Stereoselective Synthesis of Diazabicyclic β-Lactams through Intramolecular Amination of Unactivated C(sp(3))-H Bonds of Carboxamides by Palladium Catalysis.
Zhang, Shi-Jin; Sun, Wen-Wu; Cao, Pei; Dong, Xiao-Ping; Liu, Ji-Kai; Wu, Bin; The Journal of organic chemistry 81 (2016) 956–968; doi:10.1021/acs.joc.5b02532

data_4031916
_publ_section_title
;
 Stereoselective Synthesis of Diazabicyclic \b-Lactams through
 Intramolecular Amination of Unactivated C(sp(3))-H Bonds of Carboxamides
 by Palladium Catalysis.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              956
_journal_page_last               968
_journal_paper_doi               10.1021/acs.joc.5b02532
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C18 H14 N2 O'
_chemical_formula_sum            'C18 H14 N2 O'
_chemical_formula_weight         274.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.414(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2122(14)
_cell_length_b                   9.7378(12)
_cell_length_c                   11.5756(14)
_cell_measurement_reflns_used    8048
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.68
_cell_volume                     1376.5(3)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14172
_diffrn_reflns_theta_full        30.14
_diffrn_reflns_theta_max         30.14
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_correction_T_min  0.9626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.007(2)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0701P)^2^+0.4462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                3432
_reflns_number_total             3899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02532_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4031916