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_7204251
_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_moiety         'C15 H24 I N O2 '
_chemical_formula_sum            'C15 H24 I N O2'
_chemical_formula_weight         377.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 99.11(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.999(1)
_cell_length_b                   5.926(6)
_cell_length_c                   26.445(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299.2
_cell_measurement_theta_max      21.4
_cell_measurement_theta_min      18.4
_cell_volume                     1701.9(17)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction
'teXsan for Windows version 1.06 (MSC, 1997-1999)'
_computing_publication_material
'teXsan for Windows version 1.06 (MSC, 1997-1999)'
_computing_structure_refinement
'teXsan for Windows version 1.06 (MSC, 1997-1999)'
_computing_structure_solution
;
SIR92 (Altomare, et. al. 1994)
;
_diffrn_ambient_temperature      299.2
_diffrn_measurement_device       'Rigaku AFC6S'
_diffrn_measurement_method       \w-2\q
_diffrn_orient_matrix_UB_11      0.01881
_diffrn_orient_matrix_UB_12      -0.01047
_diffrn_orient_matrix_UB_13      0.03818
_diffrn_orient_matrix_UB_21      -0.01714
_diffrn_orient_matrix_UB_22      0.16491
_diffrn_orient_matrix_UB_23      0.00269
_diffrn_orient_matrix_UB_31      -0.08849
_diffrn_orient_matrix_UB_32      -0.03417
_diffrn_orient_matrix_UB_33      0.00129
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.00990
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            4544
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0.99
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.881
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             760.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.51
_refine_ls_extinction_coef       0.00000025(3)
_refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.'
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   2.525
_refine_ls_goodness_of_fit_ref   3.050
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0420
_refine_ls_wR_factor_ref         0.0400
_reflns_number_gt                2598
_reflns_number_total             4328
_reflns_threshold_expression     I>2.00\s(I)
_cod_data_source_file            b108164k.txt
_cod_data_source_block           '_cee42d-3'
_cod_original_cell_volume        1702(1)
_cod_original_sg_symbol_H-M      'P 21/c     '
_cod_original_formula_sum        'C15 H24 I N O2 '
_cod_database_code               7204251