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_4036437
_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 syn
_chemical_formula_moiety         'C20 H14 N2 O5, C7 H8'
_chemical_formula_sum            'C27 H22 N2 O5'
_chemical_formula_weight         454.46
_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-2014
_cell_angle_alpha                90
_cell_angle_beta                 94.0350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.0454(3)
_cell_length_b                   5.64100(10)
_cell_length_c                   15.4322(3)
_cell_measurement_reflns_used    7742
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.45
_cell_measurement_theta_min      2.85
_cell_volume                     1132.83(4)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.990
_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  0.0316
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9929
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.448
_diffrn_reflns_theta_min         2.870
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  0.9673
_exptl_absorpt_correction_T_min  0.7303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1660 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.926
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         3940
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.925
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0279
_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          0.0654
_refine_ls_wR_factor_ref         0.0659
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                3859
_reflns_number_total             3940
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01979_si_002.cif
_cod_data_source_block           2KKL12c_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4036437
_shelx_estimated_absorpt_t_min   0.730
_shelx_estimated_absorpt_t_max   0.967
_shelxl_version_number           2014-3
_shelx_res_checksum              70145
_shelx_hkl_checksum              15955