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_4035799
_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_formula_moiety         'C39 H32 N2 O, C0.5 H Cl'
_chemical_formula_sum            'C39.5 H33 Cl N2 O'
_chemical_formula_weight         587.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 103.665(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.869(3)
_cell_length_b                   13.815(2)
_cell_length_c                   19.332(3)
_cell_measurement_reflns_used    3142
_cell_measurement_temperature    296
_cell_measurement_theta_max      22.60
_cell_measurement_theta_min      2.45
_cell_volume                     6194.3(15)
_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 0.997
_diffrn_measured_fraction_theta_max 0.979
_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  0.0339
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18186
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.447
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0563 before and 0.0416 after correction. The Ratio of minimum to maximum transmission is 0.9013. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             2472
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         6952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1009P)^2^+0.8213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.2013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3801
_reflns_number_total             6952
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00414_si_002.cif
_cod_data_source_block           sf20170309_mc_0m
_cod_original_formula_sum        'C39.50 H33 Cl N2 O'
_cod_database_code               4035799
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.954
_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. Others
 Fixed Sof: H40A(0.5) H40B(0.5)
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
  C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C33(H33), C34(H34),
 C35(H35), C36(H36)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              39763
_shelx_hkl_checksum              74207
_olex2_submission_special_instructions 'No special instructions were received'