Intermolecular iodofunctionalization of allenamides with indoles, pyrroles, and furans: synthesis of iodine-substituted Z-enamides.
Li, Honghe; Li, Xiaoxiao; Zhao, Zhigang; Ma, Ting; Sun, Chenyang; Yang, Bowen; Chemical communications (Cambridge, England) 52 (2016) 10167–10170; doi:10.1039/c6cc05046h

data_7124847
_publ_section_title
;
 Intermolecular iodofunctionalization of allenamides with indoles,
 pyrroles, and furans: synthesis of iodine-substituted Z-enamides.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10167
_journal_page_last               10170
_journal_paper_doi               10.1039/c6cc05046h
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C31 H27 I N2 O2 S'
_chemical_formula_sum            'C31 H27 I N2 O2 S'
_chemical_formula_weight         618.50
_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
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
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_audit_update_record
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2016-01-19 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.1354(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_measurement_temperature    217.05(10)
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_cell_measurement_theta_min      4.3170
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_measurement_details
;
  1 omega  -33.00   55.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000 -180.0000 88

  2 omega   10.00  104.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -120.0000 94

  3 omega  -31.00   63.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000 -180.0000 94

  4 omega   10.00  104.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  120.0000 94

  5 omega   20.00  104.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   30.0000 84

  6 omega   20.00  104.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -60.0000 84

  7 omega   41.00  126.00   1.0000   14.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 85

  8 omega   40.00   98.00   1.0000   14.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

  9 omega   38.00   91.00   1.0000   14.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 10 omega   40.00   98.00   1.0000   14.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 11 omega   38.00   91.00   1.0000   14.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 12 omega   39.00  109.00   1.0000   14.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 13 omega   38.00   91.00   1.0000   14.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 14 omega   41.00  126.00   1.0000   14.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   60.0000 85

 15 omega   39.00  177.00   1.0000   14.3200
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -60.0000 138

 16 omega    1.00   75.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000    0.0000 74
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.1144116000
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_diffrn_orient_matrix_UB_13      -0.0406068000
_diffrn_orient_matrix_UB_21      -0.1118193000
_diffrn_orient_matrix_UB_22      0.0231687000
_diffrn_orient_matrix_UB_23      0.0403710000
_diffrn_orient_matrix_UB_31      -0.0124142000
_diffrn_orient_matrix_UB_32      0.1307816000
_diffrn_orient_matrix_UB_33      -0.0185788000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14887
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_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.606
_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.541
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1074P)^2^+0.6608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4350
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_reflns_threshold_expression     'I > 2\s(I)'
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_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C00H(H00A,H00B), C00R(H00C,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C011(H011)
2.c Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C)
;
_shelx_res_checksum              5084
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-15
_olex2_submission_special_instructions 'No special instructions were received'