#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2005233.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_2005233
loop_
_publ_author_name
'Bell, W.'
'Ferguson, G.'
'Glidewell, C.'
_publ_section_title
;
 Cyanoferrocene: a Two-Dimensional Network Generated by Short
 C---H···N Hydrogen Bonds
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1928
_journal_page_last               1930
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          '[Fe (C5 H5)(C6 H4 N1)]'
_chemical_formula_moiety         'C11 H9 Fe N'
_chemical_formula_sum            'C11 H9 Fe N'
_chemical_formula_weight         211.04
_chemical_name_systematic
;
Cyanoferrocene
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   7.6314(6)
_cell_length_b                   10.4521(15)
_cell_length_c                   11.2292(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      20.02
_cell_measurement_theta_min      11.56
_cell_volume                     895.69(18)
_computing_cell_refinement       'SET4 and CELDIM in CAD-4-PC Software'
_computing_data_collection       'CAD-4-PC Software (Enraf-Nonius, 1992)'
_computing_data_reduction
'DATRD2 in NRCVAX94 (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics    'NRCVAX94, PLATON,  PLUTON (Spek 1995b)'
_computing_publication_material
'NRCVAX94, SHELXL93 and WordPerfect (macro PREPCIF)'
_computing_structure_refinement  'NRCVAX94 and SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294.0(10)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1504
_diffrn_reflns_theta_max         29.86
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.626
_exptl_absorpt_correction_T_max  0.690
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_type
'\y scans at 4\% steps (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.289
_refine_ls_abs_structure_details 'Flack (1983) parameter = 0.03(3)'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   0.934
_refine_ls_goodness_of_fit_obs   1.015
_refine_ls_hydrogen_treatment
'H atoms riding (SHELXL93 defaults; C---H 0.93\%A)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_restrained_S_obs      1.015
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_obs          0.0375
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.07P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1039
_refine_ls_wR_factor_obs         0.0978
_reflns_number_observed          1155
_reflns_number_total             1504
_reflns_observed_criterion       >2\s(I)
_[local]_cod_data_source_file    cf1114.cif
_[local]_cod_data_source_block   9623
_cod_original_cell_volume        895.7(2)
_cod_database_code               2005233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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 0.0345(3) 0.0333(3) 0.0377(3) 0.0023(2) 0.0004(2) -0.0010(2)
N1 0.074(3) 0.069(3) 0.053(2) 0.002(2) 0.005(2) -0.012(2)
C1 0.048(2) 0.044(2) 0.050(2) 0.006(2) 0.002(2) -0.005(2)
C11 0.044(2) 0.039(2) 0.045(2) 0.004(2) 0.003(2) 0.000(2)
C12 0.032(2) 0.048(2) 0.061(3) 0.012(2) 0.004(2) 0.000(2)
C13 0.049(2) 0.055(3) 0.061(3) 0.012(2) -0.015(2) -0.007(3)
C14 0.071(3) 0.051(3) 0.043(2) 0.016(2) -0.006(2) 0.000(2)
C15 0.059(3) 0.033(2) 0.051(2) 0.003(2) 0.001(2) 0.005(2)
C21 0.059(3) 0.055(3) 0.051(3) 0.014(2) -0.018(2) -0.006(2)
C22 0.060(3) 0.042(2) 0.057(3) 0.009(2) 0.001(2) 0.012(2)
C23 0.068(3) 0.041(2) 0.060(3) 0.015(2) -0.007(2) -0.010(2)
C24 0.059(3) 0.055(3) 0.064(3) 0.017(2) 0.019(2) 0.001(3)
C25 0.037(2) 0.052(3) 0.111(5) 0.003(2) -0.007(3) -0.008(3)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Fe1 0.23818(6) 0.11232(5) 0.70318(5) 0.0352(2) Uani d . 1 Fe
N1 0.2133(5) 0.3543(4) 0.9854(4) 0.0653(12) Uani d . 1 N
C1 0.1758(6) 0.3141(4) 0.8952(4) 0.0475(10) Uani d . 1 C
Cg1 0.0880(6) 0.2223(5) 0.6843(4) . . . . . .
Cg2 0.3882(7) 0.0000(5) 0.7235(5) . . . . . .
C11 0.1260(5) 0.2658(4) 0.7809(4) 0.0426(9) Uani d . 1 C
C12 -0.0046(6) 0.1681(5) 0.7579(5) 0.0470(10) Uani d . 1 C
C13 -0.0054(6) 0.1455(5) 0.6328(4) 0.0553(12) Uani d . 1 C
C14 0.1212(7) 0.2294(5) 0.5799(4) 0.0548(12) Uani d . 1 C
C15 0.2028(6) 0.3027(4) 0.6698(4) 0.0477(11) Uani d . 1 C
C21 0.4076(7) 0.0332(5) 0.8230(4) 0.0553(12) Uani d . 1 C
C22 0.2888(6) -0.0581(4) 0.7842(4) 0.0533(11) Uani d . 1 C
C23 0.3097(7) -0.0695(5) 0.6611(5) 0.0563(13) Uani d . 1 C
C24 0.4371(7) 0.0148(5) 0.6238(5) 0.0595(13) Uani d . 1 C
C25 0.4980(7) 0.0794(5) 0.7253(6) 0.066(2) Uani d . 1 C
H12 -0.0748 0.1279 0.8143 0.056 Uiso calc R 1 H
H13 -0.0755 0.0868 0.5927 0.066 Uiso calc R 1 H
H14 0.1458 0.2348 0.4989 0.066 Uiso calc R 1 H
H15 0.2902 0.3635 0.6588 0.057 Uiso calc R 1 H
H21 0.4239 0.0589 0.9015 0.066 Uiso calc R 1 H
H22 0.2100 -0.1032 0.8313 0.064 Uiso calc R 1 H
H23 0.2475 -0.1251 0.6122 0.068 Uiso calc R 1 H
H24 0.4756 0.0266 0.5460 0.071 Uiso calc R 1 H
H25 0.5841 0.1424 0.7265 0.080 Uiso calc R 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 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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 -2 1
-1 -2 5
-2 -4 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
Cg1 Fe1 Cg2 179.2(2) y
N1 C1 C11 178.8(5) y
C1 C11 C15 125.3(4) ?
C12 C11 C15 108.4(4) ?
C1 C11 C12 126.2(4) ?
C11 C12 C13 107.2(5) ?
C12 C13 C14 107.7(5) ?
C13 C14 C15 109.4(4) ?
C11 C15 C14 107.3(4) ?
C22 C21 C25 108.5(4) ?
C21 C22 C23 107.2(5) ?
C22 C23 C24 109.1(5) ?
C23 C24 C25 107.2(5) ?
C21 C25 C24 108.1(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Fe1 Cg1 1.637(5) yes
Fe1 Cg2 1.656(5) yes
Fe1 C11 2.016(4) ?
Fe1 C12 2.038(5) ?
Fe1 C13 2.050(5) ?
Fe1 C14 2.052(4) ?
Fe1 C15 2.042(4) ?
Fe1 C21 2.041(5) ?
Fe1 C22 2.037(4) ?
Fe1 C24 2.034(5) ?
Fe1 C23 2.033(4) ?
Fe1 C25 2.028(5) ?
N1 C1 1.133(6) y
C1 C11 1.432(6) y
C11 C12 1.450(7) y
C11 C15 1.431(6) y
C12 C13 1.425(7) y
C13 C14 1.435(7) y
C14 C15 1.411(6) y
C21 C22 1.387(7) y
C21 C25 1.384(8) y
C22 C23 1.396(7) y
C23 C24 1.378(7) y
C24 C25 1.404(8) y
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
C11 Cg1 Cg2 C21 8.5(6) y
C12 Cg1 Cg2 C22 7.2(6) y
C13 Cg1 Cg2 C23 8.5(6) y
C14 Cg1 Cg2 C24 7.2(6) y
C15 Cg1 Cg2 C25 8.7(6) y
C15 C11 C12 C13 0.5(5) ?
C1 C11 C12 C13 -177.3(4) ?
C11 C12 C13 C14 -0.8(6) ?
C12 C13 C14 C15 0.9(6) ?
C13 C14 C15 C11 -0.6(5) ?
C1 C11 C15 C14 177.8(4) ?
C12 C11 C15 C14 0.0(5) ?
C25 C21 C22 C23 1.2(6) ?
C21 C22 C23 C24 -1.0(6) ?
C22 C23 C24 C25 0.4(6) ?
C22 C21 C25 C24 -1.0(6) ?
C23 C24 C25 C21 0.4(6) ?