Chiral N,N'-dioxide-Sc(NTf2)3 complex-catalyzed asymmetric bromoamination of chalones with N-bromosuccinimide as both bromine and amide source.
Wang, Zhengmeng; Lin, Lili; Zhou, Pengfei; Liu, Xiaohua; Feng, Xiaoming; Chemical communications (Cambridge, England) 53 (2017) 3462–3465; doi:10.1039/c7cc00470b

data_7119710
_publ_section_title
;
 Chiral N,N'-dioxide-Sc(NTf2)3 complex-catalyzed asymmetric bromoamination
 of chalones with N-bromosuccinimide as both bromine and amide source.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3462
_journal_page_last               3465
_journal_paper_doi               10.1039/c7cc00470b
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H15 Br N2 O5'
_chemical_formula_sum            'C19 H15 Br N2 O5'
_chemical_formula_weight         431.24
_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             2016-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-09-12 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.023(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2912(3)
_cell_length_b                   6.19457(16)
_cell_length_c                   13.4697(4)
_cell_measurement_reflns_used    3720
_cell_measurement_temperature    292.9(3)
_cell_measurement_theta_max      24.3150
_cell_measurement_theta_min      3.6170
_cell_volume                     936.93(4)
_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      292.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -23.00  105.00   1.0000   27.6800
omega____ theta____ kappa____ phi______ frames
    -       25.5845   38.0000   30.0000 128

  2 omega  -20.00   78.00   1.0000   27.6800
omega____ theta____ kappa____ phi______ frames
    -       25.5845  -99.0000   60.0000 98

  3 omega  -58.00  106.00   1.0000   27.6800
omega____ theta____ kappa____ phi______ frames
    -       25.5845  -19.0000   30.0000 164

  4 omega -117.00  -57.00   1.0000   27.6800
omega____ theta____ kappa____ phi______ frames
    -      -26.5220 -178.0000 -120.0000 60

  5 omega -101.00    8.00   1.0000   27.6800
omega____ theta____ kappa____ phi______ frames
    -      -26.5220  -57.0000 -150.0000 109

  6 omega  -20.00   26.00   1.0000   27.6800
omega____ theta____ kappa____ phi______ frames
    -      -26.5220  -99.0000  150.0000 46

  7 omega  -23.00  105.00   1.0000   27.6800
omega____ theta____ kappa____ phi______ frames
    -       25.5845   38.0000  150.0000 128

  8 omega  -48.00    5.00   1.0000   27.6800
omega____ theta____ kappa____ phi______ frames
    -       25.5845  -57.0000  -30.0000 53

  9 omega   35.00  116.00   1.0000   27.6800
omega____ theta____ kappa____ phi______ frames
    -       25.5845  178.0000    0.0000 81

 10 omega  -20.00   26.00   1.0000   27.6800
omega____ theta____ kappa____ phi______ frames
    -      -26.5220  -99.0000  -30.0000 46

 11 omega -117.00  -57.00   1.0000   27.6800
omega____ theta____ kappa____ phi______ frames
    -      -26.5220 -178.0000   90.0000 60
;
_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      0.0390371000
_diffrn_orient_matrix_UB_12      -0.0033229000
_diffrn_orient_matrix_UB_13      -0.0379441000
_diffrn_orient_matrix_UB_21      0.0496357000
_diffrn_orient_matrix_UB_22      0.0055031000
_diffrn_orient_matrix_UB_23      0.0368155000
_diffrn_orient_matrix_UB_31      0.0012340000
_diffrn_orient_matrix_UB_32      -0.1143423000
_diffrn_orient_matrix_UB_33      0.0028759000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13201
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.374
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69877
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1298 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+0.0824P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3341
_reflns_number_total             3820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc00470b2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7119710.cif.'
_cod_original_cell_volume        936.92(5)
_cod_database_code               7119710
_reflns_odcompleteness_completeness 99.76
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_shelx_res_checksum              84306
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'