Late-Stage Functionalization of Aromatic Acids with Aliphatic Aziridines: Direct Approach to Form β-Branched Arylethylamine Backbones
Zhou, Kehan; Zhu, Yan; Fan, Weitai; Chen, Yujie; Xu, Xu; Zhang, Jingyu; Zhao, Yingsheng; ACS Catalysis 9 (2019) 6738–; doi:10.1021/acscatal.9b01347

data_4514655
_publ_section_title
;
 Late-Stage Functionalization of Aromatic Acids with Aliphatic Aziridines:
 Direct Approach to Form \b-Branched Arylethylamine Backbones
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              6738
_journal_paper_doi               10.1021/acscatal.9b01347
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration S
_chemical_formula_moiety         'C18 H21 N O5 S, H2 O'
_chemical_formula_sum            'C18 H23 N O6 S'
_chemical_formula_weight         381.43
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.170(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1162(7)
_cell_length_b                   11.0214(9)
_cell_length_c                   10.5496(8)
_cell_measurement_reflns_used    1726
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.643
_cell_measurement_theta_min      2.51
_cell_volume                     943.48(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6059
_diffrn_reflns_point_group_measured_fraction_full 0.865
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.686
_diffrn_reflns_theta_min         2.510
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0403P)^2^+0.0189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.601
_reflns_Friedel_fraction_full    0.718
_reflns_Friedel_fraction_max     0.647
_reflns_number_gt                2335
_reflns_number_total             3984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01347_si_002.cif
_cod_data_source_block           190510e
_cod_database_code               4514655
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.941
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.94(12)
 0.06(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 N1(H1), O6(H6A,H6B)
3.b Ternary CH refined with riding coordinates:
 C9(H9)
3.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C16(H16), C17(H17)
3.e Tetrahedral OH refined with riding coordinates:
 O1(H1A)
3.f Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'