#------------------------------------------------------------------------------ #$Date: 2021-06-05 22:26:31 +0300 (Sat, 05 Jun 2021) $ #$Revision: 266154 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158010.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_7158010 loop_ _publ_author_name 'Pirovano, Valentina' 'Brambilla, Elisa' 'Riva, Marika' 'Leoni, Sara' 'Rizzato, Silvia' 'Garanzini, Davide' 'Abbiati, Giorgio' 'Rossi, Elisabetta' _publ_section_title ; Stereoselective synthesis of 2-spirocyclopropyl-indolin-3-ones through cyclopropanation of aza-aurones with tosylhydrazones. ; _journal_issue 17 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3925 _journal_page_last 3931 _journal_paper_doi 10.1039/d1ob00076d _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C27 H19 N O3' _chemical_formula_sum 'C27 H19 N O3' _chemical_formula_weight 405.43 _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_update_record ; 2021-01-12 deposited with the CCDC. 2021-04-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.272(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.301(2) _cell_length_b 6.870(1) _cell_length_c 29.971(6) _cell_measurement_reflns_used 2826 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 22.4 _cell_measurement_theta_min 2.3 _cell_measurement_wavelength 0.71073 _cell_volume 2103.9(7) _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SIR 2014: C. Giacovazzo et all., J. Appl. Cryst.(2015) 48, 306' _diffrn_ambient_temperature 298(2) _diffrn_detector CCD_plate _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'Bruker apex II ccd diffractometer' _diffrn_measurement_method omega-scan _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_unetI/netI 0.0307 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 12735 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 22.70 _diffrn_reflns_theta_max 22.70 _diffrn_reflns_theta_min 1.37 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max 0.7448 _exptl_absorpt_correction_T_min 0.6373 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'Sadabs 2.01 (Bruker AXS, 1999)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.2801 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 848 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.256 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.035 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 289 _refine_ls_number_reflns 2824 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0561 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+1.2343P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1359 _refine_ls_wR_factor_ref 0.1491 _reflns_Friedel_coverage 0 _reflns_number_gt 2001 _reflns_number_total 2824 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL 3n shelx.res created by SHELXL-2018/3 at 10:22:39 on 22-Dec-2020 CELL 0.71073 10.3013 6.8695 29.9706 90.000 97.272 90.000 ZERR 4.00 0.0019 0.0013 0.0055 0.000 0.003 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 108 76 4 12 MERG 2 DFIX 0.90 O3 H3o FMAP 2 PLAN 20 ACTA LIST 4 L.S. 10 TEMP 23.00 WGHT 0.064300 1.234300 FVAR 0.17856 N1 3 0.773054 0.504966 0.953715 11.00000 0.04877 0.05818 = 0.05061 -0.00523 0.00186 -0.01043 O1 4 0.504110 0.261093 0.893213 11.00000 0.05815 0.06716 = 0.06003 -0.00426 0.00326 -0.01830 O2 4 0.911026 0.719137 0.928654 11.00000 0.09319 0.10374 = 0.08561 -0.01521 0.01763 -0.04838 O3 4 0.881940 0.760201 1.004798 11.00000 0.21514 0.22760 = 0.13706 -0.04523 -0.01646 -0.07237 C1 1 0.702484 0.447148 0.909946 11.00000 0.04558 0.04868 = 0.04495 -0.00198 0.00446 -0.00741 C2 1 0.585137 0.338257 0.920527 11.00000 0.04837 0.03898 = 0.05412 0.00076 0.00679 -0.00175 C3 1 0.595468 0.326318 0.969169 11.00000 0.05586 0.03783 = 0.05066 0.00330 0.01274 0.00268 C4 1 0.709658 0.415749 0.987821 11.00000 0.05764 0.05265 = 0.05065 0.00398 0.00681 0.00625 C5 1 0.748099 0.401709 1.033926 11.00000 0.08155 0.08162 = 0.05368 -0.00065 -0.00386 0.00215 AFIX 43 H5 2 0.827273 0.453535 1.047019 11.00000 -1.20000 AFIX 0 C6 1 0.664985 0.308493 1.059533 11.00000 0.12473 0.07626 = 0.05082 0.01122 0.01144 0.00840 AFIX 43 H6 2 0.688928 0.300076 1.090450 11.00000 -1.20000 AFIX 0 C7 1 0.549207 0.228116 1.041487 11.00000 0.12554 0.05717 = 0.06506 0.00889 0.03854 -0.00105 AFIX 43 H7 2 0.494376 0.170011 1.059983 11.00000 -1.20000 AFIX 0 C8 1 0.513972 0.233710 0.995438 11.00000 0.08144 0.04347 = 0.06708 0.00055 0.02271 -0.00363 AFIX 43 H8 2 0.436650 0.175993 0.982437 11.00000 -1.20000 AFIX 0 C9 1 0.763397 0.369667 0.869504 11.00000 0.04634 0.05550 = 0.04799 -0.00166 0.00798 -0.00409 C10 1 0.701233 0.564974 0.866519 11.00000 0.05036 0.05220 = 0.05137 0.00366 0.00738 -0.00556 C11 1 0.905468 0.332520 0.869878 11.00000 0.04931 0.06977 = 0.04149 -0.00346 0.00549 -0.00226 C12 1 0.953807 0.154062 0.884442 11.00000 0.06725 0.08259 = 0.06296 -0.00559 0.00471 0.01522 AFIX 43 H12 2 0.898268 0.063375 0.895150 11.00000 -1.20000 AFIX 0 C13 1 1.082855 0.107862 0.883401 11.00000 0.07255 0.14512 = 0.09392 -0.03372 -0.00547 0.04526 AFIX 43 H13 2 1.113567 -0.014310 0.893049 11.00000 -1.20000 AFIX 0 C14 1 1.166260 0.238441 0.868449 11.00000 0.04951 0.21481 = 0.08803 -0.06524 0.00214 0.02468 AFIX 43 H14 2 1.254092 0.207317 0.868369 11.00000 -1.20000 AFIX 0 C15 1 1.119631 0.416501 0.853486 11.00000 0.05743 0.17164 = 0.07911 -0.03691 0.02229 -0.02497 AFIX 43 H15 2 1.175946 0.505932 0.842743 11.00000 -1.20000 AFIX 0 C16 1 0.989357 0.464733 0.854194 11.00000 0.06193 0.10045 = 0.06170 -0.00483 0.01342 -0.01164 AFIX 43 H16 2 0.958591 0.586267 0.844088 11.00000 -1.20000 AFIX 0 C17 1 0.576647 0.617751 0.838437 11.00000 0.06269 0.05347 = 0.04528 0.00614 0.01454 -0.00104 C18 1 0.509266 0.496138 0.808368 11.00000 0.06048 0.06727 = 0.05014 0.00600 0.01053 0.01006 AFIX 43 H18 2 0.542802 0.373068 0.803793 11.00000 -1.20000 AFIX 0 C19 1 0.387068 0.553494 0.783415 11.00000 0.06816 0.08079 = 0.03990 0.00401 0.01381 0.00206 C20 1 0.340259 0.742568 0.790371 11.00000 0.07607 0.08932 = 0.05114 0.02036 0.02122 0.01759 C21 1 0.413438 0.868151 0.819878 11.00000 0.10553 0.06867 = 0.07204 0.01314 0.03217 0.02332 AFIX 43 H21 2 0.383719 0.994141 0.823711 11.00000 -1.20000 AFIX 0 C22 1 0.528851 0.807989 0.843338 11.00000 0.08144 0.06190 = 0.05822 0.01081 0.01943 0.00705 AFIX 43 H22 2 0.576816 0.894108 0.862913 11.00000 -1.20000 AFIX 0 C23 1 0.314462 0.425764 0.753986 11.00000 0.08352 0.12520 = 0.04885 -0.00027 0.00555 0.00853 AFIX 43 H23 2 0.346561 0.302195 0.748986 11.00000 -1.20000 AFIX 0 C24 1 0.194937 0.483723 0.732372 11.00000 0.08546 0.18577 = 0.05368 0.00444 -0.00484 0.01190 AFIX 43 H24 2 0.145757 0.398238 0.712976 11.00000 -1.20000 AFIX 0 C25 1 0.146745 0.670229 0.739331 11.00000 0.08575 0.19457 = 0.06189 0.03275 0.00044 0.03606 AFIX 43 H25 2 0.065566 0.706338 0.724472 11.00000 -1.20000 AFIX 0 C26 1 0.214675 0.798268 0.766892 11.00000 0.09098 0.15277 = 0.07259 0.03981 0.01666 0.03976 AFIX 43 H26 2 0.181158 0.921901 0.770845 11.00000 -1.20000 AFIX 0 C27 1 0.857759 0.658618 0.959694 11.00000 0.06503 0.08469 = 0.06062 -0.01422 0.00569 -0.02599 H9 2 0.712370 0.269782 0.856943 11.00000 -1.20000 H10 2 0.761126 0.669459 0.871513 11.00000 -1.20000 H3O 2 0.953691 0.714216 1.024745 11.00000 -1.50000 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM 3n REM wR2 = 0.1491, GooF = S = 1.042, Restrained GooF = 1.042 for all data REM R1 = 0.0561 for 2001 Fo > 4sig(Fo) and 0.0842 for all 2824 data REM 289 parameters refined using 1 restraints END WGHT 0.0642 1.2357 REM Highest difference peak 0.256, deepest hole -0.291, 1-sigma level 0.035 Q1 1 0.8241 0.8345 0.9252 11.00000 0.05 0.26 Q2 1 0.7583 0.7193 1.0235 11.00000 0.05 0.18 Q3 1 0.9441 0.9280 1.0056 11.00000 0.05 0.18 Q4 1 0.4116 0.3999 0.7759 11.00000 0.05 0.17 Q5 1 0.2015 0.9776 0.7812 11.00000 0.05 0.17 Q6 1 0.3056 0.9296 0.8044 11.00000 0.05 0.15 Q7 1 0.4774 0.6687 0.8338 11.00000 0.05 0.13 Q8 1 1.2564 0.3025 0.8602 11.00000 0.05 0.13 Q9 1 0.7393 0.6653 0.9473 11.00000 0.05 0.12 Q10 1 0.7678 0.3984 0.9709 11.00000 0.05 0.12 Q11 1 1.0217 0.8159 0.9966 11.00000 0.05 0.11 Q12 1 0.8747 0.9608 0.9708 11.00000 0.05 0.11 Q13 1 0.7177 0.4448 0.8505 11.00000 0.05 0.11 Q14 1 0.7405 0.4634 0.9284 11.00000 0.05 0.11 Q15 1 1.1790 0.3579 0.8716 11.00000 0.05 0.10 Q16 1 0.2362 0.6120 0.7504 11.00000 0.05 0.10 Q17 1 0.7351 0.4195 0.8893 11.00000 0.05 0.10 Q18 1 0.5315 0.3496 0.9796 11.00000 0.05 0.09 Q19 1 0.5403 0.4984 0.8353 11.00000 0.05 0.09 Q20 1 0.3792 0.2554 0.7493 11.00000 0.05 0.09 ; _cod_data_source_file d1ob00076d2.cif _cod_data_source_block 3n _cod_depositor_comments 'Adding full bibliography for 7158010.cif.' _cod_original_cell_volume 2103.8(7) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7158010 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.7731(2) 0.5050(4) 0.95371(8) 0.0529(7) Uani 1 1 d . . . . . O1 O 0.5041(2) 0.2611(3) 0.89321(7) 0.0621(6) Uani 1 1 d . . . . . O2 O 0.9110(3) 0.7191(4) 0.92865(9) 0.0936(9) Uani 1 1 d . . . . . O3 O 0.8819(5) 0.7602(9) 1.00480(16) 0.197(2) Uani 1 1 d D . . . . C1 C 0.7025(3) 0.4471(4) 0.90995(9) 0.0465(7) Uani 1 1 d . . . . . C2 C 0.5851(3) 0.3383(4) 0.92053(10) 0.0471(7) Uani 1 1 d . . . . . C3 C 0.5955(3) 0.3263(4) 0.96917(10) 0.0476(8) Uani 1 1 d . . . . . C4 C 0.7097(3) 0.4157(5) 0.98782(10) 0.0536(8) Uani 1 1 d . . . . . C5 C 0.7481(4) 0.4017(6) 1.03393(11) 0.0733(10) Uani 1 1 d . . . . . H5 H 0.827273 0.453535 1.047019 0.088 Uiso 1 1 calc R U . . . C6 C 0.6650(5) 0.3085(6) 1.05953(12) 0.0839(12) Uani 1 1 d . . . . . H6 H 0.688928 0.300076 1.09045 0.101 Uiso 1 1 calc R U . . . C7 C 0.5492(5) 0.2281(5) 1.04149(13) 0.0803(12) Uani 1 1 d . . . . . H7 H 0.494376 0.170011 1.059983 0.096 Uiso 1 1 calc R U . . . C8 C 0.5140(4) 0.2337(5) 0.99544(12) 0.0629(9) Uani 1 1 d . . . . . H8 H 0.43665 0.175993 0.982437 0.075 Uiso 1 1 calc R U . . . C9 C 0.7634(3) 0.3697(5) 0.86950(10) 0.0498(8) Uani 1 1 d . . . . . C10 C 0.7012(3) 0.5650(5) 0.86652(10) 0.0512(8) Uani 1 1 d . . . . . C11 C 0.9055(3) 0.3325(5) 0.86988(9) 0.0535(8) Uani 1 1 d . . . . . C12 C 0.9538(3) 0.1541(6) 0.88444(11) 0.0712(10) Uani 1 1 d . . . . . H12 H 0.898268 0.063375 0.89515 0.085 Uiso 1 1 calc R U . . . C13 C 1.0829(5) 0.1079(9) 0.88340(15) 0.1052(16) Uani 1 1 d . . . . . H13 H 1.113567 -0.01431 0.893049 0.126 Uiso 1 1 calc R U . . . C14 C 1.1663(5) 0.2384(12) 0.86845(17) 0.118(2) Uani 1 1 d . . . . . H14 H 1.254092 0.207317 0.868369 0.142 Uiso 1 1 calc R U . . . C15 C 1.1196(4) 0.4165(10) 0.85349(14) 0.1016(16) Uani 1 1 d . . . . . H15 H 1.175946 0.505932 0.842743 0.122 Uiso 1 1 calc R U . . . C16 C 0.9894(3) 0.4647(6) 0.85419(11) 0.0742(10) Uani 1 1 d . . . . . H16 H 0.958591 0.586267 0.844088 0.089 Uiso 1 1 calc R U . . . C17 C 0.5766(3) 0.6178(5) 0.83844(10) 0.0531(8) Uani 1 1 d . . . . . C18 C 0.5093(3) 0.4961(5) 0.80837(10) 0.0590(9) Uani 1 1 d . . . . . H18 H 0.542802 0.373068 0.803793 0.071 Uiso 1 1 calc R U . . . C19 C 0.3871(3) 0.5535(6) 0.78342(10) 0.0624(9) Uani 1 1 d . . . . . C20 C 0.3403(4) 0.7426(6) 0.79037(11) 0.0710(10) Uani 1 1 d . . . . . C21 C 0.4134(4) 0.8682(6) 0.81988(13) 0.0803(11) Uani 1 1 d . . . . . H21 H 0.383719 0.994141 0.823711 0.096 Uiso 1 1 calc R U . . . C22 C 0.5289(4) 0.8080(5) 0.84334(11) 0.0663(10) Uani 1 1 d . . . . . H22 H 0.576816 0.894108 0.862913 0.08 Uiso 1 1 calc R U . . . C23 C 0.3145(4) 0.4258(7) 0.75399(12) 0.0861(12) Uani 1 1 d . . . . . H23 H 0.346561 0.302195 0.748986 0.103 Uiso 1 1 calc R U . . . C24 C 0.1949(4) 0.4837(10) 0.73237(13) 0.1095(17) Uani 1 1 d . . . . . H24 H 0.145757 0.398238 0.712976 0.131 Uiso 1 1 calc R U . . . C25 C 0.1467(5) 0.6702(11) 0.73933(16) 0.1148(19) Uani 1 1 d . . . . . H25 H 0.065566 0.706338 0.724472 0.138 Uiso 1 1 calc R U . . . C26 C 0.2147(5) 0.7983(9) 0.76689(15) 0.1049(16) Uani 1 1 d . . . . . H26 H 0.181158 0.921901 0.770845 0.126 Uiso 1 1 calc R U . . . C27 C 0.8578(3) 0.6586(6) 0.95969(12) 0.0703(10) Uani 1 1 d . . . . . H9 H 0.712(3) 0.270(5) 0.8569(12) 0.084 Uiso 1 1 d . U . . . H10 H 0.761(3) 0.669(5) 0.8715(11) 0.084 Uiso 1 1 d . U . . . H3O H 0.954(3) 0.714(6) 1.0247(13) 0.105 Uiso 1 1 d D 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 N1 0.0488(15) 0.0582(17) 0.0506(15) -0.0052(13) 0.0019(12) -0.0104(13) O1 0.0582(14) 0.0672(15) 0.0600(13) -0.0043(12) 0.0033(11) -0.0183(12) O2 0.093(2) 0.104(2) 0.0856(19) -0.0152(16) 0.0176(16) -0.0484(17) O3 0.215(5) 0.228(5) 0.137(4) -0.045(4) -0.016(3) -0.072(4) C1 0.0456(17) 0.0487(18) 0.0449(17) -0.0020(14) 0.0045(13) -0.0074(15) C2 0.0484(18) 0.0390(17) 0.0541(19) 0.0008(15) 0.0068(15) -0.0018(15) C3 0.056(2) 0.0378(17) 0.0507(18) 0.0033(14) 0.0127(15) 0.0027(15) C4 0.058(2) 0.053(2) 0.0506(19) 0.0040(16) 0.0068(16) 0.0063(17) C5 0.082(2) 0.082(3) 0.054(2) -0.0006(19) -0.0039(19) 0.002(2) C6 0.125(4) 0.076(3) 0.051(2) 0.011(2) 0.011(2) 0.008(3) C7 0.126(4) 0.057(2) 0.065(3) 0.0089(19) 0.039(2) -0.001(2) C8 0.081(2) 0.0435(19) 0.067(2) 0.0005(16) 0.0227(18) -0.0036(17) C9 0.0463(19) 0.056(2) 0.0480(18) -0.0017(15) 0.0080(14) -0.0041(16) C10 0.0504(19) 0.052(2) 0.0514(18) 0.0037(16) 0.0074(15) -0.0056(16) C11 0.0493(19) 0.070(2) 0.0415(17) -0.0035(16) 0.0055(14) -0.0023(18) C12 0.067(2) 0.083(3) 0.063(2) -0.006(2) 0.0047(17) 0.015(2) C13 0.073(3) 0.145(5) 0.094(3) -0.034(3) -0.005(3) 0.045(3) C14 0.050(3) 0.215(7) 0.088(3) -0.065(4) 0.002(2) 0.025(4) C15 0.057(3) 0.172(5) 0.079(3) -0.037(3) 0.022(2) -0.025(3) C16 0.062(2) 0.100(3) 0.062(2) -0.005(2) 0.0134(18) -0.012(2) C17 0.063(2) 0.053(2) 0.0453(18) 0.0061(16) 0.0145(16) -0.0010(17) C18 0.060(2) 0.067(2) 0.0501(19) 0.0060(17) 0.0105(16) 0.0101(18) C19 0.068(2) 0.081(3) 0.0399(18) 0.0040(18) 0.0138(17) 0.002(2) C20 0.076(3) 0.089(3) 0.051(2) 0.020(2) 0.0212(19) 0.018(2) C21 0.106(3) 0.069(3) 0.072(3) 0.013(2) 0.032(2) 0.023(2) C22 0.081(3) 0.062(2) 0.058(2) 0.0108(17) 0.0194(19) 0.007(2) C23 0.084(3) 0.125(4) 0.049(2) 0.000(2) 0.006(2) 0.009(3) C24 0.085(3) 0.186(6) 0.054(2) 0.004(3) -0.005(2) 0.012(4) C25 0.086(3) 0.195(6) 0.062(3) 0.033(4) 0.000(3) 0.036(4) C26 0.091(3) 0.153(5) 0.073(3) 0.040(3) 0.017(3) 0.040(3) C27 0.065(2) 0.085(3) 0.061(2) -0.014(2) 0.0057(18) -0.026(2) 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 0 '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 0.006 '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 C27 N1 C4 125.7(3) . . ? C27 N1 C1 124.1(3) . . ? C4 N1 C1 107.8(2) . . ? N1 C1 C2 105.6(2) . . ? N1 C1 C9 126.5(2) . . ? C2 C1 C9 114.8(2) . . ? N1 C1 C10 124.4(2) . . ? C2 C1 C10 121.8(2) . . ? C9 C1 C10 58.03(19) . . ? O1 C2 C3 127.6(3) . . ? O1 C2 C1 125.6(3) . . ? C3 C2 C1 106.5(3) . . ? C8 C3 C4 121.6(3) . . ? C8 C3 C2 128.9(3) . . ? C4 C3 C2 109.4(3) . . ? C3 C4 C5 119.5(3) . . ? C3 C4 N1 110.3(3) . . ? C5 C4 N1 130.2(3) . . ? C6 C5 C4 117.8(4) . . ? C7 C6 C5 122.8(4) . . ? C6 C7 C8 119.4(4) . . ? C3 C8 C7 118.8(4) . . ? C11 C9 C10 125.0(3) . . ? C11 C9 C1 123.8(3) . . ? C10 C9 C1 61.1(2) . . ? C9 C10 C17 126.1(3) . . ? C9 C10 C1 60.9(2) . . ? C17 C10 C1 121.6(3) . . ? C12 C11 C16 118.6(3) . . ? C12 C11 C9 118.3(3) . . ? C16 C11 C9 123.0(3) . . ? C13 C12 C11 120.9(4) . . ? C14 C13 C12 120.7(5) . . ? C13 C14 C15 119.2(4) . . ? C14 C15 C16 120.6(5) . . ? C11 C16 C15 119.9(4) . . ? C18 C17 C22 119.0(3) . . ? C18 C17 C10 124.0(3) . . ? C22 C17 C10 117.0(3) . . ? C17 C18 C19 121.3(3) . . ? C23 C19 C20 120.5(4) . . ? C23 C19 C18 121.5(4) . . ? C20 C19 C18 118.0(3) . . ? C21 C20 C19 119.9(3) . . ? C21 C20 C26 121.8(4) . . ? C19 C20 C26 118.3(4) . . ? C22 C21 C20 120.5(4) . . ? C21 C22 C17 121.3(4) . . ? C24 C23 C19 119.5(5) . . ? C23 C24 C25 120.5(5) . . ? C26 C25 C24 121.7(5) . . ? C25 C26 C20 119.5(5) . . ? O2 C27 N1 120.5(3) . . ? O2 C27 O3 119.2(4) . . ? N1 C27 O3 120.2(4) . . ? 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 C27 1.367(4) . ? N1 C4 1.420(4) . ? N1 C1 1.472(4) . ? O1 C2 1.214(3) . ? O2 C27 1.212(4) . ? O3 C27 1.514(6) . ? C1 C2 1.489(4) . ? C1 C9 1.529(4) . ? C1 C10 1.531(4) . ? C2 C3 1.451(4) . ? C3 C8 1.377(4) . ? C3 C4 1.381(4) . ? C4 C5 1.392(4) . ? C5 C6 1.378(5) . ? C6 C7 1.363(5) . ? C7 C8 1.382(5) . ? C9 C11 1.484(4) . ? C9 C10 1.484(4) . ? C10 C17 1.488(4) . ? C11 C12 1.373(5) . ? C11 C16 1.377(5) . ? C12 C13 1.371(5) . ? C13 C14 1.357(7) . ? C14 C15 1.369(7) . ? C15 C16 1.385(5) . ? C17 C18 1.354(4) . ? C17 C22 1.411(5) . ? C18 C19 1.436(4) . ? C19 C23 1.393(5) . ? C19 C20 1.410(5) . ? C20 C21 1.388(5) . ? C20 C26 1.444(5) . ? C21 C22 1.366(5) . ? C23 C24 1.376(6) . ? C24 C25 1.399(7) . ? C25 C26 1.341(7) . ? loop_ _restr_distance_atom_site_label_1 _restr_distance_atom_site_label_2 _restr_distance_target _restr_distance_target_weight_param _restr_distance_details O3 H3o 0.9 0 'generated by SHELX DFIX'