Electro-catalyzed, solvent-controlled divergent decarboxylative annulation and hydroaminomethylation of cyclic aldimines with <i>N</i>-arylglycines.
Zhang, Jie; Li, Xiaolan; Chen, Guisheng; Liu, Haidong; Luo, Haiqing; Chemical communications (Cambridge, England)  (2025) –; doi:10.1039/d4cc05582a

data_7134107
_publ_section_title
;
 Electro-catalyzed, solvent-controlled divergent decarboxylative
 annulation and hydroaminomethylation of cyclic aldimines with
 <i>N</i>-arylglycines.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d4cc05582a
_journal_year                    2025
_chemical_formula_moiety         'C14 H14 N2 O3 S'
_chemical_formula_sum            'C14 H14 N2 O3 S'
_chemical_formula_weight         290.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-31
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.11.02 svn.ra8b101fa for OlexSys, GUI svn.r6635)
;
_audit_update_record
;
2024-02-27 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3873(2)
_cell_length_b                   7.62710(10)
_cell_length_c                   15.5891(3)
_cell_measurement_reflns_used    7952
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.4880
_cell_measurement_theta_min      5.6740
_cell_volume                     1353.95(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     39.00 114.00   0.50    0.05    --   42.39  77.00 -60.00  150
  2  \w    116.00 141.00   0.50    0.14    --  108.79  96.00 -76.00   50
  3  \w    146.00 172.00   0.50    0.14    --  108.79  45.00   0.00   52
  4  \w     90.00 172.00   0.50    0.14    --  108.79  45.00 -30.00  164
  5  \w     95.00 121.00   0.50    0.14    --  108.79  45.00   0.00   52
  6  \w     36.00  62.00   0.50    0.14    --  108.79 -61.00  90.00   52
  7  \w     40.00  66.00   0.50    0.14    --  108.79-125.00 -30.00   52
  8  \w     88.00 116.00   0.50    0.14    --  108.79-125.00 -30.00   56
  9  \w     81.00 116.00   0.50    0.14    --  108.79-125.00-180.00   70
 10  \w     40.00 104.00   0.50    0.14    --  108.79 -77.00 -30.00  128
 11  \w     49.00 105.00   0.50    0.14    --  108.79 -95.00-150.00  112
 12  \w     43.00  68.00   0.50    0.14    --  108.79 -61.00 -30.00   50
 13  \w     44.00 105.00   0.50    0.14    --  108.79 -96.00 174.00  122
 14  \w     33.00  86.00   0.50    0.14    --  108.79 -95.00  90.00  106
 15  \w     47.00 109.00   0.50    0.14    --  108.79 -95.00  60.00  124
 16  \w     64.00 105.00   0.50    0.14    --  108.79 -95.00   0.00   82
 17  \w      8.00  35.00   0.50    0.05    --   42.39 -99.00  60.00   54
 18  \w     42.00  78.00   0.50    0.05    --   42.39 -99.00  60.00   72
 19  \w      0.00  48.00   0.50    0.05    --   42.39 -96.00 174.00   96
 20  \w   -136.00 -82.00   0.50    0.14    --  -96.00 -96.00 174.00  108
 21  \w    -38.00 -12.00   0.50    0.05    --  -42.39  38.00  90.00   52
 22  \w    -48.00 -22.00   0.50    0.14    --  -96.00  45.00 150.00   52
 23  \w    -71.00 -41.00   0.50    0.14    --  -96.00  61.00 150.00   60
 24  \w    -51.00 -20.00   0.50    0.14    --  -96.00  45.00  90.00   62
 25  \w    -45.00 -19.00   0.50    0.14    --  -96.00  45.00  60.00   52
 26  \w    -45.00 -20.00   0.50    0.14    --  -96.00  45.00 120.00   50
 27  \w     -6.00  28.00   0.50    0.05    --  -42.39  38.00  90.00   68
 28  \w    -71.00 -22.00   0.50    0.14    --  -96.00  61.00 -90.00   98
 29  \w    -51.00 -24.00   0.50    0.14    --  -96.00  45.00-120.00   54
 30  \w    -51.00 -19.00   0.50    0.14    --  -96.00  45.00-150.00   64
 31  \w    -80.00  30.00   0.50    0.05    --  -42.39  96.00 -76.00  220
 32  \w    -90.00 -25.00   0.50    0.14    --  -96.00 125.00-120.00  130
 33  \w    -90.00 -42.00   0.50    0.14    --  -96.00 125.00 -90.00   96
 34  \w    -77.00 -52.00   0.50    0.14    --  -96.00  96.00 -76.00   50
 35  \w    -72.00 -24.00   0.50    0.14    --  -96.00 125.00 120.00   96
 36  \w   -173.00-110.00   0.50    0.14    --  -96.00 -30.00 -90.00  126
 37  \w   -168.00 -82.00   0.50    0.14    --  -96.00 -45.00 -60.00  172
 38  \w    -99.00 -74.00   0.50    0.14    --  -96.00 -61.00-120.00   50
 39  \w   -171.00-102.00   0.50    0.14    --  -96.00 -61.00-120.00  138
 40  \w   -114.00 -18.00   0.50    0.05    --  -42.39 -57.00-180.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0689362000
_diffrn_orient_matrix_UB_12      0.1224361000
_diffrn_orient_matrix_UB_13      0.0602061000
_diffrn_orient_matrix_UB_21      -0.0939064000
_diffrn_orient_matrix_UB_22      -0.0263950000
_diffrn_orient_matrix_UB_23      0.0701242000
_diffrn_orient_matrix_UB_31      0.0688737000
_diffrn_orient_matrix_UB_32      -0.1583960000
_diffrn_orient_matrix_UB_33      0.0349708000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13463
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.261
_diffrn_reflns_theta_min         5.676
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.493
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 981 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2521
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0423P)^2^+0.4967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.861
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                2425
_reflns_number_total             2521
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05582a2.cif
_cod_data_source_block           ca-water-20231026_auto
_cod_database_code               7134107
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C11 H10 N O'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), C00A(H00C), C00C(H00E), C00E(H00F), C00F(H00G),
 C00G(H00H), C00H(H00I), C00I(H00J), C00J(H00K), C00K(H00L)
;
_shelx_res_checksum              26037
_shelx_hkl_checksum              76776
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.974
_oxdiff_exptl_absorpt_empirical_full_min 0.772