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_4134057
_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         'C20 H17 N3 O'
_chemical_formula_sum            'C20 H17 N3 O'
_chemical_formula_weight         315.36
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-05-02
_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                   7.41462(9)
_cell_length_b                   10.40955(11)
_cell_length_c                   20.8084(2)
_cell_measurement_reflns_used    19117
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      73.4190
_cell_measurement_theta_min      4.2190
_cell_volume                     1606.05(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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   -114.00 -59.00   1.00    2.50    --  -43.01 -57.00-150.00   55
  2  \w    -69.00  29.00   1.00    2.50    --  -43.01  57.00 120.00   98
  3  \w    -44.00 -15.00   1.00    2.50    --  -43.01 -57.00-150.00   29
  4  \w   -128.00  45.00   1.00    2.50    --  -43.01   0.00   0.00  173
  5  \w    -41.00 -15.00   1.00    2.50    --  -43.01 -57.00  90.00   26
  6  \w    -98.00 -20.00   1.00    2.50    --  -43.01 -37.00 -60.00   78
  7  \w     32.00  98.00   1.00    2.50    --   43.01-125.00 -60.00   66
  8  \w     11.00  36.00   1.00    2.50    --   46.00  84.00 -48.95   25
  9  \w     12.00  42.00   1.00    2.50    --   46.00  81.00 124.08   30
 10  \w     11.00  36.00   1.00    2.50    --   46.00  84.00-163.67   25
 11  \w     12.00  37.00   1.00    2.50    --   46.00  83.00  25.98   25
 12  \w     16.00  41.00   1.00    2.50    --   50.00  81.00 -26.70   25
 13  \w     25.00  55.00   1.00    2.50    --   58.00  77.00-129.20   30
 14  \w     34.00  60.00   1.00    2.50    --   62.00  76.00  12.54   26
 15  \w     29.00  60.00   1.00    2.50    --   62.00  77.00  58.79   31
 16  \w     30.00  59.00   1.00    2.50    --   62.00  77.00 121.80   29
 17  \w     35.00  61.00   1.00    2.50    --   66.00  76.00 -76.30   26
 18  \w    120.00 146.00   1.00    2.50    --   70.00  77.00 -25.32   26
 19  \w     84.00 146.00   1.00    2.50    --   70.00  77.00 159.92   62
 20  \w     37.00  69.00   1.00    2.50    --   70.00  77.00 -25.32   32
 21  \w     37.00  77.00   1.00    2.50    --   70.00  77.00 159.92   40
 22  \w     37.00  67.00   1.00    2.50    --   70.00  77.00  96.71   30
 23  \w     42.00  77.00   1.00    2.50    --   74.00  73.00-116.02   35
 24  \w     45.00  72.00   1.00   10.00    --   78.00  77.00  81.60   27
 25  \w     47.00  86.00   1.00   10.00    --   78.00  76.00 -76.02   39
 26  \w     49.00  74.00   1.00   10.00    --   82.00  77.00-170.74   25
 27  \w     50.00  84.00   1.00   10.00    --   82.00  74.00 129.72   34
 28  \w     73.00 161.00   1.00   10.00    --  105.68  77.00 120.00   88
 29  \w     71.00 118.00   1.00   10.00    --  105.68-125.00 150.00   47
 30  \w     78.00 178.00   1.00   10.00    --  105.68  61.00   0.00  100
 31  \w    120.00 161.00   1.00   10.00    --  105.68 125.00 -30.00   41
 32  \w     73.00 170.00   1.00   10.00    --  105.68  77.00 -90.00   97
 33  \w     79.00 106.00   1.00   10.00    --  105.68  61.00-150.00   27
 34  \w    114.00 176.00   1.00   10.00    --  105.68  77.00-180.00   62
 35  \w     74.00 100.00   1.00   10.00    --  105.68  77.00-180.00   26
 36  \w     74.00 133.00   1.00   10.00    --  105.68  77.00  30.00   59
 37  \w     74.00 170.00   1.00   10.00    --  105.68  77.00 150.00   96
 38  \w    132.00 158.00   1.00   10.00    --  105.68  77.00  90.00   26
 39  \w     33.00 118.00   1.00   10.00    --  105.68-125.00 -60.00   85
 40  \w     74.00 129.00   1.00   10.00    --  105.68  77.00  90.00   55
 41  \w    112.00 138.00   1.00   10.00    --  105.68  77.00 -30.00   26
 42  \w     73.00  99.00   1.00   10.00    --  105.68  77.00 -30.00   26
 43  \w     73.00 178.00   1.00   10.00    --  105.68  77.00 -60.00  105
 44  \w     73.00 173.00   1.00   10.00    --  105.68  77.00-120.00  100
 45  \w     73.00 169.00   1.00   10.00    --  105.68  77.00  60.00   96
 46  \w    141.00 168.00   1.00   10.00    --  105.68 125.00 -90.00   27
 47  \w    107.00 177.00   1.00   10.00    --  105.68 125.00  60.00   70
 48  \w     78.00 103.00   1.00   10.00    --  105.68  61.00  30.00   25
 49  \w     73.00 166.00   1.00   10.00    --  105.68  77.00-150.00   93
 50  \w     73.00  99.00   1.00   10.00    --  105.68  77.00   0.00   26
 51  \w     33.00 134.00   1.00   10.00    --  105.68 -77.00 -30.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0923620000
_diffrn_orient_matrix_UB_12      -0.1047434000
_diffrn_orient_matrix_UB_13      -0.0406530000
_diffrn_orient_matrix_UB_21      -0.0217833000
_diffrn_orient_matrix_UB_22      0.0961817000
_diffrn_orient_matrix_UB_23      -0.0557324000
_diffrn_orient_matrix_UB_31      0.1847699000
_diffrn_orient_matrix_UB_32      -0.0410567000
_diffrn_orient_matrix_UB_33      -0.0269136000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0079
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27630
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.513
_diffrn_reflns_theta_min         4.249
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.313
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018).
 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    1.304
_exptl_crystal_description       irregular
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.551
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.363
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1325 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.0159(10)
_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   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0272
_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^)+(0.0474P)^2^+0.2136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0782
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3186
_reflns_number_total             3192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12299_si_002.cif
_cod_data_source_block           qhn-1-789
_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               4134057
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C20 H17 N3 O1'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.085
_oxdiff_exptl_absorpt_empirical_full_min 0.669