Asymmetric Synthesis of Deoxypropionate Derivatives via Catalytic Hydrogenolysis of Enantioenriched Z-Ketene Heterodimers.
Chen, Shi; Ibrahim, Ahmad A.; Mondal, Mukulesh; Magee, Anthony J.; Cruz, Adam J.; Wheeler, Kraig A.; Kerrigan, Nessan J.; Organic letters 17 (2015) 3248–3251; doi:10.1021/acs.orglett.5b01391

data_1520658
_publ_section_title
;
 Asymmetric Synthesis of Deoxypropionate Derivatives via Catalytic
 Hydrogenolysis of Enantioenriched Z-Ketene Heterodimers.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3248
_journal_page_last               3251
_journal_paper_doi               10.1021/acs.orglett.5b01391
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H20 N2 O6'
_chemical_formula_sum            'C19 H20 N2 O6'
_chemical_formula_weight         372.37
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_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8624(1)
_cell_length_b                   9.6327(2)
_cell_length_c                   31.8680(6)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.509
_cell_measurement_theta_min      2.793
_cell_volume                     1799.61(6)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction
;
SAINT (Bruker, 2013) and XPREP (Bruker, 2012)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
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_computing_structure_solution    'SHELXS-13 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.973
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_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            12605
_diffrn_reflns_point_group_measured_fraction_full 0.575
_diffrn_reflns_point_group_measured_fraction_max 0.575
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_min         2.773
_exptl_absorpt_coefficient_mu    0.865
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       'transparent block'
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.074
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_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         1893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0495P)^2^+0.6676P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                1717
_reflns_number_total             1893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01391_si_003.cif
_cod_data_source_block           twin4
_cod_depositor_comments          'Adding full bibliography for 1520658.cif.'
_cod_database_code               1520658
_shelx_estimated_absorpt_t_min   0.766
_shelx_estimated_absorpt_t_max   0.939
_shelxl_version_number           2012-9
_shelx_res_checksum              18478
_shelx_hkl_checksum              43046