NIS-Mediated intermolecular hydroamination of allenamides with imidazole heterocycles: a facile protocol for the synthesis of allylic N,N-acetals
Li, Yan; Luo, Guo Li; Li, Xiao Xiao; Zhao, Zhi Gang; New Journal of Chemistry 42 (2018) 16940–; doi:10.1039/C8NJ03641A

data_7057750
_publ_section_title
;
 NIS-Mediated intermolecular hydroamination of allenamides with imidazole
 heterocycles: a facile protocol for the synthesis of allylic N,N-acetals
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16940
_journal_paper_doi               10.1039/C8NJ03641A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C24 H22 I N3 O3 S, H2 O'
_chemical_formula_sum            'C24 H24 I N3 O4 S'
_chemical_formula_weight         577.42
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-29 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.676(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4890(3)
_cell_length_b                   16.3138(7)
_cell_length_c                   17.6793(6)
_cell_measurement_reflns_used    5031
_cell_measurement_temperature    295.0(6)
_cell_measurement_theta_max      72.2260
_cell_measurement_theta_min      5.0390
_cell_volume                     2426.43(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      295.0(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -105.00 -17.00   1.00    1.00    --  -36.04 -38.00 150.00   88
  2  \w   -105.00 -17.00   1.00    1.00    --  -36.04 -38.00-120.00   88
  3  \w    -31.00  53.00   1.00    1.00    --   36.04 -57.00  60.00   84
  4  \w     23.00  89.00   1.00    1.00    --   36.04-125.00 -60.00   66
  5  \w    -35.00  65.00   1.00    1.00    --   36.04 -19.00 -60.00  100
  6  \w     39.00 109.00   1.00    2.14    --  108.71 -94.00  30.00   70
  7  \w     39.00 109.00   1.00    2.14    --  108.71 -94.00  60.00   70
  8  \w     91.00 177.00   1.00    2.14    --  108.71  45.00 -30.00   86
  9  \w     40.00 126.00   1.00    2.14    --  108.71 -45.00  90.00   86
 10  \w     39.00 109.00   1.00    2.14    --  108.71 -94.00 -30.00   70
 11  \w     37.00 134.00   1.00    2.14    --  108.71 -24.00  42.00   97
 12  \w    100.00 178.00   1.00    2.14    --  108.71 111.00 120.00   78
 13  \w     70.00 178.00   1.00    2.14    --  108.71  15.00 -90.00  108
 14  \w   -105.00 -17.00   1.00    1.00    --  -36.04 -38.00  60.00   88
 15  \w   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00  30.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1769656000
_diffrn_orient_matrix_UB_12      -0.0176064000
_diffrn_orient_matrix_UB_13      -0.0043792000
_diffrn_orient_matrix_UB_21      0.0411957000
_diffrn_orient_matrix_UB_22      0.0239881000
_diffrn_orient_matrix_UB_23      0.0846089000
_diffrn_orient_matrix_UB_31      -0.0235901000
_diffrn_orient_matrix_UB_32      -0.0895690000
_diffrn_orient_matrix_UB_33      0.0235228000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13795
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.960
_diffrn_reflns_theta_min         3.702
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.470
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.268
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0588
_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^)+(0.1186P)^2^+0.3956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1705
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4031
_reflns_number_total             4769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj03641a2.cif
_cod_data_source_block           lq-lxx-1801
_cod_depositor_comments          'Adding full bibliography for 7057750.cif.'
_cod_original_cell_volume        2426.44(15)
_cod_database_code               7057750
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.96
_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, All O(H,H) groups
2.a Free rotating group:
 O4(H4A,H4B)
2.b Ternary CH refined with riding coordinates:
 C8(H8)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C20(H20), C7(H7), C10(H10), C11(H11), C3(H3), C16(H16), C19(H19),
 C2(H2), C14(H14), C13(H13), C18(H18), C17(H17)
2.d X=CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              81862
_shelx_hkl_checksum              69526
_olex2_date_sample_data_collection 2018-05-25
_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 3.378
_oxdiff_exptl_absorpt_empirical_full_min 0.464