Regioselective 1,2-additon of allenamides with N-haloimides: synthesis of 2-halo allylic aminal derivatives
Li, Honghe; Li, Xiao-Xiao; Zhao, Zhi-Gang; Yuan, Xiao; Sun, Chenyang; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00882A

data_7155590
_publ_section_title
;
 Regioselective 1,2-additon of allenamides with N-haloimides: synthesis of
 2-halo allylic aminal derivatives
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00882A
_journal_year                    2017
_chemical_formula_moiety         'C21 H19 Cl N2 O4 S'
_chemical_formula_sum            'C21 H18 Cl N O5 S'
_chemical_formula_weight         431.87
_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             2016-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-11-14 deposited with the CCDC.
2017-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.0325(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.53511(16)
_cell_length_b                   13.4671(2)
_cell_length_c                   18.5695(3)
_cell_measurement_reflns_used    9827
_cell_measurement_temperature    293.3(2)
_cell_measurement_theta_max      72.5480
_cell_measurement_theta_min      4.9280
_cell_volume                     2079.46(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.3(2)
_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 1.000
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  120.0000 67

  2 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  120.0000 84

  3 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  150.0000 84

  4 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -120.0000 88

  5 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000    0.0000 94

  6 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000 -120.0000 88

  7 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -180.0000 94

  8 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -150.0000 88

  9 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

 10 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -90.0000 67

 11 omega   38.00   91.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 12 omega   38.00  116.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 78

 13 omega   41.00  126.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -180.0000 85

 14 omega   39.00  109.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 15 omega   38.00   91.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 16 omega   37.00  146.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 109

 17 omega   41.00  126.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   90.0000 85

 18 omega   96.00  176.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   80.0000 -176.0000 80

 19 omega   38.00   91.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 20 omega   38.00   91.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 21 omega   39.00  109.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 22 omega   38.00   91.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 23 omega   39.00  109.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 24 omega   40.00   98.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 25 omega   38.00  116.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 78

 26 omega   87.00  178.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 91

 27 omega   40.00   98.00   1.0000    3.1800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 28 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000    0.0000 84

 29 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -120.0000 94

 30 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  150.0000 94

 31 omega   20.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -60.0000 50
;
_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_UB_11      0.0984974000
_diffrn_orient_matrix_UB_12      -0.0699066000
_diffrn_orient_matrix_UB_13      -0.0384412000
_diffrn_orient_matrix_UB_21      0.0079767000
_diffrn_orient_matrix_UB_22      -0.0768754000
_diffrn_orient_matrix_UB_23      0.0621538000
_diffrn_orient_matrix_UB_31      -0.1566971000
_diffrn_orient_matrix_UB_32      -0.0478564000
_diffrn_orient_matrix_UB_33      -0.0437314000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21110
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.051
_diffrn_reflns_theta_max         67.051
_diffrn_reflns_theta_min         4.889
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.847
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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.
;
_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    1.379
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0981P)^2^+0.7563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3405
_reflns_number_total             3710
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00882a2.cif
_cod_data_source_block           xnkd-lq-111
_cod_original_cell_volume        2079.46(7)
_cod_database_code               7155590
_reflns_odcompleteness_completeness 99.92
_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. Rigid bond restraints
 N007, C00H
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
3.a Ternary CH refined with riding coordinates:
 C00A(H00A)
3.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C)
3.c Aromatic/amide H refined with riding coordinates:
 C00C(H00D), C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T)
3.d Idealised Me refined as rotating group:
 C00S(H00H,H00N,H00O)
;
_shelx_res_checksum              65841
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-16
_olex2_submission_special_instructions 'No special instructions were received'