#------------------------------------------------------------------------------ #$Date: 2020-02-27 04:09:06 +0200 (Thu, 27 Feb 2020) $ #$Revision: 248474 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557381.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_1557381 loop_ _publ_author_name 'Kim, Inwon' 'Im, Honggu' 'Lee, Hyeonyeong' 'Hong, Sungwoo' _publ_section_title ; N-Heterocyclic Carbene-Catalyzed Deaminative Cross-Coupling of Aldehydes with Katritzky Pyridinium Salts ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC00225A _journal_year 2020 _chemical_formula_sum 'C23 H23 N O2' _chemical_formula_weight 345.42 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-11-08 deposited with the CCDC. 2020-02-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 105.289(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.3351(6) _cell_length_b 20.6304(13) _cell_length_c 9.7275(6) _cell_measurement_reflns_used 9944 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 26.42 _cell_measurement_theta_min 2.87 _cell_volume 1807.1(2) _computing_cell_refinement 'Bruker APEXIII' _computing_data_collection 'Bruker APEXIII' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ORTEP _computing_publication_material CIFTAB _computing_structure_refinement SHELXL _computing_structure_solution SHELXS _diffrn_ambient_temperature 153(2) _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'Bruker Photon II' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0734 _diffrn_reflns_av_unetI/netI 0.0464 _diffrn_reflns_Laue_measured_fraction_full 0.984 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 34021 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.422 _diffrn_reflns_theta_min 2.468 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.7067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.270 _exptl_crystal_description rod _exptl_crystal_F_000 736 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM/EA/Pentane' _exptl_crystal_size_max 0.254 _exptl_crystal_size_mid 0.083 _exptl_crystal_size_min 0.068 _refine_diff_density_max 0.250 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.202 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 240 _refine_ls_number_reflns 3634 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.202 _refine_ls_R_factor_all 0.1079 _refine_ls_R_factor_gt 0.0841 _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^)+(0.0188P)^2^+2.6399P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1306 _refine_ls_wR_factor_ref 0.1379 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2926 _reflns_number_total 3634 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00225a2.cif _cod_data_source_block A19152O_014 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1557381 _shelx_shelxl_version_number 2018/3 _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_min 0.980 _shelx_estimated_absorpt_t_max 0.995 _shelx_res_file ; TITL A19152O_014 in P2(1)/c A19152O_014.res created by SHELXL-2018/3 at 15:53:27 on 29-Oct-2019 CELL 0.71073 9.33510 20.63040 9.72750 90.0000 105.2887 90.0000 ZERR 4.00 0.00060 0.00130 0.00060 0.0000 0.0023 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 92 92 4 8 ACTA TEMP -120.3 SIZE 0.068 0.083 0.254 CONF MERG 2 L.S. 8 BOND $H FMAP 2 PLAN 20 OMIT -10 7 3 OMIT 7 8 6 OMIT 4 12 8 OMIT -9 5 2 OMIT -9 6 2 OMIT 4 6 8 OMIT 2 8 10 OMIT 7 9 6 OMIT -9 2 2 OMIT -1 2 1 OMIT -8 18 2 OMIT 9 3 0 OMIT 1 8 9 OMIT 8 4 2 OMIT 9 7 3 EQIV $1 x, -y+1/2, z+1/2 HTAB N11 O13_$1 LIST 4 WGHT 0.018800 2.639900 FVAR 0.18324 C1 1 0.494238 0.383961 0.433220 11.00000 0.02099 0.01957 = 0.01756 -0.00081 0.00682 0.00163 AFIX 43 H1 2 0.435987 0.381637 0.337204 11.00000 -1.20000 AFIX 0 C2 1 0.469345 0.341481 0.532222 11.00000 0.01703 0.01787 = 0.02149 -0.00376 0.00923 -0.00083 C3 1 0.555160 0.344511 0.674990 11.00000 0.02572 0.02151 = 0.01823 0.00195 0.00733 0.00032 AFIX 43 H3 2 0.535806 0.315231 0.743310 11.00000 -1.20000 AFIX 0 C4 1 0.665162 0.388995 0.715279 11.00000 0.02598 0.02636 = 0.02055 -0.00213 0.00111 0.00228 AFIX 43 H4 2 0.722834 0.390114 0.811616 11.00000 -1.20000 AFIX 0 C5 1 0.695521 0.433556 0.617040 11.00000 0.01748 0.01927 = 0.02757 -0.00315 0.00687 0.00415 C6 1 0.607102 0.431485 0.474035 11.00000 0.01624 0.01598 = 0.02570 -0.00284 0.01063 0.00352 C7 1 0.633894 0.478064 0.376325 11.00000 0.02916 0.01910 = 0.02759 -0.00080 0.01521 0.00016 AFIX 43 H7 2 0.573990 0.477949 0.280776 11.00000 -1.20000 AFIX 0 C8 1 0.743294 0.522640 0.416901 11.00000 0.03063 0.02007 = 0.04152 0.00126 0.01976 -0.00286 AFIX 43 H8 2 0.759241 0.553343 0.349664 11.00000 -1.20000 AFIX 0 C9 1 0.833805 0.523925 0.558041 11.00000 0.02453 0.02482 = 0.04911 -0.00926 0.01283 -0.00647 AFIX 43 H9 2 0.911393 0.554920 0.585286 11.00000 -1.20000 AFIX 0 C10 1 0.809641 0.480503 0.655450 11.00000 0.02271 0.02802 = 0.03497 -0.00865 0.00243 -0.00017 AFIX 43 H10 2 0.870446 0.481826 0.750596 11.00000 -1.20000 AFIX 0 N11 3 0.357669 0.293405 0.500839 11.00000 0.02061 0.02152 = 0.01444 -0.00019 0.00696 -0.00605 H11 2 0.329304 0.280132 0.571428 11.00000 -1.20000 C12 1 0.298655 0.263928 0.375567 11.00000 0.01709 0.01325 = 0.01782 0.00134 0.00495 0.00292 O13 4 0.331787 0.276622 0.264485 11.00000 0.03133 0.02181 = 0.01710 -0.00371 0.01250 -0.00641 C14 1 0.189104 0.210054 0.382681 11.00000 0.01662 0.01835 = 0.01665 0.00027 0.00621 0.00053 AFIX 13 H14 2 0.136715 0.221167 0.456950 11.00000 -1.20000 AFIX 0 C15 1 0.076119 0.206714 0.237848 11.00000 0.02011 0.02059 = 0.01962 0.00359 0.00719 -0.00402 O16 4 0.089917 0.167059 0.149490 11.00000 0.03439 0.02627 = 0.02006 -0.00510 0.00506 0.00422 C17 1 -0.049091 0.254225 0.205895 11.00000 0.01574 0.01931 = 0.01817 0.00743 0.00694 -0.00186 C18 1 -0.048928 0.309054 0.289683 11.00000 0.02047 0.02260 = 0.02493 0.00190 0.00736 0.00086 AFIX 43 H18 2 0.031537 0.316352 0.371282 11.00000 -1.20000 AFIX 0 C19 1 -0.164480 0.352747 0.255143 11.00000 0.02749 0.02736 = 0.03860 0.00381 0.01302 0.00635 AFIX 43 H19 2 -0.163283 0.390263 0.312067 11.00000 -1.20000 AFIX 0 C20 1 -0.281957 0.341715 0.137414 11.00000 0.02050 0.03328 = 0.04833 0.01706 0.01222 0.00797 AFIX 43 H20 2 -0.361803 0.371765 0.113616 11.00000 -1.20000 AFIX 0 C21 1 -0.284522 0.287491 0.054018 11.00000 0.02057 0.04141 = 0.03020 0.01247 0.00146 -0.00325 AFIX 43 H21 2 -0.366333 0.280086 -0.026313 11.00000 -1.20000 AFIX 0 C22 1 -0.167706 0.243764 0.087380 11.00000 0.02522 0.03025 = 0.01897 0.00442 0.00484 -0.00422 AFIX 43 H22 2 -0.168792 0.206677 0.029225 11.00000 -1.20000 AFIX 0 C23 1 0.274469 0.146506 0.423808 11.00000 0.01842 0.02089 = 0.02105 0.00304 0.00625 0.00024 AFIX 23 H23A 2 0.329797 0.137168 0.352120 11.00000 -1.20000 H23B 2 0.348483 0.152861 0.516576 11.00000 -1.20000 AFIX 0 C24 1 0.180538 0.087425 0.435564 11.00000 0.02242 0.01960 = 0.01975 0.00060 0.00436 -0.00288 AFIX 13 H24 2 0.116323 0.077105 0.338348 11.00000 -1.20000 AFIX 0 C25 1 0.282732 0.029687 0.487379 11.00000 0.03396 0.02081 = 0.03764 0.00572 0.01243 0.00471 AFIX 137 H25A 2 0.223498 -0.010101 0.477140 11.00000 -1.50000 H25B 2 0.335567 0.035917 0.587828 11.00000 -1.50000 H25C 2 0.354749 0.026170 0.430439 11.00000 -1.50000 AFIX 0 C26 1 0.080104 0.099221 0.533911 11.00000 0.02834 0.02249 = 0.03495 0.00261 0.01344 -0.00051 AFIX 137 H26A 2 0.024037 0.059672 0.540236 11.00000 -1.50000 H26B 2 0.010876 0.134546 0.495655 11.00000 -1.50000 H26C 2 0.140870 0.111023 0.629031 11.00000 -1.50000 AFIX 0 HKLF 4 REM A19152O_014 in P2(1)/c REM wR2 = 0.1379, GooF = S = 1.202, Restrained GooF = 1.202 for all data REM R1 = 0.0841 for 2926 Fo > 4sig(Fo) and 0.1079 for all 3634 data REM 240 parameters refined using 0 restraints END WGHT 0.0188 2.6399 REM Highest difference peak 0.250, deepest hole -0.256, 1-sigma level 0.055 Q1 1 0.1952 0.1578 0.1606 11.00000 0.05 0.25 Q2 1 0.2524 0.2951 0.4485 11.00000 0.05 0.22 Q3 1 0.4836 0.3520 0.6181 11.00000 0.05 0.22 Q4 1 0.2439 0.2390 0.3809 11.00000 0.05 0.22 Q5 1 0.2458 0.3309 0.2018 11.00000 0.05 0.21 Q6 1 0.1358 0.2118 0.3192 11.00000 0.05 0.20 Q7 1 0.8537 0.4866 0.5831 11.00000 0.05 0.20 Q8 1 0.4473 0.3762 0.4995 11.00000 0.05 0.20 Q9 1 0.3432 0.2375 0.2127 11.00000 0.05 0.20 Q10 1 0.5217 0.3410 0.4818 11.00000 0.05 0.20 Q11 1 0.8668 0.4619 0.8117 11.00000 0.05 0.19 Q12 1 0.5227 0.4230 0.4694 11.00000 0.05 0.19 Q13 1 0.5718 0.3871 0.6859 11.00000 0.05 0.19 Q14 1 0.8561 0.5792 0.3363 11.00000 0.05 0.19 Q15 1 0.2356 0.0189 0.5788 11.00000 0.05 0.19 Q16 1 0.6417 0.3516 0.6564 11.00000 0.05 0.18 Q17 1 0.6775 0.4207 0.5208 11.00000 0.05 0.18 Q18 1 0.2373 0.1191 0.4515 11.00000 0.05 0.18 Q19 1 0.4462 0.2860 0.1607 11.00000 0.05 0.18 Q20 1 -0.1356 0.3137 0.3113 11.00000 0.05 0.18 ; _shelx_res_checksum 68440 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 C1 C 0.4942(3) 0.38396(12) 0.4332(3) 0.0190(6) Uani 1 1 d . . . . . H1 H 0.435987 0.381637 0.337204 0.023 Uiso 1 1 calc R U . . . C2 C 0.4693(3) 0.34148(12) 0.5322(3) 0.0180(6) Uani 1 1 d . . . . . C3 C 0.5552(3) 0.34451(13) 0.6750(3) 0.0215(6) Uani 1 1 d . . . . . H3 H 0.535806 0.315231 0.743310 0.026 Uiso 1 1 calc R U . . . C4 C 0.6652(3) 0.38900(14) 0.7153(3) 0.0252(6) Uani 1 1 d . . . . . H4 H 0.722834 0.390114 0.811616 0.030 Uiso 1 1 calc R U . . . C5 C 0.6955(3) 0.43356(13) 0.6170(3) 0.0213(6) Uani 1 1 d . . . . . C6 C 0.6071(3) 0.43149(12) 0.4740(3) 0.0183(6) Uani 1 1 d . . . . . C7 C 0.6339(3) 0.47806(13) 0.3763(3) 0.0238(6) Uani 1 1 d . . . . . H7 H 0.573990 0.477949 0.280776 0.029 Uiso 1 1 calc R U . . . C8 C 0.7433(3) 0.52264(14) 0.4169(3) 0.0288(7) Uani 1 1 d . . . . . H8 H 0.759241 0.553343 0.349664 0.035 Uiso 1 1 calc R U . . . C9 C 0.8338(3) 0.52392(15) 0.5580(4) 0.0322(7) Uani 1 1 d . . . . . H9 H 0.911393 0.554920 0.585286 0.039 Uiso 1 1 calc R U . . . C10 C 0.8096(3) 0.48050(14) 0.6554(3) 0.0295(7) Uani 1 1 d . . . . . H10 H 0.870446 0.481826 0.750596 0.035 Uiso 1 1 calc R U . . . N11 N 0.3577(2) 0.29341(11) 0.5008(2) 0.0184(5) Uani 1 1 d . . . . . H11 H 0.329(3) 0.2801(14) 0.571(3) 0.022 Uiso 1 1 d . U . . . C12 C 0.2987(3) 0.26393(12) 0.3756(3) 0.0160(5) Uani 1 1 d . . . . . O13 O 0.3318(2) 0.27662(9) 0.26448(19) 0.0223(4) Uani 1 1 d . . . . . C14 C 0.1891(3) 0.21005(12) 0.3827(3) 0.0169(5) Uani 1 1 d . . . . . H14 H 0.136715 0.221167 0.456950 0.020 Uiso 1 1 calc R U . . . C15 C 0.0761(3) 0.20671(13) 0.2378(3) 0.0197(6) Uani 1 1 d . . . . . O16 O 0.0899(2) 0.16706(9) 0.1495(2) 0.0273(5) Uani 1 1 d . . . . . C17 C -0.0491(3) 0.25423(12) 0.2059(3) 0.0173(6) Uani 1 1 d . . . . . C18 C -0.0489(3) 0.30905(13) 0.2897(3) 0.0224(6) Uani 1 1 d . . . . . H18 H 0.031537 0.316352 0.371282 0.027 Uiso 1 1 calc R U . . . C19 C -0.1645(3) 0.35275(15) 0.2551(3) 0.0303(7) Uani 1 1 d . . . . . H19 H -0.163283 0.390263 0.312067 0.036 Uiso 1 1 calc R U . . . C20 C -0.2820(3) 0.34171(15) 0.1374(4) 0.0334(8) Uani 1 1 d . . . . . H20 H -0.361803 0.371765 0.113616 0.040 Uiso 1 1 calc R U . . . C21 C -0.2845(3) 0.28749(16) 0.0540(3) 0.0317(7) Uani 1 1 d . . . . . H21 H -0.366333 0.280086 -0.026313 0.038 Uiso 1 1 calc R U . . . C22 C -0.1677(3) 0.24376(14) 0.0874(3) 0.0250(6) Uani 1 1 d . . . . . H22 H -0.168792 0.206677 0.029225 0.030 Uiso 1 1 calc R U . . . C23 C 0.2745(3) 0.14651(13) 0.4238(3) 0.0199(6) Uani 1 1 d . . . . . H23A H 0.329797 0.137168 0.352120 0.024 Uiso 1 1 calc R U . . . H23B H 0.348483 0.152861 0.516576 0.024 Uiso 1 1 calc R U . . . C24 C 0.1805(3) 0.08742(13) 0.4356(3) 0.0208(6) Uani 1 1 d . . . . . H24 H 0.116323 0.077105 0.338348 0.025 Uiso 1 1 calc R U . . . C25 C 0.2827(3) 0.02969(14) 0.4874(3) 0.0302(7) Uani 1 1 d . . . . . H25A H 0.223498 -0.010101 0.477140 0.045 Uiso 1 1 calc R U . . . H25B H 0.335567 0.035917 0.587828 0.045 Uiso 1 1 calc R U . . . H25C H 0.354749 0.026170 0.430439 0.045 Uiso 1 1 calc R U . . . C26 C 0.0801(3) 0.09922(14) 0.5339(3) 0.0276(7) Uani 1 1 d . . . . . H26A H 0.024037 0.059672 0.540236 0.041 Uiso 1 1 calc R U . . . H26B H 0.010876 0.134546 0.495655 0.041 Uiso 1 1 calc R U . . . H26C H 0.140870 0.111023 0.629031 0.041 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 C1 0.0210(14) 0.0196(14) 0.0176(13) -0.0008(11) 0.0068(11) 0.0016(11) C2 0.0170(14) 0.0179(13) 0.0215(14) -0.0038(11) 0.0092(11) -0.0008(11) C3 0.0257(16) 0.0215(14) 0.0182(14) 0.0019(11) 0.0073(12) 0.0003(12) C4 0.0260(16) 0.0264(15) 0.0206(15) -0.0021(12) 0.0011(12) 0.0023(13) C5 0.0175(14) 0.0193(14) 0.0276(15) -0.0032(12) 0.0069(12) 0.0041(11) C6 0.0162(14) 0.0160(13) 0.0257(14) -0.0028(11) 0.0106(12) 0.0035(11) C7 0.0292(16) 0.0191(14) 0.0276(15) -0.0008(12) 0.0152(13) 0.0002(12) C8 0.0306(17) 0.0201(15) 0.0415(18) 0.0013(13) 0.0198(15) -0.0029(13) C9 0.0245(16) 0.0248(16) 0.049(2) -0.0093(15) 0.0128(15) -0.0065(13) C10 0.0227(15) 0.0280(16) 0.0350(17) -0.0087(14) 0.0024(13) -0.0002(13) N11 0.0206(12) 0.0215(12) 0.0144(11) -0.0002(9) 0.0070(10) -0.0061(10) C12 0.0171(13) 0.0132(12) 0.0178(13) 0.0013(10) 0.0050(11) 0.0029(11) O13 0.0313(11) 0.0218(10) 0.0171(9) -0.0037(8) 0.0125(8) -0.0064(9) C14 0.0166(13) 0.0184(13) 0.0166(13) 0.0003(11) 0.0062(11) 0.0005(11) C15 0.0201(14) 0.0206(14) 0.0196(14) 0.0036(11) 0.0072(11) -0.0040(11) O16 0.0344(12) 0.0263(11) 0.0201(10) -0.0051(9) 0.0051(9) 0.0042(9) C17 0.0157(13) 0.0193(13) 0.0182(13) 0.0074(11) 0.0069(11) -0.0019(11) C18 0.0205(15) 0.0226(15) 0.0249(15) 0.0019(12) 0.0074(12) 0.0009(12) C19 0.0275(17) 0.0274(16) 0.0386(18) 0.0038(14) 0.0130(14) 0.0064(13) C20 0.0205(16) 0.0333(18) 0.048(2) 0.0171(15) 0.0122(15) 0.0080(13) C21 0.0206(15) 0.0414(19) 0.0302(16) 0.0125(14) 0.0015(13) -0.0033(14) C22 0.0252(16) 0.0302(16) 0.0190(14) 0.0044(12) 0.0048(12) -0.0042(13) C23 0.0184(14) 0.0209(14) 0.0211(14) 0.0030(11) 0.0063(11) 0.0002(11) C24 0.0224(15) 0.0196(14) 0.0197(14) 0.0006(11) 0.0044(11) -0.0029(12) C25 0.0340(17) 0.0208(15) 0.0376(18) 0.0057(13) 0.0124(14) 0.0047(13) C26 0.0283(16) 0.0225(15) 0.0350(17) 0.0026(13) 0.0134(14) -0.0005(13) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.9(2) . . ? C2 C1 H1 120.1 . . ? C6 C1 H1 120.1 . . ? C1 C2 C3 120.5(2) . . ? C1 C2 N11 123.4(2) . . ? C3 C2 N11 116.1(2) . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 121.2(3) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C10 122.7(3) . . ? C4 C5 C6 118.5(2) . . ? C10 C5 C6 118.8(3) . . ? C1 C6 C5 119.5(2) . . ? C1 C6 C7 122.0(2) . . ? C5 C6 C7 118.5(2) . . ? C8 C7 C6 121.2(3) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 120.6(3) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 119.8(3) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C5 121.1(3) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? C12 N11 C2 128.1(2) . . ? C12 N11 H11 117(2) . . ? C2 N11 H11 115(2) . . ? O13 C12 N11 124.3(2) . . ? O13 C12 C14 121.5(2) . . ? N11 C12 C14 114.1(2) . . ? C15 C14 C12 107.5(2) . . ? C15 C14 C23 112.9(2) . . ? C12 C14 C23 109.1(2) . . ? C15 C14 H14 109.1 . . ? C12 C14 H14 109.1 . . ? C23 C14 H14 109.1 . . ? O16 C15 C17 121.1(2) . . ? O16 C15 C14 120.5(2) . . ? C17 C15 C14 118.4(2) . . ? C22 C17 C18 119.3(2) . . ? C22 C17 C15 118.7(2) . . ? C18 C17 C15 122.0(2) . . ? C19 C18 C17 120.5(3) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 119.6(3) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 120.6(3) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 120.0(3) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C17 119.9(3) . . ? C21 C22 H22 120.0 . . ? C17 C22 H22 120.0 . . ? C24 C23 C14 115.7(2) . . ? C24 C23 H23A 108.3 . . ? C14 C23 H23A 108.3 . . ? C24 C23 H23B 108.3 . . ? C14 C23 H23B 108.3 . . ? H23A C23 H23B 107.4 . . ? C23 C24 C26 112.4(2) . . ? C23 C24 C25 109.1(2) . . ? C26 C24 C25 110.6(2) . . ? C23 C24 H24 108.2 . . ? C26 C24 H24 108.2 . . ? C25 C24 H24 108.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 C1 C2 1.367(4) . ? C1 C6 1.417(4) . ? C1 H1 0.9500 . ? C2 C3 1.410(4) . ? C2 N11 1.413(3) . ? C3 C4 1.356(4) . ? C3 H3 0.9500 . ? C4 C5 1.408(4) . ? C4 H4 0.9500 . ? C5 C10 1.415(4) . ? C5 C6 1.419(4) . ? C6 C7 1.419(4) . ? C7 C8 1.353(4) . ? C7 H7 0.9500 . ? C8 C9 1.410(4) . ? C8 H8 0.9500 . ? C9 C10 1.365(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? N11 C12 1.343(3) . ? N11 H11 0.84(3) . ? C12 O13 1.228(3) . ? C12 C14 1.524(3) . ? C14 C15 1.523(4) . ? C14 C23 1.532(4) . ? C14 H14 1.0000 . ? C15 O16 1.218(3) . ? C15 C17 1.494(4) . ? C17 C22 1.389(4) . ? C17 C18 1.394(4) . ? C18 C19 1.378(4) . ? C18 H18 0.9500 . ? C19 C20 1.380(4) . ? C19 H19 0.9500 . ? C20 C21 1.378(5) . ? C20 H20 0.9500 . ? C21 C22 1.386(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.523(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C26 1.525(4) . ? C24 C25 1.526(4) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 _geom_hbond_publ_flag N11 H11 O13 0.84(3) 2.21(3) 3.008(3) 158(3) 4_566 yes 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 C6 C1 C2 C3 0.0(4) . . . . ? C6 C1 C2 N11 179.0(2) . . . . ? C1 C2 C3 C4 -1.1(4) . . . . ? N11 C2 C3 C4 179.9(2) . . . . ? C2 C3 C4 C5 0.7(4) . . . . ? C3 C4 C5 C10 -179.9(3) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C2 C1 C6 C5 1.4(4) . . . . ? C2 C1 C6 C7 -177.8(2) . . . . ? C4 C5 C6 C1 -1.7(4) . . . . ? C10 C5 C6 C1 178.8(2) . . . . ? C4 C5 C6 C7 177.6(2) . . . . ? C10 C5 C6 C7 -2.0(4) . . . . ? C1 C6 C7 C8 -179.3(3) . . . . ? C5 C6 C7 C8 1.5(4) . . . . ? C6 C7 C8 C9 0.0(4) . . . . ? C7 C8 C9 C10 -1.0(4) . . . . ? C8 C9 C10 C5 0.5(4) . . . . ? C4 C5 C10 C9 -178.5(3) . . . . ? C6 C5 C10 C9 1.0(4) . . . . ? C1 C2 N11 C12 27.4(4) . . . . ? C3 C2 N11 C12 -153.6(3) . . . . ? C2 N11 C12 O13 -2.4(4) . . . . ? C2 N11 C12 C14 175.1(2) . . . . ? O13 C12 C14 C15 -32.2(3) . . . . ? N11 C12 C14 C15 150.2(2) . . . . ? O13 C12 C14 C23 90.5(3) . . . . ? N11 C12 C14 C23 -87.1(3) . . . . ? C12 C14 C15 O16 97.6(3) . . . . ? C23 C14 C15 O16 -22.7(3) . . . . ? C12 C14 C15 C17 -80.9(3) . . . . ? C23 C14 C15 C17 158.8(2) . . . . ? O16 C15 C17 C22 14.2(4) . . . . ? C14 C15 C17 C22 -167.4(2) . . . . ? O16 C15 C17 C18 -164.6(2) . . . . ? C14 C15 C17 C18 13.8(4) . . . . ? C22 C17 C18 C19 -0.4(4) . . . . ? C15 C17 C18 C19 178.4(2) . . . . ? C17 C18 C19 C20 0.7(4) . . . . ? C18 C19 C20 C21 -0.1(4) . . . . ? C19 C20 C21 C22 -0.6(4) . . . . ? C20 C21 C22 C17 0.8(4) . . . . ? C18 C17 C22 C21 -0.3(4) . . . . ? C15 C17 C22 C21 -179.1(2) . . . . ? C15 C14 C23 C24 -60.6(3) . . . . ? C12 C14 C23 C24 -180.0(2) . . . . ? C14 C23 C24 C26 -53.0(3) . . . . ? C14 C23 C24 C25 -176.0(2) . . . . ?