Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation: Application to the Synthesis of Unusual Amino Acids.
Liniger, Marc; Liu, Yiyang; Stoltz, Brian M.; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b08496

data_4126464
_publ_section_title
;
 Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation:
 Application to the Synthesis of Unusual Amino Acids.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b08496
_journal_year                    2017
_chemical_formula_moiety         'C13 H17 N O3'
_chemical_formula_sum            'C13 H17 N O3'
_chemical_formula_weight         235.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998),
 SHELXL-2014,
 and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 114.106(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3502(5)
_cell_length_b                   12.3986(5)
_cell_length_c                   10.6650(5)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100
_cell_measurement_theta_max      38.50
_cell_measurement_theta_min      2.66
_cell_volume                     1249.26(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 2014.9-0 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'XT-2014/4 (Sheldrick, 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker KAPPA APEX II ccd'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            72079
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         40.253
_diffrn_reflns_theta_min         2.660
_diffrn_source                   'sealed tube'
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0591 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.9176.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         7619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0741P)^2^+0.1552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5599
_reflns_number_total             7619
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b08496_si_007.cif
_cod_data_source_block           a14415
_cod_original_cell_volume        1249.27(10)
_cod_database_code               4126464
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'