Catalytic sp3C-H Oxidation of Peptides and Their Analogues by Radical Cation Salts: From Glycine Amides to Quinolines
Xiaodong Jia; Yaxin Wang; Fangfang Peng; Congde Huo; Liangliang Yu; Jing Liu; Xicun Wang; Journal of Organic Chemistry 78 (2013) 9450–9456; doi:10.1021/jo401018v

data_4028575
_publ_contact_author_name
;
;
_publ_section_title
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 Catalytic sp3C-H Oxidation of Peptides and Their Analogues by Radical
 Cation Salts: From Glycine Amides to Quinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9450
_journal_page_last               9456
_journal_paper_doi               10.1021/jo401018v
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C15 H13 Br N2 O'
_chemical_formula_sum            'C15 H13 Br N2 O'
_chemical_formula_weight         317.18
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-21
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.310(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.84198(13)
_cell_length_b                   24.6091(6)
_cell_length_c                   11.1667(3)
_cell_measurement_reflns_used    2780
_cell_measurement_temperature    293.96(10)
_cell_measurement_theta_max      72.4840
_cell_measurement_theta_min      3.9770
_cell_volume                     1319.77(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293.96(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9553
_diffrn_measured_fraction_theta_max 0.9903
_diffrn_measurement_details
;
  1 omega  -14.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 31

  2 omega   29.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   60.0000 28

  3 omega  -30.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   60.0000 31

  4 omega -125.00  -87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000 -180.0000 38

  5 omega -123.00  -80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000   90.0000 43

  6 omega  -49.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  125.0000 -120.0000 25

  7 omega   -4.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000  -57.0000   30.0000 82

  8 omega   31.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000 -127.0000  -67.0000 71

  9 omega -116.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -91.0000  -60.0000 37

 10 omega   92.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000    0.0000 84

 11 omega   80.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -127.0000  172.0000 26

 12 omega  101.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -150.0000 44

 13 omega   45.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -180.0000 67

 14 omega  101.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   90.0000 26

 15 omega   66.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000    0.0000 26

 16 omega   65.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000  -60.0000 26

 17 omega  110.00  168.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -120.0000 58

 18 omega   50.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000 -150.0000 35

 19 omega  107.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   60.0000 47

 20 omega   72.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -150.0000 26

 21 omega   47.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  -90.0000 100

 22 omega   50.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  -30.0000 43

 23 omega  115.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   30.0000 61

 24 omega  147.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000 -120.0000 30

 25 omega  130.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   90.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0089312000
_diffrn_orient_matrix_UB_12      0.0533750000
_diffrn_orient_matrix_UB_13      0.0714692000
_diffrn_orient_matrix_UB_21      -0.0220995000
_diffrn_orient_matrix_UB_22      0.0324882000
_diffrn_orient_matrix_UB_23      -0.1187420000
_diffrn_orient_matrix_UB_31      -0.3199630000
_diffrn_orient_matrix_UB_32      -0.0037367000
_diffrn_orient_matrix_UB_33      -0.0115552000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5750
_diffrn_reflns_theta_full        71.00
_diffrn_reflns_theta_max         72.64
_diffrn_reflns_theta_min         3.59
_diffrn_source                   'SuperNova (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    4.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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    1.596
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.7196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                2344
_reflns_number_total             2577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401018v_si_003.cif
_cod_data_source_block           exp_688
_cod_original_cell_volume        1319.76(6)
_cod_database_code               4028575
_reflns_odcompleteness_completeness 95.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H2 of N2, H2A of C2, H3 of C3, H5 of C5, H8 of C8, H9 of C9, {H10A,H10B} of
  C10, {H11A,H11B} of C11
 At 1.5 times of:
  {H15A,H15B,H15C} of C15
2. Uiso/Uaniso restraints and constraints
Uanis(C10) ~ Ueq, Uanis(C11) ~ Ueq, Uanis(C9) ~ Ueq: with sigma of 0.01 and 
sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C8(H8), C9(H9)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;