Regioselective bromination of pyrrolo[1,2-a]quinoxalines
Li, Yingqian; Liu, Yali; Hao, Di; Xu, Liang; Liu, Ping; RSC Advances 14 (2024) 36488–36496; doi:10.1039/D4RA07358D

data_7249598
_publ_section_title
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 Regioselective bromination of pyrrolo[1,2-a]quinoxalines
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              36488
_journal_page_last               36496
_journal_paper_doi               10.1039/D4RA07358D
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C11 H7 Br N2'
_chemical_formula_sum            'C11 H7 Br N2'
_chemical_formula_weight         247.10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-10-03 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4291(6)
_cell_length_b                   4.1088(2)
_cell_length_c                   16.6768(7)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      71.99
_cell_measurement_theta_min      6.59
_cell_volume                     920.18(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17823
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.037
_diffrn_reflns_theta_min         5.305
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.712
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.5195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1154 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.5991.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.21(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1791
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0206P)^2^+1.1447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0659
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                1696
_reflns_number_total             1791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra07358d2.cif
_cod_data_source_block           11
_cod_database_code               7249598
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.658
_shelx_estimated_absorpt_t_min   0.426
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.79(4)
 0.21(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10)
;
_shelx_res_checksum              88062
_olex2_submission_special_instructions 'No special instructions were received'