Intramolecular Photochemical [2+1]-Cycloadditions of Nucleophilic Siloxy Carbenes
Bunyamin, Amanda; Hua, Carol; Polyzos, Anastasios; Priebbenow, Daniel; Chemical Science  (2022) –; doi:10.1039/D2SC00203E

data_1566420
_publ_section_title
;
 Intramolecular Photochemical [2+1]-Cycloadditions of Nucleophilic Siloxy
 Carbenes&#x00A0;
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00203E
_journal_year                    2022
_chemical_formula_moiety         'C25 H33 N O6 S Si'
_chemical_formula_sum            'C25 H33 N O6 S Si'
_chemical_formula_weight         503.67
_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
_audit_creation_date             2021-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-14 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                92.8956(18)
_cell_angle_beta                 109.796(2)
_cell_angle_gamma                90.2891(18)
_cell_formula_units_Z            2
_cell_length_a                   9.1233(2)
_cell_length_b                   11.1747(2)
_cell_length_c                   13.3729(3)
_cell_measurement_reflns_used    9675
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      3.5270
_cell_measurement_theta_min      76.9880
_cell_volume                     1280.81(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_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(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_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    100.00 126.00   0.50    1.20    --  107.75  30.00  30.00   52
  2  \w    130.00 177.00   0.50    1.20    --  107.75  30.00  30.00   94
  3  \w    104.00 178.00   0.50    1.20    --  107.75  15.00 120.00  148
  4  \w    112.00 139.00   0.50    1.20    --  107.75  45.00 -30.00   54
  5  \w     99.00 134.00   0.50    1.20    --  107.75  30.00 -90.00   70
  6  \w    146.00 173.00   0.50    1.20    --  107.75  30.00 -90.00   54
  7  \w    114.00 177.00   0.50    1.20    --  107.75  15.00-180.00  126
  8  \w     62.00 118.00   0.50    1.20    --  107.75-133.00  -9.92  112
  9  \w     44.00 103.00   0.50    1.20    --  107.75 -94.00  60.00  118
 10  \w     35.00 103.00   0.50    1.20    --  107.75 -94.00 -30.00  136
 11  \w     46.00  72.00   0.50    1.20    --  107.75-125.00-120.00   52
 12  \w     86.00 112.00   0.50    1.20    --  107.75-125.00-120.00   52
 13  \w     76.00 105.00   0.50    1.20    --  107.75-104.00 -96.96   58
 14  \w     -2.00  72.00   0.50    0.30    --   47.45 -87.00  83.00  148
 15  \w     88.00 127.00   0.50    1.20    --  107.75 -87.00  83.00   78
 16  \w     74.00 106.00   0.50    1.20    --  107.75 -94.00  90.00   64
 17  \w     38.00  69.00   0.50    1.20    --  107.75 -61.00 120.00   62
 18  \w     36.00  68.00   0.50    1.20    --  107.75 -77.00  60.00   64
 19  \w     47.00  72.00   0.50    1.20    --  107.75 -77.00 -30.00   50
 20  \w     74.00 101.00   0.50    1.20    --  107.75 -77.00 -30.00   54
 21  \w     46.00  71.00   0.50    1.20    --  107.75 -61.00   0.00   50
 22  \w     37.00  69.00   0.50    1.20    --  107.75 -61.00-120.00   64
 23  \w     35.00  99.00   0.50    1.20    --  107.75 -77.00-180.00  128
 24  \w     39.00  88.00   0.50    1.20    --  107.75 -77.00-150.00   98
 25  \w     38.00  70.00   0.50    1.20    --  107.75 -61.00 -90.00   64
 26  \w     38.00  71.00   0.50    1.20    --  107.75 -61.00  90.00   66
 27  \w     95.00 174.00   0.50    1.20    --  107.75 125.00-150.00  158
 28  \w    115.00 141.00   0.50    1.20    --  107.75  87.00-159.00   52
 29  \w    -21.00  28.00   0.50    0.30    --   47.45 -19.00-180.00   98
 30  \w    -23.00  52.00   0.50    0.30    --   47.45 -57.00 -60.00  150
 31  \w   -109.00 -33.00   0.50    0.30    --  -47.45 -57.00-180.00  152
 32  \w   -119.00 -73.00   0.50    0.30    --  -47.45-125.00-150.00   92
 33  \w   -129.00-102.00   0.50    1.20    --  -86.25 -87.00  83.00   54
 34  \w    -63.00 -38.00   0.50    1.20    --  -86.25  87.00-159.00   50
 35  \w    -11.00  20.00   0.50    0.30    --  -47.45  87.00-159.00   62
 36  \w    -49.00 -15.00   0.50    1.20    --  -86.25  45.00 -60.00   68
 37  \w    -37.00 -12.00   0.50    1.20    --  -86.25  30.00 -90.00   50
 38  \w    -37.00 -12.00   0.50    1.20    --  -86.25  30.00-150.00   50
 39  \w    -46.00 -15.00   0.50    1.20    --  -86.25  45.00-180.00   62
 40  \w    -46.00 -21.00   0.50    1.20    --  -86.25  45.00  30.00   50
 41  \w    -37.00 -11.00   0.50    1.20    --  -86.25  30.00  60.00   52
 42  \w    -41.00  26.00   0.50    0.30    --  -47.45  38.00 120.00  134
 43  \w    -37.00 -11.00   0.50    1.20    --  -86.25  30.00   0.00   52
 44  \w    -13.00  13.00   0.50    0.30    --  -47.45  19.00-180.00   52
;
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15471
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.470
_diffrn_reflns_theta_min         3.518
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.906
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
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    1.306
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         5207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0332P)^2^+0.6939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4566
_reflns_number_total             5207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00203e2.cif
_cod_data_source_block           ch_dp287_auto
_cod_database_code               1566420
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.832
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C2(H2), C18(H18), C14(H14), C17(H17), C15(H15)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C10(H10A,H10B,H10C), C5AA(H5AA,H5AB,
 H5AC), C22(H22A,H22B,H22C), C12(H12A,H12B,H12C), C24(H24A,H24B,H24C), C19(H19A,
 H19B,H19C)
;
_shelx_res_checksum              42115
_shelx_hkl_checksum              71922
_olex2_submission_special_instructions 'No special instructions were received'