Synthesis of 6-alkyl analogues of the 1-azabicyclo[4.3.0]nonan-2-one system by a strategy of geminal acylation and Beckmann rearrangement
Christine E. Elliott; David O. Miller; D. Jean Burnell; J. Chem. Soc., Perkin Trans. 1  (2002) 217–226; doi:10.1039/b108164k

data_7204253
_publ_section_title
;
 Synthesis of 6-alkyl analogues of the 1-azabicyclo[4.3.0]nonan-2-one
 system by a strategy of geminal acylation and Beckmann rearrangement
;
_journal_issue                   2
_journal_name_full               'J. Chem. Soc., Perkin Trans. 1'
_journal_page_first              217
_journal_page_last               226
_journal_paper_doi               10.1039/b108164k
_journal_year                    2002
_chemical_formula_sum            'C14 H23 N O2'
_chemical_formula_weight         237.34
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_cell_angle_alpha                90
_cell_angle_beta                 90.0(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.714(1)
_cell_length_b                   6.033(1)
_cell_length_c                   21.606(1)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    299.2
_cell_measurement_theta_max      29.9
_cell_measurement_theta_min      24.3
_cell_volume                     2700.0(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan for Windows (MSC, 1997)'
_computing_publication_material  'teXsan for Windows (MSC, 1997)'
_computing_structure_refinement  'teXsan for Windows (MSC, 1997)'
_computing_structure_solution
;
SHELX97 (Sheldrick, 1997)
;
_diffrn_ambient_temperature      299.2
_diffrn_measurement_device       'Rigaku AFC6S'
_diffrn_measurement_method       \w-2\q
_diffrn_orient_matrix_UB_11      -0.01992
_diffrn_orient_matrix_UB_12      -0.00654
_diffrn_orient_matrix_UB_13      -0.04212
_diffrn_orient_matrix_UB_21      0.04380
_diffrn_orient_matrix_UB_22      0.01184
_diffrn_orient_matrix_UB_23      -0.01918
_diffrn_orient_matrix_UB_31      0.00393
_diffrn_orient_matrix_UB_32      -0.16521
_diffrn_orient_matrix_UB_33      0.00029
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.00000
_diffrn_reflns_av_sigmaI/netI    0.081
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2372
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         60.07
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        0.68
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040.00
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.00
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   3.464
_refine_ls_goodness_of_fit_ref   4.030
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     306
_refine_ls_number_reflns         1540
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.0940
_refine_ls_shift/su_max          0.0100
_refine_ls_shift/su_mean         0.0010
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00010|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.1110
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                1540
_reflns_number_total             2372
_reflns_threshold_expression     I>2.00\s(I)
_cod_data_source_file            b108164k.txt
_cod_data_source_block           '_CEE97e-1_________________'
_cod_original_cell_volume        2699.9(4)
_cod_original_sg_symbol_H-M      'P c a 21   '
_cod_original_formula_sum        'C14 H23 N O2 '
_cod_database_code               7204253