Borane-catalysed C2-selective indole reductive functionalisation.
Nicholson, Kieran; McOnie, Sarah L.; Langer, Thomas; Nichol, Gary S.; Thomas, Stephen P.; Chemical communications (Cambridge, England) 60 (2024) 10748–10751; doi:10.1039/d4cc03880k

data_7133704
_publ_section_title
;
 Borane-catalysed C2-selective indole reductive functionalisation.
;
_journal_issue                   77
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10748
_journal_page_last               10751
_journal_paper_doi               10.1039/d4cc03880k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C17 H22 N2 O2'
_chemical_formula_sum            'C17 H22 N2 O2'
_chemical_formula_weight         286.36
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-29
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-07-31 deposited with the CCDC.	2024-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.050(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5689(2)
_cell_length_b                   14.0796(4)
_cell_length_c                   12.6116(3)
_cell_measurement_reflns_used    12906
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      29.5230
_cell_measurement_theta_min      4.0740
_cell_volume                     1521.29(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.931
_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     -6.00  57.00   1.00    5.00    --   10.84-111.00  30.00   63
  2  \w    -41.00  21.00   1.00    5.00    --   -9.27  77.00-180.00   62
  3  \w    -15.00  31.00   1.00    5.00    --   -9.27 -99.00-120.00   46
  4  \w    -41.00  21.00   1.00    5.00    --   -9.27  77.00-150.00   62
  5  \w    -36.00  61.00   1.00    5.00    --   -9.27  57.00  90.00   97
  6  \w    -15.00  31.00   1.00    5.00    --   -9.27 -99.00 -60.00   46
  7  \w    -12.00  83.00   1.00    5.00    --   10.84  38.00 -90.00   95
  8  \w    -42.00  42.00   1.00    5.00    --   10.84 -77.00 -30.00   84
  9  \w    -15.00  10.00   1.00    5.00    --   -9.27 -99.00  90.00   25
 10  \w    -16.00  81.00   1.00    5.00    --   10.84  57.00  30.00   97
 11  \w    -16.00  81.00   1.00    5.00    --   10.84  57.00 120.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0758446000
_diffrn_orient_matrix_UB_12      -0.0108294000
_diffrn_orient_matrix_UB_13      0.0180880000
_diffrn_orient_matrix_UB_21      0.0223485000
_diffrn_orient_matrix_UB_22      -0.0481063000
_diffrn_orient_matrix_UB_23      0.0072541000
_diffrn_orient_matrix_UB_31      0.0245625000
_diffrn_orient_matrix_UB_32      0.0103196000
_diffrn_orient_matrix_UB_33      0.0527629000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33550
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.697
_diffrn_reflns_theta_min         3.314
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent dark orange'
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of petrol and ethyl acetate  by slow evaporation'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0412P)^2^+0.7509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3412
_reflns_number_total             4012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03880k2.cif
_cod_data_source_block           se21009
_cod_depositor_comments          'Adding full bibliography for 7133704.cif.'
_cod_database_code               7133704
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H22 N2 O2'
_chemical_oxdiff_usercomment     '@ 120 K KN06-174'
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
;
_shelx_res_checksum              83260
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id KN06-174
_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 1.209
_oxdiff_exptl_absorpt_empirical_full_min 0.815