A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N'-dioxide-metal complexes.
Lian, Xiangjin; Lin, Lili; Fu, Kai; Ma, Baiwei; Liu, Xiaohua; Feng, Xiaoming; Chemical science 8 (2017) 1238–1242; doi:10.1039/c6sc03902b

data_1544235
_publ_section_title
;
 A new approach to the asymmetric Mannich reaction catalyzed by chiral
 N,N'-dioxide-metal complexes.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              1238
_journal_page_last               1242
_journal_paper_doi               10.1039/c6sc03902b
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H25 N O3'
_chemical_formula_sum            'C22 H25 N O3'
_chemical_formula_weight         351.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/cc1km9hz
_audit_creation_date             2016-01-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-01-20 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.05221(8)
_cell_length_b                   17.0223(3)
_cell_length_c                   19.5981(3)
_cell_measurement_reflns_used    5025
_cell_measurement_temperature    217.05(10)
_cell_measurement_theta_max      72.1000
_cell_measurement_theta_min      5.1690
_cell_volume                     2019.05(5)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      217.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    4.7100
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000 -120.0000 84

  2 omega    1.00   75.00   1.0000    4.7100
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000 -120.0000 74

  3 omega   23.00   90.00   1.0000    4.7100
omega____ theta____ kappa____ phi______ frames
    -       36.4171 -125.0000  150.0000 67

  4 omega  -31.00   53.00   1.0000    4.7100
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000  -90.0000 84

  5 omega    1.00   75.00   1.0000    4.7100
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000 -180.0000 74

  6 omega   39.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

  7 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

  8 omega   38.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

  9 omega   38.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 10 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 11 omega   38.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 12 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 13 omega   37.00  146.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   90.0000 109

 14 omega   10.00  104.00   1.0000    4.7100
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  120.0000 94

 15 omega   20.00  104.00   1.0000    4.7100
omega____ theta____ kappa____ phi______ frames
    -       36.4171   57.0000   60.0000 84

 16 omega  -31.00   43.00   1.0000    4.7100
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000    0.0000 74

 17 omega   10.00  104.00   1.0000    4.7100
omega____ theta____ kappa____ phi______ frames
    -       36.4171   77.0000  -30.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0718665000
_diffrn_orient_matrix_UB_12      0.0822151000
_diffrn_orient_matrix_UB_13      0.0242757000
_diffrn_orient_matrix_UB_21      -0.0499735000
_diffrn_orient_matrix_UB_22      0.0235811000
_diffrn_orient_matrix_UB_23      -0.0742801000
_diffrn_orient_matrix_UB_31      -0.2390116000
_diffrn_orient_matrix_UB_32      -0.0296784000
_diffrn_orient_matrix_UB_33      0.0082869000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10704
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.052
_diffrn_reflns_theta_max         67.052
_diffrn_reflns_theta_min         4.512
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60907
_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_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1331 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0524
_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^)+(0.1100P)^2^+0.0540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1470
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3388
_reflns_number_total             3602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc03902b2.cif
_cod_data_source_block           fxm-lxj
_cod_depositor_comments
;Adding full bibliography for 1544235--1544236.cif.

 Adding full bibliography for 1544235--1544236.cif.
;
_cod_original_cell_volume        2019.05(6)
_cod_database_code               1544235
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00C(H00D,H00E), C00G(H00G,H00H)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C00B(H00C), C00D(H00F), C00H(H00I), C00J(H00M), C00K(H00N),
 C00L(H00O), C00M(H00P), C00N(H00Q), C00P(H00U)
2.c Idealised Me refined as rotating group:
 C00I(H00J,H00K,H00L), C00O(H00R,H00S,H00T), C00Q(H00V,H00W,H00X)
;
_shelx_res_checksum              34350
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-18
_olex2_submission_special_instructions 'No special instructions were received'