#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/40/2224004.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_2224004
loop_
_publ_author_name
'Wu, Dayu'
_publ_section_title
;
 Bis[N-(2-pyridylcarbonyl)pyridine-2-carboximidato]iron(III)
 perchlorate methanol solvate
;
_journal_coeditor_code           SI2207
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1340
_journal_paper_doi               10.1107/S1600536809040549
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Fe (C12 H8 N3 O2)2] Cl O4, C H4 O'
_chemical_formula_moiety         'C24 H16 Fe N6 O4 +, Cl O4 -, C H4 O'
_chemical_formula_sum            'C25 H20 Cl Fe N6 O9'
_chemical_formula_weight         639.77
_chemical_name_systematic
;Bis[N-(2-pyridylcarbonyl)pyridine-2-carboximidato]iron(III)
 perchlorate
methanol solvate
;
_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                109.507(4)
_cell_angle_beta                 103.394(3)
_cell_angle_gamma                100.091(3)
_cell_formula_units_Z            2
_cell_length_a                   8.799(3)
_cell_length_b                   11.603(4)
_cell_length_c                   14.356(6)
_cell_measurement_reflns_used    5465
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      27.787
_cell_measurement_theta_min      3.021
_cell_volume                     1292.0(8)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8499
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SHELXTL; Sheldrick, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             654
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         1.478
_refine_diff_density_min         -0.480
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0400
_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)+(0.0537P)²+1.8601P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                4177
_reflns_number_total             4421
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2207.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               2224004
_cod_database_fobs_code          2224004
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe1 0.58016(4) 0.81056(3) 0.23045(2) 0.01007(12) Uani d . 1 . .
O O1 0.2790(2) 0.51858(16) -0.02782(13) 0.0148(4) Uani d . 1 . .
N N2 0.5013(2) 0.68770(19) 0.09138(15) 0.0112(4) Uani d . 1 . .
O O2 0.5569(2) 0.63892(17) -0.06690(13) 0.0168(4) Uani d . 1 . .
N N1 0.3602(2) 0.73605(19) 0.23053(15) 0.0121(4) Uani d . 1 . .
N N6 0.6689(2) 0.70815(19) 0.30342(16) 0.0129(4) Uani d . 1 . .
N N3 0.7802(2) 0.84703(19) 0.19255(16) 0.0127(4) Uani d . 1 . .
N N5 0.6579(2) 0.93790(19) 0.36992(15) 0.0136(4) Uani d . 1 . .
N N4 0.5149(2) 0.95113(19) 0.19857(15) 0.0124(4) Uani d . 1 . .
C C5 0.2725(3) 0.6311(2) 0.14314(18) 0.0118(5) Uani d . 1 . .
O O4 0.7774(3) 0.97129(19) 0.54311(14) 0.0338(5) Uani d . 1 . .
O O3 0.6870(3) 1.15149(18) 0.46500(15) 0.0326(5) Uani d . 1 . .
C C7 0.5952(3) 0.6937(2) 0.02702(18) 0.0121(5) Uani d . 1 . .
C C6 0.3479(3) 0.6029(2) 0.05672(18) 0.0119(5) Uani d . 1 . .
C C9 0.8828(3) 0.7988(2) 0.0474(2) 0.0175(5) Uani d . 1 . .
H H9A 0.8652 0.7542 -0.0230 0.021 Uiso calc R 1 . .
C C4 0.1249(3) 0.5577(2) 0.13335(19) 0.0165(5) Uani d . 1 . .
H H4A 0.0705 0.4844 0.0739 0.020 Uiso calc R 1 . .
C C15 0.4363(3) 1.1664(3) 0.1802(2) 0.0202(6) Uani d . 1 . .
H H15A 0.4089 1.2379 0.1738 0.024 Uiso calc R 1 . .
C C13 0.4368(3) 0.9487(2) 0.10510(19) 0.0141(5) Uani d . 1 . .
H H13A 0.4096 0.8740 0.0464 0.017 Uiso calc R 1 . .
C C8 0.7602(3) 0.7837(2) 0.09035(19) 0.0133(5) Uani d . 1 . .
C C11 1.0553(3) 0.9449(3) 0.2156(2) 0.0211(6) Uani d . 1 . .
H H11A 1.1562 0.9995 0.2597 0.025 Uiso calc R 1 . .
C C10 1.0327(3) 0.8812(3) 0.1110(2) 0.0226(6) Uani d . 1 . .
H H10A 1.1174 0.8938 0.0838 0.027 Uiso calc R 1 . .
C C24 0.6699(3) 0.5865(2) 0.2595(2) 0.0145(5) Uani d . 1 . .
H H24A 0.6253 0.5434 0.1878 0.017 Uiso calc R 1 . .
C C14 0.3960(3) 1.0545(3) 0.0939(2) 0.0178(5) Uani d . 1 . .
H H14A 0.3417 1.0501 0.0285 0.021 Uiso calc R 1 . .
C C22 0.8026(4) 0.5867(3) 0.4249(2) 0.0273(6) Uani d . 1 . .
H H22A 0.8482 0.5458 0.4653 0.033 Uiso calc R 1 . .
C C17 0.5555(3) 1.0616(2) 0.28249(19) 0.0160(5) Uani d . 1 . .
C C18 0.6414(3) 1.0583(2) 0.3844(2) 0.0182(5) Uani d . 1 . .
C C3 0.0577(3) 0.5945(3) 0.2137(2) 0.0189(5) Uani d . 1 . .
H H3A -0.0422 0.5463 0.2089 0.023 Uiso calc R 1 . .
C C20 0.7334(3) 0.7695(2) 0.40816(19) 0.0177(5) Uani d . 1 . .
C C21 0.8008(4) 0.7121(3) 0.4710(2) 0.0257(6) Uani d . 1 . .
H H21A 0.8441 0.7564 0.5427 0.031 Uiso calc R 1 . .
C C1 0.2943(3) 0.7719(2) 0.30753(19) 0.0157(5) Uani d . 1 . .
H H1A 0.3519 0.8443 0.3672 0.019 Uiso calc R 1 . .
C C12 0.9269(3) 0.9267(2) 0.25399(19) 0.0156(5) Uani d . 1 . .
H H12A 0.9423 0.9708 0.3242 0.019 Uiso calc R 1 . .
C C23 0.7360(3) 0.5236(3) 0.3187(2) 0.0205(6) Uani d . 1 . .
H H23A 0.7352 0.4393 0.2868 0.025 Uiso calc R 1 . .
C C19 0.7269(3) 0.9048(2) 0.4504(2) 0.0188(5) Uani d . 1 . .
C C16 0.5182(3) 1.1700(3) 0.2764(2) 0.0208(6) Uani d . 1 . .
H H16A 0.5476 1.2442 0.3358 0.025 Uiso calc R 1 . .
C C2 0.1426(3) 0.7039(3) 0.3005(2) 0.0193(6) Uani d . 1 . .
H H2A 0.0985 0.7320 0.3542 0.023 Uiso calc R 1 . .
Cl Cl1 0.91561(7) 0.22764(6) 0.18640(5) 0.02052(17) Uani d . 1 . .
O O14 0.8085(2) 0.10315(19) 0.15308(18) 0.0319(5) Uani d . 1 . .
O O13 1.0750(2) 0.2169(2) 0.18132(17) 0.0346(5) Uani d . 1 . .
O O12 0.9291(3) 0.3020(2) 0.29168(18) 0.0458(6) Uani d . 1 . .
O O11 0.8522(3) 0.2870(2) 0.1189(2) 0.0512(7) Uani d . 1 . .
C C1W 0.3474(5) 0.5122(4) 0.3889(3) 0.0481(9) Uani d . 1 . .
H H1WA 0.2545 0.5255 0.4108 0.072 Uiso calc R 1 . .
H H1WB 0.3419 0.5313 0.3283 0.072 Uiso calc R 1 . .
H H1WC 0.4448 0.5668 0.4438 0.072 Uiso calc R 1 . .
O O1W 0.3486(3) 0.3837(2) 0.36481(19) 0.0415(6) Uani d . 1 . .
H H1W 0.2370 0.3263 0.3121 0.050 Uiso d R 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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
N2 Fe1 N5 . . 178.55(8) ?
N2 Fe1 N6 . . 100.02(9) ?
N5 Fe1 N6 . . 81.43(9) ?
N2 Fe1 N4 . . 96.55(9) ?
N5 Fe1 N4 . . 82.01(9) ?
N6 Fe1 N4 . . 163.43(9) ?
N2 Fe1 N1 . . 82.14(8) ?
N5 Fe1 N1 . . 97.85(9) ?
N6 Fe1 N1 . . 89.91(8) ?
N4 Fe1 N1 . . 92.51(8) ?
N2 Fe1 N3 . . 82.31(8) ?
N5 Fe1 N3 . . 97.73(9) ?
N6 Fe1 N3 . . 91.22(8) ?
N4 Fe1 N3 . . 90.84(8) ?
N1 Fe1 N3 . . 164.37(9) ?
C7 N2 C6 . . 123.1(2) ?
C7 N2 Fe1 . . 117.82(16) ?
C6 N2 Fe1 . . 118.93(16) ?
C1 N1 C5 . . 118.1(2) ?
C1 N1 Fe1 . . 127.89(17) ?
C5 N1 Fe1 . . 113.91(16) ?
C24 N6 C20 . . 118.5(2) ?
C24 N6 Fe1 . . 126.44(17) ?
C20 N6 Fe1 . . 115.01(17) ?
C12 N3 C8 . . 118.2(2) ?
C12 N3 Fe1 . . 128.32(17) ?
C8 N3 Fe1 . . 113.43(16) ?
C19 N5 C18 . . 123.3(2) ?
C19 N5 Fe1 . . 118.66(17) ?
C18 N5 Fe1 . . 118.07(16) ?
C13 N4 C17 . . 117.9(2) ?
C13 N4 Fe1 . . 127.82(17) ?
C17 N4 Fe1 . . 114.28(16) ?
N1 C5 C4 . . 122.6(2) ?
N1 C5 C6 . . 115.1(2) ?
C4 C5 C6 . . 122.3(2) ?
O2 C7 N2 . . 128.2(2) ?
O2 C7 C8 . . 122.1(2) ?
N2 C7 C8 . . 109.7(2) ?
O1 C6 N2 . . 128.2(2) ?
O1 C6 C5 . . 122.5(2) ?
N2 C6 C5 . . 109.3(2) ?
C8 C9 C10 . . 118.7(2) ?
C8 C9 H9A . . 120.6 ?
C10 C9 H9A . . 120.6 ?
C5 C4 C3 . . 119.1(2) ?
C5 C4 H4A . . 120.5 ?
C3 C4 H4A . . 120.5 ?
C14 C15 C16 . . 118.6(2) ?
C14 C15 H15A . . 120.7 ?
C16 C15 H15A . . 120.7 ?
N4 C13 C14 . . 121.8(2) ?
N4 C13 H13A . . 119.1 ?
C14 C13 H13A . . 119.1 ?
N3 C8 C9 . . 122.6(2) ?
N3 C8 C7 . . 115.4(2) ?
C9 C8 C7 . . 121.9(2) ?
C10 C11 C12 . . 119.5(2) ?
C10 C11 H11A . . 120.3 ?
C12 C11 H11A . . 120.3 ?
C9 C10 C11 . . 119.2(2) ?
C9 C10 H10A . . 120.4 ?
C11 C10 H10A . . 120.4 ?
N6 C24 C23 . . 121.5(2) ?
N6 C24 H24A . . 119.2 ?
C23 C24 H24A . . 119.2 ?
C15 C14 C13 . . 119.8(2) ?
C15 C14 H14A . . 120.1 ?
C13 C14 H14A . . 120.1 ?
C23 C22 C21 . . 119.2(3) ?
C23 C22 H22A . . 120.4 ?
C21 C22 H22A . . 120.4 ?
N4 C17 C16 . . 122.9(2) ?
N4 C17 C18 . . 115.5(2) ?
C16 C17 C18 . . 121.6(2) ?
O3 C18 N5 . . 127.9(2) ?
O3 C18 C17 . . 122.0(2) ?
N5 C18 C17 . . 110.1(2) ?
C2 C3 C4 . . 118.6(2) ?
C2 C3 H3A . . 120.7 ?
C4 C3 H3A . . 120.7 ?
N6 C20 C21 . . 122.6(2) ?
N6 C20 C19 . . 114.9(2) ?
C21 C20 C19 . . 122.6(2) ?
C20 C21 C22 . . 118.5(3) ?
C20 C21 H21A . . 120.7 ?
C22 C21 H21A . . 120.7 ?
N1 C1 C2 . . 121.8(2) ?
N1 C1 H1A . . 119.1 ?
C2 C1 H1A . . 119.1 ?
N3 C12 C11 . . 121.8(2) ?
N3 C12 H12A . . 119.1 ?
C11 C12 H12A . . 119.1 ?
C22 C23 C24 . . 119.7(3) ?
C22 C23 H23A . . 120.2 ?
C24 C23 H23A . . 120.2 ?
O4 C19 N5 . . 127.6(2) ?
O4 C19 C20 . . 122.4(2) ?
N5 C19 C20 . . 110.0(2) ?
C17 C16 C15 . . 118.8(2) ?
C17 C16 H16A . . 120.6 ?
C15 C16 H16A . . 120.6 ?
C3 C2 C1 . . 119.7(2) ?
C3 C2 H2A . . 120.2 ?
C1 C2 H2A . . 120.2 ?
O12 Cl1 O14 . . 109.89(15) ?
O12 Cl1 O11 . . 110.31(17) ?
O14 Cl1 O11 . . 108.86(14) ?
O12 Cl1 O13 . . 108.75(13) ?
O14 Cl1 O13 . . 109.36(13) ?
O11 Cl1 O13 . . 109.66(16) ?
O1W C1W H1WA . . 109.5 ?
O1W C1W H1WB . . 109.5 ?
H1WA C1W H1WB . . 109.5 ?
O1W C1W H1WC . . 109.5 ?
H1WA C1W H1WC . . 109.5 ?
H1WB C1W H1WC . . 109.5 ?
C1W O1W H1W . . 108.2 ?
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
Fe1 N2 . 1.900(2) yes
Fe1 N5 . 1.922(2) yes
Fe1 N6 . 1.974(2) yes
Fe1 N4 . 1.976(2) yes
Fe1 N1 . 1.977(2) yes
Fe1 N3 . 1.977(2) yes
O1 C6 . 1.206(3) ?
N2 C7 . 1.384(3) ?
N2 C6 . 1.391(3) ?
O2 C7 . 1.216(3) ?
N1 C1 . 1.344(3) ?
N1 C5 . 1.362(3) ?
N6 C24 . 1.343(3) ?
N6 C20 . 1.356(3) ?
N3 C12 . 1.345(3) ?
N3 C8 . 1.356(3) ?
N5 C19 . 1.379(3) ?
N5 C18 . 1.381(3) ?
N4 C13 . 1.347(3) ?
N4 C17 . 1.353(3) ?
C5 C4 . 1.371(3) ?
C5 C6 . 1.507(3) ?
O4 C19 . 1.219(3) ?
O3 C18 . 1.211(3) ?
C7 C8 . 1.499(3) ?
C9 C8 . 1.374(4) ?
C9 C10 . 1.380(4) ?
C9 H9A . 0.9300 ?
C4 C3 . 1.392(4) ?
C4 H4A . 0.9300 ?
C15 C14 . 1.381(4) ?
C15 C16 . 1.384(4) ?
C15 H15A . 0.9300 ?
C13 C14 . 1.385(4) ?
C13 H13A . 0.9300 ?
C11 C10 . 1.381(4) ?
C11 C12 . 1.381(4) ?
C11 H11A . 0.9300 ?
C10 H10A . 0.9300 ?
C24 C23 . 1.388(4) ?
C24 H24A . 0.9300 ?
C14 H14A . 0.9300 ?
C22 C23 . 1.377(4) ?
C22 C21 . 1.387(4) ?
C22 H22A . 0.9300 ?
C17 C16 . 1.379(4) ?
C17 C18 . 1.500(4) ?
C3 C2 . 1.380(4) ?
C3 H3A . 0.9300 ?
C20 C21 . 1.379(4) ?
C20 C19 . 1.500(4) ?
C21 H21A . 0.9300 ?
C1 C2 . 1.390(4) ?
C1 H1A . 0.9300 ?
C12 H12A . 0.9300 ?
C23 H23A . 0.9300 ?
C16 H16A . 0.9300 ?
C2 H2A . 0.9300 ?
Cl1 O12 . 1.433(2) ?
Cl1 O14 . 1.434(2) ?
Cl1 O11 . 1.434(2) ?
Cl1 O13 . 1.446(2) ?
C1W O1W . 1.416(4) ?
C1W H1WA . 0.9600 ?
C1W H1WB . 0.9600 ?
C1W H1WC . 0.9600 ?
O1W H1W . 1.0342 ?
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
O1W H1W O13 1_455 1.03 1.92 2.916(3) 159.6
