Enantioselective palladaelectro-catalyzed C–H olefinations and allylations for N–C axial chirality
Dhawa, Uttam; Wdowik, Tomasz; Hou, Xiaoyan; Yuan, Binbin; Oliveira, João C. A.; Ackermann, Lutz; Chemical Science  (2021) –; doi:10.1039/D1SC04687J

data_1564926
_publ_section_title
;
 Enantioselective palladaelectro-catalyzed C--H olefinations and
 allylations for N--C axial chirality
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04687J
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H18 N2 O3'
_chemical_formula_sum            'C29 H18 N2 O3'
_chemical_formula_weight         442.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-16
_audit_creation_method
;
FinalCif V85 by Daniel Kratzert, Freiburg 2021,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2021-06-16 deposited with the CCDC.	2021-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.499(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6726(8)
_cell_length_b                   9.3885(6)
_cell_length_c                   24.0690(15)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      78.938
_cell_measurement_theta_min      3.674
_cell_volume                     2185.0(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker BIS V6.2.14/2020-04-30'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            75722
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.340
_diffrn_reflns_theta_min         1.836
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_correction_T_min  0.8751
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0682 before and 0.0552 after correction.
The Ratio of minimum to maximum transmission is 0.8971.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'Crystallized from chloroform from NMR-sample.'
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 4042 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         9220
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0313P)^2^+1.8592P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                9050
_reflns_number_total             9220
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04687j2.cif
_cod_data_source_block           cu_1374_cg_0m
_cod_database_code               1564926
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30), C32(H32), C35(H35), C36(H36), C37(H37), C38(H38),
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C50(H50), C54(H54),
  C55(H55), C56(H56), C57(H57), C58(H58)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.864
_shelx_estimated_absorpt_t_max   0.932
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              491
_shelx_hkl_checksum              99428