Synthesis and comparative studies of K-region functionalized pyrene derivatives
Shahrokhi, Farshid; Fazli Estabragh, Roxana; Zhao, Yuming; New Journal of Chemistry 44 (2020) 16786–16794; doi:10.1039/D0NJ03897K

data_7060010
_publ_section_title
;
 Synthesis and comparative studies of K-region functionalized pyrene
 derivatives
;
_journal_issue                   39
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16786
_journal_page_last               16794
_journal_paper_doi               10.1039/D0NJ03897K
_journal_volume                  44
_journal_year                    2020
_chemical_compound_source        Pyrene
_chemical_formula_moiety         'C21 H14 O S4'
_chemical_formula_sum            'C21 H14 O S4'
_chemical_formula_weight         410.56
_chemical_melting_point          191.6(3)
_chemical_name_systematic
5-(4,5-bis(methylthio)-1,3-dithiol-2-ylidene)pyren-4(5H)-one
_chemical_properties_physical    Efflorescent,Oxygen-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-11 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.4856(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.15876(6)
_cell_length_b                   20.4115(3)
_cell_length_c                   16.5822(2)
_cell_measurement_reflns_used    15183
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.0620
_cell_measurement_theta_min      3.4280
_cell_volume                     1734.90(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -16.00  28.00   0.50    2.00    --  -47.82  19.00 -90.00   88
  2  \w    -16.00  28.00   0.50    2.00    --  -47.82  19.00 -60.00   88
  3  \w    -16.00  28.00   0.50    2.00    --  -47.82  19.00 -30.00   88
  4  \w    -16.00  28.00   0.50    2.00    --  -47.82  19.00 120.00   88
  5  \w    -43.00 -14.00   0.50    8.00    --  -86.25  45.00  90.00   58
  6  \w    -43.00 -14.00   0.50    8.00    --  -86.25  45.00  60.00   58
  7  \w    -82.00   0.00   0.50    2.00    --  -47.82 108.00-102.00  164
  8  \w    -43.00 -14.00   0.50    8.00    --  -86.25  45.00-120.00   58
  9  \w    -59.00  25.00   0.50    2.00    --  -47.82  57.00-180.00  168
 10  \w    -65.00 -13.00   0.50    8.00    --  -86.25  61.00 -90.00  104
 11  \w    -82.00 -13.00   0.50    8.00    --  -86.25 108.00-102.00  138
 12  \w   -119.00 -33.00   0.50    2.00    --  -47.82 -57.00-120.00  172
 13  \w   -119.00 -73.00   0.50    2.00    --  -47.82-125.00   0.00   92
 14  \w   -119.00 -73.00   0.50    2.00    --  -47.82-125.00 -30.00   92
 15  \w   -119.00 -73.00   0.50    2.00    --  -47.82-125.00-120.00   92
 16  \w   -119.00 -73.00   0.50    2.00    --  -47.82-125.00-150.00   92
 17  \w   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00-150.00  188
 18  \w   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00 -30.00  188
 19  \w     21.00  86.00   0.50    2.00    --   47.82-108.00 160.00  130
 20  \w     35.00 107.00   0.50    8.00    --  107.75-108.00 160.00  144
 21  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00   0.00   88
 22  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00  60.00   88
 23  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00 120.00   88
 24  \w     35.00 106.00   0.50    8.00    --  107.75 -97.00  58.18  142
 25  \w     35.00 112.00   0.50    8.00    --  107.75-125.00 120.00  154
 26  \w     35.00 112.00   0.50    8.00    --  107.75-125.00  60.00  154
 27  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00 -60.00   88
 28  \w     35.00 106.00   0.50    8.00    --  107.75 -94.00 -60.00  142
 29  \w     35.00 106.00   0.50    8.00    --  107.75 -94.00-180.00  142
 30  \w     35.00 112.00   0.50    8.00    --  107.75-125.00-120.00  154
 31  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00-150.00   88
 32  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00-180.00   88
 33  \w     35.00 106.00   0.50    8.00    --  107.75 -94.00-150.00  142
 34  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00 -30.00   88
 35  \w     35.00 106.00   0.50    8.00    --  107.75 -94.00 -90.00  142
 36  \w     35.00 112.00   0.50    8.00    --  107.75-125.00-150.00  154
 37  \w     35.00 106.00   0.50    8.00    --  107.75 -94.00 -30.00  142
 38  \w     35.00 106.00   0.50    8.00    --  107.75 -94.00  90.00  142
 39  \w     35.00 112.00   0.50    8.00    --  107.75-125.00  90.00  154
 40  \w     35.00  79.00   0.50    8.00    --  107.75 -61.00  30.00   88
 41  \w     95.00 178.00   0.50    8.00    --  107.75  30.00 150.00  166
 42  \w     95.00 178.00   0.50    8.00    --  107.75  45.00  30.00  166
 43  \w    104.00 178.00   0.50    8.00    --  107.75 108.00-102.00  148
 44  \w     95.00 178.00   0.50    8.00    --  107.75  45.00 -90.00  166
 45  \w     95.00 178.00   0.50    8.00    --  107.75 125.00   0.00  166
 46  \w     95.00 178.00   0.50    8.00    --  107.75  45.00 -30.00  166
 47  \w     95.00 178.00   0.50    8.00    --  107.75  30.00 120.00  166
 48  \w     95.00 178.00   0.50    8.00    --  107.75  30.00   0.00  166
 49  \w     91.00 178.00   0.50    8.00    --  107.75  61.00-120.00  174
 50  \w     35.00 112.00   0.50    8.00    --  107.75-125.00 -90.00  154
 51  \w   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00  60.00  188
 52  \w   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00 150.00  188
 53  \w   -119.00 -25.00   0.50    2.00    --  -47.82 -77.00   0.00  188
 54  \w   -159.00 -82.00   0.50    8.00    --  -86.25-108.00 160.00  154
;
_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      0.1420205000
_diffrn_orient_matrix_UB_12      0.0644182000
_diffrn_orient_matrix_UB_13      -0.0155478000
_diffrn_orient_matrix_UB_21      -0.2643811000
_diffrn_orient_matrix_UB_22      0.0356206000
_diffrn_orient_matrix_UB_23      -0.0148148000
_diffrn_orient_matrix_UB_31      0.0161429000
_diffrn_orient_matrix_UB_32      0.0167837000
_diffrn_orient_matrix_UB_33      0.0909760000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42353
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.406
_diffrn_reflns_theta_min         3.447
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90245
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/DCM'
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0654P)^2^+1.3152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3351
_reflns_number_total             3667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03897k2.cif
_cod_data_source_block           fs40
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '191.3 - 191.8' was changed
to '191.6(3)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7060010--7060012.cif.
;
_cod_database_code               7060010
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H14OS4
_chemical_oxdiff_usercomment     orange
_shelx_estimated_absorpt_t_max   0.846
_shelx_estimated_absorpt_t_min   0.440
_diffrn_oxdiff_digest_frames
;
018b4c80292012d42759a4cd63a1afbe91071145c4c
;
_diffrn_oxdiff_digest_hkl
;
0190191d136d371615d818c40f9c35fe9f7ede
;
_reflns_odcompleteness_completeness 100.00
_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
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              48939
_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 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.602