#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/74/4107423.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_4107423
loop_
_publ_author_name
'Alois Fürstner'
'Keisuke Majima'
'Rubén Martín'
'Helga Krause'
'Egmont Kattnig'
'Richard Goddard'
'Christian W. Lehmann'
_publ_section_title
;
 A Cheap Metal for a "Noble" Task: Preparative and Mechanistic Aspects of
 Cycloisomerization and Cycloaddition Reactions Catalyzed by Low-Valent
 Iron Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1992
_journal_page_last               2004
_journal_paper_doi               10.1021/ja0777180
_journal_volume                  130
_journal_year                    2008
_chemical_compound_source        tetrahydrofuran
_chemical_formula_moiety         'C9 H13 Fe 1-, Li 1+, C6 H16 N2'
_chemical_formula_sum            'C15 H29 Fe Li N2'
_chemical_formula_weight         300.19
_chemical_name_systematic
; 
 tetramethyl-ethylenediamine-lithium-bis-ethylene-cyclopentadienyl-iron
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                MJM-MC-193-01
_audit_creation_date             2007-09-05
_cell_angle_alpha                94.945(1)
_cell_angle_beta                 98.755(1)
_cell_angle_gamma                107.135(1)
_cell_formula_units_Z            2
_cell_length_a                   8.1030(2)
_cell_length_b                   9.4613(2)
_cell_length_c                   11.1671(2)
_cell_measurement_reflns_used    37181
_cell_measurement_temperature    100
_cell_measurement_theta_max      40.25
_cell_measurement_theta_min      2.91
_cell_volume                     800.77(3)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.18
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD ω-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29174
_diffrn_reflns_theta_full        37.47
_diffrn_reflns_theta_max         37.47
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_T_max  0.93035
_exptl_absorpt_correction_T_min  0.86537
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'XPREP, Siemens (1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.747
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         8064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.3209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0927
_reflns_number_gt                7358
_reflns_number_total             8064
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja0777180-file002.cif
_cod_data_source_block           5952
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     '-p 1'
_cod_database_code               4107423
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
C1 C 0.24550(13) 0.08296(11) 0.09937(8) 0.01706(15) Uani 1 1 d .
H1A H 0.3549 0.0690 0.0844 0.020 Uiso 1 1 calc R
H1B H 0.1415 0.0052 0.0552 0.020 Uiso 1 1 calc R
C2 C 0.23771(15) 0.23299(12) 0.10837(9) 0.02052(17) Uani 1 1 d .
H2A H 0.1290 0.2465 0.0694 0.025 Uiso 1 1 calc R
H2B H 0.3423 0.3102 0.0987 0.025 Uiso 1 1 calc R
C3 C -0.00482(13) 0.01458(12) 0.26109(10) 0.01976(16) Uani 1 1 d .
H3A H -0.0565 -0.0501 0.1839 0.024 Uiso 1 1 calc R
H3B H -0.0285 -0.0344 0.3323 0.024 Uiso 1 1 calc R
C4 C -0.00936(14) 0.16529(12) 0.26578(10) 0.02144(17) Uani 1 1 d .
H4A H -0.0362 0.2079 0.3398 0.026 Uiso 1 1 calc R
H4B H -0.0642 0.1922 0.1915 0.026 Uiso 1 1 calc R
C5 C 0.41514(14) 0.09306(12) 0.39037(9) 0.02041(17) Uani 1 1 d .
H5 H 0.4255 -0.0077 0.3879 0.024 Uiso 1 1 calc R
C6 C 0.50977(13) 0.21079(12) 0.33131(10) 0.02115(17) Uani 1 1 d .
H6 H 0.5946 0.2040 0.2790 0.025 Uiso 1 1 calc R
C7 C 0.46197(15) 0.34052(12) 0.36327(11) 0.02380(19) Uani 1 1 d .
H7 H 0.5057 0.4374 0.3347 0.029 Uiso 1 1 calc R
C8 C 0.33917(16) 0.30506(13) 0.44178(10) 0.0252(2) Uani 1 1 d .
H8 H 0.2831 0.3730 0.4774 0.030 Uiso 1 1 calc R
C9 C 0.31009(16) 0.15297(13) 0.45958(9) 0.02362(19) Uani 1 1 d .
H9 H 0.2327 0.0989 0.5113 0.028 Uiso 1 1 calc R
C10 C 0.33719(15) -0.35705(12) 0.21833(12) 0.02425(19) Uani 1 1 d .
H10A H 0.4037 -0.3275 0.3012 0.029 Uiso 1 1 calc R
H10B H 0.3813 -0.4291 0.1774 0.029 Uiso 1 1 calc R
C11 C 0.14469(15) -0.42955(12) 0.22220(12) 0.0253(2) Uani 1 1 d .
H11A H 0.0797 -0.4678 0.1396 0.030 Uiso 1 1 calc R
H11B H 0.1328 -0.5131 0.2684 0.030 Uiso 1 1 calc R
C12 C 0.55339(13) -0.14286(13) 0.17581(10) 0.02242(18) Uani 1 1 d .
H12A H 0.5961 -0.1135 0.2621 0.034 Uiso 1 1 calc R
H12B H 0.5725 -0.0556 0.1353 0.034 Uiso 1 1 calc R
H12C H 0.6151 -0.2060 0.1445 0.034 Uiso 1 1 calc R
C13 C 0.30230(15) -0.26866(14) 0.02096(10) 0.02500(19) Uani 1 1 d .
H13A H 0.3211 -0.1808 -0.0188 0.037 Uiso 1 1 calc R
H13B H 0.1792 -0.3237 0.0048 0.037 Uiso 1 1 calc R
H13C H 0.3664 -0.3300 -0.0097 0.037 Uiso 1 1 calc R
C14 C 0.12361(19) -0.29790(16) 0.41274(12) 0.0318(2) Uani 1 1 d .
H14A H 0.2494 -0.2586 0.4339 0.048 Uiso 1 1 calc R
H14B H 0.0842 -0.3912 0.4438 0.048 Uiso 1 1 calc R
H14C H 0.0727 -0.2284 0.4479 0.048 Uiso 1 1 calc R
C15 C -0.12328(16) -0.38184(14) 0.24819(13) 0.0299(2) Uani 1 1 d .
H15A H -0.1600 -0.3978 0.1609 0.045 Uiso 1 1 calc R
H15B H -0.1736 -0.3121 0.2837 0.045 Uiso 1 1 calc R
H15C H -0.1621 -0.4749 0.2796 0.045 Uiso 1 1 calc R
Fe1 Fe 0.239704(16) 0.160260(14) 0.273377(11) 0.01335(4) Uani 1 1 d .
Li1 Li 0.1958(3) -0.1130(2) 0.21919(18) 0.0191(3) Uani 1 1 d .
N1 N 0.36391(11) -0.22500(10) 0.15367(8) 0.01790(14) Uani 1 1 d .
N2 N 0.06935(12) -0.32166(10) 0.27931(9) 0.02052(15) Uani 1 1 d .
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'
Li Li -0.0003 0.0001 '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
C2 C1 Fe1 68.97(5) y
C2 C1 Li1 136.90(8) y
Fe1 C1 Li1 69.42(5) y
C1 C2 Fe1 69.53(5) y
C4 C3 Fe1 68.97(6) y
C4 C3 Li1 136.27(9) y
Fe1 C3 Li1 69.10(6) y
C3 C4 Fe1 69.57(6) y
C6 C5 C9 106.97(9) y
C6 C5 Fe1 70.67(6) y
C9 C5 Fe1 70.66(6) y
C6 C5 Li1 107.57(8) y
C9 C5 Li1 106.64(8) y
Fe1 C5 Li1 63.43(5) y
C7 C6 C5 108.32(10) y
C7 C6 Fe1 71.72(6) y
C5 C6 Fe1 68.98(6) y
C8 C7 C6 108.30(10) y
C8 C7 Fe1 70.61(6) y
C6 C7 Fe1 68.67(6) y
C7 C8 C9 108.04(10) y
C7 C8 Fe1 70.57(6) y
C9 C8 Fe1 68.72(6) y
C8 C9 C5 108.37(10) y
C8 C9 Fe1 71.71(6) y
C5 C9 Fe1 68.88(6) y
N1 C10 C11 111.74(9) y
N2 C11 C10 111.26(9) y
C2 Fe1 C4 88.92(4) y
C2 Fe1 C1 41.50(4) y
C4 Fe1 C1 104.02(4) y
C2 Fe1 C3 104.62(4) y
C4 Fe1 C3 41.45(4) y
C1 Fe1 C3 90.71(4) y
C2 Fe1 C5 134.84(4) y
C4 Fe1 C5 136.06(5) y
C1 Fe1 C5 108.19(4) y
C3 Fe1 C5 108.72(4) y
C2 Fe1 C6 99.40(4) y
C4 Fe1 C6 160.46(5) y
C1 Fe1 C6 93.74(4) y
C3 Fe1 C6 148.22(4) y
C5 Fe1 C6 40.35(4) y
C2 Fe1 C9 160.66(5) y
C4 Fe1 C9 100.16(5) y
C1 Fe1 C9 147.53(4) y
C3 Fe1 C9 93.30(4) y
C5 Fe1 C9 40.45(5) y
C6 Fe1 C9 67.01(5) y
C2 Fe1 C7 94.59(5) y
C4 Fe1 C7 122.57(5) y
C1 Fe1 C7 115.80(5) y
C3 Fe1 C7 153.35(5) y
C5 Fe1 C7 67.14(4) y
C6 Fe1 C7 39.61(4) y
C9 Fe1 C7 66.12(5) y
C2 Fe1 C8 123.30(5) y
C4 Fe1 C8 94.37(5) y
C1 Fe1 C8 154.60(5) y
C3 Fe1 C8 114.58(5) y
C5 Fe1 C8 67.26(4) y
C6 Fe1 C8 66.27(5) y
C9 Fe1 C8 39.58(5) y
C7 Fe1 C8 38.83(5) y
C2 Fe1 Li1 102.23(5) y
C4 Fe1 Li1 102.44(5) y
C1 Fe1 Li1 61.41(5) y
C3 Fe1 Li1 61.83(5) y
C5 Fe1 Li1 69.35(5) y
C6 Fe1 Li1 93.11(5) y
C9 Fe1 Li1 92.53(6) y
C7 Fe1 Li1 132.14(5) y
C8 Fe1 Li1 131.67(6) y
N1 Li1 N2 85.48(8) y
N1 Li1 C1 98.48(8) y
N2 Li1 C1 159.83(10) y
N1 Li1 C3 171.46(10) y
N2 Li1 C3 98.28(8) y
C1 Li1 C3 75.39(7) y
N1 Li1 Fe1 130.80(9) y
N2 Li1 Fe1 138.70(9) y
C1 Li1 Fe1 49.18(4) y
C3 Li1 Fe1 49.07(4) y
N1 Li1 C5 102.10(8) y
N2 Li1 C5 115.49(9) y
C1 Li1 C5 83.18(7) y
C3 Li1 C5 83.27(7) y
Fe1 Li1 C5 47.22(4) y
C13 N1 C12 108.27(8) y
C13 N1 C10 111.19(9) y
C12 N1 C10 108.59(8) y
C13 N1 Li1 107.51(8) y
C12 N1 Li1 117.44(8) y
C10 N1 Li1 103.79(8) y
C14 N2 C15 108.91(10) y
C14 N2 C11 110.82(10) y
C15 N2 C11 108.71(9) y
C14 N2 Li1 105.75(9) y
C15 N2 Li1 118.06(9) y
C11 N2 Li1 104.46(8) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.4349(14) y
C1 Fe1 2.0288(9) y
C1 Li1 2.354(2) y
C2 Fe1 2.0212(10) y
C3 C4 1.4339(15) y
C3 Fe1 2.0297(10) y
C3 Li1 2.368(2) y
C4 Fe1 2.0217(10) y
C5 C6 1.4285(15) y
C5 C9 1.4326(16) y
C5 Fe1 2.0597(10) y
C5 Li1 2.626(2) y
C6 C7 1.4250(16) y
C6 Fe1 2.0821(10) y
C7 C8 1.4110(18) y
C7 Fe1 2.1224(10) y
C8 C9 1.4245(17) y
C8 Fe1 2.1229(10) y
C9 Fe1 2.0834(10) y
C10 N1 1.4740(14) y
C10 C11 1.5168(16) y
C11 N2 1.4815(15) y
C12 N1 1.4733(14) y
C13 N1 1.4710(14) y
C14 N2 1.4659(16) y
C15 N2 1.4691(15) y
Fe1 Li1 2.5097(19) y
Li1 N1 2.129(2) y
Li1 N2 2.155(2) y
