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_7158255
_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         'C25 H19 Cl N2'
_chemical_formula_sum            'C25 H19 Cl N2'
_chemical_formula_weight         382.87
_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                 93.129(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0520(9)
_cell_length_b                   10.4783(11)
_cell_length_c                   18.7614(15)
_cell_measurement_reflns_used    2245
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5280
_cell_measurement_theta_min      4.0340
_cell_volume                     1973.2(3)
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -52.00  77.00   1.00    5.00    --   15.65   0.00 -90.00  129
  2  \w    -11.00  18.00   1.00    5.00    --  -16.43 -99.00 -90.00   29
  3  \w    -25.00  21.00   1.00    5.00    --  -16.43 -99.00  90.00   46
  4  \w    -25.00  10.00   1.00    5.00    --   15.65 -99.00 120.00   35
;
_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      -0.0105796000
_diffrn_orient_matrix_UB_12      0.0593225000
_diffrn_orient_matrix_UB_13      -0.0176214000
_diffrn_orient_matrix_UB_21      0.0565065000
_diffrn_orient_matrix_UB_22      0.0256905000
_diffrn_orient_matrix_UB_23      0.0192395000
_diffrn_orient_matrix_UB_31      0.0410952000
_diffrn_orient_matrix_UB_32      -0.0200682000
_diffrn_orient_matrix_UB_33      -0.0274426000
_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  0.0309
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8419
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.486
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11048
_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    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0485P)^2^+0.2327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2297
_reflns_number_total             3462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01424b2.cif
_cod_data_source_block           exp_9112
_cod_depositor_comments
'Adding full bibliography for 7158252--7158256.cif.'
_cod_database_code               7158255
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.67
_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:
 C3(H3), C5(H5), C7(H7), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              94540
_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 5.723
_oxdiff_exptl_absorpt_empirical_full_min 0.545