Synthesis and characterization of bis(dithiafulvenyl)-substituted fluorenones and fluorenylidene-1,3-dithioles
Salami, Fatemeh; Zhao, Yuming; New Journal of Chemistry 44 (2020) 9179–9189; doi:10.1039/D0NJ01495H

data_7059534
_publ_section_title
;
 Synthesis and characterization of bis(dithiafulvenyl)-substituted
 fluorenones and fluorenylidene-1,3-dithioles
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9179
_journal_page_last               9189
_journal_paper_doi               10.1039/D0NJ01495H
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C37 H28 O S8'
_chemical_formula_sum            'C37 H28 O S8'
_chemical_formula_weight         745.07
_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             2020-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-17 deposited with the CCDC.	2020-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                99.0250(10)
_cell_angle_beta                 99.0750(10)
_cell_angle_gamma                97.7900(10)
_cell_formula_units_Z            6
_cell_length_a                   12.8667(2)
_cell_length_b                   19.3354(3)
_cell_length_c                   20.7609(3)
_cell_measurement_reflns_used    28692
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.3110
_cell_measurement_theta_min      2.1820
_cell_volume                     4968.67(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_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 0.975
_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     24.00 120.00   0.50    8.00    --   47.82  79.00 -34.00  192
  2  \w     84.00 178.00   0.50   64.65    --  107.75  79.00 -34.00  188
  3  \w     95.00 178.00   0.50   64.65    --  107.75  30.00  30.00  166
  4  \w     95.00 178.00   0.50   64.65    --  107.75  45.00-120.00  166
  5  \w     95.00 178.00   0.50   64.65    --  107.75  45.00 -60.00  166
  6  \w     95.00 178.00   0.50   64.65    --  107.75  30.00  60.00  166
  7  \w     95.00 178.00   0.50   64.65    --  107.75  45.00 150.00  166
  8  \w     95.00 178.00   0.50   64.65    --  107.75  30.00 120.00  166
  9  \w     95.00 178.00   0.50   64.65    --  107.75  30.00  90.00  166
 10  \w     91.00 178.00   0.50   64.65    --  107.75  61.00 -90.00  174
 11  \w     95.00 178.00   0.50   64.65    --  107.75  30.00-150.00  166
 12  \w     35.00 132.00   0.50   64.65    --  107.75 -79.00-158.00  194
 13  \w     35.00 106.00   0.50   64.65    --  107.75 -94.00 -30.00  142
 14  \w     35.00  79.00   0.50   64.65    --  107.75 -61.00-150.00   88
 15  \w     35.00 106.00   0.50   64.65    --  107.75 -94.00-180.00  142
 16  \w     35.00  79.00   0.50   64.65    --  107.75 -61.00 -30.00   88
 17  \w     35.00 106.00   0.50   64.65    --  107.75 -94.00 -60.00  142
 18  \w     35.00 106.00   0.50   64.65    --  107.75 -94.00  90.00  142
 19  \w     35.00 106.00   0.50   64.65    --  107.75 -98.00 175.01  142
 20  \w     35.00 112.00   0.50   64.65    --  107.75-125.00 150.00  154
 21  \w     35.00 107.00   0.50   64.65    --  107.75-104.00  44.80  144
 22  \w     35.00 106.00   0.50   64.65    --  107.75 -94.00  60.00  142
 23  \w    -24.00  72.00   0.50    8.00    --   47.82 -79.00-158.00  192
 24  \w    -25.00  48.00   0.50    8.00    --   47.82 -37.00-150.00  146
 25  \w    -71.00  25.00   0.50    8.00    --  -47.82  79.00 -34.00  192
 26  \w    -16.00  28.00   0.50    8.00    --  -47.82  19.00  90.00   88
 27  \w    -43.00 -14.00   0.50   64.65    --  -86.25  45.00 150.00   58
 28  \w   -110.00 -13.00   0.50   64.65    --  -86.25  79.00 -34.00  194
 29  \w   -119.00 -33.00   0.50    8.00    --  -47.82 -57.00-150.00  172
 30  \w   -119.00 -24.00   0.50    8.00    --  -47.82 -79.00-158.00  190
 31  \w   -119.00 -73.00   0.50    8.00    --  -47.82-125.00 -60.00   92
 32  \w   -119.00 -25.00   0.50    8.00    --  -47.82 -77.00 -60.00  188
 33  \w   -119.00 -35.00   0.50    8.00    --  -47.82 -49.00  94.76  168
 34  \w   -119.00 -25.00   0.50    8.00    --  -47.82 -77.00   0.00  188
 35  \w   -119.00 -25.00   0.50    8.00    --  -47.82 -77.00 120.00  188
 36  \w   -119.00 -33.00   0.50    8.00    --  -47.82 -57.00  30.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0395654000
_diffrn_orient_matrix_UB_12      -0.0765677000
_diffrn_orient_matrix_UB_13      0.0077615000
_diffrn_orient_matrix_UB_21      0.0817421000
_diffrn_orient_matrix_UB_22      0.0103371000
_diffrn_orient_matrix_UB_23      0.0649057000
_diffrn_orient_matrix_UB_31      -0.0828405000
_diffrn_orient_matrix_UB_32      0.0268248000
_diffrn_orient_matrix_UB_33      0.0395945000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            97458
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.425
_diffrn_reflns_theta_min         2.192
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       needle
_exptl_crystal_F_000             2316
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.103
_refine_diff_density_min         -1.238
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1360
_refine_ls_number_reflns         20586
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0743
_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^)+(0.0996P)^2^+7.3384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1938
_refine_ls_wR_factor_ref         0.2122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15432
_reflns_number_total             20586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01495h2.cif
_cod_data_source_block           2-7-me-2-d_3
_cod_depositor_comments
;Adding full bibliography for 7059533--7059535.cif.

 Adding full bibliography for 7059533--7059535.cif.
;
_cod_original_cell_volume        4968.66(13)
_cod_database_code               7059534
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C37H28OS8
_shelx_estimated_absorpt_t_max   0.710
_shelx_estimated_absorpt_t_min   0.420
_diffrn_oxdiff_digest_frames
;
0114fa9b19df8bab7c0c336653d2555dbd0002532dc
;
_diffrn_oxdiff_digest_hkl
;
018c6efd305ffd80ccea5025694fd3e9a0c4a9
;
_reflns_odcompleteness_completeness 99.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C36-S7A
 1.8 with sigma of 0.02
 C34-S7 \\sim C34-S7A
 with sigma of 0.02
 S8-C35 \\sim S8A-C35
 with sigma of 0.02
 S8-C37 \\sim S8A-C37
 with sigma of 0.02
 S11-C59 \\sim S11A-C59
 with sigma of 0.02
 S11-C61 \\sim S11A-C61
 with sigma of 0.02
 S14-C70 \\sim S14A-C70
 with sigma of 0.02
 S14-C72 \\sim S14A-C72
 with sigma of 0.02
 S16-C72 \\sim S16A-C72
 with sigma of 0.02
 S16-C74 \\sim S16A-C74
 with sigma of 0.02
 S19-C96 \\sim S19A-C96
 with sigma of 0.02
 S19-C98 \\sim S19A-C98
 with sigma of 0.02
 S9-C58 \\sim S9A-C58
 with sigma of 0.02
 S9-C59 \\sim S9A-C59
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C36) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(S4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(S7) = Uanis(S7A)
Uanis(S8) = Uanis(S8A)
Uanis(S11) = Uanis(S11A)
Uanis(S14) = Uanis(S14A)
Uanis(S16) = Uanis(S16A)
Uanis(S19) = Uanis(S19A)
Uanis(S20) = Uanis(S20A)
Uanis(C36) = Uanis(C36A)
Uanis(S9) = Uanis(S9A)
Uanis(S4A) = Uanis(C25)
Uanis(C25A) = Uanis(C25)
4. Others
 Sof(S15A)=Sof(C73A)=Sof(H73D)=Sof(H73E)=Sof(H73F)=1-FVAR(1)
 Sof(S15)=Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(H73C)=FVAR(1)
 Sof(S12A)=Sof(C62A)=Sof(H62D)=Sof(H62E)=Sof(H62F)=1-FVAR(2)
 Sof(S12)=Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=FVAR(2)
 Sof(C1A)=Sof(H11A)=Sof(H11B)=Sof(H11C)=1-FVAR(3)
 Sof(C110)=Sof(H11D)=Sof(H11E)=Sof(H11F)=FVAR(3)
 Sof(S16A)=Sof(H74D)=Sof(H74E)=Sof(H74F)=1-FVAR(4)
 Sof(S16)=Sof(H74A)=Sof(H74B)=Sof(H74C)=FVAR(4)
 Sof(S8A)=Sof(H37D)=Sof(H37E)=Sof(H37F)=1-FVAR(5)
 Sof(S8)=Sof(H37A)=Sof(H37B)=Sof(H37C)=FVAR(5)
 Sof(S7A)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=1-FVAR(6)
 Sof(S7)=Sof(C36A)=Sof(H36D)=Sof(H36E)=Sof(H36F)=FVAR(6)
 Sof(S19A)=Sof(H98D)=Sof(H98E)=Sof(H98F)=1-FVAR(7)
 Sof(S19)=Sof(H98A)=Sof(H98B)=Sof(H98C)=FVAR(7)
 Sof(S20A)=Sof(C99A)=Sof(H99D)=Sof(H99E)=Sof(H99F)=1-FVAR(8)
 Sof(S20)=Sof(C99)=Sof(H99A)=Sof(H99B)=Sof(H99C)=FVAR(8)
 Sof(S14A)=1-FVAR(9)
 Sof(S14)=FVAR(9)
 Sof(S11A)=Sof(H61D)=Sof(H61E)=Sof(H61F)=1-FVAR(10)
 Sof(S11)=Sof(H61A)=Sof(H61B)=Sof(H61C)=FVAR(10)
 Sof(S4A)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(11)
 Sof(S4)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(11)
 Sof(S9A)=1-FVAR(12)
 Sof(S9)=FVAR(12)
5.a Riding coordinates:
 C98(H98D,H98E,H98F)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C15(H15), C16(H16),
 C18(H18), C19(H19), C20(H20), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32),
  C40(H40), C42(H42), C43(H43), C46(H46), C47(H47), C49(H49), C52(H52),
 C53(H53), C55(H55), C56(H56), C57(H57), C64(H64), C65(H65), C67(H67), C68(H68),
  C69(H69), C77(H77), C79(H79), C80(H80), C83(H83), C84(H84), C86(H86),
 C89(H89), C90(H90), C92(H92), C93(H93), C94(H94), C101(H101), C102(H102),
 C104(H104), C105(H105), C106(H106)
5.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C25A(H25D,H25E,H25F), C36(H36A,H36B,
 H36C), C36A(H36D,H36E,H36F), C37(H37A,H37B,H37C), C37(H37D,H37E,H37F),
 C61(H61A,H61B,H61C), C61(H61D,H61E,H61F), C62(H62A,H62B,H62C), C62A(H62D,H62E,
 H62F), C73(H73A,H73B,H73C), C73A(H73D,H73E,H73F), C74(H74A,H74B,H74C),
 C74(H74D,H74E,H74F), C98(H98A,H98B,H98C), C99(H99A,H99B,H99C), C99A(H99D,H99E,
 H99F), C110(H11D,H11E,H11F), C1A(H11A,H11B,H11C), C111(H11G,H11H,H11I)
;
_shelx_res_checksum              59974
_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 1.462
_oxdiff_exptl_absorpt_empirical_full_min 0.757