Pd-Catalyzed Site-Selective C(sp2)–H Radical Acylation of Phenylalanine Containing Peptides with Aldehydes
Correa, Arkaitz; San Segundo, Marcos; Chemical Science  (2019) –; doi:10.1039/C9SC03425K

data_1552165
_publ_section_title
;
 Pd-Catalyzed Site-Selective C(sp2)--H Radical Acylation of Phenylalanine
 Containing Peptides with Aldehydes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC03425K
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H36 N2 O11'
_chemical_formula_sum            'C36 H36 N2 O11'
_chemical_formula_weight         672.67
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-14T18:56:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-07-08 deposited with the CCDC.    2019-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.02984(8)
_cell_length_b                   10.88201(8)
_cell_length_c                   30.5021(2)
_cell_measurement_reflns_used    22656
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.488
_cell_measurement_theta_min      3.997
_cell_volume                     3329.15(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -99.00  21.00   1.00    1.00    --  -42.38   0.00  60.00  120
  2  \w     29.00  91.00   1.00    1.00    --   42.38-125.00   0.00   62
  3  \w     55.00  96.00   1.00    1.00    --  107.93-125.00-180.00   41
  4  \w     82.00 158.00   1.00    1.00    --  107.93  30.00 120.00   76
  5  \w     44.00  77.00   1.00    1.00    --  107.93 -45.00 -60.00   33
  6  \w     32.00  69.00   1.00    1.00    --  107.93 -30.00  90.00   37
  7  \w     94.00 149.00   1.00    1.00    --  107.93  45.00  60.00   55
  8  \w     40.00  65.00   1.00    1.00    --  107.93 -30.00-180.00   25
  9  \w     34.00  62.00   1.00    1.00    --  107.93 -30.00 -90.00   28
 10  \w     74.00 158.00   1.00    1.00    --  107.93 125.00 150.00   84
 11  \w     41.00  67.00   1.00    1.00    --  107.93 -61.00 150.00   26
 12  \w    102.00 127.00   1.00    1.00    --  107.93 -61.00 150.00   25
 13  \w     41.00  66.00   1.00    1.00    --  107.93 -45.00   0.00   25
 14  \w    -51.00 -14.00   1.00    1.00    --  -42.38 125.00-180.00   37
 15  \w   -114.00 -36.00   1.00    1.00    --  -42.38 -38.00  30.00   78
 16  \w     31.00  75.00   1.00    1.00    --   42.38-125.00-180.00   44
 17  \w     81.00 135.00   1.00    1.00    --  107.93 -77.00 120.00   54
 18  \w     34.00  63.00   1.00    1.00    --  107.93 -30.00-120.00   29
 19  \w     39.00  65.00   1.00    1.00    --  107.93 -30.00-150.00   26
 20  \w     62.00  96.00   1.00    1.00    --  107.93 -94.00   0.00   34
 21  \w    125.00 151.00   1.00    1.00    --  107.93  45.00-120.00   26
 22  \w     89.00 115.00   1.00    1.00    --  107.93-125.00 -90.00   26
 23  \w     39.00  70.00   1.00    1.00    --  107.93 -45.00  60.00   31
 24  \w    104.00 130.00   1.00    1.00    --  107.93 -61.00 -60.00   26
 25  \w    110.00 149.00   1.00    1.00    --  107.93  61.00 -30.00   39
 26  \w     39.00 118.00   1.00    1.00    --  107.93-125.00 120.00   79
 27  \w     40.00  73.00   1.00    1.00    --  107.93 -61.00 -60.00   33
 28  \w     41.00  66.00   1.00    1.00    --  107.93 -30.00 120.00   25
 29  \w     94.00 120.00   1.00    1.00    --  107.93  45.00-120.00   26
 30  \w     41.00  67.00   1.00    1.00    --  107.93 -45.00 150.00   26
 31  \w     55.00 114.00   1.00    1.00    --  107.93-125.00 -30.00   59
 32  \w   -119.00 -10.00   1.00    1.00    --  -42.38 -77.00  60.00  109
 33  \w   -119.00 -10.00   1.00    1.00    --  -42.38 -77.00 150.00  109
 34  \w   -116.00 -14.00   1.00    1.00    --  -42.38 -57.00 -60.00  102
 35  \w     10.00  70.00   1.00    1.00    --   42.38  77.00 -60.00   60
 36  \w    -30.00  71.00   1.00    1.00    --   42.38 -57.00  90.00  101
 37  \w     10.00 119.00   1.00    1.00    --   42.38  77.00-150.00  109
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0018545
_diffrn_orient_matrix_UB_12      -0.1188924
_diffrn_orient_matrix_UB_13      0.027417
_diffrn_orient_matrix_UB_21      0.142541
_diffrn_orient_matrix_UB_22      0.0299931
_diffrn_orient_matrix_UB_23      0.0154929
_diffrn_orient_matrix_UB_31      -0.0571321
_diffrn_orient_matrix_UB_32      0.0707977
_diffrn_orient_matrix_UB_33      0.0394877
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            37271
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_min         4.314
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.836
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.786
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       prism
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.195
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
  The Friedel pair coverage of the experiment is almost complete 
 (100%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=0.01(6)
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6308
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0406P)^2^+0.4640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0749
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_number_gt                6051
_reflns_number_total             6308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03425k2.cif
_cod_data_source_block           a20190174_acn1309
_cod_original_cell_volume        3329.14(4)
_cod_database_code               1552165