#------------------------------------------------------------------------------
#$Date: 2020-11-06 15:07:26 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157697.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7157697
loop_
_publ_author_name
'Byrne, Joseph P.'
'Albrecht, Martin'
_publ_section_title
;
 Anion-cation synergistic metal-free catalytic oxidative homocoupling of
 benzylamines by triazolium iodide salts.
;
_journal_issue                   37
_journal_name_full               'Organic & 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 174.00   0.50   20.00    --  107.11 125.00  90.00  164
  2  ω     94.00 174.00   0.50   20.00    --  107.11  15.00 150.00  160
  3  ω     94.00 174.00   0.50   20.00    --  107.11  15.00  90.00  160
  4  ω     95.00 174.00   0.50   20.00    --  107.11  45.00-150.00  158
  5  ω     94.00 174.00   0.50   20.00    --  107.11  53.00-169.00  160
  6  ω     34.00 120.00   0.50    5.00    --   47.95  53.00-169.00  172
  7  ω     35.00 124.00   0.50   20.00    --  107.11 -61.00-180.00  178
  8  ω     32.00  96.00   0.50    5.00    --   47.95-125.00 -90.00  128
  9  ω     35.00 122.00   0.50   20.00    --  107.11 -53.00  46.00  174
 10  ω     35.00 124.00   0.50   20.00    --  107.11 -61.00 150.00  178
 11  ω     33.00 120.00   0.50    5.00    --   47.95  57.00  30.00  174
 12  ω     26.00 120.00   0.50    5.00    --   47.95  77.00  90.00  188
 13  ω     26.00 120.00   0.50    5.00    --   47.95  77.00 -60.00  188
 14  ω     32.00 121.00   0.50   20.00    --  107.11 -15.00-180.00  178
 15  ω    -23.00  62.00   0.50    5.00    --   47.95 -53.00  46.00  170
 16  ω    -32.00  54.00   0.50    5.00    --  -18.75  53.00-169.00  172
 17  ω    -66.00  -9.00   0.50    5.00    --  -18.75 125.00 150.00  114
 18  ω    -90.00  -4.00   0.50    5.00    --  -18.75 -53.00  46.00  172
 19  ω    -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       'ω 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/[σ²(Fo²)+(0.1440P)²] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.750000 0.250000 0.500000 0.0543(3) Uani 1 2 d S T P . .
I2 I 0.70935(4) 0.53866(7) 0.44783(4) 0.0679(3) Uani 1 1 d . . . . .
I3 I 0.500000 0.65693(8) 0.250000 0.0614(3) Uani 1 2 d S T P . .
I4 I 0.38844(3) 0.66651(7) 0.34356(5) 0.0680(3) Uani 1 1 d . . . . .
N1 N 0.6319(3) 0.0746(8) 0.3272(4) 0.0490(14) Uani 1 1 d . . . . .
N2 N 0.6810(4) 0.1058(8) 0.2869(5) 0.0534(15) Uani 1 1 d . . . . .
N3 N 0.6705(4) 0.2410(8) 0.2638(5) 0.0511(15) Uani 1 1 d . . . . .
C1 C 0.5894(4) 0.1839(8) 0.3297(5) 0.0453(16) Uani 1 1 d . . . . .
C2 C 0.6155(4) 0.2926(9) 0.2876(5) 0.0495(16) Uani 1 1 d . . . . .
H2 H 0.598329 0.383370 0.277798 0.059 Uiso 1 1 calc R . . . .
C3 C 0.7177(5) 0.3134(12) 0.2201(7) 0.064(2) Uani 1 1 d . . . . .
H3A H 0.753566 0.348394 0.261199 0.095 Uiso 1 1 calc GR . . . .
H3B H 0.696282 0.391227 0.187939 0.095 Uiso 1 1 calc GR . . . .
H3C H 0.734482 0.248612 0.182262 0.095 Uiso 1 1 calc GR . . . .
C4 C 0.6328(5) -0.0663(10) 0.3662(7) 0.062(2) Uani 1 1 d . . . . .
H4A H 0.615812 -0.134680 0.323581 0.093 Uiso 1 1 calc GR . . . .
H4B H 0.605838 -0.065759 0.410341 0.093 Uiso 1 1 calc GR . . . .
H4C H 0.677409 -0.090783 0.390256 0.093 Uiso 1 1 calc GR . . . .
C5 C 0.5291(4) 0.1822(9) 0.3703(5) 0.0498(17) Uani 1 1 d . . . . .
C6 C 0.5140(5) 0.3032(11) 0.4112(6) 0.060(2) Uani 1 1 d . . . . .
H6 H 0.542733 0.379988 0.415311 0.072 Uiso 1 1 calc R . . . .
C7 C 0.4558(6) 0.3122(11) 0.4470(6) 0.063(2) Uani 1 1 d . . . . .
H7 H 0.445922 0.394276 0.474832 0.076 Uiso 1 1 calc R . . . .
C8 C 0.4137(5) 0.1989(12) 0.4405(6) 0.061(2) Uani 1 1 d . . . . .
H8 H 0.374615 0.204631 0.462986 0.074 Uiso 1 1 calc R . . . .
C9 C 0.4288(5) 0.0757(11) 0.4006(6) 0.060(2) Uani 1 1 d . . . . .
H9 H 0.400769 -0.002080 0.398061 0.072 Uiso 1 1 calc R . . . .
C10 C 0.4857(5) 0.0688(10) 0.3645(5) 0.0543(19) Uani 1 1 d . . . . .
H10 H 0.495059 -0.012988 0.336080 0.065 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I2 I1 I2 180.0 7_656 . ?
I4 I3 I4 176.45(4) 2_655 . ?
N2 N1 C1 113.0(7) . . ?
N2 N1 C4 116.8(7) . . ?
C1 N1 C4 130.1(7) . . ?
N1 N2 N3 104.2(7) . . ?
N2 N3 C3 119.4(7) . . ?
C2 N3 N2 112.2(7) . . ?
C2 N3 C3 128.4(8) . . ?
N1 C1 C2 104.6(7) . . ?
N1 C1 C5 126.0(7) . . ?
C2 C1 C5 129.3(8) . . ?
N3 C2 C1 106.0(8) . . ?
N3 C2 H2 127.0 . . ?
C1 C2 H2 127.0 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C1 117.6(8) . . ?
C6 C5 C10 118.9(8) . . ?
C10 C5 C1 123.4(8) . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.8(10) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.1(9) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.6(9) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(9) . . ?
C10 C9 H9 120.1 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.7(9) . . ?
C9 C10 H10 119.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.9313(7) 7_656 ?
I1 I2 2.9313(7) . ?
I3 I4 2.9212(7) 2_655 ?
I3 I4 2.9213(7) . ?
N1 N2 1.311(10) . ?
N1 C1 1.354(10) . ?
N1 C4 1.467(11) . ?
N2 N3 1.337(11) . ?
N3 C2 1.336(11) . ?
N3 C3 1.450(12) . ?
C1 C2 1.380(12) . ?
C1 C5 1.483(12) . ?
C2 H2 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.375(13) . ?
C5 C10 1.385(13) . ?
C6 H6 0.9300 . ?
C6 C7 1.404(14) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(13) . ?
C10 H10 0.9300 . ?
