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_7160222
_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         'C25 H22 N2 O'
_chemical_formula_sum            'C25 H22 N2 O'
_chemical_formula_weight         366.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-28
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-28 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9908(8)
_cell_length_b                   15.7652(5)
_cell_length_c                   5.8187(2)
_cell_measurement_reflns_used    8496
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.8170
_cell_measurement_theta_min      1.6410
_cell_volume                     1833.82(11)
_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_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_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    -11.00  14.00   0.50    7.36    --   11.50 -22.00-102.00   50
  2  \w    -13.00  12.00   0.50    7.36    --   11.50  22.00  62.00   50
  3  \w     20.00  46.00   0.50    7.36    --  -11.70  22.00  62.00   52
  4  \w     28.00  54.00   0.50    7.36    --   11.50  77.00 150.00   52
  5  \w    -77.00  35.00   0.50    7.36    --   11.50 -77.00-150.00  224
  6  \w     74.00 100.00   0.50    7.36    --   11.50  77.00 150.00   52
  7  \w    -13.00  19.00   0.50    7.36    --   11.50  77.00  30.00   64
  8  \w     59.00  85.00   0.50    7.36    --   11.50  77.00  30.00   52
  9  \w   -101.00   8.00   0.50    7.36    --  -11.70 -77.00 120.00  218
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0225205000
_diffrn_orient_matrix_UB_12      0.0325853000
_diffrn_orient_matrix_UB_13      0.0327938000
_diffrn_orient_matrix_UB_21      0.0271795000
_diffrn_orient_matrix_UB_22      -0.0285796000
_diffrn_orient_matrix_UB_23      -0.0119357000
_diffrn_orient_matrix_UB_31      0.0035849000
_diffrn_orient_matrix_UB_32      0.0120903000
_diffrn_orient_matrix_UB_33      -0.1167884000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            14236
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.049
_diffrn_reflns_theta_min         1.645
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24763
_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    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1308 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0412P)^2^+0.0739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                3673
_reflns_number_total             4140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01729c2.cif
_cod_data_source_block           ad959_20240828
_cod_depositor_comments
'Adding full bibliography for 7160220--7160222.cif.'
_cod_database_code               7160222
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H22 N2 O '
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.968
_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 O(H) groups
2.a Riding coordinates:
 N1(H1A)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 2.416
_oxdiff_exptl_absorpt_empirical_full_min 0.423