#------------------------------------------------------------------------------ #$Date: 2026-05-01 01:26:44 +0100 (Fri, 01 May 2026) $ #$Revision: 305680 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064396.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_7064396 loop_ _publ_author_name 'Muthusamy, Sengodagounder' 'Hariharan, Selvaraj' _publ_section_title ; A Visible-Light-Promoted C--H Insertion Reaction of Diazoamides with 1,3-Diketones ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D5NJ04942C _journal_year 2026 _chemical_formula_moiety 'C32 H27 N3 O' _chemical_formula_sum 'C32 H27 N3 O' _chemical_formula_weight 469.56 _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 geom _audit_creation_method SHELXL-2019/1 _audit_update_record ; 2025-09-02 deposited with the CCDC. 2026-04-29 downloaded from the CCDC. ; _cell_angle_alpha 110.5340(10) _cell_angle_beta 104.0210(10) _cell_angle_gamma 95.8980(10) _cell_formula_units_Z 2 _cell_length_a 8.9884(4) _cell_length_b 11.0210(4) _cell_length_c 14.0270(5) _cell_measurement_reflns_used 9893 _cell_measurement_temperature 300(2) _cell_measurement_theta_max 26.41 _cell_measurement_theta_min 2.45 _cell_volume 1235.23(8) _computing_cell_refinement 'Bruker APEX4/SAINT' _computing_data_collection 'Bruker APEX4' _computing_data_reduction 'Bruker APEX4/SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2019/1 (Sheldrick, 2019)' _computing_structure_solution 'SHELXL-2019/1 (Sheldrick, 2019)' _diffrn_ambient_temperature 300(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker D8 QUEST diffractometer with PHOTON II detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_unetI/netI 0.0290 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 42504 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.333 _diffrn_reflns_theta_min 2.017 _diffrn_source 'i-mu-s microfocus source' _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.7012 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (BRUKER)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.262 _exptl_crystal_description block _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.238 _exptl_crystal_size_mid 0.209 _exptl_crystal_size_min 0.199 _refine_diff_density_max 0.179 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.032 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 327 _refine_ls_number_reflns 6126 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.894 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0475 _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^)+(0.0773P)^2^+0.4321P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1258 _refine_ls_wR_factor_ref 0.1466 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4548 _reflns_number_total 6126 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj04942c3.cif _cod_data_source_block SHA_381_080125_0m_a _cod_database_code 7064396 _shelx_shelxl_version_number 2019/1 _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_estimated_absorpt_t_min 0.982 _shelx_estimated_absorpt_t_max 0.985 _shelx_res_file ; TITL SHA_381_080125_0m_a.res in P-1 SHA_381_080125_0m_a.res created by SHELXL-2019/1 at 14:42:33 on 09-Jan-2025 REM Old TITL SHA_381_080125_0m in P-1 REM SHELXT solution in P-1: R1 0.177, Rweak 0.010, Alpha 0.057 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C31 N5 CELL 0.71073 8.9884 11.0210 14.0270 110.534 104.021 95.898 ZERR 2.000 0.0004 0.0004 0.0005 0.001 0.001 0.001 LATT 1 SFAC C H N O UNIT 64 54 6 2 ACTA LIST 4 CONF TEMP 26.850 SIZE 0.199 0.209 0.238 L.S. 10 BOND $H HTAB REM LIST 4 FMAP 2 PLAN 20 WGHT 0.077300 0.432100 FVAR 1.22699 O2 4 0.875270 0.302870 0.680017 11.00000 0.03762 0.08958 = 0.05660 0.03303 0.01438 0.00178 N1 3 0.640378 0.202532 0.548905 11.00000 0.04894 0.04471 = 0.03547 0.01695 0.01447 0.00858 N3 3 0.661940 0.412247 1.000616 11.00000 0.05650 0.04147 = 0.03604 0.01162 0.01444 -0.00279 N4 3 0.735737 0.522096 0.996467 11.00000 0.05556 0.04052 = 0.04021 0.01081 0.01336 -0.00488 C1 1 0.669937 0.398996 0.457098 11.00000 0.05672 0.06002 = 0.06945 0.03468 0.03309 0.02434 AFIX 43 H1 2 0.591179 0.396661 0.489284 11.00000 -1.20000 AFIX 0 C2 1 0.749363 0.296375 0.436795 11.00000 0.04591 0.04486 = 0.03354 0.01547 0.01218 0.01201 C3 1 0.866340 0.303750 0.389262 11.00000 0.05974 0.05667 = 0.05110 0.02187 0.02710 0.02190 AFIX 43 H3 2 0.921806 0.236044 0.375339 11.00000 -1.20000 AFIX 0 C4 1 0.902260 0.409843 0.362105 11.00000 0.06557 0.06854 = 0.05813 0.02779 0.03154 0.01180 AFIX 43 H4 2 0.980810 0.412785 0.329834 11.00000 -1.20000 AFIX 0 C5 1 0.822319 0.510401 0.382688 11.00000 0.07172 0.05386 = 0.05332 0.02809 0.02040 0.00914 AFIX 43 H5 2 0.846553 0.581950 0.364634 11.00000 -1.20000 AFIX 0 C6 1 0.706450 0.505568 0.429960 11.00000 0.06999 0.05571 = 0.07703 0.03661 0.02987 0.02784 AFIX 43 H6 2 0.651994 0.573965 0.443941 11.00000 -1.20000 AFIX 0 C7 1 0.713130 0.177903 0.463951 11.00000 0.06487 0.04745 = 0.04259 0.01971 0.02551 0.02012 AFIX 23 H7A 2 0.643990 0.106218 0.400455 11.00000 -1.20000 H7B 2 0.809776 0.148958 0.484741 11.00000 -1.20000 AFIX 0 C8 1 0.483022 0.172908 0.538048 11.00000 0.04437 0.03233 = 0.03980 0.01603 0.00842 0.00688 C9 1 0.465003 0.219686 0.640877 11.00000 0.03963 0.02993 = 0.04032 0.01506 0.00912 0.00490 C10 1 0.718699 0.266826 0.655887 11.00000 0.03981 0.04326 = 0.03943 0.01827 0.01092 0.00345 C11 1 0.356053 0.109829 0.446472 11.00000 0.06154 0.04223 = 0.04121 0.01602 0.00172 0.00619 AFIX 43 H11 2 0.369836 0.079205 0.379059 11.00000 -1.20000 AFIX 0 C12 1 0.209447 0.094498 0.459437 11.00000 0.05217 0.05023 = 0.05936 0.02155 -0.00858 -0.00147 AFIX 43 H12 2 0.122489 0.052790 0.399558 11.00000 -1.20000 AFIX 0 C13 1 0.188263 0.139936 0.560040 11.00000 0.03721 0.05246 = 0.07523 0.02784 0.00514 0.00320 AFIX 43 H13 2 0.087604 0.128373 0.566269 11.00000 -1.20000 AFIX 0 C14 1 0.314449 0.201968 0.650832 11.00000 0.04062 0.04240 = 0.05636 0.02073 0.01436 0.00765 AFIX 43 H14 2 0.299251 0.231595 0.717844 11.00000 -1.20000 AFIX 0 C15 1 0.651986 0.355454 0.831840 11.00000 0.03866 0.03823 = 0.03645 0.01177 0.01104 0.00088 C16 1 0.610518 0.309932 0.904128 11.00000 0.04305 0.03957 = 0.03718 0.01118 0.01269 0.00091 C17 1 0.729097 0.489308 0.893993 11.00000 0.04192 0.04037 = 0.03886 0.01188 0.01157 -0.00129 C18 1 0.967559 0.298901 0.774863 11.00000 0.04280 0.12368 = 0.05626 0.02956 0.00963 0.01533 AFIX 137 H18A 2 1.071912 0.293543 0.770779 11.00000 -1.50000 H18B 2 0.922838 0.222728 0.784527 11.00000 -1.50000 H18C 2 0.970992 0.377719 0.834097 11.00000 -1.50000 AFIX 0 C19 1 0.524298 0.179556 0.888577 11.00000 0.05311 0.03876 = 0.03538 0.01344 0.01280 -0.00024 C20 1 0.579837 0.065770 0.848086 11.00000 0.07243 0.04802 = 0.05042 0.01429 0.02403 0.00901 AFIX 43 H20 2 0.673450 0.070743 0.831078 11.00000 -1.20000 AFIX 0 C21 1 0.495729 -0.056051 0.832807 11.00000 0.10809 0.03953 = 0.06233 0.01271 0.02463 0.01126 AFIX 43 H21 2 0.532782 -0.132575 0.804862 11.00000 -1.20000 AFIX 0 C22 1 0.359359 -0.064025 0.858517 11.00000 0.09768 0.04728 = 0.06678 0.02326 0.01691 -0.01468 AFIX 43 H22 2 0.304167 -0.145830 0.848596 11.00000 -1.20000 AFIX 0 C23 1 0.303238 0.047856 0.898889 11.00000 0.07327 0.05992 = 0.08223 0.02973 0.02806 -0.00974 AFIX 43 H23 2 0.210144 0.041954 0.916441 11.00000 -1.20000 AFIX 0 C24 1 0.384552 0.169418 0.913599 11.00000 0.06134 0.04715 = 0.06649 0.02143 0.02722 0.00123 AFIX 43 H24 2 0.345446 0.245081 0.940465 11.00000 -1.20000 AFIX 0 C25 1 0.655730 0.415036 1.103725 11.00000 0.08086 0.05704 = 0.03908 0.01560 0.02051 -0.00087 AFIX 137 H25A 2 0.582920 0.338353 1.093804 11.00000 -1.50000 H25B 2 0.622255 0.493566 1.140550 11.00000 -1.50000 H25C 2 0.757906 0.415036 1.145059 11.00000 -1.50000 AFIX 0 C26 1 0.790989 0.593667 0.862183 11.00000 0.04975 0.04038 = 0.04586 0.01368 0.01954 0.00035 C27 1 0.715846 0.603470 0.767727 11.00000 0.05994 0.04838 = 0.05734 0.02256 0.01270 0.00415 AFIX 43 H27 2 0.627550 0.539903 0.720501 11.00000 -1.20000 AFIX 0 C28 1 0.770367 0.706738 0.742524 11.00000 0.08675 0.05928 = 0.07208 0.03769 0.02848 0.01686 AFIX 43 H28 2 0.719026 0.711470 0.678247 11.00000 -1.20000 AFIX 0 C29 1 0.898479 0.801513 0.810932 11.00000 0.09317 0.05148 = 0.08624 0.03211 0.04537 0.00210 AFIX 43 H29 2 0.933286 0.871722 0.794201 11.00000 -1.20000 AFIX 0 C30 1 0.976237 0.792863 0.905015 11.00000 0.08595 0.06589 = 0.07730 0.02215 0.02494 -0.02929 AFIX 43 H30 2 1.064287 0.857097 0.951710 11.00000 -1.20000 AFIX 0 C31 1 0.923962 0.688979 0.930440 11.00000 0.06906 0.06738 = 0.05535 0.02259 0.01154 -0.02051 AFIX 43 H31 2 0.978153 0.682940 0.993573 11.00000 -1.20000 AFIX 0 C32 1 0.617716 0.281763 0.716481 11.00000 0.03870 0.03582 = 0.03634 0.01396 0.01043 0.00215 REM ##### HKLF 4 REM SHA_381_080125_0m_a.res in P-1 REM wR2 = 0.1466, GooF = S = 0.894, Restrained GooF = 0.894 for all data REM R1 = 0.0475 for 4548 Fo > 4sig(Fo) and 0.0676 for all 6126 data REM 327 parameters refined using 0 restraints END WGHT 0.0542 0.3230 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.179, deepest hole -0.202, 1-sigma level 0.032 Q1 1 0.7270 0.5045 1.1608 11.00000 0.05 0.18 Q2 1 0.5726 0.2438 0.8970 11.00000 0.05 0.17 Q3 1 0.6858 0.2500 0.7041 11.00000 0.05 0.17 Q4 1 0.6781 0.3332 1.1178 11.00000 0.05 0.16 Q5 1 0.4674 0.1690 0.5896 11.00000 0.05 0.16 Q6 1 0.7167 0.3985 0.8573 11.00000 0.05 0.16 Q7 1 0.6439 0.3210 0.8639 11.00000 0.05 0.16 Q8 1 0.8252 0.6803 0.9099 11.00000 0.05 0.15 Q9 1 0.5429 0.2263 0.6874 11.00000 0.05 0.15 Q10 1 0.3997 0.1836 0.6484 11.00000 0.05 0.15 Q11 1 0.6688 0.4294 0.8499 11.00000 0.05 0.15 Q12 1 0.6312 0.3197 0.7713 11.00000 0.05 0.14 Q13 1 0.5353 0.1241 0.8488 11.00000 0.05 0.14 Q14 1 0.9160 0.2980 0.8283 11.00000 0.05 0.14 Q15 1 1.0189 0.2115 0.7507 11.00000 0.05 0.14 Q16 1 0.4329 0.1638 0.4895 11.00000 0.05 0.13 Q17 1 0.5166 0.4164 1.1059 11.00000 0.05 0.13 Q18 1 0.7774 0.5428 0.8789 11.00000 0.05 0.13 Q19 1 0.4255 0.1632 0.8637 11.00000 0.05 0.13 Q20 1 0.8339 0.3159 0.4475 11.00000 0.05 0.13 ; _shelx_res_checksum 22192 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.87527(12) 0.30287(13) 0.68002(9) 0.0608(3) Uani 1 1 d . . . . . N1 N 0.64038(15) 0.20253(12) 0.54890(9) 0.0424(3) Uani 1 1 d . . . . . N3 N 0.66194(15) 0.41225(12) 1.00062(9) 0.0466(3) Uani 1 1 d . . . . . N4 N 0.73574(16) 0.52210(12) 0.99647(10) 0.0482(3) Uani 1 1 d . . . . . C1 C 0.6699(2) 0.39900(17) 0.45710(15) 0.0557(4) Uani 1 1 d . . . . . H1 H 0.591179 0.396661 0.489284 0.067 Uiso 1 1 calc R U . . . C2 C 0.74936(17) 0.29637(14) 0.43680(11) 0.0411(3) Uani 1 1 d . . . . . C3 C 0.8663(2) 0.30375(17) 0.38926(13) 0.0528(4) Uani 1 1 d . . . . . H3 H 0.921806 0.236044 0.375339 0.063 Uiso 1 1 calc R U . . . C4 C 0.9023(2) 0.40984(19) 0.36210(14) 0.0609(4) Uani 1 1 d . . . . . H4 H 0.980810 0.412785 0.329834 0.073 Uiso 1 1 calc R U . . . C5 C 0.8223(2) 0.51040(17) 0.38269(13) 0.0575(4) Uani 1 1 d . . . . . H5 H 0.846553 0.581950 0.364634 0.069 Uiso 1 1 calc R U . . . C6 C 0.7065(2) 0.50557(18) 0.42996(16) 0.0618(5) Uani 1 1 d . . . . . H6 H 0.651994 0.573965 0.443941 0.074 Uiso 1 1 calc R U . . . C7 C 0.7131(2) 0.17790(15) 0.46395(12) 0.0485(4) Uani 1 1 d . . . . . H7A H 0.643990 0.106218 0.400455 0.058 Uiso 1 1 calc R U . . . H7B H 0.809776 0.148958 0.484741 0.058 Uiso 1 1 calc R U . . . C8 C 0.48302(16) 0.17291(13) 0.53805(11) 0.0391(3) Uani 1 1 d . . . . . C9 C 0.46500(16) 0.21969(12) 0.64088(11) 0.0370(3) Uani 1 1 d . . . . . C10 C 0.71870(16) 0.26683(14) 0.65589(11) 0.0408(3) Uani 1 1 d . . . . . C11 C 0.3561(2) 0.10983(15) 0.44647(12) 0.0513(4) Uani 1 1 d . . . . . H11 H 0.369836 0.079205 0.379059 0.062 Uiso 1 1 calc R U . . . C12 C 0.2094(2) 0.09450(17) 0.45944(15) 0.0596(4) Uani 1 1 d . . . . . H12 H 0.122489 0.052790 0.399558 0.072 Uiso 1 1 calc R U . . . C13 C 0.18826(19) 0.13994(17) 0.56004(15) 0.0568(4) Uani 1 1 d . . . . . H13 H 0.087604 0.128373 0.566269 0.068 Uiso 1 1 calc R U . . . C14 C 0.31445(17) 0.20197(14) 0.65083(13) 0.0461(3) Uani 1 1 d . . . . . H14 H 0.299251 0.231595 0.717844 0.055 Uiso 1 1 calc R U . . . C15 C 0.65199(16) 0.35545(13) 0.83184(11) 0.0392(3) Uani 1 1 d . . . . . C16 C 0.61052(17) 0.30993(14) 0.90413(11) 0.0415(3) Uani 1 1 d . . . . . C17 C 0.72910(17) 0.48931(14) 0.89399(11) 0.0423(3) Uani 1 1 d . . . . . C18 C 0.9676(2) 0.2989(3) 0.77486(15) 0.0769(6) Uani 1 1 d . . . . . H18A H 1.071912 0.293543 0.770779 0.115 Uiso 1 1 calc R U . . . H18B H 0.922838 0.222728 0.784527 0.115 Uiso 1 1 calc R U . . . H18C H 0.970992 0.377719 0.834097 0.115 Uiso 1 1 calc R U . . . C19 C 0.52430(18) 0.17956(14) 0.88858(11) 0.0435(3) Uani 1 1 d . . . . . C20 C 0.5798(2) 0.06577(16) 0.84809(13) 0.0575(4) Uani 1 1 d . . . . . H20 H 0.673450 0.070743 0.831078 0.069 Uiso 1 1 calc R U . . . C21 C 0.4957(3) -0.05605(17) 0.83281(16) 0.0725(6) Uani 1 1 d . . . . . H21 H 0.532782 -0.132575 0.804862 0.087 Uiso 1 1 calc R U . . . C22 C 0.3594(3) -0.06403(19) 0.85852(16) 0.0741(6) Uani 1 1 d . . . . . H22 H 0.304167 -0.145830 0.848596 0.089 Uiso 1 1 calc R U . . . C23 C 0.3032(3) 0.04786(19) 0.89889(17) 0.0721(5) Uani 1 1 d . . . . . H23 H 0.210144 0.041954 0.916441 0.087 Uiso 1 1 calc R U . . . C24 C 0.3846(2) 0.16942(17) 0.91360(15) 0.0578(4) Uani 1 1 d . . . . . H24 H 0.345446 0.245081 0.940465 0.069 Uiso 1 1 calc R U . . . C25 C 0.6557(2) 0.41504(18) 1.10372(13) 0.0606(5) Uani 1 1 d . . . . . H25A H 0.582920 0.338353 1.093804 0.091 Uiso 1 1 calc R U . . . H25B H 0.622255 0.493566 1.140550 0.091 Uiso 1 1 calc R U . . . H25C H 0.757906 0.415036 1.145059 0.091 Uiso 1 1 calc R U . . . C26 C 0.79099(18) 0.59367(14) 0.86218(12) 0.0459(3) Uani 1 1 d . . . . . C27 C 0.7158(2) 0.60347(17) 0.76773(14) 0.0561(4) Uani 1 1 d . . . . . H27 H 0.627550 0.539903 0.720501 0.067 Uiso 1 1 calc R U . . . C28 C 0.7704(3) 0.70674(19) 0.74252(17) 0.0682(5) Uani 1 1 d . . . . . H28 H 0.719026 0.711470 0.678247 0.082 Uiso 1 1 calc R U . . . C29 C 0.8985(3) 0.80151(19) 0.81093(18) 0.0729(6) Uani 1 1 d . . . . . H29 H 0.933286 0.871722 0.794201 0.088 Uiso 1 1 calc R U . . . C30 C 0.9762(3) 0.7929(2) 0.90502(18) 0.0815(7) Uani 1 1 d . . . . . H30 H 1.064287 0.857097 0.951710 0.098 Uiso 1 1 calc R U . . . C31 C 0.9240(2) 0.68898(19) 0.93044(15) 0.0684(5) Uani 1 1 d . . . . . H31 H 0.978153 0.682940 0.993573 0.082 Uiso 1 1 calc R U . . . C32 C 0.61772(16) 0.28176(13) 0.71648(10) 0.0376(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 O2 0.0376(6) 0.0896(9) 0.0566(7) 0.0330(6) 0.0144(5) 0.0018(5) N1 0.0489(7) 0.0447(6) 0.0355(6) 0.0169(5) 0.0145(5) 0.0086(5) N3 0.0565(7) 0.0415(6) 0.0360(6) 0.0116(5) 0.0144(5) -0.0028(5) N4 0.0556(7) 0.0405(6) 0.0402(6) 0.0108(5) 0.0134(6) -0.0049(5) C1 0.0567(9) 0.0600(10) 0.0695(11) 0.0347(8) 0.0331(8) 0.0243(8) C2 0.0459(8) 0.0449(7) 0.0335(6) 0.0155(6) 0.0122(6) 0.0120(6) C3 0.0597(10) 0.0567(9) 0.0511(9) 0.0219(7) 0.0271(8) 0.0219(8) C4 0.0656(11) 0.0685(11) 0.0581(10) 0.0278(9) 0.0315(9) 0.0118(9) C5 0.0717(11) 0.0539(9) 0.0533(9) 0.0281(8) 0.0204(8) 0.0091(8) C6 0.0700(11) 0.0557(10) 0.0770(12) 0.0366(9) 0.0299(10) 0.0278(9) C7 0.0649(10) 0.0475(8) 0.0426(8) 0.0197(6) 0.0255(7) 0.0201(7) C8 0.0444(7) 0.0323(6) 0.0398(7) 0.0160(5) 0.0084(6) 0.0069(5) C9 0.0396(7) 0.0299(6) 0.0403(7) 0.0151(5) 0.0091(5) 0.0049(5) C10 0.0398(7) 0.0433(7) 0.0394(7) 0.0183(6) 0.0109(6) 0.0035(6) C11 0.0615(10) 0.0422(8) 0.0412(8) 0.0160(6) 0.0017(7) 0.0062(7) C12 0.0522(10) 0.0502(9) 0.0594(10) 0.0215(8) -0.0086(8) -0.0015(7) C13 0.0372(8) 0.0525(9) 0.0752(12) 0.0278(8) 0.0051(7) 0.0032(7) C14 0.0406(7) 0.0424(7) 0.0564(9) 0.0207(7) 0.0144(7) 0.0076(6) C15 0.0387(7) 0.0382(7) 0.0365(7) 0.0118(5) 0.0110(5) 0.0009(5) C16 0.0430(7) 0.0396(7) 0.0372(7) 0.0112(6) 0.0127(6) 0.0009(6) C17 0.0419(7) 0.0404(7) 0.0389(7) 0.0119(6) 0.0116(6) -0.0013(6) C18 0.0428(9) 0.1237(18) 0.0563(11) 0.0296(11) 0.0096(8) 0.0153(10) C19 0.0531(8) 0.0388(7) 0.0354(7) 0.0134(6) 0.0128(6) -0.0002(6) C20 0.0724(11) 0.0480(9) 0.0504(9) 0.0143(7) 0.0240(8) 0.0090(8) C21 0.1081(17) 0.0395(9) 0.0623(11) 0.0127(8) 0.0246(11) 0.0113(9) C22 0.0977(16) 0.0473(10) 0.0668(12) 0.0233(9) 0.0169(11) -0.0147(10) C23 0.0733(12) 0.0599(11) 0.0822(13) 0.0297(10) 0.0281(10) -0.0097(9) C24 0.0613(10) 0.0472(9) 0.0665(10) 0.0214(8) 0.0272(8) 0.0012(7) C25 0.0809(12) 0.0570(10) 0.0391(8) 0.0156(7) 0.0205(8) -0.0009(9) C26 0.0498(8) 0.0404(7) 0.0459(8) 0.0137(6) 0.0195(6) 0.0004(6) C27 0.0599(10) 0.0484(9) 0.0573(10) 0.0226(7) 0.0127(8) 0.0042(7) C28 0.0868(14) 0.0593(11) 0.0721(12) 0.0377(9) 0.0285(10) 0.0169(10) C29 0.0932(15) 0.0515(10) 0.0862(14) 0.0321(10) 0.0454(12) 0.0021(10) C30 0.0860(14) 0.0659(12) 0.0773(13) 0.0221(10) 0.0249(11) -0.0293(11) C31 0.0691(12) 0.0674(11) 0.0553(10) 0.0226(9) 0.0115(9) -0.0205(9) C32 0.0387(7) 0.0358(6) 0.0363(7) 0.0140(5) 0.0104(5) 0.0022(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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 O2 C18 117.42(13) . . ? C10 N1 C8 107.82(11) . . ? C10 N1 C7 124.96(13) . . ? C8 N1 C7 127.15(12) . . ? N4 N3 C16 112.43(11) . . ? N4 N3 C25 118.30(12) . . ? C16 N3 C25 129.15(13) . . ? C17 N4 N3 105.19(11) . . ? C2 C1 C6 120.69(15) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C1 C2 C3 117.94(14) . . ? C1 C2 C7 122.69(13) . . ? C3 C2 C7 119.37(13) . . ? C4 C3 C2 121.25(15) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C5 C4 C3 119.99(16) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.85(16) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 120.27(16) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? N1 C7 C2 114.18(12) . . ? N1 C7 H7A 108.7 . . ? C2 C7 H7A 108.7 . . ? N1 C7 H7B 108.7 . . ? C2 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? N1 C8 C11 129.98(14) . . ? N1 C8 C9 107.77(12) . . ? C11 C8 C9 122.25(14) . . ? C14 C9 C8 118.62(13) . . ? C14 C9 C32 133.45(13) . . ? C8 C9 C32 107.91(12) . . ? O2 C10 C32 133.23(13) . . ? O2 C10 N1 115.14(12) . . ? C32 C10 N1 111.62(12) . . ? C12 C11 C8 117.46(15) . . ? C12 C11 H11 121.3 . . ? C8 C11 H11 121.3 . . ? C11 C12 C13 121.48(15) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C14 C13 C12 120.97(16) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C9 119.22(15) . . ? C13 C14 H14 120.4 . . ? C9 C14 H14 120.4 . . ? C16 C15 C17 104.29(12) . . ? C16 C15 C32 127.24(12) . . ? C17 C15 C32 128.44(12) . . ? N3 C16 C15 106.94(12) . . ? N3 C16 C19 122.27(12) . . ? C15 C16 C19 130.78(12) . . ? N4 C17 C15 111.15(12) . . ? N4 C17 C26 118.11(12) . . ? C15 C17 C26 130.63(13) . . ? O2 C18 H18A 109.5 . . ? O2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 118.85(14) . . ? C20 C19 C16 120.95(14) . . ? C24 C19 C16 120.19(14) . . ? C19 C20 C21 119.97(18) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C22 C21 C20 120.38(18) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 120.25(17) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C24 120.10(19) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C19 120.45(17) . . ? C23 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? N3 C25 H25A 109.5 . . ? N3 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N3 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C31 118.34(15) . . ? C27 C26 C17 121.68(14) . . ? C31 C26 C17 119.90(15) . . ? C26 C27 C28 120.75(17) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C29 C28 C27 120.59(19) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 119.62(17) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? C29 C30 C31 120.29(18) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C30 C31 C26 120.38(19) . . ? C30 C31 H31 119.8 . . ? C26 C31 H31 119.8 . . ? C10 C32 C9 104.86(12) . . ? C10 C32 C15 128.61(13) . . ? C9 C32 C15 126.28(12) . . ? 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 O2 C10 1.3464(17) . ? O2 C18 1.405(2) . ? N1 C10 1.3745(18) . ? N1 C8 1.3770(19) . ? N1 C7 1.4521(18) . ? N3 N4 1.3462(17) . ? N3 C16 1.3550(18) . ? N3 C25 1.4506(19) . ? N4 C17 1.3379(18) . ? C1 C2 1.381(2) . ? C1 C6 1.388(2) . ? C1 H1 0.9300 . ? C2 C3 1.384(2) . ? C2 C7 1.509(2) . ? C3 C4 1.382(2) . ? C3 H3 0.9300 . ? C4 C5 1.367(3) . ? C4 H4 0.9300 . ? C5 C6 1.369(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C11 1.391(2) . ? C8 C9 1.4075(19) . ? C9 C14 1.395(2) . ? C9 C32 1.4386(19) . ? C10 C32 1.3711(19) . ? C11 C12 1.375(3) . ? C11 H11 0.9300 . ? C12 C13 1.390(3) . ? C12 H12 0.9300 . ? C13 C14 1.380(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.3858(19) . ? C15 C17 1.4183(19) . ? C15 C32 1.4690(19) . ? C16 C19 1.4772(19) . ? C17 C26 1.477(2) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.382(2) . ? C19 C24 1.388(2) . ? C20 C21 1.390(3) . ? C20 H20 0.9300 . ? C21 C22 1.362(3) . ? C21 H21 0.9300 . ? C22 C23 1.368(3) . ? C22 H22 0.9300 . ? C23 C24 1.380(2) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.380(2) . ? C26 C31 1.389(2) . ? C27 C28 1.383(2) . ? C27 H27 0.9300 . ? C28 C29 1.361(3) . ? C28 H28 0.9300 . ? C29 C30 1.376(3) . ? C29 H29 0.9300 . ? C30 C31 1.384(3) . ? C30 H30 0.9300 . ? C31 H31 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N3 N4 C17 0.90(17) . . . . ? C25 N3 N4 C17 177.37(15) . . . . ? C6 C1 C2 C3 0.3(3) . . . . ? C6 C1 C2 C7 -179.49(16) . . . . ? C1 C2 C3 C4 -0.5(2) . . . . ? C7 C2 C3 C4 179.35(15) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C2 C1 C6 C5 -0.1(3) . . . . ? C10 N1 C7 C2 -78.64(18) . . . . ? C8 N1 C7 C2 97.86(17) . . . . ? C1 C2 C7 N1 -24.2(2) . . . . ? C3 C2 C7 N1 155.97(14) . . . . ? C10 N1 C8 C11 179.28(14) . . . . ? C7 N1 C8 C11 2.3(2) . . . . ? C10 N1 C8 C9 -0.28(15) . . . . ? C7 N1 C8 C9 -177.26(12) . . . . ? N1 C8 C9 C14 179.58(12) . . . . ? C11 C8 C9 C14 0.0(2) . . . . ? N1 C8 C9 C32 0.90(15) . . . . ? C11 C8 C9 C32 -178.70(12) . . . . ? C18 O2 C10 C32 35.2(3) . . . . ? C18 O2 C10 N1 -145.47(16) . . . . ? C8 N1 C10 O2 -179.97(12) . . . . ? C7 N1 C10 O2 -2.9(2) . . . . ? C8 N1 C10 C32 -0.49(16) . . . . ? C7 N1 C10 C32 176.57(13) . . . . ? N1 C8 C11 C12 -179.30(14) . . . . ? C9 C8 C11 C12 0.2(2) . . . . ? C8 C11 C12 C13 -0.1(2) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 C9 0.4(2) . . . . ? C8 C9 C14 C13 -0.3(2) . . . . ? C32 C9 C14 C13 178.00(14) . . . . ? N4 N3 C16 C15 -0.45(18) . . . . ? C25 N3 C16 C15 -176.45(16) . . . . ? N4 N3 C16 C19 -179.20(13) . . . . ? C25 N3 C16 C19 4.8(3) . . . . ? C17 C15 C16 N3 -0.17(16) . . . . ? C32 C15 C16 N3 -178.16(14) . . . . ? C17 C15 C16 C19 178.43(15) . . . . ? C32 C15 C16 C19 0.4(3) . . . . ? N3 N4 C17 C15 -1.00(17) . . . . ? N3 N4 C17 C26 175.60(13) . . . . ? C16 C15 C17 N4 0.74(17) . . . . ? C32 C15 C17 N4 178.70(14) . . . . ? C16 C15 C17 C26 -175.30(15) . . . . ? C32 C15 C17 C26 2.7(3) . . . . ? N3 C16 C19 C20 -121.82(17) . . . . ? C15 C16 C19 C20 59.8(2) . . . . ? N3 C16 C19 C24 58.8(2) . . . . ? C15 C16 C19 C24 -119.57(19) . . . . ? C24 C19 C20 C21 0.2(3) . . . . ? C16 C19 C20 C21 -179.15(16) . . . . ? C19 C20 C21 C22 -0.7(3) . . . . ? C20 C21 C22 C23 0.5(3) . . . . ? C21 C22 C23 C24 0.1(3) . . . . ? C22 C23 C24 C19 -0.6(3) . . . . ? C20 C19 C24 C23 0.4(3) . . . . ? C16 C19 C24 C23 179.77(16) . . . . ? N4 C17 C26 C27 -139.66(16) . . . . ? C15 C17 C26 C27 36.1(2) . . . . ? N4 C17 C26 C31 37.2(2) . . . . ? C15 C17 C26 C31 -146.98(18) . . . . ? C31 C26 C27 C28 -0.9(3) . . . . ? C17 C26 C27 C28 175.97(16) . . . . ? C26 C27 C28 C29 -0.6(3) . . . . ? C27 C28 C29 C30 1.3(3) . . . . ? C28 C29 C30 C31 -0.5(4) . . . . ? C29 C30 C31 C26 -1.1(3) . . . . ? C27 C26 C31 C30 1.8(3) . . . . ? C17 C26 C31 C30 -175.18(19) . . . . ? O2 C10 C32 C9 -179.63(16) . . . . ? N1 C10 C32 C9 1.02(15) . . . . ? O2 C10 C32 C15 5.8(3) . . . . ? N1 C10 C32 C15 -173.54(13) . . . . ? C14 C9 C32 C10 -179.56(15) . . . . ? C8 C9 C32 C10 -1.16(14) . . . . ? C14 C9 C32 C15 -4.8(2) . . . . ? C8 C9 C32 C15 173.57(13) . . . . ? C16 C15 C32 C10 -129.41(17) . . . . ? C17 C15 C32 C10 53.1(2) . . . . ? C16 C15 C32 C9 57.1(2) . . . . ? C17 C15 C32 C9 -120.39(17) . . . . ?