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_7249304
_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_formula_moiety         'C14 H8 F3 I N2'
_chemical_formula_sum            'C14 H8 F3 I N2'
_chemical_formula_weight         388.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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                 102.0839(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.8694(3)
_cell_length_b                   7.34027(12)
_cell_length_c                   15.1137(2)
_cell_measurement_reflns_used    4280
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8790
_cell_measurement_theta_min      5.1710
_cell_volume                     2697.84(7)
_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 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -55.00   1.40   0.60    5.00    --  -33.50  37.00-180.00   94
  2  \w     21.00  71.40   0.60    5.00    --   36.47  57.00-180.00   84
  3  \w     48.00  77.40   0.60    5.00    --   36.47  19.00 120.00   49
  4  \w    -32.00  -5.00   0.60    5.00    --   36.47 -77.00  90.00   45
  5  \w     31.00 103.00   0.60    5.00    --   36.47  37.00-120.00  120
  6  \w     17.00  44.00   0.60    5.00    --   36.47  19.00 120.00   45
  7  \w     12.00  62.40   0.60    5.00    --   36.47  77.00  60.00   84
  8  \w     40.00  66.40   0.60    5.00    --   36.47  57.00  30.00   44
  9  \w      0.00  30.00   0.60    5.00    --   36.47 -99.00  90.00   50
 10  \w     27.00  63.00   0.60    5.00    --   36.47 -77.00  90.00   60
 11  \w     81.00 107.40   0.60    5.00    --   36.47 178.00 150.00   44
 12  \w     34.00 104.20   0.60    5.00    --   36.47  77.00  90.00  117
 13  \w     -7.00  18.20   0.60    5.00    --   36.47 106.00-159.68   42
 14  \w      9.00  54.00   0.60    5.00    --   36.47  77.00   0.00   75
 15  \w     35.00  61.40   0.60    5.00    --   36.47 -99.00  90.00   44
 16  \w    -34.00  33.20   0.60    5.00    --   36.47 -37.00 -30.00  112
 17  \w     79.00 105.40   0.60    8.50    --  108.00  77.00 -30.00   44
 18  \w     88.00 114.40   0.60    8.50    --  108.00  61.00 -30.00   44
 19  \w     82.00 111.40   0.60    8.50    --  108.00  30.00  60.00   49
 20  \w    115.00 175.00   0.60    8.50    --  108.00  77.00 -60.00  100
 21  \w     37.00 110.20   0.60    8.50    --  108.00-111.00-120.00  122
 22  \w     39.00 120.00   0.60    8.50    --  108.00 -45.00 -90.00  135
 23  \w     79.00 105.40   0.60    8.50    --  108.00  77.00 -60.00   44
 24  \w     38.00 108.20   0.60    8.50    --  108.00 -94.00 -90.00  117
 25  \w     88.00 114.40   0.60    8.50    --  108.00  61.00  30.00   44
 26  \w     82.00 115.60   0.60    8.50    --  108.00  30.00  90.00   56
 27  \w    121.00 160.60   0.60    8.50    --  108.00  45.00 120.00   66
 28  \w    112.00 174.40   0.60    8.50    --  108.00  77.00  60.00  104
 29  \w     79.00 104.20   0.60    8.50    --  108.00  77.00  60.00   42
 30  \w     88.00 114.40   0.60    8.50    --  108.00  45.00 120.00   44
 31  \w    124.00 154.60   0.60    8.50    --  108.00  77.00  30.00   51
 32  \w     89.00 115.40   0.60    8.50    --  108.00  61.00  90.00   44
 33  \w     81.00 107.40   0.60    8.50    --  108.00  77.00  90.00   44
 34  \w     84.00 114.00   0.60    8.50    --  108.00  30.00  30.00   50
 35  \w    111.00 176.40   0.60    8.50    --  108.00  77.00   0.00  109
 36  \w     83.00 109.40   0.60    8.50    --  108.00  30.00   0.00   44
 37  \w     87.00 113.40   0.60    8.50    --  108.00  30.00 -30.00   44
 38  \w     88.00 114.40   0.60    8.50    --  108.00  61.00  60.00   44
 39  \w     88.00 151.60   0.60    8.50    --  108.00  61.00   0.00  106
 40  \w     79.00 104.20   0.60    8.50    --  108.00  77.00   0.00   42
 41  \w     88.00 113.20   0.60    8.50    --  108.00  45.00  30.00   42
 42  \w     83.00 108.20   0.60    8.50    --  108.00  30.00 120.00   42
 43  \w     79.00 112.60   0.60    8.50    --  108.00  77.00  30.00   56
 44  \w     80.00 106.40   0.60    8.50    --  108.00  77.00 -90.00   44
 45  \w     67.00  96.40   0.60    8.50    --  108.00  15.00   0.00   49
 46  \w    133.00 166.00   0.60    8.50    --  108.00  15.00   0.00   55
 47  \w     66.80 109.40   0.60    8.50    --  108.00 -94.00  90.00   71
;
_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      0.0012906000
_diffrn_orient_matrix_UB_12      0.0350130000
_diffrn_orient_matrix_UB_13      0.1009321000
_diffrn_orient_matrix_UB_21      0.0629383000
_diffrn_orient_matrix_UB_22      0.0223341000
_diffrn_orient_matrix_UB_23      0.0177687000
_diffrn_orient_matrix_UB_31      -0.0070592000
_diffrn_orient_matrix_UB_32      0.2057252000
_diffrn_orient_matrix_UB_33      -0.0191227000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10691
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.969
_diffrn_reflns_theta_min         3.635
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53378
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.568
_refine_diff_density_min         -1.696
_refine_diff_density_rms         0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+4.4191P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2282
_reflns_number_total             2577
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00714j2.cif
_cod_data_source_block           202209167
_cod_depositor_comments
'Adding full bibliography for 7249304--7249307.cif.'
_cod_original_cell_volume        2697.85(7)
_cod_database_code               7249304
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2F6
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.313
_shelx_estimated_absorpt_t_min   0.141
_reflns_odcompleteness_completeness 99.92
_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. Restrained distances
 F1-F2 \\sim F1-F3 \\sim F2-F3 \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A
 with sigma of 0.04
 C14-F1 \\sim C14-F2 \\sim C14-F3 \\sim C14-F1A \\sim C14-F2A \\sim C14-F3A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F1)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F1) = Uanis(F1A)
Uanis(F2) = Uanis(F2A)
Uanis(F3) = Uanis(F3A)
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C12(H12), C13(H13)
;
_shelx_res_checksum              7005
_shelx_hkl_checksum              75470
_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 1.660
_oxdiff_exptl_absorpt_empirical_full_min 0.669