#------------------------------------------------------------------------------ #$Date: 2025-01-06 15:53:48 +0200 (Mon, 06 Jan 2025) $ #$Revision: 297135 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160196.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7160196 loop_ _publ_author_name 'Banerjee, Ankush' 'Brisco, Tiffany A.' 'Ray, Sneha' 'Datta, Arani' 'Zhang, Xiaoyu' 'Zhang, Zhen' 'Busse, Alexander A.' 'Niederstrasser, Hanspeter' 'Sumida, Krissty' 'Posner, Bruce A.' 'Wetzel, Dawn M.' 'Phillips, Margaret A.' 'Smith, Myles W.' _publ_section_title ; Synthesis of the 5/5-spiroindimicin alkaloids: development of a general synthetic approach and biological investigations. ; _journal_issue 48 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 9413 _journal_page_last 9425 _journal_paper_doi 10.1039/d4ob01552e _journal_volume 22 _journal_year 2024 _chemical_formula_moiety 'C17 H15 I N2 O6' _chemical_formula_sum 'C17 H15 I N2 O6' _chemical_formula_weight 470.21 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_block_doi 10.5517/ccdc.csd.cc2g0wgv _audit_creation_date 2023-05-23 _audit_creation_method ; Olex2 1.5 (compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380) ; _audit_update_record ; 2023-05-23 deposited with the CCDC. 2024-10-28 downloaded from the CCDC. ; _cell_angle_alpha 96.120(4) _cell_angle_beta 91.980(3) _cell_angle_gamma 96.465(4) _cell_formula_units_Z 4 _cell_length_a 10.8128(4) _cell_length_b 11.8787(6) _cell_length_c 13.9111(5) _cell_measurement_reflns_used 10217 _cell_measurement_temperature 100.00(11) _cell_measurement_theta_max 76.3520 _cell_measurement_theta_min 3.2090 _cell_volume 1763.33(13) _computing_cell_refinement 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_molecular_graphics 'Shelxtl-Plus/XP, Bruker AXS, Inc. 2009' _computing_publication_material 'Shelxtl-Plus, Bruker AXS, Inc. 2009' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(11) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.956 _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 -119.00 -35.00 0.50 4.50 -- -48.08 -53.00 28.00 168 2 \w 36.00 120.00 0.50 4.50 -- 48.08 53.00 172.00 168 3 \w -23.00 57.00 0.50 4.50 -- 48.08 -53.00 28.00 160 4 \w -176.00 -92.00 0.50 20.00 -- -105.11 -53.00 28.00 168 5 \w -63.00 -33.00 0.50 20.00 -- -105.11 53.00 172.00 60 6 \w 93.00 176.00 0.50 20.00 -- 105.11 53.00 172.00 166 7 \w -26.00 26.00 0.50 4.50 -- -48.08 19.00 120.00 104 8 \w -61.00 24.00 0.50 4.50 -- -48.08 53.00 172.00 170 9 \w -92.00 -13.00 0.50 4.50 -- -48.08 125.00 -60.00 158 10 \w -25.00 20.00 0.50 4.50 -- 48.08 -19.00-120.00 90 11 \w -24.00 39.00 0.50 4.50 -- 48.08 -38.00-150.00 126 12 \w -25.00 20.00 0.50 4.50 -- 48.08 -19.00 90.00 90 13 \w -174.00 -87.00 0.50 20.00 -- -105.11-125.00 150.00 174 14 \w -176.00 -90.00 0.50 20.00 -- -105.11 -61.00 -30.00 172 15 \w -111.00 -36.00 0.50 20.00 -- -105.11 125.00 0.00 150 16 \w -174.00 -87.00 0.50 20.00 -- -105.11-125.00 90.00 174 17 \w -125.00 -33.00 0.50 20.00 -- -105.11 143.00 84.79 184 18 \w -176.00 -90.00 0.50 20.00 -- -105.11 -61.00 -41.44 172 19 \w -176.00-100.00 0.50 20.00 -- -105.11 -95.00 120.00 152 20 \w -75.00 -33.00 0.50 20.00 -- -105.11 61.00 90.00 84 21 \w -109.00 -37.00 0.50 20.00 -- -105.11 115.00 52.19 144 22 \w -116.00 -33.00 0.50 20.00 -- -105.11 77.00 120.00 166 23 \w -177.00 -95.00 0.50 20.00 -- -105.11 -15.00 0.00 164 24 \w -111.00 -36.00 0.50 20.00 -- -105.11 125.00-120.00 150 25 \w -111.00 -36.00 0.50 20.00 -- -105.11 125.00 150.00 150 26 \w -75.00 -33.00 0.50 20.00 -- -105.11 61.00 30.00 84 27 \w -90.00 -35.00 0.50 20.00 -- -105.11 104.00-121.59 110 28 \w 33.00 105.00 0.50 20.00 -- 105.11 -95.00 0.00 144 29 \w 94.00 176.00 0.50 20.00 -- 105.11 45.00 30.00 164 30 \w 33.00 105.00 0.50 20.00 -- 105.11 -95.00 -60.00 144 31 \w 36.00 112.00 0.50 20.00 -- 105.11-125.00-180.00 152 32 \w 36.00 120.00 0.50 4.50 -- 48.08 52.00 125.81 168 33 \w 35.00 120.00 0.50 4.50 -- 48.08 56.00 -6.17 170 34 \w 36.00 120.00 0.50 4.50 -- 48.08 53.00 -56.93 168 35 \w 35.00 120.00 0.50 4.50 -- 48.08 54.00-150.17 170 36 \w 35.00 120.00 0.50 4.50 -- 48.08 56.00-114.34 170 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Single source at home/near, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0463695000 _diffrn_orient_matrix_UB_12 0.1184245000 _diffrn_orient_matrix_UB_13 0.0126135000 _diffrn_orient_matrix_UB_21 -0.1122626000 _diffrn_orient_matrix_UB_22 -0.0446662000 _diffrn_orient_matrix_UB_23 -0.0702860000 _diffrn_orient_matrix_UB_31 -0.0765030000 _diffrn_orient_matrix_UB_32 -0.0350725000 _diffrn_orient_matrix_UB_33 0.0856359000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0765 _diffrn_reflns_av_unetI/netI 0.0340 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.956 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 28722 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.956 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.890 _diffrn_reflns_theta_min 3.199 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 14.611 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.50779 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.771 _exptl_crystal_description prism _exptl_crystal_F_000 928 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.1 _refine_diff_density_max 2.519 _refine_diff_density_min -1.428 _refine_diff_density_rms 0.171 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 491 _refine_ls_number_reflns 7208 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0530 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0895P)^2^+5.9843P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1424 _refine_ls_wR_factor_ref 0.1437 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6969 _reflns_number_total 7208 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01552e2.cif _cod_data_source_block 1-ab-40bx3 _cod_depositor_comments 'Adding full bibliography for 7160196--7160199.cif.' _cod_original_cell_volume 1763.32(13) _cod_database_code 7160196 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C17H15N2O4I _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances N3-H3 = N1-H1 0.84 with sigma of 0.02 O5-H5 = O11-H11 0.84 with sigma of 0.02 3.a Aromatic/amide H refined with riding coordinates: C12(H12), C13(H13), C14(H14), C15(H15), C29(H29), C30(H30), C31(H31), C32(H32) 3.b Idealised Me refined as rotating group: C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C34(H34A,H34B,H34C) ; _shelx_res_file ; TITL 1-ab-40bx3_auto_a.res in P-1 1-ab-40bx3.res created by SHELXL-2018/3 at 14:54:01 on 23-May-2023 REM Old TITL 1-AB-40Bx3_auto in P-1 REM SHELXT solution in P-1: R1 0.108, Rweak 0.008, Alpha 0.069 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C35 N2 O7 I1 CELL 1.54184 10.812815 11.87866 13.911092 96.1205 91.9799 96.4653 ZERR 4 0.000357 0.000647 0.000497 0.0038 0.0028 0.0036 LATT 1 SFAC C H I N O UNIT 68 60 4 8 24 DFIX 0.84 N3 H3 N1 H1 DFIX 0.84 O5 H5 O11 H11 L.S. 6 PLAN 5 TEMP -173 CONF MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.089500 5.984300 FVAR 2.15068 I1 3 0.141335 0.747230 0.702438 11.00000 0.02966 0.02962 = 0.03535 0.00371 -0.00896 0.00597 I2 3 0.351558 0.722024 0.202398 11.00000 0.02524 0.03067 = 0.03756 0.00031 0.00747 0.00731 O1 5 -0.105775 0.858950 0.786207 11.00000 0.05634 0.04550 = 0.03805 0.00571 0.01310 0.01511 O2 5 -0.249972 0.918439 0.687534 11.00000 0.02936 0.04448 = 0.04875 -0.00129 0.01331 0.01020 O3 5 -0.015144 0.893683 0.294815 11.00000 0.04474 0.03506 = 0.03414 0.00628 -0.00099 0.00163 O4 5 -0.204655 0.889652 0.354313 11.00000 0.03215 0.04797 = 0.04710 0.00437 -0.01936 0.01431 O5 5 0.159141 0.773843 0.345045 11.00000 0.03920 0.04236 = 0.03749 0.00676 0.01383 0.01548 H5 2 0.124946 0.827773 0.325179 11.00000 0.04727 O6 5 0.304559 0.954379 0.488789 11.00000 0.01866 0.02679 = 0.08058 0.00958 0.00174 0.00377 O7 5 0.608504 0.616959 0.275954 11.00000 0.04247 0.05990 = 0.04189 0.01357 -0.00386 0.01487 O8 5 0.777123 0.627448 0.185096 11.00000 0.02370 0.03492 = 0.05030 0.00303 -0.01117 0.00556 O9 5 0.538487 0.659864 -0.218147 11.00000 0.04725 0.04640 = 0.03186 0.00662 0.00364 0.00563 O10 5 0.703679 0.593375 -0.156026 11.00000 0.03636 0.04588 = 0.04766 0.00515 0.01836 0.01042 O11 5 0.310532 0.642075 -0.156343 11.00000 0.03067 0.03847 = 0.03617 -0.00008 -0.01050 0.00609 H11 2 0.379361 0.652033 -0.183235 11.00000 0.05039 O12 5 0.183367 0.539057 -0.001830 11.00000 0.01754 0.02688 = 0.05772 0.00072 -0.00130 0.00338 N1 4 -0.125090 0.881917 0.531540 11.00000 0.01404 0.02393 = 0.03654 0.00197 -0.00200 0.00522 H1 2 -0.191149 0.910373 0.521674 11.00000 0.06930 N2 4 0.372467 0.783151 0.515270 11.00000 0.01599 0.02965 = 0.07413 0.00788 -0.00179 0.00251 N3 4 0.636585 0.621906 0.022961 11.00000 0.01471 0.02383 = 0.03663 0.00330 0.00376 0.00469 H3 2 0.708773 0.604981 0.017109 11.00000 0.02284 N4 4 0.129938 0.721395 0.003749 11.00000 0.01625 0.02724 = 0.07583 0.00203 -0.00189 0.00661 C1 1 -0.077874 0.855456 0.616941 11.00000 0.01620 0.02267 = 0.03385 0.00192 0.00118 0.00387 C2 1 0.033288 0.809915 0.597685 11.00000 0.01676 0.02580 = 0.02870 0.00188 -0.00277 0.00549 C3 1 0.054458 0.811726 0.498320 11.00000 0.01337 0.02234 = 0.02899 0.00338 -0.00113 0.00214 C4 1 -0.047043 0.858293 0.459159 11.00000 0.01670 0.02016 = 0.03401 0.00257 -0.00106 0.00181 C5 1 -0.141996 0.876712 0.707397 11.00000 0.03470 0.02301 = 0.04135 0.00079 0.01097 0.00196 C6 1 -0.320937 0.946506 0.770809 11.00000 0.05107 0.04468 = 0.06604 0.00366 0.02991 0.01277 AFIX 137 H6A 2 -0.274066 1.009190 0.813246 11.00000 -1.50000 H6B 2 -0.336310 0.879631 0.806201 11.00000 -1.50000 H6C 2 -0.400673 0.969776 0.749584 11.00000 -1.50000 AFIX 0 C7 1 -0.083618 0.881816 0.360979 11.00000 0.03524 0.01825 = 0.04046 0.00145 -0.01043 0.00352 C8 1 -0.253386 0.918875 0.262484 11.00000 0.05911 0.04825 = 0.06349 0.00941 -0.03421 0.00809 AFIX 137 H8A 2 -0.343282 0.922503 0.265541 11.00000 -1.50000 H8B 2 -0.237702 0.860646 0.210389 11.00000 -1.50000 H8C 2 -0.211981 0.993146 0.249705 11.00000 -1.50000 AFIX 0 C9 1 0.167215 0.773256 0.446472 11.00000 0.01781 0.02991 = 0.03426 0.00271 0.00532 0.00360 C10 1 0.287730 0.851801 0.486960 11.00000 0.01640 0.02708 = 0.05434 0.01035 0.00385 0.00233 C11 1 0.321700 0.668759 0.505783 11.00000 0.01711 0.02859 = 0.05316 0.00302 0.00545 0.00814 C12 1 0.374013 0.576601 0.534588 11.00000 0.02197 0.03528 = 0.05475 0.00582 0.00154 0.00804 AFIX 43 H12 2 0.455677 0.585523 0.563945 11.00000 -1.20000 AFIX 0 C13 1 0.304301 0.470560 0.519581 11.00000 0.03083 0.03024 = 0.04653 0.00919 0.01112 0.01054 AFIX 43 H13 2 0.339224 0.405771 0.538126 11.00000 -1.20000 AFIX 0 C14 1 0.184035 0.457227 0.477830 11.00000 0.02748 0.02700 = 0.04277 0.00005 0.01236 0.00129 AFIX 43 H14 2 0.137834 0.383714 0.467843 11.00000 -1.20000 AFIX 0 C15 1 0.130679 0.552309 0.450372 11.00000 0.02068 0.02859 = 0.03420 -0.00173 0.00545 0.00202 AFIX 43 H15 2 0.048577 0.543753 0.421860 11.00000 -1.20000 AFIX 0 C16 1 0.199427 0.658012 0.465503 11.00000 0.01989 0.02879 = 0.03341 0.00321 0.00580 0.00999 C17 1 0.497885 0.824216 0.554446 11.00000 0.01994 0.03529 = 0.13052 0.01119 -0.01856 -0.00035 AFIX 137 H17A 2 0.508461 0.907758 0.563117 11.00000 -1.50000 H17B 2 0.558716 0.797015 0.509545 11.00000 -1.50000 H17C 2 0.510947 0.795530 0.617061 11.00000 -1.50000 AFIX 0 C18 1 0.586498 0.641331 0.110280 11.00000 0.01576 0.02471 = 0.03615 0.00106 0.00149 0.00521 C19 1 0.467320 0.673108 0.093611 11.00000 0.01610 0.02446 = 0.02802 0.00052 0.00638 0.00787 C20 1 0.445372 0.670443 -0.006831 11.00000 0.01296 0.02133 = 0.03452 0.00462 0.00088 0.00283 C21 1 0.554538 0.638425 -0.049088 11.00000 0.01878 0.02119 = 0.03129 0.00243 0.00053 0.00422 C22 1 0.654479 0.626618 0.199776 11.00000 0.02673 0.02546 = 0.04216 0.00617 -0.00383 0.00579 C23 1 0.852612 0.597182 0.264492 11.00000 0.03474 0.04259 = 0.05641 0.00916 -0.02134 0.00653 AFIX 137 H23A 2 0.836565 0.643459 0.324391 11.00000 -1.50000 H23B 2 0.940960 0.611363 0.250802 11.00000 -1.50000 H23C 2 0.831315 0.516274 0.271927 11.00000 -1.50000 AFIX 0 C24 1 0.594317 0.631083 -0.149375 11.00000 0.03750 0.02253 = 0.04104 0.00125 0.00399 -0.00023 C25 1 0.751302 0.578549 -0.252708 11.00000 0.05877 0.05808 = 0.05161 0.00239 0.02817 0.00977 AFIX 137 H25A 2 0.828134 0.542149 -0.250240 11.00000 -1.50000 H25B 2 0.768810 0.653136 -0.276578 11.00000 -1.50000 H25C 2 0.688995 0.530390 -0.296335 11.00000 -1.50000 AFIX 0 C26 1 0.325968 0.694368 -0.058852 11.00000 0.02216 0.02871 = 0.03422 0.00096 -0.00169 0.00322 C27 1 0.207048 0.638667 -0.013134 11.00000 0.01431 0.03158 = 0.04770 0.00346 -0.00244 0.00745 C28 1 0.188299 0.828533 -0.012680 11.00000 0.01903 0.02716 = 0.06428 0.00419 -0.00555 0.00680 C29 1 0.143679 0.932633 0.006022 11.00000 0.02673 0.03479 = 0.09421 0.00088 -0.01119 0.01341 AFIX 43 H29 2 0.064795 0.938809 0.032855 11.00000 -1.20000 AFIX 0 C30 1 0.219576 1.028391 -0.016233 11.00000 0.03714 0.03043 = 0.08257 0.00494 -0.01942 0.01099 AFIX 43 H30 2 0.190535 1.101073 -0.005830 11.00000 -1.20000 AFIX 0 C31 1 0.335490 1.020598 -0.052879 11.00000 0.04074 0.02764 = 0.05353 0.00913 -0.01843 -0.00081 AFIX 43 H31 2 0.385181 1.087339 -0.067254 11.00000 -1.20000 AFIX 0 C32 1 0.380506 0.913015 -0.069104 11.00000 0.02702 0.03582 = 0.04223 0.00997 -0.00697 0.00458 AFIX 43 H32 2 0.460469 0.906478 -0.093888 11.00000 -1.20000 AFIX 0 C33 1 0.306278 0.819316 -0.048277 11.00000 0.02331 0.02931 = 0.03572 0.00293 -0.00917 0.00603 C34 1 0.008878 0.702329 0.045933 11.00000 0.02078 0.03637 = 0.12261 0.00404 0.00687 0.00923 AFIX 137 H34A 2 0.009240 0.750769 0.107573 11.00000 -1.50000 H34B 2 -0.008059 0.622101 0.057140 11.00000 -1.50000 H34C 2 -0.055957 0.721296 0.001454 11.00000 -1.50000 AFIX 0 HKLF 4 REM 1-ab-40bx3_auto_a.res in P-1 REM wR2 = 0.1437, GooF = S = 1.041, Restrained GooF = 1.041 for all data REM R1 = 0.0530 for 6969 Fo > 4sig(Fo) and 0.0540 for all 7208 data REM 491 parameters refined using 4 restraints END WGHT 0.0895 5.9557 REM Highest difference peak 2.519, deepest hole -1.428, 1-sigma level 0.171 Q1 1 0.3873 0.7954 0.2043 11.00000 0.05 2.52 Q2 1 0.1704 0.8207 0.7132 11.00000 0.05 2.37 Q3 1 0.1133 0.6732 0.6917 11.00000 0.05 1.90 Q4 1 0.3170 0.6579 0.2435 11.00000 0.05 1.78 Q5 1 0.3200 0.6431 0.1965 11.00000 0.05 1.71 ; _shelx_res_checksum 62928 _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 2.322 _oxdiff_exptl_absorpt_empirical_full_min 0.491 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 I1 I 0.14134(3) 0.74723(3) 0.70244(2) 0.03159(12) Uani 1 1 d . . . . . I2 I 0.35156(3) 0.72202(3) 0.20240(2) 0.03096(12) Uani 1 1 d . . . . . O1 O -0.1058(4) 0.8589(4) 0.7862(3) 0.0456(10) Uani 1 1 d . . . . . O2 O -0.2500(4) 0.9184(3) 0.6875(3) 0.0406(9) Uani 1 1 d . . . . . O3 O -0.0151(4) 0.8937(3) 0.2948(3) 0.0381(8) Uani 1 1 d . . . . . O4 O -0.2047(4) 0.8897(4) 0.3543(3) 0.0422(9) Uani 1 1 d . . . . . O5 O 0.1591(4) 0.7738(3) 0.3450(3) 0.0384(8) Uani 1 1 d D . . . . H5 H 0.125(6) 0.828(4) 0.325(5) 0.05(2) Uiso 1 1 d D . . . . O6 O 0.3046(3) 0.9544(3) 0.4888(4) 0.0417(9) Uani 1 1 d . . . . . O7 O 0.6085(4) 0.6170(4) 0.2760(3) 0.0470(10) Uani 1 1 d . . . . . O8 O 0.7771(3) 0.6274(3) 0.1851(3) 0.0366(8) Uani 1 1 d . . . . . O9 O 0.5385(4) 0.6599(4) -0.2181(3) 0.0416(9) Uani 1 1 d . . . . . O10 O 0.7037(4) 0.5934(4) -0.1560(3) 0.0425(9) Uani 1 1 d . . . . . O11 O 0.3105(3) 0.6421(3) -0.1563(3) 0.0355(8) Uani 1 1 d D . . . . H11 H 0.379(4) 0.652(7) -0.183(5) 0.05(2) Uiso 1 1 d D . . . . O12 O 0.1834(3) 0.5391(3) -0.0018(3) 0.0343(8) Uani 1 1 d . . . . . N1 N -0.1251(3) 0.8819(3) 0.5315(3) 0.0248(8) Uani 1 1 d D . . . . H1 H -0.191(5) 0.910(7) 0.522(6) 0.07(3) Uiso 1 1 d D . . . . N2 N 0.3725(4) 0.7832(4) 0.5153(4) 0.0399(11) Uani 1 1 d . . . . . N3 N 0.6366(3) 0.6219(3) 0.0230(3) 0.0248(8) Uani 1 1 d D . . . . H3 H 0.709(3) 0.605(5) 0.017(4) 0.023(13) Uiso 1 1 d D . . . . N4 N 0.1299(4) 0.7214(4) 0.0037(4) 0.0398(11) Uani 1 1 d . . . . . C1 C -0.0779(4) 0.8555(4) 0.6169(4) 0.0242(9) Uani 1 1 d . . . . . C2 C 0.0333(4) 0.8099(4) 0.5977(3) 0.0237(8) Uani 1 1 d . . . . . C3 C 0.0545(4) 0.8117(4) 0.4983(3) 0.0216(8) Uani 1 1 d . . . . . C4 C -0.0470(4) 0.8583(4) 0.4592(3) 0.0237(9) Uani 1 1 d . . . . . C5 C -0.1420(5) 0.8767(4) 0.7074(4) 0.0331(11) Uani 1 1 d . . . . . C6 C -0.3209(7) 0.9465(6) 0.7708(6) 0.0529(16) Uani 1 1 d . . . . . H6A H -0.274066 1.009190 0.813246 0.079 Uiso 1 1 calc R U . . . H6B H -0.336310 0.879631 0.806201 0.079 Uiso 1 1 calc R U . . . H6C H -0.400673 0.969776 0.749584 0.079 Uiso 1 1 calc R U . . . C7 C -0.0836(5) 0.8818(4) 0.3610(4) 0.0317(10) Uani 1 1 d . . . . . C8 C -0.2534(7) 0.9189(6) 0.2625(6) 0.0574(19) Uani 1 1 d . . . . . H8A H -0.343282 0.922503 0.265541 0.086 Uiso 1 1 calc R U . . . H8B H -0.237702 0.860646 0.210389 0.086 Uiso 1 1 calc R U . . . H8C H -0.211981 0.993146 0.249705 0.086 Uiso 1 1 calc R U . . . C9 C 0.1672(4) 0.7733(4) 0.4465(4) 0.0272(9) Uani 1 1 d . . . . . C10 C 0.2877(4) 0.8518(4) 0.4870(4) 0.0321(11) Uani 1 1 d . . . . . C11 C 0.3217(4) 0.6688(4) 0.5058(4) 0.0326(11) Uani 1 1 d . . . . . C12 C 0.3740(5) 0.5766(5) 0.5346(4) 0.0369(11) Uani 1 1 d . . . . . H12 H 0.455677 0.585523 0.563945 0.044 Uiso 1 1 calc R U . . . C13 C 0.3043(5) 0.4706(4) 0.5196(4) 0.0348(11) Uani 1 1 d . . . . . H13 H 0.339224 0.405771 0.538126 0.042 Uiso 1 1 calc R U . . . C14 C 0.1840(5) 0.4572(4) 0.4778(4) 0.0326(10) Uani 1 1 d . . . . . H14 H 0.137834 0.383714 0.467843 0.039 Uiso 1 1 calc R U . . . C15 C 0.1307(4) 0.5523(4) 0.4504(4) 0.0282(9) Uani 1 1 d . . . . . H15 H 0.048577 0.543753 0.421860 0.034 Uiso 1 1 calc R U . . . C16 C 0.1994(4) 0.6580(4) 0.4655(4) 0.0267(9) Uani 1 1 d . . . . . C17 C 0.4979(5) 0.8242(5) 0.5544(7) 0.063(2) Uani 1 1 d . . . . . H17A H 0.508461 0.907758 0.563117 0.094 Uiso 1 1 calc R U . . . H17B H 0.558716 0.797015 0.509545 0.094 Uiso 1 1 calc R U . . . H17C H 0.510947 0.795530 0.617061 0.094 Uiso 1 1 calc R U . . . C18 C 0.5865(4) 0.6413(4) 0.1103(4) 0.0255(9) Uani 1 1 d . . . . . C19 C 0.4673(4) 0.6731(4) 0.0936(3) 0.0225(8) Uani 1 1 d . . . . . C20 C 0.4454(4) 0.6704(4) -0.0068(3) 0.0228(8) Uani 1 1 d . . . . . C21 C 0.5545(4) 0.6384(4) -0.0491(3) 0.0237(8) Uani 1 1 d . . . . . C22 C 0.6545(5) 0.6266(4) 0.1998(4) 0.0312(10) Uani 1 1 d . . . . . C23 C 0.8526(6) 0.5972(5) 0.2645(5) 0.0447(14) Uani 1 1 d . . . . . H23A H 0.836565 0.643459 0.324391 0.067 Uiso 1 1 calc R U . . . H23B H 0.940960 0.611363 0.250802 0.067 Uiso 1 1 calc R U . . . H23C H 0.831315 0.516274 0.271927 0.067 Uiso 1 1 calc R U . . . C24 C 0.5943(5) 0.6311(4) -0.1494(4) 0.0341(11) Uani 1 1 d . . . . . C25 C 0.7513(7) 0.5785(6) -0.2527(5) 0.0556(17) Uani 1 1 d . . . . . H25A H 0.828134 0.542149 -0.250240 0.083 Uiso 1 1 calc R U . . . H25B H 0.768810 0.653136 -0.276578 0.083 Uiso 1 1 calc R U . . . H25C H 0.688995 0.530390 -0.296335 0.083 Uiso 1 1 calc R U . . . C26 C 0.3260(4) 0.6944(4) -0.0589(4) 0.0286(10) Uani 1 1 d . . . . . C27 C 0.2070(4) 0.6387(4) -0.0131(4) 0.0310(10) Uani 1 1 d . . . . . C28 C 0.1883(5) 0.8285(4) -0.0127(5) 0.0368(12) Uani 1 1 d . . . . . C29 C 0.1437(5) 0.9326(5) 0.0060(6) 0.0519(17) Uani 1 1 d . . . . . H29 H 0.064795 0.938809 0.032855 0.062 Uiso 1 1 calc R U . . . C30 C 0.2196(6) 1.0284(5) -0.0162(6) 0.0501(16) Uani 1 1 d . . . . . H30 H 0.190535 1.101073 -0.005830 0.060 Uiso 1 1 calc R U . . . C31 C 0.3355(6) 1.0206(5) -0.0529(5) 0.0412(13) Uani 1 1 d . . . . . H31 H 0.385181 1.087339 -0.067254 0.049 Uiso 1 1 calc R U . . . C32 C 0.3805(5) 0.9130(5) -0.0691(4) 0.0347(11) Uani 1 1 d . . . . . H32 H 0.460469 0.906478 -0.093888 0.042 Uiso 1 1 calc R U . . . C33 C 0.3063(4) 0.8193(4) -0.0483(4) 0.0295(10) Uani 1 1 d . . . . . C34 C 0.0089(5) 0.7023(5) 0.0459(7) 0.060(2) Uani 1 1 d . . . . . H34A H 0.009240 0.750769 0.107573 0.090 Uiso 1 1 calc R U . . . H34B H -0.008059 0.622101 0.057140 0.090 Uiso 1 1 calc R U . . . H34C H -0.055957 0.721296 0.001454 0.090 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 I1 0.02966(18) 0.02962(18) 0.03535(19) 0.00371(12) -0.00896(13) 0.00597(12) I2 0.02524(17) 0.03067(18) 0.03756(19) 0.00031(13) 0.00747(12) 0.00731(12) O1 0.056(3) 0.046(2) 0.038(2) 0.0057(17) 0.0131(19) 0.0151(19) O2 0.0294(18) 0.044(2) 0.049(2) -0.0013(17) 0.0133(16) 0.0102(16) O3 0.045(2) 0.0351(19) 0.0341(19) 0.0063(15) -0.0010(16) 0.0016(16) O4 0.0322(19) 0.048(2) 0.047(2) 0.0044(18) -0.0194(17) 0.0143(16) O5 0.039(2) 0.042(2) 0.037(2) 0.0068(16) 0.0138(16) 0.0155(17) O6 0.0187(16) 0.0268(18) 0.081(3) 0.0096(18) 0.0017(17) 0.0038(13) O7 0.042(2) 0.060(3) 0.042(2) 0.0136(19) -0.0039(18) 0.015(2) O8 0.0237(16) 0.0349(19) 0.050(2) 0.0030(16) -0.0112(15) 0.0056(14) O9 0.047(2) 0.046(2) 0.0319(19) 0.0066(16) 0.0036(17) 0.0056(18) O10 0.036(2) 0.046(2) 0.048(2) 0.0051(18) 0.0184(17) 0.0104(17) O11 0.0307(18) 0.0385(19) 0.0362(19) -0.0001(15) -0.0105(15) 0.0061(15) O12 0.0175(15) 0.0269(17) 0.058(2) 0.0007(15) -0.0013(15) 0.0034(13) N1 0.0140(16) 0.0239(18) 0.037(2) 0.0020(15) -0.0020(15) 0.0052(14) N2 0.0160(19) 0.030(2) 0.074(3) 0.008(2) -0.002(2) 0.0025(16) N3 0.0147(17) 0.0238(18) 0.037(2) 0.0033(15) 0.0038(15) 0.0047(14) N4 0.0163(19) 0.027(2) 0.076(3) 0.002(2) -0.002(2) 0.0066(16) C1 0.0162(19) 0.023(2) 0.034(2) 0.0019(17) 0.0012(17) 0.0039(16) C2 0.0168(19) 0.026(2) 0.029(2) 0.0019(17) -0.0028(16) 0.0055(16) C3 0.0134(18) 0.022(2) 0.029(2) 0.0034(16) -0.0011(16) 0.0021(15) C4 0.0167(19) 0.0202(19) 0.034(2) 0.0026(17) -0.0011(17) 0.0018(15) C5 0.035(3) 0.023(2) 0.041(3) 0.0008(19) 0.011(2) 0.0020(19) C6 0.051(4) 0.045(3) 0.066(4) 0.004(3) 0.030(3) 0.013(3) C7 0.035(3) 0.018(2) 0.040(3) 0.0015(18) -0.010(2) 0.0035(18) C8 0.059(4) 0.048(4) 0.063(4) 0.009(3) -0.034(3) 0.008(3) C9 0.018(2) 0.030(2) 0.034(2) 0.0027(19) 0.0053(18) 0.0036(17) C10 0.016(2) 0.027(2) 0.054(3) 0.010(2) 0.004(2) 0.0023(17) C11 0.017(2) 0.029(2) 0.053(3) 0.003(2) 0.005(2) 0.0081(17) C12 0.022(2) 0.035(3) 0.055(3) 0.006(2) 0.002(2) 0.0080(19) C13 0.031(2) 0.030(2) 0.047(3) 0.009(2) 0.011(2) 0.011(2) C14 0.027(2) 0.027(2) 0.043(3) 0.000(2) 0.012(2) 0.0013(18) C15 0.021(2) 0.029(2) 0.034(2) -0.0017(18) 0.0055(18) 0.0020(17) C16 0.020(2) 0.029(2) 0.033(2) 0.0032(18) 0.0058(18) 0.0100(17) C17 0.020(3) 0.035(3) 0.131(7) 0.011(4) -0.019(3) 0.000(2) C18 0.0158(19) 0.025(2) 0.036(2) 0.0011(18) 0.0015(17) 0.0052(16) C19 0.0161(19) 0.024(2) 0.028(2) 0.0005(16) 0.0064(16) 0.0079(15) C20 0.0130(18) 0.0213(19) 0.035(2) 0.0046(17) 0.0009(16) 0.0028(15) C21 0.0188(19) 0.021(2) 0.031(2) 0.0024(17) 0.0005(17) 0.0042(15) C22 0.027(2) 0.025(2) 0.042(3) 0.006(2) -0.004(2) 0.0058(18) C23 0.035(3) 0.043(3) 0.056(4) 0.009(3) -0.021(3) 0.007(2) C24 0.038(3) 0.023(2) 0.041(3) 0.0013(19) 0.004(2) -0.0002(19) C25 0.059(4) 0.058(4) 0.052(4) 0.002(3) 0.028(3) 0.010(3) C26 0.022(2) 0.029(2) 0.034(2) 0.0010(19) -0.0017(18) 0.0032(18) C27 0.014(2) 0.032(2) 0.048(3) 0.003(2) -0.0024(19) 0.0075(17) C28 0.019(2) 0.027(2) 0.064(4) 0.004(2) -0.006(2) 0.0068(18) C29 0.027(3) 0.035(3) 0.094(5) 0.001(3) -0.011(3) 0.013(2) C30 0.037(3) 0.030(3) 0.083(5) 0.005(3) -0.019(3) 0.011(2) C31 0.041(3) 0.028(2) 0.054(3) 0.009(2) -0.018(3) -0.001(2) C32 0.027(2) 0.036(3) 0.042(3) 0.010(2) -0.007(2) 0.005(2) C33 0.023(2) 0.029(2) 0.036(2) 0.0029(19) -0.0092(18) 0.0060(18) C34 0.021(3) 0.036(3) 0.123(7) 0.004(4) 0.007(3) 0.009(2) 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' I I -0.3257 6.8362 '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' loop_ _citation_id _citation_doi _citation_year 1 10.1021/acs.orglett.3c03131 2023 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 C5 O2 C6 114.8(5) . . ? C7 O4 C8 116.3(5) . . ? C9 O5 H5 115(5) . . ? C22 O8 C23 115.8(5) . . ? C24 O10 C25 116.4(5) . . ? C26 O11 H11 109(5) . . ? C1 N1 H1 128(6) . . ? C1 N1 C4 110.4(4) . . ? C4 N1 H1 122(6) . . ? C10 N2 C11 111.5(4) . . ? C10 N2 C17 124.4(5) . . ? C11 N2 C17 124.1(5) . . ? C18 N3 H3 123(4) . . ? C18 N3 C21 110.3(4) . . ? C21 N3 H3 127(4) . . ? C27 N4 C28 111.5(4) . . ? C27 N4 C34 123.6(5) . . ? C28 N4 C34 124.4(5) . . ? N1 C1 C2 107.0(4) . . ? N1 C1 C5 121.4(4) . . ? C2 C1 C5 131.6(5) . . ? C1 C2 I1 123.4(3) . . ? C1 C2 C3 108.5(4) . . ? C3 C2 I1 128.1(3) . . ? C2 C3 C9 126.2(4) . . ? C4 C3 C2 105.7(4) . . ? C4 C3 C9 128.0(4) . . ? N1 C4 C3 108.3(4) . . ? N1 C4 C7 117.9(4) . . ? C3 C4 C7 133.8(4) . . ? O1 C5 O2 125.1(5) . . ? O1 C5 C1 126.0(5) . . ? O2 C5 C1 108.9(5) . . ? O2 C6 H6A 109.5 . . ? O2 C6 H6B 109.5 . . ? O2 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O3 C7 O4 123.6(5) . . ? O3 C7 C4 126.3(5) . . ? O4 C7 C4 110.1(5) . . ? O4 C8 H8A 109.5 . . ? O4 C8 H8B 109.5 . . ? O4 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O5 C9 C3 114.4(4) . . ? O5 C9 C10 108.2(4) . . ? O5 C9 C16 106.9(4) . . ? C3 C9 C10 109.6(4) . . ? C16 C9 C3 115.1(4) . . ? C16 C9 C10 101.6(4) . . ? O6 C10 N2 126.3(5) . . ? O6 C10 C9 125.9(5) . . ? N2 C10 C9 107.7(4) . . ? N2 C11 C16 109.7(4) . . ? C12 C11 N2 128.4(5) . . ? C12 C11 C16 121.8(5) . . ? C11 C12 H12 120.9 . . ? C11 C12 C13 118.2(5) . . ? C13 C12 H12 120.9 . . ? C12 C13 H13 119.4 . . ? C12 C13 C14 121.2(5) . . ? C14 C13 H13 119.4 . . ? C13 C14 H14 119.9 . . ? C13 C14 C15 120.2(5) . . ? C15 C14 H14 119.9 . . ? C14 C15 H15 120.6 . . ? C16 C15 C14 118.9(4) . . ? C16 C15 H15 120.6 . . ? C11 C16 C9 109.2(4) . . ? C15 C16 C9 131.0(4) . . ? C15 C16 C11 119.8(4) . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N3 C18 C19 107.4(4) . . ? N3 C18 C22 121.3(4) . . ? C19 C18 C22 131.3(4) . . ? C18 C19 I2 124.1(3) . . ? C18 C19 C20 108.2(4) . . ? C20 C19 I2 127.7(3) . . ? C19 C20 C21 105.8(4) . . ? C19 C20 C26 126.7(4) . . ? C21 C20 C26 127.4(4) . . ? N3 C21 C20 108.3(4) . . ? N3 C21 C24 119.1(4) . . ? C20 C21 C24 132.3(4) . . ? O7 C22 O8 124.5(5) . . ? O7 C22 C18 125.0(5) . . ? O8 C22 C18 110.4(4) . . ? O8 C23 H23A 109.5 . . ? O8 C23 H23B 109.5 . . ? O8 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O9 C24 O10 122.6(5) . . ? O9 C24 C21 126.0(5) . . ? O10 C24 C21 111.3(5) . . ? O10 C25 H25A 109.5 . . ? O10 C25 H25B 109.5 . . ? O10 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O11 C26 C20 113.4(4) . . ? O11 C26 C27 101.6(4) . . ? O11 C26 C33 113.4(4) . . ? C20 C26 C27 111.7(4) . . ? C33 C26 C20 113.5(4) . . ? C33 C26 C27 102.0(4) . . ? O12 C27 N4 126.2(5) . . ? O12 C27 C26 126.5(4) . . ? N4 C27 C26 107.1(4) . . ? C29 C28 N4 127.5(5) . . ? C29 C28 C33 121.8(5) . . ? C33 C28 N4 110.6(4) . . ? C28 C29 H29 121.5 . . ? C28 C29 C30 117.0(6) . . ? C30 C29 H29 121.5 . . ? C29 C30 H30 119.1 . . ? C31 C30 C29 121.9(5) . . ? C31 C30 H30 119.1 . . ? C30 C31 H31 120.0 . . ? C30 C31 C32 120.0(5) . . ? C32 C31 H31 120.0 . . ? C31 C32 H32 120.9 . . ? C33 C32 C31 118.3(5) . . ? C33 C32 H32 120.9 . . ? C28 C33 C26 108.0(4) . . ? C32 C33 C26 131.0(5) . . ? C32 C33 C28 121.0(5) . . ? N4 C34 H34A 109.5 . . ? N4 C34 H34B 109.5 . . ? N4 C34 H34C 109.5 . . ? H34A C34 H34B 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? 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 I1 C2 2.086(4) . ? I2 C19 2.074(4) . ? O1 C5 1.199(7) . ? O2 C5 1.350(7) . ? O2 C6 1.442(7) . ? O3 C7 1.211(7) . ? O4 C7 1.323(7) . ? O4 C8 1.456(7) . ? O5 H5 0.84(2) . ? O5 C9 1.411(6) . ? O6 C10 1.209(6) . ? O7 C22 1.197(7) . ? O8 C22 1.348(6) . ? O8 C23 1.450(6) . ? O9 C24 1.214(7) . ? O10 C24 1.314(7) . ? O10 C25 1.457(7) . ? O11 H11 0.85(2) . ? O11 C26 1.426(6) . ? O12 C27 1.210(6) . ? N1 H1 0.84(2) . ? N1 C1 1.358(6) . ? N1 C4 1.363(6) . ? N2 C10 1.368(7) . ? N2 C11 1.398(7) . ? N2 C17 1.455(7) . ? N3 H3 0.83(2) . ? N3 C18 1.355(6) . ? N3 C21 1.360(6) . ? N4 C27 1.366(6) . ? N4 C28 1.400(7) . ? N4 C34 1.457(8) . ? C1 C2 1.395(6) . ? C1 C5 1.470(7) . ? C2 C3 1.411(6) . ? C3 C4 1.402(6) . ? C3 C9 1.527(6) . ? C4 C7 1.473(7) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.565(7) . ? C9 C16 1.498(7) . ? C11 C12 1.377(7) . ? C11 C16 1.405(7) . ? C12 H12 0.9500 . ? C12 C13 1.385(8) . ? C13 H13 0.9500 . ? C13 C14 1.391(8) . ? C14 H14 0.9500 . ? C14 C15 1.406(7) . ? C15 H15 0.9500 . ? C15 C16 1.377(7) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.402(6) . ? C18 C22 1.460(7) . ? C19 C20 1.406(7) . ? C20 C21 1.409(6) . ? C20 C26 1.528(6) . ? C21 C24 1.471(7) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.565(7) . ? C26 C33 1.515(7) . ? C28 C29 1.380(8) . ? C28 C33 1.396(7) . ? C29 H29 0.9500 . ? C29 C30 1.395(9) . ? C30 H30 0.9500 . ? C30 C31 1.378(9) . ? C31 H31 0.9500 . ? C31 C32 1.417(8) . ? C32 H32 0.9500 . ? C32 C33 1.360(7) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? 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 I1 C2 C3 C4 177.8(3) . . . . ? I1 C2 C3 C9 -3.7(7) . . . . ? I2 C19 C20 C21 176.3(3) . . . . ? I2 C19 C20 C26 -5.2(7) . . . . ? O5 C9 C10 O6 68.9(7) . . . . ? O5 C9 C10 N2 -108.1(5) . . . . ? O5 C9 C16 C11 110.6(5) . . . . ? O5 C9 C16 C15 -69.7(6) . . . . ? O11 C26 C27 O12 65.7(6) . . . . ? O11 C26 C27 N4 -109.0(5) . . . . ? O11 C26 C33 C28 102.6(5) . . . . ? O11 C26 C33 C32 -75.9(7) . . . . ? N1 C1 C2 I1 -177.0(3) . . . . ? N1 C1 C2 C3 1.4(5) . . . . ? N1 C1 C5 O1 -177.9(5) . . . . ? N1 C1 C5 O2 2.9(6) . . . . ? N1 C4 C7 O3 160.1(5) . . . . ? N1 C4 C7 O4 -19.3(6) . . . . ? N2 C11 C12 C13 178.5(6) . . . . ? N2 C11 C16 C9 0.3(6) . . . . ? N2 C11 C16 C15 -179.4(5) . . . . ? N3 C18 C19 I2 -176.3(3) . . . . ? N3 C18 C19 C20 1.1(5) . . . . ? N3 C18 C22 O7 -162.4(5) . . . . ? N3 C18 C22 O8 18.7(6) . . . . ? N3 C21 C24 O9 -168.5(5) . . . . ? N3 C21 C24 O10 8.5(6) . . . . ? N4 C28 C29 C30 179.7(6) . . . . ? N4 C28 C33 C26 1.7(6) . . . . ? N4 C28 C33 C32 -179.7(5) . . . . ? C1 N1 C4 C3 1.5(5) . . . . ? C1 N1 C4 C7 180.0(4) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? C1 C2 C3 C9 178.0(4) . . . . ? C2 C1 C5 O1 1.5(9) . . . . ? C2 C1 C5 O2 -177.7(5) . . . . ? C2 C3 C4 N1 -0.5(5) . . . . ? C2 C3 C4 C7 -178.8(5) . . . . ? C2 C3 C9 O5 174.2(4) . . . . ? C2 C3 C9 C10 -64.1(6) . . . . ? C2 C3 C9 C16 49.7(6) . . . . ? C3 C4 C7 O3 -21.8(8) . . . . ? C3 C4 C7 O4 158.8(5) . . . . ? C3 C9 C10 O6 -56.5(7) . . . . ? C3 C9 C10 N2 126.5(5) . . . . ? C3 C9 C16 C11 -121.1(5) . . . . ? C3 C9 C16 C15 58.6(7) . . . . ? C4 N1 C1 C2 -1.8(5) . . . . ? C4 N1 C1 C5 177.8(4) . . . . ? C4 C3 C9 O5 -7.6(7) . . . . ? C4 C3 C9 C10 114.1(5) . . . . ? C4 C3 C9 C16 -132.1(5) . . . . ? C5 C1 C2 I1 3.5(7) . . . . ? C5 C1 C2 C3 -178.1(5) . . . . ? C6 O2 C5 O1 2.6(8) . . . . ? C6 O2 C5 C1 -178.2(4) . . . . ? C8 O4 C7 O3 -2.6(7) . . . . ? C8 O4 C7 C4 176.8(5) . . . . ? C9 C3 C4 N1 -179.1(4) . . . . ? C9 C3 C4 C7 2.7(8) . . . . ? C10 N2 C11 C12 -173.8(6) . . . . ? C10 N2 C11 C16 2.7(7) . . . . ? C10 C9 C16 C11 -2.7(5) . . . . ? C10 C9 C16 C15 177.0(5) . . . . ? C11 N2 C10 O6 178.6(6) . . . . ? C11 N2 C10 C9 -4.4(7) . . . . ? C11 C12 C13 C14 -0.9(9) . . . . ? C12 C11 C16 C9 177.1(5) . . . . ? C12 C11 C16 C15 -2.7(8) . . . . ? C12 C13 C14 C15 -0.3(8) . . . . ? C13 C14 C15 C16 0.0(7) . . . . ? C14 C15 C16 C9 -178.3(5) . . . . ? C14 C15 C16 C11 1.4(7) . . . . ? C16 C9 C10 O6 -178.7(6) . . . . ? C16 C9 C10 N2 4.2(6) . . . . ? C16 C11 C12 C13 2.4(9) . . . . ? C17 N2 C10 O6 1.2(11) . . . . ? C17 N2 C10 C9 178.2(6) . . . . ? C17 N2 C11 C12 3.6(11) . . . . ? C17 N2 C11 C16 -179.9(7) . . . . ? C18 N3 C21 C20 0.1(5) . . . . ? C18 N3 C21 C24 175.0(4) . . . . ? C18 C19 C20 C21 -1.0(5) . . . . ? C18 C19 C20 C26 177.5(4) . . . . ? C19 C18 C22 O7 16.5(9) . . . . ? C19 C18 C22 O8 -162.4(5) . . . . ? C19 C20 C21 N3 0.6(5) . . . . ? C19 C20 C21 C24 -173.4(5) . . . . ? C19 C20 C26 O11 -155.8(4) . . . . ? C19 C20 C26 C27 -41.7(6) . . . . ? C19 C20 C26 C33 73.0(6) . . . . ? C20 C21 C24 O9 4.9(9) . . . . ? C20 C21 C24 O10 -178.1(5) . . . . ? C20 C26 C27 O12 -55.4(7) . . . . ? C20 C26 C27 N4 129.8(5) . . . . ? C20 C26 C33 C28 -126.2(5) . . . . ? C20 C26 C33 C32 55.4(7) . . . . ? C21 N3 C18 C19 -0.7(5) . . . . ? C21 N3 C18 C22 178.4(4) . . . . ? C21 C20 C26 O11 22.4(7) . . . . ? C21 C20 C26 C27 136.5(5) . . . . ? C21 C20 C26 C33 -108.8(5) . . . . ? C22 C18 C19 I2 4.6(7) . . . . ? C22 C18 C19 C20 -178.0(5) . . . . ? C23 O8 C22 O7 9.7(7) . . . . ? C23 O8 C22 C18 -171.4(4) . . . . ? C25 O10 C24 O9 -4.9(8) . . . . ? C25 O10 C24 C21 177.9(5) . . . . ? C26 C20 C21 N3 -177.9(4) . . . . ? C26 C20 C21 C24 8.1(8) . . . . ? C27 N4 C28 C29 -173.1(7) . . . . ? C27 N4 C28 C33 4.1(7) . . . . ? C27 C26 C33 C28 -5.9(5) . . . . ? C27 C26 C33 C32 175.7(5) . . . . ? C28 N4 C27 O12 177.4(6) . . . . ? C28 N4 C27 C26 -7.8(6) . . . . ? C28 C29 C30 C31 -1.7(11) . . . . ? C29 C28 C33 C26 179.1(6) . . . . ? C29 C28 C33 C32 -2.3(9) . . . . ? C29 C30 C31 C32 0.1(10) . . . . ? C30 C31 C32 C33 0.5(8) . . . . ? C31 C32 C33 C26 178.9(5) . . . . ? C31 C32 C33 C28 0.6(8) . . . . ? C33 C26 C27 O12 -177.0(5) . . . . ? C33 C26 C27 N4 8.2(5) . . . . ? C33 C28 C29 C30 2.7(10) . . . . ? C34 N4 C27 O12 5.1(10) . . . . ? C34 N4 C27 C26 179.8(6) . . . . ? C34 N4 C28 C29 -0.8(11) . . . . ? C34 N4 C28 C33 176.4(6) . . . . ?