#------------------------------------------------------------------------------
#$Date: 2022-10-12 00:56:34 +0300 (Wed, 12 Oct 2022) $
#$Revision: 278524 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/08/7130843.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7130843
loop_
_publ_author_name
'Chen, Zhicai'
'Zhang, Yu'
'Wang, Pu'
'Yang, Jiaxin'
'Yang, Kun'
'Li, Jianfeng'
'Yang, Jie'
'Li, Yongchun'
'Dong, Huanli'
'Guo, Xugang'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     95.00 178.00   0.50    0.29    --  107.36  57.00  30.00  166
  2  ω     87.00 178.00   0.50    0.29    --  107.36  92.00-112.00  182
  3  ω    147.00 175.00   0.50    0.29    --  107.36  38.00 150.00   56
  4  ω     94.00 144.00   0.50    0.29    --  107.36  38.00 150.00  100
  5  ω     -5.00  21.00   0.50    0.07    --  -47.45  19.00 150.00   52
  6  ω    -62.00 -37.00   0.50    0.29    -- -104.50  57.00  90.00   50
  7  ω    -61.00 -32.00   0.50    0.29    -- -104.50  57.00   0.00   58
  8  ω    -61.00 -34.00   0.50    0.29    -- -104.50  57.00  30.00   54
  9  ω    -95.00 -68.00   0.50    0.29    -- -104.50  77.00 -60.00   54
 10  ω    -60.00 -32.00   0.50    0.29    -- -104.50  57.00-120.00   56
 11  ω    -61.00 -32.00   0.50    0.29    -- -104.50  57.00-150.00   58
 12  ω    -20.00  26.00   0.50    0.07    --  -47.45  38.00-120.00   92
 13  ω     38.00 110.00   0.50    0.29    --  107.36-125.00 150.00  144
 14  ω     75.00 109.00   0.50    0.29    --  107.36-125.00 120.00   68
 15  ω     35.00  62.00   0.50    0.29    --  107.36-125.00 120.00   54
 16  ω     62.00 102.00   0.50    0.29    --  107.36 -92.00 134.00   80
 17  ω     54.00 106.00   0.50    0.29    --  107.36 -99.00  30.00  104
 18  ω     70.00 101.00   0.50    0.29    --  107.36 -99.00 -30.00   62
 19  ω     40.00  91.00   0.50    0.29    --  107.36 -99.00 -60.00  102
 20  ω     39.00  68.00   0.50    0.29    --  107.36 -99.00 -30.00   58
 21  ω    -24.00  77.00   0.50    0.07    --   47.45 -92.00 134.00  202
 22  ω     35.00  68.00   0.50    0.29    --  107.36 -57.00 -30.00   66
 23  ω     37.00  67.00   0.50    0.29    --  107.36 -57.00-150.00   60
 24  ω     41.00 109.00   0.50    0.29    --  107.36 -77.00-150.00  136
 25  ω     39.00  66.00   0.50    0.29    --  107.36 -57.00 120.00   54
 26  ω    -26.00  30.00   0.50    0.07    --   47.45 -19.00  60.00  112
 27  ω    -12.00  13.00   0.50    0.07    --   47.45 -19.00 -60.00   50
 28  ω     10.00  46.00   0.50    0.07    --   47.45 -38.00-180.00   72
 29  ω   -112.00 -75.00   0.50    0.07    --  -47.45-125.00-120.00   74
 30  ω   -113.00 -74.00   0.50    0.07    --  -47.45-125.00 -90.00   78
 31  ω   -174.00 -80.00   0.50    0.29    -- -104.50 -92.00 134.00  188
 32  ω   -147.00-120.00   0.50    0.29    -- -104.50 -62.00 177.90   54
 33  ω   -173.00-126.00   0.50    0.29    -- -104.50 -38.00  60.00   94
 34  ω   -124.00 -97.00   0.50    0.29    -- -104.50 -38.00  60.00   54
 35  ω   -131.00 -97.00   0.50    0.29    -- -104.50 -38.00 -60.00   68
 36  ω   -174.00-142.00   0.50    0.29    -- -104.50 -38.00 -60.00   64
 37  ω   -158.00-109.00   0.50    0.29    -- -104.50 -53.00-162.37   98
 38  ω    -93.00 -68.00   0.50    0.29    -- -104.50  92.00-112.00   50
 39  ω    -78.00 -48.00   0.50    0.29    -- -104.50 148.00 -35.96   60
 40  ω   -128.00 -93.00   0.50    0.29    -- -104.50 148.00 -35.96   70
 41  ω    -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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0905P)²+0.2988P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O14 O 0.5127(3) 0.03302(16) 0.25508(7) 0.0447(4) Uani 1 1 d . . . . .
O15 O -0.1613(3) 0.32205(17) 0.16730(8) 0.0505(4) Uani 1 1 d . . . . .
N7 N 0.1762(3) 0.19113(17) 0.21970(8) 0.0317(4) Uani 1 1 d . . . . .
N29 N 0.8038(4) 0.6558(2) 0.48854(9) 0.0444(5) Uani 1 1 d . . . . .
N25 N 0.1820(4) 0.9408(2) 0.40148(10) 0.0506(5) Uani 1 1 d . . . . .
C10 C 0.1953(3) 0.47305(19) 0.28720(8) 0.0272(4) Uani 1 1 d . . . . .
C20 C 0.3837(3) 0.58979(19) 0.36519(9) 0.0274(4) Uani 1 1 d . . . . .
C27 C 0.4366(4) 0.6908(2) 0.40390(9) 0.0296(4) Uani 1 1 d . . . . .
C11 C 0.4005(3) 0.37395(19) 0.31926(9) 0.0271(4) Uani 1 1 d . . . . .
C21 C 0.5163(4) 0.44363(19) 0.36627(9) 0.0282(4) Uani 1 1 d . . . . .
C19 C 0.1840(4) 0.60511(19) 0.31465(9) 0.0279(4) Uani 1 1 d . . . . .
C9 C 0.0266(4) 0.4541(2) 0.23896(9) 0.0303(4) Uani 1 1 d . . . . .
C18 C 0.0047(4) 0.7193(2) 0.29222(9) 0.0318(4) Uani 1 1 d . . . . .
H18 H -0.002751 0.808373 0.309972 0.038 Uiso 1 1 calc R . . . .
C28 C 0.6408(4) 0.6684(2) 0.45081(9) 0.0324(4) Uani 1 1 d . . . . .
C12 C 0.4886(4) 0.23418(19) 0.30909(9) 0.0290(4) Uani 1 1 d . . . . .
C22 C 0.7188(4) 0.3734(2) 0.40428(9) 0.0315(4) Uani 1 1 d . . . . .
H22 H 0.796894 0.420180 0.435941 0.038 Uiso 1 1 calc R . . . .
C13 C 0.3942(4) 0.1489(2) 0.25986(9) 0.0315(4) Uani 1 1 d . . . . .
C24 C 0.6932(4) 0.1653(2) 0.34826(9) 0.0332(4) Uani 1 1 d . . . . .
H24 H 0.757046 0.069216 0.342542 0.040 Uiso 1 1 calc R . . . .
C17 C -0.1639(4) 0.7005(2) 0.24316(10) 0.0341(4) Uani 1 1 d . . . . .
H17 H -0.287502 0.777847 0.227262 0.041 Uiso 1 1 calc R . . . .
C8 C 0.0093(4) 0.3197(2) 0.20703(10) 0.0342(4) Uani 1 1 d . . . . .
C26 C 0.2936(4) 0.8293(2) 0.40146(10) 0.0341(4) Uani 1 1 d . . . . .
C16 C -0.1548(4) 0.5710(2) 0.21712(10) 0.0338(4) Uani 1 1 d . . . . .
H16 H -0.273223 0.560838 0.183851 0.041 Uiso 1 1 calc R . . . .
C6 C 0.1185(4) 0.0790(2) 0.17831(10) 0.0354(5) Uani 1 1 d . . . . .
H6A H -0.077134 0.080944 0.170290 0.043 Uiso 1 1 calc R . . . .
H6B H 0.167695 -0.021238 0.200854 0.043 Uiso 1 1 calc R . . . .
C5 C 0.2726(4) 0.1076(2) 0.11515(10) 0.0401(5) Uani 1 1 d . . . . .
H5A H 0.468303 0.103947 0.123135 0.048 Uiso 1 1 calc R . . . .
H5B H 0.225708 0.208480 0.092920 0.048 Uiso 1 1 calc R . . . .
C23 C 0.8042(4) 0.2319(2) 0.39463(10) 0.0342(4) Uani 1 1 d . . . . .
H23 H 0.941112 0.180956 0.420440 0.041 Uiso 1 1 calc R . . . .
C4 C 0.2099(5) -0.0056(3) 0.07243(11) 0.0448(5) Uani 1 1 d . . . . .
H4A H 0.011692 -0.011067 0.069829 0.054 Uiso 1 1 calc R . . . .
H4B H 0.281369 0.031109 0.028965 0.054 Uiso 1 1 calc R . . . .
C3 C 0.3223(5) -0.1608(3) 0.09349(11) 0.0479(6) Uani 1 1 d . . . . .
H3A H 0.257090 -0.197542 0.137491 0.057 Uiso 1 1 calc R . . . .
H3B H 0.521407 -0.157696 0.093816 0.057 Uiso 1 1 calc R . . . .
C2 C 0.2386(7) -0.2686(3) 0.04948(14) 0.0654(7) Uani 1 1 d . . . . .
H2A H 0.039399 -0.270139 0.048904 0.079 Uiso 1 1 calc R . . . .
H2B H 0.304454 -0.231271 0.005590 0.079 Uiso 1 1 calc R . . . .
C1 C 0.3436(8) -0.4235(3) 0.06876(16) 0.0817(10) Uani 1 1 d . . . . .
H1A H 0.272739 -0.487534 0.040584 0.122 Uiso 1 1 calc GR . . . .
H1B H 0.286083 -0.460005 0.112840 0.122 Uiso 1 1 calc GR . . . .
H1C H 0.540928 -0.424577 0.065539 0.122 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N7 C8 134.39(16) . . ?
C13 N7 C6 112.79(15) . . ?
C8 N7 C6 112.70(15) . . ?
C19 C10 C11 108.47(16) . . ?
C9 C10 C11 130.34(17) . . ?
C9 C10 C19 121.18(16) . . ?
C27 C20 C21 126.37(17) . . ?
C27 C20 C19 127.04(16) . . ?
C21 C20 C19 106.59(15) . . ?
C20 C27 C28 123.31(16) . . ?
C20 C27 C26 123.33(17) . . ?
C26 C27 C28 113.35(16) . . ?
C21 C11 C10 108.73(15) . . ?
C12 C11 C10 130.28(17) . . ?
C12 C11 C21 120.98(17) . . ?
C11 C21 C20 108.27(15) . . ?
C22 C21 C20 130.78(17) . . ?
C22 C21 C11 120.94(16) . . ?
C10 C19 C20 107.95(15) . . ?
C18 C19 C10 120.19(18) . . ?
C18 C19 C20 131.87(17) . . ?
C10 C9 C8 127.13(17) . . ?
C10 C9 C16 117.69(17) . . ?
C16 C9 C8 115.17(17) . . ?
C19 C18 C17 118.54(17) . . ?
N29 C28 C27 177.6(2) . . ?
C11 C12 C13 127.27(17) . . ?
C11 C12 C24 116.98(17) . . ?
C24 C12 C13 115.73(16) . . ?
C21 C22 C23 117.97(18) . . ?
O14 C13 N7 117.77(17) . . ?
O14 C13 C12 117.26(17) . . ?
N7 C13 C12 124.96(16) . . ?
C23 C24 C12 122.24(17) . . ?
C16 C17 C18 121.11(17) . . ?
O15 C8 N7 117.66(17) . . ?
O15 C8 C9 117.17(17) . . ?
N7 C8 C9 125.17(17) . . ?
N25 C26 C27 177.7(2) . . ?
C17 C16 C9 121.27(19) . . ?
N7 C6 C5 112.11(16) . . ?
C6 C5 C4 112.07(17) . . ?
C24 C23 C22 120.87(17) . . ?
C3 C4 C5 115.54(19) . . ?
C4 C3 C2 111.9(2) . . ?
C1 C2 C3 113.8(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O14 C13 1.214(2) . ?
O15 C8 1.210(2) . ?
N7 C13 1.405(3) . ?
N7 C8 1.414(2) . ?
N7 C6 1.492(2) . ?
N29 C28 1.146(3) . ?
N25 C26 1.146(3) . ?
C10 C11 1.454(2) . ?
C10 C19 1.421(3) . ?
C10 C9 1.377(3) . ?
C20 C27 1.366(3) . ?
C20 C21 1.470(2) . ?
C20 C19 1.471(3) . ?
C27 C28 1.431(3) . ?
C27 C26 1.429(3) . ?
C11 C21 1.411(3) . ?
C11 C12 1.386(2) . ?
C21 C22 1.386(3) . ?
C19 C18 1.387(3) . ?
C9 C8 1.501(3) . ?
C9 C16 1.408(3) . ?
C18 C17 1.390(3) . ?
C12 C13 1.494(3) . ?
C12 C24 1.403(3) . ?
C22 C23 1.394(3) . ?
C24 C23 1.374(3) . ?
C17 C16 1.383(3) . ?
C6 C5 1.515(3) . ?
C5 C4 1.525(3) . ?
C4 C3 1.513(3) . ?
C3 C2 1.536(3) . ?
C2 C1 1.492(4) . ?
