Iodine-Promoted Radical Cyclization in Water: A Selective Reaction of 1,6-Enynes with Sulfonyl Hydrazides.
Zheng, Lan; Zhou, Zhao-Zhao; He, Yu-Tao; Li, Lian-Hua; Ma, Jun-Wei; Qiu, Yi-Feng; Zhou, Ping-Xin; Liu, Xue-Yuan; Xu, Peng-Fei; Liang, Yong-Min; The Journal of organic chemistry 81 (2016) 66–76; doi:10.1021/acs.joc.5b02161

data_4031854
_publ_section_title
;
 Iodine-Promoted Radical Cyclization in Water: A Selective Reaction of
 1,6-Enynes with Sulfonyl Hydrazides.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              66
_journal_page_last               76
_journal_paper_doi               10.1021/acs.joc.5b02161
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C26 H28 O6 S'
_chemical_formula_sum            'C26 H28 O6 S'
_chemical_formula_weight         468.54
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.000(6)
_cell_angle_beta                 91.074(5)
_cell_angle_gamma                90.000(6)
_cell_formula_units_Z            4
_cell_length_a                   10.2181(8)
_cell_length_b                   6.8051(6)
_cell_length_c                   33.7995(19)
_cell_measurement_reflns_used    2955
_cell_measurement_temperature    294.39(10)
_cell_measurement_theta_max      28.1590
_cell_measurement_theta_min      3.6560
_cell_volume                     2349.8(3)
_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      294.39(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -20.00   12.40   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0446  -99.0000 -120.0000 27

  2 omega   25.00   51.40   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0446   57.0000   90.0000 22

  3 omega  -33.00   40.20   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4977  -57.0000   60.0000 61

  4 omega    1.00   93.40   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4977   38.0000 -120.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0005492000
_diffrn_orient_matrix_UB_12      -0.1037724000
_diffrn_orient_matrix_UB_13      -0.0019473000
_diffrn_orient_matrix_UB_21      0.0691704000
_diffrn_orient_matrix_UB_22      -0.0015791000
_diffrn_orient_matrix_UB_23      0.0021672000
_diffrn_orient_matrix_UB_31      -0.0059500000
_diffrn_orient_matrix_UB_32      -0.0096404000
_diffrn_orient_matrix_UB_33      0.0207860000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            8968
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.50
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94067
_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 colourless'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0303P)^2^+0.7956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                3708
_reflns_number_total             4625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02161_si_001.cif
_cod_data_source_block           zhouzhzh0929
_cod_database_code               4031854
_reflns_odcompleteness_completeness 99.66
_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 Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22),
 C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'