4-Vinylbenzodioxinones as a new type of precursor for palladium-catalyzed (4+3) cycloaddition of azomethine imines.
Tang, Yi; Zhang, Rulei; Dong, Yujie; Yu, Songcheng; Wu, Yongjun; Xiao, Yumei; Guo, Hongchao; Chemical communications (Cambridge, England) 60 (2024) 1436–1439; doi:10.1039/d3cc06012h

data_7132592
_publ_section_title
;
 4-Vinylbenzodioxinones as a new type of precursor for palladium-catalyzed
 (4+3) cycloaddition of azomethine imines.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1436
_journal_page_last               1439
_journal_paper_doi               10.1039/d3cc06012h
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C26 H25 N3 O4 S'
_chemical_formula_sum            'C26 H25 N3 O4 S'
_chemical_formula_weight         475.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-24
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-04 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.53610(10)
_cell_length_b                   17.8100(2)
_cell_length_c                   26.2442(3)
_cell_measurement_reflns_used    54605
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.4660
_cell_measurement_theta_min      2.9570
_cell_volume                     4924.67(9)
_computing_cell_refinement       'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_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 0.995
_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     25.00 122.00   0.50    0.05    --   48.93  77.00-150.00  194
  2  \w     25.00 122.00   0.50    0.05    --   48.93  77.00 -90.00  194
  3  \w     25.00 122.00   0.50    0.05    --   48.93  77.00 -30.00  194
  4  \w     25.00 122.00   0.50    0.05    --   48.93  77.00  30.00  194
  5  \w     25.00 122.00   0.50    0.05    --   48.93  77.00  90.00  194
  6  \w     25.00 122.00   0.50    0.05    --   48.93  77.00 150.00  194
  7  \w     34.00 124.00   0.50    0.05    --   48.93  19.00  30.00  180
  8  \w     34.00 124.00   0.50    0.05    --   48.93  19.00  30.00  180
  9  \w     33.00 122.00   0.50    0.05    --   48.93  57.00  60.00  178
 10  \w     91.00 178.00   0.50    0.50    --  108.01  61.00  60.00  174
 11  \w     93.00 178.00   0.50    0.50    --  108.01  30.00  30.00  170
 12  \w     94.00 178.00   0.50    0.50    --  108.01  45.00-150.00  168
 13  \w     93.00 178.00   0.50    0.50    --  108.01  30.00 -60.00  170
 14  \w     91.00 178.00   0.50    0.50    --  108.01  61.00 -30.00  174
 15  \w     35.00  71.00   0.50    0.50    --  108.01 -61.00  90.00   72
 16  \w     38.00 112.00   0.50    0.50    --  108.01-125.00  30.00  148
 17  \w     35.00 105.00   0.50    0.50    --  108.01 -77.00   0.00  140
 18  \w     35.00  71.00   0.50    0.50    --  108.01 -61.00   0.00   72
 19  \w     38.00 112.00   0.50    0.50    --  108.01-125.00   0.00  148
 20  \w     13.00  96.00   0.50    0.05    --   48.93-125.00-150.00  166
 21  \w     38.00 112.00   0.50    0.50    --  108.01-125.00 -90.00  148
 22  \w     35.00 105.00   0.50    0.50    --  108.01 -95.00 -90.00  140
 23  \w     35.00 105.00   0.50    0.50    --  108.01 -95.00   0.00  140
 24  \w     35.00 105.00   0.50    0.50    --  108.01 -95.00 150.00  140
 25  \w    -23.00  65.00   0.50    0.05    --   48.93 -57.00  30.00  176
 26  \w    -25.00  43.00   0.50    0.05    --   48.93 -38.00 150.00  136
 27  \w    -26.00  26.00   0.50    0.05    --   48.93 -19.00  60.00  104
 28  \w    -26.00  26.00   0.50    0.05    --   48.93 -19.00  30.00  104
 29  \w    -25.00  43.00   0.50    0.05    --   48.93 -38.00 -90.00  136
 30  \w   -177.00 -89.00   0.50    0.50    -- -105.51 -54.00-122.94  176
 31  \w   -177.00 -89.00   0.50    0.50    -- -105.51 -58.00 -98.13  176
 32  \w   -177.00-134.00   0.50    0.50    -- -105.51 -63.00 118.59   86
 33  \w   -177.00 -80.00   0.50    0.50    -- -105.51 -81.00 160.59  194
 34  \w   -177.00 -88.00   0.50    0.50    -- -105.51 -62.00 174.73  178
 35  \w    -71.00 -32.00   0.50    0.50    -- -105.51  61.00  90.00   78
 36  \w    -71.00 -32.00   0.50    0.50    -- -105.51  61.00 -60.00   78
 37  \w    -93.00 -13.00   0.50    0.05    --  -46.43 125.00-150.00  160
 38  \w   -122.00 -32.00   0.50    0.50    -- -105.51 139.00  51.40  180
 39  \w   -128.00 -32.00   0.50    0.50    -- -105.51 148.00  18.40  192
 40  \w   -123.00 -32.00   0.50    0.50    -- -105.51 141.00 102.22  182
 41  \w   -123.00 -32.00   0.50    0.50    -- -105.51 141.00 102.22  182
 42  \w   -122.00 -32.00   0.50    0.50    -- -105.51 139.00 146.29  180
 43  \w   -122.00 -32.00   0.50    0.50    -- -105.51 139.00 146.29  180
 44  \w   -111.00 -35.00   0.50    0.50    -- -105.51 125.00 -90.00  152
 45  \w    -30.00  -5.00   0.50    0.05    --  -46.49  35.00  45.00   50
 46  \w   -113.00 -88.00   0.50    0.50    -- -105.44 -61.00 124.43   50
 47  \w   -119.00 -31.00   0.50    0.05    --  -46.49 -44.00-148.92  176
 48  \w   -120.00 -32.00   0.50    0.05    --  -46.49 -38.00 120.00  176
 49  \w   -120.00 -32.00   0.50    0.05    --  -46.49 -38.00 -90.00  176
 50  \w   -120.00 -32.00   0.50    0.05    --  -46.49 -38.00   0.00  176
 51  \w   -120.00 -32.00   0.50    0.05    --  -46.49 -38.00-150.00  176
 52  \w     25.00 122.00   0.50    0.05    --   48.99  77.00 120.00  194
 53  \w     25.00 122.00   0.50    0.05    --   48.99  77.00 -60.00  194
 54  \w     33.00 122.00   0.50    0.05    --   48.99  57.00 -60.00  178
 55  \w     25.00 122.00   0.50    0.05    --   48.99  77.00  60.00  194
 56  \w     25.00 122.00   0.50    0.05    --   48.99  77.00-120.00  194
 57  \w     25.00 122.00   0.50    0.05    --   48.99  77.00   0.00  194
 58  \w     25.00 122.00   0.50    0.05    --   48.99  77.00-180.00  194
 59  \w   -177.00-121.00   0.50    0.50    -- -105.44 -67.00-152.31  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0547397000
_diffrn_orient_matrix_UB_12      -0.0196469000
_diffrn_orient_matrix_UB_13      0.0527600000
_diffrn_orient_matrix_UB_21      0.0358789000
_diffrn_orient_matrix_UB_22      -0.0829746000
_diffrn_orient_matrix_UB_23      -0.0082040000
_diffrn_orient_matrix_UB_31      0.1307678000
_diffrn_orient_matrix_UB_32      0.0145071000
_diffrn_orient_matrix_UB_33      0.0243823000
_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  0.0684
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            148366
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.756
_diffrn_reflns_theta_min         3.368
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.472
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 3181 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         10285
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0778P)^2^+0.3721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                8298
_reflns_number_total             10285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06012h2.cif
_cod_data_source_block           9052_auto
_cod_depositor_comments
'Adding full bibliography for 7132590--7132592.cif.'
_cod_database_code               7132592
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         chon
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.809
_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. Restrained distances
 C25-C43
 1.2 with sigma of 0.02
 C51-C49
 1.15 with sigma of 0.002
3. Rigid bond restraints
 C51, C49
 with sigma for 1-2 distances of 0.0008 and sigma for 1-3 distances of 0.0004
4. Uiso/Uaniso restraints and constraints
Uanis(C51) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
5.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14), C32(H32), C37(H37)
5.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C45(H45A,H45B)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C28(H28), C36(H36), C40(H40), C42(H42), C44(H44), C46(H46), C48(H48),
 C50(H50), C52(H52), C13(H13), C27(H27), C7(H7), C29(H29), C31(H31), C2(H2),
 C17(H17), C35(H35), C9(H9), C19(H19), C39(H39), C5(H5), C21(H21), C43(H43),
 C11(H11), C49(H49)
5.d X=CH2 refined with riding coordinates:
 C25(H25A,H25B), C51(H51A,H51B)
5.e Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C23(H23A,H23B,H23C), C47(H47A,H47B,H47C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              29798
_shelx_hkl_checksum              84270
_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 1.442
_oxdiff_exptl_absorpt_empirical_full_min 0.532