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#$Date: 2025-08-21 13:25:49 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301846 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/65/7006558.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_7006558
loop_
_publ_author_name
'Tanase, Stefania'
'Marqués Gallego, Patricia'
'Bouwman, Elisabeth'
'Long, Gary J.'
'Rebbouh, Leila'
'Grandjean, Fernande'
'de Gelder, René'
'Mutikainen, Ilpo'
'Turpeinen, Urho'
'Reedijk, Jan'
_publ_section_title
;
 Versatility in the binding of 2-pyrazinecarboxylate with iron.
 Synthesis, structure and magnetic properties of iron(II) and iron(III)
 complexes.
;
_journal_issue                   13
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1675
_journal_page_last               1684
_journal_paper_doi               10.1039/b512048a
_journal_year                    2006
_chemical_formula_sum            'C25 H21 Fe N7 O4'
_chemical_formula_weight         539.34
_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                 118.93(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.239(2)
_cell_length_b                   28.497(2)
_cell_length_c                   10.402(4)
_cell_measurement_reflns_used    35346
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      3.10
_cell_volume                     2396.9(12)
_computing_cell_refinement       'COLLECT (Nonius, 2002)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'COLLECT (Nonius, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'SHELXTL (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0638
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            35346
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.9478
_exptl_absorpt_correction_T_min  0.8765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0376P)²+1.2197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                4072
_reflns_number_total             5486
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b512048a.txt
_cod_data_source_block           pm15
_cod_original_cell_volume        2396.9(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7006558
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_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.33229(4) 0.109197(10) 0.65612(3) 0.01867(9) Uani 1 d . . .
N11 N 0.5466(2) 0.07631(6) 0.65234(19) 0.0211(4) Uani 1 d . . .
C12 C 0.5091(3) 0.06362(7) 0.5149(2) 0.0206(4) Uani 1 d . . .
C13 C 0.6313(3) 0.04876(8) 0.4832(3) 0.0272(5) Uani 1 d . . .
H13A H 0.6009 0.0412 0.3843 0.033 Uiso 1 calc R . .
N14 N 0.7904(3) 0.04459(7) 0.5859(2) 0.0316(5) Uani 1 d . . .
C15 C 0.8231(3) 0.05527(8) 0.7221(3) 0.0309(5) Uani 1 d . . .
H15A H 0.9332 0.0516 0.7997 0.037 Uiso 1 calc R . .
C16 C 0.7041(3) 0.07156(8) 0.7558(2) 0.0261(5) Uani 1 d . . .
H16A H 0.7352 0.0795 0.8546 0.031 Uiso 1 calc R . .
C17 C 0.3290(3) 0.06500(7) 0.4017(2) 0.0222(5) Uani 1 d . . .
O18 O 0.23295(18) 0.08295(5) 0.44736(15) 0.0239(3) Uani 1 d . . .
O19 O 0.2854(2) 0.04922(6) 0.27899(17) 0.0314(4) Uani 1 d . . .
N21 N 0.2818(2) 0.04899(6) 0.75945(18) 0.0189(4) Uani 1 d . . .
C22 C 0.3447(3) 0.05443(7) 0.9054(2) 0.0193(4) Uani 1 d . . .
C23 C 0.3105(3) 0.02197(8) 0.9869(2) 0.0250(5) Uani 1 d . . .
H23A H 0.3568 0.0267 1.0897 0.030 Uiso 1 calc R . .
N24 N 0.2144(3) -0.01578(7) 0.9258(2) 0.0305(5) Uani 1 d . . .
C25 C 0.1538(3) -0.02051(8) 0.7808(3) 0.0292(5) Uani 1 d . . .
H25A H 0.0851 -0.0467 0.7327 0.035 Uiso 1 calc R . .
C26 C 0.1874(3) 0.01138(7) 0.6979(2) 0.0232(5) Uani 1 d . . .
H26A H 0.1424 0.0063 0.5953 0.028 Uiso 1 calc R . .
C27 C 0.4506(3) 0.09770(7) 0.9709(2) 0.0224(5) Uani 1 d . . .
O28 O 0.45563(19) 0.12588(5) 0.87580(16) 0.0238(3) Uani 1 d . . .
O29 O 0.5208(2) 0.10352(6) 1.10416(16) 0.0350(4) Uani 1 d . . .
N31 N 0.4052(2) 0.17809(6) 0.60746(19) 0.0219(4) Uani 1 d . . .
C32 C 0.5292(3) 0.20283(8) 0.7120(2) 0.0264(5) Uani 1 d . . .
H32A H 0.5864 0.1900 0.8081 0.032 Uiso 1 calc R . .
C33 C 0.5786(3) 0.24621(8) 0.6875(3) 0.0313(5) Uani 1 d . . .
H33A H 0.6674 0.2625 0.7653 0.038 Uiso 1 calc R . .
C34 C 0.4971(3) 0.26545(8) 0.5485(3) 0.0351(6) Uani 1 d . . .
H34A H 0.5275 0.2953 0.5288 0.042 Uiso 1 calc R . .
C35 C 0.3702(3) 0.24011(9) 0.4390(3) 0.0366(6) Uani 1 d . . .
H35A H 0.3128 0.2522 0.3418 0.044 Uiso 1 calc R . .
C36 C 0.3268(3) 0.19682(8) 0.4717(3) 0.0290(5) Uani 1 d . . .
H36A H 0.2386 0.1798 0.3955 0.035 Uiso 1 calc R . .
N41 N 0.0872(2) 0.13759(6) 0.60123(19) 0.0215(4) Uani 1 d . . .
C42 C 0.0566(3) 0.15556(8) 0.7051(3) 0.0261(5) Uani 1 d . . .
H42A H 0.1454 0.1579 0.8028 0.031 Uiso 1 calc R . .
C43 C -0.0981(3) 0.17086(9) 0.6764(3) 0.0317(5) Uani 1 d . . .
H43A H -0.1147 0.1835 0.7528 0.038 Uiso 1 calc R . .
C44 C -0.2281(3) 0.16744(8) 0.5353(3) 0.0314(5) Uani 1 d . . .
H44A H -0.3358 0.1775 0.5130 0.038 Uiso 1 calc R . .
C45 C -0.1991(3) 0.14913(8) 0.4269(3) 0.0287(5) Uani 1 d . . .
H45A H -0.2862 0.1464 0.3287 0.034 Uiso 1 calc R . .
C46 C -0.0409(3) 0.13497(8) 0.4646(2) 0.0246(5) Uani 1 d . . .
H46A H -0.0215 0.1226 0.3894 0.030 Uiso 1 calc R . .
N51 N 0.1456(3) 0.19388(11) 1.0735(3) 0.0611(7) Uani 1 d . . .
C52 C 0.0120(4) 0.21986(10) 1.0562(3) 0.0495(8) Uani 1 d . . .
H52A H 0.0131 0.2527 1.0413 0.059 Uiso 1 calc R . .
C53 C -0.1182(3) 0.20157(9) 1.0590(3) 0.0394(6) Uani 1 d . . .
H53A H -0.2081 0.2208 1.0465 0.047 Uiso 1 calc R . .
C54 C -0.1201(3) 0.15518(10) 1.0801(3) 0.0419(7) Uani 1 d . . .
H54A H -0.2128 0.1417 1.0826 0.050 Uiso 1 calc R . .
C55 C 0.0087(3) 0.12653(10) 1.0982(3) 0.0366(6) Uani 1 d . . .
H55A H 0.0046 0.0937 1.1118 0.044 Uiso 1 calc R . .
C56 C 0.1432(3) 0.14641(10) 1.0962(3) 0.0377(6) Uani 1 d . . .
H56A H 0.2342 0.1274 1.1105 0.045 Uiso 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Fe Fe 0.3463 0.8444 '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'
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'
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
_geom_angle_publ_flag
O18 Fe1 O28 170.65(6) . . ?
O18 Fe1 N21 98.15(6) . . ?
O28 Fe1 N21 76.76(6) . . ?
O18 Fe1 N41 88.97(7) . . ?
O28 Fe1 N41 98.66(7) . . ?
N21 Fe1 N41 88.78(6) . . ?
O18 Fe1 N11 76.81(7) . . ?
O28 Fe1 N11 95.64(7) . . ?
N21 Fe1 N11 94.70(6) . . ?
N41 Fe1 N11 165.69(7) . . ?
O18 Fe1 N31 96.39(6) . . ?
O28 Fe1 N31 89.01(6) . . ?
N21 Fe1 N31 165.40(6) . . ?
N41 Fe1 N31 90.19(6) . . ?
N11 Fe1 N31 89.86(6) . . ?
C16 N11 C12 116.70(18) . . ?
C16 N11 Fe1 131.76(14) . . ?
C12 N11 Fe1 111.13(14) . . ?
N11 C12 C13 120.9(2) . . ?
N11 C12 C17 116.27(18) . . ?
C13 C12 C17 122.8(2) . . ?
N14 C13 C12 122.9(2) . . ?
N14 C13 H13A 118.6 . . ?
C12 C13 H13A 118.6 . . ?
C15 N14 C13 115.1(2) . . ?
N14 C15 C16 123.1(2) . . ?
N14 C15 H15A 118.5 . . ?
C16 C15 H15A 118.5 . . ?
N11 C16 C15 121.2(2) . . ?
N11 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
O19 C17 O18 126.1(2) . . ?
O19 C17 C12 119.23(19) . . ?
O18 C17 C12 114.70(18) . . ?
C17 O18 Fe1 119.83(14) . . ?
C26 N21 C22 117.34(18) . . ?
C26 N21 Fe1 129.69(14) . . ?
C22 N21 Fe1 112.62(13) . . ?
N21 C22 C23 120.6(2) . . ?
N21 C22 C27 115.68(17) . . ?
C23 C22 C27 123.71(19) . . ?
N24 C23 C22 122.5(2) . . ?
N24 C23 H23A 118.7 . . ?
C22 C23 H23A 118.7 . . ?
C25 N24 C23 115.77(19) . . ?
N24 C25 C26 122.5(2) . . ?
N24 C25 H25A 118.8 . . ?
C26 C25 H25A 118.8 . . ?
N21 C26 C25 121.3(2) . . ?
N21 C26 H26A 119.4 . . ?
C25 C26 H26A 119.4 . . ?
O29 C27 O28 125.9(2) . . ?
O29 C27 C22 119.50(19) . . ?
O28 C27 C22 114.57(18) . . ?
C27 O28 Fe1 120.09(13) . . ?
C32 N31 C36 117.29(19) . . ?
C32 N31 Fe1 121.20(14) . . ?
C36 N31 Fe1 121.51(15) . . ?
N31 C32 C33 123.4(2) . . ?
N31 C32 H32A 118.3 . . ?
C33 C32 H32A 118.3 . . ?
C34 C33 C32 119.1(2) . . ?
C34 C33 H33A 120.4 . . ?
C32 C33 H33A 120.4 . . ?
C35 C34 C33 118.2(2) . . ?
C35 C34 H34A 120.9 . . ?
C33 C34 H34A 120.9 . . ?
C34 C35 C36 119.6(2) . . ?
C34 C35 H35A 120.2 . . ?
C36 C35 H35A 120.2 . . ?
N31 C36 C35 122.4(2) . . ?
N31 C36 H36A 118.8 . . ?
C35 C36 H36A 118.8 . . ?
C46 N41 C42 116.89(19) . . ?
C46 N41 Fe1 121.57(14) . . ?
C42 N41 Fe1 121.41(15) . . ?
N41 C42 C43 123.0(2) . . ?
N41 C42 H42A 118.5 . . ?
C43 C42 H42A 118.5 . . ?
C44 C43 C42 119.0(2) . . ?
C44 C43 H43A 120.5 . . ?
C42 C43 H43A 120.5 . . ?
C43 C44 C45 118.9(2) . . ?
C43 C44 H44A 120.6 . . ?
C45 C44 H44A 120.6 . . ?
C46 C45 C44 118.5(2) . . ?
C46 C45 H45A 120.8 . . ?
C44 C45 H45A 120.8 . . ?
N41 C46 C45 123.8(2) . . ?
N41 C46 H46A 118.1 . . ?
C45 C46 H46A 118.1 . . ?
C52 N51 C56 117.7(3) . . ?
C53 C52 N51 123.6(3) . . ?
C53 C52 H52A 118.2 . . ?
N51 C52 H52A 118.2 . . ?
C52 C53 C54 118.4(3) . . ?
C52 C53 H53A 120.8 . . ?
C54 C53 H53A 120.8 . . ?
C53 C54 C55 121.8(3) . . ?
C53 C54 H54A 119.1 . . ?
C55 C54 H54A 119.1 . . ?
C56 C55 C54 118.7(3) . . ?
C56 C55 H55A 120.6 . . ?
C54 C55 H55A 120.6 . . ?
N51 C56 C55 119.9(3) . . ?
N51 C56 H56A 120.1 . . ?
C55 C56 H56A 120.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O18 2.0468(16) . ?
Fe1 O28 2.0559(17) . ?
Fe1 N21 2.1914(17) . ?
Fe1 N41 2.2038(19) . ?
Fe1 N11 2.2081(18) . ?
Fe1 N31 2.2122(17) . ?
N11 C16 1.334(3) . ?
N11 C12 1.347(3) . ?
C12 C13 1.387(3) . ?
C12 C17 1.504(3) . ?
C13 N14 1.341(3) . ?
C13 H13A 0.9500 . ?
N14 C15 1.333(3) . ?
C15 C16 1.387(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 O19 1.224(2) . ?
C17 O18 1.297(2) . ?
N21 C26 1.333(3) . ?
N21 C22 1.347(3) . ?
C22 C23 1.391(3) . ?
C22 C27 1.515(3) . ?
C23 N24 1.343(3) . ?
C23 H23A 0.9500 . ?
N24 C25 1.338(3) . ?
C25 C26 1.387(3) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C27 O29 1.225(3) . ?
C27 O28 1.292(3) . ?
N31 C32 1.336(3) . ?
N31 C36 1.347(3) . ?
C32 C33 1.383(3) . ?
C32 H32A 0.9500 . ?
C33 C34 1.380(3) . ?
C33 H33A 0.9500 . ?
C34 C35 1.379(4) . ?
C34 H34A 0.9500 . ?
C35 C36 1.390(3) . ?
C35 H35A 0.9500 . ?
C36 H36A 0.9500 . ?
N41 C46 1.341(3) . ?
N41 C42 1.344(3) . ?
C42 C43 1.382(3) . ?
C42 H42A 0.9500 . ?
C43 C44 1.379(3) . ?
C43 H43A 0.9500 . ?
C44 C45 1.381(3) . ?
C44 H44A 0.9500 . ?
C45 C46 1.378(3) . ?
C45 H45A 0.9500 . ?
C46 H46A 0.9500 . ?
N51 C52 1.374(4) . ?
N51 C56 1.375(4) . ?
C52 C53 1.325(4) . ?
C52 H52A 0.9500 . ?
C53 C54 1.341(4) . ?
C53 H53A 0.9500 . ?
C54 C55 1.379(4) . ?
C54 H54A 0.9500 . ?
C55 C56 1.375(4) . ?
C55 H55A 0.9500 . ?
C56 H56A 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139152255
