Construction of a quaternary stereogenic center by asymmetric hydroformylation: a straightforward method to prepare chiral α-quaternary amino acids
Zhang, Dequan; Wen, Jialin; Zhang, Xumu; Chemical Science 13 (2022) 7215–7223; doi:10.1039/D2SC02139K

data_1567072
_publ_section_title
;
 Construction of a quaternary stereogenic center by asymmetric
 hydroformylation: a straightforward method to prepare chiral
 \a-quaternary amino acids
;
_journal_issue                   24
_journal_name_full               'Chemical Science'
_journal_page_first              7215
_journal_page_last               7223
_journal_paper_doi               10.1039/D2SC02139K
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H17 N5 O5'
_chemical_formula_sum            'C18 H17 N5 O5'
_chemical_formula_weight         383.36
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-12 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.288(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1241(5)
_cell_length_b                   34.022(2)
_cell_length_c                   7.3539(5)
_cell_measurement_reflns_used    9844
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.87
_cell_measurement_theta_min      2.60
_cell_volume                     1782.4(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            34224
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.095
_diffrn_reflns_theta_min         2.597
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.901
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6412
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1299 before and 0.0674 after correction. The Ratio of minimum to maximum transmission is 0.8510. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'yellowish yellow'
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6866
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0368P)^2^+0.4033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0843
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                6332
_reflns_number_total             6866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02139k2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 1567072.cif.'
_cod_database_code               1567072
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.900
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C4(H4a,H4b)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c)
;
_shelx_res_checksum              41931
_olex2_submission_special_instructions 'No special instructions were received'