#------------------------------------------------------------------------------ #$Date: 2019-10-11 06:17:53 +0300 (Fri, 11 Oct 2019) $ #$Revision: 219268 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/45/7234536.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_7234536 loop_ _publ_author_name 'Bauer, David' 'Blumberg, Markus' 'K\"ockerling, Martin' 'Mamat, Constantin' _publ_section_title ; A comparative evaluation of calix[4]arene-1,3-crown-6 as a ligand for selected divalent cations of radiopharmaceutical interest ; _journal_issue 55 _journal_name_full 'RSC Advances' _journal_page_first 32357 _journal_paper_doi 10.1039/C9RA07293D _journal_volume 9 _journal_year 2019 _chemical_formula_moiety 'C78 H86 Cl4 O16' _chemical_formula_sum 'C78 H86 Cl4 O16' _chemical_formula_weight 1421.26 _space_group_crystal_system monoclinic _space_group_IT_number 13 _space_group_name_Hall '-P 2yac' _space_group_name_H-M_alt 'P 1 2/n 1' _symmetry_space_group_name_Hall '-P 2yac' _symmetry_space_group_name_H-M 'P 1 2/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date july-6-2019 _audit_creation_method 'ciftab-2016 (M. K\"ockerling, 2016)' _audit_update_record ; 2019-08-31 deposited with the CCDC. 2019-10-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.105(1) _cell_angle_gamma 90 _cell_formula_units_Z 1 _cell_length_a 10.0307(3) _cell_length_b 14.0336(5) _cell_length_c 12.5626(4) _cell_measurement_reflns_used 9959 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 33.146 _cell_measurement_theta_min 3.2035 _cell_volume 1740.97(10) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 123(2) _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_source 'microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_unetI/netI 0.0384 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 22332 _diffrn_reflns_point_group_measured_fraction_full 0.979 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 33.175 _diffrn_reflns_theta_min 3.204 _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker-Nonius SADABS' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method none _exptl_crystal_description irregular _exptl_crystal_F_000 750 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.130 _exptl_transmission_factor_max 0.74650 _exptl_transmission_factor_min 0.67020 _refine_diff_density_max 0.448 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.058 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 6567 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0459 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.8805P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1102 _refine_ls_wR_factor_ref 0.1250 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5055 _reflns_number_total 6567 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ra07293d2.cif _cod_data_source_block DBII005 _cod_original_cell_volume 1741.0(1) _cod_database_code 7234536 _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_min 0.965 _shelx_estimated_absorpt_t_max 0.970 _shelxl_version_number 2014-1 _shelx_res_file ; TITL DBII005 in P2/n CELL 0.71073 10.0307 14.0336 12.5626 90.000 100.105 90.000 ZERR 1.000 0.0003 0.0005 0.0004 0.000 0.001 0.000 LATT 1 SYMM 1/2-X, Y, 1/2-Z SFAC C H O Cl DISP $C 0.00341 0.00169 11.32113!source kissel DISP $H -0.00002 0.00000 0.66638!source kissel DISP $O 0.01140 0.00623 32.03669!source kissel DISP $Cl 0.15068 0.16112 668.70837!source kissel UNIT 78 86 16 4 TEMP -150.140 SIZE 0.13 0.13 0.15 L.S. 30 BOND $H HTAB O1 O2 HTAB C16 O4A HTAB C16 O4B EQIV $1 -x+1, -y, -z+1 HTAB C19A Cl1A_$1 HTAB C19A Cl1B_$1 CONF LIST 4 ACTA 50 FMAP 2 PLAN 10 WGHT 0.052500 0.880500 FVAR 1.42998 0.49693 0.42810 O1 3 0.703277 0.663542 0.367905 11.00000 0.01462 0.02398 = 0.01689 -0.00804 -0.00144 0.00228 AFIX 3 H1A 2 0.638968 0.661532 0.313985 11.00000 -1.50000 AFIX 0 C1 1 0.675532 0.731143 0.438869 11.00000 0.01621 0.01601 = 0.01220 -0.00079 0.00396 -0.00224 O2 3 0.516028 0.635958 0.180777 11.00000 0.01208 0.01267 = 0.01781 0.00041 -0.00105 -0.00085 C2 1 0.547158 0.772169 0.434743 11.00000 0.01618 0.01686 = 0.01445 -0.00029 0.00503 -0.00137 O3 3 0.433155 0.493568 0.316314 11.00000 0.03129 0.01687 = 0.02194 0.00116 0.00922 0.00099 C3 1 0.529508 0.838662 0.513765 11.00000 0.02501 0.02121 = 0.01953 -0.00262 0.01003 0.00056 AFIX 3 H3A 2 0.442498 0.867952 0.511124 11.00000 -1.20000 AFIX 0 C4 1 0.635380 0.863173 0.596178 11.00000 0.03310 0.02368 = 0.01802 -0.00690 0.00961 -0.00325 AFIX 3 H4A 2 0.621400 0.908303 0.650588 11.00000 -1.20000 AFIX 0 C5 1 0.761852 0.821893 0.598802 11.00000 0.02666 0.02502 = 0.01350 -0.00439 0.00398 -0.00653 AFIX 3 H5A 2 0.834922 0.838534 0.655892 11.00000 -1.20000 AFIX 0 C6 1 0.784697 0.756589 0.520252 11.00000 0.01853 0.01923 = 0.01063 -0.00008 0.00215 -0.00437 C7 1 0.428699 0.744510 0.347656 11.00000 0.01227 0.01922 = 0.01782 0.00030 0.00478 -0.00088 AFIX 3 H7A 2 0.346150 0.765920 0.368616 11.00000 -1.20000 H7B 2 0.424792 0.676300 0.342166 11.00000 -1.20000 AFIX 0 C8 1 0.438320 0.785870 0.237443 11.00000 0.00916 0.01664 = 0.01671 -0.00068 0.00182 -0.00092 C9 1 0.484857 0.731253 0.157879 11.00000 0.00996 0.01333 = 0.01590 0.00049 -0.00082 -0.00001 C11 1 0.462985 0.864218 0.036866 11.00000 0.01571 0.01929 = 0.01903 0.00423 0.00143 0.00200 AFIX 3 H11A 2 0.470555 0.891549 -0.031874 11.00000 -1.20000 AFIX 0 C10 1 0.504511 0.770094 0.059105 11.00000 0.01202 0.01820 = 0.01323 -0.00011 -0.00067 0.00029 C12 1 0.410919 0.918940 0.112417 11.00000 0.01495 0.01536 = 0.02667 0.00323 0.00295 0.00240 AFIX 3 H12A 2 0.380262 0.982760 0.094877 11.00000 -1.20000 AFIX 0 C13 1 0.403333 0.880841 0.213352 11.00000 0.01180 0.01626 = 0.02396 -0.00107 0.00475 0.00035 AFIX 3 H13A 2 0.373923 0.920211 0.267292 11.00000 -1.20000 AFIX 0 C15 1 0.401868 0.573438 0.148007 11.00000 0.01435 0.01610 = 0.02103 -0.00153 -0.00139 -0.00293 AFIX 3 H15A 2 0.386878 0.564687 0.071037 11.00000 -1.20000 H15B 2 0.321648 0.600728 0.167327 11.00000 -1.20000 AFIX 0 C14 1 0.575794 0.715414 -0.019082 11.00000 0.01703 0.02133 = 0.01224 -0.00141 -0.00147 0.00264 AFIX 3 H14A 2 0.522863 0.718644 -0.090492 11.00000 -1.20000 H14B 2 0.584013 0.649634 0.002058 11.00000 -1.20000 AFIX 0 C16 1 0.432161 0.479365 0.203849 11.00000 0.02147 0.01479 = 0.02147 -0.00192 0.00287 -0.00218 AFIX 3 H16A 2 0.364401 0.433325 0.175429 11.00000 -1.20000 H16B 2 0.518670 0.456166 0.192669 11.00000 -1.20000 AFIX 0 PART 1 O4A 3 0.608794 0.310828 0.293503 21.00000 0.01360 0.05376 = 0.02788 0.00786 0.00223 0.01479 C17A 1 0.456788 0.409556 0.375727 21.00000 0.02197 0.02025 = 0.02623 0.01020 0.00911 0.00250 AFIX 3 H17A 2 0.412073 0.360358 0.354585 21.00000 -1.20000 H17B 2 0.467493 0.423318 0.453125 21.00000 -1.20000 AFIX 0 C18A 1 0.600356 0.370277 0.382935 21.00000 0.03219 0.03042 = 0.02408 0.00940 -0.00584 -0.01220 AFIX 23 H18A 2 0.664990 0.423796 0.384591 21.00000 -1.20000 H18B 2 0.625518 0.333489 0.450726 21.00000 -1.20000 AFIX 0 C19A 1 0.724359 0.264344 0.299300 21.00000 0.02980 0.05566 = 0.05854 0.02843 -0.00790 -0.01056 AFIX 23 H19A 2 0.711015 0.197597 0.320680 21.00000 -1.20000 H19B 2 0.792533 0.293573 0.356520 21.00000 -1.20000 AFIX 0 PART 2 O4B 3 0.696520 0.383269 0.321063 -21.00000 0.02310 0.02620 = 0.04329 0.01481 0.01258 0.00577 C17B 1 0.484078 0.410574 0.383402 -21.00000 0.02179 AFIX 3 H17C 2 0.430325 0.355232 0.338936 -21.00000 -1.20000 H17D 2 0.425795 0.413202 0.443996 -21.00000 -1.20000 AFIX 0 C18B 1 0.632928 0.406517 0.409627 -21.00000 0.02129 0.02814 = 0.03136 0.00261 0.00062 0.00215 AFIX 23 H18C 2 0.667109 0.469177 0.438681 -21.00000 -1.20000 H18D 2 0.659285 0.358616 0.467336 -21.00000 -1.20000 AFIX 0 C19B 1 0.719178 0.287121 0.303522 -21.00000 0.08301 0.01824 = 0.02741 -0.00048 0.00785 -0.00993 AFIX 23 H19C 2 0.633503 0.250554 0.293992 -21.00000 -1.20000 H19D 2 0.783624 0.259536 0.364457 -21.00000 -1.20000 AFIX 0 PART 0 CL1A 4 0.296820 0.008717 0.641833 31.00000 0.03120 0.02993 = 0.02314 -0.00564 0.00683 -0.00747 CL1B 4 0.302137 -0.008327 0.653241 -31.00000 0.05657 0.05268 = 0.04050 -0.02481 0.02666 -0.01909 C20 1 0.250000 0.070156 0.750000 10.50000 0.01758 0.02552 = 0.02289 0.00000 0.00293 0.00000 AFIX 3 H20B 2 0.324180 0.110446 0.780750 10.50000 -1.20000 AFIX 0 HKLF 4 REM DBII005 in P2/n REM R1 = 0.0459 for 5055 Fo > 4sig(Fo) and 0.0679 for all 6567 data REM 264 parameters refined using 0 restraints END WGHT 0.0523 0.8820 REM Highest difference peak 0.448, deepest hole -0.364, 1-sigma level 0.058 Q1 1 0.7362 0.7439 0.4739 11.00000 0.05 0.45 Q2 1 0.4968 0.7510 0.1090 11.00000 0.05 0.43 Q3 1 0.4720 0.7628 0.2069 11.00000 0.05 0.40 Q4 1 0.4320 0.7674 0.2925 11.00000 0.05 0.38 Q5 1 0.7726 0.7889 0.5597 11.00000 0.05 0.37 Q6 1 0.5386 0.7902 0.4820 11.00000 0.05 0.36 Q7 1 0.4424 0.8886 0.0778 11.00000 0.05 0.35 Q8 1 0.3237 0.0877 0.7959 11.00000 0.05 0.34 Q9 1 0.5864 0.8465 0.5514 11.00000 0.05 0.33 Q10 1 0.4014 0.8932 0.1581 11.00000 0.05 0.32 ; _shelx_res_checksum 62732 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, 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 O1 O 0.70328(8) 0.66354(6) 0.36790(6) 0.0190(2) Uani 1 1 d . . . . . H1A H 0.6390 0.6615 0.3140 0.029 Uiso 1 1 d R U . . . C1 C 0.6755(1) 0.73114(7) 0.43887(8) 0.0146(2) Uani 1 1 d . . . . . O2 O 0.51603(7) 0.63596(5) 0.18078(6) 0.0146(1) Uani 1 1 d . . . . . C2 C 0.5472(1) 0.77217(7) 0.43474(8) 0.0155(2) Uani 1 1 d . . . . . O3 O 0.4331(1) 0.49357(6) 0.31631(7) 0.0228(2) Uani 1 1 d . . . . . C3 C 0.5295(1) 0.83866(8) 0.51376(9) 0.0212(2) Uani 1 1 d . . . . . H3A H 0.4425 0.8680 0.5111 0.025 Uiso 1 1 d R U . . . C4 C 0.6354(1) 0.86317(9) 0.59618(9) 0.0243(2) Uani 1 1 d . . . . . H4A H 0.6214 0.9083 0.6506 0.029 Uiso 1 1 d R U . . . C5 C 0.7618(1) 0.82189(8) 0.59880(9) 0.0217(2) Uani 1 1 d . . . . . H5A H 0.8349 0.8385 0.6559 0.026 Uiso 1 1 d R U . . . C6 C 0.7847(1) 0.75659(8) 0.52025(8) 0.0162(2) Uani 1 1 d . . . . . C7 C 0.4287(1) 0.74451(8) 0.34766(8) 0.0162(2) Uani 1 1 d . . . . . H7A H 0.3462 0.7659 0.3686 0.019 Uiso 1 1 d R U . . . H7B H 0.4248 0.6763 0.3422 0.019 Uiso 1 1 d R U . . . C8 C 0.4383(1) 0.78587(7) 0.23744(8) 0.0142(2) Uani 1 1 d . . . . . C9 C 0.4849(1) 0.73125(7) 0.15788(8) 0.0134(2) Uani 1 1 d . . . . . C11 C 0.4630(1) 0.86422(8) 0.03687(9) 0.0182(2) Uani 1 1 d . . . . . H11A H 0.4706 0.8915 -0.0319 0.022 Uiso 1 1 d R U . . . C10 C 0.5045(1) 0.77009(7) 0.05910(8) 0.0148(2) Uani 1 1 d . . . . . C12 C 0.4109(1) 0.91894(8) 0.1124(1) 0.0191(2) Uani 1 1 d . . . . . H12A H 0.3803 0.9828 0.0949 0.023 Uiso 1 1 d R U . . . C13 C 0.4033(1) 0.88084(7) 0.21335(9) 0.0171(2) Uani 1 1 d . . . . . H13A H 0.3739 0.9202 0.2673 0.021 Uiso 1 1 d R U . . . C15 C 0.4019(1) 0.57344(7) 0.14801(9) 0.0177(2) Uani 1 1 d . . . . . H15A H 0.3869 0.5647 0.0710 0.021 Uiso 1 1 d R U . . . H15B H 0.3216 0.6007 0.1673 0.021 Uiso 1 1 d R U . . . C14 C 0.5758(1) 0.71541(8) -0.01908(8) 0.0173(2) Uani 1 1 d . . . . . H14A H 0.5229 0.7186 -0.0905 0.021 Uiso 1 1 d R U . . . H14B H 0.5840 0.6496 0.0021 0.021 Uiso 1 1 d R U . . . C16 C 0.4322(1) 0.47936(8) 0.20385(9) 0.0193(2) Uani 1 1 d . . . . . H16A H 0.3644 0.4333 0.1754 0.023 Uiso 1 1 d R U . . . H16B H 0.5187 0.4562 0.1927 0.023 Uiso 1 1 d R U . . . O4A_a O 0.6088(2) 0.3108(2) 0.2935(2) 0.0319(6) Uani 0.497(3) 1 d . . P A 1 C17A_a C 0.4568(6) 0.4096(4) 0.3757(4) 0.0222(8) Uani 0.497(3) 1 d . . P A 1 H17A_a H 0.4121 0.3604 0.3546 0.027 Uiso 0.497(3) 1 d R U P A 1 H17B_a H 0.4675 0.4233 0.4531 0.027 Uiso 0.497(3) 1 d R U P A 1 C18A_a C 0.6004(3) 0.3703(3) 0.3829(3) 0.0302(6) Uani 0.497(3) 1 d . . P A 1 H18A_a H 0.6650 0.4238 0.3846 0.036 Uiso 0.497(3) 1 calc R U P A 1 H18B_a H 0.6255 0.3335 0.4507 0.036 Uiso 0.497(3) 1 calc R U P A 1 C19A_a C 0.7244(7) 0.2643(6) 0.2993(7) 0.050(2) Uani 0.497(3) 1 d . . P A 1 H19A_a H 0.7110 0.1976 0.3207 0.060 Uiso 0.497(3) 1 calc R U P A 1 H19B_a H 0.7925 0.2936 0.3565 0.060 Uiso 0.497(3) 1 calc R U P A 1 O4B_b O 0.6965(2) 0.3833(1) 0.3211(2) 0.0301(5) Uani 0.503(3) 1 d . . P A 2 C17B_b C 0.4841(5) 0.4106(5) 0.3834(5) 0.022(1) Uiso 0.503(3) 1 d . . P A 2 H17C_b H 0.4303 0.3552 0.3389 0.026 Uiso 0.503(3) 1 d R U P A 2 H17D_b H 0.4258 0.4132 0.4440 0.026 Uiso 0.503(3) 1 d R U P A 2 C18B_b C 0.6329(3) 0.4065(2) 0.4096(3) 0.0274(6) Uani 0.503(3) 1 d . . P A 2 H18C_b H 0.6671 0.4692 0.4387 0.033 Uiso 0.503(3) 1 calc R U P A 2 H18D_b H 0.6593 0.3586 0.4673 0.033 Uiso 0.503(3) 1 calc R U P A 2 C19B_b C 0.719(1) 0.2871(4) 0.3035(6) 0.043(2) Uani 0.503(3) 1 d . . P A 2 H19C_b H 0.6335 0.2506 0.2940 0.052 Uiso 0.503(3) 1 calc R U P A 2 H19D_b H 0.7836 0.2595 0.3645 0.052 Uiso 0.503(3) 1 calc R U P A 2 Cl1A Cl 0.2968(4) 0.0087(3) 0.6418(3) 0.0278(8) Uani 0.43(3) 1 d . . P . . Cl1B Cl 0.3021(5) -0.0083(9) 0.6532(6) 0.0477(8) Uani 0.57(3) 1 d . . P . . C20 C 0.2500 0.0702(1) 0.7500 0.0221(3) Uani 1 2 d S T P . . H20B H 0.3242 0.1104 0.7807 0.026 Uiso 0.5 1 d R U P . . 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 O1 0.0146(3) 0.0240(4) 0.0169(3) -0.0080(3) -0.0014(3) 0.0023(3) C1 0.0162(4) 0.0160(4) 0.0122(4) -0.0008(3) 0.0040(3) -0.0022(3) O2 0.0121(3) 0.0127(3) 0.0178(3) 0.0004(2) -0.0010(3) -0.0008(2) C2 0.0162(4) 0.0169(4) 0.0145(4) -0.0003(3) 0.0050(3) -0.0014(3) O3 0.0313(5) 0.0169(4) 0.0219(4) 0.0012(3) 0.0092(3) 0.0010(3) C3 0.0250(5) 0.0212(5) 0.0195(5) -0.0026(4) 0.0100(4) 0.0006(4) C4 0.0331(6) 0.0237(5) 0.0180(5) -0.0069(4) 0.0096(4) -0.0033(5) C5 0.0267(6) 0.0250(5) 0.0135(4) -0.0044(4) 0.0040(4) -0.0065(4) C6 0.0185(5) 0.0192(4) 0.0106(4) -0.0001(3) 0.0021(3) -0.0044(4) C7 0.0123(4) 0.0192(4) 0.0178(4) 0.0003(3) 0.0048(3) -0.0009(3) C8 0.0092(4) 0.0166(4) 0.0167(4) -0.0007(3) 0.0018(3) -0.0009(3) C9 0.0100(4) 0.0133(4) 0.0159(4) 0.0005(3) -0.0008(3) 0.0000(3) C11 0.0157(4) 0.0193(5) 0.0190(5) 0.0042(4) 0.0014(4) 0.0020(4) C10 0.0120(4) 0.0182(4) 0.0132(4) -0.0001(3) -0.0007(3) 0.0003(3) C12 0.0149(4) 0.0154(4) 0.0267(5) 0.0032(4) 0.0029(4) 0.0024(4) C13 0.0118(4) 0.0163(4) 0.0240(5) -0.0011(4) 0.0047(4) 0.0004(3) C15 0.0143(4) 0.0161(4) 0.0210(5) -0.0015(4) -0.0014(4) -0.0029(3) C14 0.0170(4) 0.0213(5) 0.0122(4) -0.0014(3) -0.0015(3) 0.0026(4) C16 0.0215(5) 0.0148(4) 0.0215(5) -0.0019(4) 0.0029(4) -0.0022(4) O4A_a 0.0136(8) 0.054(1) 0.028(1) 0.0079(8) 0.0022(7) 0.0148(8) C17A_a 0.022(2) 0.020(1) 0.026(2) 0.010(1) 0.009(2) 0.002(2) C18A_a 0.032(2) 0.030(2) 0.024(1) 0.009(1) -0.006(1) -0.012(1) C19A_a 0.030(2) 0.056(4) 0.059(4) 0.028(3) -0.008(2) -0.011(2) O4B_b 0.0231(9) 0.0262(9) 0.043(1) 0.0148(8) 0.0126(8) 0.0058(7) C18B_b 0.021(1) 0.028(1) 0.031(1) 0.003(1) 0.001(1) 0.002(1) C19B_b 0.083(4) 0.018(2) 0.027(2) -0.001(2) 0.008(2) -0.010(2) Cl1A 0.031(1) 0.030(1) 0.0231(8) -0.0056(8) 0.0068(9) -0.0075(6) Cl1B 0.057(1) 0.053(2) 0.041(1) -0.025(1) 0.0267(8) -0.0191(9) C20 0.0176(7) 0.0255(7) 0.0229(7) 0.00 0.0029(6) 0 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0034 0.0017 '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' O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1507 0.1611 '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 C1 O1 H1A 109.3 . . O1 C1 C2 123.54(9) . . O1 C1 C6 115.45(9) . . C2 C1 C6 120.99(9) . . C9 O2 C15 112.75(7) . . C3 C2 C1 118.6(1) . . C3 C2 C7 120.2(1) . . C1 C2 C7 121.27(9) . . C17A_a O3 C16 112.6(2) . . C16 O3 C17B_b 113.4(3) . . C4 C3 C2 121.3(1) . . C4 C3 H3A 119.4 . . C2 C3 H3A 119.3 . . C5 C4 C3 119.3(1) . . C5 C4 H4A 120.3 . . C3 C4 H4A 120.4 . . C4 C5 C6 121.3(1) . . C4 C5 H5A 119.4 . . C6 C5 H5A 119.3 . . C5 C6 C1 118.5(1) . . C5 C6 C14 121.6(1) . 2_655 C1 C6 C14 119.88(9) . 2_655 C2 C7 C8 113.09(8) . . C2 C7 H7A 109.0 . . C8 C7 H7A 109.0 . . C2 C7 H7B 108.9 . . C8 C7 H7B 108.9 . . H7A C7 H7B 107.8 . . C13 C8 C9 117.97(9) . . C13 C8 C7 120.51(9) . . C9 C8 C7 121.51(9) . . O2 C9 C10 119.71(9) . . O2 C9 C8 117.93(9) . . C10 C9 C8 122.33(9) . . C12 C11 C10 121.3(1) . . C12 C11 H11A 119.4 . . C10 C11 H11A 119.3 . . C11 C10 C9 117.47(9) . . C11 C10 C14 120.34(9) . . C9 C10 C14 122.09(9) . . C13 C12 C11 119.8(1) . . C13 C12 H12A 120.1 . . C11 C12 H12A 120.1 . . C12 C13 C8 120.8(1) . . C12 C13 H13A 119.7 . . C8 C13 H13A 119.5 . . O2 C15 C16 108.41(8) . . O2 C15 H15A 109.9 . . C16 C15 H15A 110.0 . . O2 C15 H15B 110.1 . . C16 C15 H15B 110.0 . . H15A C15 H15B 108.4 . . C6 C14 C10 110.69(8) 2_655 . C6 C14 H14A 109.4 2_655 . C10 C14 H14A 109.5 . . C6 C14 H14B 109.5 2_655 . C10 C14 H14B 109.5 . . H14A C14 H14B 108.1 . . O3 C16 C15 107.82(9) . . O3 C16 H16A 110.1 . . C15 C16 H16A 110.2 . . O3 C16 H16B 110.1 . . C15 C16 H16B 110.1 . . H16A C16 H16B 108.5 . . C19A_a O4A_a C18A_a 115.0(4) . . O3 C17A_a C18A_a 114.0(3) . . O3 C17A_a H17A_a 119.6 . . C18A_a C17A_a H17A_a 99.6 . . O3 C17A_a H17B_a 110.1 . . C18A_a C17A_a H17B_a 94.3 . . H17A_a C17A_a H17B_a 115.8 . . O4A_a C18A_a C17A_a 110.6(3) . . O4A_a C18A_a H18A_a 109.5 . . C17A_a C18A_a H18A_a 109.5 . . O4A_a C18A_a H18B_a 109.5 . . C17A_a C18A_a H18B_a 109.5 . . H18A_a C18A_a H18B_a 108.1 . . O4A_a C19A_a C19A_a 113.6(7) . 2_655 O4A_a C19A_a H19A_a 108.9 . . C19A_a C19A_a H19A_a 108.9 2_655 . O4A_a C19A_a H19B_a 108.9 . . C19A_a C19A_a H19B_a 108.9 2_655 . H19A_a C19A_a H19B_a 107.7 . . C19B_b O4B_b C18B_b 117.2(4) . . C18B_b C17B_b O3 113.2(4) . . C18B_b C17B_b H17C_b 119.8 . . O3 C17B_b H17C_b 100.7 . . C18B_b C17B_b H17D_b 121.1 . . O3 C17B_b H17D_b 102.0 . . H17C_b C17B_b H17D_b 96.5 . . O4B_b C18B_b C17B_b 114.4(3) . . O4B_b C18B_b H18C_b 108.7 . . C17B_b C18B_b H18C_b 108.7 . . O4B_b C18B_b H18D_b 108.7 . . C17B_b C18B_b H18D_b 108.7 . . H18C_b C18B_b H18D_b 107.6 . . O4B_b C19B_b C19B_b 103.6(3) . 2_655 O4B_b C19B_b H19C_b 111.0 . . C19B_b C19B_b H19C_b 111.0 2_655 . O4B_b C19B_b H19D_b 111.0 . . C19B_b C19B_b H19D_b 111.0 2_655 . H19C_b C19B_b H19D_b 109.0 . . Cl1A C20 Cl1A 120.7(3) 2_556 . Cl1A C20 Cl1B 112.2(5) 2_556 . Cl1A C20 Cl1B 9.0(4) . . Cl1A C20 Cl1B 9.0(4) 2_556 2_556 Cl1A C20 Cl1B 112.2(5) . 2_556 Cl1B C20 Cl1B 103.8(8) . 2_556 Cl1A C20 H20B 105.9 2_556 . Cl1A C20 H20B 108.0 . . Cl1B C20 H20B 109.8 . . Cl1B C20 H20B 112.9 2_556 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C1 1.363(1) . O1 H1A 0.8499 . C1 C2 1.403(2) . C1 C6 1.407(1) . O2 C9 1.392(1) . O2 C15 1.444(1) . C2 C3 1.396(2) . C2 C7 1.518(2) . O3 C17A_a 1.393(5) . O3 C16 1.425(1) . O3 C17B_b 1.475(6) . C3 C4 1.390(2) . C3 H3A 0.9600 . C4 C5 1.390(2) . C4 H4A 0.9600 . C5 C6 1.395(2) . C5 H5A 0.9600 . C6 C14 1.516(2) 2_655 C7 C8 1.520(1) . C7 H7A 0.9601 . C7 H7B 0.9600 . C8 C13 1.398(2) . C8 C9 1.403(1) . C9 C10 1.401(1) . C11 C12 1.392(2) . C11 C10 1.398(2) . C11 H11A 0.9600 . C10 C14 1.520(2) . C12 C13 1.390(2) . C12 H12A 0.9599 . C13 H13A 0.9600 . C15 C16 1.501(2) . C15 H15A 0.9600 . C15 H15B 0.9600 . C14 C6 1.516(2) 2_655 C14 H14A 0.9600 . C14 H14B 0.9601 . C16 H16A 0.9601 . C16 H16B 0.9599 . O4A_a C19A_a 1.321(8) . O4A_a C18A_a 1.414(4) . C17A_a C18A_a 1.530(6) . C17A_a H17A_a 0.8406 . C17A_a H17B_a 0.9786 . C18A_a H18A_a 0.9900 . C18A_a H18B_a 0.9900 . C19A_a C19A_a 1.42(2) 2_655 C19A_a H19A_a 0.9900 . C19A_a H19B_a 0.9900 . O4B_b C19B_b 1.392(6) . O4B_b C18B_b 1.414(4) . C17B_b C18B_b 1.473(6) . C17B_b H17C_b 1.0489 . C17B_b H17D_b 1.0386 . C18B_b H18C_b 0.9900 . C18B_b H18D_b 0.9900 . C19B_b C19B_b 1.58(2) 2_655 C19B_b H19C_b 0.9900 . C19B_b H19D_b 0.9900 . Cl1A C20 1.742(4) . Cl1B C20 1.785(5) . C20 Cl1A 1.742(4) 2_556 C20 Cl1B 1.785(5) 2_556 C20 H20B 0.9601 . 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 O1 H1A O2 0.85 1.93 2.767(1) 167.7 . C16 H16B O4A_a 0.96 2.49 3.050(2) 117.4 . C16 H16B O4B_b 0.96 2.41 3.106(2) 128.9 . C19A_a H19A_a Cl1A 0.99 2.94 3.916(9) 170.1 3_656 C19A_a H19A_a Cl1B 0.99 2.68 3.66(2) 169.1 3_656 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_4 O1 C1 C2 C3 178.0(1) . C6 C1 C2 C3 -0.4(2) . O1 C1 C2 C7 -1.1(2) . C6 C1 C2 C7 -179.55(9) . C1 C2 C3 C4 -1.0(2) . C7 C2 C3 C4 178.1(1) . C2 C3 C4 C5 1.1(2) . C3 C4 C5 C6 0.2(2) . C4 C5 C6 C1 -1.5(2) . C4 C5 C6 C14 176.6(1) 2_655 O1 C1 C6 C5 -176.89(9) . C2 C1 C6 C5 1.6(2) . O1 C1 C6 C14 5.0(1) 2_655 C2 C1 C6 C14 -176.50(9) 2_655 C3 C2 C7 C8 106.9(1) . C1 C2 C7 C8 -73.9(1) . C2 C7 C8 C13 -78.9(1) . C2 C7 C8 C9 99.7(1) . C15 O2 C9 C10 -91.4(1) . C15 O2 C9 C8 90.5(1) . C13 C8 C9 O2 -178.21(8) . C7 C8 C9 O2 3.1(1) . C13 C8 C9 C10 3.8(2) . C7 C8 C9 C10 -174.87(9) . C12 C11 C10 C9 3.4(2) . C12 C11 C10 C14 -173.0(1) . O2 C9 C10 C11 175.71(9) . C8 C9 C10 C11 -6.3(2) . O2 C9 C10 C14 -8.0(1) . C8 C9 C10 C14 169.98(9) . C10 C11 C12 C13 1.9(2) . C11 C12 C13 C8 -4.6(2) . C9 C8 C13 C12 1.8(2) . C7 C8 C13 C12 -179.51(9) . C9 O2 C15 C16 -163.58(9) . C11 C10 C14 C6 68.4(1) 2_655 C9 C10 C14 C6 -107.8(1) 2_655 C17A_a O3 C16 C15 178.3(3) . C17B_b O3 C16 C15 -170.3(2) . O2 C15 C16 O3 68.5(1) . C16 O3 C17A_a C18A_a 68.8(4) . C17B_b O3 C17A_a C18A_a -28(2) . C19A_a O4A_a C18A_a C17A_a -172.1(4) . O3 C17A_a C18A_a O4A_a -87.2(4) . C18A_a O4A_a C19A_a C19A_a -136.7(4) 2_655 C17A_a O3 C17B_b C18B_b 170(3) . C16 O3 C17B_b C18B_b 82.5(4) . C19B_b O4B_b C18B_b C17B_b -90.1(5) . O3 C17B_b C18B_b O4B_b -71.1(5) . C18B_b O4B_b C19B_b C19B_b 176.3(6) 2_655