Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals
Liao, Hongze; Leng, Wei-Lin; Le Mai Hoang, Kim; Yao, Hui; He, Jingxi; Voo, Amanda Ying Hui; Liu, Xue-Wei; Chem. Sci.  (2017) –; doi:10.1039/C7SC02625K

data_1546765
_publ_section_title
;
 Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and
 11-oxatricyclo[5.3.1.0]undecane from glycals
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC02625K
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H28 N4 O7'
_chemical_formula_weight         520.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2016-12-05 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5338(6)
_cell_length_b                   16.6117(17)
_cell_length_c                   26.533(3)
_cell_measurement_reflns_used    9482
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      67.1449
_cell_measurement_theta_min      2.6600
_cell_volume                     2439.1(5)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_number            4341
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         3.14
_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.256
_refine_ls_abs_structure_details
;

Flack x determined using 1677 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(10)
_refine_ls_extinction_coef       0.0042(7)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0611P)^2^+2.8738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                4188
_reflns_number_total             4341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc02625k2.cif
_cod_data_source_block           liu45s
_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 
;
_cod_original_cell_volume        2439.1(4)
_cod_database_code               1546765
_shelx_res_checksum              89101