An expedient route to tricyanovinylindoles and indolylmaleimides from o-alkynylanilines utilising DMSO as a one-carbon synthon.
Chakraborty, Nikita; Dahiya, Anjali; Rakshit, Amitava; Modi, Anju; Patel, Bhisma K.; Organic & biomolecular chemistry 19 (2021) 6847–6857; doi:10.1039/d1ob01086g

data_7158184
_publ_section_title
;
 An expedient route to tricyanovinylindoles and indolylmaleimides from
 o-alkynylanilines utilising DMSO as a one-carbon synthon.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6847
_journal_page_last               6857
_journal_paper_doi               10.1039/d1ob01086g
_journal_volume                  19
_journal_year                    2021
_chemical_compound_source        NA
_chemical_formula_sum            'C20 H11 F N4'
_chemical_formula_weight         326.33
_chemical_name_systematic
2-(5-fluoro-2-(p-tolyl)-1H-indol-3-yl)ethene-1,1,2-tricarbonitrile
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-12-19 deposited with the CCDC.	2021-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.167(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4106(7)
_cell_length_b                   14.3958(14)
_cell_length_c                   9.9664(5)
_cell_measurement_reflns_used    1572
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4520
_cell_measurement_theta_min      2.8230
_cell_volume                     1632.8(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7751
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.743
_diffrn_reflns_theta_min         2.281
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       cube
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   0.980
_exptl_transmission_factor_min   0.977
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0488P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1842
_reflns_number_total             3709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01086g2.cif
_cod_data_source_block           exp_6155
_cod_depositor_comments          'Adding full bibliography for 7158184.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158184
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              54422