Designing Tetraoxa[8]circulenes To Serve as Hosts and Sensors
Petrov, Nino G.; Chartier, Patrick; Maris, Thierry; Wuest, James D.; Journal of the American Chemical Society 144 (2021) 556–572; doi:10.1021/jacs.1c11728

data_4135642
_publ_section_title
;
 Designing Tetraoxa[8]circulenes To Serve as Hosts and Sensors
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              556
_journal_page_last               572
_journal_paper_doi               10.1021/jacs.1c11728
_journal_volume                  144
_journal_year                    2021
_chemical_formula_moiety         'C60 H34 O4, 3(C8 H10)'
_chemical_formula_sum            'C84 H64 O4'
_chemical_formula_weight         1137.35
_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_contact_author_name
;
;
_audit_creation_date             2019-11-05
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                68.679(8)
_cell_angle_beta                 86.263(9)
_cell_angle_gamma                82.937(8)
_cell_formula_units_Z            2
_cell_length_a                   10.4352(14)
_cell_length_b                   17.672(2)
_cell_length_c                   19.298(3)
_cell_measurement_reflns_used    2649
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.317
_cell_measurement_theta_min      2.458
_cell_volume                     3289.2(8)
_computing_cell_refinement
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL n/a (Sheldrick, 2008)'
_computing_structure_solution    'XT n/a (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.1651
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35189
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.277
_diffrn_reflns_theta_min         2.458
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1387 before and 0.0665 after correction. The Ratio of minimum to maximum transmission is 0.7049. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     829
_refine_ls_number_reflns         12076
_refine_ls_number_restraints     397
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1875
_refine_ls_R_factor_gt           0.0932
_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^)+(0.0716P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2175
_refine_ls_wR_factor_ref         0.2420
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4184
_reflns_number_total             12076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jw22152_13_3-oxylene.cif
_cod_data_source_block           jw22152
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_database_code               4135642
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.924
_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, All O(H) groups
2. Restrained distances
 C2E-C8E = C1E-C7E
 1.5 with sigma of 0.02
 C2D-C8D = C1D-C7D = C2B-C8B = C3B-C7B
 1.5 with sigma of 0.02
 C5A-C8A = C4A-C7A
 1.5 with sigma of 0.002
3. Restrained planarity
 C1D, C2D, C3D, C4D, C5D, C6D, C7D, C8D
 with sigma of 0.002
4. Uiso/Uaniso restraints and constraints
C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim C7A \\sim C8A \\sim
C2B \\sim C1B \\sim C6B \\sim C5B \\sim C4B \\sim C3B \\sim C7B \\sim C8B \\sim
C1D \\sim C2D \\sim C3D \\sim C4D \\sim C5D \\sim C6D \\sim C7D \\sim C8D \\sim
C1E \\sim C2E \\sim C3E \\sim C4E \\sim C5E \\sim C6E \\sim C7E \\sim C8E:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C4A)
\\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C7A) \\sim Ueq,
Uanis(C8A) \\sim Ueq, Uanis(C2B) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C6B)
\\sim Ueq, Uanis(C5B) \\sim Ueq, Uanis(C4B) \\sim Ueq, Uanis(C3B) \\sim Ueq,
Uanis(C7B) \\sim Ueq, Uanis(C8B) \\sim Ueq, Uanis(C1D) \\sim Ueq, Uanis(C2D)
\\sim Ueq, Uanis(C3D) \\sim Ueq, Uanis(C4D) \\sim Ueq, Uanis(C5D) \\sim Ueq,
Uanis(C6D) \\sim Ueq, Uanis(C7D) \\sim Ueq, Uanis(C8D) \\sim Ueq, Uanis(C1E)
\\sim Ueq, Uanis(C2E) \\sim Ueq, Uanis(C3E) \\sim Ueq, Uanis(C4E) \\sim Ueq,
Uanis(C5E) \\sim Ueq, Uanis(C6E) \\sim Ueq, Uanis(C7E) \\sim Ueq, Uanis(C8E)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C7D) = Uanis(C8D)
5. Others
 Fixed Sof: C2B(0.5) C1B(0.5) H1B(0.5) C6B(0.5) H6B(0.5) C5B(0.5) H5B(0.5)
 C4B(0.5) H4B(0.5) C3B(0.5) C7B(0.5) H7BA(0.5) H7BB(0.5) H7BC(0.5) C8B(0.5)
 H8BA(0.5) H8BB(0.5) H8BC(0.5) C1D(0.25) C2D(0.25) C3D(0.25) H3D(0.25)
 C4D(0.25) H4D(0.25) C5D(0.25) H5D(0.25) C6D(0.25) H6D(0.25) C7D(0.25)
 H7DA(0.25) H7DB(0.25) H7DC(0.25) C8D(0.25) H8DA(0.25) H8DB(0.25) H8DC(0.25)
 C1E(0.25) C2E(0.25) C3E(0.25) H3E(0.25) C4E(0.25) H4E(0.25) C5E(0.25)
 H5E(0.25) C6E(0.25) H6E(0.25) C7E(0.25) H7EA(0.25) H7EB(0.25) H7EC(0.25)
 C8E(0.25) H8EA(0.25) H8EB(0.25) H8EC(0.25)
6.a Free rotating group:
 C2B(C1B,C6B,C5B,C4B,C3B), C1E(C2E,C3E,C4E,C5E,C6E)
6.b Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C27(H27), C34(H34), C47(H47), C54(H54)
6.c Me refined with riding coordinates:
 C7A(H7AA,H7AB,H7AC), C8E(H8EA,H8EB,H8EC)
6.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18), C19(H19),
 C26(H26), C29(H29), C30(H30), C31(H31), C32(H32), C36(H36), C37(H37), C38(H38),
  C39(H39), C46(H46), C49(H49), C50(H50), C51(H51), C52(H52), C56(H56),
 C57(H57), C58(H58), C59(H59), C1A(H1A), C2A(H2A), C3A(H3A), C6A(H6A), C1B(H1B),
  C6B(H6B), C5B(H5B), C4B(H4B), C3D(H3D), C4D(H4D), C5D(H5D), C6D(H6D),
 C3E(H3E), C4E(H4E), C5E(H5E), C6E(H6E)
6.e Fitted hexagon refined as free rotating group:
 C1D(C2D,C3D,C4D,C5D,C6D)
6.f Tetrahedral OH refined with riding coordinates:
 O3(H3), O4(H4)
6.g Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C7B(H7BA,H7BB,H7BC), C8B(H8BA,H8BB,H8BC), C7D(H7DA,H7DB,
 H7DC), C8D(H8DA,H8DB,H8DC), C7E(H7EA,H7EB,H7EC)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2