Synthesis of polysubstituted bicyclo[2.1.1]hexanes enabling access to new chemical space.
Reinhold, Marius; Steinebach, Justin; Golz, Christopher; Walker, Johannes C. L.; Chemical science 14 (2023) 9885–9891; doi:10.1039/d3sc03083k

data_1569750
_publ_section_title
;
 Synthesis of polysubstituted bicyclo[2.1.1]hexanes enabling access to new
 chemical space.
;
_journal_issue                   36
_journal_name_full               'Chemical science'
_journal_page_first              9885
_journal_page_last               9891
_journal_paper_doi               10.1039/d3sc03083k
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H23 N O3'
_chemical_formula_sum            'C23 H23 N O3'
_chemical_formula_weight         361.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2023-08-11
_audit_creation_method
;FinalCif V123 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-08-17 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2717(8)
_cell_length_b                   16.1815(16)
_cell_length_c                   18.3606(18)
_cell_measurement_reflns_used    9756
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      79.508
_cell_measurement_theta_min      3.640
_cell_volume                     1863.3(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
'Bruker BIS V6.2.15/2021-03-16 && APEX4 2022.1-1'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            60017
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.730
_diffrn_reflns_theta_min         3.641
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8041
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1181 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.8041.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method 'from ethyl acetate.'
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1667 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_coef       0.0029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0241
_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^)+(0.0382P)^2^+0.2625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0637
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3956
_reflns_number_total             4010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03083k2.cif
_cod_data_source_block           cu_2069_cg_0m
_cod_depositor_comments
'Adding full bibliography for 1569748--1569753.cif.'
_cod_database_code               1569750
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.784
_shelx_estimated_absorpt_t_max   0.965
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              52967