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_7132046
_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 H28 B2 O4 S2'
_chemical_formula_sum            'C20 H28 B2 O4 S2'
_chemical_formula_weight         418.16
_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
_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                86.670(2)
_cell_angle_beta                 85.723(2)
_cell_angle_gamma                71.102(2)
_cell_formula_units_Z            4
_cell_length_a                   10.9669(3)
_cell_length_b                   11.1772(2)
_cell_length_c                   19.4756(7)
_cell_measurement_reflns_used    15074
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.0270
_cell_measurement_theta_min      2.5980
_cell_volume                     2250.87(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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.827
_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     -3.00  43.00   0.50   38.45    --   12.67 -19.00   0.00   92
  2  \w    -12.00  51.00   0.50   38.45    --   12.67 -99.00  60.00  126
  3  \w     31.00  56.00   0.50   38.45    --   12.67-144.00 -21.00   50
  4  \w     15.00  63.00   0.50   38.45    --   12.67-126.00 146.00   96
  5  \w     54.00  90.00   0.50   38.45    --   12.67-179.00 150.00   72
  6  \w    -37.00 -10.00   0.50   38.45    --   12.67 -19.00   0.00   54
  7  \w    -38.00  62.00   0.50   38.45    --  -11.26  77.00 -60.00  200
  8  \w     48.00  91.00   0.50   38.45    --   12.67 179.00 -60.00   86
  9  \w    -15.00  87.00   0.50   38.45    --   12.67  77.00 150.00  204
 10  \w    -82.00   9.00   0.50   38.45    --  -11.26 -57.00-180.00  182
 11  \w    -89.00 -64.00   0.50   38.45    --  -11.26-179.00-180.00   50
;
_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      0.0082938000
_diffrn_orient_matrix_UB_12      0.0069540000
_diffrn_orient_matrix_UB_13      -0.0363143000
_diffrn_orient_matrix_UB_21      0.0017065000
_diffrn_orient_matrix_UB_22      -0.0633787000
_diffrn_orient_matrix_UB_23      -0.0033674000
_diffrn_orient_matrix_UB_31      -0.0679556000
_diffrn_orient_matrix_UB_32      0.0209681000
_diffrn_orient_matrix_UB_33      -0.0023425000
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            39866
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.480
_diffrn_reflns_theta_min         2.283
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91868
_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    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     521
_refine_ls_number_reflns         12381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0692
_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^)+(0.0331P)^2^+4.0228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1617
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9574
_reflns_number_total             12381
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03508e3.cif
_cod_data_source_block           yse052b_5
_cod_depositor_comments
;

2025-01-11
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C40 H56 B4 O8 S4'
_cod_original_formula_weight         836.32
_cod_original_formula_moiety         '2(C20 H28 B2 O4 S2)'
_cod_original_formula_units_Z            2
_cod_database_code               7132046
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C B S H O'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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:
 C25(H25), C21(H21), C28(H28), C24(H24), C1(H1), C8(H8), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C31(H31A,H31B,H31C), C12(H12A,H12B,H12C), C34(H34A,H34B,
 H34C), C32(H32A,H32B,H32C), C19(H19A,H19B,H19C), C11(H11A,H11B,H11C), C38(H38A,
 H38B,H38C), C39(H39A,H39B,H39C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C17(H17A,H17B,H17C), C33(H33A,H33B,H33C), C40(H40A,H40B,H40C), C20(H20A,H20B,
 H20C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              76442
_shelx_hkl_checksum              58070
_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 1.168
_oxdiff_exptl_absorpt_empirical_full_min 0.900