Diastereodivergent asymmetric Michael-alkylation reactions using chiral <i>N</i>,<i>N</i>'-dioxide/metal complexes.
Kuang, Yulong; Shen, Bin; Dai, Li; Yao, Qian; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Chemical science 9 (2018) 688–692; doi:10.1039/c7sc02757e

data_1547944
_publ_section_title
;
 Diastereodivergent asymmetric Michael-alkylation reactions using chiral
 <i>N</i>,<i>N</i>'-dioxide/metal complexes.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              688
_journal_page_last               692
_journal_paper_doi               10.1039/c7sc02757e
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C19 H16 Cl N O4'
_chemical_formula_sum            'C19 H16 Cl N O4'
_chemical_formula_weight         357.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-04-21 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.880(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.3416(3)
_cell_length_b                   17.2210(5)
_cell_length_c                   16.8272(5)
_cell_measurement_reflns_used    7585
_cell_measurement_temperature    293.20(10)
_cell_measurement_theta_max      72.5740
_cell_measurement_theta_min      4.2360
_cell_volume                     3557.55(17)
_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      293.20(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    4.0100
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   30.0000 74

  2 omega   23.00   90.00   1.0000    4.0100
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -60.0000 67

  3 omega   20.00  104.00   1.0000    4.0100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

  4 omega  -31.00   53.00   1.0000    4.0100
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   30.0000 84

  5 omega  -35.00   66.00   1.0000    4.0100
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000 -120.0000 101

  6 omega   20.00  104.00   1.0000    4.0100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -150.0000 84

  7 omega   39.00  109.00   1.0000   16.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

  8 omega   38.00   91.00   1.0000   16.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

  9 omega   91.00  176.00   1.0000   16.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 10 omega   38.00   91.00   1.0000   16.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 11 omega   38.00  116.00   1.0000   16.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 78

 12 omega   38.00   91.00   1.0000   16.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 13 omega   38.00   91.00   1.0000   16.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 14 omega   39.00  109.00   1.0000   16.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 15 omega   81.00  176.00   1.0000   16.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

 16 omega   41.00  126.00   1.0000   16.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -180.0000 85
;
_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      -0.0201067000
_diffrn_orient_matrix_UB_12      -0.0303926000
_diffrn_orient_matrix_UB_13      0.0831949000
_diffrn_orient_matrix_UB_21      -0.0042467000
_diffrn_orient_matrix_UB_22      -0.0837579000
_diffrn_orient_matrix_UB_23      -0.0324285000
_diffrn_orient_matrix_UB_31      0.1239075000
_diffrn_orient_matrix_UB_32      -0.0079627000
_diffrn_orient_matrix_UB_33      0.0219949000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19575
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.600
_diffrn_reflns_theta_min         4.423
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51865
_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    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1240P)^2^+0.4800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1806
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5987
_reflns_number_total             6953
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc02757e2.cif
_cod_data_source_block           fxm-shenbin-6aa
_cod_depositor_comments
;

2019-02-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel

 Adding full bibliography for 1547942--1547944.cif.
;
_cod_original_cell_volume        3557.55(18)
_cod_original_formula_moiety     '2(C19 H16 Cl N O4)'
_cod_original_formula_sum        'C38 H32 Cl2 N2 O8'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     715.55
_cod_database_code               1547944
_reflns_odcompleteness_completeness 99.88
_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 Ternary CH refined with riding coordinates:
 C00D(H00D), C00O(H00O)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00C), C00Q(H00F,H00G)
2.c Aromatic/amide H refined with riding coordinates:
 N00B(H00B), N00C(H00E), C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C015(H015),
 C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01D), C01B(H01F),
 C01C(H01G), C01E(H01E)
2.d Idealised Me refined as rotating group:
 C014(H01A,H01B,H01C), C01D(H01H,H01I,H01J)
;
_shelx_res_checksum              26106
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-04-20
_olex2_submission_special_instructions 'No special instructions were received'