Synthesis of spirocyclic heterocycles from α,β-unsaturated <i>N</i>-acyliminium ions.
Thaima, Thanphat; Yazici, Arife; Auranwiwat, Chiramet; Willis, Anthony C.; Wille, Uta; Limtharakul, Thunwadee; Pyne, Stephen G.; Organic & biomolecular chemistry 19 (2021) 259–272; doi:10.1039/d0ob02075c

data_7157776
_publ_section_title
;
 Synthesis of spirocyclic heterocycles from \a,\b-unsaturated
 <i>N</i>-acyliminium ions.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              259
_journal_page_last               272
_journal_paper_doi               10.1039/d0ob02075c
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_moiety         'C28 H26 N2 O2'
_chemical_formula_sum            'C28 H26 N2 O2'
_chemical_formula_weight         422.53
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             19-01-18
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2020-06-18 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.849(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6602(5)
_cell_length_b                   8.6837(3)
_cell_length_c                   12.1854(5)
_cell_measurement_reflns_used    6066
_cell_measurement_temperature    150
_cell_measurement_theta_max      26
_cell_measurement_theta_min      4
_cell_volume                     1126.61(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'SuperMova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18376
_diffrn_reflns_theta_full        26.364
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         3.413
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.25
_refine_ls_abs_structure_details
;
The enantiomer has been assigned by reference to an unchanging chiral
centre in the synthetic procedure.
;
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0171
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.0006592
_refine_ls_shift/su_mean         0.0000640
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.53P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0960
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0960
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2268
_reflns_number_total             2456
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.52
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0461
_oxford_refine_ls_scale          5.98(14)
_oxford_reflns_number_all        2456
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\pyn1901SNQM\Tony_pyn1901SNQM_ At 11:45 on'
_cod_data_source_file            d0ob02075c2.cif
_cod_data_source_block           pyn1901SNQM
_cod_depositor_comments
'Adding full bibliography for 7157774--7157779.cif.'
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               7157776
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S H(1,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;