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_4036145
_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_formula_moiety         'C21 H15 I O2'
_chemical_formula_sum            'C21 H15 I O2'
_chemical_formula_weight         426.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                89.483(4)
_cell_angle_beta                 88.583(4)
_cell_angle_gamma                72.496(4)
_cell_formula_units_Z            2
_cell_length_a                   5.7653(2)
_cell_length_b                   8.9351(4)
_cell_length_c                   17.7277(9)
_cell_measurement_reflns_used    4102
_cell_measurement_temperature    130.01(10)
_cell_measurement_theta_max      76.1670
_cell_measurement_theta_min      4.9770
_cell_volume                     870.66(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega  -35.00   -1.00   1.0000    1.6250
omega____ theta____ kappa____ phi______ frames
    -      -41.8673  -19.0000  -30.0000 34

  2 omega    2.00   28.00   1.0000    1.6250
omega____ theta____ kappa____ phi______ frames
    -      -41.8673   37.0000 -120.0000 26

  3 omega    6.00   83.00   1.0000    1.6250
omega____ theta____ kappa____ phi______ frames
    -       41.8673  -99.0000  -60.0000 77

  4 omega   54.00   81.00   1.0000    1.6250
omega____ theta____ kappa____ phi______ frames
    -       41.8673 -125.0000 -120.0000 27

  5 omega   24.00   51.00   1.0000    1.6250
omega____ theta____ kappa____ phi______ frames
    -       41.8673 -125.0000 -120.0000 27

  6 omega   39.00   65.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 26

  7 omega   69.00  113.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 44

  8 omega   86.00  113.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 27

  9 omega   70.00  114.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 44

 10 omega   55.00   82.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 27

 11 omega   51.00   89.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 38

 12 omega   84.00  176.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -90.0000 92

 13 omega  126.00  177.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -150.0000 51

 14 omega   93.00  174.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -150.0000 81

 15 omega   60.00   85.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 25

 16 omega  112.00  145.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   90.0000 33

 17 omega   84.00  115.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   90.0000 31

 18 omega   57.00   83.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   90.0000 26

 19 omega   59.00   89.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   90.0000 30

 20 omega   40.00   99.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 59

 21 omega   39.00  105.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 66

 22 omega   43.00   72.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 29

 23 omega   36.00   99.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 63

 24 omega   32.00   57.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 25

 25 omega   29.00   73.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 44

 26 omega   20.00   50.00   1.0000    1.6250
omega____ theta____ kappa____ phi______ frames
    -       41.8673   57.0000   90.0000 30

 27 omega   83.00  113.00   1.0000    1.6250
omega____ theta____ kappa____ phi______ frames
    -       41.8673   57.0000   90.0000 30

 28 omega  129.00  158.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 29

 29 omega  101.00  176.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   90.0000 75

 30 omega  101.00  139.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  120.0000 38

 31 omega   95.00  121.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 26

 32 omega   -6.00   30.00   1.0000    1.6250
omega____ theta____ kappa____ phi______ frames
    -      -41.8673   37.0000  150.0000 36

 33 omega  -47.00  -10.00   1.0000    1.6250
omega____ theta____ kappa____ phi______ frames
    -      -41.8673   37.0000  150.0000 37

 34 omega -118.00  -43.00   1.0000    1.6250
omega____ theta____ kappa____ phi______ frames
    -      -41.8673  -19.0000  -30.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2232897000
_diffrn_orient_matrix_UB_12      0.0471173000
_diffrn_orient_matrix_UB_13      -0.0281107000
_diffrn_orient_matrix_UB_21      0.0063420000
_diffrn_orient_matrix_UB_22      0.0799360000
_diffrn_orient_matrix_UB_23      0.0762308000
_diffrn_orient_matrix_UB_31      0.1692549000
_diffrn_orient_matrix_UB_32      -0.1551593000
_diffrn_orient_matrix_UB_33      0.0309051000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6516
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        75.000
_diffrn_reflns_theta_max         77.384
_diffrn_reflns_theta_min         4.991
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.519
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_correction_T_min  0.130
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
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
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.3458
_exptl_crystal_size_mid          0.1083
_exptl_crystal_size_min          0.0142
_refine_diff_density_max         1.773
_refine_diff_density_min         -1.101
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         6516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+2.2234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5844
_reflns_number_total             6516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00250_si_002.cif
_cod_data_source_block           rwg2015_3chklf5
_cod_original_cell_volume        870.67(7)
_cod_database_code               4036145
_chemical_oxdiff_formula         'C21 H15 O2 I'
_diffrn_oxdiff_twin_integration_method simultaneous
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.45(4) 0.303(16) 0.25(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'