Regiodivergent Lewis acid catalysis of bicyclo[1.1.0]butanes with 2-naphthols.
Fan, Lin; Wang, Pengyang; He, Chang; Chen, Xiaoyu; Dai, Linlong; Xiong, Daokai; Zhong, Guofu; Chemical science 16 (2025) 18255–18262; doi:10.1039/d5sc05468k

data_1575584
_publ_section_title
;
 Regiodivergent Lewis acid catalysis of bicyclo[1.1.0]butanes with
 2-naphthols.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              18255
_journal_page_last               18262
_journal_paper_doi               10.1039/d5sc05468k
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C24 H18 O3'
_chemical_formula_sum            'C24 H18 O3'
_chemical_formula_weight         354.38
_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             2025-08-14
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-08-18 deposited with the CCDC.	2025-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                103.8250(10)
_cell_angle_beta                 106.2590(10)
_cell_angle_gamma                106.7550(10)
_cell_formula_units_Z            2
_cell_length_a                   9.7775(2)
_cell_length_b                   9.8032(2)
_cell_length_c                   10.7751(2)
_cell_measurement_reflns_used    5849
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.213
_cell_measurement_theta_min      5.025
_cell_volume                     890.15(3)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9905
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         4.559
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.2106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1251 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.6581.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0542P)^2^+0.2006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2861
_reflns_number_total             3172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05468k2.cif
_cod_data_source_block           cu_nb_fl_cu_4y_0m
_cod_depositor_comments
'Adding full bibliography for 1575583--1575585.cif.'
_cod_database_code               1575584
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.915
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_res_checksum              80021
_olex2_submission_special_instructions 'No special instructions were received'