Lewis acid-catalyzed diastereoselective carbofunctionalization of bicyclobutanes employing naphthols.
Guin, Avishek; Bhattacharjee, Subrata; Harariya, Mahesh Singh; Biju, Akkattu T.; Chemical science 14 (2023) 6585–6591; doi:10.1039/d3sc01373a

data_1569199
_publ_section_title
;
 Lewis acid-catalyzed diastereoselective carbofunctionalization of
 bicyclobutanes employing naphthols.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              6585
_journal_page_last               6591
_journal_paper_doi               10.1039/d3sc01373a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H19 Br O3'
_chemical_formula_sum            'C22 H19 Br O3'
_chemical_formula_weight         411.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-12-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-27 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.195(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6120(7)
_cell_length_b                   13.2639(8)
_cell_length_c                   13.3533(8)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.51
_cell_volume                     1822.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            54631
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.180
_diffrn_reflns_theta_min         3.207
_exptl_absorpt_coefficient_mu    2.275
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 3247 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         9374
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0284P)^2^+0.0754P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0688
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                8106
_reflns_number_total             9374
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01373a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 1569199.cif.'
_cod_database_code               1569199
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C13(H13), C35(H35)
1.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C34(H34A,H34B), C36(H36A,H36B)
1.c Me refined with riding coordinates:
 C22(H22A,H22B,H22C), C44(H44A,H44B,H44C)
1.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C25(H25), C26(H26), C29(H29), C31(H31), C32(H32), C38(H38),
  C39(H39), C40(H40), C41(H41), C42(H42)
;
_shelx_res_checksum              70151
_shelx_hkl_checksum              17389
_olex2_submission_special_instructions 'No special instructions were received'