#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:41:29 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270500 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158317.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_7158317 loop_ _publ_author_name 'Zhu, Jun' 'Wang, Xu-Dong' 'Luo, Jian' 'Ao, Yu-Fei' 'Wang, Qi-Qiang' 'Wang, De-Xian' _publ_section_title ; Cation-chloride cotransport mediated by an ion pair transporter. ; _journal_issue 39 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 8586 _journal_page_last 8590 _journal_paper_doi 10.1039/d1ob01617b _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C30 H50 Ca N8 O11, 2(I), C H Cl3, H2 O' _chemical_formula_sum 'C31 H53 Ca Cl3 I2 N8 O12' _chemical_formula_weight 1130.04 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2018-01-31 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2021-08-17 deposited with the CCDC. 2021-09-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 117.084(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.2822(5) _cell_length_b 20.3116(5) _cell_length_c 16.7995(6) _cell_measurement_reflns_used 19460 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.5060 _cell_measurement_theta_min 1.6810 _cell_volume 4642.8(3) _computing_cell_refinement 'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'CIFTAB (Sheldrick, 2014)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 173.15 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'MM007-HF CCD(Saturn 724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_radiation_monochromator Confocal _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_unetI/netI 0.0233 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 10593 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.538 _diffrn_reflns_theta_min 1.691 _diffrn_source 'Rotating Anode' _exptl_absorpt_coefficient_mu 1.699 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.85477 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.9d (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.617 _exptl_crystal_description prism _exptl_crystal_F_000 2272 _exptl_crystal_size_max 0.338 _exptl_crystal_size_mid 0.217 _exptl_crystal_size_min 0.056 _refine_diff_density_max 1.053 _refine_diff_density_min -0.660 _refine_diff_density_rms 0.085 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 521 _refine_ls_number_reflns 10593 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0338 _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^)+(0.0272P)^2^+7.5310P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0808 _refine_ls_wR_factor_ref 0.0828 _reflns_Friedel_coverage 0.000 _reflns_number_gt 9445 _reflns_number_total 10593 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01617b2.cif _cod_data_source_block mx6776e_tw _cod_depositor_comments 'Adding full bibliography for 7158317.cif.' _cod_database_code 7158317 _shelx_shelxl_version_number 2016/6 _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. ; _shelx_estimated_absorpt_t_max 0.911 _shelx_estimated_absorpt_t_min 0.597 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.8117(12) 0.1883(12) 2. Fixed Uiso At 1.2 times of: All C(H) groups, {H10A,H10B} of O10, {H12C,H12D} of O12, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, {H11A,H11B} of O11, {H9A,H9B} of O9 3.a Riding coordinates: O10(H10A,H10B), O12(H12C,H12D) 3.b Rotating group: O9(H9A,H9B), O11(H11A,H11B) 3.c Ternary CH refined with riding coordinates: C31(H31) 3.d Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C6(H6A,H6B), C8(H8A,H8B), C9(H9C,H9D), C10(H10C,H10D), C11(H11C, H11D), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C21(H21A,H21B), C23(H23A,H23B) 3.e Aromatic/amide H refined with riding coordinates: C26(H26), C27(H27), C28(H28), C30(H30) 3.f Idealised Me refined as rotating group: C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C) ; _shelx_res_file ; TITL mx6776e_a.res in P2(1)/n mx6776e_tw.res created by SHELXL-2016/6 at 09:58:10 on 31-Jan-2018 CELL 0.71073 15.2822 20.3116 16.7995 90 117.084 90 ZERR 4 0.0005 0.0005 0.0006 0 0.005 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Ca Cl I N O UNIT 124 212 4 12 8 32 48 EQIV $1 1.5-X,-0.5+Y,1.5-Z EQIV $2 1-X,1-Y,1-Z L.S. 4 PLAN 20 SIZE 0.338 0.217 0.056 TEMP -100 HTAB O9 I1_$1 HTAB O9 I2_$1 HTAB O10 O12 HTAB O10 O12_$2 HTAB O11 I1_$2 HTAB O11 I2_$2 HTAB O12 N7 HTAB O12 N3 BOND $H LIST 4 fmap 2 acta CONF HTAB MERG 0 OMIT 14 0 4 OMIT 11 4 0 OMIT 11 8 0 OMIT 1 4 0 OMIT 4 1 14 OMIT 9 1 9 OMIT 11 15 0 OMIT 2 3 16 OMIT 7 11 4 OMIT -16 5 5 OMIT 7 4 11 OMIT 14 2 4 OMIT -11 6 12 OMIT -12 6 13 OMIT 11 11 0 OMIT 6 18 5 OMIT 11 6 0 OMIT 15 2 3 REM REM REM WGHT 0.027200 7.531000 BASF 0.18834 FVAR 3.47839 N1 6 0.417008 0.405675 0.078450 11.00000 0.02749 0.02927 = 0.02308 -0.00030 0.01548 0.00181 O1 7 0.289296 0.445993 0.092552 11.00000 0.02416 0.04551 = 0.02029 -0.00132 0.01089 0.00635 CA1 3 0.527939 0.298217 0.548996 11.00000 0.02448 0.02890 = 0.02254 0.00096 0.00751 -0.00247 C1 1 0.383131 0.423642 0.135026 11.00000 0.02338 0.02477 = 0.02363 -0.00017 0.01202 -0.00001 O2 7 0.564936 0.391439 0.344753 11.00000 0.02311 0.05542 = 0.02415 0.00999 0.01311 0.01168 C2 1 0.511132 0.383889 0.120036 11.00000 0.03098 0.02314 = 0.03118 0.00192 0.02011 0.00049 N2 6 0.565280 0.379411 0.209797 11.00000 0.02415 0.03075 = 0.02911 0.00547 0.01710 0.00448 O3 7 0.641614 0.293140 0.487025 11.00000 0.03323 0.04127 = 0.02816 0.00064 0.01534 0.00761 C3 1 0.518854 0.397033 0.255738 11.00000 0.02426 0.03046 = 0.02647 0.00378 0.01360 0.00085 N3 6 0.427574 0.422377 0.223977 11.00000 0.02432 0.03086 = 0.02209 0.00066 0.01293 0.00093 O4 7 0.560943 0.184424 0.516746 11.00000 0.03885 0.03266 = 0.03383 -0.00342 0.00221 0.00149 N4 6 0.556064 0.365943 0.070879 11.00000 0.03283 0.03252 = 0.03095 0.00118 0.02179 0.00393 C4 1 0.655316 0.337316 0.114580 11.00000 0.03181 0.03456 = 0.04084 -0.00114 0.02535 0.00217 AFIX 23 H4A 2 0.694970 0.360447 0.171736 11.00000 -1.20000 H4B 2 0.687750 0.343454 0.075787 11.00000 -1.20000 AFIX 0 O5 7 0.435349 0.214448 0.580112 11.00000 0.03211 0.03820 = 0.03931 0.01292 0.00538 -0.00642 N5 6 0.056488 0.401937 0.360548 11.00000 0.02428 0.03145 = 0.03235 -0.00326 0.01572 -0.00263 C5 1 0.650990 0.264304 0.132519 11.00000 0.04317 0.03290 = 0.05786 0.00354 0.03229 0.00611 AFIX 137 H5A 2 0.620518 0.240436 0.075614 11.00000 -1.50000 H5B 2 0.611929 0.257794 0.164716 11.00000 -1.50000 H5C 2 0.717734 0.247632 0.168787 11.00000 -1.50000 AFIX 0 O6 7 0.456163 0.335548 0.644429 11.00000 0.03031 0.04924 = 0.03083 0.00302 0.01715 -0.00714 N6 6 0.175202 0.413326 0.514836 11.00000 0.02545 0.03175 = 0.02747 0.00048 0.01536 0.00159 C6 1 0.509574 0.372256 -0.026873 11.00000 0.04534 0.04366 = 0.03228 -0.00586 0.02407 0.00246 AFIX 23 H6A 2 0.437705 0.377524 -0.050008 11.00000 -1.20000 H6B 2 0.521409 0.331714 -0.053246 11.00000 -1.20000 AFIX 0 O7 7 0.331866 0.442855 0.542447 11.00000 0.02623 0.05577 = 0.02488 -0.00305 0.01188 -0.00695 N7 6 0.220757 0.436373 0.399285 11.00000 0.02516 0.03728 = 0.02587 -0.00331 0.01433 -0.00461 C7 1 0.550830 0.431428 -0.054559 11.00000 0.09139 0.05012 = 0.03690 0.00318 0.04290 0.00067 AFIX 137 H7A 2 0.517227 0.435778 -0.119805 11.00000 -1.50000 H7B 2 0.621371 0.425117 -0.034318 11.00000 -1.50000 H7C 2 0.540404 0.471416 -0.027347 11.00000 -1.50000 AFIX 0 C8 1 0.662945 0.363864 0.381014 11.00000 0.02831 0.07972 = 0.03630 0.01991 0.01967 0.02007 AFIX 23 H8A 2 0.708544 0.395935 0.375298 11.00000 -1.20000 H8B 2 0.662530 0.323440 0.347919 11.00000 -1.20000 AFIX 0 N8 6 0.013918 0.382620 0.473597 11.00000 0.02628 0.03549 = 0.03554 0.00142 0.01913 0.00056 O8 7 0.099794 0.425594 0.253637 11.00000 0.02771 0.05349 = 0.02328 -0.00644 0.01302 -0.01378 O9 7 0.668274 0.283228 0.683051 11.00000 0.02748 0.07703 = 0.02281 0.00028 0.00921 -0.00198 AFIX 7 H9A 2 0.672213 0.278784 0.735421 11.00000 -1.50000 H9B 2 0.728044 0.281053 0.691562 11.00000 -1.50000 AFIX 0 C9 1 0.695920 0.347901 0.478364 11.00000 0.02352 0.05438 = 0.02733 0.00942 0.01042 0.00711 AFIX 23 H9C 2 0.766916 0.337232 0.507599 11.00000 -1.20000 H9D 2 0.685931 0.386796 0.508807 11.00000 -1.20000 AFIX 0 O10 7 0.539682 0.411164 0.530508 11.00000 0.02960 0.02774 = 0.02682 0.00036 0.01095 -0.00237 AFIX 3 0.8500 H10A 2 0.493732 0.427324 0.483308 11.00000 -1.20000 H10B 2 0.559242 0.449754 0.550108 11.00000 -1.20000 AFIX 0 C10 1 0.684122 0.230039 0.484106 11.00000 0.03979 0.05556 = 0.02395 -0.00347 0.00565 0.01788 AFIX 23 0.8500 H10C 2 0.730974 0.220895 0.535099 11.00000 -1.20000 H10D 2 0.706680 0.231074 0.446284 11.00000 -1.20000 AFIX 0 O11 7 0.397016 0.298824 0.403806 11.00000 0.02834 0.04641 = 0.02679 -0.00078 0.00906 -0.00403 AFIX 7 H11A 2 0.334676 0.295255 0.388406 11.00000 -1.50000 H11B 2 0.399787 0.302923 0.353526 11.00000 -1.50000 AFIX 0 C11 1 0.605029 0.179283 0.457763 11.00000 0.05402 0.04478 = 0.03113 -0.00795 0.00937 0.01452 AFIX 23 H11C 2 0.554864 0.186585 0.395224 11.00000 -1.20000 H11D 2 0.633218 0.134766 0.462055 11.00000 -1.20000 AFIX 0 C12 1 0.475311 0.143576 0.488378 11.00000 0.04850 0.02938 = 0.04896 -0.00053 -0.00275 -0.00400 AFIX 23 H12A 2 0.491112 0.097668 0.479819 11.00000 -1.20000 H12B 2 0.422455 0.159842 0.431083 11.00000 -1.20000 AFIX 0 C13 1 0.443186 0.146560 0.559708 11.00000 0.03737 0.03517 = 0.06315 0.01808 0.00010 -0.00670 AFIX 23 H13A 2 0.378776 0.124458 0.539133 11.00000 -1.20000 H13B 2 0.491503 0.123598 0.613934 11.00000 -1.20000 AFIX 0 C14 1 0.422610 0.223169 0.658455 11.00000 0.03775 0.06346 = 0.04271 0.02130 0.01386 -0.00910 AFIX 23 H14A 2 0.485421 0.215337 0.712668 11.00000 -1.20000 H14B 2 0.373042 0.191799 0.658480 11.00000 -1.20000 AFIX 0 C15 1 0.389103 0.292106 0.657403 11.00000 0.03624 0.06615 = 0.04627 0.01246 0.02297 -0.00930 AFIX 23 H15A 2 0.321748 0.297869 0.608335 11.00000 -1.20000 H15B 2 0.388257 0.302349 0.714663 11.00000 -1.20000 AFIX 0 C16 1 0.460739 0.400199 0.679398 11.00000 0.02762 0.06109 = 0.02065 -0.00692 0.00984 -0.00789 AFIX 23 H16A 2 0.509993 0.426166 0.669868 11.00000 -1.20000 H16B 2 0.483587 0.396998 0.744676 11.00000 -1.20000 AFIX 0 C17 1 0.363513 0.436644 0.637611 11.00000 0.03552 0.05927 = 0.02262 -0.01007 0.01586 -0.00648 AFIX 23 H17A 2 0.313739 0.412068 0.648054 11.00000 -1.20000 H17B 2 0.371333 0.480816 0.664944 11.00000 -1.20000 AFIX 0 C18 1 0.237890 0.429701 0.484691 11.00000 0.02175 0.03000 = 0.02743 -0.00218 0.01167 -0.00016 C19 1 0.083660 0.398994 0.449198 11.00000 0.02514 0.02485 = 0.03215 -0.00028 0.01746 0.00288 C20 1 0.128328 0.421420 0.342826 11.00000 0.02535 0.02987 = 0.02609 -0.00457 0.01364 -0.00118 C21 1 0.032982 0.382151 0.567455 11.00000 0.03740 0.03558 = 0.03770 0.00777 0.02588 0.00611 AFIX 23 H21A 2 0.103858 0.374138 0.605959 11.00000 -1.20000 H21B 2 -0.003952 0.345417 0.576762 11.00000 -1.20000 AFIX 0 C22 1 0.003745 0.446277 0.595760 11.00000 0.06191 0.04817 = 0.04406 0.00799 0.03340 0.01851 AFIX 137 H22A 2 -0.065558 0.455676 0.555952 11.00000 -1.50000 H22B 2 0.044565 0.482244 0.592198 11.00000 -1.50000 H22C 2 0.013399 0.442210 0.657357 11.00000 -1.50000 AFIX 0 C23 1 -0.086089 0.368476 0.406222 11.00000 0.02598 0.04785 = 0.04375 0.00057 0.02157 -0.00185 AFIX 23 H23A 2 -0.099093 0.392085 0.350368 11.00000 -1.20000 H23B 2 -0.132855 0.385141 0.427252 11.00000 -1.20000 AFIX 0 C24 1 -0.103567 0.295738 0.386597 11.00000 0.03961 0.05550 = 0.06218 -0.01119 0.02300 -0.01151 AFIX 137 H24A 2 -0.171636 0.288613 0.341396 11.00000 -1.50000 H24B 2 -0.091716 0.272190 0.441507 11.00000 -1.50000 H24C 2 -0.058685 0.279232 0.364158 11.00000 -1.50000 AFIX 0 C25 1 0.155647 0.464810 0.224675 11.00000 0.01879 0.04086 = 0.01931 -0.00097 0.00717 -0.00217 C26 1 0.159232 0.532102 0.237547 11.00000 0.02662 0.04184 = 0.02376 -0.00276 0.01159 0.00803 AFIX 43 H26 2 0.127722 0.551826 0.268968 11.00000 -1.20000 AFIX 0 C27 1 0.209676 0.570201 0.203726 11.00000 0.03549 0.02958 = 0.02948 0.00120 0.01152 0.00541 AFIX 43 H27 2 0.213556 0.616503 0.212683 11.00000 -1.20000 AFIX 0 C28 1 0.254650 0.541473 0.156864 11.00000 0.02917 0.03518 = 0.02572 0.00594 0.01150 0.00206 AFIX 43 H28 2 0.289139 0.567639 0.133510 11.00000 -1.20000 AFIX 0 C29 1 0.248257 0.474247 0.144909 11.00000 0.01899 0.03772 = 0.01812 0.00128 0.00707 0.00633 C30 1 0.199468 0.434139 0.178261 11.00000 0.02226 0.03105 = 0.02060 -0.00256 0.00704 0.00192 AFIX 43 H30 2 0.196168 0.387795 0.169752 11.00000 -1.20000 AFIX 0 I1 5 0.821455 0.769926 0.607495 11.00000 0.03151 0.03999 = 0.02880 0.00147 0.01665 -0.00066 I2 5 0.589483 0.772468 0.788360 11.00000 0.03009 0.04581 = 0.02729 -0.00194 0.01180 -0.00628 CL1 4 0.862046 0.507287 0.142277 11.00000 0.07473 0.08075 = 0.07489 0.00437 0.04130 0.02412 CL2 4 0.701128 0.504014 0.187177 11.00000 0.08953 0.05142 = 0.06621 -0.00484 0.04954 -0.01731 CL3 4 0.793237 0.627431 0.187755 11.00000 0.08630 0.03822 = 0.04790 -0.00043 0.02365 -0.01008 C31 1 0.760008 0.549742 0.136133 11.00000 0.05580 0.04022 = 0.03524 -0.00193 0.02180 -0.00053 AFIX 13 H31 2 0.712599 0.556313 0.071711 11.00000 -1.20000 AFIX 0 O12 7 0.396242 0.469328 0.379325 11.00000 0.02295 0.03595 = 0.02220 -0.00397 0.00915 -0.00485 AFIX 3 H12C 2 0.342272 0.457958 0.378425 11.00000 -1.20000 H12D 2 0.396242 0.459418 0.330155 11.00000 -1.20000 AFIX 0 HKLF 5 REM mx6776e_a.res in P2(1)/n REM R1 = 0.0338 for 9445 Fo > 4sig(Fo) and 0.0383 for all 10593 data REM 521 parameters refined using 0 restraints END WGHT 0.0273 7.5263 REM Instructions for potential hydrogen bonds HTAB C4 Cl2 EQIV $3 -x+3/2, y-1/2, -z+1/2 HTAB C6 I1_$3 HTAB O9 I1_$1 HTAB O9 I2_$1 HTAB C9 O10 HTAB O10 O12 HTAB O10 O12_$2 HTAB C10 I2_$1 HTAB O11 I1_$2 HTAB O11 I2_$2 HTAB C11 I2_$2 EQIV $4 x+1/2, -y+1/2, z+1/2 HTAB C13 O8_$4 HTAB C14 I1_$1 HTAB C16 O10 EQIV $5 -x+1, -y+1, -z HTAB C31 N1_$5 HTAB O12 N7 HTAB O12 N3 REM Highest difference peak 1.053, deepest hole -0.660, 1-sigma level 0.085 Q1 1 0.6181 0.7392 0.7842 11.00000 0.05 1.05 Q2 1 0.7392 0.2715 0.5415 11.00000 0.05 0.90 Q3 1 0.3484 0.2290 0.5498 11.00000 0.05 0.79 Q4 1 0.5914 0.2295 0.3814 11.00000 0.05 0.73 Q5 1 0.4949 0.2688 0.7126 11.00000 0.05 0.69 Q6 1 0.8055 0.7369 0.6342 11.00000 0.05 0.66 Q7 1 0.8540 0.6146 0.1926 11.00000 0.05 0.59 Q8 1 0.8703 0.4796 0.1788 11.00000 0.05 0.49 Q9 1 0.5388 0.7367 0.7315 11.00000 0.05 0.45 Q10 1 0.7795 0.7392 0.5632 11.00000 0.05 0.45 Q11 1 0.6415 0.2697 0.4418 11.00000 0.05 0.45 Q12 1 0.5252 0.2333 0.7002 11.00000 0.05 0.44 Q13 1 0.2904 0.2670 0.5107 11.00000 0.05 0.44 Q14 1 0.7519 0.7740 0.5851 11.00000 0.05 0.43 Q15 1 0.8303 0.7277 0.5801 11.00000 0.05 0.42 Q16 1 0.5616 0.7343 0.8050 11.00000 0.05 0.41 Q17 1 0.5924 0.4064 0.2409 11.00000 0.05 0.41 Q18 1 0.8730 0.7409 0.6153 11.00000 0.05 0.39 Q19 1 0.5328 0.2694 0.3417 11.00000 0.05 0.39 Q20 1 0.6732 0.2309 0.0493 11.00000 0.05 0.38 ; _shelx_res_checksum 59872 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 N1 N 0.41701(17) 0.40567(12) 0.07845(16) 0.0251(5) Uani 1 1 d . . . . . O1 O 0.28930(14) 0.44599(11) 0.09255(13) 0.0297(4) Uani 1 1 d . . . . . Ca1 Ca 0.52794(4) 0.29822(3) 0.54900(4) 0.02653(12) Uani 1 1 d . . . . . C1 C 0.3831(2) 0.42364(13) 0.13503(18) 0.0234(5) Uani 1 1 d . . . . . O2 O 0.56494(15) 0.39144(12) 0.34475(13) 0.0333(5) Uani 1 1 d . . . . . C2 C 0.5111(2) 0.38389(14) 0.1200(2) 0.0261(6) Uani 1 1 d . . . . . N2 N 0.56528(17) 0.37941(12) 0.20980(16) 0.0261(5) Uani 1 1 d . . . . . O3 O 0.64161(16) 0.29314(11) 0.48703(14) 0.0337(5) Uani 1 1 d . . . . . C3 C 0.5189(2) 0.39703(14) 0.25574(19) 0.0263(6) Uani 1 1 d . . . . . N3 N 0.42757(17) 0.42238(12) 0.22398(15) 0.0249(5) Uani 1 1 d . . . . . O4 O 0.56094(17) 0.18442(11) 0.51675(15) 0.0406(5) Uani 1 1 d . . . . . N4 N 0.55606(19) 0.36594(12) 0.07088(17) 0.0293(5) Uani 1 1 d . . . . . C4 C 0.6553(2) 0.33732(15) 0.1146(2) 0.0324(7) Uani 1 1 d . . . . . H4A H 0.694970 0.360447 0.171736 0.039 Uiso 1 1 calc R . . . . H4B H 0.687750 0.343454 0.075787 0.039 Uiso 1 1 calc R . . . . O5 O 0.43535(17) 0.21445(11) 0.58011(16) 0.0407(6) Uani 1 1 d . . . . . N5 N 0.05649(17) 0.40194(12) 0.36055(17) 0.0283(5) Uani 1 1 d . . . . . C5 C 0.6510(3) 0.26430(16) 0.1325(3) 0.0411(8) Uani 1 1 d . . . . . H5A H 0.620518 0.240436 0.075614 0.062 Uiso 1 1 calc GR . . . . H5B H 0.611929 0.257794 0.164716 0.062 Uiso 1 1 calc GR . . . . H5C H 0.717734 0.247632 0.168787 0.062 Uiso 1 1 calc GR . . . . O6 O 0.45616(16) 0.33555(12) 0.64443(14) 0.0356(5) Uani 1 1 d . . . . . N6 N 0.17520(17) 0.41333(12) 0.51484(16) 0.0270(5) Uani 1 1 d . . . . . C6 C 0.5096(3) 0.37226(17) -0.0269(2) 0.0380(7) Uani 1 1 d . . . . . H6A H 0.437705 0.377524 -0.050008 0.046 Uiso 1 1 calc R . . . . H6B H 0.521409 0.331714 -0.053246 0.046 Uiso 1 1 calc R . . . . O7 O 0.33187(15) 0.44286(12) 0.54245(14) 0.0355(5) Uani 1 1 d . . . . . N7 N 0.22076(18) 0.43637(13) 0.39929(16) 0.0284(5) Uani 1 1 d . . . . . C7 C 0.5508(4) 0.4314(2) -0.0546(3) 0.0542(10) Uani 1 1 d . . . . . H7A H 0.517227 0.435778 -0.119805 0.081 Uiso 1 1 calc GR . . . . H7B H 0.621371 0.425117 -0.034318 0.081 Uiso 1 1 calc GR . . . . H7C H 0.540404 0.471416 -0.027347 0.081 Uiso 1 1 calc GR . . . . C8 C 0.6629(2) 0.3639(2) 0.3810(2) 0.0462(9) Uani 1 1 d . . . . . H8A H 0.708544 0.395935 0.375298 0.055 Uiso 1 1 calc R . . . . H8B H 0.662530 0.323440 0.347919 0.055 Uiso 1 1 calc R . . . . N8 N 0.01392(18) 0.38262(13) 0.47360(18) 0.0305(5) Uani 1 1 d . . . . . O8 O 0.09979(15) 0.42559(12) 0.25364(14) 0.0343(5) Uani 1 1 d . . . . . O9 O 0.66827(17) 0.28323(13) 0.68305(15) 0.0433(6) Uani 1 1 d . . . . . H9A H 0.672213 0.278784 0.735421 0.065 Uiso 1 1 d GR . . . . H9B H 0.728044 0.281053 0.691562 0.065 Uiso 1 1 d GR . . . . C9 C 0.6959(2) 0.34790(18) 0.4784(2) 0.0355(7) Uani 1 1 d . . . . . H9C H 0.766916 0.337232 0.507599 0.043 Uiso 1 1 calc R . . . . H9D H 0.685931 0.386796 0.508807 0.043 Uiso 1 1 calc R . . . . O10 O 0.53968(15) 0.41116(10) 0.53051(13) 0.0288(4) Uani 1 1 d . . . . . H10A H 0.493732 0.427324 0.483308 0.035 Uiso 1 1 d R . . . . H10B H 0.559242 0.449754 0.550108 0.035 Uiso 1 1 d R . . . . C10 C 0.6841(3) 0.23004(18) 0.4841(2) 0.0432(9) Uani 1 1 d . . . . . H10C H 0.730974 0.220895 0.535099 0.052 Uiso 1 1 calc R . . . . H10D H 0.706680 0.231074 0.446284 0.052 Uiso 1 1 calc R . . . . O11 O 0.39702(16) 0.29882(11) 0.40381(14) 0.0352(5) Uani 1 1 d . . . . . H11A H 0.334676 0.295255 0.388406 0.053 Uiso 1 1 d GR . . . . H11B H 0.399787 0.302923 0.353526 0.053 Uiso 1 1 d GR . . . . C11 C 0.6050(3) 0.17928(19) 0.4578(2) 0.0471(9) Uani 1 1 d . . . . . H11C H 0.554864 0.186585 0.395224 0.057 Uiso 1 1 calc R . . . . H11D H 0.633218 0.134766 0.462055 0.057 Uiso 1 1 calc R . . . . C12 C 0.4753(3) 0.14358(17) 0.4884(3) 0.0518(10) Uani 1 1 d . . . . . H12A H 0.491112 0.097668 0.479819 0.062 Uiso 1 1 calc R . . . . H12B H 0.422455 0.159842 0.431083 0.062 Uiso 1 1 calc R . . . . C13 C 0.4432(3) 0.14656(18) 0.5597(3) 0.0540(11) Uani 1 1 d . . . . . H13A H 0.378776 0.124458 0.539133 0.065 Uiso 1 1 calc R . . . . H13B H 0.491503 0.123598 0.613934 0.065 Uiso 1 1 calc R . . . . C14 C 0.4226(3) 0.2232(2) 0.6585(3) 0.0497(10) Uani 1 1 d . . . . . H14A H 0.485421 0.215337 0.712668 0.060 Uiso 1 1 calc R . . . . H14B H 0.373042 0.191799 0.658480 0.060 Uiso 1 1 calc R . . . . C15 C 0.3891(3) 0.2921(2) 0.6574(3) 0.0479(9) Uani 1 1 d . . . . . H15A H 0.321748 0.297869 0.608335 0.058 Uiso 1 1 calc R . . . . H15B H 0.388257 0.302349 0.714663 0.058 Uiso 1 1 calc R . . . . C16 C 0.4607(2) 0.40020(18) 0.6794(2) 0.0369(7) Uani 1 1 d . . . . . H16A H 0.509993 0.426166 0.669868 0.044 Uiso 1 1 calc R . . . . H16B H 0.483587 0.396998 0.744676 0.044 Uiso 1 1 calc R . . . . C17 C 0.3635(2) 0.43664(19) 0.6376(2) 0.0381(8) Uani 1 1 d . . . . . H17A H 0.313739 0.412068 0.648054 0.046 Uiso 1 1 calc R . . . . H17B H 0.371333 0.480816 0.664944 0.046 Uiso 1 1 calc R . . . . C18 C 0.2379(2) 0.42970(14) 0.48469(19) 0.0262(6) Uani 1 1 d . . . . . C19 C 0.0837(2) 0.39899(14) 0.4492(2) 0.0257(6) Uani 1 1 d . . . . . C20 C 0.1283(2) 0.42142(14) 0.34283(19) 0.0264(6) Uani 1 1 d . . . . . C21 C 0.0330(2) 0.38215(16) 0.5675(2) 0.0335(7) Uani 1 1 d . . . . . H21A H 0.103858 0.374138 0.605959 0.040 Uiso 1 1 calc R . . . . H21B H -0.003952 0.345417 0.576762 0.040 Uiso 1 1 calc R . . . . C22 C 0.0037(3) 0.44628(19) 0.5958(3) 0.0478(9) Uani 1 1 d . . . . . H22A H -0.065558 0.455676 0.555952 0.072 Uiso 1 1 calc GR . . . . H22B H 0.044565 0.482244 0.592198 0.072 Uiso 1 1 calc GR . . . . H22C H 0.013399 0.442210 0.657357 0.072 Uiso 1 1 calc GR . . . . C23 C -0.0861(2) 0.36848(17) 0.4062(2) 0.0370(7) Uani 1 1 d . . . . . H23A H -0.099093 0.392085 0.350368 0.044 Uiso 1 1 calc R . . . . H23B H -0.132855 0.385141 0.427252 0.044 Uiso 1 1 calc R . . . . C24 C -0.1036(3) 0.2957(2) 0.3866(3) 0.0525(10) Uani 1 1 d . . . . . H24A H -0.171636 0.288613 0.341396 0.079 Uiso 1 1 calc GR . . . . H24B H -0.091716 0.272190 0.441507 0.079 Uiso 1 1 calc GR . . . . H24C H -0.058685 0.279232 0.364158 0.079 Uiso 1 1 calc GR . . . . C25 C 0.1556(2) 0.46481(15) 0.22467(18) 0.0269(6) Uani 1 1 d . . . . . C26 C 0.1592(2) 0.53210(16) 0.23755(19) 0.0307(6) Uani 1 1 d . . . . . H26 H 0.127722 0.551826 0.268968 0.037 Uiso 1 1 calc R . . . . C27 C 0.2097(2) 0.57020(16) 0.2037(2) 0.0328(7) Uani 1 1 d . . . . . H27 H 0.213556 0.616503 0.212683 0.039 Uiso 1 1 calc R . . . . C28 C 0.2546(2) 0.54147(15) 0.1569(2) 0.0304(6) Uani 1 1 d . . . . . H28 H 0.289139 0.567639 0.133510 0.036 Uiso 1 1 calc R . . . . C29 C 0.24826(19) 0.47425(15) 0.14491(18) 0.0255(6) Uani 1 1 d . . . . . C30 C 0.19947(19) 0.43414(15) 0.17826(18) 0.0257(6) Uani 1 1 d . . . . . H30 H 0.196168 0.387795 0.169752 0.031 Uiso 1 1 calc R . . . . I1 I 0.82145(2) 0.76993(2) 0.60750(2) 0.03231(6) Uani 1 1 d . . . . . I2 I 0.58948(2) 0.77247(2) 0.78836(2) 0.03488(6) Uani 1 1 d . . . . . Cl1 Cl 0.86205(10) 0.50729(7) 0.14228(9) 0.0740(3) Uani 1 1 d . . . . . Cl2 Cl 0.70113(10) 0.50401(5) 0.18718(8) 0.0637(3) Uani 1 1 d . . . . . Cl3 Cl 0.79324(9) 0.62743(5) 0.18776(7) 0.0601(3) Uani 1 1 d . . . . . C31 C 0.7600(3) 0.54974(17) 0.1361(2) 0.0433(8) Uani 1 1 d . . . . . H31 H 0.712599 0.556313 0.071711 0.052 Uiso 1 1 calc R . . . . O12 O 0.39624(14) 0.46933(10) 0.37932(13) 0.0275(4) Uani 1 1 d . . . . . H12C H 0.342272 0.457958 0.378425 0.033 Uiso 1 1 d R . . . . H12D H 0.396242 0.459418 0.330155 0.033 Uiso 1 1 d R . . . . 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 N1 0.0275(12) 0.0293(12) 0.0231(11) -0.0003(10) 0.0155(10) 0.0018(10) O1 0.0242(10) 0.0455(12) 0.0203(10) -0.0013(9) 0.0109(8) 0.0063(9) Ca1 0.0245(3) 0.0289(3) 0.0225(3) 0.0010(2) 0.0075(2) -0.0025(2) C1 0.0234(13) 0.0248(13) 0.0236(13) -0.0002(11) 0.0120(11) 0.0000(10) O2 0.0231(10) 0.0554(14) 0.0242(10) 0.0100(10) 0.0131(9) 0.0117(9) C2 0.0310(14) 0.0231(13) 0.0312(15) 0.0019(12) 0.0201(13) 0.0005(11) N2 0.0241(12) 0.0307(12) 0.0291(13) 0.0055(10) 0.0171(10) 0.0045(10) O3 0.0332(11) 0.0413(12) 0.0282(11) 0.0006(10) 0.0153(9) 0.0076(10) C3 0.0243(13) 0.0305(14) 0.0265(14) 0.0038(12) 0.0136(11) 0.0008(11) N3 0.0243(11) 0.0309(12) 0.0221(11) 0.0007(10) 0.0129(10) 0.0009(10) O4 0.0388(13) 0.0327(12) 0.0338(12) -0.0034(10) 0.0022(10) 0.0015(10) N4 0.0328(13) 0.0325(13) 0.0310(13) 0.0012(11) 0.0218(11) 0.0039(10) C4 0.0318(15) 0.0346(16) 0.0408(17) -0.0011(14) 0.0253(14) 0.0022(13) O5 0.0321(12) 0.0382(12) 0.0393(13) 0.0129(10) 0.0054(10) -0.0064(10) N5 0.0243(12) 0.0315(13) 0.0324(13) -0.0033(11) 0.0157(11) -0.0026(10) C5 0.0432(19) 0.0329(17) 0.058(2) 0.0035(16) 0.0323(18) 0.0061(14) O6 0.0303(11) 0.0492(13) 0.0308(11) 0.0030(10) 0.0172(9) -0.0071(10) N6 0.0255(12) 0.0317(13) 0.0275(12) 0.0005(10) 0.0154(10) 0.0016(10) C6 0.0453(19) 0.0437(18) 0.0323(17) -0.0059(14) 0.0241(15) 0.0025(15) O7 0.0262(11) 0.0558(14) 0.0249(11) -0.0031(10) 0.0119(9) -0.0069(10) N7 0.0252(12) 0.0373(13) 0.0259(12) -0.0033(11) 0.0143(10) -0.0046(10) C7 0.091(3) 0.050(2) 0.037(2) 0.0032(17) 0.043(2) 0.001(2) C8 0.0283(16) 0.080(3) 0.0363(18) 0.0199(18) 0.0197(15) 0.0201(17) N8 0.0263(12) 0.0355(13) 0.0355(14) 0.0014(11) 0.0191(11) 0.0006(10) O8 0.0277(11) 0.0535(14) 0.0233(10) -0.0064(10) 0.0130(9) -0.0138(10) O9 0.0275(11) 0.0770(18) 0.0228(11) 0.0003(11) 0.0092(9) -0.0020(12) C9 0.0235(14) 0.054(2) 0.0273(15) 0.0094(14) 0.0104(12) 0.0071(14) O10 0.0296(10) 0.0277(10) 0.0268(10) 0.0004(8) 0.0109(9) -0.0024(8) C10 0.0398(19) 0.056(2) 0.0240(16) -0.0035(15) 0.0057(14) 0.0179(16) O11 0.0283(11) 0.0464(13) 0.0268(11) -0.0008(10) 0.0091(9) -0.0040(10) C11 0.054(2) 0.045(2) 0.0311(17) -0.0080(15) 0.0094(16) 0.0145(17) C12 0.048(2) 0.0294(17) 0.049(2) -0.0005(16) -0.0027(18) -0.0040(15) C13 0.0374(19) 0.0352(18) 0.063(3) 0.0181(18) 0.0001(18) -0.0067(15) C14 0.0377(19) 0.063(2) 0.043(2) 0.0213(18) 0.0139(16) -0.0091(17) C15 0.0362(18) 0.066(2) 0.046(2) 0.0125(19) 0.0230(17) -0.0093(17) C16 0.0276(15) 0.061(2) 0.0207(14) -0.0069(14) 0.0098(12) -0.0079(14) C17 0.0355(17) 0.059(2) 0.0226(15) -0.0101(15) 0.0159(13) -0.0065(15) C18 0.0218(13) 0.0300(14) 0.0274(14) -0.0022(12) 0.0117(12) -0.0002(11) C19 0.0251(13) 0.0248(13) 0.0321(15) -0.0003(12) 0.0175(12) 0.0029(11) C20 0.0254(13) 0.0299(14) 0.0261(14) -0.0046(12) 0.0136(12) -0.0012(11) C21 0.0374(17) 0.0356(16) 0.0377(17) 0.0078(14) 0.0259(15) 0.0061(13) C22 0.062(2) 0.048(2) 0.044(2) 0.0080(17) 0.0334(19) 0.0185(18) C23 0.0260(15) 0.0479(19) 0.0438(19) 0.0006(15) 0.0216(14) -0.0018(14) C24 0.040(2) 0.056(2) 0.062(3) -0.011(2) 0.0230(19) -0.0115(17) C25 0.0188(12) 0.0409(16) 0.0193(13) -0.0010(12) 0.0072(11) -0.0022(11) C26 0.0266(14) 0.0418(17) 0.0238(14) -0.0028(13) 0.0116(12) 0.0080(13) C27 0.0355(16) 0.0296(15) 0.0295(16) 0.0012(12) 0.0115(13) 0.0054(13) C28 0.0292(15) 0.0352(16) 0.0257(14) 0.0059(12) 0.0115(12) 0.0021(12) C29 0.0190(12) 0.0377(15) 0.0181(13) 0.0013(11) 0.0071(10) 0.0063(11) C30 0.0223(13) 0.0310(14) 0.0206(13) -0.0026(11) 0.0070(11) 0.0019(11) I1 0.03151(11) 0.03999(11) 0.02880(10) 0.00147(8) 0.01665(8) -0.00066(8) I2 0.03009(11) 0.04581(12) 0.02729(11) -0.00194(9) 0.01180(8) -0.00628(8) Cl1 0.0747(8) 0.0808(8) 0.0749(8) 0.0044(7) 0.0413(7) 0.0241(6) Cl2 0.0895(8) 0.0514(6) 0.0662(7) -0.0048(5) 0.0495(6) -0.0173(5) Cl3 0.0863(8) 0.0382(5) 0.0479(5) -0.0004(4) 0.0236(5) -0.0101(5) C31 0.056(2) 0.0402(18) 0.0352(18) -0.0019(15) 0.0218(17) -0.0005(16) O12 0.0230(10) 0.0360(11) 0.0222(10) -0.0040(8) 0.0092(8) -0.0048(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 N1 C2 113.0(2) . . ? C1 O1 C29 118.1(2) . . ? O3 Ca1 O4 66.76(8) . . ? O3 Ca1 O5 132.39(9) . . ? O3 Ca1 O6 158.35(8) . . ? O5 Ca1 O4 65.68(9) . . ? O5 Ca1 O6 66.05(8) . . ? O6 Ca1 O4 129.12(9) . . ? O9 Ca1 O3 83.31(8) . . ? O9 Ca1 O4 84.23(9) . . ? O9 Ca1 O5 94.09(8) . . ? O9 Ca1 O6 84.04(8) . . ? O9 Ca1 O10 99.52(9) . . ? O9 Ca1 O11 170.02(9) . . ? O10 Ca1 O3 82.52(8) . . ? O10 Ca1 O4 148.49(8) . . ? O10 Ca1 O5 144.00(8) . . ? O10 Ca1 O6 82.34(8) . . ? O10 Ca1 O11 86.41(8) . . ? O11 Ca1 O3 89.56(8) . . ? O11 Ca1 O4 86.55(8) . . ? O11 Ca1 O5 85.55(8) . . ? O11 Ca1 O6 104.82(8) . . ? N1 C1 O1 112.3(2) . . ? N1 C1 N3 129.4(3) . . ? N3 C1 O1 118.3(2) . . ? C3 O2 C8 114.9(2) . . ? N2 C2 N1 124.3(2) . . ? N4 C2 N1 119.4(3) . . ? N4 C2 N2 116.3(3) . . ? C3 N2 C2 114.6(2) . . ? C9 O3 Ca1 125.26(18) . . ? C9 O3 C10 113.2(3) . . ? C10 O3 Ca1 118.5(2) . . ? O2 C3 N3 113.5(2) . . ? N2 C3 O2 118.9(3) . . ? N2 C3 N3 127.6(3) . . ? C1 N3 C3 111.0(2) . . ? C11 O4 Ca1 115.2(2) . . ? C11 O4 C12 111.9(3) . . ? C12 O4 Ca1 111.5(2) . . ? C2 N4 C4 120.0(3) . . ? C2 N4 C6 122.8(3) . . ? C6 N4 C4 117.2(2) . . ? N4 C4 H4A 109.5 . . ? N4 C4 H4B 109.5 . . ? N4 C4 C5 110.9(3) . . ? H4A C4 H4B 108.1 . . ? C5 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C13 O5 Ca1 120.2(2) . . ? C14 O5 Ca1 116.8(2) . . ? C14 O5 C13 113.6(3) . . ? C20 N5 C19 113.0(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C15 O6 Ca1 118.2(2) . . ? C16 O6 Ca1 127.17(17) . . ? C16 O6 C15 113.9(3) . . ? C18 N6 C19 113.7(2) . . ? N4 C6 H6A 109.5 . . ? N4 C6 H6B 109.5 . . ? N4 C6 C7 110.7(3) . . ? H6A C6 H6B 108.1 . . ? C7 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C18 O7 C17 119.3(2) . . ? C20 N7 C18 111.5(2) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 H8A 110.1 . . ? O2 C8 H8B 110.1 . . ? O2 C8 C9 108.0(2) . . ? H8A C8 H8B 108.4 . . ? C9 C8 H8A 110.1 . . ? C9 C8 H8B 110.1 . . ? C19 N8 C21 122.1(3) . . ? C19 N8 C23 120.5(3) . . ? C23 N8 C21 117.3(2) . . ? C20 O8 C25 118.4(2) . . ? Ca1 O9 H9A 127.7 . . ? Ca1 O9 H9B 127.8 . . ? H9A O9 H9B 104.5 . . ? O3 C9 C8 110.7(3) . . ? O3 C9 H9C 109.5 . . ? O3 C9 H9D 109.5 . . ? C8 C9 H9C 109.5 . . ? C8 C9 H9D 109.5 . . ? H9C C9 H9D 108.1 . . ? Ca1 O10 H10A 115.0 . . ? Ca1 O10 H10B 152.9 . . ? H10A O10 H10B 90.0 . . ? O3 C10 H10C 110.1 . . ? O3 C10 H10D 110.1 . . ? O3 C10 C11 107.8(3) . . ? H10C C10 H10D 108.5 . . ? C11 C10 H10C 110.1 . . ? C11 C10 H10D 110.1 . . ? Ca1 O11 H11A 127.5 . . ? Ca1 O11 H11B 128.0 . . ? H11A O11 H11B 104.5 . . ? O4 C11 C10 108.4(3) . . ? O4 C11 H11C 110.0 . . ? O4 C11 H11D 110.0 . . ? C10 C11 H11C 110.0 . . ? C10 C11 H11D 110.0 . . ? H11C C11 H11D 108.4 . . ? O4 C12 H12A 110.3 . . ? O4 C12 H12B 110.3 . . ? O4 C12 C13 107.1(3) . . ? H12A C12 H12B 108.5 . . ? C13 C12 H12A 110.3 . . ? C13 C12 H12B 110.3 . . ? O5 C13 C12 108.9(3) . . ? O5 C13 H13A 109.9 . . ? O5 C13 H13B 109.9 . . ? C12 C13 H13A 109.9 . . ? C12 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? O5 C14 H14A 110.3 . . ? O5 C14 H14B 110.3 . . ? O5 C14 C15 107.3(3) . . ? H14A C14 H14B 108.5 . . ? C15 C14 H14A 110.3 . . ? C15 C14 H14B 110.3 . . ? O6 C15 C14 108.2(3) . . ? O6 C15 H15A 110.0 . . ? O6 C15 H15B 110.0 . . ? C14 C15 H15A 110.0 . . ? C14 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? O6 C16 H16A 108.8 . . ? O6 C16 H16B 108.8 . . ? O6 C16 C17 113.9(3) . . ? H16A C16 H16B 107.7 . . ? C17 C16 H16A 108.8 . . ? C17 C16 H16B 108.8 . . ? O7 C17 C16 108.5(2) . . ? O7 C17 H17A 110.0 . . ? O7 C17 H17B 110.0 . . ? C16 C17 H17A 110.0 . . ? C16 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? N6 C18 O7 119.9(3) . . ? N6 C18 N7 128.0(3) . . ? N7 C18 O7 112.1(2) . . ? N5 C19 N6 124.7(2) . . ? N8 C19 N5 117.2(3) . . ? N8 C19 N6 118.1(3) . . ? N5 C20 N7 129.0(3) . . ? N5 C20 O8 112.6(2) . . ? N7 C20 O8 118.4(2) . . ? N8 C21 H21A 109.0 . . ? N8 C21 H21B 109.0 . . ? N8 C21 C22 112.8(3) . . ? H21A C21 H21B 107.8 . . ? C22 C21 H21A 109.0 . . ? C22 C21 H21B 109.0 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N8 C23 H23A 109.1 . . ? N8 C23 H23B 109.1 . . ? N8 C23 C24 112.4(3) . . ? H23A C23 H23B 107.9 . . ? C24 C23 H23A 109.1 . . ? C24 C23 H23B 109.1 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 O8 119.6(3) . . ? C26 C25 C30 122.6(3) . . ? C30 C25 O8 117.7(3) . . ? C25 C26 H26 120.7 . . ? C25 C26 C27 118.6(3) . . ? C27 C26 H26 120.7 . . ? C26 C27 H27 119.7 . . ? C26 C27 C28 120.7(3) . . ? C28 C27 H27 119.7 . . ? C27 C28 H28 120.7 . . ? C29 C28 C27 118.6(3) . . ? C29 C28 H28 120.7 . . ? C28 C29 O1 118.1(3) . . ? C28 C29 C30 122.7(3) . . ? C30 C29 O1 119.1(3) . . ? C25 C30 H30 121.6 . . ? C29 C30 C25 116.8(3) . . ? C29 C30 H30 121.6 . . ? Cl1 C31 Cl2 110.6(2) . . ? Cl1 C31 Cl3 111.4(2) . . ? Cl1 C31 H31 108.5 . . ? Cl2 C31 H31 108.5 . . ? Cl3 C31 Cl2 109.22(19) . . ? Cl3 C31 H31 108.5 . . ? H12C O12 H12D 110.3 . . ? 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 N1 C1 1.324(3) . ? N1 C2 1.356(4) . ? O1 C1 1.356(3) . ? O1 C29 1.414(3) . ? Ca1 O3 2.400(2) . ? Ca1 O4 2.478(2) . ? Ca1 O5 2.417(2) . ? Ca1 O6 2.439(2) . ? Ca1 O9 2.316(2) . ? Ca1 O10 2.333(2) . ? Ca1 O11 2.347(2) . ? C1 N3 1.331(4) . ? O2 C3 1.336(3) . ? O2 C8 1.448(4) . ? C2 N2 1.353(4) . ? C2 N4 1.343(3) . ? N2 C3 1.314(3) . ? O3 C9 1.434(4) . ? O3 C10 1.448(4) . ? C3 N3 1.348(4) . ? O4 C11 1.433(4) . ? O4 C12 1.435(4) . ? N4 C4 1.471(4) . ? N4 C6 1.468(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.521(4) . ? O5 C13 1.439(5) . ? O5 C14 1.426(5) . ? N5 C19 1.353(4) . ? N5 C20 1.322(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? O6 C15 1.442(4) . ? O6 C16 1.427(4) . ? N6 C18 1.314(4) . ? N6 C19 1.361(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.525(5) . ? O7 C17 1.450(4) . ? O7 C18 1.344(3) . ? N7 C18 1.343(4) . ? N7 C20 1.329(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.511(4) . ? N8 C19 1.346(3) . ? N8 C21 1.467(4) . ? N8 C23 1.457(4) . ? O8 C20 1.359(3) . ? O8 C25 1.406(3) . ? O9 H9A 0.8588 . ? O9 H9B 0.8590 . ? C9 H9C 0.9900 . ? C9 H9D 0.9900 . ? O10 H10A 0.8500 . ? O10 H10B 0.8500 . ? C10 H10C 0.8500 . ? C10 H10D 0.8500 . ? C10 C11 1.494(5) . ? O11 H11A 0.8691 . ? O11 H11B 0.8688 . ? C11 H11C 0.9900 . ? C11 H11D 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.489(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C15 1.488(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16 C17 1.516(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.522(5) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C23 C24 1.511(5) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.381(4) . ? C25 C30 1.386(4) . ? C26 H26 0.9500 . ? C26 C27 1.384(4) . ? C27 H27 0.9500 . ? C27 C28 1.388(4) . ? C28 H28 0.9500 . ? C28 C29 1.377(4) . ? C29 C30 1.383(4) . ? C30 H30 0.9500 . ? Cl1 C31 1.743(4) . ? Cl2 C31 1.764(4) . ? Cl3 C31 1.760(4) . ? C31 H31 1.0000 . ? O12 H12C 0.8500 . ? O12 H12D 0.8502 . ? 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 O9 H9A I1 0.86 2.60 3.461(2) 177.3 2_646 O9 H9B I2 0.86 2.66 3.516(2) 177.8 2_646 O10 H10A O12 0.85 1.91 2.754(3) 175.8 . O10 H10B O12 0.85 1.96 2.792(3) 166.5 3_666 O11 H11A I1 0.87 2.76 3.543(2) 151.2 3_666 O11 H11B I2 0.87 2.90 3.629(2) 142.6 3_666 O12 H12C N7 0.85 2.09 2.928(3) 169.9 . O12 H12D N3 0.85 2.18 3.015(3) 166.8 . 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 N1 C1 N3 C3 -1.8(4) . . . . ? N1 C2 N2 C3 1.1(4) . . . . ? N1 C2 N4 C4 -175.2(3) . . . . ? N1 C2 N4 C6 3.5(4) . . . . ? O1 C1 N3 C3 178.0(2) . . . . ? O1 C29 C30 C25 -176.3(2) . . . . ? Ca1 O3 C9 C8 -113.6(2) . . . . ? Ca1 O3 C10 C11 40.6(3) . . . . ? Ca1 O4 C11 C10 43.2(3) . . . . ? Ca1 O4 C12 C13 -56.1(3) . . . . ? Ca1 O5 C13 C12 -23.8(4) . . . . ? Ca1 O5 C14 C15 48.3(3) . . . . ? Ca1 O6 C15 C14 34.8(4) . . . . ? Ca1 O6 C16 C17 109.4(3) . . . . ? C1 N1 C2 N2 1.2(4) . . . . ? C1 N1 C2 N4 -177.9(3) . . . . ? C1 O1 C29 C28 93.4(3) . . . . ? C1 O1 C29 C30 -89.7(3) . . . . ? O2 C3 N3 C1 -176.7(2) . . . . ? O2 C8 C9 O3 70.1(4) . . . . ? C2 N1 C1 O1 179.3(2) . . . . ? C2 N1 C1 N3 -0.8(4) . . . . ? C2 N2 C3 O2 177.0(3) . . . . ? C2 N2 C3 N3 -4.5(4) . . . . ? C2 N4 C4 C5 81.8(3) . . . . ? C2 N4 C6 C7 103.3(3) . . . . ? N2 C2 N4 C4 5.6(4) . . . . ? N2 C2 N4 C6 -175.7(3) . . . . ? N2 C3 N3 C1 4.7(4) . . . . ? O3 C10 C11 O4 -53.0(3) . . . . ? C3 O2 C8 C9 -168.5(3) . . . . ? O4 C12 C13 O5 51.2(4) . . . . ? N4 C2 N2 C3 -179.7(3) . . . . ? C4 N4 C6 C7 -78.0(4) . . . . ? O5 C14 C15 O6 -51.8(4) . . . . ? O6 C16 C17 O7 -60.1(4) . . . . ? C6 N4 C4 C5 -97.0(3) . . . . ? C8 O2 C3 N2 -1.8(4) . . . . ? C8 O2 C3 N3 179.5(3) . . . . ? O8 C25 C26 C27 -176.1(3) . . . . ? O8 C25 C30 C29 175.6(2) . . . . ? C9 O3 C10 C11 -158.1(3) . . . . ? C10 O3 C9 C8 86.5(3) . . . . ? C11 O4 C12 C13 173.3(3) . . . . ? C12 O4 C11 C10 171.9(3) . . . . ? C13 O5 C14 C15 -165.0(3) . . . . ? C14 O5 C13 C12 -169.2(3) . . . . ? C15 O6 C16 C17 -60.7(4) . . . . ? C16 O6 C15 C14 -154.2(3) . . . . ? C17 O7 C18 N6 2.0(4) . . . . ? C17 O7 C18 N7 -178.7(3) . . . . ? C18 N6 C19 N5 -1.2(4) . . . . ? C18 N6 C19 N8 -179.0(3) . . . . ? C18 O7 C17 C16 134.7(3) . . . . ? C18 N7 C20 N5 -0.1(4) . . . . ? C18 N7 C20 O8 -179.8(3) . . . . ? C19 N5 C20 N7 1.7(4) . . . . ? C19 N5 C20 O8 -178.7(2) . . . . ? C19 N6 C18 O7 -177.7(3) . . . . ? C19 N6 C18 N7 3.1(4) . . . . ? C19 N8 C21 C22 94.7(4) . . . . ? C19 N8 C23 C24 94.9(4) . . . . ? C20 N5 C19 N6 -0.9(4) . . . . ? C20 N5 C19 N8 176.9(3) . . . . ? C20 N7 C18 N6 -2.6(4) . . . . ? C20 N7 C18 O7 178.2(3) . . . . ? C20 O8 C25 C26 -65.6(4) . . . . ? C20 O8 C25 C30 118.9(3) . . . . ? C21 N8 C19 N5 -175.8(3) . . . . ? C21 N8 C19 N6 2.2(4) . . . . ? C21 N8 C23 C24 -88.8(3) . . . . ? C23 N8 C19 N5 0.3(4) . . . . ? C23 N8 C19 N6 178.4(3) . . . . ? C23 N8 C21 C22 -81.6(4) . . . . ? C25 O8 C20 N5 159.7(3) . . . . ? C25 O8 C20 N7 -20.6(4) . . . . ? C25 C26 C27 C28 0.8(4) . . . . ? C26 C25 C30 C29 0.2(4) . . . . ? C26 C27 C28 C29 -0.2(4) . . . . ? C27 C28 C29 O1 176.3(2) . . . . ? C27 C28 C29 C30 -0.5(4) . . . . ? C28 C29 C30 C25 0.5(4) . . . . ? C29 O1 C1 N1 -172.4(2) . . . . ? C29 O1 C1 N3 7.7(4) . . . . ? C30 C25 C26 C27 -0.9(4) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.8117(12) 2 0.1883(12)