##############################################################################
### ###
### Electronic paper (Acta Crystallographica Section E) ###
### ###
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# #
# This CIF contains the data in a paper accepted for publication in Acta #
# Crystallographica Section E. It conforms to the requirements of Notes #
# for Authors for Section E, and has been peer reviewed under the auspices #
# of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. #
# #
# Software is freely available for graphical display of the structure(s) in #
# this CIF. For information consult the CIF home page http://www.iucr.org/ #
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# This file may be used for bona fide research purposes within the #
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data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
Chlorido{N,N'-o-phenylene-[6,6'-ethylenebis(pyridine-2-carboxamide)]}iron(III)
;
_chemical_name_common ?
_chemical_formula_moiety 'C20 H14 Cl Fe N4 O2'
_chemical_formula_sum 'C20 H14 Cl Fe N4 O2'
_chemical_formula_iupac '[Fe (C20 H14 N4 O2) Cl]'
_chemical_formula_weight 433.65
_chemical_melting_point ?
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a 11.8532(2)
_cell_length_b 8.20280(10)
_cell_length_c 19.3507(3)
_cell_angle_alpha 90.00
_cell_angle_beta 106.8890(10)
_cell_angle_gamma 90.00
_cell_volume 1800.31(5)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 9989
_cell_measurement_theta_min 2.20
_cell_measurement_theta_max 27.43
_cell_measurement_temperature 296(2)
_exptl_crystal_description Plate
_exptl_crystal_colour black
_exptl_crystal_size_max 0.44
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.600
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 884
_exptl_absorpt_coefficient_mu 1.011
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS, Sheldrick, 1996)'
_exptl_absorpt_correction_T_min 0.778
_exptl_absorpt_correction_T_max 1.000
_exptl_special_details
;
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART CCD area-detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 24687
_diffrn_reflns_av_R_equivalents 0.0406
_diffrn_reflns_av_sigmaI/netI 0.0271
_diffrn_reflns_theta_min 2.20
_diffrn_reflns_theta_max 27.51
_diffrn_reflns_theta_full 27.51
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 25
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_refine_special_details
;
Refinement of F\^2\^ against ALL reflections. The weighted
R-factor wR and goodness of fit S are based on
F\^2\^, conventional R-factors R are based on F,
with F set to zero for negative F\^2\^. The threshold expression
of F\^2\^ > \s(F\^2\^) is used only for calculating
R-factors(gt) etc. and is not relevant to the choice of
reflections for refinement. R-factors based on F\^2\^ are
statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total 4142
_reflns_number_gt 3415
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0515
_refine_ls_R_factor_gt 0.0397
_refine_ls_wR_factor_gt 0.1192
_refine_ls_wR_factor_ref 0.1263
_refine_ls_goodness_of_fit_ref 1.005
_refine_ls_restrained_S_all 1.005
_refine_ls_number_reflns 4142
_refine_ls_number_parameters 253
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+2.4383P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean <0.001
_refine_diff_density_max 0.618
_refine_diff_density_min -0.433
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
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'
'Cl' 'Cl' 0.1484 0.1585
'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'
_computing_data_collection 'SMART (Bruker, 1997)'
_computing_cell_refinement 'SAINT (Bruker, 1997)'
_computing_data_reduction 'SAINT (Bruker, 1997)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
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 0.45008(3) 0.56516(5) 0.62759(2) 0.02844(13) Uani d . 1 . .
Cl Cl1 0.49959(7) 0.48979(10) 0.74759(4) 0.0423(2) Uani d . 1 . .
O O1 0.1136(2) 0.6292(4) 0.61432(18) 0.0676(8) Uani d . 1 . .
O O2 0.5587(2) 0.2335(3) 0.51016(14) 0.0529(6) Uani d . 1 . .
N N1 0.2870(2) 0.5301(3) 0.59827(14) 0.0352(5) Uani d . 1 . .
N N2 0.4003(2) 0.7937(3) 0.64688(12) 0.0321(5) Uani d . 1 . .
N N3 0.6194(2) 0.5763(3) 0.62630(12) 0.0298(5) Uani d . 1 . .
N N4 0.44925(19) 0.3762(3) 0.57162(12) 0.0305(5) Uani d . 1 . .
C C1 0.2181(3) 0.6411(4) 0.61888(17) 0.0399(7) Uani d . 1 . .
C C2 0.2867(3) 0.7921(4) 0.64770(16) 0.0373(6) Uani d . 1 . .
C C3 0.2337(3) 0.9212(4) 0.67153(19) 0.0509(9) Uani d . 1 . .
H H3A 0.1555 0.9156 0.6719 0.061 Uiso calc R 1 . .
C C4 0.3014(4) 1.0606(5) 0.6950(2) 0.0564(10) Uani d . 1 . .
H H4A 0.2696 1.1495 0.7127 0.068 Uiso calc R 1 . .
C C5 0.4145(4) 1.0649(4) 0.69173(18) 0.0483(8) Uani d . 1 . .
H H5A 0.4594 1.1585 0.7062 0.058 Uiso calc R 1 . .
C C6 0.4643(3) 0.9306(4) 0.66690(16) 0.0377(7) Uani d . 1 . .
C C7 0.5853(3) 0.9393(4) 0.65875(18) 0.0443(7) Uani d . 1 . .
H H7A 0.6159 1.0483 0.6716 0.053 Uiso calc R 1 . .
H H7B 0.5800 0.9222 0.6083 0.053 Uiso calc R 1 . .
C C8 0.6751(3) 0.8146(4) 0.70492(17) 0.0418(7) Uani d . 1 . .
H H8A 0.7468 0.8722 0.7301 0.050 Uiso calc R 1 . .
H H8B 0.6425 0.7683 0.7411 0.050 Uiso calc R 1 . .
C C9 0.7061(2) 0.6787(4) 0.66208(15) 0.0352(6) Uani d . 1 . .
C C10 0.8207(3) 0.6559(4) 0.65877(18) 0.0453(8) Uani d . 1 . .
H H10A 0.8794 0.7287 0.6824 0.054 Uiso calc R 1 . .
C C11 0.8485(3) 0.5277(5) 0.62112(19) 0.0479(8) Uani d . 1 . .
H H11A 0.9255 0.5124 0.6195 0.057 Uiso calc R 1 . .
C C12 0.7599(3) 0.4217(4) 0.58564(17) 0.0413(7) Uani d . 1 . .
H H12A 0.7760 0.3331 0.5600 0.050 Uiso calc R 1 . .
C C13 0.6471(2) 0.4504(3) 0.58911(15) 0.0314(6) Uani d . 1 . .
C C14 0.5471(2) 0.3397(4) 0.55255(15) 0.0333(6) Uani d . 1 . .
C C15 0.2484(2) 0.3809(4) 0.56301(16) 0.0348(6) Uani d . 1 . .
C C16 0.1338(3) 0.3196(4) 0.5414(2) 0.0499(8) Uani d . 1 . .
H H16A 0.0724 0.3773 0.5509 0.060 Uiso calc R 1 . .
C C17 0.1128(3) 0.1721(5) 0.5056(2) 0.0590(10) Uani d . 1 . .
H H17A 0.0364 0.1311 0.4905 0.071 Uiso calc R 1 . .
C C18 0.2030(3) 0.0846(4) 0.4919(2) 0.0547(9) Uani d . 1 . .
H H18A 0.1870 -0.0153 0.4683 0.066 Uiso calc R 1 . .
C C19 0.3178(3) 0.1438(4) 0.51280(16) 0.0414(7) Uani d . 1 . .
H H19A 0.3789 0.0840 0.5041 0.050 Uiso calc R 1 . .
C C20 0.3393(2) 0.2947(3) 0.54712(15) 0.0328(6) Uani d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Fe1 0.0262(2) 0.0225(2) 0.0375(2) -0.00026(14) 0.01073(15) -0.00375(15)
Cl1 0.0483(4) 0.0381(4) 0.0427(4) 0.0044(3) 0.0169(3) 0.0083(3)
O1 0.0352(13) 0.0650(18) 0.109(2) 0.0042(12) 0.0307(14) -0.0117(17)
O2 0.0472(13) 0.0475(14) 0.0671(15) 0.0005(11) 0.0215(11) -0.0268(12)
N1 0.0278(11) 0.0299(13) 0.0484(14) 0.0000(9) 0.0119(10) -0.0014(10)
N2 0.0410(13) 0.0221(11) 0.0345(12) 0.0034(10) 0.0132(10) -0.0013(9)
N3 0.0287(11) 0.0274(12) 0.0334(11) -0.0026(9) 0.0091(9) -0.0020(9)
N4 0.0301(11) 0.0237(11) 0.0370(12) -0.0025(9) 0.0088(9) -0.0049(9)
C1 0.0337(15) 0.0377(17) 0.0515(17) 0.0065(12) 0.0175(13) 0.0020(14)
C2 0.0424(16) 0.0333(15) 0.0396(15) 0.0099(12) 0.0173(12) 0.0021(12)
C3 0.058(2) 0.047(2) 0.055(2) 0.0213(17) 0.0282(17) 0.0042(16)
C4 0.083(3) 0.0406(19) 0.0494(19) 0.0225(19) 0.0254(18) -0.0016(15)
C5 0.076(2) 0.0272(15) 0.0401(16) 0.0053(15) 0.0136(16) -0.0027(13)
C6 0.0547(18) 0.0249(14) 0.0325(14) 0.0017(13) 0.0108(12) 0.0010(11)
C7 0.0553(19) 0.0264(15) 0.0517(18) -0.0103(13) 0.0166(15) -0.0024(13)
C8 0.0421(16) 0.0388(17) 0.0411(16) -0.0095(13) 0.0069(13) -0.0082(13)
C9 0.0322(14) 0.0346(15) 0.0365(14) -0.0063(12) 0.0066(11) -0.0002(12)
C10 0.0314(15) 0.051(2) 0.0500(18) -0.0110(14) 0.0058(13) 0.0020(15)
C11 0.0270(14) 0.063(2) 0.0540(19) 0.0007(14) 0.0126(13) 0.0059(17)
C12 0.0330(15) 0.0472(19) 0.0462(17) 0.0054(13) 0.0154(13) 0.0001(14)
C13 0.0311(13) 0.0311(14) 0.0321(13) 0.0019(11) 0.0092(10) 0.0020(11)
C14 0.0339(14) 0.0296(14) 0.0360(14) 0.0024(11) 0.0094(11) -0.0030(11)
C15 0.0318(14) 0.0287(14) 0.0423(15) -0.0045(11) 0.0084(11) 0.0036(12)
C16 0.0325(16) 0.0450(19) 0.070(2) -0.0058(14) 0.0115(15) 0.0041(17)
C17 0.0431(19) 0.047(2) 0.079(3) -0.0221(16) 0.0051(17) 0.0039(19)
C18 0.063(2) 0.0346(18) 0.059(2) -0.0211(16) 0.0073(17) -0.0051(15)
C19 0.0493(18) 0.0317(16) 0.0420(16) -0.0082(13) 0.0114(13) -0.0036(13)
C20 0.0326(14) 0.0281(14) 0.0360(14) -0.0047(11) 0.0073(11) 0.0012(11)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 N1 . 1.871(2) yes
Fe1 N4 . 1.889(2) yes
Fe1 N3 . 2.016(2) yes
Fe1 N2 . 2.032(2) yes
Fe1 Cl1 . 2.3080(8) yes
O1 C1 . 1.220(4) ?
O2 C14 . 1.231(3) ?
N1 C1 . 1.358(4) ?
N1 C15 . 1.412(4) ?
N2 C6 . 1.348(4) ?
N2 C2 . 1.350(4) ?
N3 C9 . 1.352(4) ?
N3 C13 . 1.353(4) ?
N4 C14 . 1.349(4) ?
N4 C20 . 1.418(3) ?
C1 C2 . 1.498(5) ?
C2 C3 . 1.378(4) ?
C3 C4 . 1.395(6) ?
C3 H3A . 0.93 ?
C4 C5 . 1.361(6) ?
C4 H4A . 0.93 ?
C5 C6 . 1.399(4) ?
C5 H5A . 0.93 ?
C6 C7 . 1.490(5) ?
C7 C8 . 1.557(5) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 C9 . 1.497(4) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 C10 . 1.392(4) ?
C10 C11 . 1.373(5) ?
C10 H10A . 0.93 ?
C11 C12 . 1.383(5) ?
C11 H11A . 0.93 ?
C12 C13 . 1.378(4) ?
C12 H12A . 0.93 ?
C13 C14 . 1.498(4) ?
C15 C16 . 1.394(4) ?
C15 C20 . 1.396(4) ?
C16 C17 . 1.380(5) ?
C16 H16A . 0.93 ?
C17 C18 . 1.376(6) ?
C17 H17A . 0.93 ?
C18 C19 . 1.390(5) ?
C18 H18A . 0.93 ?
C19 C20 . 1.392(4) ?
C19 H19A . 0.93 ?
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
N1 Fe1 N4 . . 82.38(10) ?
N1 Fe1 N3 . . 161.28(10) ?
N4 Fe1 N3 . . 82.51(9) ?
N1 Fe1 N2 . . 82.39(10) ?
N4 Fe1 N2 . . 155.32(10) ?
N3 Fe1 N2 . . 107.69(10) ?
N1 Fe1 Cl1 . . 101.67(8) ?
N4 Fe1 Cl1 . . 108.32(8) ?
N3 Fe1 Cl1 . . 93.53(7) ?
N2 Fe1 Cl1 . . 93.71(7) ?
C1 N1 C15 . . 125.8(3) ?
C1 N1 Fe1 . . 117.7(2) ?
C15 N1 Fe1 . . 116.19(19) ?
C6 N2 C2 . . 119.0(3) ?
C6 N2 Fe1 . . 130.7(2) ?
C2 N2 Fe1 . . 109.69(19) ?
C9 N3 C13 . . 118.7(2) ?
C9 N3 Fe1 . . 129.3(2) ?
C13 N3 Fe1 . . 111.65(18) ?
C14 N4 C20 . . 125.7(2) ?
C14 N4 Fe1 . . 118.49(18) ?
C20 N4 Fe1 . . 115.45(18) ?
O1 C1 N1 . . 127.6(3) ?
O1 C1 C2 . . 121.5(3) ?
N1 C1 C2 . . 110.8(2) ?
N2 C2 C3 . . 123.4(3) ?
N2 C2 C1 . . 116.0(2) ?
C3 C2 C1 . . 120.6(3) ?
C2 C3 C4 . . 117.6(3) ?
C2 C3 H3A . . 121.2 ?
C4 C3 H3A . . 121.2 ?
C5 C4 C3 . . 119.1(3) ?
C5 C4 H4A . . 120.4 ?
C3 C4 H4A . . 120.4 ?
C4 C5 C6 . . 121.0(3) ?
C4 C5 H5A . . 119.5 ?
C6 C5 H5A . . 119.5 ?
N2 C6 C5 . . 119.8(3) ?
N2 C6 C7 . . 119.2(3) ?
C5 C6 C7 . . 120.9(3) ?
C6 C7 C8 . . 115.3(3) ?
C6 C7 H7A . . 108.5 ?
C8 C7 H7A . . 108.5 ?
C6 C7 H7B . . 108.5 ?
C8 C7 H7B . . 108.5 ?
H7A C7 H7B . . 107.5 ?
C9 C8 C7 . . 114.1(3) ?
C9 C8 H8A . . 108.7 ?
C7 C8 H8A . . 108.7 ?
C9 C8 H8B . . 108.7 ?
C7 C8 H8B . . 108.7 ?
H8A C8 H8B . . 107.6 ?
N3 C9 C10 . . 120.1(3) ?
N3 C9 C8 . . 118.3(3) ?
C10 C9 C8 . . 121.7(3) ?
C11 C10 C9 . . 121.0(3) ?
C11 C10 H10A . . 119.5 ?
C9 C10 H10A . . 119.5 ?
C10 C11 C12 . . 118.7(3) ?
C10 C11 H11A . . 120.6 ?
C12 C11 H11A . . 120.6 ?
C13 C12 C11 . . 118.4(3) ?
C13 C12 H12A . . 120.8 ?
C11 C12 H12A . . 120.8 ?
N3 C13 C12 . . 123.1(3) ?
N3 C13 C14 . . 115.6(2) ?
C12 C13 C14 . . 121.3(3) ?
O2 C14 N4 . . 127.6(3) ?
O2 C14 C13 . . 121.2(3) ?
N4 C14 C13 . . 111.2(2) ?
C16 C15 C20 . . 119.9(3) ?
C16 C15 N1 . . 127.5(3) ?
C20 C15 N1 . . 112.5(2) ?
C17 C16 C15 . . 119.0(3) ?
C17 C16 H16A . . 120.5 ?
C15 C16 H16A . . 120.5 ?
C18 C17 C16 . . 121.1(3) ?
C18 C17 H17A . . 119.4 ?
C16 C17 H17A . . 119.4 ?
C17 C18 C19 . . 120.8(3) ?
C17 C18 H18A . . 119.6 ?
C19 C18 H18A . . 119.6 ?
C18 C19 C20 . . 118.5(3) ?
C18 C19 H19A . . 120.7 ?
C20 C19 H19A . . 120.7 ?
C19 C20 C15 . . 120.6(3) ?
C19 C20 N4 . . 127.0(3) ?
C15 C20 N4 . . 112.4(2) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N4 Fe1 N1 C1 . . . . -176.9(2) ?
N3 Fe1 N1 C1 . . . . -140.5(3) ?
N2 Fe1 N1 C1 . . . . -16.3(2) ?
Cl1 Fe1 N1 C1 . . . . 75.9(2) ?
N4 Fe1 N1 C15 . . . . 9.6(2) ?
N3 Fe1 N1 C15 . . . . 46.0(4) ?
N2 Fe1 N1 C15 . . . . 170.1(2) ?
Cl1 Fe1 N1 C15 . . . . -97.6(2) ?
N1 Fe1 N2 C6 . . . . -173.7(3) ?
N4 Fe1 N2 C6 . . . . -121.4(3) ?
N3 Fe1 N2 C6 . . . . -9.9(3) ?
Cl1 Fe1 N2 C6 . . . . 85.0(2) ?
N1 Fe1 N2 C2 . . . . 15.76(19) ?
N4 Fe1 N2 C2 . . . . 68.1(3) ?
N3 Fe1 N2 C2 . . . . 179.57(18) ?
Cl1 Fe1 N2 C2 . . . . -85.53(19) ?
N1 Fe1 N3 C9 . . . . 150.2(3) ?
N4 Fe1 N3 C9 . . . . -173.5(3) ?
N2 Fe1 N3 C9 . . . . 29.6(3) ?
Cl1 Fe1 N3 C9 . . . . -65.4(2) ?
N1 Fe1 N3 C13 . . . . -37.0(4) ?
N4 Fe1 N3 C13 . . . . -0.60(19) ?
N2 Fe1 N3 C13 . . . . -157.53(18) ?
Cl1 Fe1 N3 C13 . . . . 107.44(18) ?
N1 Fe1 N4 C14 . . . . 164.8(2) ?
N3 Fe1 N4 C14 . . . . -4.1(2) ?
N2 Fe1 N4 C14 . . . . 112.5(3) ?
Cl1 Fe1 N4 C14 . . . . -95.4(2) ?
N1 Fe1 N4 C20 . . . . -8.8(2) ?
N3 Fe1 N4 C20 . . . . -177.7(2) ?
N2 Fe1 N4 C20 . . . . -61.1(3) ?
Cl1 Fe1 N4 C20 . . . . 91.03(19) ?
C15 N1 C1 O1 . . . . 4.1(6) ?
Fe1 N1 C1 O1 . . . . -168.8(3) ?
C15 N1 C1 C2 . . . . -174.1(3) ?
Fe1 N1 C1 C2 . . . . 13.1(3) ?
C6 N2 C2 C3 . . . . -3.4(4) ?
Fe1 N2 C2 C3 . . . . 168.4(3) ?
C6 N2 C2 C1 . . . . 175.0(3) ?
Fe1 N2 C2 C1 . . . . -13.2(3) ?
O1 C1 C2 N2 . . . . -176.9(3) ?
N1 C1 C2 N2 . . . . 1.3(4) ?
O1 C1 C2 C3 . . . . 1.5(5) ?
N1 C1 C2 C3 . . . . 179.8(3) ?
N2 C2 C3 C4 . . . . 0.8(5) ?
C1 C2 C3 C4 . . . . -177.5(3) ?
C2 C3 C4 C5 . . . . 1.6(5) ?
C3 C4 C5 C6 . . . . -1.5(5) ?
C2 N2 C6 C5 . . . . 3.4(4) ?
Fe1 N2 C6 C5 . . . . -166.4(2) ?
C2 N2 C6 C7 . . . . -173.6(3) ?
Fe1 N2 C6 C7 . . . . 16.6(4) ?
C4 C5 C6 N2 . . . . -1.0(5) ?
C4 C5 C6 C7 . . . . 175.9(3) ?
N2 C6 C7 C8 . . . . -63.1(4) ?
C5 C6 C7 C8 . . . . 119.9(3) ?
C6 C7 C8 C9 . . . . 107.4(3) ?
C13 N3 C9 C10 . . . . 1.6(4) ?
Fe1 N3 C9 C10 . . . . 174.0(2) ?
C13 N3 C9 C8 . . . . -178.2(3) ?
Fe1 N3 C9 C8 . . . . -5.7(4) ?
C7 C8 C9 N3 . . . . -62.5(4) ?
C7 C8 C9 C10 . . . . 117.7(3) ?
N3 C9 C10 C11 . . . . -1.8(5) ?
C8 C9 C10 C11 . . . . 177.9(3) ?
C9 C10 C11 C12 . . . . 0.7(5) ?
C10 C11 C12 C13 . . . . 0.6(5) ?
C9 N3 C13 C12 . . . . -0.3(4) ?
Fe1 N3 C13 C12 . . . . -174.0(2) ?
C9 N3 C13 C14 . . . . 178.4(2) ?
Fe1 N3 C13 C14 . . . . 4.7(3) ?
C11 C12 C13 N3 . . . . -0.8(5) ?
C11 C12 C13 C14 . . . . -179.4(3) ?
C20 N4 C14 O2 . . . . 1.6(5) ?
Fe1 N4 C14 O2 . . . . -171.3(3) ?
C20 N4 C14 C13 . . . . -179.7(2) ?
Fe1 N4 C14 C13 . . . . 7.5(3) ?
N3 C13 C14 O2 . . . . 171.0(3) ?
C12 C13 C14 O2 . . . . -10.3(4) ?
N3 C13 C14 N4 . . . . -7.8(4) ?
C12 C13 C14 N4 . . . . 170.9(3) ?
C1 N1 C15 C16 . . . . 1.3(5) ?
Fe1 N1 C15 C16 . . . . 174.3(3) ?
C1 N1 C15 C20 . . . . 178.5(3) ?
Fe1 N1 C15 C20 . . . . -8.6(3) ?
C20 C15 C16 C17 . . . . 1.3(5) ?
N1 C15 C16 C17 . . . . 178.3(3) ?
C15 C16 C17 C18 . . . . 0.7(6) ?
C16 C17 C18 C19 . . . . -1.0(6) ?
C17 C18 C19 C20 . . . . -0.8(5) ?
C18 C19 C20 C15 . . . . 2.8(5) ?
C18 C19 C20 N4 . . . . -179.2(3) ?
C16 C15 C20 C19 . . . . -3.1(5) ?
N1 C15 C20 C19 . . . . 179.5(3) ?
C16 C15 C20 N4 . . . . 178.7(3) ?
N1 C15 C20 N4 . . . . 1.3(4) ?
C14 N4 C20 C19 . . . . 15.3(5) ?
Fe1 N4 C20 C19 . . . . -171.7(2) ?
C14 N4 C20 C15 . . . . -166.7(3) ?
Fe1 N4 C20 C15 . . . . 6.4(3) ?
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
C3 H3A Cl1 2_556 0.93 2.80 3.595(4) 144
C10 H10A Cl1 2_656 0.93 2.71 3.617(3) 165
C11 H11A O1 1_655 0.93 2.46 3.290(5) 149
data_global
_journal_date_recd_electronic 2008-11-22
_journal_date_accepted 2008-12-07
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2009
_journal_volume 65
_journal_issue 1
_journal_page_first m44
_journal_page_last m44
_journal_paper_category QM
_journal_coeditor_code CI2736
_publ_contact_author_name 'Li Yang'
_publ_contact_author_address
;
Department of Chemical Engineering
Yibin University
Yibin 64000
People's Republic of China
;
_publ_contact_author_email 'ybuyl@163.com'
_publ_contact_author_fax '86-831-6180016'
_publ_contact_author_phone '86-831-6180016'
_publ_section_title
;\
Chlorido{N,N'-o-phenylene-[6,6'-ethylenebis(pyridine-2-\
carboxamide)]}iron(III)
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Yang, Li' .
;
Department of Chemical Engineering
Yibin University
Yibin 644000
People's Republic of China
;
'Tang, Bin' .
;
Department of Chemistry
Luzhou Medicial College
Luzhou 646000
People's Republic of China
;