Catalytic asymmetric C2-nucleophilic substitutions of C3-substituted indoles with ortho-hydroxybenzyl alcohols
Wu, Jia-Le; Wang, Jing-Yi; Wu, Ping; Mei, Guang-Jian; Shi, Feng; Organic Chemistry Frontiers 4 (2017) 2465–; doi:10.1039/C7QO00649G

data_1553866
_publ_section_title
;
 Catalytic asymmetric C2-nucleophilic substitutions of C3-substituted
 indoles with ortho-hydroxybenzyl alcohols
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2465
_journal_paper_doi               10.1039/C7QO00649G
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C28 H30 N2 O3, C3 H6 O'
_chemical_formula_sum            'C31 H36 N2 O4'
_chemical_formula_weight         500.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-07-21 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                74.369(4)
_cell_angle_beta                 82.265(4)
_cell_angle_gamma                75.011(5)
_cell_formula_units_Z            2
_cell_length_a                   8.4885(5)
_cell_length_b                   10.6796(6)
_cell_length_c                   16.8127(9)
_cell_measurement_reflns_used    521
_cell_measurement_temperature    296
_cell_measurement_theta_max      45.116
_cell_measurement_theta_min      4.421
_cell_volume                     1414.37(14)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4709
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        66.402
_diffrn_reflns_theta_max         66.402
_diffrn_reflns_theta_min         2.736
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2008/4 (Bruker,2010) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1266 before and 0.0512 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1188 before and 0.0466 after correction.
 The Ratio of minimum to maximum transmission is 0.73.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 18678 reflections, Rint = 0.0763
 (3067 with I > 3sig(I), Rint = 0.0455)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0750
_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^)+(0.0874P)^2^+0.3671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1876
_refine_ls_wR_factor_ref         0.2188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2989
_reflns_number_total             4709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00649g2.cif
_cod_data_source_block           dm16702
_cod_database_code               1553866
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.941
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.658(3) 0.342(3)
2. 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, All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              74861
_shelx_hkl_checksum              94473
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'