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_1570210
_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         '0.5(C18 H16 Cl2 N2 O), 0.5(H2 O)'
_chemical_formula_sum            'C9 H9 Cl N O'
_chemical_formula_weight         182.62
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2gr9tc
_audit_creation_date             2023-03-21
_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                 103.554(7)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.3768(13)
_cell_length_b                   6.9898(4)
_cell_length_c                   27.6891(17)
_cell_measurement_reflns_used    9067
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.28
_cell_volume                     3457.6(4)
_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      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0833
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            29127
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.280
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         5031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0719
_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^)+(0.0300P)^2^+11.7087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3730
_reflns_number_total             5031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05121h2.cif
_cod_data_source_block           v123
_cod_depositor_comments
'Adding full bibliography for 1570208--1570213.cif.'
_cod_database_code               1570210
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.926
_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 O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18)
;
_shelx_res_checksum              96115
_olex2_submission_special_instructions 'No special instructions were received'