#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006193.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_2006193
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) (C15 H14 N1 O1)]'
_chemical_formula_sum            'C20 H19 Fe N O'
_chemical_formula_weight         345.21
_chemical_name_common            ferrocenylbenzonitrile
_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                 103.990(10)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   19.244(3)
_cell_length_b                   8.8820(10)
_cell_length_c                   9.736(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1614.8(5)
_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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3016
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.937
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_type   '\y scans (Sheldrick, 1990b)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.063
_refine_ls_goodness_of_fit_obs   1.102
_refine_ls_hydrogen_treatment    'H atoms riding (C---H 0.96\%A)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_restrained_S_obs      1.102
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_obs          0.0367
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.8321P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1068
_refine_ls_wR_factor_obs         0.0919
_reflns_number_observed          2223
_reflns_number_total             2828
_reflns_observed_criterion       >4sigma(F)
_[local]_cod_data_source_file    bs1011.cif
_[local]_cod_data_source_block   1
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_database_code               2006193
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 0.0264(2) 0.0267(2) 0.0236(2) 0.0017(2) 0.00167(14) 0.00011(15)
C1 0.0239(13) 0.037(2) 0.0305(13) 0.0038(11) 0.0106(11) 0.0019(11)
C2 0.0251(13) 0.0278(14) 0.0394(14) 0.0044(11) 0.0115(11) 0.0035(11)
C3 0.0237(13) 0.0319(14) 0.0367(14) 0.0021(11) 0.0057(11) -0.0026(11)
C4 0.0314(15) 0.0318(15) 0.0395(15) 0.0103(12) 0.0027(12) 0.0061(12)
C5 0.039(2) 0.0250(14) 0.045(2) 0.0040(12) 0.0084(13) -0.0035(12)
C6 0.0279(14) 0.036(2) 0.0349(15) 0.0036(12) 0.0083(12) -0.0063(12)
C21 0.0288(14) 0.042(2) 0.0319(14) 0.0055(12) 0.0078(11) 0.0026(12)
C22 0.0261(14) 0.037(2) 0.046(2) -0.0010(12) 0.0050(12) 0.0057(13)
N23 0.049(2) 0.031(2) 0.078(2) -0.0047(12) 0.0079(14) 0.0101(13)
O24 0.0353(11) 0.0355(11) 0.0509(12) -0.0013(9) -0.0073(9) -0.0033(9)
C25 0.031(2) 0.049(2) 0.041(2) -0.0003(13) -0.0019(13) -0.0028(14)
C26 0.046(2) 0.048(2) 0.044(2) 0.0001(15) 0.0048(14) -0.0113(14)
C31 0.0278(13) 0.0327(14) 0.0232(12) 0.0059(11) 0.0039(10) 0.0043(10)
C32 0.0297(14) 0.041(2) 0.0233(12) 0.0028(12) 0.0010(10) -0.0015(11)
C33 0.0333(15) 0.049(2) 0.0262(13) 0.0107(13) 0.0091(11) 0.0045(12)
C34 0.0270(14) 0.038(2) 0.0403(15) -0.0008(12) 0.0066(12) 0.0093(12)
C35 0.0343(15) 0.0268(13) 0.0333(14) 0.0001(12) 0.0023(11) 0.0025(11)
C36 0.147(5) 0.053(2) 0.039(2) 0.026(3) 0.044(2) 0.017(2)
C37 0.046(2) 0.069(3) 0.082(3) 0.008(2) 0.024(2) 0.046(2)
C38 0.090(3) 0.028(2) 0.046(2) -0.002(2) 0.000(2) 0.0041(14)
C39 0.049(2) 0.072(3) 0.071(2) 0.030(2) 0.018(2) 0.043(2)
C40 0.104(4) 0.064(3) 0.040(2) -0.037(3) -0.034(2) 0.022(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Fe 0.62356(2) -0.00117(4) 0.38270(3) 0.02628(14) Uani d . 1 Fe
C1 0.82252(13) -0.2615(3) 0.5772(3) 0.0299(6) Uani d . 1 C
C2 0.86923(13) -0.1760(3) 0.6817(3) 0.0301(6) Uani d . 1 C
C3 0.91868(14) -0.2438(3) 0.7949(3) 0.0310(6) Uani d . 1 C
C4 0.92132(15) -0.3988(3) 0.8031(3) 0.0352(6) Uani d . 1 C
H4 0.95364(15) -0.4464(3) 0.8769(3) 0.042 Uiso calc R 1 H
C5 0.87522(15) -0.4827(3) 0.7001(3) 0.0363(6) Uani d . 1 C
H5 0.87746(15) -0.5871(3) 0.7068(3) 0.044 Uiso calc R 1 H
C6 0.82601(14) -0.4188(3) 0.5879(3) 0.0329(6) Uani d . 1 C
C21 0.77043(14) -0.1812(3) 0.4570(3) 0.0340(6) Uani d . 1 C
H21A 0.79171(14) -0.0871(3) 0.4373(3) 0.041 Uiso calc R 1 H
H21B 0.76273(14) -0.2429(3) 0.3724(3) 0.041 Uiso calc R 1 H
C22 0.86844(14) -0.0141(3) 0.6745(3) 0.0369(7) Uani d . 1 C
N23 0.86715(15) 0.1141(3) 0.6686(3) 0.0542(7) Uani d . 1 N
O24 0.96114(10) -0.1469(2) 0.8862(2) 0.0436(5) Uani d . 1 O
C25 1.01327(14) -0.2096(4) 1.0037(3) 0.0424(7) Uani d . 1 C
H25A 1.03948(14) -0.1296(4) 1.0595(3) 0.064 Uiso calc R 1 H
H25B 1.04575(14) -0.2726(4) 0.9689(3) 0.064 Uiso calc R 1 H
H25C 0.98935(14) -0.2684(4) 1.0612(3) 0.064 Uiso calc R 1 H
C26 0.7795(2) -0.5197(4) 0.4789(3) 0.0470(8) Uani d . 1 C
H26A 0.7483(2) -0.4592(4) 0.4083(3) 0.071 Uiso calc R 1 H
H26B 0.7513(2) -0.5833(4) 0.5240(3) 0.071 Uiso calc R 1 H
H26C 0.8091(2) -0.5808(4) 0.4351(3) 0.071 Uiso calc R 1 H
C31 0.69899(13) -0.1486(3) 0.4892(2) 0.0283(6) Uani d . 1 C
C32 0.68438(14) -0.0359(3) 0.5828(3) 0.0324(6) Uani d . 1 C
H32 0.71752(14) 0.0307(3) 0.6359(3) 0.039 Uiso calc R 1 H
C33 0.61029(15) -0.0433(3) 0.5808(3) 0.0358(6) Uani d . 1 C
H33 0.58656(15) 0.0179(3) 0.6323(3) 0.043 Uiso calc R 1 H
C34 0.57902(14) -0.1595(3) 0.4871(3) 0.0352(6) Uani d . 1 C
H34 0.53115(14) -0.1884(3) 0.4661(3) 0.042 Uiso calc R 1 H
C35 0.63324(14) -0.2244(3) 0.4308(3) 0.0325(6) Uani d . 1 C
H35 0.62703(14) -0.3034(3) 0.3663(3) 0.039 Uiso calc R 1 H
C36 0.6319(3) 0.0346(5) 0.1818(4) 0.0760(14) Uani d . 1 C
H36 0.6507(3) -0.0336(5) 0.1279(4) 0.091 Uiso calc R 1 H
C37 0.6693(2) 0.1431(5) 0.2682(4) 0.0642(11) Uani d . 1 C
H37 0.7180(2) 0.1619(5) 0.2823(4) 0.077 Uiso calc R 1 H
C38 0.6233(2) 0.2201(4) 0.3312(4) 0.0578(10) Uani d . 1 C
H38 0.6356(2) 0.2988(4) 0.3955(4) 0.069 Uiso calc R 1 H
C39 0.5552(2) 0.1601(5) 0.2822(4) 0.0633(11) Uani d . 1 C
H39 0.5138(2) 0.1914(5) 0.3071(4) 0.076 Uiso calc R 1 H
C40 0.5603(3) 0.0441(5) 0.1884(4) 0.0779(15) Uani d . 1 C
H40 0.5229(3) -0.0160(5) 0.1393(4) 0.093 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'
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
_geom_angle_publ_flag
C36 Fe C40 40.3(2) ?
C36 Fe C38 66.8(2) ?
C40 Fe C38 67.16(15) ?
C36 Fe C39 67.5(2) ?
C40 Fe C39 40.3(2) ?
C38 Fe C39 40.00(14) ?
C36 Fe C37 39.3(2) ?
C40 Fe C37 66.7(2) ?
C38 Fe C37 39.6(2) ?
C39 Fe C37 66.83(14) ?
C36 Fe C35 110.54(14) ?
C40 Fe C35 114.13(14) ?
C38 Fe C35 174.59(14) ?
C39 Fe C35 144.21(15) ?
C37 Fe C35 135.45(14) ?
C36 Fe C32 141.7(2) ?
C40 Fe C32 176.5(2) ?
C38 Fe C32 110.46(12) ?
C39 Fe C32 136.31(15) ?
C37 Fe C32 113.26(14) ?
C35 Fe C32 68.48(11) ?
C36 Fe C33 177.0(2) ?
C40 Fe C33 137.3(2) ?
C38 Fe C33 114.69(14) ?
C39 Fe C33 111.75(13) ?
C37 Fe C33 143.5(2) ?
C35 Fe C33 68.25(11) ?
C32 Fe C33 40.82(11) ?
C36 Fe C34 136.8(2) ?
C40 Fe C34 111.83(14) ?
C38 Fe C34 144.53(15) ?
C39 Fe C34 115.16(13) ?
C37 Fe C34 175.4(2) ?
C35 Fe C34 40.57(11) ?
C32 Fe C34 68.47(11) ?
C33 Fe C34 40.49(11) ?
C36 Fe C31 112.3(2) ?
C40 Fe C31 142.6(2) ?
C38 Fe C31 134.92(13) ?
C39 Fe C31 174.88(14) ?
C37 Fe C31 109.51(12) ?
C35 Fe C31 40.91(10) ?
C32 Fe C31 40.91(10) ?
C33 Fe C31 68.80(10) ?
C34 Fe C31 68.77(10) ?
C6 C1 C2 118.3(2) y
C6 C1 C21 122.3(2) y
C2 C1 C21 119.4(2) y
C3 C2 C1 122.0(2) y
C3 C2 C22 117.6(2) y
C1 C2 C22 120.5(2) y
O24 C3 C4 125.9(3) y
O24 C3 C2 115.3(2) y
C4 C3 C2 118.8(3) y
C3 C4 C5 119.1(3) y
C6 C5 C4 123.2(3) y
C5 C6 C1 118.6(3) y
C5 C6 C26 119.3(3) y
C1 C6 C26 122.1(3) y
C31 C21 C1 113.1(2) y
N23 C22 C2 179.4(3) y
C3 O24 C25 117.9(2) y
C35 C31 C32 107.1(2) ?
C35 C31 C21 126.3(2) ?
C32 C31 C21 126.7(2) ?
C35 C31 Fe 69.31(14) ?
C32 C31 Fe 69.46(14) ?
C21 C31 Fe 126.0(2) ?
C33 C32 C31 108.1(2) ?
C33 C32 Fe 69.63(14) ?
C31 C32 Fe 69.63(14) ?
C34 C33 C32 108.1(2) ?
C34 C33 Fe 69.79(15) ?
C32 C33 Fe 69.55(15) ?
C33 C34 C35 108.0(2) ?
C33 C34 Fe 69.7(2) ?
C35 C34 Fe 69.5(2) ?
C34 C35 C31 108.7(2) ?
C34 C35 Fe 69.9(2) ?
C31 C35 Fe 69.78(15) ?
C37 C36 C40 107.9(4) ?
C37 C36 Fe 70.6(2) ?
C40 C36 Fe 69.9(2) ?
C36 C37 C38 109.0(4) ?
C36 C37 Fe 70.1(2) ?
C38 C37 Fe 70.0(2) ?
C37 C38 C39 108.1(3) ?
C37 C38 Fe 70.4(2) ?
C39 C38 Fe 70.1(2) ?
C38 C39 C40 107.3(3) ?
C38 C39 Fe 69.9(2) ?
C40 C39 Fe 69.7(2) ?
C36 C40 C39 107.6(3) ?
C36 C40 Fe 69.8(2) ?
C39 C40 Fe 70.0(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Fe C36 2.026(3) y
Fe C40 2.027(3) y
Fe C38 2.028(3) y
Fe C39 2.030(3) y
Fe C37 2.033(3) y
Fe C35 2.035(3) y
Fe C32 2.039(3) y
Fe C33 2.040(3) y
Fe C34 2.041(3) y
Fe C31 2.042(2) y
C1 C6 1.402(4) y
C1 C2 1.406(4) y
C1 C21 1.522(4) y
C2 C3 1.406(4) y
C2 C22 1.439(4) y
C3 O24 1.359(3) y
C3 C4 1.380(4) y
C4 C5 1.385(4) y
C5 C6 1.383(4) y
C6 C26 1.507(4) y
C21 C31 1.510(3) y
C22 N23 1.141(4) y
O24 C25 1.439(3) ?
C31 C35 1.425(4) ?
C31 C32 1.426(4) ?
C32 C33 1.423(4) ?
C33 C34 1.413(4) ?
C34 C35 1.413(4) ?
C36 C37 1.365(6) ?
C36 C40 1.396(7) ?
C37 C38 1.375(5) ?
C38 C39 1.388(5) ?
C39 C40 1.396(6) ?
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 -90.6(3)
C1 C21 C31 C32 74.0(3)
C21 C1 C2 C22 -0.6(4)