#------------------------------------------------------------------------------
#$Date: 2021-01-07 09:07:49 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260822 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157773.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7157773
loop_
_publ_author_name
'Yang, Shuang'
'Chen, Yuhang'
'Yuan, Zidan'
'Bu, Feiyu'
'Jiang, Cheng'
'Ding, Zhenhua'
_publ_section_title
;
 Divergent synthesis of oxazolidines and morpholines via
 PhI(OAc)₂-mediated difunctionalization of alkenes.
;
_journal_issue                   48
_journal_name_full               'Organic & 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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.0333P)²+0.0583P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.3946(2) 0.49476(17) 0.64747(16) 0.0287(4) Uani 1 1 d . . . . .
O1 O 0.4899(7) 0.4045(5) 0.7378(5) 0.0319(10) Uani 1 1 d . . . . .
O2 O 0.1539(6) 0.4977(5) 0.6522(5) 0.0341(11) Uani 1 1 d . . . . .
O3 O 0.6663(7) 0.3601(6) 0.2440(5) 0.0417(12) Uani 1 1 d D . . . .
N1 N 0.4289(8) 0.4008(6) 0.4552(5) 0.0283(12) Uani 1 1 d . . . . .
C1 C 0.5618(10) 0.7166(8) 0.7166(7) 0.0267(14) Uani 1 1 d . . . . .
C6 C 0.4594(10) 0.8452(8) 0.7058(7) 0.0297(15) Uani 1 1 d . . . . .
H6 H 0.303686 0.814521 0.658015 0.036 Uiso 1 1 calc R . . . .
C2 C 0.7871(10) 0.7590(8) 0.7847(7) 0.0284(15) Uani 1 1 d . . . . .
H2 H 0.856394 0.668954 0.791144 0.034 Uiso 1 1 calc R . . . .
C4 C 0.8157(10) 1.0684(8) 0.8358(8) 0.0303(15) Uani 1 1 d . . . . .
C17 C 0.2447(11) 0.0003(8) 0.4116(8) 0.0343(15) Uani 1 1 d . . . . .
H17 H 0.239472 0.081066 0.518563 0.041 Uiso 1 1 calc R . . . .
C12 C 0.4457(10) 0.0234(8) 0.3300(7) 0.0297(15) Uani 1 1 d . . . . .
C5 C 0.5874(11) 1.0215(8) 0.7662(7) 0.0336(15) Uani 1 1 d . . . . .
H5 H 0.517284 1.111127 0.759528 0.040 Uiso 1 1 calc R . . . .
C3 C 0.9120(10) 0.9344(8) 0.8439(7) 0.0322(15) Uani 1 1 d . . . . .
H3 H 1.067625 0.963552 0.891292 0.039 Uiso 1 1 calc R . . . .
C16 C 0.0545(12) -0.2574(9) 0.1844(8) 0.0429(18) Uani 1 1 d . . . . .
H16 H -0.077983 -0.353065 0.135643 0.051 Uiso 1 1 calc R . . . .
C13 C 0.4461(12) -0.0965(8) 0.1735(7) 0.0373(16) Uani 1 1 d . . . . .
H13 H 0.580759 -0.083392 0.114849 0.045 Uiso 1 1 calc R . . . .
C15 C 0.0541(11) -0.1377(8) 0.3393(8) 0.0384(16) Uani 1 1 d . . . . .
H15 H -0.081098 -0.151046 0.397397 0.046 Uiso 1 1 calc R . . . .
C10 C 0.6535(10) 0.3547(8) 0.4062(7) 0.0324(15) Uani 1 1 d . . . . .
H10 H 0.786667 0.446689 0.480275 0.039 Uiso 1 1 calc R . . . .
C14 C 0.2523(13) -0.2349(9) 0.1020(8) 0.0445(18) Uani 1 1 d . . . . .
H14 H 0.255452 -0.315490 -0.005420 0.053 Uiso 1 1 calc R . . . .
C11 C 0.6592(10) 0.1731(8) 0.4101(8) 0.0353(15) Uani 1 1 d . . . . .
H11A H 0.796592 0.141304 0.355186 0.042 Uiso 1 1 calc R . . . .
H11B H 0.682800 0.182250 0.526787 0.042 Uiso 1 1 calc R . . . .
C8 C 0.3398(12) 0.4580(9) 0.3287(8) 0.0422(18) Uani 1 1 d D . . . .
H8BC H 0.191425 0.374140 0.271279 0.051 Uiso 0.3 1 calc R . P A 2
H8BD H 0.312329 0.576863 0.378849 0.051 Uiso 0.3 1 calc R . P A 2
H8A H 0.392851 0.587627 0.355668 0.051 Uiso 0.7 1 calc R . P B 1
H8B H 0.167411 0.420256 0.311136 0.051 Uiso 0.7 1 calc R . P B 1
C7 C 0.9477(11) 1.2589(7) 0.8999(8) 0.0376(16) Uani 1 1 d . . . . .
H7A H 0.880767 1.325165 0.844670 0.056 Uiso 1 1 calc GR . . . .
H7B H 1.111706 1.269208 0.878090 0.056 Uiso 1 1 calc GR . . . .
H7C H 0.937032 1.307139 1.019051 0.056 Uiso 1 1 calc GR . . . .
C9 C 0.515(3) 0.461(3) 0.217(3) 0.039(6) Uani 0.3 1 d D U P C 2
H9A H 0.604132 0.584695 0.236651 0.046 Uiso 0.3 1 calc R . P C 2
H9B H 0.442625 0.410079 0.102129 0.046 Uiso 0.3 1 calc R . P C 2
C9A C 0.4528(15) 0.3592(14) 0.1812(10) 0.039(2) Uani 0.7 1 d D U P C 1
H9AA H 0.356924 0.236590 0.128336 0.046 Uiso 0.7 1 calc R . P C 1
H9AB H 0.471290 0.419513 0.098381 0.046 Uiso 0.7 1 calc R . P C 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 106.4(2) . . ?
O1 S1 C1 107.2(3) . . ?
O2 S1 O1 120.4(2) . . ?
O2 S1 N1 105.7(2) . . ?
O2 S1 C1 107.2(3) . . ?
N1 S1 C1 109.6(3) . . ?
C10 O3 C9 109.4(9) . . ?
C9A O3 C10 110.3(5) . . ?
C10 N1 S1 120.4(3) . . ?
C8 N1 S1 120.0(4) . . ?
C8 N1 C10 108.3(5) . . ?
C6 C1 S1 118.7(4) . . ?
C6 C1 C2 121.1(5) . . ?
C2 C1 S1 120.2(4) . . ?
C1 C6 H6 120.5 . . ?
C1 C6 C5 119.0(6) . . ?
C5 C6 H6 120.5 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.3(5) . . ?
C3 C2 H2 120.4 . . ?
C5 C4 C7 119.8(5) . . ?
C3 C4 C5 117.8(6) . . ?
C3 C4 C7 122.4(5) . . ?
C12 C17 H17 119.6 . . ?
C15 C17 H17 119.6 . . ?
C15 C17 C12 120.7(6) . . ?
C17 C12 C11 121.2(5) . . ?
C13 C12 C17 118.0(6) . . ?
C13 C12 C11 120.8(6) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 C6 121.2(6) . . ?
C4 C5 H5 119.4 . . ?
C2 C3 C4 121.6(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C14 118.3(7) . . ?
C14 C16 H16 120.9 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.7(6) . . ?
C14 C13 H13 119.7 . . ?
C17 C15 C16 121.5(7) . . ?
C17 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
O3 C10 N1 103.8(4) . . ?
O3 C10 H10 109.7 . . ?
O3 C10 C11 111.1(5) . . ?
N1 C10 H10 109.7 . . ?
N1 C10 C11 112.8(5) . . ?
C11 C10 H10 109.7 . . ?
C16 C14 C13 120.9(6) . . ?
C16 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C12 C11 C10 116.4(5) . . ?
C12 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C10 C11 H11A 108.2 . . ?
C10 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
N1 C8 H8BC 110.6 . . ?
N1 C8 H8BD 110.6 . . ?
N1 C8 H8A 111.9 . . ?
N1 C8 H8B 111.9 . . ?
N1 C8 C9A 99.5(5) . . ?
H8BC C8 H8BD 108.7 . . ?
H8A C8 H8B 109.6 . . ?
C9 C8 N1 105.7(9) . . ?
C9 C8 H8BC 110.6 . . ?
C9 C8 H8BD 110.6 . . ?
C9A C8 H8A 111.9 . . ?
C9A C8 H8B 111.9 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C9 H9A 110.1 . . ?
O3 C9 H9B 110.1 . . ?
C8 C9 O3 107.8(12) . . ?
C8 C9 H9A 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.5 . . ?
O3 C9A C8 105.3(6) . . ?
O3 C9A H9AA 110.7 . . ?
O3 C9A H9AB 110.7 . . ?
C8 C9A H9AA 110.7 . . ?
C8 C9A H9AB 110.7 . . ?
H9AA C9A H9AB 108.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.438(4) . ?
S1 O2 1.434(4) . ?
S1 N1 1.620(5) . ?
S1 C1 1.767(6) . ?
O3 C10 1.415(7) . ?
O3 C9 1.433(17) . ?
O3 C9A 1.372(9) . ?
N1 C10 1.496(7) . ?
N1 C8 1.466(8) . ?
C1 C6 1.373(7) . ?
C1 C2 1.373(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.396(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(8) . ?
C4 C5 1.390(8) . ?
C4 C3 1.385(8) . ?
C4 C7 1.498(8) . ?
C17 H17 0.9500 . ?
C17 C12 1.392(8) . ?
C17 C15 1.372(9) . ?
C12 C13 1.388(8) . ?
C12 C11 1.516(8) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.377(9) . ?
C16 C14 1.380(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(10) . ?
C15 H15 0.9500 . ?
C10 H10 1.0000 . ?
C10 C11 1.525(8) . ?
C14 H14 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 H8BC 0.9900 . ?
C8 H8BD 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.418(18) . ?
C8 C9A 1.523(10) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
