#------------------------------------------------------------------------------
#$Date: 2020-11-06 15:07:26 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157695.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_7157695
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, 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  83.00   1.00    1.00    --   27.42 -38.00 -30.00  137
  2  ω    -20.00  82.00   1.00    1.00    --   27.42 -99.00-120.00  102
  3  ω    -10.00  50.00   1.00    1.00    --   27.42  57.00 120.00   60
  4  ω    -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       'ω 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/[σ²(Fo²)+(0.0342P)²+0.1751P] where P=(Fo²+2Fc²)/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 > 2σ(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
_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:
 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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.39167(2) 0.75231(2) 0.67686(2) 0.02809(11) Uani 1 1 d . . . . .
N2 N 0.60372(19) 0.8126(3) 0.8409(2) 0.0291(7) Uani 1 1 d . . . . .
C1 C 0.6379(2) 0.6733(3) 0.7380(2) 0.0236(8) Uani 1 1 d . . . . .
C4 C 0.6518(3) 0.9104(3) 0.7104(3) 0.0375(9) Uani 1 1 d . . . . .
H4A H 0.629144 0.983267 0.740892 0.056 Uiso 1 1 calc GR . . . .
H4B H 0.619073 0.904167 0.656337 0.056 Uiso 1 1 calc GR . . . .
H4C H 0.719444 0.918376 0.700460 0.056 Uiso 1 1 calc GR . . . .
N3 N 0.5906(2) 0.6976(3) 0.8692(2) 0.0296(7) Uani 1 1 d . . . . .
C9 C 0.6323(3) 0.4785(4) 0.5385(3) 0.0362(9) Uani 1 1 d . . . . .
H9 H 0.595609 0.413527 0.515488 0.043 Uiso 1 1 calc R . . . .
C6 C 0.7433(2) 0.6690(3) 0.6082(2) 0.0315(8) Uani 1 1 d . . . . .
H6 H 0.781426 0.732023 0.631906 0.038 Uiso 1 1 calc R . . . .
N1 N 0.6332(2) 0.7969(3) 0.76121(19) 0.0257(7) Uani 1 1 d . . . . .
C5 C 0.6637(2) 0.6242(3) 0.6527(2) 0.0261(8) Uani 1 1 d . . . . .
C8 C 0.7102(3) 0.5236(4) 0.4933(2) 0.0380(9) Uani 1 1 d . . . . .
H8 H 0.725505 0.490305 0.439773 0.046 Uiso 1 1 calc R . . . .
C2 C 0.6099(2) 0.6089(3) 0.8096(2) 0.0286(8) Uani 1 1 d . . . . .
H2 H 0.605107 0.521820 0.815904 0.034 Uiso 1 1 calc R . . . .
C7 C 0.7654(3) 0.6192(4) 0.5288(2) 0.0384(9) Uani 1 1 d . . . . .
H7 H 0.817850 0.650211 0.498647 0.046 Uiso 1 1 calc R . . . .
C10 C 0.6080(2) 0.5283(3) 0.6172(2) 0.0290(8) Uani 1 1 d . . . . .
H10 H 0.554732 0.498111 0.646571 0.035 Uiso 1 1 calc R . . . .
C3 C 0.5584(3) 0.6791(4) 0.9576(2) 0.0454(10) Uani 1 1 d . . . . .
H3A H 0.576076 0.751086 0.991542 0.068 Uiso 1 1 calc GR . . . .
H3B H 0.588026 0.604764 0.980861 0.068 Uiso 1 1 calc GR . . . .
H3C H 0.490060 0.669260 0.958486 0.068 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0536
4 14 -6 0.1392
18 -4 -7 0.1701
3 1 0 0.2080
0 -5 -2 0.1385
0 5 2 0.1285
-3 -1 0 0.1775
2 -3 -1 0.1114
0 0 -1 0.0516
-7 14 3 0.1773
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
N3 N2 N1 104.1(3) . . ?
N1 C1 C5 126.3(3) . . ?
N1 C1 C2 104.5(3) . . ?
C2 C1 C5 129.2(3) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
N2 N3 C2 112.9(3) . . ?
N2 N3 C3 119.0(3) . . ?
C2 N3 C3 128.1(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C10 C9 C8 121.0(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C7 C6 C5 119.6(3) . . ?
N2 N1 C1 112.7(3) . . ?
N2 N1 C4 117.5(3) . . ?
C1 N1 C4 129.7(3) . . ?
C6 C5 C1 121.7(3) . . ?
C6 C5 C10 119.7(3) . . ?
C10 C5 C1 118.6(3) . . ?
C9 C8 H8 120.5 . . ?
C9 C8 C7 119.1(4) . . ?
C7 C8 H8 120.5 . . ?
C1 C2 H2 127.1 . . ?
N3 C2 C1 105.8(3) . . ?
N3 C2 H2 127.1 . . ?
C6 C7 C8 120.9(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C10 C5 119.7(3) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
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 . . ?
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
N2 N3 1.308(5) . ?
N2 N1 1.319(4) . ?
C1 N1 1.360(5) . ?
C1 C5 1.471(5) . ?
C1 C2 1.364(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 N1 1.463(4) . ?
N3 C2 1.349(5) . ?
N3 C3 1.462(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.381(5) . ?
C9 C10 1.377(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.393(5) . ?
C6 C7 1.380(5) . ?
C5 C10 1.393(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.387(5) . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
