Approach to Monobactams and Nocardicins via Diastereoselective Kinugasa Reaction.
Kabala, Kamil; Grzeszczyk, Barbara; Stecko, Sebastian; Furman, Bartłomiej; Chmielewski, Marek; The Journal of organic chemistry 80 (2015) 12038–12046; doi:10.1021/acs.joc.5b01979

data_4036436
_publ_section_title
;
 Approach to Monobactams and Nocardicins via Diastereoselective Kinugasa
 Reaction.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12038
_journal_page_last               12046
_journal_paper_doi               10.1021/acs.joc.5b01979
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H16 N2 O6'
_chemical_formula_sum            'C21 H16 N2 O6'
_chemical_formula_weight         392.36
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                96.246(4)
_cell_angle_beta                 100.362(3)
_cell_angle_gamma                110.893(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6821(3)
_cell_length_b                   9.1960(4)
_cell_length_c                   15.8865(6)
_cell_measurement_temperature    191(2)
_cell_measurement_theta_max      66.58
_cell_measurement_theta_min      5.24
_cell_volume                     881.11(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      191(2)
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.1212
_diffrn_reflns_Laue_measured_fraction_full 0.930
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10946
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.584
_diffrn_reflns_theta_min         5.242
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  0.9190
_exptl_absorpt_correction_T_min  0.8510
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       prisms
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.383
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.383
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0611
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                3102
_reflns_number_total             4883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01979_si_005.cif
_cod_data_source_block           2KKL52t_0ma
_cod_database_code               4036436
_shelx_estimated_absorpt_t_min   0.851
_shelx_estimated_absorpt_t_max   0.919
_shelxl_version_number           2014-3
_shelx_res_checksum              96910
_shelx_hkl_checksum              54582