“Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched π-stacking
Wang, Chengyuan; Hashizume, Daisuke; Nakano, Masahiro; Ogaki, Takuya; Takenaka, Hiroyuki; Kawabata, Kohsuke; Takimiya, Kazuo; Chemical Science 11 (2020) 1573–1580; doi:10.1039/C9SC05902D

data_1557445
_publ_section_title
;
 &#x201C;Disrupt and induce&#x201D; intermolecular interactions to
 rationally design organic semiconductor crystals: from herringbone to
 rubrene-like pitched \p-stacking
;
_journal_issue                   6
_journal_name_full               'Chemical Science'
_journal_page_first              1573
_journal_page_last               1580
_journal_paper_doi               10.1039/C9SC05902D
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         '2(C7 H4 S)'
_chemical_formula_sum            'C14 H8 S2'
_chemical_formula_weight         240.32
_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
_audit_creation_date             2018-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-26 deposited with the CCDC.	2019-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.458(3)
_cell_angle_beta                 101.223(3)
_cell_angle_gamma                93.037(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8903(3)
_cell_length_b                   7.8065(4)
_cell_length_c                   11.6922(6)
_cell_measurement_reflns_used    5776
_cell_measurement_temperature    223
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.86
_cell_volume                     526.52(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      223.15
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID---RIKEN'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9414
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_min         3.855
_diffrn_source_target            Cu
_exptl_absorpt_coefficient_mu    4.256
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0689
_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^)+(0.1170P)^2^+0.1207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1962
_refine_ls_wR_factor_ref         0.2081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1374
_reflns_number_total             1881
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9sc05902d2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 1557445--1557447.cif.'
_cod_original_cell_volume        526.52(4)
_cod_database_code               1557445
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.184
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{C1A, S2A}
{C1B, S2B}
3. Uiso/Uaniso restraints and constraints
Uanis(C1A) = Uanis(S2A)
Uanis(C1B) = Uanis(S2B)
4. Others
 1*[Sof(C1A)+Sof(H1A)+Sof(S2A)+Sof(H14)+Sof(H14A)]+1*[Sof(S2B)+Sof(C1B)+
 Sof(H1B)]=1 with esd of 0.000001
 Sof(S2A)=Sof(H14A)=1-FVAR(1)
 Sof(C1A)=Sof(H1A)=Sof(H14)=FVAR(1)
 Sof(S2B)=1-FVAR(2)
 Sof(C1B)=Sof(H1B)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13),
 C14(H14), C14(H14A)
;
_diffractometer_make_and_type    'Rigaku R-AXIS RAPID'
_olex2_submission_special_instructions 'No special instructions were received'