#------------------------------------------------------------------------------ #$Date: 2025-01-22 01:06:39 +0200 (Wed, 22 Jan 2025) $ #$Revision: 297392 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/37/1573725.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_1573725 loop_ _publ_author_name 'Maekawa, Takehisa' 'Itami, Kenichiro' _publ_section_title ; Rapid access to functionalized nanographenes through a palladium-catalyzed multi-annulation sequence ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC07995G _journal_year 2025 _chemical_absolute_configuration rm _chemical_formula_sum 'C29 H17 N' _chemical_formula_weight 379.43 _chemical_melting_point ? _chemical_name_systematic benzo[c]phenanthro[9,10-a]phenanthridine _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' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2024-09-12 deposited with the CCDC. 2025-01-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.531(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.4701(3) _cell_length_b 8.8984(2) _cell_length_c 19.6220(5) _cell_measurement_reflns_used 10255 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 30.3400 _cell_measurement_theta_min 3.0000 _cell_volume 1802.89(8) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution SIR97 _diffrn_ambient_temperature 123(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_unetI/netI 0.0208 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 19052 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.000 _diffrn_reflns_theta_min 2.519 _diffrn_source 'fine-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.63995 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.398 _exptl_crystal_description block _exptl_crystal_F_000 792 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: toluene' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.146 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 3183 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0321 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.4914P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0809 _refine_ls_wR_factor_ref 0.0843 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2767 _reflns_number_total 3183 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc07995g2.cif _cod_data_source_block kk _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value 'n/a' was changed to '?' -- the value is undefined or not given. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1573725 _shelx_shelxl_version_number 2016/6 _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 0.992 _shelx_estimated_absorpt_t_max 0.992 _shelx_res_file ; TITL kk kk.res created by SHELXL-2016/6 at 20:04:47 on 09-Nov-2018 REM Yadorkari-X generated CELL 0.71073 10.4701 8.8984 19.6220 90.0000 99.5310 90.0000 ZERR 4.0 0.0003 0.0002 0.0005 0.0000 0.0030 0.0000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z REM SPGR P21/n monoclinic SFAC C H N UNIT 116 68 4 SIZE 0.10 0.10 0.10 TEMP -150.0 L.S. 4 FMAP 2 PLAN -25 ACTA CONF LIST 4 WPDB -1 BOND $H MERG 2 OMIT -10.000000 50.000000 WGHT 0.043000 0.491400 FVAR 1.25385 N1 3 0.066280 0.826253 0.508438 11.00000 0.02028 0.01765 = 0.02340 0.00020 0.00020 0.00251 C1 1 0.146868 0.904619 0.478669 11.00000 0.02394 0.01524 = 0.02194 0.00056 0.00001 0.00142 AFIX 43 H1 2 0.115758 0.994294 0.455371 11.00000 -1.20000 AFIX 0 C2 1 0.277959 0.864314 0.478915 11.00000 0.02105 0.01656 = 0.01683 -0.00353 -0.00004 -0.00183 C3 1 0.353624 0.935912 0.435134 11.00000 0.02918 0.01846 = 0.01640 0.00003 -0.00026 -0.00403 AFIX 43 H2 2 0.320559 1.021748 0.409277 11.00000 -1.20000 AFIX 0 C4 1 0.473804 0.882793 0.429678 11.00000 0.02919 0.02594 = 0.01833 -0.00256 0.00740 -0.00664 AFIX 43 H3 2 0.524368 0.931381 0.400226 11.00000 -1.20000 AFIX 0 C5 1 0.522178 0.755601 0.467991 11.00000 0.02205 0.02601 = 0.02132 -0.00544 0.00727 -0.00137 AFIX 43 H4 2 0.604172 0.715926 0.462641 11.00000 -1.20000 AFIX 0 C6 1 0.452911 0.687979 0.512924 11.00000 0.01854 0.01954 = 0.01776 -0.00250 0.00177 -0.00003 AFIX 43 H5 2 0.488509 0.603734 0.539167 11.00000 -1.20000 AFIX 0 C7 1 0.328880 0.742045 0.520765 11.00000 0.01805 0.01639 = 0.01463 -0.00408 0.00027 -0.00149 C8 1 0.245566 0.669397 0.562757 11.00000 0.01795 0.01596 = 0.01530 -0.00414 0.00190 0.00046 C9 1 0.287374 0.551464 0.613124 11.00000 0.01638 0.01783 = 0.01467 -0.00279 0.00400 0.00360 C10 1 0.412969 0.553578 0.659022 11.00000 0.01473 0.02261 = 0.01497 -0.00278 0.00505 0.00317 C11 1 0.488417 0.685602 0.668226 11.00000 0.01801 0.02375 = 0.01878 -0.00199 0.00519 0.00229 AFIX 43 H6 2 0.461475 0.771045 0.640515 11.00000 -1.20000 AFIX 0 C12 1 0.599728 0.693993 0.716140 11.00000 0.01860 0.02853 = 0.02228 -0.00481 0.00365 -0.00220 AFIX 43 H7 2 0.649361 0.783884 0.720801 11.00000 -1.20000 AFIX 0 C13 1 0.639812 0.570569 0.757913 11.00000 0.01705 0.03860 = 0.02146 -0.00364 -0.00200 0.00114 AFIX 43 H8 2 0.717871 0.575247 0.790348 11.00000 -1.20000 AFIX 0 C14 1 0.566110 0.442084 0.752053 11.00000 0.02091 0.03064 = 0.02043 0.00226 0.00170 0.00548 AFIX 43 H9 2 0.592951 0.359382 0.781589 11.00000 -1.20000 AFIX 0 C15 1 0.451531 0.430083 0.703214 11.00000 0.01643 0.02507 = 0.01539 -0.00138 0.00491 0.00383 C16 1 0.372447 0.294309 0.696289 11.00000 0.02018 0.02340 = 0.01400 -0.00041 0.00649 0.00344 C17 1 0.415874 0.157458 0.727926 11.00000 0.02197 0.02809 = 0.01571 0.00263 0.00470 0.00630 AFIX 43 H10 2 0.496011 0.154536 0.758754 11.00000 -1.20000 AFIX 0 C18 1 0.344382 0.028004 0.714998 11.00000 0.03064 0.02204 = 0.01812 0.00489 0.00973 0.00732 AFIX 43 H11 2 0.374199 -0.062670 0.737806 11.00000 -1.20000 AFIX 0 C19 1 0.228306 0.029343 0.668543 11.00000 0.02792 0.02005 = 0.02060 -0.00061 0.00906 0.00002 AFIX 43 H12 2 0.181869 -0.061481 0.657336 11.00000 -1.20000 AFIX 0 C20 1 0.181086 0.162870 0.638908 11.00000 0.02017 0.02311 = 0.01827 0.00025 0.00478 0.00123 AFIX 43 H13 2 0.101816 0.163205 0.607330 11.00000 -1.20000 AFIX 0 C21 1 0.248355 0.298824 0.654645 11.00000 0.01820 0.02132 = 0.01392 0.00068 0.00638 0.00347 C22 1 0.198481 0.441058 0.623529 11.00000 0.01779 0.02013 = 0.01208 -0.00206 0.00248 0.00169 C23 1 0.060255 0.474717 0.607756 11.00000 0.01722 0.02040 = 0.01387 -0.00443 0.00182 0.00066 C24 1 -0.034275 0.389430 0.634449 11.00000 0.02030 0.02084 = 0.01726 -0.00235 0.00267 -0.00122 AFIX 43 H14 2 -0.009288 0.298800 0.658610 11.00000 -1.20000 AFIX 0 C25 1 -0.161250 0.434592 0.626249 11.00000 0.01858 0.02691 = 0.02116 -0.00373 0.00466 -0.00373 AFIX 43 H15 2 -0.222548 0.375750 0.645153 11.00000 -1.20000 AFIX 0 C26 1 -0.200913 0.566441 0.590307 11.00000 0.01354 0.02961 = 0.02704 -0.00482 0.00180 0.00206 AFIX 43 H16 2 -0.289290 0.595993 0.583773 11.00000 -1.20000 AFIX 0 C27 1 -0.111726 0.653047 0.564493 11.00000 0.01847 0.02110 = 0.02376 -0.00173 0.00080 0.00306 AFIX 43 H17 2 -0.138975 0.742547 0.539925 11.00000 -1.20000 AFIX 0 C28 1 0.019694 0.611196 0.573884 11.00000 0.01680 0.01943 = 0.01567 -0.00382 0.00138 0.00093 C29 1 0.114057 0.704124 0.547781 11.00000 0.01839 0.01681 = 0.01615 -0.00310 0.00127 0.00148 HKLF 4 REM kk REM R1 = 0.0321 for 2767 Fo > 4sig(Fo) and 0.0382 for all 3183 data REM 271 parameters refined using 0 restraints END WGHT 0.0430 0.4914 REM Highest difference peak 0.146, deepest hole -0.182, 1-sigma level 0.036 Q1 1 0.3243 0.2880 0.6606 11.00000 0.05 0.15 Q2 1 0.0432 0.5572 0.6024 11.00000 0.05 0.15 Q3 1 0.1762 0.6561 0.5381 11.00000 0.05 0.14 Q4 1 0.4038 0.7442 0.5318 11.00000 0.05 0.14 Q5 1 0.4168 0.3577 0.6960 11.00000 0.05 0.14 Q6 1 -0.0333 0.6475 0.5859 11.00000 0.05 0.13 Q7 1 0.2354 0.5175 0.6367 11.00000 0.05 0.13 Q8 1 0.3679 0.5276 0.6249 11.00000 0.05 0.13 Q9 1 0.1219 0.4380 0.6049 11.00000 0.05 0.13 Q10 1 0.5247 0.4216 0.7118 11.00000 0.05 0.13 Q11 1 0.4022 0.0785 0.6975 11.00000 0.05 0.13 Q12 1 0.3805 0.6947 0.5106 11.00000 0.05 0.12 Q13 1 0.2933 0.7757 0.4921 11.00000 0.05 0.12 Q14 1 0.4159 0.5018 0.6884 11.00000 0.05 0.12 Q15 1 0.1923 0.2383 0.6638 11.00000 0.05 0.12 Q16 1 0.4500 0.4759 0.6631 11.00000 0.05 0.12 Q17 1 -0.0347 0.8335 0.4892 11.00000 0.05 0.12 Q18 1 0.1175 0.9713 0.4277 11.00000 0.05 0.12 Q19 1 0.0094 0.4126 0.6013 11.00000 0.05 0.11 Q20 1 0.4601 0.7020 0.4738 11.00000 0.05 0.11 Q21 1 0.0745 0.6729 0.5762 11.00000 0.05 0.11 Q22 1 0.3114 0.8308 0.5143 11.00000 0.05 0.11 Q23 1 0.3203 0.9281 0.4726 11.00000 0.05 0.11 Q24 1 0.2390 0.2191 0.6250 11.00000 0.05 0.11 Q25 1 0.2271 0.3612 0.6295 11.00000 0.05 0.11 ; _shelx_res_checksum 64735 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_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 N1 N 0.06628(9) 0.82625(11) 0.50844(5) 0.0208(2) Uani 1 1 d . . . . . C1 C 0.14687(11) 0.90462(13) 0.47867(6) 0.0208(3) Uani 1 1 d . . . . . H1 H 0.115758 0.994294 0.455371 0.025 Uiso 1 1 calc R U . . . C2 C 0.27796(11) 0.86431(13) 0.47892(6) 0.0185(3) Uani 1 1 d . . . . . C3 C 0.35362(12) 0.93591(13) 0.43513(6) 0.0218(3) Uani 1 1 d . . . . . H2 H 0.320559 1.021748 0.409277 0.026 Uiso 1 1 calc R U . . . C4 C 0.47380(12) 0.88279(14) 0.42968(6) 0.0241(3) Uani 1 1 d . . . . . H3 H 0.524368 0.931381 0.400226 0.029 Uiso 1 1 calc R U . . . C5 C 0.52218(12) 0.75560(14) 0.46799(6) 0.0227(3) Uani 1 1 d . . . . . H4 H 0.604172 0.715926 0.462641 0.027 Uiso 1 1 calc R U . . . C6 C 0.45291(11) 0.68798(13) 0.51292(6) 0.0188(3) Uani 1 1 d . . . . . H5 H 0.488509 0.603734 0.539167 0.023 Uiso 1 1 calc R U . . . C7 C 0.32888(11) 0.74204(13) 0.52076(6) 0.0166(3) Uani 1 1 d . . . . . C8 C 0.24557(11) 0.66940(12) 0.56276(6) 0.0165(2) Uani 1 1 d . . . . . C9 C 0.28737(11) 0.55146(12) 0.61312(6) 0.0161(2) Uani 1 1 d . . . . . C10 C 0.41297(11) 0.55358(13) 0.65902(6) 0.0171(3) Uani 1 1 d . . . . . C11 C 0.48842(11) 0.68560(14) 0.66823(6) 0.0199(3) Uani 1 1 d . . . . . H6 H 0.461475 0.771045 0.640515 0.024 Uiso 1 1 calc R U . . . C12 C 0.59973(11) 0.69399(14) 0.71614(6) 0.0231(3) Uani 1 1 d . . . . . H7 H 0.649361 0.783884 0.720801 0.028 Uiso 1 1 calc R U . . . C13 C 0.63981(12) 0.57057(15) 0.75791(6) 0.0263(3) Uani 1 1 d . . . . . H8 H 0.717871 0.575247 0.790348 0.032 Uiso 1 1 calc R U . . . C14 C 0.56611(11) 0.44208(15) 0.75205(6) 0.0242(3) Uani 1 1 d . . . . . H9 H 0.592951 0.359382 0.781589 0.029 Uiso 1 1 calc R U . . . C15 C 0.45153(11) 0.43008(13) 0.70321(6) 0.0187(3) Uani 1 1 d . . . . . C16 C 0.37245(11) 0.29431(13) 0.69629(6) 0.0188(3) Uani 1 1 d . . . . . C17 C 0.41587(12) 0.15746(14) 0.72793(6) 0.0217(3) Uani 1 1 d . . . . . H10 H 0.496011 0.154536 0.758754 0.026 Uiso 1 1 calc R U . . . C18 C 0.34438(12) 0.02800(14) 0.71500(6) 0.0230(3) Uani 1 1 d . . . . . H11 H 0.374199 -0.062670 0.737806 0.028 Uiso 1 1 calc R U . . . C19 C 0.22831(12) 0.02934(14) 0.66854(6) 0.0223(3) Uani 1 1 d . . . . . H12 H 0.181869 -0.061481 0.657336 0.027 Uiso 1 1 calc R U . . . C20 C 0.18109(12) 0.16287(13) 0.63891(6) 0.0203(3) Uani 1 1 d . . . . . H13 H 0.101816 0.163205 0.607330 0.024 Uiso 1 1 calc R U . . . C21 C 0.24836(11) 0.29882(13) 0.65465(6) 0.0174(3) Uani 1 1 d . . . . . C22 C 0.19848(11) 0.44106(13) 0.62353(6) 0.0167(3) Uani 1 1 d . . . . . C23 C 0.06025(11) 0.47472(13) 0.60776(6) 0.0172(3) Uani 1 1 d . . . . . C24 C -0.03428(11) 0.38943(13) 0.63445(6) 0.0195(3) Uani 1 1 d . . . . . H14 H -0.009288 0.298800 0.658610 0.023 Uiso 1 1 calc R U . . . C25 C -0.16125(11) 0.43459(14) 0.62625(6) 0.0221(3) Uani 1 1 d . . . . . H15 H -0.222548 0.375750 0.645153 0.026 Uiso 1 1 calc R U . . . C26 C -0.20091(11) 0.56644(14) 0.59031(6) 0.0236(3) Uani 1 1 d . . . . . H16 H -0.289290 0.595993 0.583773 0.028 Uiso 1 1 calc R U . . . C27 C -0.11173(11) 0.65305(14) 0.56449(6) 0.0214(3) Uani 1 1 d . . . . . H17 H -0.138975 0.742547 0.539925 0.026 Uiso 1 1 calc R U . . . C28 C 0.01969(11) 0.61120(13) 0.57388(6) 0.0174(3) Uani 1 1 d . . . . . C29 C 0.11406(11) 0.70412(13) 0.54778(6) 0.0173(3) Uani 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 N1 0.0203(5) 0.0176(5) 0.0234(5) 0.0002(4) 0.0002(4) 0.0025(4) C1 0.0239(6) 0.0152(6) 0.0219(6) 0.0006(5) 0.0000(5) 0.0014(5) C2 0.0211(6) 0.0166(6) 0.0168(6) -0.0035(5) 0.0000(5) -0.0018(5) C3 0.0292(7) 0.0185(6) 0.0164(6) 0.0000(5) -0.0003(5) -0.0040(5) C4 0.0292(7) 0.0259(7) 0.0183(6) -0.0026(5) 0.0074(5) -0.0066(5) C5 0.0221(6) 0.0260(6) 0.0213(6) -0.0054(5) 0.0073(5) -0.0014(5) C6 0.0185(6) 0.0195(6) 0.0178(6) -0.0025(5) 0.0018(5) 0.0000(5) C7 0.0180(6) 0.0164(6) 0.0146(5) -0.0041(5) 0.0003(4) -0.0015(5) C8 0.0180(6) 0.0160(6) 0.0153(6) -0.0041(5) 0.0019(5) 0.0005(5) C9 0.0164(6) 0.0178(6) 0.0147(6) -0.0028(5) 0.0040(5) 0.0036(4) C10 0.0147(6) 0.0226(6) 0.0150(6) -0.0028(5) 0.0051(5) 0.0032(5) C11 0.0180(6) 0.0238(6) 0.0188(6) -0.0020(5) 0.0052(5) 0.0023(5) C12 0.0186(6) 0.0285(7) 0.0223(6) -0.0048(5) 0.0037(5) -0.0022(5) C13 0.0171(6) 0.0386(8) 0.0215(6) -0.0036(6) -0.0020(5) 0.0011(5) C14 0.0209(6) 0.0306(7) 0.0204(6) 0.0023(5) 0.0017(5) 0.0055(5) C15 0.0164(6) 0.0251(6) 0.0154(6) -0.0014(5) 0.0049(5) 0.0038(5) C16 0.0202(6) 0.0234(6) 0.0140(6) -0.0004(5) 0.0065(5) 0.0034(5) C17 0.0220(6) 0.0281(7) 0.0157(6) 0.0026(5) 0.0047(5) 0.0063(5) C18 0.0306(7) 0.0220(6) 0.0181(6) 0.0049(5) 0.0097(5) 0.0073(5) C19 0.0279(7) 0.0200(6) 0.0206(6) -0.0006(5) 0.0091(5) 0.0000(5) C20 0.0202(6) 0.0231(6) 0.0183(6) 0.0002(5) 0.0048(5) 0.0012(5) C21 0.0182(6) 0.0213(6) 0.0139(5) 0.0007(5) 0.0064(5) 0.0035(5) C22 0.0178(6) 0.0201(6) 0.0121(5) -0.0021(4) 0.0025(4) 0.0017(5) C23 0.0172(6) 0.0204(6) 0.0139(6) -0.0044(5) 0.0018(5) 0.0007(5) C24 0.0203(6) 0.0208(6) 0.0173(6) -0.0024(5) 0.0027(5) -0.0012(5) C25 0.0186(6) 0.0269(7) 0.0212(6) -0.0037(5) 0.0047(5) -0.0037(5) C26 0.0135(6) 0.0296(7) 0.0270(7) -0.0048(5) 0.0018(5) 0.0021(5) C27 0.0185(6) 0.0211(6) 0.0238(6) -0.0017(5) 0.0008(5) 0.0031(5) C28 0.0168(6) 0.0194(6) 0.0157(6) -0.0038(5) 0.0014(5) 0.0009(5) C29 0.0184(6) 0.0168(6) 0.0162(6) -0.0031(5) 0.0013(5) 0.0015(5) 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' 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 C1 N1 C29 118.07(10) . . ? N1 C1 C2 124.10(11) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C3 C2 C7 120.32(11) . . ? C3 C2 C1 121.58(11) . . ? C7 C2 C1 117.94(11) . . ? C4 C3 C2 120.56(11) . . ? C4 C3 H2 119.7 . . ? C2 C3 H2 119.7 . . ? C3 C4 C5 119.47(11) . . ? C3 C4 H3 120.3 . . ? C5 C4 H3 120.3 . . ? C6 C5 C4 121.03(11) . . ? C6 C5 H4 119.5 . . ? C4 C5 H4 119.5 . . ? C5 C6 C7 120.87(11) . . ? C5 C6 H5 119.6 . . ? C7 C6 H5 119.6 . . ? C2 C7 C6 117.56(10) . . ? C2 C7 C8 118.01(10) . . ? C6 C7 C8 124.03(10) . . ? C29 C8 C7 116.63(10) . . ? C29 C8 C9 118.52(10) . . ? C7 C8 C9 124.44(10) . . ? C22 C9 C8 118.33(10) . . ? C22 C9 C10 118.21(10) . . ? C8 C9 C10 123.04(10) . . ? C11 C10 C15 118.10(10) . . ? C11 C10 C9 121.05(10) . . ? C15 C10 C9 120.13(10) . . ? C12 C11 C10 121.80(11) . . ? C12 C11 H6 119.1 . . ? C10 C11 H6 119.1 . . ? C11 C12 C13 119.93(12) . . ? C11 C12 H7 120.0 . . ? C13 C12 H7 120.0 . . ? C14 C13 C12 119.78(11) . . ? C14 C13 H8 120.1 . . ? C12 C13 H8 120.1 . . ? C13 C14 C15 121.53(11) . . ? C13 C14 H9 119.2 . . ? C15 C14 H9 119.2 . . ? C14 C15 C10 118.78(11) . . ? C14 C15 C16 122.15(11) . . ? C10 C15 C16 119.07(10) . . ? C17 C16 C21 118.52(11) . . ? C17 C16 C15 122.59(10) . . ? C21 C16 C15 118.87(10) . . ? C18 C17 C16 121.16(11) . . ? C18 C17 H10 119.4 . . ? C16 C17 H10 119.4 . . ? C17 C18 C19 120.20(11) . . ? C17 C18 H11 119.9 . . ? C19 C18 H11 119.9 . . ? C20 C19 C18 119.77(11) . . ? C20 C19 H12 120.1 . . ? C18 C19 H12 120.1 . . ? C19 C20 C21 121.11(11) . . ? C19 C20 H13 119.4 . . ? C21 C20 H13 119.4 . . ? C20 C21 C16 118.68(10) . . ? C20 C21 C22 121.37(10) . . ? C16 C21 C22 119.68(10) . . ? C9 C22 C23 119.19(10) . . ? C9 C22 C21 118.08(10) . . ? C23 C22 C21 122.58(10) . . ? C24 C23 C28 117.40(10) . . ? C24 C23 C22 122.76(10) . . ? C28 C23 C22 119.04(10) . . ? C25 C24 C23 121.53(11) . . ? C25 C24 H14 119.2 . . ? C23 C24 H14 119.2 . . ? C24 C25 C26 120.43(11) . . ? C24 C25 H15 119.8 . . ? C26 C25 H15 119.8 . . ? C27 C26 C25 119.68(11) . . ? C27 C26 H16 120.2 . . ? C25 C26 H16 120.2 . . ? C26 C27 C28 120.91(11) . . ? C26 C27 H17 119.5 . . ? C28 C27 H17 119.5 . . ? C27 C28 C23 119.95(11) . . ? C27 C28 C29 120.85(10) . . ? C23 C28 C29 119.18(10) . . ? N1 C29 C8 123.16(10) . . ? N1 C29 C28 116.33(10) . . ? C8 C29 C28 120.50(10) . . ? 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 N1 C1 1.3049(16) . ? N1 C29 1.3782(15) . ? C1 C2 1.4179(17) . ? C1 H1 0.9500 . ? C2 C3 1.4131(17) . ? C2 C7 1.4133(16) . ? C3 C4 1.3648(18) . ? C3 H2 0.9500 . ? C4 C5 1.4059(18) . ? C4 H3 0.9500 . ? C5 C6 1.3701(16) . ? C5 H4 0.9500 . ? C6 C7 1.4169(16) . ? C6 H5 0.9500 . ? C7 C8 1.4477(16) . ? C8 C29 1.3942(16) . ? C8 C9 1.4582(16) . ? C9 C22 1.3914(16) . ? C9 C10 1.4658(16) . ? C10 C11 1.4105(17) . ? C10 C15 1.4165(16) . ? C11 C12 1.3729(17) . ? C11 H6 0.9500 . ? C12 C13 1.3929(18) . ? C12 H7 0.9500 . ? C13 C14 1.3735(18) . ? C13 H8 0.9500 . ? C14 C15 1.4100(16) . ? C14 H9 0.9500 . ? C15 C16 1.4582(17) . ? C16 C17 1.4077(17) . ? C16 C21 1.4163(16) . ? C17 C18 1.3743(18) . ? C17 H10 0.9500 . ? C18 C19 1.3933(17) . ? C18 H11 0.9500 . ? C19 C20 1.3781(17) . ? C19 H12 0.9500 . ? C20 C21 1.4082(17) . ? C20 H13 0.9500 . ? C21 C22 1.4635(16) . ? C22 C23 1.4600(15) . ? C23 C24 1.4148(16) . ? C23 C28 1.4154(16) . ? C24 C25 1.3726(17) . ? C24 H14 0.9500 . ? C25 C26 1.3962(17) . ? C25 H15 0.9500 . ? C26 C27 1.3708(17) . ? C26 H16 0.9500 . ? C27 C28 1.4078(16) . ? C27 H17 0.9500 . ? C28 C29 1.4456(16) . ? 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 C29 N1 C1 C2 6.07(17) . . . . ? N1 C1 C2 C3 167.48(11) . . . . ? N1 C1 C2 C7 -7.93(17) . . . . ? C7 C2 C3 C4 3.76(17) . . . . ? C1 C2 C3 C4 -171.54(11) . . . . ? C2 C3 C4 C5 0.09(18) . . . . ? C3 C4 C5 C6 -2.80(18) . . . . ? C4 C5 C6 C7 1.64(17) . . . . ? C3 C2 C7 C6 -4.80(16) . . . . ? C1 C2 C7 C6 170.67(10) . . . . ? C3 C2 C7 C8 -177.81(10) . . . . ? C1 C2 C7 C8 -2.34(15) . . . . ? C5 C6 C7 C2 2.15(16) . . . . ? C5 C6 C7 C8 174.69(11) . . . . ? C2 C7 C8 C29 13.33(15) . . . . ? C6 C7 C8 C29 -159.18(11) . . . . ? C2 C7 C8 C9 -174.11(10) . . . . ? C6 C7 C8 C9 13.37(17) . . . . ? C29 C8 C9 C22 25.08(15) . . . . ? C7 C8 C9 C22 -147.34(11) . . . . ? C29 C8 C9 C10 -147.41(11) . . . . ? C7 C8 C9 C10 40.17(16) . . . . ? C22 C9 C10 C11 -157.90(11) . . . . ? C8 C9 C10 C11 14.59(16) . . . . ? C22 C9 C10 C15 12.15(15) . . . . ? C8 C9 C10 C15 -175.35(10) . . . . ? C15 C10 C11 C12 3.04(16) . . . . ? C9 C10 C11 C12 173.29(10) . . . . ? C10 C11 C12 C13 -0.90(17) . . . . ? C11 C12 C13 C14 -1.49(18) . . . . ? C12 C13 C14 C15 1.66(18) . . . . ? C13 C14 C15 C10 0.54(17) . . . . ? C13 C14 C15 C16 179.86(11) . . . . ? C11 C10 C15 C14 -2.81(16) . . . . ? C9 C10 C15 C14 -173.16(10) . . . . ? C11 C10 C15 C16 177.84(10) . . . . ? C9 C10 C15 C16 7.50(16) . . . . ? C14 C15 C16 C17 -12.21(17) . . . . ? C10 C15 C16 C17 167.12(10) . . . . ? C14 C15 C16 C21 169.51(10) . . . . ? C10 C15 C16 C21 -11.17(16) . . . . ? C21 C16 C17 C18 4.71(17) . . . . ? C15 C16 C17 C18 -173.57(11) . . . . ? C16 C17 C18 C19 1.69(17) . . . . ? C17 C18 C19 C20 -4.16(17) . . . . ? C18 C19 C20 C21 0.11(17) . . . . ? C19 C20 C21 C16 6.27(17) . . . . ? C19 C20 C21 C22 -179.78(11) . . . . ? C17 C16 C21 C20 -8.54(16) . . . . ? C15 C16 C21 C20 169.81(10) . . . . ? C17 C16 C21 C22 177.40(10) . . . . ? C15 C16 C21 C22 -4.24(15) . . . . ? C8 C9 C22 C23 -24.63(15) . . . . ? C10 C9 C22 C23 148.23(10) . . . . ? C8 C9 C22 C21 159.64(10) . . . . ? C10 C9 C22 C21 -27.50(15) . . . . ? C20 C21 C22 C9 -149.91(11) . . . . ? C16 C21 C22 C9 23.98(15) . . . . ? C20 C21 C22 C23 34.51(16) . . . . ? C16 C21 C22 C23 -151.60(10) . . . . ? C9 C22 C23 C24 -161.23(11) . . . . ? C21 C22 C23 C24 14.29(17) . . . . ? C9 C22 C23 C28 8.23(16) . . . . ? C21 C22 C23 C28 -176.25(10) . . . . ? C28 C23 C24 C25 1.81(16) . . . . ? C22 C23 C24 C25 171.43(11) . . . . ? C23 C24 C25 C26 0.71(18) . . . . ? C24 C25 C26 C27 -1.55(18) . . . . ? C25 C26 C27 C28 -0.20(18) . . . . ? C26 C27 C28 C23 2.78(17) . . . . ? C26 C27 C28 C29 -178.80(11) . . . . ? C24 C23 C28 C27 -3.50(16) . . . . ? C22 C23 C28 C27 -173.52(10) . . . . ? C24 C23 C28 C29 178.05(10) . . . . ? C22 C23 C28 C29 8.03(15) . . . . ? C1 N1 C29 C8 6.52(16) . . . . ? C1 N1 C29 C28 -173.74(10) . . . . ? C7 C8 C29 N1 -16.06(16) . . . . ? C9 C8 C29 N1 170.93(10) . . . . ? C7 C8 C29 C28 164.21(10) . . . . ? C9 C8 C29 C28 -8.80(16) . . . . ? C27 C28 C29 N1 -5.71(16) . . . . ? C23 C28 C29 N1 172.72(10) . . . . ? C27 C28 C29 C8 174.03(11) . . . . ? C23 C28 C29 C8 -7.54(16) . . . . ?