Stereoselective synthesis of 2,5-disubstituted pyrrolidines through gold-catalyzed anti-Markovnikov hydroamination-initiated tandem reactions
Ye, Long-Wu; Tan, Tong-De; Chen, Yang-Bo; Yang, Ming-Yang; Wang, Jia-Le; Su, Hao-Ze; Hong, Feng-Lin; Zhou, Jin-Mei; Chemical Communications  (2019) –; doi:10.1039/C9CC05295J

data_7123900
_publ_section_title
;
 Stereoselective synthesis of 2,5-disubstituted pyrrolidines through
 gold-catalyzed anti-Markovnikov hydroamination-initiated tandem reactions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05295J
_journal_year                    2019
_chemical_absolute_configuration
(2R,5S)-2-allyl-5-(4-bromophenyl)-1-tosylpyrrolidine
_chemical_formula_moiety         'C17 H17 Br N4 O2 S'
_chemical_formula_sum            'C17 H17 Br N4 O2 S'
_chemical_formula_weight         421.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.06 svn.r3119 for OlexSys, GUI svn.r4979)
;
_audit_update_record
;
2019-07-04 deposited with the CCDC.    2019-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.19
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.515
_cell_length_b                   13.740
_cell_length_c                   12.607
_cell_measurement_reflns_used    10179
_cell_measurement_temperature    373(2)
_cell_measurement_theta_max      54.93
_cell_measurement_theta_min      6.46
_cell_volume                     1873.809
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      373.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_av_unetI/netI     0.1692
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18427
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         27.448
_diffrn_reflns_theta_min         3.229
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.323
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.278853
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.529
_refine_diff_density_min         -1.080
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details
;
 Flack x determined using 1229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.002(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         8504
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1727
_refine_ls_R_factor_gt           0.0729
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.2339
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3855
_reflns_number_total             8504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05295j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

2025-03-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C68 H68 Br4 N16 O8 S4'
_cod_original_formula_weight         1685.26
_cod_original_formula_moiety         '4(C17 H17 Br N4 O2 S)'
_cod_original_formula_units_Z            1
_cod_original_cell_volume        1873.9
_cod_database_code               7123900
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C1AA(H1AA), C44(H44), C47(H47)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B), C38(H38A,H38B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C4AA(H4AA), C5(H5), C10(H10), C16(H16), C0AA(H0AA), C21(H21),
 C2AA(H2AA), C4(H4), C17(H17), C22(H22), C24(H24), C27(H27), C28(H28), C32(H32),
  C34(H34)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              29079
_olex2_submission_special_instructions 'No special instructions were received'