#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/31/2233196.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2233196
loop_
_publ_author_name
'Wang, Xiao-Dan'
'Hou, Guang-Feng'
'Yu, Ying-Hui'
'Gao, Jin-Sheng'
_publ_section_title
;
 Bis[1,1'-(1,3-phenylenedimethylene)di(1H-imidazol-3-ium)]
 β-octamolybdate
;
_journal_coeditor_code           HY2492
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m50
_journal_paper_doi               10.1107/S1600536811053050
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '(C14 H16 N4)2 [Mo8 O26]'
_chemical_formula_moiety         '2(C14 H16 N4 2+), Mo8 O26 4-'
_chemical_formula_sum            'C28 H32 Mo8 N8 O26'
_chemical_formula_weight         1664.14
_chemical_name_systematic
;
Bis[1,1'-(1,3-phenylenedimethylene)di(1H-imidazol-3-ium)]
β-octamolybdate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.82(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.163(2)
_cell_length_b                   12.785(3)
_cell_length_c                   14.937(3)
_cell_measurement_reflns_used    17887
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.05
_cell_volume                     2306.3(8)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21595
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    2.198
_exptl_absorpt_correction_T_max  0.8085
_exptl_absorpt_correction_T_min  0.7800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.123
_refine_diff_density_min         -1.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5261
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0219P)²+3.6973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0570
_reflns_number_gt                4579
_reflns_number_total             5261
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2492.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233196
_cod_database_fobs_code          2233196
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.6205(3) 0.5883(3) 1.0719(2) 0.0442(9) Uani d . 1 1
H H1 0.6032 0.6216 1.1237 0.053 Uiso calc R 1 1
C C2 0.6426(3) 0.6343(3) 0.9957(2) 0.0411(8) Uani d . 1 1
H H2 0.6443 0.7059 0.9850 0.049 Uiso calc R 1 1
C C3 0.6529(3) 0.4656(3) 0.9766(3) 0.0414(8) Uani d . 1 1
H H3 0.6623 0.4003 0.9512 0.050 Uiso calc R 1 1
C C4 0.6943(3) 0.5749(3) 0.8462(2) 0.0375(8) Uani d . 1 1
H H4A 0.6747 0.6456 0.8269 0.045 Uiso calc R 1 1
H H4B 0.6542 0.5268 0.8039 0.045 Uiso calc R 1 1
C C5 0.8175(3) 0.5588(3) 0.8459(2) 0.0334(7) Uani d . 1 1
C C6 0.8932(4) 0.6252(3) 0.8933(3) 0.0574(11) Uani d . 1 1
H H6 0.8687 0.6820 0.9245 0.069 Uiso calc R 1 1
C C7 1.0057(4) 0.6069(4) 0.8944(4) 0.0722(15) Uani d . 1 1
H H7 1.0564 0.6506 0.9275 0.087 Uiso calc R 1 1
C C8 1.0431(3) 0.5248(4) 0.8469(4) 0.0638(13) Uani d . 1 1
H H8 1.1188 0.5140 0.8473 0.077 Uiso calc R 1 1
C C9 0.9687(3) 0.4581(3) 0.7984(3) 0.0416(9) Uani d . 1 1
C C10 0.8560(3) 0.4767(3) 0.7982(2) 0.0332(7) Uani d . 1 1
H H10 0.8054 0.4328 0.7652 0.040 Uiso calc R 1 1
C C11 1.0073(3) 0.3659(3) 0.7484(3) 0.0517(11) Uani d . 1 1
H H11A 0.9529 0.3499 0.6974 0.062 Uiso calc R 1 1
H H11B 1.0764 0.3833 0.7254 0.062 Uiso calc R 1 1
C C12 0.9427(4) 0.2172(4) 0.8436(4) 0.0673(14) Uani d . 1 1
H H12 0.8670 0.2300 0.8342 0.081 Uiso calc R 1 1
C C13 0.9922(5) 0.1420(4) 0.8937(4) 0.0722(15) Uani d . 1 1
H H13 0.9581 0.0920 0.9264 0.087 Uiso calc R 1 1
C C14 1.1198(3) 0.2305(3) 0.8354(3) 0.0503(10) Uani d . 1 1
H H14 1.1882 0.2521 0.8202 0.060 Uiso calc R 1 1
Mo Mo1 0.547848(19) 0.90288(2) 1.084672(17) 0.02207(6) Uani d . 1 1
Mo Mo2 0.30667(2) 1.04699(2) 1.134611(18) 0.02643(7) Uani d . 1 1
Mo Mo3 0.27124(2) 0.86907(2) 0.973110(19) 0.02576(7) Uani d . 1 1
Mo Mo4 0.45286(2) 0.80953(3) 0.81444(2) 0.03626(8) Uani d . 1 1
N N1 0.6622(2) 0.5573(2) 0.93667(18) 0.0312(6) Uani d . 1 1
N N2 0.6281(3) 0.4835(3) 1.0589(2) 0.0463(8) Uani d D 1 1
N N3 1.0240(2) 0.2736(3) 0.8073(2) 0.0425(7) Uani d . 1 1
N N4 1.1028(4) 0.1517(3) 0.8884(3) 0.0622(10) Uani d D 1 1
O O1 0.6277(2) 0.9749(2) 1.01029(18) 0.0472(7) Uani d . 1 1
O O2 0.6373(2) 0.8237(2) 1.14858(18) 0.0477(7) Uani d . 1 1
O O3 0.48333(18) 0.9874(2) 1.15775(16) 0.0372(6) Uani d . 1 1
O O4 0.2810(2) 1.0400(2) 1.24323(16) 0.0439(6) Uani d . 1 1
O O5 0.1925(2) 1.1056(2) 1.08042(19) 0.0500(7) Uani d . 1 1
O O6 0.27884(17) 0.90605(17) 1.09648(15) 0.0298(5) Uani d . 1 1
O O7 0.45232(19) 0.82404(19) 1.01803(19) 0.0429(6) Uani d . 1 1
O O8 0.1530(2) 0.9344(2) 0.93423(17) 0.0417(6) Uani d . 1 1
O O9 0.2328(2) 0.7420(2) 0.97568(19) 0.0439(6) Uani d . 1 1
O O10 0.33456(19) 0.8728(2) 0.85883(16) 0.0361(5) Uani d . 1 1
O O11 0.6000(2) 0.82712(18) 0.86168(17) 0.0371(5) Uani d . 1 1
O O12 0.4326(2) 0.6786(2) 0.8263(2) 0.0548(7) Uani d . 1 1
O O13 0.4385(3) 0.8367(2) 0.70317(19) 0.0555(7) Uani d . 1 1
H H21 0.619(4) 0.433(3) 1.099(2) 0.066(14) Uiso d D 1 1
H H41 1.155(3) 0.107(4) 0.911(4) 0.10(2) Uiso d D 1 1
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'
Mo Mo -1.6832 0.6857 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 N2 . . 106.7(3)
C2 C1 H1 . . 126.6
N2 C1 H1 . . 126.6
C1 C2 N1 . . 107.6(3)
C1 C2 H2 . . 126.2
N1 C2 H2 . . 126.2
N2 C3 N1 . . 107.9(3)
N2 C3 H3 . . 126.1
N1 C3 H3 . . 126.1
N1 C4 C5 . . 110.7(3)
N1 C4 H4A . . 109.5
C5 C4 H4A . . 109.5
N1 C4 H4B . . 109.5
C5 C4 H4B . . 109.5
H4A C4 H4B . . 108.1
C10 C5 C6 . . 119.0(4)
C10 C5 C4 . . 120.1(3)
C6 C5 C4 . . 121.0(3)
C5 C6 C7 . . 119.9(4)
C5 C6 H6 . . 120.1
C7 C6 H6 . . 120.1
C8 C7 C6 . . 120.6(4)
C8 C7 H7 . . 119.7
C6 C7 H7 . . 119.7
C7 C8 C9 . . 120.3(4)
C7 C8 H8 . . 119.8
C9 C8 H8 . . 119.8
C8 C9 C10 . . 118.6(4)
C8 C9 C11 . . 121.4(4)
C10 C9 C11 . . 120.0(4)
C5 C10 C9 . . 121.5(3)
C5 C10 H10 . . 119.2
C9 C10 H10 . . 119.2
N3 C11 C9 . . 111.1(3)
N3 C11 H11A . . 109.4
C9 C11 H11A . . 109.4
N3 C11 H11B . . 109.4
C9 C11 H11B . . 109.4
H11A C11 H11B . . 108.0
C13 C12 N3 . . 107.7(4)
C13 C12 H12 . . 126.2
N3 C12 H12 . . 126.2
C12 C13 N4 . . 106.7(4)
C12 C13 H13 . . 126.7
N4 C13 H13 . . 126.7
N3 C14 N4 . . 108.6(4)
N3 C14 H14 . . 125.7
N4 C14 H14 . . 125.7
O2 Mo1 O7 . . 108.29(13)
O2 Mo1 O3 . . 108.47(12)
O7 Mo1 O3 . . 112.67(11)
O2 Mo1 O1 . . 107.09(14)
O7 Mo1 O1 . . 108.11(13)
O3 Mo1 O1 . . 111.99(12)
O4 Mo2 O5 . . 104.33(14)
O4 Mo2 O6 . . 100.96(12)
O5 Mo2 O6 . . 99.70(12)
O4 Mo2 O11 . 3_677 100.83(12)
O5 Mo2 O11 . 3_677 95.11(13)
O6 Mo2 O11 . 3_677 149.63(10)
O4 Mo2 O3 . . 96.62(11)
O5 Mo2 O3 . . 158.19(12)
O6 Mo2 O3 . . 81.93(9)
O11 Mo2 O3 3_677 . 74.76(10)
O4 Mo2 O1 . 3_677 166.93(12)
O5 Mo2 O1 . 3_677 87.85(12)
O6 Mo2 O1 . 3_677 71.84(9)
O11 Mo2 O1 3_677 3_677 82.45(9)
O3 Mo2 O1 . 3_677 71.88(10)
O9 Mo3 O8 . . 104.73(13)
O9 Mo3 O6 . . 101.50(12)
O8 Mo3 O6 . . 98.69(11)
O9 Mo3 O10 . . 100.47(12)
O8 Mo3 O10 . . 95.41(11)
O6 Mo3 O10 . . 149.84(10)
O9 Mo3 O7 . . 90.60(11)
O8 Mo3 O7 . . 164.34(12)
O6 Mo3 O7 . . 81.03(10)
O10 Mo3 O7 . . 78.34(10)
O9 Mo3 O1 . 3_677 163.48(12)
O8 Mo3 O1 . 3_677 91.69(12)
O6 Mo3 O1 . 3_677 73.73(9)
O10 Mo3 O1 . 3_677 79.36(10)
O7 Mo3 O1 . 3_677 73.12(10)
O13 Mo4 O12 . . 107.75(16)
O13 Mo4 O10 . . 105.68(13)
O12 Mo4 O10 . . 105.41(13)
O13 Mo4 O11 . . 109.38(14)
O12 Mo4 O11 . . 102.95(12)
O10 Mo4 O11 . . 124.66(10)
C3 N1 C2 . . 108.4(3)
C3 N1 C4 . . 126.6(3)
C2 N1 C4 . . 124.9(3)
C3 N2 C1 . . 109.3(3)
C3 N2 H21 . . 124(3)
C1 N2 H21 . . 127(3)
C14 N3 C12 . . 107.7(4)
C14 N3 C11 . . 125.6(3)
C12 N3 C11 . . 126.7(3)
C14 N4 C13 . . 109.4(4)
C14 N4 H41 . . 125(4)
C13 N4 H41 . . 125(4)
Mo1 O1 Mo3 . 3_677 132.92(13)
Mo1 O1 Mo2 . 3_677 138.66(13)
Mo3 O1 Mo2 3_677 3_677 88.18(8)
Mo1 O3 Mo2 . . 126.04(12)
Mo3 O6 Mo2 . . 120.84(11)
Mo1 O7 Mo3 . . 124.65(12)
Mo4 O10 Mo3 . . 135.18(14)
Mo4 O11 Mo2 . 3_677 129.54(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.336(5)
C1 N2 . 1.359(5)
C1 H1 . 0.9300
C2 N1 . 1.362(4)
C2 H2 . 0.9300
C3 N2 . 1.319(5)
C3 N1 . 1.326(4)
C3 H3 . 0.9300
C4 N1 . 1.468(4)
C4 C5 . 1.513(5)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 C10 . 1.381(5)
C5 C6 . 1.384(5)
C6 C7 . 1.387(7)
C6 H6 . 0.9300
C7 C8 . 1.374(7)
C7 H7 . 0.9300
C8 C9 . 1.383(6)
C8 H8 . 0.9300
C9 C10 . 1.391(5)
C9 C11 . 1.501(6)
C10 H10 . 0.9300
C11 N3 . 1.472(5)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 C13 . 1.320(7)
C12 N3 . 1.385(5)
C12 H12 . 0.9300
C13 N4 . 1.364(7)
C13 H13 . 0.9300
C14 N3 . 1.312(5)
C14 N4 . 1.313(6)
C14 H14 . 0.9300
Mo1 O2 . 1.695(2)
Mo1 O7 . 1.756(2)
Mo1 O3 . 1.783(2)
Mo1 O1 . 1.811(2)
Mo2 O4 . 1.690(2)
Mo2 O5 . 1.697(3)
Mo2 O6 . 1.908(2)
Mo2 O11 3_677 1.966(2)
Mo2 O3 . 2.267(2)
Mo2 O1 3_677 2.410(3)
Mo3 O9 . 1.692(2)
Mo3 O8 . 1.704(2)
Mo3 O6 . 1.894(2)
Mo3 O10 . 1.955(2)
Mo3 O7 . 2.298(2)
Mo3 O1 3_677 2.341(2)
Mo4 O13 . 1.687(3)
Mo4 O12 . 1.704(3)
Mo4 O10 . 1.842(2)
Mo4 O11 . 1.858(3)
N2 H21 . 0.901(10)
N4 H41 . 0.896(10)
O1 Mo3 3_677 2.341(2)
O1 Mo2 3_677 2.410(2)
O11 Mo2 3_677 1.966(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H21 O12 3_667 0.900(10) 1.96(2) 2.844(4) 168(4)
N4 H41 O5 1_645 0.900(10) 2.51(5) 3.003(5) 115(4)
N4 H41 O8 1_645 0.900(10) 2.23(4) 2.909(5) 132(5)
