Synthesis of functionalized spirocyclic oxetanes through Paternò-Büchi reactions of cyclic ketones and maleic acid derivatives.
Michalska, Weronika Z.; Halcovitch, Nathan R.; Coote, Susannah C.; Chemical communications (Cambridge, England) 59 (2023) 784–787; doi:10.1039/d2cc06459f

data_7131137
_publ_section_title
;
 Synthesis of functionalized spirocyclic oxetanes through
 Patern&#xf2;-B&#xfc;chi reactions of cyclic ketones and maleic acid
 derivatives.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              784
_journal_page_last               787
_journal_paper_doi               10.1039/d2cc06459f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C18 H23 N O7 S'
_chemical_formula_sum            'C18 H23 N O7 S'
_chemical_formula_weight         397.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-20 deposited with the CCDC.	2022-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.6890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.2318(2)
_cell_length_b                   8.22860(10)
_cell_length_c                   24.0575(2)
_cell_measurement_reflns_used    12407
_cell_measurement_temperature    100.00(16)
_cell_measurement_theta_max      76.1100
_cell_measurement_theta_min      4.6030
_cell_volume                     3794.38(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4563
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -65.00  30.00   1.00    1.00    --  -42.28  38.00 120.00   95
  2  \w    -87.00  -6.00   1.00    1.00    --  -42.28 125.00   0.00   81
  3  \w    -69.00  28.00   1.00    1.00    --  -42.28  57.00-150.00   97
  4  \w     20.00 115.00   1.00    1.00    --   42.28  38.00   0.00   95
  5  \w     27.00  97.00   1.00    1.00    --   42.28-125.00-150.00   70
  6  \w     36.00 135.00   1.00    4.00    --  111.00 -30.00-150.00   99
  7  \w     41.00 139.00   1.00    4.00    --  111.00 -61.00-180.00   98
  8  \w     40.00 135.00   1.00    4.00    --  111.00 -45.00  30.00   95
  9  \w    103.00 178.00   1.00    4.00    --  111.00  77.00-180.00   75
 10  \w     30.00 107.00   1.00    4.00    --  111.00 -94.00-120.00   77
 11  \w     41.00 139.00   1.00    4.00    --  111.00 -61.00 -60.00   98
 12  \w     37.00 142.00   1.00    4.00    --  111.00 -77.00  60.00  105
 13  \w     83.00 178.00   1.00    4.00    --  111.00  61.00-180.00   95
 14  \w     41.00 139.00   1.00    4.00    --  111.00 -61.00-120.00   98
 15  \w     37.00 101.00   1.00    4.00    --  111.00 -77.00  30.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0236583000
_diffrn_orient_matrix_UB_12      -0.0273973000
_diffrn_orient_matrix_UB_13      -0.0620467000
_diffrn_orient_matrix_UB_21      0.0665478000
_diffrn_orient_matrix_UB_22      0.0851059000
_diffrn_orient_matrix_UB_23      -0.0166415000
_diffrn_orient_matrix_UB_31      0.0384007000
_diffrn_orient_matrix_UB_32      -0.1644212000
_diffrn_orient_matrix_UB_33      0.0016445000
_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  0.0185
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15169
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.264
_diffrn_reflns_theta_min         3.687
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.114
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+3.6283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3868
_reflns_number_total             3948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06459f2.cif
_cod_data_source_block           sc139_autored
_cod_depositor_comments          'Adding full bibliography for 7131137.cif.'
_cod_database_code               7131137
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C H N O S '
_chemical_oxdiff_usercomment     WM-06-55
_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:
 C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              30281
_shelx_hkl_checksum              70573
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.419
_oxdiff_exptl_absorpt_empirical_full_min 0.746