TfOH-promoted synthesis of indoles and benzofurans involving cyclative transposition of vinyl ketone
Mandal, Mou; Balamurugan, Rengarajan; Chemical Communications  (2022) –; doi:10.1039/D2CC03730K

data_7130535
_publ_section_title
;
 TfOH-promoted synthesis of indoles and benzofurans involving cyclative
 transposition of vinyl ketone
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03730K
_journal_year                    2022
_chemical_formula_moiety         'C25 H21 N O3'
_chemical_formula_sum            'C25 H21 N O3'
_chemical_formula_weight         383.43
_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     dual
_audit_creation_date             2022-02-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-04-14 deposited with the CCDC.	2022-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                111.413(2)
_cell_angle_beta                 91.0600(10)
_cell_angle_gamma                102.4440(10)
_cell_formula_units_Z            4
_cell_length_a                   11.0647(2)
_cell_length_b                   12.8133(2)
_cell_length_c                   15.8157(3)
_cell_measurement_reflns_used    14553
_cell_measurement_temperature    297.8(8)
_cell_measurement_theta_max      25.2080
_cell_measurement_theta_min      2.2230
_cell_volume                     2026.78(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.8(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -56.00  11.00   0.50    5.00    --   16.22 -77.00   0.00  134
  2  \w    -30.00  19.00   0.50    5.00    --  -14.97 -94.00 -30.00   98
  3  \w     10.00  67.00   0.50    5.00    --   16.22-125.00 -30.00  114
  4  \w     12.00  46.00   0.50    5.00    --   16.22-120.00 -82.00   68
  5  \w    -36.00  13.00   0.50    5.00    --  -14.97 -94.00 -60.00   98
  6  \w     16.00  95.00   0.50    5.00    --   16.22  15.00-120.00  158
  7  \w     12.00  63.00   0.50    5.00    --   16.22  45.00-120.00  102
  8  \w     -3.00  23.00   0.50    5.00    --  -14.97  77.00 -90.00   52
  9  \w    -31.00  -5.00   0.50    5.00    --   16.22  15.00-120.00   52
 10  \w    -41.00  56.00   0.50    5.00    --  -14.97  30.00-120.00  194
 11  \w    -64.00 -12.00   0.50    5.00    --  -14.97 120.00   1.00  104
 12  \w    -51.00  43.00   0.50    5.00    --   16.22 -61.00  60.00  188
 13  \w     53.00  79.00   0.50    5.00    --   16.22-154.00 120.00   52
 14  \w    -29.00   8.00   0.50    5.00    --  -14.97 -94.00 120.00   74
 15  \w    -80.00   0.00   0.50    5.00    --  -14.97 -61.00  90.00  160
 16  \w    -32.00   8.00   0.50    5.00    --  -14.97  30.00  60.00   80
 17  \w     26.00  59.00   0.50    5.00    --  -14.97  30.00  60.00   66
 18  \w    -40.00 -13.00   0.50    5.00    --   16.22 130.00  25.97   54
 19  \w    -65.00 -29.00   0.50    5.00    --  -14.97 125.00 120.00   72
 20  \w    -68.00 -34.00   0.50    5.00    --  -14.97 125.00 150.00   68
 21  \w    -81.00 -56.00   0.50    5.00    --  -14.97 154.00 159.00   50
 22  \w    -79.00 -14.00   0.50    5.00    --  -14.97 -45.00  90.00  130
 23  \w    -63.00   3.00   0.50    5.00    --  -14.97 -61.00   0.00  132
 24  \w    -81.00  -8.00   0.50    5.00    --  -14.97 -45.00-120.00  146
 25  \w    -84.00  -7.00   0.50    5.00    --  -14.97 -30.00-120.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0244653000
_diffrn_orient_matrix_UB_12      0.0378466000
_diffrn_orient_matrix_UB_13      0.0367685000
_diffrn_orient_matrix_UB_21      -0.0295550000
_diffrn_orient_matrix_UB_22      0.0175201000
_diffrn_orient_matrix_UB_23      -0.0309618000
_diffrn_orient_matrix_UB_31      -0.0537334000
_diffrn_orient_matrix_UB_32      -0.0448330000
_diffrn_orient_matrix_UB_33      -0.0060748000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32547
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.896
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         7171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0626P)^2^+0.1543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5150
_reflns_number_total             7171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03730k4.cif
_cod_data_source_block           rb32
_cod_database_code               7130535
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C9(H9), C34(H34), C16(H16), C5(H5), C8(H8), C31(H31), C1(H1A),
  C41(H41), C33(H33), C15(H15), C3(H3), C27(H27), C13(H13), C44(H44), C14(H14),
 C48(H48), C29(H29), C40(H40), C38(H38), C39(H39), C45(H45), C23(H23), C19(H19),
  C46(H46), C47(H47), C21(H21), C20(H20), C22(H22)
2.b Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              89642
_shelx_hkl_checksum              82905
_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 1.659
_oxdiff_exptl_absorpt_empirical_full_min 0.698