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_4036438
_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         'C24 H27 N O6'
_chemical_formula_sum            'C24 H27 N O6'
_chemical_formula_weight         425.46
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 94.548(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.1669(4)
_cell_length_b                   6.0551(2)
_cell_length_c                   13.8168(4)
_cell_measurement_reflns_used    2934
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.95
_cell_measurement_theta_min      4.83
_cell_volume                     1098.10(6)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7155
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.527
_diffrn_reflns_theta_min         4.835
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_correction_T_min  0.7616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.820
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3662
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.820
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0355
_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          0.0790
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.843
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                3398
_reflns_number_total             3662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01979_si_004.cif
_cod_data_source_block           2KKL31c_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4036438
_shelx_estimated_absorpt_t_min   0.762
_shelx_estimated_absorpt_t_max   0.946
_shelxl_version_number           2014-3
_shelx_res_checksum              21898
_shelx_hkl_checksum              37332