Addition of the Lithium Anion of Diphenylmethanol Methyl/Methoxymethyl Ether to Nonracemic Sulfinimines: Two-Step Asymmetric Synthesis of Diphenylprolinol Methyl Ether and Chiral (Diphenylmethoxymethyl)amines.
Reddy, Arava Amaranadha; Prasad, Kavirayani R.; The Journal of organic chemistry 83 (2018) 10776–10785; doi:10.1021/acs.joc.8b01381

data_4035637
_publ_section_title
;
 Addition of the Lithium Anion of Diphenylmethanol Methyl/Methoxymethyl
 Ether to Nonracemic Sulfinimines: Two-Step Asymmetric Synthesis of
 Diphenylprolinol Methyl Ether and Chiral (Diphenylmethoxymethyl)amines.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10776
_journal_page_last               10785
_journal_paper_doi               10.1021/acs.joc.8b01381
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H36 Br N O3 S'
_chemical_formula_sum            'C25 H36 Br N O3 S'
_chemical_formula_weight         510.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.715(3)
_cell_length_b                   14.329(6)
_cell_length_c                   21.298(9)
_cell_measurement_reflns_used    8321
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.44
_cell_measurement_theta_min      2.89
_cell_volume                     2659.6(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  GRAPHITE
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            89731
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         26.484
_diffrn_reflns_theta_min         2.843
_diffrn_source                   'SEALED TUBE'
_exptl_absorpt_coefficient_mu    1.648
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'NOT MEASURED'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.348
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1420 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         5465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0705P)^2^+2.5866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1569
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4029
_reflns_number_total             5465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01381_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'DIRECT' was changed
to 'direct' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_atom_sites_solution_secondary' value 'DIFMAP' was changed
to 'difmap' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_diffrn_radiation_probe' value 'X-RAY' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4035637
_shelx_estimated_absorpt_t_min   0.546
_shelx_estimated_absorpt_t_max   0.719
_shelx_res_checksum              37158
_shelx_hkl_checksum              12643