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_4134059
_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_absolute_configuration rmad
_chemical_formula_moiety         'C30 H26 N6 O2'
_chemical_formula_sum            'C30 H26 N6 O2'
_chemical_formula_weight         502.57
_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             2019-10-23
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.10.11 svn.r3662 for OlexSys, GUI svn.r5962)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.62940(4)
_cell_length_b                   16.20428(8)
_cell_length_c                   16.44875(9)
_cell_measurement_reflns_used    21574
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.8340
_cell_measurement_theta_min      3.8050
_cell_volume                     2566.62(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.62a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.62a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.62a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (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 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -72.00 -24.00   1.00    2.50    --  -40.85  77.00 120.00   48
  2  \w    -78.00 -29.00   1.00    2.50    --  -40.85 -38.00  90.00   49
  3  \w   -114.00 -19.00   1.00    2.50    --  -40.85 -38.00-180.00   95
  4  \w    -82.00  37.00   1.00    2.50    --  -40.85  19.00 -60.00  119
  5  \w    -20.00  71.00   1.00    2.50    --   40.85 -77.00 150.00   91
  6  \w     37.00  94.00   1.00    2.50    --   40.85-125.00  30.00   57
  7  \w     62.00 109.00   1.00   10.00    --  112.00-111.00  60.00   47
  8  \w    144.00 175.00   1.00   10.00    --  112.00 111.00  90.00   31
  9  \w    102.00 128.00   1.00   10.00    --  112.00 -77.00  90.00   26
 10  \w    110.00 138.00   1.00   10.00    --  112.00 111.00  90.00   28
 11  \w     39.00  83.00   1.00   10.00    --  112.00-111.00 -90.00   44
 12  \w     69.00 106.00   1.00   10.00    --  112.00 -94.00 -30.00   37
 13  \w     75.00 101.00   1.00   10.00    --  112.00 178.00  30.00   26
 14  \w     72.00 108.00   1.00   10.00    --  112.00-111.00-120.00   36
 15  \w     62.00 142.00   1.00   10.00    --  112.00 178.00   0.00   80
 16  \w     85.00 171.00   1.00   10.00    --  112.00  30.00  30.00   86
 17  \w    105.00 134.00   1.00   10.00    --  112.00 111.00 120.00   29
 18  \w    104.00 176.00   1.00   10.00    --  112.00 111.00-180.00   72
 19  \w    153.00 178.00   1.00   10.00    --  112.00 111.00 120.00   25
 20  \w     96.00 135.00   1.00   10.00    --  112.00 -45.00-180.00   39
 21  \w     84.00 109.00   1.00   10.00    --  112.00-130.00 125.00   25
 22  \w     72.00  98.00   1.00   10.00    --  112.00 -45.00  90.00   26
 23  \w     84.00 112.00   1.00   10.00    --  112.00 -45.00 -60.00   28
 24  \w     39.00 108.00   1.00   10.00    --  112.00-111.00 120.00   69
 25  \w    111.00 173.00   1.00   10.00    --  112.00  77.00-120.00   62
 26  \w     98.00 156.00   1.00   10.00    --  112.00  30.00 -30.00   58
 27  \w     41.00  67.00   1.00   10.00    --  112.00-130.00 125.00   26
 28  \w    115.00 145.00   1.00   10.00    --  112.00 178.00  30.00   30
 29  \w     37.00  63.00   1.00   10.00    --  112.00 -94.00 150.00   26
 30  \w     75.00 106.00   1.00   10.00    --  112.00 -94.00 150.00   31
 31  \w     82.00 107.00   1.00   10.00    --  112.00 -94.00 -60.00   25
 32  \w     68.00 101.00   1.00   10.00    --  112.00 -77.00  90.00   33
 33  \w     82.00 133.00   1.00   10.00    --  112.00 -45.00  30.00   51
 34  \w     39.00  88.00   1.00   10.00    --  112.00 -45.00 150.00   49
 35  \w     37.00  67.00   1.00   10.00    --  112.00-111.00  30.00   30
 36  \w     37.00 138.00   1.00   10.00    --  112.00 -30.00 -90.00  101
;
_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      -0.0076132000
_diffrn_orient_matrix_UB_12      0.0902329000
_diffrn_orient_matrix_UB_13      0.0291821000
_diffrn_orient_matrix_UB_21      -0.0058442000
_diffrn_orient_matrix_UB_22      -0.0297877000
_diffrn_orient_matrix_UB_23      0.0888916000
_diffrn_orient_matrix_UB_31      0.1596632000
_diffrn_orient_matrix_UB_32      0.0031857000
_diffrn_orient_matrix_UB_33      0.0046285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26525
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.020
_diffrn_reflns_theta_min         3.829
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.601
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.62a (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    1.301
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.694
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 2278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       0.0026(2)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0245
_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^)+(0.0401P)^2^+0.3340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0659
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                5287
_reflns_number_total             5334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12299_si_005.cif
_cod_data_source_block           qhn-1-979
_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               4134059
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C30 H26 N6 O2'
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.650
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H30D)=Sof(H30E)=Sof(H30F)=1-FVAR(1)
 Sof(H30A)=Sof(H30B)=Sof(H30C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17),
 C18(H18), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
3.b Disordered Me refined as rotating group:
 C30(H30A,H30B,H30C,H30D,H30E,H30F)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              57512
_shelx_hkl_checksum              36665
_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 1.699
_oxdiff_exptl_absorpt_empirical_full_min 0.780