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_4135641
_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         'C96 H48 O4, 9(C6 H4 Cl2)'
_chemical_formula_sum            'C150 H84 Cl18 O4'
_chemical_formula_weight         2588.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_contact_author_name
;
;
_audit_creation_date             2019-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.772(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   43.4297(17)
_cell_length_b                   13.7993(6)
_cell_length_c                   20.6059(9)
_cell_measurement_reflns_used    9840
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.070
_cell_measurement_theta_min      3.369
_cell_volume                     12043.6(9)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (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 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0483
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            77769
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.117
_diffrn_reflns_theta_min         2.086
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_exptl_absorpt_coefficient_mu    4.221
_exptl_absorpt_correction_T_max  0.5220
_exptl_absorpt_correction_T_min  0.3652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1289 before and 0.0620 after correction. The Ratio of minimum to maximum transmission is 0.6996. 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    1.427
_exptl_crystal_description       Plate
_exptl_crystal_F_000             5288
_exptl_crystal_recrystallization_method 'crystallized from oPhCl2'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     977
_refine_ls_number_reflns         11403
_refine_ls_number_restraints     614
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0997P)^2^+32.5634P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1852
_refine_ls_wR_factor_ref         0.1934
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9770
_reflns_number_total             11403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jw2183_9_9PhCl2.cif
_cod_data_source_block           jw2183
_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               4135641
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.729
_shelx_estimated_absorpt_t_min   0.517
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C1H-Cl1H = C6H-Cl2H = C1G-Cl1G = C6G-Cl2G
 1.71 with sigma of 0.01
 C1B-Cl1B = C6B-Cl2B = C5F-Cl2F = C6F-Cl1F = C1I-Cl1I = C2I-Cl2I
 1.71 with sigma of 0.002
 Cl1F-Cl2F
 3.19 with sigma of 0.002
 C1C-Cl1C \\sim C2C-Cl2C \\sim C3C-Cl3C
 with sigma of 0.002
3. Restrained planarity
 Cl1F, Cl2F, C1F, C2F, C3F, C4F, C5F, C6F
 with sigma of 0.001
 Cl1G, Cl2G, C1G, C2G, C3G, C4G, C5G, C6G, Cl1H, Cl2H, C1H, C2H, C3H, C4H, C5H,
  C6H
 with sigma of 0.002
4. Uiso/Uaniso restraints and constraints
C1B \\sim C2B \\sim C3B \\sim C4B \\sim C5B \\sim C6B: within 2A with sigma of
0.002 and sigma for terminal atoms of 0.02
C1F \\sim C2F \\sim C3F \\sim C4F \\sim C5F \\sim C6F: within 2A with sigma of
0.002 and sigma for terminal atoms of 0.02
Cl1G \\sim Cl2G \\sim C1G \\sim C2G \\sim C3G \\sim C4G \\sim C5G \\sim C6G
\\sim Cl1H \\sim Cl2H \\sim C1H \\sim C2H \\sim C3H \\sim C4H \\sim C5H \\sim
C6H: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.02
Cl1A \\sim Cl2A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A
\\sim Cl1I \\sim Cl2I \\sim C1I \\sim C2I \\sim C3I \\sim C4I \\sim C5I \\sim
C6I: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.02
5. Same fragment restrains
{Cl1G, Cl2G, C1G, C2G, C3G, C4G, C5G, C6G} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1H, Cl2H, C1H, C2H, C3H, C4H, C5H, C6H}
6. Others
 Sof(Cl1F)=Sof(Cl2F)=Sof(C1F)=Sof(H1F)=Sof(C2F)=Sof(H2F)=Sof(C3F)=Sof(H3F)=
 Sof(C4F)=Sof(H4F)=Sof(C5F)=Sof(C6F)=1-FVAR(1)
 Sof(Cl1B)=Sof(Cl2B)=Sof(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=
 Sof(H4B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=FVAR(1)
 Sof(Cl1I)=Sof(Cl2I)=Sof(C1I)=Sof(C2I)=Sof(C3I)=Sof(H3I)=Sof(C4I)=Sof(H4I)=
 Sof(C5I)=Sof(H5I)=Sof(C6I)=Sof(H6I)=1-FVAR(2)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1A)=Sof(C2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=FVAR(2)
 Sof(Cl3C)=1-FVAR(3)
 Sof(Cl1C)=FVAR(3)
 Sof(Cl3D)=1-FVAR(4)
 Sof(Cl2D)=FVAR(4)
 Fixed Sof: Cl1G(0.25) Cl2G(0.25) C1G(0.25) C2G(0.25) H2G(0.25) C3G(0.25)
 H3G(0.25) C4G(0.25) H4G(0.25) C5G(0.25) H5G(0.25) C6G(0.25) Cl1H(0.25)
 Cl2H(0.25) C1H(0.25) C2H(0.25) H2H(0.25) C3H(0.25) H3H(0.25) C4H(0.25)
 H4H(0.25) C5H(0.25) H5H(0.25) C6H(0.25) H1C(0.5) H3C(0.5) H2D(0.5) H6D(0.5)
7.a Ternary CH refined with riding coordinates:
 C21(H21), C28(H28), C35(H35), C42(H42)
7.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C17(H17), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26),
 C30(H30), C31(H31), C32(H32), C33(H33), C37(H37), C38(H38), C39(H39), C40(H40),
  C44(H44), C45(H45), C46(H46), C47(H47), C2G(H2G), C3G(H3G), C4G(H4G),
 C5G(H5G), C2H(H2H), C3H(H3H), C4H(H4H), C5H(H5H), C3A(H3A), C4A(H4A), C5A(H5A),
  C6A(H6A), C3I(H3I), C4I(H4I), C5I(H5I), C6I(H6I), C2B(H2B), C3B(H3B),
 C4B(H4B), C5B(H5B), C1F(H1F), C2F(H2F), C3F(H3F), C4F(H4F), C1C(H1C), C3C(H3C),
  C4C(H4C), C5C(H5C), C6C(H6C), C2D(H2D), C3D(H3D), C4D(H4D), C5D(H5D), C6D(H6D)
7.c Fitted hexagon refined as free rotating group:
 C1G(C2G,C3G,C4G,C5G,C6G), C1H(C2H,C3H,C4H,C5H,C6H), C1A(C2A,C3A,C4A,C5A,C6A),
 C1I(C2I,C3I,C4I,C5I,C6I), C1B(C2B,C3B,C4B,C5B,C6B), C1F(C2F,C3F,C4F,C5F,C6F)
;
_cod_database_fobs_code 4135641