Pd(ii)-catalyzed intermolecular enantioselective hydroamination of styrenes
Yu, Feng; Chen, Pinhong; Liu, Guosheng; Organic Chemistry Frontiers 2 (2015) 819–; doi:10.1039/C5QO00096C

data_1553131
_publ_section_title
;
 Pd(ii)-catalyzed intermolecular enantioselective hydroamination of
 styrenes
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              819
_journal_paper_doi               10.1039/C5QO00096C
_journal_volume                  2
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H24 Cl2 N2 O Pd'
_chemical_formula_sum            'C16 H24 Cl2 N2 O Pd'
_chemical_formula_weight         437.67
_chemical_name_systematic        (POX)PdCl2
_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     direct
_audit_block_doi                 10.5517/cc14fs4h
_audit_creation_date             2014-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-03-25 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.796(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1876(18)
_cell_length_b                   9.8204(14)
_cell_length_c                   15.854(2)
_cell_measurement_reflns_used    2775
_cell_measurement_temperature    130
_cell_measurement_theta_max      28.72
_cell_measurement_theta_min      2.44
_cell_volume                     1884.2(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.1271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18529
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.495
_diffrn_reflns_theta_min         1.293
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.271
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1088 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.7888.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'organe '
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.263
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.156
_refine_ls_abs_structure_details
;
 Flack x determined using 2636 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   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         10955
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+0.8823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                7999
_reflns_number_total             10955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00096c2.cif
_cod_data_source_block           mo_dm14620_0m
_cod_database_code               1553131
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.804
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C29-C30 = C30-C31 = C30-C32
 1.52 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C29 \\sim C30 \\sim C31 \\sim C32: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
4.a Ternary CH refined with riding coordinates:
 C8(H8), C14(H14), C24(H24), C30(H30)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B), C23(H23A,H23B), C29(H29A,H29B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C18(H18), C19(H19), C20(H20)
4.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              16918
_shelx_hkl_checksum              64644
_olex2_submission_special_instructions 'No special instructions were received'