#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:40:09 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179983 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/77/7027769.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7027769
loop_
_publ_author_name
'Klaß, Katrin'
'Fröhlich, Roland'
'Erker, Gerhard'
_publ_section_title
;
 Formation and structural properties of
 1,1′,2,2′-tetra(tert-butylcarbamoyl)-ferrocene and
 -ruthenocene †
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              4457
_journal_paper_doi               10.1039/a906553i
_journal_year                    1999
_chemical_formula_sum            'C30 H46 Fe N4 O4'
_chemical_formula_weight         582.56
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   'geometrically, at N from Diff.-Fourier'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.05(1)
_cell_angle_beta                 99.78(1)
_cell_angle_gamma                107.58(1)
_cell_formula_units_Z            1
_cell_length_a                   6.793(1)
_cell_length_b                   10.902(1)
_cell_length_c                   11.208(1)
_cell_measurement_temperature    198(2)
_cell_volume                     776.41(16)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SCHAKAL-92 (Keller, 1992)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      198(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6015
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  0.9494
_exptl_absorpt_correction_T_min  0.8377
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    'refined as riding atoms'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0360
_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)+(0.0412P)²+0.3959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                3309
_reflns_number_total             3538
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            906553Isup1.cif
_cod_data_source_block           erk1128
_cod_original_cell_volume        776.41(15)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7027769
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Fe Fe 0.0000 0.0000 0.0000 0.02325(11) Uani 1 2 d S
C1 C 0.2884(2) 0.07236(15) -0.04440(13) 0.0242(3) Uani 1 1 d .
C2 C 0.2249(2) -0.06720(15) -0.05167(14) 0.0244(3) Uani 1 1 d .
C3 C 0.1925(2) -0.10384(17) 0.06664(14) 0.0275(3) Uani 1 1 d .
H3 H 0.1501 -0.1900 0.0885 0.033 Uiso 1 1 calc R
C4 C 0.2335(2) 0.00852(18) 0.14568(14) 0.0294(3) Uani 1 1 d .
H4 H 0.2223 0.0109 0.2290 0.035 Uiso 1 1 calc R
C5 C 0.2944(2) 0.11717(17) 0.07854(14) 0.0274(3) Uani 1 1 d .
H5 H 0.3328 0.2050 0.1098 0.033 Uiso 1 1 calc R
C10 C 0.3302(2) 0.15925(16) -0.14363(14) 0.0261(3) Uani 1 1 d .
O11 O 0.2317(2) 0.12735(12) -0.24944(10) 0.0353(3) Uani 1 1 d .
N12 N 0.4775(2) 0.27405(14) -0.10779(12) 0.0277(3) Uani 1 1 d .
H12 H 0.553(3) 0.281(2) -0.039(2) 0.033 Uiso 1 1 d .
C13 C 0.5455(3) 0.37617(17) -0.18908(16) 0.0365(4) Uani 1 1 d .
C14 C 0.3600(4) 0.4209(2) -0.2430(2) 0.0567(6) Uani 1 1 d .
H14A H 0.2466 0.3473 -0.2884 0.085 Uiso 1 1 calc R
H14B H 0.4050 0.4875 -0.2980 0.085 Uiso 1 1 calc R
H14C H 0.3092 0.4568 -0.1774 0.085 Uiso 1 1 calc R
C15 C 0.6348(4) 0.3261(2) -0.2902(2) 0.0553(6) Uani 1 1 d .
H15A H 0.7587 0.3024 -0.2544 0.083 Uiso 1 1 calc R
H15B H 0.6752 0.3939 -0.3447 0.083 Uiso 1 1 calc R
H15C H 0.5279 0.2501 -0.3364 0.083 Uiso 1 1 calc R
C16 C 0.7158(4) 0.4876(2) -0.11011(19) 0.0511(5) Uani 1 1 d .
H16A H 0.6574 0.5190 -0.0456 0.077 Uiso 1 1 calc R
H16B H 0.7670 0.5578 -0.1603 0.077 Uiso 1 1 calc R
H16C H 0.8326 0.4575 -0.0737 0.077 Uiso 1 1 calc R
C20 C 0.2016(2) -0.16858(16) -0.15186(14) 0.0260(3) Uani 1 1 d .
O21 O 0.2144(2) -0.27546(12) -0.12443(11) 0.0332(3) Uani 1 1 d .
N22 N 0.1685(2) -0.13576(15) -0.26554(12) 0.0317(3) Uani 1 1 d .
H22 H 0.167(3) -0.057(2) -0.2747(19) 0.038 Uiso 1 1 d .
C23 C 0.1535(3) -0.21761(18) -0.37716(15) 0.0345(4) Uani 1 1 d .
C24 C 0.3595(4) -0.2473(2) -0.37502(18) 0.0510(5) Uani 1 1 d .
H24A H 0.4735 -0.1666 -0.3746 0.076 Uiso 1 1 calc R
H24B H 0.3464 -0.3046 -0.4473 0.076 Uiso 1 1 calc R
H24C H 0.3908 -0.2898 -0.3018 0.076 Uiso 1 1 calc R
C25 C 0.1165(5) -0.1386(2) -0.48307(18) 0.0583(6) Uani 1 1 d .
H25A H -0.0177 -0.1216 -0.4856 0.087 Uiso 1 1 calc R
H25B H 0.1125 -0.1870 -0.5593 0.087 Uiso 1 1 calc R
H25C H 0.2309 -0.0565 -0.4725 0.087 Uiso 1 1 calc R
C26 C -0.0282(4) -0.3425(2) -0.3879(2) 0.0594(6) Uani 1 1 d .
H26A H -0.0003 -0.3932 -0.3203 0.089 Uiso 1 1 calc R
H26B H -0.0427 -0.3925 -0.4651 0.089 Uiso 1 1 calc R
H26C H -0.1585 -0.3223 -0.3853 0.089 Uiso 1 1 calc 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
C1 Fe C1 180.00(8) 2 .
C1 Fe C2 138.40(6) 2 .
C1 Fe C2 41.60(6) . .
C1 Fe C2 41.60(6) 2 2
C1 Fe C2 138.40(6) . 2
C2 Fe C2 180.00(8) . 2
C1 Fe C3 110.82(6) 2 .
C1 Fe C3 69.18(6) . .
C2 Fe C3 41.08(6) . .
C2 Fe C3 138.92(6) 2 .
C1 Fe C3 69.18(6) 2 2
C1 Fe C3 110.82(6) . 2
C2 Fe C3 138.92(6) . 2
C2 Fe C3 41.08(6) 2 2
C3 Fe C3 180.00(10) . 2
C1 Fe C5 138.80(6) 2 .
C1 Fe C5 41.20(6) . .
C2 Fe C5 69.19(6) . .
C2 Fe C5 110.81(6) 2 .
C3 Fe C5 68.11(7) . .
C3 Fe C5 111.89(7) 2 .
C1 Fe C5 41.20(6) 2 2
C1 Fe C5 138.80(6) . 2
C2 Fe C5 110.81(6) . 2
C2 Fe C5 69.19(6) 2 2
C3 Fe C5 111.89(7) . 2
C3 Fe C5 68.11(7) 2 2
C5 Fe C5 180.00(6) . 2
C1 Fe C4 69.20(6) 2 2
C1 Fe C4 110.80(6) . 2
C2 Fe C4 110.95(6) . 2
C2 Fe C4 69.05(6) 2 2
C3 Fe C4 139.64(7) . 2
C3 Fe C4 40.36(7) 2 2
C5 Fe C4 139.47(7) . 2
C5 Fe C4 40.53(7) 2 2
C1 Fe C4 110.80(6) 2 .
C1 Fe C4 69.20(6) . .
C2 Fe C4 69.05(6) . .
C2 Fe C4 110.95(6) 2 .
C3 Fe C4 40.36(7) . .
C3 Fe C4 139.64(7) 2 .
C5 Fe C4 40.53(7) . .
C5 Fe C4 139.47(7) 2 .
C4 Fe C4 180.00(11) 2 .
C5 C1 C2 107.18(14) . .
C5 C1 C10 123.93(14) . .
C2 C1 C10 128.81(13) . .
C5 C1 Fe 69.86(9) . .
C2 C1 Fe 69.38(8) . .
C10 C1 Fe 123.36(10) . .
C3 C2 C1 107.03(13) . .
C3 C2 C20 120.02(14) . .
C1 C2 C20 132.86(14) . .
C3 C2 Fe 69.63(9) . .
C1 C2 Fe 69.02(8) . .
C20 C2 Fe 128.80(11) . .
C4 C3 C2 109.17(15) . .
C4 C3 Fe 70.18(9) . .
C2 C3 Fe 69.29(9) . .
C3 C4 C5 107.88(14) . .
C3 C4 Fe 69.46(9) . .
C5 C4 Fe 69.49(9) . .
C4 C5 C1 108.73(14) . .
C4 C5 Fe 69.99(9) . .
C1 C5 Fe 68.94(9) . .
O11 C10 N12 123.52(15) . .
O11 C10 C1 121.85(14) . .
N12 C10 C1 114.61(13) . .
C10 N12 C13 124.60(14) . .
N12 C13 C14 109.69(17) . .
N12 C13 C16 106.38(14) . .
C14 C13 C16 109.86(18) . .
N12 C13 C15 110.39(15) . .
C14 C13 C15 110.45(18) . .
C16 C13 C15 110.00(18) . .
O21 C20 N22 124.69(15) . .
O21 C20 C2 118.65(14) . .
N22 C20 C2 116.66(14) . .
C20 N22 C23 125.66(15) . .
N22 C23 C25 106.18(15) . .
N22 C23 C26 110.49(17) . .
C25 C23 C26 110.48(19) . .
N22 C23 C24 109.85(15) . .
C25 C23 C24 109.59(19) . .
C26 C23 C24 110.17(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe C1 2.0332(15) 2
Fe C1 2.0332(15) .
Fe C2 2.0381(15) .
Fe C2 2.0381(15) 2
Fe C3 2.0426(15) .
Fe C3 2.0426(15) 2
Fe C5 2.0455(16) .
Fe C5 2.0455(16) 2
Fe C4 2.0521(15) 2
Fe C4 2.0521(15) .
C1 C5 1.435(2) .
C1 C2 1.446(2) .
C1 C10 1.495(2) .
C2 C3 1.432(2) .
C2 C20 1.501(2) .
C3 C4 1.413(2) .
C4 C5 1.419(2) .
C10 O11 1.2393(19) .
C10 N12 1.341(2) .
N12 C13 1.479(2) .
C13 C14 1.525(3) .
C13 C16 1.524(3) .
C13 C15 1.530(3) .
C20 O21 1.240(2) .
C20 N22 1.336(2) .
N22 C23 1.481(2) .
C23 C25 1.522(3) .
C23 C26 1.521(3) .
C23 C24 1.525(3) .
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_site_symmetry_1
C1 Fe C1 C5 76(100) 2
C2 Fe C1 C5 -118.30(13) .
C2 Fe C1 C5 61.70(13) 2
C3 Fe C1 C5 -80.14(10) .
C3 Fe C1 C5 99.86(10) 2
C5 Fe C1 C5 180.0 2
C4 Fe C1 C5 143.17(10) 2
C4 Fe C1 C5 -36.83(10) .
C1 Fe C1 C2 -165(100) 2
C2 Fe C1 C2 180.0 2
C3 Fe C1 C2 38.17(9) .
C3 Fe C1 C2 -141.83(9) 2
C5 Fe C1 C2 118.30(13) .
C5 Fe C1 C2 -61.70(13) 2
C4 Fe C1 C2 -98.52(10) 2
C4 Fe C1 C2 81.48(10) .
C1 Fe C1 C10 -42(100) 2
C2 Fe C1 C10 123.64(16) .
C2 Fe C1 C10 -56.36(16) 2
C3 Fe C1 C10 161.80(14) .
C3 Fe C1 C10 -18.20(14) 2
C5 Fe C1 C10 -118.06(17) .
C5 Fe C1 C10 61.94(17) 2
C4 Fe C1 C10 25.12(14) 2
C4 Fe C1 C10 -154.88(14) .
C5 C1 C2 C3 0.40(16) .
C10 C1 C2 C3 -176.34(14) .
Fe C1 C2 C3 -59.51(10) .
C5 C1 C2 C20 -176.07(15) .
C10 C1 C2 C20 7.2(3) .
Fe C1 C2 C20 124.03(17) .
C5 C1 C2 Fe 59.90(10) .
C10 C1 C2 Fe -116.83(15) .
C1 Fe C2 C3 -61.51(13) 2
C1 Fe C2 C3 118.49(13) .
C2 Fe C2 C3 -160(100) 2
C3 Fe C2 C3 180.0 2
C5 Fe C2 C3 80.14(10) .
C5 Fe C2 C3 -99.86(10) 2
C4 Fe C2 C3 -143.37(10) 2
C4 Fe C2 C3 36.63(10) .
C1 Fe C2 C1 180.0 2
C2 Fe C2 C1 82(100) 2
C3 Fe C2 C1 -118.49(13) .
C3 Fe C2 C1 61.51(13) 2
C5 Fe C2 C1 -38.35(9) .
C5 Fe C2 C1 141.65(9) 2
C4 Fe C2 C1 98.14(10) 2
C4 Fe C2 C1 -81.86(10) .
C1 Fe C2 C20 51.22(18) 2
C1 Fe C2 C20 -128.78(18) .
C2 Fe C2 C20 -47(100) 2
C3 Fe C2 C20 112.72(18) .
C3 Fe C2 C20 -67.28(18) 2
C5 Fe C2 C20 -167.13(16) .
C5 Fe C2 C20 12.87(16) 2
C4 Fe C2 C20 -30.64(16) 2
C4 Fe C2 C20 149.36(16) .
C1 C2 C3 C4 0.13(17) .
C20 C2 C3 C4 177.14(13) .
Fe C2 C3 C4 -58.99(11) .
C1 C2 C3 Fe 59.12(10) .
C20 C2 C3 Fe -123.87(13) .
C1 Fe C3 C4 -98.00(10) 2
C1 Fe C3 C4 82.00(10) .
C2 Fe C3 C4 120.63(14) .
C2 Fe C3 C4 -59.37(14) 2
C3 Fe C3 C4 75(100) 2
C5 Fe C3 C4 37.61(9) .
C5 Fe C3 C4 -142.39(9) 2
C4 Fe C3 C4 180.0 2
C1 Fe C3 C2 141.37(9) 2
C1 Fe C3 C2 -38.63(9) .
C2 Fe C3 C2 180.0 2
C3 Fe C3 C2 -46(100) 2
C5 Fe C3 C2 -83.01(10) .
C5 Fe C3 C2 96.99(10) 2
C4 Fe C3 C2 59.37(14) 2
C4 Fe C3 C2 -120.63(14) .
C2 C3 C4 C5 -0.62(17) .
Fe C3 C4 C5 -59.06(11) .
C2 C3 C4 Fe 58.45(11) .
C1 Fe C4 C3 98.06(10) 2
C1 Fe C4 C3 -81.94(10) .
C2 Fe C4 C3 -37.27(9) .
C2 Fe C4 C3 142.73(9) 2
C3 Fe C4 C3 180.0 2
C5 Fe C4 C3 -119.36(13) .
C5 Fe C4 C3 60.64(13) 2
C4 Fe C4 C3 11(100) 2
C1 Fe C4 C5 -142.58(9) 2
C1 Fe C4 C5 37.42(9) .
C2 Fe C4 C5 82.10(10) .
C2 Fe C4 C5 -97.90(10) 2
C3 Fe C4 C5 119.36(13) .
C3 Fe C4 C5 -60.64(13) 2
C5 Fe C4 C5 180.0 2
C4 Fe C4 C5 130(100) 2
C3 C4 C5 C1 0.87(17) .
Fe C4 C5 C1 -58.18(10) .
C3 C4 C5 Fe 59.04(11) .
C2 C1 C5 C4 -0.78(17) .
C10 C1 C5 C4 176.15(13) .
Fe C1 C5 C4 58.82(11) .
C2 C1 C5 Fe -59.60(10) .
C10 C1 C5 Fe 117.33(14) .
C1 Fe C5 C4 59.58(13) 2
C1 Fe C5 C4 -120.42(13) .
C2 Fe C5 C4 -81.71(10) .
C2 Fe C5 C4 98.29(10) 2
C3 Fe C5 C4 -37.46(9) .
C3 Fe C5 C4 142.54(9) 2
C5 Fe C5 C4 177(100) 2
C4 Fe C5 C4 180.0 2
C1 Fe C5 C1 180.0 2
C2 Fe C5 C1 38.71(9) .
C2 Fe C5 C1 -141.29(9) 2
C3 Fe C5 C1 82.96(10) .
C3 Fe C5 C1 -97.04(10) 2
C5 Fe C5 C1 -62(81) 2
C4 Fe C5 C1 -59.58(13) 2
C4 Fe C5 C1 120.42(13) .
C5 C1 C10 O11 -143.03(16) .
C2 C1 C10 O11 33.2(2) .
Fe C1 C10 O11 -56.1(2) .
C5 C1 C10 N12 35.3(2) .
C2 C1 C10 N12 -148.42(15) .
Fe C1 C10 N12 122.25(13) .
O11 C10 N12 C13 -1.5(3) .
C1 C10 N12 C13 -179.83(14) .
C10 N12 C13 C14 61.9(2) .
C10 N12 C13 C16 -179.30(17) .
C10 N12 C13 C15 -60.0(2) .
C3 C2 C20 O21 -20.4(2) .
C1 C2 C20 O21 155.70(16) .
Fe C2 C20 O21 -107.46(16) .
C3 C2 C20 N22 159.72(15) .
C1 C2 C20 N22 -24.2(2) .
Fe C2 C20 N22 72.66(19) .
O21 C20 N22 C23 -3.6(3) .
C2 C20 N22 C23 176.24(15) .
C20 N22 C23 C25 -179.70(19) .
C20 N22 C23 C26 60.5(2) .
C20 N22 C23 C24 -61.3(2) .
