#------------------------------------------------------------------------------ #$Date: 2019-04-25 03:46:02 +0300 (Thu, 25 Apr 2019) $ #$Revision: 214761 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/83/7058333.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_7058333 loop_ _publ_author_name 'Fujita, Hikaru' 'Jing, Haoyu' 'Krayer, Michael' 'Allu, Srinivasarao' 'Veeraraghavaiah, Gorre' 'Wu, Zhiyuan' 'Jiang, Jianbing' 'Diers, James R.' 'Magdaong, Nikki Cecil M.' 'Mandal, Amit K.' 'Roy, Arpita' 'Niedzwiedzki, Dariusz M.' 'Kirmaier, Christine' 'Bocian, David F.' 'Holten, Dewey' 'Lindsey, Jonathan S.' _publ_section_title ; Annulated bacteriochlorins for near-infrared photophysical studies ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C9NJ01113G _journal_year 2019 _chemical_formula_moiety 'C25 H26 N2 O2' _chemical_formula_sum 'C25 H26 N2 O2' _chemical_formula_weight 386.48 _chemical_name_common GVR-DHDP-NaEt _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_update_record ; 2019-02-27 deposited with the CCDC. 2019-04-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.7904(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.7670(4) _cell_length_b 7.3416(2) _cell_length_c 18.1519(4) _cell_measurement_reflns_used 6895 _cell_measurement_temperature 121.(2) _cell_measurement_theta_max 25.4929 _cell_measurement_theta_min 2.2518 _cell_volume 2093.83(9) _computing_cell_refinement 'SAINT V8.37A (Bruker AXS Inc., 2015)' _computing_data_collection 'Bruker Instrument Service v2013.12.0.0' _computing_data_reduction 'SAINT V8.37A (Bruker AXS Inc., 2015)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 786)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 121.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker-Nonius X8 Kappa APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_unetI/netI 0.0367 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 30616 _diffrn_reflns_theta_full 27.11 _diffrn_reflns_theta_max 27.11 _diffrn_reflns_theta_min 1.79 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 824 _exptl_crystal_size_max 0.199 _exptl_crystal_size_mid 0.144 _exptl_crystal_size_min 0.088 _refine_diff_density_max 0.455 _refine_diff_density_min -0.317 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 269 _refine_ls_number_reflns 4625 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0476 _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^)+(0.0566P)^2^+0.9485P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1138 _refine_ls_wR_factor_ref 0.1264 _reflns_number_gt 3389 _reflns_number_total 4625 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj01113g2.cif _cod_data_source_block rds662 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-Scan' changed to 'multi-scan' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 7058333 _shelx_res_file ; rds662_0m.res created by SHELXL-2014/7 TITL rds662_0m in P2(1)/n CELL 0.71073 15.767 7.3416 18.1519 90 94.7904 90 ZERR 4 0.0004 0.0002 0.0004 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 100 104 8 8 LIST 4 acta L.S. 10 PLAN 5 SIZE 0.088 0.144 0.199 TEMP -151.6 BOND $h conf htab EQIV $1 -x+3/2, y-1/2, -z+1/2 HTAB N2 O1_$1 HTAB N2 N1 fmap 2 WGHT 0.056600 0.948500 FVAR 0.17680 O1 4 0.655699 0.753552 0.166012 11.00000 0.01863 0.03037 = 0.03213 0.00791 0.00207 -0.00369 O2 4 0.515890 0.729825 0.181182 11.00000 0.01711 0.01966 = 0.03613 0.00529 0.00191 0.00137 N1 3 0.669064 -0.073843 0.364380 11.00000 0.02105 0.02259 = 0.02313 0.00068 0.00608 0.00132 N2 3 0.662592 0.267051 0.292127 11.00000 0.01473 0.02265 = 0.01997 0.00167 0.00284 0.00190 H2 2 0.700983 0.192480 0.314760 11.00000 -1.20000 C1 1 0.689534 -0.204419 0.409732 11.00000 0.02739 0.02189 = 0.02219 -0.00224 0.00522 -0.00076 C2 1 0.614514 -0.286976 0.446308 11.00000 0.02926 0.02149 = 0.02317 0.00082 0.00756 -0.00052 C3 1 0.540978 -0.223698 0.391340 11.00000 0.02425 0.02148 = 0.02798 -0.00022 0.00762 -0.00298 AFIX 23 H3A 2 0.524980 -0.319051 0.354186 11.00000 -1.20000 H3B 2 0.490327 -0.189865 0.417079 11.00000 -1.20000 AFIX 0 C4 1 0.579090 -0.059561 0.356200 11.00000 0.02066 0.02162 = 0.02185 -0.00384 0.00692 -0.00249 C5 1 0.538202 0.079281 0.321415 11.00000 0.01641 0.02246 = 0.02504 -0.00181 0.00430 -0.00151 AFIX 43 H5 2 0.477785 0.074620 0.317891 11.00000 -1.20000 AFIX 0 C6 1 0.576040 0.236222 0.288477 11.00000 0.01574 0.02093 = 0.02304 -0.00200 0.00352 0.00045 C7 1 0.536770 0.379664 0.250089 11.00000 0.01814 0.01871 = 0.02412 -0.00223 0.00118 -0.00112 C8 1 0.603239 0.499011 0.229671 11.00000 0.01561 0.02024 = 0.02086 -0.00175 0.00361 -0.00039 C9 1 0.679319 0.423599 0.257451 11.00000 0.01660 0.02241 = 0.01884 -0.00004 0.00362 -0.00185 AFIX 43 H9 2 0.734227 0.473522 0.252918 11.00000 -1.20000 AFIX 0 C10 1 0.778656 -0.264672 0.426847 11.00000 0.02977 0.03469 = 0.03578 0.00831 0.00325 0.00322 AFIX 137 H10A 2 0.784899 -0.390256 0.409816 11.00000 -1.50000 H10B 2 0.793161 -0.258716 0.480352 11.00000 -1.50000 H10C 2 0.816875 -0.184911 0.401696 11.00000 -1.50000 AFIX 0 C11 1 0.620428 -0.492263 0.457386 11.00000 0.04087 0.02322 = 0.03567 0.00361 0.01051 -0.00164 AFIX 137 H11A 2 0.625066 -0.551860 0.409580 11.00000 -1.50000 H11B 2 0.569264 -0.535925 0.479005 11.00000 -1.50000 H11C 2 0.670761 -0.521158 0.490703 11.00000 -1.50000 AFIX 0 C12 1 0.609229 -0.190154 0.521189 11.00000 0.04253 0.03312 = 0.02388 -0.00248 0.01117 -0.00433 AFIX 137 H12A 2 0.661431 -0.213571 0.552966 11.00000 -1.50000 H12B 2 0.560148 -0.236615 0.545140 11.00000 -1.50000 H12C 2 0.602750 -0.058754 0.513043 11.00000 -1.50000 AFIX 0 C13 1 0.596636 0.671575 0.189523 11.00000 0.01658 0.02224 = 0.01903 -0.00285 0.00034 -0.00055 C14 1 0.497364 0.893740 0.138789 11.00000 0.02709 0.01790 = 0.03081 0.00320 -0.00073 0.00183 AFIX 23 H14A 2 0.524695 0.890010 0.091653 11.00000 -1.20000 H14B 2 0.517936 1.002678 0.167043 11.00000 -1.20000 AFIX 0 C15 1 0.402957 0.897255 0.124787 11.00000 0.03144 0.03825 = 0.10455 0.02780 -0.01806 -0.00174 AFIX 137 H15A 2 0.385893 1.003567 0.094433 11.00000 -1.50000 H15B 2 0.377180 0.904597 0.171990 11.00000 -1.50000 H15C 2 0.383672 0.785916 0.098725 11.00000 -1.50000 AFIX 0 C16 1 0.442951 0.394783 0.235231 11.00000 0.01916 0.01785 = 0.02944 0.00189 0.00043 -0.00246 C17 1 0.392067 0.413930 0.292534 11.00000 0.02526 0.02693 = 0.02972 0.00103 0.00700 -0.00218 AFIX 43 H17 2 0.418368 0.425918 0.341317 11.00000 -1.20000 AFIX 0 C18 1 0.303219 0.416545 0.282189 11.00000 0.02429 0.03662 = 0.04941 0.00271 0.00701 -0.00115 AFIX 43 H18 2 0.270170 0.431617 0.323192 11.00000 -1.20000 AFIX 0 C19 1 0.264262 0.397107 0.212170 11.00000 0.02109 0.03492 = 0.05973 0.00321 0.00033 -0.00007 AFIX 43 H19 2 0.203878 0.396656 0.205099 11.00000 -1.20000 AFIX 0 C20 1 0.312147 0.377867 0.150780 11.00000 0.02348 0.01955 = 0.04042 0.00450 -0.00794 -0.00150 C21 1 0.403583 0.379677 0.161662 11.00000 0.02608 0.01394 = 0.03369 0.00291 -0.00276 -0.00103 C22 1 0.450578 0.365455 0.098523 11.00000 0.03060 0.01900 = 0.02665 0.00021 -0.00109 -0.00329 AFIX 43 H22 2 0.511020 0.365950 0.104280 11.00000 -1.20000 AFIX 0 C23 1 0.409356 0.351063 0.029543 11.00000 0.05335 0.02779 = 0.02939 0.00150 -0.00709 -0.00677 AFIX 43 H23 2 0.441925 0.346541 -0.012150 11.00000 -1.20000 AFIX 0 C24 1 0.320958 0.342826 0.018560 11.00000 0.05923 0.03388 = 0.04021 0.00369 -0.02111 -0.00625 AFIX 43 H24 2 0.293684 0.328501 -0.029766 11.00000 -1.20000 AFIX 0 C25 1 0.274650 0.355487 0.077550 11.00000 0.03622 0.02989 = 0.05014 0.00456 -0.01717 -0.00018 AFIX 43 H25 2 0.214390 0.349152 0.069732 11.00000 -1.20000 AFIX 0 HKLF 4 REM rds662_0m in P2(1)/n REM R1 = 0.0476 for 3389 Fo > 4sig(Fo) and 0.0724 for all 4625 data REM 269 parameters refined using 0 restraints END WGHT 0.0562 0.9582 REM Instructions for potential hydrogen bonds HTAB N2 O1_$1 HTAB N2 N1 REM Highest difference peak 0.455, deepest hole -0.317, 1-sigma level 0.045 Q1 1 0.4256 0.8738 0.0746 11.00000 0.05 0.46 Q2 1 0.4575 0.3660 0.1802 11.00000 0.05 0.38 Q3 1 0.2123 0.3986 0.1770 11.00000 0.05 0.35 Q4 1 0.3774 0.3970 0.2062 11.00000 0.05 0.34 Q5 1 0.2033 0.4242 0.2529 11.00000 0.05 0.34 ; _shelx_res_checksum 958 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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_refinement_flags_adp _atom_site_refinement_flags_posn _atom_site_occupancy O O1 0.65570(7) 0.75355(16) 0.16601(6) 0.0270(3) Uani d . . 1 O O2 0.51589(7) 0.72983(15) 0.18118(6) 0.0243(3) Uani d . . 1 N N1 0.66906(8) -0.07384(18) 0.36438(7) 0.0220(3) Uani d . . 1 N N2 0.66259(8) 0.26705(19) 0.29213(7) 0.0190(3) Uani d . . 1 H H2 0.7010(11) 0.192(3) 0.3148(9) 0.023 Uiso d U . 1 C C1 0.68953(11) -0.2044(2) 0.40973(9) 0.0236(4) Uani d . . 1 C C2 0.61451(11) -0.2870(2) 0.44631(9) 0.0243(4) Uani d . . 1 C C3 0.54098(11) -0.2237(2) 0.39134(9) 0.0243(4) Uani d . . 1 H H3A 0.525 -0.3191 0.3542 0.029 Uiso calc U R 1 H H3B 0.4903 -0.1899 0.4171 0.029 Uiso calc U R 1 C C4 0.57909(10) -0.0596(2) 0.35620(9) 0.0211(3) Uani d . . 1 C C5 0.53820(10) 0.0793(2) 0.32141(9) 0.0212(3) Uani d . . 1 H H5 0.4778 0.0746 0.3179 0.025 Uiso calc U R 1 C C6 0.57604(10) 0.2362(2) 0.28848(9) 0.0198(3) Uani d . . 1 C C7 0.53677(10) 0.3797(2) 0.25009(9) 0.0204(3) Uani d . . 1 C C8 0.60324(10) 0.4990(2) 0.22967(8) 0.0188(3) Uani d . . 1 C C9 0.67932(10) 0.4236(2) 0.25745(8) 0.0192(3) Uani d . . 1 H H9 0.7342 0.4735 0.2529 0.023 Uiso calc U R 1 C C10 0.77866(12) -0.2647(3) 0.42685(11) 0.0334(4) Uani d . . 1 H H10A 0.7849 -0.3903 0.4098 0.05 Uiso calc U R 1 H H10B 0.7932 -0.2587 0.4804 0.05 Uiso calc U R 1 H H10C 0.8169 -0.1849 0.4017 0.05 Uiso calc U R 1 C C11 0.62043(12) -0.4923(2) 0.45739(10) 0.0328(4) Uani d . . 1 H H11A 0.6251 -0.5519 0.4096 0.049 Uiso calc U R 1 H H11B 0.5693 -0.5359 0.479 0.049 Uiso calc U R 1 H H11C 0.6708 -0.5212 0.4907 0.049 Uiso calc U R 1 C C12 0.60923(13) -0.1902(3) 0.52119(9) 0.0327(4) Uani d . . 1 H H12A 0.6614 -0.2136 0.553 0.049 Uiso calc U R 1 H H12B 0.5601 -0.2366 0.5451 0.049 Uiso calc U R 1 H H12C 0.6028 -0.0588 0.513 0.049 Uiso calc U R 1 C C13 0.59664(10) 0.6716(2) 0.18952(8) 0.0193(3) Uani d . . 1 C C14 0.49736(11) 0.8937(2) 0.13879(10) 0.0254(4) Uani d . . 1 H H14A 0.5247 0.89 0.0917 0.031 Uiso calc U R 1 H H14B 0.5179 1.0027 0.167 0.031 Uiso calc U R 1 C C15 0.40296(13) 0.8973(3) 0.12479(16) 0.0594(7) Uani d . . 1 H H15A 0.3859 1.0036 0.0944 0.089 Uiso calc U R 1 H H15B 0.3772 0.9046 0.172 0.089 Uiso calc U R 1 H H15C 0.3837 0.7859 0.0987 0.089 Uiso calc U R 1 C C16 0.44295(10) 0.3948(2) 0.23523(9) 0.0222(4) Uani d . . 1 C C17 0.39207(11) 0.4139(2) 0.29253(10) 0.0270(4) Uani d . . 1 H H17 0.4184 0.4259 0.3413 0.032 Uiso calc U R 1 C C18 0.30322(12) 0.4165(3) 0.28219(12) 0.0366(5) Uani d . . 1 H H18 0.2702 0.4316 0.3232 0.044 Uiso calc U R 1 C C19 0.26426(12) 0.3971(3) 0.21217(12) 0.0387(5) Uani d . . 1 H H19 0.2039 0.3967 0.2051 0.046 Uiso calc U R 1 C C20 0.31215(11) 0.3779(2) 0.15078(10) 0.0284(4) Uani d . . 1 C C21 0.40358(11) 0.3797(2) 0.16166(10) 0.0249(4) Uani d . . 1 C C22 0.45058(12) 0.3655(2) 0.09852(9) 0.0256(4) Uani d . . 1 H H22 0.511 0.3659 0.1043 0.031 Uiso calc U R 1 C C23 0.40936(14) 0.3511(3) 0.02954(11) 0.0374(5) Uani d . . 1 H H23 0.4419 0.3465 -0.0122 0.045 Uiso calc U R 1 C C24 0.32096(15) 0.3428(3) 0.01856(12) 0.0459(6) Uani d . . 1 H H24 0.2937 0.3285 -0.0298 0.055 Uiso calc U R 1 C C25 0.27465(14) 0.3555(3) 0.07755(12) 0.0399(5) Uani d . . 1 H H25 0.2144 0.3492 0.0697 0.048 Uiso calc U R 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 0.0186(6) 0.0304(7) 0.0321(6) -0.0037(5) 0.0021(5) 0.0079(5) O2 0.0171(6) 0.0197(6) 0.0361(7) 0.0014(5) 0.0019(5) 0.0053(5) N1 0.0211(7) 0.0226(7) 0.0231(7) 0.0013(6) 0.0061(5) 0.0007(6) N2 0.0147(7) 0.0226(7) 0.0200(7) 0.0019(5) 0.0028(5) 0.0017(6) C1 0.0274(9) 0.0219(8) 0.0222(8) -0.0008(7) 0.0052(7) -0.0022(7) C2 0.0293(9) 0.0215(8) 0.0232(8) -0.0005(7) 0.0076(7) 0.0008(7) C3 0.0243(9) 0.0215(8) 0.0280(9) -0.0030(7) 0.0076(7) -0.0002(7) C4 0.0207(8) 0.0216(8) 0.0218(8) -0.0025(7) 0.0069(6) -0.0038(7) C5 0.0164(8) 0.0225(8) 0.0250(8) -0.0015(7) 0.0043(6) -0.0018(7) C6 0.0157(8) 0.0209(8) 0.0230(8) 0.0005(6) 0.0035(6) -0.0020(6) C7 0.0181(8) 0.0187(8) 0.0241(8) -0.0011(6) 0.0012(6) -0.0022(6) C8 0.0156(8) 0.0202(8) 0.0209(8) -0.0004(6) 0.0036(6) -0.0018(6) C9 0.0166(8) 0.0224(8) 0.0188(8) -0.0019(6) 0.0036(6) 0.0000(6) C10 0.0298(10) 0.0347(10) 0.0358(10) 0.0032(8) 0.0033(8) 0.0083(8) C11 0.0409(11) 0.0232(9) 0.0357(10) -0.0016(8) 0.0105(8) 0.0036(8) C12 0.0425(11) 0.0331(10) 0.0239(9) -0.0043(9) 0.0112(8) -0.0025(8) C13 0.0166(8) 0.0222(8) 0.0190(8) -0.0006(6) 0.0003(6) -0.0028(6) C14 0.0271(9) 0.0179(8) 0.0308(9) 0.0018(7) -0.0007(7) 0.0032(7) C15 0.0314(12) 0.0383(12) 0.105(2) -0.0017(10) -0.0181(12) 0.0278(13) C16 0.0192(8) 0.0179(8) 0.0294(9) -0.0025(6) 0.0004(7) 0.0019(7) C17 0.0253(9) 0.0269(9) 0.0297(9) -0.0022(7) 0.0070(7) 0.0010(7) C18 0.0243(10) 0.0366(11) 0.0494(12) -0.0011(8) 0.0070(8) 0.0027(9) C19 0.0211(9) 0.0349(11) 0.0597(13) -0.0001(8) 0.0003(9) 0.0032(9) C20 0.0235(9) 0.0196(9) 0.0404(10) -0.0015(7) -0.0079(8) 0.0045(7) C21 0.0261(9) 0.0139(8) 0.0337(9) -0.0010(7) -0.0028(7) 0.0029(7) C22 0.0306(10) 0.0190(8) 0.0266(9) -0.0033(7) -0.0011(7) 0.0002(7) C23 0.0533(13) 0.0278(10) 0.0294(10) -0.0068(9) -0.0071(9) 0.0015(8) C24 0.0592(15) 0.0339(11) 0.0402(12) -0.0063(10) -0.0211(11) 0.0037(9) C25 0.0362(11) 0.0299(10) 0.0501(13) -0.0002(9) -0.0172(9) 0.0046(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 118.29(13) C1 N1 C4 108.50(14) C9 N2 C6 110.43(13) C9 N2 H2 126.0(12) C6 N2 H2 123.6(12) N1 C1 C10 122.65(15) N1 C1 C2 114.28(14) C10 C1 C2 123.04(15) C11 C2 C1 114.12(14) C11 C2 C3 114.81(15) C1 C2 C3 99.63(13) C11 C2 C12 110.31(14) C1 C2 C12 107.50(14) C3 C2 C12 109.84(14) C4 C3 C2 102.12(13) C4 C3 H3A 111.3 C2 C3 H3A 111.3 C4 C3 H3B 111.3 C2 C3 H3B 111.3 H3A C3 H3B 109.2 C5 C4 N1 123.02(15) C5 C4 C3 127.92(15) N1 C4 C3 109.05(13) C4 C5 C6 127.04(15) C4 C5 H5 116.5 C6 C5 H5 116.5 N2 C6 C7 107.41(14) N2 C6 C5 123.39(14) C7 C6 C5 129.19(15) C6 C7 C8 106.80(14) C6 C7 C16 123.13(14) C8 C7 C16 130.07(14) C9 C8 C7 106.96(14) C9 C8 C13 123.68(14) C7 C8 C13 129.33(14) N2 C9 C8 108.39(14) N2 C9 H9 125.8 C8 C9 H9 125.8 C1 C10 H10A 109.5 C1 C10 H10B 109.5 H10A C10 H10B 109.5 C1 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 C2 C11 H11A 109.5 C2 C11 H11B 109.5 H11A C11 H11B 109.5 C2 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 C2 C12 H12A 109.5 C2 C12 H12B 109.5 H12A C12 H12B 109.5 C2 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 O1 C13 O2 123.43(15) O1 C13 C8 125.43(14) O2 C13 C8 111.14(13) O2 C14 C15 105.07(14) O2 C14 H14A 110.7 C15 C14 H14A 110.7 O2 C14 H14B 110.7 C15 C14 H14B 110.7 H14A C14 H14B 108.8 C14 C15 H15A 109.5 C14 C15 H15B 109.5 H15A C15 H15B 109.5 C14 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C17 C16 C21 118.70(15) C17 C16 C7 120.41(15) C21 C16 C7 120.80(15) C16 C17 C18 122.83(17) C16 C17 H17 118.6 C18 C17 H17 118.6 C19 C18 C17 119.28(18) C19 C18 H18 120.4 C17 C18 H18 120.4 C18 C19 C20 121.11(18) C18 C19 H19 119.4 C20 C19 H19 119.4 C19 C20 C25 123.06(18) C19 C20 C21 119.28(16) C25 C20 C21 117.66(18) C22 C21 C16 123.01(15) C22 C21 C20 118.23(16) C16 C21 C20 118.75(16) C23 C22 C21 120.35(17) C23 C22 H22 119.8 C21 C22 H22 119.8 C22 C23 C24 121.9(2) C22 C23 H23 119.0 C24 C23 H23 119.0 C25 C24 C23 119.01(19) C25 C24 H24 120.5 C23 C24 H24 120.5 C24 C25 C20 122.76(19) C24 C25 H25 118.6 C20 C25 H25 118.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C13 1.2157(19) O2 C13 1.3396(19) O2 C14 1.4450(19) N1 C1 1.287(2) N1 C4 1.418(2) N2 C9 1.347(2) N2 C6 1.379(2) N2 H2 0.891(18) C1 C10 1.481(2) C1 C2 1.529(2) C2 C11 1.522(2) C2 C3 1.537(2) C2 C12 1.542(2) C3 C4 1.511(2) C3 H3A 0.99 C3 H3B 0.99 C4 C5 1.336(2) C5 C6 1.449(2) C5 H5 0.95 C6 C7 1.381(2) C7 C8 1.438(2) C7 C16 1.485(2) C8 C9 1.378(2) C8 C13 1.461(2) C9 H9 0.95 C10 H10A 0.98 C10 H10B 0.98 C10 H10C 0.98 C11 H11A 0.98 C11 H11B 0.98 C11 H11C 0.98 C12 H12A 0.98 C12 H12B 0.98 C12 H12C 0.98 C14 C15 1.489(3) C14 H14A 0.99 C14 H14B 0.99 C15 H15A 0.98 C15 H15B 0.98 C15 H15C 0.98 C16 C17 1.373(2) C16 C21 1.429(2) C17 C18 1.398(2) C17 H17 0.95 C18 C19 1.372(3) C18 H18 0.95 C19 C20 1.404(3) C19 H19 0.95 C20 C25 1.419(3) C20 C21 1.439(2) C21 C22 1.420(2) C22 C23 1.366(2) C22 H22 0.95 C23 C24 1.393(3) C23 H23 0.95 C24 C25 1.349(3) C24 H24 0.95 C25 H25 0.95 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 N2 H2 O1 2_645 0.891(18) 2.302(18) 2.9038(17) 124.8(15) N2 H2 N1 . 0.891(18) 2.228(18) 2.8234(19) 123.9(14) 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 C4 N1 C1 C10 175.71(15) C4 N1 C1 C2 -6.35(19) N1 C1 C2 C11 142.86(16) C10 C1 C2 C11 -39.2(2) N1 C1 C2 C3 20.02(18) C10 C1 C2 C3 -162.05(16) N1 C1 C2 C12 -94.46(17) C10 C1 C2 C12 83.5(2) C11 C2 C3 C4 -145.90(14) C1 C2 C3 C4 -23.55(15) C12 C2 C3 C4 89.12(15) C1 N1 C4 C5 169.93(15) C1 N1 C4 C3 -10.92(18) C2 C3 C4 C5 -158.24(16) C2 C3 C4 N1 22.66(16) N1 C4 C5 C6 -1.5(3) C3 C4 C5 C6 179.56(15) C9 N2 C6 C7 -0.18(18) C9 N2 C6 C5 -179.39(14) C4 C5 C6 N2 -3.2(3) C4 C5 C6 C7 177.73(17) N2 C6 C7 C8 0.59(17) C5 C6 C7 C8 179.74(15) N2 C6 C7 C16 -179.69(14) C5 C6 C7 C16 -0.5(3) C6 C7 C8 C9 -0.79(18) C16 C7 C8 C9 179.52(16) C6 C7 C8 C13 -178.96(15) C16 C7 C8 C13 1.4(3) C6 N2 C9 C8 -0.33(17) C7 C8 C9 N2 0.69(17) C13 C8 C9 N2 178.99(14) C14 O2 C13 O1 3.3(2) C14 O2 C13 C8 -176.45(13) C9 C8 C13 O1 12.1(3) C7 C8 C13 O1 -170.02(16) C9 C8 C13 O2 -168.19(14) C7 C8 C13 O2 9.7(2) C13 O2 C14 C15 167.03(17) C6 C7 C16 C17 64.1(2) C8 C7 C16 C17 -116.2(2) C6 C7 C16 C21 -112.40(18) C8 C7 C16 C21 67.2(2) C21 C16 C17 C18 1.0(3) C7 C16 C17 C18 -175.61(16) C16 C17 C18 C19 0.8(3) C17 C18 C19 C20 -1.1(3) C18 C19 C20 C25 179.31(18) C18 C19 C20 C21 -0.4(3) C17 C16 C21 C22 177.87(15) C7 C16 C21 C22 -5.5(2) C17 C16 C21 C20 -2.4(2) C7 C16 C21 C20 174.16(14) C19 C20 C21 C22 -178.15(16) C25 C20 C21 C22 2.2(2) C19 C20 C21 C16 2.1(2) C25 C20 C21 C16 -177.55(15) C16 C21 C22 C23 179.89(16) C20 C21 C22 C23 0.2(2) C21 C22 C23 C24 -2.5(3) C22 C23 C24 C25 2.2(3) C23 C24 C25 C20 0.3(3) C19 C20 C25 C24 177.85(19) C21 C20 C25 C24 -2.5(3)