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_1569486
_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         'C36 H32 F4 O8'
_chemical_formula_sum            'C36 H32 F4 O8'
_chemical_formula_weight         668.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-27
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.2891(4)
_cell_length_b                   8.10320(10)
_cell_length_c                   36.4586(7)
_cell_measurement_reflns_used    15560
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      64.9240
_cell_measurement_theta_min      4.2750
_cell_volume                     6289.47(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_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      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -116.00 -18.00   1.00    2.28    --  -42.06 -38.00 -60.00   98
  2  \w   -116.00 -18.00   1.00    2.28    --  -42.06 -38.00  30.00   98
  3  \w   -116.00 -18.00   1.00    2.28    --  -42.06 -38.00  60.00   98
  4  \w    -70.00  31.00   1.00    2.28    --  -42.06  57.00-150.00  101
  5  \w    103.00 165.00   1.00    9.13    --   89.04  77.00  30.00   62
  6  \w     13.00 122.00   1.00    9.13    --   89.04 -77.00 -30.00  109
  7  \w     97.00 162.00   1.00    9.13    --   89.04 125.00-120.00   65
  8  \w     60.00 161.00   1.00    9.13    --   89.04  61.00  90.00  101
  9  \w     27.00 112.00   1.00    9.13    --   89.04-125.00-120.00   85
 10  \w     27.00 112.00   1.00    9.13    --   89.04-125.00  60.00   85
 11  \w     97.00 162.00   1.00    9.13    --   89.04 125.00   0.00   65
 12  \w     27.00 112.00   1.00    9.13    --   89.04-125.00-180.00   85
 13  \w     13.00 117.00   1.00    9.13    --   89.04 -30.00  60.00  104
 14  \w     27.00 112.00   1.00    9.13    --   89.04-125.00 -30.00   85
 15  \w    106.00 163.00   1.00    9.13    --   89.04  77.00 -30.00   57
 16  \w    114.00 160.00   1.00    9.13    --   89.04  77.00 120.00   46
 17  \w    107.00 164.00   1.00    9.13    --   89.04  77.00-180.00   57
 18  \w     88.00 120.00   1.00    9.13    --   89.04 141.00  30.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0013793000
_diffrn_orient_matrix_UB_12      0.0421898000
_diffrn_orient_matrix_UB_13      0.0088003000
_diffrn_orient_matrix_UB_21      0.0718429000
_diffrn_orient_matrix_UB_22      0.0010131000
_diffrn_orient_matrix_UB_23      -0.0228725000
_diffrn_orient_matrix_UB_31      -0.0087608000
_diffrn_orient_matrix_UB_32      0.0018598000
_diffrn_orient_matrix_UB_33      -0.1885310000
_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  0.0664
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            57052
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        65.105
_diffrn_reflns_theta_max         65.105
_diffrn_reflns_theta_min         4.153
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       needle
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Flack x determined using 3952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.33(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     894
_refine_ls_number_reflns         10364
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0731
_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^)+(0.1305P)^2^+4.3216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.1945
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                9451
_reflns_number_total             10364
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02417b2.cif
_cod_data_source_block           gsy610
_cod_depositor_comments
'Adding full bibliography for 1569486--1569506.cif.'
_cod_database_code               1569486
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O F'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C3, C3A, C2, C2A, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C3 \\sim C3A \\sim C2 \\sim C2A \\sim C1: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
Uanis(C3) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C2A)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(H1B)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 Sof(H2AC)=1-FVAR(1)
 Sof(H1A)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(H3C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C01H(H01H), C01I(H01I), C02G(H02O), C1(H1A), C1(H1B)
5.b Secondary CH2 refined with riding coordinates:
 C00P(H00C,H00D), C00X(H00A,H00B), C013(H01F,H01G), C01C(H01D,H01E), C020(H02K,
 H02L), C02B(H02A,H02B), C02C(H02M,H02N), C02L(H02I,H02J)
5.c Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C014(H014), C016(H016), C019(H019), C01J(H01J), C01K(H01K),
 C01P(H01P), C01Q(H01Q), C01R(H01R), C021(H021), C022(H022), C023(H023),
 C024(H024), C025(H025), C026(H026), C028(H028), C029(H029), C02D(H02D),
 C02E(H02E), C02H(H02H)
5.d Idealised Me refined as rotating group:
 C01A(H01A,H01B,H01C), C01X(H01L,H01M,H01N), C02F(H02C,H02F,H02G), C02I(H02P,
 H02Q,H02R), C02J(H02S,H02T,H02U), C02M(H02V,H02W,H02X), C2(H2A,H2B,H2C),
 C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC), C2A(H2AA,H2AB,H2AC)
;
_shelx_res_checksum              18495
_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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.649