#------------------------------------------------------------------------------ #$Date: 2024-07-24 03:59:59 +0300 (Wed, 24 Jul 2024) $ #$Revision: 293521 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/21/1572158.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_1572158 loop_ _publ_author_name 'Franc\'es-Poveda, Enrique' 'Mart\'inez de Sarasa Buchaca, Marc' 'Moya-L\'opez, Carmen' 'Vitorica-Yrezabal, I\~nigo J.' 'L\'opez-Solera, Isabel' 'Castro-Osma, Jos\'e A.' 'la Cruz-Mart\'inez, Felipe de' 'Lara-S\'anchez, Agust\'in' _publ_section_title ; Calcium-catalysed ring-opening copolymerisation of epoxides and cyclic anhydrides ; _journal_name_full 'Polymer Chemistry' _journal_paper_doi 10.1039/D4PY00379A _journal_year 2024 _chemical_formula_moiety 'C36 H46 Ca2 I2 N8 O4, 2(C H2 Cl2)' _chemical_formula_sum 'C38 H50 Ca2 Cl4 I2 N8 O4' _chemical_formula_weight 1158.62 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2024-02-24 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2024-03-18 deposited with the CCDC. 2024-07-08 downloaded from the CCDC. ; _cell_angle_alpha 106.384(11) _cell_angle_beta 100.446(11) _cell_angle_gamma 93.892(10) _cell_formula_units_Z 1 _cell_length_a 9.505(3) _cell_length_b 10.990(3) _cell_length_c 12.918(5) _cell_measurement_reflns_used 6171 _cell_measurement_temperature 296.15 _cell_measurement_theta_max 25.864 _cell_measurement_theta_min 2.196 _cell_volume 1263.0(7) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2014/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.994 _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 0.0762 _diffrn_reflns_av_unetI/netI 0.0415 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 29978 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.465 _diffrn_reflns_theta_min 2.157 _exptl_absorpt_coefficient_mu 1.703 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6511 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0979 before and 0.0603 after correction. The Ratio of minimum to maximum transmission is 0.8735. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.523 _exptl_crystal_description block _exptl_crystal_F_000 580 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.852 _refine_diff_density_min -1.149 _refine_diff_density_rms 0.083 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 270 _refine_ls_number_reflns 5188 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0444 _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^)+(0.0738P)^2^+0.9607P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1230 _refine_ls_wR_factor_ref 0.1348 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4033 _reflns_number_total 5188 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4py00379a2.cif _cod_data_source_block mo_phocai_0m_a _cod_database_code 1572158 _shelxl_version_number 2014-3 _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 0.848 _shelx_estimated_absorpt_t_min 0.749 _olex2_refinement_description ; 1.a Rotating group: O2(H2A,H2B) 1.b Ternary CH refined with riding coordinates: C12(H12), C11(H11) 1.c Secondary CH2 refined with riding coordinates: C3(H3A,H3B) 1.d Aromatic/amide H refined with riding coordinates: C18(H18), C2(H2), C14(H14), C17(H17), C16(H16), C15(H15) 1.e Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C) ; _shelx_res_file ; TITL mo_PhOCaI_0m_a.res in P-1 REM Old TITL mo_PhOCaI_0m in P-1 REM SHELXT solution in P-1: R1 0.205, Rweak 0.022, Alpha 0.046 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C18 Ca I N7 O CELL 0.71073 9.505 10.9904 12.9181 106.384 100.446 93.892 ZERR 1 0.0028 0.0033 0.0045 0.011 0.011 0.01 LATT 1 SFAC C H Ca Cl I N O UNIT 38 50 2 4 2 8 4 EQIV $1 1-X,1-Y,1-Z L.S. 10 PLAN 10 SIZE 0.18 0.12 0.1 TEMP 23 CONF FREE C12 Ca1_$1 BOND LIST 6 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.073800 0.960700 FVAR 0.62972 I1 5 0.072738 0.317128 0.539788 11.00000 0.05176 0.05927 = 0.10364 0.02961 0.03353 0.00993 CA1 3 0.349427 0.386165 0.459946 11.00000 0.03743 0.03693 = 0.05161 0.00979 0.01369 0.00759 O1 7 0.553753 0.428935 0.405701 11.00000 0.04063 0.03716 = 0.05202 0.01143 0.01758 0.01069 N2 6 0.472683 0.143647 0.286835 11.00000 0.05080 0.03317 = 0.05158 0.00849 0.01729 0.00860 O2 7 0.198316 0.494530 0.355267 11.00000 0.07495 0.08906 = 0.07204 0.03511 0.01428 0.03422 AFIX 7 H2A 2 0.116670 0.533046 0.372410 11.00000 -1.50000 H2B 2 0.207111 0.507755 0.287774 11.00000 -1.50000 AFIX 0 N3 6 0.524080 0.263171 0.539423 11.00000 0.05684 0.04810 = 0.05113 0.01980 0.01649 0.01333 N1 6 0.344146 0.183456 0.305519 11.00000 0.04602 0.04189 = 0.05720 0.00430 0.01067 0.00664 N4 6 0.605372 0.192467 0.473090 11.00000 0.04564 0.04210 = 0.05534 0.02061 0.01217 0.01154 CL2 4 1.074429 0.646799 0.154082 11.00000 0.12719 0.55791 = 0.20822 0.22563 0.05225 0.04616 C12 1 0.647061 0.345144 0.364887 11.00000 0.04087 0.03720 = 0.04568 0.01108 0.01459 0.00721 AFIX 13 H12 2 0.742624 0.375683 0.413020 11.00000 -1.20000 AFIX 0 CL1 4 0.842964 0.753264 0.061575 11.00000 0.17446 0.33143 = 0.35161 0.20413 0.08943 0.10352 C11 1 0.606623 0.205333 0.363966 11.00000 0.04722 0.03643 = 0.05339 0.01368 0.01978 0.01545 AFIX 13 H11 2 0.682870 0.157333 0.337502 11.00000 -1.20000 AFIX 0 C13 1 0.661334 0.341959 0.247796 11.00000 0.05189 0.03529 = 0.04849 0.00936 0.01626 0.00700 C19 1 0.456008 0.049318 0.188721 11.00000 0.06971 0.03544 = 0.05532 0.00669 0.01884 0.00838 C18 1 0.544622 0.357140 0.173389 11.00000 0.06439 0.06269 = 0.05339 0.01695 0.01487 0.00739 AFIX 43 H18 2 0.456658 0.370135 0.193903 11.00000 -1.20000 AFIX 0 C8 1 0.676423 0.113836 0.521142 11.00000 0.04687 0.03875 = 0.07673 0.02666 0.00108 0.00487 C6 1 0.548091 0.228118 0.630895 11.00000 0.06194 0.05776 = 0.05402 0.02484 0.00819 -0.00251 C2 1 0.311672 0.026597 0.144520 11.00000 0.08027 0.05321 = 0.05478 0.00072 0.00766 0.00125 AFIX 43 H2 2 0.266065 -0.034246 0.078657 11.00000 -1.20000 AFIX 0 C1 1 0.245475 0.111664 0.216593 11.00000 0.05158 0.05682 = 0.06306 0.00438 0.00567 0.00313 C9 1 0.769469 0.021960 0.466184 11.00000 0.06829 0.05109 = 0.11615 0.03355 0.01289 0.02512 AFIX 137 H9A 2 0.711759 -0.038723 0.400941 11.00000 -1.50000 H9B 2 0.811658 -0.022320 0.516013 11.00000 -1.50000 H9C 2 0.844535 0.068124 0.446426 11.00000 -1.50000 AFIX 0 C7 1 0.641312 0.135937 0.622630 11.00000 0.06673 0.05962 = 0.07171 0.03788 -0.00189 0.00319 H7 2 0.678588 0.106362 0.674999 11.00000 -1.20000 C14 1 0.790828 0.326624 0.216323 11.00000 0.05816 0.07357 = 0.06239 0.02248 0.02738 0.01116 AFIX 43 H14 2 0.870939 0.319345 0.266499 11.00000 -1.20000 AFIX 0 C10 1 0.478987 0.289060 0.724284 11.00000 0.09762 0.08704 = 0.05385 0.02911 0.02445 0.00614 AFIX 137 H10A 2 0.545788 0.356941 0.777629 11.00000 -1.50000 H10B 2 0.452194 0.226375 0.758383 11.00000 -1.50000 H10C 2 0.394523 0.323072 0.696920 11.00000 -1.50000 AFIX 0 C17 1 0.560453 0.352716 0.066868 11.00000 0.09286 0.08829 = 0.05243 0.02277 -0.00013 0.00268 AFIX 43 H17 2 0.481942 0.362078 0.016362 11.00000 -1.20000 AFIX 0 C5 1 0.579434 -0.007604 0.145634 11.00000 0.08614 0.05156 = 0.06864 0.00108 0.03079 0.01515 AFIX 137 H5A 2 0.640659 0.057154 0.132508 11.00000 -1.50000 H5B 2 0.543646 -0.074832 0.077829 11.00000 -1.50000 H5C 2 0.633565 -0.041829 0.198790 11.00000 -1.50000 AFIX 0 C16 1 0.687739 0.335090 0.036169 11.00000 0.10444 0.10541 = 0.05544 0.02234 0.03326 -0.00030 AFIX 43 H16 2 0.696714 0.331966 -0.035007 11.00000 -1.20000 AFIX 0 C15 1 0.802679 0.321942 0.110018 11.00000 0.08266 0.10589 = 0.07823 0.02930 0.04752 0.01819 AFIX 43 H15 2 0.890416 0.309644 0.088923 11.00000 -1.20000 AFIX 0 C4 1 0.090040 0.126364 0.208593 11.00000 0.06308 0.10531 = 0.10001 -0.01119 -0.00559 0.00878 AFIX 137 H4A 2 0.033977 0.059901 0.146573 11.00000 -1.50000 H4B 2 0.073696 0.208155 0.199083 11.00000 -1.50000 H4C 2 0.061982 0.120538 0.274951 11.00000 -1.50000 AFIX 0 C3 1 0.911819 0.681541 0.156037 11.00000 0.13854 0.32175 = 0.20187 0.15674 0.07532 0.07431 AFIX 23 H3A 2 0.910639 0.737286 0.228902 11.00000 -1.20000 H3B 2 0.849081 0.603360 0.144269 11.00000 -1.20000 AFIX 0 HKLF 4 REM mo_PhOCaI_0m_a.res in P-1 REM R1 = 0.0444 for 4033 Fo > 4sig(Fo) and 0.0589 for all 5188 data REM 270 parameters refined using 0 restraints END WGHT 0.0735 0.9614 REM Highest difference peak 0.852, deepest hole -1.149, 1-sigma level 0.083 Q1 1 0.8315 0.6154 -0.0184 11.00000 0.05 0.85 Q2 1 1.0572 0.6034 0.1360 11.00000 0.05 0.72 Q3 1 0.1366 0.3284 0.5955 11.00000 0.05 0.70 Q4 1 0.9694 0.8143 0.1783 11.00000 0.05 0.66 Q5 1 0.9114 0.8236 0.1827 11.00000 0.05 0.64 Q6 1 0.7863 0.2547 0.6138 11.00000 0.05 0.30 Q7 1 0.8778 0.6709 0.1454 11.00000 0.05 0.27 Q8 1 0.3162 0.1533 0.2732 11.00000 0.05 0.27 Q9 1 0.4709 0.1177 0.2610 11.00000 0.05 0.26 Q10 1 0.6555 0.3564 0.2934 11.00000 0.05 0.26 ; _shelx_res_checksum 49896 _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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.07274(3) 0.31713(3) 0.53979(3) 0.06805(15) Uani 1 1 d . . . . . Ca1 Ca 0.34943(8) 0.38616(7) 0.45995(6) 0.04201(19) Uani 1 1 d . . . . . O1 O 0.5538(3) 0.4289(2) 0.4057(2) 0.0424(6) Uani 1 1 d . . . . . N2 N 0.4727(4) 0.1436(3) 0.2868(3) 0.0450(7) Uani 1 1 d . . . . . O2 O 0.1983(4) 0.4945(4) 0.3553(3) 0.0754(9) Uani 1 1 d . . . . . H2A H 0.1167 0.5330 0.3724 0.113 Uiso 1 1 d R U . . . H2B H 0.2071 0.5078 0.2878 0.113 Uiso 1 1 d R U . . . N3 N 0.5241(4) 0.2632(3) 0.5394(3) 0.0500(8) Uani 1 1 d . . . . . N1 N 0.3441(4) 0.1835(3) 0.3055(3) 0.0506(8) Uani 1 1 d . . . . . N4 N 0.6054(3) 0.1925(3) 0.4731(3) 0.0459(7) Uani 1 1 d . . . . . Cl2 Cl 1.0744(4) 0.6468(7) 0.1541(3) 0.272(3) Uani 1 1 d . . . . . C12 C 0.6471(4) 0.3451(3) 0.3649(3) 0.0407(8) Uani 1 1 d . . . . . H12 H 0.7426 0.3757 0.4130 0.049 Uiso 1 1 calc R U . . . Cl1 Cl 0.8430(5) 0.7533(6) 0.0616(5) 0.256(2) Uani 1 1 d . . . . . C11 C 0.6066(4) 0.2053(3) 0.3640(3) 0.0439(8) Uani 1 1 d . . . . . H11 H 0.6829 0.1573 0.3375 0.053 Uiso 1 1 calc R U . . . C13 C 0.6613(4) 0.3420(3) 0.2478(3) 0.0451(8) Uani 1 1 d . . . . . C19 C 0.4560(5) 0.0493(4) 0.1887(4) 0.0541(10) Uani 1 1 d . . . . . C18 C 0.5446(5) 0.3571(5) 0.1734(4) 0.0599(11) Uani 1 1 d . . . . . H18 H 0.4567 0.3701 0.1939 0.072 Uiso 1 1 calc R U . . . C8 C 0.6764(4) 0.1138(4) 0.5211(4) 0.0537(10) Uani 1 1 d . . . . . C6 C 0.5481(5) 0.2281(4) 0.6309(4) 0.0572(10) Uani 1 1 d . . . . . C2 C 0.3117(6) 0.0266(5) 0.1445(4) 0.0672(12) Uani 1 1 d . . . . . H2 H 0.2661 -0.0342 0.0787 0.081 Uiso 1 1 calc R U . . . C1 C 0.2455(5) 0.1117(5) 0.2166(4) 0.0610(11) Uani 1 1 d . . . . . C9 C 0.7695(6) 0.0220(5) 0.4662(5) 0.0767(15) Uani 1 1 d . . . . . H9A H 0.7118 -0.0387 0.4009 0.115 Uiso 1 1 calc R U . . . H9B H 0.8117 -0.0223 0.5160 0.115 Uiso 1 1 calc R U . . . H9C H 0.8445 0.0681 0.4464 0.115 Uiso 1 1 calc R U . . . C7 C 0.6413(6) 0.1359(5) 0.6226(4) 0.0646(12) Uani 1 1 d . . . . . H7 H 0.679(6) 0.106(5) 0.675(4) 0.078 Uiso 1 1 d . U . . . C14 C 0.7908(5) 0.3266(5) 0.2163(4) 0.0622(11) Uani 1 1 d . . . . . H14 H 0.8709 0.3193 0.2665 0.075 Uiso 1 1 calc R U . . . C10 C 0.4790(7) 0.2891(6) 0.7243(4) 0.0770(15) Uani 1 1 d . . . . . H10A H 0.5458 0.3569 0.7776 0.115 Uiso 1 1 calc R U . . . H10B H 0.4522 0.2264 0.7584 0.115 Uiso 1 1 calc R U . . . H10C H 0.3945 0.3231 0.6969 0.115 Uiso 1 1 calc R U . . . C17 C 0.5605(7) 0.3527(6) 0.0669(4) 0.0800(15) Uani 1 1 d . . . . . H17 H 0.4819 0.3621 0.0164 0.096 Uiso 1 1 calc R U . . . C5 C 0.5794(6) -0.0076(5) 0.1456(4) 0.0701(13) Uani 1 1 d . . . . . H5A H 0.6407 0.0572 0.1325 0.105 Uiso 1 1 calc R U . . . H5B H 0.5436 -0.0748 0.0778 0.105 Uiso 1 1 calc R U . . . H5C H 0.6336 -0.0418 0.1988 0.105 Uiso 1 1 calc R U . . . C16 C 0.6877(8) 0.3351(6) 0.0362(5) 0.0873(18) Uani 1 1 d . . . . . H16 H 0.6967 0.3320 -0.0350 0.105 Uiso 1 1 calc R U . . . C15 C 0.8027(7) 0.3219(6) 0.1100(5) 0.0842(16) Uani 1 1 d . . . . . H15 H 0.8904 0.3096 0.0889 0.101 Uiso 1 1 calc R U . . . C4 C 0.0900(6) 0.1264(7) 0.2086(6) 0.101(2) Uani 1 1 d . . . . . H4A H 0.0340 0.0599 0.1466 0.152 Uiso 1 1 calc R U . . . H4B H 0.0737 0.2082 0.1991 0.152 Uiso 1 1 calc R U . . . H4C H 0.0620 0.1205 0.2750 0.152 Uiso 1 1 calc R U . . . C3 C 0.9118(13) 0.6815(16) 0.1560(11) 0.197(6) Uani 1 1 d . . . . . H3A H 0.9106 0.7373 0.2289 0.236 Uiso 1 1 calc R U . . . H3B H 0.8491 0.6034 0.1443 0.236 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0518(2) 0.0593(2) 0.1036(3) 0.02961(18) 0.03353(17) 0.00993(13) Ca1 0.0374(4) 0.0369(4) 0.0516(4) 0.0098(3) 0.0137(3) 0.0076(3) O1 0.0406(13) 0.0372(13) 0.0520(14) 0.0114(11) 0.0176(11) 0.0107(10) N2 0.0508(18) 0.0332(15) 0.0516(18) 0.0085(13) 0.0173(14) 0.0086(13) O2 0.075(2) 0.089(3) 0.072(2) 0.0351(19) 0.0143(17) 0.0342(19) N3 0.0568(19) 0.0481(18) 0.0511(18) 0.0198(15) 0.0165(15) 0.0133(15) N1 0.0460(18) 0.0419(17) 0.0572(19) 0.0043(15) 0.0107(15) 0.0066(14) N4 0.0456(17) 0.0421(17) 0.0553(18) 0.0206(14) 0.0122(14) 0.0115(13) Cl2 0.127(2) 0.558(10) 0.208(3) 0.226(5) 0.052(2) 0.046(4) C12 0.0409(18) 0.0372(18) 0.0457(19) 0.0111(15) 0.0146(15) 0.0072(14) Cl1 0.174(3) 0.331(7) 0.352(6) 0.204(6) 0.089(4) 0.104(4) C11 0.047(2) 0.0364(18) 0.053(2) 0.0137(16) 0.0198(17) 0.0155(15) C13 0.052(2) 0.0353(18) 0.048(2) 0.0094(15) 0.0163(17) 0.0070(15) C19 0.070(3) 0.0354(19) 0.055(2) 0.0067(17) 0.019(2) 0.0084(18) C18 0.064(3) 0.063(3) 0.053(2) 0.017(2) 0.015(2) 0.007(2) C8 0.047(2) 0.039(2) 0.077(3) 0.0267(19) 0.001(2) 0.0049(16) C6 0.062(3) 0.058(3) 0.054(2) 0.025(2) 0.008(2) -0.003(2) C2 0.080(3) 0.053(3) 0.055(2) 0.001(2) 0.008(2) 0.001(2) C1 0.052(2) 0.057(3) 0.063(3) 0.004(2) 0.006(2) 0.0031(19) C9 0.068(3) 0.051(3) 0.116(4) 0.034(3) 0.013(3) 0.025(2) C7 0.067(3) 0.060(3) 0.072(3) 0.038(2) -0.002(2) 0.003(2) C14 0.058(3) 0.074(3) 0.062(3) 0.022(2) 0.027(2) 0.011(2) C10 0.098(4) 0.087(4) 0.054(3) 0.029(3) 0.024(3) 0.006(3) C17 0.093(4) 0.088(4) 0.052(3) 0.023(3) 0.000(3) 0.003(3) C5 0.086(3) 0.052(3) 0.069(3) 0.001(2) 0.031(3) 0.015(2) C16 0.104(5) 0.105(5) 0.055(3) 0.022(3) 0.033(3) 0.000(4) C15 0.083(4) 0.106(4) 0.078(3) 0.029(3) 0.048(3) 0.018(3) C4 0.063(3) 0.105(5) 0.100(4) -0.011(4) -0.006(3) 0.009(3) C3 0.139(9) 0.322(19) 0.202(12) 0.157(13) 0.075(8) 0.074(11) 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 I1 Ca1 Ca1 140.31(4) . 2_666 ? I1 Ca1 C12 82.83(7) . 2_666 ? O1 Ca1 I1 177.26(7) . . ? O1 Ca1 I1 100.79(7) 2_666 . ? O1 Ca1 Ca1 39.59(6) 2_666 2_666 ? O1 Ca1 Ca1 40.18(7) . 2_666 ? O1 Ca1 O1 79.77(10) . 2_666 ? O1 Ca1 O2 92.68(12) 2_666 . ? O1 Ca1 O2 97.31(12) . . ? O1 Ca1 N3 92.06(11) 2_666 . ? O1 Ca1 N3 74.95(10) . . ? O1 Ca1 N1 79.14(10) . . ? O1 Ca1 N1 157.50(10) 2_666 . ? O1 Ca1 C12 22.74(9) 2_666 2_666 ? O1 Ca1 C12 98.34(9) . 2_666 ? O2 Ca1 I1 85.35(10) . . ? O2 Ca1 Ca1 96.49(10) . 2_666 ? O2 Ca1 N3 170.05(12) . . ? O2 Ca1 N1 97.67(13) . . ? O2 Ca1 C12 77.39(12) . 2_666 ? N3 Ca1 I1 102.33(8) . . ? N3 Ca1 Ca1 81.69(9) . 2_666 ? N3 Ca1 N1 74.96(12) . . ? N3 Ca1 C12 109.58(11) . 2_666 ? N1 Ca1 I1 99.92(8) . . ? N1 Ca1 Ca1 118.93(9) . 2_666 ? N1 Ca1 C12 174.20(11) . 2_666 ? C12 Ca1 Ca1 59.29(7) 2_666 2_666 ? Ca1 O1 Ca1 100.23(10) . 2_666 ? C12 O1 Ca1 117.9(2) . 2_666 ? C12 O1 Ca1 128.6(2) . . ? N1 N2 C11 120.4(3) . . ? N1 N2 C19 111.8(3) . . ? C19 N2 C11 127.7(3) . . ? Ca1 O2 H2A 127.7 . . ? Ca1 O2 H2B 127.8 . . ? H2A O2 H2B 104.5 . . ? N4 N3 Ca1 118.6(2) . . ? C6 N3 Ca1 135.4(3) . . ? C6 N3 N4 104.9(3) . . ? N2 N1 Ca1 118.0(2) . . ? C1 N1 Ca1 135.6(3) . . ? C1 N1 N2 104.7(3) . . ? N3 N4 C11 120.8(3) . . ? C8 N4 N3 111.8(3) . . ? C8 N4 C11 127.3(3) . . ? O1 C12 H12 107.3 . . ? O1 C12 C11 114.2(3) . . ? O1 C12 C13 112.7(3) . . ? C11 C12 H12 107.3 . . ? C13 C12 H12 107.3 . . ? C13 C12 C11 107.8(3) . . ? N2 C11 N4 110.8(3) . . ? N2 C11 C12 113.1(3) . . ? N2 C11 H11 106.2 . . ? N4 C11 C12 113.6(3) . . ? N4 C11 H11 106.2 . . ? C12 C11 H11 106.2 . . ? C18 C13 C12 120.4(4) . . ? C14 C13 C12 120.4(4) . . ? C14 C13 C18 119.1(4) . . ? N2 C19 C5 123.1(4) . . ? C2 C19 N2 106.0(4) . . ? C2 C19 C5 130.9(4) . . ? C13 C18 H18 120.4 . . ? C13 C18 C17 119.2(5) . . ? C17 C18 H18 120.4 . . ? N4 C8 C9 123.6(4) . . ? N4 C8 C7 105.8(4) . . ? C7 C8 C9 130.7(4) . . ? N3 C6 C7 110.5(4) . . ? N3 C6 C10 119.9(4) . . ? C7 C6 C10 129.6(4) . . ? C19 C2 H2 126.5 . . ? C19 C2 C1 107.1(4) . . ? C1 C2 H2 126.5 . . ? N1 C1 C2 110.4(4) . . ? N1 C1 C4 120.3(4) . . ? C2 C1 C4 129.2(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C7 C6 107.0(4) . . ? C8 C7 H7 127(4) . . ? C6 C7 H7 126(4) . . ? C13 C14 H14 119.9 . . ? C13 C14 C15 120.2(5) . . ? C15 C14 H14 119.9 . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C18 C17 H17 119.4 . . ? C16 C17 C18 121.1(5) . . ? C16 C17 H17 119.4 . . ? C19 C5 H5A 109.5 . . ? C19 C5 H5B 109.5 . . ? C19 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C17 C16 H16 120.2 . . ? C17 C16 C15 119.5(5) . . ? C15 C16 H16 120.2 . . ? C14 C15 H15 119.6 . . ? C16 C15 C14 120.8(5) . . ? C16 C15 H15 119.6 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? Cl2 C3 Cl1 115.2(7) . . ? Cl2 C3 H3A 108.5 . . ? Cl2 C3 H3B 108.5 . . ? Cl1 C3 H3A 108.5 . . ? Cl1 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Ca1 3.1161(11) . ? Ca1 Ca1 3.4667(17) 2_666 ? Ca1 O1 2.245(3) . ? Ca1 O1 2.273(3) 2_666 ? Ca1 O2 2.397(3) . ? Ca1 N3 2.471(3) . ? Ca1 N1 2.527(3) . ? Ca1 C12 3.167(4) 2_666 ? O1 Ca1 2.273(3) 2_666 ? O1 C12 1.385(4) . ? N2 N1 1.365(5) . ? N2 C11 1.454(5) . ? N2 C19 1.367(5) . ? O2 H2A 0.9405 . ? O2 H2B 0.9405 . ? N3 N4 1.372(5) . ? N3 C6 1.330(5) . ? N1 C1 1.349(5) . ? N4 C11 1.458(5) . ? N4 C8 1.348(5) . ? Cl2 C3 1.620(11) . ? C12 H12 0.9800 . ? C12 C11 1.555(5) . ? C12 C13 1.534(5) . ? Cl1 C3 1.692(12) . ? C11 H11 0.9800 . ? C13 C18 1.383(6) . ? C13 C14 1.371(6) . ? C19 C2 1.364(7) . ? C19 C5 1.489(6) . ? C18 H18 0.9300 . ? C18 C17 1.399(7) . ? C8 C9 1.500(7) . ? C8 C7 1.371(7) . ? C6 C7 1.385(7) . ? C6 C10 1.492(7) . ? C2 H2 0.9300 . ? C2 C1 1.392(7) . ? C1 C4 1.485(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C7 H7 0.86(5) . ? C14 H14 0.9300 . ? C14 C15 1.385(7) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C17 H17 0.9300 . ? C17 C16 1.349(9) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C16 H16 0.9300 . ? C16 C15 1.359(9) . ? C15 H15 0.9300 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? 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 Ca1 O1 C12 C11 128.9(3) 2_666 . . . ? Ca1 O1 C12 C11 -3.9(4) . . . . ? Ca1 O1 C12 C13 -107.7(3) 2_666 . . . ? Ca1 O1 C12 C13 119.5(3) . . . . ? Ca1 N3 N4 C11 9.9(4) . . . . ? Ca1 N3 N4 C8 -169.2(3) . . . . ? Ca1 N3 C6 C7 167.0(3) . . . . ? Ca1 N3 C6 C10 -13.9(7) . . . . ? Ca1 N1 C1 C2 165.5(3) . . . . ? Ca1 N1 C1 C4 -16.9(8) . . . . ? O1 C12 C11 N2 66.9(4) . . . . ? O1 C12 C11 N4 -60.5(4) . . . . ? O1 C12 C13 C18 -34.2(5) . . . . ? O1 C12 C13 C14 144.5(4) . . . . ? N2 N1 C1 C2 1.1(5) . . . . ? N2 N1 C1 C4 178.7(5) . . . . ? N2 C19 C2 C1 1.8(5) . . . . ? N3 N4 C11 N2 -74.1(4) . . . . ? N3 N4 C11 C12 54.5(5) . . . . ? N3 N4 C8 C9 177.8(4) . . . . ? N3 N4 C8 C7 -0.9(5) . . . . ? N3 C6 C7 C8 0.2(5) . . . . ? N1 N2 C11 N4 60.6(4) . . . . ? N1 N2 C11 C12 -68.3(4) . . . . ? N1 N2 C19 C2 -1.2(5) . . . . ? N1 N2 C19 C5 177.3(4) . . . . ? N4 N3 C6 C7 -0.7(5) . . . . ? N4 N3 C6 C10 178.4(4) . . . . ? N4 C8 C7 C6 0.4(5) . . . . ? C12 C13 C18 C17 -179.5(4) . . . . ? C12 C13 C14 C15 179.1(5) . . . . ? C11 N2 N1 Ca1 9.1(4) . . . . ? C11 N2 N1 C1 176.8(4) . . . . ? C11 N2 C19 C2 -177.6(4) . . . . ? C11 N2 C19 C5 0.9(6) . . . . ? C11 N4 C8 C9 -1.2(6) . . . . ? C11 N4 C8 C7 -179.9(4) . . . . ? C11 C12 C13 C18 92.7(4) . . . . ? C11 C12 C13 C14 -88.6(4) . . . . ? C13 C12 C11 N2 -59.1(4) . . . . ? C13 C12 C11 N4 173.5(3) . . . . ? C13 C18 C17 C16 -0.6(8) . . . . ? C13 C14 C15 C16 1.4(9) . . . . ? C19 N2 N1 Ca1 -167.6(3) . . . . ? C19 N2 N1 C1 0.1(5) . . . . ? C19 N2 C11 N4 -123.2(4) . . . . ? C19 N2 C11 C12 107.9(4) . . . . ? C19 C2 C1 N1 -1.9(6) . . . . ? C19 C2 C1 C4 -179.2(6) . . . . ? C18 C13 C14 C15 -2.3(7) . . . . ? C18 C17 C16 C15 -0.3(10) . . . . ? C8 N4 C11 N2 104.8(4) . . . . ? C8 N4 C11 C12 -126.6(4) . . . . ? C6 N3 N4 C11 -180.0(3) . . . . ? C6 N3 N4 C8 1.0(5) . . . . ? C9 C8 C7 C6 -178.1(5) . . . . ? C14 C13 C18 C17 1.9(7) . . . . ? C10 C6 C7 C8 -178.8(5) . . . . ? C17 C16 C15 C14 -0.1(10) . . . . ? C5 C19 C2 C1 -176.6(5) . . . . ?