#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:39:24 +0300 (Tue, 06 Oct 2020) $ #$Revision: 258087 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239976.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_7239976 loop_ _publ_author_name 'Barry, Kristy-Lyn' 'Grimmer, Craig D.' 'Munro, Orde Q.' 'Akerman, Matthew P.' _publ_section_title ; Self-assembled supramolecular structures of O,N,N′ tridentate imidazole--phenol Schiff base compounds ; _journal_issue 13 _journal_name_full 'RSC Advances' _journal_page_first 7867 _journal_page_last 7878 _journal_paper_doi 10.1039/C9RA10488G _journal_volume 10 _journal_year 2020 _chemical_formula_sum 'C12 H13 N3 O' _chemical_formula_weight 215.25 _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_method SHELXL-2014/7 _audit_update_record ; 2019-01-16 deposited with the CCDC. 2020-02-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.668(5) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.849(5) _cell_length_b 10.609(4) _cell_length_c 16.349(5) _cell_measurement_reflns_used 4440 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.1 _cell_measurement_theta_min 1.9 _cell_volume 2213.5(14) _computing_cell_refinement 'SAINT-Plus (Bruker, 2012)' _computing_data_collection 'APEX2 (Bruker, 2012)' _computing_data_reduction 'SAINT-Plus (Bruker, 2012)' _computing_molecular_graphics 'WinGX (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXL-2016/6 (Sheldrick, 2016)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\w and \f-scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Incoatec microsource' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_unetI/netI 0.0277 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 22148 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 29.059 _diffrn_reflns_theta_min 1.912 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_correction_T_min 0.6843 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 2012' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.292 _exptl_crystal_description needle _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.090 _refine_diff_density_max 0.417 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 301 _refine_ls_number_reflns 5907 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0466 _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^)+(0.0733P)^2^+0.6579P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1297 _refine_ls_wR_factor_ref 0.1435 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4440 _reflns_number_total 5907 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ra10488g2.cif _cod_data_source_block shelx_CCDC1 _cod_depositor_comments 'Adding full bibliography for 7239975--7239978.cif.' _cod_original_cell_volume 2213.5(15) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7239976 _shelx_shelxl_version_number 2014/7 _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 0.975 _shelx_estimated_absorpt_t_max 0.992 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL mo_MA_KLB_HL1_0m in P-1 CELL 0.71073 12.8490 10.6090 16.3490 90.000 96.668 90.000 ZERR 4.00 0.0050 0.0050 0.0050 0.005 0.005 0.005 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C N O H UNIT 96 24 8 104 MERG 3 FMAP 2 PLAN 15 SIZE 0.090 0.120 0.300 ACTA 50.00 BOND $H CONF L.S. 4 TEMP -173.00 WGHT 0.073300 0.657900 FVAR 0.07827 O1A 3 -0.101968 0.136362 0.740891 11.00000 0.02105 0.02387 = 0.02969 -0.00251 -0.01020 0.00312 O1B 3 0.102541 -0.104591 0.763933 11.00000 0.02033 0.02609 = 0.02872 -0.00297 -0.00995 0.00362 N3A 2 -0.224786 -0.033022 0.626086 11.00000 0.01940 0.02435 = 0.01829 0.00061 0.00039 0.00035 N3B 2 0.228488 0.067684 0.874232 11.00000 0.01897 0.02628 = 0.01826 0.00052 -0.00033 0.00154 N1A 2 -0.023026 -0.264725 0.674365 11.00000 0.01922 0.02657 = 0.01995 -0.00168 -0.00076 0.00184 N2A 2 -0.179292 -0.306135 0.607278 11.00000 0.01776 0.02462 = 0.01968 -0.00134 0.00084 -0.00142 N2B 2 0.182443 0.340426 0.892799 11.00000 0.01898 0.02637 = 0.01920 -0.00291 0.00119 -0.00105 N1B 2 0.023504 0.297104 0.831367 11.00000 0.01938 0.02401 = 0.02212 -0.00018 -0.00050 0.00210 C6A 1 -0.247804 0.094621 0.640006 11.00000 0.01548 0.02401 = 0.01742 0.00155 0.00155 -0.00001 C4B 1 0.116372 0.248544 0.860101 11.00000 0.01582 0.02404 = 0.01735 -0.00069 0.00054 -0.00051 C6B 1 0.251283 -0.060414 0.861470 11.00000 0.01584 0.02410 = 0.01730 0.00196 0.00136 0.00018 C4A 1 -0.113919 -0.214871 0.641943 11.00000 0.01644 0.02494 = 0.01782 -0.00121 0.00072 -0.00090 C11B 1 0.345259 -0.103784 0.904077 11.00000 0.01502 0.03228 = 0.01694 -0.00001 0.00028 0.00120 AFIX 43 H11B 4 0.385842 -0.046864 0.939539 11.00000 -1.20000 AFIX 0 C9A 1 -0.317983 0.341629 0.657639 11.00000 0.02282 0.02554 = 0.02329 0.00139 0.00283 0.00561 AFIX 43 H9A 4 -0.340802 0.425898 0.663863 11.00000 -1.20000 AFIX 0 C8B 1 0.228928 -0.267384 0.800330 11.00000 0.02162 0.02638 = 0.02212 -0.00118 0.00022 0.00206 AFIX 43 H8B 4 0.189506 -0.324830 0.764484 11.00000 -1.20000 AFIX 0 C9B 1 0.321971 -0.307136 0.844103 11.00000 0.02214 0.02924 = 0.02321 0.00065 0.00327 0.00678 AFIX 43 H9B 4 0.345140 -0.391257 0.837873 11.00000 -1.20000 AFIX 0 C8A 1 -0.226493 0.300518 0.702926 11.00000 0.02050 0.02407 = 0.02225 -0.00057 0.00013 0.00032 AFIX 43 H8A 4 -0.187879 0.357113 0.739905 11.00000 -1.20000 AFIX 0 C7A 1 -0.189884 0.177953 0.695410 11.00000 0.01540 0.02511 = 0.01875 0.00286 -0.00085 0.00050 C10B 1 0.381977 -0.225569 0.897078 11.00000 0.01748 0.03551 = 0.01836 0.00275 0.00202 0.00606 C11A 1 -0.340501 0.139388 0.596113 11.00000 0.01594 0.02996 = 0.01799 -0.00045 0.00116 -0.00020 AFIX 43 H11A 4 -0.380422 0.083249 0.559632 11.00000 -1.20000 AFIX 0 C10A 1 -0.377000 0.261343 0.603146 11.00000 0.01588 0.03427 = 0.01869 0.00241 0.00249 0.00476 C2A 1 -0.126883 -0.418048 0.618495 11.00000 0.02685 0.02260 = 0.02289 -0.00015 0.00180 -0.00093 AFIX 43 H2A 4 -0.152262 -0.498872 0.600904 11.00000 -1.20000 AFIX 0 C2B 1 0.127933 0.451336 0.884506 11.00000 0.02825 0.02426 = 0.02323 -0.00270 0.00074 -0.00107 AFIX 43 H2B 4 0.153065 0.532305 0.901998 11.00000 -1.20000 AFIX 0 C1A 1 -0.031055 -0.391171 0.659852 11.00000 0.02675 0.02525 = 0.02187 0.00087 0.00093 0.00331 AFIX 43 H1A 4 0.022055 -0.451410 0.676090 11.00000 -1.20000 AFIX 0 C7B 1 0.192005 -0.144973 0.807790 11.00000 0.01547 0.02765 = 0.01754 0.00271 -0.00006 0.00204 C12A 1 -0.477886 0.304011 0.554743 11.00000 0.02261 0.04571 = 0.02831 -0.00163 -0.00337 0.01341 AFIX 137 H12A 4 -0.497066 0.245352 0.509175 11.00000 -1.50000 H12B 4 -0.468539 0.388653 0.532724 11.00000 -1.50000 H12C 4 -0.533627 0.305762 0.590870 11.00000 -1.50000 AFIX 0 C3A 1 -0.285132 -0.291769 0.564905 11.00000 0.01660 0.03192 = 0.02902 -0.00777 -0.00144 -0.00145 AFIX 137 H3A 4 -0.330619 -0.254843 0.602684 11.00000 -1.50000 H3B 4 -0.312479 -0.374510 0.546451 11.00000 -1.50000 H3C 4 -0.283305 -0.236318 0.517152 11.00000 -1.50000 AFIX 0 C5B 1 0.137934 0.115178 0.852054 11.00000 0.01760 0.02464 = 0.02132 -0.00055 0.00041 -0.00037 AFIX 43 H5B 4 0.082962 0.061152 0.829543 11.00000 -1.20000 AFIX 0 C5A 1 -0.135065 -0.081635 0.649882 11.00000 0.01685 0.02450 = 0.02131 -0.00291 0.00005 -0.00173 AFIX 43 H5A 4 -0.080351 -0.028239 0.673631 11.00000 -1.20000 AFIX 0 C1B 1 0.030777 0.423475 0.846387 11.00000 0.02601 0.02509 = 0.02300 -0.00021 -0.00104 0.00352 AFIX 43 H1B 4 -0.023648 0.482957 0.832383 11.00000 -1.20000 AFIX 0 C12B 1 0.484470 -0.266769 0.943928 11.00000 0.02259 0.04657 = 0.02818 -0.00160 -0.00397 0.01469 AFIX 137 H22A 4 0.540977 -0.256110 0.909090 11.00000 -1.50000 H22B 4 0.479758 -0.355647 0.959414 11.00000 -1.50000 H22C 4 0.499225 -0.215304 0.993701 11.00000 -1.50000 AFIX 0 C3B 1 0.290331 0.326898 0.930896 11.00000 0.01681 0.03702 = 0.02949 -0.01041 -0.00153 -0.00150 AFIX 137 H13A 4 0.293045 0.264718 0.975423 11.00000 -1.50000 H13B 4 0.315862 0.408305 0.953361 11.00000 -1.50000 H13C 4 0.334536 0.298587 0.889490 11.00000 -1.50000 AFIX 0 H101 4 -0.065625 0.199390 0.771916 11.00000 0.05876 H102 4 0.065809 -0.172057 0.730586 11.00000 0.05742 HKLF 4 REM mo_MA_KLB_HL1_0m in P-1 REM R1 = 0.0466 for 4440 Fo > 4sig(Fo) and 0.0639 for all 5907 data REM 301 parameters refined using 0 restraints END WGHT 0.0733 0.6580 REM Highest difference peak 0.417, deepest hole -0.234, 1-sigma level 0.050 Q1 1 0.2249 -0.0995 0.8307 11.00000 0.05 0.42 Q2 1 -0.2190 0.1275 0.6663 11.00000 0.05 0.39 Q3 1 0.3005 -0.0862 0.8778 11.00000 0.05 0.35 Q4 1 0.3537 -0.2642 0.8649 11.00000 0.05 0.35 Q5 1 0.0650 0.2634 0.8440 11.00000 0.05 0.33 Q6 1 -0.2956 0.1112 0.6229 11.00000 0.05 0.33 Q7 1 -0.3484 0.2953 0.6254 11.00000 0.05 0.32 Q8 1 -0.2132 0.2348 0.7029 11.00000 0.05 0.32 Q9 1 0.2187 -0.2031 0.8013 11.00000 0.05 0.32 Q10 1 0.1313 0.1865 0.8564 11.00000 0.05 0.31 Q11 1 -0.1325 -0.1571 0.6465 11.00000 0.05 0.31 Q12 1 -0.1495 -0.2549 0.6198 11.00000 0.05 0.30 Q13 1 -0.0646 -0.2362 0.6576 11.00000 0.05 0.30 Q14 1 0.1506 0.2885 0.8827 11.00000 0.05 0.28 Q15 1 0.0857 0.4349 0.8581 11.00000 0.05 0.28 ; _shelx_res_checksum 73004 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 O1A O -0.10197(7) 0.13636(9) 0.74089(6) 0.0259(2) Uani 1 1 d . . . . . O1B O 0.10254(7) -0.10459(9) 0.76393(6) 0.0261(2) Uani 1 1 d . . . . . N3A N -0.22479(8) -0.03302(10) 0.62609(6) 0.0208(2) Uani 1 1 d . . . . . N3B N 0.22849(8) 0.06768(11) 0.87423(6) 0.0214(2) Uani 1 1 d . . . . . N1A N -0.02303(8) -0.26473(11) 0.67436(6) 0.0221(2) Uani 1 1 d . . . . . N2A N -0.17929(8) -0.30614(10) 0.60728(6) 0.0208(2) Uani 1 1 d . . . . . N2B N 0.18244(8) 0.34043(10) 0.89280(6) 0.0216(2) Uani 1 1 d . . . . . N1B N 0.02350(8) 0.29710(11) 0.83137(6) 0.0221(2) Uani 1 1 d . . . . . C6A C -0.24780(9) 0.09462(12) 0.64001(7) 0.0190(2) Uani 1 1 d . . . . . C4B C 0.11637(9) 0.24854(12) 0.86010(7) 0.0192(2) Uani 1 1 d . . . . . C6B C 0.25128(9) -0.06041(12) 0.86147(7) 0.0191(2) Uani 1 1 d . . . . . C4A C -0.11392(9) -0.21487(12) 0.64194(7) 0.0198(3) Uani 1 1 d . . . . . C11B C 0.34526(9) -0.10378(13) 0.90408(7) 0.0215(3) Uani 1 1 d . . . . . H11B H 0.3858 -0.0469 0.9395 0.026 Uiso 1 1 calc R U . . . C9A C -0.31798(10) 0.34163(13) 0.65764(8) 0.0239(3) Uani 1 1 d . . . . . H9A H -0.3408 0.4259 0.6639 0.029 Uiso 1 1 calc R U . . . C8B C 0.22893(10) -0.26738(13) 0.80033(8) 0.0236(3) Uani 1 1 d . . . . . H8B H 0.1895 -0.3248 0.7645 0.028 Uiso 1 1 calc R U . . . C9B C 0.32197(10) -0.30714(13) 0.84410(8) 0.0248(3) Uani 1 1 d . . . . . H9B H 0.3451 -0.3913 0.8379 0.030 Uiso 1 1 calc R U . . . C8A C -0.22649(10) 0.30052(12) 0.70293(8) 0.0225(3) Uani 1 1 d . . . . . H8A H -0.1879 0.3571 0.7399 0.027 Uiso 1 1 calc R U . . . C7A C -0.18988(9) 0.17795(12) 0.69541(7) 0.0200(3) Uani 1 1 d . . . . . C10B C 0.38198(10) -0.22557(13) 0.89708(7) 0.0238(3) Uani 1 1 d . . . . . C11A C -0.34050(9) 0.13939(12) 0.59611(7) 0.0214(3) Uani 1 1 d . . . . . H11A H -0.3804 0.0832 0.5596 0.026 Uiso 1 1 calc R U . . . C10A C -0.37700(9) 0.26134(13) 0.60315(7) 0.0229(3) Uani 1 1 d . . . . . C2A C -0.12688(10) -0.41805(13) 0.61849(8) 0.0242(3) Uani 1 1 d . . . . . H2A H -0.1523 -0.4989 0.6009 0.029 Uiso 1 1 calc R U . . . C2B C 0.12793(10) 0.45134(13) 0.88451(8) 0.0254(3) Uani 1 1 d . . . . . H2B H 0.1531 0.5323 0.9020 0.031 Uiso 1 1 calc R U . . . C1A C -0.03105(10) -0.39117(13) 0.65985(8) 0.0248(3) Uani 1 1 d . . . . . H1A H 0.0221 -0.4514 0.6761 0.030 Uiso 1 1 calc R U . . . C7B C 0.19200(9) -0.14497(12) 0.80779(7) 0.0204(3) Uani 1 1 d . . . . . C12A C -0.47789(11) 0.30401(15) 0.55474(9) 0.0327(3) Uani 1 1 d . . . . . H12A H -0.4971 0.2454 0.5092 0.049 Uiso 1 1 calc R U . . . H12B H -0.4685 0.3887 0.5327 0.049 Uiso 1 1 calc R U . . . H12C H -0.5336 0.3058 0.5909 0.049 Uiso 1 1 calc R U . . . C3A C -0.28513(10) -0.29177(14) 0.56490(8) 0.0262(3) Uani 1 1 d . . . . . H3A H -0.3306 -0.2548 0.6027 0.039 Uiso 1 1 calc R U . . . H3B H -0.3125 -0.3745 0.5465 0.039 Uiso 1 1 calc R U . . . H3C H -0.2833 -0.2363 0.5172 0.039 Uiso 1 1 calc R U . . . C5B C 0.13793(10) 0.11518(12) 0.85205(7) 0.0213(3) Uani 1 1 d . . . . . H5B H 0.0830 0.0612 0.8295 0.026 Uiso 1 1 calc R U . . . C5A C -0.13507(9) -0.08163(12) 0.64988(7) 0.0211(3) Uani 1 1 d . . . . . H5A H -0.0804 -0.0282 0.6736 0.025 Uiso 1 1 calc R U . . . C1B C 0.03078(10) 0.42347(13) 0.84639(8) 0.0250(3) Uani 1 1 d . . . . . H1B H -0.0236 0.4830 0.8324 0.030 Uiso 1 1 calc R U . . . C12B C 0.48447(11) -0.26677(16) 0.94393(9) 0.0330(3) Uani 1 1 d . . . . . H22A H 0.5410 -0.2561 0.9091 0.049 Uiso 1 1 calc R U . . . H22B H 0.4798 -0.3556 0.9594 0.049 Uiso 1 1 calc R U . . . H22C H 0.4992 -0.2153 0.9937 0.049 Uiso 1 1 calc R U . . . C3B C 0.29033(10) 0.32690(14) 0.93090(9) 0.0281(3) Uani 1 1 d . . . . . H13A H 0.2930 0.2647 0.9754 0.042 Uiso 1 1 calc R U . . . H13B H 0.3159 0.4083 0.9534 0.042 Uiso 1 1 calc R U . . . H13C H 0.3345 0.2986 0.8895 0.042 Uiso 1 1 calc R U . . . H101 H -0.0656(15) 0.199(2) 0.7719(12) 0.059(6) Uiso 1 1 d . . . . . H102 H 0.0658(15) -0.1721(19) 0.7306(12) 0.057(6) Uiso 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 O1A 0.0210(5) 0.0239(5) 0.0297(5) -0.0025(4) -0.0102(4) 0.0031(4) O1B 0.0203(5) 0.0261(5) 0.0287(5) -0.0030(4) -0.0099(4) 0.0036(4) N3A 0.0194(5) 0.0244(6) 0.0183(5) 0.0006(4) 0.0004(4) 0.0004(4) N3B 0.0190(5) 0.0263(6) 0.0183(5) 0.0005(4) -0.0003(4) 0.0015(4) N1A 0.0192(5) 0.0266(6) 0.0199(5) -0.0017(4) -0.0008(4) 0.0018(4) N2A 0.0178(5) 0.0246(6) 0.0197(5) -0.0013(4) 0.0008(4) -0.0014(4) N2B 0.0190(5) 0.0264(6) 0.0192(5) -0.0029(4) 0.0012(4) -0.0010(4) N1B 0.0194(5) 0.0240(6) 0.0221(5) -0.0002(4) -0.0005(4) 0.0021(4) C6A 0.0155(6) 0.0240(6) 0.0174(5) 0.0015(4) 0.0016(4) 0.0000(4) C4B 0.0158(6) 0.0240(6) 0.0173(5) -0.0007(4) 0.0005(4) -0.0005(4) C6B 0.0158(6) 0.0241(6) 0.0173(5) 0.0020(4) 0.0014(4) 0.0002(4) C4A 0.0164(6) 0.0249(7) 0.0178(5) -0.0012(4) 0.0007(4) -0.0009(4) C11B 0.0150(6) 0.0323(7) 0.0169(5) 0.0000(5) 0.0003(4) 0.0012(5) C9A 0.0228(7) 0.0255(7) 0.0233(6) 0.0014(5) 0.0028(5) 0.0056(5) C8B 0.0216(6) 0.0264(7) 0.0221(6) -0.0012(5) 0.0002(5) 0.0021(5) C9B 0.0221(7) 0.0292(7) 0.0232(6) 0.0006(5) 0.0033(5) 0.0068(5) C8A 0.0205(6) 0.0241(7) 0.0223(6) -0.0006(5) 0.0001(5) 0.0003(5) C7A 0.0154(6) 0.0251(7) 0.0188(5) 0.0029(4) -0.0009(4) 0.0005(4) C10B 0.0175(6) 0.0355(8) 0.0184(5) 0.0027(5) 0.0020(5) 0.0061(5) C11A 0.0159(6) 0.0300(7) 0.0180(5) -0.0004(5) 0.0012(4) -0.0002(5) C10A 0.0159(6) 0.0343(7) 0.0187(5) 0.0024(5) 0.0025(4) 0.0048(5) C2A 0.0269(7) 0.0226(7) 0.0229(6) -0.0001(5) 0.0018(5) -0.0009(5) C2B 0.0283(7) 0.0243(7) 0.0232(6) -0.0027(5) 0.0007(5) -0.0011(5) C1A 0.0267(7) 0.0252(7) 0.0219(6) 0.0009(5) 0.0009(5) 0.0033(5) C7B 0.0155(6) 0.0277(7) 0.0175(5) 0.0027(4) -0.0001(4) 0.0020(4) C12A 0.0226(7) 0.0457(9) 0.0283(7) -0.0016(6) -0.0034(6) 0.0134(6) C3A 0.0166(6) 0.0319(7) 0.0290(6) -0.0078(5) -0.0014(5) -0.0015(5) C5B 0.0176(6) 0.0246(7) 0.0213(6) -0.0006(5) 0.0004(5) -0.0004(4) C5A 0.0169(6) 0.0245(7) 0.0213(6) -0.0029(5) 0.0000(5) -0.0017(4) C1B 0.0260(7) 0.0251(7) 0.0230(6) -0.0002(5) -0.0010(5) 0.0035(5) C12B 0.0226(7) 0.0466(9) 0.0282(7) -0.0016(6) -0.0040(5) 0.0147(6) C3B 0.0168(6) 0.0370(8) 0.0295(7) -0.0104(6) -0.0015(5) -0.0015(5) 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' 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' H H 0.0000 0.0000 '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 C7A O1A H101 113.5(12) . . ? C7B O1B H102 112.7(11) . . ? C5A N3A C6A 122.39(11) . . ? C5B N3B C6B 122.30(11) . . ? C4A N1A C1A 106.00(11) . . ? C4A N2A C2A 106.94(11) . . ? C4A N2A C3A 128.22(11) . . ? C2A N2A C3A 124.84(11) . . ? C4B N2B C2B 106.76(11) . . ? C4B N2B C3B 128.00(11) . . ? C2B N2B C3B 125.23(11) . . ? C4B N1B C1B 106.04(11) . . ? C11A C6A N3A 115.14(11) . . ? C11A C6A C7A 117.99(12) . . ? N3A C6A C7A 126.81(11) . . ? N1B C4B N2B 110.70(11) . . ? N1B C4B C5B 121.14(11) . . ? N2B C4B C5B 128.12(11) . . ? C11B C6B N3B 115.15(11) . . ? C11B C6B C7B 118.14(12) . . ? N3B C6B C7B 126.64(11) . . ? N1A C4A N2A 110.65(11) . . ? N1A C4A C5A 121.06(11) . . ? N2A C4A C5A 128.20(11) . . ? C10B C11B C6B 123.23(12) . . ? C10B C11B H11B 118.4 . . ? C6B C11B H11B 118.4 . . ? C8A C9A C10A 121.00(12) . . ? C8A C9A H9A 119.5 . . ? C10A C9A H9A 119.5 . . ? C9B C8B C7B 121.38(12) . . ? C9B C8B H8B 119.3 . . ? C7B C8B H8B 119.3 . . ? C8B C9B C10B 120.95(13) . . ? C8B C9B H9B 119.5 . . ? C10B C9B H9B 119.5 . . ? C9A C8A C7A 121.41(12) . . ? C9A C8A H8A 119.3 . . ? C7A C8A H8A 119.3 . . ? O1A C7A C8A 121.68(11) . . ? O1A C7A C6A 119.48(11) . . ? C8A C7A C6A 118.82(11) . . ? C11B C10B C9B 117.51(12) . . ? C11B C10B C12B 120.92(12) . . ? C9B C10B C12B 121.55(13) . . ? C10A C11A C6A 123.38(12) . . ? C10A C11A H11A 118.3 . . ? C6A C11A H11A 118.3 . . ? C11A C10A C9A 117.39(11) . . ? C11A C10A C12A 121.03(12) . . ? C9A C10A C12A 121.57(12) . . ? C1A C2A N2A 106.69(12) . . ? C1A C2A H2A 126.7 . . ? N2A C2A H2A 126.7 . . ? C1B C2B N2B 106.88(12) . . ? C1B C2B H2B 126.6 . . ? N2B C2B H2B 126.6 . . ? N1A C1A C2A 109.72(12) . . ? N1A C1A H1A 125.1 . . ? C2A C1A H1A 125.1 . . ? O1B C7B C8B 121.76(11) . . ? O1B C7B C6B 119.45(11) . . ? C8B C7B C6B 118.78(11) . . ? C10A C12A H12A 109.5 . . ? C10A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C10A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? N2A C3A H3A 109.5 . . ? N2A C3A H3B 109.5 . . ? H3A C3A H3B 109.5 . . ? N2A C3A H3C 109.5 . . ? H3A C3A H3C 109.5 . . ? H3B C3A H3C 109.5 . . ? N3B C5B C4B 122.32(12) . . ? N3B C5B H5B 118.8 . . ? C4B C5B H5B 118.8 . . ? N3A C5A C4A 122.49(11) . . ? N3A C5A H5A 118.8 . . ? C4A C5A H5A 118.8 . . ? C2B C1B N1B 109.62(12) . . ? C2B C1B H1B 125.2 . . ? N1B C1B H1B 125.2 . . ? C10B C12B H22A 109.5 . . ? C10B C12B H22B 109.5 . . ? H22A C12B H22B 109.5 . . ? C10B C12B H22C 109.5 . . ? H22A C12B H22C 109.5 . . ? H22B C12B H22C 109.5 . . ? N2B C3B H13A 109.5 . . ? N2B C3B H13B 109.5 . . ? H13A C3B H13B 109.5 . . ? N2B C3B H13C 109.5 . . ? H13A C3B H13C 109.5 . . ? H13B C3B H13C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C7A 1.3523(14) . ? O1A H101 0.93(2) . ? O1B C7B 1.3519(14) . ? O1B H102 0.99(2) . ? N3A C5A 1.2815(16) . ? N3A C6A 1.4102(17) . ? N3B C5B 1.2811(16) . ? N3B C6B 1.4108(18) . ? N1A C4A 1.3345(16) . ? N1A C1A 1.3641(18) . ? N2A C4A 1.3615(16) . ? N2A C2A 1.3668(17) . ? N2A C3A 1.4607(16) . ? N2B C4B 1.3606(16) . ? N2B C2B 1.3680(18) . ? N2B C3B 1.4594(16) . ? N1B C4B 1.3341(16) . ? N1B C1B 1.3642(19) . ? C6A C11A 1.4002(17) . ? C6A C7A 1.4140(17) . ? C4B C5B 1.4507(19) . ? C6B C11B 1.3999(17) . ? C6B C7B 1.4142(17) . ? C4A C5A 1.4481(19) . ? C11B C10B 1.3847(19) . ? C11B H11B 0.9500 . ? C9A C8A 1.3850(17) . ? C9A C10A 1.3919(18) . ? C9A H9A 0.9500 . ? C8B C9B 1.3858(17) . ? C8B C7B 1.3928(19) . ? C8B H8B 0.9500 . ? C9B C10B 1.3922(19) . ? C9B H9B 0.9500 . ? C8A C7A 1.3930(19) . ? C8A H8A 0.9500 . ? C10B C12B 1.5092(18) . ? C11A C10A 1.3855(19) . ? C11A H11A 0.9500 . ? C10A C12A 1.5077(17) . ? C2A C1A 1.3643(18) . ? C2A H2A 0.9500 . ? C2B C1B 1.3614(18) . ? C2B H2B 0.9500 . ? C1A H1A 0.9500 . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? C3A H3A 0.9800 . ? C3A H3B 0.9800 . ? C3A H3C 0.9800 . ? C5B H5B 0.9500 . ? C5A H5A 0.9500 . ? C1B H1B 0.9500 . ? C12B H22A 0.9800 . ? C12B H22B 0.9800 . ? C12B H22C 0.9800 . ? C3B H13A 0.9800 . ? C3B H13B 0.9800 . ? C3B H13C 0.9800 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5A N3A C6A C11A 167.46(11) . . . . ? C5A N3A C6A C7A -15.43(19) . . . . ? C1B N1B C4B N2B -0.10(14) . . . . ? C1B N1B C4B C5B -178.06(11) . . . . ? C2B N2B C4B N1B 0.39(14) . . . . ? C3B N2B C4B N1B 179.57(11) . . . . ? C2B N2B C4B C5B 178.17(12) . . . . ? C3B N2B C4B C5B -2.6(2) . . . . ? C5B N3B C6B C11B -167.04(11) . . . . ? C5B N3B C6B C7B 16.30(19) . . . . ? C1A N1A C4A N2A -0.02(13) . . . . ? C1A N1A C4A C5A 176.76(11) . . . . ? C2A N2A C4A N1A -0.03(14) . . . . ? C3A N2A C4A N1A -179.46(11) . . . . ? C2A N2A C4A C5A -176.53(12) . . . . ? C3A N2A C4A C5A 4.0(2) . . . . ? N3B C6B C11B C10B -177.93(11) . . . . ? C7B C6B C11B C10B -0.97(18) . . . . ? C7B C8B C9B C10B -0.1(2) . . . . ? C10A C9A C8A C7A 0.33(19) . . . . ? C9A C8A C7A O1A -178.40(11) . . . . ? C9A C8A C7A C6A 0.19(19) . . . . ? C11A C6A C7A O1A 177.69(11) . . . . ? N3A C6A C7A O1A 0.66(19) . . . . ? C11A C6A C7A C8A -0.93(17) . . . . ? N3A C6A C7A C8A -177.96(11) . . . . ? C6B C11B C10B C9B 0.70(19) . . . . ? C6B C11B C10B C12B 179.41(12) . . . . ? C8B C9B C10B C11B -0.13(19) . . . . ? C8B C9B C10B C12B -178.83(12) . . . . ? N3A C6A C11A C10A 178.61(11) . . . . ? C7A C6A C11A C10A 1.24(18) . . . . ? C6A C11A C10A C9A -0.73(19) . . . . ? C6A C11A C10A C12A -179.54(12) . . . . ? C8A C9A C10A C11A -0.07(19) . . . . ? C8A C9A C10A C12A 178.74(12) . . . . ? C4A N2A C2A C1A 0.08(14) . . . . ? C3A N2A C2A C1A 179.52(11) . . . . ? C4B N2B C2B C1B -0.52(14) . . . . ? C3B N2B C2B C1B -179.73(11) . . . . ? C4A N1A C1A C2A 0.07(14) . . . . ? N2A C2A C1A N1A -0.09(14) . . . . ? C9B C8B C7B O1B 178.49(11) . . . . ? C9B C8B C7B C6B -0.13(19) . . . . ? C11B C6B C7B O1B -178.00(11) . . . . ? N3B C6B C7B O1B -1.42(19) . . . . ? C11B C6B C7B C8B 0.65(17) . . . . ? N3B C6B C7B C8B 177.23(11) . . . . ? C6B N3B C5B C4B -175.76(11) . . . . ? N1B C4B C5B N3B 175.33(11) . . . . ? N2B C4B C5B N3B -2.3(2) . . . . ? C6A N3A C5A C4A 174.63(11) . . . . ? N1A C4A C5A N3A -173.49(11) . . . . ? N2A C4A C5A N3A 2.7(2) . . . . ? N2B C2B C1B N1B 0.47(15) . . . . ? C4B N1B C1B C2B -0.23(14) . . . . ?