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_7160761
_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         'C30 H20 N2 O2'
_chemical_formula_sum            'C30 H20 N2 O2'
_chemical_formula_weight         440.48
_chemical_name_systematic        C30H20N2O2
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-11
_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                90
_cell_angle_beta                 117.568(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2374(9)
_cell_length_b                   10.3904(5)
_cell_length_c                   16.2165(9)
_cell_measurement_reflns_used    12340
_cell_measurement_temperature    293
_cell_measurement_theta_max      31.5270
_cell_measurement_theta_min      2.6360
_cell_volume                     2275.9(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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 2014/4 (Sheldrick, 2014)'
_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 0.979
_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    -69.00 118.80   0.30   20.00    --   29.89  54.00   0.00  626
  2  \w    -69.00 118.80   0.30   20.00    --   29.89  54.00  90.00  626
  3  \w    -69.00 118.80   0.30   20.00    --   29.89  54.00  90.00  626
  4  \w    -69.00 118.80   0.30   20.00    --   29.89  54.00-150.00  626
  5  \w    -20.00   6.10   0.30   20.00    --   29.89  54.00-150.00   87
  6  \w     72.00  97.80   0.30   20.00    --   29.89  54.00-150.00   86
  7  \w    -24.00   1.20   0.30   20.00    --   29.89  54.00  30.00   84
  8  \w    -62.00 -15.80   0.30   20.00    --   29.89  54.00 -60.00  154
  9  \w     -6.00  20.10   0.30   20.00    --   29.89  54.00   0.00   87
;
_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      -0.0391937000
_diffrn_orient_matrix_UB_12      -0.0141589000
_diffrn_orient_matrix_UB_13      -0.0447524000
_diffrn_orient_matrix_UB_21      -0.0191005000
_diffrn_orient_matrix_UB_22      0.0630239000
_diffrn_orient_matrix_UB_23      -0.0027662000
_diffrn_orient_matrix_UB_31      0.0292406000
_diffrn_orient_matrix_UB_32      0.0221065000
_diffrn_orient_matrix_UB_33      -0.0206970000
_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  0.0344
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            50891
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.761
_diffrn_reflns_theta_min         2.502
_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    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73095
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         8237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1127P)^2^+0.2134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1754
_refine_ls_wR_factor_ref         0.2057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5592
_reflns_number_total             8237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01242b2.cif
_cod_data_source_block           sb_537_30_08_2023
_cod_depositor_comments
'Adding full bibliography for 7160761--7160762.cif.'
_cod_database_code               7160761
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.976
_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:
 C00D(H00D), C00E(H00E), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X)
2.b Idealised Me refined as rotating group:
 C00Y(H00A,H00B,H00C)
;
_shelx_res_checksum              48869
_olex2_submission_original_sample_id SB_537
_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 1.308
_oxdiff_exptl_absorpt_empirical_full_min 0.775