Visible light-promoted [3+2] cyclization reaction of vinyl azides with perfluoroalkyl-substituted-imidoyl sulfoxonium ylides.
Yang, Ming; Meng, Yu-Xuan; Mehfooz, Haroon; Zhao, Yu-Long; Chemical communications (Cambridge, England) 60 (2024) 5407–5410; doi:10.1039/d4cc00777h

data_7132964
_publ_section_title
;
 Visible light-promoted [3+2] cyclization reaction of vinyl azides with
 perfluoroalkyl-substituted-imidoyl sulfoxonium ylides.
;
_journal_issue                   41
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5407
_journal_page_last               5410
_journal_paper_doi               10.1039/d4cc00777h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C19 H19 F3 N2'
_chemical_formula_sum            'C19 H19 F3 N2'
_chemical_formula_weight         332.36
_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     dual
_audit_creation_date             2023-11-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2023-11-08 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.938(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.340(3)
_cell_length_b                   15.240(5)
_cell_length_c                   11.008(3)
_cell_measurement_reflns_used    6176
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      63.71
_cell_measurement_theta_min      4.29
_cell_volume                     1728.2(9)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14443
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        64.159
_diffrn_reflns_theta_max         64.159
_diffrn_reflns_theta_min         4.291
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0720
_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^)+(0.1223P)^2^+0.7770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.2260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1996
_reflns_number_total             2887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00777h2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7132964.cif.'
_cod_database_code               7132964
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.886
_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:
 C00B(H00A,H00B), C00G(H00E,H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00D(H00D), C00F(H00F), C00I(H00I), C00J(H00J),
 C00K(H00K), C00M(H00M)
2.c Idealised Me refined as rotating group:
 C00N(H00H,H00L,H00N), C00O(H00O,H00P,H00Q)
;
_shelx_res_checksum              23691
_shelx_hkl_checksum              9670
_olex2_submission_special_instructions 'No special instructions were received'