Intramolecular trapping of spiro radicals to produce unusual cyclization products from usual migration substrates
Zhang, Jingming; Liu, Chengkou; Qiao, Yaqi; Wei, Minghui; Guan, Wenjing; Mao, Ziren; Qin, Hong; Fang, Zheng; Guo, Kai; Chemical Science 14 (2023) 2461–2466; doi:10.1039/D2SC05768A

data_1568385
_publ_section_title
;
 Intramolecular trapping of spiro radicals to produce unusual cyclization
 products from usual migration substrates
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              2461
_journal_page_last               2466
_journal_paper_doi               10.1039/D2SC05768A
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C24 H21 F N2 O4'
_chemical_formula_sum            'C24 H21 F N2 O4'
_chemical_formula_weight         420.43
_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_date             2021-08-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_audit_update_record
;
2022-09-14 deposited with the CCDC.	2023-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.749(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8055(7)
_cell_length_b                   11.8006(9)
_cell_length_c                   19.3349(15)
_cell_measurement_reflns_used    6818
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      59.803
_cell_measurement_theta_min      3.980
_cell_volume                     2008.2(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15972
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.382
_diffrn_reflns_theta_min         3.980
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0920 before and 0.0695 after correction.
The Ratio of minimum to maximum transmission is 0.8118.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0644P)^2^+0.4797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3327
_reflns_number_total             4434
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05768a3.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 1568385.cif.'
_cod_database_code               1568385
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.938
_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
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C15(H15), C17(H17),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              70370
_shelx_hkl_checksum              57049
_olex2_submission_special_instructions 'No special instructions were received'