# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Iron_oxalate_dihydrate_1_pure
_audit_creation_date             2014-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            Humboldtine
_chemical_name_systematic        'Iron(II) oxalate dihydrate'
_chemical_formula_moiety         'C2 H4 Fe O6'
_chemical_formula_sum            'C2 H4 Fe O6'
_chemical_formula_weight         179.90
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Fe C2 O6 H4'
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.065(12)
_cell_length_b                   5.559(2)
_cell_length_c                   9.817(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 128.03(15)
_cell_angle_gamma                90.00
_cell_volume                     518.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    956
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1220
_cell_measurement_theta_min      4.1990
_exptl_absorpt_coefficient_mu    2.862
_exptl_absorpt_correction_T_max  0.859
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.0591
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1413
_diffrn_reflns_av_unetI/netI     0.0921
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1742
_diffrn_reflns_theta_full        14.05
_diffrn_reflns_theta_max         26.20
_diffrn_reflns_theta_min         4.25
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0591
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0059923000
_diffrn_orient_matrix_UB_12      0.1267128000
_diffrn_orient_matrix_UB_13      0.0037463000
_diffrn_orient_matrix_UB_21      0.0475059000
_diffrn_orient_matrix_UB_22      0.0177649000
_diffrn_orient_matrix_UB_23      -0.0189690000
_diffrn_orient_matrix_UB_31      -0.0576264000
_diffrn_orient_matrix_UB_32      0.0012956000
_diffrn_orient_matrix_UB_33      -0.0892374000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.4449 6 2216
2 0.0600 0 534
3 0.4951 0 2216

_diffrn_oxdiff_twin_integration_method simultaneous
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                354
_reflns_number_total             466
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.082
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.246
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.307
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     43
_refine_ls_number_reflns         466
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0879
_refine_ls_restrained_S_all      1.307
_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)+(0.1236P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2302
_refine_ls_wR_factor_ref         0.2406
_refine_special_details          Twin
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O5(H5A,H5B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.0499(9) 0.6669(19) 0.8510(12) 0.018(2) Uani 1 d . . 1 . . .
O1 O -0.0863(7) -0.1288(15) 0.5762(9) 0.0239(17) Uani 1 d . . 1 . . .
O2 O 0.0857(7) 0.4673(17) 0.9237(9) 0.0248(18) Uani 1 d . . 1 . . .
O5 O 0.1791(7) 0.1721(17) 0.7566(10) 0.0304(18) Uani 1 d . . 1 . . .
H5A H 0.2542 0.2258 0.8563 0.046 Uiso 1 d . . 1 GR . .
H5B H 0.1655 0.2659 0.6751 0.046 Uiso 1 d . . 1 GR . .
Fe1 Fe 0.0000 0.1707(4) 0.7500 0.0219(8) Uani 1 d . . 2 S T P

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
C1 0.025(4) 0.005(5) 0.026(6) 0.002(5) 0.017(5) 0.001(4)
O1 0.040(4) 0.009(5) 0.014(4) -0.001(3) 0.012(3) 0.000(3)
O2 0.030(4) 0.020(5) 0.017(4) 0.003(3) 0.011(3) 0.001(3)
O5 0.036(4) 0.035(5) 0.023(4) 0.000(4) 0.020(3) 0.002(4)
Fe1 0.0315(12) 0.0104(12) 0.0223(13) 0.000 0.0159(10) 0.000

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.561(19) 2_556 ?
C1 O1 1.268(13) 2_566 ?
C1 O2 1.244(13) . ?
O1 C1 1.268(13) 2_546 ?
O1 Fe1 2.140(8) . ?
O2 Fe1 2.126(9) . ?
O5 Fe1 2.122(7) . ?
Fe1 O1 2.140(8) 2_556 ?
Fe1 O2 2.126(9) 2_556 ?
Fe1 O5 2.122(7) 2_556 ?

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
_geom_angle_publ_flag
O1 C1 C1 116.4(6) 2_566 2_556 ?
O2 C1 C1 116.9(6) . 2_556 ?
O2 C1 O1 126.8(9) . 2_566 ?
C1 O1 Fe1 114.7(7) 2_546 . ?
C1 O2 Fe1 114.0(6) . . ?
O1 Fe1 O1 77.8(4) . 2_556 ?
O2 Fe1 O1 101.9(3) . 2_556 ?
O2 Fe1 O1 179.7(3) . . ?
O2 Fe1 O1 179.7(3) 2_556 2_556 ?
O2 Fe1 O1 101.9(3) 2_556 . ?
O2 Fe1 O2 78.3(5) 2_556 . ?
O5 Fe1 O1 90.8(3) 2_556 2_556 ?
O5 Fe1 O1 90.8(3) . . ?
O5 Fe1 O1 89.6(3) . 2_556 ?
O5 Fe1 O1 89.6(3) 2_556 . ?
O5 Fe1 O2 89.4(3) . . ?
O5 Fe1 O2 90.3(3) . 2_556 ?
O5 Fe1 O2 89.4(3) 2_556 2_556 ?
O5 Fe1 O2 90.3(3) 2_556 . ?
O5 Fe1 O5 179.6(5) . 2_556 ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
15 1 -12 0.0197 14.9897 0.9957 -12.0066 -0.0086 0.9575 0.2089
-4 8 3 0.1925 -3.9831 7.9801 3.0069 1.0463 -0.1045 -0.0285
4 -8 -3 0.1385 3.9831 -7.9801 -3.0069 -1.0463 0.1045 0.0285
-9 0 -5 0.0295 -9.0373 0.0240 -4.9795 0.0385 -0.3344 0.9652
9 0 5 0.0295 9.0373 -0.0240 4.9795 -0.0385 0.3344 -0.9652
-15 -1 12 0.0437 -14.9897 -0.9957 12.0066 0.0086 -0.9575 -0.2089
_database_code_depnum_ccdc_archive 'CCDC 1010845'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_iron_oxalate_dihydrate_2_StackingFaults
_audit_creation_date             2014-04-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            'Humboldtine (stacking faults)'
_chemical_name_systematic        'Iron oxalate dihydrate'
_chemical_formula_moiety         '2.94(C0.68 H1.36 Fe0.34 O2.04)'
_chemical_formula_sum            'C2 H4 Fe O6'
_chemical_formula_weight         179.90
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Fe O6 C2 H4'
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.209(4)
_cell_length_b                   5.5526(7)
_cell_length_c                   9.865(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 128.20(6)
_cell_angle_gamma                90.00
_cell_volume                     525.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    872
_cell_measurement_temperature    297.20(14)
_cell_measurement_theta_max      26.7480
_cell_measurement_theta_min      4.1900
_exptl_absorpt_coefficient_mu    2.824
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.5126
_exptl_crystal_size_mid          0.0409
_exptl_crystal_size_min          0.0297
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2480
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         4.24
_diffrn_ambient_temperature      297.20(14)
_diffrn_detector_area_resol_mean 8.0591
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0115086000
_diffrn_orient_matrix_UB_12      0.1218706000
_diffrn_orient_matrix_UB_13      0.0272342000
_diffrn_orient_matrix_UB_21      -0.0718767000
_diffrn_orient_matrix_UB_22      0.0247105000
_diffrn_orient_matrix_UB_23      -0.0644341000
_diffrn_orient_matrix_UB_31      -0.0128803000
_diffrn_orient_matrix_UB_32      -0.0291664000
_diffrn_orient_matrix_UB_33      0.0590060000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                479
_reflns_number_total             541
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.700
_refine_diff_density_min         -4.474
_refine_diff_density_rms         0.256
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         541
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.1090
_refine_ls_restrained_S_all      1.298
_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          0.2578
_refine_ls_wR_factor_ref         0.2684
_refine_special_details          
'This crystal has plenty of stacking faults as usual for this compound.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C1-O5
 1.25 with sigma of 0.02
 O2-C2
 1.25 with sigma of 0.02
 O3-C2 = C2-O2
 1.25 with sigma of 0.02
 O6-C1_$1 = C1_$1-O5_$1
 1.25 with sigma of 0.02
 O2_$1-C2_$1 = C2_$1-O3_$1
 1.25 with sigma of 0.02
 O6_$2-C1 = C1-O5
 1.25 with sigma of 0.02
 O3-O2
 2.237 with sigma of 0.04
 O6-O5_$1
 2.237 with sigma of 0.04
 O2_$1-O3_$1
 2.237 with sigma of 0.04
 O6_$2-O5
 2.237 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(Fe1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
Uanis(O1) \\sim Ueq, Uanis(O4) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.003
Uanis(O2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(O5) \\sim
Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.003
Uanis(C2) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.003
4. Others
 Fixed Sof: C1(0.34) C2(0.66) O1(0.34) H1A(0.34) H1B(0.34) O2(0.66) O3(0.66)
 O4(0.66) H4A(0.66) H4B(0.66) O5(0.34) O6(0.34) Fe1(0.17) Fe2(0.33)
5.a Rotating group:
 O1(H1A,H1B), O4(H4A,H4B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.4495(18) 1.677(2) 0.652(2) 0.022(4) Uani 0.34 d . 1 1 D U .
C2 C 0.4495(8) 2.1448(14) 0.6498(10) 0.0210(18) Uani 0.66 d . 2 1 D U .
O1 O 0.6717(14) 2.182(2) 0.7488(18) 0.034(3) Uani 0.34 d A 1 1 . U .
H1A H 0.6576 2.0996 0.6555 0.050 Uiso 0.34 d A 1 1 GR . .
H1B H 0.7536 2.1126 0.8467 0.050 Uiso 0.34 d A 1 1 GR . .
O2 O 0.4127(10) 1.9447(16) 0.5756(11) 0.0234(19) Uani 0.66 d B 2 1 D U .
O3 O 0.4135(6) 2.3472(12) 0.5764(7) 0.0243(16) Uani 0.66 d . 2 1 D U .
O4 O 0.6726(7) 1.6549(12) 0.7507(9) 0.0338(18) Uani 0.66 d C 2 1 . U .
H4A H 0.6545 1.5757 0.6635 0.051 Uiso 0.66 d C 2 1 GR . .
H4B H 0.7439 1.5896 0.8441 0.051 Uiso 0.66 d C 2 1 GR . .
O5 O 0.416(2) 1.879(3) 0.579(3) 0.030(5) Uani 0.34 d D 1 1 D U .
O6 O 0.4134(12) 2.474(2) 0.5784(15) 0.027(3) Uani 0.34 d . 1 1 D U .
Fe1 Fe 0.5000 2.1778(6) 0.7500 0.0234(11) Uani 0.34 d . 1 2 S TU P
Fe2 Fe 0.5000 1.6489(3) 0.7500 0.0232(9) Uani 0.66 d . 2 2 S T P

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
C1 0.021(4) 0.020(5) 0.024(5) 0.000(3) 0.013(3) -0.002(3)
C2 0.022(3) 0.026(3) 0.013(3) 0.000(2) 0.010(2) 0.000(2)
O1 0.034(4) 0.031(4) 0.034(4) -0.002(3) 0.020(3) 0.002(3)
O2 0.026(3) 0.023(3) 0.014(3) -0.001(2) 0.009(2) 0.002(3)
O3 0.028(3) 0.024(3) 0.016(2) -0.0015(19) 0.011(2) 0.001(2)
O4 0.032(3) 0.041(3) 0.027(3) 0.002(2) 0.018(2) 0.003(2)
O5 0.031(5) 0.025(5) 0.029(5) 0.000(3) 0.016(4) -0.001(3)
O6 0.028(4) 0.027(4) 0.024(4) -0.001(3) 0.015(3) -0.001(3)
Fe1 0.0262(14) 0.0156(14) 0.0235(15) 0.000 0.0129(10) 0.000
Fe2 0.0265(12) 0.0212(12) 0.0137(15) 0.000 0.0083(11) 0.000

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.51(4) 2_656 ?
C1 O5 1.257(12) . ?
C1 O6 1.266(13) 1_545 ?
C2 C2 1.554(15) 2_656 ?
C2 O2 1.251(9) . ?
C2 O3 1.260(9) . ?
O1 Fe1 2.105(13) . ?
O2 Fe2 2.127(9) . ?
O3 Fe2 2.149(6) 1_565 ?
O4 Fe2 2.103(7) . ?
O5 Fe1 2.126(19) . ?
O6 C1 1.266(13) 1_565 ?
O6 Fe1 2.116(12) . ?
Fe1 O1 2.105(13) 2_656 ?
Fe1 O5 2.126(19) 2_656 ?
Fe1 O6 2.116(12) 2_656 ?
Fe2 O2 2.127(9) 2_656 ?
Fe2 O3 2.149(6) 2_646 ?
Fe2 O3 2.149(6) 1_545 ?
Fe2 O4 2.103(7) 2_656 ?

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
_geom_angle_publ_flag
O5 C1 C1 117.0(12) . 2_656 ?
O5 C1 O6 125.9(17) . 1_545 ?
O6 C1 C1 116.9(10) 1_545 2_656 ?
O2 C2 C2 117.4(5) . 2_656 ?
O2 C2 O3 125.8(8) . . ?
O3 C2 C2 116.9(4) . 2_656 ?
C2 O2 Fe2 113.2(6) . . ?
C2 O3 Fe2 114.4(5) . 1_565 ?
C1 O5 Fe1 114.3(14) . . ?
C1 O6 Fe1 114.1(11) 1_565 . ?
O1 Fe1 O1 178.6(7) 2_656 . ?
O1 Fe1 O5 89.9(8) . . ?
O1 Fe1 O5 91.1(8) 2_656 . ?
O1 Fe1 O5 91.1(8) . 2_656 ?
O1 Fe1 O5 89.9(8) 2_656 2_656 ?
O1 Fe1 O6 89.6(5) . . ?
O1 Fe1 O6 89.3(5) 2_656 . ?
O1 Fe1 O6 89.6(5) 2_656 2_656 ?
O1 Fe1 O6 89.3(5) . 2_656 ?
O5 Fe1 O5 77.3(9) . 2_656 ?
O6 Fe1 O5 102.4(5) 2_656 2_656 ?
O6 Fe1 O5 179.2(7) 2_656 . ?
O6 Fe1 O5 102.4(5) . . ?
O6 Fe1 O5 179.2(7) . 2_656 ?
O6 Fe1 O6 77.9(6) . 2_656 ?
O2 Fe2 O2 78.9(4) . 2_656 ?
O2 Fe2 O3 179.3(3) . 2_646 ?
O2 Fe2 O3 179.3(3) 2_656 1_545 ?
O2 Fe2 O3 101.8(3) . 1_545 ?
O2 Fe2 O3 101.8(3) 2_656 2_646 ?
O3 Fe2 O3 77.6(3) 1_545 2_646 ?
O4 Fe2 O2 89.4(4) . . ?
O4 Fe2 O2 89.2(4) . 2_656 ?
O4 Fe2 O2 89.2(4) 2_656 . ?
O4 Fe2 O2 89.4(4) 2_656 2_656 ?
O4 Fe2 O3 90.7(3) 2_656 2_646 ?
O4 Fe2 O3 90.7(3) . 2_646 ?
O4 Fe2 O3 90.7(3) . 1_545 ?
O4 Fe2 O3 90.7(3) 2_656 1_545 ?
O4 Fe2 O4 178.2(4) . 2_656 ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
13 0 1 0.0148 13.0000 0.0000 1.0000 0.1768 -0.9988 -0.1084
-13 0 -1 0.0148 -13.0000 -0.0000 -1.0000 -0.1768 0.9988 0.1084
12 0 -14 0.0224 12.0000 0.0000 -14.0000 -0.2432 0.0396 -0.9806
-12 0 14 0.0184 -12.0000 -0.0000 14.0000 0.2432 -0.0396 0.9806
-3 -8 0 0.2385 -3.0000 -8.0000 -0.0000 -1.0095 0.0179 0.2720
3 8 0 0.2555 3.0000 8.0000 0.0000 1.0095 -0.0179 -0.2720
_database_code_depnum_ccdc_archive 'CCDC 1010846'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_TTF-nitrate_120K
_audit_creation_date             2013-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_chemical_name_common            ?
_chemical_name_systematic        'Tetrathiafulvalene nitrate'
_chemical_formula_moiety         '2(C6 H4 S4), 2(N O3)'
_chemical_formula_sum            'C12 H8 N2 O6 S8'
_chemical_formula_weight         532.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S8 O6 N2 H8 C12'
_chemical_oxdiff_usercomment     120k-373K-120K
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.03490(14)
_cell_length_b                   16.2047(3)
_cell_length_c                   16.4670(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.657(2)
_cell_angle_gamma                90.00
_cell_volume                     1877.09(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7034
_cell_measurement_temperature    120.3(8)
_cell_measurement_theta_max      71.2030
_cell_measurement_theta_min      3.8190
_exptl_absorpt_coefficient_mu    9.166
_exptl_absorpt_correction_T_max  0.596
_exptl_absorpt_correction_T_min  0.043
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.885
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'hexagonal or needle'
_exptl_crystal_F_000             1080
_exptl_crystal_preparation       'Electrically conductive'
_exptl_crystal_size_max          0.7591
_exptl_crystal_size_mid          0.3042
_exptl_crystal_size_min          0.0588
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13939
_diffrn_reflns_theta_full        71.14
_diffrn_reflns_theta_max         71.14
_diffrn_reflns_theta_min         3.83
_diffrn_ambient_temperature      120.3(8)
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1970971000
_diffrn_orient_matrix_UB_12      -0.0085087000
_diffrn_orient_matrix_UB_13      0.0390147000
_diffrn_orient_matrix_UB_21      -0.0098840000
_diffrn_orient_matrix_UB_22      0.0943574000
_diffrn_orient_matrix_UB_23      0.0104532000
_diffrn_orient_matrix_UB_31      -0.0950901000
_diffrn_orient_matrix_UB_32      0.0077667000
_diffrn_orient_matrix_UB_33      -0.0843774000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3208
_reflns_number_total             3520
_reflns_odcompleteness_completeness 96.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.924
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.115
_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)+(0.0837P)²+1.6583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1427
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C11(H11), C12(H12), C13(H13), C2(H2), C3(H3), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.17173(11) 0.11573(5) 0.41932(5) 0.0260(2) Uani 1 1 d . . .
S4 S 0.29635(11) -0.08609(5) 0.58605(5) 0.0257(2) Uani 1 1 d . . .
S5 S 0.17985(11) 0.10532(5) 0.59584(5) 0.0256(2) Uani 1 1 d . . .
S8 S 0.28891(11) -0.07823(5) 0.40981(5) 0.0264(2) Uani 1 1 d . . .
S2 S 0.19143(11) -0.38551(4) 0.58649(5) 0.0251(2) Uani 1 1 d . . .
S3 S 0.17885(11) -0.40894(5) 0.38942(5) 0.0262(2) Uani 1 1 d . . .
S6 S 0.28104(11) -0.58191(4) 0.41147(5) 0.0247(2) Uani 1 1 d . . .
S7 S 0.29075(11) -0.55936(5) 0.60383(5) 0.0263(2) Uani 1 1 d . . .
C6 C 0.2354(4) -0.47822(18) 0.5400(2) 0.0242(6) Uani 1 1 d . . .
C14 C 0.2547(4) -0.5475(2) 0.3131(2) 0.0272(7) Uani 1 1 d . . .
H14 H 0.2729 -0.5824 0.2690 0.033 Uiso 1 1 calc . . R
C15 C 0.2292(5) -0.4219(2) 0.6838(2) 0.0287(7) Uani 1 1 d . . .
H15 H 0.2175 -0.3877 0.7289 0.034 Uiso 1 1 calc . . R
C20 C 0.2304(4) -0.48835(18) 0.4555(2) 0.0243(6) Uani 1 1 d . . .
C1 C 0.2612(4) -0.02712(19) 0.50031(19) 0.0243(6) Uani 1 1 d . . .
C9 C 0.2080(4) 0.05589(19) 0.5045(2) 0.0238(6) Uani 1 1 d . . .
C11 C 0.1404(4) 0.20172(19) 0.5538(2) 0.0278(7) Uani 1 1 d . . .
H11 H 0.1227 0.2482 0.5859 0.033 Uiso 1 1 calc . . R
C12 C 0.2071(5) -0.4685(2) 0.3031(2) 0.0289(7) Uani 1 1 d . . .
H12 H 0.1897 -0.4461 0.2515 0.035 Uiso 1 1 calc . . R
C13 C 0.3531(5) -0.17155(19) 0.4532(2) 0.0282(7) Uani 1 1 d . . .
H13 H 0.3828 -0.2173 0.4217 0.034 Uiso 1 1 calc . . R
C2 C 0.2762(5) -0.5015(2) 0.6915(2) 0.0300(7) Uani 1 1 d . . .
H2 H 0.3001 -0.5249 0.7422 0.036 Uiso 1 1 calc . . R
C3 C 0.3577(4) -0.17459(19) 0.5343(2) 0.0278(7) Uani 1 1 d . . .
H3 H 0.3926 -0.2225 0.5617 0.033 Uiso 1 1 calc . . R
C16 C 0.1366(4) 0.20593(19) 0.4728(2) 0.0283(7) Uani 1 1 d . . .
H16 H 0.1158 0.2558 0.4461 0.034 Uiso 1 1 calc . . R
O4 O 0.0891(4) -0.24401(15) 0.67422(15) 0.0390(6) Uani 1 1 d . . .
N5 N 0.0614(4) -0.22548(17) 0.74653(17) 0.0283(6) Uani 1 1 d . . .
N7 N 0.4388(4) -0.75115(16) 0.26486(17) 0.0272(6) Uani 1 1 d . . .
O8 O 0.4055(4) -0.72577(16) 0.33542(15) 0.0411(6) Uani 1 1 d . . .
O1 O 0.5100(4) -0.82078(15) 0.25468(18) 0.0409(7) Uani 1 1 d . . .
O2 O 0.0911(4) -0.27771(17) 0.80106(16) 0.0413(6) Uani 1 1 d . . .
O3 O 0.0078(4) -0.15441(16) 0.76463(17) 0.0393(6) Uani 1 1 d . . .
O5 O 0.4000(4) -0.70547(19) 0.20606(17) 0.0466(7) 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
S1 0.0305(4) 0.0274(4) 0.0201(4) 0.0032(3) 0.0013(3) -0.0002(3)
S4 0.0321(4) 0.0251(4) 0.0198(4) 0.0012(3) 0.0010(3) 0.0004(3)
S5 0.0324(4) 0.0248(4) 0.0196(4) -0.0002(3) 0.0005(3) 0.0000(3)
S8 0.0319(4) 0.0273(4) 0.0201(4) -0.0012(3) 0.0018(3) -0.0005(3)
S2 0.0293(4) 0.0212(4) 0.0248(4) -0.0012(3) 0.0015(3) 0.0004(3)
S3 0.0311(4) 0.0214(4) 0.0262(5) 0.0028(3) 0.0041(3) 0.0008(3)
S6 0.0292(4) 0.0215(4) 0.0235(4) 0.0002(3) 0.0024(3) 0.0015(3)
S7 0.0313(4) 0.0232(4) 0.0244(4) 0.0013(3) 0.0025(3) 0.0022(3)
C6 0.0245(14) 0.0215(13) 0.0266(17) 0.0011(12) 0.0024(12) -0.0007(11)
C14 0.0318(16) 0.0277(15) 0.0224(17) -0.0006(13) 0.0048(12) 0.0002(12)
C15 0.0334(16) 0.0287(16) 0.0239(18) -0.0012(13) 0.0006(13) 0.0026(12)
C20 0.0261(14) 0.0197(13) 0.0272(17) 0.0013(12) 0.0021(12) -0.0022(11)
C1 0.0272(14) 0.0255(14) 0.0204(17) 0.0001(12) 0.0025(12) -0.0027(12)
C9 0.0255(14) 0.0248(15) 0.0211(16) 0.0015(12) 0.0022(12) -0.0021(11)
C11 0.0313(16) 0.0225(14) 0.0298(18) -0.0006(12) 0.0018(13) 0.0022(12)
C12 0.0329(16) 0.0296(16) 0.0242(17) 0.0036(13) 0.0044(13) 0.0006(12)
C13 0.0323(16) 0.0235(15) 0.0288(18) -0.0015(12) 0.0034(13) 0.0006(12)
C2 0.0332(16) 0.0324(17) 0.0245(18) -0.0020(13) 0.0012(13) 0.0012(13)
C3 0.0299(15) 0.0238(15) 0.0296(18) -0.0001(12) 0.0006(13) 0.0001(11)
C16 0.0295(15) 0.0238(14) 0.0315(19) 0.0026(13) 0.0008(13) -0.0002(12)
O4 0.0651(17) 0.0321(12) 0.0199(13) -0.0016(10) 0.0000(11) 0.0053(11)
N5 0.0286(13) 0.0311(14) 0.0252(15) -0.0011(11) -0.0007(11) 0.0027(11)
N7 0.0299(13) 0.0272(13) 0.0245(15) -0.0016(11) 0.0024(11) -0.0016(10)
O8 0.0615(16) 0.0399(13) 0.0221(13) 0.0013(11) 0.0051(11) 0.0142(12)
O1 0.0419(14) 0.0292(12) 0.0516(18) -0.0111(11) 0.0026(12) 0.0026(10)
O2 0.0556(16) 0.0422(14) 0.0261(14) 0.0101(11) 0.0054(11) 0.0134(12)
O3 0.0476(15) 0.0314(12) 0.0390(15) -0.0075(11) 0.0025(12) 0.0100(11)
O5 0.0603(17) 0.0537(16) 0.0258(14) 0.0089(12) 0.0053(12) 0.0136(13)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.722(3) . ?
S1 C16 1.725(3) . ?
S4 C1 1.720(3) . ?
S4 C3 1.726(3) . ?
S5 C9 1.717(3) . ?
S5 C11 1.730(3) . ?
S8 C1 1.718(3) . ?
S8 C13 1.731(3) . ?
S2 C6 1.716(3) . ?
S2 C15 1.726(4) . ?
S3 C20 1.721(3) . ?
S3 C12 1.732(3) . ?
S6 C14 1.722(3) . ?
S6 C20 1.719(3) . ?
S7 C6 1.726(3) . ?
S7 C2 1.725(3) . ?
C6 C20 1.401(5) . ?
C14 C12 1.334(5) . ?
C15 C2 1.338(5) . ?
C1 C9 1.398(5) . ?
C11 C16 1.336(5) . ?
C13 C3 1.336(5) . ?
O4 N5 1.246(4) . ?
N5 O2 1.250(4) . ?
N5 O3 1.249(4) . ?
N7 O8 1.257(4) . ?
N7 O1 1.247(4) . ?
N7 O5 1.247(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
_geom_angle_publ_flag
C9 S1 C16 94.72(16) . . ?
C1 S4 C3 95.20(16) . . ?
C9 S5 C11 95.17(16) . . ?
C1 S8 C13 95.42(16) . . ?
C6 S2 C15 95.12(16) . . ?
C20 S3 C12 94.43(16) . . ?
C20 S6 C14 95.18(16) . . ?
C2 S7 C6 94.65(16) . . ?
S2 C6 S7 115.81(19) . . ?
C20 C6 S2 122.9(2) . . ?
C20 C6 S7 121.3(2) . . ?
C12 C14 S6 116.8(3) . . ?
C2 C15 S2 116.9(3) . . ?
S6 C20 S3 115.87(19) . . ?
C6 C20 S3 122.9(2) . . ?
C6 C20 S6 121.3(2) . . ?
S8 C1 S4 115.30(18) . . ?
C9 C1 S4 122.0(3) . . ?
C9 C1 S8 122.7(3) . . ?
S5 C9 S1 115.67(18) . . ?
C1 C9 S1 122.6(3) . . ?
C1 C9 S5 121.7(3) . . ?
C16 C11 S5 116.6(2) . . ?
C14 C12 S3 117.7(3) . . ?
C3 C13 S8 116.6(2) . . ?
C15 C2 S7 117.5(3) . . ?
C13 C3 S4 117.4(3) . . ?
C11 C16 S1 117.7(2) . . ?
O4 N5 O2 119.8(3) . . ?
O4 N5 O3 120.1(3) . . ?
O3 N5 O2 120.1(3) . . ?
O1 N7 O8 120.0(3) . . ?
O5 N7 O8 118.8(3) . . ?
O5 N7 O1 121.2(3) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 2 -11 0.1298 0.0024 1.9841 -10.9902 -0.4461 0.0723 0.9425
0 -2 11 0.1588 -0.0024 -1.9841 10.9902 0.4461 -0.0723 -0.9425
0 -11 0 0.0439 0.0019 -10.9978 0.0002 0.0932 -1.0377 -0.0856
0 11 0 0.0149 -0.0019 10.9978 -0.0002 -0.0932 1.0377 0.0856
4 0 4 0.3595 3.9964 0.0077 3.9984 -0.6317 0.0030 -0.7173
-4 0 -4 0.3595 -3.9964 -0.0077 -3.9984 0.6317 -0.0030 0.7173
4 2 -4 0.3388 3.9981 1.9960 -3.9945 -0.9608 0.1071 -0.0276
-4 -2 4 0.3148 -3.9981 -1.9960 3.9945 0.9608 -0.1071 0.0276

_exptl_crystal_recrystallization_method 'Redox reaction of precursor'
_chemical_properties_physical    Heat-sensitive
_database_code_depnum_ccdc_archive 'CCDC 1020095'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_TTF-nitrate_300K
_audit_creation_date             2013-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_chemical_name_common            ?
_chemical_name_systematic        'Tetrathiafulvalene nitrate'
_chemical_formula_moiety         '2(C6 H4 S4), 2(N O3)'
_chemical_formula_sum            'C12 H8 N2 O6 S8'
_chemical_formula_weight         532.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S8 C12 H8 N2 O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1480(3)
_cell_length_b                   16.1738(6)
_cell_length_c                   16.6234(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.867(3)
_cell_angle_gamma                90.00
_cell_volume                     1921.60(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3389
_cell_measurement_temperature    300.1(4)
_cell_measurement_theta_max      61.7540
_cell_measurement_theta_min      5.3350
_exptl_absorpt_coefficient_mu    8.954
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_correction_T_min  0.162
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'hexagonal or needle'
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.4182
_exptl_crystal_size_mid          0.2207
_exptl_crystal_size_min          0.0383
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5856
_diffrn_reflns_theta_full        61.81
_diffrn_reflns_theta_max         61.81
_diffrn_reflns_theta_min         3.81
_diffrn_ambient_temperature      300.1(4)
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0593031000
_diffrn_orient_matrix_UB_12      -0.0830062000
_diffrn_orient_matrix_UB_13      0.0372373000
_diffrn_orient_matrix_UB_21      0.0348689000
_diffrn_orient_matrix_UB_22      0.0355928000
_diffrn_orient_matrix_UB_23      0.0848433000
_diffrn_orient_matrix_UB_31      -0.2042678000
_diffrn_orient_matrix_UB_32      0.0302817000
_diffrn_orient_matrix_UB_33      0.0022318000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2621
_reflns_number_total             2839
_reflns_odcompleteness_completeness 92.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.093
_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)+(0.0845P)²+3.5951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1628
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C13(H13), C17(H17), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.20067(16) 0.58622(7) 0.41362(6) 0.0434(3) Uani 1 1 d . . .
S2 S 0.32785(16) 0.38952(7) 0.58390(6) 0.0453(3) Uani 1 1 d . . .
S3 S 0.18771(17) 0.40753(7) 0.89411(7) 0.0467(3) Uani 1 1 d . . .
S4 S 0.28326(17) 0.56869(7) 1.09990(7) 0.0475(3) Uani 1 1 d . . .
S5 S 0.27717(17) 0.58219(7) 0.90889(6) 0.0434(3) Uani 1 1 d . . .
S6 S 0.21052(17) 0.58309(7) 0.58812(6) 0.0451(3) Uani 1 1 d . . .
S7 S 0.31937(17) 0.39472(7) 0.40884(6) 0.0437(3) Uani 1 1 d . . .
S8 S 0.19600(16) 0.39328(7) 1.09031(7) 0.0449(3) Uani 1 1 d . . .
N1 N -0.0437(5) 0.7493(2) 0.2619(2) 0.0480(9) Uani 1 1 d . . .
N2 N 0.4580(6) 0.7374(3) 0.2477(2) 0.0522(10) Uani 1 1 d . . .
C3 C 0.2383(5) 0.5296(3) 0.5000(2) 0.0367(9) Uani 1 1 d . . .
C4 C 0.2913(6) 0.4467(3) 0.4980(2) 0.0362(9) Uani 1 1 d . . .
C5 C 0.2360(6) 0.4840(3) 1.0402(3) 0.0389(9) Uani 1 1 d . . .
O6 O 0.0150(7) 0.6794(3) 0.2548(3) 0.1008(17) Uani 1 1 d . . .
C7 C 0.2558(7) 0.5428(3) 0.8132(3) 0.0493(11) Uani 1 1 d . . .
H7 H 0.2727 0.5759 0.7681 0.059 Uiso 1 1 calc . . R
O8 O 0.4228(8) 0.7508(4) 0.3186(3) 0.1081(18) Uani 1 1 d . . .
C9 C 0.1497(7) 0.6751(3) 0.5426(3) 0.0482(11) Uani 1 1 d . . .
H9 H 0.1218 0.7219 0.5726 0.058 Uiso 1 1 calc . . R
C10 C 0.3654(7) 0.2985(3) 0.5335(3) 0.0511(11) Uani 1 1 d . . .
H10 H 0.3882 0.2495 0.5612 0.061 Uiso 1 1 calc . . R
C11 C 0.2300(7) 0.4350(3) 1.1848(3) 0.0546(12) Uani 1 1 d . . .
H11 H 0.2201 0.4028 1.2309 0.066 Uiso 1 1 calc . . R
O12 O 0.4367(10) 0.7900(5) 0.1996(3) 0.163(3) Uani 1 1 d . . .
C13 C 0.1445(6) 0.6762(3) 0.4627(3) 0.0480(11) Uani 1 1 d . . .
H13 H 0.1117 0.7238 0.4344 0.058 Uiso 1 1 calc . . R
C14 C 0.2322(6) 0.4903(3) 0.9565(2) 0.0376(9) Uani 1 1 d . . .
O15 O -0.0736(8) 0.7950(4) 0.2051(3) 0.121(2) Uani 1 1 d . . .
O16 O -0.0782(7) 0.7757(3) 0.3295(2) 0.0918(15) Uani 1 1 d . . .
C17 C 0.2141(7) 0.4636(3) 0.8065(3) 0.0529(12) Uani 1 1 d . . .
H17 H 0.1995 0.4387 0.7563 0.064 Uiso 1 1 calc . . R
C19 C 0.3609(7) 0.3005(3) 0.4537(3) 0.0503(11) Uani 1 1 d . . .
H19 H 0.3793 0.2529 0.4233 0.060 Uiso 1 1 calc . . R
C20 C 0.2709(7) 0.5146(3) 1.1890(3) 0.0568(13) Uani 1 1 d . . .
H20 H 0.2923 0.5405 1.2382 0.068 Uiso 1 1 calc . . R
O21 O 0.5018(8) 0.6682(4) 0.2319(5) 0.136(3) 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
S1 0.0590(7) 0.0399(6) 0.0312(6) 0.0038(4) -0.0031(5) 0.0003(5)
S2 0.0553(7) 0.0484(7) 0.0322(6) 0.0095(5) 0.0010(5) 0.0003(5)
S3 0.0609(7) 0.0308(6) 0.0485(7) -0.0082(5) 0.0057(5) -0.0001(5)
S4 0.0619(7) 0.0367(6) 0.0437(6) -0.0048(5) 0.0005(5) -0.0052(5)
S5 0.0588(7) 0.0308(6) 0.0406(6) 0.0013(4) 0.0025(5) -0.0046(5)
S6 0.0610(7) 0.0439(7) 0.0304(6) -0.0037(4) 0.0023(5) -0.0028(5)
S7 0.0592(7) 0.0403(6) 0.0315(6) -0.0035(4) -0.0036(5) -0.0001(5)
S8 0.0573(7) 0.0321(6) 0.0454(7) 0.0060(4) -0.0010(5) 0.0009(5)
N1 0.063(2) 0.041(2) 0.041(2) 0.0027(17) -0.0002(17) -0.0062(19)
N2 0.062(2) 0.052(2) 0.042(2) -0.0073(19) -0.0052(18) 0.014(2)
C3 0.044(2) 0.041(2) 0.025(2) 0.0005(17) -0.0011(16) -0.0059(19)
C4 0.042(2) 0.039(2) 0.027(2) 0.0007(17) -0.0017(16) -0.0047(19)
C5 0.042(2) 0.031(2) 0.044(2) 0.0008(18) 0.0028(17) 0.0011(18)
O6 0.092(3) 0.054(3) 0.157(5) -0.042(3) 0.001(3) 0.005(2)
C7 0.066(3) 0.042(3) 0.040(2) 0.002(2) 0.006(2) -0.002(2)
O8 0.158(5) 0.111(4) 0.055(3) -0.002(3) -0.010(3) 0.033(4)
C9 0.057(3) 0.038(2) 0.049(3) -0.002(2) 0.006(2) 0.001(2)
C10 0.056(3) 0.041(3) 0.056(3) 0.014(2) 0.002(2) 0.003(2)
C11 0.072(3) 0.052(3) 0.040(2) 0.010(2) -0.003(2) -0.004(3)
O12 0.171(6) 0.223(8) 0.096(4) 0.098(5) 0.054(4) 0.103(6)
C13 0.056(3) 0.036(2) 0.052(3) 0.004(2) 0.001(2) -0.001(2)
C14 0.044(2) 0.029(2) 0.040(2) 0.0000(17) 0.0026(17) -0.0008(18)
O15 0.142(4) 0.161(6) 0.060(3) 0.050(3) 0.022(3) 0.046(4)
O16 0.136(4) 0.093(3) 0.046(2) -0.003(2) -0.002(2) 0.042(3)
C17 0.069(3) 0.052(3) 0.039(2) -0.009(2) 0.007(2) -0.004(2)
C19 0.058(3) 0.035(2) 0.058(3) -0.001(2) 0.000(2) -0.002(2)
C20 0.069(3) 0.066(3) 0.036(3) -0.001(2) -0.003(2) -0.003(3)
O21 0.101(4) 0.081(4) 0.228(7) -0.066(4) 0.019(4) 0.012(3)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.720(4) . ?
S1 C13 1.719(5) . ?
S2 C4 1.718(4) . ?
S2 C10 1.717(5) . ?
S3 C14 1.720(4) . ?
S3 C17 1.729(5) . ?
S4 C5 1.722(4) . ?
S4 C20 1.723(5) . ?
S5 C7 1.719(5) . ?
S5 C14 1.717(4) . ?
S6 C3 1.716(4) . ?
S6 C9 1.723(5) . ?
S7 C4 1.718(4) . ?
S7 C19 1.721(5) . ?
S8 C5 1.714(4) . ?
S8 C11 1.723(5) . ?
N1 O6 1.211(6) . ?
N1 O15 1.215(6) . ?
N1 O16 1.231(5) . ?
N2 O8 1.229(6) . ?
N2 O12 1.175(7) . ?
N2 O21 1.194(6) . ?
C3 C4 1.395(6) . ?
C5 C14 1.394(6) . ?
C7 C17 1.321(7) . ?
C9 C13 1.327(7) . ?
C10 C19 1.327(7) . ?
C11 C20 1.323(7) . ?

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
_geom_angle_publ_flag
C13 S1 C3 95.1(2) . . ?
C10 S2 C4 94.5(2) . . ?
C14 S3 C17 94.5(2) . . ?
C5 S4 C20 94.6(2) . . ?
C14 S5 C7 95.3(2) . . ?
C3 S6 C9 95.3(2) . . ?
C4 S7 C19 94.7(2) . . ?
C5 S8 C11 94.9(2) . . ?
O6 N1 O15 123.3(5) . . ?
O6 N1 O16 119.2(5) . . ?
O15 N1 O16 117.5(5) . . ?
O12 N2 O8 120.0(6) . . ?
O12 N2 O21 124.1(6) . . ?
O21 N2 O8 115.8(6) . . ?
S6 C3 S1 115.2(3) . . ?
C4 C3 S1 122.1(3) . . ?
C4 C3 S6 122.7(3) . . ?
S7 C4 S2 115.8(3) . . ?
C3 C4 S2 122.4(3) . . ?
C3 C4 S7 121.8(3) . . ?
S8 C5 S4 115.7(2) . . ?
C14 C5 S4 121.2(3) . . ?
C14 C5 S8 123.1(3) . . ?
C17 C7 S5 117.0(4) . . ?
C13 C9 S6 117.0(4) . . ?
C19 C10 S2 117.8(4) . . ?
C20 C11 S8 117.2(4) . . ?
C9 C13 S1 117.4(4) . . ?
S5 C14 S3 115.4(2) . . ?
C5 C14 S3 123.1(3) . . ?
C5 C14 S5 121.5(3) . . ?
C7 C17 S3 117.7(4) . . ?
C10 C19 S7 117.1(4) . . ?
C11 C20 S4 117.6(4) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 11 0.0983 0.0028 -0.0043 11.0060 0.4100 0.9337 0.0239
0 0 -11 0.1223 -0.0028 0.0043 -11.0060 -0.4100 -0.9337 -0.0239
-4 3 -4 0.2192 -4.0020 2.9892 -4.0034 -0.1599 -0.3728 0.8991
4 -3 4 0.1282 4.0020 -2.9892 4.0034 0.1599 0.3728 -0.8991
4 -3 -6 0.1428 3.9995 -2.9853 -6.0020 -0.2129 -0.4760 -0.9208
-4 3 6 0.1968 -3.9995 2.9853 6.0020 0.2129 0.4760 0.9208
0 10 0 0.0373 -0.0010 9.9955 0.0089 -0.8293 0.3565 0.3029
0 -10 0 0.0010 0.0010 -9.9955 -0.0089 0.8293 -0.3565 -0.3029

_exptl_crystal_recrystallization_method 'Redox reaction of precursor'
_chemical_properties_physical    Heat-sensitive
_database_code_depnum_ccdc_archive 'CCDC 1020096'
