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_7157779
_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 ad
_chemical_compound_source        ' from U of Wollongong '
_chemical_formula_moiety         'C23 H35 Cl F N O2 Si'
_chemical_formula_sum            'C23 H35 Cl F N O2 Si'
_chemical_formula_weight         440.07
_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             18-08-17
_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                 108.179(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0485(6)
_cell_length_b                   7.5574(3)
_cell_length_c                   14.9506(7)
_cell_measurement_reflns_used    7046
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     1186.03(10)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_av_sigmaI/netI    0.0851
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24051
_diffrn_reflns_theta_full        74.149
_diffrn_reflns_theta_max         74.149
_diffrn_reflns_theta_min         4.212
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.121
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.66
_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    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             471.999
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.33
_refine_ls_abs_structure_details 'Flack (1983), 1322 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.0057235
_refine_ls_shift/su_mean         0.0003499
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.09P)^2^ + 0.72P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1504
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1504
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              9
_reflns_limit_k_min              -6
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3617
_reflns_number_total             3918
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.00
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0598
_oxford_refine_ls_scale          8.0(3)
_oxford_reflns_number_all        3918
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\pyn1812SNQ\Tony_pyn1812SNQ_da At 9:16 on '
_cod_data_source_file            d0ob02075c2.cif
_cod_data_source_block           pyn1812SNQ
_cod_depositor_comments
'Adding full bibliography for 7157774--7157779.cif.'
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               7157779
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, CL(1,U'S,OCC) CL(91,U[ISO],OCC) 
CONT SI(1,U'S,OCC) SI(91,U[ISO],OCC) 
CONT F(1,U'S) 
CONT O(1,U'S) O(2,U'S,OCC) O(92,U[ISO],OCC) 
CONT N(1,U'S) UNTIL C(23) 
CONT C(18,OCC) UNTIL C(23) 
CONT C(918,U[ISO],OCC) UNTIL C(923) 
CONT ENANTIO 
FIX CL(91,U[ISO]) SI(91,U[ISO]) O(92,U[ISO]) 
CONT C(918,U[ISO]) UNTIL C(923) 
EQUIV CL(1,OCC) CL(91,OCC) 
WEIGHT -1  CL(91,OCC) 
EQUIV SI(1,OCC) O(2,OCC) C(18,OCC) UNTIL C(23) 
CONT SI(91,OCC) O(92,OCC) C(918,OCC) UNTIL C(923) 
WEIGHT -1 SI(91,OCC) O(92,OCC) C(918,OCC) UNTIL C(923) 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) H(32,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,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) H   ( 172,X'S) H(173,X'S) H(174,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) H   ( 223,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C(  918,X'S) H( 9181,X'S) H( 9182,X'S) H   ( 9183,X'S) 
RIDE C(  919,X'S) H( 9191,X'S) H( 9192,X'S) H   ( 9193,X'S) 
RIDE C(  921,X'S) H( 9211,X'S) H( 9212,X'S) H   ( 9213,X'S) 
RIDE C(  922,X'S) H( 9221,X'S) H( 9222,X'S) H   ( 9223,X'S) 
RIDE C(  923,X'S) H( 9231,X'S) H( 9232,X'S) H   ( 9233,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 1.82, .02 = C(17) TO CL(91) 
REM 
DIST 1.41, .02 = C(3) TO O(92) 
DIST 1.65, .02 = O(92) TO SI(91) 
ANGLE 122 2 = C(3) TO O(92) TO SI(91) 
REM 
DIST 1.87, .02 = SI(91) TO C(918) 
DIST 1.87, .02 = SI(91) TO C(919) 
DIST 1.87, .02 = SI(91) TO C(920) 
ANGLE 110 2 = O(92) TO SI(91) TO C(918) 
ANGLE 110 2 = O(92) TO SI(91) TO C(919) 
ANGLE 110 2 = O(92) TO SI(91) TO C(920) 
ANGLE 110 2 = C(918) TO SI(91) TO C(919) 
ANGLE 110 2 = C(918) TO SI(91) TO C(920) 
ANGLE 110 2 = C(919) TO SI(91) TO C(920) 
DIST 1.52, .02 = C(920) TO C(921) 
DIST 1.52, .02 = C(920) TO C(922) 
DIST 1.52, .02 = C(920) TO C(923) 
ANGLE 110 2 = SI(91) TO C(920) TO C(921) 
ANGLE 110 2 = SI(91) TO C(920) TO C(922) 
ANGLE 110 2 = SI(91) TO C(920) TO C(923) 
ANGLE 110 2 = C(921) TO C(920) TO C(922) 
ANGLE 110 2 = C(921) TO C(920) TO C(923) 
ANGLE 110 2 = C(922) TO C(920) TO C(923) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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