Synthesis of Tetrathia-Oligothiophene Macrocycles.
Press, David J.; Gendy, Chris; Pasalkar, Samruddhi; Schechtel, Shauna; Heyne, Belinda; Sutherland, Todd C.; ACS omega 4 (2019) 3405–3408; doi:10.1021/acsomega.8b03444

data_4515130
_publ_section_title
;
 Synthesis of Tetrathia-Oligothiophene Macrocycles.
;
_journal_issue                   2
_journal_name_full               'ACS omega'
_journal_page_first              3405
_journal_page_last               3408
_journal_paper_doi               10.1021/acsomega.8b03444
_journal_volume                  4
_journal_year                    2019
_chemical_formula_moiety         'C28 H32 S8, C6 H12'
_chemical_formula_sum            'C34 H44 S8'
_chemical_formula_weight         709.17
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                84.9630(10)
_cell_angle_beta                 77.3020(10)
_cell_angle_gamma                69.1270(10)
_cell_formula_units_Z            4
_cell_length_a                   11.0663(5)
_cell_length_b                   15.3836(7)
_cell_length_c                   23.1586(10)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.83
_cell_volume                     3593.5(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            59080
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_min         2.032
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_T_max  0.9240
_exptl_absorpt_correction_T_min  0.8029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0639 before and 0.0473 after correction. The Ratio of minimum to maximum transmission is 0.8689. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.418
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     812
_refine_ls_number_reflns         17800
_refine_ls_number_restraints     276
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0476P)^2^+1.2996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13507
_reflns_number_total             17800
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            C6biTh.cif
_cod_data_source_block           1
_cod_database_code               4515130
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.777
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C6A-C5A \\sim C5A-C4A \\sim C4A-C3A \\sim C3A-C2A \\sim C2A-C1A \\sim C1A-C6A
 with sigma of 0.02
 C6A-C2A \\sim C4A-C2A \\sim C5A-C1A \\sim C5A-C3A \\sim C3A-C1A \\sim C6A-C4A
 with sigma of 0.04
 C6B-C1B \\sim C1B-C2B \\sim C2B-C3B \\sim C3B-C4B \\sim C4B-C5B \\sim C5B-C6B
 with sigma of 0.02
 C6B-C4B \\sim C2B-C4B \\sim C1B-C5B \\sim C1B-C3B \\sim C3B-C5B \\sim C6B-C2B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C6A \\sim C5A \\sim C4A \\sim C3A \\sim C2A \\sim C1A: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
C6B \\sim C1B \\sim C2B \\sim C3B \\sim C4B \\sim C5B: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C4A)
\\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C6A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C1B) \\sim Ueq, Uanis(C2B) \\sim Ueq, Uanis(C3B) \\sim Ueq, Uanis(C4B)
\\sim Ueq, Uanis(C5B) \\sim Ueq, Uanis(C6B) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C6A, C5A, C4A, C3A, C2A, C1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C6B, C1B, C2B, C3B, C4B, C5B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C6B)=Sof(H6BA)=Sof(H6BB)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=
 Sof(H2BB)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=
 Sof(H5BA)=Sof(H5BB)=1-FVAR(1)
 Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C4A)=Sof(H4AA)=
 Sof(H4AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C1A)=
 Sof(H1AA)=Sof(H1AB)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C47(H47A,H47B), C45(H45A,H45B), C46(H46A,H46B), C30(H30A,H30B), C44(H44A,
 H44B), C48(H48A,H48B), C33(H33A,H33B), C10(H10A,H10B), C43(H43A,H43B), C9(H9A,
 H9B), C32(H32A,H32B), C29(H29A,H29B), C31(H31A,H31B), C11(H11A,H11B), C13(H13A,
 H13B), C24(H24A,H24B), C27(H27A,H27B), C34(H34A,H34B), C26(H26A,H26B),
 C14(H14A,H14B), C12(H12A,H12B), C25(H25A,H25B), C28(H28A,H28B), C23(H23A,H23B),
  C6C(H6CA,H6CB), C2C(H2CA,H2CB), C1C(H1CA,H1CB), C3C(H3CA,H3CB), C4C(H4CA,
 H4CB), C5C(H5CA,H5CB), C6A(H6AA,H6AB), C5A(H5AA,H5AB), C4A(H4AA,H4AB),
 C3A(H3AA,H3AB), C2A(H2AA,H2AB), C1A(H1AA,H1AB), C6B(H6BA,H6BB), C1B(H1BA,H1BB),
  C2B(H2BA,H2BB), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C36(H36), C55(H55), C41(H41), C37(H37), C50(H50), C2(H2),
 C40(H40), C3(H3), C51(H51), C54(H54), C20(H20), C16(H16), C21(H21), C17(H17)
;
_shelx_res_checksum              4911
_shelx_hkl_checksum              20844
_olex2_submission_special_instructions 'No special instructions were received'