#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:31:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180266 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/52/7115249.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_7115249
loop_
_publ_author_name
'Bradley, Sam'
'McGowan, Patrick C.'
'Oughton, Karrie A.'
'Thornton-Pett, Mark'
'Walsh, Mark E.'
_publ_section_title
;
 Facile synthesis of amino-functionalised ferrocenes and vanadocenes
;
_journal_issue                   1
_journal_name_full               'Chemical Communications'
_journal_page_first              77
_journal_paper_doi               10.1039/a808685k
_journal_year                    1999
_chemical_formula_sum            'C22 H32 Fe N2'
_chemical_formula_weight         380.35
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             97-11-17
_audit_creation_method           'STADI4, X-RED'
_cell_angle_alpha                103.584(8)
_cell_angle_beta                 96.905(7)
_cell_angle_gamma                101.691(8)
_cell_formula_units_Z            2
_cell_length_a                   7.1259(5)
_cell_length_b                   10.7296(10)
_cell_length_c                   13.4298(11)
_cell_measurement_reflns_used    78
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      17.6
_cell_volume                     962.08(15)
_computing_cell_refinement       'STADI4 (STOE, 1996)'
_computing_data_collection       'STADI4 (STOE, 1996)'
_computing_data_reduction        'X-RED  (STOE, 1996)'
_computing_molecular_graphics    'ORTEX (McArdle, 1995)'
_computing_publication_material  'local program'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device_type  'STOE STADI4 4-circle-diffractometer'
_diffrn_measurement_method
; Scan width (omega) = 1.65 - 1.80, scan ratio 2theta:omega = 1.00
  I(Net) and sigma(I) calculated according to Blessing (1987)
;
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_radiation_detector       'NaI(Tl) scintillation counter'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  90
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0080
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3780
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  0.7429
_exptl_absorpt_correction_T_min  0.6157
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
    Psi Scan Reflections used    Mu * R = 0.20  

    H   K   L   2Theta   Chi   Imin/Imax
    3  -2   0    17.8   -83.4    0.834
   -3   2   0    17.8    83.4    0.835
    4  -2  -1    23.3   -85.3    0.834
   -4   2   1    23.3    85.3    0.824
    5  -3   0    29.6   -85.5    0.825
   -5   3   0    29.6    85.5    0.834
    6  -4   0    36.0   -83.4    0.828
   -6   4   0    36.0    83.4    0.830
   -7   4   0    41.7    86.2    0.820
    7  -4   0    41.7   -86.2    0.786
   -8   3   2    47.1    84.3    0.821
    8  -3  -2    47.1   -84.3    0.832
;
_exptl_crystal_colour            prism
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0647(24)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.066
_refine_ls_goodness_of_fit_obs   1.067
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_restrained_S_obs      1.067
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_obs          0.0248
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0380P)²+0.4452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0695
_refine_ls_wR_factor_obs         0.0668
_reflns_number_observed          3678
_reflns_number_total             3780
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            808685k.txt
_cod_data_source_block           PM1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.4452P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.4452P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        962.08(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7115249
#BEGIN Tags that were not found in dictionaries:
_audit_contact_author            'J. Richter'
#END Tags that were not found in dictionaries
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Fe Fe 0.19073(2) 0.29740(2) 0.054332(13) 0.01602(8) Uani 1 d .
C1 C 0.1168(2) 0.19955(13) -0.10311(10) 0.0185(3) Uani 1 d .
C2 C 0.2033(2) 0.12263(13) -0.04565(10) 0.0197(3) Uani 1 d .
H2 H 0.1443(2) 0.03612(13) -0.04278(10) 0.024 Uiso 1 calc R
C3 C 0.3936(2) 0.19787(14) 0.00673(10) 0.0219(3) Uani 1 d .
H3 H 0.4824(2) 0.17041(14) 0.05062(10) 0.026 Uiso 1 calc R
C4 C 0.4262(2) 0.32141(14) -0.01862(11) 0.0218(3) Uani 1 d .
H4 H 0.5411(2) 0.39061(14) 0.00499(11) 0.026 Uiso 1 calc R
C5 C 0.2560(2) 0.32271(13) -0.08566(10) 0.0205(3) Uani 1 d .
H5 H 0.2379(2) 0.39349(13) -0.11404(10) 0.025 Uiso 1 calc R
C6 C -0.0769(2) 0.15631(13) -0.17505(10) 0.0199(3) Uani 1 d .
H6 H -0.1172(2) 0.23722(13) -0.18497(10) 0.024 Uiso 1 calc R
C7 C -0.0621(2) 0.07225(15) -0.28224(11) 0.0251(3) Uani 1 d .
H7A H 0.0340(2) 0.12433(15) -0.31341(11) 0.030 Uiso 1 calc R
H7B H -0.0161(2) -0.00646(15) -0.27399(11) 0.030 Uiso 1 calc R
C8 C -0.2591(2) 0.0286(2) -0.35432(11) 0.0289(3) Uani 1 d .
H8A H -0.3008(2) 0.1073(2) -0.36607(11) 0.035 Uiso 1 calc R
H8B H -0.2468(2) -0.0264(2) -0.42245(11) 0.035 Uiso 1 calc R
N9 N -0.4065(2) -0.04680(12) -0.31037(9) 0.0256(3) Uani 1 d .
C9 C -0.5940(2) -0.0907(2) -0.38087(13) 0.0368(4) Uani 1 d .
H9A H -0.5795(5) -0.1451(11) -0.4478(4) 0.055 Uiso 1 calc R
H9B H -0.6390(10) -0.0136(2) -0.3916(8) 0.055 Uiso 1 calc R
H9C H -0.6893(6) -0.1428(11) -0.3505(5) 0.055 Uiso 1 calc R
C10 C -0.4292(2) 0.0335(2) -0.21030(12) 0.0296(3) Uani 1 d .
H10A H -0.5304(2) -0.0183(2) -0.18176(12) 0.036 Uiso 1 calc R
H10B H -0.4724(2) 0.1124(2) -0.22056(12) 0.036 Uiso 1 calc R
C11 C -0.2381(2) 0.0767(2) -0.13332(11) 0.0257(3) Uani 1 d .
H11A H -0.1987(2) -0.0021(2) -0.12016(11) 0.031 Uiso 1 calc R
H11B H -0.2565(2) 0.1314(2) -0.06643(11) 0.031 Uiso 1 calc R
C12 C 0.2661(2) 0.42762(13) 0.20217(10) 0.0188(3) Uani 1 d .
C13 C 0.1755(2) 0.29803(14) 0.20716(10) 0.0208(3) Uani 1 d .
H13 H 0.2320(2) 0.24655(14) 0.24524(10) 0.025 Uiso 1 calc R
C14 C -0.0144(2) 0.25929(15) 0.14513(11) 0.0245(3) Uani 1 d .
H14 H -0.1066(2) 0.17802(15) 0.13544(11) 0.029 Uiso 1 calc R
C15 C -0.0420(2) 0.36336(15) 0.10033(11) 0.0251(3) Uani 1 d .
H15 H -0.1550(2) 0.36362(15) 0.05503(11) 0.030 Uiso 1 calc R
C16 C 0.1308(2) 0.46742(14) 0.13567(11) 0.0221(3) Uani 1 d .
H16 H 0.1523(2) 0.54924(14) 0.11800(11) 0.027 Uiso 1 calc R
C17 C 0.4597(2) 0.51238(13) 0.26250(10) 0.0195(3) Uani 1 d .
H17 H 0.5034(2) 0.58238(13) 0.22687(10) 0.023 Uiso 1 calc R
C18 C 0.6192(2) 0.43679(15) 0.27034(11) 0.0247(3) Uani 1 d .
H18A H 0.5769(2) 0.36468(15) 0.30308(11) 0.030 Uiso 1 calc R
H18B H 0.6409(2) 0.39673(15) 0.19966(11) 0.030 Uiso 1 calc R
C19 C 0.8089(2) 0.5289(2) 0.33474(11) 0.0261(3) Uani 1 d .
H19A H 0.9102(2) 0.4784(2) 0.33865(11) 0.031 Uiso 1 calc R
H19B H 0.8540(2) 0.5989(2) 0.30043(11) 0.031 Uiso 1 calc R
N20 N 0.7818(2) 0.58932(12) 0.43989(9) 0.0247(3) Uani 1 d .
C20 C 0.9652(2) 0.6737(2) 0.50198(12) 0.0342(4) Uani 1 d .
H20A H 1.0627(6) 0.6214(3) 0.5044(8) 0.051 Uiso 1 calc R
H20B H 0.9456(5) 0.7111(10) 0.5728(3) 0.051 Uiso 1 calc R
H20C H 1.0105(10) 0.7454(7) 0.4705(6) 0.051 Uiso 1 calc R
C21 C 0.6341(2) 0.66556(15) 0.43674(11) 0.0273(3) Uani 1 d .
H21A H 0.6791(2) 0.73894(15) 0.40573(11) 0.033 Uiso 1 calc R
H21B H 0.6173(2) 0.70444(15) 0.50866(11) 0.033 Uiso 1 calc R
C22 C 0.4385(2) 0.58086(14) 0.37355(11) 0.0235(3) Uani 1 d .
H22A H 0.3450(2) 0.63714(14) 0.37006(11) 0.028 Uiso 1 calc R
H22B H 0.3862(2) 0.51325(14) 0.40862(11) 0.028 Uiso 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'
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
C15 Fe C3 169.48(6)
C15 Fe C4 148.58(6)
C3 Fe C4 40.85(6)
C15 Fe C16 40.94(6)
C3 Fe C16 148.53(6)
C4 Fe C16 115.94(6)
C15 Fe C14 40.71(6)
C3 Fe C14 130.72(6)
C4 Fe C14 169.34(6)
C16 Fe C14 68.32(6)
C15 Fe C5 116.26(6)
C3 Fe C5 68.51(6)
C4 Fe C5 40.70(5)
C16 Fe C5 108.37(6)
C14 Fe C5 149.16(6)
C15 Fe C2 130.55(6)
C3 Fe C2 40.82(5)
C4 Fe C2 68.45(6)
C16 Fe C2 169.33(5)
C14 Fe C2 109.21(6)
C5 Fe C2 68.06(5)
C15 Fe C13 68.46(6)
C3 Fe C13 108.68(6)
C4 Fe C13 130.38(6)
C16 Fe C13 68.08(6)
C14 Fe C13 40.53(6)
C5 Fe C13 168.99(5)
C2 Fe C13 117.31(5)
C15 Fe C1 108.33(5)
C3 Fe C1 68.65(5)
C4 Fe C1 68.57(5)
C16 Fe C1 130.43(5)
C14 Fe C1 116.91(5)
C5 Fe C1 40.57(5)
C2 Fe C1 40.48(5)
C13 Fe C1 149.51(5)
C15 Fe C12 68.66(5)
C3 Fe C12 116.23(5)
C4 Fe C12 108.14(5)
C16 Fe C12 40.58(5)
C14 Fe C12 68.20(5)
C5 Fe C12 130.33(5)
C2 Fe C12 149.26(5)
C13 Fe C12 40.36(5)
C1 Fe C12 169.04(5)
C2 C1 C5 107.03(12)
C2 C1 C6 126.82(12)
C5 C1 C6 125.98(12)
C2 C1 Fe 69.09(7)
C5 C1 Fe 68.88(7)
C6 C1 Fe 130.60(9)
C3 C2 C1 108.54(12)
C3 C2 Fe 68.89(7)
C1 C2 Fe 70.43(7)
C4 C3 C2 107.86(12)
C4 C3 Fe 69.72(8)
C2 C3 Fe 70.29(8)
C3 C4 C5 107.90(12)
C3 C4 Fe 69.43(8)
C5 C4 Fe 70.04(8)
C4 C5 C1 108.67(12)
C4 C5 Fe 69.26(8)
C1 C5 Fe 70.55(7)
C1 C6 C11 113.53(11)
C1 C6 C7 111.12(11)
C11 C6 C7 107.95(11)
C8 C7 C6 110.68(12)
N9 C8 C7 111.34(12)
C8 N9 C9 111.05(12)
C8 N9 C10 110.27(12)
C9 N9 C10 109.29(12)
N9 C10 C11 110.79(12)
C10 C11 C6 111.12(12)
C13 C12 C16 107.25(12)
C13 C12 C17 126.88(12)
C16 C12 C17 125.66(12)
C13 C12 Fe 69.39(7)
C16 C12 Fe 68.59(7)
C17 C12 Fe 131.19(9)
C14 C13 C12 108.31(12)
C14 C13 Fe 69.19(8)
C12 C13 Fe 70.25(7)
C15 C14 C13 108.22(12)
C15 C14 Fe 69.06(8)
C13 C14 Fe 70.28(8)
C14 C15 C16 107.73(12)
C14 C15 Fe 70.23(8)
C16 C15 Fe 69.96(8)
C15 C16 C12 108.50(13)
C15 C16 Fe 69.10(8)
C12 C16 Fe 70.84(7)
C12 C17 C18 113.99(11)
C12 C17 C22 110.21(11)
C18 C17 C22 108.29(11)
C19 C18 C17 110.70(12)
N20 C19 C18 110.81(12)
C20 N20 C21 110.11(12)
C20 N20 C19 110.46(12)
C21 N20 C19 110.78(11)
N20 C21 C22 112.03(12)
C21 C22 C17 111.06(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Fe C15 2.0369(14)
Fe C3 2.0410(13)
Fe C4 2.0448(13)
Fe C16 2.0483(13)
Fe C14 2.0524(14)
Fe C5 2.0551(13)
Fe C2 2.0595(13)
Fe C13 2.0668(13)
Fe C1 2.0774(13)
Fe C12 2.0782(13)
C1 C2 1.431(2)
C1 C5 1.433(2)
C1 C6 1.504(2)
C2 C3 1.430(2)
C3 C4 1.426(2)
C4 C5 1.426(2)
C6 C11 1.531(2)
C6 C7 1.537(2)
C7 C8 1.524(2)
C8 N9 1.461(2)
N9 C9 1.461(2)
N9 C10 1.463(2)
C10 C11 1.523(2)
C12 C13 1.430(2)
C12 C16 1.431(2)
C12 C17 1.504(2)
C13 C14 1.427(2)
C14 C15 1.422(2)
C15 C16 1.429(2)
C17 C18 1.532(2)
C17 C22 1.540(2)
C18 C19 1.526(2)
C19 N20 1.462(2)
N20 C20 1.459(2)
N20 C21 1.460(2)
C21 C22 1.526(2)
