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_1545253
_publ_section_title
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 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         'C16 H9 F13 O2'
_chemical_formula_sum            'C16 H9 F13 O2'
_chemical_formula_weight         480.23
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-02-07
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                97.92(3)
_cell_angle_beta                 99.81(3)
_cell_angle_gamma                99.47(3)
_cell_formula_units_Z            2
_cell_length_a                   5.5613(11)
_cell_length_b                   12.363(3)
_cell_length_c                   13.729(3)
_cell_measurement_reflns_used    7134
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3.06
_cell_volume                     904.0(4)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7134
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.035
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.628
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.628
_refine_ls_R_factor_all          0.2112
_refine_ls_R_factor_gt           0.1550
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4315
_refine_ls_wR_factor_ref         0.4729
_reflns_number_gt                1553
_reflns_number_total             3181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03865_si_003.cif
_cod_data_source_block           liao
_cod_depositor_comments          'Adding full bibliography for 1545253.cif.'
_cod_original_cell_volume        904.0(3)
_cod_database_code               1545253
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'