Enantioselective synthesis of α-(3-pyrrolyl)methanamines with an aza-tetrasubstituted center under metal-free conditions.
Dolas, Atul Jankiram; Yadav, Jyothi; Nagare, Yadav Kacharu; Rangan, Krishnan; Iype, Eldhose; Kumar, Indresh; Organic & biomolecular chemistry 23 (2024) 98–102; doi:10.1039/d4ob01729c

data_7160221
_publ_section_title
;
 Enantioselective synthesis of &#x3b1;-(3-pyrrolyl)methanamines with an
 aza-tetrasubstituted center under metal-free conditions.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              98
_journal_page_last               102
_journal_paper_doi               10.1039/d4ob01729c
_journal_volume                  23
_journal_year                    2024
_chemical_formula_moiety         'C13 H14 N2 O3 S'
_chemical_formula_sum            'C13 H14 N2 O3 S'
_chemical_formula_weight         278.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-06-07 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.644(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0312(2)
_cell_length_b                   16.1924(3)
_cell_length_c                   9.2203(2)
_cell_measurement_reflns_used    4146
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      79.2810
_cell_measurement_theta_min      4.9050
_cell_volume                     1336.37(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_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    -29.00  13.00   0.50    1.03    --    0.00 -57.00-120.00   84
  2  \w    -88.00 -52.00   0.50    1.03    --    0.00 -57.00-120.00   72
  3  \w    -87.00 -49.00   0.50    1.03    --    0.00 -57.00 -30.00   76
  4  \w    -39.00  20.00   0.50    1.03    --    0.00 -57.00 -30.00  118
  5  \w     36.00 139.00   0.50    4.11    --  107.20 -82.00 -30.00  206
  6  \w     84.00 150.00   0.50    4.11    --  107.20  15.00  90.00  132
  7  \w     91.00 127.00   0.50    4.11    --  107.20 -30.00 -30.00   72
  8  \w     26.00  52.00   0.50    4.11    --  107.20 -82.00 -90.00   52
  9  \w     52.00  85.00   0.50    4.11    --  107.20 -30.00 -30.00   66
 10  \w     68.00 108.00   0.50    4.11    --  107.20 -82.00 -90.00   80
 11  \w     21.00 135.00   0.50    4.11    --  107.20 -15.00-120.00  228
 12  \w     20.00  56.00   0.50    4.11    --  107.20 -30.00 -90.00   72
 13  \w     83.00 110.00   0.50    4.11    --  107.20 -30.00 -90.00   54
 14  \w     20.00 132.00   0.50    4.11    --  107.20 -61.00 -30.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0783438000
_diffrn_orient_matrix_UB_12      -0.0113111000
_diffrn_orient_matrix_UB_13      -0.1576453000
_diffrn_orient_matrix_UB_21      0.1531228000
_diffrn_orient_matrix_UB_22      -0.0020923000
_diffrn_orient_matrix_UB_23      -0.0561990000
_diffrn_orient_matrix_UB_31      0.0058049000
_diffrn_orient_matrix_UB_32      -0.0944594000
_diffrn_orient_matrix_UB_33      0.0201268000
_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  0.0296
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7241
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.568
_diffrn_reflns_theta_min         4.941
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0549P)^2^+0.6433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1129
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2508
_reflns_number_total             2808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01729c2.cif
_cod_data_source_block           exp_1355_ad-686_20230202
_cod_depositor_comments
'Adding full bibliography for 7160220--7160222.cif.'
_cod_database_code               7160221
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H14 N2 O3 S'
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.793
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              8127
_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 2.014
_oxdiff_exptl_absorpt_empirical_full_min 0.763