C3 functionalization of indolizines via In(iii)-catalyzed three-component reaction.
Jung, Youngeun; Kim, Ikyon; Organic & biomolecular chemistry 13 (2015) 10986–10994; doi:10.1039/c5ob01657f

data_7154716
_publ_section_title
;
 C3 functionalization of indolizines via In(iii)-catalyzed three-component
 reaction.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10986
_journal_page_last               10994
_journal_paper_doi               10.1039/c5ob01657f
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C27 H26 N2 O3'
_chemical_formula_sum            'C27 H26 N2 O3'
_chemical_formula_weight         426.50
_chemical_name_systematic
'methyl 3-(morpholino(phenyl)methyl)-2-phenylindolizine-1-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-06 deposited with the CCDC.
2015-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                110.392(5)
_cell_angle_beta                 108.076(5)
_cell_angle_gamma                91.105(5)
_cell_formula_units_Z            2
_cell_length_a                   10.2728(12)
_cell_length_b                   10.8678(13)
_cell_length_c                   11.3970(13)
_cell_measurement_reflns_used    4669
_cell_measurement_temperature    301.5
_cell_measurement_theta_max      25.534
_cell_measurement_theta_min      2.378
_cell_volume                     1122.1(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      301.5
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14402
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.081
_diffrn_reflns_theta_min         2.266
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0541 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.8520.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0593P)^2^+0.2177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3020
_reflns_number_total             4421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01657f2.cif
_cod_data_source_block           methyl
_cod_depositor_comments          'Adding full bibliography for 7154716.cif.'
_cod_database_code               7154716
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5(0.061) H6(0.07) H7(0.074) H8(0.067) H13A(0.131) H13B(0.131)
 H13C(0.131) H15(0.077) H16(0.102) H17(0.111) H18(0.099) H19(0.073) H20(0.052)
 H22(0.077) H23(0.094) H24(0.083) H25(0.07) H26(0.059) H28A(0.066) H28B(0.066)
 H29A(0.08) H29B(0.08) H31A(0.096) H31B(0.096) H32A(0.074) H32B(0.074)
 Fixed X: H5(0.6517) H6(0.4981) H7(0.2962) H8(0.2508) H13A(0.2098)
 H13B(0.2395) H13C(0.1304) H15(0.6125) H16(0.71) H17(0.757) H18(0.7118)
 H19(0.6192) H20(0.796) H22(0.8892) H23(1.0256) H24(1.0872) H25(1.0211)
 H26(0.8817) H28A(0.9342) H28B(0.9927) H29A(0.9276) H29B(1.0255) H31A(0.6302)
 H31B(0.6808) H32A(0.5896) H32B(0.6927)
 Fixed Y: H5(0.0207) H6(-0.1638) H7(-0.1485) H8(0.0529) H13A(0.4902)
 H13B(0.6235) H13C(0.5075) H15(0.5211) H16(0.7396) H17(0.8651) H18(0.7724)
 H19(0.5496) H20(0.3895) H22(0.4348) H23(0.3819) H24(0.1723) H25(0.0185)
 H26(0.0694) H28A(0.3552) H28B(0.2471) H29A(0.088) H29B(0.2071) H31A(0.1844)
 H31B(0.0736) H32A(0.2228) H32B(0.341)
 Fixed Z: H5(0.2977) H6(0.1553) H7(-0.0018) H8(-0.0115) H13A(-0.0467)
 H13B(0.0762) H13C(0.0541) H15(0.1495) H16(0.2342) H17(0.4542) H18(0.593)
 H19(0.5109) H20(0.4557) H22(0.3056) H23(0.1738) H24(0.1076) H25(0.1825)
 H26(0.3121) H28A(0.6505) H28B(0.5549) H29A(0.6266) H29B(0.7494) H31A(0.6891)
 H31B(0.589) H32A(0.4923) H32B(0.6125)
;
_shelx_res_checksum              56428
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'