#------------------------------------------------------------------------------ #$Date: 2019-11-13 06:22:57 +0200 (Wed, 13 Nov 2019) $ #$Revision: 227690 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/72/7157201.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_7157201 loop_ _publ_author_name 'Galeev, Andrew R.' 'Mokrushin, Ivan G.' 'Dmitriev, Maksim V.' 'Mashevskaya, Irina V.' 'Maslivets, Andrey N.' 'Rubin, Michael' _publ_section_title ; Synthesis of meta-Substituted Anilines via Three-Component Reaction of Acetone, Amines, and 1,3-Diketones ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB02120E _journal_year 2019 _chemical_formula_moiety 'C20 H17 N O3' _chemical_formula_sum 'C20 H17 N O3' _chemical_formula_weight 319.35 _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 _atom_sites_solution_primary direct _audit_creation_date 2016-04-13 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2019-03-24 deposited with the CCDC. 2019-11-12 downloaded from the CCDC. ; _cell_angle_alpha 82.664(14) _cell_angle_beta 79.063(17) _cell_angle_gamma 76.170(16) _cell_formula_units_Z 2 _cell_length_a 7.6883(17) _cell_length_b 9.4591(15) _cell_length_c 11.7328(19) _cell_measurement_reflns_used 1861 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 27.8870 _cell_measurement_theta_min 4.0570 _cell_volume 810.4(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 295.15 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.4752 _diffrn_detector_type Ruby _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.836 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -4.00 94.00 1.0000 5.5000 omega____ theta____ kappa____ phi______ frames - 14.0072 77.0000 -60.0000 98 #__ type_ start__ end____ width___ exp.time_ 2 omega -22.00 86.00 1.0000 5.5000 omega____ theta____ kappa____ phi______ frames - 14.0072 77.0000 90.0000 108 #__ type_ start__ end____ width___ exp.time_ 3 omega -45.00 57.00 1.0000 5.5000 omega____ theta____ kappa____ phi______ frames - -14.5541 77.0000 -180.0000 102 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'New Xcalibur, Ruby' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0563322000 _diffrn_orient_matrix_UB_12 -0.0152984000 _diffrn_orient_matrix_UB_13 -0.0542870000 _diffrn_orient_matrix_UB_21 -0.0003181000 _diffrn_orient_matrix_UB_22 0.0753626000 _diffrn_orient_matrix_UB_23 -0.0130852000 _diffrn_orient_matrix_UB_31 0.0781495000 _diffrn_orient_matrix_UB_32 -0.0097441000 _diffrn_orient_matrix_UB_33 0.0264836000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_unetI/netI 0.0547 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.836 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6254 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.836 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 29.439 _diffrn_reflns_theta_min 2.964 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.72059 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear yellowish yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier yellowish _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.253 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 3760 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0592 _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^)+(0.0892P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1545 _refine_ls_wR_factor_ref 0.1868 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2429 _reflns_number_total 3760 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob02120e2.cif _cod_data_source_block psu-345(md-356) _cod_database_code 7157201 _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. ; _reflns_odcompleteness_completeness 99.76 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C17(H17), C18(H18), C19(H19), C20(H20) 2.b Idealised Me refined as rotating group: C14(H14A,H14B,H14C) ; _shelx_res_file ; psu-345(md-356).res created by SHELXL-2014/7 TITL PSU-345(MD-356) in P-1 #2 REM reset to P-1 #2 CELL 0.71073 7.688311 9.459052 11.732823 82.6645 79.0632 76.1703 ZERR 2 0.001702 0.001522 0.001934 0.0137 0.0171 0.0164 LATT 1 SFAC C H N O UNIT 40 34 2 6 EQIV $1 -X,1-Y,1-Z L.S. 4 PLAN 20 TEMP 22 HTAB O3 O1_$1 BOND fmap 2 acta 52 MORE -1 BOND $H CONF OMIT -4 5 2 OMIT 0 10 6 OMIT 9 -2 2 REM REM REM WGHT 0.089200 FVAR 12.74645 O1 4 0.236588 0.745343 0.525813 11.00000 0.05463 0.04230 = 0.06859 -0.00827 0.00098 -0.01500 O2 4 0.375802 0.597147 0.387142 11.00000 0.05311 0.03786 = 0.05574 0.00216 0.00300 -0.01211 O3 4 0.013904 0.099534 0.306862 11.00000 0.05365 0.06439 = 0.08279 -0.02489 -0.01749 -0.01045 H3 2 -0.047328 0.145867 0.364966 11.00000 0.08672 N1 3 0.182139 0.133141 0.489034 11.00000 0.05700 0.04173 = 0.05326 0.00003 -0.00145 -0.02075 H1 2 0.129671 0.074966 0.529343 11.00000 0.06864 C1 1 0.047815 0.385832 0.719268 11.00000 0.03893 0.04827 = 0.04522 0.00163 -0.00782 -0.01104 C2 1 0.075202 0.263352 0.659748 11.00000 0.04176 0.04591 = 0.04836 0.00641 -0.00938 -0.01502 AFIX 43 H2 2 0.030093 0.183524 0.697004 11.00000 -1.20000 AFIX 0 C3 1 0.167714 0.255407 0.546284 11.00000 0.03863 0.03857 = 0.04897 0.00270 -0.01167 -0.00994 C4 1 0.234036 0.374575 0.491751 11.00000 0.04004 0.04092 = 0.04652 0.00209 -0.00621 -0.01014 AFIX 43 H4 2 0.297041 0.371708 0.415836 11.00000 -1.20000 AFIX 0 C5 1 0.206758 0.497899 0.549975 11.00000 0.03562 0.03956 = 0.04858 0.00266 -0.00870 -0.00742 C6 1 0.115222 0.505086 0.662711 11.00000 0.04268 0.04053 = 0.05145 -0.00221 -0.01055 -0.00791 AFIX 43 H6 2 0.098551 0.588923 0.700776 11.00000 -1.20000 AFIX 0 C7 1 -0.054796 0.390416 0.839505 11.00000 0.04723 0.05714 = 0.04861 -0.00087 -0.00498 -0.01889 C8 1 -0.033177 0.267130 0.917396 11.00000 0.06400 0.07718 = 0.05686 0.01102 -0.00704 -0.01615 AFIX 43 H8 2 0.046960 0.181318 0.894421 11.00000 -1.20000 AFIX 0 C9 1 -0.130222 0.271300 1.028983 11.00000 0.08000 0.11125 = 0.06069 0.02087 -0.00839 -0.03130 AFIX 43 H9 2 -0.113569 0.188557 1.081293 11.00000 -1.20000 AFIX 0 C10 1 -0.250235 0.395447 1.063319 11.00000 0.07546 0.13657 = 0.05268 -0.00762 0.00716 -0.04199 AFIX 43 H10 2 -0.317043 0.396825 1.138229 11.00000 -1.20000 AFIX 0 C11 1 -0.271983 0.517155 0.987814 11.00000 0.07844 0.09361 = 0.07018 -0.02177 0.01399 -0.02497 AFIX 43 H11 2 -0.352981 0.602364 1.011281 11.00000 -1.20000 AFIX 0 C12 1 -0.175028 0.514757 0.877282 11.00000 0.07186 0.06720 = 0.06179 -0.00893 0.00177 -0.02010 AFIX 43 H12 2 -0.190737 0.599058 0.826541 11.00000 -1.20000 AFIX 0 C13 1 0.272598 0.626126 0.488865 11.00000 0.03583 0.03713 = 0.05250 0.00031 -0.00834 -0.00619 C14 1 0.432244 0.716335 0.313527 11.00000 0.06140 0.04552 = 0.06268 0.00844 0.00326 -0.01547 AFIX 137 H14A 2 0.528258 0.678936 0.252529 11.00000 -1.50000 H14B 2 0.475015 0.774681 0.358724 11.00000 -1.50000 H14C 2 0.331317 0.775335 0.279949 11.00000 -1.50000 AFIX 0 C15 1 0.284234 0.109560 0.377535 11.00000 0.05103 0.03114 = 0.05343 -0.00178 -0.00813 -0.01289 C16 1 0.195669 0.093906 0.288308 11.00000 0.05162 0.03328 = 0.06413 -0.00546 -0.01342 -0.00804 C17 1 0.294129 0.068146 0.179866 11.00000 0.07401 0.05862 = 0.06012 -0.01337 -0.01632 -0.00626 AFIX 43 H17 2 0.236196 0.055883 0.120241 11.00000 -1.20000 AFIX 0 C18 1 0.478764 0.060305 0.158663 11.00000 0.07404 0.07237 = 0.05935 -0.01184 0.00682 -0.01325 AFIX 43 H18 2 0.544453 0.043204 0.084694 11.00000 -1.20000 AFIX 0 C19 1 0.566303 0.077571 0.246005 11.00000 0.05825 0.06578 = 0.07225 -0.00728 0.00067 -0.01935 AFIX 43 H19 2 0.690621 0.073047 0.231373 11.00000 -1.20000 AFIX 0 C20 1 0.468658 0.101497 0.354759 11.00000 0.05378 0.05253 = 0.05975 -0.00223 -0.00914 -0.01566 AFIX 43 H20 2 0.527710 0.112485 0.414220 11.00000 -1.20000 AFIX 0 HKLF 4 REM PSU-345(MD-356) in P-1 #2 REM R1 = 0.0592 for 2429 Fo > 4sig(Fo) and 0.0855 for all 3760 data REM 226 parameters refined using 0 restraints END WGHT 0.0892 0.0000 REM Highest difference peak 0.253, deepest hole -0.227, 1-sigma level 0.045 Q1 1 0.3233 0.8185 0.3387 11.00000 0.05 0.25 Q2 1 0.4403 0.6873 0.2191 11.00000 0.05 0.22 Q3 1 0.5822 0.7000 0.3282 11.00000 0.05 0.20 Q4 1 0.0103 0.3884 0.7888 11.00000 0.05 0.18 Q5 1 0.0258 0.4779 0.6775 11.00000 0.05 0.17 Q6 1 0.2022 0.8525 0.4614 11.00000 0.05 0.17 Q7 1 0.1011 0.4209 0.7063 11.00000 0.05 0.16 Q8 1 0.2301 0.0268 0.5412 11.00000 0.05 0.15 Q9 1 0.2323 0.3037 0.5263 11.00000 0.05 0.15 Q10 1 -0.0544 0.3319 0.8517 11.00000 0.05 0.14 Q11 1 0.1297 0.1000 0.1547 11.00000 0.05 0.14 Q12 1 0.0462 0.5391 0.5179 11.00000 0.05 0.13 Q13 1 -0.1036 0.3185 0.6352 11.00000 0.05 0.13 Q14 1 -0.1336 0.1188 0.2944 11.00000 0.05 0.13 Q15 1 -0.0467 -0.0225 0.3463 11.00000 0.05 0.13 Q16 1 0.0888 0.6239 0.7147 11.00000 0.05 0.13 Q17 1 -0.0045 0.0413 1.1582 11.00000 0.05 0.13 Q18 1 0.0056 0.6357 0.8457 11.00000 0.05 0.12 Q19 1 0.3390 0.0804 0.5329 11.00000 0.05 0.12 Q20 1 0.3575 0.1576 0.3623 11.00000 0.05 0.12 ; _shelx_res_checksum 31422 _shelx_shelxl_version_number 2014/7 _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 O1 O 0.23659(17) 0.74534(12) 0.52581(11) 0.0556(4) Uani 1 1 d . O2 O 0.37580(15) 0.59715(11) 0.38714(10) 0.0507(3) Uani 1 1 d . O3 O 0.01390(19) 0.09953(15) 0.30686(14) 0.0649(4) Uani 1 1 d . H3 H -0.047(3) 0.146(3) 0.365(2) 0.087(8) Uiso 1 1 d . N1 N 0.1821(2) 0.13314(15) 0.48903(13) 0.0504(4) Uani 1 1 d . H1 H 0.130(3) 0.075(2) 0.5293(17) 0.069(6) Uiso 1 1 d . C1 C 0.0478(2) 0.38583(18) 0.71927(14) 0.0443(4) Uani 1 1 d . C2 C 0.0752(2) 0.26335(17) 0.65975(14) 0.0451(4) Uani 1 1 d . H2 H 0.0301 0.1835 0.6970 0.054 Uiso 1 1 calc R C3 C 0.1677(2) 0.25541(16) 0.54628(13) 0.0418(4) Uani 1 1 d . C4 C 0.2340(2) 0.37458(16) 0.49175(14) 0.0429(4) Uani 1 1 d . H4 H 0.2970 0.3717 0.4158 0.052 Uiso 1 1 calc R C5 C 0.2068(2) 0.49790(16) 0.54997(13) 0.0418(4) Uani 1 1 d . C6 C 0.1152(2) 0.50509(17) 0.66271(14) 0.0449(4) Uani 1 1 d . H6 H 0.0986 0.5889 0.7008 0.054 Uiso 1 1 calc R C7 C -0.0548(2) 0.39042(19) 0.83951(15) 0.0505(4) Uani 1 1 d . C8 C -0.0332(3) 0.2671(2) 0.91740(17) 0.0678(6) Uani 1 1 d . H8 H 0.0470 0.1813 0.8944 0.081 Uiso 1 1 calc R C9 C -0.1302(3) 0.2713(3) 1.02898(19) 0.0852(7) Uani 1 1 d . H9 H -0.1136 0.1886 1.0813 0.102 Uiso 1 1 calc R C10 C -0.2502(3) 0.3954(3) 1.06332(19) 0.0875(8) Uani 1 1 d . H10 H -0.3170 0.3968 1.1382 0.105 Uiso 1 1 calc R C11 C -0.2720(3) 0.5172(3) 0.9878(2) 0.0819(7) Uani 1 1 d . H11 H -0.3530 0.6024 1.0113 0.098 Uiso 1 1 calc R C12 C -0.1750(3) 0.5148(2) 0.87728(17) 0.0676(6) Uani 1 1 d . H12 H -0.1907 0.5991 0.8265 0.081 Uiso 1 1 calc R C13 C 0.2726(2) 0.62613(17) 0.48887(14) 0.0424(4) Uani 1 1 d . C14 C 0.4322(3) 0.71634(19) 0.31353(16) 0.0589(5) Uani 1 1 d . H14A H 0.5283 0.6789 0.2525 0.088 Uiso 1 1 calc GR H14B H 0.4750 0.7747 0.3587 0.088 Uiso 1 1 calc GR H14C H 0.3313 0.7753 0.2799 0.088 Uiso 1 1 calc GR C15 C 0.2842(2) 0.10956(15) 0.37754(14) 0.0448(4) Uani 1 1 d . C16 C 0.1957(2) 0.09391(16) 0.28831(15) 0.0493(4) Uani 1 1 d . C17 C 0.2941(3) 0.0681(2) 0.17987(17) 0.0642(5) Uani 1 1 d . H17 H 0.2362 0.0559 0.1202 0.077 Uiso 1 1 calc R C18 C 0.4788(3) 0.0603(2) 0.15866(18) 0.0709(6) Uani 1 1 d . H18 H 0.5445 0.0432 0.0847 0.085 Uiso 1 1 calc R C19 C 0.5663(3) 0.0776(2) 0.24600(18) 0.0659(5) Uani 1 1 d . H19 H 0.6906 0.0730 0.2314 0.079 Uiso 1 1 calc R C20 C 0.4687(3) 0.10150(19) 0.35476(16) 0.0549(5) Uani 1 1 d . H20 H 0.5277 0.1125 0.4142 0.066 Uiso 1 1 calc R 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 0.0546(8) 0.0423(7) 0.0686(8) -0.0083(6) 0.0010(6) -0.0150(6) O2 0.0531(7) 0.0379(6) 0.0557(8) 0.0022(5) 0.0030(6) -0.0121(5) O3 0.0537(8) 0.0644(9) 0.0828(10) -0.0249(8) -0.0175(7) -0.0104(7) N1 0.0570(9) 0.0417(8) 0.0533(9) 0.0000(6) -0.0015(7) -0.0208(7) C1 0.0389(8) 0.0483(9) 0.0452(9) 0.0016(7) -0.0078(6) -0.0110(7) C2 0.0418(9) 0.0459(9) 0.0484(10) 0.0064(7) -0.0094(7) -0.0150(8) C3 0.0386(8) 0.0386(8) 0.0490(9) 0.0027(7) -0.0117(7) -0.0099(7) C4 0.0400(8) 0.0409(8) 0.0465(9) 0.0021(6) -0.0062(7) -0.0101(7) C5 0.0356(8) 0.0396(8) 0.0486(9) 0.0027(7) -0.0087(7) -0.0074(7) C6 0.0427(9) 0.0405(8) 0.0514(10) -0.0022(7) -0.0105(7) -0.0079(7) C7 0.0472(10) 0.0571(10) 0.0486(10) -0.0009(8) -0.0050(7) -0.0189(8) C8 0.0640(12) 0.0772(13) 0.0569(12) 0.0110(9) -0.0070(9) -0.0162(11) C9 0.0800(16) 0.111(2) 0.0607(14) 0.0209(13) -0.0084(11) -0.0313(16) C10 0.0755(16) 0.137(2) 0.0527(13) -0.0076(14) 0.0072(11) -0.0420(16) C11 0.0784(15) 0.0936(16) 0.0702(15) -0.0218(13) 0.0140(11) -0.0250(13) C12 0.0719(14) 0.0672(13) 0.0618(13) -0.0089(10) 0.0018(10) -0.0201(11) C13 0.0358(8) 0.0371(8) 0.0525(10) 0.0003(7) -0.0083(7) -0.0062(7) C14 0.0614(12) 0.0455(9) 0.0627(12) 0.0084(8) 0.0033(9) -0.0155(9) C15 0.0510(10) 0.0311(7) 0.0534(10) -0.0018(6) -0.0081(7) -0.0129(7) C16 0.0516(10) 0.0333(8) 0.0641(11) -0.0055(7) -0.0134(8) -0.0080(8) C17 0.0740(14) 0.0586(11) 0.0601(12) -0.0134(9) -0.0163(10) -0.0063(10) C18 0.0740(14) 0.0724(13) 0.0594(13) -0.0118(10) 0.0068(10) -0.0132(12) C19 0.0582(12) 0.0658(12) 0.0722(14) -0.0073(10) 0.0007(10) -0.0193(10) C20 0.0538(11) 0.0525(10) 0.0597(11) -0.0022(8) -0.0091(8) -0.0157(9) 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' 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 C13 O2 C14 117.76(13) C16 O3 H3 115.0(16) C3 N1 H1 111.5(14) C3 N1 C15 123.95(13) C15 N1 H1 124.5(14) C2 C1 C6 118.53(15) C2 C1 C7 120.32(15) C6 C1 C7 121.14(15) C1 C2 H2 118.9 C1 C2 C3 122.23(14) C3 C2 H2 118.9 N1 C3 C2 119.56(14) C4 C3 N1 121.92(14) C4 C3 C2 118.42(14) C3 C4 H4 120.0 C5 C4 C3 119.95(15) C5 C4 H4 120.0 C4 C5 C13 119.19(14) C6 C5 C4 121.40(14) C6 C5 C13 119.39(15) C1 C6 H6 120.3 C5 C6 C1 119.48(15) C5 C6 H6 120.3 C8 C7 C1 120.24(17) C12 C7 C1 121.86(16) C12 C7 C8 117.90(17) C7 C8 H8 119.9 C9 C8 C7 120.1(2) C9 C8 H8 119.9 C8 C9 H9 119.7 C10 C9 C8 120.6(2) C10 C9 H9 119.7 C9 C10 H10 120.1 C11 C10 C9 119.8(2) C11 C10 H10 120.1 C10 C11 H11 119.9 C10 C11 C12 120.1(2) C12 C11 H11 119.9 C7 C12 H12 119.3 C11 C12 C7 121.5(2) C11 C12 H12 119.3 O1 C13 O2 123.04(14) O1 C13 C5 124.68(15) O2 C13 C5 112.28(13) O2 C14 H14A 109.5 O2 C14 H14B 109.5 O2 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C16 C15 N1 118.82(16) C20 C15 N1 121.71(15) C20 C15 C16 119.48(16) O3 C16 C15 121.63(16) O3 C16 C17 118.96(16) C17 C16 C15 119.38(17) C16 C17 H17 119.8 C16 C17 C18 120.34(18) C18 C17 H17 119.8 C17 C18 H18 119.8 C19 C18 C17 120.48(18) C19 C18 H18 119.8 C18 C19 H19 120.4 C20 C19 C18 119.29(19) C20 C19 H19 120.4 C15 C20 H20 119.5 C19 C20 C15 121.02(18) C19 C20 H20 119.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C13 1.2109(19) O2 C13 1.3226(19) O2 C14 1.4312(19) O3 H3 0.86(2) O3 C16 1.362(2) N1 H1 0.81(2) N1 C3 1.382(2) N1 C15 1.407(2) C1 C2 1.381(2) C1 C6 1.393(2) C1 C7 1.480(2) C2 H2 0.9300 C2 C3 1.387(2) C3 C4 1.381(2) C4 H4 0.9300 C4 C5 1.380(2) C5 C6 1.377(2) C5 C13 1.475(2) C6 H6 0.9300 C7 C8 1.384(3) C7 C12 1.376(3) C8 H8 0.9300 C8 C9 1.379(3) C9 H9 0.9300 C9 C10 1.362(3) C10 H10 0.9300 C10 C11 1.357(3) C11 H11 0.9300 C11 C12 1.368(3) C12 H12 0.9300 C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C15 C16 1.393(2) C15 C20 1.377(2) C16 C17 1.370(3) C17 H17 0.9300 C17 C18 1.379(3) C18 H18 0.9300 C18 C19 1.374(3) C19 H19 0.9300 C19 C20 1.368(3) C20 H20 0.9300 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 O3 H3 O1 0.86(2) 1.93(3) 2.769(2) 165(2) 2_566 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 O3 C16 C17 C18 -179.32(16) N1 C3 C4 C5 175.99(14) N1 C15 C16 O3 -0.6(2) N1 C15 C16 C17 -178.78(14) N1 C15 C20 C19 179.58(15) C1 C2 C3 N1 -176.44(15) C1 C2 C3 C4 0.0(2) C1 C7 C8 C9 -179.37(18) C1 C7 C12 C11 178.66(18) C2 C1 C6 C5 -0.1(2) C2 C1 C7 C8 38.7(2) C2 C1 C7 C12 -140.53(19) C2 C3 C4 C5 -0.3(2) C3 N1 C15 C16 -119.89(17) C3 N1 C15 C20 60.2(2) C3 C4 C5 C6 0.5(2) C3 C4 C5 C13 -177.74(14) C4 C5 C6 C1 -0.3(2) C4 C5 C13 O1 170.26(15) C4 C5 C13 O2 -9.2(2) C6 C1 C2 C3 0.2(2) C6 C1 C7 C8 -142.73(18) C6 C1 C7 C12 38.0(3) C6 C5 C13 O1 -8.0(3) C6 C5 C13 O2 172.52(13) C7 C1 C2 C3 178.83(15) C7 C1 C6 C5 -178.65(14) C7 C8 C9 C10 1.1(3) C8 C7 C12 C11 -0.6(3) C8 C9 C10 C11 -1.3(4) C9 C10 C11 C12 0.6(4) C10 C11 C12 C7 0.3(4) C12 C7 C8 C9 -0.1(3) C13 C5 C6 C1 177.94(14) C14 O2 C13 O1 -6.1(2) C14 O2 C13 C5 173.38(14) C15 N1 C3 C2 -175.03(15) C15 N1 C3 C4 8.7(3) C15 C16 C17 C18 -1.1(3) C16 C15 C20 C19 -0.4(3) C16 C17 C18 C19 0.3(3) C17 C18 C19 C20 0.5(3) C18 C19 C20 C15 -0.5(3) C20 C15 C16 O3 179.31(14) C20 C15 C16 C17 1.2(2)