Modification of fluorene and fluorenone core <i>via</i> C-H functionalization.
Banga, Shefali; Babu, Srinivasarao Arulananda; Organic & biomolecular chemistry 23 (2025) 9692–9712; doi:10.1039/d5ob01242b

data_7160762
_publ_section_title
;
 Modification of fluorene and fluorenone core <i>via</i> C-H
 functionalization.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9692
_journal_page_last               9712
_journal_paper_doi               10.1039/d5ob01242b
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C31 H23 Cl N2 O'
_chemical_formula_sum            'C31 H23 Cl N2 O'
_chemical_formula_weight         474.96
_chemical_name_systematic        C31H23ClN2O
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-01-10 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                83.843(5)
_cell_angle_beta                 69.351(6)
_cell_angle_gamma                76.847(5)
_cell_formula_units_Z            2
_cell_length_a                   9.6750(6)
_cell_length_b                   10.6988(7)
_cell_length_c                   12.6825(8)
_cell_measurement_reflns_used    2387
_cell_measurement_temperature    293
_cell_measurement_theta_max      21.1910
_cell_measurement_theta_min      2.6000
_cell_volume                     1195.69(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.941
_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    -69.00 119.00   0.50    5.00    --   29.89  54.00-150.00  376
  2  \w    -69.00 119.00   0.50    5.00    --   29.89  54.00  60.00  376
  3  \w    -69.00 119.00   0.50    5.00    --   29.89  54.00  60.00  376
  4  \w    -69.00 119.00   0.50    5.00    --   29.89  54.00 -30.00  376
  5  \w    -69.00  56.00   0.50    5.00    --   29.89  54.00 120.00  250
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0650108000
_diffrn_orient_matrix_UB_12      -0.0257597000
_diffrn_orient_matrix_UB_13      0.0151127000
_diffrn_orient_matrix_UB_21      -0.0349394000
_diffrn_orient_matrix_UB_22      0.0319991000
_diffrn_orient_matrix_UB_23      0.0518752000
_diffrn_orient_matrix_UB_31      -0.0309408000
_diffrn_orient_matrix_UB_32      -0.0543311000
_diffrn_orient_matrix_UB_33      0.0256091000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.1170
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26590
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.780
_diffrn_reflns_theta_min         2.564
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.027
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         8344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.2241
_refine_ls_R_factor_gt           0.0907
_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^)+(0.1520P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2233
_refine_ls_wR_factor_ref         0.3301
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3083
_reflns_number_total             8344
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01242b2.cif
_cod_data_source_block           sb426
_cod_depositor_comments
'Adding full bibliography for 7160761--7160762.cif.'
_cod_database_code               7160762
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00J(H00J), C00K(H00K), C00M(H00M),
 C00O(H00O), C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z)
2.b Idealised Me refined as rotating group:
 C00Q(H00A,H00E,H00F), C00U(H00G,H00H,H00I)
;
_shelx_res_checksum              92546
_olex2_submission_original_sample_id 'sb 426'
_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 1.749
_oxdiff_exptl_absorpt_empirical_full_min 0.849