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_7056500
_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         'C13 H21 N O5'
_chemical_formula_sum            'C13 H21 N O5'
_chemical_formula_weight         271.31
_chemical_name_systematic
'1-tert-Butyl 2-methyl 7-oxoazepane-1,2-dicarboxylate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-14 deposited with the CCDC.
2017-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.8289(3)
_cell_length_b                   12.9518(4)
_cell_length_c                   20.3412(6)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.48
_cell_measurement_theta_min      3.41
_cell_volume                     2852.93(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0345
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            51777
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.471
_diffrn_reflns_theta_min         4.347
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6615
_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    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate, n-hexane'
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.209
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.00186(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+1.2862P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2645
_reflns_number_total             2819
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj02348k2.cif
_cod_data_source_block           cu_TG_CW62_13_8_0m
_cod_database_code               7056500
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.771
_shelx_estimated_absorpt_t_max   0.850
_shelx_res_checksum              65550