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_7133613
_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         'C27 H23 Cl N2 O3, 0.25(H2 O)'
_chemical_formula_sum            'C27 H23.5 Cl N2 O3.25'
_chemical_formula_weight         463.43
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-10 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                76.612(2)
_cell_angle_beta                 83.712(2)
_cell_angle_gamma                82.660(2)
_cell_formula_units_Z            4
_cell_length_a                   9.2073(3)
_cell_length_b                   14.4300(5)
_cell_length_c                   18.0454(5)
_cell_measurement_reflns_used    8574
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.67
_cell_measurement_theta_min      3.166
_cell_volume                     2305.31(13)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29955
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.894
_diffrn_reflns_theta_min         2.526
_diffrn_source_current           0.95
_diffrn_source_power             0.0475
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.738
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1550 before and 0.0948 after correction.
The Ratio of minimum to maximum transmission is 0.1250.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             970
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     609
_refine_ls_number_reflns         9422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0781
_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^)+(0.1665P)^2^+0.0469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2103
_refine_ls_wR_factor_ref         0.2210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7910
_reflns_number_total             9422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03551h2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7133612--7133614.cif.'
_cod_original_cell_volume        2305.32(13)
_cod_original_formula_sum        'C27 H23.50 Cl N2 O3.25'
_cod_database_code               7133613
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.781
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H17A,H17B} of C17, {H35A,H35B} of C35
 At 1.5 times of:
  All C(H,H,H) groups, {H7A,H7B} of C55
2. Others
 Fixed Sof: O7(0.5) H7A(0.5) H7B(0.5)
3.a Riding coordinates:
 C26(H26A,H26B,H26C), C55(H7A,H7B)
3.b Ternary CH refined with riding coordinates:
 C15(H15), C47(H47)
3.c Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C35(H35A,H35B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C21(H21), C23(H23), C29(H29), C30(H30), C32(H32), C33(H33), C39(H39),
  C41(H41), C51(H51), C52(H52), C53(H53), C54(H54), C55(H55)
3.e Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C43(H43A,H43B,H43C), C45(H45A,H45B,
 H45C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              8807
_shelx_hkl_checksum              68025
_olex2_submission_special_instructions 'No special instructions were received'