#------------------------------------------------------------------------------
#$Date: 2014-07-11 19:33:45 +0100 (Fri, 11 Jul 2014) $
#$Revision: 120075 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/57/4075720.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_4075720
loop_
_publ_author_name
'Joly, K\'evin M.'
'Kariuki, Benson M.'
'Coe, Diane M.'
'Cox, Liam R.'
_publ_section_title
;
 One-Pot Synthesis of 1,1‘-Bis(2-amino)ethyl-Substituted Ferrocenes
 from the Reaction of Spiro[2.4]hepta-4,6-diene with Lithium
 Amides:  An Expedient Route into Functionalized Ferrocenophanes
;
_journal_issue                   3
_journal_name_full               Organometallics
_journal_page_first              358
_journal_volume                  24
_journal_year                    2005
_chemical_formula_moiety         'C22 H32 Fe N2 O2, 2(H2 O)'
_chemical_formula_sum            'C22 H36 Fe N2 O4'
_chemical_formula_weight         448.38
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 102.798(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.448(3)
_cell_length_b                   12.5409(15)
_cell_length_c                   9.3747(12)
_cell_measurement_reflns_used    2347
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.38
_cell_measurement_theta_min      1.95
_cell_volume                     2229.6(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_molecular_graphics    PLATON
_computing_publication_material  PLATON
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Rigaku R-axis IIc'
_diffrn_measurement_method       'Image plate scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7624
_diffrn_reflns_theta_full        29.38
_diffrn_reflns_theta_max         29.38
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  0.8161
_exptl_absorpt_correction_T_min  0.7655
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.974
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0524
_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/[\s^2^(Fo^2^)+(0.0921P)^2^+1.6352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1710
_reflns_number_gt                2347
_reflns_number_total             2809
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    om049222msi20041104_051556.cif
_[local]_cod_data_source_block   kmj1
_[local]_cod_cif_authors_sg_H-M  C2/c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4075720
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Fe1 Fe -0.5000 0.36787(4) 0.2500 0.03476(19) Uani 1 2 d S
C1 C -0.27838(17) 0.1266(2) 0.7121(4) 0.0515(7) Uani 1 1 d .
H1A H -0.2460 0.1862 0.7347 0.062 Uiso 1 1 calc R
H1B H -0.2736 0.0965 0.6195 0.062 Uiso 1 1 calc R
C2 C -0.25925(19) 0.0434(3) 0.8301(4) 0.0638(9) Uani 1 1 d .
H2A H -0.2906 -0.0171 0.8053 0.077 Uiso 1 1 calc R
H2B H -0.2116 0.0189 0.8341 0.077 Uiso 1 1 calc R
C3 C -0.3329(2) 0.1183(3) 0.9588(4) 0.0627(9) Uani 1 1 d .
H3A H -0.3372 0.1466 1.0528 0.075 Uiso 1 1 calc R
H3B H -0.3649 0.0583 0.9358 0.075 Uiso 1 1 calc R
C4 C -0.35485(19) 0.2044(3) 0.8422(3) 0.0557(8) Uani 1 1 d .
H4A H -0.4028 0.2268 0.8403 0.067 Uiso 1 1 calc R
H4B H -0.3243 0.2659 0.8667 0.067 Uiso 1 1 calc R
C5 C -0.37104(16) 0.2488(2) 0.5877(3) 0.0466(6) Uani 1 1 d .
H5A H -0.3366 0.3059 0.6085 0.056 Uiso 1 1 calc R
H5B H -0.4162 0.2780 0.5960 0.056 Uiso 1 1 calc R
C6 C -0.37675(16) 0.2116(2) 0.4310(3) 0.0462(6) Uani 1 1 d .
H6A H -0.3309 0.1862 0.4210 0.055 Uiso 1 1 calc R
H6B H -0.4093 0.1520 0.4117 0.055 Uiso 1 1 calc R
C7 C -0.40170(14) 0.2975(2) 0.3171(3) 0.0401(5) Uani 1 1 d .
C8 C -0.39635(13) 0.4099(2) 0.3403(3) 0.0420(6) Uani 1 1 d .
H8 H -0.3787 0.4441 0.4288 0.050 Uiso 1 1 calc R
C9 C -0.42323(14) 0.4605(2) 0.2018(4) 0.0482(7) Uani 1 1 d .
H9 H -0.4256 0.5337 0.1857 0.058 Uiso 1 1 calc R
C10 C -0.44568(17) 0.3814(3) 0.0932(3) 0.0513(7) Uani 1 1 d .
H10 H -0.4650 0.3933 -0.0055 0.062 Uiso 1 1 calc R
C11 C -0.43293(15) 0.2799(2) 0.1639(3) 0.0450(6) Uani 1 1 d .
H11 H -0.4430 0.2139 0.1190 0.054 Uiso 1 1 calc R
N1 N -0.35066(12) 0.16490(18) 0.6986(3) 0.0401(5) Uani 1 1 d .
O1 O -0.26371(12) 0.0825(2) 0.9696(3) 0.0664(7) Uani 1 1 d .
O2 O -0.46536(17) 0.0125(3) 0.6426(4) 0.0983(11) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Fe1 0.0339(3) 0.0342(3) 0.0365(3) 0.000 0.0084(2) 0.000
C1 0.0409(15) 0.0611(18) 0.0533(17) 0.0111(13) 0.0121(13) 0.0070(12)
C2 0.0560(18) 0.073(2) 0.062(2) 0.0210(17) 0.0127(16) 0.0204(16)
C3 0.067(2) 0.080(2) 0.0422(16) 0.0087(15) 0.0142(16) 0.0112(17)
C4 0.0618(19) 0.0624(18) 0.0427(15) -0.0032(13) 0.0109(14) 0.0121(15)
C5 0.0542(16) 0.0402(13) 0.0447(14) 0.0024(11) 0.0091(12) 0.0082(11)
C6 0.0550(16) 0.0394(13) 0.0445(14) 0.0033(11) 0.0119(13) 0.0100(11)
C7 0.0366(12) 0.0403(12) 0.0438(13) 0.0033(10) 0.0099(11) 0.0046(10)
C8 0.0314(12) 0.0422(13) 0.0513(15) 0.0028(11) 0.0067(11) -0.0030(10)
C9 0.0381(13) 0.0486(14) 0.0606(17) 0.0143(13) 0.0170(13) -0.0041(11)
C10 0.0476(16) 0.0687(19) 0.0409(14) 0.0152(13) 0.0170(13) 0.0022(13)
C11 0.0439(14) 0.0501(14) 0.0442(14) -0.0019(11) 0.0166(12) 0.0067(11)
N1 0.0380(11) 0.0413(11) 0.0405(11) 0.0028(9) 0.0075(9) 0.0045(9)
O1 0.0524(13) 0.0934(19) 0.0498(13) 0.0185(12) 0.0035(11) 0.0105(12)
O2 0.086(2) 0.139(3) 0.0722(19) -0.0171(19) 0.0231(16) -0.054(2)
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
C10 Fe1 C10 170.25(19) 2_455 .
C10 Fe1 C11 41.84(12) 2_455 2_455
C10 Fe1 C11 146.97(14) . 2_455
C10 Fe1 C11 146.97(14) 2_455 .
C10 Fe1 C11 41.84(12) . .
C11 Fe1 C11 113.41(17) 2_455 .
C10 Fe1 C9 130.76(14) 2_455 .
C10 Fe1 C9 41.35(13) . .
C11 Fe1 C9 169.52(12) 2_455 .
C11 Fe1 C9 69.39(13) . .
C10 Fe1 C9 41.35(13) 2_455 2_455
C10 Fe1 C9 130.76(14) . 2_455
C11 Fe1 C9 69.39(13) 2_455 2_455
C11 Fe1 C9 169.52(12) . 2_455
C9 Fe1 C9 109.80(18) . 2_455
C10 Fe1 C7 114.55(13) 2_455 .
C10 Fe1 C7 69.94(12) . .
C11 Fe1 C7 106.37(11) 2_455 .
C11 Fe1 C7 41.49(11) . .
C9 Fe1 C7 68.59(11) . .
C9 Fe1 C7 148.70(12) 2_455 .
C10 Fe1 C7 69.94(12) 2_455 2_455
C10 Fe1 C7 114.55(13) . 2_455
C11 Fe1 C7 41.49(11) 2_455 2_455
C11 Fe1 C7 106.37(11) . 2_455
C9 Fe1 C7 148.70(12) . 2_455
C9 Fe1 C7 68.59(11) 2_455 2_455
C7 Fe1 C7 129.63(15) . 2_455
C10 Fe1 C8 107.61(13) 2_455 .
C10 Fe1 C8 69.77(13) . .
C11 Fe1 C8 129.38(12) 2_455 .
C11 Fe1 C8 69.19(12) . .
C9 Fe1 C8 41.02(11) . .
C9 Fe1 C8 117.51(12) 2_455 .
C7 Fe1 C8 40.24(11) . .
C7 Fe1 C8 168.46(11) 2_455 .
C10 Fe1 C8 69.77(13) 2_455 2_455
C10 Fe1 C8 107.61(13) . 2_455
C11 Fe1 C8 69.19(12) 2_455 2_455
C11 Fe1 C8 129.38(12) . 2_455
C9 Fe1 C8 117.51(12) . 2_455
C9 Fe1 C8 41.02(11) 2_455 2_455
C7 Fe1 C8 168.46(11) . 2_455
C7 Fe1 C8 40.24(11) 2_455 2_455
C8 Fe1 C8 150.53(15) . 2_455
N1 C1 C2 111.5(3) . .
O1 C2 C1 112.5(3) . .
O1 C3 C4 112.9(3) . .
N1 C4 C3 111.0(3) . .
N1 C5 C6 114.4(2) . .
C7 C6 C5 113.9(2) . .
C8 C7 C11 107.6(2) . .
C8 C7 C6 126.3(3) . .
C11 C7 C6 126.0(2) . .
C8 C7 Fe1 69.94(14) . .
C11 C7 Fe1 66.89(15) . .
C6 C7 Fe1 130.14(19) . .
C7 C8 C9 107.4(3) . .
C7 C8 Fe1 69.82(14) . .
C9 C8 Fe1 67.48(15) . .
C10 C9 C8 109.4(3) . .
C10 C9 Fe1 68.50(16) . .
C8 C9 Fe1 71.50(15) . .
C9 C10 C11 107.2(3) . .
C9 C10 Fe1 70.15(17) . .
C11 C10 Fe1 69.46(16) . .
C10 C11 C7 108.4(3) . .
C10 C11 Fe1 68.70(16) . .
C7 C11 Fe1 71.62(15) . .
C4 N1 C1 106.3(2) . .
C4 N1 C5 110.5(2) . .
C1 N1 C5 113.5(2) . .
C3 O1 C2 107.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 C10 1.999(3) 2_455
Fe1 C10 1.999(3) .
Fe1 C11 2.009(3) 2_455
Fe1 C11 2.009(3) .
Fe1 C9 2.020(3) .
Fe1 C9 2.020(3) 2_455
Fe1 C7 2.073(3) .
Fe1 C7 2.073(3) 2_455
Fe1 C8 2.074(3) .
Fe1 C8 2.074(3) 2_455
C1 N1 1.464(4) .
C1 C2 1.506(4) .
C2 O1 1.418(5) .
C3 O1 1.401(4) .
C3 C4 1.528(5) .
C4 N1 1.454(4) .
C5 N1 1.471(3) .
C5 C6 1.521(4) .
C6 C7 1.519(4) .
C7 C8 1.426(4) .
C7 C11 1.447(4) .
C8 C9 1.436(4) .
C9 C10 1.419(5) .
C10 C11 1.431(4) .
_journal_paper_doi 10.1021/om049222m