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_7249307
_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 H9 N3'
_chemical_formula_sum            'C14 H9 N3'
_chemical_formula_weight         219.24
_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             2023-01-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-07 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.175(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2378(10)
_cell_length_b                   11.8288(14)
_cell_length_c                   12.7296(17)
_cell_measurement_reflns_used    9020
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      3.19
_cell_volume                     1089.1(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27964
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.187
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1310 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.9226.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0396P)^2^+0.2428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1601
_reflns_number_total             1928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00714j2.cif
_cod_data_source_block           lqj-1
_cod_depositor_comments
'Adding full bibliography for 7249304--7249307.cif.'
_cod_database_code               7249307
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.984
_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:
 N1(H1), C4(H4), C13(H13), C12(H12), C1(H1A), C10(H10), C9(H9), C5(H5), C6(H6)
;
_shelx_res_checksum              9940
_shelx_hkl_checksum              30270
_olex2_submission_special_instructions 'No special instructions were received'