PIFA-mediated ethoxyiodination of enamides with potassium iodide.
Beltran, R.; Nocquet-Thibault, S; Blanchard, F.; Dodd, R. H.; Cariou, K.; Organic & biomolecular chemistry 14 (2016) 8448–8451; doi:10.1039/c6ob01673a

data_7155266
_publ_section_title
;
 PIFA-mediated ethoxyiodination of enamides with potassium iodide.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8448
_journal_page_last               8451
_journal_paper_doi               10.1039/c6ob01673a
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C18 H21 I N2 O6 S'
_chemical_formula_sum            'C18 H21 I N2 O6 S'
_chemical_formula_weight         520.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-29 deposited with the CCDC.
2016-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.7507(4)
_cell_length_b                   14.1829(7)
_cell_length_c                   43.847(3)
_cell_measurement_reflns_used    5883
_cell_measurement_temperature    292.8(2)
_cell_measurement_theta_max      26.8810
_cell_measurement_theta_min      3.5150
_cell_volume                     4198.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.8(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w     -9.00  84.86   0.38   60.00    --   12.50  19.00-120.00  247
  2  \w    -76.00 -22.80   0.38   60.00    --   12.50  19.00-120.00  140
  3  \w     -1.00  24.46   0.38   60.00    --  -12.90 -77.00  60.00   67
  4  \w    -60.00 -28.08   0.38   60.00    --  -12.90 -77.00  60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0711964000
_diffrn_orient_matrix_UB_12      -0.0352658000
_diffrn_orient_matrix_UB_13      0.0033853000
_diffrn_orient_matrix_UB_21      0.0187260000
_diffrn_orient_matrix_UB_22      -0.0059230000
_diffrn_orient_matrix_UB_23      -0.0158013000
_diffrn_orient_matrix_UB_31      0.0750048000
_diffrn_orient_matrix_UB_32      0.0349451000
_diffrn_orient_matrix_UB_33      0.0007342000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            19785
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.718
_diffrn_reflns_theta_min         3.374
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_description       block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.732
_refine_diff_density_min         -1.061
_refine_diff_density_rms         0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0823P)^2^+4.6521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1827
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3243
_reflns_number_total             5384
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01673a2.cif
_cod_data_source_block           mtbe051_juin2016
_cod_depositor_comments
;Adding full bibliography for 7155265--7155266.cif.

 Adding full bibliography for 7155265--7155266.cif.
;
_cod_database_code               7155266
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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, All O(H) groups
2. Others
 Sof(O5)=Sof(H5)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=1-FVAR(1)
 Sof(O4)=Sof(H4)=Sof(H4A)=Sof(C6)=Sof(H6A)=Sof(H6B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4A), C4(H4B)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_shelx_res_checksum              58656
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.774