#------------------------------------------------------------------------------ #$Date: 2023-12-14 02:38:33 +0200 (Thu, 14 Dec 2023) $ #$Revision: 288293 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247856.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_7247856 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_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D3GC03552B _journal_year 2024 _chemical_formula_moiety 'C13 H15 N O' _chemical_formula_sum 'C13 H15 N O' _chemical_formula_weight 201.26 _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 100.317(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.5190(13) _cell_length_b 12.050(2) _cell_length_c 11.678(2) _cell_measurement_reflns_used 155 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 22.1858 _cell_measurement_theta_min 2.4498 _cell_volume 1041.0(3) _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 0.1020 _diffrn_reflns_av_unetI/netI 0.0462 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 31200 _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 27.885 _diffrn_reflns_theta_min 2.449 _diffrn_source 'Microfocus sealed tube' _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker AXS, 2016)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.284 _exptl_crystal_description block _exptl_crystal_F_000 432 _exptl_crystal_size_max 0.347 _exptl_crystal_size_mid 0.188 _exptl_crystal_size_min 0.124 _refine_diff_density_max 0.229 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 139 _refine_ls_number_reflns 2483 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.078 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0505 _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^)+(0.0516P)^2^+0.5691P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1167 _refine_ls_wR_factor_ref 0.1372 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1762 _reflns_number_total 2483 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03552b2.cif _cod_data_source_block kui1366_21 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247856 _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 0.972 _shelx_estimated_absorpt_t_max 0.990 _shelx_res_file ; TITL kui1366_21 in P2(1)/c kui1366_21.res created by SHELXL-2018/3 at 12:48:01 on 08-Oct-2021 CELL 0.71073 7.5190 12.0505 11.6778 90.000 100.317 90.000 ZERR 4.000 0.0013 0.0022 0.0021 0.000 0.006 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 52 60 4 4 TEMP -173.150 SIZE 0.124 0.188 0.347 L.S. 8 ACTA LIST 4 FMAP 2 PLAN 5 WGHT 0.051600 0.569100 FVAR 0.77667 O1 4 0.325765 0.254702 0.655526 11.00000 0.03882 0.03168 = 0.02462 0.00287 0.00049 -0.00109 N1 3 0.318885 0.590029 0.558367 11.00000 0.02281 0.03099 = 0.02034 -0.00001 0.00371 -0.00047 C1 1 0.263627 0.409087 0.531211 11.00000 0.02164 0.02897 = 0.01960 -0.00138 0.00567 0.00040 C2 1 0.347679 0.488752 0.610725 11.00000 0.02114 0.02776 = 0.02038 0.00099 0.00542 0.00039 C3 1 0.371508 0.694887 0.600425 11.00000 0.02501 0.03145 = 0.02206 -0.00185 0.00339 -0.00211 AFIX 43 H3 2 0.439430 0.703304 0.676750 11.00000 -1.20000 AFIX 0 C4 1 0.325883 0.785292 0.532472 11.00000 0.02907 0.02902 = 0.02904 -0.00016 0.00376 -0.00308 AFIX 43 H4 2 0.361634 0.857017 0.561634 11.00000 -1.20000 AFIX 0 C5 1 0.224485 0.773646 0.417362 11.00000 0.03224 0.03271 = 0.02533 0.00443 0.00238 0.00352 AFIX 43 H5 2 0.194310 0.837314 0.369881 11.00000 -1.20000 AFIX 0 C6 1 0.171502 0.671642 0.376111 11.00000 0.02626 0.03517 = 0.02128 0.00046 0.00219 0.00337 AFIX 43 H6 2 0.103424 0.664202 0.299709 11.00000 -1.20000 AFIX 0 C7 1 0.216290 0.576281 0.445351 11.00000 0.01839 0.02964 = 0.01684 -0.00022 0.00266 0.00226 C8 1 0.182372 0.464829 0.426995 11.00000 0.01925 0.03188 = 0.02059 -0.00113 0.00468 0.00221 C9 1 0.452008 0.476963 0.731330 11.00000 0.02938 0.03142 = 0.02006 -0.00051 0.00084 -0.00098 AFIX 137 H9A 2 0.526483 0.409796 0.736334 11.00000 -1.50000 H9B 2 0.368013 0.471450 0.786291 11.00000 -1.50000 H9C 2 0.530095 0.541897 0.750631 11.00000 -1.50000 AFIX 0 C10 1 0.073819 0.420772 0.316141 11.00000 0.02838 0.03577 = 0.02180 -0.00046 0.00049 0.00190 AFIX 137 H10A 2 0.026617 0.482855 0.265485 11.00000 -1.50000 H10B 2 -0.027099 0.376426 0.333861 11.00000 -1.50000 H10C 2 0.150944 0.374219 0.276578 11.00000 -1.50000 AFIX 0 C11 1 0.264908 0.289771 0.557525 11.00000 0.02333 0.03198 = 0.02164 0.00006 0.00567 0.00096 C12 1 0.188568 0.208842 0.462221 11.00000 0.02751 0.03112 = 0.02299 -0.00220 0.00494 -0.00304 AFIX 23 H12A 2 0.245688 0.222749 0.393496 11.00000 -1.20000 H12B 2 0.057211 0.222398 0.438859 11.00000 -1.20000 AFIX 0 C13 1 0.218324 0.088275 0.498522 11.00000 0.04406 0.02983 = 0.02866 -0.00218 0.00936 -0.00737 AFIX 137 H13A 2 0.164897 0.040005 0.433914 11.00000 -1.50000 H13B 2 0.160987 0.073581 0.566029 11.00000 -1.50000 H13C 2 0.348286 0.073443 0.519047 11.00000 -1.50000 AFIX 0 HKLF 4 REM kui1366_21 in P2(1)/c REM wR2 = 0.1372, GooF = S = 1.078, Restrained GooF = 1.078 for all data REM R1 = 0.0505 for 1762 Fo > 4sig(Fo) and 0.0863 for all 2483 data REM 139 parameters refined using 0 restraints END WGHT 0.0516 0.5691 REM Highest difference peak 0.229, deepest hole -0.258, 1-sigma level 0.052 Q1 1 0.5918 0.4849 0.7397 11.00000 0.05 0.23 Q2 1 0.2790 0.3592 0.5396 11.00000 0.05 0.20 Q3 1 0.3069 0.4416 0.5693 11.00000 0.05 0.19 Q4 1 0.4089 0.5381 0.7857 11.00000 0.05 0.19 Q5 1 0.2350 0.5823 0.4801 11.00000 0.05 0.19 ; _shelx_res_checksum 50727 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 0.32576(18) 0.25470(11) 0.65553(11) 0.0323(3) Uani 1 1 d . . . . . N1 N 0.31888(19) 0.59003(13) 0.55837(12) 0.0247(3) Uani 1 1 d . . . . . C1 C 0.2636(2) 0.40909(15) 0.53121(14) 0.0232(4) Uani 1 1 d . . . . . C2 C 0.3477(2) 0.48875(15) 0.61072(14) 0.0229(4) Uani 1 1 d . . . . . C3 C 0.3715(2) 0.69489(15) 0.60042(15) 0.0263(4) Uani 1 1 d . . . . . H3 H 0.439430 0.703304 0.676750 0.032 Uiso 1 1 calc R U . . . C4 C 0.3259(2) 0.78529(16) 0.53247(16) 0.0292(4) Uani 1 1 d . . . . . H4 H 0.361634 0.857017 0.561634 0.035 Uiso 1 1 calc R U . . . C5 C 0.2245(3) 0.77365(16) 0.41736(16) 0.0304(4) Uani 1 1 d . . . . . H5 H 0.194310 0.837314 0.369881 0.037 Uiso 1 1 calc R U . . . C6 C 0.1715(2) 0.67164(16) 0.37611(16) 0.0278(4) Uani 1 1 d . . . . . H6 H 0.103424 0.664202 0.299709 0.033 Uiso 1 1 calc R U . . . C7 C 0.2163(2) 0.57628(15) 0.44535(14) 0.0217(4) Uani 1 1 d . . . . . C8 C 0.1824(2) 0.46483(15) 0.42699(14) 0.0238(4) Uani 1 1 d . . . . . C9 C 0.4520(2) 0.47696(16) 0.73133(15) 0.0274(4) Uani 1 1 d . . . . . H9A H 0.526483 0.409796 0.736334 0.041 Uiso 1 1 calc R U . . . H9B H 0.368013 0.471450 0.786291 0.041 Uiso 1 1 calc R U . . . H9C H 0.530095 0.541897 0.750631 0.041 Uiso 1 1 calc R U . . . C10 C 0.0738(2) 0.42077(16) 0.31614(15) 0.0291(4) Uani 1 1 d . . . . . H10A H 0.026617 0.482855 0.265485 0.044 Uiso 1 1 calc R U . . . H10B H -0.027099 0.376426 0.333861 0.044 Uiso 1 1 calc R U . . . H10C H 0.150944 0.374219 0.276578 0.044 Uiso 1 1 calc R U . . . C11 C 0.2649(2) 0.28977(16) 0.55752(15) 0.0255(4) Uani 1 1 d . . . . . C12 C 0.1886(2) 0.20884(16) 0.46222(15) 0.0272(4) Uani 1 1 d . . . . . H12A H 0.245688 0.222749 0.393496 0.033 Uiso 1 1 calc R U . . . H12B H 0.057211 0.222398 0.438859 0.033 Uiso 1 1 calc R U . . . C13 C 0.2183(3) 0.08828(16) 0.49852(16) 0.0338(5) Uani 1 1 d . . . . . H13A H 0.164897 0.040005 0.433914 0.051 Uiso 1 1 calc R U . . . H13B H 0.160987 0.073581 0.566029 0.051 Uiso 1 1 calc R U . . . H13C H 0.348286 0.073443 0.519047 0.051 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 0.0388(8) 0.0317(7) 0.0246(7) 0.0029(6) 0.0005(6) -0.0011(6) N1 0.0228(7) 0.0310(8) 0.0203(7) 0.0000(6) 0.0037(6) -0.0005(6) C1 0.0216(8) 0.0290(10) 0.0196(8) -0.0014(7) 0.0057(6) 0.0004(7) C2 0.0211(8) 0.0278(9) 0.0204(8) 0.0010(7) 0.0054(6) 0.0004(7) C3 0.0250(9) 0.0315(10) 0.0221(9) -0.0019(7) 0.0034(7) -0.0021(7) C4 0.0291(9) 0.0290(10) 0.0290(9) -0.0002(8) 0.0038(7) -0.0031(8) C5 0.0322(10) 0.0327(11) 0.0253(9) 0.0044(8) 0.0024(8) 0.0035(8) C6 0.0263(9) 0.0352(10) 0.0213(8) 0.0005(8) 0.0022(7) 0.0034(8) C7 0.0184(8) 0.0296(9) 0.0168(8) -0.0002(7) 0.0027(6) 0.0023(7) C8 0.0193(8) 0.0319(10) 0.0206(8) -0.0011(7) 0.0047(6) 0.0022(7) C9 0.0294(9) 0.0314(10) 0.0201(8) -0.0005(7) 0.0008(7) -0.0010(8) C10 0.0284(9) 0.0358(11) 0.0218(9) -0.0005(8) 0.0005(7) 0.0019(8) C11 0.0233(9) 0.0320(10) 0.0216(9) 0.0001(7) 0.0057(7) 0.0010(7) C12 0.0275(9) 0.0311(10) 0.0230(9) -0.0022(7) 0.0049(7) -0.0030(8) C13 0.0441(11) 0.0298(10) 0.0287(10) -0.0022(8) 0.0094(8) -0.0074(9) 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 N1 C3 130.06(15) . . ? C2 N1 C7 109.24(14) . . ? C3 N1 C7 120.69(15) . . ? C2 C1 C8 108.36(16) . . ? C2 C1 C11 123.02(16) . . ? C8 C1 C11 128.61(16) . . ? N1 C2 C1 107.37(15) . . ? N1 C2 C9 121.52(15) . . ? C1 C2 C9 131.12(16) . . ? C4 C3 N1 119.91(16) . . ? C3 C4 C5 120.56(18) . . ? C6 C5 C4 119.83(17) . . ? C5 C6 C7 120.72(17) . . ? C8 C7 C6 133.38(16) . . ? C8 C7 N1 108.33(15) . . ? C6 C7 N1 118.28(16) . . ? C7 C8 C1 106.69(15) . . ? C7 C8 C10 122.50(16) . . ? C1 C8 C10 130.79(17) . . ? O1 C11 C1 121.23(17) . . ? O1 C11 C12 119.48(17) . . ? C1 C11 C12 119.29(15) . . ? C11 C12 C13 113.18(16) . . ? 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 C11 1.229(2) . ? N1 C2 1.365(2) . ? N1 C3 1.387(2) . ? N1 C7 1.414(2) . ? C1 C2 1.405(2) . ? C1 C8 1.428(2) . ? C1 C11 1.470(3) . ? C2 C9 1.491(2) . ? C3 C4 1.355(3) . ? C4 C5 1.429(3) . ? C5 C6 1.354(3) . ? C6 C7 1.411(3) . ? C7 C8 1.377(3) . ? C8 C10 1.498(2) . ? C11 C12 1.513(3) . ? C12 C13 1.519(3) . ?