#------------------------------------------------------------------------------
#$Date: 2016-03-25 12:51:43 +0100 (vie 25 de mar de 2016) $
#$Revision: 179867 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/63/7016314.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_7016314
loop_
_publ_author_name
'Mochida, Tomoyuki'
'Funasako, Yusuke'
'Azumi, Hiroko'
_publ_section_title
;
 Charge-transfer complexes from decamethylferrocene and 1,4-quinone
 derivatives: neutral-ionic phase diagrams for metallocene complexes.
;
_journal_issue                   36
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9221
_journal_page_last               9228
_journal_paper_doi               10.1039/c1dt10200a
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C18 H26 Fe, 2(C10 H4 Cl2 O2)'
_chemical_formula_sum            'C38 H34 Cl4 Fe O4'
_chemical_formula_weight         750.29
_chemical_name_common
'octamethylferrocene-dichloronaphthoquinone complex'
_chemical_name_systematic
;
octamethylferrocene-dichloronaphthoquinone complex
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 96.016(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.846(3)
_cell_length_b                   8.1681(17)
_cell_length_c                   15.110(3)
_cell_measurement_reflns_used    4132
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.71
_cell_volume                     1699.5(6)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9312
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  0.7353
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0376
_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)+(0.0523P)²+0.7295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1039
_reflns_number_gt                3240
_reflns_number_total             3821
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c1dt10200a.txt
_cod_data_source_block           OctaCl2NQ_173
_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      'P 21/c'
_cod_database_code               7016314
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.6267(2) 0.1260(5) 1.0017(4) 0.1017(14) Uani 1 1 d .
C2 C 0.6046(2) 0.0520(6) 0.9178(3) 0.0948(14) Uani 1 1 d .
C3 C 0.6392(4) 0.2968(9) 1.0133(7) 0.181(4) Uani 0.80 1 d P
H3A H 0.7081 0.3244 1.0133 0.272 Uiso 0.80 1 calc PR
H3B H 0.6169 0.3297 1.0701 0.272 Uiso 0.80 1 calc PR
H3C H 0.6013 0.3546 0.9646 0.272 Uiso 0.80 1 calc PR
C4 C 0.5929(3) 0.1447(8) 0.8318(4) 0.127(2) Uani 0.80 1 d P
H4A H 0.5694 0.2554 0.8423 0.191 Uiso 0.80 1 calc PR
H4B H 0.5460 0.0880 0.7893 0.191 Uiso 0.80 1 calc PR
H4C H 0.6557 0.1512 0.8075 0.191 Uiso 0.80 1 calc PR
C5 C 0.40009(18) 0.1197(5) 1.0663(2) 0.0804(10) Uani 1 1 d .
C6 C 0.38003(17) 0.1473(5) 0.9735(2) 0.0768(10) Uani 1 1 d .
C7 C 0.36335(19) -0.0050(6) 0.9306(3) 0.0875(11) Uani 1 1 d .
C8 C 0.4198(3) 0.2457(9) 1.1309(4) 0.122(2) Uani 0.80 1 d P
H8A H 0.4542 0.3356 1.1049 0.183 Uiso 0.80 1 calc PR
H8B H 0.4602 0.2018 1.1826 0.183 Uiso 0.80 1 calc PR
H8C H 0.3585 0.2864 1.1496 0.183 Uiso 0.80 1 calc PR
C9 C 0.3736(3) 0.3058(7) 0.9266(3) 0.1018(17) Uani 0.80 1 d P
H9A H 0.3910 0.2911 0.8659 0.153 Uiso 0.80 1 calc PR
H9B H 0.4184 0.3839 0.9584 0.153 Uiso 0.80 1 calc PR
H9C H 0.3071 0.3477 0.9244 0.153 Uiso 0.80 1 calc PR
C10 C 0.3400(3) -0.0307(9) 0.8337(3) 0.1122(19) Uani 0.80 1 d P
H10A H 0.3586 -0.1419 0.8181 0.168 Uiso 0.80 1 calc PR
H10B H 0.3758 0.0488 0.8011 0.168 Uiso 0.80 1 calc PR
H10C H 0.2701 -0.0158 0.8177 0.168 Uiso 0.80 1 calc PR
C12 C 0.14610(12) -0.08253(19) 1.07903(10) 0.0260(3) Uani 1 1 d .
C13 C 0.16197(12) 0.0859(2) 1.11670(10) 0.0259(3) Uani 1 1 d .
C14 C 0.14969(12) 0.2201(2) 1.06624(10) 0.0267(3) Uani 1 1 d .
C15 C 0.11965(12) 0.2113(2) 0.96817(10) 0.0272(3) Uani 1 1 d .
C16 C 0.07970(13) 0.0312(2) 0.83743(11) 0.0286(3) Uani 1 1 d .
H16 H 0.0708 0.1264 0.8014 0.034 Uiso 1 1 calc R
C17 C 0.06701(13) -0.1225(2) 0.79933(11) 0.0317(4) Uani 1 1 d .
H17 H 0.0499 -0.1325 0.7370 0.038 Uiso 1 1 calc R
C18 C 0.07915(13) -0.2617(2) 0.85170(12) 0.0324(4) Uani 1 1 d .
H18 H 0.0705 -0.3667 0.8250 0.039 Uiso 1 1 calc R
C19 C 0.10386(13) -0.2487(2) 0.94296(11) 0.0294(3) Uani 1 1 d .
H19 H 0.1112 -0.3444 0.9788 0.035 Uiso 1 1 calc R
C20 C 0.11782(12) -0.09470(19) 0.98162(10) 0.0244(3) Uani 1 1 d .
C21 C 0.10562(12) 0.04584(19) 0.92892(10) 0.0242(3) Uani 1 1 d .
Cl1 Cl 0.19426(4) 0.09580(5) 1.22886(3) 0.03706(13) Uani 1 1 d .
Cl2 Cl 0.16465(4) 0.41346(5) 1.10888(3) 0.03869(14) Uani 1 1 d .
Fe1 Fe 0.5000 0.0000 1.0000 0.0734(2) Uani 1 2 d S
O1 O 0.15546(10) -0.20147(15) 1.12707(8) 0.0363(3) Uani 1 1 d .
O2 O 0.10700(11) 0.33534(15) 0.92429(8) 0.0422(3) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 C1 C3 123.2(6) . .
C2 C1 C7 110.2(4) . 3_657
C3 C1 C7 126.7(6) . 3_657
C1 C2 C5 106.3(3) . 3_657
C1 C2 C4 123.9(5) . .
C5 C2 C4 129.8(5) 3_657 .
C1 C3 H3A 109.5 . .
C1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C2 C4 H4A 109.5 . .
C2 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C2 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C6 C5 C8 124.4(4) . .
C6 C5 C2 108.4(4) . 3_657
C8 C5 C2 127.2(4) . 3_657
C7 C6 C5 108.6(3) . .
C7 C6 C9 123.8(4) . .
C5 C6 C9 127.6(4) . .
C6 C7 C1 106.6(4) . 3_657
C6 C7 C10 125.9(4) . .
C1 C7 C10 127.5(5) 3_657 .
C5 C8 H8A 109.5 . .
C5 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C5 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C6 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C6 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C10 H10A 109.5 . .
C7 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C7 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
O1 C12 C20 122.70(15) . .
O1 C12 C13 120.48(14) . .
C20 C12 C13 116.82(13) . .
C14 C13 C12 122.19(14) . .
C14 C13 Cl1 122.09(13) . .
C12 C13 Cl1 115.71(12) . .
C13 C14 C15 122.03(14) . .
C13 C14 Cl2 122.67(13) . .
C15 C14 Cl2 115.29(12) . .
O2 C15 C21 122.54(14) . .
O2 C15 C14 120.63(15) . .
C21 C15 C14 116.82(13) . .
C17 C16 C21 119.84(15) . .
C17 C16 H16 120.1 . .
C21 C16 H16 120.1 . .
C16 C17 C18 120.26(15) . .
C16 C17 H17 119.9 . .
C18 C17 H17 119.9 . .
C17 C18 C19 120.46(16) . .
C17 C18 H18 119.8 . .
C19 C18 H18 119.8 . .
C18 C19 C20 119.62(15) . .
C18 C19 H19 120.2 . .
C20 C19 H19 120.2 . .
C19 C20 C21 120.01(15) . .
C19 C20 C12 119.12(14) . .
C21 C20 C12 120.86(14) . .
C16 C21 C20 119.80(15) . .
C16 C21 C15 118.95(14) . .
C20 C21 C15 121.25(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.410(6) .
C1 C3 1.414(8) .
C1 C7 1.418(5) 3_657
C2 C5 1.425(6) 3_657
C2 C4 1.498(5) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 C6 1.420(4) .
C5 C8 1.425(7) .
C5 C2 1.425(6) 3_657
C6 C7 1.410(5) .
C6 C9 1.473(5) .
C7 C1 1.418(5) 3_657
C7 C10 1.482(5) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C12 O1 1.211(2) .
C12 C20 1.486(2) .
C12 C13 1.496(2) .
C13 C14 1.337(2) .
C13 Cl1 1.7086(16) .
C14 C15 1.498(2) .
C14 Cl2 1.7098(16) .
C15 O2 1.213(2) .
C15 C21 1.481(2) .
C16 C17 1.384(2) .
C16 C21 1.396(2) .
C16 H16 0.9500 .
C17 C18 1.385(3) .
C17 H17 0.9500 .
C18 C19 1.389(2) .
C18 H18 0.9500 .
C19 C20 1.392(2) .
C19 H19 0.9500 .
C20 C21 1.397(2) .
