One step stereoselective synthesis of oxazoline-fused saccharides and their conversion into the corresponding 1,2-<i>cis</i> glycosylamines bearing various protected groups.
Dong, Sanfeng; Zhao, Yitian; Shi, Yulong; Xu, Zhijian; Shen, Jingshan; Jia, Qi; Li, Yiming; Chen, Kaixian; Li, Bo; Zhu, Weiliang; Organic & biomolecular chemistry 19 (2021) 1580–1588; doi:10.1039/d0ob02477e

data_7157850
_publ_section_title
;
 One step stereoselective synthesis of oxazoline-fused saccharides and
 their conversion into the corresponding 1,2-<i>cis</i> glycosylamines
 bearing various protected groups.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1580
_journal_page_last               1588
_journal_paper_doi               10.1039/d0ob02477e
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H15 N O7'
_chemical_formula_sum            'C14 H15 N O7'
_chemical_formula_weight         309.27
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-09 deposited with the CCDC.	2021-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.803(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7659(3)
_cell_length_b                   12.6787(7)
_cell_length_c                   11.0168(6)
_cell_measurement_reflns_used    5743
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.704
_cell_measurement_theta_min      4.034
_cell_volume                     662.28(7)
_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      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6504
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        66.583
_diffrn_reflns_theta_max         66.583
_diffrn_reflns_theta_min         4.033
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1610 before and 0.0569 after correction. The Ratio of minimum to maximum transmission is 0.8278. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2250
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0331P)^2^+0.0830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                2196
_reflns_number_total             2250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02477e2.cif
_cod_data_source_block           220191102hjq_0m
_cod_depositor_comments          'Adding full bibliography for 7157850.cif.'
_cod_database_code               7157850
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.909
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C9(H9), C10(H10), C14(H14), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C4(H4A)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O1(H1), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'