Efficient iron catalyzed ligand-free access to acridines and acridinium ions
Mandal, Susanta; Chhetri, Karan; Bhuyan, Samuzal; Roy, Biswajit G.; Green Chemistry 22 (2020) 3178–3185; doi:10.1039/D0GC00617C

data_7240160
_publ_section_title
;
 Efficient iron catalyzed ligand-free access to acridines and acridinium
 ions
;
_journal_issue                   10
_journal_name_full               'Green Chemistry'
_journal_page_first              3178
_journal_page_last               3185
_journal_paper_doi               10.1039/D0GC00617C
_journal_volume                  22
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C28 H24 N O2, 2(C H Cl3), Cl'
_chemical_formula_sum            'C30 H26 Cl7 N O2'
_chemical_formula_weight         680.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc23f39z
_audit_creation_date             2019-05-05
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-23 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.397(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1043(8)
_cell_length_b                   12.8257(9)
_cell_length_c                   12.9176(9)
_cell_measurement_reflns_used    2065
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.0700
_cell_measurement_theta_min      3.7420
_cell_volume                     1621.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9326
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega  -52.00   48.00   1.0000    6.1200
omega____ theta____ kappa____ phi______ frames
    -       18.1617  -77.0000   60.0000 100

  2 omega  -52.00   48.00   1.0000    6.1200
omega____ theta____ kappa____ phi______ frames
    -       18.1617  -77.0000 -180.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0322953000
_diffrn_orient_matrix_UB_12      0.0484865000
_diffrn_orient_matrix_UB_13      0.0038263000
_diffrn_orient_matrix_UB_21      -0.0339930000
_diffrn_orient_matrix_UB_22      -0.0223662000
_diffrn_orient_matrix_UB_23      0.0365114000
_diffrn_orient_matrix_UB_31      0.0551190000
_diffrn_orient_matrix_UB_32      0.0146309000
_diffrn_orient_matrix_UB_33      0.0432119000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5391
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         3.401
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
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_refine_ls_abs_structure_Flack   -0.05(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4527
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0895
_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^)+(0.1435P)^2^+0.3537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2242
_refine_ls_wR_factor_ref         0.2535
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3332
_reflns_number_total             4527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc00617c2.cif
_cod_data_source_block           kar_07
_cod_depositor_comments
;Adding full bibliography for 7240160--7240161.cif.

 Adding full bibliography for 7240160--7240161.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7240160
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C28 H24 O2 N1'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.05(17)
 -0.05(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C30(H30), C29(H29)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C13(H13), C12(H12), C11(H11), C24(H24),
 C25(H25), C26(H26), C27(H27), C28(H28), C3(H3), C4(H4), C5(H5), C6(H6)
3.c Fitted hexagon refined as free rotating group:
 C16(C17,C18,C19,C20,C15), C14(C13,C12,C11,C10,C9), C23(C24,C25,C26,C27,C28),
 C2(C3,C4,C5,C6,C7)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              23032
_shelx_hkl_checksum              27409
_olex2_submission_special_instructions 'No special instructions were received'