Diastereomers of N-α-Phenylethyl-t-butylsulfinamide: Absolute Configurations and Predominant Conformations
Ana G. Petrovic; Prasad L. Polavarapu; Jozef Drabowicz; Piotr Łyźwa; Marian Mikołajczyk; Wanda Wieczorek; Agnieszka Balińska; Journal of Organic Chemistry 73 (2008) 3120–3129; doi:10.1021/jo702544g

data_4023361
_publ_contact_author_address
;Institute of Chemistry and Environmental Protection
Jan D\/lugosz University
ul. Armii Krajowej 13/15
42-200 Cz\;estochowa
Poland
;
_publ_contact_author_email       abalinska@poczta.onet.pl
_publ_contact_author_fax         '+48 034 3665322'
_publ_contact_author_name        'Bali\'nska Agnieszka'
_publ_contact_author_phone       '+48 034 3614918'
_publ_section_title
;
 Diastereomers of N-\a-Phenylethyl-t-butylsulfinamide:
 Absolute Configurations and Predominant Conformations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3120
_journal_page_last               3129
_journal_paper_doi               10.1021/jo702544g
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C12 H19 N O S'
_chemical_formula_sum            'C12 H19 N O S'
_chemical_formula_weight         225.35
_chemical_name_systematic
;
        N-\a-phenylethyl-t-butylsulfinamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7913(19)
_cell_length_b                   12.976(3)
_cell_length_c                   17.478(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.39
_cell_measurement_theta_min      15.94
_cell_volume                     1313.4(6)
_computing_cell_refinement       'CAD-4 Manual'
_computing_data_collection
'CAD-4 Manual (Schagen, Straver, van Meurs & Williams, 1989)'
_computing_data_reduction        'SDP (Frenz, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3051
_diffrn_reflns_theta_full        74.98
_diffrn_reflns_theta_max         74.98
_diffrn_reflns_theta_min         4.24
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.991
_exptl_absorpt_correction_T_max  0.8732
_exptl_absorpt_correction_T_min  0.6685
_exptl_absorpt_correction_type
'empirical (\y scan; North, Phillips & Mathews, 1968; Frenz, 1986)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.14
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.35
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1015P)^2^+0.0902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.129
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                2654
_reflns_number_total             2699
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702544g-File002.cif
_cod_data_source_block           psidec
_cod_database_code               4023361