General stereoretentive preparation of chiral secondary mixed alkylmagnesium reagents and their use for enantioselective electrophilic aminations.
Kremsmair, Alexander; Wilke, Henrik R.; Simon, Matthias M.; Schmidt, Quirin; Karaghiosoff, Konstantin; Knochel, Paul; Chemical science 13 (2021) 44–49; doi:10.1039/d1sc05315a

data_1565013
_publ_section_title
;
 General stereoretentive preparation of chiral secondary mixed
 alkylmagnesium reagents and their use for enantioselective electrophilic
 aminations.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              44
_journal_page_last               49
_journal_paper_doi               10.1039/d1sc05315a
_journal_volume                  13
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H20 N O S, Cl'
_chemical_formula_sum            'C15 H20 Cl N O S'
_chemical_formula_weight         297.83
_chemical_name_systematic
;
4-(1-(benzo[b]thiophen-5-yl)ethyl)morpholin-4-ium chloride
;
_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
_audit_update_record
;
2021-09-20 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2165(2)
_cell_length_b                   12.5371(4)
_cell_length_c                   16.4763(6)
_cell_measurement_reflns_used    6136
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.3090
_cell_measurement_theta_min      2.0580
_cell_volume                     1490.68(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30202
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_min         2.041
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       platelet
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1603 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         4545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0480P)^2^+0.0119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0862
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4002
_reflns_number_total             4545
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05315a2.cif
_cod_data_source_block           test1
_cod_depositor_comments          'Adding full bibliography for 1565013.cif.'
_cod_database_code               1565013
_shelx_estimated_absorpt_t_min   0.876
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2014-3
_shelx_res_checksum              63350