1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of <i>ortho</i>-substituted benzene.
Denisenko, Aleksandr; Garbuz, Pavel; Makovetska, Yelyzaveta; Shablykin, Oleh; Lesyk, Dmytro; Al-Maali, Galeb; Korzh, Rodion; Sadkova, Iryna V.; Mykhailiuk, Pavel K.; Chemical science 14 (2023) 14092–14099; doi:10.1039/d3sc05121h

data_1570209
_publ_section_title
;
 1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of
 <i>ortho</i>-substituted benzene.
;
_journal_issue                   48
_journal_name_full               'Chemical science'
_journal_page_first              14092
_journal_page_last               14099
_journal_paper_doi               10.1039/d3sc05121h
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C14 H13 F3 O2'
_chemical_formula_sum            'C14 H13 F3 O2'
_chemical_formula_weight         270.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2gr9vd
_audit_creation_date             2023-03-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-08-03 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.190(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9641(4)
_cell_length_b                   20.6944(9)
_cell_length_c                   8.0024(4)
_cell_measurement_reflns_used    3974
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.82
_cell_measurement_theta_min      2.64
_cell_volume                     1278.65(11)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.968
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0563P)^2^+1.2150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1424
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1849
_reflns_number_total             2257
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05121h2.cif
_cod_data_source_block           v109
_cod_depositor_comments
'Adding full bibliography for 1570208--1570213.cif.'
_cod_database_code               1570209
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C13(H13)
;
_shelx_res_checksum              53148
_olex2_submission_special_instructions 'No special instructions were received'