An asymmetric Mannich reaction of α-diazocarbonyl compounds and N-sulfonyl cyclic ketimines catalyzed by complexes generated from chiral and achiral phosphines with gold(i).
Zhou, Minghui; Su, Qin; Addepalli, Yesu; He, Yun; Wang, Zhen; Organic & biomolecular chemistry 16 (2018) 2923–2931; doi:10.1039/c8ob00577j

data_7156172
_publ_section_title
;
 An asymmetric Mannich reaction of \a-diazocarbonyl compounds and
 N-sulfonyl cyclic ketimines catalyzed by complexes generated from chiral
 and achiral phosphines with gold(i).
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2923
_journal_page_last               2931
_journal_paper_doi               10.1039/c8ob00577j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C14 H16 Cl N3 O6 S'
_chemical_formula_sum            'C14 H16 Cl N3 O6 S'
_chemical_formula_weight         389.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-10-18 deposited with the CCDC.
2018-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                70.829(4)
_cell_angle_beta                 76.104(4)
_cell_angle_gamma                67.503(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8621(4)
_cell_length_b                   10.1290(5)
_cell_length_c                   12.5926(5)
_cell_measurement_reflns_used    2775
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0510
_cell_measurement_theta_min      3.4790
_cell_volume                     867.55(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -25.00   23.00   0.8000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000   90.0000 60

  2 omega  -25.00    7.00   0.8000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000    0.0000 40

  3 omega  -51.00   27.40   0.8000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -38.0000   30.0000 98

  4 omega   54.00   89.20   0.8000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856 -178.0000   30.0000 44

  5 omega  -15.00   53.00   0.8000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -99.0000 -120.0000 85

  6 omega  -35.00   85.00   0.8000   55.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856    0.0000 -120.0000 150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0409718000
_diffrn_orient_matrix_UB_12      0.0757025000
_diffrn_orient_matrix_UB_13      0.0000918000
_diffrn_orient_matrix_UB_21      0.0234618000
_diffrn_orient_matrix_UB_22      0.0210507000
_diffrn_orient_matrix_UB_23      -0.0597144000
_diffrn_orient_matrix_UB_31      -0.0864479000
_diffrn_orient_matrix_UB_32      -0.0005035000
_diffrn_orient_matrix_UB_33      -0.0072572000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7194
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.917
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0621P)^2^+0.1340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2457
_reflns_number_total             3544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00577j3.cif
_cod_data_source_block           170525_s3_wz
_cod_depositor_comments          'Adding full bibliography for 7156172.cif.'
_cod_database_code               7156172
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3cl1s1
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.895
_reflns_odcompleteness_completeness 99.86
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'