Iron(III)-catalyzed tandem annulation of indolyl-substituted <i>p</i>-quinone methides with ynamides for the synthesis of cyclopenta[<i>b</i>]indoles.
Yu, Ke-Yin; Ge, Xiao-Min; Fan, Yi-Jun; Liu, Xiao-Tao; Yang, Xue; Yang, Yu-Han; Zhao, Xian-He; An, Xian-Tao; Fan, Chun-An; Chemical communications (Cambridge, England) 58 (2022) 8710–8713; doi:10.1039/d2cc03252j

data_7130463
_publ_section_title
;
 Iron(III)-catalyzed tandem annulation of indolyl-substituted
 <i>p</i>-quinone methides with ynamides for the synthesis of
 cyclopenta[<i>b</i>]indoles.
;
_journal_issue                   62
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8710
_journal_page_last               8713
_journal_paper_doi               10.1039/d2cc03252j
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C46 H47 F N2 O4 S'
_chemical_formula_sum            'C46 H47 F N2 O4 S'
_chemical_formula_weight         742.91
_chemical_melting_point          472.6(5)
_chemical_name_systematic        'Compound 3fa'
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-11-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-15 deposited with the CCDC.	2022-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                95.174(7)
_cell_angle_beta                 99.059(7)
_cell_angle_gamma                113.378(8)
_cell_formula_units_Z            2
_cell_length_a                   12.2295(10)
_cell_length_b                   12.9142(10)
_cell_length_c                   14.2096(12)
_cell_measurement_reflns_used    4921
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9740
_cell_measurement_theta_min      4.5140
_cell_volume                     2005.2(3)
_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 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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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    121.00 178.00   1.50    1.50    --  108.00  12.00 120.00   38
  2  \w     86.00 176.00   1.50    1.50    --  108.00  63.00 150.00   60
  3  \w    112.00 148.00   1.50    1.50    --  108.00 178.00 -60.00   24
  4  \w     59.00  86.00   1.50    1.50    --   54.00  77.00   0.00   18
  5  \w     34.00  59.50   1.50    1.50    --   54.00  77.00  30.00   17
  6  \w     31.00 121.00   1.50    1.50    --   54.00  77.00  60.00   60
  7  \w     58.00  89.50   1.50    1.50    --  108.00 178.00 -60.00   21
  8  \w     31.00 124.00   1.50    1.50    --   54.00  77.00 -60.00   62
  9  \w     74.00 104.00   1.50    1.50    --  108.00  25.00-120.00   20
 10  \w    118.00 178.00   1.50    1.50    --  108.00  25.00-120.00   40
 11  \w     56.00 114.50   1.50    1.50    --  108.00 -63.00-120.00   39
 12  \w     54.00 126.00   1.50    1.50    --  108.00 -38.00   0.00   48
 13  \w     52.00 115.00   1.50    1.50    --  108.00-111.00 -90.00   42
 14  \w     57.00 132.00   1.50    1.50    --  108.00 -77.00  30.00   50
 15  \w     85.00 112.00   1.50    1.50    --  108.00-111.00 150.00   18
 16  \w     50.00 129.50   1.50    1.50    --  108.00 -50.00 120.00   53
 17  \w     44.00  75.50   1.50    1.50    --  108.00  12.00 120.00   21
 18  \w     30.00  55.50   1.50    1.50    --   54.00  77.00   0.00   17
 19  \w     27.00  60.00   1.50    1.50    --    0.00  38.00 120.00   22
 20  \w     42.00 111.00   1.50    1.50    --  108.00-111.00  30.00   46
 21  \w     38.00  68.00   1.50    1.50    --  108.00 -50.00   0.00   20
 22  \w     24.00 111.00   1.50    1.50    --   54.00-125.00 -90.00   58
 23  \w     39.00 133.50   1.50    1.50    --  108.00 -38.00-150.00   63
 24  \w     39.00 112.50   1.50    1.50    --   54.00  57.00-150.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0886826000
_diffrn_orient_matrix_UB_12      0.0072887000
_diffrn_orient_matrix_UB_13      0.0929075000
_diffrn_orient_matrix_UB_21      0.1065364000
_diffrn_orient_matrix_UB_22      0.0873089000
_diffrn_orient_matrix_UB_23      -0.0357774000
_diffrn_orient_matrix_UB_31      -0.0224151000
_diffrn_orient_matrix_UB_32      0.0985340000
_diffrn_orient_matrix_UB_33      0.0499437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12108
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         4.524
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19321
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and methanol'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         6924
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0685P)^2^+0.4647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1348
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5780
_reflns_number_total             6924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03252j2.cif
_cod_data_source_block           Compound_3fa
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '472.15-473.15' was changed
to '472.6(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130463
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.850
_reflns_odcompleteness_completeness 97.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Restrained distances
 H43A-H12
 2 with sigma of 0.01
 H12-H53C
 2 with sigma of 0.01
2.a Ternary CH refined with riding coordinates:
 C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C15(H15), C20(H20), C21(H21), C24(H24), C25(H25),
 C26(H26), C27(H27), C29(H29), C31(H31), C34(H34), C35(H35), C37(H37), C41(H41),
  C50(H50), C1AA(H1AA), C0AA(H0AA)
2.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C43(H43A,H43B,
 H43C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C52(H52A,H52B,H52C), C53(H53A,
 H53B,H53C), C60(H60A,H60B,H60C)
;
_shelx_res_checksum              9562
_shelx_hkl_checksum              61651
_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 4.765
_oxdiff_exptl_absorpt_empirical_full_min 0.711