An unconventional route to an ambipolar azaheterocycle and its <i>in situ</i> generated radical anion.
Das, Sarasija; Choudhury, Anwesha; Mandal, Arnab; Kumar, Chandan; Ranjan Sahoo, Smruti; Bedi, Anjan; Shekhar Karmakar, Himadri; Gopal Ghosh, Nani; Dey, Somnath; Krishnan Iyer, Parameswar; Bhattacharyya, Sayan; Zade, Sanjio S.; Organic & biomolecular chemistry 19 (2021) 5114–5120; doi:10.1039/d1ob00826a

data_7158069
_publ_section_title
;
 An unconventional route to an ambipolar azaheterocycle and its <i>in
 situ</i> generated radical anion.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5114
_journal_page_last               5120
_journal_paper_doi               10.1039/d1ob00826a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C24 H13 Br N2 O'
_chemical_formula_sum            'C24 H13 Br N2 O'
_chemical_formula_weight         425.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-12 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.99(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.495(4)
_cell_length_b                   15.107(7)
_cell_length_c                   12.403(6)
_cell_measurement_reflns_used    4360
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      35.7220
_cell_measurement_theta_min      2.6300
_cell_volume                     1774.8(14)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16317
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         2.538
_exptl_absorpt_coefficient_mu    2.334
_exptl_crystal_colour            'dull bluish green'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
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_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0446P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2107
_reflns_number_total             4106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00826a2.cif
_cod_data_source_block           ttt
_cod_depositor_comments
'Adding full bibliography for 7158069--7158070.cif.'
_cod_original_cell_volume        1774.8(13)
_cod_database_code               7158069
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   1.00000
_shelx_estimated_absorpt_t_min   0.49489
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S)
;
_shelx_res_checksum              27837
_olex2_submission_special_instructions 'No special instructions were received'