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_1555229
_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 H26 F2 I N O4 S'
_chemical_formula_sum            'C24 H26 F2 I N O4 S'
_chemical_formula_weight         589.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-31
_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                 91.321(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.1210(6)
_cell_length_b                   15.7186(8)
_cell_length_c                   25.7853(11)
_cell_measurement_reflns_used    6089
_cell_measurement_temperature    290.92(10)
_cell_measurement_theta_max      28.6620
_cell_measurement_theta_min      3.9640
_cell_volume                     4911.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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_temperature      290.92(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   -1.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000  -90.0000 26

  2 omega  -20.00    5.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000   30.0000 25

  3 omega   51.00   96.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000 -120.0000 45

  4 omega  -25.00   19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -57.0000   60.0000 44

  5 omega  -39.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -19.0000  -90.0000 103
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0076964000
_diffrn_orient_matrix_UB_12      -0.0405451000
_diffrn_orient_matrix_UB_13      0.0114599000
_diffrn_orient_matrix_UB_21      0.0550711000
_diffrn_orient_matrix_UB_22      -0.0110844000
_diffrn_orient_matrix_UB_23      -0.0057320000
_diffrn_orient_matrix_UB_31      0.0181327000
_diffrn_orient_matrix_UB_32      0.0164321000
_diffrn_orient_matrix_UB_33      0.0243704000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20915
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.42
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.157
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         9643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                7219
_reflns_number_total             9643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02068_si_004.cif
_cod_data_source_block           zhangyq1230
_cod_database_code               1555229
_reflns_odcompleteness_completeness 99.60
_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.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C16(H16A,H16B), C33(H33A,
 H33B), C34(H34A,H34B), C37(H37A,H37B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C22(H22),
 C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C43(H43), C44(H44),
  C46(H46), C47(H47)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C36(H36A,H36B,
 H36C), C41(H41A,H41B,H41C), C48(H48A,H48B,H48C)
;
_olex2_date_sample_data_collection 2014-12-31
_olex2_submission_special_instructions 'No special instructions were received'