Visible-light-induced photocatalytic azotrifluoromethylation of alkenes with aryldiazonium salts and sodium triflinate
Xing-Long Yu; Jia-Rong Chen; Dong-Zhen Chen; Wen-Jing Xiao; Chem.Commun. 52 (2016) 8275–; doi:

data_7119655
_publ_section_title
;
 Visible-light-induced photocatalytic azotrifluoromethylation of alkenes
 with aryldiazonium salts and sodium triflinate
;
_journal_name_full               Chem.Commun.
_journal_page_first              8275
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C16 H14 F3 N3 O2'
_chemical_formula_sum            'C16 H14 F3 N3 O2'
_chemical_formula_weight         337.30
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-03-25 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.102(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.013(2)
_cell_length_b                   7.5562(16)
_cell_length_c                   21.159(5)
_cell_measurement_reflns_used    3909
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      2.73
_cell_volume                     1598.5(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 0.995
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12841
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.037
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1120 before and 0.0534 after correction.
The Ratio of minimum to maximum transmission is 0.8561.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0578
_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^)+(0.0762P)^2^+0.6387P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.1835
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2429
_reflns_number_total             3610
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc03335k2.cif
_cod_data_source_block           mo_151111_0m
_cod_database_code               7119655
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
;
_shelx_res_checksum              89190
_shelx_hkl_checksum              96365
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'