From π-conjugated macrocycles to heterocycloarenes based on benzo[2,1-<i>b</i>:3,4-<i>b</i>']dithiophene (BDTh): size- and geometry-dependent host-guest properties.
An, Dongyue; Zhang, Rong; Zhu, Jiangyu; Wang, Teng; Zhao, Yan; Lu, Xuefeng; Liu, Yunqi; Chemical science 15 (2024) 4590–4601; doi:10.1039/d3sc05074b

data_1571055
_publ_section_title
;
 From &#x3c0;-conjugated macrocycles to heterocycloarenes based on
 benzo[2,1-<i>b</i>:3,4-<i>b</i>']dithiophene (BDTh): size- and
 geometry-dependent host-guest properties.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              4590
_journal_page_last               4601
_journal_paper_doi               10.1039/d3sc05074b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         '2(C88 H88 O8 S4)'
_chemical_formula_sum            'C176 H176 O16 S8'
_chemical_formula_weight         2803.64
_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             2021-05-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-06-25 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                107.2940(10)
_cell_angle_beta                 108.1540(10)
_cell_angle_gamma                109.7120(10)
_cell_formula_units_Z            2
_cell_length_a                   19.1086(4)
_cell_length_b                   21.5706(5)
_cell_length_c                   22.0668(6)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.08
_cell_measurement_theta_min      2.52
_cell_volume                     7266.8(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      173.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1152
_diffrn_reflns_av_unetI/netI     0.0992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            82997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.389
_diffrn_reflns_theta_min         2.436
_diffrn_source_current           45.0
_diffrn_source_power             2.25
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.667
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6411
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0823 before and 0.0698 after correction.
The Ratio of minimum to maximum transmission is 0.8513.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             2976
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1953
_refine_ls_number_reflns         26462
_refine_ls_number_restraints     149
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0632
_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^)+(0.0901P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15251
_reflns_number_total             26462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05074b2.cif
_cod_data_source_block           a_a
_cod_depositor_comments
'Adding full bibliography for 1571054--1571057.cif.'
_cod_database_code               1571055
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.825
_shelx_estimated_absorpt_t_min   0.776
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C165-C166
 1.53 with sigma of 0.02
 C165-C175
 1.53 with sigma of 0.02
 C151-C152 \\sim C74-C1A
 with sigma of 0.02
 C150-C151 \\sim C150-C74
 with sigma of 0.02
 C150-C152 \\sim C150-C1A
 with sigma of 0.04
 C73-C75 \\sim C73-C75A
 with sigma of 0.02
 C75-C76 \\sim C75A-C76A
 with sigma of 0.02
 C73-C76 \\sim C73-C76A
 with sigma of 0.04
 C75-C178 \\sim C75A-C177
 with sigma of 0.04
 C76-C178 \\sim C76A-C177
 with sigma of 0.02
 C158-C160 \\sim C179-C1C
 with sigma of 0.04
 C159-C160 \\sim C1B-C1C
 with sigma of 0.02
 C158-C159 \\sim C179-C1B
 with sigma of 0.02
 C157-C158 \\sim C157-C179
 with sigma of 0.02
 C157-C159 \\sim C157-C1B
 with sigma of 0.04
 C62-C64 \\sim C62-C64A
 with sigma of 0.04
 C62-C63 \\sim C62-C63A
 with sigma of 0.02
 C63-C64 \\sim C63A-C64A
 with sigma of 0.02
 O9-C175 \\sim O9-C180
 with sigma of 0.02
 C166-C175 \\sim C1E-C180
 with sigma of 0.04
 O9-C165 \\sim O9-C1D
 with sigma of 0.04
 C166-C176 \\sim C1E-C1F
 with sigma of 0.02
 C165-C176 \\sim C1D-C1F
 with sigma of 0.04
 C166-C165 \\sim C1E-C1D
 with sigma of 0.02
 C165-C175 \\sim C1D-C180
 with sigma of 0.02
3. Rigid bond restraints
 C62, C63
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C63, C64
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O9, C175
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C158, C159
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C160, C159
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C165, C166
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C176, C166
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Rigid body (RIGU) restrains
 C158, C179, C159, C1B, C1C, C160, C157
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C150, C151, C74, C1A, C152, C149
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C180, C175, C1D, C165, C1E, C166, C1F, C176, C75, C75A, C73, C76, C76A, C178,
 C177
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(H15C)=Sof(H15D)=Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=
 Sof(H1AC)=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(C151)=Sof(H15E)=Sof(H15F)=Sof(C152)=Sof(H15G)=
 Sof(H15H)=Sof(H15I)=FVAR(1)
 Sof(H73C)=Sof(H73D)=Sof(C75A)=Sof(H75C)=Sof(H75D)=Sof(C76A)=Sof(H76C)=
 Sof(H76D)=Sof(C177)=Sof(H17W)=Sof(H17X)=Sof(H17Y)=1-FVAR(2)
 Sof(H73A)=Sof(H73B)=Sof(C75)=Sof(H75A)=Sof(H75B)=Sof(C76)=Sof(H76A)=Sof(H76B)=
 Sof(C178)=Sof(H17T)=Sof(H17U)=Sof(H17V)=FVAR(2)
 Sof(H15U)=Sof(H15V)=Sof(C179)=Sof(H17R)=Sof(H17S)=Sof(C1B)=Sof(H1BA)=
 Sof(H1BB)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=1-FVAR(3)
 Sof(H15S)=Sof(H15T)=Sof(C158)=Sof(H15W)=Sof(H15X)=Sof(C159)=Sof(H15Y)=Sof(H)=
 Sof(C160)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(3)
 Sof(H62C)=Sof(H62D)=Sof(C63A)=Sof(H63C)=Sof(H63D)=Sof(C64A)=Sof(H64D)=
 Sof(H64E)=Sof(H64F)=1-FVAR(4)
 Sof(H62A)=Sof(H62B)=Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(C64)=Sof(H64A)=Sof(H64B)=
 Sof(H64C)=FVAR(4)
 Sof(C180)=Sof(H18A)=Sof(H18B)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(C1E)=Sof(H1EA)=
 Sof(H1EB)=Sof(C1F)=Sof(H1FA)=Sof(H1FB)=Sof(H1FC)=1-FVAR(5)
 Sof(C166)=Sof(H16O)=Sof(H16P)=Sof(C165)=Sof(H16Q)=Sof(H16R)=Sof(C175)=
 Sof(H17M)=Sof(H17N)=Sof(C176)=Sof(H17O)=Sof(H17P)=Sof(H17Q)=FVAR(5)
6.a Secondary CH2 refined with riding coordinates:
 C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C61(H61A,H61B), C62(H62A,
 H62B), C62(H62C,H62D), C63(H63A,H63B), C65(H65A,H65B), C66(H66A,H66B),
 C67(H67A,H67B), C69(H69A,H69B), C70(H70A,H70B), C71(H71A,H71B), C73(H73A,H73B),
  C73(H73C,H73D), C77(H77A,H77B), C78(H78A,H78B), C79(H79A,H79B), C81(H81A,
 H81B), C82(H82A,H82B), C83(H83A,H83B), C85(H85A,H85B), C86(H86A,H86B),
 C87(H87A,H87B), C145(H14A,H14B), C146(H14C,H14D), C147(H14E,H14F), C149(H14J,
 H14K), C150(H15A,H15B), C150(H15C,H15D), C151(H15E,H15F), C153(H15J,H15K),
 C154(H15L,H15M), C155(H15N,H15O), C157(H15S,H15T), C157(H15U,H15V), C158(H15W,
 H15X), C159(H15Y,H), C161(H16D,H16E), C162(H16F,H16G), C163(H16H,H16I),
 C167(H16M,H16N), C166(H16O,H16P), C165(H16Q,H16R), C168(H16S,H16T), C169(H16U,
 H16V), C171(H17D,H17E), C172(H17F,H17G), C173(H17H,H17I), C175(H17M,H17N),
 C74(H74A,H74B), C75(H75A,H75B), C76(H76A,H76B), C75A(H75C,H75D), C76A(H76C,
 H76D), C179(H17R,H17S), C1B(H1BA,H1BB), C63A(H63C,H63D), C180(H18A,H18B),
 C1D(H1DA,H1DB), C1E(H1EA,H1EB)
6.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C16(H16), C21(H21), C24(H24), C25(H25),
 C26(H26), C38(H38), C37(H37), C41(H41), C44(H44), C49(H49), C52(H52), C53(H53),
  C54(H54), C98(H98), C99(H99), C103(H103), C106(H106), C111(H111), C114(H114),
 C115(H115), C116(H116), C126(H126), C127(H127), C131(H131), C134(H134),
 C139(H139), C142(H142), C143(H143), C144(H144)
6.c Idealised Me refined as rotating group:
 C60(H60A,H60B,H60C), C64(H64A,H64B,H64C), C68(H68A,H68B,H68C), C72(H72A,H72B,
 H72C), C80(H80A,H80B,H80C), C84(H84A,H84B,H84C), C88(H88A,H88B,H88C),
 C148(H14G,H14H,H14I), C152(H15G,H15H,H15I), C156(H15P,H15Q,H15R), C160(H16A,
 H16B,H16C), C164(H16J,H16K,H16L), C170(H17A,H17B,H17C), C174(H17J,H17K,H17L),
 C176(H17O,H17P,H17Q), C1A(H1AA,H1AB,H1AC), C178(H17T,H17U,H17V), C177(H17W,
 H17X,H17Y), C1C(H1CA,H1CB,H1CC), C64A(H64D,H64E,H64F), C1F(H1FA,H1FB,H1FC)
;
_shelx_res_checksum              54679
_shelx_hkl_checksum              15268
_olex2_submission_special_instructions 'No special instructions were received'