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_4135639
_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         'C112 H56 O4, 6(C6 H4 Cl2)'
_chemical_formula_sum            'C148 H80 Cl12 O4'
_chemical_formula_weight         2347.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_contact_author_name
;
;
_audit_creation_date             2019-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.474(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5697(9)
_cell_length_b                   17.9147(9)
_cell_length_c                   38.807(2)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    150
_cell_measurement_theta_max      55.471
_cell_measurement_theta_min      2.954
_cell_volume                     13173.4(11)
_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      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_unetI/netI     0.1080
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            67535
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.161
_diffrn_reflns_theta_min         2.046
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    1.770
_exptl_absorpt_correction_T_max  0.7510
_exptl_absorpt_correction_T_min  0.5491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1308 before and 0.0918 after correction. The Ratio of minimum to maximum transmission is 0.7312. 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    1.184
_exptl_crystal_description       Plate
_exptl_crystal_F_000             4816
_exptl_crystal_recrystallization_method 'crystallized from oPhCl2/MeOH'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1071
_refine_ls_number_reflns         67535
_refine_ls_number_restraints     517
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0892
_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^)+(0.1465P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2359
_refine_ls_wR_factor_ref         0.2532
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                43412
_reflns_number_total             67535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jw21352_8_6PhCl2.cif
_cod_data_source_block           jw21352
_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               4135639
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.765
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7037(16)
 0.2963(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C5F-Cl2F = C6F-Cl1F = C1H-Cl1H = C2H-Cl2H = C2G-Cl1G
 1.77 with sigma of 0.002
 C8C-Cl3C = C7C-Cl4C = C8D-Cl3D = C7D-Cl4D
 1.77 with sigma of 0.002
 Cl1H-Cl2H = Cl3D-Cl4D = Cl3C-Cl4C
 3.2 with sigma of 0.02
 C9C-Cl3C = C8C-Cl4C
 2.71 with sigma of 0.002
 C9D-Cl3D = C8D-Cl4D
 2.71 with sigma of 0.002
4. Restrained planarity
 Cl1H, Cl2H, C1H, C2H, C3H, C4H, C5H, C6H
 with sigma of 0.1
 Cl3C, Cl4C, C7C, C8C, C9C, C10C, C11C, C12C
 with sigma of 0.1
 Cl3D, Cl4D, C7D, C8D, C9D, C10D, C11D, C12D
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
Cl1F \\sim Cl2F \\sim 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
Cl1C \\sim Cl2C \\sim C1C \\sim C2C \\sim C3C \\sim C4C \\sim C5C \\sim C6C:
within 2A with sigma of 0.002 and sigma for terminal atoms of 0.02
Cl3C \\sim Cl4C \\sim C7C \\sim C8C \\sim C9C \\sim C10C \\sim C11C \\sim C12C
\\sim Cl3D \\sim Cl4D \\sim C7D \\sim C8D \\sim C9D \\sim C10D \\sim C11D \\sim
C12D: 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:
within 2A with sigma of 0.002 and sigma for terminal atoms of 0.02
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
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
6. Same fragment restrains
{Cl3C, Cl4C, C7C, C8C, C9C, C10C, C11C, C12C} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl3D, Cl4D, C7D, C8D, C9D, C10D, C11D, C12D}
7. Others
 Sof(Cl3D)=Sof(Cl4D)=Sof(C7D)=Sof(C8D)=Sof(C9D)=Sof(H9D)=Sof(C10D)=Sof(H10D)=
 Sof(C11D)=Sof(H11D)=Sof(C12D)=Sof(H12D)=0.5*(1-FVAR(2))
 Sof(Cl3C)=Sof(Cl4C)=Sof(C7C)=Sof(C8C)=Sof(C9C)=Sof(H9C)=Sof(C10C)=Sof(H10C)=
 Sof(C11C)=Sof(H11C)=Sof(C12C)=Sof(H12C)=0.5*FVAR(2)
 Fixed Sof: Cl1C(0.5) Cl2C(0.5) C1C(0.5) C2C(0.5) H2C(0.5) C3C(0.5) H3C(0.5)
 C4C(0.5) H4C(0.5) C5C(0.5) H5C(0.5) C6C(0.5) Cl1F(0.25) Cl2F(0.25) C1F(0.25)
 H1F(0.25) C2F(0.25) H2F(0.25) C3F(0.25) H3F(0.25) C4F(0.25) H4F(0.25)
 C5F(0.25) C6F(0.25) Cl1G(0.25) Cl2G(0.25) C1G(0.25) H1G(0.25) C2G(0.25)
 C3G(0.25) C4G(0.25) H4G(0.25) C5G(0.25) H5G(0.25) C6G(0.25) H6G(0.25)
 Cl1H(0.25) Cl2H(0.25) C1H(0.25) C2H(0.25) C3H(0.25) H3H(0.25) C4H(0.25)
 H4H(0.25) C5H(0.25) H5H(0.25) C6H(0.25) H6H(0.25) Cl1I(0.25) Cl2I(0.25)
 C1I(0.25) H1I(0.25) C2I(0.25) H2I(0.25) C3I(0.25) H3I(0.25) C4I(0.25)
 H4I(0.25) C5I(0.25) C6I(0.25)
8.a Ternary CH refined with riding coordinates:
 C11A(H11A), C22A(H22A), C25A(H25A), C36A(H36A), C11B(H11B), C22B(H22B),
 C25B(H25B), C36B(H36B)
8.b Aromatic/amide H refined with riding coordinates:
 C13A(H13A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A), C20A(H20A),
 C27A(H27A), C29A(H29A), C30A(H30A), C31A(H31A), C32A(H32A), C34A(H34A),
 C13B(H13B), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B), C20B(H20B),
 C27B(H27B), C29B(H29B), C30B(H30B), C31B(H31B), C32B(H32B), C34B(H34B),
 C2C(H2C), C3C(H3C), C4C(H4C), C5C(H5C), C9C(H9C), C10C(H10C), C11C(H11C),
 C12C(H12C), C9D(H9D), C10D(H10D), C11D(H11D), C12D(H12D), C14C(H14C),
 C15C(H15C), C17C(H17C), C18C(H18C), C1F(H1F), C2F(H2F), C3F(H3F), C4F(H4F),
 C1G(H1G), C4G(H4G), C5G(H5G), C6G(H6G), C3H(H3H), C4H(H4H), C5H(H5H), C6H(H6H),
  C1I(H1I), C2I(H2I), C3I(H3I), C4I(H4I)
8.c Fitted hexagon refined as free rotating group:
 C1C(C2C,C3C,C4C,C5C,C6C), C7C(C8C,C9C,C10C,C11C,C12C), C7D(C8D,C9D,C10D,C11D,
 C12D), C1F(C2F,C3F,C4F,C5F,C6F), C1G(C2G,C3G,C4G,C5G,C6G), C1H(C2H,C3H,C4H,C5H,
 C6H), C1I(C2I,C3I,C4I,C5I,C6I)
;