Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides.
Suzuki, Naoyuki; Hofstra, Julie L.; Poremba, Kelsey E.; Reisman, Sarah E.; Organic letters 19 (2017) 2150–2153; doi:10.1021/acs.orglett.7b00793

data_1545687
_publ_section_title
;
 Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide
 Esters with Vinyl Bromides.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2150
_journal_page_last               2153
_journal_paper_doi               10.1021/acs.orglett.7b00793
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H20 Br2 N2 Ni O2'
_chemical_formula_sum            'C23 H20 Br2 N2 Ni O2'
_chemical_formula_weight         574.94
_chemical_melting_point_gt       300
_chemical_name_common            JLH-3-168
_chemical_name_systematic        JLH-3-168
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4823(6)
_cell_length_b                   9.4823(6)
_cell_length_c                   24.418(2)
_cell_measurement_reflns_used    9737
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.04
_cell_measurement_theta_min      2.30
_cell_volume                     2195.5(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2013)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD Area Detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'Bruker APEXII CCD'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker KAPPA APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            113308
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.918
_diffrn_reflns_theta_min         0.834
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.546
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.5466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2014)'
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_refine_diff_density_max         2.381
_refine_diff_density_min         -1.019
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details
;
 Flack x determined using 4664 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         12464
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0487P)^2^+4.8435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.957
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                11041
_reflns_number_total             12464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00793_si_002.cif
_cod_data_source_block           mkt
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_melting_point_gt' since the value was specified as 'more
than' ('>') a certain temperature. The value '>300' was changed to
'300' - it should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1545687.cif.
;
_cod_database_code               1545687
_shelx_estimated_absorpt_t_max   0.569
_shelx_estimated_absorpt_t_min   0.333
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5020(14) 0.4980(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C16(H16), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C3(H3A,H3B), C17(H17A,H17B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C8(H8), C20(H20), C6(H6), C7(H7), C22(H22), C5(H5), C21(H21)
;
_shelx_res_checksum              16779
_shelx_hkl_checksum              28808
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'