Cooperative Catalysis-Enabled Asymmetric α-Arylation of Aldehydes Using 2-Indolylmethanols as Arylation Reagents.
Xu, Meng-Meng; Wang, Hai-Qing; Mao, Yu-Jia; Mei, Guang-Jian; Wang, Shu-Liang; Shi, Feng; The Journal of organic chemistry 83 (2018) 5027–5034; doi:10.1021/acs.joc.8b00228

data_4035513
_publ_section_title
;
 Cooperative Catalysis-Enabled Asymmetric \a-Arylation of Aldehydes Using
 2-Indolylmethanols as Arylation Reagents.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5027
_journal_page_last               5034
_journal_paper_doi               10.1021/acs.joc.8b00228
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C25 H23 N O'
_chemical_formula_sum            'C25 H23 N O'
_chemical_formula_weight         353.44
_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     dual
_audit_creation_date             2017-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.183(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3683(5)
_cell_length_b                   16.2170(10)
_cell_length_c                   15.0187(10)
_cell_measurement_reflns_used    5141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.804
_cell_measurement_theta_min      2.999
_cell_volume                     1999.5(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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_temperature      293.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16090
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.203
_diffrn_reflns_theta_min         4.054
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1425 before and 0.0843 after correction. The Ratio of minimum to maximum transmission is 0.7318. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0724
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1122P)^2^+0.7309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1878
_refine_ls_wR_factor_ref         0.2158
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2732
_reflns_number_total             3744
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00228_si_002.cif
_cod_data_source_block           cu_d8v17047_0m
_cod_database_code               4035513
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.947
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              63093
_shelx_hkl_checksum              86426
_olex2_submission_special_instructions 'No special instructions were received'