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_7130467
_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          482.6(5)
_chemical_name_systematic        'Compound 3ca'
_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     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                90
_cell_angle_beta                 93.7820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.55370(10)
_cell_length_b                   12.93580(10)
_cell_length_c                   30.0737(3)
_cell_measurement_reflns_used    23371
_cell_measurement_temperature    291.7(2)
_cell_measurement_theta_max      76.3230
_cell_measurement_theta_min      2.9380
_cell_volume                     4096.74(6)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.7(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.957
_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     75.00 120.00   0.50    0.07    --  104.25 134.00 140.00   90
  2  \w    125.00 150.00   0.50    0.07    --  104.25 135.00 -40.00   50
  3  \w     93.00 176.00   0.50    0.07    --  104.25  45.00  60.00  166
  4  \w     29.00  99.00   0.50    0.05    --   46.32-135.00-106.00  140
  5  \w     33.00 120.00   0.50    0.07    --  104.25-135.00-106.00  174
  6  \w     34.00 110.00   0.50    0.07    --  104.25-125.00  30.00  152
  7  \w     51.00  76.00   0.50    0.07    --  104.25-134.00  73.00   50
  8  \w     51.00  76.00   0.50    0.07    --  104.25-125.00 120.00   50
  9  \w     80.00 110.00   0.50    0.07    --  104.25-125.00 120.00   60
 10  \w     51.00  76.00   0.50    0.05    --   46.32-134.00  73.00   50
 11  \w     33.00  92.00   0.50    0.07    --  104.25 -94.00-120.00  118
 12  \w     46.00  72.00   0.50    0.07    --  104.25 -61.00 -90.00   52
 13  \w     35.00  66.00   0.50    0.07    --  104.25 -61.00-120.00   62
 14  \w    -10.00  22.00   0.50    0.05    --   46.32 -19.00 120.00   64
 15  \w   -108.00 -29.00   0.50    0.07    -- -102.00 109.00  75.72  158
 16  \w    -74.00 -30.00   0.50    0.07    -- -102.00 134.00 140.00   88
 17  \w    -98.00 -73.00   0.50    0.07    -- -102.00 135.00 -40.00   50
 18  \w    -24.00   2.00   0.50    0.05    --  -46.32  19.00-180.00   52
 19  \w    -21.00  29.00   0.50    0.05    --  -46.32  19.00 -60.00  100
 20  \w      0.00  28.00   0.50    0.05    --  -46.32  19.00 -30.00   56
 21  \w    -68.00 -42.00   0.50    0.07    -- -102.00  61.00   0.00   52
 22  \w   -175.00-101.00   0.50    0.07    -- -102.00 -15.00-120.00  148
 23  \w   -158.00-132.00   0.50    0.07    -- -102.00-125.00-150.00   52
 24  \w   -113.00 -75.00   0.50    0.07    -- -102.00-125.00-150.00   76
 25  \w   -119.00 -68.00   0.50    0.05    --  -46.32-135.00-106.00  102
 26  \w    -98.00 -70.00   0.50    0.05    --  -46.32-134.00  73.00   56
 27  \w   -117.00 -75.00   0.50    0.05    --  -46.32-125.00 120.00   84
;
_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      -0.0554474000
_diffrn_orient_matrix_UB_12      0.0339842000
_diffrn_orient_matrix_UB_13      0.0438043000
_diffrn_orient_matrix_UB_21      -0.0161406000
_diffrn_orient_matrix_UB_22      -0.1141522000
_diffrn_orient_matrix_UB_23      0.0130880000
_diffrn_orient_matrix_UB_31      0.1344194000
_diffrn_orient_matrix_UB_32      0.0002764000
_diffrn_orient_matrix_UB_33      0.0233418000
_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  0.0277
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            32293
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.437
_diffrn_reflns_theta_min         2.945
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.054
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49919
_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    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             1576
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and methanol'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.00214(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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     499
_refine_ls_number_reflns         8231
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+1.0472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7319
_reflns_number_total             8231
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03252j2.cif
_cod_data_source_block           Compound_3ca
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '482.15-483.15' was changed
to '482.6(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               7130467
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Restrained distances
 H21C-H22B
 3.1 with sigma of 0.01
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C15(H15), C19(H19), C29(H29), C30(H30), C31(H31),
 C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C42(H42), C43(H43),
  C45(H45), C46(H46)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C40(H40A,H40B,H40C), C47(H47A,H47B,H47C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.759
_oxdiff_exptl_absorpt_empirical_full_min 0.727