Synthesis of 1,2-Bis(2-aryl-1H-indol-3-yl)ethynes via 5-exo-Digonal Double Cyclization Reactions of 1,4-Bis(2-isocyanophenyl)buta-1,3-diyne with Aryl Grignard Reagents.
Ishikawa, Rino; Iwasawa, Ryosuke; Takiyama, Yuichiro; Yamauchi, Tomokazu; Iwanaga, Tetsuo; Takezaki, Makoto; Watanabe, Motonori; Teramoto, Naozumi; Shimasaki, Toshiaki; Shibata, Mitsuhiro; The Journal of organic chemistry 82 (2017) 652–663; doi:10.1021/acs.joc.6b02668

data_4032073
_publ_section_title
;
 Synthesis of 1,2-Bis(2-aryl-1H-indol-3-yl)ethynes via 5-exo-Digonal
 Double Cyclization Reactions of 1,4-Bis(2-isocyanophenyl)buta-1,3-diyne
 with Aryl Grignard Reagents.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              652
_journal_page_last               663
_journal_paper_doi               10.1021/acs.joc.6b02668
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C19 H18 N O2'
_chemical_formula_weight         292.34
_chemical_melting_point          505.6
_chemical_name_common            1,2-bis(2-phenyl-1H-indol-3-yl)ethyne_1a
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0000(15)
_cell_angle_beta                 100.0843(16)
_cell_angle_gamma                90.0000(15)
_cell_formula_units_Z            4
_cell_length_a                   7.0004(10)
_cell_length_b                   21.017(3)
_cell_length_c                   10.9249(17)
_cell_measurement_reflns_used    7828
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.2812
_cell_measurement_theta_min      5.0461
_cell_volume                     1582.5(4)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'RAXIS conversion'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9298
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         5.04
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0312P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                2916
_reflns_number_total             3574
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02668_si_001.cif
_cod_data_source_block           crystalclear
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '505.6K' was changed to '505.6' - the
value should be numeric and without a unit designator.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4032073.cif.
;
_cod_original_cell_volume        1582.6(4)
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               4032073