DABCO-catalyzed mono- and bisallylation of β,γ-unsaturated ketones with Morita–Baylis–Hillman carbonates
Yue, Guizhou; Du, Biao; Wang, Qiumi; Cheng, Silu; Ma, Lan; Lu, Cuifen; Feng, Juhua; Hu, Haipeng; Li, Sicheng; He, Qiao; New Journal of Chemistry 48 (2024) 15446–15451; doi:10.1039/D4NJ02086C

data_7063393
_publ_section_title
;
 DABCO-catalyzed mono- and bisallylation of \b,\g-unsaturated ketones with
 Morita--Baylis--Hillman carbonates
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15446
_journal_page_last               15451
_journal_paper_doi               10.1039/D4NJ02086C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C28 H25 Br O3'
_chemical_formula_sum            'C28 H25 Br O3'
_chemical_formula_weight         489.39
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-08
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2024-07-09 deposited with the CCDC.	2024-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.7710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9368(3)
_cell_length_b                   21.6415(6)
_cell_length_c                   10.4253(3)
_cell_measurement_reflns_used    9790
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      57.105
_cell_measurement_theta_min      3.977
_cell_volume                     2438.69(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30152
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.186
_diffrn_reflns_theta_min         3.977
_diffrn_source_current           2.86
_diffrn_source_power             0.1997996
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.646
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1014 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.7974.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0621P)^2^+1.3948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4529
_reflns_number_total             4984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02086c2.cif
_cod_data_source_block           lgz
_cod_depositor_comments          'Adding full bibliography for 7063393.cif.'
_cod_database_code               7063393
_shelx_shelxl_version_number     2019/1
_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:
 C6(H6), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d X=CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              65562
_olex2_submission_special_instructions 'No special instructions were received'