Selective Synthesis of N-Unsubstituted and N-Arylindoles by the Reaction of Arynes with Azirines.
Thangaraj, Manikandan; Bhojgude, Sachin Suresh; Jain, Shailja; Gonnade, Rajesh G.; Biju, Akkattu T.; The Journal of organic chemistry 81 (2016) 8604–8611; doi:10.1021/acs.joc.6b01472

data_4037100
_publ_section_title
;
 Selective Synthesis of N-Unsubstituted and N-Arylindoles by the Reaction
 of Arynes with Azirines.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8604
_journal_page_last               8611
_journal_paper_doi               10.1021/acs.joc.6b01472
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C22 H13 F6 N'
_chemical_formula_sum            'C22 H13 F6 N'
_chemical_formula_weight         405.33
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                115.263(2)
_cell_angle_beta                 91.231(3)
_cell_angle_gamma                91.976(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8272(4)
_cell_length_b                   10.8142(5)
_cell_length_c                   11.7984(5)
_cell_measurement_reflns_used    4768
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      3.26
_cell_volume                     901.90(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13532
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.910
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0749
_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^)+(0.0942P)^2^+1.5215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1967
_refine_ls_wR_factor_ref         0.2086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2484
_reflns_number_total             3175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01472_si_002.cif
_cod_data_source_block           M158NH_210316_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4037100
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.967
_shelxl_version_number           2013-3
_shelx_res_checksum              55820
_shelx_hkl_checksum              24312