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_7059533
_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         '0.5(C H2 Cl2), C42 H34 S12'
_chemical_formula_sum            'C42.5 H35 Cl S12'
_chemical_formula_weight         965.87
_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             2019-11-20
_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                89.3300(10)
_cell_angle_beta                 83.4290(10)
_cell_angle_gamma                83.1130(10)
_cell_formula_units_Z            4
_cell_length_a                   9.43840(10)
_cell_length_b                   20.8406(3)
_cell_length_c                   22.59980(10)
_cell_measurement_reflns_used    55050
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      76.8970
_cell_measurement_theta_min      2.1260
_cell_volume                     4384.35(8)
_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      173.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_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    -31.00  23.00   0.50    6.68    --  -47.82  36.00 -84.00  108
  2  \w    -12.00  21.00   0.50    6.68    --  -47.82  19.00-180.00   66
  3  \w     46.00  92.00   0.50    6.68    --   47.82  36.00 -84.00   92
  4  \w     61.00 114.00   0.50    6.68    --   47.82  57.00 -90.00  106
  5  \w     96.00 178.00   0.50   26.72    --  107.75  36.00 -84.00  164
  6  \w    106.00 175.00   0.50   26.72    --  107.75  15.00-150.00  138
  7  \w    107.00 133.00   0.50   26.72    --  107.75 125.00-180.00   52
  8  \w     95.00 156.00   0.50   26.72    --  107.75 125.00 -90.00  122
  9  \w    109.00 173.00   0.50   26.72    --  107.75  61.00  60.00  128
 10  \w    143.00 174.00   0.50   26.72    --  107.75  45.00 120.00   62
 11  \w    122.00 148.00   0.50   26.72    --  107.75 125.00  60.00   52
 12  \w     95.00 174.00   0.50   26.72    --  107.75  45.00 150.00  158
 13  \w    120.00 156.00   0.50   26.72    --  107.75  45.00  90.00   72
 14  \w    121.00 166.00   0.50   26.72    --  107.75 125.00 150.00   90
 15  \w     97.00 131.00   0.50   26.72    --  107.75  45.00 120.00   68
 16  \w     51.00  78.00   0.50   26.72    --  107.75 -61.00 -30.00   54
 17  \w     51.00 106.00   0.50   26.72    --  107.75 -94.00 -60.00  110
 18  \w     86.00 112.00   0.50   26.72    --  107.75-125.00   0.00   52
 19  \w     81.00 109.00   0.50   26.72    --  107.75-125.00  30.00   56
 20  \w     70.00  95.00   0.50   26.72    --  107.75-125.00  60.00   50
 21  \w     76.00 112.00   0.50   26.72    --  107.75-125.00  90.00   72
 22  \w     70.00 106.00   0.50   26.72    --  107.75 -94.00  60.00   72
 23  \w     67.00 102.00   0.50   26.72    --  107.75 -94.00 150.00   70
 24  \w     60.00  86.00   0.50   26.72    --  107.75-125.00 150.00   52
 25  \w     48.00  73.00   0.50   26.72    --  107.75-125.00  90.00   50
 26  \w     36.00 102.00   0.50   26.72    --  107.75 -94.00 120.00  132
 27  \w     38.00  93.00   0.50    6.68    --   47.82-125.00 150.00  110
 28  \w     38.00  64.00   0.50   26.72    --  107.75-125.00  30.00   52
 29  \w     35.00  80.00   0.50   26.72    --  107.75-125.00   0.00   90
 30  \w     80.00 110.00   0.50   26.72    --  107.75-125.00 -60.00   60
 31  \w     84.00 128.00   0.50   26.72    --  107.75-147.00-126.16   88
 32  \w     62.00  97.00   0.50   26.72    --  107.75 -94.00-150.00   70
 33  \w     49.00  77.00   0.50   26.72    --  107.75 -61.00-120.00   56
 34  \w     49.00 105.00   0.50   26.72    --  107.75 -94.00 -90.00  112
 35  \w     46.00  95.00   0.50    6.68    --   47.82-125.00 -30.00   98
 36  \w     37.00  69.00   0.50   26.72    --  107.75 -61.00 -60.00   64
 37  \w     37.00  65.00   0.50   26.72    --  107.75 -61.00 -90.00   56
 38  \w     43.00  69.00   0.50   26.72    --  107.75 -61.00-150.00   52
 39  \w     43.00 107.00   0.50   26.72    --  107.75-105.00-132.31  128
 40  \w     45.00 112.00   0.50   26.72    --  107.75-125.00 -90.00  134
 41  \w     46.00  72.00   0.50   26.72    --  107.75-125.00 -60.00   52
 42  \w     37.00 106.00   0.50   26.72    --  107.75 -94.00   0.00  138
 43  \w     38.00  63.00   0.50   26.72    --  107.75-125.00  60.00   50
 44  \w     36.00 106.00   0.50   30.00    --  107.75 -99.00  99.93  140
 45  \w     36.00  62.00   0.50   30.00    --  107.75 -94.00 150.00   52
 46  \w     35.00  62.00   0.50   30.00    --  107.75 -61.00 120.00   54
 47  \w     35.00  79.00   0.50   30.00    --  107.75 -61.00 150.00   88
 48  \w     36.00  77.00   0.50   30.00    --  107.75 -61.00  30.00   82
 49  \w     99.00 178.00   0.50   30.00    --  107.75  15.00-120.00  158
 50  \w    -15.00  19.00   0.50   16.00    --   47.82 -36.00 118.00   68
 51  \w    -15.00  26.00   0.50   16.00    --  -47.82  19.00  60.00   82
 52  \w    -42.00 -16.00   0.50   30.00    --  -86.25  45.00 120.00   52
 53  \w   -121.00 -37.00   0.50   16.00    --  -47.82 -36.00 118.00  168
 54  \w   -116.00 -73.00   0.50   16.00    --  -47.82-125.00  60.00   86
 55  \w   -141.00-116.00   0.50   30.00    --  -86.25 -36.00 118.00   50
 56  \w   -117.00 -73.00   0.50   16.00    --  -47.82-125.00 -90.00   88
 57  \w    -70.00 -15.00   0.50   16.00    --  -47.82 125.00 -90.00  110
 58  \w    -97.00 -71.00   0.50   30.00    --  -86.25  87.00  56.00   52
 59  \w    -21.00   6.00   0.50   16.00    --   14.00 103.00 -47.31   54
 60  \w    -17.00   9.00   0.50   16.00    --   18.00 102.00 153.55   52
 61  \w    -10.00  15.00   0.50   16.00    --   22.00  96.00 139.09   50
 62  \w     -4.00  21.00   0.50   16.00    --   30.00 100.00-133.90   50
 63  \w   -106.00 -54.00   0.50   16.00    --  -38.00 158.00 129.38  104
 64  \w      8.00  33.00   0.50   16.00    --   38.00  92.00-171.43   50
 65  \w     14.00  39.00   0.50   16.00    --   42.00  88.00  43.44   50
 66  \w     12.00  37.00   0.50   16.00    --   42.00  92.00  80.18   50
 67  \w     14.00  39.00   0.50   16.00    --   42.00  89.00 -56.56   50
 68  \w     13.00  38.00   0.50   16.00    --   42.00  91.00-146.36   50
 69  \w    -58.00 -26.00   0.50   16.00    --  -47.82 -77.00-150.00   64
 70  \w     36.00  95.00   0.50   16.00    --   47.82  19.00 120.00  118
 71  \w    -52.00 -26.00   0.50   16.00    --  -50.00 -79.00 144.95   52
 72  \w     27.00  53.00   0.50   16.00    --   50.00  80.00 104.47   52
 73  \w    -56.00 -30.00   0.50   16.00    --  -54.00 -80.00  28.23   52
 74  \w    -58.00 -31.00   0.50   16.00    --  -54.00 -78.00 -56.09   54
 75  \w     31.00  64.00   0.50   16.00    --   54.00  77.00 144.75   66
 76  \w     30.00  66.00   0.50   16.00    --   54.00  79.00-141.44   72
 77  \w    -80.00 -35.00   0.50   16.00    --  -58.00 -77.00 -89.73   90
 78  \w    -61.00 -35.00   0.50   16.00    --  -58.00 -79.00 -14.22   52
 79  \w    -66.00 -36.00   0.50   16.00    --  -58.00 -76.00  64.76   60
 80  \w   -130.00 -87.00   0.50   16.00    --  -58.00 -77.00 -89.73   86
 81  \w     34.00  59.00   0.50   16.00    --   58.00  80.00 -89.54   50
 82  \w    -72.00 -39.00   0.50   16.00    --  -62.00 -76.00   2.24   66
 83  \w     38.00  65.00   0.50   16.00    --   62.00  80.00 134.98   54
 84  \w   -139.00-112.00   0.50   16.00    --  -66.00 -74.00 -97.49   54
 85  \w    -67.00 -42.00   0.50   16.00    --  -66.00 -79.00  47.74   50
 86  \w    -70.00 -44.00   0.50   16.00    --  -66.00 -74.00 -97.49   52
 87  \w     43.00  68.00   0.50   16.00    --   66.00  78.00-162.57   50
 88  \w     43.00  69.00   0.50   16.00    --   66.00  78.00 150.38   52
 89  \w     43.00  68.00   0.50   16.00    --   66.00  78.00  11.56   50
 90  \w     45.00  86.00   0.50   16.00    --   66.00  72.00 -34.55   82
 91  \w    -73.00 -48.00   0.50   30.00    --  -70.00 -75.00  82.43   50
 92  \w     49.00  87.00   0.50   16.00    --   70.00  76.00-146.25   76
 93  \w     49.00  75.00   0.50   16.00    --   70.00  76.00 161.61   52
 94  \w    -72.00 -46.00   0.50   30.00    --  -70.00 -79.00-122.33   52
 95  \w     48.00  93.00   0.50   16.00    --   70.00  76.00  23.81   90
 96  \w     48.00  74.00   0.50   16.00    --   70.00  76.00 -35.72   52
 97  \w    -80.00 -76.50   0.50   30.00    --  -74.00 -74.00-109.25    7
;
_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      -0.0033218000
_diffrn_orient_matrix_UB_12      -0.0324479000
_diffrn_orient_matrix_UB_13      0.0616626000
_diffrn_orient_matrix_UB_21      -0.1585895000
_diffrn_orient_matrix_UB_22      -0.0097615000
_diffrn_orient_matrix_UB_23      -0.0020685000
_diffrn_orient_matrix_UB_31      0.0471574000
_diffrn_orient_matrix_UB_32      -0.0663018000
_diffrn_orient_matrix_UB_33      -0.0300317000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            32975
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.657
_diffrn_reflns_theta_min         1.968
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.361
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78095
_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    1.463
_exptl_crystal_description       needle
_exptl_crystal_F_000             1996
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.976
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1013
_refine_ls_number_reflns         32975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0539
_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^)+(0.1015P)^2^+2.2802P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1570
_reflns_Friedel_coverage         0.000
_reflns_number_gt                29123
_reflns_number_total             32975
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9774\% 
 around [0.00 1.00 -0.00] (reciprocal) or [-0.26 0.97 0.00] (direct)
;
_cod_data_source_file            d0nj01495h2.cif
_cod_data_source_block           36me_twin1_hklf4
_cod_depositor_comments
;
 Adding full bibliography for 7059533--7059535.cif.

2024-10-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C H2 Cl2, 2(C42 H34 S12)'
_cod_original_formula_sum        'C85 H70 Cl2 S24'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1931.75
_cod_database_code               7059533
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C85H70Cl2S24
_chemical_oxdiff_usercomment     YELLOW
_shelx_estimated_absorpt_t_max   0.742
_shelx_estimated_absorpt_t_min   0.394
_diffrn_oxdiff_digest_frames
;
01c598bda12c210a4ceaeac69551a4056007305c9c7
;
_diffrn_oxdiff_digest_hkl
;
01c84fcca60bca4bcafa3182242bcf32d5095b
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4990(7)
 0.5010(7)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20),
 C21(H21), C27(H27), C28(H28), C30(H30), C32(H32), C33(H33), C35(H35), C36(H36),
  C37(H37), C53(H53), C55(H55), C56(H56), C58(H58), C59(H59), C61(H61),
 C62(H62), C63(H63), C69(H69), C70(H70), C72(H72), C74(H74), C75(H75), C77(H77),
  C78(H78), C79(H79)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C51(H51A,H51B,H51C), C52(H52A,
 H52B,H52C), C67(H67A,H67B,H67C), C68(H68A,H68B,H68C), C83(H83A,H83B,H83C),
 C84(H84A,H84B,H84C)
;
_shelx_res_checksum              63554
_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 1.663
_oxdiff_exptl_absorpt_empirical_full_min 0.545
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2