#------------------------------------------------------------------------------ #$Date: 2016-03-26 13:44:51 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180234 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/20/7112098.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_7112098 loop_ _publ_author_name 'Jinhu Wei' 'Wenbo Xiao' 'Cong-Ying Zhou' 'Chi-Ming Che' _publ_section_title ; Ruthenium porphyrin catalyzed diimination of indoles with aryl azides as the nitrene source ; _journal_name_full Chem.Commun. _journal_page_first 3373 _journal_paper_doi 10.1039/c3cc49052a _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C21 H15 N5 O4, 0.5(C4 H8 O2)' _chemical_formula_sum 'C23 H19 N5 O5' _chemical_formula_weight 445.43 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 73.1170(10) _cell_angle_beta 73.449(2) _cell_angle_gamma 79.959(2) _cell_formula_units_Z 2 _cell_length_a 8.0842(9) _cell_length_b 12.2092(13) _cell_length_c 12.7761(14) _cell_measurement_reflns_used 6480 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 25.03 _cell_measurement_theta_min 2.64 _cell_volume 1150.9(2) _computing_cell_refinement 'SAINT v7.34A (Bruker AXS Inc, 2006)' _computing_data_collection 'SMART (Bruker AXS Inc, 1998)' _computing_data_reduction 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'MERCURY (Macrae et al., 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Bruker SMASRT 1000 CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0134 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6480 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 2.64 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 0.9852 _exptl_absorpt_correction_T_min 0.9592 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.381 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 297 _refine_ls_number_reflns 3989 _refine_ls_number_restraints 11 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0579 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1242P)^2^+0.2333P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1738 _refine_ls_wR_factor_ref 0.1956 _reflns_number_gt 2955 _reflns_number_total 3989 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL wt1999w-CMC-XiaoWenbo'sXWB-C-41#1_14-Jan-2010 CELL 0.71073 8.08420 12.20920 12.77610 73.117 73.449 79.959 ZERR 2 0.00090 0.00130 0.00140 0.001 0.002 0.002 LATT 1 SFAC C H N O UNIT 46 38 10 10 SHEL 8.000000 0.84 OMIT 0 1 2 OMIT 0 2 2 OMIT 0 2 0 OMIT -4 10 8 OMIT 5 -5 11 OMIT -2 -5 1 OMIT -1 -3 2 OMIT 2 5 1 OMIT -2 5 1 OMIT 1 4 2 OMIT 0 -1 1 L.S. 20 FMAP 2 PLAN -20 BOND $H HTAB TEMP 23.0 DFIX 1.24 0.01 C22 O5 DFIX 1.35 0.01 C22 O6 DFIX 1.48 0.01 C22 C23 DFIX 1.47 0.01 C24 O6 DFIX 1.53 0.01 C24 C25 DANG 2.50 0.02 C25 O6 DANG 2.40 0.02 C24 C22 DANG 2.25 0.02 O5 O6 DANG 2.35 0.02 O5 C23 DANG 2.45 0.02 O6 C23 FLAT O5 O6 C22 C23 MPLA 9 N1 C1 > C8 C9 N2 N4 MPLA 7 N4 C16 > C21 MPLA 3 N5 O3 O4 MPLA 7 N2 C10 > C15 MPLA 3 N3 O1 O2 ACTA SIZE 0.450 0.250 0.160 LIST 4 WGHT 0.124200 0.233300 FVAR 0.77836 O1 4 0.091909 0.159789 1.237063 11.00000 0.12169 0.12217 = 0.08130 -0.05247 -0.02503 0.02034 O2 4 0.276775 0.012884 1.239898 11.00000 0.11697 0.08044 = 0.08064 -0.01830 -0.04987 -0.00989 O3 4 0.916593 0.641733 0.599122 11.00000 0.10266 0.07261 = 0.20978 -0.02578 -0.03596 -0.03910 O4 4 1.099576 0.497864 0.637221 11.00000 0.06703 0.12442 = 0.19503 -0.02205 -0.05098 -0.03336 N1 3 0.275458 0.117341 0.562476 11.00000 0.05833 0.05957 = 0.05469 -0.01253 -0.01572 -0.02424 N2 3 0.160895 0.093079 0.755450 11.00000 0.06148 0.06981 = 0.05466 -0.01112 -0.01280 -0.02735 N3 3 0.181263 0.087029 1.192862 11.00000 0.07175 0.07275 = 0.06186 -0.01754 -0.01530 -0.01896 N4 3 0.445312 0.240958 0.720127 11.00000 0.06258 0.05883 = 0.05804 -0.01573 -0.01531 -0.02097 N5 3 0.954617 0.539186 0.629995 11.00000 0.06769 0.08455 = 0.10795 -0.02368 -0.02420 -0.02897 C1 1 0.275786 0.130766 0.665096 11.00000 0.05143 0.05002 = 0.05463 -0.01137 -0.01562 -0.01369 C2 1 0.426185 0.200901 0.643052 11.00000 0.04860 0.04493 = 0.05498 -0.00944 -0.01642 -0.00938 C3 1 0.513655 0.214881 0.523415 11.00000 0.04944 0.04621 = 0.05509 -0.01062 -0.01502 -0.00891 C4 1 0.660410 0.265887 0.453565 11.00000 0.04997 0.05914 = 0.06467 -0.01714 -0.00935 -0.01282 AFIX 43 H4 2 0.725033 0.301067 0.481907 11.00000 -1.20000 AFIX 0 C5 1 0.709143 0.263752 0.341750 11.00000 0.05958 0.07455 = 0.06542 -0.01920 0.00072 -0.01852 AFIX 43 H5 2 0.806983 0.298097 0.294131 11.00000 -1.20000 AFIX 0 C6 1 0.614132 0.211166 0.299927 11.00000 0.07925 0.08457 = 0.05610 -0.02334 -0.00191 -0.01963 AFIX 43 H6 2 0.650149 0.209931 0.224315 11.00000 -1.20000 AFIX 0 C7 1 0.466192 0.159940 0.367257 11.00000 0.07550 0.07020 = 0.05952 -0.02211 -0.01817 -0.01627 AFIX 43 H7 2 0.402262 0.125070 0.338146 11.00000 -1.20000 AFIX 0 C8 1 0.417844 0.162782 0.478777 11.00000 0.05574 0.04916 = 0.05200 -0.01089 -0.01338 -0.01046 C9 1 0.147068 0.059545 0.544075 11.00000 0.07260 0.07596 = 0.06901 -0.01653 -0.02265 -0.03238 AFIX 137 H9A 2 0.203934 -0.004729 0.514154 11.00000 -1.50000 H9B 2 0.087801 0.112437 0.491479 11.00000 -1.50000 H9C 2 0.064842 0.032833 0.614462 11.00000 -1.50000 AFIX 0 C10 1 0.171163 0.095707 0.862793 11.00000 0.05231 0.06100 = 0.05430 -0.01040 -0.00892 -0.02412 C11 1 0.059995 0.171017 0.919956 11.00000 0.07345 0.08682 = 0.06706 -0.01797 -0.02572 0.00560 AFIX 43 H11 2 -0.017714 0.224272 0.885064 11.00000 -1.20000 AFIX 0 C12 1 0.063174 0.167976 1.027199 11.00000 0.06957 0.09018 = 0.07260 -0.03184 -0.01972 0.00992 AFIX 43 H12 2 -0.009816 0.220235 1.064293 11.00000 -1.20000 AFIX 0 C13 1 0.174408 0.087567 1.079712 11.00000 0.05676 0.06376 = 0.05376 -0.01358 -0.01171 -0.01955 C14 1 0.280858 0.009639 1.027164 11.00000 0.07530 0.06234 = 0.06852 -0.01717 -0.02886 -0.00594 AFIX 43 H14 2 0.354210 -0.045710 1.064052 11.00000 -1.20000 AFIX 0 C15 1 0.278612 0.013740 0.919407 11.00000 0.07296 0.06811 = 0.06990 -0.02711 -0.02048 -0.00139 AFIX 43 H15 2 0.350799 -0.039670 0.883489 11.00000 -1.20000 AFIX 0 C16 1 0.575967 0.314376 0.695395 11.00000 0.05798 0.05420 = 0.04819 -0.01220 -0.01573 -0.01673 C17 1 0.532094 0.432630 0.669569 11.00000 0.04958 0.05895 = 0.09645 -0.01791 -0.02731 -0.00740 AFIX 43 H17 2 0.418949 0.462323 0.666755 11.00000 -1.20000 AFIX 0 C18 1 0.656321 0.505804 0.648146 11.00000 0.06142 0.04929 = 0.10495 -0.01496 -0.02762 -0.00862 AFIX 43 H18 2 0.628197 0.585055 0.629605 11.00000 -1.20000 AFIX 0 C19 1 0.821682 0.460737 0.654409 11.00000 0.05497 0.06213 = 0.07150 -0.01566 -0.02088 -0.01831 C20 1 0.867147 0.344449 0.680662 11.00000 0.05107 0.06780 = 0.07615 -0.01039 -0.02641 -0.00658 AFIX 43 H20 2 0.980463 0.315663 0.683823 11.00000 -1.20000 AFIX 0 C21 1 0.743943 0.270363 0.702362 11.00000 0.06607 0.05125 = 0.07634 -0.00900 -0.02585 -0.00594 AFIX 43 H21 2 0.773166 0.191245 0.721587 11.00000 -1.20000 AFIX 0 PART -1 C22 1 0.400063 0.399284 0.018045 10.50000 0.31856 C23 1 0.218843 0.437902 0.019509 10.50000 0.47458 AFIX 137 H23A 2 0.174128 0.487610 0.069367 10.50000 -1.50000 H23B 2 0.153349 0.372495 0.045466 10.50000 -1.50000 H23C 2 0.209500 0.479078 -0.055341 10.50000 -1.50000 AFIX 0 O5 4 0.477615 0.303709 0.008667 10.50000 0.28352 O6 4 0.518183 0.472453 0.009663 10.50000 0.38524 C24 1 0.696432 0.408719 -0.008042 10.50000 0.35819 AFIX 23 H24A 2 0.725671 0.387805 -0.079284 10.50000 -1.20000 H24B 2 0.696992 0.338391 0.051781 10.50000 -1.20000 AFIX 0 C25 1 0.834603 0.482564 -0.008830 10.50000 0.44975 AFIX 33 H25A 2 0.946636 0.439419 -0.019775 10.50000 -1.50000 H25B 2 0.806597 0.502664 0.061928 10.50000 -1.50000 H25C 2 0.836194 0.551369 -0.069132 10.50000 -1.50000 PART 0 HKLF 4 REM wt1999w-CMC-XiaoWenbo'sXWB-C-41#1_14-Jan-2010 REM R1 = 0.0579 for 2955 Fo > 4sig(Fo) and 0.0767 for all 3989 data REM 297 parameters refined using 11 restraints END WGHT 0.1229 0.2105 REM Highest difference peak 0.381, deepest hole -0.289, 1-sigma level 0.049 Q1 1 0.0153 0.4960 0.0340 11.00000 0.05 0.38 Q2 1 0.0000 0.5000 0.0000 10.50000 0.05 0.37 Q3 1 0.3346 0.4032 0.0895 11.00000 0.05 0.29 Q4 1 0.5977 0.3587 -0.0182 11.00000 0.05 0.28 Q5 1 0.8855 0.6161 0.6869 11.00000 0.05 0.22 Q6 1 0.3210 0.4023 -0.0360 11.00000 0.05 0.21 Q7 1 0.5000 0.5000 0.0000 10.50000 0.05 0.21 Q8 1 0.0142 0.1069 0.5791 11.00000 0.05 0.18 Q9 1 0.1492 -0.0215 0.6030 11.00000 0.05 0.15 Q10 1 0.1436 0.2354 1.1881 11.00000 0.05 0.15 Q11 1 1.0733 0.4473 0.7268 11.00000 0.05 0.15 Q12 1 1.0246 0.5025 0.7080 11.00000 0.05 0.14 Q13 1 0.1705 0.1529 1.0386 11.00000 0.05 0.14 Q14 1 0.0624 0.2615 0.8637 11.00000 0.05 0.13 Q15 1 0.3984 0.1994 0.4220 11.00000 0.05 0.13 Q16 1 1.1188 0.4199 0.6888 11.00000 0.05 0.13 Q17 1 0.5000 0.0000 1.0000 10.50000 0.05 0.12 Q18 1 0.5511 0.4998 0.5039 11.00000 0.05 0.11 Q19 1 0.2770 -0.0730 1.1011 11.00000 0.05 0.11 Q20 1 1.0088 0.2999 0.6119 11.00000 0.05 0.11 ; _cod_data_source_file c3cc49052a2.cif _cod_data_source_block wt1999w-shelxl _cod_database_code 7112098 loop_ _symmetry_equiv_pos_as_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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0919(3) 0.1598(2) 1.23706(19) 0.1068(8) Uani 1 1 d . . . O2 O 0.2768(3) 0.01288(18) 1.23990(17) 0.0877(6) Uani 1 1 d . . . O3 O 0.9166(3) 0.6417(2) 0.5991(3) 0.1273(10) Uani 1 1 d . . . O4 O 1.0996(3) 0.4979(2) 0.6372(3) 0.1259(10) Uani 1 1 d . . . N1 N 0.2755(2) 0.11734(16) 0.56248(15) 0.0553(5) Uani 1 1 d . . . N2 N 0.1609(3) 0.09308(18) 0.75545(16) 0.0607(5) Uani 1 1 d . . . N3 N 0.1813(3) 0.0870(2) 1.19286(18) 0.0675(6) Uani 1 1 d . . . N4 N 0.4453(3) 0.24096(17) 0.72013(16) 0.0577(5) Uani 1 1 d . . . N5 N 0.9546(3) 0.5392(2) 0.6300(2) 0.0837(7) Uani 1 1 d . . . C1 C 0.2758(3) 0.13077(18) 0.66510(18) 0.0508(5) Uani 1 1 d . . . C2 C 0.4262(3) 0.20090(17) 0.64305(18) 0.0489(5) Uani 1 1 d . . . C3 C 0.5137(3) 0.21488(18) 0.52342(18) 0.0498(5) Uani 1 1 d . . . C4 C 0.6604(3) 0.2659(2) 0.4536(2) 0.0577(6) Uani 1 1 d . . . H4 H 0.7250 0.3011 0.4819 0.069 Uiso 1 1 calc R . . C5 C 0.7091(3) 0.2638(2) 0.3418(2) 0.0682(7) Uani 1 1 d . . . H5 H 0.8070 0.2981 0.2941 0.082 Uiso 1 1 calc R . . C6 C 0.6141(4) 0.2112(3) 0.2999(2) 0.0739(7) Uani 1 1 d . . . H6 H 0.6501 0.2099 0.2243 0.089 Uiso 1 1 calc R . . C7 C 0.4662(4) 0.1599(2) 0.3673(2) 0.0657(7) Uani 1 1 d . . . H7 H 0.4023 0.1251 0.3381 0.079 Uiso 1 1 calc R . . C8 C 0.4178(3) 0.16278(18) 0.47878(18) 0.0521(5) Uani 1 1 d . . . C9 C 0.1471(4) 0.0595(2) 0.5441(2) 0.0687(7) Uani 1 1 d . . . H9A H 0.2039 -0.0047 0.5142 0.103 Uiso 1 1 calc R . . H9B H 0.0878 0.1124 0.4915 0.103 Uiso 1 1 calc R . . H9C H 0.0648 0.0328 0.6145 0.103 Uiso 1 1 calc R . . C10 C 0.1712(3) 0.0957(2) 0.86279(19) 0.0554(6) Uani 1 1 d . . . C11 C 0.0600(4) 0.1710(3) 0.9200(2) 0.0761(8) Uani 1 1 d . . . H11 H -0.0177 0.2243 0.8851 0.091 Uiso 1 1 calc R . . C12 C 0.0632(4) 0.1680(3) 1.0272(2) 0.0769(8) Uani 1 1 d . . . H12 H -0.0098 0.2202 1.0643 0.092 Uiso 1 1 calc R . . C13 C 0.1744(3) 0.0876(2) 1.07971(19) 0.0571(6) Uani 1 1 d . . . C14 C 0.2809(4) 0.0096(2) 1.0272(2) 0.0664(7) Uani 1 1 d . . . H14 H 0.3542 -0.0457 1.0641 0.080 Uiso 1 1 calc R . . C15 C 0.2786(4) 0.0137(2) 0.9194(2) 0.0684(7) Uani 1 1 d . . . H15 H 0.3508 -0.0397 0.8835 0.082 Uiso 1 1 calc R . . C16 C 0.5760(3) 0.31438(19) 0.69540(18) 0.0517(5) Uani 1 1 d . . . C17 C 0.5321(3) 0.4326(2) 0.6696(2) 0.0665(7) Uani 1 1 d . . . H17 H 0.4189 0.4623 0.6668 0.080 Uiso 1 1 calc R . . C18 C 0.6563(3) 0.5058(2) 0.6481(3) 0.0710(7) Uani 1 1 d . . . H18 H 0.6282 0.5851 0.6296 0.085 Uiso 1 1 calc R . . C19 C 0.8217(3) 0.4607(2) 0.6544(2) 0.0605(6) Uani 1 1 d . . . C20 C 0.8671(3) 0.3444(2) 0.6807(2) 0.0644(7) Uani 1 1 d . . . H20 H 0.9805 0.3157 0.6838 0.077 Uiso 1 1 calc R . . C21 C 0.7439(3) 0.2704(2) 0.7024(2) 0.0644(6) Uani 1 1 d . . . H21 H 0.7732 0.1912 0.7216 0.077 Uiso 1 1 calc R . . C22 C 0.400(3) 0.3993(16) 0.0180(15) 0.319(12) Uiso 0.50 1 d PD A -1 C23 C 0.219(3) 0.438(3) 0.020(4) 0.47(3) Uiso 0.50 1 d PD A -1 H23A H 0.1741 0.4876 0.0694 0.712 Uiso 0.50 1 calc PR A -1 H23B H 0.1533 0.3725 0.0455 0.712 Uiso 0.50 1 calc PR A -1 H23C H 0.2095 0.4791 -0.0553 0.712 Uiso 0.50 1 calc PR A -1 O5 O 0.4776(19) 0.3037(14) 0.0087(13) 0.284(6) Uiso 0.50 1 d PD A -1 O6 O 0.518(4) 0.4725(17) 0.010(3) 0.385(10) Uiso 0.50 1 d PD A -1 C24 C 0.696(4) 0.409(2) -0.008(3) 0.358(14) Uiso 0.50 1 d PD A -1 H24A H 0.7257 0.3878 -0.0793 0.430 Uiso 0.50 1 calc PR A -1 H24B H 0.6970 0.3384 0.0518 0.430 Uiso 0.50 1 calc PR A -1 C25 C 0.835(4) 0.483(4) -0.009(4) 0.45(2) Uiso 0.50 1 d PD A -1 H25A H 0.9466 0.4394 -0.0198 0.675 Uiso 0.50 1 calc PR A -1 H25B H 0.8066 0.5027 0.0619 0.675 Uiso 0.50 1 calc PR A -1 H25C H 0.8362 0.5514 -0.0691 0.675 Uiso 0.50 1 calc PR A -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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.1217(19) 0.1222(19) 0.0813(14) -0.0525(14) -0.0250(13) 0.0203(16) O2 0.1170(17) 0.0804(13) 0.0806(13) -0.0183(10) -0.0499(13) -0.0099(12) O3 0.1027(19) 0.0726(15) 0.210(3) -0.0258(17) -0.0360(19) -0.0391(14) O4 0.0670(14) 0.124(2) 0.195(3) -0.0220(19) -0.0510(16) -0.0334(14) N1 0.0583(11) 0.0596(11) 0.0547(11) -0.0125(8) -0.0157(9) -0.0242(9) N2 0.0615(12) 0.0698(12) 0.0547(12) -0.0111(9) -0.0128(9) -0.0273(10) N3 0.0718(14) 0.0727(14) 0.0619(13) -0.0175(11) -0.0153(11) -0.0190(12) N4 0.0626(12) 0.0588(11) 0.0580(11) -0.0157(9) -0.0153(9) -0.0210(9) N5 0.0677(16) 0.0845(18) 0.1079(19) -0.0237(14) -0.0242(13) -0.0290(13) C1 0.0514(12) 0.0500(12) 0.0546(13) -0.0114(10) -0.0156(10) -0.0137(10) C2 0.0486(12) 0.0449(11) 0.0550(12) -0.0094(9) -0.0164(9) -0.0094(9) C3 0.0494(12) 0.0462(11) 0.0551(12) -0.0106(9) -0.0150(10) -0.0089(9) C4 0.0500(13) 0.0591(13) 0.0647(14) -0.0171(11) -0.0094(10) -0.0128(10) C5 0.0596(15) 0.0746(16) 0.0654(16) -0.0192(13) 0.0007(12) -0.0185(13) C6 0.0793(18) 0.0846(18) 0.0561(15) -0.0233(13) -0.0019(13) -0.0196(15) C7 0.0755(17) 0.0702(15) 0.0595(14) -0.0221(12) -0.0182(12) -0.0163(13) C8 0.0557(13) 0.0492(12) 0.0520(12) -0.0109(9) -0.0134(10) -0.0105(10) C9 0.0726(17) 0.0760(16) 0.0690(16) -0.0165(13) -0.0226(13) -0.0324(13) C10 0.0523(13) 0.0610(13) 0.0543(13) -0.0104(10) -0.0089(10) -0.0241(11) C11 0.0734(17) 0.0868(19) 0.0671(16) -0.0180(14) -0.0257(13) 0.0056(15) C12 0.0696(17) 0.090(2) 0.0726(17) -0.0318(15) -0.0197(14) 0.0099(15) C13 0.0568(14) 0.0638(14) 0.0538(13) -0.0136(11) -0.0117(10) -0.0195(11) C14 0.0753(17) 0.0623(15) 0.0685(16) -0.0172(12) -0.0289(13) -0.0059(13) C15 0.0730(17) 0.0681(16) 0.0699(16) -0.0271(13) -0.0205(13) -0.0014(13) C16 0.0580(13) 0.0542(12) 0.0482(12) -0.0122(9) -0.0157(10) -0.0167(10) C17 0.0496(13) 0.0590(14) 0.0964(19) -0.0179(13) -0.0273(13) -0.0074(11) C18 0.0614(16) 0.0493(13) 0.105(2) -0.0150(13) -0.0276(14) -0.0086(11) C19 0.0550(14) 0.0621(14) 0.0715(15) -0.0157(11) -0.0209(11) -0.0183(11) C20 0.0511(13) 0.0678(15) 0.0762(16) -0.0104(12) -0.0264(12) -0.0066(11) C21 0.0661(15) 0.0513(13) 0.0763(16) -0.0090(11) -0.0259(13) -0.0059(11) 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 C1 N1 C8 111.00(17) C1 N1 C9 124.34(19) C8 N1 C9 124.62(19) C1 N2 C10 122.66(19) O1 N3 O2 122.1(2) O1 N3 C13 119.2(2) O2 N3 C13 118.7(2) C2 N4 C16 119.94(19) O4 N5 O3 122.8(3) O4 N5 C19 118.3(3) O3 N5 C19 118.8(2) N2 C1 N1 122.57(19) N2 C1 C2 131.3(2) N1 C1 C2 106.05(18) N4 C2 C3 133.5(2) N4 C2 C1 120.6(2) C3 C2 C1 105.57(17) C4 C3 C8 119.5(2) C4 C3 C2 133.8(2) C8 C3 C2 106.74(18) C5 C4 C3 119.1(2) C5 C4 H4 120.4 C3 C4 H4 120.4 C6 C5 C4 120.5(2) C6 C5 H5 119.8 C4 C5 H5 119.8 C5 C6 C7 121.9(2) C5 C6 H6 119.0 C7 C6 H6 119.0 C8 C7 C6 117.3(2) C8 C7 H7 121.3 C6 C7 H7 121.3 C7 C8 N1 127.9(2) C7 C8 C3 121.7(2) N1 C8 C3 110.40(19) N1 C9 H9A 109.5 N1 C9 H9B 109.5 H9A C9 H9B 109.5 N1 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 C15 C10 C11 118.1(2) C15 C10 N2 120.5(2) C11 C10 N2 121.0(2) C12 C11 C10 120.7(3) C12 C11 H11 119.6 C10 C11 H11 119.6 C11 C12 C13 119.7(3) C11 C12 H12 120.2 C13 C12 H12 120.2 C14 C13 C12 121.0(2) C14 C13 N3 119.6(2) C12 C13 N3 119.4(2) C13 C14 C15 119.2(2) C13 C14 H14 120.4 C15 C14 H14 120.4 C14 C15 C10 121.3(2) C14 C15 H15 119.3 C10 C15 H15 119.3 C21 C16 C17 119.8(2) C21 C16 N4 121.2(2) C17 C16 N4 118.9(2) C18 C17 C16 119.9(2) C18 C17 H17 120.0 C16 C17 H17 120.0 C19 C18 C17 119.3(2) C19 C18 H18 120.3 C17 C18 H18 120.3 C18 C19 C20 121.6(2) C18 C19 N5 119.2(2) C20 C19 N5 119.2(2) C19 C20 C21 119.6(2) C19 C20 H20 120.2 C21 C20 H20 120.2 C20 C21 C16 119.7(2) C20 C21 H21 120.2 C16 C21 H21 120.2 O5 C22 O6 109.5(12) O5 C22 C23 127.0(15) O6 C22 C23 122.8(14) C22 O6 C24 108.6(13) O6 C24 C25 111.5(14) O6 C24 H24A 109.3 C25 C24 H24A 109.3 O6 C24 H24B 109.3 C25 C24 H24B 109.3 H24A C24 H24B 108.0 C24 C25 H25A 109.5 C24 C25 H25B 109.5 H25A C25 H25B 109.5 C24 C25 H25C 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 N3 1.210(3) O2 N3 1.217(3) O3 N5 1.211(3) O4 N5 1.210(3) N1 C1 1.368(3) N1 C8 1.398(3) N1 C9 1.456(3) N2 C1 1.279(3) N2 C10 1.407(3) N3 C13 1.460(3) N4 C2 1.275(3) N4 C16 1.412(3) N5 C19 1.471(3) C1 C2 1.523(3) C2 C3 1.463(3) C3 C4 1.387(3) C3 C8 1.401(3) C4 C5 1.376(4) C4 H4 0.9300 C5 C6 1.376(4) C5 H5 0.9300 C6 C7 1.387(4) C6 H6 0.9300 C7 C8 1.375(3) C7 H7 0.9300 C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 C10 C15 1.383(4) C10 C11 1.384(4) C11 C12 1.367(4) C11 H11 0.9300 C12 C13 1.370(4) C12 H12 0.9300 C13 C14 1.361(4) C14 C15 1.368(3) C14 H14 0.9300 C15 H15 0.9300 C16 C21 1.388(3) C16 C17 1.389(3) C17 C18 1.377(3) C17 H17 0.9300 C18 C19 1.369(4) C18 H18 0.9300 C19 C20 1.369(4) C20 C21 1.378(3) C20 H20 0.9300 C21 H21 0.9300 C22 O5 1.246(9) C22 O6 1.380(10) C22 C23 1.455(9) C23 H23A 0.9600 C23 H23B 0.9600 C23 H23C 0.9600 O6 C24 1.503(10) C24 C25 1.549(10) C24 H24A 0.9700 C24 H24B 0.9700 C25 H25A 0.9600 C25 H25B 0.9600 C25 H25C 0.9600