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_7157695
_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, I'
_chemical_formula_sum            'C10 H12 I N3'
_chemical_formula_weight         301.13
_chemical_name_systematic        '1,3-dimethyl-4-phenyl-1,2,3-triazolium iodide'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-12
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9563(2)
_cell_length_b                   10.5922(2)
_cell_length_c                   15.5819(2)
_cell_measurement_reflns_used    4142
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.7480
_cell_measurement_theta_min      2.6020
_cell_volume                     2303.44(6)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.945
_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    -54.00  83.00   1.00    1.00    --   27.42 -38.00 -30.00  137
  2  \w    -20.00  82.00   1.00    1.00    --   27.42 -99.00-120.00  102
  3  \w    -10.00  50.00   1.00    1.00    --   27.42  57.00 120.00   60
  4  \w    -10.00 103.00   1.00    1.00    --   27.42  57.00   0.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0002769000
_diffrn_orient_matrix_UB_12      0.0031699000
_diffrn_orient_matrix_UB_13      -0.0454640000
_diffrn_orient_matrix_UB_21      -0.0027131000
_diffrn_orient_matrix_UB_22      0.0668136000
_diffrn_orient_matrix_UB_23      0.0021898000
_diffrn_orient_matrix_UB_31      0.0507388000
_diffrn_orient_matrix_UB_32      0.0035758000
_diffrn_orient_matrix_UB_33      -0.0001164000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13462
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.050
_diffrn_reflns_theta_min         2.614
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.748
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.332
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0342P)^2^+0.1751P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1781
_reflns_number_total             2641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01472a2.cif
_cod_data_source_block           18ma141_jpb-mephtzm
_cod_depositor_comments
'Adding full bibliography for 7157695--7157697.cif.'
_cod_database_code               7157695
_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:
 C9(H9), C6(H6), C8(H8), C2(H2), C7(H7), C10(H10)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              971
_olex2_submission_special_instructions 'No special instructions were received'