Total Synthesis of (+)-Oxo-tomaymycin
Benedetti, Françoise; Perrin, Marc-Antoine; Bosc, Sebastien; Chouteau, Franck; Champion, Nicolas; Bigot, Antony; Organic Process Research & Development  (2020) –; doi:10.1021/acs.oprd.0c00009

data_1557328
_publ_section_title
;
 Total Synthesis of (+)-Oxo-tomaymycin
;
_journal_name_full               'Organic Process Research &amp; Development'
_journal_paper_doi               10.1021/acs.oprd.0c00009
_journal_year                    2020
_chemical_absolute_configuration S
_chemical_formula_sum            'C15 H16 N2 O4'
_chemical_formula_weight         288.30
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 105.7610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9821(2)
_cell_length_b                   8.6527(3)
_cell_length_c                   11.9259(3)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      30.483
_cell_measurement_theta_min      2.948
_cell_volume                     693.40(4)
_computing_cell_refinement       'Bruker AXS Apex3 suite'
_computing_data_collection       'Bruker AXS Apex3 suite'
_computing_data_reduction        'SAINT plus v8.38A'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      302(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27529
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.512
_diffrn_reflns_theta_min         2.948
_diffrn_source                   'micro-focus source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.7192
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4184
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0719P)^2^+0.0358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3960
_reflns_number_total             4184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            op0c00009_si_002.cif
_cod_data_source_block           xsc0123_0m_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1557328
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              72240
_shelx_hkl_checksum              49914