A mild and selective Pd-mediated methodology for the synthesis of highly fluorescent 2-arylated tryptophans and tryptophan-containing peptides: a catalytic role for Pd0 nanoparticles?
Thomas J. Williams; Alan J. Reay; Adrian C. Whitwood; Ian J. S. Fairlamb; Chem.Commun. 50 (2014) 3052–; doi:10.1039/c3cc48481e

data_7112069
_publ_section_title
;
 A mild and selective Pd-mediated methodology for the synthesis of highly
 fluorescent 2-arylated tryptophans and tryptophan-containing peptides: a
 catalytic role for Pd0 nanoparticles?
;
_journal_name_full               Chem.Commun.
_journal_page_first              3052
_journal_paper_doi               10.1039/c3cc48481e
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H19 F3 N2 O3'
_chemical_formula_sum            'C21 H19 F3 N2 O3'
_chemical_formula_weight         404.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-04-24
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.900(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7492(3)
_cell_length_b                   9.0043(3)
_cell_length_c                   24.1842(7)
_cell_measurement_reflns_used    5381
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      27.8109
_cell_measurement_theta_min      3.1089
_cell_volume                     1882.30(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -97.00  -61.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7365 -178.0000   60.0000 36

  2 omega  -78.00  -51.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7365 -178.0000 -120.0000 27

  3 omega  -30.00   96.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8303    0.0000 -150.0000 126

  4 omega   35.00   77.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8303 -141.0000  -29.0000 42

  5 omega  -43.00    9.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7365   57.0000   90.0000 52

  6 omega  -92.00    8.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.7365  -77.0000  -30.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0097380000
_diffrn_orient_matrix_UB_12      0.0026536000
_diffrn_orient_matrix_UB_13      -0.0296944000
_diffrn_orient_matrix_UB_21      -0.0294622000
_diffrn_orient_matrix_UB_22      0.0732094000
_diffrn_orient_matrix_UB_23      0.0005393000
_diffrn_orient_matrix_UB_31      0.0759031000
_diffrn_orient_matrix_UB_32      0.0287956000
_diffrn_orient_matrix_UB_33      0.0013631000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14377
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         3.12
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.3796
_exptl_crystal_size_mid          0.1807
_exptl_crystal_size_min          0.0328
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         8188
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0442P)^2^+0.5706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                7201
_reflns_number_total             8188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48481e2.cif
_cod_data_source_block           ijsf1201
_cod_original_cell_volume        1882.30(10)
_cod_database_code               7112069
_chemical_oxdiff_formula         'C21 H19 F3 N2 O3'
_chemical_oxdiff_usercomment     'Toms TJW/5/143/450/1'
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82