Different hybridized oxygen atoms controlled chemoselective formation of oxocarbenium ions: synthesis of chiral heterocyclic compounds.
Wu, Xiao-Na; You, Zhi-Hao; Liu, Yan-Kai; Organic & biomolecular chemistry 16 (2018) 6507–6520; doi:10.1039/c8ob01743c

data_7156380
_publ_section_title
;
 Different hybridized oxygen atoms controlled chemoselective formation of
 oxocarbenium ions: synthesis of chiral heterocyclic compounds.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6507
_journal_page_last               6520
_journal_paper_doi               10.1039/c8ob01743c
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C22 H24 F N O5'
_chemical_formula_sum            'C22 H24 F N O5'
_chemical_formula_weight         401.42
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-09-26 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.387(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.530(3)
_cell_length_b                   5.649(2)
_cell_length_c                   23.594(9)
_cell_measurement_reflns_used    7783
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.413
_cell_measurement_theta_min      2.606
_cell_volume                     997.4(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      173
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3586
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_min         0.868
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.196
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0768
_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^)+3.4865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2055
_refine_ls_wR_factor_ref         0.2068
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                3463
_reflns_number_total             3586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01743c2.cif
_cod_data_source_block           lyk_0m
_cod_depositor_comments
'Adding full bibliography for 7156380--7156382.cif.'
_cod_database_code               7156380
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.662(5) 0.338(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C13(H13), C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              20890
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'