Synthesis of penta- and hexa(3,4-thienylene): Size-dependent structural properties of cyclic oligothiophenes
Nagase, Mai; Nakano, Sachiko; Segawa, Yasutomo; Chemical Communications  (2023) –; doi:10.1039/D3CC03508E

data_7132047
_publ_section_title
;
 Synthesis of penta- and hexa(3,4-thienylene): Size-dependent structural
 properties of cyclic oligothiophenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03508E
_journal_year                    2023
_chemical_formula_moiety         'C20 H10 S5'
_chemical_formula_sum            'C20 H10 S5'
_chemical_formula_weight         410.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-14 deposited with the CCDC.	2023-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.303(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1542(5)
_cell_length_b                   10.6118(3)
_cell_length_c                   13.9023(5)
_cell_measurement_reflns_used    4614
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.2780
_cell_measurement_theta_min      2.6400
_cell_volume                     1711.94(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.821
_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    -34.00  63.00   0.50    0.45    --  -11.26  62.00-102.00  194
  2  \w     57.00  86.00   0.50    0.45    --   12.67 179.00-180.00   58
  3  \w    -76.00  10.00   0.50    0.45    --  -11.26 -62.00 120.00  172
  4  \w    -90.00 -60.00   0.50    0.45    --  -11.26-179.00-150.00   60
  5  \w    -87.00 -45.00   0.50    0.45    --  -11.26-179.00-120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0377664000
_diffrn_orient_matrix_UB_12      0.0479788000
_diffrn_orient_matrix_UB_13      0.0262296000
_diffrn_orient_matrix_UB_21      0.0215056000
_diffrn_orient_matrix_UB_22      0.0074200000
_diffrn_orient_matrix_UB_23      -0.0418200000
_diffrn_orient_matrix_UB_31      -0.0429998000
_diffrn_orient_matrix_UB_32      0.0458963000
_diffrn_orient_matrix_UB_33      -0.0205227000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.821
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6906
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.212
_diffrn_reflns_theta_min         2.457
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         2289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0373P)^2^+1.9574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0833
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2069
_reflns_number_total             2289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03508e3.cif
_cod_data_source_block           yse037b_chcl3hex_1_
_cod_database_code               7132047
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S'
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.905
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C10(H10), C6(H6), C1(H1)
;
_shelx_res_checksum              4917
_shelx_hkl_checksum              38018
_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 1.254
_oxdiff_exptl_absorpt_empirical_full_min 0.853