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_7059535
_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         'C36 H50 S4'
_chemical_formula_sum            'C36 H50 S4'
_chemical_formula_weight         611.00
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-03
_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                90
_cell_angle_beta                 92.2020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.32000(10)
_cell_length_b                   10.2529(2)
_cell_length_c                   35.0079(5)
_cell_measurement_reflns_used    17162
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.1920
_cell_measurement_theta_min      2.4620
_cell_volume                     3342.78(9)
_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      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_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    -34.00  25.00   0.50    2.24    --  -47.95  37.00 -60.00  118
  2  \w    -16.00  28.00   0.50    2.24    --  -47.95  19.00-150.00   88
  3  \w    -43.00 -14.00   0.50   11.00    --  -86.25  45.00  30.00   58
  4  \w    -81.00   2.00   0.50    2.24    --  -47.95 106.00-171.00  166
  5  \w     19.00  85.00   0.50    2.24    --   47.95-106.00  88.00  132
  6  \w     35.00 107.00   0.50   11.00    --  107.75-106.00  88.00  144
  7  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00 120.00   88
  8  \w     35.00 106.00   0.50    8.00    --  107.75 -94.00 120.00  142
  9  \w     35.00 106.00   0.50    8.00    --  107.75 -94.00  90.00  142
 10  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00  90.00   88
 11  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00 150.00   88
 12  \w     35.00 131.00   0.50    8.00    --  107.75 -77.00  90.00  192
 13  \w     95.00 178.00   0.50    8.00    --  107.75  30.00 -90.00  166
 14  \w    105.00 178.00   0.50    8.00    --  107.75 106.00-171.00  146
 15  \w     95.00 178.00   0.50    8.00    --  107.75  45.00-120.00  166
 16  \w     95.00 178.00   0.50    8.00    --  107.75  45.00   0.00  166
 17  \w     95.00 178.00   0.50    8.00    --  107.75  45.00  90.00  166
 18  \w     95.00 178.00   0.50    8.00    --  107.75  45.00 150.00  166
 19  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00-120.00   88
 20  \w     35.00 106.00   0.50    8.00    --  107.75 -94.00-150.00  142
 21  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00-150.00   88
 22  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00 -90.00   88
 23  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00 -30.00   88
 24  \w    -81.00 -13.00   0.50    8.00    --  -86.25 106.00-171.00  136
 25  \w   -120.00 -25.00   0.50    2.00    --  -47.95 -77.00-180.00  190
 26  \w   -120.00 -73.00   0.50    2.00    --  -47.95-125.00-120.00   94
 27  \w   -120.00 -73.00   0.50    2.00    --  -47.95-125.00 -60.00   94
 28  \w   -159.00 -83.00   0.50    8.00    --  -86.25-106.00  88.00  152
 29  \w   -120.00 -73.00   0.50    2.00    --  -47.95-125.00 150.00   94
 30  \w     82.00 108.00   0.50    8.00    --  107.75-109.00-176.00   52
 31  \w    -13.00  27.00   0.50    2.00    --  -47.82  19.00  60.00   80
 32  \w     -6.00  20.00   0.50    2.00    --  -47.82  19.00 150.00   52
 33  \w     64.00  91.00   0.50    2.00    --   47.82-125.00   0.00   54
 34  \w     40.00  71.00   0.50    2.00    --   47.82-125.00-180.00   62
 35  \w    -63.00 -23.00   0.50    8.00    --  -86.25  61.00 -90.00   80
 36  \w    107.00 176.00   0.50    8.00    --  107.75  45.00 -30.00  138
 37  \w     81.00 107.00   0.50    8.00    --  107.75-102.00-118.10   52
 38  \w     59.00 104.00   0.50    8.00    --  107.75 -94.00 -90.00   90
 39  \w     40.00  66.00   0.50    8.00    --  107.75-102.00-118.10   52
 40  \w     85.00 112.00   0.50    8.00    --  107.75-125.00  90.00   54
 41  \w     36.00  61.00   0.50    8.00    --  107.75-125.00-180.00   50
 42  \w    120.00 163.00   0.50    8.00    --  107.75  45.00-180.00   86
 43  \w     80.00 106.00   0.50    8.00    --  107.75 -94.00   0.00   52
 44  \w     43.00  73.00   0.50    8.00    --  107.75-125.00  90.00   60
 45  \w     97.00 139.00   0.50    8.00    --  107.75  15.00 -30.00   84
 46  \w     51.00 106.00   0.50    8.00    --  107.75 -99.00 -41.89  110
 47  \w     40.00  84.00   0.50    8.00    --  107.75 -94.00  30.00   88
 48  \w    131.00 164.00   0.50    8.00    --  107.75 125.00  30.00   66
 49  \w     81.00 107.00   0.50    8.00    --  107.75-102.00 118.03   52
 50  \w     82.00 112.00   0.50    8.00    --  107.75-125.00 -90.00   60
 51  \w    106.00 131.00   0.50    8.00    --  107.75  61.00-180.00   50
 52  \w    143.00 169.00   0.50    8.00    --  107.75  61.00-180.00   52
 53  \w     36.00  75.00   0.50    8.00    --  107.75 -94.00   0.00   78
 54  \w     35.00  60.00   0.50    8.00    --  107.75 -61.00   0.00   50
 55  \w     57.00 106.00   0.50    8.00    --  107.75 -94.00 -30.00   98
 56  \w    -66.00 -41.00   0.50    2.00    --  -47.82 109.00 -80.00   50
 57  \w     61.00  87.00   0.50    8.00    --  107.75 -94.00-120.00   52
 58  \w   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00 -60.00  188
 59  \w   -119.00 -33.00   0.50    2.00    --  -47.82 -57.00  90.00  172
 60  \w   -119.00 -34.00   0.50    2.00    --  -47.82 -50.00-155.73  170
 61  \w   -119.00 -33.00   0.50    2.00    --  -47.82 -57.00 -30.00  172
 62  \w   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00-120.00  188
 63  \w   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00   0.00  188
 64  \w   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00  90.00  188
 65  \w   -121.00 -47.00   0.50    2.00    --  -47.82 -37.00-150.00  148
 66  \w   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00  60.00  188
 67  \w     30.00  55.00   0.50    2.00    --   47.82-109.00-176.00   50
 68  \w     30.00  55.00   0.50    2.00    --   47.82-109.00-176.00   50
 69  \w    -72.00 -47.00   0.50    8.00    --  -86.25 109.00 -80.00   50
;
_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      0.0564076000
_diffrn_orient_matrix_UB_12      -0.1115739000
_diffrn_orient_matrix_UB_13      0.0259443000
_diffrn_orient_matrix_UB_21      0.0077335000
_diffrn_orient_matrix_UB_22      0.0940805000
_diffrn_orient_matrix_UB_23      0.0343432000
_diffrn_orient_matrix_UB_31      -0.1552341000
_diffrn_orient_matrix_UB_32      -0.0359701000
_diffrn_orient_matrix_UB_33      0.0093336000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1055
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            56658
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.518
_diffrn_reflns_theta_min         2.526
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39747
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       needle
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0638
_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^)+(0.1297P)^2^+0.7120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1731
_refine_ls_wR_factor_ref         0.1868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5664
_reflns_number_total             6956
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01495h2.cif
_cod_data_source_block           9floc10
_cod_depositor_comments
;Adding full bibliography for 7059533--7059535.cif.

 Adding full bibliography for 7059533--7059535.cif.
;
_cod_database_code               7059535
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C36H50S4
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.544
_diffrn_oxdiff_digest_frames
;
01c80f1d8cba99039968c412e1943485b50733273ae
;
_diffrn_oxdiff_digest_hkl
;
01660dd7f9f0c4892459417f6274ff44d8bf38
;
_reflns_odcompleteness_completeness 98.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,
 H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B),
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B),
  C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              13844
_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 3.560
_oxdiff_exptl_absorpt_empirical_full_min 0.426