#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:51:17 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178704 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/15/4081529.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4081529
loop_
_publ_author_name
'Klapp, Lutz R. R.'
'Bruhn, Clemens'
'Leibold, Michael'
'Siemeling, Ulrich'
_publ_section_title
;
 Ferrocene-Based Bis(guanidines): Superbases for Tridentate
 N,Fe,N-Coordination
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              5862
_journal_paper_doi               10.1021/om400454v
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C20 H28 Fe N6'
_chemical_formula_sum            'C20 H28 Fe N6'
_chemical_formula_weight         408.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5867(6)
_cell_length_b                   10.9127(7)
_cell_length_c                   16.5647(9)
_cell_measurement_reflns_used    8467
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.54
_cell_measurement_theta_min      1.92
_cell_volume                     1913.71(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      ' 103 frames, detector distance = 135 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6482
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.95
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  0.9058
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-red ver. 1.31 (Stoe & Cie. 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0274
_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)+(0.0578P)²+0.0691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                1450
_reflns_number_total             1671
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400454v_si_002.cif
_cod_data_source_block           i0926
_cod_database_code               4081529
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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
C1 C -0.00773(12) 0.33041(13) 0.55896(10) 0.0225(3) Uani 1 1 d .
C2 C 0.05388(14) 0.32037(11) 0.48200(9) 0.0245(3) Uani 1 1 d .
H2A H 0.1379 0.2928 0.4731 0.029 Uiso 1 1 calc R
C3 C -0.03343(15) 0.35922(12) 0.42070(9) 0.0260(3) Uani 1 1 d .
H3A H -0.0179 0.3607 0.3642 0.031 Uiso 1 1 calc R
C4 C -0.14788(13) 0.39532(12) 0.45984(10) 0.0264(3) Uani 1 1 d .
H4A H -0.2220 0.4248 0.4339 0.032 Uiso 1 1 calc R
C5 C -0.13117(12) 0.37924(12) 0.54473(9) 0.0233(3) Uani 1 1 d .
H5A H -0.1920 0.3979 0.5851 0.028 Uiso 1 1 calc R
C6 C 0.05918(12) 0.18841(11) 0.65550(8) 0.0216(3) Uani 1 1 d .
C7 C 0.04703(18) -0.02288(13) 0.67237(11) 0.0353(4) Uani 1 1 d .
H7A H 0.0769 -0.0964 0.6429 0.042 Uiso 1 1 calc R
H7B H -0.0303 -0.0440 0.7030 0.042 Uiso 1 1 calc R
C8 C 0.14887(15) 0.02695(12) 0.72778(9) 0.0308(4) Uani 1 1 d .
H8B H 0.1420 -0.0080 0.7828 0.037 Uiso 1 1 calc R
H8A H 0.2344 0.0107 0.7061 0.037 Uiso 1 1 calc R
C9 C -0.09298(13) 0.06946(13) 0.57021(9) 0.0291(3) Uani 1 1 d .
H9A H -0.0947 0.1331 0.5285 0.035 Uiso 1 1 calc R
H9B H -0.1656 0.0798 0.6063 0.035 Uiso 1 1 calc R
H9C H -0.0970 -0.0115 0.5447 0.035 Uiso 1 1 calc R
C10 C 0.21140(16) 0.24093(11) 0.76226(9) 0.0293(3) Uani 1 1 d .
H10C H 0.2113 0.2317 0.8211 0.035 Uiso 1 1 calc R
H10B H 0.1893 0.3255 0.7482 0.035 Uiso 1 1 calc R
H10A H 0.2956 0.2218 0.7412 0.035 Uiso 1 1 calc R
N2 N 0.02411(11) 0.07976(10) 0.61678(8) 0.0248(3) Uani 1 1 d .
N3 N 0.11949(11) 0.15778(10) 0.72717(7) 0.0247(3) Uani 1 1 d .
N1 N 0.04461(11) 0.30159(9) 0.63482(7) 0.0239(3) Uani 1 1 d .
Fe1 Fe 0.0000 0.5000 0.5000 0.02036(15) Uani 1 2 d S
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'
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
N1 C1 C5 126.10(13) . .
N1 C1 C2 126.59(12) . .
C5 C1 C2 107.28(12) . .
N1 C1 Fe1 126.71(10) . .
C5 C1 Fe1 68.27(8) . .
C2 C1 Fe1 68.64(8) . .
C1 C2 C3 108.22(13) . .
C1 C2 Fe1 70.96(8) . .
C3 C2 Fe1 69.15(7) . .
C1 C2 H2A 125.9 . .
C3 C2 H2A 125.9 . .
Fe1 C2 H2A 125.6 . .
C4 C3 C2 107.82(13) . .
C4 C3 Fe1 69.49(8) . .
C2 C3 Fe1 69.98(8) . .
C4 C3 H3A 126.1 . .
C2 C3 H3A 126.1 . .
Fe1 C3 H3A 126.0 . .
C5 C4 C3 107.92(12) . .
C5 C4 Fe1 69.77(7) . .
C3 C4 Fe1 69.71(8) . .
C5 C4 H4A 126.0 . .
C3 C4 H4A 126.0 . .
Fe1 C4 H4A 126.1 . .
C4 C5 C1 108.73(13) . .
C4 C5 Fe1 69.48(7) . .
C1 C5 Fe1 71.38(8) . .
C4 C5 H5A 125.6 . .
C1 C5 H5A 125.6 . .
Fe1 C5 H5A 125.1 . .
N1 C6 N3 120.80(12) . .
N1 C6 N2 131.14(13) . .
N3 C6 N2 108.06(11) . .
N2 C7 C8 102.90(11) . .
N2 C7 H7A 111.2 . .
C8 C7 H7A 111.2 . .
N2 C7 H7B 111.2 . .
C8 C7 H7B 111.2 . .
H7A C7 H7B 109.1 . .
N3 C8 C7 101.23(12) . .
N3 C8 H8B 111.5 . .
C7 C8 H8B 111.5 . .
N3 C8 H8A 111.5 . .
C7 C8 H8A 111.5 . .
H8B C8 H8A 109.3 . .
N2 C9 H9A 109.5 . .
N2 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N2 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N3 C10 H10C 109.5 . .
N3 C10 H10B 109.5 . .
H10C C10 H10B 109.5 . .
N3 C10 H10A 109.5 . .
H10C C10 H10A 109.5 . .
H10B C10 H10A 109.5 . .
C6 N2 C9 122.11(11) . .
C6 N2 C7 108.36(12) . .
C9 N2 C7 114.28(12) . .
C6 N3 C10 120.00(11) . .
C6 N3 C8 109.81(11) . .
C10 N3 C8 117.73(12) . .
C6 N1 C1 119.81(12) . .
C4 Fe1 C4 180.0 . 5_566
C4 Fe1 C3 139.20(6) . 5_566
C4 Fe1 C3 40.80(6) 5_566 5_566
C4 Fe1 C3 40.80(6) . .
C4 Fe1 C3 139.20(6) 5_566 .
C3 Fe1 C3 180.0 5_566 .
C4 Fe1 C5 40.75(7) . .
C4 Fe1 C5 139.25(7) 5_566 .
C3 Fe1 C5 111.49(6) 5_566 .
C3 Fe1 C5 68.52(6) . .
C4 Fe1 C5 139.25(7) . 5_566
C4 Fe1 C5 40.75(7) 5_566 5_566
C3 Fe1 C5 68.51(6) 5_566 5_566
C3 Fe1 C5 111.49(6) . 5_566
C5 Fe1 C5 180.0 . 5_566
C4 Fe1 C2 111.43(5) . 5_566
C4 Fe1 C2 68.57(5) 5_566 5_566
C3 Fe1 C2 40.88(6) 5_566 5_566
C3 Fe1 C2 139.12(6) . 5_566
C5 Fe1 C2 111.76(5) . 5_566
C5 Fe1 C2 68.24(5) 5_566 5_566
C4 Fe1 C2 68.57(5) . .
C4 Fe1 C2 111.43(5) 5_566 .
C3 Fe1 C2 139.12(6) 5_566 .
C3 Fe1 C2 40.88(6) . .
C5 Fe1 C2 68.24(5) . .
C5 Fe1 C2 111.76(5) 5_566 .
C2 Fe1 C2 180.0 5_566 .
C4 Fe1 C1 68.22(5) . .
C4 Fe1 C1 111.78(5) 5_566 .
C3 Fe1 C1 111.71(6) 5_566 .
C3 Fe1 C1 68.29(6) . .
C5 Fe1 C1 40.35(5) . .
C5 Fe1 C1 139.65(5) 5_566 .
C2 Fe1 C1 139.59(6) 5_566 .
C2 Fe1 C1 40.41(6) . .
C4 Fe1 C1 111.78(5) . 5_566
C4 Fe1 C1 68.22(5) 5_566 5_566
C3 Fe1 C1 68.29(6) 5_566 5_566
C3 Fe1 C1 111.71(6) . 5_566
C5 Fe1 C1 139.65(5) . 5_566
C5 Fe1 C1 40.35(5) 5_566 5_566
C2 Fe1 C1 40.41(6) 5_566 5_566
C2 Fe1 C1 139.59(6) . 5_566
C1 Fe1 C1 180.0 . 5_566
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.409(2) .
C1 C5 1.4308(18) .
C1 C2 1.436(2) .
C1 Fe1 2.0942(15) .
C2 C3 1.437(2) .
C2 Fe1 2.0632(13) .
C2 H2A 0.9500 .
C3 C4 1.430(2) .
C3 Fe1 2.0521(14) .
C3 H3A 0.9500 .
C4 C5 1.428(2) .
C4 Fe1 2.0491(13) .
C4 H4A 0.9500 .
C5 Fe1 2.0528(13) .
C5 H5A 0.9500 .
C6 N1 1.2910(16) .
C6 N3 1.3888(18) .
C6 N2 1.3982(17) .
C7 N2 1.470(2) .
C7 C8 1.517(2) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 N3 1.4613(17) .
C8 H8B 0.9900 .
C8 H8A 0.9900 .
C9 N2 1.4644(18) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 N3 1.4519(19) .
C10 H10C 0.9800 .
C10 H10B 0.9800 .
C10 H10A 0.9800 .
Fe1 C4 2.0491(13) 5_566
Fe1 C3 2.0520(14) 5_566
Fe1 C5 2.0529(13) 5_566
Fe1 C2 2.0631(13) 5_566
Fe1 C1 2.0942(15) 5_566
