Acylamino-Directed Specific Sequential Difunctionalizations of Anilides via Metal-Free Relay Reactions for p-Oxygen and o-Nitrogen Incorporation.
Wan, Yameng; Zhang, Zhiguo; Ma, Nana; Bi, Jingjing; Zhang, Guisheng; The Journal of organic chemistry 84 (2019) 780–791; doi:10.1021/acs.joc.8b02636

data_4036006
_publ_section_title
;
 Acylamino-Directed Specific Sequential Difunctionalizations of Anilides
 via Metal-Free Relay Reactions for p-Oxygen and o-Nitrogen Incorporation.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              780
_journal_page_last               791
_journal_paper_doi               10.1021/acs.joc.8b02636
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C9 H10 N2 O5'
_chemical_formula_sum            'C9 H10 N2 O5'
_chemical_formula_weight         226.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-12
_audit_creation_method
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Olex2 1.2
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_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.2830
_cell_measurement_theta_min      4.3080
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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;
  1 omega -103.00   -5.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   30.0000 98

  2 omega  -47.00   35.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000 -120.0000 82

  3 omega   18.00   50.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000    0.0000 32

  4 omega  -11.00   54.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -120.0000 65

  5 omega   38.00   83.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 45

  6 omega   39.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 65

  7 omega   46.00   73.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 27

  8 omega   40.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 53

  9 omega   90.00  172.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 82

 10 omega   57.00  110.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 53

 11 omega  -20.00    6.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -150.0000 26

 12 omega   14.00   43.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -150.0000 29

 13 omega   58.00   84.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 26

 14 omega   63.00   89.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 26

 15 omega   75.00  102.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 27

 16 omega   43.00   98.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 55

 17 omega  143.00  171.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 28

 18 omega -106.00  -63.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -19.0000  150.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0392916000
_diffrn_orient_matrix_UB_12      0.0536478000
_diffrn_orient_matrix_UB_13      -0.0841784000
_diffrn_orient_matrix_UB_21      0.0333828000
_diffrn_orient_matrix_UB_22      0.0522923000
_diffrn_orient_matrix_UB_23      0.0865759000
_diffrn_orient_matrix_UB_31      0.3929008000
_diffrn_orient_matrix_UB_32      -0.0098432000
_diffrn_orient_matrix_UB_33      0.0011624000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
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_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.868
_diffrn_reflns_theta_min         4.090
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.486
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_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.190
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_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     148
_refine_ls_number_reflns         1901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0575
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.1548P] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_number_total             1901
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           201712262_tw
_cod_original_cell_volume        1011.18(19)
_cod_database_code               4036006
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H56N2O3
_shelx_estimated_absorpt_t_max   0.949
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_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.553(3)
 0.447(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), N1(H1)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'