Palladium-Catalyzed Radical Cascade Iododifluoromethylation/Cyclization of 1,6-Enynes with Ethyl Difluoroiodoacetate.
Wang, Yu-Qi; He, Yu-Tao; Zhang, Lu-Lu; Wu, Xin-Xing; Liu, Xue-Yuan; Liang, Yong-Min; Organic letters 17 (2015) 4280–4283; doi:10.1021/acs.orglett.5b02068

data_1555227
_publ_section_title
;
 Palladium-Catalyzed Radical Cascade Iododifluoromethylation/Cyclization
 of 1,6-Enynes with Ethyl Difluoroiodoacetate.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4280
_journal_page_last               4283
_journal_paper_doi               10.1021/acs.orglett.5b02068
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C24 H25 F3 I N O4 S'
_chemical_formula_sum            'C24 H25 F3 I N O4 S'
_chemical_formula_weight         607.41
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.921(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.4658(3)
_cell_length_b                   20.2837(7)
_cell_length_c                   19.4390(5)
_cell_measurement_reflns_used    3365
_cell_measurement_temperature    293.18(10)
_cell_measurement_theta_max      23.8440
_cell_measurement_theta_min      3.8440
_cell_volume                     5213.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.18(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -34.00   -7.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000   90.0000 27

  2 omega  -20.00   41.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000  120.0000 61

  3 omega   34.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854 -178.0000   30.0000 62

  4 omega  -52.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000  150.0000 39

  5 omega   53.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854 -178.0000  120.0000 34

  6 omega   58.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000 -180.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0071750000
_diffrn_orient_matrix_UB_12      0.0053163000
_diffrn_orient_matrix_UB_13      -0.0366719000
_diffrn_orient_matrix_UB_21      0.0250444000
_diffrn_orient_matrix_UB_22      0.0308163000
_diffrn_orient_matrix_UB_23      0.0059613000
_diffrn_orient_matrix_UB_31      0.0468905000
_diffrn_orient_matrix_UB_32      -0.0156640000
_diffrn_orient_matrix_UB_33      -0.0007263000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23268
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             2432
_refine_diff_density_max         1.106
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         10222
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0600
_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^)+(0.0448P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1529
_reflns_number_gt                5369
_reflns_number_total             10222
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02068_si_002.cif
_cod_data_source_block           zhangyq0521
_cod_database_code               1555227
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(O44) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(O63) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C16(H16A,H16B), C33(H33A,H33B),
 C34(H34A,H34B), C36(H36A,H36B), C38(H38A,H38B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C22(H22), C23(H23),
 C26(H26), C27(H27), C28(H28), C29(H29), C41(H41), C42(H42), C44(H44), C45(H45)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C39(H39A,H39B,
 H39C), C46(H46A,H46B,H46C), C62(H62A,H62B,H62C)
;
_olex2_date_sample_data_collection 2015-05-21
_olex2_submission_special_instructions 'No special instructions were received'