Directed C(sp3)–H arylation of tryptophan: transformation of the directing group into an activated amide
Nicke, Lennart; Horx, Philip; Harms, Klaus; Geyer, Armin; Chemical Science  (2019) –; doi:10.1039/C9SC03440D

data_1552176
_publ_section_title
;
 Directed C(sp3)--H arylation of tryptophan: transformation of the
 directing group into an activated amide
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC03440D
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 N3 O4'
_chemical_formula_sum            'C21 H17 N3 O4'
_chemical_formula_weight         375.38
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-03-18 deposited with the CCDC.    2019-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.828(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5853(4)
_cell_length_b                   7.0808(2)
_cell_length_c                   14.4608(7)
_cell_measurement_reflns_used    18991
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.53
_cell_measurement_theta_min      5.19
_cell_volume                     872.85(6)
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.127.0 (STOE, 2016)'
_computing_data_reduction
'X-Area Integrate 1.71.0.0 (STOE, 2016) X-Area LANA 1.68.2.0 (STOE, 2016)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  'X-Area 1.77'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14642
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.573
_diffrn_reflns_theta_min         5.189
_diffrn_source                   'GeniX 3D HF Cu'
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  0.7847
_exptl_absorpt_correction_T_min  0.1720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'STOE LANA, absorption correction by scaling of reflection intensities.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 1266 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.09(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3282
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0620P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                3030
_reflns_number_total             3282
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03440d2.cif
_cod_data_source_block           LN513
_cod_database_code               1552176
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.597
_shelx_estimated_absorpt_t_max   0.944
_shelx_res_checksum              57195