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_1544236
_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 H26 N2 O2'
_chemical_formula_sum            'C22 H26 N2 O2'
_chemical_formula_weight         350.44
_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     direct
_audit_creation_date             2016-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-05-19 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.345(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.20362(17)
_cell_length_b                   10.9688(3)
_cell_length_c                   19.3712(4)
_cell_measurement_reflns_used    7712
_cell_measurement_temperature    295.1(5)
_cell_measurement_theta_max      72.5870
_cell_measurement_theta_min      4.6250
_cell_volume                     1923.79(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
;
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      air
_diffrn_ambient_temperature      295.1(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000    0.0000 74

  2 omega  -31.00   53.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  -30.0000 84

  3 omega    7.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   19.0000  150.0000 101

  4 omega   23.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000  150.0000 67

  5 omega    7.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   19.0000  -60.0000 101

  6 omega   20.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  120.0000 84

  7 omega   18.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000  150.0000 88

  8 omega   20.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  150.0000 84

  9 omega   23.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000  -30.0000 67

 10 omega  -31.00   53.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -150.0000 84

 11 omega   10.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -180.0000 94

 12 omega   38.00   91.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 13 omega   81.00  176.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

 14 omega   87.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 91

 15 omega   90.00  175.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 85

 16 omega   81.00  176.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 95

 17 omega   91.00  176.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 85

 18 omega   71.00  111.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 40

 19 omega   94.00  121.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 27

 20 omega  149.00  176.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 27

 21 omega   46.00  106.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 60

 22 omega   87.00  118.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 31

 23 omega   90.00  116.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 26

 24 omega  124.00  171.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 47

 25 omega   82.00  108.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

 26 omega   88.00  117.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 29

 27 omega   88.00  114.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 26

 28 omega   81.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26

 29 omega   90.00  116.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 26

 30 omega  121.00  171.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 50

 31 omega   89.00  116.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 27

 32 omega   88.00  114.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 26

 33 omega   81.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 26

 34 omega   90.00  138.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 48

 35 omega   97.00  125.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 28

 36 omega   94.00  120.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 26

 37 omega  131.00  157.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 26
;
_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      -0.1448243000
_diffrn_orient_matrix_UB_12      0.0483572000
_diffrn_orient_matrix_UB_13      0.0191168000
_diffrn_orient_matrix_UB_21      -0.0841515000
_diffrn_orient_matrix_UB_22      -0.0384000000
_diffrn_orient_matrix_UB_23      -0.0728103000
_diffrn_orient_matrix_UB_31      -0.0298723000
_diffrn_orient_matrix_UB_32      -0.1261500000
_diffrn_orient_matrix_UB_33      0.0295056000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18988
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.586
_diffrn_reflns_theta_min         4.641
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84493
_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    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2365 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6766
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0532
_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^)+(0.1050P)^2^+0.1367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1523
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.813
_reflns_Friedel_fraction_max     0.770
_reflns_number_gt                6312
_reflns_number_total             6766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc03902b2.cif
_cod_data_source_block           fxm-lxj-nh-ph-5
_cod_depositor_comments
;
 Adding full bibliography for 1544235--1544236.cif.

2019-02-26
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1923.78(7)
_cod_original_formula_moiety     '2(C22 H26 N2 O2)'
_cod_original_formula_sum        'C44 H52 N4 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     700.89
_cod_database_code               1544236
_reflns_odcompleteness_completeness 99.59
_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:
 C00F(H00G,H00H), C00L(H00A,H00B), C00P(H00I,H00J), C00R(H00K,H00L), C00T(H00C,
 H00D), C00W(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), N007(H007), N008(H008), C00Q(H00Q), C00S(H00S),
 C00U(H00U), C00V(H00V), C00X(H00X), C00Y(H00Y), C011(H011), C012(H012),
 C014(H014), C015(H015), C017(H017), C018(H018), C019(H019), C01C(H01J),
 C01D(H01S), C01E(H01T), C01F(H01K), C01G(H01L)
2.c Idealised Me refined as rotating group:
 C00Z(H00M,H00N,H00O), C010(H01A,H01B,H01C), C013(H01D,H01E,H01F), C016(H01G,
 H01H,H01I), C01A(H01M,H01N,H01O), C01B(H01P,H01Q,H01R)
;
_shelx_res_checksum              61289
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-18
_olex2_submission_special_instructions 'No special instructions were received'