# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_(H2Etim)2SO4
_database_code_depnum_ccdc_archive 'CCDC 1050267'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '2-Ethylimidazolium Sulfate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 N4 O4 S'
_chemical_formula_weight         288.33

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'
S S 0.1246 0.1234 '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                   9.642(11)
_cell_length_b                   15.986(17)
_cell_length_c                   9.334(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.708(12)
_cell_angle_gamma                90
_cell_volume                     1437(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2229
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.09

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.50
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7071
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Blessing, (1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7178
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.469
_diffrn_reflns_theta_max         26.581
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1484
_reflns_number_gt                1147
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 The crystal is air sensitive (deliquescent), making
 the selection of a single crystal and data collection
 complicated.

 All non-hydrogen atoms were included in the refinement 
 using the anisotropic model. The hydrogen atoms connected
 to carbon and nitrogen atoms were placed in positions
 calculated based on the assigned hybridization of the
 parent non-hydrogen atom and included in the refined
 using a riding model.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0898P)²+0.3429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1484
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1499
_refine_ls_wR_factor_gt          0.1378
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.003

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 0.5000 0.62150(4) 0.2500 0.0448(3) Uani 1 2 d S T P . .
O1 O 0.54214(19) 0.67474(10) 0.37302(17) 0.0601(5) Uani 1 1 d . . . . .
O2 O 0.3846(3) 0.57026(14) 0.2917(2) 0.0934(8) Uani 1 1 d . . . . .
N1 N 0.3132(2) 0.41154(13) 0.2466(2) 0.0573(6) Uani 1 1 d . . . . .
H1A H 0.3423 0.4637 0.2501 0.069 Uiso 1 1 calc R U . . .
N2 N 0.2093(2) 0.29807(11) 0.2959(2) 0.0494(5) Uani 1 1 d . . . . .
H2A H 0.1567 0.2614 0.3382 0.059 Uiso 1 1 calc R U . . .
C2 C 0.3481(3) 0.3538(2) 0.1466(3) 0.0693(8) Uani 1 1 d . . . . .
H2 H 0.4073 0.3626 0.0696 0.083 Uiso 1 1 calc R U . . .
C1 C 0.2291(2) 0.37679(14) 0.3375(2) 0.0475(6) Uani 1 1 d . . . . .
C4 C 0.1731(3) 0.41752(17) 0.4642(3) 0.0703(8) Uani 1 1 d . . . . .
H4 H 0.2134 0.4666 0.5058 0.084 Uiso 1 1 calc R U . . .
C5 C 0.0507(4) 0.3770(2) 0.5217(4) 0.0941(11) Uani 1 1 d . . . . .
H5A H -0.0268 0.3793 0.4500 0.141 Uiso 1 1 calc R U . . .
H5B H 0.0249 0.4062 0.6089 0.141 Uiso 1 1 calc R U . . .
H5C H 0.0725 0.3185 0.5446 0.141 Uiso 1 1 calc R U . . .
C3 C 0.2832(3) 0.28286(18) 0.1775(3) 0.0617(7) Uani 1 1 d . . . . .
H3 H 0.2876 0.2315 0.1267 0.074 Uiso 1 1 calc R 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
S1 O2 1.450(2) . ?
S1 O2 1.450(2) 2_655 ?
S1 O1 1.471(2) 2_655 ?
S1 O1 1.471(2) . ?
N1 C1 1.323(3) . ?
N1 C2 1.366(3) . ?
N1 H1A 0.8800 . ?
N2 C1 1.328(3) . ?
N2 C3 1.366(3) . ?
N2 H2A 0.8800 . ?
C2 C3 1.333(4) . ?
C2 H2 0.9500 . ?
C1 C4 1.475(3) . ?
C4 C5 1.470(4) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C3 H3 0.9500 . ?

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
O2 S1 O2 111.2(2) . 2_655 ?
O2 S1 O1 110.46(14) . 2_655 ?
O2 S1 O1 107.72(11) 2_655 2_655 ?
O2 S1 O1 107.72(11) . . ?
O2 S1 O1 110.46(14) 2_655 . ?
O1 S1 O1 109.31(16) 2_655 . ?
C1 N1 C2 109.4(2) . . ?
C1 N1 H1A 125.3 . . ?
C2 N1 H1A 125.3 . . ?
C1 N2 C3 109.4(2) . . ?
C1 N2 H2A 125.3 . . ?
C3 N2 H2A 125.3 . . ?
C3 C2 N1 107.1(2) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
N1 C1 N2 107.1(2) . . ?
N1 C1 C4 126.0(2) . . ?
N2 C1 C4 126.8(2) . . ?
C5 C4 C1 115.4(2) . . ?
C5 C4 H4 122.3 . . ?
C1 C4 H4 122.3 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C3 N2 106.9(2) . . ?
C2 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4

_chemical_properties_physical    Deliquescent
####################################################################### 
# 
# 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_(H2Bim)2SO4
_database_code_depnum_ccdc_archive 'CCDC 1050268'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Benzimidazolium sulfate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N4 O4 S'
_chemical_formula_weight         334.35

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   14.6766(8)
_cell_length_b                   18.8388(14)
_cell_length_c                   11.8862(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3286.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5674
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.23

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6354
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Blessing (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9359
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.456
_diffrn_reflns_theta_max         28.630
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1962
_reflns_number_gt                1884
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_max     0.904
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 All non-hydrogen atoms were included in the refinement using the 
 anisotropic model. The hydrogen atoms connected to carbon and nitrogen 
 atoms were placed in positions calculated based on the assigned 
 hybridization of the parent non-hydrogen atom and included in the 
 refinement using a riding model.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+2.5173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 849 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.048(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1962
_refine_ls_number_parameters     105
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002

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 0.2500 -0.2500 0.61948(6) 0.02772(17) Uani 1 2 d S T P . .
O2 O 0.19085(14) -0.29399(10) 0.5489(2) 0.0605(6) Uani 1 1 d . . . . .
O1 O 0.19577(14) -0.20153(9) 0.68959(17) 0.0494(5) Uani 1 1 d . . . . .
N1 N 0.02506(16) -0.25962(11) 0.4755(2) 0.0456(5) Uani 1 1 d . . . . .
H1A H 0.0734 -0.2724 0.5109 0.055 Uiso 1 1 calc R U . . .
N2 N -0.08928(15) -0.26255(10) 0.35930(19) 0.0449(5) Uani 1 1 d . . . . .
H2 H -0.1262 -0.2772 0.3082 0.054 Uiso 1 1 calc R U . . .
C1 C -0.01697(19) -0.29677(13) 0.3961(2) 0.0476(7) Uani 1 1 d . . . . .
H1 H 0.0020 -0.3409 0.3701 0.057 Uiso 1 1 calc R U . . .
C2 C -0.09560(18) -0.19883(13) 0.4172(2) 0.0442(6) Uani 1 1 d . . . . .
C3 C -0.02218(18) -0.19660(13) 0.4918(2) 0.0433(5) Uani 1 1 d . . . . .
C4 C -0.0078(2) -0.13957(18) 0.5635(3) 0.0593(8) Uani 1 1 d . . . . .
H4 H 0.0406 -0.1384 0.6140 0.071 Uiso 1 1 calc R U . . .
C5 C -0.0694(3) -0.0849(2) 0.5554(4) 0.0832(12) Uani 1 1 d . . . . .
H5 H -0.0625 -0.0455 0.6018 0.100 Uiso 1 1 calc R U . . .
C6 C -0.1421(3) -0.0866(2) 0.4797(4) 0.0872(14) Uani 1 1 d . . . . .
H6 H -0.1816 -0.0481 0.4770 0.105 Uiso 1 1 calc R U . . .
C7 C -0.1574(2) -0.14332(18) 0.4089(3) 0.0649(9) Uani 1 1 d . . . . .
H7 H -0.2061 -0.1443 0.3588 0.078 Uiso 1 1 calc R 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
S1 O2 1.4642(19) 14_545 ?
S1 O2 1.4642(19) . ?
S1 O1 1.4702(17) 14_545 ?
S1 O1 1.4703(17) . ?
N1 C1 1.327(3) . ?
N1 C3 1.388(3) . ?
N1 H1A 0.8600 . ?
N2 C1 1.317(3) . ?
N2 C2 1.387(3) . ?
N2 H2 0.8600 . ?
C1 H1 0.9300 . ?
C2 C7 1.388(4) . ?
C2 C3 1.395(3) . ?
C3 C4 1.388(4) . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(5) . ?
C6 H6 0.9300 . ?
C7 H7 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
O2 S1 O2 110.1(2) 14_545 . ?
O2 S1 O1 110.81(11) 14_545 14_545 ?
O2 S1 O1 107.11(9) . 14_545 ?
O2 S1 O1 107.10(9) 14_545 . ?
O2 S1 O1 110.81(11) . . ?
O1 S1 O1 110.96(18) 14_545 . ?
C1 N1 C3 108.5(2) . . ?
C1 N1 H1A 125.7 . . ?
C3 N1 H1A 125.7 . . ?
C1 N2 C2 108.2(2) . . ?
C1 N2 H2 125.9 . . ?
C2 N2 H2 125.9 . . ?
N2 C1 N1 110.7(2) . . ?
N2 C1 H1 124.7 . . ?
N1 C1 H1 124.7 . . ?
N2 C2 C7 131.3(2) . . ?
N2 C2 C3 106.8(2) . . ?
C7 C2 C3 121.8(2) . . ?
N1 C3 C4 132.2(2) . . ?
N1 C3 C2 105.7(2) . . ?
C4 C3 C2 122.1(2) . . ?
C5 C4 C3 115.9(3) . . ?
C5 C4 H4 122.1 . . ?
C3 C4 H4 122.1 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 122.5(3) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C6 C7 C2 115.7(3) . . ?
C6 C7 H7 122.2 . . ?
C2 C7 H7 122.2 . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_(H2MeBim)2SO4
_database_code_depnum_ccdc_archive 'CCDC 1050269'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            '2-Methylbenzimidazolium Sulfate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N4 O4 S'
_chemical_formula_weight         362.40

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'
S S 0.1246 0.1234 '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                   17.398(3)
_cell_length_b                   7.4436(11)
_cell_length_c                   14.051(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.3800(10)
_cell_angle_gamma                90
_cell_volume                     1754.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2891
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.51

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6162
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Blessing, (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10151
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.428
_diffrn_reflns_theta_max         28.672
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2143
_reflns_number_gt                1633
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
 All non-hydrogen atoms were included in the refinement using the 
 anisotropic model. The hydrogen atoms connected to carbon and nitrogen 
 atoms were placed in positions calculated based on the assigned 
 hybridization of the parent non-hydrogen atom and included in the 
 refinement using a riding model.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0938P)²+0.2125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2143
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_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 0.5000 0.24180(8) 0.2500 0.0413(2) Uani 1 2 d S T P . .
O1 O 0.49851(8) 0.35439(19) 0.16417(11) 0.0623(4) Uani 1 1 d . . . . .
O2 O 0.42868(8) 0.1279(2) 0.23142(10) 0.0613(4) Uani 1 1 d . . . . .
N1 N 0.41007(9) 0.22066(19) 0.44434(11) 0.0450(4) Uani 1 1 d . . . . .
H1 H 0.4324 0.2840 0.4060 0.054 Uiso 1 1 calc R U . . .
N2 N 0.39369(8) 0.07965(19) 0.57262(11) 0.0454(4) Uani 1 1 d . . . . .
H2 H 0.4037 0.0341 0.6325 0.054 Uiso 1 1 calc R U . . .
C1 C 0.52623(11) 0.2257(3) 0.59370(16) 0.0570(5) Uani 1 1 d . . . . .
H1A H 0.5597 0.2416 0.5481 0.086 Uiso 1 1 calc R U . . .
H1B H 0.5487 0.1305 0.6411 0.086 Uiso 1 1 calc R U . . .
H1C H 0.5245 0.3384 0.6292 0.086 Uiso 1 1 calc R U . . .
C2 C 0.44433(10) 0.1754(2) 0.53727(13) 0.0439(4) Uani 1 1 d . . . . .
C3 C 0.33321(10) 0.1518(2) 0.41746(13) 0.0450(4) Uani 1 1 d . . . . .
C4 C 0.27323(12) 0.1599(3) 0.32977(15) 0.0595(5) Uani 1 1 d . . . . .
H4 H 0.2805 0.2196 0.2730 0.071 Uiso 1 1 calc R U . . .
C5 C 0.20248(13) 0.0762(3) 0.32981(18) 0.0696(6) Uani 1 1 d . . . . .
H5 H 0.1598 0.0782 0.2714 0.084 Uiso 1 1 calc R U . . .
C6 C 0.32262(10) 0.0632(2) 0.49993(14) 0.0438(4) Uani 1 1 d . . . . .
C7 C 0.25119(12) -0.0196(3) 0.49933(17) 0.0579(5) Uani 1 1 d . . . . .
H7 H 0.2438 -0.0793 0.5560 0.070 Uiso 1 1 calc R U . . .
C8 C 0.19195(13) -0.0115(3) 0.4134(2) 0.0686(6) Uani 1 1 d . . . . .
H8 H 0.1422 -0.0670 0.4103 0.082 Uiso 1 1 calc R 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
S1 O1 1.4632(13) . ?
S1 O1 1.4632(13) 2_655 ?
S1 O2 1.4678(13) . ?
S1 O2 1.4678(13) 2_655 ?
N1 C2 1.327(2) . ?
N1 C3 1.388(2) . ?
N1 H1 0.8800 . ?
N2 C2 1.328(2) . ?
N2 C6 1.385(2) . ?
N2 H2 0.8800 . ?
C1 C2 1.483(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.389(3) . ?
C3 C6 1.387(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C8 1.398(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C7 C8 1.365(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?

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 O1 110.11(13) . 2_655 ?
O1 S1 O2 110.78(9) . . ?
O1 S1 O2 107.86(7) 2_655 . ?
O1 S1 O2 107.86(7) . 2_655 ?
O1 S1 O2 110.78(9) 2_655 2_655 ?
O2 S1 O2 109.45(13) . 2_655 ?
C2 N1 C3 108.84(15) . . ?
C2 N1 H1 125.6 . . ?
C3 N1 H1 125.6 . . ?
C2 N2 C6 108.83(15) . . ?
C2 N2 H2 125.6 . . ?
C6 N2 H2 125.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 N1 109.57(15) . . ?
N2 C2 C1 125.04(17) . . ?
N1 C2 C1 125.38(17) . . ?
C4 C3 C6 121.79(18) . . ?
C4 C3 N1 131.95(18) . . ?
C6 C3 N1 106.27(15) . . ?
C5 C4 C3 116.1(2) . . ?
C5 C4 H4 121.9 . . ?
C3 C4 H4 121.9 . . ?
C4 C5 C8 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C8 C5 H5 119.1 . . ?
C7 C6 N2 131.91(18) . . ?
C7 C6 C3 121.61(18) . . ?
N2 C6 C3 106.48(15) . . ?
C8 C7 C6 116.8(2) . . ?
C8 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C7 C8 C5 121.8(2) . . ?
C7 C8 H8 119.1 . . ?
C5 C8 H8 119.1 . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_(H2PhBim)2SO4_EtOH
_database_code_depnum_ccdc_archive 'CCDC 1050270'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
'2-phenylbenzimidazolium Sulfate Ethanol Solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H28 N4 O5 S'
_chemical_formula_weight         532.60

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   16.620(4)
_cell_length_b                   8.218(2)
_cell_length_c                   19.159(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2616.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2031
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      20.12

_exptl_crystal_description       Plates
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5655
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'Blessing (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23489
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.1162
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.451
_diffrn_reflns_theta_max         25.260
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2314
_reflns_number_gt                1527
_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.
;
_vrf_RFACG01_shelx               
;
PROBLEM: The value of the R factor is > 0.10
RESPONSE: Thin plate-like crystals poorly diffracting even at 100 K,
highly disordered structure with disordered solvent molecules.
;
_vrf_PLAT088_shelx               
;
PROBLEM: Poor Data / Parameter Ratio ....................       8.66 Note  
RESPONSE: Thin plate-like crystals poorly diffracting even at 100 K,
highly disordered structure with disordered solvent molecules.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 All non-hydrogen atoms were included in the refinement using the 
 anisotropic model. The hydrogen atoms connected to carbon and nitrogen 
 atoms were placed in positions calculated based on the assigned 
 hybridization of the parent non-hydrogen atom and included in the 
 refinement using a riding model.

 The 2-phenylbenzimidazolium ion was found to be disordered over
 two sites with occupational parameters 0.42 and 0.58. The two 
 disordered sites are in a mutually antiparallel orientation. 
 The ethanol molecule is hydrogen-bonded to the sulfate ion and 
 is also disordered in two sites across a centre of symmetry, 
 each with the occupational parameter 0.5.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+11.0419P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2314
_refine_ls_number_parameters     273
_refine_ls_number_restraints     189
_refine_ls_R_factor_all          0.1497
_refine_ls_R_factor_gt           0.1023
_refine_ls_wR_factor_ref         0.2235
_refine_ls_wR_factor_gt          0.2031
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.074
_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
S1 S 0.0000 0.6451(2) -0.2500 0.0361(5) Uani 1 2 d S T P . .
O1 O -0.0466(2) 0.5463(5) -0.2980(2) 0.0521(11) Uani 1 1 d . . . . .
O2 O 0.0542(3) 0.7439(7) -0.2913(3) 0.101(2) Uani 1 1 d . . . . .
O3 O 0.0310(9) -0.3010(15) 0.5586(6) 0.118(5) Uani 0.5 1 d D . P A -1
H3B H 0.0223 -0.2825 0.6000 0.177 Uiso 0.5 1 calc R U P A -1
N1 N 0.3235(5) 0.1098(10) 0.2510(5) 0.0202(18) Uani 0.42 1 d . U P B 1
H1 H 0.3659 0.0684 0.2695 0.024 Uiso 0.42 1 calc R U P B 1
N2 N 0.1988(7) 0.1778(14) 0.2274(6) 0.026(3) Uani 0.42 1 d . U P B 1
H2 H 0.1472 0.1852 0.2298 0.032 Uiso 0.42 1 calc R U P B 1
C1 C 0.2435(6) 0.2500(11) 0.1805(4) 0.016(2) Uani 0.42 1 d G U P B 1
C2 C 0.3226(6) 0.2073(11) 0.1956(4) 0.017(3) Uani 0.42 1 d G U P B 1
C3 C 0.3848(5) 0.2624(14) 0.1533(6) 0.033(3) Uani 0.42 1 d G U P B 1
H3 H 0.4377 0.2339 0.1634 0.040 Uiso 0.42 1 calc R U P B 1
C4 C 0.3681(6) 0.3602(18) 0.0960(6) 0.050(5) Uani 0.42 1 d G U P B 1
H4 H 0.4097 0.3971 0.0677 0.060 Uiso 0.42 1 calc R U P B 1
C5 C 0.2890(8) 0.4029(18) 0.0809(6) 0.039(5) Uani 0.42 1 d G U P B 1
H5 H 0.2778 0.4683 0.0425 0.047 Uiso 0.42 1 calc R U P B 1
C6 C 0.2268(5) 0.3478(14) 0.1231(6) 0.038(4) Uani 0.42 1 d G U P B 1
H6 H 0.1739 0.3764 0.1130 0.046 Uiso 0.42 1 calc R U P B 1
C7 C 0.2470(12) 0.086(2) 0.2737(8) 0.019(4) Uani 0.42 1 d . U P B 1
C8 C 0.2210(7) -0.0056(14) 0.3330(5) 0.021(4) Uani 0.42 1 d G U P B 1
C9 C 0.2772(5) -0.0871(13) 0.3739(6) 0.026(3) Uani 0.42 1 d G U P B 1
H9 H 0.3316 -0.0817 0.3627 0.031 Uiso 0.42 1 calc R U P B 1
C10 C 0.2520(7) -0.1768(15) 0.4314(6) 0.037(4) Uani 0.42 1 d G U P B 1
H10 H 0.2895 -0.2313 0.4587 0.044 Uiso 0.42 1 calc R U P B 1
C11 C 0.1707(8) -0.185(2) 0.4481(7) 0.055(7) Uani 0.42 1 d G U P B 1
H11 H 0.1538 -0.2448 0.4866 0.066 Uiso 0.42 1 calc R U P B 1
C12 C 0.1146(5) -0.103(2) 0.4072(9) 0.043(6) Uani 0.42 1 d G U P B 1
H12 H 0.0602 -0.1087 0.4183 0.052 Uiso 0.42 1 calc R U P B 1
C13 C 0.1397(6) -0.0137(16) 0.3497(7) 0.035(4) Uani 0.42 1 d G U P B 1
H13 H 0.1022 0.0409 0.3223 0.042 Uiso 0.42 1 calc R U P B 1
N1A N 0.1828(6) 0.1274(11) 0.2638(5) 0.043(3) Uani 0.58 1 d . U P C 2
H1A H 0.1465 0.1780 0.2403 0.052 Uiso 0.58 1 calc R U P C 2
N2A N 0.2993(5) 0.0368(9) 0.2967(5) 0.046(2) Uani 0.58 1 d . . P C 2
H2A H 0.3506 0.0228 0.2970 0.055 Uiso 0.58 1 calc R U P C 2
C1A C 0.2459(5) -0.0313(11) 0.3427(5) 0.033(3) Uani 0.58 1 d G U P C 2
C2A C 0.1708(6) 0.0279(9) 0.3232(3) 0.040(3) Uani 0.58 1 d G U P C 2
C3A C 0.1030(4) -0.0129(13) 0.3619(5) 0.052(3) Uani 0.58 1 d G U P C 2
H3A H 0.0528 0.0267 0.3488 0.062 Uiso 0.58 1 calc R U P C 2
C4A C 0.1102(5) -0.1131(17) 0.4200(6) 0.062(6) Uani 0.58 1 d G U P C 2
H4A H 0.0649 -0.1404 0.4459 0.074 Uiso 0.58 1 calc R U P C 2
C5A C 0.1853(7) -0.1723(15) 0.4395(5) 0.046(4) Uani 0.58 1 d G U P C 2
H5A H 0.1901 -0.2393 0.4784 0.055 Uiso 0.58 1 calc R U P C 2
C6A C 0.2531(4) -0.1315(12) 0.4008(5) 0.050(4) Uani 0.58 1 d G U P C 2
H6A H 0.3033 -0.1711 0.4138 0.060 Uiso 0.58 1 calc R U P C 2
C7A C 0.2590(11) 0.1269(16) 0.2522(8) 0.039(4) Uani 0.58 1 d . U P C 2
C8A C 0.2945(7) 0.2205(10) 0.1955(4) 0.041(3) Uani 0.58 1 d G U P C 2
C9A C 0.2488(5) 0.3028(11) 0.1461(4) 0.044(3) Uani 0.58 1 d G U P C 2
H9A H 0.1930 0.2937 0.1465 0.053 Uiso 0.58 1 calc R U P C 2
C10A C 0.2864(6) 0.3987(13) 0.0960(5) 0.045(4) Uani 0.58 1 d G U P C 2
H10A H 0.2558 0.4538 0.0630 0.054 Uiso 0.58 1 calc R U P C 2
C11A C 0.3698(6) 0.4123(15) 0.0954(6) 0.080(5) Uani 0.58 1 d G U P C 2
H11A H 0.3949 0.4765 0.0619 0.096 Uiso 0.58 1 calc R U P C 2
C12A C 0.4155(5) 0.3300(15) 0.1449(6) 0.115(7) Uani 0.58 1 d G U P C 2
H12A H 0.4713 0.3391 0.1444 0.137 Uiso 0.58 1 calc R U P C 2
C13A C 0.3778(7) 0.2341(12) 0.1949(5) 0.076(4) Uani 0.58 1 d G U P C 2
H13A H 0.4084 0.1790 0.2280 0.092 Uiso 0.58 1 calc R U P C 2
C14 C -0.025(2) -0.424(6) 0.534(3) 0.183(12) Uani 0.5 1 d D U P . .
H14A H -0.0737 -0.3696 0.5177 0.219 Uiso 0.5 1 calc R U P A .
H14B H -0.0398 -0.4937 0.5723 0.219 Uiso 0.5 1 calc R U P . .
C15 C 0.007(2) -0.528(5) 0.475(3) 0.173(12) Uani 0.5 1 d D U P A .
H15A H -0.0332 -0.6054 0.4614 0.260 Uiso 0.5 1 calc R U P . .
H15B H 0.0203 -0.4600 0.4359 0.260 Uiso 0.5 1 calc R U P . .
H15C H 0.0542 -0.5842 0.4906 0.260 Uiso 0.5 1 calc R U P . .


_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 O2 1.448(4) . ?
S1 O2 1.448(4) 4_554 ?
S1 O1 1.451(4) . ?
S1 O1 1.451(4) 4_554 ?
O3 C14 1.455(10) . ?
O3 H3B 0.8200 . ?
N1 C2 1.329(12) . ?
N1 C7 1.36(2) . ?
N1 H1 0.8600 . ?
N2 C1 1.309(13) . ?
N2 C7 1.41(2) . ?
N2 H2 0.8600 . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.429(17) . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 C10 1.3900 . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 H10 0.9300 . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C12 C13 1.3900 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N1A C7A 1.29(2) . ?
N1A C2A 1.415(12) . ?
N1A H1A 0.8600 . ?
N2A C7A 1.313(18) . ?
N2A C1A 1.370(11) . ?
N2A H2A 0.8600 . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C2A C3A 1.3900 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9300 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9300 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A C8A 1.455(17) . ?
C8A C9A 1.3900 . ?
C8A C13A 1.3900 . ?
C9A C10A 1.3900 . ?
C9A H9A 0.9300 . ?
C10A C11A 1.3900 . ?
C10A H10A 0.9300 . ?
C11A C12A 1.3900 . ?
C11A H11A 0.9300 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9300 . ?
C13A H13A 0.9300 . ?
C14 C15 1.508(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
O2 S1 O2 111.8(6) . 4_554 ?
O2 S1 O1 107.4(3) . . ?
O2 S1 O1 109.2(2) 4_554 . ?
O2 S1 O1 109.2(2) . 4_554 ?
O2 S1 O1 107.4(3) 4_554 4_554 ?
O1 S1 O1 111.9(4) . 4_554 ?
C14 O3 H3B 109.5 . . ?
C2 N1 C7 109.4(12) . . ?
C2 N1 H1 125.3 . . ?
C7 N1 H1 125.3 . . ?
C1 N2 C7 110.5(13) . . ?
C1 N2 H2 124.7 . . ?
C7 N2 H2 124.7 . . ?
N2 C1 C2 106.3(9) . . ?
N2 C1 C6 133.7(9) . . ?
C2 C1 C6 120.0 . . ?
N1 C2 C1 109.2(9) . . ?
N1 C2 C3 130.8(9) . . ?
C1 C2 C3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 N2 104.6(14) . . ?
N1 C7 C8 127.8(15) . . ?
N2 C7 C8 127.5(16) . . ?
C9 C8 C13 120.0 . . ?
C9 C8 C7 119.9(12) . . ?
C13 C8 C7 120.1(12) . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C7A N1A C2A 106.1(13) . . ?
C7A N1A H1A 127.0 . . ?
C2A N1A H1A 127.0 . . ?
C7A N2A C1A 108.5(12) . . ?
C7A N2A H2A 125.7 . . ?
C1A N2A H2A 125.7 . . ?
N2A C1A C2A 105.4(9) . . ?
N2A C1A C6A 134.5(9) . . ?
C2A C1A C6A 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A N1A 133.0(8) . . ?
C1A C2A N1A 107.0(9) . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
N1A C7A N2A 113.0(16) . . ?
N1A C7A C8A 121.8(16) . . ?
N2A C7A C8A 125.2(15) . . ?
C9A C8A C13A 120.0 . . ?
C9A C8A C7A 123.0(10) . . ?
C13A C8A C7A 116.9(10) . . ?
C8A C9A C10A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C11A C10A C9A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C10A C11A C12A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C11A C12A C13A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C12A C13A C8A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C8A C13A H13A 120.0 . . ?
O3 C14 C15 114.3(11) . . ?
O3 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
O3 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C1 C2 -0.4(12) . . . . ?
C7 N2 C1 C6 177.5(11) . . . . ?
C7 N1 C2 C1 -0.1(12) . . . . ?
C7 N1 C2 C3 -177.8(10) . . . . ?
N2 C1 C2 N1 0.3(9) . . . . ?
C6 C1 C2 N1 -178.0(10) . . . . ?
N2 C1 C2 C3 178.3(9) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
N1 C2 C3 C4 177.5(13) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
N2 C1 C6 C5 -177.7(12) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 N1 C7 N2 -0.2(15) . . . . ?
C2 N1 C7 C8 -177.5(14) . . . . ?
C1 N2 C7 N1 0.4(16) . . . . ?
C1 N2 C7 C8 177.7(14) . . . . ?
N1 C7 C8 C9 -2(2) . . . . ?
N2 C7 C8 C9 -178.8(13) . . . . ?
N1 C7 C8 C13 178.3(13) . . . . ?
N2 C7 C8 C13 2(2) . . . . ?
C13 C8 C9 C10 0.0 . . . . ?
C7 C8 C9 C10 -179.7(14) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C8 0.0 . . . . ?
C9 C8 C13 C12 0.0 . . . . ?
C7 C8 C13 C12 179.7(14) . . . . ?
C7A N2A C1A C2A -1.3(9) . . . . ?
C7A N2A C1A C6A -177.9(9) . . . . ?
N2A C1A C2A C3A -177.2(8) . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
N2A C1A C2A N1A 1.7(7) . . . . ?
C6A C1A C2A N1A 178.8(8) . . . . ?
C7A N1A C2A C3A 177.2(9) . . . . ?
C7A N1A C2A C1A -1.5(9) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
N1A C2A C3A C4A -178.5(10) . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
N2A C1A C6A C5A 176.2(11) . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
C2A N1A C7A N2A 0.7(13) . . . . ?
C2A N1A C7A C8A -178.4(10) . . . . ?
C1A N2A C7A N1A 0.4(13) . . . . ?
C1A N2A C7A C8A 179.5(10) . . . . ?
N1A C7A C8A C9A -6.7(16) . . . . ?
N2A C7A C8A C9A 174.3(9) . . . . ?
N1A C7A C8A C13A 169.1(10) . . . . ?
N2A C7A C8A C13A -9.9(15) . . . . ?
C13A C8A C9A C10A 0.0 . . . . ?
C7A C8A C9A C10A 175.8(10) . . . . ?
C8A C9A C10A C11A 0.0 . . . . ?
C9A C10A C11A C12A 0.0 . . . . ?
C10A C11A C12A C13A 0.0 . . . . ?
C11A C12A C13A C8A 0.0 . . . . ?
C9A C8A C13A C12A 0.0 . . . . ?
C7A C8A C13A C12A -176.0(10) . . . . ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_(H2PhBim)2SO4_MeOH
_database_code_depnum_ccdc_archive 'CCDC 1050271'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
'2-phenylbenzimidazolium Sulfate Methanol Solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H30 N4 O6 S'
_chemical_formula_weight         550.62

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.933(4)
_cell_length_b                   8.0337(18)
_cell_length_c                   19.688(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2678.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1635
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      19.39

_exptl_crystal_description       Plates
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6412
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'Blessing (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24911
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.069
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2444
_reflns_number_gt                1499
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_refine_special_details          
;
 All non-hydrogen atoms were included in the refinement using the 
 anisotropic model. The hydrogen atoms connected to carbon and nitrogen 
 atoms were placed in positions calculated based on the assigned 
 hybridization of the parent non-hydrogen atom and included in the 
 refinement using a riding model. The hydrogen atom of the methanol
 molecule was placed in a position generated by the SHELX command
 AFIX 147 and was included in the refinement using the riding model.

 The sulfate ion is located on a two-fold rotation axis, and the 
 2-phenylbenzimidazolium ion was found to be disordered over
 two sites with occupational parameters 0.42 and 0.58. The two 
 disordered sites are in a mutually antiparallel orientation.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0772P)²+3.3383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2444
_refine_ls_number_parameters     242
_refine_ls_number_restraints     130
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1915
_refine_ls_wR_factor_gt          0.1590
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.050
_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
S1 S 0.5000 0.84844(16) 0.7500 0.0296(4) Uani 1 2 d S T P . .
O1 O 0.44925(14) 0.7422(3) 0.70737(12) 0.0468(8) Uani 1 1 d . . . . .
O2 O 0.45160(13) 0.9512(3) 0.79496(12) 0.0410(7) Uani 1 1 d . . . . .
O3 O 0.45844(19) 0.7713(6) 0.56516(15) 0.0925(14) Uani 1 1 d . . . . .
H3B H 0.4586 0.7662 0.6078 0.139 Uiso 1 1 calc R U . . .
N1 N 0.2985(3) 0.6697(6) 0.7221(2) 0.0255(9) Uani 0.58 1 d D U P A 1
H1 H 0.3503 0.6757 0.7234 0.031 Uiso 0.58 1 calc R U P A 1
N2 N 0.1773(3) 0.6012(5) 0.7490(2) 0.0236(8) Uani 0.58 1 d D U P A 1
H2 H 0.1365 0.5554 0.7694 0.028 Uiso 0.58 1 calc R U P A 1
C1 C 0.2513(3) 0.7453(6) 0.6752(3) 0.0251(14) Uani 0.58 1 d DG U P A 1
C2 C 0.1746(4) 0.7034(5) 0.69364(19) 0.0267(15) Uani 0.58 1 d DG . P A 1
C3 C 0.1112(2) 0.7633(7) 0.6561(3) 0.0292(16) Uani 0.58 1 d DG . P A 1
H3 H 0.0587 0.7347 0.6687 0.035 Uiso 0.58 1 calc R U P A 1
C4 C 0.1244(3) 0.8651(8) 0.6002(3) 0.034(2) Uani 0.58 1 d DG U P A 1
H4 H 0.0810 0.9061 0.5745 0.041 Uiso 0.58 1 calc R U P A 1
C5 C 0.2011(4) 0.9070(7) 0.5818(2) 0.031(2) Uani 0.58 1 d DG U P A 1
H5 H 0.2102 0.9766 0.5435 0.037 Uiso 0.58 1 calc R U P A 1
C6 C 0.2646(2) 0.8471(7) 0.6193(3) 0.0254(16) Uani 0.58 1 d DG U P A 1
H6 H 0.3170 0.8757 0.6067 0.030 Uiso 0.58 1 calc R U P A 1
C7 C 0.2526(6) 0.5835(13) 0.7665(4) 0.0166(19) Uani 0.58 1 d D U P A 1
C8 C 0.2812(4) 0.4887(6) 0.8245(2) 0.0169(14) Uani 0.58 1 d DG U P A 1
C9 C 0.2283(2) 0.4110(7) 0.8682(3) 0.0239(18) Uani 0.58 1 d DG . P A 1
H9 H 0.1732 0.4172 0.8597 0.029 Uiso 0.58 1 calc R U P A 1
C10 C 0.2561(4) 0.3244(7) 0.9245(2) 0.029(2) Uani 0.58 1 d DG . P A 1
H10 H 0.2200 0.2714 0.9543 0.034 Uiso 0.58 1 calc R U P A 1
C11 C 0.3368(4) 0.3154(10) 0.9370(3) 0.036(2) Uani 0.58 1 d DG U P A 1
H11 H 0.3558 0.2561 0.9754 0.043 Uiso 0.58 1 calc R U P A 1
C12 C 0.3897(2) 0.3930(11) 0.8932(4) 0.040(2) Uani 0.58 1 d DG U P A 1
H12 H 0.4448 0.3868 0.9018 0.048 Uiso 0.58 1 calc R U P A 1
C13 C 0.3619(3) 0.4796(8) 0.8370(3) 0.038(2) Uani 0.58 1 d DG U P A 1
H13 H 0.3980 0.5327 0.8071 0.046 Uiso 0.58 1 calc R U P A 1
N1A N 0.2041(4) 0.5291(8) 0.7914(3) 0.0255(9) Uani 0.42 1 d D . P B 2
H1A H 0.1524 0.5171 0.7909 0.031 Uiso 0.42 1 calc R U P B 2
N2A N 0.3200(4) 0.6117(8) 0.7602(3) 0.0236(8) Uani 0.42 1 d D . P B 2
H2A H 0.3584 0.6611 0.7379 0.028 Uiso 0.42 1 calc R U P B 2
C1A C 0.2532(4) 0.4596(10) 0.8382(4) 0.0251(14) Uani 0.42 1 d DG . P B 2
C2A C 0.3280(6) 0.5106(7) 0.8178(3) 0.0267(15) Uani 0.42 1 d DG . P B 2
C3A C 0.3940(4) 0.4634(11) 0.8551(5) 0.045(3) Uani 0.42 1 d DG . P B 2
H3A H 0.4451 0.4983 0.8412 0.054 Uiso 0.42 1 calc R U P B 2
C4A C 0.3852(5) 0.3650(14) 0.9127(5) 0.054(4) Uani 0.42 1 d DG . P B 2
H4A H 0.4303 0.3327 0.9381 0.065 Uiso 0.42 1 calc R U P B 2
C5A C 0.3104(7) 0.3139(13) 0.9330(4) 0.046(3) Uani 0.42 1 d DG . P B 2
H5A H 0.3044 0.2467 0.9724 0.056 Uiso 0.42 1 calc R U P B 2
C6A C 0.2444(4) 0.3612(11) 0.8958(5) 0.037(4) Uani 0.42 1 d DG . P B 2
H6A H 0.1933 0.3263 0.9097 0.045 Uiso 0.42 1 calc R U P B 2
C7A C 0.2452(11) 0.6186(18) 0.7460(6) 0.038(4) Uani 0.42 1 d D . P B 2
C8A C 0.2129(7) 0.7120(9) 0.6900(3) 0.038(3) Uani 0.42 1 d DG . P B 2
C9A C 0.2604(3) 0.7956(12) 0.6436(5) 0.037(3) Uani 0.42 1 d DG U P B 2
H9A H 0.3162 0.7865 0.6465 0.044 Uiso 0.42 1 calc R U P B 2
C10A C 0.2262(6) 0.8924(10) 0.5930(4) 0.023(2) Uani 0.42 1 d DG U P B 2
H10A H 0.2587 0.9496 0.5613 0.028 Uiso 0.42 1 calc R U P B 2
C11A C 0.1445(6) 0.9057(12) 0.5888(4) 0.063(5) Uani 0.42 1 d DG . P B 2
H11A H 0.1212 0.9719 0.5542 0.076 Uiso 0.42 1 calc R U P B 2
C12A C 0.0970(3) 0.8221(14) 0.6352(6) 0.066(5) Uani 0.42 1 d DG U P B 2
H12A H 0.0412 0.8311 0.6323 0.079 Uiso 0.42 1 calc R U P B 2
C13A C 0.1312(6) 0.7252(11) 0.6858(4) 0.054(4) Uani 0.42 1 d DG U P B 2
H13A H 0.0987 0.6681 0.7175 0.065 Uiso 0.42 1 calc R U P B 2
C14 C 0.5289(3) 0.8227(8) 0.5433(2) 0.0855(17) Uani 1 1 d . . . . .
H14A H 0.5425 0.9280 0.5656 0.128 Uiso 1 1 calc R U . . .
H14B H 0.5270 0.8393 0.4940 0.128 Uiso 1 1 calc R U . . .
H14C H 0.5688 0.7387 0.5543 0.128 Uiso 1 1 calc R 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
S1 O2 1.462(2) 3_656 ?
S1 O2 1.462(2) . ?
S1 O1 1.473(2) 3_656 ?
S1 O1 1.473(2) . ?
O3 C14 1.333(6) . ?
O3 H3B 0.8400 . ?
N1 C7 1.359(11) . ?
N1 C1 1.363(6) . ?
N1 H1 0.8800 . ?
N2 C7 1.330(12) . ?
N2 C2 1.365(5) . ?
N2 H2 0.8800 . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.455(8) . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N1A C7A 1.342(16) . ?
N1A C1A 1.361(8) . ?
N1A H1A 0.8800 . ?
N2A C7A 1.298(18) . ?
N2A C2A 1.401(7) . ?
N2A H2A 0.8800 . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C2A C3A 1.3900 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.441(11) . ?
C8A C9A 1.3900 . ?
C8A C13A 1.3900 . ?
C9A C10A 1.3900 . ?
C9A H9A 0.9500 . ?
C10A C11A 1.3900 . ?
C10A H10A 0.9500 . ?
C11A C12A 1.3900 . ?
C11A H11A 0.9500 . ?
C12A C13A 1.3900 . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
O2 S1 O2 111.2(2) 3_656 . ?
O2 S1 O1 110.18(14) 3_656 3_656 ?
O2 S1 O1 108.00(13) . 3_656 ?
O2 S1 O1 108.00(13) 3_656 . ?
O2 S1 O1 110.18(14) . . ?
O1 S1 O1 109.2(2) 3_656 . ?
C14 O3 H3B 109.5 . . ?
C7 N1 C1 109.2(6) . . ?
C7 N1 H1 125.4 . . ?
C1 N1 H1 125.4 . . ?
C7 N2 C2 107.7(5) . . ?
C7 N2 H2 126.2 . . ?
C2 N2 H2 126.2 . . ?
N1 C1 C2 105.2(5) . . ?
N1 C1 C6 134.8(5) . . ?
C2 C1 C6 120.0 . . ?
N2 C2 C1 108.8(5) . . ?
N2 C2 C3 131.1(5) . . ?
C1 C2 C3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N2 C7 N1 109.1(6) . . ?
N2 C7 C8 125.4(7) . . ?
N1 C7 C8 125.6(8) . . ?
C9 C8 C13 120.0 . . ?
C9 C8 C7 120.4(6) . . ?
C13 C8 C7 119.5(6) . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C7A N1A C1A 110.7(9) . . ?
C7A N1A H1A 124.6 . . ?
C1A N1A H1A 124.6 . . ?
C7A N2A C2A 107.1(8) . . ?
C7A N2A H2A 126.5 . . ?
C2A N2A H2A 126.5 . . ?
N1A C1A C2A 103.9(9) . . ?
N1A C1A C6A 136.1(9) . . ?
C2A C1A C6A 120.0 . . ?
C1A C2A C3A 120.0 . . ?
C1A C2A N2A 108.4(8) . . ?
C3A C2A N2A 131.5(8) . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
N2A C7A N1A 109.9(8) . . ?
N2A C7A C8A 123.9(13) . . ?
N1A C7A C8A 126.2(14) . . ?
C9A C8A C13A 120.0 . . ?
C9A C8A C7A 122.3(11) . . ?
C13A C8A C7A 117.6(11) . . ?
C8A C9A C10A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C12A C11A C10A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C12A C13A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C12A C13A C8A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C8A C13A H13A 120.0 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_(H2Bim)2SeO4
_database_code_depnum_ccdc_archive 'CCDC 1050272'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Benzimidazolium selenate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N4 O4 Se'
_chemical_formula_weight         381.25

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

_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'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'-x, -y, z+1/2'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   18.5107(19)
_cell_length_b                   18.5107(19)
_cell_length_c                   18.953(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6494.2(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9087
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.31

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             3072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    2.338
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Blessing (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68473
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.538
_diffrn_reflns_theta_max         26.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6722
_reflns_number_gt                5364
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger. Refined as a 2-component 
 inversion twin, and no satisfactory centrosymmetric alternative was found.
 
 All non-hydrogen atoms were included in the refinement using the 
 anisotropic model. The hydrogen atoms connected to carbon and nitrogen 
 atoms were placed in positions calculated based on the assigned 
 hybridization of the parent non-hydrogen atom and included in the 
 refinement using a riding model.

 The structure contains 4 symmetrically non-equivalent benzimidazolium
 cations and three symmetrically non-equivalent selenate ions with 
 occupational parameters 1, 0.5 and 0.5. The selenate ions containing
 atoms Se2 and Se3 are placed on two-fold rotation axes, explaining
 0.5 occupancy parameters.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0278P)²+2.4137P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.568(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6722
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0605
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
Se1 Se 0.14196(2) 0.38811(2) 0.24952(3) 0.01035(10) Uani 1 1 d . . . . .
Se2 Se 0.14155(2) 0.14155(2) 0.0000 0.01086(14) Uani 1 2 d S T P . .
Se3 Se 0.11527(2) -0.11527(2) 0.2500 0.01087(14) Uani 1 2 d S T P . .
O1 O 0.19377(15) 0.33830(15) 0.19901(15) 0.0155(7) Uani 1 1 d . . . . .
O2 O 0.08555(15) 0.43307(14) 0.19861(15) 0.0152(7) Uani 1 1 d . . . . .
O3 O 0.19057(15) 0.44450(15) 0.29607(16) 0.0166(7) Uani 1 1 d . . . . .
O4 O 0.09618(15) 0.33626(15) 0.30371(15) 0.0154(6) Uani 1 1 d . . . . .
O5 O 0.21115(15) 0.14448(16) -0.05347(16) 0.0195(7) Uani 1 1 d . . . . .
O6 O 0.06818(15) 0.14225(17) -0.04842(16) 0.0192(7) Uani 1 1 d . . . . .
O7 O 0.18448(15) -0.11731(17) 0.30465(17) 0.0207(7) Uani 1 1 d . . . . .
O8 O 0.04129(15) -0.11882(15) 0.29701(17) 0.0170(7) Uani 1 1 d . . . . .
N1 N 0.17803(18) 0.08359(18) 0.2450(2) 0.0166(8) Uani 1 1 d . . . . .
H1A H 0.1668 0.0386 0.2347 0.020 Uiso 1 1 calc R U . . .
N2 N 0.19045(19) 0.19981(19) 0.23475(18) 0.0164(8) Uani 1 1 d . . . . .
H2 H 0.1890 0.2435 0.2165 0.020 Uiso 1 1 calc R U . . .
N3 N 0.18333(18) 0.34285(18) 0.00954(19) 0.0156(8) Uani 1 1 d . . . . .
H3 H 0.1770 0.2976 0.0225 0.019 Uiso 1 1 calc R U . . .
N4 N 0.18202(19) 0.46032(18) 0.0125(2) 0.0157(9) Uani 1 1 d . . . . .
H4A H 0.1751 0.5047 0.0279 0.019 Uiso 1 1 calc R U . . .
N5 N 0.44579(17) 0.41924(18) 0.2529(2) 0.0154(8) Uani 1 1 d . . . . .
H5A H 0.4897 0.4046 0.2635 0.019 Uiso 1 1 calc R U . . .
N6 N 0.33043(19) 0.43995(19) 0.2617(2) 0.0172(9) Uani 1 1 d . . . . .
H6A H 0.2863 0.4409 0.2789 0.021 Uiso 1 1 calc R U . . .
N7 N 0.56497(19) 0.92988(18) 0.0116(2) 0.0168(9) Uani 1 1 d . . . . .
H7A H 0.5686 0.9747 0.0267 0.020 Uiso 1 1 calc R U . . .
N8 N 0.57329(19) 0.81330(19) 0.0085(2) 0.0172(8) Uani 1 1 d . . . . .
H8A H 0.5833 0.7687 0.0214 0.021 Uiso 1 1 calc R U . . .
C1 C 0.1680(2) 0.1403(2) 0.2037(2) 0.0164(10) Uani 1 1 d . . . . .
H1 H 0.1475 0.1384 0.1578 0.020 Uiso 1 1 calc R U . . .
C2 C 0.2094(2) 0.1074(2) 0.3074(3) 0.0152(10) Uani 1 1 d . . . . .
C3 C 0.2167(2) 0.1823(2) 0.3011(3) 0.0160(10) Uani 1 1 d . . . . .
C4 C 0.2457(2) 0.2244(3) 0.3546(3) 0.0214(12) Uani 1 1 d . . . . .
H4 H 0.2503 0.2753 0.3501 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2673(3) 0.1883(3) 0.4147(3) 0.0300(13) Uani 1 1 d . . . . .
H5 H 0.2870 0.2150 0.4530 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2609(3) 0.1132(3) 0.4206(3) 0.0325(14) Uani 1 1 d . . . . .
H6 H 0.2768 0.0903 0.4627 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2325(3) 0.0715(3) 0.3678(2) 0.0246(12) Uani 1 1 d . . . . .
H7 H 0.2287 0.0205 0.3722 0.030 Uiso 1 1 calc R U . . .
C8 C 0.1659(2) 0.4006(2) 0.0472(2) 0.0177(10) Uani 1 1 d . . . . .
H8 H 0.1448 0.3992 0.0928 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2132(2) 0.3659(2) -0.0541(3) 0.0147(10) Uani 1 1 d . . . . .
C10 C 0.2117(2) 0.4414(2) -0.0521(2) 0.0135(9) Uani 1 1 d . . . . .
C11 C 0.2360(3) 0.4826(3) -0.1084(3) 0.0210(11) Uani 1 1 d . . . . .
H11 H 0.2348 0.5339 -0.1071 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2617(3) 0.4460(3) -0.1658(3) 0.0278(13) Uani 1 1 d . . . . .
H12 H 0.2785 0.4725 -0.2055 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2637(3) 0.3699(3) -0.1674(3) 0.0320(14) Uani 1 1 d . . . . .
H13 H 0.2821 0.3463 -0.2081 0.038 Uiso 1 1 calc R U . . .
C14 C 0.2397(3) 0.3287(3) -0.1115(3) 0.0238(12) Uani 1 1 d . . . . .
H14 H 0.2414 0.2774 -0.1125 0.029 Uiso 1 1 calc R U . . .
C15 C 0.3875(2) 0.4118(2) 0.2934(2) 0.0169(10) Uani 1 1 d . . . . .
H15 H 0.3870 0.3895 0.3386 0.020 Uiso 1 1 calc R U . . .
C16 C 0.4255(2) 0.4542(2) 0.1908(3) 0.0155(10) Uani 1 1 d . . . . .
C17 C 0.3516(2) 0.4677(2) 0.1973(3) 0.0163(10) Uani 1 1 d . . . . .
C18 C 0.3131(3) 0.5029(2) 0.1447(3) 0.0213(11) Uani 1 1 d . . . . .
H18 H 0.2628 0.5118 0.1488 0.026 Uiso 1 1 calc R U . . .
C19 C 0.3515(3) 0.5242(3) 0.0863(3) 0.0249(12) Uani 1 1 d . . . . .
H19 H 0.3272 0.5488 0.0492 0.030 Uiso 1 1 calc R U . . .
C20 C 0.4259(3) 0.5106(3) 0.0800(3) 0.0233(12) Uani 1 1 d . . . . .
H20 H 0.4505 0.5263 0.0388 0.028 Uiso 1 1 calc R U . . .
C21 C 0.4643(3) 0.4754(3) 0.1316(2) 0.0197(10) Uani 1 1 d . . . . .
H21 H 0.5145 0.4661 0.1270 0.024 Uiso 1 1 calc R U . . .
C22 C 0.5880(3) 0.8719(2) 0.0453(3) 0.0187(10) Uani 1 1 d . . . . .
H22 H 0.6118 0.8723 0.0897 0.022 Uiso 1 1 calc R U . . .
C23 C 0.5339(2) 0.9083(2) -0.0518(3) 0.0161(10) Uani 1 1 d . . . . .
C24 C 0.5395(2) 0.8332(2) -0.0539(2) 0.0140(10) Uani 1 1 d . . . . .
C25 C 0.5141(3) 0.7938(3) -0.1112(2) 0.0197(11) Uani 1 1 d . . . . .
H25 H 0.5184 0.7427 -0.1132 0.024 Uiso 1 1 calc R U . . .
C26 C 0.4826(3) 0.8323(3) -0.1646(3) 0.0254(12) Uani 1 1 d . . . . .
H26 H 0.4642 0.8071 -0.2044 0.030 Uiso 1 1 calc R U . . .
C27 C 0.4767(3) 0.9082(3) -0.1620(3) 0.0258(12) Uani 1 1 d . . . . .
H27 H 0.4546 0.9329 -0.2003 0.031 Uiso 1 1 calc R U . . .
C28 C 0.5020(3) 0.9475(3) -0.1056(3) 0.0214(12) Uani 1 1 d . . . . .
H28 H 0.4978 0.9986 -0.1036 0.026 Uiso 1 1 calc R 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
Se1 O3 1.636(3) . ?
Se1 O1 1.639(3) . ?
Se1 O4 1.641(3) . ?
Se1 O2 1.647(3) . ?
Se2 O6 1.639(3) 7 ?
Se2 O6 1.639(3) . ?
Se2 O5 1.640(3) 7 ?
Se2 O5 1.640(3) . ?
Se3 O8 1.635(3) . ?
Se3 O8 1.635(3) 8 ?
Se3 O7 1.648(3) . ?
Se3 O7 1.648(3) 8 ?
N1 C1 1.323(5) . ?
N1 C2 1.390(6) . ?
N2 C1 1.315(5) . ?
N2 C3 1.386(6) . ?
N3 C8 1.324(5) . ?
N3 C9 1.394(6) . ?
N4 C8 1.320(5) . ?
N4 C10 1.387(6) . ?
N5 C15 1.331(5) . ?
N5 C16 1.395(6) . ?
N6 C15 1.322(5) . ?
N6 C17 1.381(6) . ?
N7 C22 1.321(5) . ?
N7 C23 1.390(6) . ?
N8 C22 1.318(5) . ?
N8 C24 1.387(6) . ?
C2 C7 1.392(6) . ?
C2 C3 1.397(6) . ?
C3 C4 1.387(6) . ?
C4 C5 1.381(7) . ?
C5 C6 1.400(7) . ?
C6 C7 1.368(7) . ?
C9 C14 1.378(6) . ?
C9 C10 1.399(6) . ?
C10 C11 1.386(6) . ?
C11 C12 1.367(7) . ?
C12 C13 1.411(7) . ?
C13 C14 1.378(7) . ?
C16 C21 1.389(6) . ?
C16 C17 1.397(6) . ?
C17 C18 1.388(6) . ?
C18 C19 1.374(7) . ?
C19 C20 1.405(7) . ?
C20 C21 1.372(6) . ?
C23 C28 1.385(6) . ?
C23 C24 1.395(6) . ?
C24 C25 1.390(6) . ?
C25 C26 1.367(6) . ?
C26 C27 1.411(7) . ?
C27 C28 1.376(7) . ?

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
O3 Se1 O1 110.62(15) . . ?
O3 Se1 O4 108.63(15) . . ?
O1 Se1 O4 109.80(15) . . ?
O3 Se1 O2 110.00(15) . . ?
O1 Se1 O2 108.24(15) . . ?
O4 Se1 O2 109.55(15) . . ?
O6 Se2 O6 109.1(2) 7 . ?
O6 Se2 O5 107.74(15) 7 7 ?
O6 Se2 O5 111.54(16) . 7 ?
O6 Se2 O5 111.54(16) 7 . ?
O6 Se2 O5 107.74(15) . . ?
O5 Se2 O5 109.3(2) 7 . ?
O8 Se3 O8 111.4(2) . 8 ?
O8 Se3 O7 107.92(16) . . ?
O8 Se3 O7 109.30(15) 8 . ?
O8 Se3 O7 109.30(15) . 8 ?
O8 Se3 O7 107.92(16) 8 8 ?
O7 Se3 O7 111.1(2) . 8 ?
C1 N1 C2 108.0(4) . . ?
C1 N2 C3 108.7(4) . . ?
C8 N3 C9 108.4(4) . . ?
C8 N4 C10 108.5(4) . . ?
C15 N5 C16 108.5(3) . . ?
C15 N6 C17 108.8(4) . . ?
C22 N7 C23 108.6(4) . . ?
C22 N8 C24 109.1(4) . . ?
N2 C1 N1 110.8(4) . . ?
C7 C2 N1 132.6(4) . . ?
C7 C2 C3 121.0(5) . . ?
N1 C2 C3 106.4(4) . . ?
N2 C3 C4 131.9(4) . . ?
N2 C3 C2 106.0(4) . . ?
C4 C3 C2 122.1(5) . . ?
C5 C4 C3 116.4(5) . . ?
C4 C5 C6 121.4(5) . . ?
C7 C6 C5 122.3(5) . . ?
C6 C7 C2 116.7(5) . . ?
N4 C8 N3 110.7(4) . . ?
C14 C9 N3 132.2(4) . . ?
C14 C9 C10 121.8(4) . . ?
N3 C9 C10 105.9(4) . . ?
N4 C10 C11 132.0(4) . . ?
N4 C10 C9 106.5(4) . . ?
C11 C10 C9 121.5(4) . . ?
C12 C11 C10 116.9(5) . . ?
C11 C12 C13 121.4(5) . . ?
C14 C13 C12 121.9(5) . . ?
C9 C14 C13 116.4(5) . . ?
N6 C15 N5 110.2(4) . . ?
C21 C16 N5 132.4(4) . . ?
C21 C16 C17 121.8(4) . . ?
N5 C16 C17 105.7(4) . . ?
N6 C17 C18 131.7(4) . . ?
N6 C17 C16 106.8(4) . . ?
C18 C17 C16 121.5(5) . . ?
C19 C18 C17 116.7(4) . . ?
C18 C19 C20 121.6(5) . . ?
C21 C20 C19 122.2(5) . . ?
C20 C21 C16 116.2(4) . . ?
N8 C22 N7 110.2(4) . . ?
C28 C23 N7 131.5(4) . . ?
C28 C23 C24 122.3(4) . . ?
N7 C23 C24 106.3(4) . . ?
N8 C24 C25 132.8(4) . . ?
N8 C24 C23 105.9(4) . . ?
C25 C24 C23 121.3(4) . . ?
C26 C25 C24 116.8(4) . . ?
C25 C26 C27 121.8(5) . . ?
C28 C27 C26 121.8(5) . . ?
C27 C28 C23 116.1(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 N1 -0.4(5) . . . . ?
C2 N1 C1 N2 -0.2(5) . . . . ?
C1 N1 C2 C7 -178.6(5) . . . . ?
C1 N1 C2 C3 0.7(5) . . . . ?
C1 N2 C3 C4 -179.4(5) . . . . ?
C1 N2 C3 C2 0.9(5) . . . . ?
C7 C2 C3 N2 178.5(4) . . . . ?
N1 C2 C3 N2 -1.0(5) . . . . ?
C7 C2 C3 C4 -1.3(7) . . . . ?
N1 C2 C3 C4 179.3(4) . . . . ?
N2 C3 C4 C5 -179.5(5) . . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C4 C5 C6 C7 -0.6(9) . . . . ?
C5 C6 C7 C2 -0.5(8) . . . . ?
N1 C2 C7 C6 -179.4(5) . . . . ?
C3 C2 C7 C6 1.4(7) . . . . ?
C10 N4 C8 N3 0.2(5) . . . . ?
C9 N3 C8 N4 0.3(5) . . . . ?
C8 N3 C9 C14 -179.7(5) . . . . ?
C8 N3 C9 C10 -0.7(5) . . . . ?
C8 N4 C10 C11 178.4(5) . . . . ?
C8 N4 C10 C9 -0.6(5) . . . . ?
C14 C9 C10 N4 180.0(4) . . . . ?
N3 C9 C10 N4 0.8(5) . . . . ?
C14 C9 C10 C11 0.8(7) . . . . ?
N3 C9 C10 C11 -178.4(4) . . . . ?
N4 C10 C11 C12 -179.0(5) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
C10 C11 C12 C13 -0.4(8) . . . . ?
C11 C12 C13 C14 0.3(9) . . . . ?
N3 C9 C14 C13 178.0(5) . . . . ?
C10 C9 C14 C13 -0.9(7) . . . . ?
C12 C13 C14 C9 0.4(8) . . . . ?
C17 N6 C15 N5 -0.2(5) . . . . ?
C16 N5 C15 N6 -0.2(5) . . . . ?
C15 N5 C16 C21 179.7(5) . . . . ?
C15 N5 C16 C17 0.5(5) . . . . ?
C15 N6 C17 C18 -179.5(5) . . . . ?
C15 N6 C17 C16 0.5(5) . . . . ?
C21 C16 C17 N6 -179.9(4) . . . . ?
N5 C16 C17 N6 -0.6(5) . . . . ?
C21 C16 C17 C18 0.1(7) . . . . ?
N5 C16 C17 C18 179.4(4) . . . . ?
N6 C17 C18 C19 179.6(4) . . . . ?
C16 C17 C18 C19 -0.4(7) . . . . ?
C17 C18 C19 C20 0.4(7) . . . . ?
C18 C19 C20 C21 0.0(8) . . . . ?
C19 C20 C21 C16 -0.4(7) . . . . ?
N5 C16 C21 C20 -178.8(5) . . . . ?
C17 C16 C21 C20 0.4(7) . . . . ?
C24 N8 C22 N7 1.0(5) . . . . ?
C23 N7 C22 N8 -0.8(5) . . . . ?
C22 N7 C23 C28 179.8(5) . . . . ?
C22 N7 C23 C24 0.3(5) . . . . ?
C22 N8 C24 C25 178.7(5) . . . . ?
C22 N8 C24 C23 -0.8(5) . . . . ?
C28 C23 C24 N8 -179.3(4) . . . . ?
N7 C23 C24 N8 0.3(5) . . . . ?
C28 C23 C24 C25 1.1(7) . . . . ?
N7 C23 C24 C25 -179.3(4) . . . . ?
N8 C24 C25 C26 179.7(5) . . . . ?
C23 C24 C25 C26 -0.9(7) . . . . ?
C24 C25 C26 C27 0.5(7) . . . . ?
C25 C26 C27 C28 -0.3(8) . . . . ?
C26 C27 C28 C23 0.4(8) . . . . ?
N7 C23 C28 C27 179.7(5) . . . . ?
C24 C23 C28 C27 -0.8(7) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_(H2MeBim)2SeO4_MeOH_H2O
_database_code_depnum_ccdc_archive 'CCDC 1050273'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
'2-methylbenzimidazolium selenate methanol solvate hydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H23 N4 O5.50 Se'
_chemical_formula_weight         450.35

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'
Se Se -0.0929 2.2259 '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                   25.917(2)
_cell_length_b                   8.7717(7)
_cell_length_c                   17.5915(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.3770(10)
_cell_angle_gamma                90
_cell_volume                     3933.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4913
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.76

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             1848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.948
_shelx_estimated_absorpt_T_min   0.414
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6255
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'Blessing (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22811
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.598
_diffrn_reflns_theta_max         28.829
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4797
_reflns_number_gt                3584
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 Almost all (vide infra) non-hydrogen atoms were included in the refinement 
 using the anisotropic model. The hydrogen atoms connected to carbon and 
 nitrogen atoms were placed in positions calculated based on the assigned 
 hybridization of the parent non-hydrogen atom and included in the 
 refinement using a riding model.The hydrogen atom of the O-H group
 in methanol was placed in positions calculated using the SHELX command
 HFIX 147 and included in the refinement using the ridign model. The
 hydrogen atom of the water molecule was located from the Fourier
 difference electron density map and its coordinates and isotropic
 thermal parameter (set to be 150% of the Uiso for the parent oxygen atom)
 were not refined.

 The selenate ion was found to be disordered over two sites sharing
 the selenium atom, with relative occupancies of 0.93 and 0.07. Atoms of 
 the minor disordered site were refined using the isotropic model.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+6.4346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4797
_refine_ls_number_parameters     279
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.048
_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
Se1 Se 0.11022(2) -0.57520(5) 0.15423(3) 0.01925(10) Uani 0.93 1 d . . P A 1
O1 O 0.15997(8) -0.4591(2) 0.15478(13) 0.0352(5) Uani 0.93 1 d . . P A 1
O3 O 0.11806(10) -0.6892(2) 0.22812(12) 0.0307(5) Uani 0.93 1 d . . P A 1
O2 O 0.05695(8) -0.4735(2) 0.15199(12) 0.0285(5) Uani 0.93 1 d . . P A 1
O4 O 0.10523(13) -0.6748(3) 0.07465(13) 0.0351(7) Uani 0.93 1 d . . P A 1
Se1B Se 0.1328(4) -0.5899(8) 0.1524(4) 0.044(2) Uani 0.07 1 d D . P B 2
O1B O 0.1107(12) -0.430(2) 0.1829(17) 0.12(2) Uiso 0.07 1 d D . P B 2
O2B O 0.1884(6) -0.557(3) 0.1230(15) 0.069(11) Uiso 0.07 1 d D . P B 2
O3B O 0.1423(10) -0.713(2) 0.2237(11) 0.031(9) Uiso 0.07 1 d D . P B 2
O4B O 0.0898(9) -0.659(3) 0.0807(11) 0.027(12) Uiso 0.07 1 d D . P B 2
O5 O 0.0000 0.6845(4) 0.2500 0.0824(15) Uani 1 2 d S T P . .
H5A H 0.0108 0.6169 0.2117 0.105 Uiso 1 1 d . U . . .
O6 O 0.29282(10) 0.1978(4) 0.21205(16) 0.0652(8) Uani 1 1 d . . . . .
H6A H 0.3081 0.1454 0.2494 0.098 Uiso 1 1 calc R U . . .
N1 N 0.15542(9) -0.3146(3) -0.12066(13) 0.0269(5) Uani 1 1 d . . . . .
H1 H 0.1476 -0.3201 -0.1714 0.032 Uiso 1 1 calc R U . . .
N2 N 0.16548(10) -0.3766(3) 0.00060(13) 0.0338(6) Uani 1 1 d . . . . .
H2 H 0.1652 -0.4307 0.0427 0.041 Uiso 1 1 calc R U . . .
N3 N 0.08169(9) 1.0292(3) 0.06227(13) 0.0256(5) Uani 1 1 d . . . . .
H3 H 0.0915 1.1241 0.0725 0.031 Uiso 1 1 calc R U . . .
N4 N 0.06489(9) 0.7893(3) 0.07859(13) 0.0266(5) Uani 1 1 d . . . . .
H4A H 0.0619 0.7012 0.1013 0.032 Uiso 1 1 calc R U . . .
C1 C 0.12707(15) -0.5768(4) -0.0950(2) 0.0453(8) Uani 1 1 d . . . . .
H1A H 0.1524 -0.6351 -0.1185 0.068 Uiso 1 1 calc R U . . .
H1B H 0.0945 -0.5646 -0.1327 0.068 Uiso 1 1 calc R U . . .
H1C H 0.1197 -0.6312 -0.0496 0.068 Uiso 1 1 calc R U . . .
C2 C 0.14896(11) -0.4261(3) -0.07171(17) 0.0311(6) Uani 1 1 d . . . . .
C3 C 0.17639(10) -0.1885(3) -0.07857(15) 0.0252(6) Uani 1 1 d . . . . .
C4 C 0.19022(11) -0.0440(3) -0.10050(17) 0.0299(6) Uani 1 1 d . . . . .
H4 H 0.1859 -0.0155 -0.1534 0.036 Uiso 1 1 calc R U . . .
C5 C 0.21051(12) 0.0564(4) -0.04237(19) 0.0386(7) Uani 1 1 d . . . . .
H5 H 0.2204 0.1558 -0.0558 0.046 Uiso 1 1 calc R U . . .
C6 C 0.21695(13) 0.0164(4) 0.0350(2) 0.0438(8) Uani 1 1 d . . . . .
H6 H 0.2310 0.0891 0.0732 0.053 Uiso 1 1 calc R U . . .
C7 C 0.20352(12) -0.1253(4) 0.05766(17) 0.0394(8) Uani 1 1 d . . . . .
H7 H 0.2079 -0.1523 0.1107 0.047 Uiso 1 1 calc R U . . .
C8 C 0.18299(11) -0.2288(4) -0.00068(16) 0.0294(6) Uani 1 1 d . . . . .
C9 C 0.10161(13) 0.9317(3) 0.19793(17) 0.0376(7) Uani 1 1 d . . . . .
H9A H 0.1371 0.8895 0.2111 0.056 Uiso 1 1 calc R U . . .
H9B H 0.0781 0.8754 0.2256 0.056 Uiso 1 1 calc R U . . .
H9C H 0.1021 1.0394 0.2128 0.056 Uiso 1 1 calc R U . . .
C10 C 0.08288(11) 0.9180(3) 0.11431(16) 0.0271(6) Uani 1 1 d . . . . .
C11 C 0.05172(10) 0.8168(3) 0.00009(16) 0.0249(6) Uani 1 1 d . . . . .
C12 C 0.03093(11) 0.7237(4) -0.06167(18) 0.0337(7) Uani 1 1 d . . . . .
H12 H 0.0230 0.6195 -0.0544 0.040 Uiso 1 1 calc R U . . .
C13 C 0.02239(12) 0.7887(4) -0.13348(18) 0.0414(8) Uani 1 1 d . . . . .
H13 H 0.0085 0.7281 -0.1772 0.050 Uiso 1 1 calc R U . . .
C14 C 0.03353(12) 0.9417(4) -0.14405(18) 0.0428(8) Uani 1 1 d . . . . .
H14 H 0.0273 0.9822 -0.1950 0.051 Uiso 1 1 calc R U . . .
C15 C 0.05332(11) 1.0364(4) -0.08318(18) 0.0323(7) Uani 1 1 d . . . . .
H15 H 0.0603 1.1411 -0.0907 0.039 Uiso 1 1 calc R U . . .
C16 C 0.06243(10) 0.9704(3) -0.01060(16) 0.0236(6) Uani 1 1 d . . . . .
C17 C 0.24239(13) 0.2303(5) 0.22239(19) 0.0478(9) Uani 1 1 d . . . . .
H17A H 0.2254 0.2975 0.1808 0.072 Uiso 1 1 calc R U . . .
H17B H 0.2436 0.2812 0.2723 0.072 Uiso 1 1 calc R U . . .
H17C H 0.2223 0.1354 0.2215 0.072 Uiso 1 1 calc R 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
Se1 O3 1.6237(19) . ?
Se1 O4 1.635(2) . ?
Se1 O2 1.638(2) . ?
Se1 O1 1.642(2) . ?
Se1B O4B 1.639(5) . ?
Se1B O2B 1.641(5) . ?
Se1B O1B 1.643(5) . ?
Se1B O3B 1.643(5) . ?
O6 C17 1.382(4) . ?
N1 C2 1.334(3) . ?
N1 C3 1.386(3) . ?
N2 C2 1.339(4) . ?
N2 C8 1.375(4) . ?
N3 C10 1.334(3) . ?
N3 C16 1.388(3) . ?
N4 C10 1.334(3) . ?
N4 C11 1.383(3) . ?
C1 C2 1.467(4) . ?
C3 C4 1.391(4) . ?
C3 C8 1.395(4) . ?
C4 C5 1.380(4) . ?
C5 C6 1.386(5) . ?
C6 C7 1.370(5) . ?
C7 C8 1.401(4) . ?
C9 C10 1.469(4) . ?
C11 C12 1.388(4) . ?
C11 C16 1.395(4) . ?
C12 C13 1.367(4) . ?
C13 C14 1.392(5) . ?
C14 C15 1.379(4) . ?
C15 C16 1.383(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
O3 Se1 O4 109.59(11) . . ?
O3 Se1 O2 109.75(12) . . ?
O4 Se1 O2 109.51(14) . . ?
O3 Se1 O1 113.11(12) . . ?
O4 Se1 O1 106.11(14) . . ?
O2 Se1 O1 108.68(11) . . ?
O4B Se1B O2B 109.6(6) . . ?
O4B Se1B O1B 109.7(6) . . ?
O2B Se1B O1B 109.4(6) . . ?
O4B Se1B O3B 109.5(6) . . ?
O2B Se1B O3B 109.6(6) . . ?
O1B Se1B O3B 109.1(6) . . ?
C2 N1 C3 108.8(2) . . ?
C2 N2 C8 109.9(2) . . ?
C10 N3 C16 108.8(2) . . ?
C10 N4 C11 109.0(2) . . ?
N1 C2 N2 108.6(3) . . ?
N1 C2 C1 124.6(3) . . ?
N2 C2 C1 126.8(3) . . ?
N1 C3 C4 132.4(2) . . ?
N1 C3 C8 106.8(2) . . ?
C4 C3 C8 120.7(3) . . ?
C5 C4 C3 117.3(3) . . ?
C4 C5 C6 121.9(3) . . ?
C7 C6 C5 121.6(3) . . ?
C6 C7 C8 117.2(3) . . ?
N2 C8 C3 105.8(3) . . ?
N2 C8 C7 133.0(3) . . ?
C3 C8 C7 121.2(3) . . ?
N4 C10 N3 109.4(2) . . ?
N4 C10 C9 124.4(3) . . ?
N3 C10 C9 126.1(3) . . ?
N4 C11 C12 132.1(3) . . ?
N4 C11 C16 106.5(2) . . ?
C12 C11 C16 121.4(3) . . ?
C13 C12 C11 116.9(3) . . ?
C12 C13 C14 121.5(3) . . ?
C15 C14 C13 122.3(3) . . ?
C14 C15 C16 116.3(3) . . ?
C15 C16 N3 132.1(3) . . ?
C15 C16 C11 121.6(3) . . ?
N3 C16 C11 106.3(2) . . ?

_refine_diff_density_max         0.653
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_(H2PhBim)2SeO4
_database_code_depnum_ccdc_archive 'CCDC 1050274'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            '2-phenylbenzimidazolium selenate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N4 O4 Se'
_chemical_formula_weight         533.43

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'
Se Se -0.0929 2.2259 '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                   9.611(4)
_cell_length_b                   10.852(4)
_cell_length_c                   11.918(5)
_cell_angle_alpha                83.339(6)
_cell_angle_beta                 72.175(5)
_cell_angle_gamma                88.808(5)
_cell_volume                     1175.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1471
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      19.87

_exptl_crystal_description       Rhombohedra
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_absorpt_coefficient_mu    1.639
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4940
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Blessing, (1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12318
_diffrn_reflns_av_unetI/netI     0.1190
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.807
_diffrn_reflns_theta_max         26.254
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4683
_reflns_number_gt                3123
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHEXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
 All non-hydrogen atoms were included in the refinement using the 
 anisotropic model. The hydrogen atoms connected to carbon and nitrogen 
 atoms were placed in positions calculated based on the assigned 
 hybridization of the parent non-hydrogen atom and included in the 
 refinement using a riding model.

 There are three symmetrically non-equivalent phenylbenzimidazolium ions
 in the structure, with occupational parameter of 1 (ion containing
 the nitrogen atoms N1 and N2), 0.5 (containing nitrogen atoms N3 and N4)
 and 0.5 (containing the nitrogen atoms N5 and N6). The 
 phenylbenzimidazolium cations with 0.5 occupancy are both disordered
 over two positions with a mutually antiparallel orientation of the cation.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0692P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4683
_refine_ls_number_parameters     379
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1514
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      0.999
_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
Se1 Se 1.55467(6) 0.42545(5) 0.28316(5) 0.02553(19) Uani 1 1 d . . . . .
O1 O 1.4857(4) 0.3270(3) 0.4007(3) 0.0329(9) Uani 1 1 d . . . . .
O2 O 1.4254(4) 0.5036(3) 0.2495(3) 0.0312(9) Uani 1 1 d . . . . .
O3 O 1.6654(4) 0.5231(3) 0.3081(3) 0.0362(10) Uani 1 1 d . . . . .
O4 O 1.6462(4) 0.3496(3) 0.1734(3) 0.0399(10) Uani 1 1 d . . . . .
N1 N 0.9061(5) 0.4696(4) 0.3591(4) 0.0291(10) Uani 1 1 d . . . . .
H1 H 0.8227 0.4962 0.3499 0.035 Uiso 1 1 calc R U . . .
N2 N 1.1380(4) 0.4607(4) 0.3443(4) 0.0275(10) Uani 1 1 d . . . . .
H2 H 1.2314 0.4808 0.3234 0.033 Uiso 1 1 calc R U . . .
C1 C 1.0734(3) 0.3557(3) 0.4162(3) 0.0253(12) Uani 1 1 d G . . . .
C2 C 0.9260(3) 0.3619(3) 0.4247(3) 0.0301(13) Uani 1 1 d G . . . .
C3 C 0.8308(3) 0.2661(3) 0.4891(3) 0.0352(14) Uani 1 1 d G . . . .
H3 H 0.7300 0.2703 0.4949 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8830(3) 0.1640(3) 0.5449(3) 0.0406(15) Uani 1 1 d G . . . .
H4 H 0.8180 0.0985 0.5888 0.049 Uiso 1 1 calc R U . . .
C5 C 1.0305(4) 0.1577(3) 0.5363(3) 0.0368(14) Uani 1 1 d G . . . .
H5 H 1.0662 0.0879 0.5744 0.044 Uiso 1 1 calc R U . . .
C6 C 1.1257(3) 0.2536(3) 0.4719(3) 0.0325(13) Uani 1 1 d G . . . .
H6 H 1.2264 0.2493 0.4661 0.039 Uiso 1 1 calc R U . . .
C7 C 1.0357(5) 0.5265(4) 0.3117(4) 0.0233(11) Uani 1 1 d . . . . .
C8 C 1.0597(4) 0.6456(3) 0.2372(3) 0.0275(12) Uani 1 1 d G . . . .
C9 C 1.1998(3) 0.6969(3) 0.1910(4) 0.0498(18) Uani 1 1 d G . . . .
H9 H 1.2800 0.6539 0.2070 0.060 Uiso 1 1 calc R U . . .
C10 C 1.2225(3) 0.8111(4) 0.1215(4) 0.072(2) Uani 1 1 d G . . . .
H10 H 1.3183 0.8462 0.0900 0.086 Uiso 1 1 calc R U . . .
C11 C 1.1051(4) 0.8740(3) 0.0982(4) 0.0556(19) Uani 1 1 d G . . . .
H11 H 1.1207 0.9521 0.0507 0.067 Uiso 1 1 calc R U . . .
C12 C 0.9651(3) 0.8227(3) 0.1443(4) 0.0382(15) Uani 1 1 d G . . . .
H12 H 0.8848 0.8657 0.1283 0.046 Uiso 1 1 calc R U . . .
C13 C 0.9423(3) 0.7085(3) 0.2138(3) 0.0322(13) Uani 1 1 d G . . . .
H13 H 0.8466 0.6734 0.2453 0.039 Uiso 1 1 calc R U . . .
N3 N 1.4973(9) 0.1088(7) 0.5084(9) 0.025(2) Uani 0.5 1 d . . P . .
H3A H 1.5083 0.1758 0.4571 0.030 Uiso 0.5 1 calc R U P . .
N4 N 1.4832(9) -0.0857(8) 0.5813(8) 0.0229(19) Uani 0.5 1 d . . P . .
H4A H 1.4843 -0.1672 0.5870 0.027 Uiso 0.5 1 calc R U P . .
C14 C 1.4681(9) 0.1084(14) 0.6263(5) 0.021(3) Uani 0.5 1 d G U P . .
C15 C 1.4528(10) 0.2024(6) 0.6989(13) 0.017(3) Uani 0.5 1 d G . P . .
H15 H 1.4710 0.2864 0.6649 0.020 Uiso 0.5 1 calc R U P . .
C16 C 1.4258(14) 0.1729(10) 0.8204(11) 0.024(4) Uani 0.5 1 d G . P . .
H16 H 1.4154 0.2371 0.8700 0.029 Uiso 0.5 1 calc R U P . .
C17 C 1.4141(16) 0.0494(14) 0.8692(5) 0.034(5) Uani 0.5 1 d G . P . .
H17 H 1.3956 0.0293 0.9523 0.041 Uiso 0.5 1 calc R U P . .
C18 C 1.4293(13) -0.0445(6) 0.7966(13) 0.021(3) Uani 0.5 1 d G U P . .
H18 H 1.4213 -0.1289 0.8300 0.026 Uiso 0.5 1 calc R U P . .
C19 C 1.4563(10) -0.0150(11) 0.6751(11) 0.022(3) Uani 0.5 1 d G U P . .
C20 C 1.507(3) -0.009(2) 0.4806(16) 0.020(4) Uani 0.5 1 d . U P . .
C21 C 1.5371(10) -0.0409(14) 0.3618(6) 0.025(3) Uani 0.5 1 d G . P . .
C22 C 1.5568(10) 0.0533(6) 0.2685(14) 0.024(3) Uani 0.5 1 d G U P . .
H22 H 1.5565 0.1388 0.2786 0.028 Uiso 0.5 1 calc R U P . .
C23 C 1.5815(11) 0.0240(11) 0.1536(9) 0.028(4) Uani 0.5 1 d G U P . .
H23 H 1.5949 0.0883 0.0898 0.034 Uiso 0.5 1 calc R U P . .
C24 C 1.5864(14) -0.0994(15) 0.1320(7) 0.029(4) Uani 0.5 1 d G . P . .
H24 H 1.6033 -0.1194 0.0534 0.035 Uiso 0.5 1 calc R U P . .
C25 C 1.5668(15) -0.1936(7) 0.2253(14) 0.016(3) Uani 0.5 1 d G U P . .
H25 H 1.5947 -0.2761 0.2105 0.019 Uiso 0.5 1 calc R U P . .
C26 C 1.5421(12) -0.1643(11) 0.3402(10) 0.021(4) Uani 0.5 1 d G U P . .
H26 H 1.5286 -0.2286 0.4040 0.025 Uiso 0.5 1 calc R U P . .
N5 N 1.0811(12) 0.5795(9) -0.0629(9) 0.032(2) Uani 0.5 1 d . . P . .
H5A H 1.1754 0.5968 -0.0882 0.039 Uiso 0.5 1 calc R U P . .
N6 N 0.8738(11) 0.4840(10) 0.0284(9) 0.032(2) Uani 0.5 1 d . . P . .
H6A H 0.8090 0.4294 0.0748 0.039 Uiso 0.5 1 calc R U P . .
C27 C 0.840(2) 0.5854(7) -0.0374(9) 0.029(4) Uani 0.5 1 d G . P . .
C28 C 0.9722(13) 0.6485(16) -0.0921(11) 0.030(4) Uani 0.5 1 d G . P . .
C29 C 0.9765(13) 0.7586(15) -0.1655(12) 0.038(5) Uani 0.5 1 d G . P . .
H29 H 1.0668 0.8018 -0.2029 0.045 Uiso 0.5 1 calc R U P . .
C30 C 0.849(2) 0.8057(10) -0.1841(11) 0.039(5) Uani 0.5 1 d G . P . .
H30 H 0.8517 0.8809 -0.2342 0.047 Uiso 0.5 1 calc R U P . .
C31 C 0.7166(13) 0.7425(17) -0.1293(16) 0.044(5) Uani 0.5 1 d G . P . .
H31 H 0.6293 0.7747 -0.1421 0.053 Uiso 0.5 1 calc R U P . .
C32 C 0.7123(12) 0.6324(16) -0.0560(15) 0.034(5) Uani 0.5 1 d G . P . .
H32 H 0.6221 0.5892 -0.0186 0.041 Uiso 0.5 1 calc R U P . .
C33 C 1.013(3) 0.4782(15) 0.0137(17) 0.028(3) Uani 0.5 1 d . . P . .
C34 C 1.0955(19) 0.3830(11) 0.0625(13) 0.029(4) Uani 0.5 1 d G . P . .
C35 C 1.0168(8) 0.2792(17) 0.1290(14) 0.035(5) Uani 0.5 1 d G . P . .
H35 H 0.9153 0.2716 0.1389 0.042 Uiso 0.5 1 calc R U P . .
C36 C 1.0866(18) 0.1863(11) 0.1811(11) 0.038(5) Uani 0.5 1 d G . P . .
H36 H 1.0329 0.1153 0.2266 0.045 Uiso 0.5 1 calc R U P . .
C37 C 1.2351(18) 0.1974(10) 0.1666(11) 0.043(5) Uani 0.5 1 d G . P . .
H37 H 1.2829 0.1339 0.2022 0.051 Uiso 0.5 1 calc R U P . .
C38 C 1.3138(8) 0.3012(16) 0.1000(15) 0.030(4) Uani 0.5 1 d G . P . .
H38 H 1.4153 0.3088 0.0901 0.035 Uiso 0.5 1 calc R U P . .
C39 C 1.2440(18) 0.3941(11) 0.0480(13) 0.032(5) Uani 0.5 1 d G . P . .
H39 H 1.2977 0.4650 0.0025 0.038 Uiso 0.5 1 calc R U P . .


_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
Se1 O2 1.614(3) . ?
Se1 O1 1.629(3) . ?
Se1 O3 1.630(3) . ?
Se1 O4 1.636(4) . ?
N1 C7 1.332(6) . ?
N1 C2 1.373(5) . ?
N1 H1 0.8800 . ?
N2 C7 1.329(6) . ?
N2 C1 1.377(4) . ?
N2 H2 0.8800 . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.461(5) . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N3 C14 1.345(12) . ?
N3 C20 1.35(3) . ?
N3 H3A 0.8800 . ?
N4 C20 1.34(3) . ?
N4 C19 1.385(11) . ?
N4 H4A 0.8800 . ?
C14 C15 1.3900 . ?
C14 C19 1.3900 . ?
C15 C26 0.649(8) 2_856 ?
C15 C25 0.86(5) 2_856 ?
C15 C16 1.3900 . ?
C15 C21 1.962(7) 2_856 ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C20 C21 1.437(17) . ?
C20 C19 1.77(2) 2_856 ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C21 C18 1.94(3) 2_856 ?
C22 C19 0.72(2) 2_856 ?
C22 C18 0.763(19) 2_856 ?
C22 C23 1.3900 . ?
C22 H22 0.9500 . ?
C23 C24 1.3900 . ?
C23 H23 0.9500 . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C25 C16 0.55(7) 2_856 ?
C25 C15 0.86(5) 2_856 ?
C25 C26 1.3900 . ?
C25 C14 2.025(8) 2_856 ?
C25 H25 0.9500 . ?
C26 C16 1.86(4) 2_856 ?
C26 H26 0.9500 . ?
N5 C33 1.38(2) . ?
N5 C28 1.381(13) . ?
N5 H5A 0.8800 . ?
N6 C33 1.30(3) . ?
N6 C27 1.367(14) . ?
N6 H6A 0.8800 . ?
C27 C28 1.3900 . ?
C27 C32 1.3900 . ?
C28 C29 1.3900 . ?
C29 C30 1.3900 . ?
C29 H29 0.9500 . ?
C30 C31 1.3900 . ?
C30 H30 0.9500 . ?
C31 C32 1.3900 . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.461(12) . ?
C34 C35 1.3900 . ?
C34 C39 1.3900 . ?
C35 C36 1.3900 . ?
C35 H35 0.9500 . ?
C36 C37 1.3900 . ?
C36 H36 0.9500 . ?
C37 C38 1.3900 . ?
C37 H37 0.9500 . ?
C38 C39 1.3900 . ?
C38 H38 0.9500 . ?
C39 C31 1.77(5) 2_765 ?
C39 H39 0.9500 . ?

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
O2 Se1 O1 109.80(18) . . ?
O2 Se1 O3 108.06(18) . . ?
O1 Se1 O3 110.44(19) . . ?
O2 Se1 O4 110.6(2) . . ?
O1 Se1 O4 109.12(18) . . ?
O3 Se1 O4 108.79(19) . . ?
C7 N1 C2 107.7(4) . . ?
C7 N1 H1 126.2 . . ?
C2 N1 H1 126.2 . . ?
C7 N2 C1 108.6(4) . . ?
C7 N2 H2 125.7 . . ?
C1 N2 H2 125.7 . . ?
N2 C1 C2 105.9(3) . . ?
N2 C1 C6 134.0(3) . . ?
C2 C1 C6 120.0 . . ?
N1 C2 C1 107.6(3) . . ?
N1 C2 C3 132.4(3) . . ?
C1 C2 C3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N2 C7 N1 110.2(4) . . ?
N2 C7 C8 125.5(4) . . ?
N1 C7 C8 124.3(4) . . ?
C9 C8 C13 120.0 . . ?
C9 C8 C7 119.9(3) . . ?
C13 C8 C7 120.1(3) . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C14 N3 C20 109.9(12) . . ?
C14 N3 H3A 125.1 . . ?
C20 N3 H3A 125.1 . . ?
C20 N4 C19 108.6(12) . . ?
C20 N4 H4A 125.7 . . ?
C19 N4 H4A 125.7 . . ?
N3 C14 C15 133.0(13) . . ?
N3 C14 C19 107.0(13) . . ?
C15 C14 C19 120.0 . . ?
C26 C15 C25 134(10) 2_856 2_856 ?
C26 C15 C16 127(5) 2_856 . ?
C25 C15 C16 7(4) 2_856 . ?
C26 C15 C14 8(5) 2_856 . ?
C25 C15 C14 127(5) 2_856 . ?
C16 C15 C14 120.0 . . ?
C26 C15 C21 23(5) 2_856 2_856 ?
C25 C15 C21 111(5) 2_856 2_856 ?
C16 C15 C21 104.2(2) . 2_856 ?
C14 C15 C21 15.8(2) . 2_856 ?
C26 C15 H15 113.0 2_856 . ?
C25 C15 H15 113.0 2_856 . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 120.1 . . ?
C21 C15 H15 135.8 2_856 . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
N4 C19 C18 133.4(13) . . ?
N4 C19 C14 106.6(12) . . ?
C18 C19 C14 120.0 . . ?
N4 C20 N3 108.0(12) . . ?
N4 C20 C21 128(2) . . ?
N3 C20 C21 124(2) . . ?
N4 C20 C19 150(2) . 2_856 ?
N3 C20 C19 102(2) . 2_856 ?
C21 C20 C19 22.2(11) . 2_856 ?
C22 C21 C26 120.0 . . ?
C22 C21 C20 119.4(16) . . ?
C26 C21 C20 120.6(16) . . ?
C22 C21 C18 18.5(19) . 2_856 ?
C26 C21 C18 101.5(19) . 2_856 ?
C20 C21 C18 137.9(14) . 2_856 ?
C19 C22 C18 138(8) 2_856 2_856 ?
C19 C22 C23 132(3) 2_856 . ?
C18 C22 C23 6(5) 2_856 . ?
C19 C22 C21 12(3) 2_856 . ?
C18 C22 C21 126(5) 2_856 . ?
C23 C22 C21 120.0 . . ?
C19 C22 H22 110.9 2_856 . ?
C18 C22 H22 110.9 2_856 . ?
C23 C22 H22 116.9 . . ?
C21 C22 H22 123.1 . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C16 C25 C15 162(9) 2_856 2_856 ?
C16 C25 C26 143(6) 2_856 . ?
C15 C25 C26 20(3) 2_856 . ?
C16 C25 C24 23(6) 2_856 . ?
C15 C25 C24 139(3) 2_856 . ?
C26 C25 C24 120.0 . . ?
C16 C25 C14 129(6) 2_856 2_856 ?
C15 C25 C14 33(3) 2_856 2_856 ?
C26 C25 C14 13.85(19) . 2_856 ?
C24 C25 C14 106.17(19) . 2_856 ?
C16 C25 H25 99.1 2_856 . ?
C15 C25 H25 99.1 2_856 . ?
C26 C25 H25 117.4 . . ?
C24 C25 H25 120.6 . . ?
C14 C25 H25 130.8 2_856 . ?
C25 C26 C21 120.0 . . ?
C25 C26 C16 10(3) . 2_856 ?
C21 C26 C16 110(3) . 2_856 ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
C16 C26 H26 130.2 2_856 . ?
C33 N5 C28 106.6(12) . . ?
C33 N5 H5A 126.7 . . ?
C28 N5 H5A 126.7 . . ?
C33 N6 C27 111.7(13) . . ?
C33 N6 H6A 124.2 . . ?
C27 N6 H6A 124.2 . . ?
N6 C27 C28 105.0(16) . . ?
N6 C27 C32 135.0(16) . . ?
C28 C27 C32 120.0 . . ?
N5 C28 C27 108.0(15) . . ?
N5 C28 C29 131.9(15) . . ?
C27 C28 C29 120.0 . . ?
C28 C29 C30 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C27 120.0 . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?
N6 C33 N5 108.5(8) . . ?
N6 C33 C34 129.4(17) . . ?
N5 C33 C34 122.0(18) . . ?
C35 C34 C39 120.0 . . ?
C35 C34 C33 116.7(17) . . ?
C39 C34 C33 123.3(17) . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 120.0 . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C38 120.0 . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C39 C38 C37 120.0 . . ?
C39 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C39 C34 120.0 . . ?
C38 C39 C31 16(3) . 2_765 ?
C34 C39 C31 104(3) . 2_765 ?
C38 C39 H39 120.0 . . ?
C34 C39 H39 120.0 . . ?
C31 C39 H39 135.9 2_765 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C1 C2 0.2(4) . . . . ?
C7 N2 C1 C6 177.7(3) . . . . ?
C7 N1 C2 C1 0.4(4) . . . . ?
C7 N1 C2 C3 -177.6(3) . . . . ?
N2 C1 C2 N1 -0.3(3) . . . . ?
C6 C1 C2 N1 -178.2(3) . . . . ?
N2 C1 C2 C3 177.9(3) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
N1 C2 C3 C4 177.7(4) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
N2 C1 C6 C5 -177.2(4) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C1 N2 C7 N1 0.0(6) . . . . ?
C1 N2 C7 C8 178.7(4) . . . . ?
C2 N1 C7 N2 -0.3(6) . . . . ?
C2 N1 C7 C8 -178.9(4) . . . . ?
N2 C7 C8 C9 2.1(6) . . . . ?
N1 C7 C8 C9 -179.4(4) . . . . ?
N2 C7 C8 C13 -177.0(4) . . . . ?
N1 C7 C8 C13 1.5(6) . . . . ?
C13 C8 C9 C10 0.0 . . . . ?
C7 C8 C9 C10 -179.0(4) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C8 0.0 . . . . ?
C9 C8 C13 C12 0.0 . . . . ?
C7 C8 C13 C12 179.0(4) . . . . ?
C20 N3 C14 C15 177.2(15) . . . . ?
C20 N3 C14 C19 -1.2(15) . . . . ?
N3 C14 C15 C26 22(28) . . . 2_856 ?
C19 C14 C15 C26 -160(28) . . . 2_856 ?
N3 C14 C15 C25 180(4) . . . 2_856 ?
C19 C14 C15 C25 -2(3) . . . 2_856 ?
N3 C14 C15 C16 -178.2(11) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
N3 C14 C15 C21 180(2) . . . 2_856 ?
C19 C14 C15 C21 -2.0(16) . . . 2_856 ?
C26 C15 C16 C17 3(4) 2_856 . . . ?
C25 C15 C16 C17 165(25) 2_856 . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C21 C15 C16 C17 0.6(4) 2_856 . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C20 N4 C19 C18 -177.9(15) . . . . ?
C20 N4 C19 C14 -1.2(15) . . . . ?
C17 C18 C19 N4 176.3(11) . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
N3 C14 C19 N4 1.4(7) . . . . ?
C15 C14 C19 N4 -177.2(8) . . . . ?
N3 C14 C19 C18 178.6(8) . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C19 N4 C20 N3 0(2) . . . . ?
C19 N4 C20 C21 -179(2) . . . . ?
C19 N4 C20 C19 -178(4) . . . 2_856 ?
C14 N3 C20 N4 0(2) . . . . ?
C14 N3 C20 C21 179.8(19) . . . . ?
C14 N3 C20 C19 179.5(12) . . . 2_856 ?
N4 C20 C21 C22 179.0(19) . . . . ?
N3 C20 C21 C22 0(3) . . . . ?
C19 C20 C21 C22 0(3) 2_856 . . . ?
N4 C20 C21 C26 1(3) . . . . ?
N3 C20 C21 C26 -178.4(17) . . . . ?
C19 C20 C21 C26 -178(4) 2_856 . . . ?
N4 C20 C21 C18 178(2) . . . 2_856 ?
N3 C20 C21 C18 -1(4) . . . 2_856 ?
C19 C20 C21 C18 -0.4(14) 2_856 . . 2_856 ?
C26 C21 C22 C19 176(14) . . . 2_856 ?
C20 C21 C22 C19 -2(13) . . . 2_856 ?
C18 C21 C22 C19 176(18) 2_856 . . 2_856 ?
C26 C21 C22 C18 0(4) . . . 2_856 ?
C20 C21 C22 C18 -178(5) . . . 2_856 ?
C26 C21 C22 C23 0.0 . . . . ?
C20 C21 C22 C23 -178.1(15) . . . . ?
C18 C21 C22 C23 0(4) 2_856 . . . ?
C19 C22 C23 C24 -1(4) 2_856 . . . ?
C18 C22 C23 C24 -180(100) 2_856 . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C16 174(11) . . . 2_856 ?
C23 C24 C25 C15 3(4) . . . 2_856 ?
C23 C24 C25 C26 0.0 . . . . ?
C23 C24 C25 C14 0.8(4) . . . 2_856 ?
C16 C25 C26 C21 -4(7) 2_856 . . . ?
C15 C25 C26 C21 -174(8) 2_856 . . . ?
C24 C25 C26 C21 0.0 . . . . ?
C14 C25 C26 C21 -3.2(18) 2_856 . . . ?
C15 C25 C26 C16 -170(15) 2_856 . . 2_856 ?
C24 C25 C26 C16 4(7) . . . 2_856 ?
C14 C25 C26 C16 1(7) 2_856 . . 2_856 ?
C22 C21 C26 C25 0.0 . . . . ?
C20 C21 C26 C25 178.1(15) . . . . ?
C18 C21 C26 C25 0.0(13) 2_856 . . . ?
C22 C21 C26 C16 -0.7(14) . . . 2_856 ?
C20 C21 C26 C16 177(2) . . . 2_856 ?
C18 C21 C26 C16 -0.7(5) 2_856 . . 2_856 ?
C33 N6 C27 C28 -2.8(15) . . . . ?
C33 N6 C27 C32 178.2(13) . . . . ?
C33 N5 C28 C27 -2.7(14) . . . . ?
C33 N5 C28 C29 -179.8(12) . . . . ?
N6 C27 C28 N5 3.3(11) . . . . ?
C32 C27 C28 N5 -177.5(10) . . . . ?
N6 C27 C28 C29 -179.2(9) . . . . ?
C32 C27 C28 C29 0.0 . . . . ?
N5 C28 C29 C30 176.8(13) . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
C28 C29 C30 C31 0.0 . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C30 C31 C32 C27 0.0 . . . . ?
N6 C27 C32 C31 178.9(13) . . . . ?
C28 C27 C32 C31 0.0 . . . . ?
C27 N6 C33 N5 1.1(19) . . . . ?
C27 N6 C33 C34 -176.9(18) . . . . ?
C28 N5 C33 N6 1.0(18) . . . . ?
C28 N5 C33 C34 179.2(16) . . . . ?
N6 C33 C34 C35 4(3) . . . . ?
N5 C33 C34 C35 -173.7(14) . . . . ?
N6 C33 C34 C39 -174.0(16) . . . . ?
N5 C33 C34 C39 8(2) . . . . ?
C39 C34 C35 C36 0.0 . . . . ?
C33 C34 C35 C36 -178.2(13) . . . . ?
C34 C35 C36 C37 0.0 . . . . ?
C35 C36 C37 C38 0.0 . . . . ?
C36 C37 C38 C39 0.0 . . . . ?
C37 C38 C39 C34 0.0 . . . . ?
C37 C38 C39 C31 2(5) . . . 2_765 ?
C35 C34 C39 C38 0.0 . . . . ?
C33 C34 C39 C38 178.0(14) . . . . ?
C35 C34 C39 C31 -0.5(15) . . . 2_765 ?
C33 C34 C39 C31 178(2) . . . 2_765 ?

_refine_diff_density_max         0.632
_refine_diff_density_min         -1.104
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_(H2PhBim)2SeO4_MeOH
_database_code_depnum_ccdc_archive 'CCDC 1050275'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '2-Phenylbenzimidazolium Selenate MeOH Solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H30 N4 O6 Se'
_chemical_formula_weight         597.52

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   17.3442(12)
_cell_length_b                   8.0712(6)
_cell_length_c                   19.5768(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2740.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4069
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.29

_exptl_crystal_description       Plates
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.419
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Blessing, (1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ a ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27923
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.081
_diffrn_reflns_theta_max         26.433
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2818
_reflns_number_gt                2012
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 All non-hydrogen atoms were included in the refinement using the 
 anisotropic model. The hydrogen atoms connected to carbon and nitrogen 
 atoms were placed in positions calculated based on the assigned 
 hybridization of the parent non-hydrogen atom and included in the 
 refinement using a riding model. The hydrogen atom of the methanol
 molecule was placed in a position generated by the SHELX command
 AFIX 147 and was included in the refinement using the riding model.

 The selenate ion is located on a two-fold rotation axis, and the 
 2-phenylbenzimidazolium ion was found to be disordered over
 two sites with occupational parameters 0.41 and 0.59. The two 
 disordered sites are in a mutually antiparallel orientation.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²+4.5312P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2818
_refine_ls_number_parameters     277
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.029
_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
Se1 Se 0.0000 0.13778(5) 0.2500 0.01869(12) Uani 1 2 d S T P . .
O1 O -0.05432(12) 0.2557(3) 0.20197(10) 0.0338(5) Uani 1 1 d . . . . .
O2 O 0.05301(11) 0.0233(3) 0.20003(10) 0.0290(5) Uani 1 1 d . . . . .
N1 N 0.2943(3) 0.4577(7) 0.2099(3) 0.0173(12) Uani 0.41 1 d . . P A 1
H1 H 0.3436 0.4678 0.2089 0.021 Uiso 0.41 1 calc R U P A 1
N2 N 0.1796(3) 0.3827(6) 0.2425(3) 0.0166(11) Uani 0.41 1 d . . P A 1
H2 H 0.1433 0.3368 0.2657 0.020 Uiso 0.41 1 calc R U P A 1
C1 C 0.1707(5) 0.4817(6) 0.1855(2) 0.0140(16) Uani 0.41 1 d G . P A 1
C6 C 0.1065(3) 0.5343(9) 0.1489(4) 0.022(2) Uani 0.41 1 d G U P A 1
H6 H 0.0574 0.5027 0.1627 0.026 Uiso 0.41 1 calc R U P A 1
C5 C 0.1158(4) 0.6343(11) 0.0917(4) 0.034(4) Uani 0.41 1 d G U P A 1
H5 H 0.0729 0.6696 0.0672 0.040 Uiso 0.41 1 calc R U P A 1
C4 C 0.1893(6) 0.6817(9) 0.0711(3) 0.024(3) Uani 0.41 1 d G U P A 1
H4 H 0.1955 0.7486 0.0328 0.029 Uiso 0.41 1 calc R U P A 1
C3 C 0.2535(4) 0.6291(9) 0.1077(4) 0.019(2) Uani 0.41 1 d G U P A 1
H3 H 0.3026 0.6608 0.0939 0.023 Uiso 0.41 1 calc R U P A 1
C2 C 0.2442(4) 0.5291(9) 0.1649(4) 0.016(2) Uani 0.41 1 d G U P A 1
C7 C 0.2551(4) 0.3714(9) 0.2548(4) 0.0147(16) Uani 0.41 1 d . U P A 1
C8 C 0.2879(5) 0.2724(6) 0.3113(2) 0.0135(15) Uani 0.41 1 d G U P A 1
C9 C 0.2394(2) 0.1966(9) 0.3584(4) 0.022(2) Uani 0.41 1 d G U P A 1
H9 H 0.1863 0.2115 0.3555 0.026 Uiso 0.41 1 calc R U P A 1
C10 C 0.2703(4) 0.0985(7) 0.4100(3) 0.0158(16) Uani 0.41 1 d G U P A 1
H10 H 0.2379 0.0478 0.4416 0.019 Uiso 0.41 1 calc R U P A 1
C11 C 0.3496(5) 0.0763(7) 0.4144(3) 0.031(2) Uani 0.41 1 d G U P A 1
H11 H 0.3702 0.0107 0.4489 0.037 Uiso 0.41 1 calc R U P A 1
C12 C 0.3980(2) 0.1521(9) 0.3673(4) 0.041(3) Uani 0.41 1 d G . P A 1
H12 H 0.4511 0.1372 0.3703 0.049 Uiso 0.41 1 calc R U P A 1
C13 C 0.3672(4) 0.2501(7) 0.3157(3) 0.0276(17) Uani 0.41 1 d G U P A 1
H13 H 0.3996 0.3009 0.2842 0.033 Uiso 0.41 1 calc R U P A 1
N2A N 0.3203(2) 0.3881(4) 0.2501(2) 0.0187(7) Uani 0.59 1 d . . P B 2
H2A H 0.3588 0.4311 0.2289 0.022 Uiso 0.59 1 calc R U P B 2
N1A N 0.2027(2) 0.3256(5) 0.2785(2) 0.0181(8) Uani 0.59 1 d . . P B 2
H1A H 0.1532 0.3206 0.2783 0.022 Uiso 0.59 1 calc R U P B 2
C7A C 0.2458(3) 0.4095(7) 0.2337(3) 0.0177(12) Uani 0.59 1 d . U P B 2
C2A C 0.2498(2) 0.2489(5) 0.3247(2) 0.0169(10) Uani 0.59 1 d G . P B 2
C3A C 0.23624(17) 0.1473(5) 0.3807(2) 0.0232(13) Uani 0.59 1 d G . P B 2
H3A H 0.1859 0.1218 0.3934 0.028 Uiso 0.59 1 calc R U P B 2
C4A C 0.2978(3) 0.0838(4) 0.41787(15) 0.0237(13) Uani 0.59 1 d G U P B 2
H4A H 0.2888 0.0159 0.4554 0.028 Uiso 0.59 1 calc R U P B 2
C5A C 0.3730(2) 0.1220(5) 0.3989(2) 0.0254(14) Uani 0.59 1 d G . P B 2
H5A H 0.4142 0.0796 0.4238 0.030 Uiso 0.59 1 calc R U P B 2
C6A C 0.38658(17) 0.2236(5) 0.3429(2) 0.0257(13) Uani 0.59 1 d G U P B 2
H6A H 0.4369 0.2492 0.3302 0.031 Uiso 0.59 1 calc R U P B 2
C1A C 0.3250(3) 0.2871(4) 0.30577(14) 0.0166(10) Uani 0.59 1 d G U P B 2
C8A C 0.2178(5) 0.5079(7) 0.1759(3) 0.0150(11) Uani 0.59 1 d . . P B 2
C13A C 0.1389(5) 0.5205(8) 0.1650(3) 0.0315(14) Uani 0.59 1 d . . P B 2
H13A H 0.1042 0.4689 0.1943 0.038 Uiso 0.59 1 calc R U P B 2
C12A C 0.1124(4) 0.6127(10) 0.1087(4) 0.034(2) Uani 0.59 1 d . . P B 2
H12A H 0.0598 0.6221 0.1005 0.041 Uiso 0.59 1 calc R U P B 2
C11A C 0.1636(5) 0.6882(8) 0.0665(3) 0.0300(17) Uani 0.59 1 d . . P B 2
H11A H 0.1457 0.7498 0.0296 0.036 Uiso 0.59 1 calc R U P B 2
C10A C 0.2419(4) 0.6745(6) 0.0777(3) 0.0239(12) Uani 0.59 1 d . . P B 2
H10A H 0.2763 0.7270 0.0483 0.029 Uiso 0.59 1 calc R U P B 2
C9A C 0.2695(3) 0.5836(7) 0.1319(3) 0.0206(12) Uani 0.59 1 d . . P B 2
H9A H 0.3223 0.5732 0.1389 0.025 Uiso 0.59 1 calc R U P B 2
O3 O 0.04278(15) 0.7734(4) -0.05942(12) 0.0642(9) Uani 1 1 d . . . . .
C14 C -0.0310(2) 0.8185(5) -0.03894(19) 0.0541(11) Uani 1 1 d . . . . .
H14A H -0.0311 0.8403 0.0093 0.081 Uiso 1 1 calc R U . . .
H14B H -0.0662 0.7301 -0.0489 0.081 Uiso 1 1 calc R U . . .
H14C H -0.0466 0.9165 -0.0631 0.081 Uiso 1 1 calc R U . . .
H1o H 0.0397 0.7551 -0.1134 0.023 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
Se1 O2 1.6296(19) . ?
Se1 O2 1.6297(19) 4 ?
Se1 O1 1.636(2) 4 ?
Se1 O1 1.636(2) . ?
N1 C7 1.312(9) . ?
N1 C2 1.365(8) . ?
N1 H1 0.8600 . ?
N2 C7 1.335(9) . ?
N2 C1 1.382(7) . ?
N2 H2 0.8600 . ?
C1 C6 1.3900 . ?
C1 C2 1.3900 . ?
C6 C5 1.3900 . ?
C6 H6 0.9300 . ?
C5 C4 1.3900 . ?
C5 H5 0.9300 . ?
C4 C3 1.3900 . ?
C4 H4 0.9300 . ?
C3 C2 1.3900 . ?
C3 H3 0.9300 . ?
C7 C8 1.477(9) . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 C10 1.3900 . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 H10 0.9300 . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C12 C13 1.3900 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N2A C7A 1.342(6) . ?
N2A C1A 1.364(5) . ?
N2A H2A 0.8600 . ?
N1A C7A 1.337(7) . ?
N1A C2A 1.366(5) . ?
N1A H1A 0.8600 . ?
C7A C8A 1.465(8) . ?
C2A C3A 1.3900 . ?
C2A C1A 1.3900 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9300 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9300 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9300 . ?
C6A C1A 1.3900 . ?
C6A H6A 0.9300 . ?
C8A C9A 1.387(8) . ?
C8A C13A 1.388(8) . ?
C13A C12A 1.407(10) . ?
C13A H13A 0.9300 . ?
C12A C11A 1.357(10) . ?
C12A H12A 0.9300 . ?
C11A C10A 1.381(9) . ?
C11A H11A 0.9300 . ?
C10A C9A 1.376(7) . ?
C10A H10A 0.9300 . ?
C9A H9A 0.9300 . ?
O3 C14 1.389(4) . ?
O3 H1O 1.068(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O2 Se1 O2 110.94(15) . 4 ?
O2 Se1 O1 110.47(10) . 4 ?
O2 Se1 O1 108.03(10) 4 4 ?
O2 Se1 O1 108.03(10) . . ?
O2 Se1 O1 110.48(10) 4 . ?
O1 Se1 O1 108.87(17) 4 . ?
C7 N1 C2 109.1(7) . . ?
C7 N1 H1 125.4 . . ?
C2 N1 H1 125.4 . . ?
C7 N2 C1 107.2(6) . . ?
C7 N2 H2 126.4 . . ?
C1 N2 H2 126.4 . . ?
N2 C1 C6 133.1(7) . . ?
N2 C1 C2 106.9(7) . . ?
C6 C1 C2 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N1 C2 C3 133.7(7) . . ?
N1 C2 C1 106.3(7) . . ?
C3 C2 C1 120.0 . . ?
N1 C7 N2 110.5(7) . . ?
N1 C7 C8 126.2(7) . . ?
N2 C7 C8 123.3(7) . . ?
C9 C8 C13 120.0 . . ?
C9 C8 C7 120.2(7) . . ?
C13 C8 C7 119.8(7) . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C7A N2A C1A 109.0(4) . . ?
C7A N2A H2A 125.5 . . ?
C1A N2A H2A 125.5 . . ?
C7A N1A C2A 109.2(5) . . ?
C7A N1A H1A 125.4 . . ?
C2A N1A H1A 125.4 . . ?
N1A C7A N2A 108.4(5) . . ?
N1A C7A C8A 126.5(6) . . ?
N2A C7A C8A 125.0(6) . . ?
N1A C2A C3A 133.5(5) . . ?
N1A C2A C1A 106.5(5) . . ?
C3A C2A C1A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
N2A C1A C6A 133.2(5) . . ?
N2A C1A C2A 106.8(5) . . ?
C6A C1A C2A 120.0 . . ?
C9A C8A C13A 120.6(5) . . ?
C9A C8A C7A 120.3(7) . . ?
C13A C8A C7A 119.1(7) . . ?
C8A C13A C12A 118.8(5) . . ?
C8A C13A H13A 120.6 . . ?
C12A C13A H13A 120.6 . . ?
C11A C12A C13A 120.0(6) . . ?
C11A C12A H12A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C12A C11A C10A 120.8(6) . . ?
C12A C11A H11A 119.6 . . ?
C10A C11A H11A 119.6 . . ?
C9A C10A C11A 120.5(5) . . ?
C9A C10A H10A 119.8 . . ?
C11A C10A H10A 119.8 . . ?
C10A C9A C8A 119.3(5) . . ?
C10A C9A H9A 120.3 . . ?
C8A C9A H9A 120.3 . . ?
C14 O3 H1O 106.0(2) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C1 C6 178.9(5) . . . . ?
C7 N2 C1 C2 -0.3(5) . . . . ?
N2 C1 C6 C5 -179.1(6) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C7 N1 C2 C3 -178.9(5) . . . . ?
C7 N1 C2 C1 0.4(6) . . . . ?
C4 C3 C2 N1 179.3(7) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
N2 C1 C2 N1 -0.1(5) . . . . ?
C6 C1 C2 N1 -179.4(5) . . . . ?
N2 C1 C2 C3 179.3(5) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C2 N1 C7 N2 -0.7(7) . . . . ?
C2 N1 C7 C8 178.6(6) . . . . ?
C1 N2 C7 N1 0.6(7) . . . . ?
C1 N2 C7 C8 -178.7(5) . . . . ?
N1 C7 C8 C9 175.2(5) . . . . ?
N2 C7 C8 C9 -5.6(8) . . . . ?
N1 C7 C8 C13 -7.2(9) . . . . ?
N2 C7 C8 C13 172.0(5) . . . . ?
C13 C8 C9 C10 0.0 . . . . ?
C7 C8 C9 C10 177.6(5) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C8 0.0 . . . . ?
C9 C8 C13 C12 0.0 . . . . ?
C7 C8 C13 C12 -177.6(5) . . . . ?
C2A N1A C7A N2A 0.1(5) . . . . ?
C2A N1A C7A C8A 179.8(4) . . . . ?
C1A N2A C7A N1A 0.8(5) . . . . ?
C1A N2A C7A C8A -178.9(4) . . . . ?
C7A N1A C2A C3A -179.6(3) . . . . ?
C7A N1A C2A C1A -0.9(4) . . . . ?
N1A C2A C3A C4A 178.5(4) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C7A N2A C1A C6A 179.0(3) . . . . ?
C7A N2A C1A C2A -1.4(4) . . . . ?
C5A C6A C1A N2A 179.6(4) . . . . ?
C5A C6A C1A C2A 0.0 . . . . ?
N1A C2A C1A N2A 1.4(3) . . . . ?
C3A C2A C1A N2A -179.7(3) . . . . ?
N1A C2A C1A C6A -178.9(3) . . . . ?
C3A C2A C1A C6A 0.0 . . . . ?
N1A C7A C8A C9A -177.6(4) . . . . ?
N2A C7A C8A C9A 2.0(7) . . . . ?
N1A C7A C8A C13A 0.7(8) . . . . ?
N2A C7A C8A C13A -179.6(5) . . . . ?
C9A C8A C13A C12A -0.6(8) . . . . ?
C7A C8A C13A C12A -178.9(5) . . . . ?
C8A C13A C12A C11A -0.3(9) . . . . ?
C13A C12A C11A C10A 0.6(9) . . . . ?
C12A C11A C10A C9A 0.1(8) . . . . ?
C11A C10A C9A C8A -1.0(7) . . . . ?
C13A C8A C9A C10A 1.2(7) . . . . ?
C7A C8A C9A C10A 179.5(4) . . . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-4

