Facile access to 1,2-disubstituted benzimidazoles and 2,3-dihydro-1H-perimidines using a biogenically synthesized single phase δ-MnO2 NP catalyst and its dye removal study
R., Nandini; R., Thrilokraj; Kshirsagar, Umesh A.; Hegde, Rajeev V.; Ghosh, Arnab; Patil, Siddappa A.; Malecki, Jan Grzegorz; Dateer, Ramesh B.; New Journal of Chemistry 48 (2024) 1327–1335; doi:10.1039/D3NJ03803C

data_7062906
_publ_section_title
;
 Facile access to 1,2-disubstituted benzimidazoles and
 2,3-dihydro-1H-perimidines using a biogenically synthesized single phase
 \d-MnO2 NP catalyst and its dye removal study
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1327
_journal_page_last               1335
_journal_paper_doi               10.1039/D3NJ03803C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C22 H20 N2'
_chemical_formula_sum            'C22 H20 N2'
_chemical_formula_weight         312.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2gn1jq
_audit_creation_date             2022-12-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-07-21 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9094(6)
_cell_length_b                   11.0437(7)
_cell_length_c                   15.9662(8)
_cell_measurement_reflns_used    3025
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.5890
_cell_measurement_theta_min      4.2630
_cell_volume                     1747.28(18)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.907
_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    -68.00 -41.00   1.00   91.17    --  -10.68-179.00  60.00   27
  2  \w    -60.00  17.00   1.00   91.17    --  -10.68 -57.00-120.00   77
  3  \w    -74.00  30.00   1.00   91.17    --  -10.68 -19.00 -60.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0513967000
_diffrn_orient_matrix_UB_12      0.0393151000
_diffrn_orient_matrix_UB_13      0.0147269000
_diffrn_orient_matrix_UB_21      0.0433445000
_diffrn_orient_matrix_UB_22      0.0202567000
_diffrn_orient_matrix_UB_23      0.0324496000
_diffrn_orient_matrix_UB_31      0.0245472000
_diffrn_orient_matrix_UB_32      0.0466111000
_diffrn_orient_matrix_UB_33      -0.0264996000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9179
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.270
_diffrn_reflns_theta_min         3.690
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.188
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.081
_refine_diff_density_min         -0.087
_refine_diff_density_rms         0.020
_refine_ls_abs_structure_details
;
 Flack x determined using 870 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0414P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.789
_reflns_number_gt                2496
_reflns_number_total             4045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03803c2.cif
_cod_data_source_block           o9a_auto
_cod_depositor_comments          'Adding full bibliography for 7062906.cif.'
_cod_original_cell_volume        1747.30(18)
_cod_database_code               7062906
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H20 N2'
_olex2_refinement_description
;
;
_shelx_res_checksum              7490
_shelx_hkl_checksum              85866
_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 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.722