Brønsted acid-mediated mono- and di-substitution of quinoxalines with indoles: a pathway to indolocarbazole-quinoxaline scaffolds.
Valvi, Mangesh Biramya; Badhani, Gaurav; More, Karan Prakash; Adimurthy, Subbarayappa; Chemical communications (Cambridge, England) 61 (2025) 4698–4701; doi:10.1039/d4cc06606e

data_7134270
_publ_section_title
;
 Br&#xf8;nsted acid-mediated mono- and di-substitution of quinoxalines
 with indoles: a pathway to indolocarbazole-quinoxaline scaffolds.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4698
_journal_page_last               4701
_journal_paper_doi               10.1039/d4cc06606e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C24 H20 N4'
_chemical_formula_sum            'C24 H20 N4'
_chemical_formula_weight         364.44
_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_date             2023-02-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-12-05 deposited with the CCDC.	2025-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                62.717(3)
_cell_angle_beta                 71.571(4)
_cell_angle_gamma                89.138(3)
_cell_formula_units_Z            2
_cell_length_a                   9.2942(8)
_cell_length_b                   10.9020(8)
_cell_length_c                   11.0378(9)
_cell_measurement_reflns_used    5030
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.139
_cell_measurement_theta_min      2.215
_cell_volume                     931.76(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            45073
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.127
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0949 before and 0.0796 after correction.
The Ratio of minimum to maximum transmission is 0.9372.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3266
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0771P)^2^+0.1931P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2231
_reflns_number_total             3266
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06606e2.cif
_cod_data_source_block           mbv_70a_0m_a
_cod_depositor_comments
'Adding full bibliography for 7134269--7134270.cif.'
_cod_original_cell_volume        931.76(13)
_cod_database_code               7134270
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.990
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), C1(H1A), C2(H2A), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23), C24(H24)
;
_shelx_res_checksum              23844
_shelx_hkl_checksum              83203
_olex2_submission_special_instructions 'No special instructions were received'