#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:59:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178631 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/42/4074214.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_4074214
loop_
_publ_author_name
'Braga, Dario'
'Grepioni, Fabrizia'
'Polito, Marco'
'Chierotti, Michele R.'
'Ellena, Silvano'
'Gobetto, Roberto'
_publ_section_title
;
 A Solid−Gas Route to Polymorph Conversion in Crystalline
 [FeII(η5-C5H4COOH)2]. A Diffraction and Solid-State NMR Study
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              4627
_journal_paper_doi               10.1021/om060468w
_journal_volume                  25
_journal_year                    2006
_chemical_formula_moiety         'C12 H8 Fe O4, 2(C2 H8 N)'
_chemical_formula_sum            'C16 H24 Fe N2 O4'
_chemical_formula_weight         364.22
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 99.453(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.474(4)
_cell_length_b                   7.7710(10)
_cell_length_c                   10.4850(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1725.9(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_sigmaI/netI    0.0810
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3070
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.51
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_T_max  0.851
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.051
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0520
_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)+(0.0765P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                1025
_reflns_number_total             1526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om060468wsi20060529_042015.cif
_cod_data_source_block           c2c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Psi-scan' changed to
'psi-scan' 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      'C 2/c'
_cod_database_code               4074214
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Fe1 Fe 0.2500 -0.2500 -0.5000 0.0219(2) Uani 1 2 d S
O1 O 0.39542(15) -0.1230(4) -0.6320(3) 0.0446(8) Uani 1 1 d .
O2 O 0.43160(13) -0.2606(5) -0.4483(3) 0.0521(9) Uani 1 1 d .
C1 C 0.31267(18) -0.4483(5) -0.4622(4) 0.0289(9) Uani 1 1 d .
H1 H 0.3368 -0.4735 -0.3824 0.024(10) Uiso 1 1 d R
C2 C 0.2520(2) -0.5120(5) -0.5099(4) 0.0322(8) Uani 1 1 d .
H2 H 0.2292 -0.5883 -0.4670 0.040(12) Uiso 1 1 d R
C3 C 0.23193(19) -0.4422(5) -0.6349(4) 0.0327(9) Uani 1 1 d .
H3 H 0.1937 -0.4640 -0.6883 0.040(12) Uiso 1 1 d R
C4 C 0.28064(19) -0.3328(6) -0.6641(4) 0.0310(9) Uani 1 1 d .
H4 H 0.2798 -0.2700 -0.7399 0.039(12) Uiso 1 1 d R
C5 C 0.33094(17) -0.3342(5) -0.5572(4) 0.0254(8) Uani 1 1 d .
C6 C 0.39022(17) -0.2316(6) -0.5454(4) 0.0330(9) Uani 1 1 d .
N1 N 0.55292(16) -0.1844(5) -0.4530(3) 0.0353(8) Uani 1 1 d .
H1A H 0.5642 -0.0768 -0.4270 0.067(17) Uiso 1 1 d R
H1B H 0.5112 -0.1950 -0.4530 0.031(11) Uiso 1 1 d R
C7 C 0.5652(3) -0.2085(8) -0.5862(5) 0.0555(15) Uani 1 1 d .
H7A H 0.5413 -0.1259 -0.6422 0.077(19) Uiso 1 1 d R
H7B H 0.5529 -0.3226 -0.6151 0.09(2) Uiso 1 1 d R
H7C H 0.6094 -0.1927 -0.5878 0.050(14) Uiso 1 1 d R
C8 C 0.5865(3) -0.3059(8) -0.3602(5) 0.0531(14) Uani 1 1 d .
H8A H 0.5764 -0.2838 -0.2759 0.075(18) Uiso 1 1 d R
H8B H 0.6312 -0.2933 -0.3577 0.054(15) Uiso 1 1 d R
H8C H 0.5741 -0.4211 -0.3861 0.069(18) Uiso 1 1 d R
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'
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'
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
C5 Fe1 C5 180.0 . 7_544
C5 Fe1 C2 111.20(17) . 7_544
C5 Fe1 C2 68.80(17) 7_544 7_544
C5 Fe1 C2 68.80(17) . .
C5 Fe1 C2 111.20(17) 7_544 .
C2 Fe1 C2 180.0 7_544 .
C5 Fe1 C1 41.20(15) . .
C5 Fe1 C1 138.80(15) 7_544 .
C2 Fe1 C1 139.67(16) 7_544 .
C2 Fe1 C1 40.33(16) . .
C5 Fe1 C1 138.80(15) . 7_544
C5 Fe1 C1 41.20(15) 7_544 7_544
C2 Fe1 C1 40.33(16) 7_544 7_544
C2 Fe1 C1 139.67(16) . 7_544
C1 Fe1 C1 180.000(1) . 7_544
C5 Fe1 C4 139.19(15) . 7_544
C5 Fe1 C4 40.81(15) 7_544 7_544
C2 Fe1 C4 68.33(17) 7_544 7_544
C2 Fe1 C4 111.67(17) . 7_544
C1 Fe1 C4 111.55(16) . 7_544
C1 Fe1 C4 68.45(16) 7_544 7_544
C5 Fe1 C4 40.81(15) . .
C5 Fe1 C4 139.19(15) 7_544 .
C2 Fe1 C4 111.67(17) 7_544 .
C2 Fe1 C4 68.33(17) . .
C1 Fe1 C4 68.45(16) . .
C1 Fe1 C4 111.55(16) 7_544 .
C4 Fe1 C4 180.000(1) 7_544 .
C5 Fe1 C3 111.30(15) . 7_544
C5 Fe1 C3 68.70(15) 7_544 7_544
C2 Fe1 C3 40.59(16) 7_544 7_544
C2 Fe1 C3 139.41(16) . 7_544
C1 Fe1 C3 111.85(16) . 7_544
C1 Fe1 C3 68.15(16) 7_544 7_544
C4 Fe1 C3 40.59(16) 7_544 7_544
C4 Fe1 C3 139.41(16) . 7_544
C5 Fe1 C3 68.70(15) . .
C5 Fe1 C3 111.30(15) 7_544 .
C2 Fe1 C3 139.41(16) 7_544 .
C2 Fe1 C3 40.59(16) . .
C1 Fe1 C3 68.15(16) . .
C1 Fe1 C3 111.85(16) 7_544 .
C4 Fe1 C3 139.41(16) 7_544 .
C4 Fe1 C3 40.59(16) . .
C3 Fe1 C3 180.000(1) 7_544 .
C2 C1 C5 108.3(3) . .
C2 C1 Fe1 69.8(2) . .
C5 C1 Fe1 69.3(2) . .
C2 C1 H1 126.3 . .
C5 C1 H1 125.4 . .
Fe1 C1 H1 125.9 . .
C1 C2 C3 108.5(4) . .
C1 C2 Fe1 69.9(2) . .
C3 C2 Fe1 70.1(2) . .
C1 C2 H2 125.7 . .
C3 C2 H2 125.8 . .
Fe1 C2 H2 126.5 . .
C2 C3 C4 107.8(3) . .
C2 C3 Fe1 69.3(2) . .
C4 C3 Fe1 69.5(2) . .
C2 C3 H3 126.2 . .
C4 C3 H3 126.0 . .
Fe1 C3 H3 126.6 . .
C3 C4 C5 108.4(3) . .
C3 C4 Fe1 69.9(2) . .
C5 C4 Fe1 69.4(2) . .
C3 C4 H4 126.0 . .
C5 C4 H4 125.6 . .
Fe1 C4 H4 126.2 . .
C4 C5 C1 107.0(3) . .
C4 C5 C6 126.1(3) . .
C1 C5 C6 126.9(4) . .
C4 C5 Fe1 69.8(2) . .
C1 C5 Fe1 69.5(2) . .
C6 C5 Fe1 124.2(3) . .
O2 C6 O1 124.8(4) . .
O2 C6 C5 116.8(4) . .
O1 C6 C5 118.4(3) . .
C8 N1 C7 113.8(4) . .
C8 N1 H1A 108.7 . .
C7 N1 H1A 108.9 . .
C8 N1 H1B 108.9 . .
C7 N1 H1B 108.7 . .
H1A N1 H1B 107.7 . .
N1 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N1 C7 H7C 109.4 . .
H7A C7 H7C 109.4 . .
H7B C7 H7C 109.5 . .
N1 C8 H8A 109.6 . .
N1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N1 C8 H8C 109.3 . .
H8A C8 H8C 109.4 . .
H8B C8 H8C 109.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 C5 2.038(3) .
Fe1 C5 2.038(3) 7_544
Fe1 C2 2.040(4) 7_544
Fe1 C2 2.040(4) .
Fe1 C1 2.041(4) .
Fe1 C1 2.041(4) 7_544
Fe1 C4 2.044(4) 7_544
Fe1 C4 2.044(4) .
Fe1 C3 2.050(4) 7_544
Fe1 C3 2.050(4) .
O1 C6 1.258(5) .
O2 C6 1.257(5) .
C1 C2 1.407(6) .
C1 C5 1.435(5) .
C1 H1 0.9303 .
C2 C3 1.418(6) .
C2 H2 0.9306 .
C3 C4 1.420(6) .
C3 H3 0.9302 .
C4 C5 1.423(5) .
C4 H4 0.9302 .
C5 C6 1.490(6) .
N1 C8 1.459(6) .
N1 C7 1.475(5) .
N1 H1A 0.8999 .
N1 H1B 0.9005 .
C7 H7A 0.9596 .
C7 H7B 0.9597 .
C7 H7C 0.9601 .
C8 H8A 0.9600 .
C8 H8B 0.9599 .
C8 H8C 0.9600 .
