Organocatalytic C3-functionalization of indolizines: synthesis of biologically important indolizine derivatives.
Zhang, Yi-Zhu; Sheng, Feng-Tao; Zhu, Zuoquan; Li, Zhi-Ming; Zhang, Shu; Tan, Wei; Shi, Feng; Organic & biomolecular chemistry 18 (2020) 5688–5696; doi:10.1039/d0ob01230k

data_7157582
_publ_section_title
;
 Organocatalytic C3-functionalization of indolizines: synthesis of
 biologically important indolizine derivatives.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5688
_journal_page_last               5696
_journal_paper_doi               10.1039/d0ob01230k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C29 H20 F3 N O2'
_chemical_formula_sum            'C29 H20 F3 N O2'
_chemical_formula_weight         471.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-06-01
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-09 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                88.838(5)
_cell_angle_beta                 68.455(5)
_cell_angle_gamma                79.684(6)
_cell_formula_units_Z            2
_cell_length_a                   10.333(4)
_cell_length_b                   10.460(4)
_cell_length_c                   11.583(5)
_cell_measurement_reflns_used    1508
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.369
_cell_measurement_theta_min      2.646
_cell_volume                     1144.2(8)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6041
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_min         2.672
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0592 before and 0.0299 after correction.
The Ratio of minimum to maximum transmission is 0.9142.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0797P)^2^+0.2071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1617
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2817
_reflns_number_total             4240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01230k2.cif
_cod_data_source_block           sf20190530a_0m
_cod_depositor_comments          'Adding full bibliography for 7157582.cif.'
_cod_database_code               7157582
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H17(0.5) H23(0.5) O2(0.5) H2(0.5) O2A(0.5) H2A(0.5)
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2A(H2A)
;
_shelx_res_checksum              96232
_shelx_hkl_checksum              82901
_olex2_submission_special_instructions 'No special instructions were received'