Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity.
Kashima, Kenichi; Teraoka, Kota; Uekusa, Hidehiro; Shibata, Yu; Tanaka, Ken; Organic letters 18 (2016) 2170–2173; doi:10.1021/acs.orglett.6b00791

data_1543112
_publ_section_title
;
 Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of
 Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho
 Substituents on Regio- and Enantioselectivity.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2170
_journal_page_last               2173
_journal_paper_doi               10.1021/acs.orglett.6b00791
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H36 Cl N O10'
_chemical_formula_sum            'C31 H36 Cl N O10'
_chemical_formula_weight         618.06
_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
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_cell_angle_alpha                90
_cell_angle_beta                 91.4160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8859(2)
_cell_length_b                   26.1897(5)
_cell_length_c                   13.3329(2)
_cell_measurement_reflns_used    30069
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.32
_cell_volume                     3101.87(10)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
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_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36545
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_min         3.316
_diffrn_source                   'rotating anode X-ray tube'
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       platelet
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_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.184
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_refine_ls_abs_structure_details
;
 Flack x determined using 4274 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         11003
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0605P)^2^+0.7594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                10131
_reflns_number_total             11003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00791_si_002.cif
_cod_data_source_block           shelx_a
_cod_depositor_comments          'Adding full bibliography for 1543112.cif.'
_cod_database_code               1543112
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.769
_shelx_estimated_absorpt_t_max   0.866
_shelx_res_checksum              32614
_shelx_hkl_checksum              55503