Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid structures through double cyclodehydration and aromatization and their unique optical properties with blue emission
Bae, Gi Hun; Kim, Suzi; Lee, Na Keum; Dagar, Anuradha; Lee, Jeong Hwa; Lee, Jeeyeon; Kim, Ikyon; RSC Advances 10 (2020) 7265–7288; doi:10.1039/D0RA01140A

data_7239962
_publ_section_title
;
 Facile approach to benzo[d]imidazole-pyrrolo[1,2-a]pyrazine hybrid
 structures through double cyclodehydration and aromatization and their
 unique optical properties with blue emission
;
_journal_issue                   12
_journal_name_full               'RSC Advances'
_journal_page_first              7265
_journal_page_last               7288
_journal_paper_doi               10.1039/D0RA01140A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C19 H12 F N3'
_chemical_formula_sum            'C19 H12 F N3'
_chemical_formula_weight         301.32
_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             2019-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-29 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.930(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5685(6)
_cell_length_b                   8.4986(6)
_cell_length_c                   16.7749(14)
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    292.08(10)
_cell_measurement_theta_max      22.2400
_cell_measurement_theta_min      3.0720
_cell_volume                     1495.67(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.08(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.889
_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    -25.00   0.00   1.00    1.83    --  -11.04 -91.00   2.00   25
  2  \w    -45.00 -20.00   1.00    1.83    --  -11.04  91.00 115.00   25
  3  \w    -14.00  11.00   1.00    1.83    --   11.51 -91.00   2.00   25
  4  \w    -16.00  10.00   1.00    1.83    --  -11.04 -99.00 -90.00   26
  5  \w    -87.00  15.00   1.00    1.83    --  -11.04 -77.00-120.00  102
  6  \w    -50.00  -3.00   1.00    1.83    --  -11.04 -38.00 120.00   47
  7  \w    -12.00  84.00   1.00    1.83    --   11.51  38.00-180.00   96
  8  \w    -60.00  36.00   1.00    1.83    --   11.51 -38.00  90.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0067258000
_diffrn_orient_matrix_UB_12      -0.0735470000
_diffrn_orient_matrix_UB_13      0.0200025000
_diffrn_orient_matrix_UB_21      -0.0257459000
_diffrn_orient_matrix_UB_22      0.0329828000
_diffrn_orient_matrix_UB_23      0.0333954000
_diffrn_orient_matrix_UB_31      -0.0621760000
_diffrn_orient_matrix_UB_32      -0.0216436000
_diffrn_orient_matrix_UB_33      -0.0172588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17305
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.579
_diffrn_reflns_theta_min         2.166
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.247
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0079(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.2295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1534
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1865
_reflns_number_total             3729
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra01140a2.cif
_cod_data_source_block           exp_1357-2
_cod_depositor_comments          'Adding full bibliography for 7239962.cif.'
_cod_database_code               7239962
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C19 H12 F N3'
_chemical_oxdiff_usercomment     BP-008
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.964
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H00B), C3(H00C), C6(H00D), C21(H00E), C12(H00F), C19(H00G), C22(H00H),
 C15(H00I), C7(H00K), C20(H00L), C16(H00M), C17(H00N)
;
_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 1.286
_oxdiff_exptl_absorpt_empirical_full_min 0.763