Enantioselective synthesis of α-tetrasubstituted (3-indolizinyl) (diaryl)methanamines via chiral phosphoric acid catalysis
Zhong, Jialing; Pan, Rihuang; Lin, Xufeng; RSC Advances 12 (2022) 20499–20506; doi:10.1039/D2RA03750E

data_7245213
_publ_section_title
;
 Enantioselective synthesis of \a-tetrasubstituted (3-indolizinyl)
 (diaryl)methanamines via chiral phosphoric acid catalysis
;
_journal_issue                   32
_journal_name_full               'RSC Advances'
_journal_page_first              20499
_journal_page_last               20506
_journal_paper_doi               10.1039/D2RA03750E
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H19 Cl N2 O3, 1/3(C2 H6 O)'
_chemical_formula_sum            'C28.66667 H21 Cl N2 O3.33333'
_chemical_formula_weight         482.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-21 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 125.773(8)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   24.5506(14)
_cell_length_b                   14.4941(4)
_cell_length_c                   24.9660(13)
_cell_measurement_reflns_used    13715
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.3280
_cell_measurement_theta_min      1.8448
_cell_volume                     7207.8(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details
;
  1 omega  -52.00   26.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   96.0000  119.0000 78

  2 omega  -86.00   15.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000  -60.0000 101

  3 omega  -67.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -77.0000   30.0000 111

  4 omega  -38.00   64.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   38.0000  -60.0000 102

  5 omega  -22.00   90.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  -90.0000 112

  6 omega  -22.00   62.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000   30.0000 84

  7 omega  -37.00   15.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  111.0000 -165.0000 52
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0189865000
_diffrn_orient_matrix_UB_12      0.0405707000
_diffrn_orient_matrix_UB_13      0.0156731000
_diffrn_orient_matrix_UB_21      -0.0301182000
_diffrn_orient_matrix_UB_22      0.0255316000
_diffrn_orient_matrix_UB_23      -0.0141207000
_diffrn_orient_matrix_UB_31      0.0002205000
_diffrn_orient_matrix_UB_32      -0.0098974000
_diffrn_orient_matrix_UB_33      0.0279526000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            63847
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.393
_diffrn_reflns_theta_min         1.849
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.333
_exptl_crystal_description       needle
_exptl_crystal_F_000             3008
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 4049 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.039(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     951
_refine_ls_number_reflns         17756
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0593P)^2^+1.1635P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                11396
_reflns_number_total             17756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra03750e2.cif
_cod_data_source_block           220420_zjl220420
_cod_depositor_comments
;

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C86 H63 Cl3 N6 O10'
_cod_original_formula_weight         1446.77
_cod_original_formula_moiety         '3(C28 H19 Cl N2 O3), C2 H6 O'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        7207.8(8)
_cod_database_code               7245213
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C h n o cl'
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.912
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C85(H85A,H85B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), N2(H2), C68(H68), C64(H64), C10(H10), C21(H21), C74(H74), N4(H4A),
 C8(H8), C36(H36), C73(H73), C4(H4), C25(H25), C77(H77), C1(H1), C20(H20),
 C35(H35), C76(H76), C29(H29), C3(H3), C7(H7), C63(H63), C60(H60), C26(H26),
 C59(H59), C58(H58), C57(H57), C38(H38), C17(H17), C27(H27), C32(H32), C18(H18),
  C2(H2A), C30(H30), C31(H31), C81(H81), C45(H45), C83(H83), C28(H28), C84(H84),
  C82(H82), C49(H49), C53(H53), C46(H46), C48(H48), C55(H55), C56(H56), C54(H54)
2.c Idealised Me refined as rotating group:
 C70(H70A,H70B,H70C), C14(H14A,H14B,H14C), C86(H86A,H86B,H86C), C42(H42A,H42B,
 H42C)
2.d Idealised tetrahedral OH refined as rotating group:
 O10(H10A)
;
_shelx_res_checksum              8372
_olex2_submission_special_instructions 'No special instructions were received'