#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/33/2213393.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_2213393
loop_
_publ_author_name
'Zhang, Chun-Xia'
'Ma, Cheng-Bing'
'Hu, Ming-Qiang'
'Chen, Chang-Neng'
'Liu, Qiu-Tian'
_publ_section_title
;
 Bis(benzimidazolium)
 diaquabis(pyridine-2,4-dicarboxylato-κ²N,O)manganese(II)
 dihydrate
;
_journal_coeditor_code           HK2212
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1424
_journal_page_last               m1426
_journal_paper_doi               10.1107/S1600536807016352
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac
'(C7 H7 N2)2 [Mn (C7 H3 O4 N)2 (H2 O)2], 2H2 O'
_chemical_formula_moiety
'2(C7 H7 N2 +), C14 H10 Mn N2 O10 2-, 2(H2 O)'
_chemical_formula_sum            'C28 H28 Mn N6 O12'
_chemical_formula_weight         695.50
_chemical_name_systematic
;Bis(benzimidazolium)
 diaquabis(pyridine-2,4-dicarboxylato-κ²N,O)manganese(II)
dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.539(6)
_cell_angle_beta                 101.032(6)
_cell_angle_gamma                111.508(5)
_cell_formula_units_Z            1
_cell_length_a                   8.4882(18)
_cell_length_b                   9.0617(19)
_cell_length_c                   10.7716(19)
_cell_measurement_reflns_used    1565
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.82
_cell_volume                     741.1(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2000)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    SHELXL97
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ω
_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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5758
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.82
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  .949
_exptl_absorpt_correction_T_min  .882
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             359
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .10
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0612P)²+0.2861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1290
_reflns_number_gt                2518
_reflns_number_total             3336
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2212.cif
_cod_data_source_block           I
_cod_database_code               2213393
_cod_database_fobs_code          2213393
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Mn Mn1 0.5000 0.5000 1.0000 0.03100(18) Uani d S 1
N N1 0.2762(3) 0.5338(3) 0.87778(19) 0.0293(5) Uani d . 1
N N2 0.5380(3) 0.7591(3) 0.5869(2) 0.0358(5) Uani d . 1
H H2A 0.6166 0.7396 0.6371 0.043 Uiso calc R 1
N N3 0.3660(3) 0.7646(3) 0.4112(2) 0.0340(5) Uani d . 1
H H1A 0.3167 0.7499 0.3306 0.041 Uiso calc R 1
C C1 0.2079(4) 0.9105(4) 0.5182(3) 0.0424(7) Uani d . 1
H H1B 0.1319 0.9113 0.4439 0.051 Uiso calc R 1
C C2 0.3267(3) 0.8397(3) 0.5131(2) 0.0298(5) Uani d . 1
C C3 0.4381(3) 0.8372(3) 0.6256(3) 0.0310(6) Uani d . 1
C C4 0.4359(4) 0.9056(4) 0.7470(3) 0.0410(7) Uani d . 1
H H4A 0.5096 0.9034 0.8221 0.049 Uiso calc R 1
C C5 0.3180(5) 0.9770(4) 0.7498(3) 0.0499(8) Uani d . 1
H H5A 0.3124 1.0249 0.8290 0.060 Uiso calc R 1
C C6 0.2083(4) 0.9793(4) 0.6384(4) 0.0531(9) Uani d . 1
H H6A 0.1314 1.0294 0.6450 0.064 Uiso calc R 1
C C7 0.4923(4) 0.7194(3) 0.4593(3) 0.0383(6) Uani d . 1
H H7A 0.5424 0.6668 0.4101 0.046 Uiso calc R 1
C C8 0.0067(3) 0.6130(3) 0.7543(2) 0.0270(5) Uani d . 1
C C9 0.0775(3) 0.6628(3) 0.8871(2) 0.0276(5) Uani d . 1
H H9A 0.0356 0.7240 0.9364 0.033 Uiso calc R 1
C C10 0.2101(3) 0.6208(3) 0.9453(2) 0.0259(5) Uani d . 1
C C11 0.2063(4) 0.4837(3) 0.7502(2) 0.0338(6) Uani d . 1
H H11A 0.2502 0.4227 0.7028 0.041 Uiso calc R 1
C C12 0.0712(4) 0.5196(3) 0.6867(2) 0.0331(6) Uani d . 1
H H12A 0.0240 0.4807 0.5983 0.040 Uiso calc R 1
C C13 0.2878(3) 0.6649(3) 1.0904(2) 0.0274(5) Uani d . 1
C C14 -0.1358(3) 0.6591(3) 0.6849(2) 0.0309(6) Uani d . 1
O O1 -0.1882(3) 0.7465(2) 0.75482(18) 0.0386(5) Uani d . 1
O O2 -0.1924(3) 0.6113(3) 0.56707(18) 0.0461(5) Uani d . 1
O O3 0.2246(2) 0.7398(2) 1.15757(16) 0.0360(5) Uani d . 1
O O4 0.4100(2) 0.6229(2) 1.13554(16) 0.0342(4) Uani d . 1
O O5 0.6890(3) 0.7362(3) 0.9736(2) 0.0399(5) Uani d . 1
H H5C 0.732(5) 0.733(4) 0.901(4) 0.070(12) Uiso d . 1
H H5B 0.785(6) 0.781(5) 1.035(4) 0.071(13) Uiso d . 1
O O6 1.0010(3) 0.9022(3) 1.1599(3) 0.0575(7) Uani d . 1
H H6B 1.070(7) 0.871(6) 1.159(5) 0.103(18) Uiso d . 1
H H6C 1.053(6) 1.011(6) 1.174(4) 0.094(16) Uiso d . 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'
Mn Mn 0.3368 0.7283 '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
_geom_angle_publ_flag
O4 Mn1 O4 2_667 . 180.00(7) ?
O4 Mn1 N1 2_667 2_667 75.73(7) yes
O4 Mn1 N1 . 2_667 104.27(7) ?
O4 Mn1 N1 2_667 . 104.27(7) ?
O4 Mn1 N1 . . 75.73(7) ?
N1 Mn1 N1 2_667 . 180.0000(10) ?
O4 Mn1 O5 2_667 2_667 91.45(8) ?
O4 Mn1 O5 . 2_667 88.55(8) yes
N1 Mn1 O5 2_667 2_667 90.88(8) ?
N1 Mn1 O5 . 2_667 89.12(8) yes
O4 Mn1 O5 2_667 . 88.55(8) ?
O4 Mn1 O5 . . 91.45(8) ?
N1 Mn1 O5 2_667 . 89.12(8) ?
N1 Mn1 O5 . . 90.88(8) ?
O5 Mn1 O5 2_667 . 180.0 ?
C11 N1 C10 . . 118.1(2) ?
C11 N1 Mn1 . . 128.86(16) ?
C10 N1 Mn1 . . 113.01(15) ?
C7 N2 C3 . . 108.3(2) ?
C7 N2 O1 . 1_655 129.05(17) ?
C3 N2 O1 . 1_655 121.83(17) ?
C7 N2 H2A . . 125.8 ?
C3 N2 H2A . . 125.8 ?
C7 N3 C2 . . 108.0(2) ?
C7 N3 O3 . 1_554 126.61(18) ?
C2 N3 O3 . 1_554 125.17(16) ?
C7 N3 H1A . . 126.0 ?
C2 N3 H1A . . 126.0 ?
C6 C1 C2 . . 116.5(3) ?
C6 C1 H1B . . 121.7 ?
C2 C1 H1B . . 121.7 ?
N3 C2 C1 . . 132.4(2) ?
N3 C2 C3 . . 106.5(2) ?
C1 C2 C3 . . 121.1(2) ?
N2 C3 C4 . . 131.8(3) ?
N2 C3 C2 . . 106.3(2) ?
C4 C3 C2 . . 121.9(2) ?
C5 C4 C3 . . 116.1(3) ?
C5 C4 H4A . . 122.0 ?
C3 C4 H4A . . 122.0 ?
C6 C5 C4 . . 121.8(3) ?
C6 C5 H5A . . 119.1 ?
C4 C5 H5A . . 119.1 ?
C1 C6 C5 . . 122.6(3) ?
C1 C6 H6A . . 118.7 ?
C5 C6 H6A . . 118.7 ?
N3 C7 N2 . . 110.8(2) ?
N3 C7 H7A . . 124.6 ?
N2 C7 H7A . . 124.6 ?
C12 C8 C9 . . 117.7(2) ?
C12 C8 C14 . . 120.5(2) ?
C9 C8 C14 . . 121.8(2) ?
C10 C9 C8 . . 119.6(2) ?
C10 C9 H9A . . 120.2 ?
C8 C9 H9A . . 120.2 ?
N1 C10 C9 . . 122.3(2) ?
N1 C10 C13 . . 115.35(19) ?
C9 C10 C13 . . 122.3(2) ?
N1 C11 C12 . . 122.3(2) ?
N1 C11 H11A . . 118.8 ?
C12 C11 H11A . . 118.8 ?
C8 C12 C11 . . 120.0(2) ?
C8 C12 H12A . . 120.0 ?
C11 C12 H12A . . 120.0 ?
O3 C13 O4 . . 124.4(2) ?
O3 C13 C10 . . 117.4(2) ?
O4 C13 C10 . . 118.2(2) ?
O2 C14 O1 . . 124.9(2) ?
O2 C14 C8 . . 118.5(2) ?
O1 C14 C8 . . 116.6(2) ?
C13 O4 Mn1 . . 117.45(15) ?
Mn1 O5 O1 . 1_655 119.38(10) ?
Mn1 O5 O6 . 1 119.15(11) ?
O1 O5 O6 1_655 1 99.95(10) ?
Mn1 O5 H5C . . 117(2) ?
O6 O5 H5C 1 . 99(2) ?
Mn1 O5 H5B . . 115(3) ?
O1 O5 H5B 1_655 . 102(3) ?
H5C O5 H5B . . 102(3) ?
O3 O6 O1 1_655 2_677 113.10(10) ?
O1 O6 H6B 2_677 . 105(4) ?
O3 O6 H6C 1_655 . 116(3) ?
H6B O6 H6C . . 107(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 O4 2_667 2.1534(17) yes
Mn1 O4 . 2.1534(17) ?
Mn1 N1 2_667 2.235(2) yes
Mn1 N1 . 2.235(2) ?
Mn1 O5 2_667 2.243(2) yes
Mn1 O5 . 2.243(2) ?
N1 C11 . 1.339(3) ?
N1 C10 . 1.348(3) ?
N2 C7 . 1.323(4) ?
N2 C3 . 1.379(3) ?
N2 H2A . 0.8600 ?
N3 C7 . 1.321(3) ?
N3 C2 . 1.384(3) ?
N3 H1A . 0.8600 ?
C1 C6 . 1.370(5) ?
C1 C2 . 1.385(3) ?
C1 H1B . 0.9300 ?
C2 C3 . 1.395(4) ?
C3 C4 . 1.389(4) ?
C4 C5 . 1.379(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.379(5) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9300 ?
C8 C12 . 1.378(3) ?
C8 C9 . 1.392(3) ?
C8 C14 . 1.514(3) ?
C9 C10 . 1.380(3) ?
C9 H9A . 0.9300 ?
C10 C13 . 1.519(3) ?
C11 C12 . 1.383(3) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
C13 O3 . 1.255(3) yes
C13 O4 . 1.263(3) yes
C14 O2 . 1.232(3) yes
C14 O1 . 1.281(3) yes
O5 H5C . 0.93(4) ?
O5 H5B . 0.87(4) ?
O6 H6B . 0.74(5) ?
O6 H6C . 0.90(5) ?
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 H2A O1 1_655 0.86 1.86 2.705(3) 167.4
N3 H1A O3 1_554 0.86 1.86 2.713(3) 174.2
O5 H5C O1 1_655 0.93(4) 1.83(4) 2.751(3) 174(3)
O5 H5B O6 1 0.87(4) 1.90(4) 2.767(4) 173(4)
O6 H6B O3 1_655 0.74(5) 2.07(5) 2.797(3) 169(5)
O6 H6C O1 2_677 0.90(5) 2.04(5) 2.927(4) 168(4)
