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_4031855
_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         'C27 H27 Cl I N O4 S2'
_chemical_formula_sum            'C27 H27 Cl I N O4 S2'
_chemical_formula_weight         655.97
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-24
_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                 95.082(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.9991(4)
_cell_length_b                   9.4815(2)
_cell_length_c                   18.3873(5)
_cell_measurement_reflns_used    3325
_cell_measurement_temperature    293.64(10)
_cell_measurement_theta_max      24.7600
_cell_measurement_theta_min      4.0740
_cell_volume                     2778.31(12)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.64(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   -3.00   57.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   19.0000  -60.0000 60

  2 omega    4.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000 -150.0000 70

  3 omega    6.00   68.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000  -60.0000 62

  4 omega   40.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000   90.0000 46
;
_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      -0.0316314000
_diffrn_orient_matrix_UB_12      0.0051344000
_diffrn_orient_matrix_UB_13      -0.0294539000
_diffrn_orient_matrix_UB_21      -0.0303109000
_diffrn_orient_matrix_UB_22      -0.0236744000
_diffrn_orient_matrix_UB_23      0.0231236000
_diffrn_orient_matrix_UB_31      -0.0078478000
_diffrn_orient_matrix_UB_32      0.0707852000
_diffrn_orient_matrix_UB_33      0.0098749000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11710
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.432
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87088
_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    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+1.2748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                4076
_reflns_number_total             5460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02161_si_002.cif
_cod_data_source_block           zhenl0603
_cod_original_cell_volume        2778.32(12)
_cod_database_code               4031855
_reflns_odcompleteness_completeness 99.68
_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), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19),
 C22(H22), C23(H23), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_olex2_date_sample_data_collection 2015-06-03
_olex2_submission_special_instructions 'No special instructions were received'