Synthesis of Pyrrolo[2,1,5-cd]indolizine Rings via Visible-Light-Induced Intermolecular [3+2] Cycloaddition of Indolizines and Alkynes.
Zhang, Yu; Yu, Yue; Liang, Bing-Bing; Pei, Yong-Yan; Liu, Xiang; Yao, Hua-Gang; Cao, Hua; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01253

data_4038641
_publ_section_title
;
 Synthesis of Pyrrolo[2,1,5-cd]indolizine Rings via Visible-Light-Induced
 Intermolecular [3+2] Cycloaddition of Indolizines and Alkynes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01253
_journal_year                    2020
_chemical_formula_moiety         'C24 H14 F3 N O'
_chemical_formula_sum            'C24 H14 F3 N O'
_chemical_formula_weight         389.36
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.72(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.308(7)
_cell_length_b                   10.085(2)
_cell_length_c                   8.125(2)
_cell_measurement_reflns_used    877
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      23.1250
_cell_measurement_theta_min      2.7710
_cell_volume                     1737.3(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -68.00  28.00   1.00   10.00    --   11.74 -19.00  90.00   96
  2  \w    -29.00  66.00   1.00   10.00    --   11.74  19.00 -60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0321409000
_diffrn_orient_matrix_UB_12      -0.0143816000
_diffrn_orient_matrix_UB_13      0.0073642000
_diffrn_orient_matrix_UB_21      -0.0092674000
_diffrn_orient_matrix_UB_22      0.0480773000
_diffrn_orient_matrix_UB_23      -0.0614736000
_diffrn_orient_matrix_UB_31      0.0006057000
_diffrn_orient_matrix_UB_32      -0.0493513000
_diffrn_orient_matrix_UB_33      -0.0620800000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.1164
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7224
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.236
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0883
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1596P)^2^+16.0455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1954
_refine_ls_wR_factor_ref         0.2242
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1949
_reflns_number_total             3062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01253_si_001.cif
_cod_data_source_block           exp_1892
_cod_original_cell_volume        1737.4(8)
_cod_database_code               4038641
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C2, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C2 \\sim C3: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C17(H17), C13(H13), C16(H16), C00D(H00D), C21(H21), C22(H22),
 C11(H11), C14(H14), C19(H19), C4(H4), C23(H23), C3(H3), C2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.681
_oxdiff_exptl_absorpt_empirical_full_min 0.491