Selective synthesis of (1H-benzo[d]imidazol-2-yl)(phenyl)methanone and quinoxaline from aromatic aldehyde and o-phenylenediamine.
Zhan, Zhenzhen; Ma, Haojie; Cui, Xinfeng; Jiang, Pengbo; Pu, Jinghong; Zhang, Yixin; Huang, Guosheng; Organic & biomolecular chemistry 17 (2019) 5148–5152; doi:10.1039/c9ob00531e

data_7156807
_publ_section_title
;
 Selective synthesis of (1H-benzo[d]imidazol-2-yl)(phenyl)methanone and
 quinoxaline from aromatic aldehyde and o-phenylenediamine.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5148
_journal_page_last               5152
_journal_paper_doi               10.1039/c9ob00531e
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C14 H10 N2 O'
_chemical_formula_sum            'C14 H10 N2 O'
_chemical_formula_weight         222.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-12-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-15 deposited with the CCDC.    2019-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.761(3)
_cell_length_b                   9.9736(8)
_cell_length_c                   15.8257(19)
_cell_measurement_reflns_used    630
_cell_measurement_temperature    292.86(10)
_cell_measurement_theta_max      26.0770
_cell_measurement_theta_min      3.7640
_cell_volume                     2329.9(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.86(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -9.00   36.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  -60.0000 45

  2 omega  -33.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  120.0000 99
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0055648000
_diffrn_orient_matrix_UB_12      -0.0244413000
_diffrn_orient_matrix_UB_13      0.0417698000
_diffrn_orient_matrix_UB_21      -0.0474746000
_diffrn_orient_matrix_UB_22      0.0104275000
_diffrn_orient_matrix_UB_23      -0.0033573000
_diffrn_orient_matrix_UB_31      -0.0053614000
_diffrn_orient_matrix_UB_32      -0.0658719000
_diffrn_orient_matrix_UB_33      -0.0160913000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5227
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.43
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.1442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1848
_reflns_number_gt                1140
_reflns_number_total             2291
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00531e1.cif
_cod_data_source_block           zhanzhzh_1214
_cod_depositor_comments          'Adding full bibliography for 7156807.cif.'
_cod_original_cell_volume        2329.8(5)
_cod_database_code               7156807
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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), C2(H2a), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_olex2_date_sample_data_collection 2018-12-14
_olex2_submission_special_instructions 'No special instructions were received'