Synthesis of N-Acetoxy-N-arylamides via Diacetoxyiodobenzene Promoted Double Acylation Reaction of Hydroxylamines with Aldehydes
Zhang, Huaiyuan; Su, Yingpeng; Wang, Ke-Hu; Huang, Danfeng; Li, Jun; Hu, Yulai; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00855D

data_7155670
_publ_section_title
;
 Synthesis of N-Acetoxy-N-arylamides via Diacetoxyiodobenzene Promoted
 Double Acylation Reaction of Hydroxylamines with Aldehydes
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00855D
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H12 N2 O5'
_chemical_formula_sum            'C15 H12 N2 O5'
_chemical_formula_weight         300.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-12-05 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.558(2)
_cell_length_b                   16.971(4)
_cell_length_c                   8.182(3)
_cell_measurement_reflns_used    618
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.5990
_cell_measurement_theta_min      5.9930
_cell_volume                     1466.0(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details
;
  1 omega   95.00  123.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 14

  2 omega   98.00  138.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -120.0000 20

  3 omega  113.00  157.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -180.0000 22

  4 omega   60.00   92.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 16

  5 omega   39.00   65.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 13

  6 omega   35.00   69.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   60.0000 17

  7 omega   45.00  121.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 38

  8 omega  152.00  178.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 13

  9 omega  105.00  133.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 14

 10 omega   46.00   92.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 23

 11 omega   38.00   90.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 26

 12 omega   37.00   93.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   90.0000 28

 13 omega   38.00  116.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 39

 14 omega   19.00   83.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000    0.0000 32

 15 omega   36.00   86.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 25

 16 omega   39.00   77.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -180.0000 19

 17 omega   41.00   69.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0084971000
_diffrn_orient_matrix_UB_12      -0.0849778000
_diffrn_orient_matrix_UB_13      0.0651129000
_diffrn_orient_matrix_UB_21      -0.0387462000
_diffrn_orient_matrix_UB_22      0.0290087000
_diffrn_orient_matrix_UB_23      0.1712765000
_diffrn_orient_matrix_UB_31      -0.1403278000
_diffrn_orient_matrix_UB_32      -0.0135001000
_diffrn_orient_matrix_UB_33      -0.0437372000
_diffrn_radiation_monochromator  mirror
_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     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4142
_diffrn_reflns_point_group_measured_fraction_full 0.832
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.885
_diffrn_reflns_theta_min         5.212
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 320 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2257
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0909P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1872
_reflns_Friedel_coverage         0.586
_reflns_Friedel_fraction_full    0.674
_reflns_Friedel_fraction_max     0.650
_reflns_number_gt                1297
_reflns_number_total             2257
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00855d2.cif
_cod_data_source_block           xray_0827
_cod_original_cell_volume        1466.1(7)
_cod_database_code               7155670
_reflns_odcompleteness_completeness 95.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              29476
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-08-27
_olex2_submission_special_instructions 'No special instructions were received'