Simple inorganic base promoted C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-<i>a</i>]pyridines as functional AIEgens used for detecting picric acid.
Yang, Kai; Luo, Shi-He; Chen, Si-Hong; Cao, Xi-Ying; Zhou, Yong-Jun; Lin, Yan-Lan; Huo, Yan-Ping; Wang, Zhao-Yang; Organic & biomolecular chemistry 19 (2021) 8133–8139; doi:10.1039/d1ob01424b

data_7158252
_publ_section_title
;
 Simple inorganic base promoted C-N and C-C formation: synthesis of
 benzo[4,5]imidazo[1,2-<i>a</i>]pyridines as functional AIEgens used for
 detecting picric acid.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8133
_journal_page_last               8139
_journal_paper_doi               10.1039/d1ob01424b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C18 H14 N2'
_chemical_formula_sum            'C18 H14 N2'
_chemical_formula_weight         258.31
_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             2021-03-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-03-26 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.867(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6034(8)
_cell_length_b                   12.7690(11)
_cell_length_c                   10.6190(9)
_cell_measurement_reflns_used    1430
_cell_measurement_temperature    297
_cell_measurement_theta_max      22.7740
_cell_measurement_theta_min      3.8010
_cell_volume                     1343.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -51.00  13.00   1.00    7.50    --   15.49 -38.00 -30.00   64
  2  \w    -25.00  16.00   1.00    7.50    --  -16.28 -99.00 120.00   41
  3  \w    -85.00   2.00   1.00    7.50    --  -16.28 -38.00-120.00   87
  4  \w    -21.00  22.00   1.00    7.50    --  -16.28 -99.00-120.00   43
  5  \w    -63.00 -30.00   1.00    7.50    --  -16.28 -57.00  90.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0311066000
_diffrn_orient_matrix_UB_12      0.0490277000
_diffrn_orient_matrix_UB_13      0.0228924000
_diffrn_orient_matrix_UB_21      -0.0011333000
_diffrn_orient_matrix_UB_22      0.0113250000
_diffrn_orient_matrix_UB_23      -0.0658061000
_diffrn_orient_matrix_UB_31      -0.0644863000
_diffrn_orient_matrix_UB_32      0.0234525000
_diffrn_orient_matrix_UB_33      -0.0160529000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6242
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.384
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0611
_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^)+(0.0489P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1372
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1571
_reflns_number_total             2366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01424b2.cif
_cod_data_source_block           exp_9111
_cod_depositor_comments
'Adding full bibliography for 7158252--7158256.cif.'
_cod_database_code               7158252
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C14(H14),
 C15(H15), C18(H18)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              49817
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.810