Divergent Pd-catalyzed cross-coupling of allenyloxazolidinones to give chiral 1,3-dienes and vinyloxazolidinones
Brown, Ronald W.; Zamani, Farzad; Gardiner, Michael G.; Yu, Haibo; Pyne, Stephen G.; Hyland, Christopher J. T.; Chemical Science  (2019) –; doi:10.1039/C9SC03215K

data_1552240
_publ_section_title
;
 Divergent Pd-catalyzed cross-coupling of allenyloxazolidinones to give
 chiral 1,3-dienes and vinyloxazolidinones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC03215K
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H16 N2 O6 S'
_chemical_formula_weight         352.36
_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   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2019-05-28 deposited with the CCDC.    2019-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.952(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7486(2)
_cell_length_b                   10.2915(3)
_cell_length_c                   11.4126(4)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      66.69
_cell_measurement_theta_min      3.89
_cell_volume                     789.68(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13713
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.682
_diffrn_reflns_theta_min         3.888
_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0749 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.9145.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.633
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1224 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0432P)^2^+0.2043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0703
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2678
_reflns_number_total             2764
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03215k2.cif
_cod_data_source_block           17mg016_0m
_cod_database_code               1552240
_shelxl_version_number           2014-3
_shelx_res_checksum              71790