3,6-Fluoren[5]arenes: synthesis, structure and complexation with fullerenes C<sub>60</sub> and C<sub>70</sub>.
Wang, Jia-Qi; Han, Ying; Chen, Chuan-Feng; Chemical communications (Cambridge, England) 57 (2021) 3987–3990; doi:10.1039/d1cc00916h

data_7128043
_publ_section_title
;
 3,6-Fluoren[5]arenes: synthesis, structure and complexation with
 fullerenes C<sub>60</sub> and C<sub>70</sub>.
;
_journal_issue                   33
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3987
_journal_page_last               3990
_journal_paper_doi               10.1039/d1cc00916h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         '3(C H Cl3), C120 H150 O10'
_chemical_formula_sum            'C123 H153 Cl9 O10'
_chemical_formula_weight         2110.49
_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     dual
_audit_creation_date             2020-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-14 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                95.436(2)
_cell_angle_beta                 95.461(2)
_cell_angle_gamma                92.331(2)
_cell_formula_units_Z            2
_cell_length_a                   12.9917(4)
_cell_length_b                   21.9009(5)
_cell_length_c                   22.5682(3)
_cell_measurement_reflns_used    13741
_cell_measurement_temperature    169.99(11)
_cell_measurement_theta_max      69.0710
_cell_measurement_theta_min      2.6890
_cell_volume                     6355.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_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    -56.00 -23.00   0.50    0.05    --  -46.95  55.00 -66.00   66
  2  \w   -116.00 -42.00   0.50    0.05    --  -46.95 -55.00 150.00  148
  3  \w     38.00 117.00   0.50    0.05    --   46.95  55.00 -66.00  158
  4  \w    -12.00  50.00   0.50    0.05    --   46.95 -55.00 150.00  124
  5  \w   -151.00 -84.00   0.50    0.20    --  -99.00 -55.00 150.00  134
  6  \w    -52.00 -26.00   0.50    0.20    --  -99.00  55.00 -66.00   52
  7  \w     33.00  66.00   0.50    0.20    --  103.25 -55.00 150.00   66
  8  \w     91.00 169.00   0.50    0.20    --  103.25  55.00 -66.00  156
  9  \w   -119.00 -93.00   0.50    0.05    --  -46.95-125.00 -60.00   52
 10  \w     -6.00  25.00   0.50    0.05    --  -46.95  55.00 -66.00   62
 11  \w    -57.00  -1.00   0.50    0.05    --  -46.95  57.00  90.00  112
 12  \w   -119.00 -84.00   0.50    0.05    --  -46.95-125.00  90.00   70
 13  \w    -37.00  21.00   0.50    0.05    --  -46.95  38.00 -60.00  116
 14  \w    -25.00  19.00   0.50    0.05    --   46.95 -19.00   0.00   88
 15  \w    -68.00 -42.00   0.50    0.20    --  -99.00  61.00 150.00   52
 16  \w    -82.00 -55.00   0.50    0.20    --  -99.00 125.00 -90.00   54
 17  \w   -100.00 -70.00   0.50    0.20    --  -99.00  77.00  90.00   60
 18  \w   -112.00 -82.00   0.50    0.20    --  -99.00 125.00 -30.00   60
 19  \w    -80.00 -31.00   0.50    0.20    --  -99.00 147.00 127.32   98
 20  \w    -51.00 -26.00   0.50    0.20    --  -99.00  77.00  90.00   50
 21  \w    -58.00 -26.00   0.50    0.20    --  -99.00 115.00  78.94   64
 22  \w   -131.00-106.00   0.50    0.20    --  -99.00 153.00-126.42   50
 23  \w   -164.00 -91.00   0.50    0.20    --  -99.00 -64.00-120.26  146
 24  \w   -126.00 -28.00   0.50    0.20    --  -99.00 144.00  18.93  196
 25  \w   -127.00 -84.00   0.50    0.20    --  -99.00 147.00 127.32   86
 26  \w    -60.00 -28.00   0.50    0.20    --  -99.00 125.00 -30.00   64
 27  \w    -68.00 -36.00   0.50    0.20    --  -99.00  61.00  90.00   64
 28  \w   -106.00 -80.00   0.50    0.20    --  -99.00 115.00  78.94   52
 29  \w   -158.00 -80.00   0.50    0.20    --  -99.00 -68.00  12.99  156
 30  \w    121.00 169.00   0.50    0.20    --  103.25  30.00 -90.00   96
 31  \w     91.00 117.00   0.50    0.20    --  103.25  30.00 -90.00   52
 32  \w     80.00 152.00   0.50    0.20    --  103.25 125.00  30.00  144
 33  \w     46.00  81.00   0.50    0.20    --  103.25 -94.00 150.00   70
 34  \w     63.00  89.00   0.50    0.20    --  103.25 -94.00  30.00   52
 35  \w     32.00  70.00   0.50    0.20    --  103.25 -61.00 -60.00   76
 36  \w     88.00 164.00   0.50    0.20    --  103.25  61.00  30.00  152
 37  \w     32.00 106.00   0.50    0.20    --  103.25 -94.00 120.00  148
 38  \w     31.00 109.00   0.50    0.20    --  103.25-125.00  30.00  156
 39  \w     71.00  97.00   0.50    0.20    --  103.25 -94.00-180.00   52
 40  \w    131.00 161.00   0.50    0.20    --  103.25  45.00-180.00   60
 41  \w     99.00 125.00   0.50    0.20    --  103.25  45.00-180.00   52
 42  \w     65.00 102.00   0.50    0.20    --  103.25 -94.00  90.00   74
 43  \w     49.00  97.00   0.50    0.20    --  103.25-125.00   0.00   96
 44  \w     88.00 126.00   0.50    0.20    --  103.25  61.00-150.00   76
 45  \w     32.00 106.00   0.50    0.20    --  103.25 -94.00-150.00  148
 46  \w     40.00  99.00   0.50    0.20    --  103.25 -94.00 -90.00  118
;
_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      -0.0096097000
_diffrn_orient_matrix_UB_12      0.0635445000
_diffrn_orient_matrix_UB_13      0.0340731000
_diffrn_orient_matrix_UB_21      -0.0914820000
_diffrn_orient_matrix_UB_22      -0.0257646000
_diffrn_orient_matrix_UB_23      0.0303398000
_diffrn_orient_matrix_UB_31      0.0759227000
_diffrn_orient_matrix_UB_32      -0.0174282000
_diffrn_orient_matrix_UB_33      0.0516484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            93801
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.870
_diffrn_reflns_theta_min         2.689
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2248
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1457
_refine_ls_number_reflns         25361
_refine_ls_number_restraints     543
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0930
_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^)+(0.1461P)^2^+4.1986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2534
_refine_ls_wR_factor_ref         0.2809
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16723
_reflns_number_total             25361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00916h2.cif
_cod_data_source_block           tx3531_sq
_cod_depositor_comments          'Adding full bibliography for 7128043.cif.'
_cod_database_code               7128043
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOCl
_reflns_odcompleteness_completeness 99.72
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C94-C93 = C95-C94 = C94A-C94
 1.54 with sigma of 0.01
 C9A-C8 = C9-C8 = C8-C7
 1.54 with sigma of 0.01
 C43-C42 = C44A-C43 = C44-C43
 1.54 with sigma of 0.01
 C115-C114 = C1B-C1C = C114-C113 = C14-C1A = C113-C112 = C112-C104 = C104-C14
 1.54 with sigma of 0.01
 C1D-C104 = C116-C104 = C117-C116 = C1E-C1D = C1F-C1E = C118-C117 = C1G-C1F =
 C119-C118
 1.54 with sigma of 0.01
 C91A-C90 = C91-C90
 1.54 with sigma of 0.01
 C45A-C33 = C45-C33 = C46-C45 = C46A-C45A = C47A-C46A = C48A-C47A = C48-C47
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C94 \\sim C95 \\sim C94A: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C8 \\sim C9 \\sim C9A: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C43 \\sim C44 \\sim C44A: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C14 \\sim C112 \\sim C1A \\sim C113 \\sim C1B \\sim C115 \\sim C114 \\sim C1C:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C116 \\sim C1D \\sim C1E \\sim C117 \\sim C1G \\sim C118 \\sim C1F \\sim C119:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C91 \\sim C91A \\sim C90: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C45 \\sim C46 \\sim C47 \\sim C45A \\sim C46A \\sim C47A \\sim C48A \\sim C48:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C94) \\sim Ueq, Uanis(C95) \\sim Ueq, Uanis(C94A) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(C43) \\sim Ueq,
Uanis(C44) \\sim Ueq, Uanis(C44A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C14) \\sim Ueq, Uanis(C112) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C113)
\\sim Ueq, Uanis(C114) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C1C) \\sim Ueq,
Uanis(C115) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C116) \\sim Ueq, Uanis(C1D) \\sim Ueq, Uanis(C1E) \\sim Ueq, Uanis(C117)
\\sim Ueq, Uanis(C118) \\sim Ueq, Uanis(C1G) \\sim Ueq, Uanis(C1F) \\sim Ueq,
Uanis(C119) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C91) \\sim Ueq, Uanis(C91A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C45) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C45A) \\sim Ueq, Uanis(C46A)
\\sim Ueq, Uanis(C47A) \\sim Ueq, Uanis(C48A) \\sim Ueq, Uanis(C46) \\sim Ueq,
Uanis(C48) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H8BC)=Sof(H8BD)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=1-FVAR(1)
 Sof(H8AA)=Sof(H8AB)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=FVAR(1)
 Sof(H43C)=Sof(H43D)=Sof(C44A)=Sof(H44D)=Sof(H44E)=Sof(H44F)=1-FVAR(2)
 Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(2)
 Sof(H94C)=Sof(H94D)=Sof(C94A)=Sof(H94E)=Sof(H94F)=Sof(H94G)=1-FVAR(3)
 Sof(H94A)=Sof(H94B)=Sof(C95)=Sof(H95A)=Sof(H95B)=Sof(H95C)=FVAR(3)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C1B)=Sof(H1BA)=
 Sof(H1BB)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=1-FVAR(4)
 Sof(C112)=Sof(H11D)=Sof(H11E)=Sof(C113)=Sof(H11F)=Sof(H11G)=Sof(C114)=
 Sof(H11H)=Sof(H11I)=Sof(C115)=Sof(H11J)=Sof(H11K)=Sof(H11L)=FVAR(4)
 Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(C1F)=Sof(H1FA)=
 Sof(H1FB)=Sof(C1G)=Sof(H1GA)=Sof(H1GB)=Sof(H1GC)=1-FVAR(5)
 Sof(C117)=Sof(H11M)=Sof(H11N)=Sof(C118)=Sof(H11O)=Sof(H11P)=Sof(C119)=
 Sof(H11Q)=Sof(H11R)=Sof(H11S)=Sof(C116)=Sof(H11T)=Sof(H11U)=FVAR(5)
 Sof(H90C)=Sof(H90D)=Sof(C91A)=Sof(H91D)=Sof(H91E)=Sof(H91F)=1-FVAR(6)
 Sof(H90A)=Sof(H90B)=Sof(C91)=Sof(H91A)=Sof(H91B)=Sof(H91C)=FVAR(6)
 Sof(C45A)=Sof(H45C)=Sof(H45D)=Sof(C46A)=Sof(H46C)=Sof(H46D)=Sof(C47A)=
 Sof(H47C)=Sof(H47D)=Sof(C48A)=Sof(H48D)=Sof(H48E)=Sof(H48F)=1-FVAR(7)
 Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(C47)=Sof(H47A)=
 Sof(H47B)=Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=FVAR(7)
5.a Ternary CH refined with riding coordinates:
 C121(H121), C122(H122), C123(H123)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C25(H25A,
 H25B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C43(H43C,H43D),
 C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C49(H49A,H49B), C64(H64A,H64B),
  C65(H65A,H65B), C66(H66A,H66B), C68(H68A,H68B), C69(H69A,H69B), C70(H70A,
 H70B), C72(H72A,H72B), C88(H88A,H88B), C89(H89A,H89B), C90(H90A,H90B),
 C90(H90C,H90D), C92(H92A,H92B), C93(H93A,H93B), C94(H94A,H94B), C94(H94C,H94D),
  C96(H96A,H96B), C112(H11D,H11E), C113(H11F,H11G), C114(H11H,H11I), C1D(H1DA,
 H1DB), C117(H11M,H11N), C118(H11O,H11P), C120(H12A,H12B), C8(H8AA,H8AB),
 C8(H8BC,H8BD), C14(H14A,H14B), C1A(H1AA,H1AB), C1B(H1BA,H1BB), C116(H11T,H11U),
  C1E(H1EA,H1EB), C1F(H1FA,H1FB), C45A(H45C,H45D), C46A(H46C,H46D), C47A(H47C,
 H47D)
5.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C20(H20), C21(H21), C29(H29), C32(H32), C36(H36),
 C39(H39), C53(H53), C56(H56), C59(H59), C61(H61), C75(H75), C77(H77), C83(H83),
  C86(H86), C98(H98), C101(H101), C107(H107), C110(H110)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C24(H24A,H24B,H24C), C26(H26A,H26B,
 H26C), C40(H40A,H40B,H40C), C48(H48A,H48B,H48C), C50(H50A,H50B,H50C), C63(H63A,
 H63B,H63C), C67(H67A,H67B,H67C), C71(H71A,H71B,H71C), C76(H76A,H76B,H76C),
 C87(H87A,H87B,H87C), C91(H91A,H91B,H91C), C103(H10A,H10B,H10C), C111(H11A,H11B,
 H11C), C115(H11J,H11K,H11L), C119(H11Q,H11R,H11S), C9(H9A,H9B,H9C), C9A(H9AA,
 H9AB,H9AC), C95(H95A,H95B,H95C), C94A(H94E,H94F,H94G), C44(H44A,H44B,H44C),
 C44A(H44D,H44E,H44F), C1C(H1CA,H1CB,H1CC), C1G(H1GA,H1GB,H1GC), C91A(H91D,H91E,
 H91F), C48A(H48D,H48E,H48F)
;
_shelx_res_checksum              98224
_shelx_fab_checksum              18500
_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 1.650
_oxdiff_exptl_absorpt_empirical_full_min 0.572