# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1-OTf
_database_code_depnum_ccdc_archive 'CCDC 2018732'
loop_
_audit_author_name
_audit_author_address
'Alessandra Forni'
;CNR SCITEC
Italy
;
_audit_update_record             
;
2020-07-24 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
#data_gdc1n

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1,3-dimethyl-2-(4-methylphenyl)-1H-benzimidazolium triflate'
_chemical_formula_moiety         'C16 H17 N2, C F3 O3 S'
_chemical_formula_sum            'C17 H17 F3 N2 O3 S'
_chemical_formula_weight         386.38

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5128(5)
_cell_length_b                   8.6916(5)
_cell_length_c                   13.7154(8)
_cell_angle_alpha                104.2767(9)
_cell_angle_beta                 91.5096(9)
_cell_angle_gamma                91.7180(9)
_cell_volume                     867.02(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6780
_cell_measurement_theta_min      2.418
_cell_measurement_theta_max      30.382

_exptl_crystal_description       lamina
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   0.880
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker, 1997
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            19531
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.533
_diffrn_reflns_theta_max         30.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5294
_reflns_number_gt                3976
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  SHELXL-2014/7

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²+0.1729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5294
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S1 S 0.36432(5) 0.17385(4) 0.74083(3) 0.04410(11) Uani 1 1 d . . . . .
F1 F 0.23921(17) 0.35071(14) 0.90788(9) 0.0794(4) Uani 1 1 d . . . . .
F2 F 0.52326(18) 0.35179(16) 0.90426(9) 0.0888(4) Uani 1 1 d . . . . .
F3 F 0.37507(19) 0.48061(12) 0.81770(9) 0.0786(3) Uani 1 1 d . . . . .
O1 O 0.3726(2) 0.04236(14) 0.78571(10) 0.0716(4) Uani 1 1 d . . . . .
O2 O 0.51506(18) 0.20090(17) 0.68501(10) 0.0703(4) Uani 1 1 d . . . . .
O3 O 0.19562(16) 0.18881(13) 0.69274(9) 0.0562(3) Uani 1 1 d . . . . .
N1 N 0.73393(15) 0.69116(13) 0.58945(8) 0.0393(2) Uani 1 1 d . . . . .
N2 N 0.81742(15) 0.52903(13) 0.68008(8) 0.0391(2) Uani 1 1 d . . . . .
C1 C 0.80155(18) 0.44067(15) 0.58094(10) 0.0405(3) Uani 1 1 d . . . . .
C2 C 0.8314(2) 0.28034(17) 0.53855(13) 0.0509(4) Uani 1 1 d . . . . .
H2 H 0.8683 0.2123 0.5772 0.061 Uiso 1 1 calc R U . . .
C3 C 0.8026(2) 0.22965(19) 0.43565(13) 0.0589(4) Uani 1 1 d . . . . .
H3 H 0.8203 0.1239 0.4039 0.071 Uiso 1 1 calc R U . . .
C4 C 0.7477(2) 0.3319(2) 0.37800(12) 0.0613(5) Uani 1 1 d . . . . .
H4 H 0.7300 0.2921 0.3089 0.074 Uiso 1 1 calc R U . . .
C5 C 0.7187(2) 0.4907(2) 0.41976(11) 0.0533(4) Uani 1 1 d . . . . .
H5 H 0.6814 0.5586 0.3811 0.064 Uiso 1 1 calc R U . . .
C6 C 0.74886(18) 0.54216(16) 0.52347(10) 0.0409(3) Uani 1 1 d . . . . .
C7 C 0.6759(2) 0.83253(19) 0.55909(12) 0.0528(4) Uani 1 1 d . . . . .
H7A H 0.6367 0.9091 0.6169 0.079 Uiso 1 1 calc R U . . .
H7B H 0.5794 0.8032 0.5100 0.079 Uiso 1 1 calc R U . . .
H7C H 0.7735 0.8779 0.5304 0.079 Uiso 1 1 calc R U . . .
C8 C 0.8847(2) 0.46659(18) 0.76294(12) 0.0516(4) Uani 1 1 d . . . . .
H8A H 0.9243 0.5532 0.8181 0.077 Uiso 1 1 calc R U . . .
H8B H 0.9826 0.3997 0.7408 0.077 Uiso 1 1 calc R U . . .
H8C H 0.7914 0.4058 0.7844 0.077 Uiso 1 1 calc R U . . .
C9 C 0.77685(17) 0.67986(15) 0.68298(9) 0.0362(3) Uani 1 1 d . . . . .
C10 C 0.78136(17) 0.81081(15) 0.77404(9) 0.0366(3) Uani 1 1 d . . . . .
C11 C 0.69298(19) 0.79531(16) 0.85924(10) 0.0429(3) Uani 1 1 d . . . . .
H11 H 0.6281 0.7021 0.8583 0.051 Uiso 1 1 calc R U . . .
C12 C 0.7016(2) 0.91834(18) 0.94522(11) 0.0460(3) Uani 1 1 d . . . . .
H12 H 0.6421 0.9070 1.0018 0.055 Uiso 1 1 calc R U . . .
C13 C 0.79747(19) 1.05847(16) 0.94860(11) 0.0441(3) Uani 1 1 d . . . . .
C14 C 0.8847(2) 1.07280(16) 0.86356(12) 0.0475(3) Uani 1 1 d . . . . .
H14 H 0.9491 1.1663 0.8648 0.057 Uiso 1 1 calc R U . . .
C15 C 0.8782(2) 0.95102(16) 0.77672(11) 0.0441(3) Uani 1 1 d . . . . .
H15 H 0.9381 0.9627 0.7204 0.053 Uiso 1 1 calc R U . . .
C16 C 0.8067(3) 1.1913(2) 1.04280(13) 0.0615(5) Uani 1 1 d . . . . .
H16A H 0.9284 1.2280 1.0584 0.092 Uiso 1 1 calc R U . . .
H16B H 0.7605 1.1535 1.0976 0.092 Uiso 1 1 calc R U . . .
H16C H 0.7372 1.2772 1.0326 0.092 Uiso 1 1 calc R U . . .
C17 C 0.3763(2) 0.34650(18) 0.84832(12) 0.0500(3) Uani 1 1 d . . . . .


_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
S1 O1 1.4276(13) . ?
S1 O2 1.4291(13) . ?
S1 O3 1.4375(12) . ?
S1 C17 1.8241(15) . ?
F1 C17 1.3270(19) . ?
F2 C17 1.3211(19) . ?
F3 C17 1.3330(19) . ?
N1 C9 1.3422(17) . ?
N1 C6 1.3945(16) . ?
N1 C7 1.4658(18) . ?
N2 C9 1.3461(16) . ?
N2 C1 1.3870(16) . ?
N2 C8 1.4600(18) . ?
C1 C6 1.380(2) . ?
C1 C2 1.3987(19) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3922(19) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.4665(16) . ?
C10 C11 1.3920(19) . ?
C10 C15 1.3924(18) . ?
C11 C12 1.3813(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(2) . ?
C13 C16 1.5040(19) . ?
C14 C15 1.3833(19) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O1 S1 O2 116.17(9) . . ?
O1 S1 O3 114.81(8) . . ?
O2 S1 O3 114.09(8) . . ?
O1 S1 C17 103.72(8) . . ?
O2 S1 C17 102.63(8) . . ?
O3 S1 C17 102.93(7) . . ?
C9 N1 C6 108.47(11) . . ?
C9 N1 C7 127.19(11) . . ?
C6 N1 C7 124.31(12) . . ?
C9 N2 C1 108.44(11) . . ?
C9 N2 C8 127.58(11) . . ?
C1 N2 C8 123.72(12) . . ?
C6 C1 N2 107.19(11) . . ?
C6 C1 C2 122.18(13) . . ?
N2 C1 C2 130.62(14) . . ?
C3 C2 C1 115.69(16) . . ?
C3 C2 H2 122.2 . . ?
C1 C2 H2 122.2 . . ?
C2 C3 C4 122.00(15) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 122.40(15) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 115.64(16) . . ?
C4 C5 H5 122.2 . . ?
C6 C5 H5 122.2 . . ?
C1 C6 C5 122.07(13) . . ?
C1 C6 N1 106.73(11) . . ?
C5 C6 N1 131.20(14) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 N2 109.17(11) . . ?
N1 C9 C10 125.71(12) . . ?
N2 C9 C10 125.12(12) . . ?
C11 C10 C15 119.30(12) . . ?
C11 C10 C9 120.65(12) . . ?
C15 C10 C9 120.03(12) . . ?
C12 C11 C10 120.03(13) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 121.10(14) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 118.45(12) . . ?
C14 C13 C16 120.91(15) . . ?
C12 C13 C16 120.65(15) . . ?
C13 C14 C15 121.43(13) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 119.69(13) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F2 C17 F1 107.51(14) . . ?
F2 C17 F3 107.19(14) . . ?
F1 C17 F3 106.33(14) . . ?
F2 C17 S1 112.03(12) . . ?
F1 C17 S1 112.74(11) . . ?
F3 C17 S1 110.70(11) . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.045

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_preparation       Luminescent,Luminescent

####################################################################### 
# 
# 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_1-NO3H2O
_database_code_depnum_ccdc_archive 'CCDC 2018734'
loop_
_audit_author_name
_audit_author_address
'Alessandra Forni'
;CNR SCITEC
Italy
;
_audit_update_record             
;
2020-07-24 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
#data_gdc3

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;1,3-dimethyl-2-(4-methylphenyl)-1H-benzimidazolium nitrate
 hydrate
;
_chemical_formula_moiety         'C16 H17 N2, N O3, O'
_chemical_formula_sum            'C16 H17 N3 O4'
_chemical_formula_weight         315.32

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.456(2)
_cell_length_b                   9.299(3)
_cell_length_c                   12.571(3)
_cell_angle_alpha                75.967(4)
_cell_angle_beta                 77.518(4)
_cell_angle_gamma                70.952(4)
_cell_volume                     790.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3788
_cell_measurement_theta_min      2.358
_cell_measurement_theta_max      30.32

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker, 1997
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            14379
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.689
_diffrn_reflns_theta_max         30.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4815
_reflns_number_gt                2538
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  SHELXL-2014/7

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1524P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4811
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.2593
_refine_ls_wR_factor_gt          0.2153
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.1128(2) 1.03955(18) 0.69239(13) 0.0473(4) Uani 1 1 d . . . . .
N2 N 0.3051(2) 0.85876(18) 0.60275(13) 0.0447(4) Uani 1 1 d . . . . .
C1 C 0.2437(3) 0.9899(2) 0.52334(15) 0.0460(5) Uani 1 1 d . . . . .
C2 C 0.2807(3) 1.0173(3) 0.40820(17) 0.0560(5) Uani 1 1 d . . . . .
H2 H 0.3624 0.9416 0.3692 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1893(4) 1.1635(3) 0.35483(19) 0.0650(6) Uani 1 1 d . . . . .
H3 H 0.2088 1.1858 0.2777 0.078 Uiso 1 1 calc R U . . .
C4 C 0.0697(4) 1.2779(3) 0.4121(2) 0.0639(6) Uani 1 1 d . . . . .
H4 H 0.0133 1.3750 0.3725 0.077 Uiso 1 1 calc R U . . .
C5 C 0.0326(3) 1.2515(2) 0.52539(19) 0.0573(5) Uani 1 1 d . . . . .
H5 H -0.0488 1.3279 0.5638 0.069 Uiso 1 1 calc R U . . .
C6 C 0.1225(3) 1.1045(2) 0.58046(16) 0.0466(5) Uani 1 1 d . . . . .
C7 C -0.0157(3) 1.1170(3) 0.78113(19) 0.0632(6) Uani 1 1 d . . . . .
H7A H -0.0399 1.0406 0.8447 0.095 Uiso 1 1 calc R U . . .
H7B H -0.1346 1.1790 0.7556 0.095 Uiso 1 1 calc R U . . .
H7C H 0.0436 1.1822 0.8011 0.095 Uiso 1 1 calc R U . . .
C8 C 0.4393(3) 0.7126(2) 0.57712(19) 0.0570(5) Uani 1 1 d . . . . .
H8A H 0.4971 0.6535 0.6414 0.085 Uiso 1 1 calc R U . . .
H8B H 0.5374 0.7335 0.5173 0.085 Uiso 1 1 calc R U . . .
H8C H 0.3716 0.6548 0.5558 0.085 Uiso 1 1 calc R U . . .
C9 C 0.2240(3) 0.8912(2) 0.70346(15) 0.0439(4) Uani 1 1 d . . . . .
C10 C 0.2460(3) 0.7859(2) 0.81027(16) 0.0463(5) Uani 1 1 d . . . . .
C11 C 0.2962(3) 0.8312(2) 0.89566(17) 0.0507(5) Uani 1 1 d . . . . .
H11 H 0.3240 0.9250 0.8830 0.061 Uiso 1 1 calc R U . . .
C12 C 0.3044(3) 0.7357(2) 0.99897(17) 0.0540(5) Uani 1 1 d . . . . .
H12 H 0.3401 0.7653 1.0550 0.065 Uiso 1 1 calc R U . . .
C13 C 0.2599(3) 0.5965(2) 1.02020(16) 0.0526(5) Uani 1 1 d . . . . .
C14 C 0.2162(3) 0.5514(2) 0.93361(18) 0.0548(5) Uani 1 1 d . . . . .
H14 H 0.1909 0.4567 0.9461 0.066 Uiso 1 1 calc R U . . .
C15 C 0.2096(3) 0.6437(2) 0.82953(17) 0.0509(5) Uani 1 1 d . . . . .
H15 H 0.1808 0.6109 0.7726 0.061 Uiso 1 1 calc R U . . .
C16 C 0.2569(4) 0.4980(3) 1.13440(18) 0.0676(7) Uani 1 1 d . . . . .
H16A H 0.3398 0.5188 1.1738 0.101 Uiso 1 1 calc R U . . .
H16B H 0.3007 0.3906 1.1285 0.101 Uiso 1 1 calc R U . . .
H16C H 0.1284 0.5217 1.1737 0.101 Uiso 1 1 calc R U . . .
N3 N 0.4037(4) 0.2914(3) 0.7372(2) 0.0794(7) Uani 1 1 d . . . . .
O1 O 0.2554(4) 0.3616(3) 0.6980(2) 0.1140(9) Uani 1 1 d . . . . .
O2 O 0.4160(6) 0.1780(4) 0.8134(3) 0.1441(11) Uani 1 1 d . . . . .
O3 O 0.5484(3) 0.3343(3) 0.6984(2) 0.1099(8) Uani 1 1 d . . . . .
O4 O 0.7063(9) 0.9015(7) 0.9334(5) 0.253(3) Uani 1 1 d . . . . .


_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 C9 1.349(2) . ?
N1 C6 1.386(2) . ?
N1 C7 1.469(3) . ?
N2 C9 1.340(2) . ?
N2 C1 1.391(2) . ?
N2 C8 1.462(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.389(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.463(3) . ?
C10 C15 1.390(3) . ?
C10 C11 1.402(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 C16 1.504(3) . ?
C14 C15 1.381(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N3 O1 1.224(3) . ?
N3 O3 1.233(3) . ?
N3 O2 1.234(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
C9 N1 C6 108.62(16) . . ?
C9 N1 C7 126.70(17) . . ?
C6 N1 C7 124.34(17) . . ?
C9 N2 C1 108.71(16) . . ?
C9 N2 C8 127.10(17) . . ?
C1 N2 C8 124.18(17) . . ?
C6 C1 C2 121.21(19) . . ?
C6 C1 N2 106.72(17) . . ?
C2 C1 N2 132.1(2) . . ?
C3 C2 C1 116.2(2) . . ?
C3 C2 H2 121.9 . . ?
C1 C2 H2 121.9 . . ?
C2 C3 C4 122.4(2) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 116.8(2) . . ?
C4 C5 H5 121.6 . . ?
C6 C5 H5 121.6 . . ?
N1 C6 C1 106.81(17) . . ?
N1 C6 C5 131.4(2) . . ?
C1 C6 C5 121.78(19) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 N1 109.14(16) . . ?
N2 C9 C10 127.05(17) . . ?
N1 C9 C10 123.81(17) . . ?
C15 C10 C11 119.53(18) . . ?
C15 C10 C9 120.53(17) . . ?
C11 C10 C9 119.89(17) . . ?
C12 C11 C10 119.77(19) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 121.0(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.35(18) . . ?
C14 C13 C16 120.9(2) . . ?
C12 C13 C16 120.8(2) . . ?
C15 C14 C13 121.7(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C10 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 N3 O3 118.9(3) . . ?
O1 N3 O2 123.0(3) . . ?
O3 N3 O2 118.1(3) . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.060

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_1-ICH2Cl2
_database_code_depnum_ccdc_archive 'CCDC 2018735'
loop_
_audit_author_name
_audit_author_address
'Alessandra Forni'
;CNR SCITEC
Italy
;
_audit_update_record             
;
2020-07-24 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
#data_gdc4  

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;1,3-dimethyl-2-(4-methylphenyl)-1H-benzimidazolium iodide
 dichloromethane solvate
;
_chemical_formula_moiety         '2(C16 H17 N2), 2(I), C H2 Cl2'
_chemical_formula_sum            'C33 H36 Cl2 I2 N4'
_chemical_formula_weight         813.36

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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                   17.3639(9)
_cell_length_b                   7.5370(4)
_cell_length_c                   26.8262(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.8189(7)
_cell_angle_gamma                90
_cell_volume                     3377.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.349
_cell_measurement_theta_max      30.487

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.048
_shelx_estimated_absorpt_T_min   0.480
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker, 1997
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            31951
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.578
_diffrn_reflns_theta_max         30.511
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5159
_reflns_number_gt                4935
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  SHELXL-2014/7

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0217P)²+4.5019P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5159
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0482
_refine_ls_wR_factor_gt          0.0476
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.64090(2) 0.07651(2) 0.38871(2) 0.02618(3) Uani 1 1 d . . . . .
N1 N 0.53039(6) 0.66859(14) 0.41292(4) 0.01813(19) Uani 1 1 d . . . . .
N2 N 0.43500(6) 0.77681(15) 0.44355(4) 0.01884(19) Uani 1 1 d . . . . .
C1 C 0.50020(7) 0.74303(17) 0.48599(5) 0.0193(2) Uani 1 1 d . . . . .
C2 C 0.50968(9) 0.76295(19) 0.53903(5) 0.0241(2) Uani 1 1 d . . . . .
H2 H 0.4680 0.8070 0.5523 0.029 Uiso 1 1 calc R U . . .
C3 C 0.58374(9) 0.7145(2) 0.57118(5) 0.0282(3) Uani 1 1 d . . . . .
H3 H 0.5929 0.7248 0.6076 0.034 Uiso 1 1 calc R U . . .
C4 C 0.64556(9) 0.6509(2) 0.55157(5) 0.0274(3) Uani 1 1 d . . . . .
H4 H 0.6955 0.6212 0.5751 0.033 Uiso 1 1 calc R U . . .
C5 C 0.63574(8) 0.62997(19) 0.49873(5) 0.0239(2) Uani 1 1 d . . . . .
H5 H 0.6775 0.5865 0.4854 0.029 Uiso 1 1 calc R U . . .
C6 C 0.56082(7) 0.67661(17) 0.46637(5) 0.0191(2) Uani 1 1 d . . . . .
C7 C 0.57366(8) 0.58987(18) 0.37852(5) 0.0235(2) Uani 1 1 d . . . . .
H7A H 0.5359 0.5627 0.3450 0.035 Uiso 1 1 calc R U . . .
H7B H 0.6000 0.4804 0.3941 0.035 Uiso 1 1 calc R U . . .
H7C H 0.6140 0.6738 0.3735 0.035 Uiso 1 1 calc R U . . .
C8 C 0.35870(8) 0.8510(2) 0.44731(6) 0.0249(3) Uani 1 1 d . . . . .
H8A H 0.3326 0.9137 0.4151 0.037 Uiso 1 1 calc R U . . .
H8B H 0.3686 0.9341 0.4765 0.037 Uiso 1 1 calc R U . . .
H8C H 0.3239 0.7549 0.4528 0.037 Uiso 1 1 calc R U . . .
C9 C 0.45479(7) 0.73057(16) 0.40005(5) 0.0181(2) Uani 1 1 d . . . . .
C10 C 0.40196(7) 0.73795(17) 0.34721(5) 0.0193(2) Uani 1 1 d . . . . .
C11 C 0.32534(8) 0.66428(18) 0.33646(5) 0.0218(2) Uani 1 1 d . . . . .
H11 H 0.3057 0.6210 0.3639 0.026 Uiso 1 1 calc R U . . .
C12 C 0.27803(8) 0.65442(19) 0.28571(5) 0.0240(3) Uani 1 1 d . . . . .
H12 H 0.2259 0.6047 0.2787 0.029 Uiso 1 1 calc R U . . .
C13 C 0.30574(8) 0.71623(19) 0.24478(5) 0.0241(2) Uani 1 1 d . . . . .
C14 C 0.38062(8) 0.7989(2) 0.25614(5) 0.0252(3) Uani 1 1 d . . . . .
H14 H 0.3989 0.8482 0.2288 0.030 Uiso 1 1 calc R U . . .
C15 C 0.42876(8) 0.80996(18) 0.30688(5) 0.0227(2) Uani 1 1 d . . . . .
H15 H 0.4796 0.8662 0.3141 0.027 Uiso 1 1 calc R U . . .
C16 C 0.25724(10) 0.6887(3) 0.18959(6) 0.0337(3) Uani 1 1 d . . . . .
H16A H 0.2689 0.5712 0.1778 0.051 Uiso 1 1 calc R U . . .
H16B H 0.2711 0.7801 0.1675 0.051 Uiso 1 1 calc R U . . .
H16C H 0.2001 0.6968 0.1875 0.051 Uiso 1 1 calc R U . . .
Cl1A Cl 0.42883(14) 0.3655(3) 0.25926(7) 0.0426(4) Uani 0.5 1 d . . P . .
Cl1B Cl 0.42518(14) 0.3252(3) 0.27315(7) 0.0388(3) Uani 0.5 1 d . . P . .
C17 C 0.5000 0.2146(3) 0.2500 0.0317(4) Uani 1 2 d S T P . .
H17 H 0.4736(12) 0.148(3) 0.2196(8) 0.038 Uiso 1 1 d . U . . .


_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 C9 1.3468(16) . ?
N1 C6 1.3875(15) . ?
N1 C7 1.4651(17) . ?
N2 C9 1.3489(16) . ?
N2 C1 1.3928(15) . ?
N2 C8 1.4668(17) . ?
C1 C6 1.3920(18) . ?
C1 C2 1.3951(17) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3979(17) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.4647(16) . ?
C10 C11 1.3972(17) . ?
C10 C15 1.3985(17) . ?
C11 C12 1.3869(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3938(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3984(19) . ?
C13 C16 1.5048(19) . ?
C14 C15 1.3922(18) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
Cl1A C17 1.746(3) . ?
Cl1B C17 1.791(2) . ?
C17 Cl1A 1.746(3) 2_655 ?
C17 Cl1B 1.791(2) 2_655 ?
C17 H17 0.96(2) . ?

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
C9 N1 C6 108.65(10) . . ?
C9 N1 C7 127.62(11) . . ?
C6 N1 C7 123.54(11) . . ?
C9 N2 C1 108.54(10) . . ?
C9 N2 C8 127.29(11) . . ?
C1 N2 C8 124.17(11) . . ?
C6 C1 N2 106.65(11) . . ?
C6 C1 C2 122.22(12) . . ?
N2 C1 C2 131.12(12) . . ?
C3 C2 C1 115.93(13) . . ?
C3 C2 H2 122.0 . . ?
C1 C2 H2 122.0 . . ?
C2 C3 C4 122.08(13) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 121.85(13) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 116.08(13) . . ?
C4 C5 H5 122.0 . . ?
C6 C5 H5 122.0 . . ?
N1 C6 C1 106.99(11) . . ?
N1 C6 C5 131.19(12) . . ?
C1 C6 C5 121.82(12) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 N2 109.16(10) . . ?
N1 C9 C10 124.81(11) . . ?
N2 C9 C10 125.97(11) . . ?
C11 C10 C15 119.57(11) . . ?
C11 C10 C9 119.64(11) . . ?
C15 C10 C9 120.72(11) . . ?
C12 C11 C10 119.98(12) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 121.07(12) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 118.51(12) . . ?
C12 C13 C16 120.55(12) . . ?
C14 C13 C16 120.91(12) . . ?
C15 C14 C13 120.97(12) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C10 119.70(12) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Cl1A C17 Cl1A 98.75(18) 2_655 . ?
Cl1A C17 Cl1B 110.78(13) 2_655 . ?
Cl1A C17 Cl1B 110.78(13) . 2_655 ?
Cl1B C17 Cl1B 124.55(17) . 2_655 ?
Cl1A C17 H17 114.3(13) 2_655 . ?
Cl1A C17 H17 105.5(13) . . ?
Cl1B C17 H17 108.2(13) . . ?
Cl1B C17 H17 99.9(13) 2_655 . ?

_refine_diff_density_max         0.913
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.059

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_preparation       Luminescent


####################################################################### 
# 
# 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_1-NO3EtOH
_database_code_depnum_ccdc_archive 'CCDC 2018733'
loop_
_audit_author_name
_audit_author_address
'Alessandra Forni'
;CNR SCITEC
Italy
;
_audit_update_record             
;
2020-07-24 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
#data_gdc5lt  

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;1,3-dimethyl-2-(4-methylphenyl)-1H-benzimidazolium nitrate
 ethanol solvate
;
_chemical_formula_moiety         'C16 H17 N2, N O3, 0.5(C2 H6 O)'
_chemical_formula_sum            'C17 H20 N3 O3.50'
_chemical_formula_weight         322.36

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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                   46.7400(18)
_cell_length_b                   7.5898(3)
_cell_length_c                   28.5740(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.8120(10)
_cell_angle_gamma                90
_cell_volume                     9703.3(7)
_cell_formula_units_Z            24
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.665
_cell_measurement_theta_max      30.468

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             4104
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker, 1997
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            88189
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -66
_diffrn_reflns_limit_h_max       66
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.489
_diffrn_reflns_theta_max         30.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             14792
_reflns_number_gt                10977
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  SHELXL-2014/7

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0827P)²+4.0300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         14792
_refine_ls_number_parameters     690
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1A O 0.83942(2) 0.63320(13) 0.63763(4) 0.0350(2) Uani 1 1 d . . . . .
O2A O 0.79857(2) 0.78532(14) 0.62417(4) 0.0368(2) Uani 1 1 d D . . . .
O3A O 0.82519(2) 0.80096(14) 0.57338(4) 0.0388(2) Uani 1 1 d . . . . .
N1A N 0.74689(2) 0.48043(12) 0.56788(3) 0.02044(18) Uani 1 1 d . . . . .
N2A N 0.79001(2) 0.34319(13) 0.58867(3) 0.02165(19) Uani 1 1 d . . . . .
N3A N 0.82116(2) 0.73972(13) 0.61158(4) 0.0253(2) Uani 1 1 d . . . . .
O1B O 0.67158(2) 0.17611(14) 0.61662(4) 0.0351(2) Uani 1 1 d . . . . .
O2B O 0.62722(2) 0.29167(14) 0.59817(4) 0.0355(2) Uani 1 1 d . . . . .
O3B O 0.65600(2) 0.34331(14) 0.55224(4) 0.0402(2) Uani 1 1 d . . . . .
N1B N 0.57992(2) 0.99799(13) 0.55113(3) 0.02167(19) Uani 1 1 d . . . . .
N2B N 0.62420(2) 0.87494(13) 0.56859(3) 0.02266(19) Uani 1 1 d . . . . .
N3B N 0.65164(2) 0.27069(14) 0.58928(4) 0.0266(2) Uani 1 1 d . . . . .
O1C O 0.50105(2) 0.16108(13) 0.41575(4) 0.0391(2) Uani 1 1 d . . . . .
O2C O 0.48517(2) 0.38834(14) 0.37057(4) 0.0448(3) Uani 1 1 d . . . . .
O3C O 0.52676(2) 0.26186(15) 0.36971(4) 0.0426(3) Uani 1 1 d . . . . .
N1C N 0.54125(2) 0.66420(13) 0.39418(4) 0.0241(2) Uani 1 1 d . . . . .
N2C N 0.58459(2) 0.53105(13) 0.42006(3) 0.02189(19) Uani 1 1 d . . . . .
N3C N 0.50415(2) 0.27093(14) 0.38496(4) 0.0276(2) Uani 1 1 d . . . . .
C1A C 0.78405(2) 0.38724(15) 0.53952(4) 0.0211(2) Uani 1 1 d . . . . .
C2A C 0.80008(3) 0.35675(16) 0.50609(4) 0.0256(2) Uani 1 1 d . . . . .
H2A H 0.8189 0.2987 0.5152 0.031 Uiso 1 1 calc R U . . .
C3A C 0.78713(3) 0.41561(17) 0.45888(4) 0.0276(2) Uani 1 1 d . . . . .
H3A H 0.7974 0.3986 0.4350 0.033 Uiso 1 1 calc R U . . .
C4A C 0.75917(3) 0.49997(16) 0.44542(4) 0.0274(2) Uani 1 1 d . . . . .
H4A H 0.7509 0.5368 0.4125 0.033 Uiso 1 1 calc R U . . .
C5A C 0.74318(3) 0.53127(15) 0.47855(4) 0.0242(2) Uani 1 1 d . . . . .
H5A H 0.7243 0.5887 0.4694 0.029 Uiso 1 1 calc R U . . .
C6A C 0.75654(2) 0.47317(14) 0.52625(4) 0.0205(2) Uani 1 1 d . . . . .
C7A C 0.71916(3) 0.56504(16) 0.56998(4) 0.0254(2) Uani 1 1 d . . . . .
H7A1 H 0.7030 0.4782 0.5625 0.038 Uiso 1 1 calc R U . . .
H7A2 H 0.7141 0.6610 0.5460 0.038 Uiso 1 1 calc R U . . .
H7A3 H 0.7218 0.6126 0.6028 0.038 Uiso 1 1 calc R U . . .
C8A C 0.81528(3) 0.23339(17) 0.61463(5) 0.0280(2) Uani 1 1 d . . . . .
H8A1 H 0.8120 0.1895 0.6449 0.042 Uiso 1 1 calc R U . . .
H8A2 H 0.8337 0.3034 0.6224 0.042 Uiso 1 1 calc R U . . .
H8A3 H 0.8171 0.1335 0.5939 0.042 Uiso 1 1 calc R U . . .
C9A C 0.76736(2) 0.40105(14) 0.60491(4) 0.0206(2) Uani 1 1 d . . . . .
C10A C 0.76579(3) 0.38296(15) 0.65514(4) 0.0221(2) Uani 1 1 d . . . . .
C11A C 0.73977(3) 0.32060(16) 0.66466(4) 0.0256(2) Uani 1 1 d . . . . .
H11A H 0.7228 0.2892 0.6384 0.031 Uiso 1 1 calc R U . . .
C12A C 0.73891(3) 0.30494(16) 0.71264(4) 0.0278(2) Uani 1 1 d . . . . .
H12A H 0.7213 0.2623 0.7190 0.033 Uiso 1 1 calc R U . . .
C13A C 0.76351(3) 0.35077(16) 0.75177(4) 0.0271(2) Uani 1 1 d . . . . .
C14A C 0.78907(3) 0.41553(17) 0.74171(4) 0.0268(2) Uani 1 1 d . . . . .
H14A H 0.8058 0.4494 0.7679 0.032 Uiso 1 1 calc R U . . .
C15A C 0.79036(3) 0.43122(16) 0.69402(4) 0.0248(2) Uani 1 1 d . . . . .
H15A H 0.8080 0.4748 0.6878 0.030 Uiso 1 1 calc R U . . .
C16A C 0.76266(3) 0.3292(2) 0.80373(5) 0.0359(3) Uani 1 1 d . . . . .
H16A H 0.7429 0.3640 0.8061 0.054 Uiso 1 1 calc R U . . .
H16B H 0.7780 0.4039 0.8253 0.054 Uiso 1 1 calc R U . . .
H16C H 0.7665 0.2057 0.8136 0.054 Uiso 1 1 calc R U . . .
C1B C 0.61623(3) 0.91686(15) 0.51916(4) 0.0225(2) Uani 1 1 d . . . . .
C2B C 0.63116(3) 0.89286(16) 0.48396(4) 0.0266(2) Uani 1 1 d . . . . .
H2B H 0.6505 0.8409 0.4917 0.032 Uiso 1 1 calc R U . . .
C3B C 0.61635(3) 0.94887(17) 0.43706(4) 0.0289(3) Uani 1 1 d . . . . .
H3B H 0.6258 0.9360 0.4120 0.035 Uiso 1 1 calc R U . . .
C4B C 0.58777(3) 1.02405(16) 0.42570(4) 0.0283(2) Uani 1 1 d . . . . .
H4B H 0.5783 1.0589 0.3930 0.034 Uiso 1 1 calc R U . . .
C5B C 0.57292(3) 1.04913(16) 0.46076(4) 0.0251(2) Uani 1 1 d . . . . .
H5B H 0.5536 1.1010 0.4530 0.030 Uiso 1 1 calc R U . . .
C6B C 0.58796(2) 0.99387(15) 0.50789(4) 0.0216(2) Uani 1 1 d . . . . .
C7B C 0.55250(3) 1.07781(17) 0.55625(5) 0.0264(2) Uani 1 1 d . . . . .
H7B1 H 0.5370 0.9871 0.5521 0.040 Uiso 1 1 calc R U . . .
H7B2 H 0.5456 1.1692 0.5313 0.040 Uiso 1 1 calc R U . . .
H7B3 H 0.5565 1.1307 0.5888 0.040 Uiso 1 1 calc R U . . .
C8B C 0.65089(3) 0.77392(18) 0.59335(5) 0.0303(3) Uani 1 1 d . . . . .
H8B1 H 0.6493 0.7326 0.6250 0.045 Uiso 1 1 calc R U . . .
H8B2 H 0.6686 0.8490 0.5985 0.045 Uiso 1 1 calc R U . . .
H8B3 H 0.6527 0.6724 0.5732 0.045 Uiso 1 1 calc R U . . .
C9B C 0.60220(3) 0.92671(15) 0.58713(4) 0.0221(2) Uani 1 1 d . . . . .
C10B C 0.60255(2) 0.90806(15) 0.63826(4) 0.0221(2) Uani 1 1 d . . . . .
C11B C 0.57894(3) 0.82361(16) 0.64990(4) 0.0263(2) Uani 1 1 d . . . . .
H11B H 0.5624 0.7805 0.6247 0.032 Uiso 1 1 calc R U . . .
C12B C 0.57986(3) 0.80317(17) 0.69852(4) 0.0275(2) Uani 1 1 d . . . . .
H12B H 0.5638 0.7457 0.7063 0.033 Uiso 1 1 calc R U . . .
C13B C 0.60387(3) 0.86500(16) 0.73627(4) 0.0252(2) Uani 1 1 d . . . . .
C14B C 0.62696(3) 0.95297(16) 0.72395(4) 0.0250(2) Uani 1 1 d . . . . .
H14B H 0.6433 0.9986 0.7492 0.030 Uiso 1 1 calc R U . . .
C15B C 0.62651(3) 0.97484(16) 0.67558(4) 0.0242(2) Uani 1 1 d . . . . .
H15B H 0.6424 1.0348 0.6678 0.029 Uiso 1 1 calc R U . . .
C16B C 0.60489(3) 0.83605(19) 0.78902(4) 0.0329(3) Uani 1 1 d . . . . .
H16D H 0.5855 0.8668 0.7935 0.049 Uiso 1 1 calc R U . . .
H16E H 0.6205 0.9106 0.8101 0.049 Uiso 1 1 calc R U . . .
H16F H 0.6094 0.7120 0.7976 0.049 Uiso 1 1 calc R U . . .
C1C C 0.57349(3) 0.54623(15) 0.46003(4) 0.0226(2) Uani 1 1 d . . . . .
C2C C 0.58561(3) 0.49579(16) 0.50866(4) 0.0273(2) Uani 1 1 d . . . . .
H2C H 0.6046 0.4409 0.5200 0.033 Uiso 1 1 calc R U . . .
C3C C 0.56826(3) 0.53044(17) 0.53947(5) 0.0320(3) Uani 1 1 d . . . . .
H3C H 0.5757 0.4986 0.5730 0.038 Uiso 1 1 calc R U . . .
C4C C 0.54007(3) 0.61118(18) 0.52291(5) 0.0345(3) Uani 1 1 d . . . . .
H4C H 0.5288 0.6312 0.5453 0.041 Uiso 1 1 calc R U . . .
C5C C 0.52836(3) 0.66220(18) 0.47454(5) 0.0309(3) Uani 1 1 d . . . . .
H5C H 0.5094 0.7176 0.4632 0.037 Uiso 1 1 calc R U . . .
C6C C 0.54579(3) 0.62817(15) 0.44350(4) 0.0236(2) Uani 1 1 d . . . . .
C7C C 0.51608(3) 0.76746(18) 0.36463(5) 0.0319(3) Uani 1 1 d . . . . .
H7C1 H 0.5202 0.8044 0.3343 0.048 Uiso 1 1 calc R U . . .
H7C2 H 0.5133 0.8718 0.3830 0.048 Uiso 1 1 calc R U . . .
H7C3 H 0.4979 0.6954 0.3567 0.048 Uiso 1 1 calc R U . . .
C8C C 0.61318(3) 0.44899(17) 0.42162(5) 0.0274(2) Uani 1 1 d . . . . .
H8C1 H 0.6117 0.3934 0.3900 0.041 Uiso 1 1 calc R U . . .
H8C2 H 0.6182 0.3595 0.4474 0.041 Uiso 1 1 calc R U . . .
H8C3 H 0.6289 0.5391 0.4284 0.041 Uiso 1 1 calc R U . . .
C9C C 0.56467(3) 0.60208(15) 0.38076(4) 0.0219(2) Uani 1 1 d . . . . .
C10C C 0.56770(3) 0.61034(15) 0.33131(4) 0.0232(2) Uani 1 1 d . . . . .
C11C C 0.54418(3) 0.55205(16) 0.29175(4) 0.0246(2) Uani 1 1 d . . . . .
H11C H 0.5268 0.5023 0.2971 0.030 Uiso 1 1 calc R U . . .
C12C C 0.54655(3) 0.56761(16) 0.24464(4) 0.0264(2) Uani 1 1 d . . . . .
H12C H 0.5306 0.5281 0.2179 0.032 Uiso 1 1 calc R U . . .
C13C C 0.57190(3) 0.63997(16) 0.23575(4) 0.0281(2) Uani 1 1 d . . . . .
C14C C 0.59561(3) 0.69156(17) 0.27570(5) 0.0303(3) Uani 1 1 d . . . . .
H14C H 0.6134 0.7366 0.2704 0.036 Uiso 1 1 calc R U . . .
C15C C 0.59358(3) 0.67793(16) 0.32297(4) 0.0277(2) Uani 1 1 d . . . . .
H15C H 0.6098 0.7146 0.3497 0.033 Uiso 1 1 calc R U . . .
C16C C 0.57365(3) 0.6648(2) 0.18434(5) 0.0374(3) Uani 1 1 d . . . . .
H16G H 0.5697 0.7884 0.1748 0.056 Uiso 1 1 calc R U . . .
H16H H 0.5587 0.5898 0.1620 0.056 Uiso 1 1 calc R U . . .
H16I H 0.5936 0.6323 0.1828 0.056 Uiso 1 1 calc R U . . .
O4A O 0.82058(3) 0.79637(16) 0.73056(4) 0.0420(4) Uani 0.890(4) 1 d D U P A -1
H4A1 H 0.8151 0.7757 0.7004 0.063 Uiso 0.890(4) 1 calc DR U P A -1
C17A C 0.82736(6) 0.9764(2) 0.73842(7) 0.0440(5) Uani 0.890(4) 1 d D U P A -1
H17A H 0.8094 1.0486 0.7237 0.053 Uiso 0.890(4) 1 calc R U P A -1
H17B H 0.8431 1.0105 0.7232 0.053 Uiso 0.890(4) 1 calc R U P A -1
C18A C 0.83814(10) 1.0054(5) 0.79287(11) 0.0565(11) Uani 0.890(4) 1 d D U P A
-1
H18A H 0.8217 0.9844 0.8070 0.085 Uiso 0.890(4) 1 calc R U P A -1
H18B H 0.8452 1.1270 0.7996 0.085 Uiso 0.890(4) 1 calc R U P A -1
H18C H 0.8545 0.9239 0.8075 0.085 Uiso 0.890(4) 1 calc R U P A -1
O4B O 0.8065(4) 0.928(3) 0.7117(7) 0.119(7) Uani 0.110(4) 1 d D U P A -2
H4B1 H 0.8077 0.9572 0.6839 0.178 Uiso 0.110(4) 1 calc DR U P A -2
C17B C 0.8353(5) 0.910(4) 0.7438(9) 0.084(6) Uani 0.110(4) 1 d D U P A -2
H17C H 0.8505 0.9511 0.7282 0.101 Uiso 0.110(4) 1 calc R U P A -2
H17D H 0.8395 0.7856 0.7537 0.101 Uiso 0.110(4) 1 calc R U P A -2
C18B C 0.8357(5) 1.023(4) 0.7870(8) 0.045(6) Uani 0.110(4) 1 d D U P A -2
H18D H 0.8554 1.0156 0.8112 0.068 Uiso 0.110(4) 1 calc R U P A -2
H18E H 0.8314 1.1450 0.7765 0.068 Uiso 0.110(4) 1 calc R U P A -2
H18F H 0.8205 0.9805 0.8018 0.068 Uiso 0.110(4) 1 calc R U P A -2
O5 O 0.46512(5) 0.0528(3) 0.20533(9) 0.0453(5) Uani 0.5 1 d . . P B -1
H5 H 0.4688 0.1259 0.1858 0.068 Uiso 0.5 1 calc R U P B -1
C19 C 0.4827(2) 0.0792(12) 0.2480(4) 0.045(2) Uani 0.5 1 d . . P B -1
H19A H 0.4786 -0.0091 0.2707 0.054 Uiso 0.5 1 calc R U P B -1
H19B H 0.4787 0.1973 0.2594 0.054 Uiso 0.5 1 calc R U P B -1
C20 C 0.5147(3) 0.0679(15) 0.2495(4) 0.059(3) Uani 0.5 1 d . . P B -1
H20A H 0.5272 0.0891 0.2830 0.089 Uiso 0.5 1 calc R U P B -1
H20B H 0.5189 -0.0497 0.2389 0.089 Uiso 0.5 1 calc R U P B -1
H20C H 0.5190 0.1568 0.2276 0.089 Uiso 0.5 1 calc R U P B -1


_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
O1A N3A 1.2523(14) . ?
O2A N3A 1.2587(13) . ?
O3A N3A 1.2495(14) . ?
N1A C9A 1.3462(14) . ?
N1A C6A 1.3898(14) . ?
N1A C7A 1.4631(14) . ?
N2A C9A 1.3468(14) . ?
N2A C1A 1.3911(14) . ?
N2A C8A 1.4606(15) . ?
O1B N3B 1.2541(14) . ?
O2B N3B 1.2493(13) . ?
O3B N3B 1.2611(14) . ?
N1B C9B 1.3477(15) . ?
N1B C6B 1.3919(14) . ?
N1B C7B 1.4625(14) . ?
N2B C9B 1.3447(14) . ?
N2B C1B 1.3894(14) . ?
N2B C8B 1.4608(15) . ?
O1C N3C 1.2507(14) . ?
O2C N3C 1.2406(15) . ?
O3C N3C 1.2562(14) . ?
N1C C9C 1.3457(15) . ?
N1C C6C 1.3902(15) . ?
N1C C7C 1.4618(16) . ?
N2C C9C 1.3468(15) . ?
N2C C1C 1.3891(14) . ?
N2C C8C 1.4633(15) . ?
C1A C6A 1.3931(16) . ?
C1A C2A 1.3933(16) . ?
C2A C3A 1.3832(17) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.4053(19) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3855(17) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3964(16) . ?
C5A H5A 0.9500 . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A C10A 1.4646(15) . ?
C10A C15A 1.3961(16) . ?
C10A C11A 1.4028(16) . ?
C11A C12A 1.3882(16) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.3964(18) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3965(17) . ?
C13A C16A 1.5056(17) . ?
C14A C15A 1.3865(16) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C1B C2B 1.3921(16) . ?
C1B C6B 1.3948(16) . ?
C2B C3B 1.3855(18) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.4016(19) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3871(17) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3913(16) . ?
C5B H5B 0.9500 . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C9B C10B 1.4633(15) . ?
C10B C11B 1.3966(16) . ?
C10B C15B 1.3992(16) . ?
C11B C12B 1.3861(16) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3940(17) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3977(17) . ?
C13B C16B 1.5104(16) . ?
C14B C15B 1.3861(16) . ?
C14B H14B 0.9500 . ?
C15B H15B 0.9500 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C1C C6C 1.3901(17) . ?
C1C C2C 1.3937(16) . ?
C2C C3C 1.3837(18) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.405(2) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.3864(19) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.3911(16) . ?
C5C H5C 0.9500 . ?
C7C H7C1 0.9800 . ?
C7C H7C2 0.9800 . ?
C7C H7C3 0.9800 . ?
C8C H8C1 0.9800 . ?
C8C H8C2 0.9800 . ?
C8C H8C3 0.9800 . ?
C9C C10C 1.4617(15) . ?
C10C C15C 1.3965(17) . ?
C10C C11C 1.4012(16) . ?
C11C C12C 1.3872(16) . ?
C11C H11C 0.9500 . ?
C12C C13C 1.3944(17) . ?
C12C H12C 0.9500 . ?
C13C C14C 1.3974(18) . ?
C13C C16C 1.5065(17) . ?
C14C C15C 1.3849(17) . ?
C14C H14C 0.9500 . ?
C15C H15C 0.9500 . ?
C16C H16G 0.9800 . ?
C16C H16H 0.9800 . ?
C16C H16I 0.9800 . ?
O4A C17A 1.406(2) . ?
O4A H4A1 0.8400 . ?
C17A C18A 1.507(3) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
O4B C17B 1.400(5) . ?
O4B H4B1 0.8400 . ?
C17B C18B 1.498(5) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
O5 C19 1.274(11) . ?
O5 H5 0.8400 . ?
C19 C20 1.483(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C9A N1A C6A 108.79(9) . . ?
C9A N1A C7A 126.92(9) . . ?
C6A N1A C7A 124.28(9) . . ?
C9A N2A C1A 108.76(9) . . ?
C9A N2A C8A 127.73(10) . . ?
C1A N2A C8A 123.11(10) . . ?
O3A N3A O1A 120.70(10) . . ?
O3A N3A O2A 119.88(11) . . ?
O1A N3A O2A 119.43(10) . . ?
C9B N1B C6B 108.74(9) . . ?
C9B N1B C7B 126.58(10) . . ?
C6B N1B C7B 124.57(10) . . ?
C9B N2B C1B 108.84(9) . . ?
C9B N2B C8B 127.27(10) . . ?
C1B N2B C8B 123.58(10) . . ?
O2B N3B O1B 120.28(11) . . ?
O2B N3B O3B 119.60(11) . . ?
O1B N3B O3B 120.11(10) . . ?
C9C N1C C6C 108.77(10) . . ?
C9C N1C C7C 127.48(10) . . ?
C6C N1C C7C 123.53(10) . . ?
C9C N2C C1C 108.66(9) . . ?
C9C N2C C8C 126.91(10) . . ?
C1C N2C C8C 124.43(10) . . ?
O2C N3C O1C 119.65(11) . . ?
O2C N3C O3C 121.15(11) . . ?
O1C N3C O3C 119.19(11) . . ?
N2A C1A C6A 106.66(9) . . ?
N2A C1A C2A 131.44(11) . . ?
C6A C1A C2A 121.89(11) . . ?
C3A C2A C1A 116.40(11) . . ?
C3A C2A H2A 121.8 . . ?
C1A C2A H2A 121.8 . . ?
C2A C3A C4A 121.60(11) . . ?
C2A C3A H3A 119.2 . . ?
C4A C3A H3A 119.2 . . ?
C5A C4A C3A 122.26(11) . . ?
C5A C4A H4A 118.9 . . ?
C3A C4A H4A 118.9 . . ?
C4A C5A C6A 115.83(11) . . ?
C4A C5A H5A 122.1 . . ?
C6A C5A H5A 122.1 . . ?
N1A C6A C1A 106.75(9) . . ?
N1A C6A C5A 131.21(11) . . ?
C1A C6A C5A 122.02(10) . . ?
N1A C7A H7A1 109.5 . . ?
N1A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
N1A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
N2A C8A H8A1 109.5 . . ?
N2A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
N2A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
N1A C9A N2A 109.02(9) . . ?
N1A C9A C10A 125.92(10) . . ?
N2A C9A C10A 125.05(10) . . ?
C15A C10A C11A 119.60(10) . . ?
C15A C10A C9A 119.50(10) . . ?
C11A C10A C9A 120.90(10) . . ?
C12A C11A C10A 119.66(11) . . ?
C12A C11A H11A 120.2 . . ?
C10A C11A H11A 120.2 . . ?
C11A C12A C13A 121.14(11) . . ?
C11A C12A H12A 119.4 . . ?
C13A C12A H12A 119.4 . . ?
C12A C13A C14A 118.56(11) . . ?
C12A C13A C16A 120.80(11) . . ?
C14A C13A C16A 120.64(12) . . ?
C15A C14A C13A 121.04(11) . . ?
C15A C14A H14A 119.5 . . ?
C13A C14A H14A 119.5 . . ?
C14A C15A C10A 119.99(11) . . ?
C14A C15A H15A 120.0 . . ?
C10A C15A H15A 120.0 . . ?
C13A C16A H16A 109.5 . . ?
C13A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C13A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
N2B C1B C2B 131.40(11) . . ?
N2B C1B C6B 106.76(9) . . ?
C2B C1B C6B 121.84(11) . . ?
C3B C2B C1B 116.37(12) . . ?
C3B C2B H2B 121.8 . . ?
C1B C2B H2B 121.8 . . ?
C2B C3B C4B 121.66(11) . . ?
C2B C3B H3B 119.2 . . ?
C4B C3B H3B 119.2 . . ?
C5B C4B C3B 122.10(12) . . ?
C5B C4B H4B 119.0 . . ?
C3B C4B H4B 119.0 . . ?
C4B C5B C6B 116.06(11) . . ?
C4B C5B H5B 122.0 . . ?
C6B C5B H5B 122.0 . . ?
C5B C6B N1B 131.44(11) . . ?
C5B C6B C1B 121.97(10) . . ?
N1B C6B C1B 106.58(10) . . ?
N1B C7B H7B1 109.5 . . ?
N1B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
N1B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
N2B C8B H8B1 109.5 . . ?
N2B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
N2B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
N2B C9B N1B 109.07(10) . . ?
N2B C9B C10B 125.20(10) . . ?
N1B C9B C10B 125.74(10) . . ?
C11B C10B C15B 119.89(10) . . ?
C11B C10B C9B 120.04(10) . . ?
C15B C10B C9B 120.07(10) . . ?
C12B C11B C10B 119.49(11) . . ?
C12B C11B H11B 120.3 . . ?
C10B C11B H11B 120.3 . . ?
C11B C12B C13B 121.51(11) . . ?
C11B C12B H12B 119.2 . . ?
C13B C12B H12B 119.2 . . ?
C12B C13B C14B 118.24(11) . . ?
C12B C13B C16B 120.61(11) . . ?
C14B C13B C16B 121.15(11) . . ?
C15B C14B C13B 121.22(11) . . ?
C15B C14B H14B 119.4 . . ?
C13B C14B H14B 119.4 . . ?
C14B C15B C10B 119.62(11) . . ?
C14B C15B H15B 120.2 . . ?
C10B C15B H15B 120.2 . . ?
C13B C16B H16D 109.5 . . ?
C13B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C13B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
N2C C1C C6C 106.88(10) . . ?
N2C C1C C2C 131.01(11) . . ?
C6C C1C C2C 122.11(11) . . ?
C3C C2C C1C 115.98(12) . . ?
C3C C2C H2C 122.0 . . ?
C1C C2C H2C 122.0 . . ?
C2C C3C C4C 122.25(12) . . ?
C2C C3C H3C 118.9 . . ?
C4C C3C H3C 118.9 . . ?
C5C C4C C3C 121.27(12) . . ?
C5C C4C H4C 119.4 . . ?
C3C C4C H4C 119.4 . . ?
C4C C5C C6C 116.64(12) . . ?
C4C C5C H5C 121.7 . . ?
C6C C5C H5C 121.7 . . ?
C1C C6C N1C 106.65(10) . . ?
C1C C6C C5C 121.75(11) . . ?
N1C C6C C5C 131.59(12) . . ?
N1C C7C H7C1 109.5 . . ?
N1C C7C H7C2 109.5 . . ?
H7C1 C7C H7C2 109.5 . . ?
N1C C7C H7C3 109.5 . . ?
H7C1 C7C H7C3 109.5 . . ?
H7C2 C7C H7C3 109.5 . . ?
N2C C8C H8C1 109.5 . . ?
N2C C8C H8C2 109.5 . . ?
H8C1 C8C H8C2 109.5 . . ?
N2C C8C H8C3 109.5 . . ?
H8C1 C8C H8C3 109.5 . . ?
H8C2 C8C H8C3 109.5 . . ?
N1C C9C N2C 109.00(10) . . ?
N1C C9C C10C 125.09(10) . . ?
N2C C9C C10C 125.91(10) . . ?
C15C C10C C11C 119.65(10) . . ?
C15C C10C C9C 120.77(10) . . ?
C11C C10C C9C 119.57(10) . . ?
C12C C11C C10C 119.45(11) . . ?
C12C C11C H11C 120.3 . . ?
C10C C11C H11C 120.3 . . ?
C11C C12C C13C 121.39(11) . . ?
C11C C12C H12C 119.3 . . ?
C13C C12C H12C 119.3 . . ?
C12C C13C C14C 118.47(11) . . ?
C12C C13C C16C 121.02(11) . . ?
C14C C13C C16C 120.51(11) . . ?
C15C C14C C13C 120.92(12) . . ?
C15C C14C H14C 119.5 . . ?
C13C C14C H14C 119.5 . . ?
C14C C15C C10C 120.06(11) . . ?
C14C C15C H15C 120.0 . . ?
C10C C15C H15C 120.0 . . ?
C13C C16C H16G 109.5 . . ?
C13C C16C H16H 109.5 . . ?
H16G C16C H16H 109.5 . . ?
C13C C16C H16I 109.5 . . ?
H16G C16C H16I 109.5 . . ?
H16H C16C H16I 109.5 . . ?
C17A O4A H4A1 109.5 . . ?
O4A C17A C18A 107.4(2) . . ?
O4A C17A H17A 110.2 . . ?
C18A C17A H17A 110.2 . . ?
O4A C17A H17B 110.2 . . ?
C18A C17A H17B 110.2 . . ?
H17A C17A H17B 108.5 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C17B O4B H4B1 109.5 . . ?
O4B C17B C18B 105.3(11) . . ?
O4B C17B H17C 110.7 . . ?
C18B C17B H17C 110.7 . . ?
O4B C17B H17D 110.7 . . ?
C18B C17B H17D 110.7 . . ?
H17C C17B H17D 108.8 . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C19 O5 H5 109.5 . . ?
O5 C19 C20 112.6(6) . . ?
O5 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
O5 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.054

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_preparation       Luminescent

