Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles: synthesis of spiroheterocycles.
Dong, Yujie; Liu, Jun; Ning, Rongjin; Yang, Fazhou; Zhang, Cheng; Guo, Hongchao; Chemical communications (Cambridge, England) 60 (2024) 10516–10519; doi:10.1039/d4cc03551h

data_7133614
_publ_section_title
;
 Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2]
 cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles: synthesis
 of spiroheterocycles.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10516
_journal_page_last               10519
_journal_paper_doi               10.1039/d4cc03551h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C33 H26 Cl N3 O2'
_chemical_formula_sum            'C33 H26 Cl N3 O2'
_chemical_formula_weight         532.046
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-09-08 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.387(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1281(2)
_cell_length_b                   17.8377(2)
_cell_length_c                   13.6750(2)
_cell_measurement_reflns_used    9845
_cell_measurement_temperature    173
_cell_measurement_theta_max      75.7000
_cell_measurement_theta_min      4.1010
_cell_volume                     2651.29(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9786
_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    -62.00  28.00   1.00    2.22    --  -41.81  57.00   0.00   90
  2  \w   -114.00 -14.00   1.00    2.22    --  -41.81 -57.00-150.00  100
  3  \w     20.00 108.00   1.00    2.22    --   41.81  38.00 150.00   88
  4  \w      9.00  68.00   1.00    2.22    --   41.81 -99.00  60.00   59
  5  \w     34.00  92.00   1.00    2.22    --   41.81-125.00-120.00   58
  6  \w     27.00 173.00   1.00    8.70    --  110.95   0.00-150.00  146
  7  \w     48.00 100.00   1.00    8.70    --  110.95 -77.00-150.00   52
  8  \w    118.00 169.00   1.00    8.70    --  110.95  77.00  30.00   51
  9  \w    121.00 147.00   1.00    8.70    --  110.95 125.00-120.00   26
 10  \w     54.00 139.00   1.00    8.70    --  110.95 -30.00 -30.00   85
 11  \w     47.00 105.00   1.00    8.70    --  110.95 -95.00  90.00   58
 12  \w     81.00 108.00   1.00    8.70    --  110.95-107.00 -71.00   27
 13  \w     41.00 131.00   1.00    8.70    --  110.95 -45.00  90.00   90
 14  \w     80.00 106.00   1.00    8.70    --  110.95-125.00   0.00   26
 15  \w     38.00 123.00   1.00    8.70    --  110.95 -45.00-120.00   85
 16  \w     67.00 106.00   1.00    8.70    --  110.95 -95.00 150.00   39
 17  \w     32.00 108.00   1.00    8.70    --  110.95-105.00  43.92   76
;
_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      -0.0611381000
_diffrn_orient_matrix_UB_12      0.0774620000
_diffrn_orient_matrix_UB_13      0.0005928000
_diffrn_orient_matrix_UB_21      -0.1213882000
_diffrn_orient_matrix_UB_22      -0.0320907000
_diffrn_orient_matrix_UB_23      -0.0616074000
_diffrn_orient_matrix_UB_31      -0.0402640000
_diffrn_orient_matrix_UB_32      -0.0207286000
_diffrn_orient_matrix_UB_33      0.0975008000
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.9969
_diffrn_reflns_Laue_measured_fraction_max 0.9786
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18334
_diffrn_reflns_point_group_measured_fraction_full 0.9969
_diffrn_reflns_point_group_measured_fraction_max 0.9786
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         75.82
_diffrn_reflns_theta_min         4.07
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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    1.333
_exptl_crystal_description       prism
_exptl_crystal_F_000             1116.697
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.3971
_refine_diff_density_min         -0.4884
_refine_diff_density_rms         0.0690
_refine_ls_d_res_high            0.7951
_refine_ls_d_res_low             10.8690
_refine_ls_goodness_of_fit_ref   1.0494
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    49
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0494
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+1.1727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                4809
_reflns_number_total             5394
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc03551h2.cif
_cod_data_source_block           20230425ZengYuan-4_auto
_cod_depositor_comments
'Adding full bibliography for 7133612--7133614.cif.'
_cod_database_code               7133614
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C26(H26a,H26b), C25(H25a,H25b)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C5(H5), C6(H6), C29(H29), C33(H33), C20(H20), C30(H30), C14(H14),
 C22(H22), C3(H3), C23(H23), C32(H32), C31(H31), C21(H21), C10(H10), C2(H2),
 C13(H13), C12(H12), C11(H11)
;
_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 1.289
_oxdiff_exptl_absorpt_empirical_full_min 0.449