An elegant approach for the synthesis of multisubstituted imidazole <i>via</i> FeCl<sub>3</sub>/SiO<sub>2</sub> catalyzed activation of acetals: a photophysical study of an imidazole-carbazole hybrid.
Das, Barnali; Bhattacharyya, Arghyadeep; Paul, Bhaswati; Natarajan, Ramalingam; Majumdar, Swapan; RSC advances 14 (2024) 33512–33523; doi:10.1039/d4ra06436d

data_7249490
_publ_section_title
;
 An elegant approach for the synthesis of multisubstituted imidazole
 <i>via</i> FeCl<sub>3</sub>/SiO<sub>2</sub> catalyzed activation of
 acetals: a photophysical study of an imidazole-carbazole hybrid.
;
_journal_issue                   45
_journal_name_full               'RSC advances'
_journal_page_first              33512
_journal_page_last               33523
_journal_paper_doi               10.1039/d4ra06436d
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C35 H27 N3, 1[CH2Cl2]'
_chemical_formula_sum            'C36 H29 Cl2 N3'
_chemical_formula_weight         574.52
_chemical_name_systematic        RN_BP_BDS110
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-06-07 deposited with the CCDC.	2024-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                113.447(9)
_cell_angle_beta                 91.736(10)
_cell_angle_gamma                95.668(10)
_cell_formula_units_Z            2
_cell_length_a                   10.137(2)
_cell_length_b                   11.456(3)
_cell_length_c                   13.238(3)
_cell_measurement_reflns_used    8922
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      4.24
_cell_volume                     1399.4(6)
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_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 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            45395
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.414
_diffrn_reflns_theta_min         4.237
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.323
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0992 before and 0.0678 after correction.
The Ratio of minimum to maximum transmission is 0.8586.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichlomethane-hexane'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0649
_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^)+(0.1459P)^2^+0.2365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2066
_refine_ls_wR_factor_ref         0.2120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4430
_reflns_number_total             4889
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra06436d2.cif
_cod_data_source_block           rn_bp_bds110_2_0m_a
_cod_original_cell_volume        1399.5(6)
_cod_database_code               7249490
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.854
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C36(H36), C3(H3), C4(H4), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              80737
_shelx_fab_checksum              29327
_olex2_submission_special_instructions 'No special instructions were received'