Synthesis of a bicyclic oxo-γ-lactam from a simple caprolactam derivative
Weck, Christian; Obst, Franziska; Nauha, Elisa; Schofield, Christopher J.; Gruber, Tobias; New J. Chem. 41 (2017) 9984–9989; doi:10.1039/C7NJ02348K

data_7056501
_publ_section_title
;
 Synthesis of a bicyclic oxo-\g-lactam from a simple caprolactam
 derivative
;
_journal_issue                   18
_journal_name_full               'New J. Chem.'
_journal_page_first              9984
_journal_page_last               9989
_journal_paper_doi               10.1039/C7NJ02348K
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C12 H19 N O5'
_chemical_formula_sum            'C12 H19 N O5'
_chemical_formula_weight         257.28
_chemical_name_systematic
'tert-Butyl 7,8-dioxo-6-azabicyclo[3.2.1]octane-6-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-18 deposited with the CCDC.
2017-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                88.877(5)
_cell_angle_beta                 80.145(5)
_cell_angle_gamma                82.187(5)
_cell_formula_units_Z            2
_cell_length_a                   6.1511(6)
_cell_length_b                   6.3794(7)
_cell_length_c                   17.5260(18)
_cell_measurement_reflns_used    5983
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.16
_cell_measurement_theta_min      2.56
_cell_volume                     671.28(12)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker D8 Venture Photon'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7972
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.382
_diffrn_reflns_theta_min         2.559
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane, ethyl acetate'
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.068
_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     173
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0677
_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^)+(0.0839P)^2^+0.7946P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1764
_refine_ls_wR_factor_ref         0.1859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2422
_reflns_number_total             2624
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj02348k2.cif
_cod_data_source_block           cu_TG_CWLR_019_8_2_0m
_cod_database_code               7056501
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.749
_shelx_estimated_absorpt_t_max   0.961
_shelx_res_checksum              38813