Enantioselective C,P-Palladacycle-Catalyzed Arylation of Imines
Huang, Yinhua; Wang, Lijun; Li, Junbao; Qiu, Huayu; Leung, Pak-Hing; ACS Omega  (2020) –; doi:10.1021/acsomega.0c01124

data_4517806
_publ_section_title
;
 Enantioselective C,P-Palladacycle-Catalyzed Arylation of Imines
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.0c01124
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H21 N O3 S'
_chemical_formula_sum            'C21 H21 N O3 S'
_chemical_formula_weight         367.45
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-21 deposited with the CCDC.	2019-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.625(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2589(17)
_cell_length_b                   21.876(5)
_cell_length_c                   10.255(2)
_cell_measurement_reflns_used    3433
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.014
_cell_measurement_theta_min      2.474
_cell_volume                     1846.8(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14312
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.741
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.565
_diffrn_reflns_theta_min         1.862
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0691 before and 0.0525 after correction. The Ratio of minimum to maximum transmission is 0.8680. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2017 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         8392
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.1611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1080
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    0.794
_reflns_Friedel_fraction_max     0.609
_reflns_number_gt                6245
_reflns_number_total             8392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c01124_si_002.cif
_cod_data_source_block           mo191219c
_cod_database_code               4517806
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.962
_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. Restrained distances
 N1-H1
 1.1 with sigma of 0.02
 N2-H2A
 1.1 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C29(H29)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C26(H26),
  C27(H27), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C37(H37),
 C38(H38), C39(H39), C40(H40)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C42(H42A,H42B,H42C)
;
_shelx_res_checksum              6567
_shelx_hkl_checksum              68482
_olex2_submission_special_instructions 'No special instructions were received'