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_7156381
_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_absolute_configuration ad
_chemical_formula_moiety         '4(C31 H32 N2 O4), 4(C4 H8 O2)'
_chemical_formula_sum            'C140 H160 N8 O24'
_chemical_formula_weight         2338.75
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-08-14 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   7.9683(3)
_cell_length_b                   16.3532(6)
_cell_length_c                   23.8547(9)
_cell_measurement_reflns_used    6473
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.332
_cell_measurement_theta_min      4.588
_cell_volume                     3108.4(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9202
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.416
_diffrn_reflns_theta_min         5.410
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         5132
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.6404P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.614
_reflns_Friedel_fraction_full    0.797
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                4893
_reflns_number_total             5132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01743c2.cif
_cod_data_source_block           cu_20160411xl_lyk_0m
_cod_depositor_comments
'Adding full bibliography for 7156380--7156382.cif.'
_cod_database_code               7156381
_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
 C17A-C16 = C16-C17
 1.5 with sigma of 0.02
3. Others
 Sof(H16C)=Sof(H16D)=Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15C)=Sof(H15D)=
 Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(H16A)=Sof(H16B)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C17)=
 Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C2(H2), C3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C27(H27A,H27B), C1(H1A,H1B), C16(H16A,H16B), C16(H16C,H16D),
 C14(H14A,H14B), C14(H14C,H14D), C15(H15A,H15B), C34(H34A,H34B), C15A(H15C,H15D)
4.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C20(H20), C7(H7), C21(H21), C28(H28), C11(H11), C31(H31), C13(H13),
 C30(H30), C24(H24), C22(H22), C23(H23), C12(H12), C29(H29)
4.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C17A(H17D,H17E,
 H17F)
;
_shelx_res_checksum              67910
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'