#------------------------------------------------------------------------------ #$Date: 2024-07-05 20:24:05 +0300 (Fri, 05 Jul 2024) $ #$Revision: 293165 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247855.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_7247855 loop_ _publ_author_name 'Zeng, Kui' 'Pandit, Neeraj Kumar' 'Oliveira, Jo\~ao C. A.' 'Dechert, Sebastian' 'Ackermann, Lutz' 'Zhang, Kai' _publ_section_title ; Weak-coordination-auxiliary aminocatalysis enables directed [3 + 2] cyclization for 2-acylindolizines ; _journal_issue 9 _journal_name_full 'Green Chemistry' _journal_page_first 5253 _journal_page_last 5259 _journal_paper_doi 10.1039/D3GC03552B _journal_volume 26 _journal_year 2024 _chemical_formula_moiety 'C18 H17 N O2' _chemical_formula_sum 'C18 H17 N O2' _chemical_formula_weight 279.32 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-10-12 deposited with the CCDC. 2023-12-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.717(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.985(2) _cell_length_b 8.521(2) _cell_length_c 21.601(5) _cell_measurement_reflns_used 365 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 22.2987 _cell_measurement_theta_min 1.9099 _cell_volume 1459.6(6) _computing_cell_refinement 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_data_collection 'Bruker Instrument Service vV6.2.10' _computing_data_reduction 'SAINT V8.40A (Bruker Nano, Inc., 2019)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2012)' _computing_publication_material 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.3910 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker D8 Quest' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_unetI/netI 0.0206 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 35121 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.824 _diffrn_reflns_theta_min 2.568 _diffrn_source 'Microfocus sealed tube' _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker AXS, 2016)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.271 _exptl_crystal_description block _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.233 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.257 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 193 _refine_ls_number_reflns 3462 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0378 _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^)+(0.0374P)^2^+0.7008P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.0942 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2967 _reflns_number_total 3462 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03552b2.cif _cod_data_source_block kui1417_21 _cod_depositor_comments 'Adding full bibliography for 7247855--7247856.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247855 _shelx_shelxl_version_number 2018/3 _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 0.974 _shelx_estimated_absorpt_t_max 0.995 _shelx_res_file ; TITL kui1417_21 in P2(1)/c kui1417_21.res created by SHELXL-2018/3 at 12:51:18 on 11-Oct-2021 CELL 0.71073 7.9852 8.5207 21.6008 90.000 96.717 90.000 ZERR 4.000 0.0020 0.0020 0.0050 0.000 0.009 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 72 68 4 8 TEMP -173.150 SIZE 0.060 0.233 0.320 ACTA L.S. 8 LIST 4 FMAP 2 PLAN 5 WGHT 0.037400 0.700800 FVAR 0.69083 O1 4 0.301565 0.897854 0.434859 11.00000 0.01904 0.02970 = 0.03533 0.00726 0.00964 0.00374 O2 4 1.054497 0.298939 0.437587 11.00000 0.02045 0.01480 = 0.02299 0.00138 0.00074 0.00414 N1 3 0.726788 0.934786 0.311556 11.00000 0.01505 0.01443 = 0.01597 0.00024 0.00071 0.00011 C1 1 0.536098 0.906692 0.378580 11.00000 0.01448 0.01599 = 0.01754 -0.00076 -0.00009 0.00038 C2 1 0.682893 0.841884 0.359301 11.00000 0.01524 0.01504 = 0.01601 0.00011 0.00033 -0.00096 C3 1 0.860916 0.918769 0.276460 11.00000 0.01557 0.01930 = 0.01868 -0.00187 0.00208 0.00086 AFIX 43 H3 2 0.937354 0.833644 0.284142 11.00000 -1.20000 AFIX 0 C4 1 0.882628 1.024512 0.231318 11.00000 0.01850 0.02402 = 0.01843 -0.00062 0.00293 -0.00224 AFIX 43 H4 2 0.974953 1.013584 0.207620 11.00000 -1.20000 AFIX 0 C5 1 0.767180 1.153184 0.218935 11.00000 0.02218 0.02210 = 0.01845 0.00405 -0.00013 -0.00350 AFIX 43 H5 2 0.783203 1.226867 0.187150 11.00000 -1.20000 AFIX 0 C6 1 0.634973 1.169253 0.252805 11.00000 0.01921 0.01721 = 0.01880 0.00196 -0.00218 -0.00031 AFIX 43 H6 2 0.559250 1.254797 0.244768 11.00000 -1.20000 AFIX 0 C7 1 0.609234 1.058698 0.300256 11.00000 0.01584 0.01452 = 0.01739 -0.00027 -0.00138 0.00123 C8 1 0.488610 1.041796 0.341225 11.00000 0.01546 0.01693 = 0.01740 -0.00055 -0.00014 0.00104 C9 1 0.340749 1.149830 0.343557 11.00000 0.02099 0.02385 = 0.02593 0.00452 0.00330 0.00761 AFIX 137 H9A 2 0.356923 1.244576 0.319232 11.00000 -1.50000 H9B 2 0.331666 1.178924 0.386931 11.00000 -1.50000 H9C 2 0.237224 1.096447 0.326030 11.00000 -1.50000 AFIX 0 C10 1 0.445254 0.852376 0.430684 11.00000 0.01663 0.01714 = 0.02003 -0.00143 0.00196 -0.00170 C11 1 0.529894 0.743768 0.479966 11.00000 0.02383 0.03935 = 0.02287 0.00996 0.00700 0.00603 AFIX 137 H11A 2 0.520173 0.635252 0.464941 11.00000 -1.50000 H11B 2 0.475185 0.753624 0.518094 11.00000 -1.50000 H11C 2 0.649282 0.771910 0.488860 11.00000 -1.50000 AFIX 0 C12 1 0.779134 0.698151 0.378210 11.00000 0.01673 0.01591 = 0.01526 0.00037 0.00233 0.00154 C13 1 0.703969 0.550567 0.369772 11.00000 0.01605 0.01861 = 0.02138 0.00139 -0.00109 -0.00080 AFIX 43 H13 2 0.591260 0.543082 0.350295 11.00000 -1.20000 AFIX 0 C14 1 0.790702 0.413805 0.389309 11.00000 0.02036 0.01487 = 0.02120 0.00078 0.00101 -0.00178 AFIX 43 H14 2 0.737033 0.314454 0.383808 11.00000 -1.20000 AFIX 0 C15 1 0.957452 0.424643 0.417064 11.00000 0.01880 0.01606 = 0.01371 0.00079 0.00379 0.00398 C16 1 1.035626 0.571121 0.424845 11.00000 0.01441 0.02013 = 0.01586 -0.00152 0.00143 0.00045 AFIX 43 H16 2 1.149328 0.578288 0.443314 11.00000 -1.20000 AFIX 0 C17 1 0.947527 0.705844 0.405661 11.00000 0.01708 0.01600 = 0.01639 -0.00177 0.00282 -0.00107 AFIX 43 H17 2 1.001643 0.804997 0.411123 11.00000 -1.20000 AFIX 0 C18 1 0.975676 0.148054 0.433558 11.00000 0.02503 0.01495 = 0.03196 0.00238 0.00263 0.00306 AFIX 137 H18A 2 0.937422 0.123847 0.389833 11.00000 -1.50000 H18B 2 0.878754 0.148537 0.457511 11.00000 -1.50000 H18C 2 1.056820 0.068347 0.450566 11.00000 -1.50000 AFIX 0 HKLF 4 REM kui1417_21 in P2(1)/c REM wR2 = 0.0942, GooF = S = 1.026, Restrained GooF = 1.026 for all data REM R1 = 0.0378 for 2967 Fo > 4sig(Fo) and 0.0469 for all 3462 data REM 193 parameters refined using 0 restraints END WGHT 0.0374 0.7008 REM Highest difference peak 0.257, deepest hole -0.222, 1-sigma level 0.042 Q1 1 0.5242 1.0391 0.3109 11.00000 0.05 0.26 Q2 1 0.4991 0.9781 0.3625 11.00000 0.05 0.25 Q3 1 0.6231 0.8784 0.3786 11.00000 0.05 0.24 Q4 1 0.7264 0.7713 0.3698 11.00000 0.05 0.23 Q5 1 0.4985 0.8718 0.4018 11.00000 0.05 0.22 ; _shelx_res_checksum 9756 loop_ _space_group_symop_operation_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 O1 O 0.30156(11) 0.89785(11) 0.43486(4) 0.0275(2) Uani 1 1 d . . . . . O2 O 1.05450(10) 0.29894(9) 0.43759(4) 0.01956(19) Uani 1 1 d . . . . . N1 N 0.72679(11) 0.93479(11) 0.31156(4) 0.0152(2) Uani 1 1 d . . . . . C1 C 0.53610(14) 0.90669(13) 0.37858(5) 0.0162(2) Uani 1 1 d . . . . . C2 C 0.68289(14) 0.84188(13) 0.35930(5) 0.0155(2) Uani 1 1 d . . . . . C3 C 0.86092(14) 0.91877(14) 0.27646(5) 0.0178(2) Uani 1 1 d . . . . . H3 H 0.937354 0.833644 0.284142 0.021 Uiso 1 1 calc R U . . . C4 C 0.88263(15) 1.02451(14) 0.23132(5) 0.0203(2) Uani 1 1 d . . . . . H4 H 0.974953 1.013584 0.207620 0.024 Uiso 1 1 calc R U . . . C5 C 0.76718(15) 1.15318(14) 0.21894(5) 0.0211(2) Uani 1 1 d . . . . . H5 H 0.783203 1.226867 0.187150 0.025 Uiso 1 1 calc R U . . . C6 C 0.63497(14) 1.16925(14) 0.25281(5) 0.0188(2) Uani 1 1 d . . . . . H6 H 0.559250 1.254797 0.244768 0.023 Uiso 1 1 calc R U . . . C7 C 0.60923(14) 1.05870(13) 0.30026(5) 0.0162(2) Uani 1 1 d . . . . . C8 C 0.48861(14) 1.04180(13) 0.34122(5) 0.0168(2) Uani 1 1 d . . . . . C9 C 0.34075(15) 1.14983(15) 0.34356(6) 0.0235(3) Uani 1 1 d . . . . . H9A H 0.356923 1.244576 0.319232 0.035 Uiso 1 1 calc R U . . . H9B H 0.331666 1.178924 0.386931 0.035 Uiso 1 1 calc R U . . . H9C H 0.237224 1.096447 0.326030 0.035 Uiso 1 1 calc R U . . . C10 C 0.44525(14) 0.85238(13) 0.43068(5) 0.0179(2) Uani 1 1 d . . . . . C11 C 0.52989(16) 0.74377(17) 0.47997(6) 0.0283(3) Uani 1 1 d . . . . . H11A H 0.520173 0.635252 0.464941 0.043 Uiso 1 1 calc R U . . . H11B H 0.475185 0.753624 0.518094 0.043 Uiso 1 1 calc R U . . . H11C H 0.649282 0.771910 0.488860 0.043 Uiso 1 1 calc R U . . . C12 C 0.77913(14) 0.69815(13) 0.37821(5) 0.0159(2) Uani 1 1 d . . . . . C13 C 0.70397(14) 0.55057(14) 0.36977(5) 0.0189(2) Uani 1 1 d . . . . . H13 H 0.591260 0.543082 0.350295 0.023 Uiso 1 1 calc R U . . . C14 C 0.79070(15) 0.41381(13) 0.38931(5) 0.0189(2) Uani 1 1 d . . . . . H14 H 0.737033 0.314454 0.383808 0.023 Uiso 1 1 calc R U . . . C15 C 0.95745(14) 0.42464(13) 0.41706(5) 0.0160(2) Uani 1 1 d . . . . . C16 C 1.03563(14) 0.57112(13) 0.42484(5) 0.0168(2) Uani 1 1 d . . . . . H16 H 1.149328 0.578288 0.443314 0.020 Uiso 1 1 calc R U . . . C17 C 0.94753(14) 0.70584(13) 0.40566(5) 0.0164(2) Uani 1 1 d . . . . . H17 H 1.001643 0.804997 0.411123 0.020 Uiso 1 1 calc R U . . . C18 C 0.97568(16) 0.14805(14) 0.43356(6) 0.0240(3) Uani 1 1 d . . . . . H18A H 0.937422 0.123847 0.389833 0.036 Uiso 1 1 calc R U . . . H18B H 0.878754 0.148537 0.457511 0.036 Uiso 1 1 calc R U . . . H18C H 1.056820 0.068347 0.450566 0.036 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 O1 0.0190(4) 0.0297(5) 0.0353(5) 0.0073(4) 0.0096(4) 0.0037(4) O2 0.0204(4) 0.0148(4) 0.0230(4) 0.0014(3) 0.0007(3) 0.0041(3) N1 0.0151(4) 0.0144(5) 0.0160(4) 0.0002(3) 0.0007(3) 0.0001(3) C1 0.0145(5) 0.0160(5) 0.0175(5) -0.0008(4) -0.0001(4) 0.0004(4) C2 0.0152(5) 0.0150(5) 0.0160(5) 0.0001(4) 0.0003(4) -0.0010(4) C3 0.0156(5) 0.0193(5) 0.0187(5) -0.0019(4) 0.0021(4) 0.0009(4) C4 0.0185(5) 0.0240(6) 0.0184(5) -0.0006(4) 0.0029(4) -0.0022(5) C5 0.0222(6) 0.0221(6) 0.0185(5) 0.0041(5) -0.0001(4) -0.0035(5) C6 0.0192(5) 0.0172(5) 0.0188(5) 0.0020(4) -0.0022(4) -0.0003(4) C7 0.0158(5) 0.0145(5) 0.0174(5) -0.0003(4) -0.0014(4) 0.0012(4) C8 0.0155(5) 0.0169(5) 0.0174(5) -0.0005(4) -0.0001(4) 0.0010(4) C9 0.0210(6) 0.0239(6) 0.0259(6) 0.0045(5) 0.0033(5) 0.0076(5) C10 0.0166(5) 0.0171(5) 0.0200(5) -0.0014(4) 0.0020(4) -0.0017(4) C11 0.0238(6) 0.0394(8) 0.0229(6) 0.0100(5) 0.0070(5) 0.0060(6) C12 0.0167(5) 0.0159(5) 0.0153(5) 0.0004(4) 0.0023(4) 0.0015(4) C13 0.0161(5) 0.0186(6) 0.0214(6) 0.0014(4) -0.0011(4) -0.0008(4) C14 0.0204(6) 0.0149(5) 0.0212(5) 0.0008(4) 0.0010(4) -0.0018(4) C15 0.0188(5) 0.0161(5) 0.0137(5) 0.0008(4) 0.0038(4) 0.0040(4) C16 0.0144(5) 0.0201(6) 0.0159(5) -0.0015(4) 0.0014(4) 0.0004(4) C17 0.0171(5) 0.0160(5) 0.0164(5) -0.0018(4) 0.0028(4) -0.0011(4) C18 0.0250(6) 0.0149(6) 0.0320(7) 0.0024(5) 0.0026(5) 0.0031(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 C15 O2 C18 117.17(9) . . ? C2 N1 C3 129.19(10) . . ? C2 N1 C7 109.65(9) . . ? C3 N1 C7 121.16(9) . . ? C2 C1 C8 108.96(10) . . ? C2 C1 C10 127.06(10) . . ? C8 C1 C10 123.93(10) . . ? N1 C2 C1 106.90(10) . . ? N1 C2 C12 120.90(10) . . ? C1 C2 C12 132.07(10) . . ? C4 C3 N1 119.97(11) . . ? C3 C4 C5 120.56(11) . . ? C6 C5 C4 119.87(11) . . ? C5 C6 C7 120.46(11) . . ? C8 C7 N1 107.94(9) . . ? C8 C7 C6 134.09(11) . . ? N1 C7 C6 117.96(10) . . ? C7 C8 C1 106.54(10) . . ? C7 C8 C9 124.32(10) . . ? C1 C8 C9 129.14(10) . . ? O1 C10 C1 120.20(11) . . ? O1 C10 C11 119.23(11) . . ? C1 C10 C11 120.55(10) . . ? C13 C12 C17 118.18(10) . . ? C13 C12 C2 120.57(10) . . ? C17 C12 C2 121.24(10) . . ? C14 C13 C12 121.47(10) . . ? C13 C14 C15 119.25(11) . . ? O2 C15 C16 115.67(10) . . ? O2 C15 C14 124.29(10) . . ? C16 C15 C14 120.03(10) . . ? C17 C16 C15 120.04(10) . . ? C16 C17 C12 121.00(10) . . ? 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 O1 C10 1.2243(14) . ? O2 C15 1.3652(13) . ? O2 C18 1.4296(15) . ? N1 C2 1.3776(14) . ? N1 C3 1.3894(15) . ? N1 C7 1.4149(14) . ? C1 C2 1.4023(16) . ? C1 C8 1.4313(16) . ? C1 C10 1.4826(16) . ? C2 C12 1.4778(15) . ? C3 C4 1.3536(17) . ? C4 C5 1.4373(17) . ? C5 C6 1.3598(17) . ? C6 C7 1.4246(16) . ? C7 C8 1.3896(16) . ? C8 C9 1.5026(16) . ? C10 C11 1.5093(17) . ? C12 C13 1.3961(16) . ? C12 C17 1.4062(16) . ? C13 C14 1.3955(16) . ? C14 C15 1.3979(16) . ? C15 C16 1.3968(16) . ? C16 C17 1.3843(16) . ?