#------------------------------------------------------------------------------ #$Date: 2023-12-07 04:14:00 +0200 (Thu, 07 Dec 2023) $ #$Revision: 288110 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247843.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_7247843 loop_ _publ_author_name 'Luo, Zheng' 'Hu, Huayou' 'Wang, Chao' 'Yang, Zhen' 'Wang, Yefei' _publ_section_title ; A domino reaction for the synthesis of pyrrolo[2,1-a]isoquinolines from 2-aryl-pyrrolidines and alkynes promoted by a four-component catalytic system under aerobic conditions ; _journal_issue 50 _journal_name_full 'RSC Advances' _journal_page_first 35617 _journal_page_last 35620 _journal_paper_doi 10.1039/D3RA07653A _journal_volume 13 _journal_year 2023 _chemical_formula_moiety 'C26 H23 N O6' _chemical_formula_sum 'C26 H23 N O6' _chemical_formula_weight 445.45 _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 ; 2023-10-06 deposited with the CCDC. 2023-12-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.105(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.3722(4) _cell_length_b 10.3911(4) _cell_length_c 18.8309(8) _cell_measurement_reflns_used 3927 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.33 _cell_measurement_theta_min 2.66 _cell_volume 2212.62(15) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'PHOTON 100 CMOS detector' _diffrn_measurement_method 'omega scan' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_unetI/netI 0.0398 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 12879 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.357 _diffrn_reflns_theta_min 2.802 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6375 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2014)' _exptl_crystal_density_diffrn 1.337 _exptl_crystal_description block _exptl_crystal_F_000 936 _exptl_crystal_size_max 0.440 _exptl_crystal_size_mid 0.360 _exptl_crystal_size_min 0.290 _refine_diff_density_max 0.228 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 302 _refine_ls_number_reflns 4045 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0441 _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^)+(0.0504P)^2^+1.1565P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1014 _refine_ls_wR_factor_ref 0.1213 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3034 _reflns_number_total 4045 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra07653a2.cif _cod_data_source_block 1_CCDC1 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7247843 _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_estimated_absorpt_t_min 0.959 _shelx_estimated_absorpt_t_max 0.973 _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1 in P2(1)/n CELL 0.71073 11.3722 10.3911 18.8309 90.000 96.105 90.000 ZERR 4.00 0.0004 0.0004 0.0008 0.000 0.002 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 104 92 4 24 L.S. 10 BOND $h size 0.44 0.36 0.29 acta omit 1 1 0 FMAP 2 PLAN 20 TEMP -100.150 WGHT 0.050400 1.156500 FVAR 0.19873 MOLE 1 C1 1 0.218757 0.556621 1.035141 11.00000 0.02227 0.02067 = 0.02475 -0.00214 0.00154 -0.00115 C2 1 0.265281 0.458880 1.079176 11.00000 0.02280 0.02035 = 0.02600 -0.00034 0.00207 -0.00107 C3 1 0.342503 0.384535 1.041307 11.00000 0.02057 0.01901 = 0.02621 0.00012 -0.00100 -0.00084 C4 1 0.342630 0.438736 0.974337 11.00000 0.01816 0.01711 = 0.02780 -0.00206 0.00042 0.00151 C5 1 0.402801 0.406926 0.912946 11.00000 0.02007 0.01860 = 0.02718 -0.00170 0.00109 -0.00188 C6 1 0.494585 0.316152 0.917176 11.00000 0.02536 0.02397 = 0.03115 -0.00136 0.00196 0.00204 AFIX 43 H6 2 0.517268 0.273106 0.961004 11.00000 -1.20000 AFIX 0 C7 1 0.551955 0.289142 0.858112 11.00000 0.02385 0.02580 = 0.03844 -0.00422 0.00462 0.00492 AFIX 43 H7 2 0.614359 0.227942 0.861474 11.00000 -1.20000 AFIX 0 C8 1 0.519029 0.350968 0.793581 11.00000 0.02915 0.03303 = 0.03442 -0.00601 0.00895 -0.00015 AFIX 43 H8 2 0.558182 0.331098 0.752827 11.00000 -1.20000 AFIX 0 C9 1 0.430153 0.440524 0.788745 11.00000 0.03094 0.03089 = 0.02642 -0.00003 0.00295 0.00204 AFIX 43 H9 2 0.408256 0.481990 0.744343 11.00000 -1.20000 AFIX 0 C10 1 0.370425 0.472522 0.848273 11.00000 0.02317 0.02224 = 0.02738 -0.00236 0.00096 -0.00100 C11 1 0.282424 0.574386 0.845616 11.00000 0.02426 0.02451 = 0.02706 0.00014 0.00159 0.00187 C12 1 0.235199 0.611721 0.905512 11.00000 0.02317 0.01863 = 0.02786 0.00101 -0.00140 -0.00049 C13 1 0.137622 0.659474 1.056585 11.00000 0.02377 0.02184 = 0.02313 0.00037 0.00074 0.00091 C14 1 -0.055612 0.695843 1.087011 11.00000 0.02639 0.03244 = 0.05819 -0.00837 0.01051 0.00485 AFIX 137 H14A 2 -0.018608 0.740335 1.129535 11.00000 -1.50000 H14B 2 -0.123483 0.645865 1.099587 11.00000 -1.50000 H14C 2 -0.082383 0.759277 1.050296 11.00000 -1.50000 AFIX 0 C15 1 0.246497 0.448551 1.155036 11.00000 0.02544 0.02379 = 0.02792 0.00022 0.00115 -0.00263 C16 1 0.303189 0.335108 1.261923 11.00000 0.06276 0.04768 = 0.02540 0.00930 0.00437 -0.00020 AFIX 137 H16A 2 0.356601 0.398709 1.286520 11.00000 -1.50000 H16B 2 0.329002 0.248339 1.276832 11.00000 -1.50000 H16C 2 0.222605 0.349616 1.274147 11.00000 -1.50000 AFIX 0 C17 1 0.403034 0.263725 1.067817 11.00000 0.02391 0.02376 = 0.02890 0.00243 0.00380 0.00085 C18 1 0.372214 0.042715 1.089006 11.00000 0.05736 0.02203 = 0.09604 0.01877 -0.00417 0.00416 AFIX 137 H18A 2 0.443258 0.019122 1.066756 11.00000 -1.50000 H18B 2 0.311784 -0.023945 1.078920 11.00000 -1.50000 H18C 2 0.392002 0.050517 1.140762 11.00000 -1.50000 AFIX 0 C19 1 0.243965 0.639712 0.775171 11.00000 0.04630 0.04006 = 0.02977 0.00635 0.00472 0.01794 AFIX 23 H19A 2 0.314351 0.657780 0.750058 11.00000 -1.20000 H19B 2 0.205830 0.722877 0.784276 11.00000 -1.20000 AFIX 0 C20 1 0.157510 0.556175 0.727683 11.00000 0.07011 0.06984 = 0.03673 -0.00987 -0.01468 0.03111 AFIX 137 H20A 2 0.193837 0.472385 0.720283 11.00000 -1.50000 H20B 2 0.138108 0.598747 0.681484 11.00000 -1.50000 H20C 2 0.085112 0.543792 0.750813 11.00000 -1.50000 AFIX 0 C21 1 0.155845 0.724956 0.908257 11.00000 0.02617 0.02075 = 0.02273 0.00196 0.00024 0.00451 C22 1 0.205513 0.847247 0.916379 11.00000 0.02761 0.02536 = 0.03342 0.00302 0.00382 0.00156 AFIX 43 H22 2 0.288994 0.857071 0.920077 11.00000 -1.20000 AFIX 0 C23 1 0.134167 0.954445 0.919098 11.00000 0.04043 0.01992 = 0.03947 0.00159 0.00388 0.00173 AFIX 43 H23 2 0.168735 1.037502 0.925020 11.00000 -1.20000 AFIX 0 C24 1 0.011999 0.940913 0.913185 11.00000 0.03739 0.02745 = 0.03287 0.00226 0.00302 0.01321 AFIX 43 H24 2 -0.037123 1.014458 0.915326 11.00000 -1.20000 AFIX 0 C25 1 -0.037732 0.819763 0.904162 11.00000 0.02590 0.03661 = 0.03655 0.00246 0.00076 0.00735 AFIX 43 H25 2 -0.121294 0.810383 0.899495 11.00000 -1.20000 AFIX 0 C26 1 0.033516 0.711985 0.901885 11.00000 0.02715 0.02488 = 0.03128 0.00069 -0.00070 0.00061 AFIX 43 H26 2 -0.001309 0.629055 0.895957 11.00000 -1.20000 AFIX 0 N1 3 0.265235 0.544456 0.970470 11.00000 0.02149 0.01801 = 0.02319 0.00082 0.00151 0.00165 O1 4 0.029557 0.610213 1.059844 11.00000 0.02281 0.02177 = 0.04124 -0.00497 0.00498 0.00068 O2 4 0.166366 0.768235 1.072275 11.00000 0.03027 0.02136 = 0.03295 -0.00365 0.00313 -0.00023 O3 4 0.305194 0.347887 1.185604 11.00000 0.04771 0.03166 = 0.02661 0.00798 0.00432 0.00767 O4 4 0.187965 0.521915 1.186369 11.00000 0.04211 0.03714 = 0.03302 -0.00065 0.00860 0.00791 O5 4 0.327152 0.164935 1.060222 11.00000 0.03271 0.01993 = 0.05936 0.00709 -0.00441 0.00030 O6 4 0.504482 0.252346 1.091042 11.00000 0.02592 0.03682 = 0.06531 0.01348 -0.00980 0.00201 HKLF 4 REM 1 in P2(1)/n REM R1 = 0.0441 for 3034 Fo > 4sig(Fo) and 0.0701 for all 4045 data REM 302 parameters refined using 0 restraints END WGHT 0.0494 1.0251 REM Highest difference peak 0.228, deepest hole -0.230, 1-sigma level 0.049 Q1 1 -0.0247 0.7862 1.0990 11.00000 0.05 0.23 Q2 1 0.2956 0.4061 1.0634 11.00000 0.05 0.21 Q3 1 -0.1340 0.6697 1.0597 11.00000 0.05 0.20 Q4 1 0.4149 0.3138 0.8996 11.00000 0.05 0.20 Q5 1 0.4585 0.0376 1.1174 11.00000 0.05 0.19 Q6 1 0.3688 0.3408 1.0488 11.00000 0.05 0.18 Q7 1 0.1997 0.5020 1.2588 11.00000 0.05 0.18 Q8 1 0.3402 0.7172 0.7643 11.00000 0.05 0.18 Q9 1 0.2835 0.4529 1.2760 11.00000 0.05 0.17 Q10 1 0.5596 0.3012 0.9721 11.00000 0.05 0.17 Q11 1 0.1662 0.5164 0.8654 11.00000 0.05 0.16 Q12 1 -0.0651 0.6652 1.1506 11.00000 0.05 0.16 Q13 1 0.2638 0.2233 1.2667 11.00000 0.05 0.16 Q14 1 0.1574 0.6568 0.5685 11.00000 0.05 0.16 Q15 1 0.3884 0.4415 1.0429 11.00000 0.05 0.15 Q16 1 -0.0943 0.6371 1.1426 11.00000 0.05 0.15 Q17 1 0.3648 0.3759 0.8902 11.00000 0.05 0.15 Q18 1 -0.0021 0.8799 0.8915 11.00000 0.05 0.15 Q19 1 0.1526 0.7263 0.9872 11.00000 0.05 0.15 Q20 1 0.4074 0.4548 0.8818 11.00000 0.05 0.15 ; _shelx_res_checksum 34141 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 C1 C 0.21876(16) 0.55662(18) 1.03514(10) 0.0226(4) Uani 1 1 d . . . . . C2 C 0.26528(17) 0.45888(18) 1.07918(10) 0.0231(4) Uani 1 1 d . . . . . C3 C 0.34250(16) 0.38453(18) 1.04131(10) 0.0222(4) Uani 1 1 d . . . . . C4 C 0.34263(16) 0.43874(18) 0.97434(10) 0.0212(4) Uani 1 1 d . . . . . C5 C 0.40280(16) 0.40693(18) 0.91295(10) 0.0221(4) Uani 1 1 d . . . . . C6 C 0.49458(17) 0.31615(19) 0.91718(11) 0.0269(4) Uani 1 1 d . . . . . H6 H 0.5173 0.2731 0.9610 0.032 Uiso 1 1 calc R U . . . C7 C 0.55195(17) 0.2891(2) 0.85811(11) 0.0293(5) Uani 1 1 d . . . . . H7 H 0.6144 0.2279 0.8615 0.035 Uiso 1 1 calc R U . . . C8 C 0.51903(18) 0.3510(2) 0.79358(12) 0.0318(5) Uani 1 1 d . . . . . H8 H 0.5582 0.3311 0.7528 0.038 Uiso 1 1 calc R U . . . C9 C 0.43015(18) 0.4405(2) 0.78874(11) 0.0294(5) Uani 1 1 d . . . . . H9 H 0.4083 0.4820 0.7443 0.035 Uiso 1 1 calc R U . . . C10 C 0.37043(17) 0.47252(19) 0.84827(10) 0.0244(4) Uani 1 1 d . . . . . C11 C 0.28242(17) 0.57439(19) 0.84562(10) 0.0254(4) Uani 1 1 d . . . . . C12 C 0.23520(17) 0.61172(18) 0.90551(10) 0.0235(4) Uani 1 1 d . . . . . C13 C 0.13762(17) 0.65947(19) 1.05658(10) 0.0230(4) Uani 1 1 d . . . . . C14 C -0.05561(19) 0.6958(2) 1.08701(14) 0.0386(6) Uani 1 1 d . . . . . H14A H -0.0186 0.7403 1.1295 0.058 Uiso 1 1 calc R U . . . H14B H -0.1235 0.6459 1.0996 0.058 Uiso 1 1 calc R U . . . H14C H -0.0824 0.7593 1.0503 0.058 Uiso 1 1 calc R U . . . C15 C 0.24650(17) 0.44855(19) 1.15504(10) 0.0258(4) Uani 1 1 d . . . . . C16 C 0.3032(2) 0.3351(2) 1.26192(12) 0.0453(6) Uani 1 1 d . . . . . H16A H 0.3566 0.3987 1.2865 0.068 Uiso 1 1 calc R U . . . H16B H 0.3290 0.2483 1.2768 0.068 Uiso 1 1 calc R U . . . H16C H 0.2226 0.3496 1.2741 0.068 Uiso 1 1 calc R U . . . C17 C 0.40303(17) 0.26373(19) 1.06782(11) 0.0255(4) Uani 1 1 d . . . . . C18 C 0.3722(3) 0.0427(2) 1.08901(17) 0.0594(8) Uani 1 1 d . . . . . H18A H 0.4433 0.0191 1.0668 0.089 Uiso 1 1 calc R U . . . H18B H 0.3118 -0.0239 1.0789 0.089 Uiso 1 1 calc R U . . . H18C H 0.3920 0.0505 1.1408 0.089 Uiso 1 1 calc R U . . . C19 C 0.2440(2) 0.6397(2) 0.77517(11) 0.0387(6) Uani 1 1 d . . . . . H19A H 0.3144 0.6578 0.7501 0.046 Uiso 1 1 calc R U . . . H19B H 0.2058 0.7229 0.7843 0.046 Uiso 1 1 calc R U . . . C20 C 0.1575(3) 0.5562(3) 0.72768(14) 0.0604(8) Uani 1 1 d . . . . . H20A H 0.1938 0.4724 0.7203 0.091 Uiso 1 1 calc R U . . . H20B H 0.1381 0.5987 0.6815 0.091 Uiso 1 1 calc R U . . . H20C H 0.0851 0.5438 0.7508 0.091 Uiso 1 1 calc R U . . . C21 C 0.15585(17) 0.72496(18) 0.90826(10) 0.0234(4) Uani 1 1 d . . . . . C22 C 0.20551(18) 0.84725(19) 0.91638(11) 0.0288(5) Uani 1 1 d . . . . . H22 H 0.2890 0.8571 0.9201 0.035 Uiso 1 1 calc R U . . . C23 C 0.1342(2) 0.9544(2) 0.91910(12) 0.0333(5) Uani 1 1 d . . . . . H23 H 0.1687 1.0375 0.9250 0.040 Uiso 1 1 calc R U . . . C24 C 0.01200(19) 0.9409(2) 0.91319(11) 0.0326(5) Uani 1 1 d . . . . . H24 H -0.0371 1.0145 0.9153 0.039 Uiso 1 1 calc R U . . . C25 C -0.03773(19) 0.8198(2) 0.90416(12) 0.0332(5) Uani 1 1 d . . . . . H25 H -0.1213 0.8104 0.8995 0.040 Uiso 1 1 calc R U . . . C26 C 0.03352(17) 0.7120(2) 0.90189(11) 0.0280(5) Uani 1 1 d . . . . . H26 H -0.0013 0.6291 0.8960 0.034 Uiso 1 1 calc R U . . . N1 N 0.26523(13) 0.54446(14) 0.97047(8) 0.0210(4) Uani 1 1 d . . . . . O1 O 0.02956(11) 0.61021(13) 1.05984(8) 0.0285(3) Uani 1 1 d . . . . . O2 O 0.16637(12) 0.76823(13) 1.07228(7) 0.0282(3) Uani 1 1 d . . . . . O3 O 0.30519(14) 0.34789(14) 1.18560(8) 0.0353(4) Uani 1 1 d . . . . . O4 O 0.18797(14) 0.52192(15) 1.18637(8) 0.0371(4) Uani 1 1 d . . . . . O5 O 0.32715(13) 0.16493(13) 1.06022(9) 0.0380(4) Uani 1 1 d . . . . . O6 O 0.50448(13) 0.25235(15) 1.09104(9) 0.0437(4) 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 C1 0.0223(10) 0.0207(10) 0.0248(10) -0.0021(8) 0.0015(8) -0.0012(8) C2 0.0228(10) 0.0204(10) 0.0260(10) -0.0003(8) 0.0021(8) -0.0011(8) C3 0.0206(9) 0.0190(10) 0.0262(10) 0.0001(8) -0.0010(8) -0.0008(8) C4 0.0182(9) 0.0171(9) 0.0278(10) -0.0021(8) 0.0004(7) 0.0015(8) C5 0.0201(9) 0.0186(9) 0.0272(10) -0.0017(8) 0.0011(8) -0.0019(8) C6 0.0254(10) 0.0240(10) 0.0312(11) -0.0014(8) 0.0020(8) 0.0020(9) C7 0.0239(10) 0.0258(11) 0.0384(12) -0.0042(9) 0.0046(9) 0.0049(9) C8 0.0292(11) 0.0330(12) 0.0344(12) -0.0060(9) 0.0089(9) -0.0001(10) C9 0.0309(11) 0.0309(11) 0.0264(11) 0.0000(9) 0.0030(8) 0.0020(9) C10 0.0232(10) 0.0222(10) 0.0274(10) -0.0024(8) 0.0010(8) -0.0010(8) C11 0.0243(10) 0.0245(10) 0.0271(11) 0.0001(8) 0.0016(8) 0.0019(9) C12 0.0232(10) 0.0186(10) 0.0279(10) 0.0010(8) -0.0014(8) -0.0005(8) C13 0.0238(10) 0.0218(10) 0.0231(10) 0.0004(8) 0.0007(8) 0.0009(8) C14 0.0264(11) 0.0324(12) 0.0582(15) -0.0084(11) 0.0105(10) 0.0048(10) C15 0.0254(10) 0.0238(10) 0.0279(10) 0.0002(9) 0.0012(8) -0.0026(9) C16 0.0628(16) 0.0477(15) 0.0254(12) 0.0093(11) 0.0044(11) -0.0002(13) C17 0.0239(10) 0.0238(10) 0.0289(10) 0.0024(8) 0.0038(8) 0.0008(9) C18 0.0574(17) 0.0220(12) 0.096(2) 0.0188(13) -0.0042(15) 0.0042(12) C19 0.0463(13) 0.0401(13) 0.0298(12) 0.0063(10) 0.0047(10) 0.0179(11) C20 0.0701(19) 0.0698(19) 0.0367(14) -0.0099(13) -0.0147(13) 0.0311(16) C21 0.0262(10) 0.0208(10) 0.0227(10) 0.0020(8) 0.0002(8) 0.0045(8) C22 0.0276(11) 0.0254(11) 0.0334(11) 0.0030(9) 0.0038(9) 0.0016(9) C23 0.0404(13) 0.0199(10) 0.0395(12) 0.0016(9) 0.0039(10) 0.0017(10) C24 0.0374(12) 0.0274(11) 0.0329(11) 0.0023(9) 0.0030(9) 0.0132(10) C25 0.0259(11) 0.0366(13) 0.0366(12) 0.0025(10) 0.0008(9) 0.0074(10) C26 0.0272(10) 0.0249(10) 0.0313(11) 0.0007(9) -0.0007(8) 0.0006(9) N1 0.0215(8) 0.0180(8) 0.0232(8) 0.0008(6) 0.0015(6) 0.0017(7) O1 0.0228(7) 0.0218(7) 0.0412(8) -0.0050(6) 0.0050(6) 0.0007(6) O2 0.0303(8) 0.0214(7) 0.0329(8) -0.0037(6) 0.0031(6) -0.0002(6) O3 0.0477(9) 0.0317(8) 0.0266(8) 0.0080(6) 0.0043(7) 0.0077(7) O4 0.0421(9) 0.0371(9) 0.0330(8) -0.0006(7) 0.0086(7) 0.0079(7) O5 0.0327(8) 0.0199(8) 0.0594(10) 0.0071(7) -0.0044(7) 0.0003(7) O6 0.0259(8) 0.0368(9) 0.0653(12) 0.0135(8) -0.0098(7) 0.0020(7) 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 C2 C1 N1 107.67(16) . . ? C2 C1 C13 124.87(17) . . ? N1 C1 C13 127.39(16) . . ? C1 C2 C3 108.49(17) . . ? C1 C2 C15 123.45(17) . . ? C3 C2 C15 127.63(17) . . ? C4 C3 C2 107.33(16) . . ? C4 C3 C17 127.11(18) . . ? C2 C3 C17 125.36(17) . . ? C3 C4 N1 107.74(16) . . ? C3 C4 C5 133.21(18) . . ? N1 C4 C5 119.05(16) . . ? C6 C5 C10 119.90(18) . . ? C6 C5 C4 121.46(18) . . ? C10 C5 C4 118.60(17) . . ? C7 C6 C5 120.32(19) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 120.34(19) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.02(19) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 121.43(19) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C5 C10 C9 117.96(18) . . ? C5 C10 C11 119.82(17) . . ? C9 C10 C11 122.14(18) . . ? C12 C11 C10 120.77(18) . . ? C12 C11 C19 119.85(18) . . ? C10 C11 C19 119.38(17) . . ? C11 C12 N1 119.72(17) . . ? C11 C12 C21 123.41(18) . . ? N1 C12 C21 116.82(16) . . ? O2 C13 O1 125.03(18) . . ? O2 C13 C1 125.29(17) . . ? O1 C13 C1 109.57(16) . . ? O1 C14 H14A 109.5 . . ? O1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 C15 O3 124.03(19) . . ? O4 C15 C2 125.00(18) . . ? O3 C15 C2 110.96(17) . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O6 C17 O5 123.31(18) . . ? O6 C17 C3 126.77(18) . . ? O5 C17 C3 109.89(16) . . ? O5 C18 H18A 109.5 . . ? O5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C11 C19 C20 111.5(2) . . ? C11 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? C11 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 108.0 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C26 C21 C22 119.24(18) . . ? C26 C21 C12 121.72(17) . . ? C22 C21 C12 119.03(17) . . ? C23 C22 C21 120.44(19) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 120.1(2) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 119.63(19) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 120.44(19) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 120.14(19) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? C1 N1 C4 108.76(15) . . ? C1 N1 C12 129.37(16) . . ? C4 N1 C12 121.47(16) . . ? C13 O1 C14 115.66(16) . . ? C15 O3 C16 116.08(17) . . ? C17 O5 C18 115.64(17) . . ? 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 C1 C2 1.380(3) . ? C1 N1 1.384(2) . ? C1 C13 1.495(3) . ? C2 C3 1.418(3) . ? C2 C15 1.471(3) . ? C3 C4 1.381(3) . ? C3 C17 1.492(3) . ? C4 N1 1.405(2) . ? C4 C5 1.443(3) . ? C5 C6 1.403(3) . ? C5 C10 1.410(3) . ? C6 C7 1.377(3) . ? C6 H6 0.9500 . ? C7 C8 1.390(3) . ? C7 H7 0.9500 . ? C8 C9 1.370(3) . ? C8 H8 0.9500 . ? C9 C10 1.411(3) . ? C9 H9 0.9500 . ? C10 C11 1.454(3) . ? C11 C12 1.356(3) . ? C11 C19 1.513(3) . ? C12 N1 1.419(2) . ? C12 C21 1.487(3) . ? C13 O2 1.205(2) . ? C13 O1 1.339(2) . ? C14 O1 1.448(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O4 1.207(2) . ? C15 O3 1.338(2) . ? C16 O3 1.446(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 O6 1.195(2) . ? C17 O5 1.339(2) . ? C18 O5 1.453(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.527(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C26 1.390(3) . ? C21 C22 1.392(3) . ? C22 C23 1.382(3) . ? C22 H22 0.9500 . ? C23 C24 1.389(3) . ? C23 H23 0.9500 . ? C24 C25 1.383(3) . ? C24 H24 0.9500 . ? C25 C26 1.386(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ?