An efficient, stereocontrolled and versatile synthetic route to bicyclic partially saturated privileged scaffolds.
Stewart, Hannah L.; Hanby, Abigail R.; King, Thomas A.; Bond, Andrew D.; Moss, Thomas A.; Sore, Hannah F.; Spring, David R.; Chemical communications (Cambridge, England) 56 (2020) 6818–6821; doi:10.1039/d0cc02728f

data_7126510
_publ_section_title
;
 An efficient, stereocontrolled and versatile synthetic route to bicyclic
 partially saturated privileged scaffolds.
;
_journal_issue                   50
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6818
_journal_page_last               6821
_journal_paper_doi               10.1039/d0cc02728f
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H22 F3 N4 +, Cl -'
_chemical_formula_sum            'C25 H22 Cl F3 N4'
_chemical_formula_weight         470.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2019-05-08 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.160(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6933(4)
_cell_length_b                   12.7845(10)
_cell_length_c                   15.7666(13)
_cell_measurement_reflns_used    3058
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      65.15
_cell_measurement_theta_min      2.84
_cell_volume                     1132.95(15)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1006
_diffrn_reflns_av_unetI/netI     0.1281
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10800
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        66.770
_diffrn_reflns_theta_max         66.770
_diffrn_reflns_theta_min         2.839
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    1.887
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
Flack x determined using 654 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1503
_refine_ls_R_factor_gt           0.0854
_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^)+(0.0522P)^2^+2.3325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.2028
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                2319
_reflns_number_total             3903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02728f2.cif
_cod_data_source_block           DS_B1_0025
_cod_depositor_comments          'Adding full bibliography for 7126510.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7126510
_cambridge_user_name             'Hanna Stewart'
_cambridge_user_crsid            hlo28
_cambridge_supervisor_name       'David Spring'
_cambridge_supervisor_crsid      drs36
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             HLS732
_cambridge_data_id               DS_B1_0025
_shelx_estimated_absorpt_t_min   0.360
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              67923
_shelx_hkl_checksum              95167