Tuning the Selectivity of Monoamine Transporter Inhibitors by the Stereochemistry of the Nitrogen Lone Pair
Miles P. Smith; Kenneth M. Johnson; Mei Zhang; Judith L. Flippen-Anderson; Alan P. Kozikowski; Journal of the American Chemical Society 120 (1998) 9072–9073; doi:10.1021/ja981423s

data_4116833
_publ_section_title
;
 Tuning the Selectivity of Monoamine Transporter Inhibitors by the
 Stereochemistry of the Nitrogen Lone Pair
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9072
_journal_page_last               9073
_journal_paper_doi               10.1021/ja981423s
_journal_volume                  120
_journal_year                    1998
_chemical_formula_moiety         'C17 H22 N+ . C10 H15 S O4-'
_chemical_formula_sum            'C27 H37 N O4 S'
_chemical_formula_weight         471.64
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 104.35(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.629(2)
_cell_length_b                   10.343(2)
_cell_length_c                   14.836(3)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.59
_cell_measurement_theta_min      5.30
_cell_volume                     1282.8(5)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         ' sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2298
_diffrn_reflns_theta_max         57.25
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        1.2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.374
_exptl_absorpt_correction_T_max  0.9279
_exptl_absorpt_correction_T_min  0.8037
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       rod
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
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_refine_ls_goodness_of_fit_obs   1.064
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         1865
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.048
_refine_ls_restrained_S_obs      1.072
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_obs          0.0696
_refine_ls_shift/esd_max         0.380
_refine_ls_shift/esd_mean        0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1470P)^2^+0.5218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2110
_refine_ls_wR_factor_obs         0.1902
_reflns_number_observed          1510
_reflns_number_total             1865
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja981423s_2.cif
_cod_data_source_block           gu16z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1470P)^2^+0.5218P] 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^)+(0.1470P)^2^+0.5218P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1282.9(5)
_cod_database_code               4116833