Catalytic Asymmetric Nazarov Cyclization of Heteroaryl Vinyl Ketones through a Crystallographically Defined Chiral Dinuclear Nickel Complex.
Takeda, Takuya; Harada, Shinji; Nishida, Atsushi; Organic letters 17 (2015) 5184–5187; doi:10.1021/acs.orglett.5b02497

data_1555335
_publ_section_title
;
 Catalytic Asymmetric Nazarov Cyclization of Heteroaryl Vinyl Ketones
 through a Crystallographically Defined Chiral Dinuclear Nickel Complex.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5184
_journal_page_last               5187
_journal_paper_doi               10.1021/acs.orglett.5b02497
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C51 H46 F12 N6 Ni O16 S4'
_chemical_formula_sum            'C51 H46 F12 N6 Ni O16 S4'
_chemical_formula_weight         1413.88
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.4654(11)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   13.6455(3)
_cell_length_b                   18.1359(5)
_cell_length_c                   24.9551(6)
_cell_measurement_reflns_used    14246
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.09
_cell_measurement_theta_min      3.04
_cell_volume                     5979.9(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1448
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            64005
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.217
_diffrn_reflns_theta_min         3.047
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.752
_exptl_absorpt_correction_T_max  0.759
_exptl_absorpt_correction_T_min  0.528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2888.00
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.70
_refine_ls_abs_structure_details
;
 Flack x determined using 1405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     1678
_refine_ls_number_reflns         21038
_refine_ls_number_restraints     2020
_refine_ls_R_factor_all          0.3164
_refine_ls_R_factor_gt           0.1394
_refine_ls_shift/su_max          0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3280
_refine_ls_wR_factor_ref         0.4540
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                5100
_reflns_number_total             21038
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol5b02497_si_002.cif
_cod_data_source_block           141114takeda04
_cod_original_cell_volume        5980.0(3)
_cod_database_code               1555335
_shelx_res_checksum              34609
_shelx_hkl_checksum              84282