Asymmetric synthesis of highly sterically congested α-tertiary amines <i>via</i> organocatalyzed kinetic resolution.
Jiang, Qianwen; Xie, Wansen; Yang, Xiaoyu; Chemical communications (Cambridge, England) 59 (2023) 4762–4765; doi:10.1039/d3cc00653k

data_7131479
_publ_section_title
;
 Asymmetric synthesis of highly sterically congested &#x3b1;-tertiary
 amines <i>via</i> organocatalyzed kinetic resolution.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4762
_journal_page_last               4765
_journal_paper_doi               10.1039/d3cc00653k
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 N'
_chemical_formula_sum            'C21 H20 N'
_chemical_formula_weight         286.38
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-02-07 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.3035(4)
_cell_length_b                   14.6331(5)
_cell_length_c                   19.5647(6)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      77.16
_cell_measurement_theta_min      4.94
_cell_volume                     3236.10(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            48265
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.398
_diffrn_reflns_theta_min         3.772
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  0.0891
_exptl_absorpt_correction_T_min  0.0105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1735 before and 0.1178 after correction.
The Ratio of minimum to maximum transmission is 0.1178.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 2589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0665
_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^)+(0.1338P)^2^+0.0206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1737
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                6317
_reflns_number_total             6839
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00653k2.cif
_cod_data_source_block           cu_7_4_s_0m
_cod_depositor_comments          'Adding full bibliography for 7131479.cif.'
_cod_database_code               7131479
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.904
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C008(H008), C00A(H00G), C00E(H00J), C00F(H00K),
 C00H(H00H), C00I(H00I), C00M(H00M), C00N(H00N), C00P(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014),
 C015(H015), C016(H016), C017(H017), C018(H018)
2.b Idealised Me refined as rotating group:
 C009(H00A,H00B,H00C), C00B(H00D,H00E,H00F), C00K(H00L,H00O,H00P), C00Y(H00Y,H,
 HA)
;
_shelx_res_checksum              6469
_shelx_hkl_checksum              67843
_olex2_submission_special_instructions 'No special instructions were received'