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_7127840
_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         'C25 H17 N O2'
_chemical_formula_sum            'C25 H17 N O2'
_chemical_formula_weight         363.39
_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             2020-10-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-10-29 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                98.888(5)
_cell_angle_beta                 91.797(6)
_cell_angle_gamma                103.272(6)
_cell_formula_units_Z            2
_cell_length_a                   6.7666(6)
_cell_length_b                   8.5442(5)
_cell_length_c                   16.8887(12)
_cell_measurement_reflns_used    2401
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2940
_cell_measurement_theta_min      5.2860
_cell_volume                     936.66(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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.960
_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     75.00 101.00   1.00    1.00    --   36.08 178.00 -30.00   26
  2  \w      3.00  71.00   1.00    1.00    --   36.08 -99.00-180.00   68
  3  \w    -19.00  21.00   1.00    1.00    --   36.08 -57.00-120.00   40
  4  \w     10.00  93.00   1.00    1.00    --   36.08  77.00 -60.00   83
  5  \w     19.00 102.00   1.00    1.00    --   36.08  38.00  60.00   83
  6  \w     48.00  74.00   1.00    1.00    --   36.08 -99.00 -30.00   26
  7  \w      9.00 100.00   1.00    1.00    --   36.08  77.00  90.00   91
  8  \w     50.00  76.00   1.00    1.00    --   36.08  57.00-150.00   26
  9  \w     77.00 104.00   1.00    1.00    --   36.08  77.00 120.00   27
 10  \w     40.00 146.00   1.00    1.00    --  108.00 -15.00-120.00  106
 11  \w     92.00 118.00   1.00    1.00    --  108.00 -61.00   0.00   26
 12  \w     51.00  84.00   1.00    1.00    --  108.00 -61.00   0.00   33
 13  \w     87.00 163.00   1.00    1.00    --  108.00  30.00 -90.00   76
 14  \w    135.00 175.00   1.00    1.00    --  108.00  61.00  60.00   40
 15  \w     43.00 119.00   1.00    1.00    --  108.00 -30.00  60.00   76
 16  \w     90.00 118.00   1.00    1.00    --  108.00  61.00  60.00   28
 17  \w     66.00 109.00   1.00    1.00    --  108.00 -95.00 -60.00   43
 18  \w     95.00 126.00   1.00    1.00    --  108.00 -61.00 120.00   31
 19  \w     73.00  99.00   1.00    1.00    --  108.00 -95.00-120.00   26
 20  \w     40.00 110.00   1.00    1.00    --  108.00 -95.00 150.00   70
 21  \w     41.00  75.00   1.00    1.00    --  108.00 -95.00 -90.00   34
 22  \w     73.00 146.00   1.00    1.00    --  108.00 178.00-180.00   73
 23  \w     59.00 125.00   1.00    1.00    --  108.00 -45.00  90.00   66
 24  \w     43.00 123.00   1.00    1.00    --  108.00 -61.00 -90.00   80
 25  \w     88.00 113.00   1.00    1.00    --  108.00-111.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1407102000
_diffrn_orient_matrix_UB_12      0.0980216000
_diffrn_orient_matrix_UB_13      -0.0542562000
_diffrn_orient_matrix_UB_21      0.1875748000
_diffrn_orient_matrix_UB_22      -0.0183004000
_diffrn_orient_matrix_UB_23      0.0485546000
_diffrn_orient_matrix_UB_31      -0.0006128000
_diffrn_orient_matrix_UB_32      -0.1592184000
_diffrn_orient_matrix_UB_33      -0.0571346000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5793
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.190
_diffrn_reflns_theta_min         5.315
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58072
_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            yellow
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.472(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0554
_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^)+(0.1038P)^2^+0.2170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3087
_reflns_number_total             3550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc08039j2.cif
_cod_data_source_block           20200106-1
_cod_depositor_comments
'Adding full bibliography for 7127839--7127840.cif.'
_cod_database_code               7127840
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.28
_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:
 C00C(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S)
2.b Idealised Me refined as rotating group:
 C00B(H00A,H00B,H00C)
;
_shelx_res_checksum              18941
_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 2.714
_oxdiff_exptl_absorpt_empirical_full_min 0.739