#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/69/2236920.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_2236920
loop_
_publ_author_name
'Tomyn, Stefania'
'Haukka, Matti'
'Nedelkov, Ruslan'
_publ_section_title
;
 Diammine{N-[2-(hydroxyimino)propionyl]-N'-[2-(oxidoimino)propionyl]propane-1,3-diaminido-κ⁴N,N',N'',N'''}iron(III)
;
_journal_coeditor_code           HY2607
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1568
_journal_page_last               m1569
_journal_paper_doi               10.1107/S160053681204826X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Fe (C9 H13 N4 O4) (N H3)2]'
_chemical_formula_moiety         'C9 H19 Fe N6 O4'
_chemical_formula_sum            'C9 H19 Fe N6 O4'
_chemical_formula_weight         331.15
_chemical_name_systematic
;
Diammine{N-[2-(hydroxyimino)propionyl]-N'-[2-
(oxidoimino)propionyl]propane-1,3-diaminido-
κ⁴N,N',N'',N'''}iron(III)
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 108.994(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9111(3)
_cell_length_b                   7.2255(3)
_cell_length_c                   10.6194(4)
_cell_measurement_reflns_used    2700
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     646.52(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;XP in SHELXTL (Sheldrick, 2008) and
Mercury (Macrae et al., 2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans with κ offset'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12359
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    1.192
_exptl_absorpt_correction_T_max  0.9536
_exptl_absorpt_correction_T_min  0.7953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             346.0
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.461
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0299
_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)+(0.0280P)²+0.7141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                1361
_reflns_number_total             1599
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2607.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2236920
_cod_database_fobs_code          2236920
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe1 0.84000(4) 0.7500 0.68148(4) 0.01316(12) Uani d S 1 2 . .
O O1 1.1762(2) 0.7500 0.72129(19) 0.0199(4) Uani d S 1 2 . .
H H1O 1.1180 0.7500 0.6258 0.030 Uiso d SR 1 2 . .
O O2 0.9831(2) 0.7500 1.07989(18) 0.0220(4) Uani d S 1 2 . .
O O3 0.4412(2) 0.7500 0.36943(19) 0.0196(4) Uani d S 1 2 . .
O O4 0.9952(2) 0.7500 0.48443(18) 0.0162(4) Uani d S 1 2 . .
N N5 0.85135(18) 1.0255(2) 0.67972(15) 0.0151(3) Uani d . 1 1 . .
H H5D 0.9063 1.0618 0.6252 0.023 Uiso calc R 1 1 . .
H H5E 0.9016 1.0674 0.7637 0.023 Uiso calc R 1 1 . .
H H5F 0.7514 1.0730 0.6494 0.023 Uiso calc R 1 1 . .
N N1 1.0616(3) 0.7500 0.7808(2) 0.0148(4) Uani d S 1 2 . .
N N2 0.8273(3) 0.7500 0.8580(2) 0.0149(4) Uani d S 1 2 . .
N N3 0.6183(3) 0.7500 0.5839(2) 0.0146(4) Uani d S 1 2 . .
N N4 0.8536(2) 0.7500 0.5050(2) 0.0135(4) Uani d S 1 2 . .
C C1 1.1043(3) 0.7500 0.9092(3) 0.0166(5) Uani d S 1 2 . .
C C2 1.2708(3) 0.7500 0.9983(3) 0.0243(6) Uani d S 1 2 A .
H H2A 1.2741 0.7215 1.0894 0.036 Uiso calc PR 0.50 1 . .
H H2B 1.3177 0.8722 0.9964 0.036 Uiso calc PR 0.50 1 . .
H H2C 1.3310 0.6563 0.9681 0.036 Uiso calc PR 0.50 1 . .
C C3 0.9631(3) 0.7500 0.9576(3) 0.0162(5) Uani d S 1 2 A .
C C4 0.6775(3) 0.7500 0.8870(3) 0.0191(6) Uani d S 1 2 A 1
H H4A 0.6940 0.8119 0.9736 0.023 Uiso calc PR 0.50 1 A 1
H H4B 0.6456 0.6205 0.8952 0.023 Uiso calc PR 0.50 1 A 1
C C5 0.5460(4) 0.8461(6) 0.7819(4) 0.0181(8) Uani d P 0.50 1 A 1
H H5A 0.5811 0.9733 0.7708 0.022 Uiso calc PR 0.50 1 A 1
H H5B 0.4534 0.8564 0.8136 0.022 Uiso calc PR 0.50 1 A 1
C C6 0.4926(3) 0.7500 0.6449(3) 0.0187(6) Uani d S 1 2 A 1
H H6A 0.4618 0.6207 0.6555 0.022 Uiso calc PR 0.50 1 A 1
H H6B 0.3981 0.8145 0.5852 0.022 Uiso calc PR 0.50 1 A 1
C C7 0.5789(3) 0.7500 0.4522(3) 0.0152(5) Uani d S 1 2 A .
C C8 0.7221(3) 0.7500 0.4066(3) 0.0152(5) Uani d S 1 2 A .
C C9 0.7113(3) 0.7500 0.2641(3) 0.0229(6) Uani d S 1 2 . .
H H9A 0.7349 0.8742 0.2386 0.034 Uiso calc PR 0.50 1 A .
H H9B 0.6038 0.7142 0.2092 0.034 Uiso calc PR 0.50 1 . .
H H9C 0.7880 0.6616 0.2505 0.034 Uiso calc PR 0.50 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'
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
N3 Fe1 N1 . . 179.44(10)
N3 Fe1 N2 . . 98.66(9)
N1 Fe1 N2 . . 80.78(9)
N3 Fe1 N4 . . 81.55(9)
N1 Fe1 N4 . . 99.01(9)
N2 Fe1 N4 . . 179.79(9)
N3 Fe1 N5 . . 92.39(4)
N1 Fe1 N5 . . 87.63(5)
N2 Fe1 N5 . . 91.64(5)
N4 Fe1 N5 . . 88.35(5)
N3 Fe1 N5 . 4_575 92.39(5)
N1 Fe1 N5 . 4_575 87.63(4)
N2 Fe1 N5 . 4_575 91.64(5)
N4 Fe1 N5 . 4_575 88.35(5)
N5 Fe1 N5 . 4_575 173.75(9)
N1 O1 H1O . . 104.8
Fe1 N5 H5D . . 109.5
Fe1 N5 H5E . . 109.5
H5D N5 H5E . . 109.5
Fe1 N5 H5F . . 109.5
H5D N5 H5F . . 109.5
H5E N5 H5F . . 109.5
C1 N1 O1 . . 118.8(2)
C1 N1 Fe1 . . 118.60(18)
O1 N1 Fe1 . . 122.60(16)
C3 N2 C4 . . 119.4(2)
C3 N2 Fe1 . . 116.91(18)
C4 N2 Fe1 . . 123.68(17)
C7 N3 C6 . . 119.2(2)
C7 N3 Fe1 . . 116.37(17)
C6 N3 Fe1 . . 124.43(17)
C8 N4 O4 . 4_575 121.3(2)
C8 N4 O4 . . 121.3(2)
C8 N4 Fe1 . . 117.49(18)
O4 N4 Fe1 4_575 . 121.24(16)
O4 N4 Fe1 . . 121.24(16)
N1 C1 C2 . . 124.4(3)
N1 C1 C3 . . 111.7(2)
C2 C1 C3 . . 123.9(2)
C1 C2 H2A . . 109.5
C1 C2 H2B . . 109.5
H2A C2 H2B . . 109.5
C1 C2 H2C . . 109.5
H2A C2 H2C . . 109.5
H2B C2 H2C . . 109.5
O2 C3 N2 . . 127.8(3)
O2 C3 C1 . . 120.1(2)
N2 C3 C1 . . 112.0(2)
N2 C4 C5 . . 112.9(2)
N2 C4 H4A . . 109.0
C5 C4 H4A . . 109.0
N2 C4 H4B . . 109.0
C5 C4 H4B . . 109.0
H4A C4 H4B . . 107.8
C4 C5 C6 . . 114.8(3)
C4 C5 H5A . . 108.6
C6 C5 H5A . . 108.6
C4 C5 H5B . . 108.6
C6 C5 H5B . . 108.6
H5A C5 H5B . . 107.5
N3 C6 C5 . . 111.8(2)
N3 C6 H6A . . 109.3
C5 C6 H6A . . 109.3
N3 C6 H6B . . 109.3
C5 C6 H6B . . 109.3
H6A C6 H6B . . 107.9
O3 C7 N3 . . 127.0(2)
O3 C7 C8 . . 120.8(2)
N3 C7 C8 . . 112.2(2)
N4 C8 C9 . . 124.4(2)
N4 C8 C7 . . 112.4(2)
C9 C8 C7 . . 123.2(2)
C8 C9 H9A . . 109.5
C8 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C8 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Fe1 N3 . 1.909(2)
Fe1 N1 . 1.912(2)
Fe1 N2 . 1.914(2)
Fe1 N4 . 1.917(2)
Fe1 N5 . 1.9932(16)
O1 N1 . 1.364(3)
O1 H1O . 0.9769
O2 C3 . 1.252(3)
O3 C7 . 1.255(3)
O4 O4 4_575 0.000(4)
O4 N4 . 1.349(3)
N5 H5D . 0.9100
N5 H5E . 0.9100
N5 H5F . 0.9100
N1 C1 . 1.291(3)
N2 C3 . 1.323(3)
N2 C4 . 1.464(3)
N3 C7 . 1.327(3)
N3 C6 . 1.465(3)
N4 C8 . 1.292(3)
N4 O4 4_575 1.349(3)
C1 C2 . 1.478(4)
C1 C3 . 1.506(4)
C2 H2A . 0.9800
C2 H2B . 0.9800
C2 H2C . 0.9800
C4 C5 . 1.500(4)
C4 H4A . 0.9900
C4 H4B . 0.9900
C5 C6 . 1.541(4)
C5 H5A . 0.9900
C5 H5B . 0.9900
C6 H6A . 0.9900
C6 H6B . 0.9900
C7 C8 . 1.505(4)
C8 C9 . 1.485(4)
C9 H9A . 0.9800
C9 H9B . 0.9800
C9 H9C . 0.9800
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
O1 H1O O4 . 0.98 1.54 2.508(3) 168
N5 H5D O4 2_756 0.91 2.15 3.015(2) 158
N5 H5E O2 2_757 0.91 2.11 2.979(2) 160
N5 H5F O3 2_656 0.91 2.10 2.969(2) 160
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_4
_geom_torsion
N5 Fe1 N1 C1 . . 92.04(4)
N5 Fe1 N1 C1 4_575 . -92.04(4)
N5 Fe1 N1 O1 . . -87.96(4)
N5 Fe1 N1 O1 4_575 . 87.96(4)
N5 Fe1 N2 C3 . . -87.34(4)
N5 Fe1 N2 C3 4_575 . 87.34(4)
N5 Fe1 N2 C4 . . 92.66(4)
N5 Fe1 N2 C4 4_575 . -92.66(4)
N5 Fe1 N3 C7 . . 87.98(5)
N5 Fe1 N3 C7 4_575 . -87.98(5)
N5 Fe1 N3 C6 . . -92.02(5)
N5 Fe1 N3 C6 4_575 . 92.02(5)
N5 Fe1 N4 C8 . . -92.66(4)
N5 Fe1 N4 C8 4_575 . 92.66(4)
N5 Fe1 N4 O4 . 4_575 87.34(4)
N5 Fe1 N4 O4 4_575 4_575 -87.34(4)
N5 Fe1 N4 O4 . . 87.34(4)
N5 Fe1 N4 O4 4_575 . -87.34(4)
C3 N2 C4 C5 . . 149.83(18)
Fe1 N2 C4 C5 . . -30.17(18)
N2 C4 C5 C6 . . 66.1(3)
C7 N3 C6 C5 . . -150.96(17)
Fe1 N3 C6 C5 . . 29.04(17)
C4 C5 C6 N3 . . -65.3(3)
