#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:51:31 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179600 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/64/4506427.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_4506427
loop_
_publ_author_name
'Clapsaddle, Brady J.'
'Caamaño, Samira'
'Hebert, Gretchen N.'
'Bayless, Michael B.'
'Kobayashi, Yoshihiro'
'Miller, Susie M.'
'Anderson, Oren P.'
'Strauss, Steven H.'
_publ_section_title
;
 Structures of
 1,1′,3,3′-Tetra(2-methyl-2-nonyl)ferrocenium(1+)
 Oxoanion(1−) Salts. Layered Materials with Alternating Ionic and
 Low-Dielectric Paraffin-Like Domains Through Which Anion Diffusion is
 Rapid
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3868
_journal_paper_doi               10.1021/cg3000872
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C50 H90 Fe'
_chemical_formula_weight         747.07
_chemical_name_common            1,1',3,3'-tetra(2-methyl-2-nonyl)ferrocene
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 101.7360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.7606(8)
_cell_length_b                   8.7418(4)
_cell_length_c                   28.8086(12)
_cell_measurement_temperature    170(2)
_cell_volume                     4625.9(3)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      170(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_sigmaI/netI    0.1653
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11942
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light orang'
_exptl_crystal_density_diffrn    1.073
_exptl_crystal_description       plate
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.40
_refine_diff_density_max         1.450
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.865
_refine_ls_goodness_of_fit_obs   1.059
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         5316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.871
_refine_ls_restrained_S_obs      1.059
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_obs          0.0675
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0536P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1622
_refine_ls_wR_factor_obs         0.1385
_reflns_number_observed          2693
_reflns_number_total             5317
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            cg3000872_si_002.cif
_cod_data_source_block           shs52m
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.0000P] 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^)+(0.0536P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4506427
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Fe Fe 0.5000 0.46660(7) 0.2500 0.0262(2) Uani 1 d S
C1 C 0.4831(2) 0.5819(3) 0.18474(11) 0.0268(8) Uani 1 d .
C2 C 0.4163(2) 0.5515(4) 0.19902(10) 0.0266(7) Uani 1 d .
H2A H 0.3810(2) 0.6316(4) 0.20476(10) 0.032 Uiso 1 calc R
C3 C 0.4072(2) 0.3937(4) 0.20462(11) 0.0276(8) Uani 1 d .
C4 C 0.4708(2) 0.3210(4) 0.19414(11) 0.0288(8) Uani 1 d .
H4A H 0.4803(2) 0.2084(4) 0.19456(11) 0.035 Uiso 1 calc R
C5 C 0.5166(2) 0.4355(3) 0.18217(11) 0.0276(8) Uani 1 d .
H5A H 0.5649(2) 0.4177(3) 0.17338(11) 0.033 Uiso 1 calc R
C6 C 0.5105(2) 0.7288(4) 0.16616(11) 0.0308(8) Uani 1 d .
C7 C 0.5902(2) 0.7593(4) 0.18866(13) 0.0455(10) Uani 1 d .
H7A H 0.6060(2) 0.8545(4) 0.17588(13) 0.068 Uiso 1 calc R
H7B H 0.6203(2) 0.6744(4) 0.18143(13) 0.068 Uiso 1 calc R
H7C H 0.5956(2) 0.7686(4) 0.22309(13) 0.068 Uiso 1 calc R
C8 C 0.4652(2) 0.8652(4) 0.17757(12) 0.0411(9) Uani 1 d .
H8A H 0.4831(2) 0.9596(4) 0.16553(12) 0.062 Uiso 1 calc R
H8B H 0.4697(2) 0.8731(4) 0.21197(12) 0.062 Uiso 1 calc R
H8C H 0.4140(2) 0.8498(4) 0.16247(12) 0.062 Uiso 1 calc R
C9 C 0.5036(2) 0.7160(4) 0.11244(11) 0.0337(8) Uani 1 d .
H9A H 0.5230(2) 0.8114(4) 0.10124(11) 0.040 Uiso 1 calc R
H9B H 0.5355(2) 0.6313(4) 0.10625(11) 0.040 Uiso 1 calc R
C10 C 0.4283(2) 0.6889(4) 0.08238(12) 0.0361(9) Uani 1 d .
H10A H 0.4082(2) 0.5932(4) 0.09296(12) 0.043 Uiso 1 calc R
H10B H 0.3960(2) 0.7739(4) 0.08761(12) 0.043 Uiso 1 calc R
C11 C 0.4277(2) 0.6770(4) 0.03000(11) 0.0369(9) Uani 1 d .
H11A H 0.4553(2) 0.7644(4) 0.02069(11) 0.044 Uiso 1 calc R
H11B H 0.4534(2) 0.5821(4) 0.02426(11) 0.044 Uiso 1 calc R
C12 C 0.3529(2) 0.6756(4) -0.00119(12) 0.0392(9) Uani 1 d .
H12A H 0.3261(2) 0.7673(4) 0.00602(12) 0.047 Uiso 1 calc R
H12B H 0.3264(2) 0.5845(4) 0.00674(12) 0.047 Uiso 1 calc R
C13 C 0.3524(2) 0.6735(4) -0.05403(12) 0.0377(9) Uani 1 d .
H13A H 0.3820(2) 0.7604(4) -0.06149(12) 0.045 Uiso 1 calc R
H13B H 0.3762(2) 0.5781(4) -0.06157(12) 0.045 Uiso 1 calc R
C14 C 0.2778(2) 0.6832(4) -0.08568(12) 0.0431(9) Uani 1 d .
H14A H 0.2536(2) 0.7780(4) -0.07807(12) 0.052 Uiso 1 calc R
H14B H 0.2482(2) 0.5954(4) -0.07879(12) 0.052 Uiso 1 calc R
C15 C 0.2793(2) 0.6831(5) -0.13800(13) 0.0531(11) Uani 1 d .
H15A H 0.2294(2) 0.6896(5) -0.15654(13) 0.080 Uiso 1 calc R
H15B H 0.3020(2) 0.5884(5) -0.14604(13) 0.080 Uiso 1 calc R
H15C H 0.3074(2) 0.7711(5) -0.14531(13) 0.080 Uiso 1 calc R
C16 C 0.3415(2) 0.3073(4) 0.21400(11) 0.0287(8) Uani 1 d .
C17 C 0.3636(2) 0.1726(4) 0.24772(13) 0.0424(10) Uani 1 d .
H17A H 0.3199(2) 0.1196(4) 0.25293(13) 0.064 Uiso 1 calc R
H17B H 0.3914(2) 0.2104(4) 0.27807(13) 0.064 Uiso 1 calc R
H17C H 0.3937(2) 0.1014(4) 0.23378(13) 0.064 Uiso 1 calc R
C18 C 0.2929(2) 0.4140(4) 0.23619(12) 0.0378(9) Uani 1 d .
H18A H 0.2507(2) 0.3569(4) 0.24209(12) 0.057 Uiso 1 calc R
H18B H 0.2763(2) 0.4989(4) 0.21447(12) 0.057 Uiso 1 calc R
H18C H 0.3207(2) 0.4544(4) 0.26621(12) 0.057 Uiso 1 calc R
C19 C 0.2982(2) 0.2414(4) 0.16728(12) 0.0344(8) Uani 1 d .
H19A H 0.3307(2) 0.1711(4) 0.15441(12) 0.041 Uiso 1 calc R
H19B H 0.2581(2) 0.1788(4) 0.17486(12) 0.041 Uiso 1 calc R
C20 C 0.2654(2) 0.3516(4) 0.12819(12) 0.0366(9) Uani 1 d .
H20A H 0.2334(2) 0.4246(4) 0.14042(12) 0.044 Uiso 1 calc R
H20B H 0.3049(2) 0.4108(4) 0.11844(12) 0.044 Uiso 1 calc R
C21 C 0.2219(2) 0.2693(4) 0.08550(12) 0.0397(9) Uani 1 d .
H21A H 0.2556(2) 0.2044(4) 0.07175(12) 0.048 Uiso 1 calc R
H21B H 0.1867(2) 0.2005(4) 0.09641(12) 0.048 Uiso 1 calc R
C22 C 0.1807(2) 0.3702(4) 0.04698(13) 0.0416(9) Uani 1 d .
H22A H 0.2157(2) 0.4368(4) 0.03509(13) 0.050 Uiso 1 calc R
H22B H 0.1476(2) 0.4369(4) 0.06059(13) 0.050 Uiso 1 calc R
C23 C 0.1365(2) 0.2819(4) 0.00562(12) 0.0407(9) Uani 1 d .
H23A H 0.1701(2) 0.2185(4) -0.00863(12) 0.049 Uiso 1 calc R
H23B H 0.1033(2) 0.2117(4) 0.01794(12) 0.049 Uiso 1 calc R
C24 C 0.0917(2) 0.3793(4) -0.03286(13) 0.0500(11) Uani 1 d .
H24A H 0.0571(2) 0.4410(4) -0.01895(13) 0.060 Uiso 1 calc R
H24B H 0.1246(2) 0.4511(4) -0.04491(13) 0.060 Uiso 1 calc R
C25 C 0.0497(2) 0.2885(5) -0.07392(13) 0.0567(12) Uani 1 d .
H25A H 0.0220(2) 0.3584(5) -0.09747(13) 0.085 Uiso 1 calc R
H25B H 0.0161(2) 0.2189(5) -0.06249(13) 0.085 Uiso 1 calc R
H25C H 0.0836(2) 0.2290(5) -0.08848(13) 0.085 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'
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
C4 Fe C4 102.7(2) . 2_655
C4 Fe C3 41.14(12) . .
C4 Fe C3 111.46(13) 2_655 .
C4 Fe C3 111.46(13) . 2_655
C4 Fe C3 41.14(12) 2_655 2_655
C3 Fe C3 143.9(2) . 2_655
C4 Fe C2 146.35(12) . 2_655
C4 Fe C2 67.55(12) 2_655 2_655
C3 Fe C2 172.24(12) . 2_655
C3 Fe C2 39.90(12) 2_655 2_655
C4 Fe C2 67.55(12) . .
C4 Fe C2 146.34(12) 2_655 .
C3 Fe C2 39.90(12) . .
C3 Fe C2 172.24(12) 2_655 .
C2 Fe C2 137.7(2) 2_655 .
C4 Fe C5 40.17(12) . .
C4 Fe C5 126.81(13) 2_655 .
C3 Fe C5 68.13(12) . .
C3 Fe C5 106.89(12) 2_655 .
C2 Fe C5 118.94(12) 2_655 .
C2 Fe C5 67.13(12) . .
C4 Fe C5 126.80(13) . 2_655
C4 Fe C5 40.17(12) 2_655 2_655
C3 Fe C5 106.89(12) . 2_655
C3 Fe C5 68.14(12) 2_655 2_655
C2 Fe C5 67.13(12) 2_655 2_655
C2 Fe C5 118.94(12) . 2_655
C5 Fe C5 164.8(2) . 2_655
C4 Fe C1 67.99(12) . .
C4 Fe C1 167.05(12) 2_655 .
C3 Fe C1 67.98(12) . .
C3 Fe C1 132.28(12) 2_655 .
C2 Fe C1 114.84(12) 2_655 .
C2 Fe C1 39.97(11) . .
C5 Fe C1 40.36(11) . .
C5 Fe C1 152.73(12) 2_655 .
C4 Fe C1 167.05(12) . 2_655
C4 Fe C1 67.98(12) 2_655 2_655
C3 Fe C1 132.28(12) . 2_655
C3 Fe C1 67.98(12) 2_655 2_655
C2 Fe C1 39.97(11) 2_655 2_655
C2 Fe C1 114.84(12) . 2_655
C5 Fe C1 152.73(13) . 2_655
C5 Fe C1 40.36(11) 2_655 2_655
C1 Fe C1 122.6(2) . 2_655
C2 C1 C5 105.7(3) . .
C2 C1 C6 129.9(3) . .
C5 C1 C6 123.5(3) . .
C2 C1 Fe 68.4(2) . .
C5 C1 Fe 68.3(2) . .
C6 C1 Fe 136.1(2) . .
C3 C2 C1 110.6(3) . .
C3 C2 Fe 69.9(2) . .
C1 C2 Fe 71.6(2) . .
C2 C3 C4 106.5(3) . .
C2 C3 C16 129.3(3) . .
C4 C3 C16 123.8(3) . .
C2 C3 Fe 70.2(2) . .
C4 C3 Fe 68.8(2) . .
C16 C3 Fe 131.0(2) . .
C5 C4 C3 108.2(3) . .
C5 C4 Fe 70.7(2) . .
C3 C4 Fe 70.1(2) . .
C4 C5 C1 109.0(3) . .
C4 C5 Fe 69.1(2) . .
C1 C5 Fe 71.4(2) . .
C1 C6 C7 111.7(3) . .
C1 C6 C9 109.2(3) . .
C7 C6 C9 108.4(3) . .
C1 C6 C8 109.7(3) . .
C7 C6 C8 108.0(3) . .
C9 C6 C8 109.6(3) . .
C10 C9 C6 117.7(3) . .
C11 C10 C9 113.4(3) . .
C12 C11 C10 114.4(3) . .
C11 C12 C13 114.4(3) . .
C14 C13 C12 114.8(3) . .
C13 C14 C15 113.5(3) . .
C3 C16 C17 111.8(3) . .
C3 C16 C18 110.2(3) . .
C17 C16 C18 108.1(3) . .
C3 C16 C19 109.6(3) . .
C17 C16 C19 107.1(3) . .
C18 C16 C19 109.9(3) . .
C20 C19 C16 118.4(3) . .
C21 C20 C19 111.9(3) . .
C22 C21 C20 115.7(3) . .
C21 C22 C23 113.5(3) . .
C24 C23 C22 115.1(3) . .
C25 C24 C23 113.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe C4 2.037(3) .
Fe C4 2.037(3) 2_655
Fe C3 2.054(3) .
Fe C3 2.054(3) 2_655
Fe C2 2.058(3) 2_655
Fe C2 2.058(3) .
Fe C5 2.059(3) .
Fe C5 2.059(3) 2_655
Fe C1 2.100(3) .
Fe C1 2.100(3) 2_655
C1 C2 1.421(4) .
C1 C5 1.435(4) .
C1 C6 1.520(4) .
C2 C3 1.403(4) .
C3 C4 1.438(4) .
C3 C16 1.516(4) .
C4 C5 1.407(4) .
C6 C7 1.527(4) .
C6 C9 1.531(4) .
C6 C8 1.538(4) .
C9 C10 1.519(4) .
C10 C11 1.510(5) .
C11 C12 1.505(4) .
C12 C13 1.521(5) .
C13 C14 1.510(4) .
C14 C15 1.513(5) .
C16 C17 1.529(4) .
C16 C18 1.532(4) .
C16 C19 1.536(4) .
C19 C20 1.514(4) .
C20 C21 1.513(4) .
C21 C22 1.502(5) .
C22 C23 1.517(4) .
C23 C24 1.510(5) .
C24 C25 1.508(5) .
