Iron-catalyzed intramolecular acyl nitrene/alkyne metalation for the synthesis of pyrrolo[2,1-a]isoindol-5-ones.
Lai, Xiaojing; Liu, Jin-Biao; Wang, Yu-Chao; Qiu, Guanyinsheng; Chemical communications (Cambridge, England) 57 (2021) 2077–2080; doi:10.1039/d0cc08039j

data_7127839
_publ_section_title
;
 Iron-catalyzed intramolecular acyl nitrene/alkyne metalation for the
 synthesis of pyrrolo[2,1-a]isoindol-5-ones.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2077
_journal_page_last               2080
_journal_paper_doi               10.1039/d0cc08039j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C20 H15 N O2'
_chemical_formula_sum            'C20 H15 N O2'
_chemical_formula_weight         301.33
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-29 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.299(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0940(3)
_cell_length_b                   17.4703(8)
_cell_length_c                   11.2484(5)
_cell_measurement_reflns_used    2163
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.1530
_cell_measurement_theta_min      4.7200
_cell_volume                     1569.67(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_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     21.00 103.00   1.00    1.90    --   36.58  57.00 150.00   82
  2  \w    -35.00  66.00   1.00    1.90    --   36.58 -19.00 -30.00  101
  3  \w     11.00  53.00   1.00    1.90    --   36.58  77.00  60.00   42
  4  \w     -1.00  52.00   1.00    1.90    --   36.58 -38.00-120.00   53
  5  \w     51.00  76.00   1.00    1.90    --   36.58 -99.00-120.00   25
  6  \w     82.00 107.00   1.00    1.90    --   36.58 178.00  90.00   25
  7  \w     48.00  95.00   1.00    7.60    --  108.00 -95.00   0.00   47
  8  \w     40.00  66.00   1.00    7.60    --  108.00 -77.00 -30.00   26
  9  \w     95.00 166.00   1.00    7.60    --  108.00  45.00  60.00   71
 10  \w    140.00 169.00   1.00    7.60    --  108.00  61.00 120.00   29
 11  \w     81.00 167.00   1.00    7.60    --  108.00  77.00  90.00   86
 12  \w     41.00  80.00   1.00    7.60    --  108.00 -95.00  90.00   39
 13  \w    103.00 178.00   1.00    7.60    --  108.00 111.00   0.00   75
 14  \w     86.00 135.00   1.00    7.60    --  108.00 -77.00 -30.00   49
 15  \w     37.00  87.00   1.00    7.60    --  108.00 -15.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0033535000
_diffrn_orient_matrix_UB_12      0.0705582000
_diffrn_orient_matrix_UB_13      -0.0818738000
_diffrn_orient_matrix_UB_21      0.0707632000
_diffrn_orient_matrix_UB_22      0.0488081000
_diffrn_orient_matrix_UB_23      0.1105558000
_diffrn_orient_matrix_UB_31      0.1793503000
_diffrn_orient_matrix_UB_32      -0.0205908000
_diffrn_orient_matrix_UB_33      -0.0179369000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5992
_diffrn_reflns_point_group_measured_fraction_full 0.767
_diffrn_reflns_point_group_measured_fraction_max 0.734
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.595
_diffrn_reflns_theta_min         3.982
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1175 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         4565
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0650P)^2^+0.0400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.458
_reflns_Friedel_fraction_full    0.517
_reflns_Friedel_fraction_max     0.478
_reflns_number_gt                4118
_reflns_number_total             4565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc08039j2.cif
_cod_data_source_block           20200102-1
_cod_depositor_comments
'Adding full bibliography for 7127839--7127840.cif.'
_cod_database_code               7127839
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.868
_reflns_odcompleteness_completeness 99.86
_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:
 C25(H25), C21(H21), C17(H17), C5(H5), C36(H36), C39(H39), C22(H22), C20(H20),
 C24(H24), C18(H18), C23(H23), C38(H38), C19(H19), C1(H1), C37(H37), C2(H2),
 C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C32(H32A,H32B,H32C), C015(H01A,H01B,H01C), C12(H12A,H12B,
 H12C)
;
_shelx_res_checksum              22512
_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 1.308
_oxdiff_exptl_absorpt_empirical_full_min 0.680