Divergent synthesis of oxazolidines and morpholines <i>via</i> PhI(OAc)<sub>2</sub>-mediated difunctionalization of alkenes.
Yang, Shuang; Chen, Yuhang; Yuan, Zidan; Bu, Feiyu; Jiang, Cheng; Ding, Zhenhua; Organic & biomolecular chemistry 18 (2020) 9873–9882; doi:10.1039/d0ob01987a

data_7157773
_publ_section_title
;
 Divergent synthesis of oxazolidines and morpholines <i>via</i>
 PhI(OAc)<sub>2</sub>-mediated difunctionalization of alkenes.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9873
_journal_page_last               9882
_journal_paper_doi               10.1039/d0ob01987a
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C17 H19 N O3 S'
_chemical_formula_sum            'C17 H19 N O3 S'
_chemical_formula_weight         317.39
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-20 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                109.210(3)
_cell_angle_beta                 90.208(3)
_cell_angle_gamma                103.829(2)
_cell_formula_units_Z            1
_cell_length_a                   5.9286(5)
_cell_length_b                   8.2863(7)
_cell_length_c                   8.6201(8)
_cell_measurement_reflns_used    1482
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.144
_cell_measurement_theta_min      2.512
_cell_volume                     386.74(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0824
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4236
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.665
_diffrn_reflns_theta_min         2.512
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0833 before and 0.0589 after correction. The Ratio of minimum to maximum transmission is 0.8878. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 635 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2448
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0333P)^2^+0.0583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.692
_reflns_Friedel_fraction_max     0.674
_reflns_number_gt                1945
_reflns_number_total             2448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01987a2.cif
_cod_data_source_block           22019814dzh1_0m
_cod_depositor_comments          'Adding full bibliography for 7157773.cif.'
_cod_original_cell_volume        386.73(6)
_cod_database_code               7157773
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C8 \\sim C8-C9A
 with sigma of 0.02
 O3-C9 \\sim O3-C9A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C9A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Fixed Sof: H8BC(0.3) H8BD(0.3) H8A(0.7) H8B(0.7) C9(0.3) H9A(0.3) H9B(0.3)
 C9A(0.7) H9AA(0.7) H9AB(0.7)
5.a Ternary CH refined with riding coordinates:
 C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C8(H8BC,H8BD), C8(H8A,H8B), C9(H9A,H9B), C9A(H9AA,H9AB)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C17(H17), C5(H5), C3(H3), C16(H16), C13(H13), C15(H15),
 C14(H14)
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_olex2_submission_special_instructions 'No special instructions were received'