Chemoselective Double Annulation of Two Different Isocyanides: Rapid Access to Trifluoromethylated Indole-Fused Heterocycles.
Gao, Yuelei; Hu, Zhongyan; Dong, Jinhuan; Liu, Jun; Xu, Xianxiu; Organic letters 19 (2017) 5292–5295; doi:10.1021/acs.orglett.7b02582

data_1547165
_publ_section_title
;
 Chemoselective Double Annulation of Two Different Isocyanides: Rapid
 Access to Trifluoromethylated Indole-Fused Heterocycles.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5292
_journal_page_last               5295
_journal_paper_doi               10.1021/acs.orglett.7b02582
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H17 F3 N2 O, 0.25(C4 H10 O)'
_chemical_formula_sum            'C25 H19.5 F3 N2 O1.25'
_chemical_formula_weight         424.92
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                96.034(5)
_cell_angle_beta                 99.172(5)
_cell_angle_gamma                99.186(5)
_cell_formula_units_Z            8
_cell_length_a                   10.3304(12)
_cell_length_b                   17.890(2)
_cell_length_c                   23.784(3)
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.66
_cell_measurement_theta_min      2.33
_cell_volume                     4245.1(9)
_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      291.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            83277
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_min         2.351
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             1764
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1132
_refine_ls_number_reflns         20924
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1776
_refine_ls_R_factor_gt           0.0729
_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^)+(0.0799P)^2^+1.3016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.2102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9757
_reflns_number_total             20924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02582_si_002.cif
_cod_data_source_block           01
_cod_depositor_comments
;
          Adding full bibliography for 1547165.cif.

2019-01-24
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '4(C24 H17 F3 N2 O), C4 H10 O'
_cod_original_formula_sum        'C100 H78 F12 N8 O5'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1699.70
_cod_database_code               1547165
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
O5 \\sim C97 \\sim C98 \\sim C99 \\sim C100: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.01
C18 \\sim C19 \\sim C20 \\sim H20 \\sim C21 \\sim C22 \\sim H22 \\sim C23 \\sim
C24 \\sim H24A \\sim H24B \\sim H24C \\sim H97A: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C98(H98A,H98B), C99(H99A,H99B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C29(H29),
  C30(H30), C31(H31), C32(H32), C35(H35), C36(H36), C37(H37), C38(H38),
 C39(H39), C43(H43), C44(H44), C46(H46), C47(H47), C49(H49), C54(H54), C55(H55),
  C56(H56), C57(H57), C59(H59), C60(H60), C61(H61), C62(H62), C63(H63),
 C67(H67), C68(H68), C70(H70), C71(H71), C73(H73), C78(H78), C79(H79), C80(H80),
  C81(H81), C83(H83), C84(H84), C85(H85), C86(H86), C87(H87), C91(H91),
 C92(H92), C94(H94), C95(H95)
3.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C48(H48A,H48B,H48C), C72(H72A,H72B,H72C), C96(H96A,H96B,
 H96C), C97(H97A,H97B,H97C), C100(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'