Copper(I)-Catalyzed Asymmetric Pinacolboryl Addition of N-Boc-imines Using a Chiral Sulfoxide-Phosphine Ligand.
Wang, Ding; Cao, Peng; Wang, Bing; Jia, Tao; Lou, Yazhou; Wang, Min; Liao, Jian; Organic letters 17 (2015) 2420–2423; doi:10.1021/acs.orglett.5b00934

data_1529349
_publ_section_title
;
 Copper(I)-Catalyzed Asymmetric Pinacolboryl Addition of N-Boc-imines
 Using a Chiral Sulfoxide-Phosphine Ligand.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2420
_journal_page_last               2423
_journal_paper_doi               10.1021/acs.orglett.5b00934
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C36 H62 Cl2 Cu2 O6 P2 S2'
_chemical_formula_sum            'C36 H62 Cl2 Cu2 O6 P2 S2'
_chemical_formula_weight         914.90
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-05-13
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.328(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6416(3)
_cell_length_b                   13.3076(6)
_cell_length_c                   17.3445(5)
_cell_measurement_reflns_used    3079
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.4760
_cell_measurement_theta_min      3.3250
_cell_volume                     2454.20(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -23.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  -99.0000 -150.0000 38

  2 omega  -14.00   21.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  -99.0000   30.0000 35

  3 omega  -62.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174    0.0000    0.0000 94

  4 omega  -13.00   40.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174   19.0000 -150.0000 53
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0129884000
_diffrn_orient_matrix_UB_12      -0.0468728000
_diffrn_orient_matrix_UB_13      -0.0180299000
_diffrn_orient_matrix_UB_21      0.0134530000
_diffrn_orient_matrix_UB_22      0.0211864000
_diffrn_orient_matrix_UB_23      -0.0362943000
_diffrn_orient_matrix_UB_31      0.0640300000
_diffrn_orient_matrix_UB_32      -0.0139909000
_diffrn_orient_matrix_UB_33      0.0057085000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_laue_measured_fraction_full 0.996
_diffrn_reflns_laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10538
_diffrn_reflns_point_group_measured_fraction_full 0.784
_diffrn_reflns_point_group_measured_fraction_max 0.772
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.972
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.161
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description
;
;
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.007(10)
_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     469
_refine_ls_number_reflns         7748
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0590P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.482
_reflns_friedel_fraction_full    0.550
_reflns_friedel_fraction_max     0.526
_reflns_number_gt                6094
_reflns_number_total             7748
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00934_si_001.cif
_cod_data_source_block           140512_s3_sws_lj
_cod_depositor_comments
;

2019-03-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C18 H31 Cl Cu O3 P S'
_cod_original_formula_weight         457.45
_cod_original_formula_moiety         '0.5(C36 H62 Cl2 Cu2 O6 P2 S2)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        2454.20(14)
_cod_database_code               1529349
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2o3s1cu1cl1
_shelx_estimated_absorpt_t_max   0.801
_shelx_estimated_absorpt_t_min   0.722
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Ternary CH refined with riding coordinates:
 C25(H25), C28(H28), C31(H31), C34(H34)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,
 H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C),
 C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              1055
_shelx_hkl_checksum              47178