Intermolecular Palladium(0)-Catalyzed Atropo-enantioselective C-H Arylation of Heteroarenes.
Nguyen, Qui-Hien; Guo, Shu-Min; Royal, Titouan; Baudoin, Olivier; Cramer, Nicolai; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b12299

data_4134058
_publ_section_title
;
 Intermolecular Palladium(0)-Catalyzed Atropo-enantioselective C-H
 Arylation of Heteroarenes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b12299
_journal_year                    2020
_chemical_formula_moiety         'C26 H21 N3 O'
_chemical_formula_sum            'C26 H21 N3 O'
_chemical_formula_weight         391.46
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.90611(7)
_cell_length_b                   11.94278(10)
_cell_length_c                   20.9620(2)
_cell_measurement_reflns_used    22682
_cell_measurement_temperature    139.99(10)
_cell_measurement_theta_max      72.5460
_cell_measurement_theta_min      4.1940
_cell_volume                     1979.25(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      139.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -98.00 -42.00   1.00    2.00    --  -40.85 -77.00  30.00   56
  2  \w   -114.00 -16.00   1.00    2.00    --  -40.85 -38.00 -60.00   98
  3  \w    -41.00  -8.00   1.00    2.00    --  -40.85 -77.00  30.00   33
  4  \w    -92.00  -3.00   1.00    2.00    --  -40.85 125.00 120.00   89
  5  \w   -113.00 -13.00   1.00    2.00    --  -40.85 -57.00 120.00  100
  6  \w   -106.00 -13.00   1.00    2.00    --  -40.85 -57.00-150.00   93
  7  \w     24.00  89.00   1.00    2.00    --   40.85-125.00  30.00   65
  8  \w     12.00  37.00   1.00    2.00    --   46.00  83.00 146.07   25
  9  \w     11.00  36.00   1.00    2.00    --   46.00  84.00   1.71   25
 10  \w     16.00  41.00   1.00    2.00    --   50.00  81.00-154.21   25
 11  \w     16.00  41.00   1.00    2.00    --   50.00  81.00 101.77   25
 12  \w     16.00  41.00   1.00    2.00    --   50.00  82.00 -87.36   25
 13  \w     31.00  58.00   1.00    2.00    --   62.00  77.00 -62.07   27
 14  \w     33.00  59.00   1.00    2.00    --   62.00  75.00-167.61   26
 15  \w     29.00  56.00   1.00    2.00    --   62.00  77.00  -1.28   27
 16  \w     97.00 133.00   1.00    2.00    --   62.00  76.00 138.32   36
 17  \w     31.00  56.00   1.00    2.00    --   62.00  76.00 138.32   25
 18  \w     35.00  60.00   1.00    2.00    --   66.00  75.00  27.26   25
 19  \w     39.00  68.00   1.00    2.00    --   66.00  75.00 159.54   29
 20  \w     34.00  67.00   1.00    2.00    --   66.00  76.00  98.70   33
 21  \w    102.00 140.00   1.00    2.00    --   66.00  75.00  27.26   38
 22  \w    101.00 142.00   1.00    2.00    --   70.00  75.00-140.75   41
 23  \w     38.00  65.00   1.00    2.00    --   70.00  75.00-140.75   27
 24  \w     37.00  65.00   1.00    2.00    --   70.00  77.00  31.61   28
 25  \w     43.00  79.00   1.00    8.00    --   74.00  72.00  52.53   36
 26  \w     42.00  76.00   1.00    8.00    --   74.00  76.00-114.06   34
 27  \w     41.00  81.00   1.00    8.00    --   74.00  77.00 -54.31   40
 28  \w     53.00  79.00   1.00    8.00    --   82.00  61.00 105.75   26
 29  \w     60.00  88.00   1.00    8.00    --   90.00  65.00-150.77   28
 30  \w     58.00  84.00   1.00    8.00    --   90.00  74.00 113.47   26
 31  \w     65.00 155.00   1.00    8.00    --   94.00  64.00  44.55   90
 32  \w     68.00 159.00   1.00    8.00    --   94.00  66.00-114.68   91
 33  \w     73.00 177.00   1.00    8.00    --  105.15  77.00 120.00  104
 34  \w     73.00 166.00   1.00    8.00    --  105.15  77.00 -90.00   93
 35  \w     77.00 104.00   1.00    8.00    --  105.15  60.00 -49.90   27
 36  \w    103.00 172.00   1.00    8.00    --  105.15 111.00-150.00   69
 37  \w     75.00 177.00   1.00    8.00    --  105.15  77.00-180.00  102
 38  \w     73.00 138.00   1.00    8.00    --  105.15  77.00-150.00   65
 39  \w     55.00 115.00   1.00    8.00    --  105.15 -45.00  90.00   60
 40  \w     77.00 146.00   1.00    8.00    --  105.15  77.00  90.00   69
 41  \w    123.00 178.00   1.00    8.00    --  105.15  77.00  30.00   55
 42  \w     73.00  99.00   1.00    8.00    --  105.15  77.00  30.00   26
 43  \w     38.00 108.00   1.00    8.00    --  105.15 -94.00 120.00   70
 44  \w     78.00 113.00   1.00    8.00    --  105.15  61.00 -30.00   35
 45  \w     74.00 108.00   1.00    8.00    --  105.15 -94.00-120.00   34
 46  \w     73.00 178.00   1.00    8.00    --  105.15  77.00  60.00  105
 47  \w     73.00 131.00   1.00    8.00    --  105.15  77.00-120.00   58
 48  \w     38.00 112.00   1.00    8.00    --  105.15-111.00  60.00   74
 49  \w     73.00 148.00   1.00    8.00    --  105.15  77.00 150.00   75
 50  \w    108.00 145.00   1.00    8.00    --  105.15 178.00 -30.00   37
 51  \w     73.00 145.00   1.00    8.00    --  105.15  77.00 -30.00   72
 52  \w     74.00 178.00   1.00    8.00    --  105.15  77.00   0.00  104
 53  \w     37.00 110.00   1.00    8.00    --  105.15-111.00   0.00   73
 54  \w    121.00 157.00   1.00    8.00    --  105.15  60.00 -49.90   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1352409000
_diffrn_orient_matrix_UB_12      -0.0591729000
_diffrn_orient_matrix_UB_13      -0.0407498000
_diffrn_orient_matrix_UB_21      0.0891227000
_diffrn_orient_matrix_UB_22      -0.1130181000
_diffrn_orient_matrix_UB_23      0.0111912000
_diffrn_orient_matrix_UB_31      -0.1083157000
_diffrn_orient_matrix_UB_32      -0.0190732000
_diffrn_orient_matrix_UB_33      0.0601374000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34686
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.820
_diffrn_reflns_theta_min         4.218
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics as
 implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       irregular
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1623 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_coef       0.0025(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   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         3921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0471P)^2^+0.1904P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0756
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3870
_reflns_number_total             3921
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12299_si_004.cif
_cod_data_source_block           qhn-1-874-876
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4134058
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C26 H21 N3 O1'
_chemical_oxdiff_usercomment     'dirty crystals'
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.834
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.547
_oxdiff_exptl_absorpt_empirical_full_min 0.737