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_7204252
_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         'C16 H30 I N O2 Si '
_chemical_formula_sum            'C16 H30 I N O2 Si'
_chemical_formula_weight         423.41
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.151(3)
_cell_length_b                   21.506(3)
_cell_length_c                   7.204(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299.2
_cell_measurement_theta_max      12.1
_cell_measurement_theta_min      10.6
_cell_volume                     2037.5(10)
_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      0.07536
_diffrn_orient_matrix_UB_12      0.00584
_diffrn_orient_matrix_UB_13      0.00638
_diffrn_orient_matrix_UB_21      0.00947
_diffrn_orient_matrix_UB_22      -0.04612
_diffrn_orient_matrix_UB_23      0.00358
_diffrn_orient_matrix_UB_31      0.00371
_diffrn_orient_matrix_UB_32      -0.00092
_diffrn_orient_matrix_UB_33      -0.13862
_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  0.04170
_diffrn_reflns_av_sigmaI/netI    0.085
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5259
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        -19.30
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.635
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             864.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.41
_refine_ls_extinction_coef       0.00000084(8)
_refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.'
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.407
_refine_ls_goodness_of_fit_ref   1.670
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00016|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0540
_refine_ls_wR_factor_ref         0.0450
_reflns_number_gt                1381
_reflns_number_total             2631
_reflns_threshold_expression     I>2.00\s(I)
_cod_data_source_file            b108164k.txt
_cod_data_source_block           '_cee54b-4'
_cod_original_cell_volume        2037.5(7)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C16 H30 I N O2 Si '
_cod_database_code               7204252