Atropisomeric Chiral Diiododienes (Z,Z)-2,3-Di(1-iodoalkylidene)tetralins: Synthesis, Enantiomeric Resolution, and Application in Asymmetric Catalysis
Ogasawara, Masamichi; Sasa, Hirotaka; Hu, Hao; Amano, Yuta; Nakajima, Hikaru; Takenaga, Naoko; Nakajima, Kiyohiko; Kita, Yasuyuki; Takahashi, Tamotsu; Dohi, Toshifumi; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b01876

data_1546558
_publ_section_title
;
 Atropisomeric Chiral Diiododienes
 (Z,Z)-2,3-Di(1-iodoalkylidene)tetralins: Synthesis, Enantiomeric
 Resolution, and Application in Asymmetric Catalysis
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b01876
_journal_year                    2017
_chemical_formula_moiety         'C20 H26 I2'
_chemical_formula_sum            'C20 H26 I2'
_chemical_formula_weight         520.23
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.5861(14)
_cell_length_b                   11.262(3)
_cell_length_c                   27.326(6)
_cell_measurement_reflns_used    18148
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.10
_cell_volume                     2026.8(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19997
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.101
_exptl_absorpt_correction_T_max  0.733
_exptl_absorpt_correction_T_min  0.358
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008.00
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.700
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1961 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4640
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0307P)^2^+0.5579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0649
_reflns_number_gt                4201
_reflns_number_total             4640
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol7b01876_si_002.cif
_cod_data_source_block           mo01r
_cod_database_code               1546558