#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006194.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_2006194
loop_
_publ_author_name
'Zhang, H.'
'Lu, Y.'
'Biehl, E.'
_publ_section_title
;
 2-(Ferrocenylmethyl)-6-methoxy-3-methylbenzonitrile and
 10-(Ferrocenylmethyl)phenanthrene-9-carbonitrile
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              720
_journal_page_last               723
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          '[Fe (C5 H5)(C21 H14 N1)]'
_chemical_formula_sum            'C26 H19 Fe N'
_chemical_formula_weight         401.27
_chemical_name_common            ferrocenylphenanthrenecarbonitrile
_chemical_name_systematic
;
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.
_cell_angle_beta                 96.63(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   12.328(3)
_cell_length_b                   19.923(5)
_cell_length_c                   7.710(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1881.0(8)
_computing_cell_refinement       'R3m/V diffractometer control program'
_computing_data_collection       'R3m/V diffractometer control program'
_computing_data_reduction        'R3m/V diffractometer control program'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1990b)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      220(2)
_diffrn_measurement_device       R3m/V
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0641
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3577
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   '\y scans (Sheldrick, 1990b)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.027
_refine_ls_goodness_of_fit_obs   1.119
_refine_ls_hydrogen_treatment    'H atoms riding (C---H 0.96\%A)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_restrained_S_obs      1.119
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_obs          0.0501
_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^(Fo^2^)+(0.0515P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1294
_refine_ls_wR_factor_obs         0.1007
_reflns_number_observed          2077
_reflns_number_total             3311
_reflns_observed_criterion       >4sigma(F)
_[local]_cod_data_source_file    bs1011.cif
_[local]_cod_data_source_block   2
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_database_code               2006194
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
Fe 0.0350(3) 0.0440(3) 0.0428(3) 0.0042(3) -0.0028(2) 0.0024(3)
C1 0.040(2) 0.045(2) 0.034(2) 0.004(2) 0.009(2) 0.000(2)
C2 0.038(2) 0.039(2) 0.050(2) 0.001(2) 0.009(2) 0.000(2)
C3 0.049(3) 0.063(3) 0.069(3) -0.006(2) 0.002(2) -0.009(3)
C4 0.045(3) 0.096(5) 0.083(4) -0.020(3) 0.002(3) -0.035(3)
C5 0.035(2) 0.108(5) 0.065(3) 0.002(3) -0.002(2) -0.013(3)
C6 0.041(2) 0.082(3) 0.055(3) 0.009(2) -0.003(2) -0.004(3)
C7 0.055(2) 0.051(3) 0.049(3) 0.014(2) 0.002(2) 0.007(2)
C8 0.083(3) 0.039(2) 0.051(3) 0.007(3) 0.005(2) 0.003(2)
C9 0.068(3) 0.046(3) 0.057(3) -0.010(2) 0.007(2) -0.007(2)
C10 0.046(2) 0.053(3) 0.038(2) -0.001(2) 0.002(2) -0.005(2)
C11 0.042(2) 0.048(3) 0.042(2) -0.005(2) 0.012(2) -0.007(2)
C12 0.034(2) 0.056(3) 0.039(2) 0.004(2) 0.005(2) -0.006(2)
C13 0.040(2) 0.044(2) 0.031(2) 0.005(2) 0.005(2) 0.001(2)
C14 0.036(2) 0.037(2) 0.030(2) 0.005(2) 0.008(2) 0.001(2)
C21 0.041(2) 0.048(2) 0.039(2) 0.007(2) 0.002(2) 0.004(2)
C22 0.053(3) 0.048(3) 0.079(3) -0.003(2) 0.009(2) 0.002(3)
N23 0.084(3) 0.044(2) 0.139(5) -0.003(2) 0.010(3) 0.009(3)
C31 0.034(2) 0.042(2) 0.037(2) 0.011(2) -0.007(2) 0.000(2)
C32 0.039(2) 0.054(3) 0.053(3) 0.000(2) -0.008(2) -0.007(2)
C33 0.056(3) 0.080(4) 0.039(3) 0.019(2) 0.004(2) -0.007(2)
C34 0.054(3) 0.073(3) 0.053(3) 0.014(2) 0.012(2) 0.022(3)
C35 0.046(2) 0.045(2) 0.048(3) 0.006(2) 0.005(2) 0.006(2)
C36 0.051(3) 0.109(5) 0.043(3) 0.011(3) -0.005(2) 0.014(3)
C37 0.081(4) 0.073(4) 0.077(4) 0.007(3) -0.022(3) 0.033(3)
C38 0.070(3) 0.082(4) 0.075(4) 0.039(3) -0.012(3) -0.004(3)
C39 0.035(2) 0.106(4) 0.074(3) 0.000(3) -0.010(2) 0.005(4)
C40 0.063(3) 0.073(3) 0.065(3) -0.002(3) -0.020(3) -0.010(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
Fe 0.21576(4) 0.38203(3) 0.17350(8) 0.0411(2) Uani d . 1 Fe
C1 0.5715(3) 0.3267(2) 0.1892(5) 0.0391(9) Uani d . 1 C
C2 0.6439(3) 0.3755(2) 0.2522(5) 0.0419(9) Uani d . 1 C
C3 0.8218(3) 0.4120(2) 0.4111(6) 0.0610(13) Uani d . 1 C
H3 0.8032(3) 0.4566(2) 0.3878(6) 0.073 Uiso calc R 1 H
C4 0.9189(4) 0.3970(3) 0.5075(7) 0.075(2) Uani d . 1 C
H4 0.9652(4) 0.4313(3) 0.5518(7) 0.090 Uiso calc R 1 H
C5 0.9484(3) 0.3308(3) 0.5390(7) 0.0702(15) Uani d . 1 C
H5 1.0148(3) 0.3206(3) 0.6036(7) 0.084 Uiso calc R 1 H
C6 0.8799(3) 0.2800(3) 0.4754(6) 0.0598(13) Uani d . 1 C
H6 0.9009(3) 0.2357(3) 0.4972(6) 0.072 Uiso calc R 1 H
C7 0.7303(4) 0.1719(2) 0.3318(5) 0.0521(11) Uani d . 1 C
H7 0.7977(4) 0.1602(2) 0.3911(5) 0.062 Uiso calc R 1 H
C8 0.6603(4) 0.1224(2) 0.2698(6) 0.0579(12) Uani d . 1 C
H8 0.6797(4) 0.0777(2) 0.2889(6) 0.070 Uiso calc R 1 H
C9 0.5594(4) 0.1385(2) 0.1773(6) 0.0570(12) Uani d . 1 C
H9 0.5120(4) 0.1046(2) 0.1332(6) 0.068 Uiso calc R 1 H
C10 0.5309(3) 0.2044(2) 0.1524(5) 0.0459(10) Uani d . 1 C
H10 0.4634(3) 0.2149(2) 0.0916(5) 0.055 Uiso calc R 1 H
C11 0.7499(3) 0.3607(2) 0.3471(5) 0.0435(10) Uani d . 1 C
C12 0.7791(3) 0.2934(2) 0.3783(5) 0.0428(10) Uani d . 1 C
C13 0.7038(3) 0.2402(2) 0.3088(5) 0.0383(9) Uani d . 1 C
C14 0.6013(3) 0.2571(2) 0.2168(5) 0.0341(9) Uani d . 1 C
C21 0.4597(3) 0.3468(2) 0.0976(5) 0.0431(10) Uani d . 1 C
H21A 0.4658(3) 0.3896(2) 0.0393(5) 0.052 Uiso calc R 1 H
H21B 0.4357(3) 0.3136(2) 0.0095(5) 0.052 Uiso calc R 1 H
C22 0.6152(4) 0.4457(3) 0.2269(7) 0.0598(12) Uani d . 1 C
N23 0.5948(3) 0.5012(2) 0.2102(7) 0.0891(15) Uani d . 1 N
C31 0.3760(3) 0.3525(2) 0.2257(5) 0.0387(9) Uani d . 1 C
C32 0.3546(3) 0.4108(2) 0.3235(6) 0.0498(11) Uani d . 1 C
H32 0.3893(3) 0.4520(2) 0.3184(6) 0.060 Uiso calc R 1 H
C33 0.2720(4) 0.3954(2) 0.4291(6) 0.0584(13) Uani d . 1 C
H33 0.2428(4) 0.4247(2) 0.5055(6) 0.070 Uiso calc R 1 H
C34 0.2416(4) 0.3283(2) 0.3987(6) 0.0597(13) Uani d . 1 C
H34 0.1890(4) 0.3053(2) 0.4527(6) 0.072 Uiso calc R 1 H
C35 0.3038(3) 0.3014(2) 0.2729(5) 0.0464(10) Uani d . 1 C
H35 0.2987(3) 0.2580(2) 0.2285(5) 0.056 Uiso calc R 1 H
C36 0.1844(4) 0.3967(3) -0.0887(6) 0.0687(15) Uani d . 1 C
H36 0.2328(4) 0.3888(3) -0.1705(6) 0.082 Uiso calc R 1 H
C37 0.1718(4) 0.4570(3) 0.0015(8) 0.079(2) Uani d . 1 C
H37 0.2110(4) 0.4963(3) -0.0105(8) 0.095 Uiso calc R 1 H
C38 0.0913(4) 0.4483(3) 0.1116(7) 0.077(2) Uani d . 1 C
H38 0.0671(4) 0.4804(3) 0.1859(7) 0.093 Uiso calc R 1 H
C39 0.0534(3) 0.3825(3) 0.0902(7) 0.0728(14) Uani d . 1 C
H39 -0.0010(3) 0.3633(3) 0.1483(7) 0.087 Uiso calc R 1 H
C40 0.1095(4) 0.3501(3) -0.0314(7) 0.0689(14) Uani d . 1 C
H40 0.0997(4) 0.3059(3) -0.0685(7) 0.083 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C37 Fe C33 125.0(2) ?
C37 Fe C39 67.1(2) ?
C33 Fe C39 121.4(2) ?
C37 Fe C34 161.7(2) ?
C33 Fe C34 40.3(2) ?
C39 Fe C34 108.9(2) ?
C37 Fe C40 67.9(2) ?
C33 Fe C40 155.8(2) ?
C39 Fe C40 39.9(2) ?
C34 Fe C40 121.5(2) ?
C37 Fe C32 107.9(2) ?
C33 Fe C32 40.6(2) ?
C39 Fe C32 155.9(2) ?
C34 Fe C32 67.9(2) ?
C40 Fe C32 162.5(2) ?
C37 Fe C36 40.5(2) ?
C33 Fe C36 161.8(2) ?
C39 Fe C36 67.5(2) ?
C34 Fe C36 156.5(2) ?
C40 Fe C36 40.7(2) ?
C32 Fe C36 125.1(2) ?
C37 Fe C35 156.4(2) ?
C33 Fe C35 68.3(2) ?
C39 Fe C35 125.8(2) ?
C34 Fe C35 40.5(2) ?
C40 Fe C35 108.3(2) ?
C32 Fe C35 68.4(2) ?
C36 Fe C35 121.2(2) ?
C37 Fe C38 40.0(2) ?
C33 Fe C38 107.8(2) ?
C39 Fe C38 40.1(2) ?
C34 Fe C38 125.5(2) ?
C40 Fe C38 67.7(2) ?
C32 Fe C38 120.8(2) ?
C36 Fe C38 67.9(2) ?
C35 Fe C38 162.2(2) ?
C37 Fe C31 121.1(2) ?
C33 Fe C31 68.6(2) ?
C39 Fe C31 162.4(2) ?
C34 Fe C31 68.3(2) ?
C40 Fe C31 125.5(2) ?
C32 Fe C31 40.78(15) ?
C36 Fe C31 107.7(2) ?
C35 Fe C31 40.79(15) ?
C38 Fe C31 155.7(2) ?
C2 C1 C14 119.0(3) y
C2 C1 C21 119.6(3) y
C14 C1 C21 121.4(3) y
C1 C2 C22 119.9(4) y
C1 C2 C11 123.1(4) y
C22 C2 C11 117.0(4) y
C4 C3 C11 120.5(5) y
C3 C4 C5 120.1(4) y
C6 C5 C4 120.2(4) y
C5 C6 C12 121.4(5) y
C8 C7 C13 121.9(4) y
C7 C8 C9 120.3(4) y
C10 C9 C8 119.4(4) y
C9 C10 C14 121.7(4) y
C12 C11 C3 119.8(4) y
C12 C11 C2 118.6(4) y
C3 C11 C2 121.6(4) y
C6 C12 C11 118.0(4) y
C6 C12 C13 122.8(4) y
C11 C12 C13 119.2(3) y
C7 C13 C14 118.3(4) y
C7 C13 C12 121.6(3) y
C14 C13 C12 120.1(3) y
C10 C14 C13 118.4(3) y
C10 C14 C1 121.7(3) y
C13 C14 C1 119.9(3) y
C31 C21 C1 111.4(3) y
N23 C22 C2 178.3(5) y
C35 C31 C32 106.6(4) ?
C35 C31 C21 127.3(4) ?
C32 C31 C21 126.1(4) ?
C35 C31 Fe 68.9(2) ?
C32 C31 Fe 68.8(2) ?
C21 C31 Fe 127.3(3) ?
C33 C32 C31 108.6(4) ?
C33 C32 Fe 69.6(2) ?
C31 C32 Fe 70.4(2) ?
C34 C33 C32 107.9(4) ?
C34 C33 Fe 70.0(3) ?
C32 C33 Fe 69.9(2) ?
C33 C34 C35 108.7(4) ?
C33 C34 Fe 69.7(3) ?
C35 C34 Fe 69.9(2) ?
C34 C35 C31 108.0(4) ?
C34 C35 Fe 69.6(2) ?
C31 C35 Fe 70.3(2) ?
C37 C36 C40 107.0(5) ?
C37 C36 Fe 69.5(3) ?
C40 C36 Fe 69.6(3) ?
C38 C37 C36 108.8(5) ?
C38 C37 Fe 70.4(3) ?
C36 C37 Fe 70.0(3) ?
C37 C38 C39 107.4(5) ?
C37 C38 Fe 69.7(3) ?
C39 C38 Fe 69.7(3) ?
C40 C39 C38 109.3(5) ?
C40 C39 Fe 70.2(3) ?
C38 C39 Fe 70.2(3) ?
C39 C40 C36 107.5(5) ?
C39 C40 Fe 69.9(3) ?
C36 C40 Fe 69.7(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Fe C37 2.029(5) y
Fe C33 2.030(4) y
Fe C39 2.031(4) y
Fe C34 2.033(4) y
Fe C40 2.034(4) y
Fe C32 2.034(4) y
Fe C36 2.035(4) y
Fe C35 2.038(4) y
Fe C38 2.038(4) y
Fe C31 2.056(3) y
C1 C2 1.370(5) y
C1 C14 1.444(5) y
C1 C21 1.527(5) y
C2 C22 1.450(6) y
C2 C11 1.453(5) y
C3 C4 1.368(6) y
C3 C11 1.405(6) y
C4 C5 1.381(7) y
C5 C6 1.371(6) y
C6 C12 1.400(5) y
C7 C8 1.360(6) y
C7 C13 1.407(5) y
C8 C9 1.398(6) y
C9 C10 1.367(5) y
C10 C14 1.415(5) y
C11 C12 1.401(5) y
C12 C13 1.470(5) y
C13 C14 1.416(5) y
C21 C31 1.513(5) y
C22 N23 1.138(5) y
C31 C35 1.427(5) ?
C31 C32 1.425(5) ?
C32 C33 1.409(6) ?
C33 C34 1.400(6) ?
C34 C35 1.410(6) ?
C36 C37 1.406(7) ?
C36 C40 1.415(7) ?
C37 C38 1.390(7) ?
C38 C39 1.395(7) ?
C39 C40 1.386(7) ?
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
C2 C1 C21 C31 -90.1(5)
C1 C21 C31 C32 87.5(5)
C21 C1 C2 C22 -1.8(6)