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_1575585
_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         'C27 H22 O2'
_chemical_formula_sum            'C27 H22 O2'
_chemical_formula_weight         378.44
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-14 deposited with the CCDC.	2025-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.006(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5568(10)
_cell_length_b                   22.582(4)
_cell_length_c                   13.2604(19)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.37
_cell_volume                     1960.7(5)
_computing_cell_refinement       'SAINT V8.41 (Bruker, 2024)'
_computing_data_collection       'APEX6 V2024.9-0 (Bruker, 2024)'
_computing_data_reduction        'SAINT V8.41 (Bruker, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      300.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            53355
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         2.370
_diffrn_source                   TXS
_diffrn_source_current           1.6
_diffrn_source_power             0.08
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1438 before and 0.0661 after correction.
The Ratio of minimum to maximum transmission is 0.9559.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0518P)^2^+0.4896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3429
_reflns_number_total             4494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05468k2.cif
_cod_data_source_block           mo_250112lu_lgpz0655399_2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1575583--1575585.cif.
;
_cod_database_code               1575585
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.990
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C13(H13), C23(H23), C3(H3), C17(H17), C14(H14), C27(H27), C5(H5),
 C16(H16), C2(H2), C15(H15), C24(H24), C1(H1A), C26(H26), C6(H6), C25(H25)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              23695
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU