# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_18ma141_jpb-mephtzm
_database_code_depnum_ccdc_archive 'CCDC 2016764'
loop_
_audit_author_name
_audit_author_address
'Juerg Hauser'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_audit_creation_date             2018-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        '1,3-dimethyl-4-phenyl-1,2,3-triazolium iodide'
_chemical_formula_moiety         'C10 H12 N3, I'
_chemical_formula_sum            'C10 H12 I N3'
_chemical_formula_weight         301.13
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'

_cell_length_a                   13.9563(2)
_cell_length_b                   10.5922(2)
_cell_length_c                   15.5819(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2303.44(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4142
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.7480
_cell_measurement_theta_min      2.6020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
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

_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.105
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1781
_reflns_number_total             2641
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.068
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 . ?

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 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_19ma002_jpb400
_database_code_depnum_ccdc_archive 'CCDC 2016765'
loop_
_audit_author_name
_audit_author_address
'Juerg Hauser'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_audit_creation_date             2019-01-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
'1,3-dimethyl-4-phenyl-1,2,3-triazolium tetrafluoroborate'
_chemical_formula_moiety         'C10 H12 N3, B F4'
_chemical_formula_sum            'C10 H12 B F4 N3'
_chemical_formula_weight         261.04
_chemical_melting_point          ?
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'

_cell_length_a                   14.45770(10)
_cell_length_b                   10.55260(10)
_cell_length_c                   15.71970(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2398.30(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12105
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      76.8700
_cell_measurement_theta_min      5.6270
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.716
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19564
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.042
_diffrn_reflns_theta_min         5.629
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 120.00   0.50    0.05    --   47.95  47.00  61.00  170
  2  ω     35.00 120.00   0.50    0.18    --  107.11-128.00  44.00  170
  3  ω     87.00 174.00   0.50    0.18    --  107.11  73.00-121.00  174
  4  ω    -31.00  54.00   0.50    0.05    --  -18.75  45.00 -90.00  170
  5  ω    -66.00  -9.00   0.50    0.05    --  -18.75 125.00 150.00  114
  6  ω     32.00  96.00   0.50    0.05    --   47.95-125.00 -30.00  128
  7  ω     35.00 117.00   0.50    0.18    --  107.11-125.00 120.00  164
  8  ω     36.00 120.00   0.50    0.18    --  107.11 -45.00-150.00  168
  9  ω     91.00 174.00   0.50    0.18    --  107.11  61.00-180.00  166
 10  ω     35.00 129.00   0.50    0.18    --  107.11 -73.00 109.00  188
 11  ω     33.00 120.00   0.50    0.05    --   47.95  57.00-120.00  174
 12  ω     26.00 120.00   0.50    0.05    --   47.95  77.00 -60.00  188
 13  ω     26.00 120.00   0.50    0.05    --   47.95  77.00 150.00  188
 14  ω     95.00 143.00   0.50    0.18    --  107.11  30.00 150.00   96
 15  ω     94.00 174.00   0.50    0.18    --  107.11  15.00  90.00  160
 16  ω     94.00 174.00   0.50    0.18    --  107.11  15.00   0.00  160
;
_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      0.0861397000
_diffrn_orient_matrix_UB_12      0.0831880000
_diffrn_orient_matrix_UB_13      0.0144899000
_diffrn_orient_matrix_UB_21      -0.0095945000
_diffrn_orient_matrix_UB_22      -0.0188170000
_diffrn_orient_matrix_UB_23      0.0967793000
_diffrn_orient_matrix_UB_31      0.0619988000
_diffrn_orient_matrix_UB_32      -0.1184693000
_diffrn_orient_matrix_UB_33      -0.0051826000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2221
_reflns_number_total             2490
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (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)'
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     200
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.131
_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)+(0.0712P)²+1.0157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1343
_refine_special_details          ?
_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. Restrained distances
 B2-F3 \\sim B2A-F3A
 with sigma of 0.02
 B2-F4 \\sim B2A-F4A
 with sigma of 0.02
 B2-F5 \\sim B2A-F5A
 with sigma of 0.02
 B2-F6 \\sim B2A-F6A
 with sigma of 0.02
 F3-F4 \\sim F3A-F4A
 with sigma of 0.04
 F3-F5 \\sim F3A-F5A
 with sigma of 0.04
 F3-F6 \\sim F3A-F6A
 with sigma of 0.04
 F4-F5 \\sim F4A-F5A
 with sigma of 0.04
 F4-F6 \\sim F4A-F6A
 with sigma of 0.04
 F5-F6 \\sim F5A-F6A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
F3 \\sim F4 \\sim F5 \\sim F6 \\sim B2 \\sim F3A \\sim F4A \\sim F5A \\sim F6A
\\sim B2A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 F3, F4, F5, F6, B2, F3A, F4A, F5A, F6A, B2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(B2A)=1-FVAR(1)
 Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=Sof(B2)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
6.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.87616(8) 0.81629(12) 0.23717(8) 0.0274(3) Uani 1 1 d . . . . .
N2 N 0.90615(9) 0.82903(12) 0.15843(8) 0.0323(3) Uani 1 1 d . . . . .
N3 N 0.91156(9) 0.71211(13) 0.12984(8) 0.0316(3) Uani 1 1 d . . . . .
C1 C 0.86274(9) 0.69300(13) 0.25935(9) 0.0264(3) Uani 1 1 d . . . . .
C2 C 0.88601(10) 0.62577(14) 0.18831(9) 0.0307(3) Uani 1 1 d . . . . .
H2 H 0.884519 0.538217 0.181682 0.037 Uiso 1 1 calc R . . . .
C3 C 0.94519(15) 0.68914(19) 0.04324(11) 0.0478(5) Uani 1 1 d . . . . .
H3A H 0.941800 0.766259 0.010992 0.072 Uiso 1 1 calc GR . . . .
H3B H 0.907601 0.625529 0.016578 0.072 Uiso 1 1 calc GR . . . .
H3C H 1.008191 0.660596 0.045427 0.072 Uiso 1 1 calc GR . . . .
C4 C 0.86289(12) 0.93048(15) 0.28810(11) 0.0381(4) Uani 1 1 d . . . . .
H4A H 0.891416 1.001202 0.260036 0.057 Uiso 1 1 calc GR . . . .
H4B H 0.890604 0.918869 0.343042 0.057 Uiso 1 1 calc GR . . . .
H4C H 0.797923 0.946487 0.294713 0.057 Uiso 1 1 calc GR . . . .
C5 C 0.83378(10) 0.64665(13) 0.34345(9) 0.0278(3) Uani 1 1 d . . . . .
C6 C 0.75663(11) 0.69518(16) 0.38487(10) 0.0350(4) Uani 1 1 d . . . . .
H6 H 0.722172 0.759799 0.360099 0.042 Uiso 1 1 calc R . . . .
C7 C 0.73133(12) 0.64628(18) 0.46378(11) 0.0418(4) Uani 1 1 d . . . . .
H7 H 0.680237 0.679254 0.492095 0.050 Uiso 1 1 calc R . . . .
C8 C 0.78146(12) 0.54936(17) 0.50022(11) 0.0415(4) Uani 1 1 d . . . . .
H8 H 0.764102 0.517224 0.552949 0.050 Uiso 1 1 calc R . . . .
C9 C 0.85753(13) 0.49980(16) 0.45851(11) 0.0409(4) Uani 1 1 d . . . . .
H9 H 0.890896 0.433830 0.482947 0.049 Uiso 1 1 calc R . . . .
C10 C 0.88403(11) 0.54835(15) 0.38037(10) 0.0347(4) Uani 1 1 d . . . . .
H10 H 0.935416 0.515316 0.352535 0.042 Uiso 1 1 calc R . . . .
F3 F 0.9261(4) 0.2438(6) 0.2524(2) 0.0607(13) Uani 0.652(15) 1 d D U P A 1
F4 F 0.8111(3) 0.3400(5) 0.1833(4) 0.0591(13) Uani 0.652(15) 1 d D U P A 1
F5 F 0.9523(4) 0.3430(5) 0.1276(4) 0.0474(11) Uani 0.652(15) 1 d D U P A 1
F6 F 0.8715(6) 0.1603(3) 0.1312(3) 0.0779(15) Uani 0.652(15) 1 d D U P A 1
B2 B 0.8899(5) 0.2690(6) 0.1736(4) 0.0298(13) Uani 0.652(15) 1 d D U P A 1
F3A F 0.9318(8) 0.2165(11) 0.2394(7) 0.075(2) Uani 0.348(15) 1 d D U P A 2
F4A F 0.8206(8) 0.3504(8) 0.2065(9) 0.067(3) Uani 0.348(15) 1 d D U P A 2
F5A F 0.9397(9) 0.3268(12) 0.1141(8) 0.061(3) Uani 0.348(15) 1 d D U P A 2
F6A F 0.8309(7) 0.1751(11) 0.1354(6) 0.074(2) Uani 0.348(15) 1 d D U P A 2
B2A B 0.8831(10) 0.2658(13) 0.1727(9) 0.037(3) Uani 0.348(15) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
N1 N2 1.3182(18) . ?
N1 C1 1.3609(19) . ?
N1 C4 1.4594(19) . ?
N2 N3 1.3155(19) . ?
N3 C2 1.346(2) . ?
N3 C3 1.466(2) . ?
C1 C2 1.365(2) . ?
C1 C5 1.470(2) . ?
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 1.389(2) . ?
C5 C10 1.393(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9300 . ?
F3 B2 1.371(6) . ?
F4 B2 1.372(6) . ?
F5 B2 1.395(7) . ?
F6 B2 1.352(6) . ?
F3A B2A 1.365(13) . ?
F4A B2A 1.377(13) . ?
F5A B2A 1.391(13) . ?
F6A B2A 1.353(13) . ?

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
N2 N1 C1 112.64(12) . . ?
N2 N1 C4 118.30(13) . . ?
C1 N1 C4 129.05(13) . . ?
N3 N2 N1 104.17(12) . . ?
N2 N3 C2 112.65(12) . . ?
N2 N3 C3 119.49(14) . . ?
C2 N3 C3 127.84(14) . . ?
N1 C1 C2 104.60(13) . . ?
N1 C1 C5 126.09(13) . . ?
C2 C1 C5 129.25(14) . . ?
N3 C2 C1 105.93(13) . . ?
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 121.83(14) . . ?
C6 C5 C10 119.86(14) . . ?
C10 C5 C1 118.28(13) . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.46(15) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.48(16) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.11(15) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.04(16) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.05(15) . . ?
C9 C10 H10 120.0 . . ?
F3 B2 F4 108.8(5) . . ?
F3 B2 F5 109.3(6) . . ?
F4 B2 F5 106.7(5) . . ?
F6 B2 F3 110.9(5) . . ?
F6 B2 F4 110.8(6) . . ?
F6 B2 F5 110.3(5) . . ?
F3A B2A F4A 106.9(11) . . ?
F3A B2A F5A 112.5(12) . . ?
F4A B2A F5A 109.9(12) . . ?
F6A B2A F3A 110.6(11) . . ?
F6A B2A F4A 105.1(11) . . ?
F6A B2A F5A 111.6(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_19ma021_jpb478-i3
_database_code_depnum_ccdc_archive 'CCDC 2016766'
loop_
_audit_author_name
_audit_author_address
'Juerg Hauser'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_audit_creation_date             2019-02-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
'1,3-dimethyl-4-phenyl-1,2,3-triazolium triiodide'
_chemical_formula_moiety         'C10 H12 N3, I3'
_chemical_formula_sum            'C10 H12 I3 N3'
_chemical_formula_weight         554.93
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'

_cell_length_a                   20.4846(8)
_cell_length_b                   9.4451(3)
_cell_length_c                   15.8942(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.242(4)
_cell_angle_gamma                90
_cell_volume                     3035.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7504
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.3690
_cell_measurement_theta_min      4.3700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2608
_reflns_number_total             3110
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         2.170
_refine_diff_density_min         -0.963
_refine_diff_density_rms         0.285
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0652
_refine_ls_restrained_S_all      1.102
_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
_refine_special_details          Twin
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 . ?

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 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
