C(sp<sup>2</sup>)-H cyclobutylation of hydroxyarenes enabled by silver-π-acid catalysis: diastereocontrolled synthesis of 1,3-difunctionalized cyclobutanes.
Tang, Lei; Huang, Qi-Nan; Wu, Feng; Xiao, Yuanjiu; Zhou, Jin-Lan; Xu, Tong-Tong; Wu, Wen-Biao; Qu, Shuanglin; Feng, Jian-Jun; Chemical science 14 (2023) 9696–9703; doi:10.1039/d3sc03258b

data_1569755
_publ_section_title
;
 C(sp<sup>2</sup>)-H cyclobutylation of hydroxyarenes enabled by
 silver-&#x3c0;-acid catalysis: diastereocontrolled synthesis of
 1,3-difunctionalized cyclobutanes.
;
_journal_issue                   36
_journal_name_full               'Chemical science'
_journal_page_first              9696
_journal_page_last               9703
_journal_paper_doi               10.1039/d3sc03258b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C28 H24 O3'
_chemical_formula_sum            'C28 H24 O3'
_chemical_formula_weight         408.47
_chemical_name_systematic
'methyl 3-(2-hydroxy-7-phenylnaphthalen-1-yl)-3-phenylcyclobutane-1-carboxylate'
_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             2022-10-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-05-15 deposited with the CCDC.	2023-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                74.896(6)
_cell_angle_beta                 74.919(6)
_cell_angle_gamma                77.645(6)
_cell_formula_units_Z            2
_cell_length_a                   9.7676(15)
_cell_length_b                   10.6234(16)
_cell_length_c                   12.9739(16)
_cell_measurement_reflns_used    747
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      23.73
_cell_measurement_theta_min      2.73
_cell_volume                     1239.4(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0422
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27581
_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         28.304
_diffrn_reflns_theta_min         2.186
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6786
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_preparation       CH2Cl2
_exptl_crystal_recrystallization_method CH2Cl2
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         6151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0945P)^2^+0.6822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4807
_reflns_number_total             6151
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03258b2.cif
_cod_data_source_block           p-1
_cod_depositor_comments          'Adding full bibliography for 1569755.cif.'
_cod_database_code               1569755
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.983
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C23(H23), C1(H1A), C11(H11), C8(H8), C12(H12), C5(H5), C9(H9),
 C19(H19), C22(H22), C2(H2), C20(H20), C4(H4), C3(H3), C21(H21)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              36182
_shelx_fab_checksum              34350
_olex2_submission_special_instructions 'No special instructions were received'