#------------------------------------------------------------------------------ #$Date: 2022-02-04 21:52:51 +0200 (Fri, 04 Feb 2022) $ #$Revision: 272710 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061065.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_7061065 loop_ _publ_author_name 'Hazarika, Hemanta' 'Chutia, Kangkana' 'Das, Babulal' 'Gogoi, Pranjal' _publ_section_title ; One-pot synthesis of 3-substituted-3-hydroxyindolin-2-ones: three component coupling of N-protected isatin, aryne precursor and 1,3-cyclodione under metal-free conditions ; _journal_issue 1 _journal_name_full 'New Journal of Chemistry' _journal_page_first 86 _journal_page_last 96 _journal_paper_doi 10.1039/D1NJ04295E _journal_volume 46 _journal_year 2022 _chemical_formula_sum 'C29 H27 N O4' _chemical_formula_weight 453.51 _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-2014/7 _audit_update_record ; 2021-10-09 deposited with the CCDC. 2021-11-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.443(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.578(4) _cell_length_b 11.198(3) _cell_length_c 15.831(5) _cell_measurement_reflns_used 3013 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 24.994 _cell_measurement_theta_min 1.905 _cell_volume 2399.8(12) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1298 _diffrn_reflns_av_unetI/netI 0.0501 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 62998 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 24.994 _diffrn_reflns_theta_max 24.994 _diffrn_reflns_theta_min 1.905 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.255 _exptl_crystal_description plates _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.231 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.044 _refine_ls_extinction_coef 0.0104(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 311 _refine_ls_number_reflns 4212 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0534 _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^)+(0.0699P)^2^+0.6262P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1358 _refine_ls_wR_factor_ref 0.1561 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3013 _reflns_number_total 4212 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj04295e2.cif _cod_data_source_block HH-187_0ma_a _cod_depositor_comments 'Adding full bibliography for 7061065.cif.' _cod_original_cell_volume 2399.8(13) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7061065 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; HH-187_0ma_a.res created by SHELXL-2014/7 TITL HH-187_0ma_a.res in P2(1)/n CELL 0.71073 13.5779 11.1981 15.8310 90.000 94.443 90.000 ZERR 4.000 0.0041 0.0034 0.0049 0.000 0.004 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 116 108 4 16 OMIT -3 50 L.S. 50 ACTA BOND $H FMAP 2 PLAN 2 TEMP 0.000 WGHT 0.069900 0.626200 EXTI 0.010373 FVAR 0.54038 O4 4 0.369756 0.294725 0.555437 11.00000 0.06473 0.05683 = 0.05181 0.01148 0.00296 0.01580 O1 4 0.277193 0.635492 0.590769 11.00000 0.10403 0.04397 = 0.06063 -0.00500 0.00142 -0.00133 AFIX 147 H1 2 0.242197 0.659089 0.549600 11.00000 -1.50000 AFIX 0 O3 4 0.198073 0.613727 0.433434 11.00000 0.08494 0.05972 = 0.06650 0.00069 -0.00629 0.02745 O2 4 0.458348 0.514418 0.646329 11.00000 0.05523 0.10859 = 0.07556 -0.00254 0.00061 -0.02579 N1 3 0.341435 0.414548 0.715319 11.00000 0.04901 0.07327 = 0.04383 0.00482 -0.00447 -0.00076 C7 1 0.344685 0.360817 0.484935 11.00000 0.04596 0.04679 = 0.04705 0.00682 -0.00195 -0.00044 C14 1 0.299544 0.464877 0.498672 11.00000 0.04866 0.04308 = 0.04602 0.00251 -0.00064 0.00025 C13 1 0.254853 0.529582 0.425570 11.00000 0.05495 0.04359 = 0.05498 0.00398 -0.00324 0.00372 C17 1 0.202174 0.446389 0.627701 11.00000 0.04763 0.04988 = 0.05041 -0.00409 0.00037 0.00223 C15 1 0.284870 0.509051 0.587683 11.00000 0.05531 0.04170 = 0.04983 0.00109 -0.00037 0.00027 C22 1 0.239147 0.391289 0.701561 11.00000 0.04841 0.05114 = 0.05004 -0.00193 0.00239 -0.00063 C1 1 0.449439 0.215744 0.561459 11.00000 0.05600 0.04597 = 0.05172 0.00302 -0.00602 0.00519 C9 1 0.285879 0.355202 0.330022 11.00000 0.05802 0.05090 = 0.04781 -0.00220 -0.00289 0.00163 C16 1 0.374068 0.479751 0.651221 11.00000 0.05349 0.06654 = 0.04862 -0.00612 0.00033 -0.00965 C25 1 0.386875 0.414187 0.869837 11.00000 0.04603 0.06423 = 0.05089 0.00668 -0.00772 -0.00093 C8 1 0.360372 0.309667 0.400333 11.00000 0.05835 0.04571 = 0.05463 0.00118 0.00119 0.00525 AFIX 23 H8A 2 0.355612 0.223365 0.403353 11.00000 -1.20000 H8B 2 0.426574 0.329387 0.385889 11.00000 -1.20000 AFIX 0 C12 1 0.279910 0.490357 0.339423 11.00000 0.06508 0.05295 = 0.05021 0.00700 -0.00190 0.00872 AFIX 23 H12A 2 0.342907 0.524944 0.327676 11.00000 -1.20000 H12B 2 0.230283 0.520950 0.297587 11.00000 -1.20000 AFIX 0 C26 1 0.407054 0.344794 0.941061 11.00000 0.06374 0.06178 = 0.06059 0.00977 -0.00372 -0.00349 AFIX 43 H26 2 0.428963 0.266739 0.935332 11.00000 -1.20000 AFIX 0 C6 1 0.538172 0.242300 0.530293 11.00000 0.05623 0.05148 = 0.07942 0.01476 -0.00774 -0.00199 AFIX 43 H6 2 0.546758 0.313319 0.501307 11.00000 -1.20000 AFIX 0 C21 1 0.181210 0.325277 0.751346 11.00000 0.06960 0.06017 = 0.06207 0.00382 0.01124 -0.00580 AFIX 43 H21 2 0.207504 0.288287 0.800642 11.00000 -1.20000 AFIX 0 C18 1 0.103345 0.436748 0.602511 11.00000 0.05205 0.07415 = 0.06720 -0.00684 -0.00470 0.00715 AFIX 43 H18 2 0.077253 0.473418 0.553023 11.00000 -1.20000 AFIX 0 C2 1 0.436552 0.113585 0.606822 11.00000 0.06180 0.06139 = 0.07224 0.01881 -0.00070 0.00131 AFIX 43 H2 2 0.376312 0.097422 0.628643 11.00000 -1.20000 AFIX 0 C24 1 0.354682 0.528897 0.879928 11.00000 0.07640 0.06440 = 0.06295 0.00837 -0.00570 0.00655 AFIX 43 H24 2 0.340692 0.577119 0.832690 11.00000 -1.20000 AFIX 0 C27 1 0.395154 0.389670 1.020270 11.00000 0.07791 0.08823 = 0.05477 0.01417 0.00084 -0.01134 AFIX 43 H27 2 0.408874 0.341756 1.067708 11.00000 -1.20000 AFIX 0 C23 1 0.404462 0.363943 0.783790 11.00000 0.06493 0.08574 = 0.05426 0.00274 -0.00715 0.01634 AFIX 23 H23A 2 0.472811 0.377914 0.772816 11.00000 -1.20000 H23B 2 0.394158 0.278251 0.784721 11.00000 -1.20000 AFIX 0 C10 1 0.323213 0.324864 0.244268 11.00000 0.08557 0.08144 = 0.05312 -0.00711 0.00073 0.01410 AFIX 137 H10A 2 0.330871 0.239939 0.239705 11.00000 -1.50000 H10B 2 0.385770 0.363060 0.239156 11.00000 -1.50000 H10C 2 0.276520 0.352481 0.199917 11.00000 -1.50000 AFIX 0 C20 1 0.082398 0.316212 0.725091 11.00000 0.06976 0.07607 = 0.08560 -0.01061 0.02451 -0.01915 AFIX 43 H20 2 0.041154 0.271833 0.757305 11.00000 -1.20000 AFIX 0 C4 1 0.602308 0.058849 0.587298 11.00000 0.06320 0.05835 = 0.09795 0.01277 -0.01439 0.01045 AFIX 43 H4 2 0.654333 0.005030 0.595519 11.00000 -1.20000 AFIX 0 C29 1 0.342936 0.573155 0.959786 11.00000 0.07741 0.07075 = 0.08568 -0.01534 -0.00394 0.00350 AFIX 43 H29 2 0.320851 0.651012 0.966158 11.00000 -1.20000 AFIX 0 C28 1 0.363659 0.502928 1.029857 11.00000 0.06831 0.09657 = 0.05955 -0.00786 0.00304 -0.01298 AFIX 43 H28 2 0.356072 0.533108 1.083696 11.00000 -1.20000 AFIX 0 C19 1 0.043195 0.371236 0.652332 11.00000 0.04876 0.09440 = 0.09353 -0.02044 0.00820 -0.01015 AFIX 43 H19 2 -0.023965 0.364485 0.636463 11.00000 -1.20000 AFIX 0 C11 1 0.184433 0.299281 0.336764 11.00000 0.06663 0.07985 = 0.08133 -0.00572 -0.00789 -0.01347 AFIX 137 H11A 2 0.162924 0.314120 0.392157 11.00000 -1.50000 H11B 2 0.188372 0.214730 0.327592 11.00000 -1.50000 H11C 2 0.138112 0.333775 0.294787 11.00000 -1.50000 AFIX 0 C5 1 0.614303 0.161673 0.542786 11.00000 0.05335 0.06623 = 0.10115 0.01431 -0.00507 0.00454 AFIX 43 H5 2 0.674508 0.177283 0.520733 11.00000 -1.20000 AFIX 0 C3 1 0.514616 0.035036 0.619565 11.00000 0.07925 0.05742 = 0.09177 0.02453 -0.00762 0.00588 AFIX 43 H3 2 0.507120 -0.034602 0.650427 11.00000 -1.20000 AFIX 0 HKLF 4 REM HH-187_0ma_a.res in P2(1)/n REM R1 = 0.0534 for 3013 Fo > 4sig(Fo) and 0.0767 for all 4212 data REM 311 parameters refined using 0 restraints END WGHT 0.0709 0.6221 REM Highest difference peak 0.231, deepest hole -0.301, 1-sigma level 0.044 Q1 1 0.2426 0.4431 0.5745 11.00000 0.05 0.23 Q2 1 0.3333 0.3053 0.6140 11.00000 0.05 0.23 ; _shelx_res_checksum 29558 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 O4 O 0.36976(11) 0.29472(13) 0.55544(9) 0.0579(4) Uani 1 1 d . . . . . O1 O 0.27719(14) 0.63549(13) 0.59077(10) 0.0698(5) Uani 1 1 d . . . . . H1 H 0.2422 0.6591 0.5496 0.105 Uiso 1 1 calc R U . . . O3 O 0.19807(13) 0.61373(15) 0.43343(10) 0.0710(5) Uani 1 1 d . . . . . O2 O 0.45835(12) 0.51442(18) 0.64633(11) 0.0800(5) Uani 1 1 d . . . . . N1 N 0.34143(12) 0.41455(17) 0.71532(10) 0.0558(5) Uani 1 1 d . . . . . C7 C 0.34468(14) 0.36082(18) 0.48494(12) 0.0469(5) Uani 1 1 d . . . . . C14 C 0.29954(15) 0.46488(17) 0.49867(12) 0.0461(5) Uani 1 1 d . . . . . C13 C 0.25485(16) 0.52958(19) 0.42557(13) 0.0516(5) Uani 1 1 d . . . . . C17 C 0.20217(15) 0.44639(19) 0.62770(13) 0.0495(5) Uani 1 1 d . . . . . C15 C 0.28487(15) 0.50905(18) 0.58768(12) 0.0492(5) Uani 1 1 d . . . . . C22 C 0.23915(15) 0.39129(19) 0.70156(13) 0.0499(5) Uani 1 1 d . . . . . C1 C 0.44944(15) 0.21574(19) 0.56146(13) 0.0518(5) Uani 1 1 d . . . . . C9 C 0.28588(16) 0.35520(19) 0.33002(12) 0.0526(5) Uani 1 1 d . . . . . C16 C 0.37407(16) 0.4798(2) 0.65122(13) 0.0564(6) Uani 1 1 d . . . . . C25 C 0.38688(15) 0.4142(2) 0.86984(13) 0.0543(5) Uani 1 1 d . . . . . C8 C 0.36037(16) 0.30967(19) 0.40033(13) 0.0531(5) Uani 1 1 d . . . . . H8A H 0.3556 0.2234 0.4034 0.064 Uiso 1 1 calc R U . . . H8B H 0.4266 0.3294 0.3859 0.064 Uiso 1 1 calc R U . . . C12 C 0.27991(17) 0.4904(2) 0.33942(13) 0.0564(6) Uani 1 1 d . . . . . H12A H 0.3429 0.5249 0.3277 0.068 Uiso 1 1 calc R U . . . H12B H 0.2303 0.5210 0.2976 0.068 Uiso 1 1 calc R U . . . C26 C 0.40705(17) 0.3448(2) 0.94106(14) 0.0625(6) Uani 1 1 d . . . . . H26 H 0.4290 0.2667 0.9353 0.075 Uiso 1 1 calc R U . . . C6 C 0.53817(16) 0.2423(2) 0.53029(15) 0.0631(6) Uani 1 1 d . . . . . H6 H 0.5468 0.3133 0.5013 0.076 Uiso 1 1 calc R U . . . C21 C 0.18121(18) 0.3253(2) 0.75135(15) 0.0636(6) Uani 1 1 d . . . . . H21 H 0.2075 0.2883 0.8006 0.076 Uiso 1 1 calc R U . . . C18 C 0.10334(17) 0.4367(2) 0.60251(15) 0.0650(6) Uani 1 1 d . . . . . H18 H 0.0773 0.4734 0.5530 0.078 Uiso 1 1 calc R U . . . C2 C 0.43655(18) 0.1136(2) 0.60682(15) 0.0654(6) Uani 1 1 d . . . . . H2 H 0.3763 0.0974 0.6286 0.079 Uiso 1 1 calc R U . . . C24 C 0.35468(18) 0.5289(2) 0.87993(16) 0.0685(7) Uani 1 1 d . . . . . H24 H 0.3407 0.5771 0.8327 0.082 Uiso 1 1 calc R U . . . C27 C 0.39515(19) 0.3897(3) 1.02027(15) 0.0739(7) Uani 1 1 d . . . . . H27 H 0.4089 0.3418 1.0677 0.089 Uiso 1 1 calc R U . . . C23 C 0.40446(18) 0.3639(3) 0.78379(14) 0.0689(7) Uani 1 1 d . . . . . H23A H 0.4728 0.3779 0.7728 0.083 Uiso 1 1 calc R U . . . H23B H 0.3942 0.2783 0.7847 0.083 Uiso 1 1 calc R U . . . C10 C 0.3232(2) 0.3249(2) 0.24427(14) 0.0736(7) Uani 1 1 d . . . . . H10A H 0.3309 0.2399 0.2397 0.110 Uiso 1 1 calc R U . . . H10B H 0.3858 0.3631 0.2392 0.110 Uiso 1 1 calc R U . . . H10C H 0.2765 0.3525 0.1999 0.110 Uiso 1 1 calc R U . . . C20 C 0.0824(2) 0.3162(2) 0.72509(18) 0.0762(8) Uani 1 1 d . . . . . H20 H 0.0412 0.2718 0.7573 0.091 Uiso 1 1 calc R U . . . C4 C 0.60231(19) 0.0588(2) 0.58730(18) 0.0742(7) Uani 1 1 d . . . . . H4 H 0.6543 0.0050 0.5955 0.089 Uiso 1 1 calc R U . . . C29 C 0.3429(2) 0.5732(3) 0.95979(18) 0.0785(7) Uani 1 1 d . . . . . H29 H 0.3209 0.6510 0.9662 0.094 Uiso 1 1 calc R U . . . C28 C 0.36366(18) 0.5029(3) 1.02986(16) 0.0749(7) Uani 1 1 d . . . . . H28 H 0.3561 0.5331 1.0837 0.090 Uiso 1 1 calc R U . . . C19 C 0.04320(18) 0.3712(3) 0.65233(19) 0.0788(8) Uani 1 1 d . . . . . H19 H -0.0240 0.3645 0.6365 0.095 Uiso 1 1 calc R U . . . C11 C 0.18443(18) 0.2993(3) 0.33676(17) 0.0766(7) Uani 1 1 d . . . . . H11A H 0.1629 0.3141 0.3922 0.115 Uiso 1 1 calc R U . . . H11B H 0.1884 0.2147 0.3276 0.115 Uiso 1 1 calc R U . . . H11C H 0.1381 0.3338 0.2948 0.115 Uiso 1 1 calc R U . . . C5 C 0.61430(18) 0.1617(2) 0.54279(18) 0.0741(7) Uani 1 1 d . . . . . H5 H 0.6745 0.1773 0.5207 0.089 Uiso 1 1 calc R U . . . C3 C 0.5146(2) 0.0350(2) 0.61956(18) 0.0769(7) Uani 1 1 d . . . . . H3 H 0.5071 -0.0346 0.6504 0.092 Uiso 1 1 calc R U . . . 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 O4 0.0647(9) 0.0568(9) 0.0518(8) 0.0115(7) 0.0030(7) 0.0158(8) O1 0.1040(14) 0.0440(9) 0.0606(10) -0.0050(7) 0.0014(9) -0.0013(9) O3 0.0849(11) 0.0597(10) 0.0665(10) 0.0007(8) -0.0063(8) 0.0274(9) O2 0.0552(10) 0.1086(15) 0.0756(12) -0.0025(10) 0.0006(8) -0.0258(10) N1 0.0490(10) 0.0733(12) 0.0438(9) 0.0048(9) -0.0045(7) -0.0008(9) C7 0.0460(11) 0.0468(12) 0.0470(11) 0.0068(9) -0.0019(9) -0.0004(9) C14 0.0487(11) 0.0431(11) 0.0460(11) 0.0025(9) -0.0006(9) 0.0002(9) C13 0.0550(12) 0.0436(12) 0.0550(12) 0.0040(9) -0.0032(9) 0.0037(10) C17 0.0476(11) 0.0499(12) 0.0504(11) -0.0041(10) 0.0004(9) 0.0022(9) C15 0.0553(12) 0.0417(11) 0.0498(11) 0.0011(9) -0.0004(9) 0.0003(9) C22 0.0484(11) 0.0511(12) 0.0500(11) -0.0019(9) 0.0024(9) -0.0006(10) C1 0.0560(12) 0.0460(12) 0.0517(12) 0.0030(9) -0.0060(9) 0.0052(10) C9 0.0580(13) 0.0509(13) 0.0478(11) -0.0022(9) -0.0029(9) 0.0016(10) C16 0.0535(13) 0.0665(15) 0.0486(12) -0.0061(10) 0.0003(9) -0.0096(11) C25 0.0460(11) 0.0642(15) 0.0509(12) 0.0067(10) -0.0077(9) -0.0009(10) C8 0.0584(12) 0.0457(12) 0.0546(12) 0.0012(9) 0.0012(10) 0.0052(10) C12 0.0651(14) 0.0529(13) 0.0502(12) 0.0070(10) -0.0019(10) 0.0087(11) C26 0.0637(14) 0.0618(15) 0.0606(14) 0.0098(11) -0.0037(11) -0.0035(12) C6 0.0562(13) 0.0515(13) 0.0794(16) 0.0148(12) -0.0077(11) -0.0020(11) C21 0.0696(15) 0.0602(14) 0.0621(14) 0.0038(11) 0.0112(11) -0.0058(12) C18 0.0520(13) 0.0742(16) 0.0672(14) -0.0068(12) -0.0047(11) 0.0071(12) C2 0.0618(14) 0.0614(15) 0.0722(15) 0.0188(12) -0.0007(11) 0.0013(12) C24 0.0764(16) 0.0644(16) 0.0629(15) 0.0084(12) -0.0057(12) 0.0066(13) C27 0.0779(17) 0.088(2) 0.0548(14) 0.0142(13) 0.0008(12) -0.0113(15) C23 0.0649(14) 0.0857(18) 0.0543(13) 0.0027(12) -0.0071(11) 0.0163(13) C10 0.0856(17) 0.0814(18) 0.0531(13) -0.0071(12) 0.0007(12) 0.0141(14) C20 0.0698(16) 0.0761(18) 0.0856(18) -0.0106(15) 0.0245(14) -0.0191(14) C4 0.0632(15) 0.0584(16) 0.0979(19) 0.0128(14) -0.0144(14) 0.0104(12) C29 0.0774(17) 0.0707(17) 0.0857(19) -0.0153(15) -0.0039(14) 0.0035(14) C28 0.0683(16) 0.097(2) 0.0595(15) -0.0079(15) 0.0030(12) -0.0130(15) C19 0.0488(13) 0.094(2) 0.094(2) -0.0204(16) 0.0082(13) -0.0101(14) C11 0.0666(15) 0.0798(18) 0.0813(17) -0.0057(14) -0.0079(13) -0.0135(14) C5 0.0533(13) 0.0662(16) 0.1011(19) 0.0143(15) -0.0051(13) 0.0045(12) C3 0.0792(18) 0.0574(15) 0.0918(19) 0.0245(14) -0.0076(14) 0.0059(13) 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 C7 O4 C1 122.99(15) . . ? C15 O1 H1 109.5 . . ? C16 N1 C22 111.04(17) . . ? C16 N1 C23 124.45(19) . . ? C22 N1 C23 124.17(19) . . ? C14 C7 O4 115.33(17) . . ? C14 C7 C8 125.41(18) . . ? O4 C7 C8 119.03(17) . . ? C7 C14 C13 118.05(18) . . ? C7 C14 C15 121.78(17) . . ? C13 C14 C15 119.84(17) . . ? O3 C13 C14 121.75(19) . . ? O3 C13 C12 120.37(18) . . ? C14 C13 C12 117.88(18) . . ? C18 C17 C22 119.5(2) . . ? C18 C17 C15 131.2(2) . . ? C22 C17 C15 109.30(17) . . ? O1 C15 C17 113.02(17) . . ? O1 C15 C14 111.79(16) . . ? C17 C15 C14 113.20(17) . . ? O1 C15 C16 104.16(17) . . ? C17 C15 C16 101.50(16) . . ? C14 C15 C16 112.39(16) . . ? C21 C22 C17 122.7(2) . . ? C21 C22 N1 127.7(2) . . ? C17 C22 N1 109.66(17) . . ? C2 C1 C6 121.5(2) . . ? C2 C1 O4 115.83(19) . . ? C6 C1 O4 122.48(19) . . ? C12 C9 C10 109.41(19) . . ? C12 C9 C11 110.25(19) . . ? C10 C9 C11 109.61(19) . . ? C12 C9 C8 107.26(17) . . ? C10 C9 C8 109.06(18) . . ? C11 C9 C8 111.20(19) . . ? O2 C16 N1 125.8(2) . . ? O2 C16 C15 125.7(2) . . ? N1 C16 C15 108.46(18) . . ? C24 C25 C26 118.5(2) . . ? C24 C25 C23 121.9(2) . . ? C26 C25 C23 119.5(2) . . ? C7 C8 C9 113.18(17) . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.8 . . ? C13 C12 C9 113.46(17) . . ? C13 C12 H12A 108.9 . . ? C9 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C9 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C27 C26 C25 120.7(2) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C1 C6 C5 118.6(2) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C22 C21 C20 117.1(2) . . ? C22 C21 H21 121.5 . . ? C20 C21 H21 121.5 . . ? C17 C18 C19 118.7(2) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C1 C2 C3 118.8(2) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C25 C24 C29 120.3(2) . . ? C25 C24 H24 119.8 . . ? C29 C24 H24 119.8 . . ? C28 C27 C26 120.5(2) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? N1 C23 C25 113.90(19) . . ? N1 C23 H23A 108.8 . . ? C25 C23 H23A 108.8 . . ? N1 C23 H23B 108.8 . . ? C25 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C19 C20 C21 121.6(2) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C28 C29 C24 120.3(3) . . ? C28 C29 H29 119.8 . . ? C24 C29 H29 119.8 . . ? C27 C28 C29 119.6(2) . . ? C27 C28 H28 120.2 . . ? C29 C28 H28 120.2 . . ? C20 C19 C18 120.4(2) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? 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 O4 C7 1.360(2) . ? O4 C1 1.395(2) . ? O1 C15 1.421(3) . ? O1 H1 0.8200 . ? O3 C13 1.230(2) . ? O2 C16 1.217(3) . ? N1 C16 1.352(3) . ? N1 C22 1.413(3) . ? N1 C23 1.444(3) . ? C7 C14 1.342(3) . ? C7 C8 1.487(3) . ? C14 C13 1.457(3) . ? C14 C15 1.521(3) . ? C13 C12 1.497(3) . ? C17 C18 1.374(3) . ? C17 C22 1.382(3) . ? C17 C15 1.505(3) . ? C15 C16 1.548(3) . ? C22 C21 1.372(3) . ? C1 C2 1.369(3) . ? C1 C6 1.370(3) . ? C9 C12 1.524(3) . ? C9 C10 1.524(3) . ? C9 C11 1.524(3) . ? C9 C8 1.532(3) . ? C25 C24 1.370(3) . ? C25 C26 1.379(3) . ? C25 C23 1.510(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C26 C27 1.372(3) . ? C26 H26 0.9300 . ? C6 C5 1.375(3) . ? C6 H6 0.9300 . ? C21 C20 1.377(4) . ? C21 H21 0.9300 . ? C18 C19 1.388(4) . ? C18 H18 0.9300 . ? C2 C3 1.380(3) . ? C2 H2 0.9300 . ? C24 C29 1.379(4) . ? C24 H24 0.9300 . ? C27 C28 1.351(4) . ? C27 H27 0.9300 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C20 C19 1.376(4) . ? C20 H20 0.9300 . ? C4 C3 1.358(4) . ? C4 C5 1.366(4) . ? C4 H4 0.9300 . ? C29 C28 1.371(4) . ? C29 H29 0.9300 . ? C28 H28 0.9300 . ? C19 H19 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C5 H5 0.9300 . ? C3 H3 0.9300 . ?