#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:35:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180086 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/32/7053226.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_7053226
loop_
_publ_author_name
'Ba, Fatou'
'Cabon, Nolwenn'
'Le Poul, Pascal'
'Kahlal, Samia'
'Saillard, Jean-Yves'
'Le Poul, Nicolas'
'Golhen, Stéphane'
'Caro, Bertrand'
'Robin-Le Guen, Françoise'
_publ_section_title
;
 Diferrocenylpyrylium salts and electron rich bispyran from oxidative
 coupling of ferrocenylpyran. Example of redox systems switched by proton
 transfer
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2066
_journal_paper_doi               10.1039/c3nj41126e
_journal_volume                  37
_journal_year                    2013
_chemical_formula_sum            'C56 H48 F12 Fe2 O5 P2'
_chemical_formula_weight         1202.58
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.308(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.956(2)
_cell_length_b                   16.995(4)
_cell_length_c                   15.106(3)
_cell_measurement_reflns_used    5930
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      0.998
_cell_volume                     3019.9(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare al, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.909
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  CCD
_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  0.1697
_diffrn_reflns_av_sigmaI/netI    0.1622
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14912
_diffrn_reflns_theta_full        25.61
_diffrn_reflns_theta_max         25.61
_diffrn_reflns_theta_min         5.32
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.043(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.2380
_refine_ls_R_factor_gt           0.1191
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3143
_refine_ls_wR_factor_ref         0.3952
_reflns_number_gt                2085
_reflns_number_total             5186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3nj41126e.txt
_cod_data_source_block           4(2+)
_cod_original_cell_volume        3019.6(10)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7053226
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.28228(14) -0.08375(9) 1.09999(11) 0.0813(8) Uani 1 1 d .
C2 C 0.0506(8) -0.0056(5) 0.9953(6) 0.059(2) Uani 1 1 d .
C2' C 0.2073(9) 0.1020(5) 0.8308(7) 0.069(3) Uani 1 1 d .
C3 C 0.1207(9) -0.0780(5) 1.0249(7) 0.075(3) Uani 1 1 d .
C3' C 0.1440(8) 0.0454(5) 0.8650(7) 0.066(2) Uani 1 1 d .
H3' H 0.1183 0.0012 0.8311 0.079 Uiso 1 1 calc R
C4' C 0.1185(8) 0.0553(5) 0.9520(7) 0.063(2) Uani 1 1 d .
C5' C 0.1528(9) 0.1240(5) 1.0023(7) 0.072(3) Uani 1 1 d .
H5' H 0.1309 0.1329 1.0575 0.086 Uiso 1 1 calc R
C11 C 0.2379(9) 0.1044(6) 0.7428(7) 0.075(3) Uani 1 1 d .
C12 C 0.1967(13) 0.0485(7) 0.6787(8) 0.105(4) Uani 1 1 d .
H12 H 0.1511 0.0083 0.6943 0.127 Uiso 1 1 calc R
C6' C 0.2208(9) 0.1781(5) 0.9665(7) 0.070(3) Uani 1 1 d .
C13 C 0.2204(16) 0.0499(11) 0.5922(10) 0.132(5) Uani 1 1 d .
H13 H 0.1958 0.0104 0.5507 0.159 Uiso 1 1 calc R
C14 C 0.2870(14) 0.1177(10) 0.5701(10) 0.120(5) Uani 1 1 d .
H14 H 0.3028 0.1236 0.5124 0.144 Uiso 1 1 calc R
C15 C 0.3240(12) 0.1703(8) 0.6335(9) 0.101(4) Uani 1 1 d .
H15 H 0.3686 0.2115 0.6189 0.121 Uiso 1 1 calc R
C16 C 0.3013(9) 0.1680(6) 0.7173(7) 0.077(3) Uani 1 1 d .
H16 H 0.3270 0.2079 0.7581 0.093 Uiso 1 1 calc R
C5 C 0.2761(10) 0.2460(5) 1.0109(7) 0.078(3) Uani 1 1 d .
C6 C 0.2436(14) 0.2710(7) 1.0917(9) 0.112(5) Uani 1 1 d .
H6 H 0.1860 0.2454 1.1145 0.134 Uiso 1 1 calc R
C7 C 0.300(2) 0.3353(10) 1.1365(12) 0.172(9) Uani 1 1 d .
H7 H 0.2822 0.3516 1.1909 0.206 Uiso 1 1 calc R
C8 C 0.3855(14) 0.3761(8) 1.1002(10) 0.123(5) Uani 1 1 d .
H8 H 0.4243 0.4184 1.1306 0.148 Uiso 1 1 calc R
C9 C 0.4078(15) 0.3523(8) 1.0226(11) 0.133(6) Uani 1 1 d .
H9 H 0.4606 0.3809 0.9975 0.159 Uiso 1 1 calc R
C10 C 0.3587(11) 0.2882(6) 0.9758(9) 0.097(4) Uani 1 1 d .
H10 H 0.3798 0.2731 0.9219 0.117 Uiso 1 1 calc R
C29 C 0.1968(13) -0.1188(7) 0.9775(9) 0.105(4) Uani 1 1 d .
H29 H 0.2153 -0.1059 0.9220 0.126 Uiso 1 1 calc R
C30 C 0.2381(16) -0.1840(9) 1.0344(13) 0.139(6) Uani 1 1 d .
H30 H 0.2882 -0.2219 1.0201 0.166 Uiso 1 1 calc R
C31 C 0.1956(14) -0.1838(8) 1.1110(12) 0.117(5) Uani 1 1 d .
H31 H 0.2116 -0.2201 1.1576 0.141 Uiso 1 1 calc R
C32 C 0.1214(10) -0.1179(7) 1.1077(8) 0.089(3) Uani 1 1 d .
H32 H 0.0805 -0.1035 1.1520 0.106 Uiso 1 1 calc R
C33 C 0.3422(14) 0.0249(8) 1.1509(12) 0.117(5) Uani 1 1 d .
H33 H 0.3003 0.0713 1.1467 0.140 Uiso 1 1 calc R
C34 C 0.4019(15) 0.0000(11) 1.0867(13) 0.137(6) Uani 1 1 d .
H34 H 0.4080 0.0258 1.0334 0.164 Uiso 1 1 calc R
C35 C 0.4556(14) -0.0775(12) 1.1192(19) 0.174(9) Uani 1 1 d .
H35 H 0.5020 -0.1094 1.0911 0.208 Uiso 1 1 calc R
C36 C 0.4185(14) -0.0911(11) 1.2046(14) 0.141(6) Uani 1 1 d .
H36 H 0.4354 -0.1347 1.2419 0.170 Uiso 1 1 calc R
C37 C 0.3509(14) -0.0248(9) 1.2202(12) 0.128(5) Uani 1 1 d .
H37 H 0.3181 -0.0174 1.2710 0.154 Uiso 1 1 calc R
F1 F 0.0580(10) 0.2006(6) 1.3462(8) 0.185(5) Uani 1 1 d .
F2 F -0.0721(8) 0.1267(6) 1.2673(8) 0.161(4) Uani 1 1 d .
F3 F 0.0718(8) 0.0620(7) 1.2180(9) 0.201(6) Uani 1 1 d .
F4 F 0.1937(8) 0.1439(6) 1.2901(10) 0.198(5) Uani 1 1 d .
F5 F 0.0697(15) 0.0739(7) 1.3551(9) 0.230(7) Uani 1 1 d .
F6 F 0.0529(12) 0.1920(9) 1.2033(9) 0.223(6) Uani 1 1 d .
P P 0.0655(3) 0.13372(17) 1.2810(2) 0.0816(10) Uani 1 1 d .
O1' O 0.2460(6) 0.1653(3) 0.8834(4) 0.0679(17) Uani 1 1 d .
O1W O -0.111(4) -0.343(2) 1.301(3) 0.33(3) Uani 0.50 1 d P
O3W O -0.0159(14) -0.2994(16) 1.175(3) 0.27(2) Uani 0.50 1 d P
O2W O 0.566(2) 0.051(3) 0.5216(19) 0.236(18) Uani 0.50 1 d P
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
C30 Fe1 C31 39.2(6) .
C30 Fe1 C32 67.4(7) .
C31 Fe1 C32 41.2(5) .
C30 Fe1 C29 41.7(5) .
C31 Fe1 C29 69.3(6) .
C32 Fe1 C29 69.0(6) .
C30 Fe1 C3 68.2(5) .
C31 Fe1 C3 68.9(5) .
C32 Fe1 C3 40.7(4) .
C29 Fe1 C3 41.0(5) .
C30 Fe1 C34 132.1(9) .
C31 Fe1 C34 166.3(7) .
C32 Fe1 C34 152.5(6) .
C29 Fe1 C34 111.0(7) .
C3 Fe1 C34 120.9(6) .
C30 Fe1 C35 106.7(8) .
C31 Fe1 C35 123.8(7) .
C32 Fe1 C35 162.4(7) .
C29 Fe1 C35 118.4(9) .
C3 Fe1 C35 154.6(8) .
C34 Fe1 C35 43.2(7) .
C30 Fe1 C36 115.6(7) .
C31 Fe1 C36 103.5(7) .
C32 Fe1 C36 124.4(7) .
C29 Fe1 C36 151.4(6) .
C3 Fe1 C36 163.7(7) .
C34 Fe1 C36 69.4(8) .
C35 Fe1 C36 41.6(8) .
C30 Fe1 C33 170.5(9) .
C31 Fe1 C33 150.3(8) .
C32 Fe1 C33 120.0(7) .
C29 Fe1 C33 132.9(6) .
C3 Fe1 C33 112.9(5) .
C34 Fe1 C33 38.7(6) .
C35 Fe1 C33 68.1(8) .
C36 Fe1 C33 66.3(6) .
C30 Fe1 C37 149.5(7) .
C31 Fe1 C37 117.2(7) .
C32 Fe1 C37 108.2(6) .
C29 Fe1 C37 167.6(6) .
C3 Fe1 C37 129.3(6) .
C34 Fe1 C37 65.4(7) .
C35 Fe1 C37 67.9(9) .
C36 Fe1 C37 40.1(6) .
C33 Fe1 C37 37.2(5) .
C2 C2 C4' 122.7(10) 3_557
C2 C2 C3 125.7(10) 3_557
C4' C2 C3 111.6(8) .
C3' C2' O1' 118.8(9) .
C3' C2' C11 127.7(9) .
O1' C2' C11 113.4(8) .
C32 C3 C29 107.7(10) .
C32 C3 C2 124.4(10) .
C29 C3 C2 128.0(10) .
C32 C3 Fe1 68.6(6) .
C29 C3 Fe1 68.6(7) .
C2 C3 Fe1 128.1(7) .
C2' C3' C4' 119.3(8) .
C5' C4' C3' 120.6(8) .
C5' C4' C2 116.9(8) .
C3' C4' C2 122.4(8) .
C6' C5' C4' 117.9(9) .
C12 C11 C16 118.4(10) .
C12 C11 C2' 120.6(10) .
C16 C11 C2' 120.7(9) .
C13 C12 C11 122.7(13) .
O1' C6' C5' 119.5(8) .
O1' C6' C5 113.6(8) .
C5' C6' C5 126.8(10) .
C12 C13 C14 116.0(14) .
C15 C14 C13 119.2(13) .
C14 C15 C16 124.4(12) .
C15 C16 C11 119.2(11) .
C6 C5 C10 119.8(9) .
C6 C5 C6' 118.1(10) .
C10 C5 C6' 122.1(10) .
C5 C6 C7 117.9(12) .
C8 C7 C6 121.1(14) .
C9 C8 C7 117.9(13) .
C8 C9 C10 124.7(13) .
C9 C10 C5 118.5(11) .
C30 C29 C3 104.8(13) .
C30 C29 Fe1 67.6(8) .
C3 C29 Fe1 70.4(6) .
C29 C30 C31 111.8(13) .
C29 C30 Fe1 70.7(8) .
C31 C30 Fe1 71.2(9) .
C32 C31 C30 107.5(13) .
C32 C31 Fe1 70.1(7) .
C30 C31 Fe1 69.6(10) .
C31 C32 C3 108.2(12) .
C31 C32 Fe1 68.7(8) .
C3 C32 Fe1 70.7(7) .
C37 C33 C34 112.5(16) .
C37 C33 Fe1 72.6(9) .
C34 C33 Fe1 69.6(10) .
C33 C34 C35 106.5(16) .
C33 C34 Fe1 71.6(9) .
C35 C34 Fe1 68.1(9) .
C36 C35 C34 104.3(16) .
C36 C35 Fe1 69.8(9) .
C34 C35 Fe1 68.7(9) .
C37 C36 C35 106.9(16) .
C37 C36 Fe1 71.7(9) .
C35 C36 Fe1 68.6(10) .
C33 C37 C36 109.7(17) .
C33 C37 Fe1 70.2(9) .
C36 C37 Fe1 68.1(10) .
F6 P F5 176.0(9) .
F6 P F1 90.2(8) .
F5 P F1 91.2(8) .
F6 P F4 87.4(8) .
F5 P F4 96.3(9) .
F1 P F4 91.9(6) .
F6 P F3 92.7(9) .
F5 P F3 85.9(9) .
F1 P F3 176.9(8) .
F4 P F3 89.2(5) .
F6 P F2 89.5(7) .
F5 P F2 86.7(8) .
F1 P F2 87.8(5) .
F4 P F2 176.9(8) .
F3 P F2 91.3(5) .
C6' O1' C2' 123.6(7) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 C30 1.994(16) .
Fe1 C31 2.014(15) .
Fe1 C32 2.032(12) .
Fe1 C29 2.037(13) .
Fe1 C3 2.061(10) .
Fe1 C34 2.052(16) .
Fe1 C35 2.043(17) .
Fe1 C36 2.060(17) .
Fe1 C33 2.078(14) .
Fe1 C37 2.108(16) .
C2 C2 1.257(18) 3_557
C2 C4' 1.533(12) .
C2 C3 1.510(13) .
C2' C3' 1.380(13) .
C2' O1' 1.368(11) .
C2' C11 1.441(15) .
C3 C32 1.422(15) .
C3 C29 1.434(16) .
C3' C4' 1.411(13) .
C4' C5' 1.412(13) .
C5' C6' 1.398(13) .
C11 C12 1.383(15) .
C11 C16 1.413(14) .
C12 C13 1.386(19) .
C6' O1' 1.359(11) .
C6' C5 1.436(13) .
C13 C14 1.47(2) .
C14 C15 1.327(18) .
C15 C16 1.341(15) .
C5 C6 1.411(15) .
C5 C10 1.400(14) .
C6 C7 1.396(19) .
C7 C8 1.42(2) .
C8 C9 1.311(17) .
C9 C10 1.372(16) .
C29 C30 1.435(19) .
C30 C31 1.34(2) .
C31 C32 1.424(18) .
C33 C37 1.334(19) .
C33 C34 1.37(2) .
C34 C35 1.51(2) .
C35 C36 1.46(3) .
C36 C37 1.43(2) .
F1 P 1.517(8) .
F2 P 1.626(10) .
F3 P 1.557(8) .
F4 P 1.524(10) .
F5 P 1.507(11) .
F6 P 1.522(11) .
