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_7130464
_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          471.6(5)
_chemical_name_systematic        'Compound 3da'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 95.1050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.54220(10)
_cell_length_b                   12.89340(10)
_cell_length_c                   30.3311(4)
_cell_measurement_reflns_used    19259
_cell_measurement_temperature    302.48(10)
_cell_measurement_theta_max      76.0260
_cell_measurement_theta_min      2.9090
_cell_volume                     4106.40(7)
_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      302.48(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_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     61.00  86.00   0.50    0.05    --  104.25-160.00  58.00   50
  2  \w     64.00  89.00   0.50    0.05    --   46.32-160.00  58.00   50
  3  \w     92.00 174.00   0.50    0.05    --  104.25  45.00  90.00  164
  4  \w     87.00 112.00   0.50    0.05    --   46.32 160.00  89.00   50
  5  \w     91.00 118.00   0.50    0.05    --  104.25 117.00 -62.00   54
  6  \w     27.00  52.00   0.50    0.05    --   46.32-117.00-149.00   50
  7  \w     33.00  88.00   0.50    0.05    --  104.25-125.00 -90.00  110
  8  \w     75.00 100.00   0.50    0.05    --  104.25 -94.00-120.00   50
  9  \w     32.00 108.00   0.50    0.05    --  104.25-117.00-149.00  152
 10  \w     34.00 108.00   0.50    0.05    --  104.25 -77.00-150.00  148
 11  \w     45.00  71.00   0.50    0.05    --  104.25 -61.00 -90.00   52
 12  \w     43.00  69.00   0.50    0.05    --  104.25 -61.00-120.00   52
 13  \w     36.00  73.00   0.50    0.05    --  104.25 -61.00-150.00   74
 14  \w    -28.00  29.00   0.50    0.05    --   46.32 -19.00 -90.00  114
 15  \w   -132.00 -82.00   0.50    0.05    -- -102.00 160.00  89.00  100
 16  \w    -98.00 -73.00   0.50    0.05    --  -46.32 160.00  89.00   50
 17  \w    -89.00 -14.00   0.50    0.05    --  -46.32 117.00 -62.00  150
 18  \w    -93.00 -68.00   0.50    0.05    -- -102.00 117.00 -62.00   50
 19  \w    -65.00 -29.00   0.50    0.05    -- -102.00  61.00  60.00   72
 20  \w    -60.00 -29.00   0.50    0.05    -- -102.00  61.00  30.00   62
 21  \w    -55.00 -30.00   0.50    0.05    -- -102.00  61.00-150.00   50
 22  \w    -25.00  29.00   0.50    0.05    --  -46.32  19.00  90.00  108
 23  \w    -62.00 -36.00   0.50    0.05    -- -102.00  61.00 120.00   52
 24  \w    -69.00 -43.00   0.50    0.05    -- -102.00  61.00 150.00   52
 25  \w   -153.00-125.00   0.50    0.05    -- -102.00 -15.00  90.00   56
 26  \w   -175.00 -93.00   0.50    0.05    -- -102.00 -15.00  30.00  164
 27  \w   -113.00 -88.00   0.50    0.05    -- -102.00 -15.00  90.00   50
 28  \w   -119.00 -24.00   0.50    0.05    --  -46.32 -77.00 150.00  190
 29  \w   -109.00 -84.00   0.50    0.05    --  -46.32-160.00  58.00   50
 30  \w   -107.00 -57.00   0.50    0.05    -- -102.00-160.00  58.00  100
 31  \w   -108.00 -74.00   0.50    0.05    --  -46.32-125.00 -30.00   68
 32  \w   -151.00-126.00   0.50    0.05    -- -102.00-117.00-149.00   50
;
_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      -0.1356758000
_diffrn_orient_matrix_UB_12      -0.0154052000
_diffrn_orient_matrix_UB_13      0.0140069000
_diffrn_orient_matrix_UB_21      0.0546170000
_diffrn_orient_matrix_UB_22      -0.0126279000
_diffrn_orient_matrix_UB_23      0.0485281000
_diffrn_orient_matrix_UB_31      -0.0118478000
_diffrn_orient_matrix_UB_32      0.1177958000
_diffrn_orient_matrix_UB_33      0.0070184000
_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  0.0525
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            36576
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.396
_diffrn_reflns_theta_min         2.925
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.051
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78377
_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    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             1576
_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          0.11
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         8265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0678P)^2^+0.5730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6721
_reflns_number_total             8265
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03252j2.cif
_cod_data_source_block           Compound_3da
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '471.15-472.15' was changed
to '471.6(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               7130464
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C4(H4)
1.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C14(H14), C18(H18), C29(H29), C30(H30), C31(H31),
 C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C41(H41), C42(H42),
  C44(H44), C45(H45)
1.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C)
1.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              38682
_shelx_hkl_checksum              12400
_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 2.235
_oxdiff_exptl_absorpt_empirical_full_min 0.459