A visible-light-induced intermolecular [3 + 2] alkenylation‒cyclization strategy: metal-free construction of pyrrolo[2,1,5-cd]indolizine rings
Liang, Yaofeng; Teng, Lili; Wang, Yajun; He, Qiuxing; Cao, Hua; Green Chemistry 21 (2019) 4025–; doi:10.1039/C9GC01766F

data_7233001
_publ_section_title
;
 A visible-light-induced intermolecular [3 + 2] alkenylation--cyclization
 strategy: metal-free construction of pyrrolo[2,1,5-cd]indolizine rings
;
_journal_issue                   15
_journal_name_full               'Green Chemistry'
_journal_page_first              4025
_journal_paper_doi               10.1039/C9GC01766F
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C19 H15 N O2'
_chemical_formula_sum            'C19 H15 N O2'
_chemical_formula_weight         289.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-13 deposited with the CCDC.    2019-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.305(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.9198(2)
_cell_length_b                   25.3323(11)
_cell_length_c                   7.1542(3)
_cell_measurement_reflns_used    2410
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2820
_cell_measurement_theta_min      6.4760
_cell_volume                     704.63(6)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_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     17.00  82.00   1.00    1.00    --   40.73  38.00-120.00   65
  2  \w     95.00 135.00   1.00    1.00    --  106.95 125.00 -30.00   40
  3  \w    135.00 173.00   1.00    1.00    --  106.95  45.00  30.00   38
  4  \w     99.00 160.00   1.00    1.00    --  106.95 125.00-150.00   61
  5  \w     84.00 132.00   1.00    1.00    --  106.95 -30.00-150.00   48
  6  \w     51.00  92.00   1.00    1.00    --  106.95 -95.00 -30.00   41
  7  \w     76.00 112.00   1.00    1.00    --  106.95 -45.00  30.00   36
  8  \w     43.00 115.00   1.00    1.00    --  106.95 -30.00 -60.00   72
  9  \w     36.00  82.00   1.00    1.00    --  106.95 -30.00-150.00   46
 10  \w      4.00  36.00   1.00    1.00    --   40.73 -99.00 -30.00   32
 11  \w    -65.00 -13.00   1.00    1.00    --  -40.73 -57.00  90.00   52
 12  \w   -110.00 -70.00   1.00    1.00    --  -40.73 -57.00  90.00   40
 13  \w    -82.00  29.00   1.00    1.00    --  -41.23  19.00-180.00  111
 14  \w     76.00 104.00   1.00    1.00    --   41.23  38.00 150.00   28
 15  \w     33.00  59.00   1.00    1.00    --   41.23  38.00 150.00   26
 16  \w     21.00  47.00   1.00    1.00    --   41.23 -99.00-120.00   26
 17  \w     74.00 133.00   1.00    1.00    --  106.95  77.00  90.00   59
 18  \w     81.00 108.00   1.00    1.00    --  106.95  77.00  60.00   27
;
_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      0.2770233000
_diffrn_orient_matrix_UB_12      0.0040857000
_diffrn_orient_matrix_UB_13      0.1725799000
_diffrn_orient_matrix_UB_21      0.2115052000
_diffrn_orient_matrix_UB_22      0.0372737000
_diffrn_orient_matrix_UB_23      -0.1106706000
_diffrn_orient_matrix_UB_31      -0.1884228000
_diffrn_orient_matrix_UB_32      0.0478868000
_diffrn_orient_matrix_UB_33      0.0713890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3274
_diffrn_reflns_point_group_measured_fraction_full 0.820
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.339
_diffrn_reflns_theta_min         6.237
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41660
_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            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2230
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0543P)^2^+0.2345P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.583
_reflns_Friedel_fraction_full    0.636
_reflns_Friedel_fraction_max     0.596
_reflns_number_gt                2173
_reflns_number_total             2230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc01766f2.cif
_cod_data_source_block           157
_cod_depositor_comments          'Adding full bibliography for 7233001.cif.'
_cod_original_cell_volume        704.62(6)
_cod_database_code               7233001
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.913
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C2(H2), C16(H16), C9(H9), C6(H6), C5(H5), C7(H7), C15(H15)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
;
_olex2_date_sample_data_collection 2019-03-06
_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 3.457
_oxdiff_exptl_absorpt_empirical_full_min 0.687