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_1572014
_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         'C26 H35 N O3 Si'
_chemical_formula_sum            'C26 H35 N O3 Si'
_chemical_formula_weight         437.64
_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             2024-02-14
_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                84.659(2)
_cell_angle_beta                 88.405(2)
_cell_angle_gamma                83.737(2)
_cell_formula_units_Z            2
_cell_length_a                   6.03320(10)
_cell_length_b                   11.3990(3)
_cell_length_c                   17.7451(3)
_cell_measurement_reflns_used    13988
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.5250
_cell_measurement_theta_min      2.4880
_cell_volume                     1207.63(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.939
_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    -51.00 -19.00   0.50    0.23    --  -91.75  45.00 -60.00   64
  2  \w    -71.00 -19.00   0.50    0.23    --  -91.75  61.00 -60.00  104
  3  \w    -71.00 -19.00   0.50    0.23    --  -91.75  61.00-150.00  104
  4  \w    -71.00 -19.00   0.50    0.23    --  -91.75  61.00-180.00  104
  5  \w    -51.00 -19.00   0.50    0.23    --  -91.75  45.00-180.00   64
  6  \w    -51.00 -19.00   0.50    0.23    --  -91.75  45.00 -30.00   64
  7  \w    -51.00 -19.00   0.50    0.23    --  -91.75  45.00   0.00   64
  8  \w    -51.00 -19.00   0.50    0.23    --  -91.75  45.00  30.00   64
  9  \w    -85.00 -22.00   0.50    0.23    --  -91.75 125.00 -30.00  126
 10  \w   -119.00 -83.00   0.50    0.06    --  -46.90 -57.00-150.00   72
 11  \w   -119.00 -83.00   0.50    0.06    --  -46.90 -57.00-180.00   72
 12  \w    -80.00 -19.00   0.50    0.23    --  -91.75  95.00-129.00  122
 13  \w    -79.00  26.00   0.50    0.06    --  -46.90  95.00-129.00  210
 14  \w   -119.00 -83.00   0.50    0.06    --  -46.90 -57.00  90.00   72
 15  \w   -164.00-101.00   0.50    0.23    --  -91.75 -77.00 150.00  126
 16  \w   -164.00-101.00   0.50    0.23    --  -91.75 -77.00  90.00  126
 17  \w   -164.00-101.00   0.50    0.23    --  -91.75 -77.00-180.00  126
 18  \w   -164.00 -86.00   0.50    0.23    --  -91.75 -58.00-155.85  156
 19  \w   -164.00-100.00   0.50    0.23    --  -91.75 -94.00 -90.00  128
 20  \w   -164.00-100.00   0.50    0.23    --  -91.75 -94.00-120.00  128
 21  \w   -164.00 -83.00   0.50    0.23    --  -91.75 -95.00 120.00  162
 22  \w     32.00 119.00   0.50    0.06    --   46.90  54.00-171.48  174
 23  \w     83.00 119.00   0.50    0.06    --   46.90  57.00 -90.00   72
 24  \w     32.00 119.00   0.50    0.06    --   46.90  52.00-122.86  174
 25  \w     32.00 109.00   0.50    0.06    --   46.90  49.00 -66.17  154
 26  \w     31.00 119.00   0.50    0.06    --   46.90  55.00  96.75  176
 27  \w     32.00 119.00   0.50    0.06    --   46.90  53.00   0.59  174
 28  \w    -28.00  30.00   0.50    0.06    --   46.90 -19.00 120.00  116
 29  \w     34.00 101.00   0.50    0.23    --  106.91 -77.00  60.00  134
 30  \w     93.00 178.00   0.50    0.23    --  106.91  45.00 150.00  170
 31  \w    105.00 178.00   0.50    0.23    --  106.91  95.00-129.00  146
 32  \w    -28.00  30.00   0.50    0.06    --   46.90 -19.00-150.00  116
 33  \w    -27.00  43.00   0.50    0.06    --   46.90 -37.00-150.00  140
 34  \w     34.00  94.00   0.50    0.06    --   46.90-125.00-180.00  120
 35  \w     37.00 112.00   0.50    0.23    --  106.91-125.00-180.00  150
 36  \w     37.00 112.00   0.50    0.23    --  106.91-125.00 -90.00  150
 37  \w     34.00 106.00   0.50    0.23    --  106.91 -94.00-180.00  144
 38  \w     36.00 107.00   0.50    0.23    --  106.91-105.00 -38.48  142
 39  \w     34.00 106.00   0.50    0.23    --  106.91 -94.00 -30.00  144
 40  \w     37.00 112.00   0.50    0.23    --  106.91-125.00  90.00  150
 41  \w     34.00 105.00   0.50    0.23    --  106.91 -95.00 120.00  142
 42  \w     -9.00  79.00   0.50    0.06    --   46.90 -95.00 120.00  176
;
_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      0.0718354000
_diffrn_orient_matrix_UB_12      -0.0263460000
_diffrn_orient_matrix_UB_13      -0.0812330000
_diffrn_orient_matrix_UB_21      -0.1381141000
_diffrn_orient_matrix_UB_22      -0.1065897000
_diffrn_orient_matrix_UB_23      0.0065764000
_diffrn_orient_matrix_UB_31      -0.2043851000
_diffrn_orient_matrix_UB_32      0.0811339000
_diffrn_orient_matrix_UB_33      -0.0310365000
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22726
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.687
_diffrn_reflns_theta_min         2.501
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.062
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.796
_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    1.204
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0481P)^2^+0.5289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4388
_reflns_number_total             4794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03558e2.cif
_cod_data_source_block           hpd842_auto
_cod_depositor_comments
'Adding full bibliography for 1572014--1572015.cif.'
_cod_database_code               1572014
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Si'
_chemical_oxdiff_usercomment     784
_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:
 C7(H7), C5(H5), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C19(H19), C18(H18), C3(H3), C4(H4), C25(H25), C21(H21), C24(H24),
 C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C13(H13A,H13B,
 H13C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              8526
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.824