Visible-Light-Induced Atom Transfer Radical Addition and Cyclization of Perfluoroalkyl Halides with 1,n-Enynes
Wang, Shuo-Wen; Yu, Jian; Zhou, Qin-Yi; Chen, Si-Yu; Xu, Zhen-Hua; Tang, Shi; ACS Sustainable Chemistry & Engineering 7 (2019) 10154–; doi:10.1021/acssuschemeng.9b02178

data_4515223
_publ_section_title
;
 Visible-Light-Induced Atom Transfer Radical Addition and Cyclization of
 Perfluoroalkyl Halides with 1,n-Enynes
;
_journal_issue                   11
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_page_first              10154
_journal_paper_doi               10.1021/acssuschemeng.9b02178
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         '2(C23 H17 F9 I N O)'
_chemical_formula_sum            'C46 H34 F18 I2 N2 O2'
_chemical_formula_weight         1242.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                89.5500(10)
_cell_angle_beta                 78.0930(10)
_cell_angle_gamma                81.195(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6843(5)
_cell_length_b                   15.0889(7)
_cell_length_c                   16.5780(8)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    153
_cell_measurement_theta_max      27.506
_cell_measurement_theta_min      2.491
_cell_volume                     2341.7(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20923
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         2.275
_exptl_absorpt_coefficient_mu    1.455
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1022 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.5468. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.830
_refine_diff_density_min         -0.834
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         10697
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+2.0493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8880
_reflns_number_total             10697
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc9b02178_si_002.cif
_cod_data_source_block           a
_cod_database_code               4515223
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.760
_shelx_estimated_absorpt_t_min   0.712
_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. Restrained distances
 F14-C22 \\sim F14A-C22
 with sigma of 0.02
3. Others
 Sof(F14A)=1-FVAR(1)
 Sof(F14)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C42(H42A,H42B)
4.b Aromatic/amide H refined with riding coordinates:
 C37(H37), C12(H12), C10(H10), C11(H11), C36(H36), C6(H6), C13(H13), C2(H2),
 C34(H34), C35(H35), C25(H25), C29(H29), C5(H5), C3(H3), C4(H4), C26(H26),
 C27(H27), C28(H28)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C41(H41A,H41B,H41C), C15(H15A,H15B,H15C), C38(H38A,H38B,
 H38C)
;
_shelx_res_checksum              21897
_shelx_hkl_checksum              30976
_olex2_submission_special_instructions 'No special instructions were received'