#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:20:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178646 $
#$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, Kévin 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_paper_doi               10.1021/om049222m
_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/[σ²(Fo²)+(0.0921P)²+1.6352P] where P=(Fo²+2Fc²)/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)
_cod_data_source_file            om049222msi20041104_051556.cif
_cod_data_source_block           kmj1
_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_original_sg_symbol_H-M      C2/c
_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_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) .
