Photoswitchable and long-lived seven-membered cyclic singlet diradicals for the bioorthogonal photoclick reaction.
Hu, Fuqiang; Zhang, Cefei; Liu, Zhihao; Xie, Xinyu; Zhao, Xiaohu; Luo, Yanju; Fu, Jielin; Li, Baolin; Hu, Changwei; Su, Zhishan; Yu, Zhipeng; Chemical science 14 (2023) 13254–13264; doi:10.1039/d3sc03675h

data_1570242
_publ_section_title
;
 Photoswitchable and long-lived seven-membered cyclic singlet diradicals
 for the bioorthogonal photoclick reaction.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              13254
_journal_page_last               13264
_journal_paper_doi               10.1039/d3sc03675h
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H14 O3'
_chemical_formula_sum            'C22 H14 O3'
_chemical_formula_weight         326.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-03-07 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.607(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.4416(17)
_cell_length_b                   16.332(2)
_cell_length_c                   15.0321(19)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.26
_cell_volume                     3253.7(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            64736
_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         25.387
_diffrn_reflns_theta_min         2.552
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9508
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3, Hexane'
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.267
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0287P)^2^+1.1420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4819
_reflns_number_total             5977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03675h2.cif
_cod_data_source_block           yzp044
_cod_depositor_comments
;
Adding full bibliography for 1570241--1570242.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C44 H28 O6'
_cod_original_formula_weight         652.66
_cod_original_formula_moiety         '2(C22 H14 O3)'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1570242
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              64766
_shelx_hkl_checksum              41996