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_7130536
_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         'C26 H21 N O3'
_chemical_formula_sum            'C26 H21 N O3'
_chemical_formula_weight         395.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-31
_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                90
_cell_angle_beta                 116.246(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4449(8)
_cell_length_b                   5.9085(2)
_cell_length_c                   19.6048(8)
_cell_measurement_reflns_used    8517
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.7700
_cell_measurement_theta_min      1.9740
_cell_volume                     2020.19(16)
_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      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_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    -10.00  68.00   0.50    6.00    --   16.22  30.00   0.00  156
  2  \w    -37.00  22.00   0.50    6.00    --  -14.97 -94.00 -30.00  118
  3  \w     36.00  68.00   0.50    6.00    --   16.22-125.00  30.00   64
  4  \w    -37.00  21.00   0.50    6.00    --  -14.97 -94.00  60.00  116
  5  \w    -63.00  98.00   0.50    6.00    --   16.22   9.00 -19.00  322
  6  \w     33.00  86.00   0.50    6.00    --   16.22  45.00-120.00  106
  7  \w     54.00  88.00   0.50    6.00    --   16.22  30.00-150.00   68
  8  \w     -8.00  50.00   0.50    6.00    --   16.22  30.00-150.00  116
  9  \w     -8.00  26.00   0.50    6.00    --   16.22  45.00-120.00   68
 10  \w    -50.00 -11.00   0.50    6.00    --  -14.97 125.00-180.00   78
 11  \w    -45.00 -11.00   0.50    6.00    --  -14.97 125.00-120.00   68
 12  \w    -94.00  67.00   0.50    6.00    --  -14.97   9.00 -19.00  322
 13  \w    -69.00 -43.00   0.50    6.00    --  -14.97 125.00 150.00   52
 14  \w    -86.00 -16.00   0.50    6.00    --  -14.97  -9.00 165.00  140
 15  \w    -65.00  -8.00   0.50    6.00    --   16.22  -9.00 165.00  114
 16  \w    -35.00  19.00   0.50    6.00    --  -14.97 -94.00-180.00  108
;
_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      -0.0379148000
_diffrn_orient_matrix_UB_12      -0.0041394000
_diffrn_orient_matrix_UB_13      -0.0296665000
_diffrn_orient_matrix_UB_21      0.0147321000
_diffrn_orient_matrix_UB_22      -0.0133368000
_diffrn_orient_matrix_UB_23      -0.0270310000
_diffrn_orient_matrix_UB_31      -0.0003239000
_diffrn_orient_matrix_UB_32      -0.1191975000
_diffrn_orient_matrix_UB_33      0.0040500000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24726
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.982
_diffrn_reflns_theta_min         1.975
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39986
_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 orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.1038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1502
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2574
_reflns_number_total             4222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03730k4.cif
_cod_data_source_block           rb38
_cod_original_cell_volume        2020.18(16)
_cod_database_code               7130536
_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   0.983
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C11(H11), C5(H5), C1(H1), C12(H12), C14(H14), C22(H22),
 C19(H19), C20(H20), C23(H23), C13(H13), C4(H4), C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              8244
_shelx_hkl_checksum              55649
_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 3.585
_oxdiff_exptl_absorpt_empirical_full_min 0.392