Iridium-catalyzed C3-selective asymmetric allylation of 7-azaindoles with secondary allylic alcohols.
Sawano, Takahiro; Matsui, Takeshi; Koga, Marina; Ishikawa, Eri; Takeuchi, Ryo; Chemical communications (Cambridge, England) 57 (2021) 9684–9687; doi:10.1039/d1cc03968g

data_7128921
_publ_section_title
;
 Iridium-catalyzed C3-selective asymmetric allylation of 7-azaindoles with
 secondary allylic alcohols.
;
_journal_issue                   76
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9684
_journal_page_last               9687
_journal_paper_doi               10.1039/d1cc03968g
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 Br N2'
_chemical_formula_sum            'C17 H15 Br N2'
_chemical_formula_weight         327.22
_chemical_melting_point          405
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-04-26 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.34(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.928(5)
_cell_length_b                   17.983(10)
_cell_length_c                   9.771(6)
_cell_measurement_reflns_used    8141
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      3.00
_cell_volume                     1566.1(16)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.1017
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15324
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.447
_diffrn_reflns_theta_min         3.005
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.624
_exptl_absorpt_correction_T_max  0.269
_exptl_absorpt_correction_T_min  0.188
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664.00
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.37
_refine_ls_abs_structure_details
;
 Flack x determined using 1347 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(11)
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7098
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0611P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                4128
_reflns_number_total             7098
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d1cc03968g2.cif
_cod_data_source_block           SawaMari120C
_cod_depositor_comments
'Adding full bibliography for 7128920--7128921.cif.'
_cod_database_code               7128921
_shelx_res_checksum              83767