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_7160220
_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_absolute_configuration unk
_chemical_formula_moiety         'C20 H18 N2 O'
_chemical_formula_sum            'C20 H18 N2 O'
_chemical_formula_weight         302.36
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-04-09 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   15.2367(5)
_cell_length_b                   15.2367(5)
_cell_length_c                   18.0166(5)
_cell_measurement_reflns_used    4064
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      78.3210
_cell_measurement_theta_min      4.1470
_cell_volume                     3622.3(2)
_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 1.3 (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      93(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_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    -18.00  39.00   0.50   16.00    --    0.00  37.00-180.00  114
  2  \w    -47.00  19.00   0.50   16.00    --    0.00 -37.00 120.00  132
  3  \w     38.00 127.00   0.50   65.00    --  107.20 -30.00 -30.00  178
  4  \w     23.00  90.00   0.50   65.00    --  107.20 -30.00-120.00  134
  5  \w     51.00 135.00   0.50   65.00    --  107.20 -82.00-180.00  168
  6  \w    122.00 195.00   0.50   65.00    --  107.20  82.00  30.00  146
  7  \w    107.00 139.00   0.50   65.00    --  107.20 -82.00 120.00   64
  8  \w     20.00  81.00   0.50   65.00    --  107.20 -82.00 120.00  122
;
_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      0.0798981000
_diffrn_orient_matrix_UB_12      -0.0336171000
_diffrn_orient_matrix_UB_13      -0.0028946000
_diffrn_orient_matrix_UB_21      0.0834298000
_diffrn_orient_matrix_UB_22      0.1104856000
_diffrn_orient_matrix_UB_23      -0.0136290000
_diffrn_orient_matrix_UB_31      0.0165776000
_diffrn_orient_matrix_UB_32      0.0169647000
_diffrn_orient_matrix_UB_33      0.0844289000
_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  0.0527
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14266
_diffrn_reflns_point_group_measured_fraction_full 0.631
_diffrn_reflns_point_group_measured_fraction_max 0.598
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.158
_diffrn_reflns_theta_min         4.153
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75807
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         6302
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0670
_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^)+(0.1200P)^2^+0.5054P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.1859
_reflns_Friedel_coverage         0.230
_reflns_Friedel_fraction_full    0.262
_reflns_Friedel_fraction_max     0.224
_reflns_number_gt                5291
_reflns_number_total             6302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01729c2.cif
_cod_data_source_block           exp_898-ad-28
_cod_depositor_comments
'Adding full bibliography for 7160220--7160222.cif.'
_cod_original_cell_volume        3622.3(3)
_cod_database_code               7160220
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H18 N2 O'
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.914
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C119(H11A,H11B), C19(H19A,H19B), C219(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 N101(H101), N1(H1), N201(H201), C115(H115), C202(H202), C203(H203), C2(H2),
 C114(H114), C15(H15), C113(H113), C18(H18), C210(H210), C21(H21), C204(H204),
 C112(H112), C214(H214), C217(H217), C17(H17), C118(H118), C211(H211),
 C117(H117), C4(H4), C110(H110), C212(H212), C111(H111), C215(H215), C105(H105),
  C102(H102), C213(H213), C218(H218), C3(H3), C14(H14), C5(H5), C13(H13),
 C12(H12), C10(H10), C104(H104), C103(H103), C11(H11)
2.c Idealised Me refined as rotating group:
 C220(H22A,H22B,H22C), C20(H20A,H20B,H20C), C120(H12A,H12B,H12C)
;
_shelx_res_checksum              88894
_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 1.970
_oxdiff_exptl_absorpt_empirical_full_min 0.709