Chemodivergent Tandem Cyclizations of 2-Indolylmethanols with Tryptophols: C-N versus C-C Bond Formation.
Wang, Jing-Yi; Wu, Ping; Wu, Jia-Le; Mei, Guang-Jian; Shi, Feng; The Journal of organic chemistry 83 (2018) 5931–5946; doi:10.1021/acs.joc.8b00414

data_4035798
_publ_section_title
;
 Chemodivergent Tandem Cyclizations of 2-Indolylmethanols with
 Tryptophols: C-N versus C-C Bond Formation.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5931
_journal_page_last               5946
_journal_paper_doi               10.1021/acs.joc.8b00414
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C39 H32 N2 O'
_chemical_formula_sum            'C39 H32 N2 O'
_chemical_formula_weight         544.66
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.228(6)
_cell_length_b                   16.224(8)
_cell_length_c                   18.542(9)
_cell_measurement_reflns_used    3470
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.56
_cell_measurement_theta_min      2.197
_cell_volume                     3378(3)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19183
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.749
_diffrn_reflns_theta_min         2.530
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0545 before and 0.0442 after correction. The Ratio of minimum to maximum transmission is 0.8651. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.071
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1454 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         6988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0762
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1673P)^2^+0.1382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2088
_refine_ls_wR_factor_ref         0.2341
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                4639
_reflns_number_total             6988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00414_si_003.cif
_cod_data_source_block           sf20170627_wjl_1_0m
_cod_database_code               4035798
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.984
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1B), C2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17),
 C18(H18), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37),
 C38(H38), C39(H39)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              14322
_shelx_hkl_checksum              90515
_shelx_fab_checksum              15725
_olex2_submission_special_instructions 'No special instructions were received'