Stereospecific Synthesis of cis-2,5-disubstituted pyrrolidines via N,O-acetals Formed by Hydroamination Cyclization-Hydroalkoxylation of Homopropargylic Sulfonamides in HFIP.
Wang, Weilin; Cao, Xiaohui; Xiao, Weiguo; Shi, Xiaoyu; Zuo, Xiaodan; Liu, Lingyan; Chang, Weixing; Li, Jing; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00403

data_4038423
_publ_section_title
;
 Stereospecific Synthesis of cis-2,5-disubstituted pyrrolidines via
 N,O-acetals Formed by Hydroamination Cyclization-Hydroalkoxylation of
 Homopropargylic Sulfonamides in HFIP.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00403
_journal_year                    2020
_chemical_formula_sum            'C20 H18 F7 N O3 S'
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_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
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_cell_angle_alpha                90
_cell_angle_beta                 102.94(3)
_cell_angle_gamma                90
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_cell_length_a                   15.825(3)
_cell_length_b                   7.3310(15)
_cell_length_c                   18.791(4)
_cell_measurement_reflns_used    3425
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9384
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_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
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_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
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_diffrn_reflns_point_group_measured_fraction_full 0.998
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_diffrn_reflns_theta_full        25.015
_diffrn_reflns_theta_max         25.015
_diffrn_reflns_theta_min         1.524
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       block
_exptl_crystal_F_000             978
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0059(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3745
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0650
_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^)+(0.1075P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2796
_reflns_number_total             3745
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00403_si_003.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

2025-07-29
Absurd formula changed by that obtained from coordinates
                 miguel
;
_cod_original_formula_weight         489.25
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C7.50 H7.50 F7.50 N7.50 O7.50 S0.75'
_cod_database_code               4038423
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.972
_shelx_res_checksum              67844
_shelx_hkl_checksum              60806