BBr<sub>3</sub>-mediated dearomative spirocyclization of biaryl ynones: facile access to spiro[5.5]dienones.
Jaiswal, Gaurav; Pan, Subhas Chandra; Organic & biomolecular chemistry 22 (2024) 3602–3605; doi:10.1039/d4ob00274a

data_7159905
_publ_section_title
;
 BBr<sub>3</sub>-mediated dearomative spirocyclization of biaryl ynones:
 facile access to spiro[5.5]dienones.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3602
_journal_page_last               3605
_journal_paper_doi               10.1039/d4ob00274a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C25 H15 Cl O2'
_chemical_formula_sum            'C25 H15 Cl O2'
_chemical_formula_weight         382.82
_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
_audit_creation_date             2023-09-04
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2024-02-08 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.373(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.591(10)
_cell_length_b                   7.190(4)
_cell_length_c                   15.695(9)
_cell_measurement_reflns_used    9404
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      2.81
_cell_volume                     1869.0(19)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0399
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31619
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.322
_diffrn_reflns_theta_min         2.459
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0280P)^2^+0.9323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3032
_reflns_number_total             3785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00274a2.cif
_cod_data_source_block           scp_a
_cod_depositor_comments          'Adding full bibliography for 7159905.cif.'
_cod_original_cell_volume        1868.9(19)
_cod_database_code               7159905
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C4(H4), C25(H25), C18(H18), C12(H12), C21(H21), C1(H1),
 C13(H13), C24(H24), C8(H8), C23(H23), C3(H3), C22(H22), C2(H2)
;
_shelx_res_checksum              65065
_shelx_hkl_checksum              46811
_olex2_submission_special_instructions 'No special instructions were received'