Diastereoselective Hydroxymethylation of Cyclic N-tert-Butanesulfinylketimines Using Methoxymethanol as Formaldehyde Source.
Priede, Martins; Kazak, Mihail; Kalnins, Toms; Shubin, Kirill; Suna, Edgars; The Journal of organic chemistry 79 (2014) 3715–3724; doi:10.1021/jo500506u

data_4029264
_publ_section_title
;
 Diastereoselective Hydroxymethylation of Cyclic
 N-tert-Butanesulfinylketimines Using Methoxymethanol as Formaldehyde
 Source.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3715
_journal_page_last               3724
_journal_paper_doi               10.1021/jo500506u
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C13 H19 N O2 S2'
_chemical_formula_sum            'C13 H19 N O2 S2'
_chemical_formula_weight         285.41
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.99610(10)
_cell_length_b                   9.1613(2)
_cell_length_c                   25.6885(7)
_cell_measurement_reflns_used    2147
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.9
_cell_volume                     1411.12(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0023
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            3750
_diffrn_reflns_theta_full        29.5
_diffrn_reflns_theta_max         29.5
_diffrn_reflns_theta_min         1.5
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.6419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0963
_reflns_d_resolution_high        0.7204
_reflns_number_gt                3385
_reflns_number_total             3746
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            3f.cif
_cod_data_source_block           MKW_I_286
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029264.cif.
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4029264
_shelx_title                     ' Compound MKW_I_286'
_shelx_refln_list_code           4
_shelx_f_calc_maximum            78.54
_shelx_f_squared_multiplier      1.000