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_1555230
_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_absolute_configuration ad
_chemical_formula_moiety         'C23 H25 F2 I N2 O4 S'
_chemical_formula_sum            'C23 H25 F2 I N2 O4 S'
_chemical_formula_weight         590.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-15
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.1416(7)
_cell_length_b                   10.1959(3)
_cell_length_c                   20.5376(6)
_cell_measurement_reflns_used    3601
_cell_measurement_temperature    293.78(10)
_cell_measurement_theta_max      24.5940
_cell_measurement_theta_min      3.7770
_cell_volume                     5055.2(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      293.78(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -19.00   23.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000    0.0000 42

  2 omega  -32.00   11.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479    0.0000   60.0000 43

  3 omega   10.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000  120.0000 66
;
_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      0.0227052000
_diffrn_orient_matrix_UB_12      -0.0343335000
_diffrn_orient_matrix_UB_13      -0.0137761000
_diffrn_orient_matrix_UB_21      -0.0135955000
_diffrn_orient_matrix_UB_22      -0.0603616000
_diffrn_orient_matrix_UB_23      0.0061950000
_diffrn_orient_matrix_UB_31      -0.0127772000
_diffrn_orient_matrix_UB_32      0.0031714000
_diffrn_orient_matrix_UB_33      -0.0310785000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12547
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.395
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65446
_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_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.042(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         8050
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0239P)^2^+0.2728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                5976
_reflns_number_total             8050
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02068_si_003.cif
_cod_data_source_block           wangyq_0611
_cod_database_code               1555230
_chemical_oxdiff_formula         'C H N O'
_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:
 C1(H1A,H1B), C4(H4A,H4B), C12(H12A,H12B), C15(H15A,H15B), C24(H24A,H24B),
 C27(H27A,H27B), C35(H35A,H35B), C38(H38A,H38B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C21(H21), C22(H22),
 C30(H30), C31(H31), C32(H32), C33(H33), C41(H41), C42(H42), C44(H44), C45(H45)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C34(H34A,H34B,
 H34C), C39(H39A,H39B,H39C), C46(H46A,H46B,H46C)
;
_olex2_date_sample_data_collection 2015-06-11
_olex2_submission_special_instructions 'No special instructions were received'