# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2024 ####################################################################### # # 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_tm399 _database_code_depnum_ccdc_archive 'CCDC 2339798' loop_ _audit_author_name _audit_author_address 'Michel Giorgi' ;Aix Marseille University France ; _audit_update_record ; 2024-03-12 deposited with the CCDC. 2024-05-20 downloaded from the CCDC. ; _audit_creation_date 2023-09-15 _audit_creation_method ; Olex2 1.5 (compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) ; _shelx_SHELXL_version_number 2019/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'F6 P, C42 H63 N8 O4' _chemical_formula_sum 'C42 H63 F6 N8 O4 P' _chemical_formula_weight 888.97 _chemical_melting_point ? _chemical_oxdiff_formula 'c42 h63 f6 n8 o4 p1' 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' F F 0.0727 0.0534 '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' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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. ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.7061(5) _cell_length_b 35.5623(12) _cell_length_c 9.8813(3) _cell_angle_alpha 90 _cell_angle_beta 106.416(4) _cell_angle_gamma 90 _cell_volume 4620.0(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7465 _cell_measurement_temperature 180.00(10) _cell_measurement_theta_max 69.8720 _cell_measurement_theta_min 3.7800 _shelx_estimated_absorpt_T_max 0.955 _shelx_estimated_absorpt_T_min 0.820 _exptl_absorpt_coefficient_mu 1.150 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83817 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour violet _exptl_crystal_colour_primary violet _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description prism _exptl_crystal_F_000 1888 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0744 _diffrn_reflns_av_unetI/netI 0.0563 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.978 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 20778 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.978 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 69.962 _diffrn_reflns_theta_min 3.362 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 180.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.3045 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -84.00 -59.00 1.00 5.00 -- 0.00-159.00-163.00 25 2 \w -57.00 -30.00 1.00 5.00 -- 0.00 118.00 75.00 27 3 \w -142.00 -98.00 1.00 10.00 -- -54.86-159.00-163.00 44 4 \w -137.00-112.00 1.00 10.00 -- -54.86-118.00 -11.00 25 5 \w -67.00 -42.00 1.00 10.00 -- -54.86 118.00 75.00 25 6 \w 110.00 150.00 1.00 10.00 -- 54.86 159.00-132.00 40 7 \w 42.00 67.00 1.00 20.00 -- 109.71-118.00 -11.00 25 8 \w 115.00 140.00 1.00 20.00 -- 109.71 118.00 75.00 25 9 \w 93.00 118.00 1.00 20.00 -- 109.71 159.00-132.00 25 10 \w 87.00 135.00 1.00 20.00 -- 109.71-159.00-163.00 48 11 \w -7.00 21.00 1.00 5.00 -- 0.00 -77.00-120.00 28 12 \w -2.00 40.00 1.00 5.00 -- 0.00 77.00 -60.00 42 13 \w 12.00 52.00 1.00 5.00 -- 0.00 -99.00 150.00 40 14 \w 59.00 100.00 1.00 5.00 -- 0.00-178.00 -90.00 41 15 \w -115.00 -84.00 1.00 10.00 -- -54.86 -94.00 30.00 31 16 \w -155.00 -83.00 1.00 10.00 -- -54.86 -94.00 150.00 72 17 \w 105.00 147.00 1.00 10.00 -- 54.86 125.00 150.00 42 18 \w 104.00 151.00 1.00 10.00 -- 54.86 77.00 -30.00 47 19 \w 108.00 157.00 1.00 10.00 -- 54.86 77.00 0.00 49 20 \w 104.00 150.00 1.00 10.00 -- 54.86 77.00-120.00 46 21 \w 100.00 138.00 1.00 10.00 -- 54.86 125.00-180.00 38 22 \w 103.00 132.00 1.00 10.00 -- 54.86 77.00 60.00 29 23 \w 103.00 150.00 1.00 20.00 -- 109.71 77.00 0.00 47 24 \w 115.00 176.00 1.00 20.00 -- 109.71 111.00 120.00 61 25 \w 110.00 143.00 1.00 20.00 -- 109.71 178.00 150.00 33 26 \w 103.00 139.00 1.00 20.00 -- 109.71 77.00-150.00 36 27 \w 58.00 109.00 1.00 20.00 -- 109.71-111.00 0.00 51 28 \w 98.00 155.00 1.00 20.00 -- 109.71 -77.00 120.00 57 29 \w 103.00 178.00 1.00 20.00 -- 109.71 77.00 90.00 75 30 \w 5.00 94.00 1.00 20.00 -- 109.71 -77.00 120.00 89 31 \w 146.00 173.00 1.00 20.00 -- 109.71 77.00-150.00 27 32 \w 77.00 128.00 1.00 20.00 -- 109.71 178.00 -60.00 51 33 \w 103.00 177.00 1.00 20.00 -- 109.71 77.00 -60.00 74 34 \w 107.00 132.00 1.00 20.00 -- 109.71 77.00 150.00 25 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0506069000 _diffrn_orient_matrix_UB_12 -0.0355060000 _diffrn_orient_matrix_UB_13 -0.0436725000 _diffrn_orient_matrix_UB_21 -0.1044766000 _diffrn_orient_matrix_UB_22 -0.0239708000 _diffrn_orient_matrix_UB_23 0.0381626000 _diffrn_orient_matrix_UB_31 -0.1138138000 _diffrn_orient_matrix_UB_32 0.0062667000 _diffrn_orient_matrix_UB_33 -0.1018851000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 6602 _reflns_number_total 8558 _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. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _refine_diff_density_max 0.613 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.103 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 627 _refine_ls_number_reflns 8558 _refine_ls_number_restraints 102 _refine_ls_R_factor_all 0.1501 _refine_ls_R_factor_gt 0.1313 _refine_ls_restrained_S_all 1.126 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+45.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2814 _refine_ls_wR_factor_ref 0.2901 _refine_special_details ? _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C44-C45 1.48 with sigma of 0.002 C38-C39 1.48 with sigma of 0.002 C40-C41 1.48 with sigma of 0.002 C38-C43 1.48 with sigma of 0.002 C43-C44 1.48 with sigma of 0.002 C39-C40 1.48 with sigma of 0.002 3. Uiso/Uaniso restraints and constraints C44 \\sim C45: within 1.7A with sigma of 0.0001 and sigma for terminal atoms of 0.0002 within 1.7A C40 \\sim C41: within 1.7A with sigma of 0.0001 and sigma for terminal atoms of 0.0002 within 1.7A C41 \\sim C42: within 1.7A with sigma of 0.0001 and sigma for terminal atoms of 0.0002 within 1.7A C45 \\sim C46: within 1.7A with sigma of 0.0001 and sigma for terminal atoms of 0.0002 within 1.7A C43 \\sim C44: within 1.7A with sigma of 0.0001 and sigma for terminal atoms of 0.0002 within 1.7A C39 \\sim C40: within 1.7A with sigma of 0.0001 and sigma for terminal atoms of 0.0002 within 1.7A 4. Rigid body (RIGU) restrains P1, F1, F2, F3, F4, F5, F6, F7, F8 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002 5. Others Fixed Sof: F1(0.75) F2(0.75) F3(0.75) F4(0.75) F5(0.25) F6(0.25) F7(0.25) F8(0.25) H38A(0.5) H38B(0.5) H38C(0.5) H38D(0.5) C39(0.5) H39A(0.5) H39B(0.5) C40(0.5) H40A(0.5) H40B(0.5) C41(0.5) H41A(0.5) H41B(0.5) C42(0.5) H42A(0.5) H42B(0.5) H42C(0.5) C43(0.5) H43A(0.5) H43B(0.5) C44(0.5) H44A(0.5) H44B(0.5) C45(0.5) H45A(0.5) H45B(0.5) C46(0.5) H46A(0.5) H46B(0.5) H46C(0.5) 6.a Secondary CH2 refined with riding coordinates: C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A, H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C38(H38C,H38D), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B), C43(H43A, H43B), C44(H44A,H44B), C45(H45A,H45B) 6.b Aromatic/amide H refined with riding coordinates: N1(H1), N2(H2), N5(H5), N8(H8), C3(H3), C6(H6), C8(H8A), C9(H9), C12(H12), C19(H19), C22(H22) 6.c Idealised Me refined with riding coordinates: C42(H42A,H42B,H42C), C46(H46A,H46B,H46C) 6.d Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C26(H26A,H26B, H26C), C34(H34A,H34B,H34C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary ? 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 P1 P 0.64828(14) 0.54719(6) 0.77740(19) 0.0422(5) Uani 1 1 d . . . . . F9 F 0.6770(4) 0.54047(17) 0.9424(5) 0.0743(16) Uani 1 1 d . . . . . F10 F 0.6228(5) 0.5540(2) 0.6153(5) 0.097(2) Uani 1 1 d . . . . . F1 F 0.6713(11) 0.5047(2) 0.7570(10) 0.098(3) Uani 0.75 1 d . . P A 1 F2 F 0.5351(6) 0.5363(4) 0.7701(11) 0.113(3) Uani 0.75 1 d . . P A 1 F3 F 0.6184(13) 0.5884(3) 0.7984(10) 0.114(3) Uani 0.75 1 d . . P A 1 F4 F 0.7583(7) 0.5573(5) 0.7846(12) 0.117(4) Uani 0.75 1 d . . P A 1 F5 F 0.588(3) 0.5132(8) 0.744(3) 0.094(8) Uani 0.25 1 d . . P A 2 F6 F 0.564(2) 0.5707(10) 0.777(4) 0.097(9) Uani 0.25 1 d . . P A 2 F7 F 0.716(2) 0.5865(8) 0.823(3) 0.076(6) Uani 0.25 1 d . . P A 2 F8 F 0.759(2) 0.5290(10) 0.795(2) 0.078(6) Uani 0.25 1 d . . P A 2 O1 O 0.4120(3) 0.52919(14) -0.0388(5) 0.0403(12) Uani 1 1 d . . . . . O2 O 0.2627(3) 0.55242(15) -0.0667(5) 0.0441(12) Uani 1 1 d . . . . . O3 O 0.1968(4) 0.6541(2) 0.1796(9) 0.093(3) Uani 1 1 d . . . . . O4 O 0.3109(4) 0.68334(16) 0.3388(6) 0.0566(15) Uani 1 1 d . . . . . N1 N 0.7066(4) 0.60469(16) 0.1730(6) 0.0388(14) Uani 1 1 d . . . . . H1 H 0.650131 0.600137 0.105972 0.047 Uiso 1 1 calc R U . . . N2 N 0.5652(4) 0.55029(15) 0.1769(5) 0.0295(12) Uani 1 1 d . . . . . H2 H 0.548483 0.535811 0.101620 0.035 Uiso 1 1 calc R U . . . N3 N 0.3537(4) 0.55088(16) -0.0039(5) 0.0307(12) Uani 1 1 d . . . . . N4 N 0.2849(4) 0.65728(19) 0.2535(7) 0.0466(16) Uani 1 1 d . . . . . N5 N 0.4951(4) 0.65431(15) 0.4374(6) 0.0346(12) Uani 1 1 d . . . . . H5 H 0.454653 0.673023 0.443840 0.041 Uiso 1 1 calc R U . . . N6 N 0.9486(4) 0.54244(15) 0.5609(5) 0.0288(11) Uani 1 1 d . . . . . N7 N 0.8058(3) 0.48598(15) 0.5598(5) 0.0255(11) Uani 1 1 d . . . . . N8 N 1.0421(4) 0.43918(16) 0.9872(6) 0.0359(13) Uani 1 1 d . . . . . H8 H 1.103863 0.441084 1.045001 0.043 Uiso 1 1 calc R U . . . C1 C 0.7378(4) 0.57664(18) 0.2704(6) 0.0285(13) Uani 1 1 d . . . . . C2 C 0.6645(4) 0.54751(17) 0.2708(6) 0.0252(12) Uani 1 1 d . . . . . C3 C 0.6869(4) 0.51743(18) 0.3612(6) 0.0259(13) Uani 1 1 d . . . . . H3 H 0.637624 0.498271 0.355467 0.031 Uiso 1 1 calc R U . . . C4 C 0.7822(4) 0.51470(17) 0.4622(6) 0.0232(12) Uani 1 1 d . . . . . C5 C 0.8969(4) 0.48584(17) 0.6621(6) 0.0259(13) Uani 1 1 d . . . . . C6 C 0.9233(4) 0.45984(18) 0.7736(6) 0.0291(13) Uani 1 1 d . . . . . H6 H 0.876499 0.440664 0.779781 0.035 Uiso 1 1 calc R U . . . C7 C 1.0172(4) 0.46183(19) 0.8750(7) 0.0310(14) Uani 1 1 d . . . . . C8 C 1.0905(4) 0.48933(19) 0.8624(7) 0.0311(14) Uani 1 1 d . . . . . H8A H 1.156025 0.489826 0.928575 0.037 Uiso 1 1 calc R U . . . C9 C 1.0659(4) 0.51456(19) 0.7559(7) 0.0311(14) Uani 1 1 d . . . . . H9 H 1.115388 0.532518 0.748047 0.037 Uiso 1 1 calc R U . . . C10 C 0.9690(4) 0.51514(17) 0.6555(6) 0.0274(13) Uani 1 1 d . . . . . C11 C 0.8544(4) 0.54360(18) 0.4660(6) 0.0250(12) Uani 1 1 d . . . . . C12 C 0.8310(4) 0.57370(18) 0.3690(6) 0.0289(13) Uani 1 1 d . . . . . H12 H 0.881042 0.592413 0.372056 0.035 Uiso 1 1 calc R U . . . C13 C 0.7537(6) 0.6411(2) 0.1645(8) 0.0411(17) Uani 1 1 d . . . . . C14 C 0.6785(7) 0.6627(2) 0.0485(9) 0.060(2) Uani 1 1 d . . . . . H14A H 0.670374 0.649973 -0.041946 0.089 Uiso 1 1 calc R U . . . H14B H 0.703742 0.688286 0.043567 0.089 Uiso 1 1 calc R U . . . H14C H 0.612601 0.663776 0.069023 0.089 Uiso 1 1 calc R U . . . C15 C 0.8523(7) 0.6370(3) 0.1254(11) 0.065(2) Uani 1 1 d . . . . . H15A H 0.904207 0.625917 0.204696 0.098 Uiso 1 1 calc R U . . . H15B H 0.875120 0.661775 0.103420 0.098 Uiso 1 1 calc R U . . . H15C H 0.841349 0.620604 0.042690 0.098 Uiso 1 1 calc R U . . . C16 C 0.7690(7) 0.6629(2) 0.3003(9) 0.057(2) Uani 1 1 d . . . . . H16A H 0.797123 0.687754 0.290441 0.085 Uiso 1 1 calc R U . . . H16B H 0.816230 0.649234 0.377711 0.085 Uiso 1 1 calc R U . . . H16C H 0.703513 0.665854 0.320863 0.085 Uiso 1 1 calc R U . . . C17 C 0.4952(4) 0.57461(17) 0.1996(6) 0.0254(12) Uani 1 1 d . . . . . C18 C 0.3929(4) 0.57662(18) 0.1110(6) 0.0254(13) Uani 1 1 d . . . . . C19 C 0.3274(4) 0.60374(19) 0.1353(6) 0.0299(14) Uani 1 1 d . . . . . H19 H 0.259111 0.604461 0.077305 0.036 Uiso 1 1 calc R U . . . C20 C 0.3599(4) 0.62996(18) 0.2432(7) 0.0308(14) Uani 1 1 d . . . . . C21 C 0.4602(4) 0.62903(18) 0.3342(6) 0.0274(13) Uani 1 1 d . . . . . C22 C 0.5232(4) 0.60002(18) 0.3118(6) 0.0280(13) Uani 1 1 d . . . . . H22 H 0.588836 0.597493 0.376686 0.034 Uiso 1 1 calc R U . . . C23 C 0.5953(5) 0.6529(2) 0.5394(7) 0.0397(16) Uani 1 1 d . . . . . H23A H 0.645294 0.643381 0.492370 0.048 Uiso 1 1 calc R U . . . H23B H 0.593653 0.635166 0.615833 0.048 Uiso 1 1 calc R U . . . C24 C 0.6294(6) 0.6913(2) 0.6028(9) 0.051(2) Uani 1 1 d . . . . . H24A H 0.623147 0.709706 0.525736 0.061 Uiso 1 1 calc R U . . . H24B H 0.583940 0.699463 0.659216 0.061 Uiso 1 1 calc R U . . . C25 C 0.7368(7) 0.6910(3) 0.6947(10) 0.063(2) Uani 1 1 d . . . . . H25A H 0.782418 0.683654 0.637322 0.075 Uiso 1 1 calc R U . . . H25B H 0.743556 0.671796 0.769487 0.075 Uiso 1 1 calc R U . . . C26 C 0.7702(10) 0.7288(3) 0.7628(15) 0.114(5) Uani 1 1 d . . . . . H26A H 0.767610 0.747604 0.689354 0.172 Uiso 1 1 calc R U . . . H26B H 0.839908 0.726896 0.824568 0.172 Uiso 1 1 calc R U . . . H26C H 0.724629 0.736394 0.818559 0.172 Uiso 1 1 calc R U . . . C27 C 0.7330(4) 0.45439(19) 0.5453(6) 0.0306(14) Uani 1 1 d . . . . . H27A H 0.663072 0.464343 0.527636 0.037 Uiso 1 1 calc R U . . . H27B H 0.749448 0.439603 0.633732 0.037 Uiso 1 1 calc R U . . . C28 C 0.7392(5) 0.42915(19) 0.4226(7) 0.0339(14) Uani 1 1 d . . . . . H28A H 0.720742 0.444180 0.334688 0.041 Uiso 1 1 calc R U . . . H28B H 0.810467 0.420735 0.439006 0.041 Uiso 1 1 calc R U . . . C29 C 0.6709(5) 0.3947(2) 0.4017(7) 0.0395(16) Uani 1 1 d . . . . . H29A H 0.603448 0.402072 0.411210 0.047 Uiso 1 1 calc R U . . . H29B H 0.700766 0.376004 0.475915 0.047 Uiso 1 1 calc R U . . . C30 C 0.6577(6) 0.3770(2) 0.2567(7) 0.0434(17) Uani 1 1 d . . . . . H30A H 0.612287 0.393431 0.185088 0.052 Uiso 1 1 calc R U . . . H30B H 0.724795 0.376838 0.237637 0.052 Uiso 1 1 calc R U . . . C31 C 0.6154(6) 0.3377(2) 0.2360(7) 0.0417(17) Uani 1 1 d . . . . . H31A H 0.545105 0.337804 0.244306 0.050 Uiso 1 1 calc R U . . . H31B H 0.656992 0.321184 0.311026 0.050 Uiso 1 1 calc R U . . . C32 C 0.6148(6) 0.3220(2) 0.0934(8) 0.0461(18) Uani 1 1 d . . . . . H32A H 0.684667 0.323737 0.083881 0.055 Uiso 1 1 calc R U . . . H32B H 0.570653 0.338168 0.019459 0.055 Uiso 1 1 calc R U . . . C33 C 0.5789(7) 0.2818(2) 0.0660(9) 0.059(2) Uani 1 1 d . . . . . H33A H 0.509744 0.279571 0.077903 0.070 Uiso 1 1 calc R U . . . H33B H 0.624659 0.265189 0.136483 0.070 Uiso 1 1 calc R U . . . C34 C 0.5767(10) 0.2688(3) -0.0808(11) 0.083(3) Uani 1 1 d . . . . . H34A H 0.522253 0.281950 -0.150582 0.125 Uiso 1 1 calc R U . . . H34B H 0.564141 0.241627 -0.088733 0.125 Uiso 1 1 calc R U . . . H34C H 0.642153 0.274348 -0.098007 0.125 Uiso 1 1 calc R U . . . C35 C 0.9741(5) 0.4116(2) 1.0202(8) 0.0374(16) Uani 1 1 d . . . . . H35A H 0.954476 0.393051 0.942569 0.045 Uiso 1 1 calc R U . . . H35B H 0.911516 0.424416 1.026827 0.045 Uiso 1 1 calc R U . . . C36 C 1.0222(5) 0.3911(2) 1.1575(8) 0.0397(16) Uani 1 1 d . . . . . H36A H 1.078571 0.375208 1.146046 0.048 Uiso 1 1 calc R U . . . H36B H 1.051205 0.409790 1.232418 0.048 Uiso 1 1 calc R U . . . C37 C 0.9469(6) 0.3670(3) 1.2019(9) 0.060(2) Uani 1 1 d . . . . . H37A H 0.891299 0.383301 1.213398 0.072 Uiso 1 1 calc R U . . . H37B H 0.916748 0.349115 1.124498 0.072 Uiso 1 1 calc R U . . . C38 C 0.9867(6) 0.3451(3) 1.3338(10) 0.062(2) Uani 1 1 d D . . . . H38A H 1.043954 0.329436 1.323318 0.074 Uiso 0.5 1 calc R U P B 1 H38B H 1.014921 0.363026 1.411534 0.074 Uiso 0.5 1 calc R U P B 1 H38C H 1.042312 0.328763 1.321926 0.074 Uiso 0.5 1 calc R U P C 2 H38D H 1.017225 0.362973 1.410807 0.074 Uiso 0.5 1 calc R U P C 2 C39 C 0.914(2) 0.3201(14) 1.377(4) 0.1771(12) Uani 0.5 1 d D U P D 1 H39A H 0.854952 0.334974 1.384042 0.213 Uiso 0.5 1 calc R U P D 1 H39B H 0.889872 0.300457 1.304476 0.213 Uiso 0.5 1 calc R U P D 1 C40 C 0.963(3) 0.3021(10) 1.515(3) 0.1771(12) Uani 0.5 1 d D U P D 1 H40A H 1.028953 0.292117 1.507996 0.213 Uiso 0.5 1 calc R U P D 1 H40B H 0.979514 0.322739 1.584754 0.213 Uiso 0.5 1 calc R U P D 1 C41 C 0.917(3) 0.2719(10) 1.579(3) 0.1771(12) Uani 0.5 1 d D U P D 1 H41A H 0.858539 0.282185 1.607700 0.213 Uiso 0.5 1 calc R U P D 1 H41B H 0.967563 0.262453 1.664846 0.213 Uiso 0.5 1 calc R U P D 1 C42 C 0.880(3) 0.2387(11) 1.473(3) 0.1771(12) Uani 0.5 1 d . U P D 1 H42A H 0.844315 0.248799 1.379941 0.266 Uiso 0.5 1 calc R U P D 1 H42B H 0.833173 0.222660 1.506571 0.266 Uiso 0.5 1 calc R U P D 1 H42C H 0.938428 0.223832 1.466593 0.266 Uiso 0.5 1 calc R U P D 1 C43 C 0.9139(17) 0.3211(11) 1.380(4) 0.1329(11) Uani 0.5 1 d D U P D 2 H43A H 0.868442 0.338157 1.413255 0.160 Uiso 0.5 1 calc R U P D 2 H43B H 0.871216 0.308237 1.294995 0.160 Uiso 0.5 1 calc R U P D 2 C44 C 0.949(2) 0.2919(8) 1.490(4) 0.1329(11) Uani 0.5 1 d D U P D 2 H44A H 0.977460 0.304212 1.582701 0.160 Uiso 0.5 1 calc R U P D 2 H44B H 1.003916 0.276966 1.468904 0.160 Uiso 0.5 1 calc R U P D 2 C45 C 0.8650(18) 0.2666(9) 1.497(4) 0.1329(11) Uani 0.5 1 d D U P D 2 H45A H 0.830427 0.256564 1.402419 0.160 Uiso 0.5 1 calc R U P D 2 H45B H 0.814476 0.280518 1.532341 0.160 Uiso 0.5 1 calc R U P D 2 C46 C 0.910(2) 0.2347(8) 1.597(4) 0.1330(11) Uani 0.5 1 d . U P D 2 H46A H 0.959971 0.221144 1.561417 0.199 Uiso 0.5 1 calc R U P D 2 H46B H 0.855765 0.217439 1.603203 0.199 Uiso 0.5 1 calc R U P D 2 H46C H 0.943505 0.244916 1.690720 0.199 Uiso 0.5 1 calc R U P D 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0349(9) 0.0573(11) 0.0297(9) 0.0006(8) 0.0013(7) 0.0039(8) F9 0.091(4) 0.093(4) 0.036(3) 0.007(3) 0.013(3) 0.021(3) F10 0.113(5) 0.134(6) 0.035(3) 0.013(3) 0.005(3) 0.017(4) F1 0.159(8) 0.071(4) 0.071(6) -0.012(4) 0.045(7) 0.021(5) F2 0.052(4) 0.192(9) 0.093(7) 0.002(8) 0.018(5) -0.020(5) F3 0.208(11) 0.063(4) 0.066(6) 0.013(4) 0.030(8) 0.038(5) F4 0.049(4) 0.191(9) 0.095(7) 0.034(9) -0.008(4) -0.041(5) F5 0.106(13) 0.079(8) 0.069(16) 0.002(11) -0.020(16) -0.034(9) F6 0.055(9) 0.090(11) 0.16(3) 0.048(15) 0.059(14) 0.026(7) F7 0.082(12) 0.090(9) 0.060(14) -0.033(11) 0.024(12) -0.033(8) F8 0.069(8) 0.128(14) 0.040(11) 0.006(13) 0.019(9) 0.049(9) O1 0.023(2) 0.054(3) 0.035(3) -0.013(2) -0.005(2) 0.001(2) O2 0.017(2) 0.064(3) 0.042(3) -0.009(2) -0.006(2) -0.005(2) O3 0.027(3) 0.109(6) 0.120(6) -0.052(5) -0.018(3) 0.026(3) O4 0.044(3) 0.050(3) 0.071(4) -0.017(3) 0.008(3) 0.009(3) N1 0.033(3) 0.043(3) 0.029(3) 0.004(2) -0.010(2) -0.003(2) N2 0.017(2) 0.041(3) 0.023(3) -0.010(2) -0.006(2) 0.005(2) N3 0.018(2) 0.045(3) 0.026(3) 0.000(2) 0.000(2) -0.004(2) N4 0.025(3) 0.060(4) 0.050(4) -0.008(3) 0.003(3) 0.007(3) N5 0.030(3) 0.036(3) 0.036(3) -0.007(2) 0.007(2) 0.002(2) N6 0.018(2) 0.040(3) 0.022(3) -0.003(2) -0.005(2) -0.001(2) N7 0.011(2) 0.042(3) 0.020(2) -0.002(2) -0.0018(19) -0.004(2) N8 0.015(2) 0.049(3) 0.037(3) 0.005(3) -0.002(2) 0.000(2) C1 0.019(3) 0.040(4) 0.022(3) -0.005(3) -0.002(2) 0.001(2) C2 0.012(3) 0.039(3) 0.019(3) -0.006(2) -0.005(2) 0.003(2) C3 0.013(3) 0.039(3) 0.023(3) -0.005(2) -0.001(2) -0.001(2) C4 0.007(2) 0.041(3) 0.019(3) -0.003(2) -0.002(2) 0.000(2) C5 0.012(3) 0.036(3) 0.027(3) -0.004(2) 0.001(2) -0.001(2) C6 0.013(3) 0.039(4) 0.030(3) 0.000(3) -0.002(2) -0.004(2) C7 0.011(3) 0.043(4) 0.037(4) -0.003(3) 0.005(3) 0.003(2) C8 0.012(3) 0.046(4) 0.030(3) -0.004(3) -0.004(2) -0.001(2) C9 0.017(3) 0.042(4) 0.029(3) -0.003(3) -0.002(2) -0.002(3) C10 0.013(3) 0.035(3) 0.031(3) -0.005(3) 0.000(2) -0.001(2) C11 0.011(3) 0.040(3) 0.022(3) -0.004(2) 0.001(2) -0.001(2) C12 0.021(3) 0.038(3) 0.023(3) -0.003(3) -0.003(2) -0.002(2) C13 0.040(4) 0.042(4) 0.038(4) 0.002(3) 0.007(3) 0.001(3) C14 0.063(6) 0.052(5) 0.052(5) 0.014(4) -0.003(4) 0.003(4) C15 0.062(6) 0.070(6) 0.073(6) 0.013(5) 0.035(5) 0.004(5) C16 0.072(6) 0.042(4) 0.051(5) -0.003(4) 0.008(4) 0.005(4) C17 0.016(3) 0.036(3) 0.020(3) 0.002(2) 0.000(2) -0.001(2) C18 0.012(3) 0.041(3) 0.022(3) 0.000(2) 0.002(2) -0.002(2) C19 0.012(3) 0.048(4) 0.027(3) 0.005(3) 0.003(2) 0.002(2) C20 0.014(3) 0.039(4) 0.039(4) 0.000(3) 0.006(3) 0.003(2) C21 0.018(3) 0.040(4) 0.024(3) -0.001(3) 0.007(2) -0.004(2) C22 0.020(3) 0.041(4) 0.019(3) -0.001(2) -0.001(2) 0.001(3) C23 0.036(4) 0.044(4) 0.036(4) -0.009(3) 0.006(3) -0.003(3) C24 0.044(4) 0.046(4) 0.061(5) -0.014(4) 0.012(4) -0.006(3) C25 0.052(5) 0.066(6) 0.059(6) -0.017(4) -0.004(4) -0.013(4) C26 0.096(9) 0.080(8) 0.131(12) -0.034(8) -0.028(8) -0.032(7) C27 0.016(3) 0.046(4) 0.026(3) 0.002(3) -0.001(2) -0.008(3) C28 0.026(3) 0.042(4) 0.031(3) -0.004(3) 0.004(3) -0.006(3) C29 0.038(4) 0.045(4) 0.032(4) -0.002(3) 0.004(3) -0.011(3) C30 0.053(5) 0.044(4) 0.033(4) -0.004(3) 0.012(3) -0.012(3) C31 0.038(4) 0.049(4) 0.036(4) -0.003(3) 0.006(3) -0.010(3) C32 0.052(5) 0.046(4) 0.042(4) -0.008(3) 0.016(4) -0.012(3) C33 0.066(6) 0.055(5) 0.060(5) -0.015(4) 0.027(5) -0.019(4) C34 0.114(9) 0.076(7) 0.071(7) -0.036(6) 0.042(7) -0.033(6) C35 0.014(3) 0.050(4) 0.046(4) 0.001(3) 0.004(3) 0.000(3) C36 0.024(3) 0.051(4) 0.040(4) 0.002(3) 0.002(3) 0.001(3) C37 0.038(4) 0.080(6) 0.059(5) 0.018(5) 0.007(4) -0.005(4) C38 0.036(4) 0.078(6) 0.064(6) 0.023(5) 0.002(4) -0.006(4) C39 0.1897(18) 0.1698(18) 0.1199(18) 0.0939(18) -0.0407(18) -0.0798(18) C40 0.1897(18) 0.1698(18) 0.1199(18) 0.0939(18) -0.0407(18) -0.0798(18) C41 0.1897(18) 0.1698(18) 0.1199(18) 0.0939(18) -0.0407(18) -0.0798(18) C42 0.1897(18) 0.1698(18) 0.1199(18) 0.0939(18) -0.0407(18) -0.0798(18) C43 0.0856(18) 0.1337(18) 0.1815(18) 0.0848(18) 0.0411(18) -0.0108(18) C44 0.0856(18) 0.1337(18) 0.1815(18) 0.0848(18) 0.0411(18) -0.0108(18) C45 0.0856(18) 0.1337(18) 0.1815(18) 0.0848(18) 0.0411(18) -0.0108(18) C46 0.0857(18) 0.1337(18) 0.1815(18) 0.0848(18) 0.0411(18) -0.0108(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F9 1.583(5) . ? P1 F10 1.559(5) . ? P1 F1 1.569(8) . ? P1 F2 1.581(9) . ? P1 F3 1.551(9) . ? P1 F4 1.532(9) . ? P1 F5 1.45(2) . ? P1 F6 1.43(2) . ? P1 F7 1.67(2) . ? P1 F8 1.62(2) . ? O1 N3 1.228(7) . ? O2 N3 1.227(6) . ? O3 N4 1.227(8) . ? O4 N4 1.235(8) . ? N1 H1 0.8800 . ? N1 C1 1.368(8) . ? N1 C13 1.460(9) . ? N2 H2 0.8800 . ? N2 C2 1.418(7) . ? N2 C17 1.357(8) . ? N3 C18 1.440(8) . ? N4 C20 1.438(8) . ? N5 H5 0.8800 . ? N5 C21 1.341(8) . ? N5 C23 1.457(8) . ? N6 C10 1.322(8) . ? N6 C11 1.365(7) . ? N7 C4 1.379(8) . ? N7 C5 1.366(7) . ? N7 C27 1.482(7) . ? N8 H8 0.8800 . ? N8 C7 1.334(8) . ? N8 C35 1.452(8) . ? C1 C2 1.444(9) . ? C1 C12 1.374(8) . ? C2 C3 1.372(9) . ? C3 H3 0.9500 . ? C3 C4 1.404(7) . ? C4 C11 1.420(8) . ? C5 C6 1.405(9) . ? C5 C10 1.450(8) . ? C6 H6 0.9500 . ? C6 C7 1.392(8) . ? C7 C8 1.433(9) . ? C8 H8A 0.9500 . ? C8 C9 1.352(9) . ? C9 H9 0.9500 . ? C9 C10 1.416(8) . ? C11 C12 1.412(9) . ? C12 H12 0.9500 . ? C13 C14 1.516(10) . ? C13 C15 1.514(11) . ? C13 C16 1.512(10) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.429(8) . ? C17 C22 1.397(8) . ? C18 C19 1.384(9) . ? C19 H19 0.9500 . ? C19 C20 1.392(9) . ? C20 C21 1.415(8) . ? C21 C22 1.403(9) . ? C22 H22 0.9500 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C23 C24 1.518(10) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C24 C25 1.496(11) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C25 C26 1.517(13) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C27 C28 1.530(9) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.519(9) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C29 C30 1.528(9) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C30 C31 1.506(10) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C31 C32 1.512(10) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C33 1.513(10) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C33 C34 1.515(12) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C35 C36 1.516(9) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C36 C37 1.501(10) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C37 C38 1.483(11) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C38 H38C 0.9900 . ? C38 H38D 0.9900 . ? C38 C39 1.480(2) . ? C38 C43 1.480(2) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C39 C40 1.480(2) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C40 C41 1.480(2) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C41 C42 1.57(5) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C43 C44 1.480(2) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C44 C45 1.480(2) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C45 C46 1.51(4) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 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 F9 P1 F7 83.7(9) . . ? F9 P1 F8 82.8(8) . . ? F10 P1 F9 178.6(4) . . ? F10 P1 F1 90.7(4) . . ? F10 P1 F2 93.4(5) . . ? F10 P1 F7 95.4(9) . . ? F10 P1 F8 96.0(8) . . ? F1 P1 F9 89.2(4) . . ? F1 P1 F2 89.3(7) . . ? F2 P1 F9 88.0(4) . . ? F3 P1 F9 90.2(4) . . ? F3 P1 F10 90.0(5) . . ? F3 P1 F1 176.1(8) . . ? F3 P1 F2 86.9(8) . . ? F4 P1 F9 91.8(5) . . ? F4 P1 F10 86.7(5) . . ? F4 P1 F1 90.0(7) . . ? F4 P1 F2 179.3(8) . . ? F4 P1 F3 93.8(8) . . ? F5 P1 F9 93.9(12) . . ? F5 P1 F10 87.1(12) . . ? F5 P1 F7 177.3(17) . . ? F5 P1 F8 98(2) . . ? F6 P1 F9 93.1(15) . . ? F6 P1 F10 87.9(15) . . ? F6 P1 F5 95(2) . . ? F6 P1 F7 84.3(17) . . ? F6 P1 F8 167(2) . . ? F8 P1 F7 82.5(16) . . ? C1 N1 H1 115.4 . . ? C1 N1 C13 129.2(5) . . ? C13 N1 H1 115.4 . . ? C2 N2 H2 119.0 . . ? C17 N2 H2 119.0 . . ? C17 N2 C2 122.0(5) . . ? O1 N3 C18 119.6(5) . . ? O2 N3 O1 122.4(5) . . ? O2 N3 C18 118.0(5) . . ? O3 N4 O4 121.4(6) . . ? O3 N4 C20 119.9(6) . . ? O4 N4 C20 118.7(6) . . ? C21 N5 H5 117.7 . . ? C21 N5 C23 124.5(6) . . ? C23 N5 H5 117.7 . . ? C10 N6 C11 118.6(5) . . ? C4 N7 C27 118.3(4) . . ? C5 N7 C4 120.4(5) . . ? C5 N7 C27 121.2(5) . . ? C7 N8 H8 117.8 . . ? C7 N8 C35 124.4(5) . . ? C35 N8 H8 117.8 . . ? N1 C1 C2 116.5(5) . . ? N1 C1 C12 126.7(6) . . ? C12 C1 C2 116.8(6) . . ? N2 C2 C1 119.2(5) . . ? C3 C2 N2 118.5(5) . . ? C3 C2 C1 122.3(5) . . ? C2 C3 H3 119.7 . . ? C2 C3 C4 120.6(6) . . ? C4 C3 H3 119.7 . . ? N7 C4 C3 122.4(5) . . ? N7 C4 C11 119.5(5) . . ? C3 C4 C11 118.0(5) . . ? N7 C5 C6 124.2(5) . . ? N7 C5 C10 117.1(5) . . ? C6 C5 C10 118.7(5) . . ? C5 C6 H6 119.6 . . ? C7 C6 C5 120.8(6) . . ? C7 C6 H6 119.6 . . ? N8 C7 C6 122.4(6) . . ? N8 C7 C8 117.6(5) . . ? C6 C7 C8 120.0(6) . . ? C7 C8 H8A 120.2 . . ? C9 C8 C7 119.6(5) . . ? C9 C8 H8A 120.2 . . ? C8 C9 H9 118.9 . . ? C8 C9 C10 122.2(6) . . ? C10 C9 H9 118.9 . . ? N6 C10 C5 123.3(5) . . ? N6 C10 C9 118.4(6) . . ? C9 C10 C5 118.4(6) . . ? N6 C11 C4 120.9(5) . . ? N6 C11 C12 118.6(5) . . ? C12 C11 C4 120.5(5) . . ? C1 C12 C11 121.8(6) . . ? C1 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? N1 C13 C14 106.0(6) . . ? N1 C13 C15 111.7(7) . . ? N1 C13 C16 110.9(6) . . ? C15 C13 C14 108.8(7) . . ? C16 C13 C14 107.8(7) . . ? C16 C13 C15 111.5(7) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 C18 123.2(5) . . ? N2 C17 C22 119.6(5) . . ? C22 C17 C18 117.1(5) . . ? C17 C18 N3 122.3(5) . . ? C19 C18 N3 117.6(5) . . ? C19 C18 C17 120.0(6) . . ? C18 C19 H19 119.4 . . ? C18 C19 C20 121.2(5) . . ? C20 C19 H19 119.4 . . ? C19 C20 N4 115.3(5) . . ? C19 C20 C21 120.9(6) . . ? C21 C20 N4 123.8(6) . . ? N5 C21 C20 122.7(6) . . ? N5 C21 C22 120.7(5) . . ? C22 C21 C20 116.6(6) . . ? C17 C22 C21 123.9(5) . . ? C17 C22 H22 118.1 . . ? C21 C22 H22 118.1 . . ? N5 C23 H23A 109.2 . . ? N5 C23 H23B 109.2 . . ? N5 C23 C24 112.0(6) . . ? H23A C23 H23B 107.9 . . ? C24 C23 H23A 109.2 . . ? C24 C23 H23B 109.2 . . ? C23 C24 H24A 109.1 . . ? C23 C24 H24B 109.1 . . ? H24A C24 H24B 107.9 . . ? C25 C24 C23 112.3(7) . . ? C25 C24 H24A 109.1 . . ? C25 C24 H24B 109.1 . . ? C24 C25 H25A 109.1 . . ? C24 C25 H25B 109.1 . . ? C24 C25 C26 112.6(9) . . ? H25A C25 H25B 107.8 . . ? C26 C25 H25A 109.1 . . ? C26 C25 H25B 109.1 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N7 C27 H27A 109.8 . . ? N7 C27 H27B 109.8 . . ? N7 C27 C28 109.6(5) . . ? H27A C27 H27B 108.2 . . ? C28 C27 H27A 109.8 . . ? C28 C27 H27B 109.8 . . ? C27 C28 H28A 108.7 . . ? C27 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? C29 C28 C27 114.2(5) . . ? C29 C28 H28A 108.7 . . ? C29 C28 H28B 108.7 . . ? C28 C29 H29A 109.3 . . ? C28 C29 H29B 109.3 . . ? C28 C29 C30 111.4(6) . . ? H29A C29 H29B 108.0 . . ? C30 C29 H29A 109.3 . . ? C30 C29 H29B 109.3 . . ? C29 C30 H30A 108.1 . . ? C29 C30 H30B 108.1 . . ? H30A C30 H30B 107.3 . . ? C31 C30 C29 116.8(6) . . ? C31 C30 H30A 108.1 . . ? C31 C30 H30B 108.1 . . ? C30 C31 H31A 109.3 . . ? C30 C31 H31B 109.3 . . ? C30 C31 C32 111.7(6) . . ? H31A C31 H31B 107.9 . . ? C32 C31 H31A 109.3 . . ? C32 C31 H31B 109.3 . . ? C31 C32 H32A 108.4 . . ? C31 C32 H32B 108.4 . . ? C31 C32 C33 115.5(7) . . ? H32A C32 H32B 107.5 . . ? C33 C32 H32A 108.4 . . ? C33 C32 H32B 108.4 . . ? C32 C33 H33A 109.2 . . ? C32 C33 H33B 109.2 . . ? C32 C33 C34 112.2(7) . . ? H33A C33 H33B 107.9 . . ? C34 C33 H33A 109.2 . . ? C34 C33 H33B 109.2 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34B 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N8 C35 H35A 109.1 . . ? N8 C35 H35B 109.1 . . ? N8 C35 C36 112.4(5) . . ? H35A C35 H35B 107.9 . . ? C36 C35 H35A 109.1 . . ? C36 C35 H35B 109.1 . . ? C35 C36 H36A 109.2 . . ? C35 C36 H36B 109.2 . . ? H36A C36 H36B 107.9 . . ? C37 C36 C35 112.1(6) . . ? C37 C36 H36A 109.2 . . ? C37 C36 H36B 109.2 . . ? C36 C37 H37A 108.2 . . ? C36 C37 H37B 108.2 . . ? H37A C37 H37B 107.3 . . ? C38 C37 C36 116.4(7) . . ? C38 C37 H37A 108.2 . . ? C38 C37 H37B 108.2 . . ? C37 C38 H38A 108.0 . . ? C37 C38 H38B 108.0 . . ? C37 C38 H38C 107.9 . . ? C37 C38 H38D 107.9 . . ? H38A C38 H38B 107.2 . . ? H38C C38 H38D 107.2 . . ? C39 C38 C37 117.2(12) . . ? C39 C38 H38A 108.0 . . ? C39 C38 H38B 108.0 . . ? C43 C38 C37 117.5(13) . . ? C43 C38 H38C 107.9 . . ? C43 C38 H38D 107.9 . . ? C38 C39 H39A 109.4 . . ? C38 C39 H39B 109.4 . . ? H39A C39 H39B 108.0 . . ? C40 C39 C38 111.1(15) . . ? C40 C39 H39A 109.4 . . ? C40 C39 H39B 109.4 . . ? C39 C40 H40A 106.1 . . ? C39 C40 H40B 106.1 . . ? H40A C40 H40B 106.3 . . ? C41 C40 C39 125(2) . . ? C41 C40 H40A 106.1 . . ? C41 C40 H40B 106.1 . . ? C40 C41 H41A 109.4 . . ? C40 C41 H41B 109.4 . . ? C40 C41 C42 111(3) . . ? H41A C41 H41B 108.0 . . ? C42 C41 H41A 109.4 . . ? C42 C41 H41B 109.4 . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42B 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C38 C43 H43A 107.0 . . ? C38 C43 H43B 107.0 . . ? H43A C43 H43B 106.7 . . ? C44 C43 C38 121.5(17) . . ? C44 C43 H43A 107.0 . . ? C44 C43 H43B 107.0 . . ? C43 C44 H44A 109.3 . . ? C43 C44 H44B 109.3 . . ? C43 C44 C45 111.5(18) . . ? H44A C44 H44B 108.0 . . ? C45 C44 H44A 109.3 . . ? C45 C44 H44B 109.3 . . ? C44 C45 H45A 110.1 . . ? C44 C45 H45B 110.1 . . ? C44 C45 C46 108(2) . . ? H45A C45 H45B 108.4 . . ? C46 C45 H45A 110.1 . . ? C46 C45 H45B 110.1 . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46B 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 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 O1 N3 C18 C17 -8.8(9) . . . . ? O1 N3 C18 C19 172.0(6) . . . . ? O2 N3 C18 C17 173.6(6) . . . . ? O2 N3 C18 C19 -5.7(8) . . . . ? O3 N4 C20 C19 7.3(11) . . . . ? O3 N4 C20 C21 -172.9(8) . . . . ? O4 N4 C20 C19 -173.8(7) . . . . ? O4 N4 C20 C21 6.0(11) . . . . ? N1 C1 C2 N2 -2.6(8) . . . . ? N1 C1 C2 C3 178.7(6) . . . . ? N1 C1 C12 C11 179.1(6) . . . . ? N2 C2 C3 C4 -176.0(5) . . . . ? N2 C17 C18 N3 4.9(9) . . . . ? N2 C17 C18 C19 -175.9(6) . . . . ? N2 C17 C22 C21 172.3(6) . . . . ? N3 C18 C19 C20 -179.2(6) . . . . ? N4 C20 C21 N5 -1.4(10) . . . . ? N4 C20 C21 C22 178.7(6) . . . . ? N5 C21 C22 C17 -174.5(6) . . . . ? N5 C23 C24 C25 -173.3(7) . . . . ? N6 C11 C12 C1 179.9(6) . . . . ? N7 C4 C11 N6 3.0(9) . . . . ? N7 C4 C11 C12 -178.6(5) . . . . ? N7 C5 C6 C7 -179.1(6) . . . . ? N7 C5 C10 N6 3.5(9) . . . . ? N7 C5 C10 C9 -176.8(6) . . . . ? N7 C27 C28 C29 177.5(5) . . . . ? N8 C7 C8 C9 -175.4(6) . . . . ? N8 C35 C36 C37 171.5(7) . . . . ? C1 N1 C13 C14 -171.9(7) . . . . ? C1 N1 C13 C15 69.8(10) . . . . ? C1 N1 C13 C16 -55.3(10) . . . . ? C1 C2 C3 C4 2.7(9) . . . . ? C2 N2 C17 C18 -176.5(6) . . . . ? C2 N2 C17 C22 5.5(9) . . . . ? C2 C1 C12 C11 0.2(9) . . . . ? C2 C3 C4 N7 176.5(5) . . . . ? C2 C3 C4 C11 -0.9(9) . . . . ? C3 C4 C11 N6 -179.5(5) . . . . ? C3 C4 C11 C12 -1.2(9) . . . . ? C4 N7 C5 C6 173.6(6) . . . . ? C4 N7 C5 C10 -4.9(8) . . . . ? C4 N7 C27 C28 74.3(7) . . . . ? C4 C11 C12 C1 1.5(9) . . . . ? C5 N7 C4 C3 -175.5(6) . . . . ? C5 N7 C4 C11 1.8(8) . . . . ? C5 N7 C27 C28 -102.0(6) . . . . ? C5 C6 C7 N8 175.5(6) . . . . ? C5 C6 C7 C8 -3.4(10) . . . . ? C6 C5 C10 N6 -175.0(6) . . . . ? C6 C5 C10 C9 4.6(9) . . . . ? C6 C7 C8 C9 3.6(10) . . . . ? C7 N8 C35 C36 -177.6(6) . . . . ? C7 C8 C9 C10 0.6(10) . . . . ? C8 C9 C10 N6 175.0(6) . . . . ? C8 C9 C10 C5 -4.6(10) . . . . ? C10 N6 C11 C4 -4.4(9) . . . . ? C10 N6 C11 C12 177.2(6) . . . . ? C10 C5 C6 C7 -0.7(9) . . . . ? C11 N6 C10 C5 1.1(9) . . . . ? C11 N6 C10 C9 -178.5(6) . . . . ? C12 C1 C2 N2 176.3(5) . . . . ? C12 C1 C2 C3 -2.4(9) . . . . ? C13 N1 C1 C2 166.3(6) . . . . ? C13 N1 C1 C12 -12.5(12) . . . . ? C17 N2 C2 C1 -75.2(8) . . . . ? C17 N2 C2 C3 103.6(7) . . . . ? C17 C18 C19 C20 1.6(9) . . . . ? C18 C17 C22 C21 -5.8(9) . . . . ? C18 C19 C20 N4 178.0(6) . . . . ? C18 C19 C20 C21 -1.8(10) . . . . ? C19 C20 C21 N5 178.4(6) . . . . ? C19 C20 C21 C22 -1.5(9) . . . . ? C20 C21 C22 C17 5.5(9) . . . . ? C21 N5 C23 C24 157.4(7) . . . . ? C22 C17 C18 N3 -177.1(5) . . . . ? C22 C17 C18 C19 2.1(9) . . . . ? C23 N5 C21 C20 175.6(6) . . . . ? C23 N5 C21 C22 -4.5(10) . . . . ? C23 C24 C25 C26 -177.9(9) . . . . ? C27 N7 C4 C3 8.1(8) . . . . ? C27 N7 C4 C11 -174.5(5) . . . . ? C27 N7 C5 C6 -10.2(9) . . . . ? C27 N7 C5 C10 171.3(5) . . . . ? C27 C28 C29 C30 164.1(6) . . . . ? C28 C29 C30 C31 164.5(7) . . . . ? C29 C30 C31 C32 -174.9(7) . . . . ? C30 C31 C32 C33 176.8(7) . . . . ? C31 C32 C33 C34 177.8(8) . . . . ? C35 N8 C7 C6 -3.2(10) . . . . ? C35 N8 C7 C8 175.8(6) . . . . ? C35 C36 C37 C38 178.8(8) . . . . ? C36 C37 C38 C39 -178(3) . . . . ? C36 C37 C38 C43 180(2) . . . . ? C37 C38 C39 C40 -176(3) . . . . ? C37 C38 C43 C44 166(3) . . . . ? C38 C39 C40 C41 -171(4) . . . . ? C38 C43 C44 C45 -168(4) . . . . ? C39 C40 C41 C42 52(6) . . . . ? C43 C44 C45 C46 172(4) . . . . ? _shelx_res_file ; TITL tm399_auto_a.res in P2(1)/c tm399.res created by SHELXL-2019/3 at 15:16:26 on 15-Sep-2023 REM Old TITL tm399_auto in P2(1)/m REM SHELXT solution in P2(1)/c REM R1 0.269, Rweak 0.163, Alpha 0.104, Orientation a =c, b =-b, c =a REM Formula found by SHELXT: C35 N5 F4 F2 P CELL 1.54184 13.7061 35.5623 9.8813 90 106.416 90 ZERR 4 0.0005 0.0012 0.0003 0 0.004 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O P UNIT 168 252 24 32 16 4 RIGU 0.002 0.002 P1 F1 > F8 DFIX 1.48 0.002 C44 C45 DFIX 1.48 0.002 C38 C39 DFIX 1.48 0.002 C40 C41 DFIX 1.48 0.002 C38 C43 SIMU 0.0001 0.0002 1.7 C44 C45 DFIX 1.48 0.002 C43 C44 SIMU 0.0001 0.0002 1.7 C40 C41 SIMU 0.0001 0.0002 1.7 C41 C42 SIMU 0.0001 0.0002 1.7 C45 C46 DFIX 1.48 0.002 C39 C40 SIMU 0.0001 0.0002 1.7 C43 C44 SIMU 0.0001 0.0002 1.7 C39 C40 L.S. 10 PLAN 8 SIZE 0.04 0.14 0.18 TEMP -93 CONF MORE -1 BOND $H fmap 2 acta OMIT -14 1 4 OMIT -12 1 2 OMIT -12 3 2 OMIT -12 6 2 OMIT -3 5 1 OMIT 1 1 10 OMIT 1 8 0 OMIT 2 4 0 OMIT 3 1 8 OMIT 3 6 0 REM REM REM WGHT 0.000000 45.000000 FVAR 0.25028 P1 6 0.648277 0.547189 0.777399 11.00000 0.03486 0.05730 = 0.02969 0.00061 0.00133 0.00393 F9 3 0.677025 0.540469 0.942377 11.00000 0.09105 0.09283 = 0.03631 0.00727 0.01336 0.02058 F10 3 0.622832 0.553988 0.615279 11.00000 0.11341 0.13356 = 0.03495 0.01340 0.00544 0.01681 PART 1 F1 3 0.671287 0.504669 0.757024 10.75000 0.15874 0.07091 = 0.07071 -0.01160 0.04468 0.02122 F2 3 0.535064 0.536255 0.770053 10.75000 0.05178 0.19195 = 0.09306 0.00210 0.01839 -0.02004 F3 3 0.618352 0.588376 0.798424 10.75000 0.20778 0.06321 = 0.06620 0.01318 0.03041 0.03834 F4 3 0.758283 0.557265 0.784616 10.75000 0.04909 0.19118 = 0.09466 0.03417 -0.00811 -0.04149 PART 2 F5 3 0.588196 0.513167 0.744155 10.25000 0.10617 0.07911 = 0.06942 0.00153 -0.02019 -0.03405 F6 3 0.563782 0.570682 0.777354 10.25000 0.05487 0.08988 = 0.16436 0.04783 0.05949 0.02576 F7 3 0.716225 0.586467 0.823020 10.25000 0.08190 0.08995 = 0.06006 -0.03318 0.02419 -0.03258 F8 3 0.759488 0.528966 0.795199 10.25000 0.06888 0.12798 = 0.03957 0.00642 0.01915 0.04868 PART 0 O1 5 0.411961 0.529187 -0.038789 11.00000 0.02299 0.05437 = 0.03525 -0.01313 -0.00542 0.00066 O2 5 0.262712 0.552422 -0.066667 11.00000 0.01743 0.06414 = 0.04175 -0.00882 -0.00601 -0.00470 O3 5 0.196758 0.654060 0.179644 11.00000 0.02685 0.10917 = 0.12042 -0.05177 -0.01833 0.02617 O4 5 0.310939 0.683335 0.338785 11.00000 0.04367 0.04979 = 0.07101 -0.01655 0.00762 0.00922 N1 4 0.706612 0.604688 0.173004 11.00000 0.03287 0.04271 = 0.02919 0.00387 -0.01028 -0.00308 AFIX 43 H1 2 0.650131 0.600137 0.105972 11.00000 -1.20000 AFIX 0 N2 4 0.565212 0.550287 0.176891 11.00000 0.01717 0.04125 = 0.02303 -0.00974 -0.00585 0.00454 AFIX 43 H2 2 0.548483 0.535811 0.101620 11.00000 -1.20000 AFIX 0 N3 4 0.353677 0.550878 -0.003939 11.00000 0.01753 0.04501 = 0.02560 -0.00035 -0.00020 -0.00374 N4 4 0.284892 0.657281 0.253486 11.00000 0.02508 0.06022 = 0.04970 -0.00813 0.00280 0.00748 N5 4 0.495103 0.654310 0.437361 11.00000 0.03034 0.03574 = 0.03631 -0.00692 0.00729 0.00248 AFIX 43 H5 2 0.454653 0.673023 0.443840 11.00000 -1.20000 AFIX 0 N6 4 0.948574 0.542444 0.560932 11.00000 0.01799 0.03972 = 0.02190 -0.00273 -0.00549 -0.00109 N7 4 0.805828 0.485982 0.559811 11.00000 0.01070 0.04243 = 0.01960 -0.00167 -0.00181 -0.00425 N8 4 1.042094 0.439184 0.987173 11.00000 0.01538 0.04942 = 0.03702 0.00451 -0.00229 0.00006 AFIX 43 H8 2 1.103863 0.441084 1.045001 11.00000 -1.20000 AFIX 0 C1 1 0.737837 0.576641 0.270365 11.00000 0.01888 0.03976 = 0.02198 -0.00456 -0.00203 0.00088 C2 1 0.664538 0.547509 0.270822 11.00000 0.01230 0.03881 = 0.01905 -0.00627 -0.00464 0.00331 C3 1 0.686943 0.517426 0.361206 11.00000 0.01263 0.03905 = 0.02256 -0.00530 -0.00074 -0.00090 AFIX 43 H3 2 0.637624 0.498271 0.355467 11.00000 -1.20000 AFIX 0 C4 1 0.782178 0.514702 0.462158 11.00000 0.00655 0.04066 = 0.01885 -0.00328 -0.00207 -0.00010 C5 1 0.896869 0.485839 0.662103 11.00000 0.01206 0.03559 = 0.02714 -0.00418 0.00102 -0.00137 C6 1 0.923298 0.459841 0.773581 11.00000 0.01274 0.03942 = 0.03007 -0.00017 -0.00230 -0.00383 AFIX 43 H6 2 0.876499 0.440664 0.779781 11.00000 -1.20000 AFIX 0 C7 1 1.017185 0.461833 0.875036 11.00000 0.01122 0.04318 = 0.03749 -0.00256 0.00501 0.00327 C8 1 1.090498 0.489331 0.862409 11.00000 0.01239 0.04564 = 0.02951 -0.00373 -0.00368 -0.00106 AFIX 43 H8A 2 1.156025 0.489826 0.928575 11.00000 -1.20000 AFIX 0 C9 1 1.065943 0.514564 0.755863 11.00000 0.01677 0.04204 = 0.02902 -0.00275 -0.00227 -0.00226 AFIX 43 H9 2 1.115388 0.532518 0.748047 11.00000 -1.20000 AFIX 0 C10 1 0.969008 0.515136 0.655516 11.00000 0.01268 0.03474 = 0.03098 -0.00535 0.00012 -0.00051 C11 1 0.854386 0.543599 0.466031 11.00000 0.01058 0.04017 = 0.02210 -0.00412 0.00109 -0.00067 C12 1 0.831017 0.573696 0.369037 11.00000 0.02062 0.03785 = 0.02283 -0.00258 -0.00260 -0.00158 AFIX 43 H12 2 0.881042 0.592413 0.372056 11.00000 -1.20000 AFIX 0 C13 1 0.753717 0.641112 0.164528 11.00000 0.04019 0.04230 = 0.03797 0.00195 0.00651 0.00100 C14 1 0.678455 0.662695 0.048540 11.00000 0.06328 0.05217 = 0.05170 0.01369 -0.00265 0.00301 AFIX 137 H14A 2 0.670374 0.649973 -0.041946 11.00000 -1.50000 H14B 2 0.703742 0.688286 0.043567 11.00000 -1.50000 H14C 2 0.612601 0.663776 0.069023 11.00000 -1.50000 AFIX 0 C15 1 0.852288 0.636988 0.125382 11.00000 0.06222 0.07021 = 0.07266 0.01314 0.03475 0.00435 AFIX 137 H15A 2 0.904207 0.625917 0.204696 11.00000 -1.50000 H15B 2 0.875120 0.661775 0.103420 11.00000 -1.50000 H15C 2 0.841349 0.620604 0.042690 11.00000 -1.50000 AFIX 0 C16 1 0.768989 0.662906 0.300334 11.00000 0.07153 0.04222 = 0.05118 -0.00307 0.00833 0.00509 AFIX 137 H16A 2 0.797123 0.687754 0.290441 11.00000 -1.50000 H16B 2 0.816230 0.649234 0.377711 11.00000 -1.50000 H16C 2 0.703513 0.665854 0.320863 11.00000 -1.50000 AFIX 0 C17 1 0.495167 0.574611 0.199620 11.00000 0.01614 0.03637 = 0.02046 0.00250 0.00008 -0.00061 C18 1 0.392930 0.576624 0.111012 11.00000 0.01165 0.04067 = 0.02232 0.00019 0.00229 -0.00242 C19 1 0.327422 0.603738 0.135314 11.00000 0.01231 0.04824 = 0.02735 0.00494 0.00282 0.00200 AFIX 43 H19 2 0.259111 0.604461 0.077305 11.00000 -1.20000 AFIX 0 C20 1 0.359866 0.629961 0.243236 11.00000 0.01381 0.03905 = 0.03883 0.00026 0.00623 0.00317 C21 1 0.460212 0.629034 0.334238 11.00000 0.01775 0.04034 = 0.02438 -0.00094 0.00664 -0.00430 C22 1 0.523207 0.600016 0.311771 11.00000 0.02032 0.04100 = 0.01865 -0.00102 -0.00087 0.00091 AFIX 43 H22 2 0.588836 0.597493 0.376686 11.00000 -1.20000 AFIX 0 C23 1 0.595319 0.652930 0.539378 11.00000 0.03575 0.04386 = 0.03649 -0.00888 0.00551 -0.00307 AFIX 23 H23A 2 0.645294 0.643381 0.492370 11.00000 -1.20000 H23B 2 0.593653 0.635166 0.615833 11.00000 -1.20000 AFIX 0 C24 1 0.629373 0.691265 0.602774 11.00000 0.04399 0.04627 = 0.06083 -0.01400 0.01191 -0.00568 AFIX 23 H24A 2 0.623147 0.709706 0.525736 11.00000 -1.20000 H24B 2 0.583940 0.699463 0.659216 11.00000 -1.20000 AFIX 0 C25 1 0.736804 0.690953 0.694704 11.00000 0.05197 0.06579 = 0.05905 -0.01653 -0.00354 -0.01279 AFIX 23 H25A 2 0.782418 0.683654 0.637322 11.00000 -1.20000 H25B 2 0.743556 0.671796 0.769487 11.00000 -1.20000 AFIX 0 C26 1 0.770192 0.728812 0.762824 11.00000 0.09566 0.08003 = 0.13075 -0.03415 -0.02811 -0.03194 AFIX 137 H26A 2 0.767610 0.747604 0.689354 11.00000 -1.50000 H26B 2 0.839908 0.726896 0.824568 11.00000 -1.50000 H26C 2 0.724629 0.736394 0.818559 11.00000 -1.50000 AFIX 0 C27 1 0.733013 0.454393 0.545274 11.00000 0.01555 0.04622 = 0.02604 0.00193 -0.00067 -0.00770 AFIX 23 H27A 2 0.663072 0.464343 0.527636 11.00000 -1.20000 H27B 2 0.749448 0.439603 0.633732 11.00000 -1.20000 AFIX 0 C28 1 0.739212 0.429148 0.422594 11.00000 0.02638 0.04202 = 0.03074 -0.00423 0.00377 -0.00590 AFIX 23 H28A 2 0.720742 0.444180 0.334688 11.00000 -1.20000 H28B 2 0.810467 0.420735 0.439006 11.00000 -1.20000 AFIX 0 C29 1 0.670877 0.394743 0.401684 11.00000 0.03784 0.04486 = 0.03215 -0.00216 0.00394 -0.01077 AFIX 23 H29A 2 0.603448 0.402072 0.411210 11.00000 -1.20000 H29B 2 0.700766 0.376004 0.475915 11.00000 -1.20000 AFIX 0 C30 1 0.657670 0.377010 0.256720 11.00000 0.05292 0.04438 = 0.03295 -0.00359 0.01243 -0.01161 AFIX 23 H30A 2 0.612287 0.393431 0.185088 11.00000 -1.20000 H30B 2 0.724795 0.376838 0.237637 11.00000 -1.20000 AFIX 0 C31 1 0.615402 0.337674 0.235954 11.00000 0.03794 0.04921 = 0.03555 -0.00283 0.00624 -0.01027 AFIX 23 H31A 2 0.545105 0.337804 0.244306 11.00000 -1.20000 H31B 2 0.656992 0.321184 0.311026 11.00000 -1.20000 AFIX 0 C32 1 0.614825 0.322033 0.093448 11.00000 0.05151 0.04642 = 0.04209 -0.00751 0.01608 -0.01153 AFIX 23 H32A 2 0.684667 0.323737 0.083881 11.00000 -1.20000 H32B 2 0.570653 0.338168 0.019459 11.00000 -1.20000 AFIX 0 C33 1 0.578858 0.281788 0.066035 11.00000 0.06629 0.05475 = 0.06022 -0.01491 0.02686 -0.01936 AFIX 23 H33A 2 0.509744 0.279571 0.077903 11.00000 -1.20000 H33B 2 0.624659 0.265189 0.136483 11.00000 -1.20000 AFIX 0 C34 1 0.576657 0.268780 -0.080781 11.00000 0.11391 0.07559 = 0.07095 -0.03559 0.04235 -0.03316 AFIX 137 H34A 2 0.522253 0.281950 -0.150582 11.00000 -1.50000 H34B 2 0.564141 0.241627 -0.088733 11.00000 -1.50000 H34C 2 0.642153 0.274348 -0.098007 11.00000 -1.50000 AFIX 0 C35 1 0.974142 0.411611 1.020218 11.00000 0.01354 0.05003 = 0.04590 0.00071 0.00400 -0.00024 AFIX 23 H35A 2 0.954476 0.393051 0.942569 11.00000 -1.20000 H35B 2 0.911516 0.424416 1.026827 11.00000 -1.20000 AFIX 0 C36 1 1.022194 0.391141 1.157459 11.00000 0.02352 0.05086 = 0.04049 0.00165 0.00230 0.00132 AFIX 23 H36A 2 1.078571 0.375208 1.146046 11.00000 -1.20000 H36B 2 1.051205 0.409790 1.232418 11.00000 -1.20000 AFIX 0 C37 1 0.946894 0.366955 1.201940 11.00000 0.03752 0.07969 = 0.05876 0.01778 0.00728 -0.00519 AFIX 23 H37A 2 0.891299 0.383301 1.213398 11.00000 -1.20000 H37B 2 0.916748 0.349115 1.124498 11.00000 -1.20000 AFIX 0 C38 1 0.986738 0.345057 1.333779 11.00000 0.03559 0.07818 = 0.06391 0.02294 0.00161 -0.00616 PART 1 AFIX 23 H38A 2 1.043954 0.329436 1.323318 10.50000 -1.20000 H38B 2 1.014921 0.363026 1.411534 10.50000 -1.20000 AFIX 23 PART 2 H38C 2 1.042312 0.328763 1.321926 10.50000 -1.20000 H38D 2 1.017225 0.362973 1.410807 10.50000 -1.20000 AFIX 0 PART 1 C39 1 0.914427 0.320124 1.377035 10.50000 0.18967 0.16979 = 0.11994 0.09391 -0.04073 -0.07976 AFIX 23 H39A 2 0.854952 0.334974 1.384042 10.50000 -1.20000 H39B 2 0.889872 0.300457 1.304476 10.50000 -1.20000 AFIX 0 C40 1 0.963059 0.302122 1.514643 10.50000 0.18968 0.16979 = 0.11994 0.09391 -0.04073 -0.07975 AFIX 23 H40A 2 1.028953 0.292117 1.507996 10.50000 -1.20000 H40B 2 0.979514 0.322739 1.584754 10.50000 -1.20000 AFIX 0 C41 1 0.916883 0.271908 1.579155 10.50000 0.18968 0.16979 = 0.11994 0.09390 -0.04073 -0.07975 AFIX 23 H41A 2 0.858539 0.282185 1.607700 10.50000 -1.20000 H41B 2 0.967563 0.262453 1.664846 10.50000 -1.20000 AFIX 0 C42 1 0.879726 0.238695 1.473157 10.50000 0.18968 0.16979 = 0.11994 0.09390 -0.04073 -0.07975 AFIX 133 H42A 2 0.844315 0.248799 1.379941 10.50000 -1.50000 H42B 2 0.833173 0.222660 1.506571 10.50000 -1.50000 H42C 2 0.938428 0.223832 1.466593 10.50000 -1.50000 AFIX 0 PART 2 C43 1 0.913919 0.321081 1.380091 10.50000 0.08564 0.13372 = 0.18152 0.08477 0.04112 -0.01077 AFIX 23 H43A 2 0.868442 0.338157 1.413255 10.50000 -1.20000 H43B 2 0.871216 0.308237 1.294995 10.50000 -1.20000 AFIX 0 C44 1 0.949068 0.291926 1.489988 10.50000 0.08564 0.13373 = 0.18152 0.08476 0.04111 -0.01077 AFIX 23 H44A 2 0.977460 0.304212 1.582701 10.50000 -1.20000 H44B 2 1.003916 0.276966 1.468904 10.50000 -1.20000 AFIX 0 C45 1 0.865013 0.266599 1.497315 10.50000 0.08565 0.13373 = 0.18153 0.08476 0.04111 -0.01077 AFIX 23 H45A 2 0.830427 0.256564 1.402419 10.50000 -1.20000 H45B 2 0.814476 0.280518 1.532341 10.50000 -1.20000 AFIX 0 C46 1 0.910034 0.234713 1.596951 10.50000 0.08566 0.13374 = 0.18153 0.08476 0.04110 -0.01077 AFIX 133 H46A 2 0.959971 0.221144 1.561417 10.50000 -1.50000 H46B 2 0.855765 0.217439 1.603203 10.50000 -1.50000 H46C 2 0.943505 0.244916 1.690720 10.50000 -1.50000 AFIX 0 HKLF 4 REM tm399_auto_a.res in P2(1)/c REM wR2 = 0.2901, GooF = S = 1.124, Restrained GooF = 1.126 for all data REM R1 = 0.1313 for 6602 Fo > 4sig(Fo) and 0.1501 for all 8558 data REM 627 parameters refined using 102 restraints END WGHT 0.1207 37.9499 REM Highest difference peak 0.613, deepest hole -0.605, 1-sigma level 0.103 Q1 1 0.7850 0.5423 0.4616 11.00000 0.05 0.61 Q2 1 0.6890 0.5517 0.6989 11.00000 0.05 0.60 Q3 1 0.5006 0.5469 0.1978 11.00000 0.05 0.52 Q4 1 0.6743 0.5750 0.2820 11.00000 0.05 0.51 Q5 1 0.8034 0.5148 0.5576 11.00000 0.05 0.51 Q6 1 0.8005 0.4566 0.5446 11.00000 0.05 0.50 Q7 1 0.8490 0.5148 0.4522 11.00000 0.05 0.48 Q8 1 0.7191 0.5410 0.8598 11.00000 0.05 0.48 ; _shelx_res_checksum 98291 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.140 _oxdiff_exptl_absorpt_empirical_full_min 0.728