Silver(i) catalyzed intramolecular cyclization of N-(2-(alk-1-yn-1-yl))-1H-tetrazoles leading to the formation of N-cyano-2-substituted indoles under ambient conditions
Panaka, Sangeetha; Trivedi, Rajiv; Sony, T.; Prabhakar, S.; Raju Chowhan, L.; Org. Chem. Front. 4 (2017) 1574–; doi:10.1039/C7QO00109F

data_1553739
_publ_section_title
;
 Silver(i) catalyzed intramolecular cyclization of
 N-(2-(alk-1-yn-1-yl))-1H-tetrazoles leading to the formation of
 N-cyano-2-substituted indoles under ambient conditions
;
_journal_issue                   8
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              1574
_journal_paper_doi               10.1039/C7QO00109F
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C15 H9 F N2'
_chemical_formula_sum            'C15 H9 F N2'
_chemical_formula_weight         236.25
_chemical_name_systematic        5-fluoro-2-phenyl-1H-indole-1-carbonitrile
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-06-22 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   25.513(13)
_cell_length_b                   13.881(8)
_cell_length_c                   6.794(4)
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      4.49
_cell_volume                     2406(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1085
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            20801
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             976.00
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.470
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.1134
_refine_ls_shift/su_max          0.106
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1402P)^2^+2.7382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3222
_reflns_number_gt                1690
_reflns_number_total             2754
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c7qo00109f7.cif
_cod_data_source_block           RT-SP-11A
_cod_database_code               1553739
_solvent_exptl_crystal_recrystallization_method DMSO