Structural insight into imidazopyridines and benzimidazoles: the importance of the hydrogen bond, π-stacking interactions and intramolecular charge transfer effect for fluorescence
Li, Haonan; Gao, Chenping; Li, Zhibin; Guo, Yanchun; Cao, Shuxia; Zhao, Yufen; CrystEngComm 26 (2024) 5380–5392; doi:10.1039/D4CE00714J

data_7249305
_publ_section_title
;
 Structural insight into imidazopyridines and benzimidazoles: the
 importance of the hydrogen bond, \p-stacking interactions and
 intramolecular charge transfer effect for fluorescence
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              5380
_journal_page_last               5392
_journal_paper_doi               10.1039/D4CE00714J
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H12 N2'
_chemical_formula_sum            'C17 H12 N2'
_chemical_formula_weight         244.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-04 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4481(3)
_cell_length_b                   12.5608(7)
_cell_length_c                   13.0832(8)
_cell_measurement_reflns_used    1705
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9890
_cell_measurement_theta_min      5.9440
_cell_volume                     1223.99(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -93.00 -67.00   1.00    4.50    --  -33.50 -19.00 120.00   26
  2  \w    -55.00  -3.00   1.00    4.50    --  -33.50 -19.00 120.00   52
  3  \w     -5.00  29.00   1.00    4.50    --  -33.50  57.00  90.00   34
  4  \w     76.00 107.00   1.00    4.50    --   36.47 178.00  90.00   31
  5  \w     -3.00  41.00   1.00    4.50    --   36.47 -99.00  30.00   44
  6  \w     47.00 103.00   1.00   13.50    --  108.00 -94.00 -30.00   56
  7  \w     42.00  68.00   1.00   13.50    --  108.00 -61.00  30.00   26
  8  \w     40.00  86.00   1.00   13.50    --  108.00 -94.00  90.00   46
  9  \w     95.00 177.00   1.00   14.00    --  108.00  45.00 -60.00   82
 10  \w     97.00 176.00   1.00   14.00    --  108.00  61.00-180.00   79
 11  \w     51.00 106.00   1.00   14.00    --  108.00-111.00-150.00   55
 12  \w     64.00 105.00   1.00    4.50    --   36.47  57.00-180.00   41
 13  \w     27.00  60.00   1.00    4.50    --   36.47 -99.00  90.00   33
 14  \w     24.00  78.00   1.00    4.50    --   36.47  57.00 -90.00   54
 15  \w     98.00 124.00   1.00   14.00    --  108.00 -45.00 -90.00   26
 16  \w     47.00  91.00   1.00   14.00    --  108.00 -45.00 -90.00   44
 17  \w     91.00 133.00   1.00   14.00    --  108.00  61.00 120.00   42
 18  \w     56.00  95.00   1.00   14.00    --  108.00 -30.00-150.00   39
 19  \w     65.00  91.00   1.00    4.50    --   36.47 178.00  30.00   26
 20  \w     52.00  77.00   1.00    4.50    --   36.47 -99.00   0.00   25
 21  \w      9.00  35.00   1.00    4.50    --   36.47 -99.00   0.00   26
 22  \w     94.00 120.00   1.00   14.00    --  108.00  45.00 120.00   26
 23  \w    127.00 177.00   1.00   14.00    --  108.00  45.00  30.00   50
 24  \w    141.00 167.00   1.00   14.00    --  108.00  61.00  90.00   26
 25  \w     45.00  72.00   1.00   14.00    --  108.00 -61.00-180.00   27
 26  \w     89.00 128.00   1.00   14.00    --  108.00 -61.00 -90.00   39
 27  \w    143.00 178.00   1.00   14.00    --  108.00  45.00 120.00   35
 28  \w    146.00 176.00   1.00   14.00    --  108.00 111.00  60.00   30
 29  \w    101.00 127.00   1.00   14.00    --  108.00 -45.00 -30.00   26
 30  \w     88.00 114.00   1.00   14.00    --  108.00  61.00 -90.00   26
 31  \w    153.00 178.00   1.00   14.00    --  108.00  45.00 -90.00   25
 32  \w     94.00 120.00   1.00   14.00    --  108.00  61.00 150.00   26
;
_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      -0.0567865000
_diffrn_orient_matrix_UB_12      -0.0277558000
_diffrn_orient_matrix_UB_13      -0.1100831000
_diffrn_orient_matrix_UB_21      0.0944749000
_diffrn_orient_matrix_UB_22      -0.1086400000
_diffrn_orient_matrix_UB_23      0.0094287000
_diffrn_orient_matrix_UB_31      -0.1749546000
_diffrn_orient_matrix_UB_32      -0.0496919000
_diffrn_orient_matrix_UB_33      0.0408152000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6812
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.988
_diffrn_reflns_theta_min         4.881
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.326
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 697 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0455P)^2^+0.0136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                1975
_reflns_number_total             2344
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00714j2.cif
_cod_data_source_block           202209166
_cod_depositor_comments
'Adding full bibliography for 7249304--7249307.cif.'
_cod_original_cell_volume        1223.99(12)
_cod_database_code               7249305
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.897
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17)
;
_shelx_res_checksum              73410
_shelx_hkl_checksum              2628
_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 1.202
_oxdiff_exptl_absorpt_empirical_full_min 0.918