A fast and direct iodide-catalyzed oxidative 2-selenylation of tryptophan.
Gao, Yu-Ting; Liu, Shao-Dong; Cheng, Liang; Liu, Li; Chemical communications (Cambridge, England) 57 (2021) 3504–3507; doi:10.1039/d1cc00700a

data_7127997
_publ_section_title
;
 A fast and direct iodide-catalyzed oxidative 2-selenylation of
 tryptophan.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3504
_journal_page_last               3507
_journal_paper_doi               10.1039/d1cc00700a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C23 H20 F6 N2 O3 Se'
_chemical_formula_sum            'C23 H20 F6 N2 O3 Se'
_chemical_formula_weight         565.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-01-26 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                109.3780(10)
_cell_angle_beta                 91.5750(10)
_cell_angle_gamma                100.5370(10)
_cell_formula_units_Z            2
_cell_length_a                   9.17100(10)
_cell_length_b                   10.0901(3)
_cell_length_c                   13.7727(3)
_cell_measurement_reflns_used    15572
_cell_measurement_temperature    169.99(11)
_cell_measurement_theta_max      75.2810
_cell_measurement_theta_min      3.4070
_cell_volume                     1176.65(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.953
_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   -114.00 -54.00   0.50    0.05    --  -47.32 -58.00 174.00  120
  2  \w    -61.00  22.00   0.50    0.05    --  -47.32  58.00 -44.00  166
  3  \w    -22.00  47.00   0.50    0.05    --   47.32 -58.00 174.00  138
  4  \w     45.00 118.00   0.50    0.05    --   47.32  58.00 -44.00  146
  5  \w   -148.00 -84.00   0.50    0.20    --  -99.00 -58.00 174.00  128
  6  \w    -63.00 -33.00   0.50    0.20    --  -99.00  58.00 -44.00   60
  7  \w     88.00 169.00   0.50    0.20    --  103.25  58.00 -44.00  162
  8  \w     32.00  70.00   0.50    0.20    --  103.25 -58.00 174.00   76
  9  \w    -20.00  28.00   0.50    0.05    --  -47.32  19.00 -90.00   96
 10  \w     19.00  92.00   0.50    0.05    --   47.32-125.00  60.00  146
 11  \w     22.00  72.00   0.50    0.05    --   47.32-125.00 -60.00  100
 12  \w   -108.00 -26.00   0.50    0.20    --  -99.00 125.00  30.00  164
 13  \w    -72.00 -46.00   0.50    0.20    --  -99.00 125.00-120.00   52
 14  \w   -168.00 -89.00   0.50    0.20    --  -99.00 -64.00-127.15  158
 15  \w    -58.00 -28.00   0.50    0.20    --  -99.00 125.00   0.00   60
 16  \w   -115.00 -82.00   0.50    0.20    --  -99.00 -66.00 -38.40   66
 17  \w   -111.00 -45.00   0.50    0.20    --  -99.00 125.00  60.00  132
 18  \w   -112.00 -75.00   0.50    0.20    --  -99.00 125.00-120.00   74
 19  \w   -166.00-119.00   0.50    0.20    --  -99.00 -66.00 -38.40   94
 20  \w   -104.00 -41.00   0.50    0.20    --  -99.00 125.00-150.00  126
 21  \w   -124.00 -90.00   0.50    0.20    --  -99.00 142.00 -56.99   68
 22  \w   -124.00 -47.00   0.50    0.20    --  -99.00 142.00 149.15  154
 23  \w    -68.00 -26.00   0.50    0.20    --  -99.00  61.00 150.00   84
 24  \w    -55.00 -29.00   0.50    0.20    --  -99.00 142.00 -56.99   52
 25  \w   -112.00 -62.00   0.50    0.20    --  -99.00 125.00   0.00  100
 26  \w     31.00  56.00   0.50    0.20    --  103.25 -61.00  30.00   50
 27  \w     92.00 163.00   0.50    0.20    --  103.25  45.00-120.00  142
 28  \w     83.00 109.00   0.50    0.20    --  103.25-125.00 150.00   52
 29  \w     31.00  71.00   0.50    0.20    --  103.25 -94.00   0.00   80
 30  \w     87.00 155.00   0.50    0.20    --  103.25  61.00  30.00  136
 31  \w    117.00 155.00   0.50    0.20    --  103.25  15.00-180.00   76
 32  \w     73.00 104.00   0.50    0.20    --  103.25 -94.00 -60.00   62
 33  \w     32.00  58.00   0.50    0.20    --  103.25 -94.00 -60.00   52
 34  \w     91.00 127.00   0.50    0.20    --  103.25  30.00  90.00   72
 35  \w    133.00 168.00   0.50    0.20    --  103.25  30.00  90.00   70
 36  \w     41.00 106.00   0.50    0.20    --  103.25 -94.00  90.00  130
 37  \w    120.00 146.00   0.50    0.20    --  103.25   0.00-120.00   52
 38  \w     44.00  70.00   0.50    0.20    --  103.25   0.00-120.00   52
 39  \w     31.00  95.00   0.50    0.20    --  103.25 -77.00 120.00  128
 40  \w     38.00 101.00   0.50    0.20    --  103.25 -94.00 -90.00  126
 41  \w     31.00  74.00   0.50    0.20    --  103.25 -61.00 -30.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1357861000
_diffrn_orient_matrix_UB_12      0.0472725000
_diffrn_orient_matrix_UB_13      0.0244425000
_diffrn_orient_matrix_UB_21      -0.0194217000
_diffrn_orient_matrix_UB_22      -0.0613194000
_diffrn_orient_matrix_UB_23      0.0523062000
_diffrn_orient_matrix_UB_31      0.1031775000
_diffrn_orient_matrix_UB_32      0.0880829000
_diffrn_orient_matrix_UB_33      0.0605907000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16758
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.393
_diffrn_reflns_theta_min         3.417
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.704
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+7.2259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1983
_refine_ls_wR_factor_ref         0.1986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4557
_reflns_number_total             4667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00700a2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7127997.cif.'
_cod_database_code               7127997
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N F Se'
_chemical_oxdiff_usercomment     CHNOFSe
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C17(H17), C19(H19), C21(H21)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              65467
_shelx_hkl_checksum              39330
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.826