Ni(ii)-catalyzed asymmetric addition of arylboronic acids to cyclic imines.
Quan, Mao; Tang, Liang; Shen, Jiaqi; Yang, Guoqiang; Zhang, Wanbin; Chemical communications (Cambridge, England) 53 (2017) 609–612; doi:10.1039/c6cc08759k

data_7119255
_publ_section_title
;
 Ni(ii)-catalyzed asymmetric addition of arylboronic acids to cyclic
 imines.
;
_journal_issue                   3
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              609
_journal_page_last               612
_journal_paper_doi               10.1039/c6cc08759k
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H28 Cl2 N Ni O P'
_chemical_formula_sum            'C30 H28 Cl2 N Ni O P'
_chemical_formula_weight         579.11
_chemical_name_systematic
;
 ? 
;
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-15
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_audit_update_record
;
2015-10-29 deposited with the CCDC.
2016-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1361(3)
_cell_length_b                   20.7607(8)
_cell_length_c                   14.8742(7)
_cell_measurement_reflns_used    5897
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5055
_cell_measurement_theta_min      2.8030
_cell_volume                     3130.0(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0023287000
_diffrn_orient_matrix_UB_12      0.0117665000
_diffrn_orient_matrix_UB_13      -0.0447323000
_diffrn_orient_matrix_UB_21      0.0255759000
_diffrn_orient_matrix_UB_22      0.0297094000
_diffrn_orient_matrix_UB_23      0.0158187000
_diffrn_orient_matrix_UB_31      0.0651248000
_diffrn_orient_matrix_UB_32      -0.0120797000
_diffrn_orient_matrix_UB_33      -0.0046337000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20639
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.81
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.32
_platon_squeeze_details
;
;
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack (1983), 2498 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.017(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                4851
_reflns_number_total             5722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc08759k2.cif
_cod_data_source_block           150715_qm0715
_cod_database_code               7119255
_chemical_oxdiff_formula         'c10 h10 n2 o8 Ni1 Cl1'
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Ternary CH refined with riding coordinates:
 C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C24(H24), C29(H29), C20(H20), C8(H8), C2(H2), C4(H4),
 C30(H30), C22(H22), C27(H27), C21(H21), C26(H26), C23(H23), C11(H11), C28(H28),
  C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;