#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/05/2010517.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_2010517
loop_
_publ_author_name
'Dickman, Michael H.'
_publ_section_title
;Bis(1,2-diaminobenzene-N)bis(1,1,1,5,5,5-hexafluoropentane-2,4-dionato-O,O')iron(II),
 -cobalt(II) and -nickel(II) at low temperature
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              58
_journal_page_last               60
_journal_paper_doi               10.1107/S0108270199013487
_journal_volume                  56
_journal_year                    2000
_chemical_formula_iupac          '[Fe (C5 H F6 O2)2 (C6 H8 N2)2]'
_chemical_formula_sum            'C22 H18 F12 Fe N4 O4'
_chemical_formula_weight         686.25
_chemical_name_systematic
;
trans-bis(1,2-Diaminobenzene-N)bis(1,1,1,5,5,5-
  hexafluoropentane-2,4-dionato-O,O')iron(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           'edit of SHELXL-97'
_cell_angle_alpha                90.00
_cell_angle_beta                 99.0020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.81480(10)
_cell_length_b                   10.9332(2)
_cell_length_c                   15.4893(3)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.29
_cell_volume                     1307.12(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SMART
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full .966
_diffrn_measured_fraction_theta_max .966
_diffrn_measurement_device_type  'Bruker SMART area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .022
_diffrn_reflns_av_sigmaI/netI    .0179
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13875
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    .701
_exptl_absorpt_correction_T_max  .735
_exptl_absorpt_correction_T_min  .620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .37
_exptl_crystal_size_min          .16
_refine_diff_density_max         1.06
_refine_diff_density_min         -.80
_refine_ls_extinction_coef       .0150(16)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          .045
_refine_ls_R_factor_gt           .040
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0555P)²+1.4920P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .107
_reflns_number_gt                2818
_reflns_number_total             3129
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            da1091.cif
_cod_data_source_block           (I)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2010517
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'
loop_
_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
_atom_site_type_symbol
Fe1 .0000 .0000 .0000 .02108(14) Uani d S 1 . . Fe
O1 .06852(18) .04011(13) .13074(8) .0249(3) Uani d . 1 . . O
O2 .11676(19) .16135(13) -.02403(8) .0245(3) Uani d . 1 . . O
N1 .2516(2) -.10817(16) .00874(11) .0242(3) Uani d . 1 . . N
N2 .3923(2) .02931(17) -.11703(12) .0272(4) Uani d . 1 . . N
C1 .2929(2) -.16728(18) -.06870(12) .0231(4) Uani d . 1 . . C
C2 .3557(2) -.09625(18) -.13270(12) .0234(4) Uani d . 1 . . C
C3 .3902(3) -.1534(2) -.20878(13) .0296(4) Uani d . 1 . . C
C4 .3647(3) -.2782(2) -.22122(16) .0367(5) Uani d . 1 . . C
C5 .3024(3) -.3477(2) -.15869(17) .0379(5) Uani d . 1 . . C
C6 .2662(3) -.2919(2) -.08231(15) .0309(4) Uani d . 1 . . C
C7 .1583(3) .1376(2) .26449(13) .0350(5) Uani d . 1 . . C
C8 .1351(2) .13691(18) .16382(12) .0229(4) Uani d . 1 . . C
C9 .1894(3) .23942(18) .12125(12) .0241(4) Uani d . 1 . . C
C10 .1760(2) .24310(17) .03073(12) .0214(4) Uani d . 1 . . C
C11 .2351(3) .35817(19) -.01294(13) .0289(4) Uani d . 1 . . C
F1 .2707(2) .0490(2) .29646(10) .0627(5) Uani d . 1 . . F
F2 .0142(2) .1112(2) .29299(10) .0646(6) Uani d . 1 . . F
F3 .2281(4) .23925(19) .30001(10) .0853(8) Uani d . 1 . . F
F4 .3088(2) .44170(13) .04305(9) .0444(4) Uani d . 1 . . F
F5 .0991(2) .41101(14) -.06257(10) .0488(4) Uani d . 1 . . F
F6 .3479(2) .32971(14) -.06576(10) .0479(4) Uani d . 1 . . F
H1N1 .344(4) -.067(3) .0322(17) .033(7) Uiso d . 1 . . H
H2N1 .234(3) -.167(2) .0447(17) .028(6) Uiso d . 1 . . H
H1N2 .403(4) .068(3) -.1672(19) .037(7) Uiso d . 1 . . H
H2N2 .319(3) .066(2) -.0894(18) .032(7) Uiso d . 1 . . H
H3 .433(3) -.104(2) -.2505(18) .034(7) Uiso d . 1 . . H
H4 .388(4) -.318(3) -.270(2) .053(9) Uiso d . 1 . . H
H5 .285(4) -.433(3) -.169(2) .052(9) Uiso d . 1 . . H
H6 .224(4) -.341(3) -.0370(19) .041(7) Uiso d . 1 . . H
H9 .241(3) .306(2) .1549(17) .032(6) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe .3463 .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
_geom_angle_publ_flag
O2 Fe1 O2 . 3 180.0 no
O2 Fe1 O1 . 3 93.41(5) no
O2 Fe1 O1 3 3 86.59(5) no
O2 Fe1 O1 . . 86.59(5) yes
O2 Fe1 O1 3 . 93.41(5) yes
O1 Fe1 O1 3 . 180.0 no
O2 Fe1 N1 . . 93.04(6) yes
O2 Fe1 N1 3 . 86.96(6) yes
O1 Fe1 N1 3 . 92.12(6) yes
O1 Fe1 N1 . . 87.88(6) yes
O2 Fe1 N1 . 3 86.96(6) no
O2 Fe1 N1 3 3 93.04(6) no
O1 Fe1 N1 3 3 87.88(6) no
O1 Fe1 N1 . 3 92.12(6) no
N1 Fe1 N1 . 3 180.0 no
C8 O1 Fe1 . . 127.55(12) no
C10 O2 Fe1 . . 127.74(12) no
C10 O2 H2N2 . . 114.7(7) no
Fe1 O2 H2N2 . . 92.6(7) no
C10 O2 N2 . . 115.34(12) no
Fe1 O2 N2 . . 92.55(6) no
H2N2 O2 N2 . . .9(7) no
C1 N1 Fe1 . . 119.06(12) yes
C1 N1 N2 . 3_655 105.82(12) no
Fe1 N1 N2 . 3_655 125.02(8) no
C1 N1 H1N1 . . 107.4(17) no
Fe1 N1 H1N1 . . 113.5(18) no
N2 N1 H1N1 3_655 . 15.8(18) no
C1 N1 H2N1 . . 106.2(17) no
Fe1 N1 H2N1 . . 101.5(17) no
N2 N1 H2N1 3_655 . 94.3(17) no
H1N1 N1 H2N1 . . 108(2) no
C2 N2 O2 . . 113.09(12) no
C2 N2 H1N2 . . 110.4(18) no
O2 N2 H1N2 . . 110.3(18) no
C2 N2 H2N2 . . 113.6(18) no
O2 N2 H2N2 . . 2.3(18) no
H1N2 N2 H2N2 . . 112(3) no
C6 C1 C2 . . 119.66(19) no
C6 C1 N1 . . 121.19(18) no
C2 C1 N1 . . 119.12(17) no
C3 C2 C1 . . 118.82(19) no
C3 C2 N2 . . 121.22(19) no
C1 C2 N2 . . 119.85(18) no
C4 C3 C2 . . 121.0(2) no
C4 C3 H3 . . 121.7(16) no
C2 C3 H3 . . 117.4(16) no
C5 C4 C3 . . 120.2(2) no
C5 C4 H4 . . 117(2) no
C3 C4 H4 . . 122(2) no
C4 C5 C6 . . 119.6(2) no
C4 C5 H5 . . 119.0(19) no
C6 C5 H5 . . 121.4(19) no
C1 C6 C5 . . 120.7(2) no
C1 C6 H6 . . 119.2(17) no
C5 C6 H6 . . 120.1(17) no
F2 C7 F3 . . 111.6(2) no
F2 C7 F1 . . 105.3(2) no
F3 C7 F1 . . 104.4(2) no
F2 C7 C8 . . 111.72(18) no
F3 C7 C8 . . 113.66(18) no
F1 C7 C8 . . 109.55(19) no
O1 C8 C9 . . 128.38(17) no
O1 C8 C7 . . 113.16(17) no
C9 C8 C7 . . 118.45(18) no
C10 C9 C8 . . 121.20(18) no
C10 C9 H9 . . 119.3(16) no
C8 C9 H9 . . 119.4(16) no
O2 C10 C9 . . 128.01(18) no
O2 C10 C11 . . 112.75(16) no
C9 C10 C11 . . 119.24(17) no
F4 C11 F6 . . 107.52(18) no
F4 C11 F5 . . 107.59(18) no
F6 C11 F5 . . 106.88(18) no
F4 C11 C10 . . 113.96(16) no
F6 C11 C10 . . 110.72(17) no
F5 C11 C10 . . 109.87(17) no
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 O2 . 2.0468(13) yes
Fe1 O2 3 2.0468(13) no
Fe1 O1 3 2.0593(13) no
Fe1 O1 . 2.0593(13) yes
Fe1 N1 . 2.2803(17) yes
Fe1 N1 3 2.2803(17) no
O1 C8 . 1.253(2) no
O2 C10 . 1.269(2) no
O2 H2N2 . 2.26(3) no
O2 N2 . 3.125(2) no
N1 C1 . 1.443(2) yes
N1 N2 3_655 3.137(3) no
N1 H1N1 . .88(3) no
N1 H2N1 . .87(3) no
N2 C2 . 1.415(3) yes
N2 H1N2 . .90(3) no
N2 H2N2 . .86(3) no
C1 C6 . 1.390(3) yes
C1 C2 . 1.407(3) yes
C2 C3 . 1.397(3) yes
C3 C4 . 1.387(3) yes
C3 H3 . .94(3) no
C4 C5 . 1.378(4) yes
C4 H4 . .91(3) no
C5 C6 . 1.398(3) yes
C5 H5 . .95(3) no
C6 H6 . .98(3) no
C7 F2 . 1.305(3) no
C7 F3 . 1.320(3) no
C7 F1 . 1.348(3) no
C7 C8 . 1.542(3) no
C8 C9 . 1.399(3) no
C9 C10 . 1.390(3) no
C9 H9 . .95(3) no
C10 C11 . 1.533(3) no
C11 F4 . 1.328(2) no
C11 F6 . 1.330(3) no
C11 F5 . 1.341(3) no
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
_geom_hbond_publ_flag
N1 H1N1 N2 3_655 .88(3) 2.30(3) 3.137(3) 158(2) yes
N1 H2N1 F3 2_545 .87(3) 2.59(3) 3.382(2) 151(2) yes
N2 H2N2 O2 . .86(3) 2.26(3) 3.125(2) 177(2) yes
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
_geom_torsion_publ_flag
Fe1 N1 C1 C2 77.0(2) no
N1 C1 C2 N2 5.6(3) no
Fe1 N1 C1 C6 -100.86(19) no
N1 C1 C6 C5 178.30(19) no
C1 C6 C5 C4 -.2(3) no
C6 C5 C4 C3 -.5(4) no
C5 C4 C3 C2 .8(3) no
C4 C3 C2 C1 -.5(3) no
C3 C2 C1 N1 -178.00(17) no
