Catalytic Asymmetric Aza-ene Reaction of 3-Indolylmethanols with Cyclic Enaminones: Enantioselective Approach to C3-Functionalized Indoles.
Tan, Wei; Du, Bai-Xiang; Li, Xin; Zhu, Xu; Shi, Feng; Tu, Shu-Jiang; The Journal of organic chemistry 79 (2014) 4635–4643; doi:10.1021/jo500644v

data_4029419
_publ_section_title
;
 Catalytic Asymmetric Aza-ene Reaction of 3-Indolylmethanols with Cyclic
 Enaminones: Enantioselective Approach to C3-Functionalized Indoles.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4635
_journal_page_last               4643
_journal_paper_doi               10.1021/jo500644v
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C31 H28 Cl N3 O2'
_chemical_formula_weight         510.01
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   14.5913(9)
_cell_length_b                   14.5913(9)
_cell_length_c                   24.0429(16)
_cell_measurement_reflns_used    4046
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.04
_cell_measurement_theta_min      2.54
_cell_volume                     4433.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1097
_diffrn_reflns_av_unetI/netI     0.1305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            45481
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.485
_diffrn_reflns_theta_min         1.611
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_platon_squeeze_details
;
;
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
; 
 Flack x determined using 1135 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       0.0081(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         8858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1722
_refine_ls_R_factor_gt           0.0772
_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^)+(0.0800P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1958
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3535
_reflns_number_total             8858
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo500644v_si_003.cif
_cod_data_source_block           SF140411_TW_0m
_cod_depositor_comments
'Adding full bibliography for 4029418--4029419.cif.'
_cod_original_cell_volume        4433.1(6)
_cod_database_code               4029419
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.977
_shelxl_version_number           2013-4
_shelx_res_checksum              91437
_shelx_hkl_checksum              24168