A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for the synthesis of tetrasubstituted 2-pyrones
Wang, Yu-Hao; Zhang, De-Hua; Cao, Ze-Hun; Li, Wang-Lai; Huang, Yi-Yong; RSC Advances 11 (2021) 8867–8870; doi:10.1039/D0RA10686K

data_7242328
_publ_section_title
;
 A formal [3 + 3] cycloaddition of allenyl imide and activated ketones for
 the synthesis of tetrasubstituted 2-pyrones
;
_journal_issue                   15
_journal_name_full               'RSC Advances'
_journal_page_first              8867
_journal_page_last               8870
_journal_paper_doi               10.1039/D0RA10686K
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C16 H15 Br O4'
_chemical_formula_sum            'C16 H15 Br O4'
_chemical_formula_weight         351.18
_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             2019-09-29
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2020-09-14 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                86.131(2)
_cell_angle_beta                 89.164(2)
_cell_angle_gamma                89.851(2)
_cell_formula_units_Z            8
_cell_length_a                   7.9474(12)
_cell_length_b                   17.258(3)
_cell_length_c                   21.615(3)
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      29.66
_cell_measurement_theta_min      2.29
_cell_volume                     2957.6(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0939
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33017
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.463
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.792
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.3299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/3 (Bruker,2014/3)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.362
_refine_diff_density_min         -1.310
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     769
_refine_ls_number_reflns         10907
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.1649
_refine_ls_R_factor_gt           0.1220
_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^)+(0.0001P)^2^+43.7470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2111
_refine_ls_wR_factor_ref         0.2308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7891
_reflns_number_total             10907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra10686k2.cif
_cod_data_source_block           t
_cod_database_code               7242328
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.768
_shelx_estimated_absorpt_t_min   0.730
_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. Uiso/Uaniso restraints and constraints 
Uanis(C1B) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for 
terminal atoms of 0.02 
Uanis(C1C) \\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.005 and sigma for 
terminal atoms of 0.01 
3.a Secondary CH2 refined with riding coordinates: 
 C13(H13A,H13B), C13A(H13C,H13D), C13B(H13E,H13F), C13C(H13G,H13H) 
3.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C5(H5), C6(H6), C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), 
 C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B), C2C(H2C), C3C(H3C), C5C(H5C), C6C(H6C) 
3.c Idealised Me refined as rotating group: 
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C14A(H14D,H14E, 
 H14F), C15A(H15D,H15E,H15F), C16A(H16D,H16E,H16F), C14B(H14G,H14H,H14I), 
 C15B(H15G,H15H,H15I), C16B(H16G,H16H,H16I), C14C(H14J,H14K,H14L), C15C(H15J, 
 H15K,H15L), C16C(H16J,H16K,H16L) 
;
_shelx_res_checksum              82485
_olex2_submission_special_instructions 'No special instructions were received'