Effect of electron-withdrawing groups on molecular properties of naphthyl and anthryl bithiophenes as potential n-type semiconductors
Feriancová, Lucia; Cigáň, Marek; Gmucová, Katarína; Kožíšek, Jozef; Nádaždy, Vojtech; Putala, Martin; New Journal of Chemistry 45 (2021) 9794–9804; doi:10.1039/D1NJ01100F

data_7060607
_publ_section_title
;
 Effect of electron-withdrawing groups on molecular properties of naphthyl
 and anthryl bithiophenes as potential n-type semiconductors
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9794
_journal_page_last               9804
_journal_paper_doi               10.1039/D1NJ01100F
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C24 H22 O S2'
_chemical_formula_sum            'C24 H22 O S2'
_chemical_formula_weight         390.53
_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
_audit_creation_date             2021-02-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2021-02-25 deposited with the CCDC.	2021-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.9880(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   41.2198(6)
_cell_length_b                   5.82020(10)
_cell_length_c                   8.0162(2)
_cell_measurement_reflns_used    56134
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.49
_cell_measurement_theta_min      3.22
_cell_volume                     1922.86(6)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 HPAD
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris 300K Pilatus3R'
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details
;
 1615 frames, detector distance = 40 mm
;
_diffrn_measurement_device       '4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            33369
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.897
_diffrn_reflns_theta_min         3.217
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_target            Cu
_diffrn_source_type              'Xenocs Cu tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.583
_exptl_absorpt_correction_T_max  0.1630
_exptl_absorpt_correction_T_min  0.1050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00150(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+1.1706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0788
_reflns_d_resolution_high        0.811
_reflns_d_resolution_low         13.320
_reflns_number_gt                3392
_reflns_number_total             3522
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj01100f2.cif
_cod_data_source_block           IIB
_cod_depositor_comments
'Adding full bibliography for 7060607--7060608.cif.'
_cod_database_code               7060607
_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:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              95830