Catalytic Asymmetric Conjugate Addition of Indoles to para-Quinone Methide Derivatives.
Wang, Jin-Rong; Jiang, Xiao-Li; Hang, Qing-Qing; Zhang, Shu; Mei, Guang-Jian; Shi, Feng; The Journal of organic chemistry 84 (2019) 7829–7839; doi:10.1021/acs.joc.9b00710

data_4034670
_publ_section_title
;
 Catalytic Asymmetric Conjugate Addition of Indoles to para-Quinone
 Methide Derivatives.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7829
_journal_page_last               7839
_journal_paper_doi               10.1021/acs.joc.9b00710
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H35 N O3'
_chemical_formula_sum            'C30 H35 N O3'
_chemical_formula_weight         457.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.70720(10)
_cell_length_b                   15.9416(2)
_cell_length_c                   18.7685(3)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.966
_cell_measurement_theta_min      4.758
_cell_volume                     2605.19(6)
_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      169.91
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32922
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.946
_diffrn_reflns_theta_min         4.098
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1078 before and 0.0545 after correction. The Ratio of minimum to maximum transmission is 0.8360. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1844 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0287P)^2^+0.3544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4542
_reflns_number_total             4944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00710_si_002.cif
_cod_data_source_block           190123sf_0m
_cod_database_code               4034670
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3A), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C22(H22)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              17717
_shelx_hkl_checksum              44367
_olex2_submission_special_instructions 'No special instructions were received'