2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants.
Paul, Shashwati; Adelfinsky, Daniel; Salome, Christophe; Fessard, Thomas; Brown, M. Kevin; Chemical science 14 (2023) 8070–8075; doi:10.1039/d3sc02695g

data_1569507
_publ_section_title
;
 2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane
 variants.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              8070
_journal_page_last               8075
_journal_paper_doi               10.1039/d3sc02695g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H20 N2 O'
_chemical_formula_sum            'C22 H20 N2 O'
_chemical_formula_weight         328.40
_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_creation_date             2021-05-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-05-19 deposited with the CCDC.	2023-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                71.2030(10)
_cell_angle_beta                 79.0020(10)
_cell_angle_gamma                83.4110(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2901(2)
_cell_length_b                   10.5132(3)
_cell_length_c                   11.8680(4)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    143.0
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.85
_cell_volume                     843.87(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      143.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker VENTURE D8'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0267
_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       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            57033
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.050
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_preparation       synthesized
_exptl_crystal_recrystallization_method
'Slow evaporation of a mixture of ethyl acetate and pentane'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3879
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0579P)^2^+0.3404P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3014
_reflns_number_total             3879
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02695g2.cif
_cod_data_source_block           mo_21144_0m
_cod_depositor_comments          'Adding full bibliography for 1569507.cif.'
_cod_database_code               1569507
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C6-C5 \\sim C6-C5A
 with sigma of 0.02
 C1-C3 \\sim C1A-C3A
 with sigma of 0.04
 C6-C1 \\sim C6-C1A
 with sigma of 0.02
 C2-C4 \\sim C2A-C4A
 with sigma of 0.04
 C5-C4 \\sim C5A-C4A
 with sigma of 0.02
 C1-C2 \\sim C1A-C2A
 with sigma of 0.02
 C3-C2 \\sim C3A-C2A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C6-C2 \\sim C6-C2A
 with sigma of 0.04
 C6-C4 \\sim C6-C4A
 with sigma of 0.04
 C5-C3 \\sim C5A-C3A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C3A) = Uanis(C3)
Uanis(C5A) = Uanis(C5)
Uanis(C1A) = Uanis(C1)
Uanis(C4) = Uanis(C4A)
Uanis(C2A) = Uanis(C2)
4. Others
 Sof(C5A)=Sof(H5A)=Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=
 Sof(C1A)=Sof(H1AA)=1-FVAR(1)
 Sof(C5)=Sof(H5)=Sof(C1)=Sof(H1A)=Sof(C3)=Sof(H3)=Sof(C2)=Sof(H2)=Sof(C4)=
 Sof(H4)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C7(H7), C11(H11), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C17(H17), C20(H20), C16(H16), C21(H21), C22(H22), C5(H5),
 C1(H1A), C3(H3), C2(H2), C4(H4), C5A(H5A), C4A(H4A), C3A(H3A), C2A(H2A),
 C1A(H1AA)
;
_shelx_res_checksum              30816
_olex2_submission_original_sample_id SHP-II-171
_olex2_submission_special_instructions 'No special instructions were received'