The synthesis of 3-amino-3-methylbicyclo[3.3.1]nonanes: Endo-selectivity in the Ritter reaction of 1,3,5,7α-tetramethylbicyclo[3.3.1]nonan-3-ol
Jirgensons, Aigars; Kauss, Valerjans; Mishnev, Anatolij F.; Kalvinsh, Ivars; Journal of the Chemical Society, Perkin Transactions 1  (1999) 3527–; doi:10.1039/a904394b

data_7213112
_publ_section_title
;
 The synthesis of 3-amino-3-methylbicyclo[3.3.1]nonanes: Endo-selectivity
 in the Ritter reaction of 1,3,5,7\a-tetramethylbicyclo[3.3.1]nonan-3-ol
;
_journal_issue                   23
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3527
_journal_paper_doi               10.1039/a904394b
_journal_year                    1999
_chemical_formula_analytical     'C14 H25 N O'
_chemical_formula_moiety         'C14 H25 N O'
_chemical_formula_structural     'C14 H25 N O'
_chemical_formula_sum            'C14 H25 N O'
_chemical_formula_weight         223.35
_chemical_melting_point          382.0(10)
_chemical_name_systematic
; N-formyl-1,3beta,5,7alpha-tetramethylbicyclo[3.3.1]nonan-3alpha-amine
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                88.19(3)
_cell_angle_beta                 84.38(3)
_cell_angle_gamma                85.53(3)
_cell_formula_units_Z            4
_cell_length_a                   8.883(2)
_cell_length_b                   12.104(2)
_cell_length_c                   13.479(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     1437.5(5)
_computing_cell_refinement       'Syntex P2~1~ software 1975'
_computing_data_collection       'Syntex P2~1~ software 1975'
_computing_data_reduction        'XTL system software'
_computing_molecular_graphics    'ORTEP II implemented on IBM-PC/AT'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Syntex P2~1~ diffractometer'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2147
_diffrn_reflns_theta_max         21.04
_diffrn_reflns_theta_min         1.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  2h
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.032
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.114
_refine_ls_goodness_of_fit_obs   1.164
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_restrained_S_obs      1.164
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_obs          0.0846
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1149P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2150
_refine_ls_wR_factor_obs         0.1832
_reflns_number_observed          1510
_reflns_number_total             2000
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            904394bsup1.cif
_cod_data_source_block           kaus
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '381-383' was changed to '382.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1149P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1149P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7213112