#------------------------------------------------------------------------------ #$Date: 2019-04-14 03:42:31 +0300 (Sun, 14 Apr 2019) $ #$Revision: 214633 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/67/7156780.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_7156780 loop_ _publ_author_name 'Hu, Wei-Bo' 'Wang, Guo' 'qiang, hui' 'guo, yunzhe' 'yang, jie' 'Wen, Ke' _publ_section_title ; Systematic rim cyano functionalization of pillar[5]arene and corresponding host−guest property varieties ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB00396G _journal_year 2019 _chemical_formula_moiety 'C H2 Cl2, C45 H32 N6 O4, C H Cl3' _chemical_formula_sum 'C47 H35 Cl5 N6 O4' _chemical_formula_weight 925.06 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_date 2018-02-01 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2018-09-30 deposited with the CCDC. 2019-04-12 downloaded from the CCDC. ; _cell_angle_alpha 91.438(3) _cell_angle_beta 99.204(2) _cell_angle_gamma 99.741(2) _cell_formula_units_Z 2 _cell_length_a 11.8381(5) _cell_length_b 12.1136(5) _cell_length_c 16.2757(8) _cell_measurement_reflns_used 7223 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 26.26 _cell_measurement_theta_min 2.47 _cell_volume 2267.44(18) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 150.0 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1333 _diffrn_reflns_av_unetI/netI 0.0931 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 52356 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.072 _diffrn_reflns_theta_min 2.234 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.370 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.355 _exptl_crystal_description block _exptl_crystal_F_000 952 _refine_diff_density_max 1.301 _refine_diff_density_min -1.432 _refine_diff_density_rms 0.139 _refine_ls_extinction_coef 0.011(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/1 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 564 _refine_ls_number_reflns 9894 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.191 _refine_ls_R_factor_all 0.1953 _refine_ls_R_factor_gt 0.1147 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3011 _refine_ls_wR_factor_ref 0.3600 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5280 _reflns_number_total 9894 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob00396g2.cif _cod_data_source_block mo_6cn_0m _cod_database_code 7156780 _shelx_shelxl_version_number 2018/1 _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, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C47(H47) 2.b Secondary CH2 refined with riding coordinates: C46(H46A,H46B), C1(H1A,H1B), C10(H10A,H10B), C19(H19A,H19B), C28(H28A,H28B), C37(H37A,H37B) 2.c Aromatic/amide H refined with riding coordinates: C4(H4), C7(H7), C13(H13), C16(H16), C22(H22), C25(H25), C31(H31), C34(H34), C39(H39), C42(H42) 2.d Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C) ; _shelx_res_file ; TITL mo_6CN_0m in P-1 mo_6cn_0m.res created by SHELXL-2018/1 at 14:38:50 on 01-Feb-2018 CELL 0.71073 11.8381 12.1136 16.2757 91.4383 99.2036 99.7406 ZERR 2 0.0005 0.0005 0.0008 0.0025 0.0024 0.0023 LATT 1 SFAC C H Cl N O UNIT 94 70 10 12 8 L.S. 20 PLAN 10 TEMP -123.15 BOND fmap 2 acta OMIT -4 2 4 OMIT 2 0 0 OMIT -2 2 3 OMIT 1 -5 2 OMIT -5 1 0 OMIT -1 -2 1 OMIT 2 3 5 OMIT 1 2 0 OMIT 4 0 0 OMIT -3 -2 3 OMIT 0 2 0 OMIT 0 0 2 OMIT -2 1 2 OMIT -2 2 1 OMIT 3 0 4 OMIT 0 -2 2 OMIT -1 -1 1 OMIT -1 -3 2 OMIT -12 3 6 OMIT -3 3 3 OMIT -3 6 0 OMIT 3 3 6 OMIT -5 3 3 OMIT -4 0 3 OMIT 1 1 8 OMIT 0 -2 3 OMIT 0 -1 6 OMIT -2 2 8 OMIT -2 -3 1 OMIT 3 2 4 OMIT -2 4 4 OMIT -1 2 7 OMIT -1 2 6 OMIT -1 1 5 OMIT -2 -3 4 OMIT 1 0 1 OMIT 0 -1 4 OMIT -1 -1 6 OMIT -2 4 3 OMIT 3 -4 4 OMIT -2 2 6 OMIT 2 2 2 OMIT 2 2 5 OMIT 4 3 4 OMIT 2 2 3 OMIT -2 4 1 OMIT 2 2 4 OMIT -5 4 6 REM REM REM WGHT 0.200000 EXTI 0.011096 FVAR 0.49355 CL1 3 0.001736 1.105384 -0.161344 11.00000 0.06686 0.05327 = 0.06494 0.00420 0.00333 0.01645 C46 1 0.139493 1.158211 -0.169898 11.00000 0.08644 0.08775 = 0.07349 0.00322 -0.00630 0.02659 AFIX 23 H46A 2 0.190540 1.108187 -0.142702 11.00000 -1.20000 H46B 2 0.161747 1.232146 -0.138966 11.00000 -1.20000 AFIX 0 O1 5 -0.112540 0.818345 -0.147188 11.00000 0.01744 0.03613 = 0.02672 0.00115 -0.00137 0.00412 O2 5 0.297467 0.823056 -0.269673 11.00000 0.01892 0.04034 = 0.03084 -0.00313 0.00393 0.00249 O3 5 0.336402 1.384920 0.066000 11.00000 0.02939 0.03389 = 0.02284 0.00466 0.00163 0.01022 O4 5 0.259651 1.511564 -0.259105 11.00000 0.04560 0.04775 = 0.02534 0.01133 0.00626 0.02077 N1 4 0.265246 0.922173 0.110673 11.00000 0.03085 0.03997 = 0.03700 0.00676 0.00809 0.00397 N2 4 0.550081 1.251818 -0.240863 11.00000 0.04529 0.04072 = 0.04494 0.00328 0.02236 0.01027 N3 4 -0.060945 1.354896 -0.032407 11.00000 0.04307 0.03185 = 0.03082 0.00114 0.00449 0.01181 N4 4 -0.137077 1.433317 -0.517917 11.00000 0.06446 0.05376 = 0.02716 0.00764 -0.00365 -0.01170 N5 4 -0.402363 0.798403 -0.224302 11.00000 0.03059 0.04943 = 0.04707 0.01304 0.00525 0.00243 N6 4 -0.011664 1.196212 -0.488298 11.00000 0.04411 0.04287 = 0.03742 0.00902 0.01604 0.01290 C1 1 -0.133951 0.780681 -0.317104 11.00000 0.02229 0.02141 = 0.03133 -0.00122 -0.00236 0.00644 AFIX 23 H1A 2 -0.192659 0.732921 -0.290385 11.00000 -1.20000 H1B 2 -0.128388 0.741523 -0.370050 11.00000 -1.20000 AFIX 0 C2 1 -0.017445 0.797403 -0.260342 11.00000 0.02346 0.01595 = 0.02811 -0.00352 -0.00636 0.00282 C3 1 -0.009072 0.817322 -0.174791 11.00000 0.01525 0.02115 = 0.02852 0.00535 0.00222 0.00455 C4 1 0.098295 0.834391 -0.122741 11.00000 0.02164 0.01454 = 0.02641 -0.00030 -0.00009 0.00467 AFIX 43 H4 2 0.102647 0.846196 -0.064311 11.00000 -1.20000 AFIX 0 C5 1 0.198809 0.834199 -0.155969 11.00000 0.01954 0.01851 = 0.02472 0.00071 -0.00398 0.00508 C6 1 0.193005 0.819474 -0.241699 11.00000 0.02052 0.02020 = 0.02764 -0.00107 0.00163 0.00597 C7 1 0.084455 0.798626 -0.294310 11.00000 0.02537 0.02251 = 0.02770 0.00094 -0.00121 0.00721 AFIX 43 H7 2 0.080101 0.785422 -0.352608 11.00000 -1.20000 AFIX 0 C8 1 -0.107678 0.840398 -0.059860 11.00000 0.02082 0.04064 = 0.03374 0.00464 0.00594 0.00843 AFIX 137 H8A 2 -0.063416 0.915736 -0.043362 11.00000 -1.50000 H8B 2 -0.069543 0.784871 -0.028677 11.00000 -1.50000 H8C 2 -0.186741 0.835702 -0.047685 11.00000 -1.50000 AFIX 0 C9 1 0.292494 0.795111 -0.354923 11.00000 0.03341 0.10988 = 0.04453 -0.02509 0.01901 0.00725 AFIX 137 H9A 2 0.253592 0.848055 -0.388582 11.00000 -1.50000 H9B 2 0.248890 0.718861 -0.368510 11.00000 -1.50000 H9C 2 0.371544 0.798987 -0.366948 11.00000 -1.50000 AFIX 0 C10 1 0.316004 0.849876 -0.097602 11.00000 0.01792 0.02446 = 0.02716 -0.00032 -0.00424 0.00544 AFIX 23 H10A 2 0.305929 0.813648 -0.044775 11.00000 -1.20000 H10B 2 0.371232 0.813543 -0.123800 11.00000 -1.20000 AFIX 0 C11 1 0.364477 0.973096 -0.079609 11.00000 0.01091 0.02454 = 0.02673 0.00353 -0.00471 0.00458 C12 1 0.358296 1.030661 -0.005096 11.00000 0.01343 0.02305 = 0.02131 0.00255 -0.00220 0.00761 C13 1 0.400375 1.145130 0.009481 11.00000 0.01072 0.02313 = 0.02573 0.00204 -0.00160 0.00488 AFIX 43 H13 2 0.394591 1.181310 0.060727 11.00000 -1.20000 AFIX 0 C14 1 0.450913 1.207151 -0.050413 11.00000 0.00908 0.02431 = 0.02766 -0.00097 -0.00211 0.00518 C15 1 0.457734 1.149956 -0.123940 11.00000 0.01338 0.02254 = 0.02465 0.00293 0.00012 0.00422 C16 1 0.416314 1.034896 -0.138692 11.00000 0.01313 0.02730 = 0.02226 -0.00113 -0.00069 0.00443 AFIX 43 H16 2 0.423670 0.998666 -0.189527 11.00000 -1.20000 AFIX 0 C17 1 0.306045 0.969313 0.059529 11.00000 0.01677 0.02438 = 0.03062 0.00264 0.00323 0.00560 C18 1 0.509377 1.208519 -0.189136 11.00000 0.02451 0.02556 = 0.03374 -0.00202 0.01043 0.00462 C19 1 0.491656 1.333282 -0.035457 11.00000 0.01428 0.02337 = 0.03164 0.00241 -0.00043 -0.00005 AFIX 23 H19A 2 0.518849 1.351611 0.024849 11.00000 -1.20000 H19B 2 0.557699 1.357471 -0.065099 11.00000 -1.20000 AFIX 0 C20 1 0.392899 1.395962 -0.066377 11.00000 0.02097 0.01339 = 0.03048 0.00087 -0.00234 0.00020 C21 1 0.314701 1.416876 -0.014991 11.00000 0.02142 0.01777 = 0.02038 -0.00164 0.00139 0.00046 C22 1 0.219736 1.465343 -0.046230 11.00000 0.02224 0.01590 = 0.02579 -0.00015 -0.00187 0.00008 AFIX 43 H22 2 0.166278 1.477983 -0.010756 11.00000 -1.20000 AFIX 0 C23 1 0.201171 1.495849 -0.128552 11.00000 0.02347 0.01752 = 0.02668 -0.00023 -0.00564 0.00451 C24 1 0.281740 1.477717 -0.179311 11.00000 0.03422 0.02287 = 0.02079 0.00151 0.00055 0.00520 C25 1 0.376719 1.429127 -0.147745 11.00000 0.02592 0.02584 = 0.02695 -0.00032 0.00727 0.00389 AFIX 43 H25 2 0.431623 1.418410 -0.182534 11.00000 -1.20000 AFIX 0 C26 1 0.277578 1.429010 0.124760 11.00000 0.03149 0.03470 = 0.03078 0.00166 0.00547 0.00629 AFIX 137 H26A 2 0.194263 1.398663 0.111109 11.00000 -1.50000 H26B 2 0.289730 1.510940 0.123230 11.00000 -1.50000 H26C 2 0.307960 1.407993 0.180679 11.00000 -1.50000 AFIX 0 C27 1 0.344987 1.504548 -0.311217 11.00000 0.08751 0.12448 = 0.03493 0.02891 0.02864 0.06604 AFIX 137 H27A 2 0.318400 1.530248 -0.366435 11.00000 -1.50000 H27B 2 0.356403 1.426602 -0.316644 11.00000 -1.50000 H27C 2 0.418615 1.551987 -0.286269 11.00000 -1.50000 AFIX 0 C28 1 0.094567 1.546178 -0.163822 11.00000 0.03018 0.01790 = 0.02837 -0.00170 -0.00182 0.00735 AFIX 23 H28A 2 0.059642 1.571658 -0.116962 11.00000 -1.20000 H28B 2 0.119860 1.612817 -0.194674 11.00000 -1.20000 AFIX 0 C29 1 0.002465 1.464892 -0.221639 11.00000 0.02231 0.01863 = 0.02469 0.00160 0.00006 0.00833 C30 1 -0.071807 1.378538 -0.190670 11.00000 0.02451 0.02297 = 0.01900 0.00187 0.00095 0.01016 C31 1 -0.153982 1.300788 -0.242835 11.00000 0.02131 0.02447 = 0.02412 0.00331 0.00361 0.01003 AFIX 43 H31 2 -0.199943 1.241273 -0.219796 11.00000 -1.20000 AFIX 0 C32 1 -0.168745 1.310461 -0.329223 11.00000 0.01708 0.02362 = 0.02381 0.00198 0.00404 0.00801 C33 1 -0.099859 1.400244 -0.360076 11.00000 0.02601 0.02537 = 0.02336 0.00474 0.00304 0.00631 C34 1 -0.014586 1.474733 -0.307286 11.00000 0.02944 0.02469 = 0.02253 0.00295 -0.00190 0.00575 AFIX 43 H34 2 0.032628 1.533219 -0.330400 11.00000 -1.20000 AFIX 0 C35 1 -0.063045 1.365991 -0.102430 11.00000 0.02617 0.02370 = 0.02154 -0.00202 0.00294 0.00631 C36 1 -0.118550 1.417975 -0.448122 11.00000 0.03475 0.02698 = 0.02701 0.00565 -0.00198 -0.00537 C37 1 -0.257588 1.223070 -0.384220 11.00000 0.02514 0.02968 = 0.02117 0.00237 0.00060 0.00576 AFIX 23 H37A 2 -0.336223 1.226776 -0.372082 11.00000 -1.20000 H37B 2 -0.256766 1.239070 -0.443493 11.00000 -1.20000 AFIX 0 C38 1 -0.230973 1.107177 -0.369267 11.00000 0.02237 0.02554 = 0.01437 -0.00065 -0.00475 0.00515 C39 1 -0.295893 1.032781 -0.323427 11.00000 0.01235 0.02969 = 0.02418 -0.00014 0.00086 0.00316 AFIX 43 H39 2 -0.360603 1.053960 -0.303301 11.00000 -1.20000 AFIX 0 C40 1 -0.266947 0.926791 -0.306549 11.00000 0.01975 0.02593 = 0.02199 0.00175 -0.00466 0.00160 C41 1 -0.172380 0.891579 -0.335338 11.00000 0.01903 0.02892 = 0.01891 -0.00023 -0.00484 0.00483 C42 1 -0.108626 0.965780 -0.381087 11.00000 0.01899 0.03019 = 0.02041 -0.00090 -0.00095 0.01045 AFIX 43 H42 2 -0.043505 0.945034 -0.400904 11.00000 -1.20000 AFIX 0 C43 1 -0.137928 1.069883 -0.398590 11.00000 0.01939 0.02932 = 0.01925 -0.00248 -0.00183 0.00468 C44 1 -0.339612 0.853605 -0.260322 11.00000 0.02025 0.03624 = 0.02970 0.00452 -0.00216 0.00420 C45 1 -0.067325 1.142407 -0.447628 11.00000 0.03001 0.03491 = 0.02637 0.00063 0.00571 0.01389 C47 1 -0.396583 0.781726 -0.551540 11.00000 0.23599 0.50225 = 0.10402 -0.09426 -0.04563 0.28591 AFIX 13 H47 2 -0.430063 0.758650 -0.611068 11.00000 -1.20000 AFIX 0 CL3A 3 -0.418311 0.904019 -0.539549 11.00000 0.24878 0.23574 = 0.45480 -0.21534 -0.23721 0.13033 CL3 3 -0.485591 0.674044 -0.485619 11.00000 0.36649 0.79725 = 0.50123 0.43747 0.29937 0.37889 CL5A 3 -0.263440 0.758749 -0.539994 11.00000 0.11700 0.29859 = 0.11474 -0.04349 0.00544 0.03264 CL0A 3 0.165956 1.175161 -0.273138 11.00000 0.10930 0.23800 = 0.06620 0.01404 -0.00065 -0.07400 HKLF 4 REM mo_6CN_0m in P-1 REM R1 = 0.1147 for 5280 Fo > 4sig(Fo) and 0.1953 for all 9894 data REM 564 parameters refined using 0 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 1.301, deepest hole -1.432, 1-sigma level 0.139 Q1 1 -0.6177 0.5069 -0.6262 11.00000 0.05 1.30 Q2 1 -0.4625 0.6927 -0.4649 11.00000 0.05 0.95 Q3 1 -0.3894 0.6774 -0.4800 11.00000 0.05 0.69 Q4 1 0.2399 1.1744 -0.3324 11.00000 0.05 0.66 Q5 1 0.2223 1.1220 -0.3291 11.00000 0.05 0.66 Q6 1 -0.4204 0.5927 -0.4178 11.00000 0.05 0.66 Q7 1 -0.2785 0.9032 -0.6248 11.00000 0.05 0.60 Q8 1 -0.3415 0.9610 -0.6344 11.00000 0.05 0.60 Q9 1 0.1249 1.1014 -0.2056 11.00000 0.05 0.59 Q10 1 0.1179 1.1843 -0.2183 11.00000 0.05 0.55 ; _shelx_res_checksum 80014 _olex2_submission_special_instructions 'No special instructions were received' 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 Cl1 Cl 0.00174(17) 1.10538(15) -0.16134(12) 0.0618(6) Uani 1 1 d . C46 C 0.1395(8) 1.1582(8) -0.1699(6) 0.083(3) Uani 1 1 d . H46A H 0.190540 1.108187 -0.142702 0.100 Uiso 1 1 calc R H46B H 0.161747 1.232146 -0.138966 0.100 Uiso 1 1 calc R O1 O -0.1125(3) 0.8183(3) -0.1472(2) 0.0274(8) Uani 1 1 d . O2 O 0.2975(3) 0.8231(3) -0.2697(2) 0.0305(8) Uani 1 1 d . O3 O 0.3364(3) 1.3849(3) 0.0660(2) 0.0284(8) Uani 1 1 d . O4 O 0.2597(3) 1.5116(3) -0.2591(2) 0.0379(9) Uani 1 1 d . N1 N 0.2652(4) 0.9222(4) 0.1107(3) 0.0359(11) Uani 1 1 d . N2 N 0.5501(4) 1.2518(4) -0.2409(3) 0.0417(12) Uani 1 1 d . N3 N -0.0609(4) 1.3549(4) -0.0324(3) 0.0348(11) Uani 1 1 d . N4 N -0.1371(5) 1.4333(5) -0.5179(3) 0.0522(14) Uani 1 1 d . N5 N -0.4024(4) 0.7984(4) -0.2243(3) 0.0429(12) Uani 1 1 d . N6 N -0.0117(4) 1.1962(4) -0.4883(3) 0.0397(12) Uani 1 1 d . C1 C -0.1340(4) 0.7807(4) -0.3171(3) 0.0255(11) Uani 1 1 d . H1A H -0.192659 0.732921 -0.290385 0.031 Uiso 1 1 calc R H1B H -0.128388 0.741523 -0.370050 0.031 Uiso 1 1 calc R C2 C -0.0174(4) 0.7974(4) -0.2603(3) 0.0238(10) Uani 1 1 d . C3 C -0.0091(4) 0.8173(4) -0.1748(3) 0.0216(10) Uani 1 1 d . C4 C 0.0983(4) 0.8344(4) -0.1227(3) 0.0212(10) Uani 1 1 d . H4 H 0.102647 0.846196 -0.064311 0.025 Uiso 1 1 calc R C5 C 0.1988(4) 0.8342(4) -0.1560(3) 0.0216(10) Uani 1 1 d . C6 C 0.1930(4) 0.8195(4) -0.2417(3) 0.0228(10) Uani 1 1 d . C7 C 0.0845(4) 0.7986(4) -0.2943(3) 0.0255(11) Uani 1 1 d . H7 H 0.080101 0.785422 -0.352608 0.031 Uiso 1 1 calc R C8 C -0.1077(4) 0.8404(5) -0.0599(3) 0.0312(12) Uani 1 1 d . H8A H -0.063416 0.915736 -0.043362 0.047 Uiso 1 1 calc GR H8B H -0.069543 0.784871 -0.028677 0.047 Uiso 1 1 calc GR H8C H -0.186741 0.835702 -0.047685 0.047 Uiso 1 1 calc GR C9 C 0.2925(6) 0.7951(7) -0.3549(4) 0.062(2) Uani 1 1 d . H9A H 0.253592 0.848055 -0.388582 0.094 Uiso 1 1 calc GR H9B H 0.248890 0.718861 -0.368510 0.094 Uiso 1 1 calc GR H9C H 0.371544 0.798987 -0.366948 0.094 Uiso 1 1 calc GR C10 C 0.3160(4) 0.8499(4) -0.0976(3) 0.0239(10) Uani 1 1 d . H10A H 0.305929 0.813648 -0.044775 0.029 Uiso 1 1 calc R H10B H 0.371232 0.813543 -0.123800 0.029 Uiso 1 1 calc R C11 C 0.3645(4) 0.9731(4) -0.0796(3) 0.0214(10) Uani 1 1 d . C12 C 0.3583(4) 1.0307(4) -0.0051(3) 0.0193(10) Uani 1 1 d . C13 C 0.4004(3) 1.1451(4) 0.0095(3) 0.0201(10) Uani 1 1 d . H13 H 0.394591 1.181310 0.060727 0.024 Uiso 1 1 calc R C14 C 0.4509(3) 1.2072(4) -0.0504(3) 0.0207(10) Uani 1 1 d . C15 C 0.4577(4) 1.1500(4) -0.1239(3) 0.0204(10) Uani 1 1 d . C16 C 0.4163(4) 1.0349(4) -0.1387(3) 0.0212(10) Uani 1 1 d . H16 H 0.423670 0.998666 -0.189527 0.025 Uiso 1 1 calc R C17 C 0.3060(4) 0.9693(4) 0.0595(3) 0.0237(10) Uani 1 1 d . C18 C 0.5094(4) 1.2085(4) -0.1891(3) 0.0274(11) Uani 1 1 d . C19 C 0.4917(4) 1.3333(4) -0.0355(3) 0.0239(10) Uani 1 1 d . H19A H 0.518849 1.351611 0.024849 0.029 Uiso 1 1 calc R H19B H 0.557699 1.357471 -0.065099 0.029 Uiso 1 1 calc R C20 C 0.3929(4) 1.3960(4) -0.0664(3) 0.0227(10) Uani 1 1 d . C21 C 0.3147(4) 1.4169(4) -0.0150(3) 0.0205(10) Uani 1 1 d . C22 C 0.2197(4) 1.4653(4) -0.0462(3) 0.0224(10) Uani 1 1 d . H22 H 0.166278 1.477983 -0.010756 0.027 Uiso 1 1 calc R C23 C 0.2012(4) 1.4958(4) -0.1286(3) 0.0236(10) Uani 1 1 d . C24 C 0.2817(4) 1.4777(4) -0.1793(3) 0.0264(11) Uani 1 1 d . C25 C 0.3767(4) 1.4291(4) -0.1477(3) 0.0260(11) Uani 1 1 d . H25 H 0.431623 1.418410 -0.182534 0.031 Uiso 1 1 calc R C26 C 0.2776(5) 1.4290(5) 0.1248(3) 0.0322(12) Uani 1 1 d . H26A H 0.194263 1.398663 0.111109 0.048 Uiso 1 1 calc GR H26B H 0.289730 1.510940 0.123230 0.048 Uiso 1 1 calc GR H26C H 0.307960 1.407993 0.180679 0.048 Uiso 1 1 calc GR C27 C 0.3450(7) 1.5045(8) -0.3112(4) 0.074(3) Uani 1 1 d . H27A H 0.318400 1.530248 -0.366435 0.111 Uiso 1 1 calc GR H27B H 0.356403 1.426602 -0.316644 0.111 Uiso 1 1 calc GR H27C H 0.418615 1.551987 -0.286269 0.111 Uiso 1 1 calc GR C28 C 0.0946(4) 1.5462(4) -0.1638(3) 0.0259(11) Uani 1 1 d . H28A H 0.059642 1.571658 -0.116962 0.031 Uiso 1 1 calc R H28B H 0.119860 1.612817 -0.194674 0.031 Uiso 1 1 calc R C29 C 0.0025(4) 1.4649(4) -0.2216(3) 0.0217(10) Uani 1 1 d . C30 C -0.0718(4) 1.3785(4) -0.1907(3) 0.0217(10) Uani 1 1 d . C31 C -0.1540(4) 1.3008(4) -0.2428(3) 0.0226(10) Uani 1 1 d . H31 H -0.199943 1.241273 -0.219796 0.027 Uiso 1 1 calc R C32 C -0.1687(4) 1.3105(4) -0.3292(3) 0.0209(10) Uani 1 1 d . C33 C -0.0999(4) 1.4002(4) -0.3601(3) 0.0248(10) Uani 1 1 d . C34 C -0.0146(4) 1.4747(4) -0.3073(3) 0.0261(11) Uani 1 1 d . H34 H 0.032628 1.533219 -0.330400 0.031 Uiso 1 1 calc R C35 C -0.0630(4) 1.3660(4) -0.1024(3) 0.0237(10) Uani 1 1 d . C36 C -0.1185(5) 1.4180(4) -0.4481(3) 0.0316(12) Uani 1 1 d . C37 C -0.2576(4) 1.2231(4) -0.3842(3) 0.0256(11) Uani 1 1 d . H37A H -0.336223 1.226776 -0.372082 0.031 Uiso 1 1 calc R H37B H -0.256766 1.239070 -0.443493 0.031 Uiso 1 1 calc R C38 C -0.2310(4) 1.1072(4) -0.3693(3) 0.0215(10) Uani 1 1 d . C39 C -0.2959(4) 1.0328(4) -0.3234(3) 0.0224(10) Uani 1 1 d . H39 H -0.360603 1.053960 -0.303301 0.027 Uiso 1 1 calc R C40 C -0.2669(4) 0.9268(4) -0.3065(3) 0.0237(10) Uani 1 1 d . C41 C -0.1724(4) 0.8916(4) -0.3353(3) 0.0231(10) Uani 1 1 d . C42 C -0.1086(4) 0.9658(4) -0.3811(3) 0.0230(10) Uani 1 1 d . H42 H -0.043505 0.945034 -0.400904 0.028 Uiso 1 1 calc R C43 C -0.1379(4) 1.0699(4) -0.3986(3) 0.0232(10) Uani 1 1 d . C44 C -0.3396(4) 0.8536(4) -0.2603(3) 0.0295(11) Uani 1 1 d . C45 C -0.0673(4) 1.1424(5) -0.4476(3) 0.0294(11) Uani 1 1 d . C47 C -0.3966(19) 0.782(3) -0.5515(10) 0.265(16) Uani 1 1 d . H47 H -0.430063 0.758650 -0.611068 0.318 Uiso 1 1 calc R Cl3A Cl -0.4183(6) 0.9040(6) -0.5395(6) 0.340(6) Uani 1 1 d . Cl3 Cl -0.4856(10) 0.6740(14) -0.4856(8) 0.490(13) Uani 1 1 d . Cl5A Cl -0.2634(4) 0.7587(5) -0.5400(3) 0.180(2) Uani 1 1 d . Cl0A Cl 0.1660(3) 1.1752(4) -0.27314(18) 0.1518(17) Uani 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0669(11) 0.0533(11) 0.0649(12) 0.0042(9) 0.0033(9) 0.0164(9) C46 0.086(6) 0.088(6) 0.073(6) 0.003(5) -0.006(5) 0.027(5) O1 0.0174(15) 0.036(2) 0.0267(19) 0.0012(15) -0.0014(14) 0.0041(14) O2 0.0189(16) 0.040(2) 0.031(2) -0.0031(16) 0.0039(14) 0.0025(15) O3 0.0294(18) 0.034(2) 0.0228(18) 0.0047(15) 0.0016(14) 0.0102(15) O4 0.046(2) 0.048(2) 0.025(2) 0.0113(17) 0.0063(17) 0.0208(19) N1 0.031(2) 0.040(3) 0.037(3) 0.007(2) 0.008(2) 0.004(2) N2 0.045(3) 0.041(3) 0.045(3) 0.003(2) 0.022(2) 0.010(2) N3 0.043(3) 0.032(3) 0.031(3) 0.001(2) 0.004(2) 0.012(2) N4 0.064(4) 0.054(3) 0.027(3) 0.008(2) -0.004(2) -0.012(3) N5 0.031(2) 0.049(3) 0.047(3) 0.013(2) 0.005(2) 0.002(2) N6 0.044(3) 0.043(3) 0.037(3) 0.009(2) 0.016(2) 0.013(2) C1 0.022(2) 0.021(2) 0.031(3) -0.001(2) -0.002(2) 0.0064(19) C2 0.023(2) 0.016(2) 0.028(3) -0.0035(19) -0.006(2) 0.0028(18) C3 0.015(2) 0.021(2) 0.029(3) 0.0054(19) 0.0022(19) 0.0045(17) C4 0.022(2) 0.015(2) 0.026(3) -0.0003(18) -0.0001(19) 0.0047(17) C5 0.020(2) 0.019(2) 0.025(3) 0.0007(19) -0.0040(19) 0.0051(18) C6 0.021(2) 0.020(2) 0.028(3) -0.0011(19) 0.0016(19) 0.0060(18) C7 0.025(2) 0.023(2) 0.028(3) 0.001(2) -0.001(2) 0.0072(19) C8 0.021(2) 0.041(3) 0.034(3) 0.005(2) 0.006(2) 0.008(2) C9 0.033(3) 0.110(6) 0.045(4) -0.025(4) 0.019(3) 0.007(4) C10 0.018(2) 0.024(2) 0.027(3) 0.000(2) -0.0042(19) 0.0054(18) C11 0.0109(19) 0.025(2) 0.027(3) 0.004(2) -0.0047(18) 0.0046(17) C12 0.0134(19) 0.023(2) 0.021(2) 0.0026(19) -0.0022(17) 0.0076(17) C13 0.0107(19) 0.023(2) 0.026(2) 0.0020(19) -0.0016(18) 0.0049(17) C14 0.0091(19) 0.024(2) 0.028(3) -0.001(2) -0.0021(18) 0.0052(17) C15 0.013(2) 0.023(2) 0.025(2) 0.0029(19) 0.0001(18) 0.0042(17) C16 0.013(2) 0.027(3) 0.022(2) -0.0011(19) -0.0007(18) 0.0044(18) C17 0.017(2) 0.024(2) 0.031(3) 0.003(2) 0.003(2) 0.0056(19) C18 0.025(2) 0.026(3) 0.034(3) -0.002(2) 0.010(2) 0.005(2) C19 0.014(2) 0.023(2) 0.032(3) 0.002(2) -0.0004(19) 0.0000(18) C20 0.021(2) 0.013(2) 0.030(3) 0.0009(19) -0.0023(19) 0.0002(17) C21 0.021(2) 0.018(2) 0.020(2) -0.0016(18) 0.0014(18) 0.0005(18) C22 0.022(2) 0.016(2) 0.026(3) -0.0001(19) -0.0019(19) 0.0001(18) C23 0.023(2) 0.018(2) 0.027(3) -0.0002(19) -0.006(2) 0.0045(18) C24 0.034(3) 0.023(2) 0.021(3) 0.002(2) 0.001(2) 0.005(2) C25 0.026(2) 0.026(3) 0.027(3) 0.000(2) 0.007(2) 0.004(2) C26 0.031(3) 0.035(3) 0.031(3) 0.002(2) 0.005(2) 0.006(2) C27 0.088(6) 0.124(7) 0.035(4) 0.029(4) 0.029(4) 0.066(5) C28 0.030(2) 0.018(2) 0.028(3) -0.002(2) -0.002(2) 0.0073(19) C29 0.022(2) 0.019(2) 0.025(3) 0.0016(19) 0.0001(19) 0.0083(18) C30 0.025(2) 0.023(2) 0.019(2) 0.0019(19) 0.0009(19) 0.0102(19) C31 0.021(2) 0.024(2) 0.024(3) 0.003(2) 0.0036(19) 0.0100(19) C32 0.017(2) 0.024(2) 0.024(3) 0.0020(19) 0.0040(18) 0.0080(18) C33 0.026(2) 0.025(3) 0.023(3) 0.005(2) 0.003(2) 0.006(2) C34 0.029(2) 0.025(3) 0.023(3) 0.003(2) -0.002(2) 0.006(2) C35 0.026(2) 0.024(2) 0.022(3) -0.002(2) 0.003(2) 0.0063(19) C36 0.035(3) 0.027(3) 0.027(3) 0.006(2) -0.002(2) -0.005(2) C37 0.025(2) 0.030(3) 0.021(3) 0.002(2) 0.001(2) 0.006(2) C38 0.022(2) 0.026(2) 0.014(2) -0.0007(18) -0.0048(18) 0.0052(19) C39 0.012(2) 0.030(3) 0.024(3) 0.000(2) 0.0009(18) 0.0032(18) C40 0.020(2) 0.026(3) 0.022(2) 0.002(2) -0.0047(19) 0.0016(19) C41 0.019(2) 0.029(3) 0.019(2) 0.000(2) -0.0048(18) 0.0048(19) C42 0.019(2) 0.030(3) 0.020(2) -0.001(2) -0.0010(18) 0.0104(19) C43 0.019(2) 0.029(3) 0.019(2) -0.0025(19) -0.0018(18) 0.0047(19) C44 0.020(2) 0.036(3) 0.030(3) 0.005(2) -0.002(2) 0.004(2) C45 0.030(3) 0.035(3) 0.026(3) 0.001(2) 0.006(2) 0.014(2) C47 0.24(2) 0.50(4) 0.104(11) -0.094(17) -0.046(12) 0.29(3) Cl3A 0.249(6) 0.236(6) 0.455(11) -0.215(7) -0.237(7) 0.130(5) Cl3 0.366(13) 0.80(3) 0.501(18) 0.44(2) 0.299(14) 0.379(17) Cl5A 0.117(3) 0.299(6) 0.115(3) -0.043(3) 0.005(2) 0.033(3) Cl0A 0.109(2) 0.238(4) 0.0662(17) 0.014(2) -0.0006(15) -0.074(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Cl Cl 0.1484 0.1585 '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 Cl1 C46 Cl0A 115.1(5) C3 O1 C8 117.2(3) C6 O2 C9 117.0(4) C21 O3 C26 117.7(4) C24 O4 C27 117.6(4) C2 C1 C41 111.2(4) C3 C2 C1 120.8(4) C3 C2 C7 119.2(4) C7 C2 C1 119.9(4) O1 C3 C2 115.4(4) O1 C3 C4 123.8(4) C4 C3 C2 120.8(4) C5 C4 C3 120.1(5) C4 C5 C6 120.1(4) C4 C5 C10 119.4(4) C6 C5 C10 120.5(4) O2 C6 C5 116.3(4) O2 C6 C7 123.7(4) C5 C6 C7 120.0(4) C2 C7 C6 119.7(5) C11 C10 C5 110.3(4) C12 C11 C10 122.8(4) C16 C11 C10 120.1(4) C16 C11 C12 117.1(4) C11 C12 C17 119.3(4) C13 C12 C11 122.1(4) C13 C12 C17 118.6(4) C14 C13 C12 120.6(4) C13 C14 C19 120.2(4) C15 C14 C13 117.3(4) C15 C14 C19 122.5(4) C14 C15 C16 122.3(4) C14 C15 C18 120.6(4) C16 C15 C18 117.1(4) C11 C16 C15 120.5(4) N1 C17 C12 179.3(5) N2 C18 C15 178.3(5) C20 C19 C14 110.5(4) C21 C20 C19 120.9(4) C25 C20 C19 120.3(4) C25 C20 C21 118.7(4) O3 C21 C20 116.4(4) O3 C21 C22 123.3(4) C22 C21 C20 120.2(4) C21 C22 C23 121.3(4) C22 C23 C24 118.3(4) C22 C23 C28 121.4(4) C24 C23 C28 120.3(4) O4 C24 C23 115.4(4) O4 C24 C25 124.4(4) C25 C24 C23 120.1(4) C24 C25 C20 121.2(4) C29 C28 C23 113.6(4) C30 C29 C28 121.6(4) C34 C29 C28 121.4(4) C34 C29 C30 117.0(4) C29 C30 C35 120.3(4) C31 C30 C29 122.4(4) C31 C30 C35 117.3(4) C30 C31 C32 119.9(4) C31 C32 C33 117.9(4) C31 C32 C37 118.5(4) C33 C32 C37 123.6(4) C32 C33 C36 119.5(4) C34 C33 C32 121.5(4) C34 C33 C36 119.0(4) C29 C34 C33 121.2(5) N3 C35 C30 177.2(5) N4 C36 C33 177.6(6) C38 C37 C32 110.6(4) C39 C38 C37 121.4(4) C39 C38 C43 116.7(4) C43 C38 C37 121.9(4) C38 C39 C40 120.9(4) C39 C40 C44 117.7(4) C41 C40 C39 121.6(4) C41 C40 C44 120.7(4) C40 C41 C1 124.4(4) C42 C41 C1 118.4(4) C42 C41 C40 117.1(4) C43 C42 C41 121.3(4) C38 C43 C45 119.7(4) C42 C43 C38 122.3(4) C42 C43 C45 117.9(4) N5 C44 C40 176.4(5) N6 C45 C43 177.4(6) Cl3A C47 Cl3 112.9(11) Cl3A C47 Cl5A 119(2) Cl5A C47 Cl3 108.5(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C46 1.677(10) C46 Cl0A 1.769(10) O1 C3 1.372(5) O1 C8 1.430(6) O2 C6 1.379(6) O2 C9 1.410(7) O3 C21 1.380(6) O3 C26 1.414(6) O4 C24 1.370(6) O4 C27 1.431(8) N1 C17 1.145(6) N2 C18 1.132(7) N3 C35 1.148(6) N4 C36 1.148(7) N5 C44 1.155(7) N6 C45 1.146(7) C1 C2 1.512(6) C1 C41 1.511(6) C2 C3 1.392(7) C2 C7 1.403(7) C3 C4 1.391(6) C4 C5 1.384(7) C5 C6 1.391(7) C5 C10 1.531(6) C6 C7 1.406(7) C10 C11 1.509(7) C11 C12 1.402(7) C11 C16 1.390(7) C12 C13 1.393(6) C12 C17 1.460(7) C13 C14 1.394(7) C14 C15 1.388(7) C14 C19 1.523(7) C15 C16 1.398(6) C15 C18 1.450(7) C19 C20 1.526(6) C20 C21 1.392(7) C20 C25 1.387(7) C21 C22 1.387(6) C22 C23 1.392(7) C23 C24 1.398(7) C23 C28 1.530(6) C24 C25 1.389(7) C28 C29 1.519(7) C29 C30 1.407(7) C29 C34 1.387(7) C30 C31 1.393(7) C30 C35 1.437(7) C31 C32 1.399(7) C32 C33 1.399(7) C32 C37 1.517(7) C33 C34 1.395(7) C33 C36 1.442(7) C37 C38 1.507(6) C38 C39 1.394(6) C38 C43 1.404(6) C39 C40 1.406(7) C40 C41 1.405(7) C40 C44 1.440(7) C41 C42 1.384(7) C42 C43 1.388(7) C43 C45 1.452(7) C47 Cl3A 1.56(2) C47 Cl3 1.98(3) C47 Cl5A 1.629(16)