Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of α,ω-Diynes with Unsymmetrical 1,2-Disubstituted Alkenes.
Aida, Yukimasa; Sugiyama, Haruki; Uekusa, Hidehiro; Shibata, Yu; Tanaka, Ken; Organic letters 18 (2016) 2672–2675; doi:10.1021/acs.orglett.6b01116

data_1543356
_publ_section_title
;
 Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of \a,\w-Diynes
 with Unsymmetrical 1,2-Disubstituted Alkenes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2672
_journal_page_last               2675
_journal_paper_doi               10.1021/acs.orglett.6b01116
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration sym
_chemical_formula_moiety         'C29 H22 O4'
_chemical_formula_sum            'C29 H22 O4'
_chemical_formula_weight         434.46
_chemical_name_common            YA375-F1
_chemical_name_systematic        YA375-F1
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
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_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                65.909(1)
_cell_angle_beta                 85.150(1)
_cell_angle_gamma                82.591(1)
_cell_formula_units_Z            1
_cell_length_a                   5.1050(1)
_cell_length_b                   9.9850(2)
_cell_length_c                   11.8359(2)
_cell_measurement_reflns_used    6212
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.14
_cell_measurement_theta_min      4.1
_cell_volume                     545.829(18)
_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)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.983
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6252
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.144
_diffrn_reflns_theta_min         4.094
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.162
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.222
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.222
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.1641P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.698
_reflns_Friedel_fraction_max     0.694
_reflns_number_gt                3177
_reflns_number_total             3339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01116_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 1543356.cif.'
_cod_database_code               1543356
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.855
_shelx_estimated_absorpt_t_max   0.895
_shelx_res_checksum              1094
_shelx_hkl_checksum              79840