Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of 1,6-Enynes with Cyclopropylideneacetamides.
Yoshizaki, Soichi; Nakamura, Yu; Masutomi, Koji; Yoshida, Tomoka; Noguchi, Keiichi; Shibata, Yu; Tanaka, Ken; Organic letters 18 (2016) 388–391; doi:10.1021/acs.orglett.5b03387

data_1542670
_publ_section_title
;
 Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of 1,6-Enynes with
 Cyclopropylideneacetamides.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              388
_journal_page_last               391
_journal_paper_doi               10.1021/acs.orglett.5b03387
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H32 N2 O3 S'
_chemical_formula_sum            'C24 H32 N2 O3 S'
_chemical_formula_weight         428.57
_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
_cell_angle_alpha                90
_cell_angle_beta                 103.8850(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9083(3)
_cell_length_b                   5.97938(11)
_cell_length_c                   23.1232(4)
_cell_measurement_reflns_used    31449
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.70
_cell_volume                     2269.47(7)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            40842
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_min         3.698
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.496
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1901 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         7894
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0729P)^2^+0.1288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.899
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                5634
_reflns_number_total             7894
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03387_si_001.cif
_cod_data_source_block           I
_cod_original_cell_volume        2269.46(7)
_cod_database_code               1542670
_shelx_estimated_absorpt_t_min   0.470
_shelx_estimated_absorpt_t_max   0.957
_shelxl_version_number           2014-3
_shelx_res_checksum              52798
_shelx_hkl_checksum              75566