Dynamic kinetic asymmetric transformations of β-halo-α-keto esters by N,N'-dioxide/Ni(ii)-catalyzed carbonyl-ene reaction.
Liu, Wen; Cao, Weidi; Hu, Haipeng; Lin, Lili; Feng, Xiaoming; Chemical communications (Cambridge, England) 54 (2018) 8901–8904; doi:10.1039/c8cc04993a

data_7121983
_publ_section_title
;
 Dynamic kinetic asymmetric transformations of \b-halo-\a-keto esters by
 N,N'-dioxide/Ni(ii)-catalyzed carbonyl-ene reaction.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8901
_journal_page_last               8904
_journal_paper_doi               10.1039/c8cc04993a
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H20 Br N O4'
_chemical_formula_sum            'C24 H20 Br N O4'
_chemical_formula_weight         466.32
_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             2017-04-18
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_audit_update_record
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2017-10-07 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.421(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.71336(13)
_cell_length_b                   14.1891(3)
_cell_length_c                   12.7481(3)
_cell_measurement_reflns_used    3612
_cell_measurement_temperature    137
_cell_measurement_theta_max      72.1840
_cell_measurement_theta_min      4.6890
_cell_volume                     1024.80(4)
_computing_cell_refinement
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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)
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_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)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
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  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -180.0000 84

  2 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   90.0000 84

  3 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   60.0000 84

  4 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000    0.0000 67

  5 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000   60.0000 101

  6 omega   40.00   98.00   1.0000    3.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

  7 omega   39.00  109.00   1.0000    3.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

  8 omega   38.00   91.00   1.0000    3.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

  9 omega   38.00   91.00   1.0000    3.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 10 omega   41.00  126.00   1.0000    3.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   90.0000 85

 11 omega   38.00   91.00   1.0000    3.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 12 omega  100.00  178.00   1.0000    3.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 78

 13 omega   39.00   92.00   1.0000    3.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000   93.0000 53

 14 omega   38.00   91.00   1.0000    3.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 15 omega   38.00   91.00   1.0000    3.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 16 omega   38.00   91.00   1.0000    3.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 17 omega    2.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   90.0000 -120.6548 30

 18 omega   20.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -150.0000 53

 19 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  150.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.0545971000
_diffrn_orient_matrix_UB_12      0.0505775000
_diffrn_orient_matrix_UB_13      -0.1073697000
_diffrn_orient_matrix_UB_21      -0.2664079000
_diffrn_orient_matrix_UB_22      -0.0073649000
_diffrn_orient_matrix_UB_23      0.0077737000
_diffrn_orient_matrix_UB_31      0.0086804000
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_diffrn_orient_matrix_UB_33      0.0570947000
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_limit_h_max       6
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_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5995
_diffrn_reflns_point_group_measured_fraction_full 0.719
_diffrn_reflns_point_group_measured_fraction_max 0.688
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.950
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_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.998
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_exptl_absorpt_correction_type   multi-scan
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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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
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_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       plate
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.5
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_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.726
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_refine_ls_abs_structure_details
;
 Flack x determined using 722 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(18)
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     273
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_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0900P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_data_source_block           fxm-lw-sub-2-137k
_cod_depositor_comments          'Adding full bibliography for 7121983.cif.'
_cod_database_code               7121983
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
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_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C12(H12), C16(H16), C19(H19), C21(H21), C22(H22),
 C24(H24), C26(H26), C27(H27), C29(H29), C35(H35)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              92185
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-04-18
_olex2_submission_special_instructions 'No special instructions were received'