Palladium-Catalyzed Fluoroalkylative Cyclization of Olefins.
Liao, Jianhua; Fan, Lianfeng; Guo, Wei; Zhang, Zhenming; Li, Jiawei; Zhu, Chuanle; Ren, Yanwei; Wu, Wanqing; Jiang, Huanfeng; Organic letters 19 (2017) 1008–1011; doi:10.1021/acs.orglett.6b03865

data_1545436
_publ_section_title
;
 Palladium-Catalyzed Fluoroalkylative Cyclization of Olefins.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1008
_journal_page_last               1011
_journal_paper_doi               10.1021/acs.orglett.6b03865
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C13 H13 F2 N O5'
_chemical_formula_sum            'C13 H13 F2 N O5'
_chemical_formula_weight         301.24
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                81.350(4)
_cell_angle_beta                 80.175(4)
_cell_angle_gamma                82.598(4)
_cell_formula_units_Z            2
_cell_length_a                   5.5051(3)
_cell_length_b                   9.6610(4)
_cell_length_c                   12.4968(6)
_cell_measurement_reflns_used    3187
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8480
_cell_measurement_theta_min      5.5020
_cell_volume                     643.80(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_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     21.00  71.00   1.00    1.00    --   41.89  37.00  90.00   50
  2  \w     55.00 173.00   1.00    1.00    --  107.79  15.00 150.00  118
  3  \w    121.00 178.00   1.00    1.00    --  107.79  61.00  30.00   57
  4  \w     80.00 178.00   1.00    1.00    --  107.79  61.00-180.00   98
  5  \w     59.00 102.00   1.00    1.00    --  107.79 -94.00 -60.00   43
  6  \w     42.00 108.00   1.00    1.00    --  107.79 -94.00  30.00   66
  7  \w     60.00  89.00   1.00    1.00    --  107.79 -61.00  60.00   29
  8  \w     39.00  65.00   1.00    1.00    --  107.79 -94.00  90.00   26
  9  \w     54.00 119.00   1.00    1.00    --  107.79 -61.00  90.00   65
 10  \w     39.00 115.00   1.00    1.00    --  107.79-125.00 -90.00   76
 11  \w     36.00 127.00   1.00    1.00    --  107.79 -45.00-120.00   91
 12  \w     26.00  90.00   1.00    1.00    --   41.89-125.00   0.00   64
 13  \w    -64.00  31.00   1.00    1.00    --  -41.89  57.00-150.00   95
 14  \w   -107.00 -19.00   1.00    1.00    --  -41.89 -37.00  60.00   88
 15  \w   -113.00 -81.00   1.00    1.00    --  -41.89-133.00-155.00   32
;
_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      -0.1444395000
_diffrn_orient_matrix_UB_12      0.1213357000
_diffrn_orient_matrix_UB_13      -0.0656837000
_diffrn_orient_matrix_UB_21      0.1426323000
_diffrn_orient_matrix_UB_22      -0.0475663000
_diffrn_orient_matrix_UB_23      -0.1077547000
_diffrn_orient_matrix_UB_31      -0.2009166000
_diffrn_orient_matrix_UB_32      -0.0965747000
_diffrn_orient_matrix_UB_33      -0.0015947000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3990
_diffrn_reflns_theta_full        74.08
_diffrn_reflns_theta_max         74.08
_diffrn_reflns_theta_min         3.62
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         1.024
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0684
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0746P)^2^+1.2391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                2417
_reflns_number_total             2499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03865_si_002.cif
_cod_data_source_block           1606145
_cod_original_cell_volume        643.81(5)
_cod_database_code               1545436
_chemical_oxdiff_formula         'C26 H22 O2 Cl N2 S'
_chemical_oxdiff_usercomment     'HG LJH '
_reflns_odcompleteness_completeness 99.70
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C15(H15)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.712