Synthesis and thermoelectric properties of 2- and 2,8-substituted tetrathiotetracenes
Garrett, Mary Robert; Durán-Peña, María Jesús; Lewis, William; Pudzs, Kaspars; Užulis, Jānis; Mihailovs, Igors; Tyril, Björk; Shine, Jonathan; Smith, Emily F.; Rutkis, Martins; Woodward, Simon; Journal of Materials Chemistry C 6 (2018) 3403–; doi:10.1039/C8TC00073E

data_7237270
_publ_section_title
;
 Synthesis and thermoelectric properties of 2- and 2,8-substituted
 tetrathiotetracenes
;
_journal_issue                   13
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3403
_journal_paper_doi               10.1039/C8TC00073E
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C20 H16 O'
_chemical_formula_sum            'C20 H16 O'
_chemical_formula_weight         272.33
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-13 deposited with the CCDC.
2018-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.872(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.178(6)
_cell_length_b                   6.0436(9)
_cell_length_c                   8.6187(14)
_cell_measurement_reflns_used    2186
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0860
_cell_measurement_theta_min      5.0700
_cell_volume                     1358.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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    -33.00  33.00   0.50   15.00    --    0.00 -82.00 -60.00  132
  2  \w    -32.00  89.00   0.50   15.00    --    0.00  19.00   0.00  242
  3  \w    -33.00  33.00   0.50   15.00    --    0.00 -82.00 150.00  132
  4  \w     13.00  69.00   0.50   60.00    --  102.40 -30.00   0.00  112
  5  \w     13.00  69.00   0.50   60.00    --  102.40 -30.00  60.00  112
  6  \w     13.00  69.00   0.50   60.00    --  102.40 -30.00 150.00  112
  7  \w     13.00  69.00   0.50   60.00    --  102.40 -30.00 -60.00  112
  8  \w     79.00 192.00   0.50   60.00    --  102.40  45.00 -60.00  226
  9  \w     13.00  77.00   0.50   60.00    --  102.40 -45.00-150.00  128
 10  \w     13.00 134.00   0.50   60.00    --  102.40 -77.00 120.00  242
 11  \w     13.00 136.00   0.50   60.00    --  102.40 -82.00-180.00  246
 12  \w     13.00 134.00   0.50   60.00    --  102.40 -77.00  90.00  242
 13  \w     13.00  69.00   0.50   60.00    --  102.40 -30.00 -30.00  112
 14  \w     13.00 136.00   0.50   60.00    --  102.40 -82.00 120.00  246
 15  \w     20.00 136.00   0.50   60.00    --  102.40 -82.00 150.00  232
 16  \w     20.00  69.00   0.50   60.00    --  102.40 -30.00-150.00   98
 17  \w     23.00 124.00   0.50   60.00    --  102.40 -61.00 120.00  202
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0137615000
_diffrn_orient_matrix_UB_12      0.2335693000
_diffrn_orient_matrix_UB_13      -0.0544836000
_diffrn_orient_matrix_UB_21      -0.0567914000
_diffrn_orient_matrix_UB_22      0.0694187000
_diffrn_orient_matrix_UB_23      -0.0028322000
_diffrn_orient_matrix_UB_31      0.0090875000
_diffrn_orient_matrix_UB_32      0.0752424000
_diffrn_orient_matrix_UB_33      0.1709104000
_diffrn_radiation_collimation    'VariMax VHF mirror optic'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10732
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         5.087
_diffrn_source                   'rotating anode'
_diffrn_source_current           30
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'MicroMax 007 HF'
_diffrn_source_voltage           40
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.023
_refine_diff_density_max         1.146
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.713
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.713
_refine_ls_R_factor_all          0.1896
_refine_ls_R_factor_gt           0.1423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4282
_refine_ls_wR_factor_ref         0.4701
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1332
_reflns_number_total             2377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8tc00073e2.cif
_cod_data_source_block           mrgswa
_cod_database_code               7237270
_nottingham_internal_coll_name   MRGSWA
_nottingham_internal_coll_number 17033
_nottingham_internal_coll_client MRG/SW
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '15.00, 60.00'
_nottingham_internal_coll_frame_width 0.50
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   16/05/2017
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_process_date 21/06/2017
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 21/6/2017
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 20/9/2017
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 8/11/2017
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 8/11/2017
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C20 H16 O'
_chemical_oxdiff_usercomment
'MRGSWA #17033 MM-460 IN FOMBLIN FILM ON A MICROMOUNT FOR MRG/SW'
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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:
 C1(H1), C3(H3), C4(H4), C6(H6), C8(H8), C10(H10), C12(H12), C13(H13),
 C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              39542
_olex2_date_sample_data_collection 2017-05-16
_olex2_date_sample_submission    2017-05-11
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.944
_oxdiff_exptl_absorpt_empirical_full_min 0.592