A Class of Electron-Deficient Units: Fluorenone Imide and Its Electron-Withdrawing Group-Functionalized Derivatives
Chen, Zhicai; Zhang, Yu; Wang, Pu; Yang, Jiaxin; Yang, Kun; Li, Jianfeng; Yang, Jie; Li, Yongchun; Dong, Huanli; Guo, Xugang; Chemical Communications  (2022) –; doi:10.1039/D2CC04922H

data_7130843
_publ_section_title
;
 A Class of Electron-Deficient Units: Fluorenone Imide and Its
 Electron-Withdrawing Group-Functionalized Derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04922H
_journal_year                    2022
_chemical_formula_moiety         'C24 H19 N3 O2'
_chemical_formula_sum            'C24 H19 N3 O2'
_chemical_formula_weight         381.42
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2022-04-10 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                80.708(2)
_cell_angle_beta                 88.385(2)
_cell_angle_gamma                88.576(2)
_cell_formula_units_Z            2
_cell_length_a                   4.96443(14)
_cell_length_b                   9.1287(2)
_cell_length_c                   21.2708(6)
_cell_measurement_reflns_used    5009
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      75.2990
_cell_measurement_theta_min      2.1460
_cell_volume                     950.74(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     95.00 178.00   0.50    0.29    --  107.36  57.00  30.00  166
  2  \w     87.00 178.00   0.50    0.29    --  107.36  92.00-112.00  182
  3  \w    147.00 175.00   0.50    0.29    --  107.36  38.00 150.00   56
  4  \w     94.00 144.00   0.50    0.29    --  107.36  38.00 150.00  100
  5  \w     -5.00  21.00   0.50    0.07    --  -47.45  19.00 150.00   52
  6  \w    -62.00 -37.00   0.50    0.29    -- -104.50  57.00  90.00   50
  7  \w    -61.00 -32.00   0.50    0.29    -- -104.50  57.00   0.00   58
  8  \w    -61.00 -34.00   0.50    0.29    -- -104.50  57.00  30.00   54
  9  \w    -95.00 -68.00   0.50    0.29    -- -104.50  77.00 -60.00   54
 10  \w    -60.00 -32.00   0.50    0.29    -- -104.50  57.00-120.00   56
 11  \w    -61.00 -32.00   0.50    0.29    -- -104.50  57.00-150.00   58
 12  \w    -20.00  26.00   0.50    0.07    --  -47.45  38.00-120.00   92
 13  \w     38.00 110.00   0.50    0.29    --  107.36-125.00 150.00  144
 14  \w     75.00 109.00   0.50    0.29    --  107.36-125.00 120.00   68
 15  \w     35.00  62.00   0.50    0.29    --  107.36-125.00 120.00   54
 16  \w     62.00 102.00   0.50    0.29    --  107.36 -92.00 134.00   80
 17  \w     54.00 106.00   0.50    0.29    --  107.36 -99.00  30.00  104
 18  \w     70.00 101.00   0.50    0.29    --  107.36 -99.00 -30.00   62
 19  \w     40.00  91.00   0.50    0.29    --  107.36 -99.00 -60.00  102
 20  \w     39.00  68.00   0.50    0.29    --  107.36 -99.00 -30.00   58
 21  \w    -24.00  77.00   0.50    0.07    --   47.45 -92.00 134.00  202
 22  \w     35.00  68.00   0.50    0.29    --  107.36 -57.00 -30.00   66
 23  \w     37.00  67.00   0.50    0.29    --  107.36 -57.00-150.00   60
 24  \w     41.00 109.00   0.50    0.29    --  107.36 -77.00-150.00  136
 25  \w     39.00  66.00   0.50    0.29    --  107.36 -57.00 120.00   54
 26  \w    -26.00  30.00   0.50    0.07    --   47.45 -19.00  60.00  112
 27  \w    -12.00  13.00   0.50    0.07    --   47.45 -19.00 -60.00   50
 28  \w     10.00  46.00   0.50    0.07    --   47.45 -38.00-180.00   72
 29  \w   -112.00 -75.00   0.50    0.07    --  -47.45-125.00-120.00   74
 30  \w   -113.00 -74.00   0.50    0.07    --  -47.45-125.00 -90.00   78
 31  \w   -174.00 -80.00   0.50    0.29    -- -104.50 -92.00 134.00  188
 32  \w   -147.00-120.00   0.50    0.29    -- -104.50 -62.00 177.90   54
 33  \w   -173.00-126.00   0.50    0.29    -- -104.50 -38.00  60.00   94
 34  \w   -124.00 -97.00   0.50    0.29    -- -104.50 -38.00  60.00   54
 35  \w   -131.00 -97.00   0.50    0.29    -- -104.50 -38.00 -60.00   68
 36  \w   -174.00-142.00   0.50    0.29    -- -104.50 -38.00 -60.00   64
 37  \w   -158.00-109.00   0.50    0.29    -- -104.50 -53.00-162.37   98
 38  \w    -93.00 -68.00   0.50    0.29    -- -104.50  92.00-112.00   50
 39  \w    -78.00 -48.00   0.50    0.29    -- -104.50 148.00 -35.96   60
 40  \w   -128.00 -93.00   0.50    0.29    -- -104.50 148.00 -35.96   70
 41  \w    -77.00  25.00   0.50    0.07    --  -47.45  92.00-112.00  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0966475000
_diffrn_orient_matrix_UB_12      -0.0190025000
_diffrn_orient_matrix_UB_13      -0.0663476000
_diffrn_orient_matrix_UB_21      -0.0839212000
_diffrn_orient_matrix_UB_22      0.1655070000
_diffrn_orient_matrix_UB_23      -0.0131422000
_diffrn_orient_matrix_UB_31      0.2828998000
_diffrn_orient_matrix_UB_32      0.0387414000
_diffrn_orient_matrix_UB_33      -0.0285388000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10550
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.986
_diffrn_reflns_theta_min         2.105
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0017(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0905P)^2^+0.2988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2905
_reflns_number_total             3433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04922h2.cif
_cod_data_source_block           tx10669_auto
_cod_database_code               7130843
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N F'
_chemical_oxdiff_usercomment     CHONS
_diffrn_oxdiff_digest_frames
;
01f79092db6192077c01da9585326c3d9900037f473
;
_diffrn_oxdiff_digest_hkl
;
0188160c9a500e2355883a69a9fe53bf4545ea
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B), C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C22(H22), C24(H24), C17(H17), C16(H16), C23(H23)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.764