#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:14:00 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179959 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/53/7025380.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_7025380
loop_
_publ_author_name
'Keene, Tony D.'
'Zimmermann, Iwan'
'Neels, Antonia'
'Sereda, Olha'
'Hauser, Jürg'
'Bonin, Michel'
'Hursthouse, Michael B.'
'Price, Daniel J.'
'Decurtins, Silvio'
_publ_section_title
;
 Heterocyclic amine directed synthesis of metal(II)-oxalates:
 investigating the magnetic properties of two complete series of chains
 with S = 5/2 to S = 1/2.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4937
_journal_page_last               4950
_journal_paper_doi               10.1039/b927522c
_journal_volume                  39
_journal_year                    2010
_chemical_formula_moiety         'C48 H36 Fe3 N12 O12'
_chemical_formula_sum            'C48 H36 Fe3 N12 O12'
_chemical_formula_weight         1140.44
_chemical_melting_point          ?
_chemical_name_common
;
Iron(II) bis-benzimidazole oxalate
;
_chemical_name_systematic
;
catena-[(μ₂oxalato)-bis(benzimidazole)-iron(II)]
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 94.530(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.945(2)
_cell_length_b                   12.3461(9)
_cell_length_c                   18.550(2)
_cell_measurement_reflns_used    6413
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      29.37
_cell_measurement_theta_min      1.91
_cell_volume                     4781.8(8)
_computing_cell_refinement       'CELL (Stoe IPDS Software, 2000)'
_computing_data_collection       'EXPOSE (Stoe IPDS Software, 2000)'
_computing_data_reduction        'INTEGRATE (Stoe IPDS Software, 2000)'
_computing_molecular_graphics    'Diamond 2 (Brandenberg, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'phi oscillation'
_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  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0817
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18399
_diffrn_reflns_theta_full        26.09
_diffrn_reflns_theta_max         26.09
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.976
_exptl_absorpt_correction_T_max  0.5647
_exptl_absorpt_correction_T_min  0.5417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. R.H. Blessing, Acta Cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2328
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         1.572
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.856
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.856
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0462
_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)+(0.0674P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1294
_reflns_number_gt                2131
_reflns_number_total             4673
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b927522c.txt
_cod_data_source_block           compound2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'n/a' was changed to '?' - the value
is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        4781.9(8)
_cod_original_sg_symbol_H-M      'C 2 /c'
_cod_database_code               7025380
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Fe1 Fe 0.5000 0.86329(8) 0.2500 0.0297(3) Uani 1 2 d S
Fe2 Fe 0.66678(3) 0.63376(5) 0.08367(3) 0.02174(17) Uani 1 1 d .
O5 O 0.76667(13) 0.6465(2) 0.06176(15) 0.0251(7) Uani 1 1 d .
O3 O 0.56599(13) 0.6491(2) 0.09861(15) 0.0262(7) Uani 1 1 d .
O2 O 0.59706(14) 0.8483(3) 0.23087(15) 0.0299(8) Uani 1 1 d .
C1 C 0.6098(2) 0.7816(4) 0.1829(2) 0.0248(10) Uani 1 1 d .
C3 C 0.7780(2) 0.7153(4) 0.0162(2) 0.0222(10) Uani 1 1 d .
C2 C 0.5530(2) 0.7157(4) 0.1460(2) 0.0243(10) Uani 1 1 d .
O1 O 0.66358(13) 0.7639(3) 0.16280(15) 0.0297(8) Uani 1 1 d .
O4 O 0.49902(13) 0.7350(3) 0.16644(16) 0.0310(8) Uani 1 1 d .
N11 N 0.64572(16) 0.5095(3) 0.00451(18) 0.0265(9) Uani 1 1 d .
N21 N 0.69818(17) 0.5307(3) 0.17270(18) 0.0277(9) Uani 1 1 d .
N31 N 0.47873(19) 0.9808(3) 0.1648(2) 0.0376(10) Uani 1 1 d .
C11 C 0.6847(2) 0.4390(4) -0.0298(2) 0.0332(12) Uani 1 1 d .
C31 C 0.5124(2) 1.0748(4) 0.1507(2) 0.0307(11) Uani 1 1 d .
O6 O 0.66818(13) 0.7668(2) 0.00762(14) 0.0268(7) Uani 1 1 d .
C21 C 0.6656(2) 0.4757(4) 0.2242(2) 0.0252(9) Uani 1 1 d .
C33 C 0.5055(3) 1.2243(5) 0.0649(3) 0.0597(17) Uani 1 1 d .
H33 H 0.4853 1.2591 0.0249 0.072 Uiso 1 1 calc R
C22 C 0.7094(2) 0.4169(4) 0.2688(2) 0.0297(10) Uani 1 1 d .
C13 C 0.6749(3) 0.3025(5) -0.1254(3) 0.0687(19) Uani 1 1 d .
H13 H 0.6499 0.2635 -0.1600 0.082 Uiso 1 1 calc R
C12 C 0.6482(2) 0.3775(4) -0.0801(3) 0.0390(13) Uani 1 1 d .
C34 C 0.5597(3) 1.2645(4) 0.1005(3) 0.0537(15) Uani 1 1 d .
H34 H 0.5776 1.3276 0.0836 0.064 Uiso 1 1 calc R
C36 C 0.5669(2) 1.1191(4) 0.1868(3) 0.0404(12) Uani 1 1 d .
H36 H 0.5876 1.0853 0.2269 0.048 Uiso 1 1 calc R
C23 C 0.6920(2) 0.3541(4) 0.3257(2) 0.0433(13) Uani 1 1 d .
H23 H 0.7221 0.3165 0.3556 0.052 Uiso 1 1 calc R
C26 C 0.6010(2) 0.4723(4) 0.2356(2) 0.0332(11) Uani 1 1 d .
H26 H 0.5708 0.5108 0.2065 0.040 Uiso 1 1 calc R
N22 N 0.76799(18) 0.4400(3) 0.24430(19) 0.0365(10) Uani 1 1 d .
H22 H 0.8044 0.4161 0.2623 0.044 Uiso 1 1 calc R
N12 N 0.58672(19) 0.4099(3) -0.07457(19) 0.0381(10) Uani 1 1 d .
H12 H 0.5532 0.3845 -0.0984 0.046 Uiso 1 1 calc R
C25 C 0.5836(2) 0.4092(4) 0.2922(2) 0.0384(12) Uani 1 1 d .
H25 H 0.5407 0.4062 0.3016 0.046 Uiso 1 1 calc R
C24 C 0.6279(2) 0.3501(4) 0.3356(2) 0.0421(13) Uani 1 1 d .
H24 H 0.6138 0.3070 0.3723 0.050 Uiso 1 1 calc R
C35 C 0.5888(2) 1.2149(4) 0.1606(3) 0.0438(13) Uani 1 1 d .
H35 H 0.6247 1.2473 0.1844 0.053 Uiso 1 1 calc R
C14 C 0.7394(4) 0.2897(6) -0.1163(4) 0.102(3) Uani 1 1 d .
H14 H 0.7590 0.2395 -0.1447 0.122 Uiso 1 1 calc R
C16 C 0.7511(2) 0.4251(5) -0.0211(3) 0.0587(17) Uani 1 1 d .
H16 H 0.7765 0.4646 0.0128 0.070 Uiso 1 1 calc R
C15 C 0.7770(3) 0.3499(6) -0.0654(4) 0.101(3) Uani 1 1 d .
H15 H 0.8211 0.3389 -0.0612 0.121 Uiso 1 1 calc R
N32 N 0.4297(3) 1.0659(5) 0.0707(2) 0.0764(18) Uani 1 1 d .
H32 H 0.4018 1.0793 0.0353 0.092 Uiso 1 1 calc R
C32 C 0.4820(3) 1.1280(5) 0.0919(3) 0.0484(15) Uani 1 1 d .
C27 C 0.7585(2) 0.5063(4) 0.1875(2) 0.0315(11) Uani 1 1 d .
H27 H 0.7914 0.5322 0.1612 0.038 Uiso 1 1 calc R
C17 C 0.5882(2) 0.4887(4) -0.0251(2) 0.0335(11) Uani 1 1 d .
H17 H 0.5519 0.5254 -0.0128 0.040 Uiso 1 1 calc R
C37 C 0.4300(3) 0.9808(6) 0.1151(3) 0.0637(18) Uani 1 1 d .
H37 H 0.3990 0.9268 0.1114 0.076 Uiso 1 1 calc R
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'
Fe Fe 0.3463 0.8444 '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
O2 Fe1 O2 169.87(18) . 2_655
O2 Fe1 N31 92.09(13) . 2_655
O2 Fe1 N31 94.70(13) 2_655 2_655
O2 Fe1 N31 94.70(13) . .
O2 Fe1 N31 92.09(13) 2_655 .
N31 Fe1 N31 95.9(2) 2_655 .
O2 Fe1 O4 76.95(11) . .
O2 Fe1 O4 95.71(11) 2_655 .
N31 Fe1 O4 168.44(13) 2_655 .
N31 Fe1 O4 88.76(14) . .
O2 Fe1 O4 95.71(11) . 2_655
O2 Fe1 O4 76.95(11) 2_655 2_655
N31 Fe1 O4 88.76(14) 2_655 2_655
N31 Fe1 O4 168.44(13) . 2_655
O4 Fe1 O4 88.72(17) . 2_655
N11 Fe2 N21 97.85(14) . .
N11 Fe2 O3 90.01(12) . .
N21 Fe2 O3 101.33(12) . .
N11 Fe2 O6 96.26(12) . .
N21 Fe2 O6 158.62(13) . .
O3 Fe2 O6 94.63(11) . .
N11 Fe2 O5 94.19(12) . .
N21 Fe2 O5 86.90(12) . .
O3 Fe2 O5 170.18(11) . .
O6 Fe2 O5 76.11(11) . .
N11 Fe2 O1 166.40(12) . .
N21 Fe2 O1 86.71(13) . .
O3 Fe2 O1 76.51(11) . .
O6 Fe2 O1 83.26(11) . .
O5 Fe2 O1 98.85(11) . .
C3 O5 Fe2 114.7(3) . .
C2 O3 Fe2 114.7(3) . .
C1 O2 Fe1 116.2(3) . .
O1 C1 O2 125.5(4) . .
O1 C1 C2 117.3(4) . .
O2 C1 C2 117.1(4) . .
O5 C3 O6 125.8(4) . 7_665
O5 C3 C3 118.0(5) . 7_665
O6 C3 C3 116.2(5) 7_665 7_665
O4 C2 O3 126.5(4) . .
O4 C2 C1 116.6(4) . .
O3 C2 C1 116.9(3) . .
C1 O1 Fe2 114.3(3) . .
C2 O4 Fe1 113.1(3) . .
C17 N11 C11 103.9(4) . .
C17 N11 Fe2 124.0(3) . .
C11 N11 Fe2 131.9(3) . .
C27 N21 C21 105.2(3) . .
C27 N21 Fe2 122.0(3) . .
C21 N21 Fe2 132.8(3) . .
C37 N31 C31 104.1(4) . .
C37 N31 Fe1 127.8(4) . .
C31 N31 Fe1 128.1(3) . .
N11 C11 C12 109.9(4) . .
N11 C11 C16 129.9(4) . .
C12 C11 C16 120.2(4) . .
C32 C31 C36 120.2(5) . .
C32 C31 N31 109.5(4) . .
C36 C31 N31 130.3(4) . .
C3 O6 Fe2 114.7(3) 7_665 .
C26 C21 C22 120.0(4) . .
C26 C21 N21 131.0(4) . .
C22 C21 N21 109.0(4) . .
C34 C33 C32 116.2(5) . .
C34 C33 H33 121.9 . .
C32 C33 H33 121.9 . .
N22 C22 C23 131.8(4) . .
N22 C22 C21 105.0(4) . .
C23 C22 C21 123.1(4) . .
C14 C13 C12 116.4(6) . .
C14 C13 H13 121.8 . .
C12 C13 H13 121.8 . .
N12 C12 C11 105.3(4) . .
N12 C12 C13 131.9(5) . .
C11 C12 C13 122.8(5) . .
C33 C34 C35 122.1(5) . .
C33 C34 H34 118.9 . .
C35 C34 H34 118.9 . .
C35 C36 C31 117.0(5) . .
C35 C36 H36 121.5 . .
C31 C36 H36 121.5 . .
C24 C23 C22 116.3(4) . .
C24 C23 H23 121.9 . .
C22 C23 H23 121.9 . .
C25 C26 C21 116.9(4) . .
C25 C26 H26 121.5 . .
C21 C26 H26 121.5 . .
C27 N22 C22 108.0(4) . .
C27 N22 H22 126.0 . .
C22 N22 H22 126.0 . .
C17 N12 C12 107.2(4) . .
C17 N12 H12 126.4 . .
C12 N12 H12 126.4 . .
C26 C25 C24 122.3(4) . .
C26 C25 H25 118.8 . .
C24 C25 H25 118.8 . .
C23 C24 C25 121.4(4) . .
C23 C24 H24 119.3 . .
C25 C24 H24 119.3 . .
C36 C35 C34 122.2(5) . .
C36 C35 H35 118.9 . .
C34 C35 H35 118.9 . .
C13 C14 C15 121.7(6) . .
C13 C14 H14 119.1 . .
C15 C14 H14 119.1 . .
C15 C16 C11 116.7(5) . .
C15 C16 H16 121.7 . .
C11 C16 H16 121.7 . .
C16 C15 C14 122.2(6) . .
C16 C15 H15 118.9 . .
C14 C15 H15 118.9 . .
C37 N32 C32 107.4(5) . .
C37 N32 H32 126.3 . .
C32 N32 H32 126.3 . .
N32 C32 C31 105.6(5) . .
N32 C32 C33 132.2(5) . .
C31 C32 C33 122.2(5) . .
N21 C27 N22 112.7(4) . .
N21 C27 H27 123.6 . .
N22 C27 H27 123.6 . .
N11 C17 N12 113.7(4) . .
N11 C17 H17 123.2 . .
N12 C17 H17 123.2 . .
N31 C37 N32 113.4(5) . .
N31 C37 H37 123.3 . .
N32 C37 H37 123.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 O2 2.099(3) .
Fe1 O2 2.099(3) 2_655
Fe1 N31 2.166(4) 2_655
Fe1 N31 2.166(4) .
Fe1 O4 2.215(3) .
Fe1 O4 2.215(3) 2_655
Fe2 N11 2.145(4) .
Fe2 N21 2.147(4) .
Fe2 O3 2.159(3) .
Fe2 O6 2.167(3) .
Fe2 O5 2.168(3) .
Fe2 O1 2.181(3) .
O5 C3 1.235(5) .
O3 C2 1.249(5) .
O2 C1 1.256(5) .
C1 O1 1.233(5) .
C1 C2 1.556(5) .
C3 O6 1.263(5) 7_665
C3 C3 1.534(9) 7_665
C2 O4 1.243(5) .
N11 C17 1.308(5) .
N11 C11 1.383(5) .
N21 C27 1.307(5) .
N21 C21 1.394(5) .
N31 C37 1.320(6) .
N31 C31 1.394(6) .
C11 C12 1.385(6) .
C11 C16 1.397(7) .
C31 C32 1.385(7) .
C31 C36 1.389(6) .
O6 C3 1.263(5) 7_665
C21 C26 1.385(6) .
C21 C22 1.391(6) .
C33 C34 1.362(8) .
C33 C32 1.394(8) .
C33 H33 0.9300 .
C22 N22 1.373(5) .
C22 C23 1.382(6) .
C13 C14 1.357(9) .
C13 C12 1.397(7) .
C13 H13 0.9300 .
C12 N12 1.360(6) .
C34 C35 1.371(7) .
C34 H34 0.9300 .
C36 C35 1.371(6) .
C36 H36 0.9300 .
C23 C24 1.369(7) .
C23 H23 0.9300 .
C26 C25 1.379(6) .
C26 H26 0.9300 .
N22 C27 1.337(5) .
N22 H22 0.8600 .
N12 C17 1.337(6) .
N12 H12 0.8600 .
C25 C24 1.387(6) .
C25 H25 0.9300 .
C24 H24 0.9300 .
C35 H35 0.9300 .
C14 C15 1.395(9) .
C14 H14 0.9300 .
C16 C15 1.381(7) .
C16 H16 0.9300 .
C15 H15 0.9300 .
N32 C37 1.335(7) .
N32 C32 1.369(7) .
N32 H32 0.8600 .
C27 H27 0.9300 .
C17 H17 0.9300 .
C37 H37 0.9300 .
