The SN2 Reaction in the Solid State. An Unusual, BAl2 Aminolysis of an Ester Group in Crystalline (\±)-2-Amino-2'-hydroxy-3'-(methoxycarbonyl)- 1,1'-binaphthyl Elucidated by X-ray Diffraction and Isotopic Labeling. New Experimental Evidence for Linearity in SN2 Substitution
Martin Smrčina; Štěpán Vyskočil; Vladimír Hanuš; Miroslav Polášek; Vratislav Langer; Benjamin G. M. Chew; David B. Zax; Hugh Verrier; Kevin Harper; Thomas A. Claxton; Pavel Kočovský; Journal of the American Chemical Society 118 (1996) 487–488; doi:10.1021/ja951920y

data_4117101
_publ_section_title
;
 The SN2 Reaction in the Solid State. An Unusual, BAl2 Aminolysis of an
 Ester Group in Crystalline (\+-)-2-Amino-2'-hydroxy-3'-(methoxycarbonyl)-
 1,1'-binaphthyl Elucidated by X-ray Diffraction and Isotopic Labeling.
 New Experimental Evidence for Linearity in SN2 Substitution
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              487
_journal_page_last               488
_journal_paper_doi               10.1021/ja951920y
_journal_volume                  118
_journal_year                    1996
_chemical_formula_sum            'C22 H17 N O3'
_chemical_formula_weight         343.37
_chemical_name_systematic
;
 (+-)-2-amino-2'-hydroxy-3'-(methoxycarbonyl)-1,1'-binaphtyl
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.319(2)
_cell_length_b                   8.8990(10)
_cell_length_c                   34.051(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      13.20
_cell_measurement_theta_min      5.53
_cell_volume                     3429.9(8)
_computing_cell_refinement       'Enraf-Nonius Express'
_computing_data_collection       'Enraf-Nonius Express'
_computing_data_reduction        'MSC TEXSAN'
_computing_molecular_graphics    'MSC TEXSAN'
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(1)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.6574
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            1505
_diffrn_reflns_theta_max         19.61
_diffrn_reflns_theta_min         2.97
_diffrn_standards_decay_%        0.8
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       prism
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.916
_refine_ls_goodness_of_fit_obs   1.006
_refine_ls_hydrogen_treatment    'riding on pivot atoms with common Uiso'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         1505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.916
_refine_ls_restrained_S_obs      1.006
_refine_ls_R_factor_all          0.3578
_refine_ls_R_factor_obs          0.0424
_refine_ls_shift/esd_max         0.008
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2354
_refine_ls_wR_factor_obs         0.0973
_reflns_number_observed          410
_reflns_number_total             1505
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja951920y.cif
_cod_data_source_block           JA951920Y-164
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1000P)^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^)+(0.1000P)^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_database_code               4117101