Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.
Zhu, Jie S.; Son, Jung-Ho; Teuthorn, Andrew P.; Haddadin, Makhluf J.; Kurth, Mark J.; Tantillo, Dean J.; The Journal of organic chemistry 82 (2017) 10875–10882; doi:10.1021/acs.joc.7b01521

data_4032914
_publ_section_title
;
 Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected
 Anthranil Products from Davis-Beirut Reaction.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10875
_journal_page_last               10882
_journal_paper_doi               10.1021/acs.joc.7b01521
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C29 H20 Cl2 N6 O3'
_chemical_formula_weight         571.41
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
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_cell_angle_beta                 112.3410(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.7261(6)
_cell_length_b                   14.1348(4)
_cell_length_c                   20.9034(7)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      7.84
_cell_volume                     5390.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       17
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_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20005
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_diffrn_reflns_point_group_measured_fraction_max 0.949
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_exptl_absorpt_coefficient_mu    2.530
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         9401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0667
_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^)+(0.1021P)^2^+10.4888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1876
_refine_ls_wR_factor_ref         0.1934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8562
_reflns_number_total             9401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01521_si_003.cif
_cod_data_source_block           (1H-benzo(d)imidazol-2-yl)methanone_7
_cod_depositor_comments
;
Adding full bibliography for 4032912--4032914.cif.

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C58 H40 Cl4 N12 O6'
_cod_original_formula_weight         1142.82
_cod_original_formula_units_Z            4
_cod_database_code               4032914
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.435
_shelx_estimated_absorpt_t_max   0.640
_shelx_res_checksum              24058
_shelx_hkl_checksum              44712