#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007142.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_2007142
loop_
_publ_author_name
'Zhang, H.'
'Lu, Y.'
'Biehl, E.'
_publ_section_title
;
 2-[(2,5-Dimethoxyphenyl)(ferrocenyl)methyl]-3,6-dimethoxybenzonitrile
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              462
_journal_page_last               464
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac          '[Fe (C5 H5) (C23 H22 N1 O4)]'
_chemical_formula_sum            'C28 H27 Fe N O4'
_chemical_formula_weight         497.36
_chemical_name_common            ferrocenylbenzonitrile
_chemical_name_systematic
;
3,6-Dimethoxy-2-[\a-ferrocenyl-\a-(2',5'-dimethoxy-
phenyl)]methylbenzonitrile
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.004(2)
_cell_length_b                   19.108(2)
_cell_length_c                   20.328(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     4662.7(10)
_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_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4108
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.68
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   '\y scan (SHELXTL-Plus; Sheldrick, 1990)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.02
_refine_ls_goodness_of_fit_obs   1.086
_refine_ls_hydrogen_treatment    'H atoms riding (C---H 0.96\%A)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_restrained_S_obs      1.086
_refine_ls_R_factor_all          0.081
_refine_ls_R_factor_obs          0.043
_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^)+(0.0401P)^2^+1.35P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.102
_refine_ls_wR_factor_obs         0.086
_reflns_number_observed          2794
_reflns_number_total             4108
_reflns_observed_criterion       >4sigma(F)
_[local]_cod_data_source_file    bk1350.cif
_[local]_cod_data_source_block   eb-ylfe5
_cod_database_code               2007142
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.0377(3) 0.0272(2) 0.0207(2) -0.0033(2) -0.0007(2) -0.0010(2)
C1 0.028(2) 0.026(2) 0.023(2) 0.0017(13) -0.0028(13) -0.0022(13)
C11 0.022(2) 0.034(2) 0.026(2) 0.0045(13) -0.0042(13) -0.0051(14)
C12 0.025(2) 0.040(2) 0.032(2) 0.002(2) -0.0054(15) -0.008(2)
C13 0.035(2) 0.044(2) 0.039(2) 0.012(2) -0.003(2) -0.016(2)
C14 0.038(2) 0.061(2) 0.028(2) 0.013(2) 0.002(2) -0.009(2)
C15 0.034(2) 0.048(2) 0.027(2) 0.005(2) -0.0010(15) 0.003(2)
C16 0.031(2) 0.035(2) 0.029(2) 0.0073(15) -0.0039(14) -0.0045(14)
O12 0.0412(14) 0.0313(12) 0.0431(14) 0.0046(11) 0.0041(11) -0.0067(10)
C17 0.047(2) 0.033(2) 0.059(2) 0.008(2) -0.005(2) -0.011(2)
O15 0.061(2) 0.055(2) 0.0300(12) 0.0061(14) 0.0107(11) 0.0084(12)
C18 0.056(2) 0.079(3) 0.038(2) 0.007(2) 0.017(2) 0.012(2)
C21 0.027(2) 0.027(2) 0.020(2) 0.0044(13) -0.0027(13) -0.0100(13)
C22 0.034(2) 0.031(2) 0.020(2) 0.0061(15) -0.0039(14) -0.0065(13)
C23 0.027(2) 0.046(2) 0.030(2) 0.009(2) -0.0064(15) -0.010(2)
C24 0.025(2) 0.053(2) 0.031(2) -0.002(2) -0.0016(15) -0.013(2)
C25 0.033(2) 0.039(2) 0.023(2) -0.005(2) -0.0006(14) -0.0120(14)
C26 0.025(2) 0.029(2) 0.025(2) 0.0032(14) -0.0057(14) -0.0072(14)
O22 0.0392(13) 0.0363(12) 0.0315(12) 0.0099(10) -0.0093(11) 0.0019(10)
C27 0.059(2) 0.050(2) 0.049(2) 0.020(2) -0.011(2) 0.005(2)
O25 0.0357(13) 0.0541(15) 0.0422(14) -0.0155(12) -0.0030(12) 0.0057(12)
C28 0.043(2) 0.069(3) 0.041(2) -0.023(2) 0.005(2) -0.005(2)
C29 0.035(2) 0.027(2) 0.031(2) -0.0039(14) -0.004(2) -0.0036(14)
N30 0.053(2) 0.033(2) 0.048(2) -0.0013(14) -0.012(2) 0.0000(14)
C31 0.031(2) 0.030(2) 0.0186(14) 0.0008(15) -0.0023(14) -0.0008(12)
C32 0.031(2) 0.048(2) 0.031(2) -0.007(2) 0.0046(14) -0.008(2)
C33 0.056(2) 0.045(2) 0.026(2) -0.024(2) 0.004(2) -0.005(2)
C34 0.065(3) 0.026(2) 0.031(2) 0.001(2) -0.004(2) -0.0030(15)
C35 0.044(2) 0.033(2) 0.031(2) 0.007(2) -0.009(2) -0.0026(14)
C36 0.113(4) 0.033(2) 0.032(2) 0.002(2) -0.014(2) 0.009(2)
C37 0.088(3) 0.065(3) 0.035(2) -0.013(3) -0.029(2) 0.011(2)
C38 0.110(4) 0.047(2) 0.025(2) -0.023(3) 0.010(2) -0.008(2)
C39 0.072(3) 0.061(3) 0.044(2) -0.022(2) 0.028(2) -0.010(2)
C40 0.098(4) 0.054(3) 0.033(2) -0.037(3) 0.011(2) 0.003(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 0.21152(4) 0.33481(2) 0.28593(2) 0.02851(13) Uani d . 1 Fe
C1 0.2367(2) 0.43008(14) 0.41537(14) 0.0257(7) Uani d . 1 C
H1 0.1976(2) 0.46376(14) 0.38724(14) 0.031 Uiso calc R 1 H
C11 0.1847(2) 0.4380(2) 0.48395(15) 0.0271(7) Uani d . 1 C
C12 0.1628(3) 0.5058(2) 0.5081(2) 0.0324(7) Uani d . 1 C
C13 0.1123(3) 0.5146(2) 0.5689(2) 0.0393(8) Uani d . 1 C
H13 0.0978(3) 0.5596(2) 0.5843(2) 0.047 Uiso calc R 1 H
C14 0.0830(3) 0.4572(2) 0.6070(2) 0.0424(9) Uani d . 1 C
H14 0.0496(3) 0.4636(2) 0.6478(2) 0.051 Uiso calc R 1 H
C15 0.1037(3) 0.3906(2) 0.5841(2) 0.0361(8) Uani d . 1 C
C16 0.1543(3) 0.3812(2) 0.52280(14) 0.0316(7) Uani d . 1 C
H16 0.1680(3) 0.3361(2) 0.50768(14) 0.038 Uiso calc R 1 H
O12 0.1950(2) 0.56011(11) 0.46787(11) 0.0385(6) Uani d . 1 O
C17 0.1675(3) 0.6294(2) 0.4879(2) 0.0460(9) Uani d . 1 C
H17A 0.1945(3) 0.6621(2) 0.4558(2) 0.069 Uiso calc R 1 H
H17B 0.2014(3) 0.6390(2) 0.5297(2) 0.069 Uiso calc R 1 H
H17C 0.0881(3) 0.6337(2) 0.4917(2) 0.069 Uiso calc R 1 H
O15 0.0780(2) 0.32975(13) 0.61734(11) 0.0485(6) Uani d . 1 O
C18 0.0248(3) 0.3373(2) 0.6798(2) 0.0580(11) Uani d . 1 C
H18A 0.0110(3) 0.2919(2) 0.6983(2) 0.087 Uiso calc R 1 H
H18B -0.0446(3) 0.3616(2) 0.6743(2) 0.087 Uiso calc R 1 H
H18C 0.0722(3) 0.3635(2) 0.7088(2) 0.087 Uiso calc R 1 H
C21 0.3587(2) 0.45186(15) 0.41411(14) 0.0246(7) Uani d . 1 C
C22 0.4417(3) 0.4172(2) 0.45022(14) 0.0284(7) Uani d . 1 C
C23 0.5517(3) 0.4392(2) 0.4471(2) 0.0342(8) Uani d . 1 C
H23 0.6058(3) 0.4149(2) 0.4705(2) 0.041 Uiso calc R 1 H
C24 0.5826(3) 0.4966(2) 0.4097(2) 0.0363(8) Uani d . 1 C
H24 0.6568(3) 0.5106(2) 0.4086(2) 0.044 Uiso calc R 1 H
C25 0.5038(3) 0.5331(2) 0.37418(15) 0.0317(7) Uani d . 1 C
C26 0.3927(2) 0.5099(2) 0.37653(14) 0.0267(7) Uani d . 1 C
O22 0.4066(2) 0.36169(11) 0.48826(10) 0.0356(5) Uani d . 1 O
C27 0.4893(3) 0.3139(2) 0.5112(2) 0.0525(10) Uani d . 1 C
H27A 0.4545(3) 0.2779(2) 0.5369(2) 0.079 Uiso calc R 1 H
H27B 0.5425(3) 0.3385(2) 0.5378(2) 0.079 Uiso calc R 1 H
H27C 0.5267(3) 0.2932(2) 0.4742(2) 0.079 Uiso calc R 1 H
O25 0.5234(2) 0.59028(12) 0.33563(11) 0.0440(6) Uani d . 1 O
C28 0.6339(3) 0.6190(2) 0.3372(2) 0.0511(10) Uani d . 1 C
H28A 0.6377(3) 0.6588(2) 0.3084(2) 0.077 Uiso calc R 1 H
H28B 0.6863(3) 0.5842(2) 0.3230(2) 0.077 Uiso calc R 1 H
H28C 0.6515(3) 0.6334(2) 0.3813(2) 0.077 Uiso calc R 1 H
C29 0.3126(3) 0.5482(2) 0.3382(2) 0.0312(7) Uani d . 1 C
N30 0.2497(3) 0.57800(15) 0.30596(14) 0.0446(7) Uani d . 1 N
C31 0.2158(3) 0.35894(15) 0.38475(13) 0.0265(7) Uani d . 1 C
C32 0.1088(3) 0.3343(2) 0.36574(15) 0.0365(8) Uani d . 1 C
H32 0.0425(3) 0.3592(2) 0.36960(15) 0.044 Uiso calc R 1 H
C33 0.1195(3) 0.2658(2) 0.34001(15) 0.0425(9) Uani d . 1 C
H33 0.0618(3) 0.2377(2) 0.32460(15) 0.051 Uiso calc R 1 H
C34 0.2332(3) 0.2477(2) 0.34191(15) 0.0406(8) Uani d . 1 C
H34 0.2640(3) 0.2058(2) 0.32737(15) 0.049 Uiso calc R 1 H
C35 0.2921(3) 0.3044(2) 0.36981(15) 0.0360(8) Uani d . 1 C
H35 0.3685(3) 0.3058(2) 0.37720(15) 0.043 Uiso calc R 1 H
C36 0.1860(4) 0.4207(2) 0.2282(2) 0.0597(12) Uani d . 1 C
H36 0.1509(4) 0.4619(2) 0.2411(2) 0.072 Uiso calc R 1 H
C37 0.1335(4) 0.3609(2) 0.2005(2) 0.0627(12) Uani d . 1 C
H37 0.0577(4) 0.3559(2) 0.1924(2) 0.075 Uiso calc R 1 H
C38 0.2158(4) 0.3105(2) 0.1876(2) 0.0609(12) Uani d . 1 C
H38 0.2041(4) 0.2666(2) 0.1691(2) 0.073 Uiso calc R 1 H
C39 0.3190(4) 0.3380(2) 0.2076(2) 0.0591(11) Uani d . 1 C
H39 0.3875(4) 0.3155(2) 0.2049(2) 0.071 Uiso calc R 1 H
C40 0.3000(4) 0.4063(2) 0.2325(2) 0.0615(12) Uani d . 1 C
H40 0.3542(4) 0.4364(2) 0.2490(2) 0.074 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'
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'
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
C34 Fe C37 137.45(15) ?
C34 Fe C32 68.16(14) ?
C37 Fe C32 113.7(2) ?
C34 Fe C36 178.2(2) ?
C37 Fe C36 40.82(15) ?
C32 Fe C36 111.7(2) ?
C34 Fe C33 40.43(14) ?
C37 Fe C33 111.6(2) ?
C32 Fe C33 40.62(13) ?
C36 Fe C33 138.4(2) ?
C34 Fe C40 141.1(2) ?
C37 Fe C40 67.8(2) ?
C32 Fe C40 137.8(2) ?
C36 Fe C40 40.1(2) ?
C33 Fe C40 178.2(2) ?
C34 Fe C35 40.55(12) ?
C37 Fe C35 177.4(2) ?
C32 Fe C35 67.74(14) ?
C36 Fe C35 141.19(15) ?
C33 Fe C35 67.88(14) ?
C40 Fe C35 112.8(2) ?
C34 Fe C39 112.3(2) ?
C37 Fe C39 67.6(2) ?
C32 Fe C39 177.70(15) ?
C36 Fe C39 67.9(2) ?
C33 Fe C39 141.1(2) ?
C40 Fe C39 40.5(2) ?
C35 Fe C39 111.0(2) ?
C34 Fe C38 110.89(15) ?
C37 Fe C38 40.2(2) ?
C32 Fe C38 142.1(2) ?
C36 Fe C38 68.0(2) ?
C33 Fe C38 113.06(14) ?
C40 Fe C38 67.7(2) ?
C35 Fe C38 137.4(2) ?
C39 Fe C38 40.1(2) ?
C34 Fe C31 68.58(12) ?
C37 Fe C31 142.0(2) ?
C32 Fe C31 40.59(12) ?
C36 Fe C31 112.59(13) ?
C33 Fe C31 68.51(12) ?
C40 Fe C31 110.81(13) ?
C35 Fe C31 40.47(11) ?
C39 Fe C31 137.23(15) ?
C38 Fe C31 177.1(2) ?
C31 C1 C21 113.4(2) y
C31 C1 C11 113.2(2) y
C21 C1 C11 112.3(2) y
C16 C11 C12 118.1(3) y
C16 C11 C1 123.0(3) y
C12 C11 C1 118.9(3) y
O12 C12 C13 124.0(3) y
O12 C12 C11 115.7(3) y
C13 C12 C11 120.2(3) y
C12 C13 C14 120.7(3) y
C15 C14 C13 119.8(3) y
C14 C15 O15 124.9(3) y
C14 C15 C16 119.9(3) y
O15 C15 C16 115.2(3) y
C11 C16 C15 121.3(3) y
C12 O12 C17 117.8(3) y
C15 O15 C18 116.8(3) y
C22 C21 C26 116.7(3) y
C22 C21 C1 123.0(3) y
C26 C21 C1 120.2(3) y
O22 C22 C23 123.3(3) y
O22 C22 C21 116.1(3) y
C23 C22 C21 120.6(3) y
C24 C23 C22 121.3(3) y
C25 C24 C23 120.3(3) y
O25 C25 C24 126.0(3) y
O25 C25 C26 115.8(3) y
C24 C25 C26 118.2(3) y
C25 C26 C21 122.8(3) y
C25 C26 C29 117.1(3) y
C21 C26 C29 120.0(3) y
C22 O22 C27 117.6(3) y
C22 O22 C35 88.3(2) n
C27 O22 C35 110.5(2) n
C25 O25 C28 116.9(3) y
N30 C29 C26 178.1(3) y
C35 C31 C32 106.4(3) ?
C35 C31 C1 129.8(3) ?
C32 C31 C1 123.9(3) ?
C35 C31 Fe 69.1(2) ?
C32 C31 Fe 68.8(2) ?
C1 C31 Fe 127.2(2) ?
C33 C32 C31 108.9(3) ?
C33 C32 Fe 69.8(2) ?
C31 C32 Fe 70.6(2) ?
C34 C33 C32 107.8(3) ?
C34 C33 Fe 69.5(2) ?
C32 C33 Fe 69.5(2) ?
C33 C34 C35 107.9(3) ?
C33 C34 Fe 70.1(2) ?
C35 C34 Fe 70.2(2) ?
C34 C35 C31 109.0(3) ?
C34 C35 Fe 69.3(2) ?
C31 C35 Fe 70.4(2) ?
C34 C35 O22 146.8(2) ?
C31 C35 O22 81.7(2) ?
Fe C35 O22 141.93(14) ?
C40 C36 C37 107.4(4) ?
C40 C36 Fe 70.0(2) ?
C37 C36 Fe 69.3(2) ?
C38 C37 C36 108.3(4) ?
C38 C37 Fe 70.6(2) ?
C36 C37 Fe 69.8(2) ?
C37 C38 C39 108.1(4) ?
C37 C38 Fe 69.2(2) ?
C39 C38 Fe 69.9(2) ?
C38 C39 C40 107.8(4) ?
C38 C39 Fe 70.0(2) ?
C40 C39 Fe 69.4(2) ?
C36 C40 C39 108.4(4) ?
C36 C40 Fe 69.9(2) ?
C39 C40 Fe 70.1(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Fe C31 2.062(3) y
Fe C32 2.038(3) y
Fe C33 2.042(3) y
Fe C34 2.034(3) y
Fe C35 2.045(3) y
Fe C36 2.041(4) y
Fe C37 2.034(4) y
Fe C38 2.052(3) y
Fe C39 2.051(3) y
Fe C40 2.043(4) y
C1 C31 1.516(4) y
C1 C21 1.523(4) y
C1 C11 1.535(4) y
C11 C16 1.391(4) y
C11 C12 1.409(4) y
C12 O12 1.376(4) y
C12 C13 1.388(4) y
C13 C14 1.389(5) y
C14 C15 1.377(4) y
C15 O15 1.380(4) y
C15 C16 1.398(4) y
O12 C17 1.424(4) y
O15 C18 1.429(4) y
C21 C22 1.403(4) y
C21 C26 1.408(4) y
C22 O22 1.379(4) y
C22 C23 1.388(4) y
C23 C24 1.385(4) y
C24 C25 1.379(4) y
C25 O25 1.365(4) y
C25 C26 1.406(4) y
C26 C29 1.437(4) y
O22 C27 1.428(4) y
O22 C35 2.981(4) n
O25 C28 1.436(4) y
C29 N30 1.151(4) y
C31 C35 1.420(4) ?
C31 C32 1.422(4) ?
C32 C33 1.416(4) ?
C33 C34 1.408(5) ?
C34 C35 1.413(4) ?
C36 C40 1.399(6) ?
C36 C37 1.421(5) ?
C37 C38 1.403(6) ?
C38 C39 1.406(6) ?
C39 C40 1.417(5) ?
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
C1 C11 C12 O12 -2.6(4)
C1 C21 C22 O22 -0.6(4)
C1 C21 C26 C29 -1.2(4)
C17 O12 O15 C18 -3.9(3)
C27 O22 O25 C28 -23.3(3)