Synthesis of indole-linked β-cyano-enones: a pathway to indolyl-2-pyrrolones.
Mondal, Nurabul; Kumari, Vidya; Ali, Danish; Choudhury, Lokman H.; Organic & biomolecular chemistry 23 (2025) 3913–3924; doi:10.1039/d5ob00328h

data_7160452
_publ_section_title
;
 Synthesis of indole-linked &#x3b2;-cyano-enones: a pathway to
 indolyl-2-pyrrolones.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3913
_journal_page_last               3924
_journal_paper_doi               10.1039/d5ob00328h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C25 H16 N2 O2'
_chemical_formula_sum            'C25 H16 N2 O2'
_chemical_formula_weight         376.40
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-10
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-10 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                101.017(8)
_cell_angle_beta                 101.391(7)
_cell_angle_gamma                93.642(7)
_cell_formula_units_Z            2
_cell_length_a                   9.2194(12)
_cell_length_b                   10.0506(14)
_cell_length_c                   10.4838(14)
_cell_measurement_reflns_used    3531
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.77
_cell_measurement_theta_min      2.27
_cell_volume                     929.6(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12101
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.001
_diffrn_reflns_theta_max         25.001
_diffrn_reflns_theta_min         2.266
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1618 before and 0.0845 after correction.
The Ratio of minimum to maximum transmission is 0.7687.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.242
_refine_ls_R_factor_all          0.1669
_refine_ls_R_factor_gt           0.1078
_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^)+2.0385P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2020
_reflns_number_total             3197
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00328h2.cif
_cod_data_source_block           blank_0m
_cod_depositor_comments
'Adding full bibliography for 7160452--7160454.cif.'
_cod_database_code               7160452
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.992
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C2(H2A), C16(H16), C25(H25), C3(H3), C21(H21), C12(H12),
 C4(H4), C15(H15), C22(H22), C24(H24), C23(H23), C14(H14), C5(H5), C13(H13)
;
_shelx_res_checksum              27660
_olex2_submission_special_instructions 'No special instructions were received'