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_7130466
_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         'C47 H50 N2 O4 S'
_chemical_formula_sum            'C47 H50 N2 O4 S'
_chemical_formula_weight         738.95
_chemical_melting_point          472.6(5)
_chemical_name_systematic        'Compound 3ea'
_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
_atom_sites_solution_primary     dual
_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                105.888(2)
_cell_angle_beta                 96.944(2)
_cell_angle_gamma                114.393(2)
_cell_formula_units_Z            2
_cell_length_a                   12.4470(2)
_cell_length_b                   13.1078(3)
_cell_length_c                   15.0372(2)
_cell_measurement_reflns_used    10961
_cell_measurement_temperature    302.34(10)
_cell_measurement_theta_max      76.1110
_cell_measurement_theta_min      3.9640
_cell_volume                     2070.93(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.34(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_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     34.00 114.00   0.50    0.38    --   46.57  37.00 -47.00  160
  2  \w    132.00 162.00   0.50    0.83    --  104.25  45.00 -30.00   60
  3  \w     96.00 128.00   0.50    0.83    --  104.25  45.00 -30.00   64
  4  \w     92.00 174.00   0.50    0.83    --  104.25  37.00 -47.00  164
  5  \w     91.00 172.00   0.50    0.83    --  104.25  15.00  60.00  162
  6  \w     -8.00  29.00   0.50    0.38    --   46.57 -19.00   0.00   74
  7  \w    -11.00  69.00   0.50    0.38    --   46.57 -77.00 150.00  160
  8  \w      0.00  44.00   0.50    0.38    --   46.57 -37.00 156.00   88
  9  \w     32.00  58.00   0.50    0.83    --  104.25-125.00 150.00   52
 10  \w     38.00  64.00   0.50    0.83    --  104.25-125.00 120.00   52
 11  \w     35.00 107.00   0.50    0.83    --  104.25-107.00 164.46  144
 12  \w     87.00 112.00   0.50    0.83    --  104.25-125.00 120.00   50
 13  \w     45.00  95.00   0.50    0.83    --  104.25 -94.00  30.00  100
 14  \w     32.00  98.00   0.50    0.83    --  104.25-125.00   0.00  132
 15  \w     38.00 108.00   0.50    0.83    --  104.25-125.00 -90.00  140
 16  \w     33.00  82.00   0.50    0.83    --  104.25 -94.00 -90.00   98
 17  \w     38.00  97.00   0.50    0.83    --  104.25 -94.00-180.00  118
 18  \w     36.00  63.00   0.50    0.83    --  104.25 -61.00-180.00   54
 19  \w     35.00  69.00   0.50    0.83    --  104.25 -61.00 -60.00   68
 20  \w     32.00  60.00   0.50    0.83    --  104.25 -61.00 -30.00   56
 21  \w     34.00  60.00   0.50    0.83    --  104.25 -61.00  30.00   52
 22  \w   -125.00 -38.00   0.50    0.83    -- -102.00 143.00  52.63  174
 23  \w    -98.00 -72.00   0.50    0.83    -- -102.00 125.00 150.00   52
 24  \w    -68.00 -29.00   0.50    0.83    -- -102.00 125.00 150.00   78
 25  \w   -121.00 -60.00   0.50    0.83    -- -102.00 138.00 -28.28  122
 26  \w   -122.00 -86.00   0.50    0.83    -- -102.00 139.00 -84.10   72
 27  \w    -94.00 -68.00   0.50    0.83    -- -102.00 125.00-120.00   52
 28  \w   -107.00 -78.00   0.50    0.83    -- -102.00 108.00 -90.30   58
 29  \w    -62.00 -30.00   0.50    0.83    -- -102.00 125.00-120.00   64
 30  \w    -40.00  -8.00   0.50    0.38    --  -46.57  37.00 -47.00   64
 31  \w    -50.00  11.00   0.50    0.38    --  -46.57  57.00 -30.00  122
 32  \w   -103.00 -67.00   0.50    0.83    -- -102.00  77.00 120.00   72
 33  \w    -61.00 -35.00   0.50    0.83    -- -102.00  61.00  90.00   52
 34  \w   -175.00-138.00   0.50    0.83    -- -102.00 -61.00-120.00   74
 35  \w   -175.00 -89.00   0.50    0.83    -- -102.00 -15.00-120.00  172
 36  \w   -129.00-100.00   0.50    0.83    -- -102.00 -61.00-120.00   58
 37  \w   -120.00 -43.00   0.50    0.38    --  -46.57 -37.00 156.00  154
 38  \w   -175.00-107.00   0.50    0.83    -- -102.00 -37.00 156.00  136
 39  \w   -112.00 -86.00   0.50    0.38    --  -46.57-125.00 -90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0202667000
_diffrn_orient_matrix_UB_12      0.1080707000
_diffrn_orient_matrix_UB_13      -0.0306581000
_diffrn_orient_matrix_UB_21      0.1028745000
_diffrn_orient_matrix_UB_22      -0.0110926000
_diffrn_orient_matrix_UB_23      -0.0426487000
_diffrn_orient_matrix_UB_31      -0.0943082000
_diffrn_orient_matrix_UB_32      -0.0854422000
_diffrn_orient_matrix_UB_33      -0.0972576000
_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  0.0484
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26451
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.392
_diffrn_reflns_theta_min         3.171
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.042
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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    1.185
_exptl_crystal_description       needle
_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          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         8323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0659P)^2^+0.2917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1344
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6456
_reflns_number_total             8323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03252j2.cif
_cod_data_source_block           Compound_3ea
_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_original_cell_volume        2070.93(7)
_cod_database_code               7130466
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C15(H15)
1.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C31(H31),
 C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C42(H42), C43(H43),
  C45(H45), C46(H46)
1.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C40(H40A,H40B,H40C), C47(H47A,H47B,H47C)
1.d Idealised tetrahedral OH refined as rotating group:
 O007(H007)
;
_shelx_res_checksum              66081
_shelx_hkl_checksum              55733
_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 2.624
_oxdiff_exptl_absorpt_empirical_full_min 0.257