Cu(i)-catalyzed enantioselective and stereospecific borylative annulation of cyclic 1,3-dione-tethered 1,3-enynes.
Ramudu, G. Raghu; Patil, Vaibhav B.; Nanubolu, Jagadeesh Babu; Chegondi, Rambabu; Chemical science 16 (2025) 14988–14994; doi:10.1039/d5sc03007b

data_1575091
_publ_section_title
;
 Cu(i)-catalyzed enantioselective and stereospecific borylative annulation
 of cyclic 1,3-dione-tethered 1,3-enynes.
;
_journal_issue                   33
_journal_name_full               'Chemical science'
_journal_page_first              14988
_journal_page_last               14994
_journal_paper_doi               10.1039/d5sc03007b
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C29 H32 B Br O4'
_chemical_formula_sum            'C29 H32 B Br O4'
_chemical_formula_weight         535.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-04-14 deposited with the CCDC.	2025-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.661(2)
_cell_length_b                   19.722(5)
_cell_length_c                   20.481(5)
_cell_measurement_reflns_used    8684
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      19.934
_cell_measurement_theta_min      2.862
_cell_volume                     2690.6(12)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32534
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.868
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    1.560
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Isopropanol and Dichloromethane'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1055 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6169
_refine_ls_number_restraints     279
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0552P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3313
_reflns_number_total             6169
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03007b2.cif
_cod_data_source_block           KB1112_0m
_cod_depositor_comments
'Adding full bibliography for 1575090--1575091.cif.'
_cod_original_cell_volume        2690.4(13)
_cod_database_code               1575091
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.696
_shelx_estimated_absorpt_t_max   0.767
_shelx_res_checksum              47734