#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:10:12 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247620 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125638.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_7125638 loop_ _publ_author_name 'Ajarul, Sk' 'Kayet, Anirban' 'Pati, Tanmay K.' 'Maiti, Dilip K.' _publ_section_title ; A competitive and highly selective 7-, 6- and 5-annulation with 1,3-migration through C-H and N-H - alkyne coupling. ; _journal_issue 3 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 474 _journal_page_last 477 _journal_paper_doi 10.1039/c9cc07360d _journal_volume 56 _journal_year 2020 _chemical_formula_sum 'C23 H17 N O2' _chemical_formula_weight 339.38 _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 _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2019-04-19 deposited with the CCDC. 2019-11-28 downloaded from the CCDC. ; _cell_angle_alpha 73.867(4) _cell_angle_beta 70.650(4) _cell_angle_gamma 78.883(4) _cell_formula_units_Z 2 _cell_length_a 9.2441(16) _cell_length_b 9.5954(16) _cell_length_c 10.6672(18) _cell_measurement_reflns_used 890 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.176 _cell_measurement_theta_min 2.223 _cell_volume 852.3(3) _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type CCD _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_unetI/netI 0.0294 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 21150 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.176 _diffrn_reflns_theta_min 2.223 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABAS _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 356 _exptl_transmission_factor_max 0.755 _exptl_transmission_factor_min 0.639 _refine_diff_density_max 0.222 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 239 _refine_ls_number_reflns 3744 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0494 _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^)+(0.0632P)^2^+0.3097P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1318 _refine_ls_wR_factor_ref 0.1445 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3048 _reflns_number_total 3744 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc07360d2.cif _cod_data_source_block shelx _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 6909 2019-04-08 15:41:33Z antanas Adding full bibliography for 7125638--7125639.cif. ; _cod_database_code 7125638 _shelx_shelxl_version_number 2017/1 _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_res_file ; TITL ASPG_216A_0m_a.res in P-1 shelx.res created by SHELXL-2017/1 at 15:13:59 on 06-Sep-2018 CELL 0.71073 9.2441 9.5954 10.6672 73.867 70.650 78.883 ZERR 2.00 0.0016 0.0016 0.0018 0.004 0.004 0.004 LATT 1 SFAC C H N O UNIT 46 34 2 4 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 10 TEMP 0.00 WGHT 0.063200 0.309700 FVAR 1.90604 O1 4 0.333982 0.109708 0.583548 11.00000 0.05029 0.05148 = 0.05929 -0.02950 -0.02661 0.00732 O2 4 0.113797 0.202933 0.893280 11.00000 0.05519 0.05948 = 0.04950 0.00354 -0.00315 -0.00955 N1 3 0.566492 0.042490 0.623858 11.00000 0.04572 0.03424 = 0.04336 -0.01711 -0.01849 0.00393 C1 1 0.087914 0.656904 0.533132 11.00000 0.06948 0.03958 = 0.06399 -0.00562 -0.02327 0.00868 AFIX 43 H1 2 0.060879 0.744874 0.477584 11.00000 -1.20000 AFIX 0 C2 1 -0.025029 0.581177 0.634529 11.00000 0.04759 0.05247 = 0.08253 -0.01519 -0.02093 0.01220 AFIX 43 H3 2 -0.128263 0.618154 0.647527 11.00000 -1.20000 AFIX 0 C3 1 0.014643 0.450887 0.716635 11.00000 0.03990 0.04833 = 0.05588 -0.01255 -0.00635 -0.00047 AFIX 43 H4 2 -0.061892 0.400110 0.785205 11.00000 -1.20000 AFIX 0 C4 1 0.168952 0.394752 0.697461 11.00000 0.03912 0.03481 = 0.03712 -0.01267 -0.00825 -0.00013 C5 1 0.209781 0.258274 0.791275 11.00000 0.04239 0.03761 = 0.03507 -0.01096 -0.00740 -0.00576 C6 1 0.373871 0.187015 0.761292 11.00000 0.04374 0.02829 = 0.03422 -0.00686 -0.01160 -0.00271 C7 1 0.468750 0.184727 0.836445 11.00000 0.05244 0.02748 = 0.03147 -0.00401 -0.01306 -0.00640 C8 1 0.411911 0.263391 0.952661 11.00000 0.06606 0.04486 = 0.03439 -0.01156 -0.01529 -0.00653 AFIX 23 H10 2 0.315386 0.229214 1.014409 11.00000 -1.20000 H9 2 0.486563 0.239611 1.003500 11.00000 -1.20000 AFIX 0 C9 1 0.387808 0.427146 0.901644 11.00000 0.05030 0.04314 = 0.03578 -0.01757 -0.01188 -0.00609 C10 1 0.244989 0.504509 0.944340 11.00000 0.05193 0.05681 = 0.05099 -0.02387 -0.00245 -0.00771 AFIX 43 H8 2 0.163942 0.455522 1.008037 11.00000 -1.20000 AFIX 0 C11 1 0.220745 0.653237 0.893974 11.00000 0.06301 0.05553 = 0.07777 -0.03224 -0.01566 0.00716 AFIX 43 H5 2 0.124312 0.703888 0.924352 11.00000 -1.20000 AFIX 0 C12 1 0.338939 0.725931 0.799259 11.00000 0.08564 0.04141 = 0.07667 -0.01805 -0.02628 -0.00472 AFIX 43 H2 2 0.322340 0.825727 0.763572 11.00000 -1.20000 AFIX 0 C13 1 0.482503 0.651156 0.756834 11.00000 0.06964 0.05000 = 0.06987 -0.01418 -0.01038 -0.01979 AFIX 43 H6 2 0.563161 0.700791 0.693281 11.00000 -1.20000 AFIX 0 C14 1 0.506932 0.503162 0.808238 11.00000 0.04942 0.04942 = 0.05849 -0.01984 -0.00902 -0.00844 AFIX 43 H7 2 0.604550 0.453675 0.779909 11.00000 -1.20000 AFIX 0 C15 1 0.623563 0.109791 0.802283 11.00000 0.04979 0.02910 = 0.03726 -0.00055 -0.01889 -0.00750 C16 1 0.734882 0.104785 0.868029 11.00000 0.06713 0.04680 = 0.04735 -0.00326 -0.02977 -0.01213 AFIX 43 H11 2 0.709915 0.152269 0.938741 11.00000 -1.20000 AFIX 0 C17 1 0.879647 0.030938 0.829404 11.00000 0.05879 0.05861 = 0.06234 0.00422 -0.03629 -0.01204 AFIX 43 H12 2 0.951257 0.029145 0.874024 11.00000 -1.20000 AFIX 0 C18 1 0.919395 -0.040812 0.724367 11.00000 0.04955 0.05501 = 0.06736 -0.00083 -0.02607 -0.00044 AFIX 43 H13 2 1.017120 -0.091304 0.699562 11.00000 -1.20000 AFIX 0 C19 1 0.815366 -0.037689 0.656911 11.00000 0.04805 0.04288 = 0.05508 -0.01034 -0.01896 0.00410 AFIX 43 H14 2 0.842320 -0.085733 0.586380 11.00000 -1.20000 AFIX 0 C20 1 0.668674 0.038056 0.694714 11.00000 0.04475 0.02814 = 0.04093 -0.00301 -0.01719 -0.00395 C21 1 0.421230 0.112642 0.650332 11.00000 0.04348 0.02918 = 0.03975 -0.00989 -0.01502 -0.00167 C22 1 0.281137 0.471199 0.595011 11.00000 0.04064 0.04109 = 0.04613 -0.00580 -0.00701 -0.00114 AFIX 43 H15 2 0.384455 0.434003 0.580569 11.00000 -1.20000 AFIX 0 C23 1 0.240674 0.602599 0.513901 11.00000 0.05985 0.04262 = 0.05302 -0.00001 -0.00947 -0.00442 AFIX 43 H16 2 0.316861 0.654530 0.446100 11.00000 -1.20000 AFIX 0 H1A 2 0.601699 -0.007629 0.553329 11.00000 0.04962 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM ASPG_216A_0m_a.res in P-1 REM R1 = 0.0494 for 3048 Fo > 4sig(Fo) and 0.0620 for all 3744 data REM 239 parameters refined using 0 restraints END WGHT 0.0631 0.3096 REM Highest difference peak 0.222, deepest hole -0.193, 1-sigma level 0.042 Q1 1 0.1856 0.3249 0.7314 11.00000 0.05 0.22 Q2 1 0.1516 0.6048 0.5002 11.00000 0.05 0.21 Q3 1 0.4344 0.2158 0.8988 11.00000 0.05 0.19 Q4 1 0.6585 0.0977 0.7209 11.00000 0.05 0.18 Q5 1 0.0983 0.4414 0.7330 11.00000 0.05 0.18 Q6 1 0.0914 0.4018 0.6890 11.00000 0.05 0.17 Q7 1 0.2932 0.2188 0.7714 11.00000 0.05 0.17 Q8 1 0.6394 0.0578 0.7629 11.00000 0.05 0.17 Q9 1 0.0419 0.5816 0.5702 11.00000 0.05 0.16 Q10 1 0.4007 0.1514 0.8234 11.00000 0.05 0.16 Q11 1 0.4066 0.1734 0.6922 11.00000 0.05 0.15 Q12 1 0.2116 0.4418 0.6803 11.00000 0.05 0.15 Q13 1 0.8348 0.1173 0.7975 11.00000 0.05 0.14 Q14 1 0.3139 0.4557 0.8898 11.00000 0.05 0.14 Q15 1 0.8902 0.0099 0.6635 11.00000 0.05 0.14 Q16 1 0.0230 0.4848 0.6265 11.00000 0.05 0.14 Q17 1 0.9141 0.0439 0.7433 11.00000 0.05 0.14 Q18 1 0.7653 0.0422 0.6381 11.00000 0.05 0.14 Q19 1 0.0458 0.6431 0.6330 11.00000 0.05 0.14 Q20 1 0.4277 0.4645 0.8273 11.00000 0.05 0.13 ; _shelx_res_checksum 88873 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 _atom_site_refinement_flags_adp O1 O 0.33398(13) 0.10971(13) 0.58355(12) 0.0493(3) Uani 1 1 d . . O2 O 0.11380(15) 0.20293(14) 0.89328(13) 0.0608(4) Uani 1 1 d . . N1 N 0.56649(15) 0.04249(13) 0.62386(13) 0.0392(3) Uani 1 1 d . . C1 C 0.0879(2) 0.6569(2) 0.5331(2) 0.0602(5) Uani 1 1 d . . H1 H 0.060879 0.744874 0.477584 0.072 Uiso 1 1 calc R U C2 C -0.0250(2) 0.5812(2) 0.6345(2) 0.0630(5) Uani 1 1 d . . H3 H -0.128263 0.618154 0.647527 0.076 Uiso 1 1 calc R U C3 C 0.01464(19) 0.45089(19) 0.71664(19) 0.0506(4) Uani 1 1 d . . H4 H -0.061892 0.400110 0.785205 0.061 Uiso 1 1 calc R U C4 C 0.16895(17) 0.39475(15) 0.69746(14) 0.0374(3) Uani 1 1 d . . C5 C 0.20978(18) 0.25827(16) 0.79128(15) 0.0387(3) Uani 1 1 d . . C6 C 0.37387(17) 0.18701(14) 0.76129(14) 0.0356(3) Uani 1 1 d . . C7 C 0.46875(18) 0.18473(15) 0.83645(14) 0.0373(3) Uani 1 1 d . . C8 C 0.4119(2) 0.26339(18) 0.95266(16) 0.0478(4) Uani 1 1 d . . H10 H 0.315386 0.229214 1.014409 0.057 Uiso 1 1 calc R U H9 H 0.486563 0.239611 1.003500 0.057 Uiso 1 1 calc R U C9 C 0.38781(19) 0.42715(17) 0.90164(15) 0.0414(3) Uani 1 1 d . . C10 C 0.2450(2) 0.5045(2) 0.94434(18) 0.0539(4) Uani 1 1 d . . H8 H 0.163942 0.455522 1.008037 0.065 Uiso 1 1 calc R U C11 C 0.2207(2) 0.6532(2) 0.8940(2) 0.0652(5) Uani 1 1 d . . H5 H 0.124312 0.703888 0.924352 0.078 Uiso 1 1 calc R U C12 C 0.3389(3) 0.7259(2) 0.7993(2) 0.0667(5) Uani 1 1 d . . H2 H 0.322340 0.825727 0.763572 0.080 Uiso 1 1 calc R U C13 C 0.4825(3) 0.6512(2) 0.7568(2) 0.0638(5) Uani 1 1 d . . H6 H 0.563161 0.700791 0.693281 0.077 Uiso 1 1 calc R U C14 C 0.5069(2) 0.50316(19) 0.80824(19) 0.0522(4) Uani 1 1 d . . H7 H 0.604550 0.453675 0.779909 0.063 Uiso 1 1 calc R U C15 C 0.62356(18) 0.10979(15) 0.80228(15) 0.0382(3) Uani 1 1 d . . C16 C 0.7349(2) 0.10479(19) 0.86803(18) 0.0512(4) Uani 1 1 d . . H11 H 0.709915 0.152269 0.938741 0.061 Uiso 1 1 calc R U C17 C 0.8796(2) 0.0309(2) 0.8294(2) 0.0582(5) Uani 1 1 d . . H12 H 0.951257 0.029145 0.874024 0.070 Uiso 1 1 calc R U C18 C 0.9194(2) -0.0408(2) 0.7244(2) 0.0586(5) Uani 1 1 d . . H13 H 1.017120 -0.091304 0.699562 0.070 Uiso 1 1 calc R U C19 C 0.8154(2) -0.03769(18) 0.65691(19) 0.0492(4) Uani 1 1 d . . H14 H 0.842320 -0.085733 0.586380 0.059 Uiso 1 1 calc R U C20 C 0.66867(17) 0.03806(15) 0.69471(15) 0.0378(3) Uani 1 1 d . . C21 C 0.42123(17) 0.11264(15) 0.65033(15) 0.0367(3) Uani 1 1 d . . C22 C 0.28114(19) 0.47120(17) 0.59501(16) 0.0455(4) Uani 1 1 d . . H15 H 0.384455 0.434003 0.580569 0.055 Uiso 1 1 calc R U C23 C 0.2407(2) 0.60260(19) 0.51390(19) 0.0562(5) Uani 1 1 d . . H16 H 0.316861 0.654530 0.446100 0.067 Uiso 1 1 calc R U H1A H 0.602(2) -0.008(2) 0.5533(19) 0.050(5) Uiso 1 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0503(7) 0.0515(7) 0.0593(7) -0.0295(5) -0.0266(6) 0.0073(5) O2 0.0552(7) 0.0595(8) 0.0495(7) 0.0035(6) -0.0031(6) -0.0096(6) N1 0.0457(7) 0.0342(6) 0.0434(7) -0.0171(5) -0.0185(6) 0.0039(5) C1 0.0695(12) 0.0396(9) 0.0640(11) -0.0056(8) -0.0233(10) 0.0087(8) C2 0.0476(10) 0.0525(10) 0.0825(14) -0.0152(9) -0.0209(10) 0.0122(8) C3 0.0399(8) 0.0483(9) 0.0559(10) -0.0126(7) -0.0064(7) -0.0005(7) C4 0.0391(7) 0.0348(7) 0.0371(7) -0.0127(6) -0.0083(6) -0.0001(6) C5 0.0424(8) 0.0376(7) 0.0351(7) -0.0110(6) -0.0074(6) -0.0058(6) C6 0.0437(8) 0.0283(6) 0.0342(7) -0.0069(5) -0.0116(6) -0.0027(5) C7 0.0524(9) 0.0275(6) 0.0315(7) -0.0040(5) -0.0131(6) -0.0064(6) C8 0.0661(11) 0.0449(9) 0.0344(7) -0.0116(6) -0.0153(7) -0.0065(7) C9 0.0503(9) 0.0431(8) 0.0358(7) -0.0176(6) -0.0119(6) -0.0061(6) C10 0.0519(10) 0.0568(10) 0.0510(9) -0.0239(8) -0.0024(8) -0.0077(8) C11 0.0630(12) 0.0555(11) 0.0778(13) -0.0322(10) -0.0157(10) 0.0072(9) C12 0.0856(15) 0.0414(9) 0.0767(13) -0.0180(9) -0.0263(12) -0.0047(9) C13 0.0696(13) 0.0500(10) 0.0699(12) -0.0142(9) -0.0104(10) -0.0198(9) C14 0.0494(9) 0.0494(9) 0.0585(10) -0.0198(8) -0.0090(8) -0.0084(7) C15 0.0498(8) 0.0291(7) 0.0373(7) -0.0006(5) -0.0189(6) -0.0075(6) C16 0.0671(11) 0.0468(9) 0.0473(9) -0.0033(7) -0.0298(8) -0.0121(8) C17 0.0588(11) 0.0586(11) 0.0623(11) 0.0042(9) -0.0363(9) -0.0120(8) C18 0.0495(10) 0.0550(10) 0.0674(12) -0.0008(9) -0.0261(9) -0.0004(8) C19 0.0481(9) 0.0429(8) 0.0551(9) -0.0103(7) -0.0190(8) 0.0041(7) C20 0.0447(8) 0.0281(6) 0.0409(7) -0.0030(5) -0.0172(6) -0.0039(6) C21 0.0435(8) 0.0292(6) 0.0398(7) -0.0099(5) -0.0150(6) -0.0017(5) C22 0.0406(8) 0.0411(8) 0.0461(8) -0.0058(6) -0.0070(7) -0.0011(6) C23 0.0598(11) 0.0426(9) 0.0530(10) 0.0000(7) -0.0095(8) -0.0044(8) 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 C21 N1 C20 124.46(12) C21 N1 H1A 119.1(11) C20 N1 H1A 116.4(11) C23 C1 C2 120.07(16) C23 C1 H1 120.0 C2 C1 H1 120.0 C3 C2 C1 120.08(17) C3 C2 H3 120.0 C1 C2 H3 120.0 C2 C3 C4 120.24(16) C2 C3 H4 119.9 C4 C3 H4 119.9 C22 C4 C3 119.18(14) C22 C4 C5 121.35(13) C3 C4 C5 119.41(14) O2 C5 C4 121.29(14) O2 C5 C6 119.03(14) C4 C5 C6 119.68(12) C7 C6 C21 122.06(13) C7 C6 C5 123.23(13) C21 C6 C5 114.62(12) C6 C7 C15 119.29(13) C6 C7 C8 119.65(14) C15 C7 C8 121.05(14) C9 C8 C7 112.14(12) C9 C8 H10 109.2 C7 C8 H10 109.2 C9 C8 H9 109.2 C7 C8 H9 109.2 H10 C8 H9 107.9 C10 C9 C14 118.22(16) C10 C9 C8 120.84(15) C14 C9 C8 120.91(15) C11 C10 C9 121.10(17) C11 C10 H8 119.5 C9 C10 H8 119.5 C12 C11 C10 119.83(18) C12 C11 H5 120.1 C10 C11 H5 120.1 C11 C12 C13 119.92(18) C11 C12 H2 120.0 C13 C12 H2 120.0 C14 C13 C12 120.17(19) C14 C13 H6 119.9 C12 C13 H6 119.9 C13 C14 C9 120.73(17) C13 C14 H7 119.6 C9 C14 H7 119.6 C20 C15 C16 116.84(15) C20 C15 C7 118.32(13) C16 C15 C7 124.82(14) C17 C16 C15 121.22(17) C17 C16 H11 119.4 C15 C16 H11 119.4 C16 C17 C18 120.41(16) C16 C17 H12 119.8 C18 C17 H12 119.8 C19 C18 C17 120.33(17) C19 C18 H13 119.8 C17 C18 H13 119.8 C18 C19 C20 119.61(17) C18 C19 H14 120.2 C20 C19 H14 120.2 N1 C20 C19 118.82(14) N1 C20 C15 119.61(13) C19 C20 C15 121.57(14) O1 C21 N1 120.95(13) O1 C21 C6 122.81(13) N1 C21 C6 116.23(13) C23 C22 C4 120.29(15) C23 C22 H15 119.9 C4 C22 H15 119.9 C1 C23 C22 120.13(17) C1 C23 H16 119.9 C22 C23 H16 119.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C21 1.2488(18) O2 C5 1.2141(18) N1 C21 1.3571(19) N1 C20 1.3802(19) N1 H1A 0.94(2) C1 C23 1.375(3) C1 C2 1.377(3) C1 H1 0.9300 C2 C3 1.376(3) C2 H3 0.9300 C3 C4 1.392(2) C3 H4 0.9300 C4 C22 1.380(2) C4 C5 1.480(2) C5 C6 1.507(2) C6 C7 1.364(2) C6 C21 1.4517(19) C7 C15 1.450(2) C7 C8 1.523(2) C8 C9 1.512(2) C8 H10 0.9700 C8 H9 0.9700 C9 C10 1.383(2) C9 C14 1.384(2) C10 C11 1.381(3) C10 H8 0.9300 C11 C12 1.368(3) C11 H5 0.9300 C12 C13 1.377(3) C12 H2 0.9300 C13 C14 1.376(3) C13 H6 0.9300 C14 H7 0.9300 C15 C20 1.406(2) C15 C16 1.412(2) C16 C17 1.376(3) C16 H11 0.9300 C17 C18 1.387(3) C17 H12 0.9300 C18 C19 1.371(3) C18 H13 0.9300 C19 C20 1.396(2) C19 H14 0.9300 C22 C23 1.380(2) C22 H15 0.9300 C23 H16 0.9300 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 C23 C1 C2 C3 -0.1(3) C1 C2 C3 C4 -0.2(3) C2 C3 C4 C22 -0.2(3) C2 C3 C4 C5 176.92(17) C22 C4 C5 O2 168.80(16) C3 C4 C5 O2 -8.2(2) C22 C4 C5 C6 -10.4(2) C3 C4 C5 C6 172.57(14) O2 C5 C6 C7 -69.9(2) C4 C5 C6 C7 109.28(16) O2 C5 C6 C21 106.55(16) C4 C5 C6 C21 -74.24(17) C21 C6 C7 C15 2.0(2) C5 C6 C7 C15 178.22(12) C21 C6 C7 C8 -179.31(13) C5 C6 C7 C8 -3.1(2) C6 C7 C8 C9 -67.03(19) C15 C7 C8 C9 111.65(16) C7 C8 C9 C10 121.46(17) C7 C8 C9 C14 -56.8(2) C14 C9 C10 C11 0.9(3) C8 C9 C10 C11 -177.41(17) C9 C10 C11 C12 0.6(3) C10 C11 C12 C13 -1.5(3) C11 C12 C13 C14 0.8(3) C12 C13 C14 C9 0.8(3) C10 C9 C14 C13 -1.6(3) C8 C9 C14 C13 176.70(16) C6 C7 C15 C20 -1.9(2) C8 C7 C15 C20 179.42(13) C6 C7 C15 C16 177.14(14) C8 C7 C15 C16 -1.5(2) C20 C15 C16 C17 -1.0(2) C7 C15 C16 C17 179.94(15) C15 C16 C17 C18 -0.1(3) C16 C17 C18 C19 0.7(3) C17 C18 C19 C20 -0.1(3) C21 N1 C20 C19 -179.78(14) C21 N1 C20 C15 0.0(2) C18 C19 C20 N1 178.71(15) C18 C19 C20 C15 -1.0(2) C16 C15 C20 N1 -178.18(13) C7 C15 C20 N1 0.9(2) C16 C15 C20 C19 1.6(2) C7 C15 C20 C19 -179.32(13) C20 N1 C21 O1 -178.63(14) C20 N1 C21 C6 0.0(2) C7 C6 C21 O1 177.58(14) C5 C6 C21 O1 1.1(2) C7 C6 C21 N1 -1.1(2) C5 C6 C21 N1 -177.59(12) C3 C4 C22 C23 0.9(2) C5 C4 C22 C23 -176.19(16) C2 C1 C23 C22 0.8(3) C4 C22 C23 C1 -1.2(3)