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_1568612
_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_absolute_configuration ad
_chemical_formula_moiety         '0.57(C17 H16 Br2 O2)'
_chemical_formula_sum            'C9.714 H9.143 Br1.143 O1.143'
_chemical_formula_weight         235.50
_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'
_symmetry_Int_Tables_number      19
_audit_creation_date             2022-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-27 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            7
_cell_length_a                   10.6752(2)
_cell_length_b                   11.9710(4)
_cell_length_c                   12.2865(4)
_cell_measurement_reflns_used    11138
_cell_measurement_temperature    100
_cell_measurement_theta_max      35.9100
_cell_measurement_theta_min      2.3610
_cell_volume                     1570.13(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_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    -31.00  84.00   1.00    7.50    --   38.99 -86.00-159.00  115
  2  \w     84.00 130.00   1.00    7.50    --   38.99 110.00  43.00   46
  3  \w   -130.00 -84.00   1.00    7.50    --  -39.46-110.00 -51.00   46
  4  \w   -100.00 -37.00   1.00    7.50    --   -0.23 178.00-150.00   63
  5  \w     -6.00  56.00   1.00    7.50    --   -0.23-110.00 -51.00   62
  6  \w    -42.00  43.00   1.00    7.50    --   -0.23 -77.00-180.00   85
  7  \w     -5.00  42.00   1.00    7.50    --   38.99  77.00 -90.00   47
  8  \w     -5.00  42.00   1.00    7.50    --   38.99  77.00-180.00   47
  9  \w     -5.00  42.00   1.00    7.50    --   38.99  77.00  90.00   47
 10  \w   -140.00 -82.00   1.00    7.50    --  -39.46 -77.00 -30.00   58
 11  \w    -42.00  -8.00   1.00    7.50    --   -0.23 -77.00 120.00   34
;
_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      0.0096886000
_diffrn_orient_matrix_UB_12      0.0577477000
_diffrn_orient_matrix_UB_13      0.0098326000
_diffrn_orient_matrix_UB_21      -0.0315884000
_diffrn_orient_matrix_UB_22      -0.0048446000
_diffrn_orient_matrix_UB_23      0.0505403000
_diffrn_orient_matrix_UB_31      0.0576911000
_diffrn_orient_matrix_UB_32      -0.0123440000
_diffrn_orient_matrix_UB_33      0.0260371000
_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  0.0813
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26846
_diffrn_reflns_theta_full        28.2788
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.38
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  1.00000
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.7433
_exptl_crystal_description       sphere
_exptl_crystal_F_000             814.2057
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         0.9974
_refine_diff_density_min         -0.8464
_refine_diff_density_rms         0.1245
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.015(11)
_refine_ls_d_res_high            0.7501
_refine_ls_d_res_low             8.5741
_refine_ls_goodness_of_fit_ref   1.0319
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0319
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0290P)^2^+0.1374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0715
_reflns_Friedel_coverage         1.000
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              16
_reflns_limit_l_min              -16
_reflns_number_gt                3619
_reflns_number_total             3897
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2sc06131g2.cif
_cod_data_source_block           MKT_NMR_01_03_2021_autored
_cod_depositor_comments
'Adding full bibliography for 1568611--1568612.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1568612
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.23
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00C(H00C), C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I)
2.c Idealised Me refined as rotating group:
 C00J(H00a,H00b,H00f), C00K(H00j,H00k,H00l), C00L(H00m,H00n,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 2.004
_oxdiff_exptl_absorpt_empirical_full_min 0.616