Silver-Catalyzed Three-Component Difunctionalization of Alkenes via Radical Pathways: Access to CF<sub>3</sub>-Functionalized Alkyl-Substituted 1,4-Naphthoquinone Derivatives.
Wang, Qijun; Wang, Bo; Deng, Hao; Shangguan, Yu; Lin, Yan; Zhang, Yaqi; Zhang, Zheming; Xiao, Yumei; Guo, Hongchao; Zhang, Cheng; The Journal of organic chemistry 84 (2019) 1006–1014; doi:10.1021/acs.joc.8b02997

data_4035964
_publ_section_title
;
 Silver-Catalyzed Three-Component Difunctionalization of Alkenes via
 Radical Pathways: Access to CF<sub>3</sub>-Functionalized
 Alkyl-Substituted 1,4-Naphthoquinone Derivatives.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1006
_journal_page_last               1014
_journal_paper_doi               10.1021/acs.joc.8b02997
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C26 H20 F3 N O2, C2 H3 N'
_chemical_formula_sum            'C28 H23 F3 N2 O2'
_chemical_formula_weight         476.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6805(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.6415(5)
_cell_length_b                   8.72785(14)
_cell_length_c                   18.2127(3)
_cell_measurement_reflns_used    5794
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7050
_cell_measurement_theta_min      2.4160
_cell_volume                     4711.41(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -59.00   1.00   1.00    1.03    --  -40.98  38.00 -90.00   60
  2  \w   -117.00  -7.00   1.00    1.03    --  -40.98 -19.00-120.00  110
  3  \w     24.00  49.00   1.00    1.03    --   40.98-125.00-180.00   25
  4  \w     36.00 103.00   1.00    1.50    --  107.58 -45.00 -90.00   67
  5  \w     79.00 108.00   1.00    1.50    --  107.58-125.00  30.00   29
  6  \w     39.00  65.00   1.00    1.50    --  107.58-125.00  30.00   26
  7  \w     39.00 128.00   1.00    1.50    --  107.58 -45.00  60.00   89
  8  \w    114.00 169.00   1.00    1.50    --  107.58  45.00-150.00   55
  9  \w     26.00 160.00   1.00    1.50    --  107.58 -15.00  30.00  134
 10  \w    111.00 177.00   1.00    1.50    --  107.58 125.00 150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0465746000
_diffrn_orient_matrix_UB_12      0.0783271000
_diffrn_orient_matrix_UB_13      -0.0007210000
_diffrn_orient_matrix_UB_21      -0.0114817000
_diffrn_orient_matrix_UB_22      -0.0795615000
_diffrn_orient_matrix_UB_23      0.0729387000
_diffrn_orient_matrix_UB_31      0.0200116000
_diffrn_orient_matrix_UB_32      0.1367308000
_diffrn_orient_matrix_UB_33      0.0428316000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9094
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.879
_diffrn_reflns_theta_min         2.982
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0994P)^2^+2.5459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1540
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4153
_reflns_number_total             4651
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02997_si_002.cif
_cod_data_source_block           exp_1272
_cod_original_cell_volume        4711.42(13)
_cod_database_code               4035964
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C6(H6), C25(H25), C3(H3), C5(H5), C21(H21), C12(H12),
 C4(H4), C22(H22), C13(H13), C24(H24), C15(H15), C14(H14)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.958
_oxdiff_exptl_absorpt_empirical_full_min 0.523