Regio- and stereoselective iodoacyloxylations of alkynes.
Priebbenow, Daniel L.; Gable, Robert W.; Baell, Jonathan; The Journal of organic chemistry 80 (2015) 4412–4418; doi:10.1021/acs.joc.5b00250

data_4036144
_publ_section_title
;
 Regio- and stereoselective iodoacyloxylations of alkynes.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4412
_journal_page_last               4418
_journal_paper_doi               10.1021/acs.joc.5b00250
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H18 I N O4'
_chemical_formula_sum            'C20 H18 I N O4'
_chemical_formula_weight         463.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
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_atom_sites_solution_hydrogens   geom
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Olex2 1.2
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_cell_measurement_reflns_used    11793
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
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;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
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omega____ theta____ kappa____ phi______ frames
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  2 omega  -48.00   33.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
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  3 omega  -61.00  -14.00   1.0000    1.2600
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  4 omega   61.00   87.00   1.0000    1.2600
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  5 omega   61.00   93.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
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  6 omega   83.00  108.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
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  7 omega   75.00  112.00   1.0000    5.0350
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  8 omega   40.00   95.00   1.0000    5.0350
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  9 omega   37.00  116.00   1.0000    5.0350
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 10 omega   60.00  114.00   1.0000    5.0350
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 11 omega  105.00  130.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -90.0000 25

 12 omega   74.00  115.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
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 13 omega   65.00  107.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 42

 14 omega   62.00   89.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
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 15 omega   44.00   70.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -90.0000 26

 16 omega   36.00  116.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 80

 17 omega   49.00   75.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 26

 18 omega   60.00  177.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -150.0000 117

 19 omega  100.00  131.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 31

 20 omega   63.00  124.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -30.0000 61

 21 omega   96.00  141.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -90.0000 45

 22 omega  142.00  169.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 27

 23 omega  140.00  167.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 27

 24 omega  136.00  168.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   90.0000 32

 25 omega  127.00  169.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  120.0000 42

 26 omega  104.00  130.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 26

 27 omega   90.00  127.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 37

 28 omega   87.00  126.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   90.0000 39

 29 omega   40.00  123.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000    0.0000 83

 30 omega   42.00   74.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 32

 31 omega   34.00   94.00   1.0000    5.0350
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -90.0000 60

 32 omega   39.00   94.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -       41.8673 -125.0000 -180.0000 55

 33 omega -113.00  -87.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -      -41.8673  -57.0000  -30.0000 26

 34 omega -116.00  -21.00   1.0000    1.2600
omega____ theta____ kappa____ phi______ frames
    -      -41.8673  -37.0000  150.0000 95
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_diffrn_reflns_theta_full        67.684
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_diffrn_source                   'sealed X-ray tube'
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Numerical absorption correction based on gaussian integration over
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
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 Flack x determined using 1620 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
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_refine_ls_abs_structure_Flack   -0.020(2)
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_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
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_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0178
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0190P)^2^+0.6355P] where P=(Fo^2^+2Fc^2^)/3'
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_cod_data_source_file            jo5b00250_si_003.cif
_cod_data_source_block           rwg2015_1cugau
_cod_database_code               4036144
_chemical_oxdiff_formula         'C20 H18 N O4 I'
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_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'