Oxidative bridgehead functionalization of (4 + 3) cycloadducts obtained from oxidopyridinium ions
Sungnoi, Wanna; Harmata, Michael; RSC Advances 12 (2022) 28572–28575; doi:10.1039/D2RA05189C

data_1567734
_publ_section_title
;
 Oxidative bridgehead functionalization of (4 + 3) cycloadducts obtained
 from oxidopyridinium ions
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              28572
_journal_page_last               28575
_journal_paper_doi               10.1039/D2RA05189C
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C26 H39 F6 N O4 Si'
_chemical_formula_sum            'C26 H39 F6 N O4 Si'
_chemical_formula_weight         571.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-10 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                105.3326(16)
_cell_angle_beta                 99.3403(19)
_cell_angle_gamma                101.6075(17)
_cell_formula_units_Z            2
_cell_length_a                   7.2552(2)
_cell_length_b                   13.8552(4)
_cell_length_c                   15.7314(5)
_cell_measurement_reflns_used    9791
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      73.55
_cell_measurement_theta_min      2.99
_cell_volume                     1454.49(8)
_computing_cell_refinement       'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_computing_data_collection       'Bruker Apex3 V.2018.1-0'
_computing_data_reduction        'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            51591
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.291
_diffrn_reflns_theta_min         2.992
_diffrn_source                   'Incoatec IMuS microfocus Cu tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.335
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1257 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.8764.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       needle
_exptl_crystal_F_000             604
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol/water'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0446P)^2^+0.6809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5225
_reflns_number_total             5717
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra05189c2.cif
_cod_data_source_block           8a
_cod_database_code               1567734
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.598
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C10(H10), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C21(H21A,H21B), C22(H22A,H22B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C14(H14A,H14B,H14C), C25(H25A,H25B,H25C), C15(H15A,H15B,
 H15C), C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              84334
_olex2_submission_special_instructions 'No special instructions were received'