#------------------------------------------------------------------------------ #$Date: 2017-06-01 08:18:58 +0300 (Thu, 01 Jun 2017) $ #$Revision: 197130 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/83/7228350.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_7228350 loop_ _publ_author_name 'Castillo, Juan-Carlos' 'Rosero, Hern\'an-Alejandro' 'Portilla, Jaime' _publ_section_title ; Simple access toward 3-halo- and 3-nitro-pyrazolo[1,5-a]pyrimidines through a one-pot sequence ; _journal_issue 45 _journal_name_full 'RSC Adv.' _journal_page_first 28483 _journal_paper_doi 10.1039/C7RA04336H _journal_volume 7 _journal_year 2017 _chemical_formula_sum 'C150 H162 N36' _chemical_formula_weight 2469.15 _chemical_melting_point_gt 573 _chemical_name_systematic 1,3,5-tris(2-(tert-Butyl)pyrazolo[1,5-a]pyrimidin-7-yl)benzene _space_group_IT_number 148 _space_group_name_Hall '-R 3' _symmetry_cell_setting hexagonal _symmetry_space_group_name_Hall '-R 3' _symmetry_space_group_name_H-M 'R -3 :H' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-04-06 deposited with the CCDC. 2017-05-22 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_formula_units_Z 3 _cell_length_a 14.6829(3) _cell_length_b 14.6829(3) _cell_length_c 57.9972(11) _cell_measurement_reflns_used 23754 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 34.5670 _cell_measurement_theta_min 2.3820 _cell_volume 10828.3(4) _computing_cell_refinement 'Bruker APEX2 v2011.4-0' _computing_data_collection 'Bruker APEX2 v2011.4-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution Sir2011 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 512 _diffrn_detector_type 'PILATUS 200K' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.953 _diffrn_measurement_device_type '1/4chi goniometer' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_measurement_specimen_support 'magnetic support with MicroMount' _diffrn_radiation_monochromator 'Confocal Max Flux optic' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.953 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 92 _diffrn_reflns_limit_l_min -93 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.953 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 35.048 _diffrn_reflns_theta_min 1.639 _diffrn_source 'Microfocus rotating anode X-ray tube' _diffrn_source_current 24 _diffrn_source_power 50 _diffrn_source_size '0.2 mm x 0.2 mm fine focus' _diffrn_source_type 'Rigaku MicroMax-007HF' _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.764 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.136 _exptl_crystal_description block _exptl_crystal_F_000 3942 _exptl_crystal_preparation ', Luminescent' _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Methanol' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _platon_squeeze_details ; SQUEEZE implemented in Platon: Spek, A.L. J. Appl. Cryst. 2003, 36, 7-13. ; _refine_diff_density_max 0.531 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.095 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 295 _refine_ls_number_reflns 10167 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.190 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0672 _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^)+(0.0681P)^2^+32.3341P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2033 _refine_ls_wR_factor_ref 0.2055 _reflns_Friedel_coverage 0.000 _reflns_number_gt 8956 _reflns_number_total 10167 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra04336h2.cif _cod_data_source_block ar-sr _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_melting_point_gt' since the value was specified as 'more than' ('>') a certain temperature. The value '> 573' was changed to '573' - it should be numeric and without a unit designator. '_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_original_sg_symbol_H-M R-3 _cod_database_code 7228350 _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 0.993 _shelx_estimated_absorpt_t_max 0.993 _shelx_res_file ; ar-sr.res created by SHELXL-2014/7 TITL AR in R-3 CELL 0.71073 14.682894 14.682894 57.997194 90.0000 90.0000 120.0000 ZERR 3.00 0.000258 0.000258 0.001059 0.0000 0.0000 0.0000 LATT 3 SYMM -y, x-y, z SYMM -x+y,-x, z SFAC C H N UNIT 450 486 108 LIST 4 L.S. 12 BOND ACTA CONF SIZE 0.10 0.10 0.10 FMAP 2 PLAN 5 WGHT 0.068100 32.334099 FVAR 1.64288 MOLE 1 N1A 3 0.889621 0.715376 0.121235 11.00000 0.01621 0.01456 = 0.01926 -0.00042 0.00433 0.00718 N2A 3 0.817618 0.710752 0.136322 11.00000 0.01255 0.01183 = 0.01640 -0.00042 0.00171 0.00484 N3A 3 0.647268 0.588002 0.151160 11.00000 0.01655 0.01527 = 0.02045 0.00101 0.00373 0.00460 C1A 1 0.849417 0.616055 0.113759 11.00000 0.01850 0.01442 = 0.01718 -0.00087 0.00188 0.00779 C2A 1 0.753645 0.548047 0.124054 11.00000 0.01995 0.01260 = 0.01799 -0.00113 0.00179 0.00529 AFIX 43 H2A 2 0.712736 0.475849 0.121801 11.00000 -1.20000 AFIX 0 C3A 1 0.731878 0.609614 0.138267 11.00000 0.01527 0.01171 = 0.01613 0.00019 0.00060 0.00423 C4A 1 0.650641 0.667960 0.161966 11.00000 0.01614 0.01643 = 0.02133 0.00118 0.00438 0.00567 AFIX 43 H4A 2 0.592883 0.655370 0.170897 11.00000 -1.20000 AFIX 0 C5A 1 0.735513 0.771319 0.160976 11.00000 0.01441 0.01471 = 0.02201 -0.00041 0.00358 0.00633 AFIX 43 H5A 2 0.733327 0.824545 0.169210 11.00000 -1.20000 AFIX 0 C6A 1 0.821305 0.793320 0.147862 11.00000 0.01335 0.01159 = 0.01837 -0.00080 0.00045 0.00573 C7A 1 0.908127 0.591334 0.095926 11.00000 0.02512 0.01771 = 0.02034 -0.00148 0.00494 0.01099 C8A 1 0.946963 0.673825 0.076835 11.00000 0.03997 0.02933 = 0.02932 0.00790 0.01676 0.01951 AFIX 137 H8AA 2 0.984621 0.657772 0.065529 11.00000 -1.50000 H8AB 2 0.992778 0.741998 0.083298 11.00000 -1.50000 H8AC 2 0.887926 0.673613 0.069666 11.00000 -1.50000 AFIX 0 C9A 1 1.002285 0.592224 0.107245 11.00000 0.03443 0.04728 = 0.03107 -0.00418 0.00393 0.02878 AFIX 137 H9AA 2 1.041090 0.578300 0.095825 11.00000 -1.50000 H9AB 2 0.978111 0.539049 0.118979 11.00000 -1.50000 H9AC 2 1.046942 0.659885 0.114058 11.00000 -1.50000 AFIX 0 C10A 1 0.835354 0.484084 0.085459 11.00000 0.03821 0.02243 = 0.03256 -0.00719 0.00995 0.01236 AFIX 137 H10A 2 0.775026 0.483604 0.078934 11.00000 -1.50000 H10B 2 0.813006 0.431189 0.097224 11.00000 -1.50000 H10C 2 0.872037 0.469678 0.073603 11.00000 -1.50000 AFIX 0 C11A 1 0.913838 0.898686 0.146345 11.00000 0.01192 0.01120 = 0.02022 -0.00035 0.00072 0.00482 C12A 1 0.898817 0.984919 0.146291 11.00000 0.01253 0.01272 = 0.02211 -0.00117 0.00028 0.00658 AFIX 43 H12A 2 0.831028 0.974799 0.146218 11.00000 -1.20000 AFIX 0 MOLE 2 N1B 3 0.458078 0.043436 0.043058 11.00000 0.01504 0.01442 = 0.01848 -0.00134 -0.00002 0.00568 N2B 3 0.532535 0.037508 0.030534 11.00000 0.01564 0.01164 = 0.01657 -0.00097 -0.00213 0.00642 N3B 3 0.579244 -0.089972 0.018284 11.00000 0.02351 0.01593 = 0.02290 -0.00319 -0.00361 0.01163 C1B 1 0.392719 -0.055566 0.049911 11.00000 0.01730 0.01424 = 0.01847 -0.00055 -0.00203 0.00466 C2B 1 0.423051 -0.125672 0.041809 11.00000 0.02032 0.01311 = 0.02211 -0.00029 -0.00295 0.00571 AFIX 43 H2B 2 0.389179 -0.197901 0.044263 11.00000 -1.20000 AFIX 0 C3B 1 0.514016 -0.065405 0.029360 11.00000 0.01910 0.01247 = 0.01846 -0.00150 -0.00432 0.00728 C4B 1 0.662323 -0.010993 0.008816 11.00000 0.02213 0.01809 = 0.02241 -0.00309 -0.00122 0.01244 AFIX 43 H4B 2 0.708853 -0.025541 0.000979 11.00000 -1.20000 AFIX 0 C5B 1 0.685595 0.093711 0.009723 11.00000 0.01843 0.01538 = 0.02071 -0.00264 -0.00119 0.00950 AFIX 43 H5B 2 0.745919 0.145890 0.002573 11.00000 -1.20000 AFIX 0 C6B 1 0.620196 0.119734 0.021055 11.00000 0.01513 0.01264 = 0.01608 -0.00115 -0.00222 0.00703 C7B 1 0.298858 -0.078216 0.064537 11.00000 0.01714 0.01973 = 0.02335 -0.00173 0.00104 0.00374 C8B 1 0.333283 0.000433 0.084273 11.00000 0.02060 0.02798 = 0.02640 -0.00757 0.00112 0.00641 AFIX 137 H8BA 2 0.369658 0.070619 0.078183 11.00000 -1.50000 H8BB 2 0.379329 -0.009678 0.094358 11.00000 -1.50000 H8BC 2 0.272582 -0.010024 0.092728 11.00000 -1.50000 AFIX 0 C9B 1 0.217999 -0.068750 0.049812 11.00000 0.02138 0.06896 = 0.02879 -0.00357 -0.00174 0.02144 AFIX 137 H9BA 2 0.249032 0.000997 0.043551 11.00000 -1.50000 H9BB 2 0.158521 -0.082402 0.059158 11.00000 -1.50000 H9BC 2 0.195517 -0.118882 0.037453 11.00000 -1.50000 AFIX 0 C10B 1 0.249579 -0.188677 0.074350 11.00000 0.04600 0.02174 = 0.05810 0.00918 0.02686 0.00734 AFIX 137 H10D 2 0.223389 -0.238817 0.061978 11.00000 -1.50000 H10E 2 0.192638 -0.200928 0.084413 11.00000 -1.50000 H10F 2 0.301544 -0.196141 0.082863 11.00000 -1.50000 AFIX 0 C11B 1 0.641650 0.228503 0.022739 11.00000 0.01498 0.01205 = 0.01560 -0.00059 -0.00066 0.00709 C12B 1 0.562216 0.253584 0.022899 11.00000 0.01344 0.01303 = 0.01711 -0.00015 -0.00127 0.00626 AFIX 43 H12B 2 0.492227 0.200223 0.023116 11.00000 -1.20000 AFIX 0 MOLE 3 C1S 1 0.951931 0.012821 0.018460 10.50000 0.09825 0.08766 = 0.06231 0.00254 0.01911 0.04800 AFIX 3 H1S 2 0.932274 0.030912 0.032789 10.50000 -1.20000 AFIX 0 C2S 1 0.943432 0.049917 -0.000640 10.50000 0.10255 0.11099 = 0.10342 0.03373 0.00151 0.05976 AFIX 3 H2S 2 0.892964 0.072695 -0.002590 10.50000 -1.20000 AFIX 0 HKLF 4 REM AR in R-3 REM R1 = 0.0672 for 8956 Fo > 4sig(Fo) and 0.0727 for all 10167 data REM 295 parameters refined using 0 restraints END WGHT 0.0680 32.3481 REM Highest difference peak 0.531, deepest hole -0.367, 1-sigma level 0.095 Q1 1 0.6001 0.2399 0.0242 11.00000 0.05 0.53 Q2 1 0.9040 0.0689 0.0237 11.00000 0.05 0.53 Q3 1 1.0000 0.0000 0.0000 10.16667 0.05 0.52 Q4 1 0.5676 0.6385 0.1610 11.00000 0.05 0.48 Q5 1 1.0989 0.8215 0.1152 11.00000 0.05 0.47 ; _shelx_res_checksum 12380 loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' 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 N1A N 0.88962(9) 0.71538(9) 0.12123(2) 0.0169(2) Uani 1 1 d . . . N2A N 0.81762(9) 0.71075(8) 0.13632(2) 0.01415(19) Uani 1 1 d . . . N3A N 0.64727(10) 0.58800(10) 0.15116(2) 0.0189(2) Uani 1 1 d . . . C1A C 0.84942(11) 0.61606(10) 0.11376(2) 0.0169(2) Uani 1 1 d . . . C2A C 0.75365(11) 0.54805(10) 0.12405(2) 0.0181(2) Uani 1 1 d . . . H2A H 0.7127 0.4758 0.1218 0.022 Uiso 1 1 calc R U . C3A C 0.73188(10) 0.60961(10) 0.13827(2) 0.0155(2) Uani 1 1 d . . . C4A C 0.65064(11) 0.66796(11) 0.16197(3) 0.0191(2) Uani 1 1 d . . . H4A H 0.5929 0.6554 0.1709 0.023 Uiso 1 1 calc R U . C5A C 0.73551(10) 0.77132(10) 0.16098(2) 0.0175(2) Uani 1 1 d . . . H5A H 0.7333 0.8245 0.1692 0.021 Uiso 1 1 calc R U . C6A C 0.82131(10) 0.79332(10) 0.14786(2) 0.0147(2) Uani 1 1 d . . . C7A C 0.90813(12) 0.59133(11) 0.09593(3) 0.0209(3) Uani 1 1 d . . . C8A C 0.94696(16) 0.67383(15) 0.07684(3) 0.0319(4) Uani 1 1 d . . . H8AA H 0.9846 0.6578 0.0655 0.048 Uiso 1 1 calc R U . H8AB H 0.9928 0.7420 0.0833 0.048 Uiso 1 1 calc R U . H8AC H 0.8879 0.6736 0.0697 0.048 Uiso 1 1 calc R U . C9A C 1.00228(16) 0.59222(18) 0.10725(3) 0.0339(4) Uani 1 1 d . . . H9AA H 1.0411 0.5783 0.0958 0.051 Uiso 1 1 calc R U . H9AB H 0.9781 0.5390 0.1190 0.051 Uiso 1 1 calc R U . H9AC H 1.0469 0.6599 0.1141 0.051 Uiso 1 1 calc R U . C10A C 0.83535(16) 0.48408(14) 0.08546(3) 0.0323(4) Uani 1 1 d . . . H10A H 0.7750 0.4836 0.0789 0.048 Uiso 1 1 calc R U . H10B H 0.8130 0.4312 0.0972 0.048 Uiso 1 1 calc R U . H10C H 0.8720 0.4697 0.0736 0.048 Uiso 1 1 calc R U . C11A C 0.91384(10) 0.89869(10) 0.14634(2) 0.0149(2) Uani 1 1 d . . . C12A C 0.89882(10) 0.98492(10) 0.14629(2) 0.0157(2) Uani 1 1 d . . . H12A H 0.8310 0.9748 0.1462 0.019 Uiso 1 1 calc R U . N1B N 0.45808(9) 0.04344(9) 0.04306(2) 0.0167(2) Uani 1 1 d . . . N2B N 0.53254(9) 0.03751(9) 0.03053(2) 0.01480(19) Uani 1 1 d . . . N3B N 0.57924(10) -0.08997(10) 0.01828(2) 0.0200(2) Uani 1 1 d . . . C1B C 0.39272(11) -0.05557(11) 0.04991(2) 0.0181(2) Uani 1 1 d . . . C2B C 0.42305(11) -0.12567(11) 0.04181(3) 0.0197(2) Uani 1 1 d . . . H2B H 0.3892 -0.1979 0.0443 0.024 Uiso 1 1 calc R U . C3B C 0.51402(11) -0.06541(10) 0.02936(2) 0.0169(2) Uani 1 1 d . . . C4B C 0.66232(12) -0.01099(11) 0.00882(3) 0.0198(2) Uani 1 1 d . . . H4B H 0.7089 -0.0255 0.0010 0.024 Uiso 1 1 calc R U . C5B C 0.68559(11) 0.09371(11) 0.00972(2) 0.0177(2) Uani 1 1 d . . . H5B H 0.7459 0.1459 0.0026 0.021 Uiso 1 1 calc R U . C6B C 0.62020(10) 0.11973(10) 0.02106(2) 0.0146(2) Uani 1 1 d . . . C7B C 0.29886(12) -0.07822(12) 0.06454(3) 0.0225(3) Uani 1 1 d . . . C8B C 0.33328(13) 0.00043(14) 0.08427(3) 0.0275(3) Uani 1 1 d . . . H8BA H 0.3697 0.0706 0.0782 0.041 Uiso 1 1 calc R U . H8BB H 0.3793 -0.0097 0.0944 0.041 Uiso 1 1 calc R U . H8BC H 0.2726 -0.0100 0.0927 0.041 Uiso 1 1 calc R U . C9B C 0.21800(15) -0.0687(2) 0.04981(3) 0.0402(5) Uani 1 1 d . . . H9BA H 0.2490 0.0010 0.0436 0.060 Uiso 1 1 calc R U . H9BB H 0.1585 -0.0824 0.0592 0.060 Uiso 1 1 calc R U . H9BC H 0.1955 -0.1189 0.0375 0.060 Uiso 1 1 calc R U . C10B C 0.2496(2) -0.18868(16) 0.07435(5) 0.0462(6) Uani 1 1 d . . . H10D H 0.2234 -0.2388 0.0620 0.069 Uiso 1 1 calc R U . H10E H 0.1926 -0.2009 0.0844 0.069 Uiso 1 1 calc R U . H10F H 0.3015 -0.1961 0.0829 0.069 Uiso 1 1 calc R U . C11B C 0.64165(10) 0.22850(10) 0.02274(2) 0.0141(2) Uani 1 1 d . . . C12B C 0.56222(10) 0.25358(10) 0.02290(2) 0.0147(2) Uani 1 1 d . . . H12B H 0.4922 0.2002 0.0231 0.018 Uiso 1 1 calc R U . C1S C 0.9519(7) 0.0128(8) 0.01846(14) 0.082(2) Uani 0.5 1 d . . P H1S H 0.9323 0.0309 0.0328 0.098 Uiso 0.5 1 d R U P C2S C 0.9434(10) 0.0499(11) -0.0006(2) 0.103(3) Uani 0.5 1 d . . P H2S H 0.8930 0.0727 -0.0026 0.123 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 N1A 0.0162(5) 0.0146(5) 0.0193(5) -0.0004(4) 0.0043(4) 0.0072(4) N2A 0.0125(4) 0.0118(4) 0.0164(4) -0.0004(3) 0.0017(3) 0.0048(3) N3A 0.0166(5) 0.0153(5) 0.0204(5) 0.0010(4) 0.0037(4) 0.0046(4) C1A 0.0185(5) 0.0144(5) 0.0172(5) -0.0009(4) 0.0019(4) 0.0078(4) C2A 0.0199(6) 0.0126(5) 0.0180(5) -0.0011(4) 0.0018(4) 0.0053(4) C3A 0.0153(5) 0.0117(5) 0.0161(5) 0.0002(4) 0.0006(4) 0.0042(4) C4A 0.0161(5) 0.0164(5) 0.0213(6) 0.0012(4) 0.0044(4) 0.0057(4) C5A 0.0144(5) 0.0147(5) 0.0220(6) -0.0004(4) 0.0036(4) 0.0063(4) C6A 0.0134(5) 0.0116(5) 0.0184(5) -0.0008(4) 0.0005(4) 0.0057(4) C7A 0.0251(6) 0.0177(6) 0.0203(6) -0.0015(4) 0.0049(5) 0.0110(5) C8A 0.0400(9) 0.0293(8) 0.0293(8) 0.0079(6) 0.0168(7) 0.0195(7) C9A 0.0344(9) 0.0473(11) 0.0311(8) -0.0042(7) 0.0039(7) 0.0288(8) C10A 0.0382(9) 0.0224(7) 0.0326(8) -0.0072(6) 0.0099(7) 0.0124(7) C11A 0.0119(5) 0.0112(5) 0.0202(5) -0.0004(4) 0.0007(4) 0.0048(4) C12A 0.0125(5) 0.0127(5) 0.0221(6) -0.0012(4) 0.0003(4) 0.0066(4) N1B 0.0150(5) 0.0144(4) 0.0185(5) -0.0013(4) 0.0000(4) 0.0057(4) N2B 0.0156(4) 0.0116(4) 0.0166(4) -0.0010(3) -0.0021(3) 0.0064(4) N3B 0.0235(5) 0.0159(5) 0.0229(5) -0.0032(4) -0.0036(4) 0.0116(4) C1B 0.0173(5) 0.0142(5) 0.0185(5) -0.0005(4) -0.0020(4) 0.0047(4) C2B 0.0203(6) 0.0131(5) 0.0221(6) -0.0003(4) -0.0030(5) 0.0057(4) C3B 0.0191(5) 0.0125(5) 0.0185(5) -0.0015(4) -0.0043(4) 0.0073(4) C4B 0.0221(6) 0.0181(6) 0.0224(6) -0.0031(5) -0.0012(5) 0.0124(5) C5B 0.0184(5) 0.0154(5) 0.0207(6) -0.0026(4) -0.0012(4) 0.0095(4) C6B 0.0151(5) 0.0126(5) 0.0161(5) -0.0012(4) -0.0022(4) 0.0070(4) C7B 0.0171(6) 0.0197(6) 0.0234(6) -0.0017(5) 0.0010(5) 0.0037(5) C8B 0.0206(6) 0.0280(7) 0.0264(7) -0.0076(6) 0.0011(5) 0.0064(6) C9B 0.0214(7) 0.0690(15) 0.0288(8) -0.0036(9) -0.0017(6) 0.0214(9) C10B 0.0460(12) 0.0217(8) 0.0581(13) 0.0092(8) 0.0269(10) 0.0073(8) C11B 0.0150(5) 0.0121(5) 0.0156(5) -0.0006(4) -0.0007(4) 0.0071(4) C12B 0.0134(5) 0.0130(5) 0.0171(5) -0.0001(4) -0.0013(4) 0.0063(4) C1S 0.098(7) 0.088(5) 0.062(4) 0.003(4) 0.019(4) 0.048(5) C2S 0.103(8) 0.111(8) 0.103(7) 0.034(6) 0.002(5) 0.060(6) 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' N N 0.0061 0.0033 '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 C1A N1A N2A 104.31(11) . . N1A N2A C6A 126.38(11) . . N1A N2A C3A 112.03(11) . . C6A N2A C3A 121.51(11) . . C4A N3A C3A 115.98(12) . . N1A C1A C2A 112.31(12) . . N1A C1A C7A 119.41(12) . . C2A C1A C7A 128.28(12) . . C3A C2A C1A 105.67(12) . . N3A C3A C2A 132.04(12) . . N3A C3A N2A 122.23(12) . . C2A C3A N2A 105.65(11) . . N3A C4A C5A 124.41(13) . . C6A C5A C4A 119.63(12) . . N2A C6A C5A 116.23(12) . . N2A C6A C11A 120.91(11) . . C5A C6A C11A 122.85(12) . . C1A C7A C10A 109.54(13) . . C1A C7A C9A 109.20(13) . . C10A C7A C9A 110.23(15) . . C1A C7A C8A 109.85(12) . . C10A C7A C8A 108.84(14) . . C9A C7A C8A 109.17(15) . . C12A C11A C12A 119.89(13) 2_765 . C12A C11A C6A 121.54(11) 2_765 . C12A C11A C6A 118.46(11) . . C11A C12A C11A 120.11(13) 3_675 . C1B N1B N2B 104.66(11) . . N1B N2B C6B 126.52(11) . . N1B N2B C3B 111.70(11) . . C6B N2B C3B 121.65(12) . . C4B N3B C3B 115.82(12) . . N1B C1B C2B 112.43(13) . . N1B C1B C7B 119.08(13) . . C2B C1B C7B 128.48(13) . . C3B C2B C1B 105.50(12) . . N3B C3B C2B 131.98(13) . . N3B C3B N2B 122.30(13) . . C2B C3B N2B 105.70(12) . . N3B C4B C5B 124.33(13) . . C6B C5B C4B 120.38(13) . . N2B C6B C5B 115.48(12) . . N2B C6B C11B 122.00(11) . . C5B C6B C11B 122.52(12) . . C1B C7B C10B 109.97(15) . . C1B C7B C8B 109.62(12) . . C10B C7B C8B 109.20(16) . . C1B C7B C9B 109.42(13) . . C10B C7B C9B 109.30(17) . . C8B C7B C9B 109.30(16) . . C12B C11B C12B 119.70(12) . 2_655 C12B C11B C6B 122.51(11) . . C12B C11B C6B 117.70(11) 2_655 . C11B C12B C11B 120.29(12) . 3_665 C2S C1S C2S 60.8(5) . 12_545 C2S C1S C1S 100.3(9) . 3_765 C2S C1S C1S 115.8(6) 12_545 3_765 C2S C1S C1S 118.8(7) . 2_645 C2S C1S C1S 76.7(9) 12_545 2_645 C1S C1S C1S 59.996(1) 3_765 2_645 C2S C1S C2S 50.5(5) . 11_665 C2S C1S C2S 95.7(9) 12_545 11_665 C1S C1S C2S 51.4(7) 3_765 11_665 C1S C1S C2S 97.5(7) 2_645 11_665 C1S C2S C2S 64.5(8) . 12_545 C1S C2S C2S 83.4(10) . 11_665 C2S C2S C2S 119.7(2) 12_545 11_665 C1S C2S C1S 118.1(11) . 11_665 C2S C2S C1S 96.6(10) 12_545 11_665 C2S C2S C1S 54.7(8) 11_665 11_665 C1S C2S C1S 97.7(10) . 12_545 C2S C2S C1S 46.1(7) 12_545 12_545 C2S C2S C1S 95.3(8) 11_665 12_545 C1S C2S C1S 52.0(8) 11_665 12_545 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1A C1A 1.3425(17) . N1A N2A 1.3476(15) . N2A C6A 1.3620(16) . N2A C3A 1.3904(16) . N3A C4A 1.3097(18) . N3A C3A 1.3450(18) . C1A C2A 1.3881(19) . C1A C7A 1.502(2) . C2A C3A 1.3739(19) . C4A C5A 1.4029(19) . C5A C6A 1.3648(18) . C6A C11A 1.4646(18) . C7A C10A 1.519(2) . C7A C9A 1.525(3) . C7A C8A 1.526(2) . C11A C12A 1.3885(18) 2_765 C11A C12A 1.3896(18) . C12A C11A 1.3884(18) 3_675 N1B C1B 1.3405(17) . N1B N2B 1.3511(16) . N2B C6B 1.3647(17) . N2B C3B 1.3968(17) . N3B C4B 1.311(2) . N3B C3B 1.3437(19) . C1B C2B 1.392(2) . C1B C7B 1.507(2) . C2B C3B 1.381(2) . C4B C5B 1.3992(19) . C5B C6B 1.3664(19) . C6B C11B 1.4684(17) . C7B C10B 1.518(3) . C7B C8B 1.522(2) . C7B C9B 1.524(3) . C11B C12B 1.3876(18) . C11B C12B 1.3931(18) 2_655 C12B C11B 1.3931(18) 3_665 C1S C2S 1.268(12) . C1S C2S 1.403(15) 12_545 C1S C1S 1.414(14) 3_765 C1S C1S 1.414(14) 2_645 C1S C2S 1.747(16) 11_665 C2S C2S 1.357(10) 12_545 C2S C2S 1.357(10) 11_665 C2S C1S 1.403(15) 11_665 C2S C1S 1.747(16) 12_545 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_4 C1A N1A N2A C6A -177.26(13) . . C1A N1A N2A C3A -0.58(15) . . N2A N1A C1A C2A -0.76(16) . . N2A N1A C1A C7A 178.40(12) . . N1A C1A C2A C3A 1.78(17) . . C7A C1A C2A C3A -177.29(14) . . C4A N3A C3A C2A -176.69(15) . . C4A N3A C3A N2A -0.5(2) . . C1A C2A C3A N3A 174.67(15) . . C1A C2A C3A N2A -1.99(15) . . N1A N2A C3A N3A -175.40(13) . . C6A N2A C3A N3A 1.5(2) . . N1A N2A C3A C2A 1.66(15) . . C6A N2A C3A C2A 178.53(12) . . C3A N3A C4A C5A -0.6(2) . . N3A C4A C5A C6A 0.7(2) . . N1A N2A C6A C5A 175.12(13) . . C3A N2A C6A C5A -1.27(19) . . N1A N2A C6A C11A -6.0(2) . . C3A N2A C6A C11A 177.65(12) . . C4A C5A C6A N2A 0.2(2) . . C4A C5A C6A C11A -178.65(13) . . N1A C1A C7A C10A -164.29(15) . . C2A C1A C7A C10A 14.7(2) . . N1A C1A C7A C9A 74.91(18) . . C2A C1A C7A C9A -106.08(18) . . N1A C1A C7A C8A -44.8(2) . . C2A C1A C7A C8A 134.23(17) . . N2A C6A C11A C12A -39.55(19) . 2_765 C5A C6A C11A C12A 139.29(14) . 2_765 N2A C6A C11A C12A 144.14(13) . . C5A C6A C11A C12A -37.0(2) . . C12A C11A C12A C11A -0.4(3) 2_765 3_675 C6A C11A C12A C11A 175.92(9) . 3_675 C1B N1B N2B C6B -175.68(12) . . C1B N1B N2B C3B 0.30(14) . . N2B N1B C1B C2B -0.66(16) . . N2B N1B C1B C7B 179.93(12) . . N1B C1B C2B C3B 0.77(16) . . C7B C1B C2B C3B -179.88(14) . . C4B N3B C3B C2B -177.32(15) . . C4B N3B C3B N2B 0.7(2) . . C1B C2B C3B N3B 177.74(15) . . C1B C2B C3B N2B -0.54(15) . . N1B N2B C3B N3B -178.32(12) . . C6B N2B C3B N3B -2.1(2) . . N1B N2B C3B C2B 0.16(15) . . C6B N2B C3B C2B 176.37(12) . . C3B N3B C4B C5B 0.2(2) . . N3B C4B C5B C6B 0.2(2) . . N1B N2B C6B C5B 177.98(12) . . C3B N2B C6B C5B 2.36(18) . . N1B N2B C6B C11B -2.7(2) . . C3B N2B C6B C11B -178.36(12) . . C4B C5B C6B N2B -1.45(19) . . C4B C5B C6B C11B 179.28(13) . . N1B C1B C7B C10B -168.22(16) . . C2B C1B C7B C10B 12.5(2) . . N1B C1B C7B C8B -48.15(19) . . C2B C1B C7B C8B 132.54(16) . . N1B C1B C7B C9B 71.71(18) . . C2B C1B C7B C9B -107.60(19) . . N2B C6B C11B C12B -33.16(19) . . C5B C6B C11B C12B 146.07(14) . . N2B C6B C11B C12B 150.41(12) . 2_655 C5B C6B C11B C12B -30.37(19) . 2_655 C12B C11B C12B C11B 1.3(3) 2_655 3_665 C6B C11B C12B C11B -175.05(8) . 3_665 C1S C1S C2S C2S 113.9(9) 3_765 12_545 C1S C1S C2S C2S 52.5(12) 2_645 12_545 C2S C1S C2S C2S 127.5(7) 11_665 12_545 C2S C1S C2S C2S -127.5(7) 12_545 11_665 C1S C1S C2S C2S -13.6(11) 3_765 11_665 C1S C1S C2S C2S -74.9(15) 2_645 11_665 C2S C1S C2S C1S -83.7(10) 12_545 11_665 C1S C1S C2S C1S 30.2(17) 3_765 11_665 C1S C1S C2S C1S -31(2) 2_645 11_665 C2S C1S C2S C1S 43.8(7) 11_665 11_665 C2S C1S C2S C1S -33.0(6) 12_545 12_545 C1S C1S C2S C1S 80.9(9) 3_765 12_545 C1S C1S C2S C1S 19.6(13) 2_645 12_545 C2S C1S C2S C1S 94.5(7) 11_665 12_545 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.086 77 22 ' ' 2 0.000 0.000 0.500 294 92 ' ' 3 0.000 0.000 0.914 77 22 ' ' 4 0.333 0.667 0.167 296 92 ' ' 5 0.333 0.667 0.580 77 22 ' ' 6 0.333 0.667 0.753 77 22 ' ' 7 0.667 0.333 0.833 296 92 ' ' 8 0.667 0.333 0.247 77 22 ' ' 9 0.667 0.333 0.420 77 22 ' '