Synthesis of highly substituted 2-hydroxybenzophenones through skeletal clipping of 3-benzofuranones
Zhang, Chuan-Bao; Xu, Jiying; Wang, Xiao-Qing; Deng, Yi-Hang; Dou, Pei-Hao; Xu, Wen-Li; Han, Qiu-Xia; Zhao, Lili; Fu, Ji-Ya; Chemical Communications 61 (2025) 5645–5648; doi:10.1039/D5CC00396B

data_7134325
_publ_section_title
;
 Synthesis of highly substituted 2-hydroxybenzophenones through skeletal
 clipping of 3-benzofuranones
;
_journal_issue                   30
_journal_name_full               'Chemical Communications'
_journal_page_first              5645
_journal_page_last               5648
_journal_paper_doi               10.1039/D5CC00396B
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C28 H16 F2 N4 O2'
_chemical_formula_sum            'C28 H16 F2 N4 O2'
_chemical_formula_weight         478.45
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-08-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-12 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.719(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9992(9)
_cell_length_b                   11.0091(12)
_cell_length_c                   29.001(3)
_cell_measurement_reflns_used    1884
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.762
_cell_measurement_theta_min      2.629
_cell_volume                     2871.9(5)
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_reduction        'SAINT V8.18C (?, 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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14496
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.099
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         2.323
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              Microfocus
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0532 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.9238.
The \l/2 correction factor is 0.0015.
;
_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    1.107
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5097
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0682P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1498
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2607
_reflns_number_total             5097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00396b2.cif
_cod_data_source_block           mpt8752_0m
_cod_depositor_comments
'Adding full bibliography for 7134325--7134326.cif.'
_cod_database_code               7134325
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.968
_diffrn_source_source            'Incoatc Ius 3.0 '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid bond restraints
 F1, C22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C18, C21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C34, C27
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Rotating group:
 N1(H1A,H1B)
4.b Ternary CH refined with riding coordinates:
 C16(H16), C29(H29)
4.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C26(H26), C35(H35), C23(H23), C21(H21), C20(H20), C24(H24),
 C27(H27), C25(H25), C30(H30), C34(H34), C33(H33)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              75251
_shelx_hkl_checksum              34086
_shelx_fab_checksum              16221
_olex2_submission_special_instructions 'No special instructions were received'