.29(13) . . ? C8 C16 C17 101.95(13) . . ? C13 C16 C17 111.53(12) . . ? C8 C16 H16 110.3 . . ? C13 C16 H16 110.3 . . ? C17 C16 H16 110.3 . . ? C16 C17 C19 117.23(13) . . ? C16 C17 C18 102.82(13) . . ? C19 C17 C18 115.58(13) . . ? C16 C17 H17 106.8 . . ? C19 C17 H17 106.8 . . ? C18 C17 H17 106.8 . . ? C9 C18 C17 107.11(13) . . ? C9 C18 H18A 110.3 . . ? C17 C18 H18A 110.3 . . ? C9 C18 H18B 110.3 . . ? C17 C18 H18B 110.3 . . ? H18A C18 H18B 108.5 . . ? C20 C19 C32 116.21(13) . . ? C20 C19 C17 109.17(13) . . ? C32 C19 C17 107.61(13) . . ? C20 C19 C24 98.81(12) . . ? C32 C19 C24 112.48(13) . . ? C17 C19 C24 112.49(13) . . ? N C20 C19 109.89(13) . . ? N C20 C21 115.40(14) . . ? C19 C20 C21 100.11(12) . . ? N C20 H20 110.3 . . ? C19 C20 H20 110.3 . . ? C21 C20 H20 110.3 . . ? C13 C21 C20 112.12(13) . . ? C13 C21 C22 107.80(13) . . ? C20 C21 C22 104.31(13) . . ? C13 C21 H21 110.8 . . ? C20 C21 H21 110.8 . . ? C22 C21 H21 110.8 . . ? O8 C22 C21 109.39(13) . . ? O8 C22 C24 117.93(13) . . ? C21 C22 C24 104.58(13) . . ? O8 C22 H22 108.2 . . ? C21 C22 H22 108.2 . . ? C24 C22 H22 108.2 . . ? O8 C23 H23A 109.5 . . ? O8 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O8 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C19 110.07(13) . . ? C25 C24 C22 112.29(13) . . ? C19 C24 C22 102.19(12) . . ? C25 C24 H24 110.7 . . ? C19 C24 H24 110.7 . . ? C22 C24 H24 110.7 . . ? C26 C25 C28 110.33(14) . . ? C26 C25 C30 106.45(14) . . ? C28 C25 C30 111.97(14) . . ? C26 C25 C24 111.46(13) . . ? C28 C25 C24 107.84(13) . . ? C30 C25 C24 108.83(13) . . ? O9 C26 C25 107.40(14) . . ? O9 C26 H26A 110.2 . . ? C25 C26 H26A 110.2 . . ? O9 C26 H26B 110.2 . . ? C25 C26 H26B 110.2 . . ? H26A C26 H26B 108.5 . . ? O9 C27 H27A 109.5 . . ? O9 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O9 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N C28 C25 113.06(13) . . ? N C28 H28A 109.0 . . ? C25 C28 H28A 109.0 . . ? N C28 H28B 109.0 . . ? C25 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? N C29 H29A 109.5 . . ? N C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O10 C30 C31 110.25(14) . . ? O10 C30 C25 112.68(14) . . ? C31 C30 C25 112.24(13) . . ? O10 C30 H30 107.1 . . ? C31 C30 H30 107.1 . . ? C25 C30 H30 107.1 . . ? C30 C31 C32 112.60(13) . . ? C30 C31 H31A 109.1 . . ? C32 C31 H31A 109.1 . . ? C30 C31 H31B 109.1 . . ? C32 C31 H31B 109.1 . . ? H31A C31 H31B 107.8 . . ? O11 C32 C31 107.75(13) . . ? O11 C32 C19 109.47(13) . . ? C31 C32 C19 116.17(14) . . ? O11 C32 H32 107.7 . . ? C31 C32 H32 107.7 . . ? C19 C32 H32 107.7 . . ? O11 C33 H33A 109.5 . . ? O11 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O11 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 C8 O2 C1 O1 -3.8(2) . . . . ? C8 O2 C1 C2 177.17(13) . . . . ? O1 C1 C2 C7 -6.8(3) . . . . ? O2 C1 C2 C7 172.18(16) . . . . ? O1 C1 C2 C3 174.92(18) . . . . ? O2 C1 C2 C3 -6.1(2) . . . . ? C7 C2 C3 C4 0.0(3) . . . . ? C1 C2 C3 C4 178.27(17) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C4 C5 C6 C7 0.9(3) . . . . ? C5 C6 C7 C2 -0.5(3) . . . . ? C3 C2 C7 C6 0.0(3) . . . . ? C1 C2 C7 C6 -178.25(18) . . . . ? C1 O2 C8 C9 179.24(14) . . . . ? C1 O2 C8 C16 -67.43(19) . . . . ? O2 C8 C9 O3 -74.00(16) . . . . ? C16 C8 C9 O3 163.66(13) . . . . ? O2 C8 C9 C18 167.75(13) . . . . ? C16 C8 C9 C18 45.42(15) . . . . ? O2 C8 C9 C10 50.20(17) . . . . ? C16 C8 C9 C10 -72.13(16) . . . . ? C11 O4 C10 C9 -164.73(15) . . . . ? C11 O4 C10 C12 70.52(19) . . . . ? O3 C9 C10 O4 33.83(18) . . . . ? C8 C9 C10 O4 -91.99(15) . . . . ? C18 C9 C10 O4 155.96(14) . . . . ? O3 C9 C10 C12 155.08(14) . . . . ? C8 C9 C10 C12 29.27(19) . . . . ? C18 C9 C10 C12 -82.79(18) . . . . ? O4 C10 C12 O5 -95.51(15) . . . . ? C9 C10 C12 O5 145.15(14) . . . . ? O4 C10 C12 C13 136.64(14) . . . . ? C9 C10 C12 C13 17.3(2) . . . . ? C14 O6 C13 C21 69.62(18) . . . . ? C14 O6 C13 C16 -176.60(14) . . . . ? C14 O6 C13 C12 -57.23(18) . . . . ? O5 C12 C13 O6 104.49(15) . . . . ? C10 C12 C13 O6 -130.33(14) . . . . ? O5 C12 C13 C21 -17.21(19) . . . . ? C10 C12 C13 C21 107.97(16) . . . . ? O5 C12 C13 C16 -144.24(14) . . . . ? C10 C12 C13 C16 -19.1(2) . . . . ? C13 O6 C14 O7 2.0(3) . . . . ? C13 O6 C14 C15 -178.78(15) . . . . ? O2 C8 C16 C13 -45.68(19) . . . . ? C9 C8 C16 C13 71.02(16) . . . . ? O2 C8 C16 C17 -165.16(13) . . . . ? C9 C8 C16 C17 -48.46(14) . . . . ? O6 C13 C16 C8 89.05(15) . . . . ? C21 C13 C16 C8 -157.17(13) . . . . ? C12 C13 C16 C8 -25.84(18) . . . . ? O6 C13 C16 C17 -157.22(13) . . . . ? C21 C13 C16 C17 -43.45(17) . . . . ? C12 C13 C16 C17 87.89(16) . . . . ? C8 C16 C17 C19 159.68(14) . . . . ? C13 C16 C17 C19 39.66(19) . . . . ? C8 C16 C17 C18 31.73(15) . . . . ? C13 C16 C17 C18 -88.30(15) . . . . ? O3 C9 C18 C17 -145.49(14) . . . . ? C8 C9 C18 C17 -25.06(16) . . . . ? C10 C9 C18 C17 92.21(16) . . . . ? C16 C17 C18 C9 -4.11(17) . . . . ? C19 C17 C18 C9 -133.10(14) . . . . ? C16 C17 C19 C20 -52.15(18) . . . . ? C18 C17 C19 C20 69.38(17) . . . . ? C16 C17 C19 C32 -179.09(13) . . . . ? C18 C17 C19 C32 -57.56(17) . . . . ? C16 C17 C19 C24 56.47(18) . . . . ? C18 C17 C19 C24 178.00(13) . . . . ? C29 N C20 C19 172.00(14) . . . . ? C28 N C20 C19 -58.56(18) . . . . ? C29 N C20 C21 -75.75(18) . . . . ? C28 N C20 C21 53.68(19) . . . . ? C32 C19 C20 N -52.43(18) . . . . ? C17 C19 C20 N -174.31(13) . . . . ? C24 C19 C20 N 68.07(15) . . . . ? C32 C19 C20 C21 -174.29(13) . . . . ? C17 C19 C20 C21 63.83(15) . . . . ? C24 C19 C20 C21 -53.80(14) . . . . ? O6 C13 C21 C20 175.33(12) . . . . ? C16 C13 C21 C20 66.17(16) . . . . ? C12 C13 C21 C20 -63.42(18) . . . . ? O6 C13 C21 C22 61.09(16) . . . . ? C16 C13 C21 C22 -48.07(16) . . . . ? C12 C13 C21 C22 -177.66(13) . . . . ? N C20 C21 C13 166.34(13) . . . . ? C19 C20 C21 C13 -75.80(15) . . . . ? N C20 C21 C22 -77.28(16) . . . . ? C19 C20 C21 C22 40.58(15) . . . . ? C23 O8 C22 C21 137.55(17) . . . . ? C23 O8 C22 C24 -103.20(19) . . . . ? C13 C21 C22 O8 -124.45(14) . . . . ? C20 C21 C22 O8 116.20(14) . . . . ? C13 C21 C22 C24 108.34(14) . . . . ? C20 C21 C22 C24 -11.00(16) . . . . ? C20 C19 C24 C25 -72.51(15) . . . . ? C32 C19 C24 C25 50.71(17) . . . . ? C17 C19 C24 C25 172.42(13) . . . . ? C20 C19 C24 C22 46.96(14) . . . . ? C32 C19 C24 C22 170.18(13) . . . . ? C17 C19 C24 C22 -68.11(15) . . . . ? O8 C22 C24 C25 -25.8(2) . . . . ? C21 C22 C24 C25 95.97(15) . . . . ? O8 C22 C24 C19 -143.68(14) . . . . ? C21 C22 C24 C19 -21.93(15) . . . . ? C19 C24 C25 C26 -176.96(13) . . . . ? C22 C24 C25 C26 69.91(18) . . . . ? C19 C24 C25 C28 61.80(17) . . . . ? C22 C24 C25 C28 -51.32(17) . . . . ? C19 C24 C25 C30 -59.86(17) . . . . ? C22 C24 C25 C30 -172.99(13) . . . . ? C27 O9 C26 C25 178.04(15) . . . . ? C28 C25 C26 O9 169.58(14) . . . . ? C30 C25 C26 O9 -68.72(16) . . . . ? C24 C25 C26 O9 49.80(18) . . . . ? C29 N C28 C25 174.41(14) . . . . ? C20 N C28 C25 43.72(19) . . . . ? C26 C25 C28 N -165.34(14) . . . . ? C30 C25 C28 N 76.30(17) . . . . ? C24 C25 C28 N -43.40(18) . . . . ? C26 C25 C30 O10 -52.51(17) . . . . ? C28 C25 C30 O10 68.14(17) . . . . ? C24 C25 C30 O10 -172.75(13) . . . . ? C26 C25 C30 C31 -177.68(14) . . . . ? C28 C25 C30 C31 -57.04(18) . . . . ? C24 C25 C30 C31 62.07(17) . . . . ? O10 C30 C31 C32 -179.56(14) . . . . ? C25 C30 C31 C32 -53.05(18) . . . . ? C33 O11 C32 C31 85.25(17) . . . . ? C33 O11 C32 C19 -147.57(14) . . . . ? C30 C31 C32 O11 166.85(14) . . . . ? C30 C31 C32 C19 43.68(19) . . . . ? C20 C19 C32 O11 -52.32(18) . . . . ? C17 C19 C32 O11 70.38(16) . . . . ? C24 C19 C32 O11 -165.17(13) . . . . ? C20 C19 C32 C31 69.96(18) . . . . ? C17 C19 C32 C31 -167.34(13) . . . . ? C24 C19 C32 C31 -42.90(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O3 H3A O4 0.85(3) 1.98(2) 2.5597(18) 125(2) . yes O5 H5A O7 0.84(3) 2.06(3) 2.7920(19) 145(2) . yes O10 H10A O1 0.88(3) 2.16(3) 3.0140(19) 163(3) 3_655 yes _refine_diff_density_max 0.182 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.039 _shelx_res_file ; TITL shelxt_a.res in P2(1)2(1)2(1) s20phar2.res created by SHELXL-2018/3 at 11:47:20 on 05-Mar-2020 CELL 1.54184 12.70194 15.37677 15.55588 90.000 90.000 90.000 ZERR 4.00 0.00013 0.00017 0.00017 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N O UNIT 132 180 4 44 ACTA FMAP 2 PLAN 5 BOND $H CONF EQIV $2 -x+1, y+1/2, -z+1/2 HTAB O3 O4 HTAB O5 O7 HTAB O10 O1_$2 TEMP -123 SIZE 0.116 0.136 0.282 LIST 4 L.S. 10 WGHT 0.038500 0.574900 FVAR 4.37946 N 3 0.526431 0.860695 0.267705 11.00000 0.02096 0.01721 = 0.02330 -0.00291 0.00233 -0.00348 O1 4 0.174800 0.474126 0.277567 11.00000 0.02461 0.01999 = 0.04352 -0.00138 0.00871 0.00142 O2 4 0.107685 0.608878 0.265376 11.00000 0.01890 0.01802 = 0.02715 -0.00002 0.00288 -0.00264 O3 4 0.062995 0.732488 0.121625 11.00000 0.01880 0.03344 = 0.02462 -0.00139 -0.00467 -0.00033 H3A 2 0.013074 0.743999 0.155832 11.00000 0.02941 O4 4 0.032012 0.783237 0.276283 11.00000 0.01995 0.02557 = 0.03034 -0.00428 0.00041 0.00219 O5 4 0.239494 0.837301 0.375300 11.00000 0.02882 0.01944 = 0.02490 -0.00652 -0.00283 0.00018 H5A 2 0.259030 0.820022 0.424304 11.00000 0.04186 O6 4 0.294625 0.624289 0.380653 11.00000 0.02197 0.01793 = 0.02046 0.00253 0.00136 -0.00243 O7 4 0.294445 0.712171 0.497375 11.00000 0.03986 0.02808 = 0.02242 -0.00117 -0.00161 -0.00268 O8 4 0.567331 0.653643 0.370399 11.00000 0.02611 0.02674 = 0.02763 0.00695 -0.00587 -0.00073 O9 4 0.732472 0.603912 0.195036 11.00000 0.02733 0.02297 = 0.03749 -0.00585 -0.00811 0.00800 O10 4 0.777316 0.810285 0.123530 11.00000 0.02045 0.02643 = 0.03314 -0.00401 0.00540 -0.00548 H10A 2 0.777040 0.859027 0.153586 11.00000 0.05640 O11 4 0.410973 0.865638 0.073907 11.00000 0.02557 0.01920 = 0.02409 0.00325 0.00376 0.00387 C1 1 0.112940 0.529161 0.300092 11.00000 0.01827 0.01654 = 0.02862 -0.00239 -0.00139 -0.00279 C2 1 0.031220 0.519816 0.367623 11.00000 0.01763 0.02246 = 0.02514 -0.00157 -0.00132 -0.00233 C3 1 -0.030161 0.590839 0.392359 11.00000 0.02929 0.02291 = 0.02630 -0.00278 0.00190 -0.00102 AFIX 43 H3 2 -0.018625 0.646269 0.367087 11.00000 -1.20000 AFIX 0 C4 1 -0.107800 0.580236 0.453764 11.00000 0.03343 0.03102 = 0.03009 -0.00750 0.00779 0.00021 AFIX 43 H4 2 -0.149847 0.628516 0.470295 11.00000 -1.20000 AFIX 0 C5 1 -0.124737 0.500029 0.491271 11.00000 0.02727 0.04089 = 0.02546 -0.00396 0.00450 -0.00902 AFIX 43 H5 2 -0.177592 0.493384 0.533977 11.00000 -1.20000 AFIX 0 C6 1 -0.064650 0.429577 0.466525 11.00000 0.02838 0.03220 = 0.04194 0.01076 0.00248 -0.00567 AFIX 43 H6 2 -0.076965 0.374239 0.491749 11.00000 -1.20000 AFIX 0 C7 1 0.013528 0.439045 0.405119 11.00000 0.02263 0.02374 = 0.04574 0.00491 0.00464 0.00007 AFIX 43 H7 2 0.054997 0.390404 0.388652 11.00000 -1.20000 AFIX 0 C8 1 0.181918 0.635519 0.200929 11.00000 0.01897 0.02014 = 0.02011 -0.00264 0.00196 -0.00274 AFIX 13 H8 2 0.178608 0.595559 0.150284 11.00000 -1.20000 AFIX 0 C9 1 0.154185 0.727853 0.174046 11.00000 0.01885 0.02183 = 0.02158 -0.00052 -0.00302 -0.00166 C10 1 0.141395 0.786368 0.254110 11.00000 0.02039 0.01872 = 0.02353 -0.00093 -0.00028 0.00009 AFIX 13 H10 2 0.159914 0.847438 0.237998 11.00000 -1.20000 AFIX 0 C11 1 -0.002057 0.848820 0.334014 11.00000 0.02908 0.03578 = 0.04169 -0.01045 0.00138 0.00834 AFIX 137 H11A 2 0.019887 0.905894 0.312453 11.00000 -1.50000 H11B 2 0.029358 0.838768 0.390690 11.00000 -1.50000 H11C 2 -0.078960 0.847122 0.338798 11.00000 -1.50000 AFIX 0 C12 1 0.208498 0.759414 0.332839 11.00000 0.02076 0.01738 = 0.02129 -0.00267 0.00032 -0.00114 AFIX 13 H12 2 0.159729 0.728545 0.373034 11.00000 -1.20000 AFIX 0 C13 1 0.303080 0.696243 0.316802 11.00000 0.01970 0.01639 = 0.01757 0.00127 0.00027 -0.00098 C14 1 0.292591 0.640823 0.465599 11.00000 0.02349 0.02611 = 0.02105 0.00225 0.00013 -0.00247 C15 1 0.286136 0.557517 0.515385 11.00000 0.05651 0.02976 = 0.02649 0.00689 0.00077 -0.00592 AFIX 137 H15A 2 0.227525 0.522423 0.493590 11.00000 -1.50000 H15B 2 0.274573 0.570540 0.576327 11.00000 -1.50000 H15C 2 0.352091 0.525130 0.508783 11.00000 -1.50000 AFIX 0 C16 1 0.295281 0.645862 0.231156 11.00000 0.01861 0.01586 = 0.02054 -0.00186 0.00142 -0.00274 AFIX 13 H16 2 0.329692 0.587641 0.236715 11.00000 -1.20000 AFIX 0 C17 1 0.345500 0.697999 0.155463 11.00000 0.01968 0.01855 = 0.01820 -0.00146 0.00141 -0.00262 AFIX 13 H17 2 0.361991 0.655016 0.109139 11.00000 -1.20000 AFIX 0 C18 1 0.251480 0.754529 0.122330 11.00000 0.02089 0.02588 = 0.02069 0.00289 -0.00183 -0.00192 AFIX 23 H18A 2 0.266657 0.817082 0.130896 11.00000 -1.20000 H18B 2 0.239678 0.744101 0.060272 11.00000 -1.20000 AFIX 0 C19 1 0.449611 0.748660 0.174657 11.00000 0.01763 0.01601 = 0.01938 0.00031 0.00130 -0.00206 C20 1 0.433442 0.806257 0.253936 11.00000 0.01912 0.01659 = 0.01968 -0.00082 0.00131 -0.00165 AFIX 13 H20 2 0.369370 0.843324 0.246656 11.00000 -1.20000 AFIX 0 C21 1 0.413772 0.735399 0.323361 11.00000 0.02023 0.01675 = 0.01844 -0.00043 -0.00060 -0.00246 AFIX 13 H21 2 0.426733 0.759087 0.382286 11.00000 -1.20000 AFIX 0 C22 1 0.494335 0.662500 0.301441 11.00000 0.01880 0.01861 = 0.02311 0.00145 -0.00082 -0.00195 AFIX 13 H22 2 0.455000 0.606484 0.295524 11.00000 -1.20000 AFIX 0 C23 1 0.589409 0.565669 0.390461 11.00000 0.03345 0.03917 = 0.06247 0.02560 -0.00975 -0.00100 AFIX 137 H23A 2 0.523436 0.534921 0.402426 11.00000 -1.50000 H23B 2 0.635052 0.563082 0.441189 11.00000 -1.50000 H23C 2 0.625016 0.538132 0.341650 11.00000 -1.50000 AFIX 0 C24 1 0.538630 0.688155 0.210549 11.00000 0.01799 0.01595 = 0.02182 -0.00028 0.00000 -0.00091 AFIX 13 H24 2 0.547046 0.635452 0.173517 11.00000 -1.20000 AFIX 0 C25 1 0.643800 0.739151 0.216710 11.00000 0.01804 0.01909 = 0.02267 -0.00217 0.00011 -0.00210 C26 1 0.734111 0.680519 0.247090 11.00000 0.02084 0.02244 = 0.02842 -0.00144 -0.00157 -0.00150 AFIX 23 H26A 2 0.802337 0.710973 0.240726 11.00000 -1.20000 H26B 2 0.724527 0.665065 0.308373 11.00000 -1.20000 AFIX 0 C27 1 0.814768 0.545945 0.215333 11.00000 0.03267 0.03107 = 0.03789 -0.00069 -0.00586 0.01065 AFIX 137 H27A 2 0.809832 0.494380 0.178528 11.00000 -1.50000 H27B 2 0.809051 0.528455 0.275733 11.00000 -1.50000 H27C 2 0.882637 0.574698 0.205848 11.00000 -1.50000 AFIX 0 C28 1 0.627533 0.815020 0.280227 11.00000 0.01950 0.02142 = 0.02325 -0.00218 0.00024 -0.00428 AFIX 23 H28A 2 0.630504 0.792189 0.339683 11.00000 -1.20000 H28B 2 0.685850 0.857158 0.273306 11.00000 -1.20000 AFIX 0 C29 1 0.511279 0.925552 0.334534 11.00000 0.02886 0.02128 = 0.03095 -0.00775 0.00265 -0.00335 AFIX 137 H29A 2 0.568909 0.967875 0.332471 11.00000 -1.50000 H29B 2 0.510595 0.897007 0.390858 11.00000 -1.50000 H29C 2 0.444116 0.955506 0.325336 11.00000 -1.50000 AFIX 0 C30 1 0.674371 0.771618 0.125935 11.00000 0.01798 0.02069 = 0.02431 -0.00372 0.00336 -0.00384 AFIX 13 H30 2 0.676224 0.719561 0.087435 11.00000 -1.20000 AFIX 0 C31 1 0.593999 0.833377 0.089323 11.00000 0.02255 0.01993 = 0.02236 0.00100 0.00409 -0.00307 AFIX 23 H31A 2 0.613325 0.847469 0.029263 11.00000 -1.20000 H31B 2 0.595220 0.888133 0.122784 11.00000 -1.20000 AFIX 0 C32 1 0.482722 0.795978 0.090849 11.00000 0.02113 0.01631 = 0.02003 0.00019 0.00155 0.00143 AFIX 13 H32 2 0.476840 0.753374 0.042518 11.00000 -1.20000 AFIX 0 C33 1 0.395378 0.881584 -0.014904 11.00000 0.03035 0.03071 = 0.02587 0.00451 -0.00226 0.00605 AFIX 137 H33A 2 0.461393 0.901873 -0.040612 11.00000 -1.50000 H33B 2 0.340957 0.926145 -0.022254 11.00000 -1.50000 H33C 2 0.372997 0.827762 -0.043266 11.00000 -1.50000 AFIX 0 HKLF 4 REM shelxt_a.res in P2(1)2(1)2(1) REM wR2 = 0.0683, GooF = S = 1.039, Restrained GooF = 1.039 for all data REM R1 = 0.0268 for 5983 Fo > 4sig(Fo) and 0.0271 for all 6062 data REM 424 parameters refined using 0 restraints END WGHT 0.0385 0.5749 REM Highest difference peak 0.182, deepest hole -0.168, 1-sigma level 0.039 Q1 1 0.3991 0.7220 0.1698 11.00000 0.05 0.18 Q2 1 0.5547 0.6018 0.4357 11.00000 0.05 0.18 Q3 1 0.5414 0.8140 0.0929 11.00000 0.05 0.18 Q4 1 0.2880 0.5040 0.4811 11.00000 0.05 0.17 Q5 1 0.3590 0.7182 0.3193 11.00000 0.05 0.16 ; _shelx_res_checksum 49677 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc/DCM' ####################################################################### # # 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_condelphine _database_code_depnum_ccdc_archive 'CCDC 1990875' loop_ _audit_author_name _audit_author_address 'Gabriele Kociok-Kohn' ;University of Bath United Kingdom ; _audit_update_record ; 2020-03-17 deposited with the CCDC. 2020-05-04 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common condelphine _chemical_melting_point ? _chemical_formula_moiety 'C25 H39 N O6' _chemical_formula_sum 'C25 H39 N O6' _chemical_formula_weight 449.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 21' _space_group_name_Hall 'P 2yb' _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, y+1/2, -z' _cell_length_a 8.92530(9) _cell_length_b 13.08371(15) _cell_length_c 9.80866(10) _cell_angle_alpha 90 _cell_angle_beta 93.4553(9) _cell_angle_gamma 90 _cell_volume 1143.33(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 15011 _cell_measurement_theta_min 4.5290 _cell_measurement_theta_max 72.9710 _exptl_crystal_description tabloid _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_F_000 488 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.388 _exptl_crystal_size_mid 0.374 _exptl_crystal_size_min 0.094 _exptl_absorpt_coefficient_mu 0.747 _shelx_estimated_absorpt_T_min 0.760 _shelx_estimated_absorpt_T_max 0.933 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -8 0 0.1935 -6 0 0 0.2038 -1 8 0 0.1626 0 0 6 0.0618 0 0 -6 0.0318 4 -5 0 0.2416 6 1 0 0.1681 4 6 0 0.2152 2 0 6 0.1133 -1 -7 4 0.1726 -2 0 -6 0.1029 -3 -7 0 0.2342 3 8 0 0.2032 -2 0 6 0.0997 -1 4 6 0.1106 0 -6 -5 0.1318 -1 -3 -6 0.0754 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.0301 -8.4881 0.2304 -0.3733 0.2272 0.8995 -5.7863 -0.0070 0.0922 0.7651 -0.4688 0.4414 -0.8739 8.3894 -0.2134 0.4885 -0.2978 -0.8202 -0.2470 0.3608 6.3607 -0.5220 -0.8529 -0.0090 0.2470 -0.3608 -6.3607 0.5220 0.8529 0.0090 4.4157 -5.4786 0.0746 -0.8273 0.5066 0.2428 5.7644 0.7427 -0.1043 -0.7302 0.4461 -0.5175 3.9410 6.2213 -0.2173 -0.2461 0.1493 -0.9577 2.2891 0.1236 5.6853 -0.8105 -0.5580 -0.1781 -0.6926 -6.5656 4.0095 -0.5426 -0.3724 0.7529 -2.3306 -0.2724 -5.6598 0.8075 0.5560 0.1971 -2.7350 -7.4457 -0.3875 0.0876 0.0616 0.9942 2.6293 7.5615 0.0185 -0.0355 -0.0258 -0.9990 -2.1839 0.4065 6.0244 -0.2309 -0.9638 0.1330 -0.9258 3.8459 5.6350 -0.2197 -0.9192 -0.3267 -0.1308 -5.8676 -4.5809 0.1816 0.7613 0.6225 -0.6690 -3.0108 -5.8513 0.4874 0.7957 0.3596 _exptl_absorpt_correction_T_min 0.467 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _oxdiff_exptl_absorpt_empirical_full_min 0.696 _oxdiff_exptl_absorpt_empirical_full_max 1.187 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _diffrn_ambient_temperature 150.00(10) _diffrn_ambient_environment N~2~ _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_monochromator mirror _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, EosS2' _diffrn_measurement_method '\w scans' _diffrn_detector 'CCD plate' _diffrn_detector_type EosS2 _diffrn_detector_area_resol_mean 8.1150 _diffrn_reflns_number 18838 _diffrn_reflns_av_unetI/netI 0.0182 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.516 _diffrn_reflns_theta_max 72.905 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.949 _diffrn_reflns_point_group_measured_fraction_full 0.959 _reflns_number_total 4338 _reflns_number_gt 4299 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.818 _reflns_Friedel_fraction_max 0.895 _reflns_Friedel_fraction_full 0.914 _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 1.171.40.67a (Rigaku OD, 2019)' _computing_cell_refinement 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_refinement ; SHELXL-2018/3 (Sheldrick, 2018) Sheldrick GM (2008) Acta Crystallogr A64:112--122 and C. B. H\"ubschle, G. M. Sheldrick and B. Dittrich ShelXle: a Qt graphical user interface for SHELXL J. Appl. Cryst., 44, (2011) 1281-1284. ; _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _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^)+(0.0486P)^2^+0.1687P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary dual _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 1907 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.02(5) _chemical_absolute_configuration ad _refine_ls_number_reflns 4338 _refine_ls_number_parameters 301 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0757 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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_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 C1 C 0.1617(2) 0.4297(2) 0.7683(2) 0.0316(5) Uani 1 1 d . . . . . H1A H 0.110321 0.432631 0.677214 0.047 Uiso 1 1 calc R U . . . H1B H 0.097449 0.459935 0.835116 0.047 Uiso 1 1 calc R U . . . H1C H 0.183026 0.358347 0.792738 0.047 Uiso 1 1 calc R U . . . C2 C 0.3060(2) 0.48823(17) 0.76793(19) 0.0244(4) Uani 1 1 d . . . . . C3 C 0.50370(19) 0.53410(14) 0.62900(17) 0.0176(3) Uani 1 1 d . . . . . H3 H 0.514675 0.602330 0.674456 0.021 Uiso 1 1 calc R U . . . C4 C 0.62693(18) 0.46184(14) 0.68406(17) 0.0160(3) Uani 1 1 d . . . . . H4 H 0.636184 0.463741 0.786142 0.019 Uiso 1 1 calc R U . . . C5 C 0.59767(19) 0.35234(14) 0.63271(18) 0.0181(4) Uani 1 1 d . . . . . H5 H 0.696214 0.316680 0.627151 0.022 Uiso 1 1 calc R U . . . C6 C 0.5791(3) 0.27585(19) 0.8533(2) 0.0368(5) Uani 1 1 d . . . . . H6A H 0.679720 0.248284 0.842162 0.055 Uiso 1 1 calc R U . . . H6B H 0.520007 0.226064 0.901940 0.055 Uiso 1 1 calc R U . . . H6C H 0.587077 0.339533 0.905813 0.055 Uiso 1 1 calc R U . . . C7 C 0.51091(19) 0.34563(15) 0.49208(18) 0.0180(3) Uani 1 1 d . . . . . H7A H 0.407508 0.322978 0.507705 0.022 Uiso 1 1 calc R U . . . H7B H 0.557911 0.290918 0.439539 0.022 Uiso 1 1 calc R U . . . C8 C 0.49881(18) 0.44226(14) 0.39964(17) 0.0156(3) Uani 1 1 d . . . . . C9 C 0.53713(18) 0.54257(14) 0.47852(17) 0.0154(3) Uani 1 1 d . . . . . H9 H 0.480882 0.601315 0.434898 0.019 Uiso 1 1 calc R U . . . C10 C 0.70794(18) 0.56573(14) 0.49010(17) 0.0150(3) Uani 1 1 d . . . . . H10 H 0.720168 0.640828 0.506088 0.018 Uiso 1 1 calc R U . . . C11 C 0.76587(18) 0.50979(14) 0.62397(16) 0.0172(4) Uani 1 1 d . . . . . H11A H 0.839521 0.456220 0.603372 0.021 Uiso 1 1 calc R U . . . H11B H 0.814673 0.558916 0.689311 0.021 Uiso 1 1 calc R U . . . C12 C 0.80008(17) 0.53728(13) 0.36715(16) 0.0138(3) Uani 1 1 d . . . . . C13 C 0.76434(17) 0.42650(13) 0.32550(16) 0.0130(3) Uani 1 1 d . . . . . H13 H 0.775626 0.380561 0.406954 0.016 Uiso 1 1 calc R U . . . C14 C 0.8524(2) 0.28439(15) 0.18566(19) 0.0208(4) Uani 1 1 d . . . . . H14A H 0.915177 0.268951 0.108430 0.025 Uiso 1 1 calc R U . . . H14B H 0.746710 0.269618 0.155613 0.025 Uiso 1 1 calc R U . . . C15 C 0.8992(2) 0.21500(16) 0.3051(2) 0.0280(4) Uani 1 1 d . . . . . H15A H 0.910777 0.144915 0.272083 0.042 Uiso 1 1 calc R U . . . H15B H 0.822200 0.216546 0.372189 0.042 Uiso 1 1 calc R U . . . H15C H 0.994911 0.238812 0.348060 0.042 Uiso 1 1 calc R U . . . C16 C 0.85140(19) 0.45462(15) 0.09359(17) 0.0185(4) Uani 1 1 d . . . . . H16A H 0.755306 0.437243 0.043247 0.022 Uiso 1 1 calc R U . . . H16B H 0.933776 0.436841 0.034653 0.022 Uiso 1 1 calc R U . . . C17 C 0.85549(19) 0.57002(14) 0.12212(18) 0.0173(4) Uani 1 1 d . . . . . C18 C 0.8061(2) 0.62454(15) -0.01091(18) 0.0207(4) Uani 1 1 d . . . . . H18A H 0.876702 0.608387 -0.081941 0.025 Uiso 1 1 calc R U . . . H18B H 0.704934 0.600642 -0.043419 0.025 Uiso 1 1 calc R U . . . C19 C 0.7412(3) 0.78582(18) -0.1040(2) 0.0322(5) Uani 1 1 d . . . . . H19A H 0.802486 0.773875 -0.182086 0.048 Uiso 1 1 calc R U . . . H19B H 0.739909 0.859057 -0.083154 0.048 Uiso 1 1 calc R U . . . H19C H 0.638524 0.762102 -0.126315 0.048 Uiso 1 1 calc R U . . . C20 C 1.0179(2) 0.60475(16) 0.16766(19) 0.0217(4) Uani 1 1 d . . . . . H20A H 1.088036 0.547704 0.153072 0.026 Uiso 1 1 calc R U . . . H20B H 1.046445 0.662463 0.109318 0.026 Uiso 1 1 calc R U . . . C21 C 1.0352(2) 0.63775(16) 0.31678(19) 0.0223(4) Uani 1 1 d . . . . . H21A H 1.143023 0.647297 0.343622 0.027 Uiso 1 1 calc R U . . . H21B H 0.983934 0.704083 0.327727 0.027 Uiso 1 1 calc R U . . . C22 C 0.96908(18) 0.55871(14) 0.41001(17) 0.0166(3) Uani 1 1 d . . . . . H22 H 0.972020 0.589297 0.503559 0.020 Uiso 1 1 calc R U . . . C23 C 0.74274(18) 0.59178(14) 0.23330(17) 0.0149(3) Uani 1 1 d . . . . . H23 H 0.729638 0.666831 0.247798 0.018 Uiso 1 1 calc R U . . . C24 C 0.59009(18) 0.53835(14) 0.19714(16) 0.0167(3) Uani 1 1 d . . . . . H24A H 0.505777 0.580891 0.225706 0.020 Uiso 1 1 calc R U . . . H24B H 0.576500 0.525786 0.097630 0.020 Uiso 1 1 calc R U . . . C25 C 0.59768(18) 0.43614(14) 0.27685(16) 0.0148(3) Uani 1 1 d . . . . . H25 H 0.566163 0.377794 0.215816 0.018 Uiso 1 1 calc R U . . . N N 0.86672(16) 0.39329(12) 0.21950(15) 0.0158(3) Uani 1 1 d . . . . . O1 O 0.37342(18) 0.52363(16) 0.86661(15) 0.0393(4) Uani 1 1 d . . . . . O2 O 0.35350(13) 0.49521(10) 0.64037(12) 0.0202(3) Uani 1 1 d . . . . . O3 O 0.50735(16) 0.29563(11) 0.72284(13) 0.0248(3) Uani 1 1 d . . . . . O4 O 0.34977(13) 0.44756(12) 0.33701(13) 0.0217(3) Uani 1 1 d . . . . . H4A H 0.286(3) 0.457(2) 0.392(3) 0.033(7) Uiso 1 1 d . . . . . O5 O 0.80336(17) 0.73126(11) 0.01152(14) 0.0275(3) Uani 1 1 d . . . . . O6 O 1.05778(13) 0.46779(11) 0.41952(13) 0.0208(3) Uani 1 1 d . . . . . H6 H 1.025(4) 0.430(3) 0.351(3) 0.049(9) 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 C1 0.0230(9) 0.0398(13) 0.0325(10) 0.0117(10) 0.0069(8) 0.0015(8) C2 0.0203(9) 0.0310(11) 0.0224(9) 0.0025(8) 0.0048(7) 0.0054(8) C3 0.0168(8) 0.0188(9) 0.0173(8) -0.0027(7) 0.0018(6) -0.0010(7) C4 0.0163(7) 0.0172(9) 0.0142(7) -0.0007(6) -0.0009(6) -0.0015(6) C5 0.0171(7) 0.0178(9) 0.0192(8) 0.0005(7) -0.0001(6) -0.0021(6) C6 0.0530(14) 0.0332(13) 0.0227(10) 0.0091(9) -0.0111(9) -0.0153(10) C7 0.0175(8) 0.0189(9) 0.0175(8) -0.0032(7) 0.0002(6) -0.0052(7) C8 0.0108(7) 0.0194(9) 0.0162(7) -0.0023(7) -0.0023(6) -0.0014(6) C9 0.0141(8) 0.0170(9) 0.0153(8) -0.0010(6) 0.0012(6) 0.0013(6) C10 0.0152(8) 0.0149(8) 0.0147(7) -0.0021(6) -0.0007(6) -0.0016(6) C11 0.0166(8) 0.0208(9) 0.0140(7) -0.0010(7) -0.0019(6) -0.0043(7) C12 0.0121(7) 0.0156(8) 0.0134(7) -0.0003(6) -0.0005(6) -0.0007(6) C13 0.0118(7) 0.0150(8) 0.0122(7) -0.0016(6) -0.0003(6) -0.0006(6) C14 0.0231(8) 0.0189(10) 0.0203(8) -0.0033(7) 0.0005(7) 0.0029(7) C15 0.0369(11) 0.0194(10) 0.0276(10) 0.0021(8) 0.0013(8) 0.0068(8) C16 0.0210(8) 0.0207(10) 0.0141(7) -0.0003(7) 0.0023(6) 0.0008(7) C17 0.0189(8) 0.0187(9) 0.0144(7) 0.0012(7) 0.0005(6) -0.0008(7) C18 0.0262(9) 0.0204(10) 0.0152(8) 0.0010(7) -0.0007(7) -0.0007(7) C19 0.0374(11) 0.0314(12) 0.0273(10) 0.0116(9) -0.0020(8) 0.0073(9) C20 0.0198(8) 0.0265(10) 0.0189(8) 0.0044(7) 0.0016(6) -0.0043(7) C21 0.0202(8) 0.0244(10) 0.0220(9) 0.0007(8) -0.0004(7) -0.0089(7) C22 0.0143(8) 0.0200(9) 0.0153(7) -0.0004(7) -0.0019(6) -0.0035(6) C23 0.0153(8) 0.0148(8) 0.0144(7) 0.0007(6) -0.0012(6) 0.0000(6) C24 0.0151(7) 0.0201(9) 0.0146(7) -0.0001(7) -0.0018(6) 0.0014(7) C25 0.0131(7) 0.0165(8) 0.0146(7) -0.0023(7) -0.0019(6) -0.0001(6) N 0.0162(7) 0.0167(7) 0.0148(7) -0.0010(6) 0.0019(5) 0.0032(5) O1 0.0331(8) 0.0643(12) 0.0210(7) -0.0076(7) 0.0059(6) -0.0050(8) O2 0.0147(6) 0.0275(7) 0.0185(6) -0.0007(5) 0.0030(5) 0.0008(5) O3 0.0303(7) 0.0253(7) 0.0182(6) 0.0036(5) -0.0027(5) -0.0108(5) O4 0.0103(5) 0.0351(8) 0.0194(6) -0.0042(6) -0.0019(5) 0.0007(5) O5 0.0395(8) 0.0211(8) 0.0211(6) 0.0054(6) -0.0052(5) 0.0009(6) O6 0.0138(5) 0.0269(8) 0.0211(6) 0.0013(5) -0.0032(5) 0.0002(5) _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 C2 1.498(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O1 1.201(3) . ? C2 O2 1.348(2) . ? C3 O2 1.444(2) . ? C3 C4 1.524(2) . ? C3 C9 1.527(2) . ? C3 H3 1.0000 . ? C4 C5 1.536(3) . ? C4 C11 1.538(2) . ? C4 H4 1.0000 . ? C5 O3 1.438(2) . ? C5 C7 1.543(2) . ? C5 H5 1.0000 . ? C6 O3 1.420(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.556(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O4 1.4329(19) . ? C8 C25 1.537(2) . ? C8 C9 1.551(2) . ? C9 C10 1.552(2) . ? C9 H9 1.0000 . ? C10 C12 1.546(2) . ? C10 C11 1.564(2) . ? C10 H10 1.0000 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.534(2) . ? C12 C23 1.553(2) . ? C12 C22 1.567(2) . ? C13 N 1.490(2) . ? C13 C25 1.540(2) . ? C13 H13 1.0000 . ? C14 N 1.467(2) . ? C14 C15 1.521(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 N 1.472(2) . ? C16 C17 1.536(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.529(2) . ? C17 C23 1.554(2) . ? C17 C20 1.559(2) . ? C18 O5 1.414(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O5 1.423(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.524(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.523(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 O6 1.429(2) . ? C22 H22 1.0000 . ? C23 C24 1.553(2) . ? C23 H23 1.0000 . ? C24 C25 1.549(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25 1.0000 . ? O4 H4A 0.82(3) . ? O6 H6 0.87(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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 O2 123.47(18) . . ? O1 C2 C1 125.73(18) . . ? O2 C2 C1 110.80(17) . . ? O2 C3 C4 114.04(15) . . ? O2 C3 C9 109.66(13) . . ? C4 C3 C9 102.04(13) . . ? O2 C3 H3 110.3 . . ? C4 C3 H3 110.3 . . ? C9 C3 H3 110.3 . . ? C3 C4 C5 110.95(14) . . ? C3 C4 C11 101.09(14) . . ? C5 C4 C11 112.32(14) . . ? C3 C4 H4 110.7 . . ? C5 C4 H4 110.7 . . ? C11 C4 H4 110.7 . . ? O3 C5 C4 111.73(14) . . ? O3 C5 C7 104.51(14) . . ? C4 C5 C7 114.36(15) . . ? O3 C5 H5 108.7 . . ? C4 C5 H5 108.7 . . ? C7 C5 H5 108.7 . . ? O3 C6 H6A 109.5 . . ? O3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 C8 119.22(15) . . ? C5 C7 H7A 107.5 . . ? C8 C7 H7A 107.5 . . ? C5 C7 H7B 107.5 . . ? C8 C7 H7B 107.5 . . ? H7A C7 H7B 107.0 . . ? O4 C8 C25 103.21(12) . . ? O4 C8 C9 110.12(14) . . ? C25 C8 C9 108.37(13) . . ? O4 C8 C7 108.61(14) . . ? C25 C8 C7 113.03(14) . . ? C9 C8 C7 113.04(14) . . ? C3 C9 C8 111.75(14) . . ? C3 C9 C10 101.05(13) . . ? C8 C9 C10 112.82(13) . . ? C3 C9 H9 110.3 . . ? C8 C9 H9 110.3 . . ? C10 C9 H9 110.3 . . ? C12 C10 C9 117.55(13) . . ? C12 C10 C11 112.20(14) . . ? C9 C10 C11 104.11(13) . . ? C12 C10 H10 107.5 . . ? C9 C10 H10 107.5 . . ? C11 C10 H10 107.5 . . ? C4 C11 C10 106.21(13) . . ? C4 C11 H11A 110.5 . . ? C10 C11 H11A 110.5 . . ? C4 C11 H11B 110.5 . . ? C10 C11 H11B 110.5 . . ? H11A C11 H11B 108.7 . . ? C13 C12 C10 108.87(13) . . ? C13 C12 C23 98.98(12) . . ? C10 C12 C23 112.66(14) . . ? C13 C12 C22 114.96(14) . . ? C10 C12 C22 107.25(13) . . ? C23 C12 C22 114.04(13) . . ? N C13 C12 109.57(13) . . ? N C13 C25 115.42(13) . . ? C12 C13 C25 100.76(13) . . ? N C13 H13 110.2 . . ? C12 C13 H13 110.2 . . ? C25 C13 H13 110.2 . . ? N C14 C15 112.92(15) . . ? N C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? N C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N C16 C17 112.52(14) . . ? N C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? N C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 107.51(14) . . ? C18 C17 C23 110.35(14) . . ? C16 C17 C23 107.38(14) . . ? C18 C17 C20 108.90(14) . . ? C16 C17 C20 110.51(15) . . ? C23 C17 C20 112.08(14) . . ? O5 C18 C17 109.56(14) . . ? O5 C18 H18A 109.8 . . ? C17 C18 H18A 109.8 . . ? O5 C18 H18B 109.8 . . ? C17 C18 H18B 109.8 . . ? H18A C18 H18B 108.2 . . ? O5 C19 H19A 109.5 . . ? O5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C17 113.36(15) . . ? C21 C20 H20A 108.9 . . ? C17 C20 H20A 108.9 . . ? C21 C20 H20B 108.9 . . ? C17 C20 H20B 108.9 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 111.30(16) . . ? C22 C21 H21A 109.4 . . ? C20 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? C20 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? O6 C22 C21 111.79(14) . . ? O6 C22 C12 112.91(14) . . ? C21 C22 C12 111.24(14) . . ? O6 C22 H22 106.8 . . ? C21 C22 H22 106.8 . . ? C12 C22 H22 106.8 . . ? C24 C23 C12 103.07(14) . . ? C24 C23 C17 110.70(13) . . ? C12 C23 C17 108.34(13) . . ? C24 C23 H23 111.5 . . ? C12 C23 H23 111.5 . . ? C17 C23 H23 111.5 . . ? C25 C24 C23 105.21(13) . . ? C25 C24 H24A 110.7 . . ? C23 C24 H24A 110.7 . . ? C25 C24 H24B 110.7 . . ? C23 C24 H24B 110.7 . . ? H24A C24 H24B 108.8 . . ? C8 C25 C13 110.54(13) . . ? C8 C25 C24 109.93(14) . . ? C13 C25 C24 103.84(13) . . ? C8 C25 H25 110.8 . . ? C13 C25 H25 110.8 . . ? C24 C25 H25 110.8 . . ? C14 N C16 109.71(14) . . ? C14 N C13 113.10(14) . . ? C16 N C13 113.37(13) . . ? C2 O2 C3 116.15(14) . . ? C6 O3 C5 114.14(15) . . ? C8 O4 H4A 112.9(18) . . ? C18 O5 C19 112.40(16) . . ? C22 O6 H6 105(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 O2 C3 C4 C5 46.30(18) . . . . ? C9 C3 C4 C5 -71.85(16) . . . . ? O2 C3 C4 C11 165.61(13) . . . . ? C9 C3 C4 C11 47.46(15) . . . . ? C3 C4 C5 O3 -89.09(17) . . . . ? C11 C4 C5 O3 158.59(14) . . . . ? C3 C4 C5 C7 29.37(19) . . . . ? C11 C4 C5 C7 -82.96(18) . . . . ? O3 C5 C7 C8 138.57(15) . . . . ? C4 C5 C7 C8 16.1(2) . . . . ? C5 C7 C8 O4 -139.35(15) . . . . ? C5 C7 C8 C25 106.74(18) . . . . ? C5 C7 C8 C9 -16.8(2) . . . . ? O2 C3 C9 C8 -50.02(18) . . . . ? C4 C3 C9 C8 71.21(16) . . . . ? O2 C3 C9 C10 -170.24(14) . . . . ? C4 C3 C9 C10 -49.02(16) . . . . ? O4 C8 C9 C3 93.94(16) . . . . ? C25 C8 C9 C3 -153.84(13) . . . . ? C7 C8 C9 C3 -27.74(19) . . . . ? O4 C8 C9 C10 -152.99(14) . . . . ? C25 C8 C9 C10 -40.78(18) . . . . ? C7 C8 C9 C10 85.32(17) . . . . ? C3 C9 C10 C12 155.53(15) . . . . ? C8 C9 C10 C12 36.1(2) . . . . ? C3 C9 C10 C11 30.74(17) . . . . ? C8 C9 C10 C11 -88.72(16) . . . . ? C3 C4 C11 C10 -27.41(16) . . . . ? C5 C4 C11 C10 90.91(16) . . . . ? C12 C10 C11 C4 -130.25(15) . . . . ? C9 C10 C11 C4 -2.10(17) . . . . ? C9 C10 C12 C13 -49.84(19) . . . . ? C11 C10 C12 C13 70.82(16) . . . . ? C9 C10 C12 C23 58.9(2) . . . . ? C11 C10 C12 C23 179.56(14) . . . . ? C9 C10 C12 C22 -174.80(14) . . . . ? C11 C10 C12 C22 -54.15(18) . . . . ? C10 C12 C13 N -172.56(13) . . . . ? C23 C12 C13 N 69.65(15) . . . . ? C22 C12 C13 N -52.25(17) . . . . ? C10 C12 C13 C25 65.34(15) . . . . ? C23 C12 C13 C25 -52.44(14) . . . . ? C22 C12 C13 C25 -174.34(13) . . . . ? N C16 C17 C18 -168.30(14) . . . . ? N C16 C17 C23 -49.56(18) . . . . ? N C16 C17 C20 72.96(18) . . . . ? C16 C17 C18 O5 178.09(15) . . . . ? C23 C17 C18 O5 61.27(19) . . . . ? C20 C17 C18 O5 -62.15(19) . . . . ? C18 C17 C20 C21 130.66(17) . . . . ? C16 C17 C20 C21 -111.46(18) . . . . ? C23 C17 C20 C21 8.3(2) . . . . ? C17 C20 C21 C22 49.3(2) . . . . ? C20 C21 C22 O6 70.81(19) . . . . ? C20 C21 C22 C12 -56.4(2) . . . . ? C13 C12 C22 O6 -7.55(19) . . . . ? C10 C12 C22 O6 113.65(15) . . . . ? C23 C12 C22 O6 -120.89(15) . . . . ? C13 C12 C22 C21 119.08(16) . . . . ? C10 C12 C22 C21 -119.72(16) . . . . ? C23 C12 C22 C21 5.7(2) . . . . ? C13 C12 C23 C24 44.46(15) . . . . ? C10 C12 C23 C24 -70.43(17) . . . . ? C22 C12 C23 C24 167.02(14) . . . . ? C13 C12 C23 C17 -72.88(15) . . . . ? C10 C12 C23 C17 172.24(14) . . . . ? C22 C12 C23 C17 49.69(18) . . . . ? C18 C17 C23 C24 69.19(18) . . . . ? C16 C17 C23 C24 -47.71(18) . . . . ? C20 C17 C23 C24 -169.26(15) . . . . ? C18 C17 C23 C12 -178.49(14) . . . . ? C16 C17 C23 C12 64.61(16) . . . . ? C20 C17 C23 C12 -56.93(19) . . . . ? C12 C23 C24 C25 -19.75(16) . . . . ? C17 C23 C24 C25 95.90(16) . . . . ? O4 C8 C25 C13 -178.25(14) . . . . ? C9 C8 C25 C13 64.99(18) . . . . ? C7 C8 C25 C13 -61.12(18) . . . . ? O4 C8 C25 C24 67.69(16) . . . . ? C9 C8 C25 C24 -49.07(16) . . . . ? C7 C8 C25 C24 -175.17(13) . . . . ? N C13 C25 C8 164.88(14) . . . . ? C12 C13 C25 C8 -77.23(16) . . . . ? N C13 C25 C24 -77.27(17) . . . . ? C12 C13 C25 C24 40.63(15) . . . . ? C23 C24 C25 C8 105.68(14) . . . . ? C23 C24 C25 C13 -12.59(16) . . . . ? C15 C14 N C16 167.84(15) . . . . ? C15 C14 N C13 -64.5(2) . . . . ? C17 C16 N C14 176.44(14) . . . . ? C17 C16 N C13 48.93(19) . . . . ? C12 C13 N C14 173.12(13) . . . . ? C25 C13 N C14 -74.03(19) . . . . ? C12 C13 N C16 -61.17(17) . . . . ? C25 C13 N C16 51.7(2) . . . . ? O1 C2 O2 C3 9.4(3) . . . . ? C1 C2 O2 C3 -169.64(16) . . . . ? C4 C3 O2 C2 69.3(2) . . . . ? C9 C3 O2 C2 -177.01(15) . . . . ? C4 C5 O3 C6 -66.7(2) . . . . ? C7 C5 O3 C6 169.14(17) . . . . ? C17 C18 O5 C19 -172.99(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O4 H4A O2 0.82(3) 2.52(3) 3.0383(18) 122(2) . yes O4 H4A O6 0.82(3) 2.07(3) 2.7877(17) 145(2) 1_455 yes O6 H6 N 0.87(3) 1.92(3) 2.703(2) 150(3) . yes _refine_diff_density_max 0.184 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.048 _shelx_res_file ; TITL shelxt_a.res in P2(1) s20phar1.res created by SHELXL-2018/3 at 14:59:11 on 25-Feb-2020 CELL 1.54184 8.92530 13.08371 9.80866 90.000 93.4553 90.000 ZERR 2.00 0.00009 0.00015 0.00010 0.000 0.0009 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O UNIT 50 78 2 12 ACTA FMAP 2 PLAN 10 BOND $H CONF TEMP -123 EQIV $1 x-1, y, z HTAB O4 O2 HTAB O4 O6_$1 HTAB O6 N SIZE 0.094 0.374 0.388 LIST 4 L.S. 10 WGHT 0.048600 0.168700 FVAR 10.07065 C1 1 0.161723 0.429727 0.768280 11.00000 0.02302 0.03982 = 0.03248 0.01171 0.00694 0.00151 AFIX 137 H1A 2 0.110321 0.432631 0.677214 11.00000 -1.50000 H1B 2 0.097449 0.459935 0.835116 11.00000 -1.50000 H1C 2 0.183026 0.358347 0.792738 11.00000 -1.50000 AFIX 0 C2 1 0.306004 0.488233 0.767933 11.00000 0.02032 0.03103 = 0.02235 0.00251 0.00484 0.00536 C3 1 0.503701 0.534101 0.629001 11.00000 0.01676 0.01876 = 0.01733 -0.00274 0.00175 -0.00099 AFIX 13 H3 2 0.514675 0.602330 0.674456 11.00000 -1.20000 AFIX 0 C4 1 0.626928 0.461845 0.684062 11.00000 0.01634 0.01717 = 0.01421 -0.00073 -0.00089 -0.00155 AFIX 13 H4 2 0.636184 0.463741 0.786142 11.00000 -1.20000 AFIX 0 C5 1 0.597668 0.352337 0.632710 11.00000 0.01707 0.01782 = 0.01915 0.00051 -0.00009 -0.00214 AFIX 13 H5 2 0.696214 0.316680 0.627151 11.00000 -1.20000 AFIX 0 C6 1 0.579093 0.275846 0.853289 11.00000 0.05302 0.03321 = 0.02267 0.00913 -0.01107 -0.01528 AFIX 137 H6A 2 0.679720 0.248284 0.842162 11.00000 -1.50000 H6B 2 0.520007 0.226064 0.901940 11.00000 -1.50000 H6C 2 0.587077 0.339533 0.905813 11.00000 -1.50000 AFIX 0 C7 1 0.510910 0.345631 0.492082 11.00000 0.01746 0.01887 = 0.01750 -0.00321 0.00018 -0.00524 AFIX 23 H7A 2 0.407508 0.322978 0.507705 11.00000 -1.20000 H7B 2 0.557911 0.290918 0.439539 11.00000 -1.20000 AFIX 0 C8 1 0.498813 0.442263 0.399640 11.00000 0.01081 0.01945 = 0.01620 -0.00231 -0.00235 -0.00138 C9 1 0.537133 0.542570 0.478521 11.00000 0.01406 0.01704 = 0.01527 -0.00101 0.00115 0.00131 AFIX 13 H9 2 0.480882 0.601315 0.434898 11.00000 -1.20000 AFIX 0 C10 1 0.707937 0.565725 0.490102 11.00000 0.01518 0.01493 = 0.01469 -0.00211 -0.00071 -0.00163 AFIX 13 H10 2 0.720168 0.640828 0.506088 11.00000 -1.20000 AFIX 0 C11 1 0.765869 0.509785 0.623966 11.00000 0.01655 0.02084 = 0.01396 -0.00100 -0.00185 -0.00427 AFIX 23 H11A 2 0.839521 0.456220 0.603372 11.00000 -1.20000 H11B 2 0.814673 0.558916 0.689311 11.00000 -1.20000 AFIX 0 C12 1 0.800076 0.537276 0.367153 11.00000 0.01206 0.01564 = 0.01345 -0.00034 -0.00049 -0.00067 C13 1 0.764337 0.426500 0.325503 11.00000 0.01177 0.01500 = 0.01218 -0.00164 -0.00033 -0.00064 AFIX 13 H13 2 0.775626 0.380561 0.406954 11.00000 -1.20000 AFIX 0 C14 1 0.852372 0.284391 0.185663 11.00000 0.02310 0.01885 = 0.02025 -0.00331 0.00051 0.00287 AFIX 23 H14A 2 0.915177 0.268951 0.108430 11.00000 -1.20000 H14B 2 0.746710 0.269618 0.155613 11.00000 -1.20000 AFIX 0 C15 1 0.899231 0.214996 0.305120 11.00000 0.03689 0.01939 = 0.02757 0.00211 0.00131 0.00682 AFIX 137 H15A 2 0.910777 0.144915 0.272083 11.00000 -1.50000 H15B 2 0.822200 0.216546 0.372189 11.00000 -1.50000 H15C 2 0.994911 0.238812 0.348060 11.00000 -1.50000 AFIX 0 C16 1 0.851401 0.454620 0.093591 11.00000 0.02100 0.02070 = 0.01406 -0.00030 0.00229 0.00083 AFIX 23 H16A 2 0.755306 0.437243 0.043247 11.00000 -1.20000 H16B 2 0.933776 0.436841 0.034653 11.00000 -1.20000 AFIX 0 C17 1 0.855495 0.570017 0.122120 11.00000 0.01886 0.01866 = 0.01445 0.00118 0.00046 -0.00082 C18 1 0.806102 0.624543 -0.010908 11.00000 0.02619 0.02038 = 0.01523 0.00100 -0.00067 -0.00072 AFIX 23 H18A 2 0.876702 0.608387 -0.081941 11.00000 -1.20000 H18B 2 0.704934 0.600642 -0.043419 11.00000 -1.20000 AFIX 0 C19 1 0.741234 0.785821 -0.104001 11.00000 0.03735 0.03135 = 0.02730 0.01158 -0.00203 0.00726 AFIX 137 H19A 2 0.802486 0.773875 -0.182086 11.00000 -1.50000 H19B 2 0.739909 0.859057 -0.083154 11.00000 -1.50000 H19C 2 0.638524 0.762102 -0.126315 11.00000 -1.50000 AFIX 0 C20 1 1.017909 0.604750 0.167661 11.00000 0.01978 0.02653 = 0.01893 0.00437 0.00163 -0.00426 AFIX 23 H20A 2 1.088036 0.547704 0.153072 11.00000 -1.20000 H20B 2 1.046445 0.662463 0.109318 11.00000 -1.20000 AFIX 0 C21 1 1.035223 0.637755 0.316782 11.00000 0.02018 0.02435 = 0.02203 0.00071 -0.00035 -0.00892 AFIX 23 H21A 2 1.143023 0.647297 0.343622 11.00000 -1.20000 H21B 2 0.983934 0.704083 0.327727 11.00000 -1.20000 AFIX 0 C22 1 0.969078 0.558707 0.410007 11.00000 0.01433 0.01999 = 0.01527 -0.00037 -0.00188 -0.00351 AFIX 13 H22 2 0.972020 0.589297 0.503559 11.00000 -1.20000 AFIX 0 C23 1 0.742742 0.591785 0.233298 11.00000 0.01530 0.01480 = 0.01436 0.00066 -0.00117 0.00003 AFIX 13 H23 2 0.729638 0.666831 0.247798 11.00000 -1.20000 AFIX 0 C24 1 0.590092 0.538346 0.197137 11.00000 0.01512 0.02010 = 0.01456 -0.00009 -0.00178 0.00138 AFIX 23 H24A 2 0.505777 0.580891 0.225706 11.00000 -1.20000 H24B 2 0.576500 0.525786 0.097630 11.00000 -1.20000 AFIX 0 C25 1 0.597685 0.436138 0.276854 11.00000 0.01314 0.01650 = 0.01456 -0.00226 -0.00192 -0.00009 AFIX 13 H25 2 0.566163 0.377794 0.215816 11.00000 -1.20000 AFIX 0 N 3 0.866717 0.393288 0.219496 11.00000 0.01616 0.01669 = 0.01476 -0.00103 0.00188 0.00324 O1 4 0.373416 0.523625 0.866610 11.00000 0.03313 0.06432 = 0.02099 -0.00761 0.00586 -0.00501 O2 4 0.353504 0.495206 0.640368 11.00000 0.01465 0.02749 = 0.01855 -0.00065 0.00298 0.00084 O3 4 0.507347 0.295632 0.722836 11.00000 0.03034 0.02526 = 0.01820 0.00361 -0.00273 -0.01077 O4 4 0.349768 0.447563 0.337011 11.00000 0.01028 0.03507 = 0.01939 -0.00417 -0.00186 0.00067 H4A 2 0.285909 0.457115 0.392296 11.00000 0.03337 O5 4 0.803364 0.731260 0.011524 11.00000 0.03952 0.02105 = 0.02111 0.00541 -0.00522 0.00090 O6 4 1.057777 0.467793 0.419523 11.00000 0.01381 0.02693 = 0.02106 0.00128 -0.00324 0.00019 H6 2 1.024982 0.430200 0.351008 11.00000 0.04900 HKLF 4 REM shelxt_a.res in P2(1) REM wR2 = 0.0759, GooF = S = 1.062, Restrained GooF = 1.062 for all data REM R1 = 0.0299 for 4299 Fo > 4sig(Fo) and 0.0301 for all 4338 data REM 301 parameters refined using 1 restraints END WGHT 0.0486 0.1687 REM Highest difference peak 0.184, deepest hole -0.220, 1-sigma level 0.048 Q1 1 0.5536 0.4413 0.3374 11.00000 0.05 0.18 Q2 1 0.8015 0.5829 0.1752 11.00000 0.05 0.17 Q3 1 0.7514 0.5532 0.4257 11.00000 0.05 0.15 Q4 1 0.8835 0.5491 0.3823 11.00000 0.05 0.14 Q5 1 0.6766 0.4231 0.3000 11.00000 0.05 0.13 Q6 1 0.9982 0.2972 -0.0414 11.00000 0.05 0.13 Q7 1 0.8236 0.5976 0.0533 11.00000 0.05 0.13 Q8 1 0.4944 0.7215 -0.1811 11.00000 0.05 0.13 Q9 1 0.6648 0.5668 0.2118 11.00000 0.05 0.13 Q10 1 0.9361 0.5818 0.1390 11.00000 0.05 0.13 ; _shelx_res_checksum 81821 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc/DCM'