Crystal structures of (<i>R</i>~S~)-<i>N</i>-[(1<i>R</i>,2<i>S</i>)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (<i>R</i>~S~)-<i>N</i>-[(1<i>S</i>,2<i>R</i>)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcohols
Carbone, Matthew R.; Centola, Garrick A.; Haas, Adam; McClelland, Kevin P.; Moskowitz, Michael D.; Verderame, Angelo M.; Olezeski, Mikael S.; Papa, Louis J.; Dorn, Stephanie C. M.; Brennessel, William W.; Weix, Daniel J.; Acta Crystallographica Section E 70 (2014) 365–369; doi:10.1107/S1600536814022570

data_2240119
_publ_section_title
;
 Crystal structures of
 (<i>R</i>~S~)-<i>N</i>-[(1<i>R</i>,2<i>S</i>)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide
 and
 (<i>R</i>~S~)-<i>N</i>-[(1<i>S</i>,2<i>R</i>)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide:
 two related protected 1,2-amino alcohols
;
_journal_coeditor_code           SU2794
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              365
_journal_page_last               369
_journal_paper_doi               10.1107/S1600536814022570
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C23 H33 N O2 S'
_chemical_formula_moiety         'C23 H33 N O2 S'
_chemical_formula_sum            'C23 H33 N O2 S'
_chemical_formula_weight         387.56
_chemical_name_common            wwb03
_chemical_name_systematic
(<i>R</i>~S~)-<i>N</i>-[(1<i>S</i>,2<i>R</i>)-2-Benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 103.519(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.535(3)
_cell_length_b                   7.984(2)
_cell_length_c                   13.481(4)
_cell_measurement_reflns_used    4086
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      2.22
_cell_volume                     1102.5(5)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD platform'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18025
_diffrn_reflns_theta_full        29.575
_diffrn_reflns_theta_max         29.591
_diffrn_reflns_theta_min         1.988
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.317
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1713 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         6191
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0563P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                4675
_reflns_number_total             6191
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            su2794sup1.cif
_cod_data_source_block           2
_cod_database_code               2240119
_cod_database_fobs_code          2240119
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.984
_shelx_hkl_checksum              31896
_shelx_res_checksum              21413
_shelxl_version_number           2.014