Iron-catalyzed peroxidation of fluorenes and 9-alkyl-9<i>H</i>-fluorenes and oxidative cleavage of the CC bond in 9-alkylidene-fluorenes.
Saha, Ratnakar; Hembram, Bhairab Chand; Panda, Asutosh; Bagh, Bidraha; Organic & biomolecular chemistry 23 (2025) 4232–4239; doi:10.1039/d5ob00102a

data_7160447
_publ_section_title
;
 Iron-catalyzed peroxidation of fluorenes and 9-alkyl-9<i>H</i>-fluorenes
 and oxidative cleavage of the C&#xe001;C bond in 9-alkylidene-fluorenes.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4232
_journal_page_last               4239
_journal_paper_doi               10.1039/d5ob00102a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C15 H23 Cl2 Fe N3 O2'
_chemical_formula_sum            'C15 H23 Cl2 Fe N3 O2'
_chemical_formula_weight         404.11
_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     iterative
_audit_creation_date             2023-06-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-09-12 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.263(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2505(3)
_cell_length_b                   14.1312(4)
_cell_length_c                   12.6158(3)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.8990
_cell_measurement_theta_min      4.6680
_cell_volume                     1826.00(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_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    -78.00   7.00   0.50    0.79    --  -38.50 109.00-113.00  170
  2  \w     14.00  89.00   0.50    0.79    --   49.56-109.00 150.00  150
  3  \w    103.00 174.00   0.50    3.17    --  107.46 109.00-113.00  142
  4  \w     41.00 108.00   0.50    3.17    --  107.46-109.00 150.00  134
  5  \w   -101.00 -27.00   0.50    0.79    --  -38.50 -57.00  60.00  148
  6  \w   -105.00 -35.00   0.50    0.79    --  -38.50 -37.00 -90.00  140
  7  \w     46.00 116.00   0.50    0.79    --   49.56  37.00-120.00  140
  8  \w     38.00 113.00   0.50    0.79    --   49.56  57.00  60.00  150
  9  \w    -17.00  53.00   0.50    0.79    --   49.56 -37.00  60.00  140
 10  \w     39.00 107.00   0.50    3.17    --  107.46 -94.00-180.00  136
 11  \w     39.00 111.00   0.50    3.17    --  107.46 -30.00  90.00  144
 12  \w     43.00 112.00   0.50    3.17    --  107.46 -45.00 150.00  138
 13  \w    103.00 172.00   0.50    3.17    --  107.46  45.00 -90.00  138
 14  \w     95.00 170.00   0.50    3.17    --  107.46  61.00 150.00  150
 15  \w     97.00 158.00   0.50    3.17    --  107.46 125.00  30.00  122
 16  \w     68.00  94.00   0.50    3.17    --  107.46 -94.00-120.00   52
 17  \w     54.00 100.00   0.50    3.17    --  107.46 -94.00   0.00   92
 18  \w     47.00 110.00   0.50    3.17    --  107.46 -30.00 -30.00  126
 19  \w     43.00 111.00   0.50    3.17    --  107.46 -45.00 -90.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0178753000
_diffrn_orient_matrix_UB_12      0.1007182000
_diffrn_orient_matrix_UB_13      0.0448697000
_diffrn_orient_matrix_UB_21      0.0477309000
_diffrn_orient_matrix_UB_22      0.0338593000
_diffrn_orient_matrix_UB_23      -0.1079093000
_diffrn_orient_matrix_UB_31      -0.1415288000
_diffrn_orient_matrix_UB_32      0.0241841000
_diffrn_orient_matrix_UB_33      -0.0358593000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14189
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.625
_diffrn_reflns_theta_min         4.701
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.722
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0078(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0809P)^2^+0.4562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3508
_reflns_number_total             3803
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00102a2.cif
_cod_data_source_block           bb-rs-py-2morph-fe-cl2_auto
_cod_depositor_comments          'Adding full bibliography for 7160447.cif.'
_cod_database_code               7160447
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O Fe Cl'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B), C5(H5A,H5B), C12(H12A,H12B), C1(H1A,H1B),
 C4(H4A,H4B), C14(H14A,H14B), C2(H2A,H2B), C3(H3A,H3B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C7(H7)
;
_shelx_res_checksum              45551
_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 1.484
_oxdiff_exptl_absorpt_empirical_full_min 0.644