Atroposelective brominations to access chiral biaryl scaffolds using high-valent Pd-catalysis.
Linde, Sif T.; Corti, Vasco; Lauridsen, Vibeke H.; Lamhauge, Johannes N.; Jørgensen, Karl Anker; Rezayee, Nomaan M.; Chemical science 14 (2023) 3676–3681; doi:10.1039/d2sc06131g

data_1568611
_publ_section_title
;
 Atroposelective brominations to access chiral biaryl scaffolds using
 high-valent Pd-catalysis.
;
_journal_issue                   13
_journal_name_full               'Chemical science'
_journal_page_first              3676
_journal_page_last               3681
_journal_paper_doi               10.1039/d2sc06131g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C18 H8 Br Cl F2 O3'
_chemical_formula_sum            'C18 H8 Br Cl F2 O3'
_chemical_formula_weight         425.615
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-22 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                80.772(5)
_cell_angle_beta                 79.030(6)
_cell_angle_gamma                72.149(6)
_cell_formula_units_Z            2
_cell_length_a                   8.3118(7)
_cell_length_b                   8.4520(5)
_cell_length_c                   12.0667(8)
_cell_measurement_reflns_used    4231
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.3430
_cell_measurement_theta_min      3.4930
_cell_volume                     787.41(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.8761
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      4.00  88.00   0.75    3.58    --   14.97  55.00  40.00  112
  2  \w    -58.00  43.25   0.75    3.58    --   14.97 -55.00-102.00  135
  3  \w    -12.00  86.25   0.75    3.58    --   14.97  57.00-180.00  131
  4  \w    -17.00  13.00   0.75    3.58    --  -15.75 -77.00 150.00   40
  5  \w    -11.00  14.50   0.75    3.58    --  -15.75  77.00   0.00   34
  6  \w   -104.00 -77.75   0.75    3.58    --  -15.75-178.00  30.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0065414000
_diffrn_orient_matrix_UB_12      -0.0634527000
_diffrn_orient_matrix_UB_13      -0.0340009000
_diffrn_orient_matrix_UB_21      0.0768387000
_diffrn_orient_matrix_UB_22      -0.0484266000
_diffrn_orient_matrix_UB_23      0.0203772000
_diffrn_orient_matrix_UB_31      -0.0477099000
_diffrn_orient_matrix_UB_32      -0.0386725000
_diffrn_orient_matrix_UB_33      0.0453548000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.9972
_diffrn_reflns_Laue_measured_fraction_max 0.8761
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8373
_diffrn_reflns_point_group_measured_fraction_full 0.9972
_diffrn_reflns_point_group_measured_fraction_max 0.8761
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.91
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull whiteish colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_description       irregular
_exptl_crystal_F_000             420.138
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.2433
_refine_diff_density_min         -1.1602
_refine_diff_density_rms         0.1305
_refine_ls_d_res_high            0.6917
_refine_ls_d_res_low             6.1064
_refine_ls_goodness_of_fit_ref   1.0351
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0351
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.4722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3693
_reflns_number_total             4361
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2sc06131g2.cif
_cod_data_source_block           MKT_Sif_7_4_2022_pre2_autored
_cod_depositor_comments
'Adding full bibliography for 1568611--1568612.cif.'
_cod_database_code               1568611
_chemical_oxdiff_formula         C20H8O2ClBrF2
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L),
 C00M(H00M), C00O(H00O)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.756