#------------------------------------------------------------------------------ #$Date: 2024-04-27 04:58:03 +0300 (Sat, 27 Apr 2024) $ #$Revision: 291384 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023110.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2023110 loop_ _publ_author_name 'El Moutaouakil Ala Allah, Abderrazzak' 'Guerrab, Walid' 'Mague, Joel T.' 'Alsubari, Abdulsalam' 'Alzahrani, Abdullah Yahya Abdullah' 'Ramli, Youssef' _publ_section_title ; Synthesis, crystal structure and Hirshfeld surface analysis of 2-[(4-hydroxyphenyl)amino]-5,5-diphenyl-1H-imidazol-4(5H)-one ; _journal_coeditor_code VM2300 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E Crystallographic Communications' _journal_paper_doi 10.1107/S2056989024003499 _journal_volume 80 _journal_year 2024 _chemical_formula_iupac 'C21 H17 N3 O2' _chemical_formula_moiety 'C21 H17 N3 O2' _chemical_formula_sum 'C21 H17 N3 O2' _chemical_formula_weight 343.38 _chemical_name_systematic ; 2-[(4-Hydroxyphenyl)amino]-5,5-diphenyl-1H-imidazol-4(5H)-one ; _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 _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2019/1 _cell_angle_alpha 90 _cell_angle_beta 100.948(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 17.764(3) _cell_length_b 8.4429(12) _cell_length_c 11.6601(16) _cell_measurement_reflns_used 3889 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 26.1505 _cell_measurement_theta_min 2.3356 _cell_volume 1717.0(4) _computing_cell_refinement ; SAINT (Bruker, 2021) ; _computing_data_collection ; APEX4 (Bruker, 2021) ; _computing_data_reduction ; SAINT (Bruker, 2021) ; _computing_molecular_graphics ; DIAMOND (Brandenburg & Putz, 2012) ; _computing_publication_material ; SHELXTL (Sheldrick, 2008b) ; _computing_structure_refinement ; SHELXL2018/1 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 7.3910 _diffrn_measured_fraction_theta_full 0.967 _diffrn_measured_fraction_theta_max 0.968 _diffrn_measurement_device 'Bruker D8 QUEST PHOTON 3 diffractometer' _diffrn_measurement_device_type 'Bruker D8 QUEST PHOTON 3 diffractometer' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_unetI/netI 0.0561 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 16776 _diffrn_reflns_theta_full 26.459 _diffrn_reflns_theta_max 26.459 _diffrn_reflns_theta_min 2.336 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 30.0 _diffrn_source_power 1.50 _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (TWINABS; Sheldrick, 2009) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.377 _exptl_crystal_size_mid 0.210 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.227 _refine_diff_density_min -0.219 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 248 _refine_ls_number_reflns 5347 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.1042 _refine_ls_R_factor_gt 0.0546 _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^)+(0.0457P)^2^+0.5709P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1125 _refine_ls_wR_factor_ref 0.1319 _reflns_number_gt 3329 _reflns_number_total 5347 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file vm2300.cif _cod_data_source_block I _cod_original_cell_volume 1716.9(4) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2023110 _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 0.968 _shelx_estimated_absorpt_t_max 0.998 _shelx_hkl_file ; 2 0 0 876.231 28.9088 -2 2 0 0 876.231 28.9088 1 3 0 0 1613.91 20.4973 -2 3 0 0 1613.91 20.4973 1 4 0 0 6950.72 99.1515 -2 4 0 0 6950.72 99.1515 1 5 0 0 2144.18 27.2032 -2 5 0 0 2144.18 27.2032 1 6 0 0 551.766 7.38051 -2 6 0 0 551.766 7.38051 1 7 0 0 2.77989 0.72097 -2 7 0 0 2.77989 0.72097 1 8 0 0 586.366 10.7612 -2 8 0 0 586.366 10.7612 1 9 0 0 926.669 16.3103 -2 9 0 0 926.669 16.3103 1 10 0 0 17.9350 1.69610 -2 10 0 0 17.9350 1.69610 1 11 0 0 27.8277 2.01930 -2 11 0 0 27.8277 2.01930 1 12 0 0 175.472 4.80632 -2 12 0 0 175.472 4.80632 1 13 0 0 20.9589 2.13253 -2 13 0 0 20.9589 2.13253 1 14 0 0 33.6682 2.62339 -2 14 0 0 33.6682 2.62339 1 15 0 0 47.3571 2.93482 -2 15 0 0 47.3571 2.93482 1 16 0 0 127.304 4.61618 -2 16 0 0 127.304 4.61618 1 17 0 0 77.0469 4.90633 -2 17 0 0 77.0469 4.90633 1 18 0 0 12.9446 7.15742 -2 18 0 0 12.9446 7.15742 1 19 0 0 18.7786 7.62441 -2 19 0 0 18.7786 7.62441 1 20 0 0 22.6276 7.69181 -2 20 0 0 22.6276 7.69181 1 21 0 0 65.0689 10.9500 -2 21 0 0 65.0689 10.9500 1 0 1 0 2.13049 0.32564 1 1 1 0 3372.93 40.8431 -2 1 1 0 3372.93 40.8431 1 2 1 0 20.7525 0.72603 -2 2 1 0 20.7525 0.72603 1 3 1 0 69.1500 1.06225 -2 3 1 0 69.1500 1.06225 1 4 1 0 4308.21 36.4487 -2 4 1 0 4308.21 36.4487 1 5 1 0 1068.99 10.0860 -2 5 1 0 1068.99 10.0860 1 6 1 0 2932.21 28.6423 -2 6 1 0 2932.21 28.6423 1 7 1 0 129.853 1.88012 -2 7 1 0 129.853 1.88012 1 8 1 0 446.482 5.48781 -2 8 1 0 446.482 5.48781 1 9 1 0 325.071 4.33125 -2 9 1 0 325.071 4.33125 1 10 1 0 204.721 3.40103 -2 10 1 0 204.721 3.40103 1 11 1 0 31.5424 1.45758 -2 11 1 0 31.5424 1.45758 1 12 1 0 33.8506 1.57953 -2 12 1 0 33.8506 1.57953 1 13 1 0 1.26703 1.01906 -2 13 1 0 1.26703 1.01906 1 14 1 0 0.35785 1.08457 -2 14 1 0 0.35785 1.08457 1 15 1 0 3.24436 1.59318 -2 15 1 0 3.24436 1.59318 1 16 1 0 21.4274 2.54933 -2 16 1 0 21.4274 2.54933 1 17 1 0 41.1203 3.12008 -2 17 1 0 41.1203 3.12008 1 18 1 0 133.238 6.10483 -2 18 1 0 133.238 6.10483 1 19 1 0 3.20318 2.57861 -2 19 1 0 3.20318 2.57861 1 20 1 0 38.8416 6.58094 -2 20 1 0 38.8416 6.58094 1 21 1 0 33.1598 6.57194 -2 21 1 0 33.1598 6.57194 1 0 2 0 9999.99 224.778 -2 0 2 0 9999.99 224.778 1 1 2 0 695.087 6.62891 -2 1 2 0 695.087 6.62891 1 2 2 0 567.333 5.51981 -2 2 2 0 567.333 5.51981 1 3 2 0 4.00531 0.47437 -2 3 2 0 4.00531 0.47437 1 4 2 0 117.331 2.83756 -2 4 2 0 117.331 2.83756 1 5 2 0 252.909 4.91454 -2 5 2 0 252.909 4.91454 1 6 2 0 19.2193 0.98871 -2 6 2 0 19.2193 0.98871 1 7 2 0 1114.41 14.9916 -2 7 2 0 1114.41 14.9916 1 8 2 0 16.9311 0.97185 -2 8 2 0 16.9311 0.97185 1 9 2 0 157.382 2.42206 -2 9 2 0 157.382 2.42206 1 10 2 0 4.49223 0.75803 -2 10 2 0 4.49223 0.75803 1 11 2 0 35.1576 1.39162 -2 11 2 0 35.1576 1.39162 1 12 2 0 57.4006 1.79234 -2 12 2 0 57.4006 1.79234 1 13 2 0 7.49667 1.91117 -2 13 2 0 7.49667 1.91117 1 14 2 0 56.0545 3.26939 -2 14 2 0 56.0545 3.26939 1 15 2 0 38.4686 2.93986 -2 15 2 0 38.4686 2.93986 1 16 2 0 64.7791 3.68955 -2 16 2 0 64.7791 3.68955 1 17 2 0 70.8617 3.98613 -2 17 2 0 70.8617 3.98613 1 18 2 0 4.69381 2.21092 -2 18 2 0 4.69381 2.21092 1 19 2 0 1.38210 2.34395 -2 19 2 0 1.38210 2.34395 1 20 2 0 4.97294 2.87884 -2 20 2 0 4.97294 2.87884 1 21 2 0 2.92285 3.49256 -2 21 2 0 2.92285 3.49256 1 0 3 0 -0.4909 0.63143 1 1 3 0 102.103 1.73438 -2 1 3 0 102.103 1.73438 1 2 3 0 265.192 3.81540 -2 2 3 0 265.192 3.81540 1 3 3 0 128.459 1.76365 -2 3 3 0 128.459 1.76365 1 4 3 0 195.281 3.47238 -2 4 3 0 195.281 3.47238 1 5 3 0 3.10012 1.23632 -2 5 3 0 3.10012 1.23632 1 6 3 0 501.370 10.9305 -2 6 3 0 501.370 10.9305 1 7 3 0 78.2793 2.83115 -2 7 3 0 78.2793 2.83115 1 8 3 0 251.628 5.57258 -2 8 3 0 251.628 5.57258 1 9 3 0 71.3278 2.88607 -2 9 3 0 71.3278 2.88607 1 10 3 0 2.65034 1.39777 -2 10 3 0 2.65034 1.39777 1 11 3 0 2.66724 1.64181 -2 11 3 0 2.66724 1.64181 1 12 3 0 1.21403 1.55761 -2 12 3 0 1.21403 1.55761 1 13 3 0 127.235 4.49677 -2 13 3 0 127.235 4.49677 1 14 3 0 211.230 7.41370 -2 14 3 0 211.230 7.41370 1 15 3 0 41.5459 3.33858 -2 15 3 0 41.5459 3.33858 1 16 3 0 24.3383 3.00550 -2 16 3 0 24.3383 3.00550 1 17 3 0 85.2776 4.45804 -2 17 3 0 85.2776 4.45804 1 18 3 0 1.14326 2.44451 -2 18 3 0 1.14326 2.44451 1 19 3 0 -1.8828 2.35816 -2 19 3 0 -1.8828 2.35816 1 20 3 0 3.87724 2.66787 -2 20 3 0 3.87724 2.66787 1 0 4 0 390.659 7.70324 -2 0 4 0 390.659 7.70324 1 1 4 0 375.407 5.26575 -2 1 4 0 375.407 5.26575 1 2 4 0 -1.4107 0.62713 -2 2 4 0 -1.4107 0.62713 1 3 4 0 106.378 2.10102 -2 3 4 0 106.378 2.10102 1 4 4 0 39.3203 1.08955 -2 4 4 0 39.3203 1.08955 1 5 4 0 154.862 2.72639 -2 5 4 0 154.862 2.72639 1 6 4 0 -0.2001 1.20849 -2 6 4 0 -0.2001 1.20849 1 7 4 0 17.1055 1.78937 -2 7 4 0 17.1055 1.78937 1 8 4 0 146.576 4.21439 -2 8 4 0 146.576 4.21439 1 9 4 0 61.8703 2.96402 -2 9 4 0 61.8703 2.96402 1 10 4 0 -0.6840 1.44319 -2 10 4 0 -0.6840 1.44319 1 11 4 0 9.45116 1.93532 -2 11 4 0 9.45116 1.93532 1 12 4 0 45.2387 3.10258 -2 12 4 0 45.2387 3.10258 1 13 4 0 67.9574 4.28250 -2 13 4 0 67.9574 4.28250 1 14 4 0 151.928 5.29225 -2 14 4 0 151.928 5.29225 1 15 4 0 3.70108 2.23249 -2 15 4 0 3.70108 2.23249 1 16 4 0 4.86377 2.24609 -2 16 4 0 4.86377 2.24609 1 17 4 0 8.02946 2.58841 -2 17 4 0 8.02946 2.58841 1 18 4 0 1.69422 2.51752 -2 18 4 0 1.69422 2.51752 1 19 4 0 5.28098 2.71695 -2 19 4 0 5.28098 2.71695 1 20 4 0 -0.1470 2.85294 -2 20 4 0 -0.1470 2.85294 1 0 5 0 -0.5211 1.03793 1 1 5 0 169.919 3.41134 -2 1 5 0 169.919 3.41134 1 2 5 0 8.58339 1.06001 -2 2 5 0 8.58339 1.06001 1 3 5 0 78.9900 2.00930 -2 3 5 0 78.9900 2.00930 1 4 5 0 115.416 2.14436 -2 4 5 0 115.416 2.14436 1 5 5 0 331.132 5.08319 -2 5 5 0 331.132 5.08319 1 6 5 0 20.0752 2.07850 -2 6 5 0 20.0752 2.07850 1 7 5 0 5.49616 1.70774 -2 7 5 0 5.49616 1.70774 1 8 5 0 96.0500 3.67773 -2 8 5 0 96.0500 3.67773 1 9 5 0 181.973 5.13323 -2 9 5 0 181.973 5.13323 1 10 5 0 310.219 7.31878 -2 10 5 0 310.219 7.31878 1 11 5 0 180.644 6.42763 -2 11 5 0 180.644 6.42763 1 12 5 0 24.8808 2.77111 -2 12 5 0 24.8808 2.77111 1 13 5 0 4.56831 2.29674 -2 13 5 0 4.56831 2.29674 1 14 5 0 62.7752 3.97724 -2 14 5 0 62.7752 3.97724 1 15 5 0 12.7434 2.75018 -2 15 5 0 12.7434 2.75018 1 16 5 0 46.4813 3.81402 -2 16 5 0 46.4813 3.81402 1 17 5 0 10.1155 2.97144 -2 17 5 0 10.1155 2.97144 1 18 5 0 -2.4093 2.58749 -2 18 5 0 -2.4093 2.58749 1 19 5 0 -2.6030 3.21525 -2 19 5 0 -2.6030 3.21525 1 0 6 0 67.6515 3.14900 -2 0 6 0 67.6515 3.14900 1 1 6 0 9.24808 1.13662 -2 1 6 0 9.24808 1.13662 1 2 6 0 53.1209 1.86042 -2 2 6 0 53.1209 1.86042 1 3 6 0 0.37487 0.84149 -2 3 6 0 0.37487 0.84149 1 4 6 0 1.77546 0.82358 -2 4 6 0 1.77546 0.82358 1 5 6 0 4.54564 1.65152 -2 5 6 0 4.54564 1.65152 1 6 6 0 30.9832 2.56902 -2 6 6 0 30.9832 2.56902 1 7 6 0 126.855 4.39902 -2 7 6 0 126.855 4.39902 1 8 6 0 59.2229 3.33395 -2 8 6 0 59.2229 3.33395 1 9 6 0 140.875 7.20780 -2 9 6 0 140.875 7.20780 1 10 6 0 200.839 5.96877 -2 10 6 0 200.839 5.96877 1 11 6 0 99.8544 4.42010 -2 11 6 0 99.8544 4.42010 1 12 6 0 0.34778 2.01070 -2 12 6 0 0.34778 2.01070 1 13 6 0 2.91076 2.28837 -2 13 6 0 2.91076 2.28837 1 14 6 0 14.2199 2.88061 -2 14 6 0 14.2199 2.88061 1 15 6 0 0.43074 2.47657 -2 15 6 0 0.43074 2.47657 1 16 6 0 -0.7775 2.36573 -2 16 6 0 -0.7775 2.36573 1 17 6 0 31.0205 3.72962 -2 17 6 0 31.0205 3.72962 1 0 7 0 0.08573 1.53848 1 1 7 0 7.57813 1.25113 -2 1 7 0 7.57813 1.25113 1 2 7 0 0.32565 1.10936 -2 2 7 0 0.32565 1.10936 1 3 7 0 0.53566 1.92549 -2 3 7 0 0.53566 1.92549 1 4 7 0 -0.1455 1.71869 -2 4 7 0 -0.1455 1.71869 1 5 7 0 27.4378 3.09488 -2 5 7 0 27.4378 3.09488 1 6 7 0 17.4700 2.46053 -2 6 7 0 17.4700 2.46053 1 7 7 0 74.2396 3.84014 -2 7 7 0 74.2396 3.84014 1 8 7 0 38.4606 3.15427 -2 8 7 0 38.4606 3.15427 1 9 7 0 54.7984 3.58964 -2 9 7 0 54.7984 3.58964 1 10 7 0 4.93014 2.12028 -2 10 7 0 4.93014 2.12028 1 11 7 0 16.4317 2.70880 -2 11 7 0 16.4317 2.70880 1 12 7 0 14.0671 2.73078 -2 12 7 0 14.0671 2.73078 1 13 7 0 0.55534 2.46328 -2 13 7 0 0.55534 2.46328 1 14 7 0 35.8642 3.60692 -2 14 7 0 35.8642 3.60692 1 15 7 0 5.70334 2.78284 -2 15 7 0 5.70334 2.78284 1 16 7 0 7.37954 3.69106 -2 16 7 0 7.37954 3.69106 1 0 8 0 13.5460 2.26443 -2 0 8 0 13.5460 2.26443 1 1 8 0 30.8121 2.71292 -2 1 8 0 30.8121 2.71292 1 2 8 0 3.88912 2.05623 -2 2 8 0 3.88912 2.05623 1 3 8 0 41.5266 3.52327 -2 3 8 0 41.5266 3.52327 1 4 8 0 39.4007 4.18097 -2 4 8 0 39.4007 4.18097 1 5 8 0 2.46008 2.58549 -2 5 8 0 2.46008 2.58549 1 6 8 0 72.6760 4.03125 -2 6 8 0 72.6760 4.03125 1 7 8 0 1.84133 2.14290 -2 7 8 0 1.84133 2.14290 1 8 8 0 10.9614 2.60296 -2 8 8 0 10.9614 2.60296 1 9 8 0 3.40750 2.18180 -2 9 8 0 3.40750 2.18180 1 10 8 0 5.74552 2.22710 -2 10 8 0 5.74552 2.22710 1 11 8 0 1.06690 2.22500 -2 11 8 0 1.06690 2.22500 1 12 8 0 -1.7365 2.16952 -2 12 8 0 -1.7365 2.16952 1 13 8 0 4.58374 2.83041 -2 13 8 0 4.58374 2.83041 1 14 8 0 10.9504 3.15559 -2 14 8 0 10.9504 3.15559 1 0 9 0 2.72701 6.59941 1 1 9 0 -6.0976 4.90803 -2 1 9 0 -6.0976 4.90803 1 2 9 0 2.83546 2.75314 -2 2 9 0 2.83546 2.75314 1 3 9 0 14.4612 3.09594 -2 3 9 0 14.4612 3.09594 1 4 9 0 1.52940 2.30693 -2 4 9 0 1.52940 2.30693 1 5 9 0 17.5697 2.87673 -2 5 9 0 17.5697 2.87673 1 6 9 0 7.50884 2.37274 -2 6 9 0 7.50884 2.37274 1 7 9 0 14.4292 3.17592 -2 7 9 0 14.4292 3.17592 1 8 9 0 3.62557 3.13394 -2 8 9 0 3.62557 3.13394 1 9 9 0 7.48390 2.63487 -2 9 9 0 7.48390 2.63487 1 10 9 0 2.99304 2.54141 -2 10 9 0 2.99304 2.54141 1 11 9 0 2.83184 3.42033 -2 11 9 0 2.83184 3.42033 1 1 10 0 -6.6794 6.20399 -2 1 10 0 -6.6794 6.20399 1 2 10 0 -13.038 5.52929 -2 2 10 0 -13.038 5.52929 1 3 10 0 12.8515 6.68846 -2 3 10 0 12.8515 6.68846 1 4 10 0 15.2323 4.89573 -2 4 10 0 15.2323 4.89573 1 5 10 0 1.69319 2.75848 -2 5 10 0 1.69319 2.75848 1 6 10 0 1.49371 3.26457 -2 6 10 0 1.49371 3.26457 1 7 10 0 -3.6861 3.73864 -2 7 10 0 -3.6861 3.73864 1 -21 0 1 11.1407 7.16103 1 -21 0 1 5.33922 5.90187 2 -20 0 1 6.52984 6.22389 2 -20 0 1 8.43229 6.80536 1 -19 0 1 15.2653 12.8994 1 -19 0 1 6.88055 5.89395 2 -18 0 1 7.67240 6.43110 2 -18 0 1 17.3676 12.7204 1 -17 0 1 1.86137 4.30970 1 -17 0 1 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3.21848 2 -11 3 13 -1.6971 4.16689 1 3 3 13 -9.3949 11.7709 -2 -11 3 13 -9.3949 11.7709 1 -11 3 13 3.06003 3.50957 2 2 3 13 -15.035 11.1051 -2 -10 3 13 -15.035 11.1051 1 -10 3 13 4.26150 4.29509 1 -10 3 13 -5.2999 3.67499 2 -9 3 13 -1.5392 3.18663 2 1 3 13 -0.0017 11.4875 -2 -9 3 13 -0.0017 11.4875 1 -9 3 13 0.04519 2.53997 1 -8 3 13 -1.1266 2.45153 1 -8 3 13 -0.4046 2.98898 2 -7 3 13 -1.8444 2.58774 1 -7 3 13 -1.4470 2.53583 2 -6 3 13 0.90801 2.61049 1 -6 3 13 0.25157 2.80073 2 -5 3 13 -0.8280 2.54485 1 -5 3 13 -0.7876 2.76176 2 -3 3 13 7.43450 11.8595 -2 -5 3 13 7.43450 11.8595 1 -4 3 13 -2.2120 2.40946 1 -4 3 13 0.47407 2.49811 2 -4 3 13 4.34004 11.4423 -2 -4 3 13 4.34004 11.4423 1 -3 3 13 23.1159 3.66427 1 -3 3 13 8.00101 2.80970 2 -5 3 13 23.4229 12.7969 -2 -3 3 13 23.4229 12.7969 1 -2 3 13 6.13202 2.86137 2 -6 3 13 11.0392 11.9482 -2 -2 3 13 11.0392 11.9482 1 -2 3 13 11.7769 3.20409 1 -1 3 13 3.17502 2.80516 2 -1 3 13 12.7795 3.30422 1 -7 3 13 -3.9501 8.92779 -2 -1 3 13 -3.9501 8.92779 1 0 3 13 21.0504 3.59414 1 -8 3 13 35.6779 13.2911 -2 0 3 13 35.6779 13.2911 1 0 3 13 13.3362 3.17836 2 -8 3 13 -14.994 10.1837 -2 1 3 13 -14.994 10.1837 1 1 3 13 2.01850 2.54231 2 1 3 13 -1.9803 3.03960 1 2 3 13 21.3174 4.69116 1 -9 3 13 4.82250 11.3037 -2 2 3 13 4.82250 11.3037 1 2 3 13 11.4444 3.44876 2 3 3 13 9.74494 3.04105 2 3 3 13 22.2732 4.51691 1 4 3 13 -6.0540 5.61230 2 4 3 13 -5.1478 5.53588 1 1 4 13 -3.4204 11.9849 -2 -9 4 13 -3.4204 11.9849 1 -9 4 13 2.16746 2.79505 1 -9 4 13 -4.3787 2.94373 2 -8 4 13 -0.0245 3.21830 1 0 4 13 -4.6788 11.8060 -2 -8 4 13 -4.6788 11.8060 1 -8 4 13 3.52119 3.74916 2 -7 4 13 3.57260 3.35986 2 -7 4 13 9.09244 3.36720 1 -1 4 13 -4.7533 12.4222 -2 -7 4 13 -4.7533 12.4222 1 -2 4 13 -4.9042 12.2564 -2 -6 4 13 -4.9042 12.2564 1 -6 4 13 0.83547 2.61110 1 -6 4 13 -7.7476 4.03942 2 -5 4 13 0.09927 4.31640 2 -5 4 13 -1.7896 3.13444 1 -2 4 13 -0.1728 10.3193 -2 -5 4 13 -0.1728 10.3193 1 -4 4 13 2.43692 3.08866 2 -4 4 13 5.05826 3.28909 1 -3 4 13 -1.8210 9.64243 -2 -4 4 13 -1.8210 9.64243 1 -3 4 13 0.41800 4.77307 1 -5 4 13 -0.5913 8.99756 -2 -3 4 13 -0.5913 8.99756 1 -3 4 13 1.42543 3.15632 2 -2 4 13 -1.2949 3.85257 1 -2 4 13 -2.6954 2.99877 2 -6 4 13 10.2067 10.3914 -2 -2 4 13 10.2067 10.3914 1 -1 4 13 -0.4255 2.66354 2 -1 4 13 -0.0133 3.36087 1 -6 4 13 -6.4111 10.6365 -2 -1 4 13 -6.4111 10.6365 1 0 4 13 5.64553 3.38982 2 -7 4 13 -18.016 9.89604 -2 0 4 13 -18.016 9.89604 1 0 4 13 -0.1543 3.45338 1 1 4 13 4.69747 4.22201 1 1 4 13 1.36697 3.24629 2 -10 0 14 3.85490 4.84817 2 2 0 14 6.73588 7.92072 -2 -10 0 14 6.73588 7.92072 1 -10 0 14 -8.7892 6.71518 1 -1 0 14 11.1975 7.32281 -2 -7 0 14 11.1975 7.32281 1 -2 0 14 -4.2777 5.23472 -2 -6 0 14 -4.2777 5.23472 1 -3 0 14 15.3092 5.52777 -2 -5 0 14 15.3092 5.52777 1 -4 0 14 -7.2947 4.79482 -2 -4 0 14 -7.2947 4.79482 1 -5 0 14 18.5727 5.51820 -2 -3 0 14 18.5727 5.51820 1 -6 0 14 -6.5788 7.12142 -2 -2 0 14 -6.5788 7.12142 1 -7 0 14 33.7548 8.80705 -2 -1 0 14 33.7548 8.80705 1 -8 0 14 -9.3024 6.99837 -2 0 0 14 -9.3024 6.99837 1 -9 0 14 26.8007 9.08680 -2 1 0 14 26.8007 9.08680 1 -10 1 14 3.87966 5.44057 2 0 1 14 41.7005 8.99419 -2 -8 1 14 41.7005 8.99419 1 -1 1 14 4.20262 7.72257 -2 -7 1 14 4.20262 7.72257 1 -2 1 14 18.8562 7.72621 -2 -6 1 14 18.8562 7.72621 1 -3 1 14 8.67103 4.29351 -2 -5 1 14 8.67103 4.29351 1 -4 1 14 39.5102 4.37280 -2 -4 1 14 39.5102 4.37280 1 -5 1 14 8.17552 3.93209 -2 -3 1 14 8.17552 3.93209 1 -6 1 14 41.4773 6.36100 -2 -2 1 14 41.4773 6.36100 1 -7 1 14 2.28906 6.91905 -2 -1 1 14 2.28906 6.91905 1 -8 1 14 42.7948 8.74052 -2 0 1 14 42.7948 8.74052 1 -9 1 14 -1.2750 5.42470 -2 1 1 14 -1.2750 5.42470 1 0 2 14 0.73844 5.09748 -2 -8 2 14 0.73844 5.09748 1 -1 2 14 24.1260 7.95544 -2 -7 2 14 24.1260 7.95544 1 -2 2 14 6.04507 7.46803 -2 -6 2 14 6.04507 7.46803 1 -3 2 14 51.4595 9.03421 -2 -5 2 14 51.4595 9.03421 1 -4 2 14 10.8749 7.42162 -2 -4 2 14 10.8749 7.42162 1 -5 2 14 18.0915 6.46670 -2 -3 2 14 18.0915 6.46670 1 -6 2 14 -0.4263 5.25684 -2 -2 2 14 -0.4263 5.25684 1 -7 2 14 19.9015 8.52676 -2 -1 2 14 19.9015 8.52676 1 -8 2 14 1.21415 5.34664 -2 0 2 14 1.21415 5.34664 1 -4 3 14 7.58341 9.30214 -2 -4 3 14 7.58341 9.30214 1 -5 3 14 -8.4928 9.82109 -2 -3 3 14 -8.4928 9.82109 1 0 0 0 0.00 0.00 0 ; _shelx_hkl_checksum 35901 _shelx_res_file ; TITL jtm1530_a.res in P2(1)/c jtm1530_5.res created by SHELXL-2019/1 at 14:58:43 on 01-Apr-2022 REM Old TITL jtm1530 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.218, Rweak 0.068, Alpha 0.072 REM 0.763 for 244 systematic absences, Orientation as input REM Formula found by SHELXT: C21 N3 O2 CELL 0.71073 17.7639 8.4429 11.6601 90.000 100.948 90.000 ZERR 4.000 0.0025 0.0012 0.0016 0.000 0.004 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 84 68 12 8 TEMP -123 SIZE 0.02 0.21 0.377 L.S. 5 BOND $H LIST 4 FMAP 2 PLAN 5 CONF EQIV $1 -x+1, -y+1, -z+1 HTAB O2 N1_$1 EQIV $2 x, -y+1/2, z+1/2 HTAB N2 O1_$2 EQIV $3 -x+1, y-1/2, -z+3/2 HTAB N3 O2_$3 MPLA C4 > C9 MPLA N1 N2 C1 > C3 MPLA C10 > C15 MPLA N1 N2 C1 > C3 MPLA C16 > C21 ACTA 58 OMIT 0 0 2 DFIX 0.91 0.01 N2 H2 N3 H3 DFIX 0.84 0.01 O2 H2A WGHT 0.045700 0.570900 BASF 0.29014 FVAR 0.72371 O1 4 0.764400 0.125564 0.592600 11.00000 0.06891 0.06188 = 0.02676 -0.00295 0.00639 0.01888 O2 4 0.437717 0.822986 0.487783 11.00000 0.06902 0.05765 = 0.05995 0.00001 -0.01990 0.01404 H2A 2 0.403342 0.767274 0.443838 11.00000 0.09155 N1 3 0.686010 0.297964 0.667271 11.00000 0.04281 0.05021 = 0.02695 0.00118 -0.00007 0.00836 N2 3 0.733571 0.265791 0.860272 11.00000 0.04238 0.04763 = 0.02318 -0.00069 -0.00034 0.01009 H2 2 0.745262 0.302618 0.933884 11.00000 0.04675 N3 3 0.633278 0.444984 0.805154 11.00000 0.04459 0.05333 = 0.03356 0.00315 0.00593 0.01504 H3 2 0.626164 0.448163 0.878807 11.00000 0.05675 C1 1 0.784059 0.167532 0.804953 11.00000 0.03696 0.03914 = 0.02548 -0.00074 0.00362 0.00740 C2 1 0.744370 0.192698 0.675472 11.00000 0.04242 0.04204 = 0.02954 0.00272 0.00311 0.00378 C3 1 0.682996 0.340120 0.778348 11.00000 0.03360 0.04362 = 0.03200 0.00182 0.00346 0.00140 C4 1 0.866367 0.233517 0.828336 11.00000 0.04227 0.03977 = 0.03669 -0.00173 0.00910 0.00168 C5 1 0.915384 0.195329 0.930769 11.00000 0.05151 0.09456 = 0.04926 0.01568 -0.00411 -0.01953 AFIX 43 H5 2 0.898781 0.124191 0.984000 11.00000 -1.20000 AFIX 0 C6 1 0.988070 0.258449 0.957431 11.00000 0.05565 0.12588 = 0.06798 0.01444 -0.01280 -0.02547 AFIX 43 H6 2 1.020691 0.231765 1.029192 11.00000 -1.20000 AFIX 0 C7 1 1.013496 0.358549 0.881951 11.00000 0.04535 0.10215 = 0.08214 -0.01127 0.01143 -0.01610 AFIX 43 H7 2 1.063708 0.401801 0.900559 11.00000 -1.20000 AFIX 0 C8 1 0.966689 0.396087 0.780073 11.00000 0.06218 0.08539 = 0.08207 0.01069 0.02645 -0.01855 AFIX 43 H8 2 0.984311 0.465610 0.726783 11.00000 -1.20000 AFIX 0 C9 1 0.893140 0.333985 0.752641 11.00000 0.05642 0.07207 = 0.05451 0.01173 0.01028 -0.00325 AFIX 43 H9 2 0.860949 0.361313 0.680653 11.00000 -1.20000 AFIX 0 C10 1 0.783762 -0.004751 0.841302 11.00000 0.03133 0.04444 = 0.03104 0.00183 -0.00141 0.00038 C11 1 0.753739 -0.054259 0.937085 11.00000 0.04453 0.05688 = 0.04503 0.00884 0.00620 0.00094 AFIX 43 H11 2 0.728488 0.019425 0.978410 11.00000 -1.20000 AFIX 0 C12 1 0.760713 -0.211549 0.972263 11.00000 0.06407 0.07156 = 0.05946 0.02705 0.00651 -0.01040 AFIX 43 H12 2 0.740132 -0.244907 1.037771 11.00000 -1.20000 AFIX 0 C13 1 0.796925 -0.319047 0.913560 11.00000 0.06192 0.04767 = 0.07960 0.01348 -0.01732 -0.00794 AFIX 43 H13 2 0.801641 -0.426344 0.938423 11.00000 -1.20000 AFIX 0 C14 1 0.826348 -0.271185 0.818754 11.00000 0.06139 0.04910 = 0.07271 -0.00147 0.00097 0.00799 AFIX 43 H14 2 0.851184 -0.345553 0.777377 11.00000 -1.20000 AFIX 0 C15 1 0.819950 -0.115950 0.783584 11.00000 0.05074 0.04862 = 0.04964 0.00043 0.00809 0.00651 AFIX 43 H15 2 0.840871 -0.084081 0.718038 11.00000 -1.20000 AFIX 0 C16 1 0.582834 0.538652 0.720227 11.00000 0.04041 0.04324 = 0.03807 0.00248 0.00383 0.00957 C17 1 0.508423 0.491849 0.680722 11.00000 0.04552 0.05368 = 0.05954 0.01007 0.00336 -0.00046 AFIX 43 H17 2 0.490481 0.394955 0.707081 11.00000 -1.20000 AFIX 0 C18 1 0.459517 0.585929 0.602428 11.00000 0.03717 0.06501 = 0.06069 0.00246 -0.00251 0.00365 AFIX 43 H18 2 0.407891 0.553935 0.575721 11.00000 -1.20000 AFIX 0 C19 1 0.485363 0.724871 0.563429 11.00000 0.04726 0.04940 = 0.04323 -0.00373 -0.00478 0.01096 C20 1 0.560025 0.772201 0.602008 11.00000 0.05608 0.04807 = 0.06329 0.00741 -0.00187 -0.00110 AFIX 43 H20 2 0.578193 0.867915 0.574152 11.00000 -1.20000 AFIX 0 C21 1 0.608619 0.678831 0.682045 11.00000 0.04014 0.05881 = 0.05623 0.00449 -0.00523 0.00080 AFIX 43 H21 2 0.659858 0.712093 0.710447 11.00000 -1.20000 AFIX 0 HKLF 5 REM jtm1530_a.res in P2(1)/c REM wR2 = 0.1319, GooF = S = 1.035, Restrained GooF = 1.036 for all data REM R1 = 0.0546 for 3329 Fo > 4sig(Fo) and 0.1042 for all 5347 data REM 248 parameters refined using 3 restraints END WGHT 0.0456 0.5726 REM Highest difference peak 0.227, deepest hole -0.219, 1-sigma level 0.044 Q1 1 0.8297 0.1933 0.8159 11.00000 0.05 0.23 Q2 1 0.8700 0.3162 0.8202 11.00000 0.05 0.20 Q3 1 0.7837 0.0828 0.8232 11.00000 0.05 0.19 Q4 1 0.5773 0.9420 0.5699 11.00000 0.05 0.16 Q5 1 0.9225 -0.0486 0.9767 11.00000 0.05 0.16 ; _shelx_res_checksum 14529 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_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.76440(12) 0.1256(2) 0.59260(16) 0.0529(6) Uani d 1 . . O O2 0.43772(15) 0.8230(3) 0.4878(2) 0.0664(7) Uani d 1 . . H H2A 0.4033(16) 0.767(4) 0.444(3) 0.092(14) Uiso d 1 . . N N1 0.68601(13) 0.2980(3) 0.66727(18) 0.0409(6) Uani d 1 . . N N2 0.73357(13) 0.2658(3) 0.86027(18) 0.0386(6) Uani d 1 . . H H2 0.7453(16) 0.303(3) 0.9339(13) 0.047(9) Uiso d 1 . . N N3 0.63328(14) 0.4450(3) 0.8052(2) 0.0440(6) Uani d 1 . . H H3 0.6262(16) 0.448(3) 0.8788(13) 0.057(10) Uiso d 1 . . C C1 0.78406(15) 0.1675(3) 0.8050(2) 0.0342(6) Uani d 1 . . C C2 0.74437(17) 0.1927(3) 0.6755(2) 0.0385(7) Uani d 1 . . C C3 0.68300(16) 0.3401(3) 0.7783(2) 0.0368(7) Uani d 1 . . C C4 0.86637(16) 0.2335(3) 0.8283(2) 0.0394(7) Uani d 1 . . C C5 0.91538(19) 0.1953(5) 0.9308(3) 0.0669(11) Uani d 1 . . H H5 0.898781 0.124191 0.984000 0.080 Uiso calc 1 . . C C6 0.9881(2) 0.2584(5) 0.9574(3) 0.0864(13) Uani d 1 . . H H6 1.020691 0.231765 1.029192 0.104 Uiso calc 1 . . C C7 1.0135(2) 0.3585(5) 0.8820(4) 0.0766(12) Uani d 1 . . H H7 1.063708 0.401801 0.900559 0.092 Uiso calc 1 . . C C8 0.9667(2) 0.3961(5) 0.7801(4) 0.0749(11) Uani d 1 . . H H8 0.984311 0.465610 0.726783 0.090 Uiso calc 1 . . C C9 0.8931(2) 0.3340(4) 0.7526(3) 0.0610(9) Uani d 1 . . H H9 0.860949 0.361313 0.680653 0.073 Uiso calc 1 . . C C10 0.78376(15) -0.0048(3) 0.8413(2) 0.0366(7) Uani d 1 . . C C11 0.75374(17) -0.0543(4) 0.9371(3) 0.0491(8) Uani d 1 . . H H11 0.728488 0.019425 0.978410 0.059 Uiso calc 1 . . C C12 0.7607(2) -0.2115(4) 0.9723(3) 0.0657(10) Uani d 1 . . H H12 0.740132 -0.244907 1.037771 0.079 Uiso calc 1 . . C C13 0.7969(2) -0.3190(4) 0.9136(4) 0.0671(11) Uani d 1 . . H H13 0.801641 -0.426344 0.938423 0.081 Uiso calc 1 . . C C14 0.8263(2) -0.2712(4) 0.8188(3) 0.0626(9) Uani d 1 . . H H14 0.851184 -0.345553 0.777377 0.075 Uiso calc 1 . . C C15 0.81995(18) -0.1159(4) 0.7836(3) 0.0499(8) Uani d 1 . . H H15 0.840871 -0.084081 0.718038 0.060 Uiso calc 1 . . C C16 0.58283(16) 0.5387(3) 0.7202(2) 0.0410(7) Uani d 1 . . C C17 0.50842(17) 0.4918(4) 0.6807(3) 0.0538(8) Uani d 1 . . H H17 0.490481 0.394955 0.707081 0.065 Uiso calc 1 . . C C18 0.45952(18) 0.5859(4) 0.6024(3) 0.0558(9) Uani d 1 . . H H18 0.407891 0.553935 0.575721 0.067 Uiso calc 1 . . C C19 0.48536(18) 0.7249(4) 0.5634(2) 0.0484(8) Uani d 1 . . C C20 0.56002(19) 0.7722(4) 0.6020(3) 0.0575(9) Uani d 1 . . H H20 0.578193 0.867915 0.574152 0.069 Uiso calc 1 . . C C21 0.60862(18) 0.6788(4) 0.6820(3) 0.0536(8) Uani d 1 . . H H21 0.659858 0.712093 0.710447 0.064 Uiso calc 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0689(15) 0.0619(14) 0.0268(11) 0.0189(11) 0.0064(10) -0.0030(10) O2 0.0690(17) 0.0577(15) 0.0600(15) 0.0140(13) -0.0199(13) 0.0000(13) N1 0.0428(15) 0.0502(15) 0.0270(12) 0.0084(12) -0.0001(11) 0.0012(11) N2 0.0424(14) 0.0476(15) 0.0232(12) 0.0101(12) -0.0003(11) -0.0007(12) N3 0.0446(15) 0.0533(16) 0.0336(14) 0.0150(13) 0.0059(12) 0.0031(13) C1 0.0370(16) 0.0391(16) 0.0255(13) 0.0074(13) 0.0036(12) -0.0007(12) C2 0.0424(17) 0.0420(17) 0.0295(15) 0.0038(14) 0.0031(13) 0.0027(13) C3 0.0336(16) 0.0436(17) 0.0320(15) 0.0014(13) 0.0035(13) 0.0018(13) C4 0.0423(17) 0.0398(16) 0.0367(16) 0.0017(14) 0.0091(14) -0.0017(14) C5 0.052(2) 0.095(3) 0.049(2) -0.020(2) -0.0041(17) 0.0157(19) C6 0.056(2) 0.126(4) 0.068(2) -0.025(2) -0.013(2) 0.014(3) C7 0.045(2) 0.102(3) 0.082(3) -0.016(2) 0.011(2) -0.011(3) C8 0.062(2) 0.085(3) 0.082(3) -0.019(2) 0.026(2) 0.011(2) C9 0.056(2) 0.072(2) 0.055(2) -0.0032(19) 0.0103(17) 0.0117(19) C10 0.0313(15) 0.0444(17) 0.0310(15) 0.0004(13) -0.0014(12) 0.0018(13) C11 0.0445(18) 0.057(2) 0.0450(18) 0.0009(16) 0.0062(15) 0.0088(16) C12 0.064(2) 0.072(3) 0.059(2) -0.010(2) 0.0065(19) 0.027(2) C13 0.062(2) 0.048(2) 0.080(3) -0.0079(19) -0.017(2) 0.013(2) C14 0.061(2) 0.049(2) 0.073(2) 0.0080(17) 0.0010(19) -0.001(2) C15 0.0507(19) 0.049(2) 0.0496(19) 0.0065(15) 0.0081(16) 0.0004(16) C16 0.0404(18) 0.0432(18) 0.0381(16) 0.0096(14) 0.0038(14) 0.0025(14) C17 0.0455(19) 0.054(2) 0.060(2) -0.0005(16) 0.0034(17) 0.0101(17) C18 0.0372(17) 0.065(2) 0.061(2) 0.0037(17) -0.0025(16) 0.0025(18) C19 0.0473(19) 0.049(2) 0.0432(17) 0.0110(16) -0.0048(15) -0.0037(16) C20 0.056(2) 0.0481(19) 0.063(2) -0.0011(16) -0.0019(18) 0.0074(17) C21 0.0401(18) 0.059(2) 0.056(2) 0.0008(17) -0.0052(16) 0.0045(17) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C19 O2 H2A . . 109(2) ? C3 N1 C2 . . 105.9(2) ? C3 N2 C1 . . 109.7(2) ? C3 N2 H2 . . 121.4(18) ? C1 N2 H2 . . 124.7(18) ? C3 N3 C16 . . 124.0(2) ? C3 N3 H3 . . 117.9(19) ? C16 N3 H3 . . 117.5(19) ? N2 C1 C10 . . 112.8(2) ? N2 C1 C4 . . 111.0(2) ? C10 C1 C4 . . 110.6(2) ? N2 C1 C2 . . 98.5(2) ? C10 C1 C2 . . 112.2(2) ? C4 C1 C2 . . 111.3(2) ? O1 C2 N1 . . 125.3(2) ? O1 C2 C1 . . 123.7(2) ? N1 C2 C1 . . 111.0(2) ? N3 C3 N2 . . 122.1(3) ? N3 C3 N1 . . 123.3(2) ? N2 C3 N1 . . 114.6(3) ? C9 C4 C5 . . 117.6(3) ? C9 C4 C1 . . 122.9(2) ? C5 C4 C1 . . 119.5(3) ? C4 C5 C6 . . 121.1(3) ? C4 C5 H5 . . 119.4 ? C6 C5 H5 . . 119.4 ? C7 C6 C5 . . 120.5(3) ? C7 C6 H6 . . 119.7 ? C5 C6 H6 . . 119.7 ? C8 C7 C6 . . 119.4(3) ? C8 C7 H7 . . 120.3 ? C6 C7 H7 . . 120.3 ? C7 C8 C9 . . 120.6(4) ? C7 C8 H8 . . 119.7 ? C9 C8 H8 . . 119.7 ? C4 C9 C8 . . 120.8(3) ? C4 C9 H9 . . 119.6 ? C8 C9 H9 . . 119.6 ? C15 C10 C11 . . 118.1(3) ? C15 C10 C1 . . 119.3(3) ? C11 C10 C1 . . 122.4(3) ? C12 C11 C10 . . 119.9(3) ? C12 C11 H11 . . 120.0 ? C10 C11 H11 . . 120.0 ? C13 C12 C11 . . 120.7(3) ? C13 C12 H12 . . 119.7 ? C11 C12 H12 . . 119.7 ? C12 C13 C14 . . 119.7(3) ? C12 C13 H13 . . 120.2 ? C14 C13 H13 . . 120.2 ? C13 C14 C15 . . 120.0(3) ? C13 C14 H14 . . 120.0 ? C15 C14 H14 . . 120.0 ? C14 C15 C10 . . 121.5(3) ? C14 C15 H15 . . 119.2 ? C10 C15 H15 . . 119.2 ? C17 C16 C21 . . 119.9(3) ? C17 C16 N3 . . 120.4(3) ? C21 C16 N3 . . 119.6(3) ? C16 C17 C18 . . 120.0(3) ? C16 C17 H17 . . 120.0 ? C18 C17 H17 . . 120.0 ? C19 C18 C17 . . 120.2(3) ? C19 C18 H18 . . 119.9 ? C17 C18 H18 . . 119.9 ? C18 C19 C20 . . 120.2(3) ? C18 C19 O2 . . 121.6(3) ? C20 C19 O2 . . 118.1(3) ? C19 C20 C21 . . 119.5(3) ? C19 C20 H20 . . 120.3 ? C21 C20 H20 . . 120.3 ? C16 C21 C20 . . 120.2(3) ? C16 C21 H21 . . 119.9 ? C20 C21 H21 . . 119.9 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 . 1.230(3) ? O2 C19 . 1.377(3) ? O2 H2A . 0.859(12) ? N1 C3 . 1.354(3) ? N1 C2 . 1.355(3) ? N2 C3 . 1.337(3) ? N2 C1 . 1.459(3) ? N2 H2 . 0.899(12) ? N3 C3 . 1.329(3) ? N3 C16 . 1.439(3) ? N3 H3 . 0.892(12) ? C1 C10 . 1.515(4) ? C1 C4 . 1.540(4) ? C1 C2 . 1.555(4) ? C4 C9 . 1.373(4) ? C4 C5 . 1.376(4) ? C5 C6 . 1.377(5) ? C5 H5 . 0.9500 ? C6 C7 . 1.358(5) ? C6 H6 . 0.9500 ? C7 C8 . 1.352(5) ? C7 H7 . 0.9500 ? C8 C9 . 1.388(5) ? C8 H8 . 0.9500 ? C9 H9 . 0.9500 ? C10 C15 . 1.383(4) ? C10 C11 . 1.390(4) ? C11 C12 . 1.388(4) ? C11 H11 . 0.9500 ? C12 C13 . 1.369(5) ? C12 H12 . 0.9500 ? C13 C14 . 1.370(5) ? C13 H13 . 0.9500 ? C14 C15 . 1.372(4) ? C14 H14 . 0.9500 ? C15 H15 . 0.9500 ? C16 C17 . 1.373(4) ? C16 C21 . 1.373(4) ? C17 C18 . 1.385(4) ? C17 H17 . 0.9500 ? C18 C19 . 1.369(4) ? C18 H18 . 0.9500 ? C19 C20 . 1.376(4) ? C20 C21 . 1.390(4) ? C20 H20 . 0.9500 ? C21 H21 . 0.9500 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O2 H2A N1 3_666 0.859(12) 1.929(16) 2.763(3) 163(4) yes N2 H2 O1 4_566 0.899(12) 1.916(13) 2.814(3) 176(3) yes N3 H3 O2 2_646 0.892(12) 2.34(2) 3.104(4) 143(2) yes C17 H17 Cg4 2_646 0.95 2.92 3.831(4) 162 y C21 H21 Cg3 1_565 0.95 2.93 3.822(4) 157 y 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C3 N2 C1 C10 . . . . -123.8(2) ? C3 N2 C1 C4 . . . . 111.5(3) ? C3 N2 C1 C2 . . . . -5.3(3) ? C3 N1 C2 O1 . . . . 179.0(3) ? C3 N1 C2 C1 . . . . -1.4(3) ? N2 C1 C2 O1 . . . . -176.3(3) ? C10 C1 C2 O1 . . . . -57.4(4) ? C4 C1 C2 O1 . . . . 67.1(4) ? N2 C1 C2 N1 . . . . 4.1(3) ? C10 C1 C2 N1 . . . . 123.0(3) ? C4 C1 C2 N1 . . . . -112.5(3) ? C16 N3 C3 N2 . . . . 173.9(3) ? C16 N3 C3 N1 . . . . -7.2(5) ? C1 N2 C3 N3 . . . . -175.7(3) ? C1 N2 C3 N1 . . . . 5.3(3) ? C2 N1 C3 N3 . . . . 178.7(3) ? C2 N1 C3 N2 . . . . -2.3(3) ? N2 C1 C4 C9 . . . . -94.0(3) ? C10 C1 C4 C9 . . . . 140.0(3) ? C2 C1 C4 C9 . . . . 14.6(4) ? N2 C1 C4 C5 . . . . 83.9(3) ? C10 C1 C4 C5 . . . . -42.0(4) ? C2 C1 C4 C5 . . . . -167.4(3) ? C9 C4 C5 C6 . . . . 1.4(5) ? C1 C4 C5 C6 . . . . -176.7(3) ? C4 C5 C6 C7 . . . . -1.0(6) ? C5 C6 C7 C8 . . . . 0.1(6) ? C6 C7 C8 C9 . . . . 0.3(6) ? C5 C4 C9 C8 . . . . -1.0(5) ? C1 C4 C9 C8 . . . . 177.0(3) ? C7 C8 C9 C4 . . . . 0.1(6) ? N2 C1 C10 C15 . . . . 170.7(2) ? C4 C1 C10 C15 . . . . -64.3(3) ? C2 C1 C10 C15 . . . . 60.5(3) ? N2 C1 C10 C11 . . . . -14.7(3) ? C4 C1 C10 C11 . . . . 110.3(3) ? C2 C1 C10 C11 . . . . -124.8(3) ? C15 C10 C11 C12 . . . . 0.1(4) ? C1 C10 C11 C12 . . . . -174.6(3) ? C10 C11 C12 C13 . . . . 0.0(5) ? C11 C12 C13 C14 . . . . -0.3(5) ? C12 C13 C14 C15 . . . . 0.5(5) ? C13 C14 C15 C10 . . . . -0.4(5) ? C11 C10 C15 C14 . . . . 0.1(4) ? C1 C10 C15 C14 . . . . 175.0(3) ? C3 N3 C16 C17 . . . . 97.0(4) ? C3 N3 C16 C21 . . . . -85.6(4) ? C21 C16 C17 C18 . . . . 0.0(5) ? N3 C16 C17 C18 . . . . 177.5(3) ? C16 C17 C18 C19 . . . . 0.6(5) ? C17 C18 C19 C20 . . . . -0.2(5) ? C17 C18 C19 O2 . . . . -178.4(3) ? C18 C19 C20 C21 . . . . -0.9(5) ? O2 C19 C20 C21 . . . . 177.4(3) ? C17 C16 C21 C20 . . . . -1.1(5) ? N3 C16 C21 C20 . . . . -178.6(3) ? C19 C20 C21 C16 . . . . 1.5(5) ?