Photoinduced [4 + 2]-cycloaddition reactions of vinyldiazo compounds for the construction of heterocyclic and bicyclic rings.
Bao, Ming; Bohórquez, Arnold R Romero; Arman, Hadi; Doyle, Michael P.; Chemical science 15 (2024) 12042–12046; doi:10.1039/d4sc03558e

data_1572015
_publ_section_title
;
 Photoinduced [4 + 2]-cycloaddition reactions of vinyldiazo compounds for
 the construction of heterocyclic and bicyclic rings.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              12042
_journal_page_last               12046
_journal_paper_doi               10.1039/d4sc03558e
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C35 H41 N3 O4 Si'
_chemical_formula_sum            'C35 H41 N3 O4 Si'
_chemical_formula_weight         595.80
_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     dual
_audit_creation_date             2024-04-03
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-04-05 deposited with the CCDC.	2024-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.5720(10)
_cell_angle_beta                 92.7850(10)
_cell_angle_gamma                107.3760(10)
_cell_formula_units_Z            4
_cell_length_a                   14.0714(2)
_cell_length_b                   14.8588(2)
_cell_length_c                   16.3784(2)
_cell_measurement_reflns_used    23130
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9960
_cell_measurement_theta_min      4.1390
_cell_volume                     3263.25(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_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   -122.00 -30.00   0.50    0.42    --  -46.65 -16.00  72.00  184
  2  \w     30.00 123.00   0.50    0.42    --   46.65  16.00-118.00  186
  3  \w    -28.00  29.00   0.50    0.42    --   46.65 -16.00  72.00  114
  4  \w   -167.00 -75.00   0.50    1.66    --  -91.75 -16.00  72.00  184
  5  \w     90.00 178.00   0.50    1.66    --  106.91  16.00-118.00  176
  6  \w   -118.00 -83.00   0.50    0.42    --  -46.65 -57.00 120.00   70
  7  \w    -29.00  30.00   0.50    0.42    --  -46.65  16.00-118.00  118
  8  \w   -118.00 -83.00   0.50    0.42    --  -46.65 -57.00   0.00   70
  9  \w    -30.00  29.00   0.50    0.42    --  -46.65  19.00 -60.00  118
 10  \w    -86.00 -13.00   0.50    0.42    --  -46.65 125.00-120.00  146
 11  \w     83.00 120.00   0.50    0.42    --   46.65  57.00   0.00   74
 12  \w    -25.00  63.00   0.50    0.42    --   46.65 -57.00  60.00  176
 13  \w     34.00  93.00   0.50    0.42    --   46.65-125.00 120.00  118
 14  \w    -51.00 -19.00   0.50    1.66    --  -91.75  45.00-150.00   64
 15  \w    -51.00 -19.00   0.50    1.66    --  -91.75  45.00  60.00   64
 16  \w   -164.00-100.00   0.50    1.66    --  -91.75 -94.00 150.00  128
 17  \w    -51.00 -19.00   0.50    1.66    --  -91.75  45.00-180.00   64
 18  \w    -51.00 -19.00   0.50    1.66    --  -91.75  45.00-120.00   64
 19  \w   -164.00 -90.00   0.50    1.66    --  -91.75 -60.00-110.28  148
 20  \w   -164.00-101.00   0.50    1.66    --  -91.75 -77.00-180.00  126
 21  \w   -162.00 -87.00   0.50    1.66    --  -91.75-125.00-180.00  150
 22  \w   -101.00 -19.00   0.50    1.66    --  -91.75  77.00  30.00  164
 23  \w   -164.00-101.00   0.50    1.66    --  -91.75 -77.00-150.00  126
 24  \w   -164.00-100.00   0.50    1.66    --  -91.75 -94.00  60.00  128
 25  \w    -85.00 -22.00   0.50    1.66    --  -91.75 125.00 -60.00  126
 26  \w    -71.00 -19.00   0.50    1.66    --  -91.75  61.00 120.00  104
 27  \w     34.00  71.00   0.50    1.66    --  106.91 -61.00 120.00   74
 28  \w     37.00 112.00   0.50    1.66    --  106.91-125.00  60.00  150
 29  \w     37.00 112.00   0.50    1.66    --  106.91-125.00 120.00  150
 30  \w     37.00 112.00   0.50    1.66    --  106.91-125.00  30.00  150
 31  \w     34.00 106.00   0.50    1.66    --  106.91 -94.00-120.00  144
 32  \w     34.00 106.00   0.50    1.66    --  106.91 -94.00 150.00  144
 33  \w     34.00  71.00   0.50    1.66    --  106.91 -61.00  60.00   74
 34  \w     37.00 112.00   0.50    1.66    --  106.91-125.00-180.00  150
 35  \w     38.00 108.00   0.50    1.66    --  106.91-111.00 -62.55  140
 36  \w     34.00 106.00   0.50    1.66    --  106.91 -94.00-180.00  144
 37  \w     37.00 112.00   0.50    1.66    --  106.91-125.00 -30.00  150
 38  \w     34.00  71.00   0.50    1.66    --  106.91 -61.00-120.00   74
 39  \w     34.00 106.00   0.50    1.66    --  106.91 -94.00  30.00  144
 40  \w     34.00  71.00   0.50    1.66    --  106.91 -61.00-150.00   74
 41  \w     39.00 119.00   0.50    1.66    --  106.91-134.00 -95.97  160
 42  \w     92.00 178.00   0.50    1.66    --  106.91  30.00 -30.00  172
 43  \w     34.00  71.00   0.50    1.66    --  106.91 -61.00  30.00   74
 44  \w     34.00 106.00   0.50    1.66    --  106.91 -94.00  90.00  144
 45  \w   -118.00 -31.00   0.50    0.42    --  -46.65 -55.00  26.88  174
 46  \w     31.00 120.00   0.50    0.42    --   46.65  55.00 158.42  178
 47  \w     31.00 120.00   0.50    0.42    --   46.65  54.00  -6.07  178
 48  \w     31.00 120.00   0.50    0.42    --   46.65  55.00-134.99  178
 49  \w     31.00 120.00   0.50    0.42    --   46.65  55.00 115.64  178
 50  \w     31.00 120.00   0.50    0.42    --   46.65  53.00 -74.43  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0591211000
_diffrn_orient_matrix_UB_12      -0.1024211000
_diffrn_orient_matrix_UB_13      0.0181468000
_diffrn_orient_matrix_UB_21      0.0950006000
_diffrn_orient_matrix_UB_22      -0.0299968000
_diffrn_orient_matrix_UB_23      -0.0077993000
_diffrn_orient_matrix_UB_31      0.0260408000
_diffrn_orient_matrix_UB_32      0.0204948000
_diffrn_orient_matrix_UB_33      0.0921092000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23211
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.829
_diffrn_reflns_theta_min         2.702
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.966
_exptl_absorpt_correction_T_max  0.117
_exptl_absorpt_correction_T_min  0.007
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       plate
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.900
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     788
_refine_ls_number_reflns         23211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0300P)^2^+3.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20241
_reflns_number_total             23211
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.5296\% 
around [-0.00 -0.00 1.00] (reciprocal) or [0.06 0.03 1.00] (direct)
;
_cod_data_source_file            d4sc03558e2.cif
_cod_data_source_block           hpd873_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 1572014--1572015.cif.'
_cod_database_code               1572015
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Si'
_chemical_oxdiff_usercomment     627
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5668(7)
 0.4332(7)
2. 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
3.a Ternary CH refined with riding coordinates:
 C4(H4), C39(H39)
3.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C2(H2A,H2B), C55(H55A,H55B), C56(H56A,H56B), C20(H20A,H20B),
 C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C64(H64), C18(H18), C53(H53), C43(H43), C29(H29), C47(H47), C8(H8),
 C44(H44), C12(H12), C16(H16), C45(H45), C23(H23), C17(H17), C50(H50), C9(H9),
 C27(H27), C62(H62), C49(H49), C58(H58), C15(H15), C10(H10), C46(H46), C61(H61),
  C60(H60), C51(H51), C52(H52), C24(H24), C26(H26), C11(H11), C25(H25), C59(H59)
3.d Idealised Me refined as rotating group:
 C63(H63A,H63B,H63C), C68(H68A,H68B,H68C), C28(H28A,H28B,H28C), C33(H33A,H33B,
 H33C), C70(H70A,H70B,H70C), C69(H69A,H69B,H69C), C34(H34A,H34B,H34C), C31(H31A,
 H31B,H31C), C66(H66A,H66B,H66C), C30(H30A,H30B,H30C), C35(H35A,H35B,H35C),
 C65(H65A,H65B,H65C)
;
_shelx_res_checksum              80279
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 2.083
_oxdiff_exptl_absorpt_empirical_full_min 0.472
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2