Anion-cation synergistic metal-free catalytic oxidative homocoupling of benzylamines by triazolium iodide salts.
Byrne, Joseph P.; Albrecht, Martin; Organic & biomolecular chemistry 18 (2020) 7379–7387; doi:10.1039/d0ob01472a

data_7157697
_publ_section_title
;
 Anion-cation synergistic metal-free catalytic oxidative homocoupling of
 benzylamines by triazolium iodide salts.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7379
_journal_page_last               7387
_journal_paper_doi               10.1039/d0ob01472a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C10 H12 N3, I3'
_chemical_formula_sum            'C10 H12 I3 N3'
_chemical_formula_weight         554.93
_chemical_name_systematic
'1,3-dimethyl-4-phenyl-1,2,3-triazolium triiodide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-16 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.242(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.4846(8)
_cell_length_b                   9.4451(3)
_cell_length_c                   15.8942(7)
_cell_measurement_reflns_used    7504
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.3690
_cell_measurement_theta_min      4.3700
_cell_volume                     3035.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_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     92.00 174.00   0.50   20.00    --  107.11 125.00  90.00  164
  2  \w     94.00 174.00   0.50   20.00    --  107.11  15.00 150.00  160
  3  \w     94.00 174.00   0.50   20.00    --  107.11  15.00  90.00  160
  4  \w     95.00 174.00   0.50   20.00    --  107.11  45.00-150.00  158
  5  \w     94.00 174.00   0.50   20.00    --  107.11  53.00-169.00  160
  6  \w     34.00 120.00   0.50    5.00    --   47.95  53.00-169.00  172
  7  \w     35.00 124.00   0.50   20.00    --  107.11 -61.00-180.00  178
  8  \w     32.00  96.00   0.50    5.00    --   47.95-125.00 -90.00  128
  9  \w     35.00 122.00   0.50   20.00    --  107.11 -53.00  46.00  174
 10  \w     35.00 124.00   0.50   20.00    --  107.11 -61.00 150.00  178
 11  \w     33.00 120.00   0.50    5.00    --   47.95  57.00  30.00  174
 12  \w     26.00 120.00   0.50    5.00    --   47.95  77.00  90.00  188
 13  \w     26.00 120.00   0.50    5.00    --   47.95  77.00 -60.00  188
 14  \w     32.00 121.00   0.50   20.00    --  107.11 -15.00-180.00  178
 15  \w    -23.00  62.00   0.50    5.00    --   47.95 -53.00  46.00  170
 16  \w    -32.00  54.00   0.50    5.00    --  -18.75  53.00-169.00  172
 17  \w    -66.00  -9.00   0.50    5.00    --  -18.75 125.00 150.00  114
 18  \w    -90.00  -4.00   0.50    5.00    --  -18.75 -53.00  46.00  172
 19  \w    -66.00  -9.00   0.50    5.00    --  -18.75 125.00-180.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0329172000
_diffrn_orient_matrix_UB_12      0.0493832000
_diffrn_orient_matrix_UB_13      0.0755479000
_diffrn_orient_matrix_UB_21      0.0484299000
_diffrn_orient_matrix_UB_22      -0.0924052000
_diffrn_orient_matrix_UB_23      0.0608333000
_diffrn_orient_matrix_UB_31      0.0487774000
_diffrn_orient_matrix_UB_32      0.1249971000
_diffrn_orient_matrix_UB_33      0.0152306000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14247
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.246
_diffrn_reflns_theta_min         4.374
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    48.371
_exptl_absorpt_correction_T_max  0.24283
_exptl_absorpt_correction_T_min  0.14288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.429
_exptl_crystal_description       block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.074
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.044
_refine_diff_density_max         2.170
_refine_diff_density_min         -0.963
_refine_diff_density_rms         0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0652
_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^)+(0.1440P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1910
_refine_ls_wR_factor_ref         0.1977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2608
_reflns_number_total             3110
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01472a2.cif
_cod_data_source_block           19ma021_jpb478-i3
_cod_depositor_comments
'Adding full bibliography for 7157695--7157697.cif.'
_cod_database_code               7157697
_shelx_shelxl_version_number     2018/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              14954
_olex2_submission_special_instructions 'No special instructions were received'