#------------------------------------------------------------------------------
#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117172.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7117172
loop_
_publ_author_name
'Cristina Mottillo'
'Tomislav Friscic'
_publ_section_title
;
 Supramolecular imidazolium frameworks: direct analogues of metal azolate
 frameworks with charge-inverted node-and-linker structure
;
_journal_name_full               Chem.Commun.
_journal_page_first              8924
_journal_paper_doi               10.1039/C5cc01645B
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C17 H23 N4 O5.5 Se'
_chemical_formula_weight         450.35
_chemical_name_common
'2-methylbenzimidazolium selenate methanol solvate hydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-02-24 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.3770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.917(2)
_cell_length_b                   8.7717(7)
_cell_length_c                   17.5915(14)
_cell_measurement_reflns_used    4913
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      2.35
_cell_volume                     3933.8(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22811
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.829
_diffrn_reflns_theta_min         1.598
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.948
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing (1995)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       Hexagonal
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4797
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0376P)²+6.4346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3584
_reflns_number_total             4797
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc01645b2.cif
_cod_data_source_block           (H2MeBim)2SeO4_MeOH_H2O
_cod_original_formula_sum        'C17 H23 N4 O5.50 Se'
_cod_database_code               7117172
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.414
_shelx_estimated_absorpt_t_max   0.829
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . .
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'
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
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) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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) .
