Tetrahomo corona[4]arene-based spirophanes: synthesis, structure, and properties.
Guo, Shen-Yi; Zhang, Zhuo-Ang; Tong, Shuo; Guo, Qing-Hui; Hua, Ruimao; Wang, Mei-Xiang; Chemical science 14 (2023) 8393–8400; doi:10.1039/d3sc02417b

data_1569496
_publ_section_title
;
 Tetrahomo corona[4]arene-based spirophanes: synthesis, structure, and
 properties.
;
_journal_issue                   31
_journal_name_full               'Chemical science'
_journal_page_first              8393
_journal_page_last               8400
_journal_paper_doi               10.1039/d3sc02417b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         '3(C6 H4 S4), C42 H34 N8 O6 S2, C H2 Cl0.5'
_chemical_formula_sum            'C61 H48 Cl0.5 N8 O6 S14'
_chemical_formula_weight         1455.64
_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             2023-03-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-05-08 deposited with the CCDC.	2023-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                83.2409(18)
_cell_angle_beta                 87.432(2)
_cell_angle_gamma                63.772(2)
_cell_formula_units_Z            2
_cell_length_a                   13.7566(3)
_cell_length_b                   14.5509(3)
_cell_length_c                   18.1357(4)
_cell_measurement_reflns_used    24601
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      77.6350
_cell_measurement_theta_min      2.3830
_cell_volume                     3233.74(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_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_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.950
_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     51.00 115.00   0.50    0.21    --   48.14-158.00 143.00  128
  2  \w     94.00 132.00   0.50    0.82    --  106.93-158.00 143.00   76
  3  \w     35.00 110.00   0.50    0.82    --  106.93-125.00 150.00  150
  4  \w     82.00 108.00   0.50    0.82    --  106.93-125.00   0.00   52
  5  \w     36.00  61.00   0.50    0.82    --  106.93-125.00   0.00   50
  6  \w     48.00 108.00   0.50    0.82    --  106.93-107.00 -38.39  120
  7  \w     44.00 109.00   0.50    0.82    --  106.93-119.00 -62.00  130
  8  \w     78.00 111.00   0.50    0.82    --  106.93-125.00-120.00   66
  9  \w     55.00  84.00   0.50    0.82    --  106.93 -99.00-180.00   58
 10  \w     21.00  91.00   0.50    0.21    --   48.14-119.00 -62.00  140
 11  \w     39.00 105.00   0.50    0.82    --  106.93 -99.00  60.00  132
 12  \w     36.00  89.00   0.50    0.82    --  106.93 -99.00 150.00  106
 13  \w    -24.00  28.00   0.50    0.21    --   48.14 -19.00  30.00  104
 14  \w     35.00  66.00   0.50    0.82    --  106.93 -57.00 150.00   62
 15  \w     42.00  68.00   0.50    0.82    --  106.93 -57.00 120.00   52
 16  \w     35.00  67.00   0.50    0.82    --  106.93 -57.00 -30.00   64
 17  \w     40.00 106.00   0.50    0.82    --  106.93 -77.00 -60.00  132
 18  \w     39.00  65.00   0.50    0.82    --  106.93 -57.00-180.00   52
 19  \w    -24.00  43.00   0.50    0.21    --   48.14 -38.00-180.00  134
 20  \w     53.00 119.00   0.50    0.21    --   48.14  57.00 -30.00  132
 21  \w    126.00 155.00   0.50    0.82    --  106.93 125.00-120.00   58
 22  \w     96.00 177.00   0.50    0.82    --  106.93  38.00  90.00  162
 23  \w    104.00 177.00   0.50    0.82    --  106.93  19.00 120.00  146
 24  \w     64.00  89.00   0.50    0.21    --   48.14 158.00 176.00   50
 25  \w     76.00 109.00   0.50    0.82    --  106.93 158.00 176.00   66
 26  \w    106.00 131.00   0.50    0.82    --  106.93 119.00  22.00   50
 27  \w     85.00 110.00   0.50    0.82    --  106.93 125.00-120.00   50
 28  \w   -127.00-100.00   0.50    0.82    -- -104.00-119.00 -62.00   54
 29  \w   -120.00 -76.00   0.50    0.21    --  -48.14-125.00   0.00   88
 30  \w   -110.00 -79.00   0.50    0.21    --  -48.14-125.00  30.00   62
 31  \w    -84.00 -57.00   0.50    0.21    --  -48.14-158.00 143.00   54
 32  \w   -130.00-105.00   0.50    0.82    -- -104.00-158.00 143.00   50
 33  \w   -174.00 -92.00   0.50    0.82    -- -104.00 -57.00  30.00  164
 34  \w   -127.00 -97.00   0.50    0.82    -- -104.00 -38.00   0.00   60
 35  \w   -174.00-133.00   0.50    0.82    -- -104.00 -38.00   0.00   82
 36  \w   -124.00 -96.00   0.50    0.82    -- -104.00 -38.00-150.00   56
 37  \w   -166.00-140.00   0.50    0.82    -- -104.00 -38.00-150.00   52
 38  \w   -172.00 -94.00   0.50    0.82    -- -104.00 -19.00-120.00  156
 39  \w    -24.00  25.00   0.50    0.21    --  -48.14  19.00-150.00   98
 40  \w    -61.00 -36.00   0.50    0.82    -- -104.00  57.00 -30.00   50
 41  \w    -59.00 -32.00   0.50    0.82    -- -104.00  57.00   0.00   54
 42  \w    -64.00 -39.00   0.50    0.82    -- -104.00  57.00  30.00   50
 43  \w    -64.00 -32.00   0.50    0.82    -- -104.00  57.00  60.00   64
 44  \w    -64.00 -39.00   0.50    0.82    -- -104.00  57.00 120.00   50
 45  \w    -75.00 -50.00   0.50    0.21    --  -48.14 119.00  22.00   50
 46  \w   -107.00 -62.00   0.50    0.82    -- -104.00 119.00  22.00   90
 47  \w    -58.00 -33.00   0.50    0.82    -- -104.00 119.00  22.00   50
 48  \w   -120.00 -34.00   0.50    0.82    -- -104.00 137.00 159.54  172
 49  \w   -133.00 -70.00   0.50    0.82    -- -104.00 158.00 176.00  126
 50  \w    -85.00 -58.00   0.50    0.21    --  -48.14 158.00 176.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0470052000
_diffrn_orient_matrix_UB_12      0.0314216000
_diffrn_orient_matrix_UB_13      -0.0795066000
_diffrn_orient_matrix_UB_21      -0.1090963000
_diffrn_orient_matrix_UB_22      0.0060227000
_diffrn_orient_matrix_UB_23      0.0297416000
_diffrn_orient_matrix_UB_31      -0.0383988000
_diffrn_orient_matrix_UB_32      0.1143445000
_diffrn_orient_matrix_UB_33      0.0105783000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44015
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.175
_diffrn_reflns_theta_min         2.453
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       block
_exptl_crystal_F_000             1501
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.163
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     912
_refine_ls_number_reflns         13170
_refine_ls_number_restraints     93
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0743
_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^)+(0.1614P)^2^+1.5069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2201
_refine_ls_wR_factor_ref         0.2322
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11087
_reflns_number_total             13170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02417b2.cif
_cod_data_source_block           gsy-10c-ttf-acetone-hex_auto
_cod_depositor_comments
'Adding full bibliography for 1569486--1569506.cif.'
_cod_original_cell_volume        3233.74(14)
_cod_original_formula_sum        'C61 H48 Cl0.50 N8 O6 S14'
_cod_database_code               1569496
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S'
_shelx_estimated_absorpt_t_max   0.864
_shelx_estimated_absorpt_t_min   0.081
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C2-C7
 1.35 with sigma of 0.02
 S3-C12
 1.73 with sigma of 0.02
 C7-S6
 1.78 with sigma of 0.02
 S4-C5
 1.73 with sigma of 0.02
 C7-S4
 1.78 with sigma of 0.02
 S1-C15
 1.73 with sigma of 0.02
 C2-S1
 1.78 with sigma of 0.02
 C2-S3
 1.78 with sigma of 0.02
 C15-C12
 1.35 with sigma of 0.02
 C10-C5
 1.35 with sigma of 0.02
 C10-S6
 1.75 with sigma of 0.02
 C10A-C5A
 1.35 with sigma of 0.02
 S3A-C12A
 1.75 with sigma of 0.02
 C2A-S1A
 1.75 with sigma of 0.02
 S4A-C5A
 1.75 with sigma of 0.02
 C15A-C12A
 1.35 with sigma of 0.02
 C10A-S6A
 1.75 with sigma of 0.02
 C2A-S3A
 1.75 with sigma of 0.02
 S6A-C7A
 1.75 with sigma of 0.02
 C15A-S1A
 1.75 with sigma of 0.02
 C7A-S4A
 1.75 with sigma of 0.02
 C2A-C7A
 1.35 with sigma of 0.02
 Cl1-C1
 1.75 with sigma of 0.01
 C1_$1-C1
 1.55 with sigma of 0.01
3. Rigid bond restraints
 C2, S1, C15, S3, C7, C12, S4A, S1A, C7A, C2A, C12A, C15A, S4, S6, S6A, S3A,
 C5A, C5, C10, C10A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, Cl1, C1A, C1, C1A, Cl1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C1)
\\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(Cl1) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
5. Others
 Sof(S6A)=Sof(S4A)=Sof(S3A)=Sof(S1A)=Sof(C7A)=Sof(C2A)=Sof(C12A)=Sof(H12A)=
 Sof(C15A)=Sof(H15A)=Sof(C5A)=Sof(H5A)=Sof(C10A)=Sof(H10A)=1-FVAR(1)
 Sof(S1)=Sof(S3)=Sof(C2)=Sof(S4)=Sof(C7)=Sof(S6)=Sof(C5)=Sof(H5)=Sof(C12)=
 Sof(H12)=Sof(C15)=Sof(H15)=Sof(C10)=Sof(H10)=FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=1-FVAR(2)
 Sof(C1)=Sof(H1A)=Sof(H1B)=FVAR(2)
 Fixed Sof: Cl1(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C70(H70A,H70B), C38(H38A,H38B), C48(H48A,H48B), C23(H23A,H23B), C61(H61A,
 H61B), C27(H27A,H27B), C54(H54A,H54B), C34(H34A,H34B), C1(H1A,H1B), C1A(H1AA,
 H1AB)
6.b Aromatic/amide H refined with riding coordinates:
 C41(H41), C44(H44), C60(H60), C36(H36), C59(H59), C25(H25), C18(H18),
 C57(H57), C19(H19), C56(H56), C78(H78), C77(H77), C8(H8), C71(H71), C9(H9),
 C13(H13), C4(H4), C14(H14), C73(H73), C3(H3), C72(H72), C31(H31), C74(H74),
 C30(H30), C76(H76), C75(H75), C5(H5), C12(H12), C15(H15), C10(H10), C12A(H12A),
  C15A(H15A), C5A(H5A), C10A(H10A)
;
_shelx_res_checksum              46306
_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 7.328
_oxdiff_exptl_absorpt_empirical_full_min 0.231